EP4152954A1 - Sweetener and flavor compositions - Google Patents

Sweetener and flavor compositions

Info

Publication number
EP4152954A1
EP4152954A1 EP20936550.1A EP20936550A EP4152954A1 EP 4152954 A1 EP4152954 A1 EP 4152954A1 EP 20936550 A EP20936550 A EP 20936550A EP 4152954 A1 EP4152954 A1 EP 4152954A1
Authority
EP
European Patent Office
Prior art keywords
composition
less
ppm
glycosylated
extract
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP20936550.1A
Other languages
German (de)
French (fr)
Other versions
EP4152954A4 (en
Inventor
Jingang Shi
Hansheng Wang
Thomas Eidenberger
Xiaorui ZHANG
Weiyao Shi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EPC Natural Products Co Ltd
Original Assignee
EPC Natural Products Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by EPC Natural Products Co Ltd filed Critical EPC Natural Products Co Ltd
Publication of EP4152954A1 publication Critical patent/EP4152954A1/en
Publication of EP4152954A4 publication Critical patent/EP4152954A4/en
Pending legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/60—Sweeteners
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/84—Flavour masking or reducing agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/24—Condensed ring systems having three or more rings
    • C07H15/256—Polyterpene radicals
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/33—Artificial sweetening agents containing sugars or derivatives
    • A23L27/36—Terpene glycosides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2200/00—Function of food ingredients
    • A23V2200/15—Flavour affecting agent
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/24—Non-sugar sweeteners
    • A23V2250/258—Rebaudioside
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/24—Non-sugar sweeteners
    • A23V2250/262—Stevioside

Definitions

  • the present disclosure relates generally to sweeteners and flavoring agents, and their use in food, beverage, feed, pharmaceutical and personal care products.
  • Caloric sugars are widely used in the food and beverage industry. However, there is a growing trend toward use of more healthy alternatives, including non-caloric or low caloric sweeteners.
  • Popular non-caloric sweeteners include high intensity synthetic sweeteners, such as aspartame (e.g., NutraSweet, Equal) , sucralose (Splenda) , and acesulfame potassium (also known as acesulfame K, or Ace-K) , as well as high intensity natural sweeteners, which are typically derived from plants such as Stevia plants, sweet tea plants and monk fruit plants.
  • the present application relates to a composition
  • a composition comprising one or more products selected from the group consisting of rubusoside (RU) , sweet tea components (STCs) , sweet tea extracts (STEs) , morgrosides (MGs) monk fruit components (MFCs) , monk fruit extracts (MFEs) , steviol glycosides (SGs) , Stevia extracts (SEs) , glycosylated rubusoside (GRU) , glycosylated sweet tea components (GSTCs) , glycosylated sweet tea extracts (GSTEs) , glycosylated monk fruit components (GMFCs) , glycosylated morgrosides (GMGs) , glycosylated monk fruit extracts (GMFEs) , glycosylated stevia glycosides (GSGs) , and glycosylated stevia extracts (GSEs) , wherein the one or more products are present in the composition in
  • the sweetener or flavoring composition comprises a STE containing enriched rubusoside (RU) .
  • the sweetener or flavoring composition comprises a STE containing enriched diterpene glycoside.
  • the sweetener or flavoring composition comprises an STE that comprises one or more sweet tea derived components (STC) selected from the group consisting of rubusoside (RU) , suavioside (SU) , steviolmonoside, rebaudioside A, 13-O- ⁇ -D-glucosyl-steviol, isomers of rebaudioside B, isomers of stevioside, panicloside IV, poweroside, ent-16 ⁇ , 17-dihydroxy-kaurane-19-oic acid, ent-13-hydroxy-kaurane-16-en-19-oic acid, ent-kaurane-16-en-19-oic-13-O- ⁇ -D-glucoside, ent-16 ⁇ , 17-dihydroxy-kaurane-3-one, ent-16 ⁇ , 17-dihydroxy-kaurane-19-oic acid, ent-kaurane-16 ⁇ , 17-diol-3-one-17-O- ⁇ -D-glucoside, ent-16
  • the sweetener or flavoring composition comprises a STE that comprisies one or more suaviosides slected from the group consisting of SU-A, SU-B, SU-C1, SU-D1, SU-D2, SU-E, SU-F, SU-G, SU-H, SU-I, and SU-J.
  • the sweetener or flavoring composition comprises a STE wherein the STE is purified RU.
  • the sweetener or flavoring composition comprises a GSTE.
  • the sweetener or flavoring composition comprises a GSTE containing enriched glycosylated rubusoside (RU) .
  • the sweetener or flavoring composition comprises a GSTE containing enriched glycosylated diterpene glycoside.
  • the sweetener or flavoring composition comprises a GSTE, wherein the GSTE is glycosylated RU.
  • the STE comprises enriched RU. In some related embodiments, the STE comprises enriched diterpene glycoside. In some related embodiments, the STE comprises one or more STCs selected from the group consisting of RU, SU, steviolmonoside, rebaudioside A, 13-O- ⁇ -D-glucosyl-steviol, isomers of rebaudioside B, isomers of stevioside, panicloside IV, poweroside, ent-16 ⁇ , 17-dihydroxy-kaurane-19-oic acid, ent-13-hydroxy-kaurane-16-en-19-oic acid, ent-kaurane-16-en-19-oic-13-O- ⁇ -D-glucoside, ent-16 ⁇ , 17-dihydroxy-kaurane-3-one, ent-16 ⁇ , 17-dihydroxy-kaurane-19-oic acid, ent-kaurane-16 ⁇ , 17-diol-3-one-17-O- ⁇ -D-
  • the STE comprisies one or more suavosides slected from the group consisting of SU-A, SU-B, SU-C1, SU-D1, SU-D2, SU-E, SU-F, SU-G, SU-H, SU-I, and SU-J.
  • the GSTE is a glycosylation product of an STE that comprises enriched RU. In some related embodiments, the GSTE is a glycosylation product of a STE that comprises enriched diterpene glycoside. In some related embodiments, the GSTE is a glycosylation product of a STE that comprises one or more STCs selected from the group consisting of RU, SU, steviolmonoside, rebaudioside A, 13-O- ⁇ -D-glucosyl-steviol, isomers of rebaudioside B, isomers of stevioside, panicloside IV, poweroside, ent-16 ⁇ , 17-dihydroxy-kaurane-19-oic acid, ent-13-hydroxy-kaurane-16-en-19-oic acid, ent-kaurane-16-en-19-oic-13- O- ⁇ -D-glucoside, ent-16 ⁇ , 17-dihydroxy-kaurane-3-one, ent-16 ⁇ , 17-dihydroxy-ka
  • the GSTE is a glycosylation product of a STE that comprisies one or more suavosides slected from the group consisting of SU-A, SU-B, SU-C1, SU-D1, SU-D2, SU-E, SU-F, SU-G, SU-H, SU-I, and SU-J.
  • Hydrolyzed starch are often used for glycosylation of STEs, SEs, MFEs, SGs, MGs, rubusoside, and suaviosides.
  • hydrolyzed starch hydrolyzed starch
  • STEs STEs
  • SEs MFEs
  • SGs SGs
  • MGs rubusoside
  • suaviosides suaviosides.
  • unreacted starch and/or dextrin derivatives possess cariogenic potential and the propensity for tooth decay if these agents remain present in the glycosylated (or natural sweetener) compositions that are orally administered.
  • sweetener compositions in which unreacted sugar donors are reduced.
  • the present application provides a sweetener or flavor composition
  • a sweetener or flavor composition comprising: (a) one or more glycosylated substances selected from glycosylated sweet tea extracts, glycosylated rubusoside, glycosylated suaviosides, glycosylated stevia glycosides, glycosylated stevia extracts, glycosylated monk fruit extracts, and/or glycosylated mogrosides; (b) one or more unreacted substances of sweet tea extracts, rubusoside, suaviosides, stevia extracts, stevia glycosides, monk fruit extracts, and/or mogrosides; and (c) one or more unreacted sugar donors or residues thereof, where the sugar donors or residues thereof are present in the sweetener or flavor composition in an amount greater than zero, but less than 15%, less than 10%, less than 5%, less than 4%, less than 3%, less than 2%, less than 1%, less than 0.5%, less than
  • the present application provides a method for measuring the amount of unreacted sugar donors in a sweetener or flavor composition, as well as a method for removing unreacted sugar donors in a sweetener or flavor composition.
  • a consumable product comprising one or more components selected from the group consisting of RU, GRU, STEs, GSTEs, STCs, GSTCs, Mgs, GMGs, MFCs, GMFCs, SEs, GSEs, SCs, GSCs, SGs, and GSGs in a total amount of 0.00001-99.9 wt%.
  • the consumable product is selected from the group consisting of beverage products, confections, condiments, dairy products, cereal compositions, chewing compositions, tabletop sweetener compositions, medicinal compositions, oral hygient compositions, cosmetic compositions, and smokable compositions.
  • the consumable product is a beverage and the beverage comprises the one or more components in an amount of 0.01-5000 ppm.
  • the consumable product is a food product and the food product comprises the one or more components in an amount of 0.01-5000 ppm.
  • the consumable product is a personal care product and personal care product comprises the one or more components in an amount of 0.01-5000 ppm.
  • the consumable product containing the above described sweetener or flavor composition is an oral hygiene product selected from the group consisting of toothpaste, tooth polish, tooth whitening agent, mouthwash, mouth rinse, mouth spray, breath fresheners, and dentifrice.
  • the oral hygiene product comprises a sweetener composition
  • a sweetener composition comprising (1) one or more components selected from the group consisting ofRU, GRU, STEs, GSTEs, STCs, GSTCs, MGs, GMGs, MFCs, GMFCs, SEs, GSEs, SCs, GSCs, SGs and GSGs of the present application, and (2) sugar donors or residues thereof in an amount that is greater than zero, but is less than 15%, less than 10%, less than 5%, less than 4%, less than 3%, less than 2%, less than 1%, less than 0.5%, less than 0.1%, less than 0.05%, or less than 0.01% (wt/wt) of the sweetener composition.
  • the present application provides a consumable product comprising one or more components selected from the group consisting of RU, GRU, SGs, GSGs, SEs, GSEs, STEs, GSTEs, STCs and GSTCs of the present application.
  • the one or more components are present in the consumable product in a concentration ranging from 0.0001 wt %to 99.9999 wt %, 0.0001 wt %to 75 wt %, 0.0001 wt % to 50 wt %, 0.0001 wt %to 25 wt %, 0.0001 wt %to 10 wt %, 0.0001 wt %to 5 wt %, 0.0001 wt %to 1 wt %, 0.0001 wt %to 0.5 wt %, 0.0001 wt %to 0.2 wt %, 0.0001 wt %to 0.05 wt %, 0.0001 wt %to 0.01 wt %, 0.0001 wt %to 0.005 wt %, or any range derived from any two of these values.
  • the consumable product is a beverage product in which the one or more components are present in a final concentration range of 1-15,000 ppm.
  • the present application provides a method for modifying a consumable product, comprising adding to the consumable product (e.g., beverage, food, oral hygiene or personal care product) one or more components selected from the group consisting of RU, GRU, STEs, GSTEs, STCs, GSTCs, MGs, GMGs, MFCs, GMFCs, SEs, GSEs, SCs, GSCs, SGs, and GSGs of the present application.
  • the consumable product e.g., beverage, food, oral hygiene or personal care product
  • the one or more components are added to the consumable product at a final concentration ranging from 0.0001 wt %to 99.9999 wt %, 0.0001 wt %to 75 wt %, 0.0001 wt %to 50 wt %, 0.0001 wt %to 25 wt %, 0.0001 wt %to 10 wt %, 0.0001 wt %to 5 wt %, 0.0001 wt %to 1 wt %, 0.0001 wt %to 0.5 wt %, 0.0001 wt %to 0.2 wt %, 0.0001 wt %to 0.05 wt %, 0.0001 wt %to 0.01 wt %, 0.0001 wt %to 0.005 wt %, or any range derived from any two of these values.
  • the consumable product is a beverage product
  • FIG. 1 is a representative time-intensity curve showing a relative appearance-time profile associated with taste tasting, including onset, maximum sweetness, lingering on and lingering off phases.
  • FIGS. 2A and 2B show the sugar equivalence (SugarE) as a function of concentration (ppm) in Example 3 for RU20 and GRU20, respectively, including the SugarE at which bitterness can be perceived
  • FIG. 3A shows the relationship between the sensory evaluation results and the ratio of sucralose to GTRU20 in Example 7.
  • FIG. 3B shows the relationship between the overall likability results as a function of the ratio of sucralose to GTRU20 in Example 7.
  • FIG. 4A shows the relationship between the sensory evaluation results and the ratio of RA97 to GTRU20 in Example 8.
  • FIG. 4B shows the relationship between the overall likability results as a function of the ratio of RA97 to GTRU20 in Example 8.
  • FIGS. 5A and 5B show the sugar equivalence (SugarE) as a function of concentration (ppm) in Example 9 for RU90 and GRU90, respectively.
  • FIG. 6A shows the relationship between the sensory evaluation results and the ratio of acesulfame-K to GRU90 in Example 10.
  • FIG. 6B shows the relationship between the overall likability results in Example 10 as a function of the ratio of acesulfame-K to GRU90.
  • FIG. 7A-7F show sweetness profiles as a function of time corresponding to samples containing different rubusoside (RU) compositions containing 15 ppm thaumatin compared to 15 ppm thaumatin alone in Example 13.
  • FIG. 7A control containing 15 ppm thaumatin only;
  • FIG. 7B 50 ppm RU20 + 15 ppm thaumatin;
  • FIG. 7C 50 ppm RU90 + 15 ppm thaumatin;
  • FIG. 7D 50 ppm GRU20 + 15 ppm thaumatin;
  • FIG. 7E 50 ppm GRU90 + 15 ppm thaumatin;
  • FIG. 7F 50 ppm TRU20 + 15 ppm thaumatin.
  • FIGS. 8A and 8B show GC/MS chromatograms of RU90 and GRU90 samples in Example 14, respectively.
  • Unknown 1 shows an MS spectrum indicative for Suavioside B.
  • Unknown 2 shows an MS spectrum indicative for Suavioside H.
  • Unknown 3 shows an MS spectrum tentative for 9-Hydroxy-Suavioside J.
  • Unknown 4 shows an MS spectrum indicative for Suavioside K. m/z across (+x Glc) indicates glucosylated rubusoside and the number of added glucose units. In most cases the peak shape indicates co-elution of compounds with the same m/z value but different glucosylation patterns.
  • FIGS. 9A and 9B show GC/MS chromatograms of RU20 and GRU20 samples in Example 14, respectively.
  • Unknown 1 shows an MS spectrum indicative for Suavioside B.
  • Unknown 2 shows an MS spectrum indicative for Suavioside H.
  • Unknown 3 shows an MS spectrum tentative for 9-Hydroxy-Suavioside J.
  • Unknown 4 shows an MS spectrum indicative for Suavioside K. m/z across (+x Glc) indicates glucosylated rubusoside and the number of added glucose units. In most cases the peak shape indicates co-elution of compounds with the same m/z value but different glucosylation patterns.
  • FIG. 10 shows a chromatogram (MS-Trace) depicting spectra indicative of a molar mass 966 or less in the GRU20 sample in Example 14 showing Rub-lGlc (2 isomers) and Rub-2Glc (2 isomers) .
  • FIG. 11 shows a two chromatograms, including an upper trace for RU20 at a wavelength (UV) of 254 nm, and a lower trace for GRU20 indicative of phenolic acids and polyphenols as described in Example 14.
  • FIGs. 12A-12C show representative chromatograms of RU20 as described in Example 14.
  • FIGs. 13A-13D show representative chromatograms of GRU20 in Example 14.
  • FIGs. 14A-14C show representative chromatograms of RU90 as described in Example 14.
  • FIGs. 15A-15D show representative chromatograms of GRU90 as described in Example 14.
  • FIG. 16 shows representative chromatograms of RU20 SIM neg as described in Example 14. MS 497, 335, and 317 peaks are indicative of suaviosides with an isosteviol skeleton.
  • FIG. 17 shows representative chromatograms of TRU20, SIM neg as described in Example 14. MS 497, 335, and 317 peaks are indicative of suaviosides with an isosteviol skeleton.
  • FIG. 18 shows representative chromatograms of GRU20, SIM neg as described in Example 14. MS 497, 335, and 317 peaks are indicative of suaviosides with an isosteviol skeleton.
  • FIG. 19 shows representative chromatograms of GTRU20, SIM neg as described in Example 14. MS 497, 335, and 317 peaks are indicative for suaviosides with an isosteviol skeleton.
  • FIG. 20 shows representative chromatograms of RU20 as described in Example 14, including a positive MS 439 peak.
  • FIG. 21 shows the different phases in the time intensity profiles in Example 15, including phase 1 reflecting the time of onset and increasing intensity of sweetness/acidity as a joint measure; phase 2 reflects the balanced sweetness/acidity phase; and phase 3 reflects the decay of acidity and sweetness lingering.
  • the combined phases provide an estimate for the overall sweetness/acidity perception.
  • FIG. 22A shows time-intensity profiles for sweetness/acidity perception in the TRU20-and GTRU20-1emonade samples in Example 15.
  • FIG. 22B shows time-intensity profiles for sweetness/acidity perception in RU 90-and GRU90-1emonade samples in Example 15.
  • FIG. 23A shows time-intensity profiles for sweetness/acidity perception in the TRU20-and GTRU20-Fanta Zero samples in Example 15.
  • FIG. 23B shows time-intensity profiles for sweetness/acidity perception in RU 90-and GRU90-Fanta Zero samples in Example 15.
  • FIG. 24A shows the results from sensory evaluations of product compositions containing mixtures of GSTV85 and GRU90 in different ratios.
  • FIG. 24B shows the overall likability of the product compositions in FIG. 24A.
  • FIG. 25 shows the results from sensory evaluations on adding glycosylated steviol glycosides (GSG) product 22-02 in Example 22 in Cherry Blossom whitening Lion toothpaste.
  • GSG glycosylated steviol glycosides
  • FIG. 26 shows the results from sensory evaluations on adding glycosylated steviol glycosides (GSG) product 22-03 in Example 22 in White &White Lion toothpaste.
  • GSG glycosylated steviol glycosides
  • FIG. 27 shows the results from sensory evaluations on adding glycosylated steviol glycosides (GSG) product 22-03 in Example 22 in toothpaste.
  • GSG glycosylated steviol glycosides
  • FIG. 28A shows the HPLC chromatograms of maltodextin standard and glucose standard.
  • FIG. 28B shows the HPLC chromatogram of samples from Example 22.
  • FIG. 29 shows a combined water steam distillation and solvent extraction/concentration device.
  • ST plant Chinese sweet tea plant” , “sweet tea plant” , and “Rubus suavissimus plant” are used interchangeably with reference to a Rubus suavissimus plant.
  • sweet tea extract refers to extract prepared from the whole ST plant, in the aerial part of an ST plant, in the leaves of an ST plant, in the flowers of an ST plant, in the fruit of an ST plant, in the seeds of an ST plant, in the roots of an ST plant, branches of an ST plant, and/or any other portions of an ST plant. It should also be understood that a sweet tea extract (STE) can be purified and/or separated into one or more sweet tea components (STC) .
  • STC sweet tea components
  • sweet tea component refers to a component of a STE.
  • a STC such as rubusoside, may be purified from a natural source, produced by a chemical or enzymatic process (e.g., converted from stevioside with glycosyl hydrolase) , or produced by fermentation.
  • STC examples include, but are not limited to, rubusoside (RU) , suaviosides (SUs) , steviolmonoside, rebaudioside A, 13-O- ⁇ -D-glucosyl-steviol, isomers of rebaudioside B, isomers of stevioside, panicloside IV, poweroside, ent-16 ⁇ , 17-dihydroxy-kaurane-19-oic acid, ent-13-hydroxy-kaurane-16-en-19-oic acid, ent-kaurane-16-en-19-oic-13-O- ⁇ -D-glucoside, ent-16 ⁇ , 17-dihydroxy-kaurane-3-one, ent-16 ⁇ , 17-dihydroxy-kaurane-19-oic acid, ent-kaurane-16 ⁇ , 17-diol-3-one-17-O- ⁇ -D-glucoside, ent-16 ⁇ , 17-dihydroxy-kaurane-3-one, ent-kaurane-16
  • suavosides include, but are not limited to, SU-A, SU-B, SU-C1, SU-D1, SU-D2, SU-E, SU-F, SU-G, SU-H, SU-I, and SU-J.
  • non-Stevia sweet tea component or “NS-STC” refers to a STC that is not present in detectable amount in a naturally growing Stevia plant.
  • NS-STC include, but are not limited to, sauviosides.
  • suaviosides refers to a group of kaurane-type diterpene glycosides that can can be isolated from the leaves of Rubus suavissimus.
  • suaviosides include, but are not limited to, SU-A, SU-B, SU-C1, SU-D1, SU-D2, SU-E, SU-F, SU-G, SU-H, SU-I, and SU-J.
  • the chemical structure of some suaviosides are shown in Table 14-7.
  • non-Stevia sweet tea extract or “NS-STE” refers to a STE that comprises a NS-STC.
  • glycosylation product of a STE refers to a glycosylation product of a STE.
  • glycosylation product of a STC.
  • glycosylation product of a NS-STC refers to a glycosylation product of a NS-STC.
  • rubusoside or “RU” are used interchangeably with reference to a steviol glycoside that is steviol in which both the carboxy group and the tertiary allylic hydroxy group have been converted to their corresponding beta-D-glucosides.
  • Rubusoside may be extracted from a natural source, e.g., leaves from Rubus suavissimus, produced by a chemical or enzymatic process, or produced by fermentation.
  • steviol glycoside a glycoside of steviol, a diterpene compound found in Stevia leaves.
  • Non-limiting examples of steviol glycosides are shown in Tables A or B below.
  • the steviol glycosides for use in the present application are not limited by source or origin. Steviol glycosides may be extracted from Stevia leaves, synthesized by enzymatic processes or chemical syntheses, or produced by fermentation.
  • rebaudioside A, ” “Reb A, ” and “RA” are equivalent terms referring to the same molecule. The same condition applies to all lettered rebaudiosides.
  • Stepvia extract (SE) refers to a plant extract from Stevia that contains varying percentages of SGs.
  • Stepvia component (SC) refers to a component of a SE.
  • GSC glycosylation product
  • glycosylated steviol glycoside and “GSG” are used interchangeably with reference to an SG containing one or more additional glucose residues added relative to the parental SGs (including partially glycosylated steviol glycosides) present in e.g., Stevia leaves.
  • a “GSG” may be produced from any known or unknown SG by enzymatic synthesis, chemical synthesis or fermentation. It should be understood that GSG (s) essentially contain a glycosylated steviol glycoside (s) , but may also contain unreacted steviol glycosides, dextrins and other non-steviol glycoside substances when using extracts in the starting materials. It should also be understood that the GSG (s) can be purified and/or separated into purified/isolated components.
  • YYxx refers to a composition, where YY refers to a given (such as RA) or collection of compounds (e.g., SGs) , where "xx" is typically a percent by weight number between 1 and 100 denoting the level of purity of a given compound (such as RA) or collection of compounds, where the weight percentage of YY in the dried product is equal to or greater than xx.
  • YYxx+WWzz refers to a composition, where each one of “YY” and “WW” refers to a given compound (such as RA) or collection of compounds (e.g., SGs) , and where each of "xx” and “zz” refers to a percent by weight number between 1 and 100 denoting the level of purity of a given compound (such as RA) or collection of compounds, where the weight percentage of YY in the dried product is equal to or greater than xx, and where the weight percentage of WW in the dried product is equal to or greater than zz.
  • YYx refers to a Stevia composition containing YY in amount of ⁇ x%and ⁇ (x+10) %with the following exceptions: the acronym “RA100” specifically refers to pure RA; the acronym “RA99.5” specifically refers to a composition where the amount of RA is ⁇ 99.5 wt %, but ⁇ 100 wt %; the acronym “RA99” specifically refers to a composition where the amount of RA is ⁇ 99 wt %, but ⁇ 100 wt %; the acronym “RA98” specifically refers to a composition where the amount of RA is ⁇ 98 wt %, but ⁇ 99 wt %; the acronym “RA97” specifically refers to a composition where the amount of RA is ⁇ 97 wt %, but ⁇ 98 wt %; the acronym “RA95” specifically refers to a composition where the amount of RA is ⁇ 95 wt %, but ⁇ 97 wt %; the acronym “
  • Stevia extracts include, but are not limited to, including, but are not limited to RA20, RA40, RA50, RA60, RA80, RA 90, RA95, RA97, RA98, RA99, RA99.5, RB8, RB10, RB15, RC15, RD6, and combinations thereof.
  • the acronym “RUx” is used with reference to a sweet tea extract (ST-E) that is defined by its concentration of RU. More particularly, the acronym “RUx” refers to a sweet tea extract (ST-E) containing rubusoside (RU) in amount of ⁇ x%and ⁇ (x+10) %, except as otherwise noted, where e.g., the acronym “RU100” specifically refers to pure RU; the acronym “RU99.5” specifically refers to a composition where the amount of RA is ⁇ 99.5 wt %, but ⁇ 100 wt %; the acronym “RU99” specifically refers to a composition where the amount of RU is ⁇ 99 wt %, but ⁇ 100 wt %; the acronym “RU98” specifically refers to a composition where the amount of RU is ⁇ 98 wt %, but ⁇ 99 wt %; the acronym “RU97” specifically refers to a composition where the amount of RU is ⁇ 97 w
  • Sweet tea extracts include, but are not limited to, RU 10, RU20, RU30, RU40, RU50, RU60, RU80, RU90, RU95, RU97, RU98, RU99, RU99.5, or any integer defining a lower limit of RU wt %.
  • GSG-RAxx refers to a GSG composition prepared in an enzymatically catalyzed glycosylation process with RAxx as the starting SG material. More generally, acronyms of the type “GSG-YYxx” refer to a composition of the present application where YY refers to a compound (such as RA, RB, RC or RD) , or a composition (e.g., RA20) , or a mixture of compositions (e.g., RA40+RB8) .
  • GSG-RA20 refers to the glycosylation products formed from RA20.
  • GYYxx refers to a glycosylated product of YYxx.
  • GRU20 refers to the glycosylation products formed from RU20.
  • GX refers to a glycosyl group “G” where “X” is a value from 1 to 20 and refers to the number of glycosyl groups present in the molecule.
  • Stevioside G1 ST-G1
  • GST, Stevioside G2
  • ST-G3 ST-G3
  • Stevioside G4 ST-G4
  • Stevioside G5 ST-G5
  • Stevioside G6 ST-G6
  • ST-G7 has seven (7) groups present
  • Stevioside G8 (ST-G8) has eight (8) glycosyl groups present
  • Stevioside G9 ST-G9) has nine (9) glycosyl groups present
  • purified RU refers to a RU preparation that contains at least 50%RU by weight.
  • Purified RU may be prepared from a natural source, such a Stevia extract or a sweet tea extract, or produced by a chemical or enzymatic process, or fermentation.
  • the term “purified RU” refers to a RU prepration that contains at least 60%, 70%, 80%, 85%, 90%, 95%, 96%, 97%, 98%, or 99%RU by weight.
  • enriched RU refers to a RU preparation that contains at least 5%RU by weight.
  • Enriched RU may be prepared from a natural source, such a Stevia extract or a sweet tea extract, or produced by a chemical or enzymatic process, or fermentation.
  • the term “enriched RU” refers to a RU prepration that contains at least 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%or 45%RU by weight.
  • enriched stevioside composition refers to a
  • non-RU STC refers to a sweet tea component that is not RU.
  • a non-RU STC may be purified from a natural source, or produced by a chemical or enzymatic process, or fermentation.
  • the non-RU STC can be a volatile compound or a non-volatile compound.
  • glycosylation reaction refers to molecules having a RU backbone (as shown in Table 1 with a molecular weight of 641) and additional sugar units added in a glycosylation reaction under man-made conditions. Glycosylated RUs include, but are not limited to, molecules having a RU backbone and 1-50 additional sugar units.
  • sucrose unit refers to a monosaccharide unit.
  • glycoside refers to a molecule in which a sugar (the “glycone” part or “glycone component” of the glycoside) is bonded to a non-sugar (the “aglycone” part or “aglycone component” ) via a glycosidic bond.
  • terpene is used with reference to a large and diverse class of organic hydrocarbon molecules classified according to the number of isoprene units in the molecule. Although terpenoids are sometimes used interchangeably with “terpenes” , terpenoids (or isoprenoids) are modified terpenes as they contain additional functional groups, usually oxygen-containing.
  • pene includes hemiterpenes (isoprene, single isoprene unit) , monoterpenes (two isoprene units) , sesquiterpenes (three isoprene units) , diterpenes (four isoprene units) , sesterterpenes (five isoprene units) , triterpenes (six isoprene units) , sesquarterpenes (seven isoprene units) , tetraterpenes (eight isoprene units) and polyterpenes (long chains of many isoprene units) .
  • terpenoid is used with reference to a large and diverse class of organic molecules derived from terpenes, more specifically five-carbon isoprenoid units assembled and modified in a variety of ways and classified in groups based on the number of isoprenoid units used in group members.
  • terpenoids are sometimes used interchangeably with “terpenes”
  • terpenoids or isoprenoids
  • terpenoids are modified terpenes as they contain additional functional groups, usually oxygen-containing.
  • the term “terpenoids” includes hemiterpenoids, monoterpenoids, sesquiterpenoids, diterpenoids, sesterterpenoids, triterpenoids, tetraterpenoids and polyterpenoids.
  • terpene glycoside and “terpene sweetener” refer to a compound having a terpene aglycone linked by a glycosidic bond to a glycone.
  • Terpene glycosides include, but are not limited to, diterpene glycosides, such as steviol glycosides and suaviosides, and triterpene compounds, such as mogrosides.
  • Exemplary diterpene glycosides from Rubus suavissimus include steviol glycosides, such as rubusoside, steviol monoside, rebaudioside A, isomers of rebaudioside B, isomers of stevioside, as well as kaurane-type diterpene glycosides found in sweet tea plants, such as the sweet tasting suaviosides B (SU-B) , SU-G, SU-H, SU-I and SU-J, respectively.
  • Additional SUs include bitter suaviosides, such as SU-C1, SU-D2, SU-F and tasteless suaviosides, such as SU-D1 and SU-E.
  • Exemplary triterpene glycosides from plants or extracts derived from Siraitia grosvenorii include mogrol glycosides, mogrosides, mogroside II, mogroside II B, mogroside II E, mogroside III, mogroside III A2, mogroside IV, mogroside V, mogroside VI, neomogroside, grosmomoside siamenoside I, 7-oxo-mogroside II E, 11-oxo-mogroside A1, 11-deoxy-mogroside III, -oxomogroside IV A, 7-oxo-mogroside V, 11-oxo-mogroside V and others.
  • steviol glycoside, ” and “SG” are used interchangeably with reference to a glycoside of steviol, a diterpene compound shown in Formula I, wherein one or more sugar residues are attached to the compound of Formula I.
  • the carbonyl oxygen at C 19 forms a glycoside ester bond with a sugar (-C (O) -sugar) ; a hydroxyl group linked to C19 at position 17 can form an O-glycoside linkage with a sugar (-CH2-O-sugar) ; and the C1, C2, C3, C6, C7, C11, C12, C15 CH2 groups can directly form C-glycoside linkages with a sugar (-CH2-sugar) .
  • C-glycosides can alos be formed at the two methyl groups.
  • Steviol glycosides also include glycosides of isomers of steviol (isosteviol) and derivatives of steviol, such as 12 ⁇ -hydroxy-steviol and 15 ⁇ -hydroxy-steviol.
  • isosteviol glycosides of isomers of steviol
  • derivatives of steviol such as 12 ⁇ -hydroxy-steviol and 15 ⁇ -hydroxy-steviol.
  • the chemical structure of isosteviol is shown in Formula II.
  • Formulas III and IV show the possible conformations of a typical sugar molecule exemplified by glucose that can form glycosidic bonds.
  • a glycosidic bond involves the hydroxyl-group at the sugar carbon atom numbered 1 (so-called anomeric carbon atom) and either a hydroxyl-group at the steviol/isosteviol molecule building up a so-called O-glycoside or glycosidic ester. Linkage at the carbon atoms given in Table A yields C-glycosides.
  • the sugar part can be selected from any sugar with 3-7 carbon atoms, derived for either dihydroxy-acetone (ketoses) or glycerin-aldehyde (aldoses) .
  • the sugars can occur in open chain or in cyclic form, as D-or L-enantiomers and in ⁇ -or ⁇ -conformation.
  • steviol glycosides examples include, but are not limited to, compounds listed in Table B and isomers thereof.
  • the steviol glycosides for use in the present application are not limited by source or origin. Steviol glycosides may be extracted from Stevia plants, Sweet tea leaves, synthesized by enzymatic processes or chemical syntheses, or produced by fermentation.
  • SG-1 to 16 SGs without a specific name
  • SG-Unk1-6 SGs without detailed structural proof
  • Glc Glucose
  • Rha Rhamnose
  • Xyl Xylose
  • Ara Arabinose.
  • rebaudioside A As used herein, the terms “rebaudioside A, ” “Reb A, ” and “RA” are equivalent terms referring to the same molecule. The same condition applies to all lettered rebaudiosides.
  • steviol glycoside composition and “SG composition” are used interchangeably with reference to a composition comprising one or more SGs.
  • non-sweet tea steviol glycosides or “NST-SG” are used interchangeably with reference to steviol glycosides that are not present in sweet tea plant.
  • oligosaccharide refers to a single unit of a polyhydroxyaldehyde forming an intramolecular hemiacetal the structure of which including a six-membered ring of five carbon atoms and one oxygen atom. Monosaccharides may be present in different diasteromeric forms, such as ⁇ or ⁇ anomers, and D or L isomers.
  • An “oligosaccharide” consists of short chains of covalently linked monosaccharide units. Oligosaccharides comprise disaccharides which include two monosaccharide units, as well as trisaccharides which include three monosaccharide units.
  • a “polysaccharide” consists of long chains of covalently linked monosaccharide units.
  • glycosidic bond and “glycosidic linkage” refer to a type of chemical bond or linkage formed between the anomeric hydroxyl group of a saccharide or saccharide derivative (glycone) and the hydroxyl group of another saccharide or a non-saccharide organic compound (aglycone) such as an alcohol.
  • aglycone a non-saccharide organic compound
  • the reducing end of the di-or polysaccharide lies towards the last anomeric carbon of the structure, and the terminal end is in the opposite direction.
  • the term “enzymatically catalyzed” refers to a method that is performed under the catalytic action of an enzyme, in particular of a glycosidase or a glycosyltransferase.
  • the method can be performed in the presence of said glycosidase or glycosyltransferase in isolated (purified, enriched) or crude form.
  • glycosidic linkage refers to an enzyme that catalyzes the formation of a glycosidic linkage to form a glycoside.
  • a GT catalyzes the transfer of saccharide moieties from an activated nucleotide sugar (also known as the “glycosyl donor or “sugar donor” ) to a nucleophilic glycosyl acceptor molecule, the nucleophile of which can be oxygen-carbon-, nitrogen-, or sulfur-based.
  • glycosyl transfer can be a carbohydrate, glycoside, oligosaccharide, or polysaccharide.
  • glycosyltransferase also includes variants, mutants and enzymatically active portions of glycosyltransferases.
  • glycosidase also includes variants, mutants and enzymatically active portions of glycosidases.
  • sugar donor or “glycosyl donor” refer to a compound or substance from natural or synthetic sources comprising one or more saccharide moieties for transfer to a an oxygen-carbon-, nitrogen-, or sulfur-based nucleophilic glycosyl acceptor molecule in a glycosylation reaction.
  • Dextrin refers to a linear low-molecular weight water-soluble glucose polymer which is produced by the hydrolysis of starch that can serve as a sugar donor in a glycosylation reaction.
  • Dextrins are mixtures of polymers of D-glucose units linked primarily by ⁇ - (1-4) glycosidic bonds and to a lesser extent ⁇ - (1-6) glycosidic bonds. Dextrins are typically produced by enzymatic hydrolysis of starch or application of heat under acid conditions, resulting in a mixture of polyglucose molecules of different chain lengths.
  • “Maltodextrins” are the product of the dextrinization of starch using enzymes coupled with acid hydrolysis or heating; “pyrodextrins” are the product of dextrinization of starch using heat and acid. As used herein, the term “dextrin” includes maltodextrins, pyrodextrins and water-soluble glucose polymers having 3 or more glucose units. Dextrins can be obtained from various natural products, such as wheat, rice, maize and tapioca.
  • glycosylated steviol glycoside and “GSG” are used interchangeably with reference to molecules that (1) contain a SG backbone and one or more additional sugar residues, and (2) are artificially produced by enzymatic synthesis, chemical synthesis or fermentation.
  • glycosylated steviol glycoside composition and “GSG composition” are used interchangeably with reference to a composition comprising one or more GSGs.
  • a glycosylation product of X may contain unreacted starting materials.
  • a glycosylation product of a sweet tea extract may contain glycosylated sweet tea components, unreacted sweet tea components, and unreacted sugar donors such as maltodextrins.
  • a suitable method for measuring the amount of unreacted sugar donors, including dextrins and maltodextrins are described in the section entitled “Assay for determining residual maltodextrin and TSG (9) content in Example 22.
  • Suitable methods for removing unreacted sugar donors, including dextrins and maltodextrins are described in the section entitled “Process for preparing reduced maltodextrin GSG product compositions” and subsequent modification thereto in Example 22.
  • sweet tea glycoside or “STG” are used interchangeably with reference to a glycoside derived from sweet tea plants or known to be present in sweet tea plants.
  • STG include, but are not limited to, rubusoside, suaviosides such as SU-A, SU-B, SU-C1, SU-D1, SU-D2, SU-E, SU-F, SU-G, SU-H, SU-I, and SU-J, steviolmonoside, rebaudioside A, 13-O- ⁇ -D-glucosyl-steviol, isomers of rebaudioside B, isomers of stevioside, panicloside IV and cognitiveoside.
  • non-stevia sweet tea glycoside or “NS-STG” refers to STGs that are not present in Stevia plant or stevia extracts.
  • Examples of NS-STG include, but are not limited to, sauviosides.
  • glycosylated sweet tea glycoside and “GSTG” are used interchangeably with reference to molecules that (1) contain a NS-STG backbone and one or more additional sugar residues, and (2) are artificially produced by enzymatic conversion, fermentation or chemical synthesis.
  • glycosylated non-stevia sweet tea glycoside and “GNS-STG” are used interchangeably with reference to molecules that (1) contain a NS-STG backbone and one or more additional sugar residues, and (2) are artificially produced by enzymatic synthesis, chemical synthesis or fermentation.
  • glycosylated rubusoside “glycosylated RU” and “GRU” are used interchangeably with reference to an exogenously glycosylated rubusoside
  • glycosylated suavioside e.g., glycosylated SU
  • GSU glycosylated suavioside
  • Rubusoside may be mono-glucosylated or di-glucosylated.
  • a chemical structure of mono-glucosylated rubusoside is shown in Formula (V) below. Table C shows various types of linkages that can occur in a mono-glucosylated rubusoside according to the present application.
  • mogroside refers to a triterpene-glycoside and is recognized in the art and is intended to include the major and minor constituents of mogroside extracts.
  • Extracts from the fruits of Siraitia grosvenorii also known as Momordica grosvenori (Swingle) , Luo Han Guo or monk fruit etc. provide a family of triterpene-glycosides and are referred to as mogroside (s) ( “MGs” ) .
  • the extracts include, for example, mogroside V, mogroside IV, siamenoside I, and 11-oxomogroside V.
  • Constituents of the mogroside extracts are referred to by the designation “MG” followed by symbol, such as “V” , therefore mogroside V is “MGV” .
  • Siamenoside I would be “SSI”
  • 11-oxomogroside V would be “OGV” .
  • Monk fruit extracts can contain, for example, a mogroside such as MGV, in an amount of 3%by weight, 5%by weight, 20%by weight, 40%by weight, 50%by weight, 60%by weight or higher but containing other mogrosides or non-mogrosides in the extracts.
  • a mogroside such as MGV
  • other components include other mogrosides such as mogroside II, mogroside IIIA, mogroside IIIE, mogroside IVA, mogroside IVE, siamenoside I, and 11-oxomogroside V.
  • some other polysaccharides or flavonoids may be present.
  • the mogroside (s) of interest can be purified before use.
  • glycosylated mogroside refers to a mogroside that is glycosylated at least at one or more positions in addition to those positions glycosylated in native form, obtained, for example, by synthetic manipulation or by enzymatic processes.
  • glycosyltransferase preferably, CGTase enzyme (cyclodextringlycosyltransferase)
  • GMGs or GMFEs containing glycosylated mogroside (s) contain short chain compounds obtained by hydrolyzation of glycosylated product and also comprises non-glycosylated ingredients which are the residue of non-reacted mogrosides, or unreacted components other than mogrosides contained in the monk fruit extract.
  • a suitable procedure to prepare glycosylated mogrosides (GMGs) or glycosylated monk fruit extracts (MFEs) includes i) dissolving dextrin in water (e.g., reverse osmosis) , ii) adding the mogrosides or extract to the solubilized dextrin to obtain a mixture, wherein the ratio of dextrin to mogrosides/extract is optimized in a ratio of between 100 ⁇ 1 to 1 ⁇ 100 with suitable ranges including 3 ⁇ 1, 2 ⁇ 1, 1.5 ⁇ 1 and 1 ⁇ 1, iii) adding CGTase enzyme to the mixture followed by incubating the mixture at 60°C for a desired length of reaction time to glycosylate mogrosides with glucose molecules derived from dextrin.
  • GMG (s) essentially contains glycosylated mogroside (s) , but also contains unreacted mogrosides, dextrin and other non-mogroside substances found in extracts. It should also be understood that the GMG (s) can be purified and/or separated into purified/isolated components before use.
  • G-X refers to a glycosylation product of composition X, i.e., a product prepared in an enzymatically catalyzed glycosylation process with X and one or more sugar donors as the starting materials.
  • G-RU20 refers to the glycosylation products formed from RU20
  • G- (RU20+RB8) refers to the glycosylation products formed from RU20+RB8.
  • thaumatin as used herein, is used generically with reference to thaumatin I, II, III, a, b, c, etc. and/or combinations thereof.
  • non-volatile refers to a compound having a negligible vapor pressure at room temperature, and/or exhibits a vapor pressure of less than about 2 mm of mercury at 20 °C.
  • volatile refers to a compound having a measurable vapor pressure at room temperature, and/or exhibits a vapor pressure of, or greater than, about 2 mm of mercury at 20 °C.
  • sweetener generally refers to a consumable product, which produces a sweet taste when consumed alone.
  • sweeteners include, but are not limited to, high-intensity sweeteners, bulk sweeteners, sweetening agents, and low sweetness products produced by synthesis, fermentation or enzymatic conversion methods.
  • high-intensity sweetener refers to any synthetic or semi-synthetic sweetener or sweetener found in nature.
  • High-intensity sweeteners are compounds or mixtures of compounds which are sweeter than sucrose.
  • High-intensity sweeteners are typically many times (e.g., 20 times and more, 30 times and more, 50 times and more or 100 times sweeter than sucrose) .
  • sucralose is about 600 times sweeter than sucrose
  • sodium cyclamate is about 30 times sweeter
  • Aspartame is about 160-200 times sweeter
  • thaumatin is about 2000 times sweeter then sucrose (the sweeteness depends on the tested concentration compared with sucrose) .
  • High-intensity sweeteners are commonly used as sugar substitutes or sugar alternatives because they are many times sweeter than sugar but contribute only a few to no calories when added to foods. High-intensity sweeteners may also be used to enhance the flavor of foods. High-intensity sweeteners generally will not raise blood sugar levels.
  • high intensity natural sweetener refers to sweeteners found in nature, typically in plants, which may be in raw, extracted, purified, refined, or any other form, singularly or in combination thereof.
  • High intensity natural sweeteners characteristically have higher sweetness potency, but fewer calories than sucrose, fructose, or glucose.
  • Examples of high intensity natural sweetener include, but are not limited to, sweet tea extracts, stevia extracts, swingle extracts, steviol glycosides, suaviosides, morgosides, mixtures, salts and derivatives thereof.
  • high intensity synthetic sweetener or “high intensity artificial sweetener” refers to high intensity sweeteners that are not found in nature.
  • High intensity synthetic sweeteners include “high intensity semi-synthetic sweeteners” or “high intensity semi-artificial sweeteners” , which are synthesized from, artificially modified from, or derived from, high intensity natural sweeteners.
  • high intensity synthetic sweeteners include, but are not limited to, sucralose, aspartame, acesulfame-K, neotame, saccharin and aspartame, glycyrrhizic acid ammonium salt, sodium cyclamate, saccharin, advantame, neohesperidin dihydrochalcone (NHDC) and mixtures, salts and derivatives thereof.
  • sweetening agent refers to a high intensity sweetener.
  • the term “bulk sweetener” refers to a sweetener, which typically adds both bulk and sweetness to a confectionery composition and includes, but is not limited to, sugars, sugar alcohols, sucrose, commonly referred to as “table sugar, ” fructose, commonly referred to as “fruit sugar, ” honey, unrefined sweeteners, syrups, such as agave syrup or agave nectar, maple syrup, com syrup and high fructose com syrup (or HFCS) .
  • sweetener enhancer refers to a compound (or composition) capable of enhancing or intensifying sensitivity of the sweet taste.
  • sweetener enhancer is synonymous with a “sweetness enhancer, ” “sweet taste potentiator, ” “sweetness potentiator, ” and/or “sweetness intensifier. ”
  • a sweetener enhancer enhances the sweet taste, flavor, mouth feel and/or the taste profile of a sweetener without giving a detectable sweet taste by the sweetener enhancer itself at an acceptable use concentration.
  • the sweetener enhancer provided herein may provide a sweet taste at a higher concentration by itself. Certain sweetener enhancers provided herein may also be used as sweetening agents.
  • Sweetener enhancers can be used as food additives or flavors to reduce the amounts of sweeteners in foods while maintaining the same level of sweetness. Sweetener enhancers work by interacting with sweet receptors on the tongue, helping the receptor to stay switched “on” once activated by the sweetener, so that the receptors respond to a lower concentration of sweetener. These ingredients could be used to reduce the calorie content of foods and beverages, as well as save money by using less sugar and/or less othersweeteners. Examples of sweetener enhancers include, but are not limited to, brazzein, miraculin, curculin, pentadin, mabinlin, thaumatin, and mixtures thereof.
  • sweetening agents or sweeteners can be used as sweetener enhancers or flavors when their dosages in food and beverage are low.
  • sweetener enhancers can be utilized as sweeteners where their dosages in foods and beverages are higher than dosages regulated by FEMA, EFSA or other related authorities.
  • low sweetness products including those produced by synthesis, fermentation or enzymatic conversion refer to products that have less sweetness or similar sweetness than sucrose.
  • low sweetness products produced by extraction, synthesis, fermentation or enzymatic conversion method include, but are not limited to, sorbitol, xylitol, mannitol, erythritol, trehalose, raffmose, cellobiose, tagatose, DOLCIA PRIMA TM allulose, inulin, N-- [N- [3- (3-hydroxy-4-methoxyphenyl) propyl] -alpha-aspartyl] -L-phenylalanine 1-methyl ester, glycyrrhizin, and mixtures thereof.
  • “sugar alcohols” or “polyols” are sweetening and bulking ingredients used in manufacturing of foods and beverages. As sugar substitutes, they supply fewer calories (about a halfto one-third fewer calories) than sugar, are converted to glucose slowly, and are not characterized as causing spiked increases in blood glucose levels.
  • Sorbitol, xylitol, and lactitol are exemplary sugar alcohols (or polyols) . These are generally less sweet than sucrose, but have similar bulk properties and can be used in a wide range of food and beverage products. In some case, their sweetness profile can be fine-tuned by being mixed together with high-intensity sweeteners.
  • flavor and “flavor characteristic” are used interchangeably with reference to the combined sensory perception of one or more components of taste, odor, and/or texture.
  • flavoring agent e.g., a sweetener, such as a SG and or GSG containing composition, can be used as a flavoring agent at concentrations that are below the sweetness recognition threshold of the sweetener.
  • natural flavoring substance refers to a flavoring substance obtained by physical processes that may result in unavoidable but unintentional changes in the chemical structure of the components of the flavoring (e.g., distillation and solvent extraction) , or by enzymatic or microbiological processes, from material of plant or animal origin.
  • synthetic flavoring substance refers to a flavoring substance formed by chemical synthesis.
  • enhancement includes augmenting, intensifying, accentuating, magnifying, and potentiating the sensory perception of a flavor characteristic without changing the nature or quality thereof.
  • modify includes altering, varying, suppressing, depressing, fortifying and supplementing the sensory perception of a flavor characteristic where the quality or duration of such characteristic was deficient.
  • the phrase “sensory profile” or “taste profile” is defmed as the temporal profile of all basic tastes of a sweetener.
  • the onset and decay of sweetness when a sweetener is consumed, as perceived by trained human tasters and measured in seconds from first contact with a taster′s tongue ( “onset” ) to a cutoff point (typically 180 seconds after onset) is called the “temporal profile of sweetness. ”
  • a plurality of such human tasters is called a “sensory panel” .
  • sensory panels can also judge the temporal profile of the other “basic tastes” : bitterness, saltiness, sourness, piquance (aka spiciness) , and umami (aka savoriness or meatiness) .
  • the onset and decay of bitterness when a sweetener is consumed, as perceived by trained human tasters and measured in seconds from first perceived taste to the last perceived aftertaste at the cutoff point is called the “temporal profile of bitterness” .
  • sucrose equivalence or “SugarE” is the amount of non-sucrose sweetener required to provide the sweetness of a given percentage of sucrose in the same food, beverage, or solution.
  • a non-diet soft drink typically contains 12 grams of sucrose per 100 ml of water, i.e., 12%sucrose. This means that to be commercially accepted, diet soft drinks must generally have the same sweetness as a 12%sucrose soft drink, i.e., a diet soft drink must have a 12%SugarE.
  • Soft drink dispensing equipment assumes a SugarE of 12%, since such equipment is set up for use with sucrose-based syrups.
  • off-tast refers to an amount or degree of taste that is not characteristically or usually found in a beverage product or a consumable product of the present disclosure.
  • an off-taste is an undesirable taste of a sweetened consumable to consumers, such as, a bitter taste, a licorice-like taste, a metallic taste, an aversive taste, an astringent taste, a delayed sweetness onset, a lingering sweet aftertaste, and the like, etc.
  • personal care product refers to a medicinal, oral hygiene, or cosmetic product comprising a composition in accordance with the present application.
  • orally consumable product refers to a composition that can be drunk, eaten, swallowed, inhaled, ingested or otherwise in contact with the mouth or nose of man or animal, including compositions which are taken into and subsequently ejected from the mouth or nose.
  • Orally consumable products are safe for human or animal consumption when used in a generally acceptable range.
  • Orally consumable products include, but are not limited to mouthwashes, mouth rinses, breath fresheners, toothpastes, tooth polishes, dentifrices, mouth sprays, teeth whitening agents, soaps, perfumes, and the like. Food, feed, pharmaceuticals are also included.
  • ppm parts per million
  • One aspect of the present application provides sweetening and flavoring compositions that comprise one or more products selected from the group consisting of rubusosides (RU) , sweet tea components (STCs) , sweet tea extracts (STEs) , morgrosides (MGs) , monk fruit components (MFCs) , monk fruit extracts (MFEs) , steviol glycosides (SGs) , Stevia components (SCs) , Stevia extracts (SEs) , glycosylated rubusoside (GRU) , glycosylated sweet tea components (GSTCs) , glycosylated sweet tea extracts (GSTEs) , glycosylated morgrosides (GMGs) , glycosylated monk fruit components (GMFCs) , glycosylated monk fruit extracts (GMFEs) , glycosylated stevia glycosides (GSGs) , glycosylated Stevia components (GSCs) and glycosylated
  • the present application provides stevia-based sweetening and flavoring compositions that comprise (A) a SG, SE and/or SC, (B) a GSG, GSE and/or GSC, or any combinations of (A) and (B) .
  • the present application provides stevia-based sweetening and flavoring compositions that comprise (A) a MG, MFC and/or MFE, (B) a GMG, GMFC and/or GMFE, or any combinations of (A) and (B) .
  • the present application provides sweet tea-based sweetening and flavoring compositions that comprise (A) a sweet tea extract (STE) or at least one sweet tea component (STC) , (B) a glycosylated STE or at least one glycosylated STC, or any combinations of (A) - (B) .
  • the STE described above is a NS-STE.
  • the STC described above is a NS-STC.
  • Sweet tea plants and extracts therefrom include a wide variety of biochemically active STCs, including steviol glycosides, non-steviol glycosides substances, diterpenes, diterpenoids, triterpenes, triterpenoids, carotenoids (tetraterpenoids) , flavonoids, isoflavonoids, polyphenols, tannins, carotenoids, free amino acids, vitamins, and the like.
  • biochemically active STCs including steviol glycosides, non-steviol glycosides substances, diterpenes, diterpenoids, triterpenes, triterpenoids, carotenoids (tetraterpenoids) , flavonoids, isoflavonoids, polyphenols, tannins, carotenoids, free amino acids, vitamins, and the like.
  • STs Sweet tea extracts
  • STCs sweet tea components
  • SEs Stevia extracts
  • SCs Stevia components
  • MFEs Monk fruit extracts
  • MFCs Monk fruit components
  • a sweetener or flavoring composition comprises one or more STEs, one or more STCs, one or more SEs, one or more SGs, one or more SCs, one or more MFEs, one or more MGs, and/or or one or more MFCs in an amount of 000.1-99.9 wt%of the composition.
  • one or more STEs, one or more STCs, one or more SEs, one or more SGs, one or more SCs, one or more MFEs, one or more MGs, and/or or one or more MFCs are present in an amount of 0.001-99 wt %, 0.001-75 wt %, 0.001-50 wt%, 0.001-25 wt%, 0.001-10 wt %, 0.001-5 wt %, 0.001-2 wt %, 0.001-1 wt %, 0.001-0.1 wt %, 0.001-0.01 wt %, 0.01-99 wt %, 0.01-75 wt %, 0.01-50 wt%, 0.01-25 wt%., 0.01-10 wt %, 0.01-5 wt %, 0.01-2 wt %, 0.01-1 wt %, 0.1-99 wt %, 0.1
  • the sweetener or flavoring composition comprises a STE that contains enriched RU.
  • the sweetener or flavoring composition comprises a STE that contains an enriched diterpene glycoside.
  • the sweetener or flavoring composition comprises one or more STCs selected from the group consisting of RU, SU, steviolmonoside, rebaudioside A, 13-O- ⁇ -D-glucosyl-steviol, isomers of rebaudioside B, isomers of stevioside, panicloside IV, poweroside, ent-16 ⁇ , 17-dihydroxy-kaurane-19-oic acid, ent-13 -hydroxy-kaurane-16-en-19-oic acid, ent-kaurane-16-en-19-oic-13-O- ⁇ -D-glucoside, ent-16 ⁇ , 17-dihydroxy-kaurane-3-one, ent-16 ⁇ , 17-dihydroxy-kaurane-19-oic acid, ent-kaurane-16 ⁇ , 17-diol-3-one-17-O- ⁇ -D-glucoside, ent-16 ⁇ , 17-dihydroxy-kaurane-3-one, ent-kaurane-16 ⁇ ,
  • the sweetener or flavoring composition comprises one or more suavosides slected from the group consisting of SU-A, SU-B, SU-C1, SU-D1, SU-D2, SU-E, SU-F, SU-G, SU-H, SU-I, and SU-J.
  • the sweetener or flavoring composition comprises purified RU.
  • the sweetener or flavoring composition comprises a STE having a RU content of 1-99 wt%, 1-95 wt%, 1-90 wt%, 1-80 wt%, 1-70 wt%, 1-60 wt%, 1-50 wt%, 1-40 wt%, 1-30 wt%, 1-20 wt%, 1-10 wt%, 1-5 wt%, 5-99 wt%, 5-95 wt%, 5-90 wt%, 5-80 wt%, 5-70 wt%, 5-60 wt%, 5-50 wt%, 5-40 wt%, 5-30 wt%, 5-20 wt%, 5-10 wt%, 10-99 wt%, 10-95 wt%, 10-90 wt%, 10-80 wt%, 10-70 wt%, 10-60 wt%, 10-50 wt%, 10-40 wt%, 10-30 wt%, 10-20 wt%, 10-20
  • the sweetener or flavoring composition comprises a STE having a RU content of at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or any range defined by any pair of these integers.
  • the sweetener or flavoring composition comprises one or more flavonoid glycosides, isoflavone glycosides, saponin glycosides, phenol glycosides, cynophore glycosides, anthraquinone glycosides, cardiac glycosides, bitter glycosides, coumarin glycosides, or sulfur glycosides.
  • flavonoids include, but are not limited to, anthocyanidins; anthoxanthins, including flavones, such as luteolin, apigenin, tangeritin; and flavonols, such as quercetin, kaempferol, myricetin, fisetin, galangin, isorhamnetin, pachypodol, rhamnazin, pyranoflavonols, furanoflavonols; flavanones, such as hesperetin, naringenin, eriodictyol, and homoeriodictyol; flavanonols, such as taxifolin (or dihydroquercetin) and dihydrokaempferol; and flavans, including flavanols, such as catechin, gallocatechin, catechin 3-gallate, gallocatechin 3-gallate, epicatechin, epigallocatechin (EGC) , epicatechin 3-gallate, epigal
  • Exemplary isoflavonoids include isoflavones, such as genistein, daidzein, glycitein, isoflavanes, isoflavandiols, isoflavenes, coumestans, pterocarpans, and glycosides thereof.
  • Exemplary polyphenols include gallic acid, ellagic acid, quercetin, isoquercitrin, rutin, citrus flavonoids, catechins, proanthocyanidins, procyanidins, anthocyanins, reservatrol, isoflavones, curcumin, hesperidin, naringin, and chlorogenic acid, and and glycosides thereof.
  • Exemplary tannins include gallic acid esters, ellagic acid esters, ellagitannins, including rubusuaviins A, B, C, D, -E, and -F; punicalagins, such as pedunculagin and 1 ( ⁇ ) -O-galloyl pedunculagin; strictinin, sanguiin H-5, sanguiin H-6, 1-desgalloyl sanguiin H-6.
  • lambertianin A castalagins, vescalagins, castalins, casuarictins, grandimins, punicalins, roburin A, tellimagrandin II, terflavin B; gallotannins, including digalloyl glucose and 1, 3, 6-trigalloyl glucose; flavan-3-ols, oligostilbenoids, proanthocyanidins, polyflavonoid tannins, catechol-type tannins, pyrocatecollic type tannins, flavolans, and glycosides thereof.
  • Exemplary carotenoids include carotenes, including ⁇ -, ⁇ -, ⁇ -, ⁇ -, and ⁇ -carotenes, lycopene, neurosporene, phytofluene, phytoene; and xanthophylls, including canthaxanthin, cryptoxanthin, zeaxanthin, astaxanthin, lutein, rubixanthin, and glycosides thereof.
  • the sweetener or flavoring composition comprises one or more diterpenes, diterpenoids, triterpenes and/or triterpenoids.
  • Exemplary diterpenes and diterpenoids include steviol, ent-16 ⁇ , 17-dihydroxy-kaurane-19-oic acid, ent-13 -hydroxy-kaurane-16-en-19-oic acid, ent-16 ⁇ , 17-dihydroxy-kaurane-3-one, ent-16 ⁇ , 17-dihydroxy-kaurane-19-oic acid, ent-16 ⁇ , 17-dihydroxy-kaurane-3-one, ent-kaurane-3 ⁇ , 16 ⁇ , 17-3-triol, ent-13, 17-dihydroxy-kaurane-15-en-19-oic acid, and glycosides thereof.
  • Exemplary triterpenes and triterpenoids include oleanolic acid, ursolic acid, saponin, and glycoside thereof.
  • the STE/STC containing sweetener or flavoring composition further comprises a stevia extract. In some embodiments, the STE/STC containing sweetener or flavoring composition further comprises a one or more non-sweet tea steviol glycosides. In some embodiments, the STE/STC containing sweetener or flavoring composition further comprises thaumatin.
  • Glycosylated STEs glycosylated STCs, glycosylated SEs, glycosylated SGs, glycosylated SCs, glycosylated MGs, glycosylated MFEs and glycosylated MFCs
  • the sweetener or flavoring composition of the present application comprises one or more glycosylated STEs (GSTEs) , one or more glycosylated STCs (GSTCs) , one or more glycosylated SEs (GSEs) , one or more glycosylated SGs (GSGs) , one or more glycosylated SCs (GSCs) , one or more glycosylated MGs (GMGs) , one or more glycosylated MFEs (GMFEs) , and/or one or more glycosylated glycosylated MFCs (GMFCs) , where the glycosylated components are present in the sweetener or flavor composition in an amount of 000.1-99.9 wt%.
  • the one or more GSTEs, one or more GSTCs, one or more GSEs, one or more GSGs, one or more GSCs, one or more GMGs, one or more GMFEs, and/or one or more GMFCs are present in the sweetener or flavoring composition in an amount of 0.001-99 wt %, 0.001-75 wt %, 0.001-50 wt%, 0.001-25 wt%, 0.001-10 wt %, 0.001-5 wt %, 0.001-2 wt %, 0.001-1 wt %, 0.001-0.1 wt %, 0.001-0.01 wt %, 0.01-99 wt %, 0.01-75 wt %, 0.01-50 wt%, 0.01-25 wt%., 0.01-10 wt %, 0.01-5 wt %, 0.01-2 wt %, 0.01-1 wt %,
  • the glycosylated STE is prepared from a STE that contains enriched RU.
  • the glycosylated STE is prepared from a STE that contains an enriched diterpene glycoside.
  • the one or more glycosylated STCs are selected from the glycosylation products ofRU, SU, steviolmonoside, rebaudioside A, 13-O- ⁇ -D-glucosyl-steviol, isomers of rebaudioside B, isomers of stevioside, panicloside IV, poweroside, ent-16 ⁇ , 17-dihydroxy-kaurane-19-oic acid, ent-13-hydroxy-kaurane-16-en-19-oic acid, ent-kaurane-16-en-19-oic-13-O- ⁇ -D-glucoside, ent-16 ⁇ , 17-dihydroxy-kaurane-3-one, ent-16 ⁇ , 17-dihydroxy-kaurane-19-oic acid, ent-kaurane-16 ⁇ , 17-diol-3-one-17-O- ⁇ -D-glucoside, ent-16 ⁇ , 17-dihydroxy-kaurane-3-one, ent-kaurane-3-one-17-
  • the one or more glycosylated STCs comprise one or more of the glycosylation products of SU-A, SU-B, SU-C1, SU-D1, SU-D2, SU-E, SU-F, SU-G, SU-H, SU-I, and SU-J.
  • the one or more glycosylated STCs comprise glycosylation product of purified RU.
  • the sweetener or flavoring composition comprises the glycosylation product of a STE having a RU content of 1-99 wt%, 1-95 wt%, 1-90 wt%, 1-80 wt%, 1-70 wt%, 1-60 wt%, 1-50 wt%, 1-40 wt%, 1-30 wt%, 1-20 wt%, 1-10 wt%, 1-5 wt%, 5-99 wt%, 5-95 wt%, 5-90 wt%, 5-80 wt%, 5-70 wt%, 5-60 wt%, 5-50 wt%, 5-40 wt%, 5-30 wt%, 5-20 wt%, 5-10 wt%, 10-99 wt%, 10-95 wt%, 10-90 wt%, 10-80 wt%, 10-70 wt%, 10-60 wt%, 10- 50 wt%, 10-40 wt%, 10-30 wt%,
  • the sweetener or flavoring composition comprises the glycosylation product of a STE having a RU content of at least 1%, at least 2%, at least 5%, at least 10%, at least 15%, at least 20%, at least 25%, at least 30%, at least 35%, at least 40%, at least 45%, at least 50%, at least 55%, at least 60%, at least 65%, at least 70%, at least 75%, at least 80%, at least 85%, at least 90%, at least 95%, at least 90%, or any range defined by any pair of these integers.
  • the sweetener or flavoring composition comprises one or more glycosylated flavonoid glycosides, glycosylated isoflavone glycosides, glycosylated saponin glycosides, glycosylated phenol glycosides, glycosylated cynophore glycosides, glycosylated anthraquinone glycosides, glycosylated cardiac glycosides, glycosylated bitter glycosides, glycosylated coumarin glycosides, or glycosylated sulfur glycosides.
  • the GSTE/GSTC containing sweetener or flavoring composition further comprises a glycosylated stevia extract. In some embodiments, the the GSTE/GSTC containing sweetener or flavoring composition further comprises a one or more glycosylated non-sweet tea steviol glycosides. In some embodiments, the the GSTE/GSTC containing sweetener or flavoring composition further comprises thaumatin.
  • glycosylated products described in the present application such as GSTEs, GSTCs, GSEs, GSGs, GSCs, GMGs, GMFEs and GMFCs can be formed by exogenous glycosylation reactions in the presence of a glycosyltransferase.
  • glycosidic linkage As used herein, a “glycosyltransferase” refers to an enzyme that catalyzes the formation of a glycosidic linkage to form a glycoside.
  • a glycoside is any molecule in which a sugar group is bonded through its anomeric carbon to another group via a glycosidic bond.
  • Glycosides can be linked by an O- (an O-glycoside) , N- (a glycosylamine) , S- (a thioglycoside) , or C- (a C-glycoside) glycosidic bond.
  • the sugar group is known as the glycone and the non-sugar group is known as the aglycone.
  • glycone can be part of a single sugar group (monosaccharide) or several sugar groups (oligosaccharide) .
  • a glycosyltransferase according to the present application further embraces “glycosyltransferase variants” engineered for enhanced activities.
  • Glycosyltransferases utilize “activated” sugar phosphates as glycosyl donors, and catalyze glycosyl group transfer to an acceptor molecule comprising a nucleophilic group, usually an alcohol.
  • a retaining glycosyltransferases is one which transfers a sugar residue with the retention of anomeric configuration.
  • Retaining glycosyltransferase enzymes retain the stereochemistry of the donor glycosidic linkage after transfer to an acceptor molecule.
  • An inverting glycosyltransferase is one which transfers a sugar residue with the inversion of anomeric configuration.
  • Glycosyltransferases are classified based on amino acid sequence similarities. Glycosyltransferases are classified by the Nomenclature Committee of the International Union of Biochemistry and Molecular Biology (NC-IUBMB) in the enzyme class of EC 2.4.1 on the basis of the reaction catalyzed and the specificity.
  • Glycosyltransferases can utilize a range of donor substrates. Based on the type of donor sugar transferred, these enzymes are grouped into families based on sequence similarities. Exemplary glyosyltransferases include glucanotransferases, N-acetylglucosaminyltransferases, N-acetylgalactosaminyltransferases, fucosyltransferases, mannosyltransferases, galactosyltransferases, sialyltransferases sialyltransferases, galactosyltransferases, fucosyltransferase, Leloir glycosyltransferases, non-Leloir glycosyltransferases, and other glycosyltransferases in the enzyme class of EC 2.4.1.
  • the Carbohydrate-Active Enzymes database (CAZy) provides a continuously updated list of the glycosyltransferase families.
  • the glycosylation products described in the present application are formed from a reaction mixture comprising an exogenous glycosyltransferase classified as an EC 2.4.1 enzyme, including but not limited to members selected from the group consisting of cyclomaltodextrin glucanotransferase (CGTase; EC 2.4.1.19) , amylosucrase (EC 2.4.1.4) , dextransucrase (EC 2.4.1.5) , amylomaltase, sucrose: sucrose fructosyltransferase (EC 2.4.1.99) , 4- ⁇ -glucanotransferase (EC 2.4.1.25) , lactose synthase (EC 2.4.1.22) , sucrose-1, 6- ⁇ -glucan 3 (6) - ⁇ -glucosyltransferase, maltose synthase (EC 2.4.1.139) , alternasucras
  • CCTase cyclomaltodextr
  • Cyclomaltodextrin glucanotransferase also known as CGTase, is an enzyme assigned with enzyme classification number EC 2.4.1.19, which is capable of catalyzing the hydrolysis and formation of (1 ⁇ 4) - ⁇ -D-glucosidic bonds, and in particular the formation of cyclic maltodextrins from polysaccharides as well as the disproportionation of linear oligosaccharides.
  • Dextransucrase is an enzyme assigned with enzyme classification number EC 2.4.1.5, and is also known as sucrose 6-glucosyltransferase, SGE, CEP, sucrose-1, 6- ⁇ -glucan glucosyltransferase or sucrose: 1, 6- ⁇ -D-glucan 6- ⁇ -D-glucosyltransferase.
  • a glucosyltransferase (DsrE) from Leuconostoc mesenteroides, NRRL B-1299 has a second catalytic domain ( "CD2" ) capable of adding alpha-1, 2 branching to dextrans (U.S. Pat. Nos. 7,439,049 and 5,141,858; U.S. Patent Appl. Publ. No. 2009-0123448; Bozonnet et al., J. Bacteria 184: 5753-5761, 2002) .
  • CD2 second catalytic domain
  • Glycosyltransferases and other glycosylating enzymes for use in the present application may be derived from any source and may be used in a purified form, in an enriched concentrate or as a crude enzyme preparation.
  • the glycosylation reaction is carried out by glycosylating an aglycone or glycoside substrate using e.g., a nucleotide sugar donor (e.g., sugar mono-or diphosphonucleotide) or “Leloir donor” in conjunction with a “Leloir glycosyltransferase” (after Nobel prize winner, Luis Leloir) that catalyzes the transfer of a monosaccharide unit from the nucleotide-sugar ( “glycosyl donor’ ) to a “glycosyl acceptor” , typically a hydroxyl group in an aglycone or glycoside substrate.
  • a nucleotide sugar donor e.g., sugar mono-or diphosphonucleotide
  • Leloir donor e.g., sugar mono-or diphosphonucleotide
  • a “Leloir glycosyltransferase” after Nobel prize winner, Luis Leloir
  • the glycosylation product of the present application is formed from a reaction mixture comprising a nucleotide sugar.
  • the glycosylation reactions may involve the use of a specific Leloir glycosyltransferase in conjunction with a wide range of sugar nucleotides donors, including e.g., UDP-glucose, GDP-glucose, ADP-glucose, CDP-glucose, TDP-glucose or IDT-glucose in combination with a glucose-dependent glycosyltransferase (GDP-glycosyltransferases; GGTs) , ADP-glucose-dependent glycosyltransferase (ADP-glycosyltransferases; AGTs) , CDP-glucose-dependent glycosyltransferase (CDP-glycosyltransferases; CGTs) , TDP-glucose-dependent glycosyltransferase (TDP-glycosyltransferases; TGTs) or IDP-glucose-dependent
  • the exogenous glycosylation reaction is carried out using an exogenous Leloir-type UDP-glycosyltransferase enzyme of the classification EC 2.4.1.17, which catalyzes the transfer of glucose from UDP- ⁇ -D-glucuronate (also known as UDP-glucose) to an acceptor, releasing UDP and forming acceptor ⁇ -D-glucuronoside.
  • the glycosyltransferases include, but are not limited to, enzymes classified in the GT1 family.
  • the glycosylation reaction is catalyzed by an exogenous UDP-glucose-dependent glycosyltransferase.
  • the glycosylaton reaction is catalyzed by a glycosyltransferase capable of transferring a non-glucose nonosaccharide, such as fructose, galactose, ribose, arabinose, xylose, mannose, psicose, fucose and rhamnose, and derivative thereof, to the receipient.
  • a glycosyltransferase capable of transferring a non-glucose nonosaccharide, such as fructose, galactose, ribose, arabinose, xylose, mannose, psicose, fucose and rhamnose, and derivative thereof, to the receipient.
  • U.S. Patent No. 9,567,619 describes several UDP-dependent glycosyltransferases that can be used to transfer monosaccharides to rubusoside, including UGT76G1 UDP glycosyltransferase, HV1 UDP-glycosyltransferase, and EUGT11, a UDP glycosyltransferase-sucrose synthase fusion enzyme.
  • the EUGT11 fusion enzyme contains a uridine diphospho glycosyltransferase domain coupled to a sucrose synthase domain and can exhibit 1, 2- ⁇ glycosidic linkage and 1, 6- ⁇ glycosidic linkage enzymatic activities, as well as sucrose synthase activity.
  • UGT76G1 UDP glycosyltransferase contains a 1, 3-O-glucose glycosylation activity which can transfer a second glucose moiety to the C-3′ of 13-O-glucose ofrubusoside to produce rebaudioside G ( “Reb G” )
  • HV1 UDP-glycosyltransferase contains a 1, 2-O-glucose glycosylation activity which can transfer a second glucoside moiety to the C-2′ of 19-O-glucose of rubusoside to produce rebaudioside KA ( “Reb KA”)
  • the EUGT11 fusion enzyme contains a 1, 2-O-glucose glycosylation activity which transfers a second glucose moiety to the C-2′ of 19-O-glucose ofrubusoside to produce rebaudioside KA or transfer a second glucose moiety to the C-2′ of 13-O-glucose ofrubusoside to produce
  • HV1 and EUGT11 can transfer a second sugar moiety to the C-2′ of 19-O-glucose of rebaudioside G to produce rebaudioside V ( “Reb V” ) and can additionally transfer a second glucose moiety to the C-2′ of 13-O-glucose of rebaudioside KA to produce rebaudioside E ( “Reb E” ) .
  • these enzymes can be used to generate a variety of steviol glycosides known to be present in Stevia rebaudiana, including rebaudioisde D ( “Reb D” ) and rebaudioside M ( “Reb M” ) .
  • Monosaccharides that can be transferred to a saccharide or nonsaccharide acceptor include, but are not limited to glucose, fructose, galactose, ribose, arabinose, xylose, mannose, psicose, fucose and rhamnose, and derivative thereof, as well as acidic sugars, such as sialic acid, glucuronic acid and galacturonic acid.
  • glycosylation of RU and/or other STCs is driven by an exogenous glycosyl hydrolase or glycosidase from the enzyme class of EC 3.2.1.
  • GHs normally cleave a glycosidic bond.
  • they can be used to form glycosides by selecting conditions that favor synthesis via reverse hydrolysis. Reverse hydrolysis is frequently applied e.g., in the synthesis of aliphatic alkylmonoglucosides.
  • Glycosyl hydrolases have a wide range of donor substrates employing usually monosaccharides, oligosaccharides or/and engineered substrates (i.e., substrates carrying various functional groups) . They often display activity towards a large variety of carbohydrate and non-carbohydrate acceptors. Glycosidases usually catalyze the hydrolysis of glycosidic linkages with either retention or inversion of stereochemical configuration in the product.
  • the glycosylation products of the present application are formed from a reaction mixture comprising an exogenous glycosyl hydrolase classified as an EC 3.2.1 enzyme, including but not limited to alpha-glucosidase, beta-glucosidase and beta-fructofuranosidase.
  • Exemplary glycosyl hydrolases for use in the present application include, but are not limited to a-amylases (EC 3.2.1.1) , ⁇ -glucosidases (EC 3.2.1.20) , ⁇ -glucosidases (EC 3.2.1.21) , ⁇ -galactosidases (EC 3.2.1.22) , ⁇ -galactosidases (EC 3.2.1.23) , ⁇ -mannosidase (EC 3.2.1.24) , ⁇ -mannosidase (EC 3.2.1.25) , ⁇ -fructofuranosidase (EC 3.2.1.26) , amylo-1, 6-glucosidases (EC 3.2.1.33) , ⁇ -D-fucosidases (EC 3.2.1.38) , ⁇ -L-rhamnosidases (EC 3.21.40) , glucan 1, 6- ⁇ -glucosidases (EC
  • the glycosylation products of the present application are formed using a class of glycoside hydrolases or glycosyltransferases known as “transglycosylases. ”
  • transglycosylase and “transglycosidase” (TG) are used interchangeably with reference to a glycoside hydrolase (GH) or glycosyltransferase (GT) enzyme capable of transferring a monosaccharide moiety from one molecule to another.
  • GH glycoside hydrolase
  • GT glycosyltransferase
  • a GH can catalyse the formation of a new glycosidic bond either by transglycosylation or by reverse hydrolysis (i.e., condensation) .
  • the acceptor for transglycosylase reaction acceptor can be saccharide acceptor or a nonsaccharide acceptor.
  • a transglycosidase can transfer a monosaccharide moiety to a diverse set of aglycones, including e.g., nonsaccharide acceptors, such as aromatic and aliphatic alcohols.
  • Transglycosidases can transfer a wide variety of monosaccharides (D-or L-configurations) to saccharide acceptors, including glycosides, as well as nonsaccharide acceptors, including a wide variety of flavonoid aglycones, such as naringenin, quercetin, hesperetin.
  • Monosaccharides that can be transferred to a saccharide or nonsaccharide acceptor include, but are not limited to glucose, fructose, galactose, ribose, arabinose, xylose, mannose, psicose, fucose and rhamnose, and derivative thereof, as well as acidic sugars, such as sialic acid, glucuronic acid and galacturonic acid.
  • transglucosidase is used when the monosaccharide moiety is a glucose moiety.
  • Transglycosidases include GHs or GTs from the enzyme classes of EC 3.2.1 or 2.4.1, respectively.
  • TGs are classified into various GH families on the basis of sequence similarity.
  • a large number of retaining glycosidases catalyze both hydrolysis and transglycosylation reactions. In particular, these enzymes catalyze the intra-or intermolecular substitution of the anomeric position of a glycoside.
  • glycosidases can be used to form glycosidic linkages using a glycosyl donor activated by a good anomeric leaving group (e.g., nitrophenyl glycoside) .
  • a good anomeric leaving group e.g., nitrophenyl glycoside
  • thermodynamically controlled reverse hydrolysis uses high concentrations of free sugars.
  • Transglycosidases corresponding to any of the GH families with notable transglycosylase activity may be used in the present application, and may include the use of e.g., members of the GH2 family, including LacZ ⁇ -galactosidase, which converts lactose to allolactose; GH13 family, which includes cyclodextran glucanotransferases that convert linear amylose to cyclodextrins, glycogen debranching enzyme, which transfers three glucose residues from the four-residue glycogen branch to a nearby branch, and trehalose synthase, which catalyzes the interconversion of maltose and trehalose; GH16 family, including xyloglucan endotransglycosylases, which cuts and rejoins xyloglucan chains in the plant cell wall; GH31, for example ⁇ -transglucosidases, which catalyze the transfer of individual glucosyl residue
  • the glycosyltransferase is a transglucosylase from the glycoside hydrolase 70 (GH70) family.
  • GH70 enzymes are transglucosylases produced by lactic acid bacteria from, e.g., Streptococcus, Leuconostoc, Shoeslla or Lactobacillus genera. Together with the families GH13 and GH77 enzymes, they form the clan GH-H. Most of the enzymes classified in this family use sucrose as the D-glucopyranosyl donor to synthesize ⁇ -D-glucans of high molecular mass (>10 6 Da) with the concomitant release of D-fructose. They are also referred to as glucosyltransferases or glucansucrases.
  • ⁇ -D-glucans varying in size, structure, degree of branching and spatial arrangements can thus be produced by GH70 family members.
  • GH70 glucansucrases can transfer D-glucosyl units from sucrose onto hydroxyl acceptor groups.
  • Glucansucrases catalyze the formation of linear as well as branched ⁇ -D-glucan chains with various types of glycosidic linkages, namely ⁇ -1, 2; ⁇ -1, 3; ⁇ -1, 4; and/or ⁇ -1, 6.
  • sucrose analogues such as ⁇ -D-glucopyranosyl fluoride, p-nitrophenyl ⁇ -D-glucopyranoside, ⁇ -D-glucopyranosyl ⁇ -L-sorofuranoside and lactulosucrose can be utilized as D-glucopyranosyl donors.
  • acceptors may be recognized by glucansucrases, including carbohydrates, alcohols, polyols or flavonoids to yield oligosaccharides or gluco-conjugates.
  • Exemplary glucansucrases for use in the present application include e.g., dextransucrase (sucrose: 1, 6- ⁇ -D-glucosyltransferase; EC 2.4.1.5) , altemansucrase (sucrose: 1, 6 (1, 3) - ⁇ -D-glucan-6 (3) - ⁇ -D-glucosyltransferase, EC 2.4.1.140) , mutansucrase (sucrose: 1, 3- ⁇ -D-glucan-3- ⁇ -D-glucosyltransferase; EC 2.4.1.125) , and reuteransucrase (sucrose: 1, 4 (6- ⁇ -D-glucan-4 (6) - ⁇ -D-glucosyltransferase; EC 2.4.1. -) .
  • the structure of the resultant glucosylated product is dependent upon the enzyme specificity.
  • a fructosyltransferase may be used to catalyze the transfer of one or more fructose units, optionally comprising terminal glucose, of the following sequence: (Fru) n-Glc consisting of one or more of: ⁇ 2, 1, ⁇ 2, 6, ⁇ 1, 2 and ⁇ -1, 2 glycosidic bonds, wherein n typically is 3-10.
  • Variants include Inulin type ⁇ -1, 2 and Levan type ⁇ -2, 6 linkages between fructosyl units in the main chain.
  • Exemplary fructosytransferase for use in the present application include e.g., ⁇ -fructofuranosidase (EC 3.2.1.26) , inulosucrase (EC 2.4.1.9) levansucrase (EC 2.4.1.10) , or endoinulinase.
  • a galactosyltransferase or ⁇ -galactosidase may be used to catalyze the transfer of multiple saccharide units, in which one of the units is a terminal glucose and the remaining units are galactose and disaccharides comprising two units of galactose.
  • the transglycosidase is an enzyme having trans-fucosidase, trans-sialidase, trans-lacto-N-biosidase and/or trans-N-acetyllactosaminidase activity.
  • the glycosylation reactions may utilize a combination of any of glycosyltransferases described herein in combination with any one of the glycosyl hydrolases or transglycosidases described herein.
  • the transglycosylase and the glycosyl hydrolase or translygosidase may be present in a range of ratios (w/w) , wherein the transglycosylase/glycosyl hydrolase ratio (w/w) ranges from 100 ⁇ 1, 80 ⁇ 1, 60 ⁇ 1, 40 ⁇ 1, 30 ⁇ 1, 25 ⁇ 1, 20 ⁇ 1, 15 ⁇ 1, 10 ⁇ 1, 9 ⁇ 1, 8 ⁇ 1, 7 ⁇ 1, 6 ⁇ 1, 5 ⁇ 1, 4 ⁇ 1, 3 ⁇ 1, 2 ⁇ 1, 1 ⁇ 1, 1 ⁇ 2, 1 ⁇ 3, 1 ⁇ 4, 1 ⁇ 5, 1 ⁇ 6, 1 ⁇ 7, 1 ⁇ 8, 1 ⁇ 9, 1 ⁇ 10, 1 ⁇ 15, 1 ⁇ 20, 1 ⁇ 25, 1 ⁇ 30, 1 ⁇ 40, 1 ⁇ 50, 1 ⁇ 60, 1 ⁇ 80, 1 ⁇ 100, or any ratio derived from any two of the transglycosylase/
  • the composition typically comprises one or more dextrins remaining after the glycosylation reaction.
  • Dextrins are hydrolysate products of starch that provide a substrate for glycosylation so as to produce a more cost-effective SG/GSG composition having improved solubility and/or an improved taste profile.
  • the dextrins are produced from a starch.
  • the starches used may be the naturally occurring starches, such as potato starch, waxy potato starch, corn starch, rice starch, pea starch, banana starch, horse chestnut starch, wheat starch, amylose, amylomaize, amylopectin, pullulan, lactose, and combinations thereof.
  • modified starches for example pregelatinized starch, thin-boiling starch, oxidized starch, citrate starch, high-fructose corn syrup, hydrogenated starch hydrosylate, hydroxyethyl starch, hydroxypropyl distarch phosphate, maltitol, acetate starch, acetylated distarch adipate, starch ethers, starch esters, starch phosphates, phosphated distarch phosphate, and pentastarch.
  • the starch may have, for example, low viscosity, moderate viscosity or high viscosity, and be cationic or anionic, and cold water-soluble or hot water-soluble.
  • Dextrins may be linear or circular.
  • the dextrin may be selected from the group of tapioca dextrin, potato dextrin, corn dextrin, yellow dextrin, white dextrin, borax dextrin, maltodextrin and cyclodextrins (CD) , such as alpha, beta, and/or gamma cyclodextrin.
  • the dextrin is a CD or tapioca dextrin.
  • CDs are a family of compounds made up of sugar molecules bound together in a ring, cyclic oligosaccharides. They are composed of 5 or more alpha-D-glucopyranoside units linked 1->4, as in amylose. CDs are also referred to as cycloamyloses.
  • Dextrins can make up 1 wt %, 2 wt %, 3 wt %, 4 wt %, 5 wt %, 6 wt %, 7 wt %, 8wt %, 9wt %, 10wt %, 11 wt %, 12 wt %, 13 wt %, 14 wt %, 15 wt %, 16 wt %, 17 wt %, 18 wt %, 19 wt %, 20 wt %, 21 wt %, 22 wt %, 23 wt %, 24 wt %, 25 wt %, 26 wt %, 27 wt %, 28 wt %, 29 wt %, 30 wt %, 31 wt %, 32 wt %, 33 wt %, 34 wt %, 35 wt %, 36 wt
  • the composition of the present application comprises (1) glycosylated stevia glycosides or glycosylated sweet tea extract and (2) maltodextrin, wherein the total amount of oligosaccharides with 3-5 glucose units (DP 3-5) is less than 1 wt %, less than 0.8 wt %, less than 0.7 wt %, and wherein the total total amount of oligosaccharides with more than 5 glucose units (DP >5) is less than 0.5 wt %.
  • Testing methods for determination of dextrins may utilize any method well known in the art, such as HPLC.
  • HPLC HPLC device manufactured by Shimadzu with a refractometric detector and a column recommended for assaying oligosaccharides (i.e., Luna 5 micrometer NH2 100A 250 x 4.60 mm; Phenomenex) may be used to assay maltodextrins.
  • a 65 ⁇ 35 acetonitrile-water system was used as an eluent, flow rate 3 ml/min, analysis time around 10 min, temperature 40°C.
  • Maltodextrin contents (%) can be determined based on comparisons of the peak areas obtained in the examined samples with those from a reference solution (external standard method) .
  • compositions of the present application disclosed herein may be solubilized in an aqueous solution.
  • the aqueous solution can include water and/or an alcohol, such as one or more of methanol, ethanol, propanol, isopropanol, n-butanol, isobutanol, sec-butanol, tert-butanol, n-pentanol, isopentanol, neopentanol, or combinations thereof.
  • the water alcohol solution can be less than 60%alcohol, less than 50%alcohol, less than 40%alcohol, less than 30%alcohol, less than 20%alcohol, less than 10%alcohol, less than 5%alcohol, less than 2%alcohol, or less than 1%alcohol by volume.
  • a glycosylating enzyme may be dissolved in the reaction mixture or immobilized on a solid support which is contacted with the reaction mixture. If the enzyme is immobilized, it may be attached to an inert carrier.
  • suitable carrier materials are known in the art. Examples for suitable carrier materials are clays, clay minerals such as kaolinite, diatomeceous earth, perlite, silica, alumina, sodium carbonate, calcium carbonate, cellulose powder, anion exchanger materials, synthetic polymers, such as polystyrene, acrylic resins, phenol formaldehyde resins, polyurethanes and polyolefins, such as polyethylene and polypropylene.
  • the carrier materials usually are used in the form of fine powders, wherein porous forms are preferred.
  • the particle size of the carrier material usually does not exceed 5 mm, in particular 2 mm.
  • suitable carrier materials are calcium alginate and carrageenan. Enzymes may directly be linked by glutaraldehyde. A wide range of immobilization methods are known in the art. Ratio of reactants can be adjusted based on the desired performance of the final product.
  • the temperature of the glycosylation reaction can be in the range of 1-100°C, preferably 40-80°C, more preferably 50-70°C.
  • the enzymatically catalyzed reaction can be carried out batch wise, semi-batch wise or continuously. Reactants can be supplied at the start of reaction or can be supplied subsequently, either semi-continuously or continuously.
  • the catalytic amount of glycosidase or glycosyltransferase required for the method of the invention depends on the reaction conditions, such as temperature, solvents and amount of substrate.
  • the reaction can be performed in aqueous media such as buffer.
  • a buffer adjusts the pH of the reaction mixture to a value suitable for effective enzymatic catalysis.
  • the pH is in the range of about pH 4 to about pH 9, for example of about pH 5 to about pH 7.
  • Suitable buffers comprise, but are not limited to, sodium acetate, tris (hydroxymethyl) aminomethane ( “Tris” ) and phosphate buffers.
  • the reaction may take place in the presence of a solvent mixture of water and a water miscible organic solvent at a weight ratio of water to organic solvent of from 0.1 ⁇ 1 to 9 ⁇ 1, for example from 1 ⁇ 1 to 3 ⁇ 1.
  • the organic solvent is no primary or secondary alcohol and, accordingly, is non-reactive towards the polysaccharide.
  • Suitable organic solvents comprise alkanones, alkylnitriles, tertiary alcohols and cyclic ethers, and mixtures thereof, for example acetone, acetonitrile, t-pentanol, t-butanol, 1, 4-dioxane and tetrahydrofuran, and mixtures thereof.
  • the use of organic solvents is not preferred.
  • Glycosylation products such as GSGs, GSEs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, may include both reacted and unreacted components from the starting materials (i.e., the mixture of materials before the initiation of the glycosylation reaction) .
  • the glycosylated component e.g., glycosylated RU
  • the glycosylation product composition or glycosylate
  • the glycosylated components are present in the glycosylation product composition in an amount greater than 0.01 wt%, 0.1 wt%, 1 wt%, 2 wt%, 5 wt%, 10 wt%, 20 wt%, 30 wt%, 40 wt%, 50 wt%, 60 wt%, 70 wt%, 80 wt%, 90 wt%, 95 wt%, or 99 wt%.
  • the glycosylation product composition comprise glycosylated RU in an amount ranging 1-5 wt%, 1-10 wt%, 1-15 wt%, 1-20 wt%, 1-30 wt %, 1-40 wt %, 1-50 wt%, 1-60 wt %, 1-70 wt%, 1-80 wt%, 1-90 wt%, 1-95 wt%, 1-99 wt%, 5-10 wt%, 5-15 wt%, 5-20 wt%, 5-30 wt %, 5-40 wt %, 5-50 wt%, 5-60 wt %, 5-70 wt%, 5-80 wt%, 5-90 wt%, 5-95 wt%, 5-99 wt%, 10-15 wt%, 10-20 wt%, 10-30 wt %, 10-40 wt %, 10-50 wt%, 10-60 wt %, 10-70 wt
  • the glycosylation product composition comprises unreacted sugar donors such as dextrins in an amount of greater than zero but less than 30%, 20%, 15%, 10%, 8%, 5%, 4%, 3%, 2%, 1%, 0.5%, 0.2%, 0.1%, 0.05%, 0.02%, 0.01%, 0.005%, 0.002%, or 0.001% (w/w) of the glycosylation product.
  • a methof for preparing low dextrin glycosylates includes the steps of: (a) dissolving glycosylated products; (b) adsorbing the glycosylated products to a suitable resin to the point of saturation; (c) washing the product-bound resin with an organic solvent and/or aqueous organic solvent at a concentration sufficient to elute the products (or desorb the resin therefrom) ; (d) collecting the desorbed glycosylation products, which can be further treated with resins or active carbon for discoloration and/or odor removal; and (e) drying the desorbed glycosylation products.
  • This method may be used for all types of glycosylates, including those containing GSGs, GSEs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs. Exemplary methods for preparing low dextrin glycosylation reaction products are further described in Example 22.
  • the glycosylation products such as GSGs, GSEs, GSTEs, GSTCs include glycosylated RU.
  • the glycosylated RU may comprise RU molecules with different lavel of glycosylation, including but are not limited to, glycosylated RU molecules that contain a RU backbone (as described in Table 1 with a molecular weight of 641) with 1-50 additional monosaccharide units that are added to the RU backbone during a man-made glycosylation reaction.
  • the additional monosaccharide units are glucose units.
  • the additional monosaccharide units are non-glucose units, such as fructose, xylose and galactose units.
  • the additional monosaccharide units are a mixture of glucose units and non-glucose units.
  • the composition of the present application comprises (1) glycosylated stevia glycosides or glycosylated sweet tea extract and (2) maltodextrin, wherein the total amount of oligosaccharides with 3-5 glucose units (DP 3-5) is less than 2 wt %, less than 1.5 wt %, less than 1.2 wt %, less than 1 wt %, less than 0.8 wt %, less than 0.7 wt %, less than 0.6 wt %, or less than 0.5 wt %, and wherein the total total amount of oligosaccharides with more than 5 glucose units (DP >5) is less than 0.5 wt %, less than 0.4 wt %, less than 0.3 wt %, less than 0.2 wt %, or less than 0.1 wt %.
  • the composition of the present application comprises (1) glycosylated stevia glycosides or glycosylated sweet tea extract and (2) maltodextrin, wherein the total amount of oligosaccharides with 3-5 glucose units (DP 3-5) is in the range of 0.0001-2 wt %, 0.0001-1.5 wt %, 0.0001-1.2 wt %, 0.0001-1 wt %, 0.0001-0.8 wt %, 0.0001-0.7 wt %, 0.0001-0.6 wt %, 0.0001-0.5 wt %, 0.01-2 wt %, 0.01-1.5 wt %, 0.01-1.2 wt %, 0.01-1 wt %, 0.01-0.8 wt %, 0.01-0.7 wt %, 0.01-0.6 wt %, 0.01-0.5 wt %, 0.1-2 wt %, 0.1-1.5 wt %,
  • the glycosylation products such as GSGs, GSEs, GSTEs, GSTCs comprise glycosylated RU in an amount of less than 80%, 75%, 70%, 65%, 60%, 55%, 50%, 45%, 40%, 35%, 30%, 25%, 20%, 15%or 10%by weight of the glycosylation products.
  • the glycosylation products such as GSGs, GSEs, GSTEs, GSTCs, comprise glycosylated RU in an amount of greater than 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%or 95%by weight of the glycosylation products.
  • the glycosylated RU comprises unreacted dextrins in an amount of greater than zero but less than 30%, 20%, 15%, 10%, 8%, 5%, 4%, 3%, 2%, 1%, 0.5%, 0.2%, 0.1%, 0.05%, 0.02%, 0.01%, 0.005%, 0.002%, or 0.001% (w/w) .
  • the glycosylated RU comprises mono-glucose RU (RU-1G) in an amount of greater than 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%or 90% (w/w) of the total GRU.
  • the glycosylated RU comprises di-glucose RU (RU-2G) in an amount of greater than 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%or 90% (w/w) of the total GRU.
  • the glycosylated RU comprises tri-glucose RU (RU-3G) in an amount of greater than 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%or 90% (w/w) of the total GRU.
  • the glycosylated RU comprises tetra-glucose RU (RU-4G) in an amount of greater than 10%, 20%, 30%, 40%, 50%60%, 70%, 80%or 90% (w/w) of the total GRU.
  • the glycosylated RU comprises penta-glucose RU (RU-5G) in an amount of greater than 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%or 90% (w/w) of the total GRU.
  • RU-5G penta-glucose RU
  • the glycosylation product comprises unreacted RU residue in an amount of greater than zero but less than 30%, 20%, 15%, 10%, 8%, 5%, 4%, 3%, 2%, 1%, 0.5%, 0.2%, 0.1%, 0.05%, 0.02%, 0.01%, 0.005%, 0.002%, or 0.001% (w/w) of the glycosylation product.
  • the glycosylation product comprises unreacted suaviosides in an amount of greater than zero but less than 20%, 15%, 10%, 8%, 5%, 4%, 3%, 2%, 1%, 0.5%, 0.2%, 0.1%, 0.05%, 0.02%, 0.01%, 0.005%, 0.002%, or 0.001% (w/w) of the glycosylation product.
  • the glycosylation products such as GSGs, GSEs, GSTEs, GSTCs
  • the glycosylation products such as GSGs, GSEs, GSTEs, GSTCs, comprise steviol monoside in an amount of less than 60%, 55%, 50%, 45%, 40%, 35%, 30%, 25%, 20%, 15%, 10%or 5%by weight of the glycosylation products.
  • the glycosylation products such as GSGs, GSEs, GSTEs, GSTCs
  • the glycosylation products comprise less than 50%, 30%, 10%, 8%, 6%, 4%or 2%mono-glycosylated RU (i.e., RU backbone with one added monosaccharide unit) by weight of the glycosylation products.
  • the glycosylation products such as GSGs, GSEs, GSTEs, GSTCs, comprise greater than 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%or 60%mono-glycosylated RU by weight of the glycosylation products.
  • the glycosylation products such as GSGs, GSEs, GSTEs, GSTCs
  • the glycosylation products comprise less than 50%, 40%, 15%, 12%, 10%, 8%, 6%, 4%or 2%bi-glycosylated RU (i.e., RU backbone with two added monosaccharide units) by weight of the glycosylation products.
  • the glycosylation products such as GSGs, GSEs, GSTEs, GSTCs, comprise greater than 1%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%or 50%bi-glycosylated RU by weight of the glycosylation products.
  • the glycosylation products such as GSGs, GSEs, GSTEs, GSTCs
  • the glycosylation products comprise less than 20%, 15%, 5%, 4%, 3%, 2%, 1%tri-glycosylated RU (i.e., RU backbone with three added monosaccharide units) by weight of the glycosylation products.
  • the glycosylation products such as GSGs, GSEs, GSTEs, GSTCs, comprise greater than 5%, 10%, 15%, 20%, 25%, 30%, 35%or 40%tri-glycosylated RU by weight of the glycosylation products.
  • the glycosylation products such as GSGs, GSEs, GSTEs, GSTCs, comprise mono-glycosylated RU, bi-glycosylated RU and triglycosylated RU in a total amount of less than 30%, 25%, 20%, 15%or 10%by weight of the glycosylation products.
  • the glycosylation products such as GSGs, GSEs, GSTEs, GSTCs, comprise mono-glycosylated RU, bi-glycosylated RU and triglycosylated RU in a total amount of greater than 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%or 90%by weight of the glycosylation products.
  • the glycosylation products such as GSGs, GSEs, GSTEs, GSTCs, comprise RU in an amount of less than 30%, 25%, 20%, 15%, 10%, 5%, 4%, 3%, 2%or 1%by weight of the glycosylation products.
  • the glycosylation products such as GSGs, GSEs, GSTEs, GSTCs, comprise RU in an amount of greated than 1%, 2%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%or 80%by weight of the glycosylation products.
  • the components can have ratios of from 1 ⁇ 99, 2 ⁇ 98, 3 ⁇ 97, 4 ⁇ 96, 5 ⁇ 95, 6 ⁇ 94, 7 ⁇ 93, 8 ⁇ 92, 9 ⁇ 91, 10 ⁇ 90, 11 ⁇ 89, 12 ⁇ 88, 13 ⁇ 87, 14 ⁇ 86, 15 ⁇ 85, 16 ⁇ 84, 17 ⁇ 83, 18 ⁇ 82, 19 ⁇ 81, 20 ⁇ 80, 21 ⁇ 79, 22 ⁇ 78, 23 ⁇ 77, 24 ⁇ 76, 25 ⁇ 75, 26 ⁇ 74, 27 ⁇ 73, 28 ⁇ 72, 29 ⁇ 71, 30 ⁇ 70, 31 ⁇ 69, 32 ⁇ 68, 33 ⁇ 67, 34 ⁇ 66, 35 ⁇ 65, 36 ⁇ 64, 37 ⁇ 63, 38 ⁇ 62, 39 ⁇ 61, 40 ⁇ 60, 41 ⁇ 59, 42 ⁇ 58, 43 ⁇ 57, 44 ⁇ 56, 45 ⁇ 55, 46 ⁇ 54, 47 ⁇ 53, 48 ⁇ 52, 49 ⁇ 51 and 50 ⁇ 50, and all ranges therebetween wherein the ratios are from 1 ⁇ 99 and vice versa, e.g., a ratio of from 1
  • the different components can be GSGs, GSEs, STEs, STCs, RU, G-STEs, G-STCs, G-SU, sweeteners, non-nutritive sweeteners, individual components of sweeteners, such as RA, RB, RD, RM, etc., components of stevia extracts, components of mogroside extracts, etc.
  • the components can have ratios of from 1 ⁇ 1 ⁇ 98, 1 ⁇ 2 ⁇ 97, 1 ⁇ 3 ⁇ 96, 1 ⁇ 4 ⁇ 95, 1 ⁇ 5 ⁇ 94, 1 ⁇ 6 ⁇ 93, 1 ⁇ 7 ⁇ 92, 1 ⁇ 8 ⁇ 91, 1 ⁇ 9 ⁇ 90, 1 ⁇ 10 ⁇ 89, 1 ⁇ 11 ⁇ 88, 1 ⁇ 12 ⁇ 87, 1 ⁇ 13 ⁇ 86, 1 ⁇ 14 ⁇ 85, 1 ⁇ 15 ⁇ 84, 1 ⁇ 16 ⁇ 83, 1 ⁇ 17 ⁇ 82, 1 ⁇ 18 ⁇ 81, 1 ⁇ 19 ⁇ 80, 1 ⁇ 20 ⁇ 79, 1 ⁇ 21 ⁇ 78, 1 ⁇ 22 ⁇ 77, 1 ⁇ 23 ⁇ 76, 1 ⁇ 24 ⁇ 75, 1 ⁇ 25 ⁇ 74, 1 ⁇ 26 ⁇ 73, 1 ⁇ 27 ⁇ 72, 1 ⁇ 28 ⁇ 71, 1 ⁇ 29 ⁇ 70, 1 ⁇ 30 ⁇ 69, 1 ⁇ 31 ⁇ 68, 1 ⁇ 32 ⁇ 67, 2 ⁇ 3 ⁇ 95, 2 ⁇ 4 ⁇ 94, 2 ⁇ 5 ⁇ 93, 2 ⁇ 6 ⁇ 92, 2 ⁇ 7 ⁇ 91, 2 ⁇ 8 ⁇ 90, 2 ⁇ 9 ⁇ 89
  • the different components can be GSGs, GSEs, STEs, STCs, RU, G-STEs, G-STCs, G-SU, sweeteners, non-nutritive sweeteners, individual components of sweeteners, such as RA, RB, RD, RM, etc., components of stevia extracts, components of mogroside extracts, etc.
  • the present disclosure is not limited to compositions having only two or three different components, and that the exemplary ratios are non-limiting. Rather, the same formula can be followed for establishing ratios of as many different components as are contained within a given composition.
  • the components can have ratios of from 1 ⁇ 1 ⁇ 1 ⁇ 1 ⁇ 1 ⁇ 1 ⁇ 1 ⁇ 1 ⁇ 1 ⁇ 1 ⁇ 1 ⁇ 1 ⁇ 1 ⁇ 1 ⁇ 1 ⁇ 1 ⁇ 1 ⁇ 81 to 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5 ⁇ 5, and all possible combinations of ratios therebetween.
  • a composition of the present disclosure may have up to and including a combination of all compounds.
  • the SGs, SEs, STEs, STCs and compositions derived therefrom contain volatile and unvolatile terpine and/or terpinoid substances that can be further purified in order to obtain substance providing a tasteful, sweet and/or aromatic profile.
  • Treatment of SGs, SEs, GSGs, GSEs, STEs, STCs, GSTEs, and GSTCs using column chromatography, separation resins, and/or other separation methods, such as distillation, can be employed to retain most of the tasteful aroma terpine and/or terpinoid substances containing oxygen in the structure, while removing other unpleasant taste substances.
  • High intensity sweeteners like natural sweeteners such as stevia extract, monk fruit extract etc, and synthetic sweeteners such as sucralose, acesulfame-K, aspartame, sodium saccharin etc. are characterized by their slow on-site, less high-peak sweetness, lower tongue heaviness, sweet aftertaste, less mouth coating, slipperiness, and high bitter aftertaste, metallic aftertaste.
  • An extraordinary or good beverage must have synchronized or harmonized sweetness temporal profile, acidity temporal profile and aroma temporal profile. However, it is painful for food and beverage formulators when using these high intensity sweeteners to make these three dimensions synchronized, especially for sugar reduced, sugar free products.
  • the formulation sequence seeks to achieve balanced sweetness and sourness, followed by the addition of flavor.
  • the deficiencies associated with high intensity sweeteners renders current diet products less palatable to consumers.
  • flavor, acidity and sweetness are not sufficiently integrated in diet products; such non-synchronized products leave either an initial bad taste/flavor which makes them less prone to be swallowed, or they leave an undesirable aftertaste or after flavor.
  • the temporal profile of the flavor (s) is very short, or the flavor comes first before sweet or sour taste, or is associated with bitterness, lingering, and/or a metallic taste. All of so-called “good tasting” natural sweeteners, such as Reb D and Reb M, as well as synthetic sweeteners, such as Ac-K and sucralose, create metallic and lingering tastes, which are difficult for consumers to accept.
  • Oral acceptability constitues a big decision for consumers. For example, where a product or drink is bitter, a baby or child may use their mouth or tongue to repel the food or beverage therefrom. Mouth is the scout to identify the risk. Ideally, a food or beverage should create a synchronized aroma/taste leading one to relax and release their alertness and suspiciousness, and promote swallowing of the food or beverage.
  • An additional embodiment of a food or beverage comprises rubusoside and one or more components selected from GSGs, GSEs, G-STEs, G-STCs, and high intensity sweeteners, 1) where rubusoside is less than 100 ppm; or 2) where total rubusoside and glycosylated rubusoside is less than 1,000 ppm, less than 800 ppm, 600 ppm, less than 500 ppm, less than 400 ppm, less than 200 ppm, less than 100 ppm, less than 50 ppm, less than 20 ppm or less than 10 ppm.
  • the food or beverage comprising a GSE, GSG, G-STE, and/or G-STC comprises mono-glycosylated rubusoside and unconverted rubusoside, where the mono-glycosylated rubusoside in the total glycosylate rubusosides is more than 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%or 95%.
  • a further embodiment of a food or beverage comprises rubusoside and glycosylated rubusoside, where the mono-glycosylated rubusoside is more than 1 ppm, 10 ppm, 50 ppm, 100 ppm, 150 ppm, 200 ppm, 250 ppm, 300 ppm, 500 ppm, 1,000 ppm or 10,000 ppm.
  • a further embodiment of a food or beverage comprises glycosylated rubusoside, where the mono-glycosylated rubusoside is present but in an amount that is less than 10,000 ppm, 5,000 ppm, 1,000 ppm, 500 ppm, 300 ppm, 250 ppm, 100 ppm, 50 ppm, 10 ppm, 5 ppm or 1 ppm.
  • mono-glycosylated rubusoside is present in an amount of 0.01-10,000 ppm, 0.01-5,000 ppm, 0.01-1,000 ppm, 0.01-500 ppm, 0.01-300 ppm, 0.01-250 ppm, 0.01-100 ppm, 0.01-50 ppm, 0.01-10 ppm, 0.01-5 ppm, 0.01-1 ppm, 0.1-10,000 ppm, 0.1-5,000 ppm, 0.1-1,000 ppm, 0.1-500 ppm, 0.1-300 ppm, 0.1-250 ppm, 0.1-100 ppm, 0.1-50 ppm, 0.1-10 ppm, 0.1-5 ppm or 0.1-1 ppm, 1-10,000 ppm, 1-5,000 ppm, 1-1,000 ppm, 1-500 ppm, 1-300 ppm, 1-250 ppm, 1-100 ppm, 1-50 ppm, 0.1-10 ppm, 0.1-5 ppm or 0.1-1 ppm,
  • the nasal cavity has a large surface area and is a good approach for brain nutrition and medicines.
  • Sublingual administration has certain advantages over oral administration. Being more direct, it is often faster and effective.
  • the intranasal and sublingual route of drug administration has been used for a variety of medications.
  • Current invention provide a solution to make intranasal and sublingual nutrition and medicines more palatable.
  • An embodiment of intranasal or sublingual composition comprises one or more ingredients selected from G-STEs and G-STCs.
  • bitter tastes remains a primary goal for the food and beverage industry.
  • Bitterness has been a challenge with a wide range of foodstuffs, including fruits, such as grapefruit, passionfruit, oranges; vegetables, including cucumbers and avocados; beverage products, including beer, coffee, and chocolate; and protein products, including dairy and soy products.
  • the inventor of the present application has successfully developed compositions comprising one or more ingredients selected from G-STEs and G-STCs, which can mask the bitterness of food and beverage products.
  • SGs, GSGs, SE, GSE, STE, STC, GSTE and GSTC comprises rubusoside and or glycosylated rubusosides, could enhance the astringency, accelerate the quick acidity sensation.
  • An embodiment of a consumable comprises one or more substances selected from SGs, SE, GSE, GSGs, STE, STC, GSTE and GSTC comprises rubusoside and or glycosylated rubusosides, which could enhance the astringency and quick acid onsite sensation.
  • the consumable is contains tea extract, tea concentrate, cranberry juice, cranberry flavor, cranberry concentrate, grapefruit juice, grapefruit concentrate, grapefruit flavor, lemon and or lime flavor/juice/concentrate.
  • a consumable contains one or more substances selected from STE, STC, GSTE, and GSTC, s and quinic acid, where the quinic acid is above 0.1ppm, 1ppm, 5ppm, 10ppm, 50ppm, 100ppm, 200ppm, 500ppm, 1,000ppm, 2,000ppm, 5,000ppm, 10,000ppm, 50,000ppm or 100,000ppm.
  • rubusoside is one of STC, it should be understandable in whole specification that STC includes rubusoside or other sweet tea components originated from other sources including but not limited to stevia extract, stevia glycosides, or fermentation, enzymatic conversion, synthetic method.
  • An embodiment of a consumable comprises one or more substances selected from STE, STC, GSTE and GSTC, and stevia extract comprises one or more stevia glycosides selected from Reb A, Reb B, Reb C, Reb D, Reb E, Reb I, Reb M, Reb O, which solubility and or sweetness of stevia extract is increased.
  • composition comprises GSG, GSE, GSTE or GSTC, where the ratio of one-added glucose to two added glucose to rubusoside is more than 1.
  • composition comprises SGs, SE, STE or STC, where the rubusoside content is less than 90%, less than 70%, less than 50%, less than 30%, less than 20%, less than 15%, less than 10%, less than 5%, the non-rubusoside substances originated from sweet tea plant are above 5%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%or 95%.
  • composition comprises GSG, GSE, G-STE or G-STC, where total glycosylated rubusosides is less than 90%, less than 70%, less than 50%, less than 30%, less than 20%, less than 15%, less than 10%, less than 5%, the non-rubusoside substances or their glycosylated form originated from sweet tea plant are above 5%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%or 95%.
  • aqueous solubility is not only an obstacle to extend their application for stevia glycosides, but also for many other pharmaceutical active substances, herb extract, for instance, carotenoids like lutein, zeaxanthin, lutein esters, epilutein, polyphenols like apple polyphenols, kiwi polyphenols, grape seed polyphenols, flavonoids such as flavonoids extracted from gingko biloba, alkaloids such as devil’s claw extract etc.
  • the inventor found high intensity sweetener extracts, such as stevia extract, sweet tea extract, monk fruit extract could improve the solubility of substances which have poor water solubility; preferably the crude extract comprises non-stevia glycosides or non-sweetening substances.
  • composition comprising a) one or more ingredient selected from sweet tea extract, stevia extract, monk fruit extract, licorice extract, their glycosylated products; and b) one or more ingredient selected from herb extract or pharmaceutical active ingredients, where a) could improve the solubility and bioavailability of b) .
  • Flavors from edible products such as fruits, berries, herbs and species are useful to enhance the palatability of food and beverage.
  • the prevailing mindset of flavor industry takes volatile substances to bring the olfactory smell as key factor to measure the quality of flavor.
  • the inventor found flavors containing flavor substances from fruit juice, berries juice, fresh herb or species juices could have substantially positive impact on retronasal flavors when adding into a food or beverage.
  • the flavor compositions comprises less volatile substances are important to influence the palatability of food and beverage.
  • composition comprising a) one or more ingredient selected from sweet tea extract, stevia extract, monk fruit extract and licorice extract, their glycosylated products; and b) one or more flavor extracted or concentrated ingredient selected from fruits juices, berries juices, herb and species fresh juices, where b) comprises less volatile or non-volatile substances from juices, and the composition could improve the palatability of food and beverage substantially.
  • An additional embodiment of such composition comprises water soluble juicy substances, such as fruit concentration or juice concentrate or extract from water melon, bilberry, citrus, orange, lime, lemon, kiwi, apple etc.
  • a SG, GSG, SE, GSE, STE, STC, GSTE or GSTC can be enriched for the presence of aromatic terpene substances containing oxygen in the structure.
  • a citrus or tangerine taste is enhanced by heat-treating a terpine-and/or terpinoid rich STE under acidic conditions comprising e.g., citric acid, tartaric acid, fumaric acid, lactic acid, malic acid etc., more preferably citric acid.
  • substances such as linalool can react with citric acid.
  • Vacuum distillation of fractions or column chromatography employing macroporous resins and/or silica gels, including ion exchange resins produced by Dow and Sunresin can be used for further purification.
  • a SG, GSG, SE, GSE, STE, STC, GSTE or GSTC composition further includes flavor substances from the sweet tea plant or other natural sweetener plants described herein, including leaves, roots, seeds, etc. therefrom.
  • the present application provides a stevioside-enriched composition or extract.
  • stevioside-enriched refers to a composition or Stevia extract containing or processed to contain more than 50%stevioside.
  • the present application provides a rubusoside-enriched composition originated from Stevia extract (RU-Stevia) .
  • the term “rubusoside-enriched composition” refers to a composition or extract containing, or processed to contain, more than 50%rubusoside.
  • the RU-Stevia composition is obtained by bio-conversion of stevioside to rubusoside using a stevioside-enriched Stevia composition or extract (containing stevioside more than 40%) , including sweetener and flavor compositions thereof.
  • the term “GRU-Stevia” composition is used with reference to a glycosylate composition formed from an RU-Stevia composition.
  • a sweetener or flavor composition includes one or more components selected from the group consisting of 9-OH Suav J, suavioside A, Suavioside B, Suavioside E, uavioside F, Suavioside H, Suavioside K, Suavioside L, Suavioside O, Steviol, Reb A, and Rubososide.
  • an RU-Stevia sweetener or flavor composition comprises Stevia composition having a rubusoside content of at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or any range defined by any pair of these integers.
  • an RU-Stevia sweetener or flavor composition includes rubusoside and sauviosides, where the total content of sauviosides is at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or any range defined by any pair of these integers.
  • an RU-Stevia sweetener or flavor composition comprises Reb A, rubusoside and one or more sauviosides, where the Reb A content is less than 50%, less than 40%, less than 30%, less than 20%, less than 10%, less than 5%, less than 1%.
  • an RU-Stevia sweetener, flavor sweetener or flavor composition comprises one or more substances selected from 9-OH Suav J, suavioside A, Suavioside B, Suavioside E, Suavioside F, Suavioside H, Suavioside K, Suavioside L, Suavioside O, Steviol, Reb A, Rubososide, and stevioside, where the stevioside content is present but in an amount of less than 50 wt %, less than 40 wt %, less than 30 wt %, less than 20 wt %, less than 10 wt %, less than 5 wt %, less than 2 wt %, or less than 1 wt %of the composition.
  • an RU-Stevia sweetener, flavor sweetener or flavor composition comprises one or more substances selected from 9-OH Suav J, suavioside A, Suavioside B, Suavioside E, Suavioside F, Suavioside H, Suavioside K, Suavioside L, Suavioside O, Steviol, Reb A, Rubososide, and stevioside, where the stevioside content is present but in an amount of 0.01-50 wt %, 0.01-40 wt %, 0.01-30 wt %, 0.01-20 wt %, 0.01-10 wt %, 0.01-5 wt %, 0.01-2 wt %, or 0.01-1 wt %of the composition.
  • a GRU-Stevia composition is prepared from an RU-Stevia composition comprising one or more substances selected from 9-OH Suav J, suavioside A, Suavioside B, Suavioside E, Suavioside F, Suavioside H, Suavioside K, Suavioside L, Suavioside O, Steviol, Reb A, and Rubososide.
  • the sweetener or flavor composition comprises GRU-Stevia and a sweetener composition, where the sweetener composition includes one or more substances selected from high intensity synthetic sweeteners, high intensity natural sweetners, bulk sweetners, and low sweetness products.
  • the sweetener or flavor composition comprises glycosylated rubusosides and a sweetener, where the sweetener is selected from high intensity synthetic sweeteners, high intensity natural sweetners, bulk sweeteners, and low sweetness products, where the content of glycosylated rubusosides is at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt
  • a GRU-Stevia sweetener or flavor composition comprises GRU-Stevia, unreated RU-stevia, and unreacted sugar donors.
  • the sweetner or flavor composition comprises: (a) GSGs; and (b) SGs, where (a) the GSGs are prepared from an SG composition comprising Reb A in an amount less than 20%, less than 10%, less than 5%, or less than 1%.
  • the sweeetner or flavor composition comprises GSGs, where the total GSG content is at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or any range defined by any pair of these integers.
  • the sweetener or flavor composition comprises GSGs, where the glycosylated Reb B content is at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or any range defined by any pair of these integers.
  • the sweetener or flavor composition comprises GSGs, where the glycosylated Reb C content is at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or any range defined by any pair of these integers.
  • the sweetener or flavor composition comprises GSGs, where the glycosylated Reb D content is at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or any range defined by any pair of these integers.
  • the sweetener or flavor composition comprises GSGs, where the glycosylated Reb E content is at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or any range defined by any pair of these integers.
  • the sweetener or flavor composition comprises GSGs, where the glycosylated Reb M content is at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or any range defined by any pair of these integers.
  • the sweetener or flavor composition comprises GSGs, where the glycosylated steviolmonoside content is at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or any range defined by any pair of these integers.
  • the sweetener or flavor composition comprises GSGs, where the glycosylated steviolbioside content is at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or any range defined by any pair of these integers.
  • the sweetener or flavor composition comprises GSGs, where the glycosylated dulcoside A content is at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or any range defined by any pair of these integers.
  • the sweetener or flavor composition comprises glycosylated sauviosides, where the total glycosylated sauvioside content is at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or any range defined by any pair of these integers.
  • the sweetener or flavor composition comprises (a) GSGs; and (b) stevia glycosides, where the GSGs are from SG compositions comprising stevioside in an amount greater than 30%wt%, greater than 40%wt%, greater than 50%wt%, greater than 60%wt%, greater than 70%wt%, greater than 80%wt%, greater than 90%wt%, or greater than 95%wt%, more preferably where the stevioside content is greater than 60 wt%, greater than 70 wt%, greater than 80 wt%, greater than 90 wt%, greater than 95 wt%, and most preferably where the rubusoside content is greater than 90 wt%or greater than 95 wt%.
  • the SG composition will at least include some (or detectable) levels of stevioside.
  • the sweetener or flavor composition comprises (a) GSGs and (b) SGs, where the GSGs are prepared from stevia glycoside compositions comprising rubusoside in an amount greater than 5 wt%, greater than 10 wt%, greater than 30 wt%, greater than 40 wt%, greater than 50 wt%, greater than 60 wt%, greater than 70 wt%, greater than 80 wt%, greater than 90 wt%, or greater than 95 wt%, more preferably where the rubusoside content is greater than 60 wt%, greater than 70 wt%, greater than 80 wt%, greater than 90 wt%, greater than 95 wt%, and most preferably where the rubusoside content is greater than 80 wt%, greater than 90 wt%, greater than 95 wt%; and where the SGs include one or more components selected from Reb A, Reb B, stevioside, Reb C, Reb D, Reb E, Reb F,
  • a consumable product comprises GSGs as described in the present application, including GSGs present in the consumable product in a range from 0.1 ⁇ 1,5000 ppm.
  • compositions and methods described herein are useful in a wide range of consumable products.
  • a non-limiting outline of products for application of the sweet tea-based sweetener or flavoring compositions described herein includes the following:
  • Dairy based drinks flavored and/or fermented
  • Dairy-based desserts e.g., ice cream, ice milk, pudding, fruit or flavored yogurt
  • Fat emulsions other than 2.2 including mixed and/or flavored products based on fat emulsions.
  • Fruit-based desserts including fruit-flavored water-based desserts
  • Vegetables including mushrooms and fungi, roots and tubers, pulses and legumes
  • nuts and seeds including mushrooms and fungi, roots and tubers, pulses and legumes
  • Cocoa mixes (powder and syrups)
  • Cocoa based spreads including fillings
  • Cocoa and chocolate products e.g., milk chocolate bars, chocolate flakes, white chocolate
  • Cereals and cereal products including flours and starches from roots and tubers, and pulses and legumes, excluding bakery wares
  • Cereals and starch-based desserts e.g., rice pudding, tapioca pudding
  • Batters e.g., for fish or poultry
  • Bread-type products including bread stuffing and breadcrumbs
  • Fine bakery products e.g., doughnuts, sweet rolls, scones and muffins
  • Table -top sweeteners including those containing high-intensity sweeteners, other than 11.1-11.3
  • Emulsified sauces e.g., mayonnaise, salad dressing
  • Non-emulsified sauces e.g., ketchup, cheese sauce, cream sauce, brown gravy
  • Non-carbonated drinks including punches
  • Alcoholic beverages including alcohol-free and low-alcoholic counterparts
  • Processed nuts including coated nuts and nut mixtures (with e.g., dried fruit)
  • the present application provides an orally consumable product comprising one or more sweet tea-based sweetener or flavoring compositions of the present application described herein.
  • consumables refers to substances which are contacted with the mouth of man or animal, including substances, which are taken into and subsequently ejected from the mouth, substances which are drunk, eaten, swallowed or otherwise ingested, and are safe for human or animal consumption when used in a generally acceptable range.
  • the sweetener or flavoring compositions of the present application can be added to an orally consumable product to provide a sweetened product or a flavored product.
  • the sweetener or flavoring compositions of the present application can be incorporated into any oral consumable product, including but not limited to, for example, beverages and beverage products, food products or foodstuffs (e.g., confections, condiments, baked goods, cereal compositions, dairy products, chewing compositions, and tabletop sweetener compositions) , pharmaceutical compositions, smoking compositions, oral hygiene compositions, dental compositions, and the like. Consumables can be sweetened or unsweetened.
  • Consumables employing the sweetener or flavoring compositions of the present application are also suitable for use in processed agricultural products, livestock products or seafood; processed meat products such as sausage and the like; retort food products, pickles, preserves boiled in soy sauce, delicacies, side dishes; soups; snacks, such as potato chips, cookies, or the like; as shredded filler, leaf, stem, stalk, homogenized leaf cured and animal feed.
  • a beverage or beverage product comprises a composition of the present application, or a sweetener composition comprising the same.
  • the beverage may be sweetened or unsweetened.
  • the composition of the present application, or sweetener composition comprising the same may be added to a beverage to sweeten the beverage or enhance its existing sweetness or flavor profile.
  • the composition of the present application comprises one or more substances selected from the group consisting of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs.
  • a “beverage” or “beverage product, ” is used herein with reference to a ready-to-drink beverage, beverage concentrate, beverage syrup, or powdered beverage.
  • Suitable ready-to-drink beverages include carbonated and non-carbonated beverages.
  • Carbonated beverages include, but are not limited to, frozen carbonated beverages, enhanced sparkling beverages, cola, fruit-flavored sparkling beverages (e.g., lemon-lime, orange, grape, strawberry and pineapple) , ginger-ale, soft drinks and root beer.
  • Non-carbonated beverages include, but are not limited to, fruit juice, fruit-flavored juice, juice drinks, nectars, vegetable juice, vegetable-flavored juice, sports drinks, energy drinks, enhanced water drinks, enhanced water with vitamins, near water drinks (e.g., water with natural or synthetic flavorants) , coconut water, tea type drinks (e.g., black tea, green tea, red tea, oolong tea) , coffee, cocoa drink, broths, beverages comprising milk components (e.g., milk beverages, coffee comprising milk components, cafe au lair, milk tea, fruit milk beverages) , beverages comprising cereal extracts, and smoothies.
  • fruit juice fruit-flavored juice, juice drinks, nectars, vegetable juice, vegetable-flavored juice, sports drinks, energy drinks, enhanced water drinks, enhanced water with vitamins, near water drinks (e.g., water with natural or synthetic flavorants) , coconut water, tea type drinks (e.g., black tea, green tea, red tea, oolong tea) , coffee, cocoa drink, broths, beverages comprising milk
  • Beverages may be frozen, semi-frozen ( “slush” ) , non-frozen, ready-to-drink, concentrated (powdered, frozen, or syrup) , dairy, non-dairy, probiotic, prebiotice, herbal, non-herbal, caffeinated, non-caffeinated, alcoholic, non-alcoholic, flavored, non-flavored, vegetable-based, fruit-based, root/tuber/corm-based, nut-based, other plant-based, cola-based, chocolate-based, meat-based, seafood-based, other animal-based, algae-based, calorie enhanced, calorie-reduced, and calorie-free.
  • the resulting beverages may be dispensed in open containers, cans, bottles or other packaging.
  • Such beverages and beverage preparations can be in ready-to-drink, ready-to-cook, ready-to-mix, raw, or ingredient form and can use the composition as a sole sweetener or as a co-sweetener.
  • the present embodiments provide new methods to provide water soluble solutions, syrups and powders for flavoring agents.
  • the current embodiments provide new types of combined multi components which are compatible for a designed flavor.
  • the embodiments surprisingly create sugar reduced sweeteners which have better taste than sugar including, for example, sweetening agents such as Stevia extract, steviol glycosides, STE, monk fruit, licorice, etc. and synthetic sweetener such as sucralose.
  • sweetening agents such as Stevia extract, steviol glycosides, STE, monk fruit, licorice, etc.
  • synthetic sweetener such as sucralose.
  • Beverage concentrates and beverage syrups can be prepared with an initial volume of liquid matrix (e.g., water) and the desired beverage ingredients. Full strength beverages are then prepared by adding further volumes of water. Powdered beverages are prepared by dry-mixing all of the beverage ingredients in the absence of a liquid matrix. Full strength beverages are then prepared by adding the full volume of water.
  • liquid matrix e.g., water
  • Powdered beverages are prepared by dry-mixing all of the beverage ingredients in the absence of a liquid matrix.
  • Full strength beverages are then prepared by adding the full volume of water.
  • Beverages comprise a matrix, i.e., the basic ingredient in which the ingredients -including the compositions of the present application -are dissolved.
  • a beverage comprises water of beverage quality as the matrix, such as, for example deionized water, distilled water, reverse osmosis water, carbon-treated water, purified water, demineralized water or combinations thereof, can be used.
  • Additional suitable matrices include, but are not limited to phosphoric acid, phosphate buffer, citric acid, citrate buffer and carbon-treated water.
  • beverage concentrations below can be provided by the composition of the present application or sweetener composition of the present application.
  • the STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs described herein could also partially or totally replace thickeners used in the food and beverage industry. There is a synergy between the STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, and thickeners to obtain a balance of taste and cost.
  • the size of bubbles in a carbonated beverage can significantly affect the mouth feel and flavor of the beverage. It is desirable to manipulate one or more properties of the bubbles produced in a beverage. Such properties can include the size of bubbles produced, the shape of bubbles, the amount of bubbles generated, and the rate at which bubbles are released or otherwise generated. Taste tests revealed a preference for carbonated beverages containing bubbles of smaller size.
  • compositions of STEs, STCs, GSTEs, and GSTCs, with or without other additives such as sweetening agents and/or thaumatin, can be used as additives to manipulate the size of bubbles, preferably for reducing the size of bubbles.
  • STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs especially STEs, STCs, GSTEs and GSTCs can significantly improve the overall taste profile of food and beverages to have a better mouth feel, a creamy taste, a reduction of bitterness of other ingredients in food and beverage, such as astringency of tea, protein, or their extracts, acidic nature and bitterness of coffee, etc.
  • sweetening agents or sweeteners such as sucralose, acesulfame-K, aspartame, steviol glycosides, swingle extract, sweet tea extracts, allulose, sodium saccharin, sodium cyclamate or siratose.
  • a probiotic beverage normally is made by fermenting milk, or skimmed milk powder, sucrose and/or glucose with selected bacteria strains, by manufacturers such as Yakult or Weichuan.
  • a large amount of sugar is added to the probiotic beverage to provide nutrients to the probiotics in order to keep them alive during shelf life.
  • the main function of such a large amount of sugar is also needed to counteract the sourness of probiotic beverage and enhance its taste.
  • Sweetness and the thickness are the two key attributes that are most affected for the acceptability of the beverage. It is a challenge for the manufacturers to produce tasteful probiotic beverages of reduced sugar versions.
  • the final concentration of any of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs in the beverage may be 0.0001 ppm, 0.001 ppm, 0.01 ppm, 0.1 ppm, 1 ppm, 2 ppm, 5 ppm, 10 ppm, 15 ppm, 20 ppm, 25 ppm, 30 ppm, 35 ppm, 40 ppm, 45 ppm, 50 ppm, 55 ppm, 60 ppm, 65 ppm, 70 ppm, 75 ppm, 80 ppm, 85 ppm, 90 ppm, 100 ppm, 110 ppm, 120, ppm, 130 ppm, 140 ppm, 150 ppm, 160 ppm, 170 ppm, 180
  • any of the STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs may be present in the beverage at a final concentration ranging from 1 ppm to 15,000 ppm, from 1 ppm to 10,000 ppm, from 1 ppm to 5,000 ppm, from 10 ppm to 1,000 ppm, from 50 ppm to 900 ppm, from 50 ppm to 600 ppm, from 50 ppm to 500 ppm, from 50 ppm to 400 ppm, from 50 ppm to 300 ppm, from 50 ppm to 200 ppm, from 100 ppm to 600 ppm, from 100 ppm to 500 ppm, from 100 ppm to 400 ppm, from 100 ppm to 300 ppm, from 100 ppm to 200 ppm, from 100 ppm to 300
  • final concentration′′ refers to the concentration of, for example, any one of the aforementioned components present in any final composition or final orally consumable product (i.e., after all ingredients and/or compounds have been added to produce the composition or to produce the orally consumable product) .
  • the consumable product comprising one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application is a confection.
  • a “confection” refers to a sweet, a lollipop, a confectionery, or similar term.
  • the confection generally contains a base composition component and a sweetener component.
  • a “base composition” refers to any composition which can be a food item and provides a matrix for carrying the sweetener component.
  • the confection may be in the form of any food that is typically perceived to be rich in sugar or is typically sweet.
  • the confection may be a bakery product, such as a pastry, Bavarian cream, blancmange, cake, brownie, cookie, mousse and the like; a dessert, such as yogurt, a jelly, a drinkable jelly, a pudding; a sweetened food product eaten at tea time or following meals; a frozen food; a cold confection, such as ice, ice milk, lacto-ice and the like (food products in which sweeteners and various other types of raw materials are added to milk products, and the resulting mixture is agitated and frozen) ; ice confections, such as sherbets, dessert ices and the like (food products in which various other types of raw materials are added to a sugary liquid, and the resulting mixture is agitated and frozen) ; general confections, e.g., baked confections or steamed confections such as crackers, biscuits, buns with bean-jam filling, halvah, alfajor, and the like; rice cakes and snacks; table top products;
  • a bakery product such as
  • Suitable base compositions for embodiments of this application may include flour, yeast, water, salt, butter, eggs, milk, milk powder, liquor, gelatin, nuts, chocolate, citric acid, tartaric acid, fumaric acid, natural flavors, artificial flavors, colorings, polyols, sorbitol, isomalt, maltitol, lactitol, malic acid, magnesium stearate, lecithin, hydrogenated glucose syrup, glycerine, natural or synthetic gum, starch, and the like, or combinations thereof.
  • Such components generally are recognized as safe (GRAS) and/or are U.S. Food and Drug Administration (FDA) -approved.
  • the STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be present in the condiment at a final weight concentration of 0.0001 wt %, 0.001 wt %, 0.01 wt %, 0.1 wt %, 1 wt %, 2 wt %, 3 wt %, 4 wt %, 5 wt %, 6 wt %, 7 wt %, 8 wt %., 9wt %, 10wt %, 11 wt %, 12 wt %, 13 wt %, 14wt %, 15 wt %, 16wt %, 17 wt %, 18 wt %, 19 wt %,
  • the STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be present in any of the condiments described herein at a final weight percentage range from 0.001 wt %to 99 wt %, 0.001 wt %to 75 wt %, 0.001 wt %to 50 wt%, 0.001 wt %to 25 wt%, 0.001 wt %to 10 wt %, 0.001 wt %to 5 wt %, 0.001 wt %to 2 wt %, 0.001 wt %to 1 wt %, 0.001 wt %to 0.1 wt %, 0.001 wt %to 0.01 wt %, 0.
  • the base composition of the confection may optionally include other artificial or natural sweeteners, bulk sweeteners, or combinations thereof.
  • Bulk sweeteners include both caloric and non-caloric compounds.
  • Non-limiting examples of bulk sweeteners include sucrose, dextrose, maltose, dextrin, dried invert sugar, fructose or fruit sugar, levulose, honey, unrefined sweetener, galactose, syrups, such as agave syrup or agave nectar, maple syrup, corn syrup, including high fructose corn syrup (HFCS) ; solids, tagatose, polyols (e.g., sorbitol, mannitol, xylitol, lactitol, erythritol, and maltitol) , hydrogenated starch hydrolysates, isomalt, trehalose, or mixtures thereof.
  • the amount of bulk sweetener present in the confection ranges widely depending on the particular embodiment of
  • the consumable product that contains STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application is a condiment.
  • Condiments, as used herein, are compositions used to enhance or improve the flavor of a food or beverage.
  • Non-limiting examples of condiments include ketchup (catsup) ; mustard; barbecue sauce; butter; chili sauce; chutney; cocktail sauce; curry; dips; fish sauce; horseradish; hot sauce; jellies, jams, marmalades, or preserves; mayonnaise; peanut butter; relish; remoulade; salad dressings (e.g., oil and vinegar, Caesar, French, ranch, noted cheese, Russian, Thousand Island, Italian, and balsamic vinaigrette) , salsa; sauerkraut; soy sauce; steak sauce; syrups; tartar sauce; and Worcestershire sauce.
  • ketchup catsup
  • mustard barbecue sauce
  • butter chili sauce
  • chutney cocktail sauce
  • curry dips
  • fish sauce horseradish
  • hot sauce jellies, jams, marmalades, or preserves
  • mayonnaise peanut butter; relish; remoulade
  • salad dressings e.g., oil and vinegar, Caesar, French, ranch, noted cheese, Russian, Thousand Island, Italian
  • Condiment bases generally comprise a mixture of different ingredients, non-limiting examples of which include vehicles (e.g., water and vinegar) ; spices or seasonings (e.g., salt, pepper, garlic, mustard seed, onion, paprika, turmeric, or combinations thereof) ; fruits, vegetables, or their products (e.g., tomatoes or tomato-based products (paste, puree) , fruit juices, fruit juice peels, or combinations thereof) ; oils or oil emulsions, particularly vegetable oils; thickeners (e.g., xanthan gum, food starch, other hydrocolloids, or combinations thereof) ; and emulsifying agents (e.g., egg yolk solids, protein, gum arabic, carob bean gum, guar gum, gum karaya, gum tragacanth, carageenan, pectin, propylene glycol esters of alginic acid, sodium carboxymethyl-cellulose, polysorbates, or combinations thereof) .
  • condiments also comprise caloric sweeteners, such as sucrose, high fructose corn syrup, molasses, honey, or brown sugar.
  • caloric sweeteners such as sucrose, high fructose corn syrup, molasses, honey, or brown sugar.
  • an composition containing one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application is used instead of traditional caloric sweeteners.
  • the condiment composition optionally may include other natural and/or synthetic high-potency sweeteners, bulk sweeteners, pH modifying agents (e.g., lactic acid, citric acid, phosphoric acid, hydrochloric acid, acetic acid, or combinations thereof) , fillers, functional agents (e.g., pharmaceutical agents, nutrients, or components of a food or plant) , flavoring agents, colorings, or combinations thereof.
  • pH modifying agents e.g., lactic acid, citric acid, phosphoric acid, hydrochloric acid, acetic acid, or combinations thereof
  • fillers e.g., lactic acid, citric acid, phosphoric acid, hydrochloric acid, acetic acid, or combinations thereof
  • functional agents e.g., pharmaceutical agents, nutrients, or components of a food or plant
  • MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be present in the confection at a final weight concentration of 0.0001 wt %, 0.001 wt %, 0.01 wt %, 0.1 wt %, 1 wt %, 2 wt %, 3 wt %, 4 wt %, 5 wt %, 6 wt %, 7 wt %, 8 wt %, 9wt %, 10wt %, 11 wt %, 12 wt %, 13 wt %, 14wt %, 15 wt %, 16 wt %, 17 wt %, 18 wt %, 19 wt %,
  • STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be present in any of the confections described herein, at a final weight percentage range from 0.001 wt %to 99 wt %, 0.001 wt %to 75 wt %, 0.001 wt %to 50 wt%, 0.001 wt %to 25 wt%, 0.001 wt %to 10 wt %, 0.001 wt %to 5 wt %, 0.001 wt %to 2 wt %, 0.001 wt %to 1 wt %, 0.001 wt %to 0.1 wt %, 0.001 wt %to 0.01 wt %, 0.
  • dairy products can be made using the STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present invention.
  • Such products include without limitation, milk, whole milk, buttermilk, skim milk, infant formula, condensed milk, dried milk, evaporated milk, fermented milk, butter, clarified butter, cottage cheese, cream cheese, and various types of cheese.
  • the STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be present in the solid dairy composition at a final weight concentration of 0.0001 wt %, 0.001 wt %, 0.01 wt %, 0.1 wt %, 1 wt %, 2 wt %, 3 wt %, 4 wt %, 5 wt %, 6 wt %, 7 wt %, 8wt %, 9wt %, 10 wt %, 11 wt %, 12 wt %, 13 wt %, 14 wt %, 15 wt %, 16wt %, 17wt %, 18wt %, 19wt %
  • the STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be present in any of the confections described herein, at a weight percentage range from 0.001 wt %to 99 wt %, 0.001 wt %to 75 wt %, 0.001 wt %to 50 wt%, 0.001 wt %to 25 wt%, 0.001 wt %to 10 wt %, 0.001 wt %to 5 wt %, 0.001 wt %to 2 wt %, 0.001 wt %to 1 wt %, 0.001 wt %to 0.1 wt %, 0.001 wt %to 0.01 wt %, 0.
  • the STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be present in the liquid dairy composition at a final concentration of 0.0001 ppm, 0.001 ppm, 0.01 ppm, 0.1 ppm, 1 ppm, 2 ppm, 5 ppm, 10 ppm, 15 ppm, 20 ppm, 25 ppm, 30 ppm, 35 ppm, 40 ppm, 45 ppm, 50 ppm, 55 ppm, 60 ppm, 65 ppm, 70 ppm, 75 ppm, 80 ppm, 85 ppm, 90 ppm, 100 ppm, 110 ppm, 120, ppm, 130 ppm, 140 ppm, 150 ppm, 160
  • the STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be present in the liquid dairy composition at a final concentration ranging from 1 ppm to 15,000 ppm, from 1 ppm to 10,000 ppm, from 1 ppm to 5,000 ppm, from 10 ppm to 1,000 ppm, from 50 ppm to 900 ppm, from 50 ppm to 600 ppm, from 50 ppm to 500 ppm, from 50 ppm to 400 ppm, from 50 ppm to 300 ppm, from 50 ppm to 200 ppm, from 100 ppm to 600 ppm, from 100 ppm to 500 ppm, from 100 ppm to 400 ppm, from 100 ppm to 300 ppm, from 100 ppm to 200 ppm, from 100
  • the consumable product comprising one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application is a cereal composition.
  • Cereal compositions typically are eaten either as staple foods or as snacks.
  • Non-limiting examples of cereal compositions for use in some embodiments include ready-to-eat cereals as well as hot cereals. Ready-to-eat cereals are cereals which may be eaten without further processing (i.e., cooking) by the consumer. Examples of ready-to-eat cereals include breakfast cereals and snack bars.
  • Breakfast cereals typically are processed to produce a shredded, flaky, puffy, or extruded form.
  • Breakfast cereals generally are eaten cold and are often mixed with milk and/or fruit.
  • Snack bars include, for example, energy bars, rice cakes, granola bars, and nutritional bars.
  • Hot cereals generally are cooked, usually in either milk or water, before being eaten.
  • Non-limiting examples of hot cereals include grits, porridge, polenta, rice, oatmeal, and rolled oats.
  • Cereal compositions generally comprise at least one cereal ingredient.
  • the term “cereal ingredient” denotes materials such as whole or part grains, whole or part seeds, and whole or part grass.
  • Non-limiting examples of cereal ingredients for use in some embodiments include maize, wheat, rice, barley, bran, bran endosperm, bulgur, sorghums, millets, oats, rye, triticale, buckwheat, fonio, quinoa, bean, soybean, amaranth, teff, spelt, and kaniwa.
  • the cereal composition comprises one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application and at least one cereal ingredient.
  • the STEs, STCs, GSTEs and GSTCs of present application may be added to the cereal composition in a variety of ways, such as, for example, as a coating, as a frosting, as a glaze, or as a matrix blend (i.e., added as an ingredient to the cereal formulation prior to the preparation of the final cereal product) .
  • one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application are added to the cereal composition as a matrix blend.
  • one or more STEs, STCs, GSTEs and GSTCs are blended with a hot cereal prior to cooking to provide a sweetened hot cereal product.
  • one or more STEs, STCs, GSTEs, and GSTCs are blended with the cereal matrix before the cereal is extruded.
  • one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs are added to the cereal composition as a coating, such as, for example, in combination with food grade oil and applying the mixture onto the cereal.
  • one or more STEs, STCs, SGs, SEs, SCs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMFEs and GMFCs, and the food grade oil are applied to the cereal separately, by applying either the oil or the sweetener first.
  • Non-limiting examples of food grade oils for use some embodiments include vegetable oils such as corn oil, soybean oil, cottonseed oil, peanut oil, coconut oil, canola oil, olive oil, sesame seed oil, palm oil, palm kernel oil, or mixtures thereof.
  • food grade fats may be used in place of the oils, provided that the fat is melted prior to applying the fat onto the cereal.
  • one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs are added to the cereal composition as a glaze.
  • Non-limiting examples of glazing agents for use in some embodiments include corn syrup, honey syrups and honey syrup solids, maple syrups and maple syrup solids, sucrose, isomalt, polydextrose, polyols, hydrogenated starch hydrolysate, aqueous solutions thereof, or mixtures thereof.
  • one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs are added as a glaze by combining with a glazing agent and a food grade oil or fat and applying the mixture to the cereal.
  • a gum system such as, for example, gum acacia, carboxymethyl cellulose, or algin, may be added to the glaze to provide structural support.
  • the glaze also may include a coloring agent, and also may include a flavor.
  • one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs are added to the cereal composition as a frosting.
  • one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs are combined with water and a frosting agent and then applied to the cereal.
  • Non-limiting examples of frosting agents for use in some embodiments include maltodextrin, sucrose, starch, polyols, or mixtures thereof.
  • the frosting also may include a food grade oil, a food grade fat, a coloring agent, and/or a flavor.
  • the one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs are present in the cereal composition at a final weight concentration of 0.0001 wt %, 0.001 wt %, 0.01 wt %, 0.1 wt %, 1 wt %, 2wt %, 3 wt %, 4wt %, 5 wt %, 6wt %, 7wt %, 8 wt %, 9 wt %, 10wt %, 11 wt %, 12 wt %, 13 wt %, 14wt %, 15 wt %, 16wt %, 17 wt %, 18 wt %, 19 wt %, 20 wt
  • one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs may be present in any of the cereal compositions described herein, at a weight percentage range from 0.001 wt %to 99 wt %, 0.001 wt %to 75 wt %, 0.001 wt %to 50 wt%, 0.001 wt %to 25 wt%, 0.001 wt %to 10 wt %, 0.001 wt %to 5 wt %, 0.001 wt %to 2 wt %, 0.001 wt %to 1 wt %, 0.001 wt %to 0.1 wt %, 0.001 wt %to 0.01 wt %, 0.01
  • the consumable product comprising one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application is a chewing composition.
  • the term “chewing compositions” include chewing gum compositions, chewing tobacco, smokeless tobacco, snuff, chewing gum and other compositions which are masticated and subsequently expectorated.
  • Chewing gum compositions generally comprise a water-soluble portion and a water-insoluble chewable gum base portion.
  • the water soluble portion which typically includes one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application, dissipates with a portion of the flavoring agent over a period of time during chewing while the insoluble gum base portion is retained in the mouth.
  • the insoluble gum base generally determines whether a gum is considered chewing gum, bubble gum, or a functional gum.
  • the insoluble gum base which is generally present in the chewing gum composition in an amount in the range of about 15 to about 35 weight percent of the chewing gum composition, generally comprises combinations of elastomers, softeners (plasticizers) , emulsifiers, resins, and fillers.
  • Such components generally are considered food grade, recognized as safe (GRA) , and/or are U.S. Food and Drug Administration (FDA) -approved.
  • Elastomers the primary component of the gum base, provide the rubbery, cohesive nature to gums and can include one or more natural rubbers (e.g., smoked latex, liquid latex, or guayule) ; natural gums (e.g., jelutong, perillo, sorva, massaranduba balata, massaranduba chocolate, nispero, rosindinha, chicle, and gutta hang kang) ; or synthetic elastomers (e.g., butadiene-styrene copolymers, isobutylene-isoprene copolymers, polybutadiene, polyisobutylene, and vinyl polymeric elastomers) .
  • the elastomer is present in the gum base in an amount in the range of about 3 to about 50 weight percent of the gum base.
  • Resins are used to vary the firmness of the gum base and aid in softening the elastomer component of the gum base.
  • suitable resins include a rosin ester, a terpene resin (e.g., a terpene resin from ⁇ -pinene, ⁇ -pinene and/or D-limonene) , polyvinyl acetate, polyvinyl alcohol, ethylene vinyl acetate, and vinyl acetate-vinyl laurate copolymers.
  • Non-limiting examples of rosin esters include a glycerol ester of a partially hydrogenated rosin, a glycerol ester of a polymerized rosin, a glycerol ester of a partially dimerized rosin, a glycerol ester of rosin, a pentaerythritol ester of a partially hydrogenated rosin, a methyl ester of rosin, or a methyl ester of a partially hydrogenated rosin.
  • the resin is present in the gum base in an amount in the range of about 5 to about 75 weight percent of the gum base.
  • Softeners which also are known as plasticizers, are used to modify the ease of chewing and/or mouth feel of the chewing gum composition.
  • softeners comprise oils, fats, waxes, and emulsifiers.
  • oils and fats include tallow, hydrogenated tallow, large, hydrogenated or partially hydrogenated vegetable oils (e.g., soybean, canola, cottonseed, sunflower, palm, coconut, corn, safflower, or palm kernel oils) , cocoa butter, glycerol monostearate, glycerol triacetate, glycerol abietate, lecithin, monoglycerides, diglycerides, triglycerides acetylated monoglycerides, and free fatty acids.
  • vegetable oils e.g., soybean, canola, cottonseed, sunflower, palm, coconut, corn, safflower, or palm kernel oils
  • cocoa butter glycerol monostearate
  • Non-limiting examples of waxes include polypropylene/polyethylene/Fisher-Tropsch waxes, paraffin, and microcrystalline and natural waxes (e.g., candelilla, beeswax and carnauba) .
  • microcrystalline waxes especially those with a high degree of crystallinity and a high melting point, also may be considered as bodying agents or textural modifiers.
  • the softeners are present in the gum base in an amount in the range of about 0.5 to about 25 weight percent of the gum base.
  • Emulsifiers are used to form a uniform dispersion of the insoluble and soluble phases of the chewing gum composition and also have plasticizing properties.
  • Suitable emulsifiers include glycerol monostearate (GMS) , lecithin (phosphatidyl choline) , polyglycerol polyricinoleic acid (PPGR) , mono and diglycerides of fatty acids, glycerol distearate, tracetin, acetylated monoglyceride, glycerol triacetate, and magnesium stearate.
  • the emulsifiers are present in the gum base in an amount in the range of about 2 to about 30 weight percent of the gum base.
  • the chewing gum composition also may comprise adjuvants or fillers in either the gum base and/or the soluble portion of the chewing gum composition.
  • Suitable adjuvants and fillers include lecithin, inulin, polydextrin, calcium carbonate, magnesium carbonate, magnesium silicate, ground limestone, aluminum hydroxide, aluminum silicate, talc, clay, alumina, titanium dioxide, and calcium phosphate.
  • lecithin can be used as an inert filler to decrease the stickiness of the chewing gum composition.
  • lactic acid copolymers, proteins (e.g., gluten and/or zein) and/or guar can be used to create a gum that is more readily biodegradable.
  • the adjuvants or fillers are generally present in the gum base in an amount up to about 20 weight percent of the gum base.
  • Other optional ingredients include coloring agents, whiteners, preservatives, and flavors.
  • the gum base comprises about 5 to about 95 weight percent of the chewing gum composition, more desirably about 15 to about 50 weight percent of the chewing gum composition, and even more desirably from about 20 to about 30 weight percent of the chewing gum composition.
  • the soluble portion of the chewing gum composition may optionally include other artificial or natural sweeteners, bulk sweeteners, softeners, emulsifiers, flavoring agents, coloring agents, adjuvants, fillers, functional agents (e.g., pharmaceutical agents or nutrients) , or combinations thereof. Suitable examples of softeners and emulsifiers are described above.
  • Bulk sweeteners include both caloric and non-caloric compounds.
  • Non-limiting examples of bulk sweeteners include sucrose, dextrose, maltose, dextrin, dried invert sugar, fructose, high fructose corn syrup, levulose, galactose, corn syrup solids, tagatose, polyols (e.g., sorbitol, mannitol, xylitol, lactitol, erythritol, and maltitol) , hydrogenated starch hydrolysates, isomalt, trehalose, or mixtures thereof.
  • the bulk sweetener is present in the chewing gum composition in an amount in the range of about 1 to about 75 weight percent of the chewing gum composition.
  • Flavoring agents may be used in either the insoluble gum base or soluble portion of the chewing gum composition. Such flavoring agents may be natural or artificial flavors.
  • the flavoring agent comprises an essential oil, such as an oil produced from a plant or a fruit, peppermint oil, spearmint oil, other mint oils, clove oil, cinnamon oil, oil of wintergreen, bay, thyme, cedar leaf, nutmeg, allspice, sage, mace, and almonds.
  • the flavoring agent comprises a plant extract or a fruit essence such as apple, banana, watermelon, pear, peach, grape, strawberry, raspberry, cherry, plum, pineapple, apricot, or mixtures thereof.
  • the flavoring agent comprises a citrus flavor, such as an extract, essence, or oil of lemon, lime, orange, tangerine, grapefruit, citron, or kumquat.
  • the chewing gum composition comprises one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application and a gum base.
  • the one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be present in the chewing gum composition at a final weight concentration of 0.0001 wt %, 0.001 wt %, 0.01 wt %, 0.1 wt %, 1 wt %, 2 wt %, 3 wt %, 4wt %, 5 wt %, 6wt %, 7wt %, 8 wt %, 9wt %, 10 wt %, 11 wt %, 12 wt %, 13 wt %, 14 wt %, 15 wt %, 16 wt %, 17 wt %, 18 wt %
  • the one or STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be present in any of the chewing gum compositions described herein, at a weight percentage range from 0.001 wt %to 99 wt %, 0.001 wt %to 75 wt %, 0.001 wt %to 50 wt%, 0.001 wt %to 25 wt%, 0.001 wt %to 10 wt %, 0.001 wt %to 5 wt %, 0.001 wt %to 2 wt %, 0.001 wt %to 1 wt %, 0.001 wt %to 0.1 wt %, 0.001 wt %to 0.01 w
  • the present application provides an orally consumable product comprising one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application in the form of an orally consumable tabletop sweetener composition.
  • the orally consumable tabletop sweetener composition has a taste similar to molasses.
  • the tabletop sweetener composition may further include at least one bulking agent, additive, anti-caking agent, functional ingredient or combination thereof.
  • Suitable “bulking agents” include, but are not limited to, maltodextrin (10 DE, 18 DE, or 5 DE) , corn syrup solids (20 or 36 DE) , sucrose, fructose, glucose, invert sugar, sorbitol, xylose, ribulose, mannose, xylitol, mannitol, galactitol, erythritol, maltitol, lactitol, isomalt, maltose, tagatose, lactose, inulin, glycerol, propylene glycol, polyols, polydextrose, fructooligosaccharides, cellulose and cellulose derivatives, and the like, or mixtures thereof.
  • granulated sugar sucrose
  • other caloric sweeteners such as crystalline fructose, other carbohydrates, or sugar alcohol
  • sugar alcohol can be used as a bulking agent due to their provision of good content uniformity without the addition of significant calories.
  • anti-caking agent and “flow agent” refers to any composition which assists in content uniformity and uniform dissolution.
  • non-limiting examples of anti-caking agents include cream of tartar, aluminium silicate (Kaolin) , calcium aluminium silicate, calcium carbonate, calcium silicate, magnesium carbonate, magnesium silicate, mono-, di-and tri-calcium orthophosphate, potassium aluminium silicate, silicon dioxide, soldium aluminium silicate, salts of stearic acid, microcrystalline cellulose (Avicel, FMC BioPolymer, Philadelphia, Pennsylvania) , and tricalcium phosphate.
  • the anti-caking agents are present in the tabletop sweetener composition in an amount from about 0.001 to about 3 %by weight of the tabletop sweetener composition.
  • the tabletop sweetener compositions can be packaged in any form known in the art.
  • Non-limiting forms include, but are not limited to, powder form, granular form, packets, tablets, sachets, pellets, cubes, solids, and liquids.
  • the tabletop sweetener composition is a single-serving (portion control) packet comprising a dry-blend.
  • Dry-blend formulations generally may comprise powder or granules.
  • the tabletop sweetener composition may be in a packet of any size, an illustrative non-limiting example of conventional portion control tabletop sweetener packets are approximately 2.5 by 1.5 inches and hold approximately 1 gram of a sweetener composition having a sweetness equivalent to 2 teaspoons of granulated sugar ( ⁇ 8 g) .
  • a dry-blend tabletop sweetener formulation may comprise a Composition of the present application in an amount from about 1% (w/w) to about 10 % (w/w) of the tabletop sweetener composition.
  • Solid tabletop sweetener embodiments include cubes and tablets.
  • a non-limiting example of conventional cubes is equivalent in size to a standard cube of granulated sugar, which is approximately 2.2 x 2.2 x 2.2 cm 3 and weighs approximately 8 g.
  • a solid tabletop sweetener is in the form of a tablet or any other form known to those skilled in the art.
  • a tabletop sweetener composition also may be embodied in the form of a liquid, wherein one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application are combined with a liquid carrier.
  • suitable non-limiting examples of carrier agents for liquid tabletop sweeteners include water, alcohol, polyol, glycerin base or citric acid base dissolved in water, or mixtures thereof.
  • the sweetness equivalent of a tabletop sweetener composition for any of the forms described herein or known in the art may be varied to obtain a desired sweetness profile.
  • a tabletop sweetener composition may have a degree of sweetness comparable to that of an equivalent amount of standard sugar.
  • the tabletop sweetener composition may comprise a sweetness of up to 100 times that of an equivalent amount of sugar.
  • the tabletop sweetener composition may comprise a sweetness of up to 90 times, 80 times, 70 times, 60 times, 50 times, 40 times, 30 times, 20 times, 10 times, 9 times, 8 times, 7 times, 6 times, 5 times, 4 times, 3 times, and 2 times that of an equivalent amount of sugar.
  • one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be present in the tabletop sweetener composition at a final weight concentration of 0.0001 wt %, 0.001 wt %, 0.01 wt %, 0.1 wt %, 1 wt %, 2 wt %, 3 wt %, 4 wt %, 5 wt %, 6 wt %, 7 wt %, 8 wt %, 9 wt %, 10 wt %, 11 wt %, 12 wt %, 13 wt %, 14 wt %, 15 wt %, 16 wt %, 17 wt %
  • one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be present in any of the tabletop sweetener compositions described herein, at a weight percentage range from 0.001 wt %to 99 wt %, 0.001 wt %to 75 wt %, 0.001 wt %to 50 wt%, 0.001 wt %to 25 wt%, 0.001 wt %to 10 wt %, 0.001 wt %to 5 wt %, 0.001 wt %to 2 wt %, 0.001 wt %to 1 wt %, 0.001 wt %to 0.1 wt %, 0.001 wt %to 0.01
  • one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be used in medicinal compositions.
  • the term “medicinal composition” includes solids, gases and liquids which are ingestible materials having medicinal value, such as cough syrups, cough drops, medicinal sprays, vitamins, and chewable medicinal tablets that are administered orally or used in the oral cavity in the form of e.g., a pill, tablet, spray, capsule, syrup, drop, troche agent, powder, and the like.
  • one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be used in an oral hygiene composition.
  • the “oral hygiene composition” includes mouthwashes, mouth rinses, breath fresheners, toothpastes, tooth polishes, dentifrices, mouth sprays, teeth whitening agents, soaps, perfumes, and the like.
  • the oral hygiene product comprises a sweetener composition
  • a sweetener composition comprising (1) one or more components selected from the group consisting of RU, GRU, STEs, GSTEs, STCs, GSTCs, MGs, GMGs, MFCs, GMFCs, SEs, GSEs, SCs, GSCs, SGs and GSGs of the present application, and (2) sugar donors or residues thereof in an amount that is greater than zero, but is less than 15%, less than 10%, less than 5%, less than 4%, less than 3%, less than 2%, less than 1%, less than 0.5%, less than 0.1%, less than 0.05%, or less than 0.01% (wt/wt) of the sweetener composition.
  • one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application is utilized in a cosmetic composition for enhancing the aroma of a cosmetic or skin-care product.
  • cosmetic composition means a composition that is formulated for topical application to skin, which has a pleasant colour, odour and feel, and which does not cause unacceptable discomfort (stinging, tautness or redness) liable to discourage the consumer from using it.
  • Cosmetic composition may be preferably formulated in the form of an emulsion, e.g., W/O (water-in-oil) , O/W (oil-in-water) , W/O/W (water-in-oil-in-water) , O/W/O (oil-in-water-in-oil) emulsion, PIT emulsion, Pickering emulsion, emulsion with a low oil content, micro-or nanoemulsion, a solution, e.g., in oil (fatty oils or fatty acid esters, in particular C 6 -C 32 fatty acid C 2 -C 30 esters) or silicone oil, dispersion, suspension, creme, lotion or milk, depending on the production method and ingredients, a gel (including hydrogel, hydrodispersion gel, oleogel) , spray (e.g., pump spray or spray with propellant) or a foam or an impregnating solution for cosmetic wipes, a detergent, e.g
  • a skin care product such as e.g., an emulsion (as described above) , ointment, paste, gel (as described above) , oil, balsam, serum, powder (e.g., face powder, body powder) , a mask, a pencil, stick, roll-on, pump, aerosol (foaming, non-foaming or post-foaming) , a deodorant and/or antiperspirant, mouthwash and mouth rinse, a foot care product (including keratolytic, deodorant) , an insect repellent, a sunscreen, aftersun preparation, a shaving product, aftershave balm, pre-and aftershave lotion, a depilatory agent, a hair care product such as e.g., shampoo (including 2-in-1 shampoo, anti-dandruff shampoo, baby shampoo, shampoo for dry scalps, concentrated shampoo) , conditioner, hair tonic, hair water, hair rinse, styling creme,
  • a hair care product such as
  • one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be used in a smokable composition.
  • smokable composition includes any material that can be smoked or inhaled, such as tobacco and cannabis, as well as any smokable material that is burned to provide desirable aromas (e.g., charcoal briquettes for grilling foods, incense etc) .
  • the smoking compositions may encompass cigarettes, electronic cigarettes (e-cigarettes) , cigars, pipe and cigar tobacco, chew tobacco, vaporizable liquids, and all forms of tobacco such as shredded filler, leaf, stem, stalk, homogenized leaf cured, reconstituted binders, reconstituted tobacco from tobacco dust, fines, or other sources in sheet, pellet or other forms.
  • “Smokable compositions” also include cannabis compositions (e.g., flower materials, leaf materials, extracts, oils, edible candies, vaporizable liquids, cannabis-infused beverages, etc. ) and tobacco substitutes formulated from non-tobacco materials.
  • the one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, and methods described herein are useful for improved taste and aroma profiles of many comsumable products relative to control samples.
  • the phrase “taste profile” which is interchangeable with “sensory profile” and “sweetness profile” , may be defined as the temporal profile of all basic tastes of a sweetener.
  • the “temporal profile” may be considered to represent the intensity of sweetness perceived over time in tasting of the composition by a human, especially a trained “taster” .
  • Carbohydrate and polyol sweeteners typically exhibit a quick onset followed by a rapid decrease in sweetness, which disappers realtively quickly on swallowing a food or beverage containing the same.
  • high intensity natural sweeteners typically have a slower sweet taste onset reaching a maximal response more slowly, followed by a decline in intensity more slowly than with carbohydrate and polyol sweeteners. This decline in sweetness is often referred to as “sweetness linger” and is a major limitation associated with the use of high intensity natural sweeteners.
  • the terms “improve” , “improved” and “improvement” are used interchangeably with reference to a perceived advantageous change in a composition or consumable product upon introduction of one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application from the original taste profile of the composition or consumable product without the added one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs in any aspect, such as less bitterness, better sweetness, better sour taste, better aroma, better mouth feel, better flavor, less aftertaste, etc.
  • the terms “improve” or “improvement” can refer to a slight change
  • the one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application and methods described herein are useful for improving the taste and aroma profiles for other synthetic sweeteners, such as sucralose, ACE-K, aspartame, sodium saccharin, and mixtures thereof, and for natural high intensity sweeteners such as steviol glycosides, Stevia extracts, monk fruit extract, monk fruit components, licorice extract, licorice components.
  • synthetic sweeteners such as sucralose, ACE-K, aspartame, sodium saccharin, and mixtures thereof
  • natural high intensity sweeteners such as steviol glycosides, Stevia extracts, monk fruit extract, monk fruit components, licorice extract, licorice components.
  • the one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be evaluated with reference to the degree of their sucrose equivalence. Accordingly, the STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs compositions of the present application may be diluted or modified with respect to its ingredients to conform this sucrose equivalence.
  • the onset and decay of sweetness when one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application are consumed can be perceived by trained human tasters and measured in seconds from first contact with a taster′s tongue ( ′′onset′′ ) to a cutoff point (typically 180 seconds after onset) to provide a ′′temporal profile of sweetness′′ .
  • a plurality of such human tasters is called a ′′sensory panel.
  • sensory panels can also judge the temporal profile of the other ′′basic tastes′′ : bitterness, saltiness, sourness, piquance (aka spiciness) , and umami (aka savoriness or meatiness) .
  • bitterness saltiness
  • sourness piquance
  • umami aka savoriness or meatiness
  • Aromas from aroma producing substances are volatile compounds which are perceived by the odor receptor sites of the smell organ, i.e., the olfactory tissue of the nasal cavity.
  • aroma substances like the concept of taste substances, is to be used loosely, since a compound might contribute to the typical odor or taste of one food, while in another food it may cause a faulty odor or taste, or both, resulting in an off-flavor.
  • sensory profile may include evaluation of aroma as well.
  • mouth feel involves the physical and chemical interaction of a consumable in the mouth. More specifically, as used herein, the term “mouth feel” refers to the fullness sensation experienced in the mouth, which relates to the body and texture of the consumable such as its viscosity. Mouth feel is one of the most important organoleptic properties and the major criteria that consumers use to judge the quality and freshness of foods. Subtle changes in a food and beverage product’s formulation can change mouth feel significantly. Simply taking out sugar and adding a high intensity sweetener can cause noticeable alterations in mouth feel, making a formerly good product unacceptable to consumers. Sugar not only sweetens, it also builds body and viscosity in food and beverage products, and leaves a slight coating on the tongue. For example, reducing salt levels in soup changes not only taste, but can alter mouth feel as well. Primarily it is the mouth feel that is always the compliant with non-sugar sweeteners.
  • sweetness detection threshold refers to the minimum concentration at which panelists consisting of 1-10 persons are able to detect sweetness in a composition, liquid or solid. This is further defined as provided in the Examples herein and are conducted by the methods described in Sensory Testing for Flavorings with Modifying Properties by Christie L. Harman, John B. Hallagan, and the FEMA Science, Committee Sensory Data Task Force, November 2013, Volume 67, No. 11 and Appendix A attached thereto, the teachings of which are incorporated herein by reference.
  • Theshold of sweetness refers to a concentration of a material below which sweetness cannot be detected, but can still impart a flavor to a consumable (including water) .
  • the sample meets the threshold.
  • concentrations of the substance below the sweetness level are considered a flavoring agent.
  • flavoring agents described herein including STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, can be used in combination with other materials, including non-ST steviol glycosides, to encapsulate and reduce or eliminate the unwanted off taste present in the composition.
  • the processes described herein can be used to preserve flavors.
  • a sample may be tested by e.g., a panel of 1-10 people.
  • a trained taster may independently taste the sample (s) first. The taster may be asked to describe the taste profile and score 0-5 according to the increasing sugar like, bitterness, aftertaste and lingering taste profiles. The taster may be allowed to re-taste, and then make notes for the sensory attributes perceived.
  • another group of 1-10 tasters may similarly taste the sample (s) , record its taste attributes and discuss the samples openly to find a suitable description. Where more than 1 taster disagrees with the results, the tasting may be repeated. For example, a “5” for sugar like is the best score for having a taste that is sugar like and conversely a value of 0 or near zero is not sugar like. Similarly, a “5” for bitterness, aftertaste and lingering is not desired. A value of zero or near zero means that the bitterness, aftertaste and/or lingering is reduced or is removed.
  • Other taste attributes may include astringency and overall likabilityability.
  • vanilla, maltol or other flavor modifier product can be added to the compositions described herein to further improve the taste.
  • FMPs such as maltol, ethyl-maltol, vanillin, ethyl vanillin, m-methylphenol, and m-n-propylphenol can further enhance the mouth feel, sweetness and aroma of the STC, STE compositions described herein.
  • Such compositions may be used in any of the food or beverage products described herein.
  • the flavor substances in the sweet tea plant should also contain any new possible flavor substances from new sweet tea varieties by hybridizing, grafting and other cultivating methods.
  • Flavor oils include spearmint oil, cinnamon oil, oil of wintergreen (methyl salicylate) , peppermint oil, Japanese mint oil, clove oil, bay oil, anise oil, eucalyptus oil, thyme oil, cedar leaf oil, oil of nutmeg, allspice, oil of sage, mace, oil of bitter almonds, and cassia oil; useful flavoring agents include artificial, natural and synthetic fruit flavors, such as vanilla, and citrus oils including lemon, orange, lime, grapefruit, yuzu, sudachi, and fruit essences including apple, pear, peach, grape, raspberry, blackberry, gooseberry, blueberry, strawberry, cherry, plum, prune, raisin, cola, guarana, neroli, pineapple, apricot, banana, melon, apricot, cherry, tropical fruit, mango, mangosteen, pomegranate, papaya, and so forth.
  • useful flavoring agents include artificial, natural and synthetic fruit flavors, such as vanilla, and citrus oils including
  • Additional exemplary flavors imparted by a flavoring agent include a milk flavor, a butter flavor, a cheese flavor, a cream flavor, and a yogurt flavor; a vanilla flavor; tea or coffee flavors, such as a green tea flavor, an oolong tea flavor, a tea flavor, a cocoa flavor, a chocolate flavor, and a coffee flavor; mint flavors, such as a peppermint flavor, a spearmint flavor, and a Japanese mint flavor; spicy flavors, such as an asafetida flavor, an ajowan flavor, an anise flavor, an angelica flavor, a fennel flavor, an allspice flavor, a cinnamon flavor, a chamomile flavor, a mustard flavor, a cardamom flavor, a caraway flavor, a cumin flavor, a clove flavor, a pepper flavor, a coriander flavor, a sassafras flavor, a savory flavor, a Zanthoxyli Fructus flavor, a perilla flavor
  • any flavoring agent or food additive such as those described in ′′Chemicals Used in Food Processing′′ , Publication No 1274, pages 63-258, by the National Academy of Sciences, can be used. This publication is incorporated herein by reference.
  • flavoring agent or “flavorant” herein refers to a compound or an ingestibly acceptable salt or solvate thereof that induces a flavor or taste in an animal or a human.
  • the flavoring agent can be natural, semi-synthetic, or synthetic.
  • Suitable flavorants and flavoring agentt additives for use in the compositions of the present application include, but are not limited to, vanillin, vanilla extract, mango extract, cinnamon, citrus, coconut, ginger, viridiflorol, almond, bay, thyme, cedar leaf, nutmeg, allspice, sage, mace, menthol (including menthol without mint) , an essential oil, such as an oil produced from a plant or a fruit, such as peppermint oil, spearmint oil, other mint oils, clove oil, cinnamon oil, oil of wintergreen, or an oil of almonds; a plant extract, fruit extract or fruit essence from grape skin extract, grape seed extract, apple, banana, watermelon, pear, peach, grape, strawberry, raspberry, cherry, plum, pineapple, apricot, a flavoring agent comprising a citrus flavor, such as an extract, essence, or oil of lemon, lime, orange, tangerine, grapefruit, citron, kumquat, or combinations thereof.
  • Non-limiting examples of proprietary flavorants include Dohler TM Natural Flavoring Sweetness Enhancer K14323 (Dohler TM , Darmstadt, Germany) , Symrise TM Natural Flavor Mask for Sweeteners 161453 and 164126 (Symrise TM , Holzminden, Germany) , Natural Advantage TM Bitterness Blockers 1, 2, 9 and 10 (Natural Advantage TM , Freehold, New Jersey, U.S.A. ) , and Sucramask TM (Creative Research Management, Stockton, California, U.S.A. ) .
  • the flavoring agent is present in the sweetener or flavoring composition of the present application in an amount effective to provide a final concentration of about 0.1 ppm, 0.5 ppm, 1 ppm, 2 ppm, 5 ppm, 10 ppm, 15 ppm, 20 ppm, 25 ppm, 30 ppm, 35 ppm, 40 ppm, 45 ppm, 50 ppm, 55 ppm, 60 ppm, 65 ppm, 70 ppm, 75 ppm, 80 ppm, 85 ppm, 90 ppm, 100 ppm, 110 ppm, 120 ppm, 130 ppm, 140 ppm, 150 ppm, 160 ppm, 170 ppm, 180 ppm, 190 ppm, 200 ppm, 220 ppm, 240 ppm, 260 ppm, 280 ppm, 300 ppm, 320 ppm, 340 ppm, 360
  • the flavoring agent is present in the composition of the present application in an amount effective to provide a final concentration ranging from 10 ppm to 1000 ppm, from 50 ppm to 900 ppm, from 50 ppm to 600 ppm, from 50 ppm to 500 ppm, from 50 ppm to 400 ppm, from 50 ppm to 300 ppm, from 50 ppm to 200 ppm, from 75 ppm to 600 ppm, from 75 ppm to 500 ppm, from 75 ppm to 400 ppm, from 75 ppm to 300 ppm, from 75 ppm to 200 ppm, from 75 ppm to 100 ppm, from 100 ppm to 600 ppm, from 100 ppm to 500 ppm, from 100 ppm to 400 ppm, from 100 ppm to 300 ppm, from 100 ppm to 200 ppm, from 125 ppm to 600 ppm, from 125 ppm to 500 ppm, from 10 ppm to
  • STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs can bind the volatiles of various flavors used in food, beverages, cosmetics, feeds and pharmaceuticals.
  • STEs, STCs, GSTEs and GSTCs formed by the methods disclosed herein can be widely soluble in water, water/alcohol, alcohol, and other organic solvents used for the flavor industry at different temperatures.
  • the sweet tea composition can naturally encapsulate the flavor produced during the processes described herein. Therefore, it is also an excellent carrier or encapsulation material for flavors, including but not limited to flavors and spices originated from plants such as bark, flowers, fruits, leaves, animals such as concentrated meat and sea food soups etc., and their extracts such as essential oils etc.
  • a processed flavor is added to solution containing one or more composition selected from STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, then dried into a powder by any method, including but not limited spray-drying, crystallization, tray-drying, freeze drying etc.
  • spray-drying crystallization, tray-drying, freeze drying etc.
  • the advantage of the present embodiments is that encapsulated flavors by STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs could be kept at room temperature or even higher temperatures without much loss of flavor.
  • specially designed compositions can enhance a foam for a specific application such as foamed/frothy coffee.
  • an anti-foaming agent could be added together or separately during the reaction processes descried herein, such that the product could be used to prevent foaming for beverage bottling applications.
  • flavors could be absorbed in or to the inner surface of pores of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs powders. Flavors are preserved and can be released when in solution.
  • the present embodiments avoid the use of starch, or dextrin as a carrier which can bring wheat taste to the flavors.
  • compositions comprises one more ingredient selected from STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs as a moisture preserver.
  • An embodiment comprises A) one or more ingredients selected from STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs; and B) one or more ingredients selected from following components:
  • a GMG or mixtures of GMGs (1) A GMG or mixtures of GMGs.
  • a GMG, a GSG and an SG A GMG, a GSG and an SG.
  • a GMG, a GSG and an MG A GMG, a GSG and an MG.
  • a GMG, an SG and an MG A GMG, an SG and an MG.
  • a GMG A GMG, a GSG, an SG and an MG.
  • GSG glycosylated steviol glycoside
  • a swingle extract (mogroside extract) .
  • a mogroside (MG) or a mixture of MGs (16) A mogroside (MG) or a mixture of MGs.
  • a glycosylated mogroside (GMG) .
  • An embodiment of composition comprises A) and B) , where the ratio of A) to B) is from 1 ⁇ 99 to 99 ⁇ 1.
  • a further embodiment of food and beverage comprises A) and B) .
  • An additional embodiment of food and beverage comprises A) and B) , where total amount of A) + B) is from 1ppm to 10,000 ppm.
  • Foods and beverages that contain tea powder or tea extract, or flavored tea have a bitter taste or astringent mouth feel.
  • a flavoring agent (s) in combination with one or more ingredient selected from STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs is provided. It has been found that substances including rubusoside surprisingly protects the flavoring agent. Not to be limited by any theory, there is a surprising protective effect exerted by the sweet tea or rubusoside-rich derived products on the flavoring agent (s) .
  • the inventors have surprisingly found that the combination of one or more ingredient selected from STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs and flavoring agent (s) result in a composition with minimal smell.
  • the above observations are not meant to be limited to powders.
  • the one or more ingredient selected from STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, and the flavoring agent (s) can be part of a liquid composition, such as a syrup.
  • the processes of the embodiments described herein are useful for improvement of taste and aroma profile for other natural sweeteners, including but not limited to licorice, thaumatin etc., their mixtures, their mixtures with sweet tea or rubusoside-rich derived products, etc.
  • the processes of the embodiments described herein are used for improvement of taste and aroma profile for other synthetic sweeteners, including but not limited to AC-K, aspartame, sodium saccharin, sucralose or their mixtures.
  • Ginger works well in alcoholic beverages as a mixer, in ginger beer itself, in confections, muffins and cookies.
  • Ginseng is one of the top 10 best selling herbal dietary supplements in US, but ginseng-containing products have been mostly limited to beverages, despite a growing functional food market.
  • the original ginseng flavors include bitterness and earthiness and must be minimized in order to establish potential success in the US market.
  • the embodiments described herein can successfully solve this issue and make new ginseng food products such as cookies, snacks, cereals energy bars, chocolates and coffee with great taste.
  • the inventors have found that adding STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs could significantly improve the taste profile of these flavors and their added products.
  • Flavonoids are an important and widespread group of plant natural products that possess many biological activities. These compounds are part of the wide range of substances called “polyphenols” , which are widely known mainly by their antioxidant properties, and are present in human dietary sources showing great health benefits.
  • Neohesperidine and naringin which are flavanone glycosides present in citrus fruits and grapefruit, are responsible for the bitterness of citrus juices.
  • These substances and their derivates such as neohesperidine chalcone, naringin chalcone, phloracetophenone, neohesperidine dihydrochalcone, naringin dihydrochalcone etc. can be good candidates for bitterness or sweetener enhancers.
  • the inventors surprisingly found adding these components in the compositions described herein could help the masking the bitterness or aftertaste of other ingredients and made the taste cleaner.
  • One embodiment includes the compositions described herein and further comprises flavonoids, more preferably flavonoids containing flavonone glycosides. The ratio of flavonoids in the composition could be in range of from about 0.1 ppm to 99.9%.
  • R is selected from the group consisting of hydrogen and hydroxy
  • R′ is selected from the group consisting of hydroxy, methoxy, ethoxy and propoxy
  • R′′ is selected from the group consisting of neohesperidoxyl, B-rutinosyl and ⁇ -D-glucosyl
  • M is a mono-or divalent metal selected from the group consisting of an alkali metal and an alkaline earth metal
  • n is an integer from 1 to 2 corresponding to the valence of the selected metal M.
  • Typical compounds of the above formula are the alkali or alkaline earth metal monosalts of the following:
  • Neohesperidin dihydrochalcone having the formula:
  • naringin dihydrochalcone of the formula:
  • the alkali metal includes sodium, potassium, lithium, rubidium, caesium, and ammonium
  • the term alkaline earth metal includes calcium, strontium and barium.
  • Other alkali amino acids can serve as as counterions.
  • compositions described herein furhter comprises one or more salts of dihydrochalone.
  • composition described herein can further comprise one or more products selected from Trilobatin, phyllodulcin, Osladin, Polypodoside A, Eriodictyol, Homoeriodicyol sodium salt, hesperidin or hesperetin, Neohesperidin dihydrochalcone, naringin dihydrocholcone, or advantame to provide additional flavors and products.
  • Another embodiment comprises of the compositions described herein and one or more of the aforementioned products, wherein the ratio of one or more products selected in the composition can be in the range of from about 0.1%to about 99.9%.
  • Advantame is high potency synthetic sweetener and can be used as a flavor enhancer. The inventors found that adding advantame into the compositions described herein can boost the flavor and taste profile of a food or beverage.
  • One embodiment provides compositions described herein which further comprise advantame, wherein the amount of advantame can be in the range of from about 0.01ppm to about 100 ppm.
  • Feeds such as rapeseed meal which has a bitter taste, are used as good protein sources for cattle, sheep, and horses. Even chickens are known for their taste discrimination, as chickens are selective to their feeds. Green, natural or organic farming of animals become more and more popular. Therefore, there is a need to find a solution to satisfy market requirements.
  • An embodiment of feed or feed additives comprises the compositions described herein.
  • compositions described herein provide useful applications in improving the palatability of medicines, traditional Chinese medicine, food supplements, beverage, food containing herbs, particularly those with unpleasant long-lasting active ingredients not easily masked by sugar or glucose syrups, let alone sweetening agents or synthetic high intensity sweeteners.
  • traditional Chinese medicine, or food supplements can be combined with one or more of compositions described herein, especially when used as a masking agent.
  • odoriferous aquatic foodstuffs include spirulina powder or its enriched protein extract, protein extracted from duckweeds (lemnoideae family) , fish protein, fish meal etc.
  • odoriferous aquatic foodstuffs include spirulina powder or its enriched protein extract, protein extracted from duckweeds (lemnoideae family) , fish protein, fish meal etc.
  • compositions described herein could be added in these products to minimize the odors to make them more acceptable to consumers including feeds for animals.
  • Embodiments of consumables comprise components from aquaplants and or seafood, and any of the compositions described herein.
  • Foods and beverages containing acids can irritate the tongue.
  • products containing acetic acid can irritate the tongue and make that product unpalatable.
  • acetic acid can be naturally occurring, for instance it is originated from fermentation of fruits such as apple, pear, persimmon etc., grains such as rice, wheat etc. It could be also synthetic. However, the taste of acetic acid is strong and sour and tends to bum the throat. Therefore, there is a need to find a solution to harmonize it.
  • One embodiment provides a composition comprising acetic acid and any of the compositions described herein.
  • Another embodiment provides a method to harmonize the taste of acetic acid by using any of the compositions described herein.
  • Another embodiment provides a consumable that comprises acetic acid and any of the compositions described herein.
  • Another embodiment provides the use of any the compositions described herein in beverages containing acetic acid, where the dosage of the composition (s) described herein is above 10 ( -9 ) ppb.
  • Embodiments of the composition (s) described herein include, for example, one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, combinations of thaumatin and one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, combinations of one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs and high intensity sweeteners, combinations of thaumatin, STEs, STCs,
  • thermo-reaction treatment can result in improved taste of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs.
  • Thermo-treatment is like caramelization of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs.
  • the temperature range can be from 0-1000°C, in particular from about 20 to about 200°C, more particularly from about 60 to about 120°C.
  • the period of treatment can be from be from a few seconds to a few days, more particularly about one day and even more particularly from about 1 hour to about 5 hours.
  • Embodiments provide food and beverages containing alcohol comprising composition selected from one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs.
  • beer or beer containing products can include one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs
  • a vegetable burger comprises thaumatin, one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, combinations of one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs and thaumatin, combinations of one or more of STE, STC, GSTE, GSTCand high intensity sweetener, or combinations of thaumatin, one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCand high intensity sweetener, or combinations of thaumatin, one or more of STEs, S
  • Grilled foods often incorporate sugar to enhance the taste.
  • sugar creates strong colors during grilling, and when the fried foods become cold, the sugar syrup becomes sticky.
  • the inventors found that by adding the compositions described herein to the food to be grilled, these disadvantages can be overcome.
  • embodiments include grilled foods that include thaumatin, one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, combinations of one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs and thaumatin, combinations of one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs and high intensity sweetener, or combinations of thaumatin, one or more of STEs, STCs
  • composition comprises A) one or more ingredients selected from STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs and B) one or more substances selected from fibers such as polydextrose; inulin, Promitor produced by Tate&Lyle; monosaccharide-derived polyols such as erythritol, mannitol, xylitol, and sorbitol; disaccharide-derived alcohols such as isomalt, lactitol, and maltitol; and hydrogenated starch hydrolysates, synthetic high intensity sweeteners such as sodium saccharin, sucralose, aspartame, acesulfame-K, N-- [N- [3- (3-hydroxy-4-methoxyphenyl) propyl] -alpha-aspartyl
  • composition comprises A) and B) , where ratio of A) to B) is from 1 ⁇ 99 to 99 ⁇ 1.
  • An additional embodiment of composition comprises A) and B) , where the final product is in powder or liquid form.
  • a certain embodiment of a food and beverage syrup comprises A) and B) .
  • composition comprises A) one or more ingredients selected from GSGs, GSEs, STEs, STCs, GSTEs and GSTCs; and B) a stevia glycoside composition contains one or more stevia glycosides selected from Reb A, Reb B, Reb C, Reb D, Reb E, Reb I, Reb M, Reb N, Reb O, Stevioside.
  • An additional embodiment of composition of A) and B) where ratio of A) to B) is from 1 ⁇ 99 to 99 ⁇ 1.
  • a further embodiment of food and beverage comprises A) and or B) , where the total concentration of A) is in range of 1ppm to 10,000 ppm; and or B) where the total concentration of B) is in range of 1ppm to 2,000 ppm.
  • a certain embodiment of a food and beverage syrup comprises A) and B) .
  • An embodiment comprises A) one or more of GSGs, GSEs, STEs, STCs, GSTEs and GSTCs; and B) one or more stevia glycosides selected from Reb A, Reb B, Reb C, Reb D, Reb E, Reb I, Reb M, Reb N, Reb O, Stevioside, where A) could improve the solubility of B) .
  • Rubusoside could inhibit absorption of glucose and fructose in intestine.
  • stevia extract, stevia glycosides, sweet tea extract, and sweet tea component may block the absorption of lactose, gluten, absorption by humans in intestine and nasal cavity.
  • An embodiment of a product comprising one or more ingredient selected from SGs, SEs, SCs, GSEs, GSGs, STEs, STCs, GSTEs and GSTCs is used to improve the tolerance of lactose, gluten.
  • the volatile substances from sweet tea could form aerosol when formulated in food and beverage. These substances could inhibit the absorption of pollen or other substances which could bring the allergies to humans.
  • the product could be consumable, or health supplement or medical formulation such as sprayer.
  • compositions comprising one or more terpenoid glycosides (TGs) .
  • TGs include steviol glycosides and other high intensity natural sweetening agents from plants, including glycosides, which may serve as sugar substitutes, and which are further described below.
  • a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond.
  • the sugar group is known as the glycone and the non-sugar group as the aglycone or genin part of the glycoside.
  • Glycosides are prevalent in nature and represent a significant portion of all the pharmacologically active constituents of botanicals. As a class, aglycones are much less water-soluble than their glycoside counterparts.
  • glycosides of the present application can be classified as ⁇ -glycosides or ⁇ -glycosides.
  • Some enzymes such as can only hydrolyze ⁇ -linkages; others, such as emulsin, can only affect ⁇ -linkages.
  • linkages present between glycone and aglycone a C-linked glycosidic bond, which cannot be hydrolyzed by acids or enzymes" ; an O-linked glycosidic bond; an N-linked glycosidic bond; or an S-linked glycosidic bond.
  • the glycone can consist of a single sugar group (monosaccharide) or several sugar groups (oligosaccharide) .
  • Exemplary glycones include glucose, galactose, fructose, mannose, rhamnose, rutinose, xylose, lactose, arabinose, glucuronic acid etc.
  • An aglycone is the compound remaining after the glycosyl group on a glycoside is replaced by a hydrogen atom.
  • glycosides When combining a glycone with an aglycone, a number of different glycosides may be formed, including steviol glycosides, terpenoid glycosides, alcoholic glycosides, anthraquinone glycosides, coumarin glycosides, chromone glycosides, cucurbitane glycosides, cyanogenic glycosides, flavonoid glycosides, phenolic glycosides, steroidal glycosides, iridoid glycosides, and thioglycosides.
  • flavone aglycone refers to an unglycosylated flavonoid.
  • Flavonoid aglycones include flavone aglycones, flavanol aglycones, flavanone aglycones, isoflavone aglycones and mixtures thereof.
  • flavone aglycone refers to unglycosylated flavones, flavanols, flavanones and isoflavones, respectively.
  • the flavonoid aglycone may be selected from the group consisting of apigenin, luteolin, quercetin, kaempferol, myricetin, naringenin, pinocembrin, hesperetin, genistein, and mixtures thereof.
  • Terpenoid glycosides for use in the present application, include e.g., steviol glycosides, Stevia extracts , mogrosides (MGs) , Siraitia grosvenorii (luo han guo or monk fruit) plant extracts, rubusosides (RUs) , Rubus suavissimus (Chinese sweet tea) plant extracts; flavanoid glycosides, such as neohesperidin dihydrochalcone (NHDC) ; osladin, a sapogenin steroid glycoside from the rhizome of Polypodium vulgare; trilobatin, a dihydrochalcone glucoside from apple leaves; eriodictyol, a bitter-masking flavonoid glycoside extracted from yerba santa (Eriodictyon californicum) , one of the four flavanones extracted from this plant as having taste-modifying properties, along homoeriodict
  • Lithocarpus litseifolius folium (latin name) is a kind of species of sweet tea. Phlorizin and trilobatin are the main ingredients. Phlorizin is a glucoside of phloretin, a dihydrochalcone. Phlorhizin is abundant in the leaves of another kind of Sweet Tea (Lithocarpus polystachyus Rehd) , too.
  • the composition of the present application is a flavor composition comprises one or more glycosylated non-sweet terpenoids in STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs in an amount of above 0.01 ppm, 0.1 ppm, 1ppm, 10ppm, 100ppm, 1,000ppm, 1%, 5%, 10%, 20%, 50%or 90%by weight.
  • the flavor composition comprises one or more glycosylated non-sweet terpenoids in GSGs, GSTEs and GSTCs in an amount of above 0.01 ppm, 0.1 ppm, 1ppm, 10ppm, 100ppm, 1,000ppm, 1%, 5%, 10%, 20%, 50%, 90%, where the content of glycosylated non-sweet terpenoids is higher than the natural sources or their natural extracts.
  • Glycosylated stevia glycosides or stevia extracts contains higher glycosylated non-sweet terpenoids than their feeding material of stevia glycosides and Stevia extract before glycosylation.
  • GSTEs, GSTCs contain higher glycosylated non-sweet terpeonoids than their STEs and STCs before glycosylation.
  • the consumable product is a beverage and the beverage comprises the one or more glycosylated non-sweet terpenoids in STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs in an amount of 0.01-5000 ppm.
  • terpenoid glycoside or high intensity natural sweetening agent such as an SG, a Stevia extract, a mogroside, a swingle extract, a sweet tea extract, NHDC, or any glycosylated derivative thereof, that the example is meant to be inclusive and applicable to all of the other terpenoid glycosides or high intensity natural sweetening agents in these classes.
  • sweetening agent such as a terpenoid glycoside sweetener, steviol glycoside sweetener, high intensity natural sweetener, sweetener enhancer, high intensity synthetic sweetener, reducing sugar, or non-reducing sugar, that the example is meant to be inclusive and applicable to all of the other sweeteners or sweetening agents in any given class.
  • An embodiment of flavor composition comprises glycosylated treated ingredients to have content of glyocosides higher than their natural plant sources before glycosylation treatment, where the ingredients are originated from plant sources such as leaves, flowers, fruits, berries, barks, seeds etc.
  • compositions further include one or more components selected from stevia extract, stevia glycosides, glycosylated stevia extract, glycosylated stevia glycosides, sweet tea extract, sweet tea components, glycosylated sweet tea extract, glycosylated sweet tea components, monk fruit extract, monk fruit component, glycosylated monk fruit extract, glycosylated monk fruit component, licorice root extract, licorice root component, glycosylated licorice root extract, glycosylated licorice root component.
  • An embodiment of all these types of glycosylated treated plant ingredients are used in food and beverage.
  • Flavonoids are widely contained in citrus such as lemon, conferring the typical taste and biological activities to lemon.
  • Citrus extract could be glycosylated.
  • An embodiment of a flavor composition comprises glycosylated substances in citrus extracts higher than its original natural sources.
  • a further embodiment of a consumable comprises lemon extract with enriched glycosylated substances in amount of higher than 0.01 ppm, 0.1ppm, 1ppm, 5ppm, 100ppm, 1,000ppm, 5,000ppm, 1%, 5%or 10%by weight.
  • retronasal aroma composition comprises water soluble volatile substances.
  • the consumable product is a beverage or food
  • the beverage or food comprises a) the one or more Stevia extracts, SGs, glycosylated Stevia extract, GSGs, STEs, GSTEs, STCs and GSTCs and b) water soluble volatile substances from fruit juices, berries, species, where the water soluble volatile substances in an amount of 0.01-5000 ppm.
  • Rubusoside 20% (RU20, Guilin Layin Natural Ingredients Corp. The concent of RU is 20.68%Lot# STL02-151005) , CaO (Sinopharm Chemical Reagent Co., Ltd)
  • a glycosylated reaction product composition was prepared using Rubusoside 20% (the product of Example 1, TRU20) according to the following method:
  • a panel of 6 trained testers evaluated the samples and gave scores of 1-5 according to the followed standards. The average score of the panel members was taken as the score of each factor.
  • Evaluation standard A 5%sucrose solution with neutral water was prepared. This solution was used as a standard solution to which the kokumi degree was set as 5.
  • a 250 ppm RA (available from Sweet Green Fields) solution was prepared with neutral water. This solution was used as a standard solution to which the kokumi degree was set as 1.
  • yeast extract available from Leiber, 44400P-145
  • a 250 ppm aqueous solution of RA97 such that the degree of kokumi of the resulting solution was consistent with the standard solution of kokumi degree of 5 (5%sucrose) .
  • a solution of 100 ppm the yeast extract dissolved in 250 ppm RA97 was substantially identical to the degree of kokumi of the 5%sucrose solution.
  • the criteria for determining the degree of kokumi are as follows.
  • the sample to be evaluated was dissolved in neutral deionized water.
  • the tester placed 20-30 mL of the evaluation solution in their mouth. After 5 seconds the solution was spit out. After a mouthwash step with water, the standard solution was taken. If the degree of Kokumi was similar, the Kokumi degree of the sample solution could be determined as the Kokumi degree value of the standard solution. Otherwise it was necessary to take additional standard solutions and try again until the Kokumi degree value was determined.
  • the sample to be evaluated was dissolved in neutral deionized water.
  • the tester placed 20-30 mL of the evaluation solution in their mouth. After 5 seconds the sample was spit out. After a rinse step with water, the standard solution was tasted. If the bitter taste was similar, the bitterness of the sample could be determined as the bitterness value of the standard solution. Otherwise it was necessary to take additional standard solution (s) and try again until the bitterness value was determined.
  • the sample to be evaluated was dissolved in neutral deionized water.
  • the tester placed 20-30 mL of the evaluation solution in their mouth, and timing was started to record the bitterness start time and peak time.
  • the test solution was then spit out. Recording of time continued for the time when the bitterness disappeared completely.
  • the time at which the bitterness completely disappeared was compared to the time in the table below to determine the value of bitterness lingering.
  • the sample to be evaluated was dissolved in neutral deionized water.
  • the tester placed 20-30 mL of the evaluation solution in their mouth, and timing was started to record the sweetness start time and peak time.
  • the test solution was then spit out. Recording of time continued for the time when the sweetness disappeared completely. The time at which the sweetness completely disappeared was compared to the time in the table below to determine the value of sweet lingering.
  • Sucralose available from Anhui Jinhe Industrial Co., Ltd and Lot# is 201810013 was used as a standard reference.
  • the specific metallic aftertaste scoring standards are shown in the table below.
  • the sample to be evaluated was dissolved in neutral deionized water.
  • the tester placed 20-30 mL of the evaluation solution in their mouth. After 5 seconds, the solution was spit out. After a rinse step with water the standard solution was tasted. If the metallic aftertaste was similar, the metallic aftertaste of the sample was determined as the metallic aftertaste score of the standard liquid, otherwise it was necessary to take additional standard liquid samples and taste it again until the metallic aftertaste score was determined.
  • sucrose equivalence or SugarE is the amount of non-sucrose sweetener required to provide the sweetness of a given percentage of sucrose in the same solution.
  • Evaluation method The sample to be evaluated was dissolved in neutral deionized water. The tester placed 20-30 mL of the evaluation solution in their mouth. After 5 seconds the solution was spit out. After a mouthwash step with water, the standard solution was taken. If the degree of SugarE was similar, the SugarE degree of the sample solution can be determined as the SugarE degree value of the standard solution. Otherwise it was necessary to take additional standard solutions and try again until the SugarE degree value was determined.
  • Each person of the test panel had to drink sample solutions with defined concentrations. During the test, all persons had a time clock. They had to note the appearance-time for four specific points of a time-intensity curves (onset, maximum sweetness, lingering on and lingering off) . The results were recorded and make a graph, mean values were calculated from at least 6 individual test persons.
  • FIG. 1 shows a schematic diagram of the time-intensity curve.
  • Maltodextrin available from BAOLIBAO BIOLOGY Co., Ltd was used as a standard reference.
  • the specific starch taste scoring standards are shown in the table below.
  • the sample to be evaluated was dissolved in neutral deionized water.
  • the tester placed 20-30 mL of the evaluation solution in their mouth. After 5 seconds, the solution was spit out. After a rinse step with water the standard solution was tasted. If the starch taste was similar, the starch taste of the sample was determined as the starch taste score of the standard liquid, otherwise it was necessary to take additional standard liquid samples and taste it again until the starch taste score was determined.
  • RU20, GTRU20, from Examples 1 to 2 were weighed and uniformly mixed according to the weights shown in Tables 3-8 and 3-9; dissolved in 100ml pure water; and subjected to a sweetness and overall likability evaluation test.
  • Example 4 Evaluation of the taste profiles of RU20, GTRU20 in a 40%sugar reduction system
  • RU20 Guilin Layin Natural Ingredients Corp. The concent of RU is 20.68%; Lot#: STL02-151005; GTRU20, the product of Example 2.
  • sample solutions RU20, GTRU20, and 6%sugar solution were mixed according to the weights shown in Table 4-1 below.
  • Example 3 The samples in example below were evaluated by the method in Example 3. Each panelist was asked to evaluate by his preference on six aspects -flavor, sweet lingering, mouth feel, bitterness, bitterness lingering and overall likability. It should be noted that according to the sensory evaluation method, the evaluation of the mouth feel, sweet lingering, bitterness, bitterness lingering and overall likability is based on the iso-sweetness, 10%SugarE. The evaluation results are shown in Table 4-2.
  • iii) 0.75 ml CGTase enzyme and 15ml deionized water were added to the mixture of ii) and incubated at 69°C for 20 hours to glycosylate the RU90 composition via glucose molecules derived from tapioca dextrin.
  • RU90 available from EPC Natural Products Co., Ltd. The content of RU is 92.8%; GRU90, the product of Example 5.
  • GRU90 showed significantly decreased bitterness and bitterness lingering compared to RU90.
  • GRU90 provided a significantly pleasant flavor that served to improve their full body mouth feel.
  • GRU90 a significantly more pleasant taste, as well as remarkably improved overall likability compared to RU20.
  • GTRU20 and sucralose (available from Anhui Jinhe Industrial Co., Ltd and Lot# is 201810013) were weighed and uniformly mixed according to the weight shown in Table 7-1, dissolved in 100 ml pure water, and subjected to a sensory evaluation test.
  • FIG. 3A The relationship between the sensory evaluation results to the ratio of sucralose to GTRU20 in this example is shown in FIG. 3A.
  • FIG. 3B The relationship between the overall likability results to the ratio of sucralose to GTRU20 in this example is shown in FIG. 3B.
  • GTRU20 and RA97 available from Sweet Green Fields. The content is 97.15%. Lot# 3050123) were weighed and uniformly mixed according to the weight shown in Table 8-1, dissolved in 100ml pure water, and subjected to a sensory evaluation test.
  • FIG. 4A The relationship between the sensory evaluation results to the ratio of RA97 to GTRU20 in this example is shown in FIG. 4A.
  • FIG. 4B The relationship between the overall likability results to the ratio of RA97 to GTRU20 in this example is shown in FIG. 4B.
  • RU90 and GRU90 from Examples 5-6 were weighed and uniformly mixed according to the weights shown in Table 9-1 and 9-2 dissolved in 100ml pure water; and subjected to a sweetness and overall likability evaluation test.
  • Example 10 improves the taste and mouth feel of acesulfame-K
  • GRU90 and acesulfame-K (available from JINGDA PERFUME) were weighed and uniformly mixed according to the weight shown in Table 10-1, dissolved in 100 ml pure water, and subjected to a mouth feel evaluation test.
  • FIG. 6A The relationship between the sensory evaluation results to the ratio of acesulfame-K to GRU90 in this example is shown in FIG. 6A.
  • FIG. 6B The relationship between the overall likability results to the ratio of acesulfame-K to GRU90 in this example is shown in FIG. 6B.
  • Steviol glycosides RA20/TSG (9) 95, Lot No. EPC-309-1-0, Reb A 28.98%, Stevioside 60.36%, available from Sweet Green Fields.
  • ⁇ -galactosidase Lactase DS 100, Lot No. LAMR0351901K, 111000ALU/g, available from AmanoEnzyme Inc.
  • Stevioside can be converted to rubusoside by the effect of ⁇ -galactosidase. Under certain conditions, the conversion ratio is close to 100%.
  • the converted product in solution or powder form
  • the rubusoside can be enriched by crystallization etc. to any desired purity.
  • rubusosides can be prepared from a Stevia extract to a purity of more than 40%, 90%or 95%. Any type of these compositioins can be used as sweetener or flavor ingredient in food and beverage products. Any type of these composition can be further subjected to a glycosylation reaction to produce a glycosylated product.
  • Some embodiments of the present application relate to a Stevia extract comprising rubusoside and Reb A, wherein the Reb A content is less than 50%, 40%, 30%, 20%, 10%, 5%by weight of the Stevia extract.
  • a further embodiment of the Stevia extract comprises rubusoside and Reb A, wherein the total amount of rubusoside and Reb A is above 50%by weight of the Stevia extract, where ratio of rubusoside to Reb A is greater than 1 ⁇ 2 or 1 ⁇ 1.
  • Some embodiments of the present application relate to a Stevia extract comprising rubusoside, Reb A, and one or more other stevia glycosides selected from the group consisting of stevioside, Reb B, Reb C, Reb D, Reb E, Reb I, Reb M, Reb N and Reb O, wherein the total amount of the one or more other stevia glycosides is less than 50%, 40%, 30%, 20%, 10%, 5%, 2%, 1%, 0.5%by weight of the Stevia extract.
  • the Stevia extract comprises stevioside in an amount that is less than 50%, 40%, 30%, 20%, 10%, 5%, 2%, 1%, 0.5%by weight of the Stevia extract.
  • Some embodiments of the present application relate to a glycosylated Stevia extract composition that comprises glycosylated Reb A and glycosylated rubusoside, unreacted Reb A and unreacted rubusoside.
  • the total content of glycosylated rubusoside and glycosylated Reb A is above 1%, 5%, 10%, 40%, 50%, 60%, 70%, 80%, 85%, 90%, 95%by weight of the composition.
  • compositions that comprises (1) glycosylated rubusoside originated from a Stevia extract, and/or (2) glycosylated rubusoside enzymatic converted from stevisoide.
  • the glycosylated rubuososide is present in an amount of greater than 1%, 5%, 10%, 20%, 30%, 40%, 50%, 60%, 80%, 90%or 95%by weight of the composition.
  • the composition further comprises unreacted rubusoside and sugar donors, such as starch or dextrins.
  • the dextrins is present in an amount of less than 30%, 20%, 15%, 10%, or 5%by weight of the composition.
  • This sample is enzymatic transglucosylated RU20.
  • This sample is treated sweet tea extract RU20.
  • This sample is enzymatic transglucosylated TRU20.
  • This sample is enzymatic transglucosylated RU90.
  • Reference standards to qualify the analytical method for steviolglycosides (Reb A, Reb B, Reb C, Reb D, Reb E, Reb F, Reb G, Reb I, Reb M, Reb N, Reb O, Stevioside, Isoreb A, Isostevioside) were obtained from Chromadex (LGC Germany) .
  • Solvents and reagents HPLC grade
  • VWR Vienna
  • Sigma-Aldrich Vienna
  • Davisil Grade 633 high-purity grade silica gel, pore size 200-425 mesh particle size was obtained from Sigma-Aldrich (Vienna) .
  • the method was qualified by fractionation of steviolglycoside standards and enzymatically reacted steviol-glycosides. An elution yield of >97 %of steviol-glycosides and of >95 %enzymatically reacted steviol-glycosides was observed, the carry over between the fraction was calculated to less than 3 %.
  • the pooled, evaporated samples were used for analysis of steviol-related compounds as well as for non-volatile non-steviol-related compounds.
  • the HPLC system consisted of an Agilent 1100 system (autosampler, ternary gradient pump, column thermostat, VWD-UV/VIS detector, DAD-UV/VIS detector) connected in-line to an Agilent mass spectrometer (ESI-MS quadrupole G1956A VL) .
  • Agilent 1100 system autosampler, ternary gradient pump, column thermostat, VWD-UV/VIS detector, DAD-UV/VIS detector
  • ESI-MS quadrupole G1956A VL Agilent mass spectrometer
  • the detectors were set to 210 nm (VWD) , to 205 and 254 nm (DAD with spectra collection between 200-600 nm) and to ESI negative mode TIC m/z 300-1500, Fragmentor 200, Gain 2 (MS, 300 °C, nitrogen 12 l/min, nebulizer setting 50 psig. Capillary voltage 4500 V) .
  • Detection at 205 and 210 nm were used to quantify the chromatograms, the MS-spectra were used to determine the molar mass and structural information of individual peaks. Detection at 254 nm was used to identify non-steviolglycoside peaks.
  • Samples were quantified by external standardization against reference compounds of Reb A or stevioside, in case where no authentic reference standard was available, the peak area was quantified against the reference standard with the most similar mass and corrected for the molar mass differences.
  • Steviol-glycosides and enzymatically reacted steviol-glycosides were identified by comparison of retention times to authentic reference standards and/or by evaluation of the mass spectra obtained (including interpretation of the fragmentation pattern and double charged ions triggered by the presence of dichloromethane) .
  • Steviol-glycosides were quantified against external standards. In case that no reference standard was available quantification was performed against the reference standard with the most similar molar mass.
  • the steam distillation was performed for 120 minutes.
  • the ethyl acetate was collected and injected onto the GC/MS system.
  • Tables 14-1 to 14-3 show the test results for steviol-glycosides and glucosylated steviol-glycosides.
  • Tables 14-4 and 14-5 show the suavioside related compounds detected in the samples.
  • Table 14-6 shows volatile compounds observed in the samples.
  • FIGS. 8-11 show chromatograms of exemplifying samples.
  • Table 14-7 shows representative structures of suaviosides.
  • FIGS. 12-20 show chromatograms of various samples.
  • the base samples with 20 %rubusoside (whether or not treated) contains mainly rubusoside and steviol-monoside in a ratio of around 10 ⁇ 1 together with traces of suaviosides.
  • the base sample with 92 %rubusoside contains mainly rubusoside and traces of suaviosides (see Table 14-4) . It is therefore acceptable to allocate glucosylated steviol-glycosides as stemming mostly from rubusoside.
  • Steviol-monoside with one added glucose can be determined due to chromatographic separation from Rubusoside, in all other glycosylation patterns it can only be differentiated between different molar masses, but not the basic molecule (rubusoside or steviol-monoside) . As shown in Tables 14-1 to 14-3, the glycosylated samples show for most molar masses 2 peaks which are interpreted as rubusoside isomers.
  • FIGS. 8A and 8B present comparative fingerprints and Tables 14-4 and 14-5 provide quantitative estimates for steviol-related compounds, tentatively from the group of suaviosides.
  • Table 14-6 shows the qualitative results for the volatile compounds detected in the RU20, RU90, TRU20, GRU20 and GRU90 samples.
  • Table 14-2 Steviolglycosides detected in the TRU20 sample and the GTRU20 sample therefrom.
  • FIGs. 8A-8B show chromatograms (MS-TIC Mode) corresponding to the volatile compounds detected in the RU90 and GRU90 samples, respectively.
  • Unknown 1 shows an MS peak indicative of Suavioside B
  • Unknown 2 shows an MS peak indicative of Suavioside H
  • Unknown 3 shows an MS peak tentatively indicative of 9-Hydroxy-Suavioside J
  • Unknown 4 shows an MS peak indicative of Suavioside K.
  • m/z across (+x Glc) indicates glucosylated rubusoside and the number of added glucose units. In most cases the peak shape indicates co-elution of compounds with the same m/z value but different glucosylation patterns.
  • FIGs. 9A-9B show chromatograms (MS-TIC Mode) corresponding to the volatile compounds detected in the RU20 and GRU20 samples, respectively.

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Abstract

Provided is a composition comprising one or more products selected from the group consisting of rubusoside (RU), sweet tea components (STCs), sweet tea extracts (STEs), monk fruit components (MFCs), monk fruit extracts (MFEs), steviol glycosides (SGs), stevia extracts (SEs), glycosylated rubusoside (GRU), glycosylated sweet tea components (GSTCs), glycosylated sweet tea extracts (GSTEs), glycosylated monk fruit components (GMFCs), glycosylated monk fruit extracts (GMFEs), glycosylated steviol glycosides (GSGs), and glycosylated stevia extracts (GSEs), wherein the one or more products are present in the composition in a total amount of 0.1-99.9 wt%, and wherein the composition is a sweetener composition, a flavoring composition, or both. Further provided are the methods of making and using such compositions to improve the taste and/or flavor of a consumable product.

Description

    SWEETENER AND FLAVOR COMPOSITIONS
  • This application is a Continuation-In-Part of U.S. Application Serial Number 16/434,292, filed June 7, 2019, which claims priority to U.S. Provisional Patent Application Serial Number 62/857,875, filed June 6, 2019, U.S. Provisional Patent Application Serial Number 62,729,524, filed September 11, 2018, and U.S. Provisional Patent Application Serial Number 62/683,154, filed June 11, 2018. This application further claims priority to U.S. Provisional Patent Application Serial Number 63/026,910, filed May 19, 2020 and U.S. Provisional Patent Application Serial Number 63/062,645, filed August 7, 2020. The contents of the above-cited applications are incorporated herein in their entirety for all purposes.
    • FIELD
  • The present disclosure relates generally to sweeteners and flavoring agents, and their use in food, beverage, feed, pharmaceutical and personal care products.
    • BACKGROUND
  • Caloric sugars are widely used in the food and beverage industry. However, there is a growing trend toward use of more healthy alternatives, including non-caloric or low caloric sweeteners. Popular non-caloric sweeteners include high intensity synthetic sweeteners, such as aspartame (e.g., NutraSweet, Equal) , sucralose (Splenda) , and acesulfame potassium (also known as acesulfame K, or Ace-K) , as well as high intensity natural sweeteners, which are typically derived from plants such as Stevia plants, sweet tea plants and monk fruit plants.
  • Despite the widespread use of non-caloric sweeteners, which are gaining in popularity, many consumers are reluctant to use these products, since their taste properties are often considered to insufficiently mimick the taste profile of caloric sugares, such as sucrose. Therefore, there is a need in further developing and enhancing the taste properties of natural and synthetic sweeteners to better reproduce the taste properties associated with conventional sugar products, so as to provide increased consumer satisfaction.
  • SUMMARY
  • In one aspect, the present application relates to a composition comprising one or more products selected from the group consisting of rubusoside (RU) , sweet tea components (STCs) , sweet tea extracts (STEs) , morgrosides (MGs) monk fruit components (MFCs) , monk fruit extracts (MFEs) , steviol glycosides (SGs) , Stevia extracts (SEs) , glycosylated rubusoside (GRU) , glycosylated sweet tea components (GSTCs) , glycosylated sweet tea extracts (GSTEs) , glycosylated monk fruit components (GMFCs) , glycosylated morgrosides (GMGs) , glycosylated monk fruit extracts (GMFEs) , glycosylated stevia glycosides (GSGs) , and glycosylated stevia extracts (GSEs) , wherein the one or more products are present in the composition in a total amount of 0.1-99.9 wt%, and wherein the composition is a sweetener composition, a flavoring composition, or both, as well as methods of making and using such compositions to improve the taste and/or flavor of a consumable product.
  • In some embodiments, the sweetener or flavoring composition comprises a STE containing enriched rubusoside (RU) .
  • In some embodiments, the sweetener or flavoring composition comprises a STE containing enriched diterpene glycoside.
  • In some embodiments, the sweetener or flavoring composition comprises an STE that comprises one or more sweet tea derived components (STC) selected from the group consisting of rubusoside (RU) , suavioside (SU) , steviolmonoside, rebaudioside A, 13-O-β-D-glucosyl-steviol, isomers of rebaudioside B, isomers of stevioside, panicloside IV, sugeroside, ent-16α, 17-dihydroxy-kaurane-19-oic acid, ent-13-hydroxy-kaurane-16-en-19-oic acid, ent-kaurane-16-en-19-oic-13-O-β-D-glucoside, ent-16β, 17-dihydroxy-kaurane-3-one, ent-16α, 17-dihydroxy-kaurane-19-oic acid, ent-kaurane-16β, 17-diol-3-one-17-O-β-D-glucoside, ent-16α, 17-dihydroxy-kaurane-3-one, ent-kaurane-3α, 16β, 17-3-triol, ent-13, 17-dihydroxy-kaurane-15-en-19-oic acid, ellagic acid, gallic acid, oleanolic acid, ursolic acid, rutin, quercetin, and isoquercitrin.
  • In some embodiments, the sweetener or flavoring composition comprises a STE that comprisies one or more suaviosides slected from the group consisting of SU-A, SU-B, SU-C1, SU-D1, SU-D2, SU-E, SU-F, SU-G, SU-H, SU-I, and SU-J.
  • In some embodiments, the sweetener or flavoring composition comprises a STE wherein the STE is purified RU.
  • In some embodiments, the sweetener or flavoring composition comprises a GSTE.
  • In some embodiments, the sweetener or flavoring composition comprises a GSTE containing enriched glycosylated rubusoside (RU) .
  • In some embodiments, the sweetener or flavoring composition comprises a GSTE containing enriched glycosylated diterpene glycoside.
  • In some embodiments, the sweetener or flavoring composition comprises a GSTE, wherein the GSTE is glycosylated RU.
  • In some related embodiments, the STE comprises enriched RU. In some related embodiments, the STE comprises enriched diterpene glycoside. In some related embodiments, the STE comprises one or more STCs selected from the group consisting of RU, SU, steviolmonoside, rebaudioside A, 13-O-β-D-glucosyl-steviol, isomers of rebaudioside B, isomers of stevioside, panicloside IV, sugeroside, ent-16α, 17-dihydroxy-kaurane-19-oic acid, ent-13-hydroxy-kaurane-16-en-19-oic acid, ent-kaurane-16-en-19-oic-13-O-β-D-glucoside, ent-16β, 17-dihydroxy-kaurane-3-one, ent-16α, 17-dihydroxy-kaurane-19-oic acid, ent-kaurane-16β, 17-diol-3-one-17-O-β-D-glucoside, ent-16α, 17-dihydroxy-kaurane-3-one, ent-kaurane-3α, 16β, 17-3-triol, ent-13, 17-dihydroxy-kaurane-15-en-19-oic acid, ellagic acid, gallic acid, oleanolic acid, ursolic acid, rutin, quercetin, and isoquercitrin. In some related embodiments, the STE comprisies one or more suavosides slected from the group consisting of SU-A, SU-B, SU-C1, SU-D1, SU-D2, SU-E, SU-F, SU-G, SU-H, SU-I, and SU-J.
  • In some related embodiments, the GSTE is a glycosylation product of an STE that comprises enriched RU. In some related embodiments, the GSTE is a glycosylation product of a STE that comprises enriched diterpene glycoside. In some related embodiments, the GSTE is a glycosylation product of a STE that comprises one or more STCs selected from the group consisting of RU, SU, steviolmonoside, rebaudioside A, 13-O-β-D-glucosyl-steviol, isomers of rebaudioside B, isomers of stevioside, panicloside IV, sugeroside, ent-16α, 17-dihydroxy-kaurane-19-oic acid, ent-13-hydroxy-kaurane-16-en-19-oic acid, ent-kaurane-16-en-19-oic-13- O-β-D-glucoside, ent-16β, 17-dihydroxy-kaurane-3-one, ent-16α, 17-dihydroxy-kaurane-19-oic acid, ent-kaurane-16β, 17-diol-3-one-17-O-β-D-glucoside, ent-16α, 17-dihydroxy-kaurane-3-one, ent-kaurane-3α, 16β, 17-3-triol, ent-13, 17-dihydroxy-kaurane-15-en-19-oic acid, ellagic acid, gallic acid, oleanolic acid, ursolic acid, rutin, quercetin, and isoquercitrin. In some related embodiments, the GSTE is a glycosylation product of a STE that comprisies one or more suavosides slected from the group consisting of SU-A, SU-B, SU-C1, SU-D1, SU-D2, SU-E, SU-F, SU-G, SU-H, SU-I, and SU-J.
  • Hydrolyzed starch (dextrins) are often used for glycosylation of STEs, SEs, MFEs, SGs, MGs, rubusoside, and suaviosides. However, when orally administered such glycosylated compositions there are appreciable levels of glycoside chains of dextrins that are further hydrolyzed by salivary amylase, resulting in smaller units that are readily metabolized by the microorganisms of the oral cavity. The presence of unreacted starch and/or dextrin derivatives possess cariogenic potential and the propensity for tooth decay if these agents remain present in the glycosylated (or natural sweetener) compositions that are orally administered. Thus, there is need for sweetener compositions in which unreacted sugar donors are reduced.
  • Accordingly, in another aspect, the present application provides a sweetener or flavor composition comprising: (a) one or more glycosylated substances selected from glycosylated sweet tea extracts, glycosylated rubusoside, glycosylated suaviosides, glycosylated stevia glycosides, glycosylated stevia extracts, glycosylated monk fruit extracts, and/or glycosylated mogrosides; (b) one or more unreacted substances of sweet tea extracts, rubusoside, suaviosides, stevia extracts, stevia glycosides, monk fruit extracts, and/or mogrosides; and (c) one or more unreacted sugar donors or residues thereof, where the sugar donors or residues thereof are present in the sweetener or flavor composition in an amount greater than zero, but less than 15%, less than 10%, less than 5%, less than 4%, less than 3%, less than 2%, less than 1%, less than 0.5%, less than 0.1%, less than 0.05%, less than 0.01%or less than 0.001% (wt/wt) .
  • In a related embodiment, the present application provides a method for measuring the amount of unreacted sugar donors in a sweetener or flavor composition, as well as a method for removing unreacted sugar donors in a sweetener or flavor composition.
  • Another aspect of the present application relates to a consumable product comprising one or more components selected from the group consisting of RU, GRU, STEs, GSTEs, STCs, GSTCs, Mgs, GMGs, MFCs, GMFCs, SEs, GSEs, SCs, GSCs, SGs, and GSGs in a total amount of 0.00001-99.9 wt%.
  • In some embodiments, the consumable product is selected from the group consisting of beverage products, confections, condiments, dairy products, cereal compositions, chewing compositions, tabletop sweetener compositions, medicinal compositions, oral hygient compositions, cosmetic compositions, and smokable compositions.
  • In some embodiments, the consumable product is a beverage and the beverage comprises the one or more components in an amount of 0.01-5000 ppm.
  • In some embodiments, the consumable product is a food product and the food product comprises the one or more components in an amount of 0.01-5000 ppm.
  • In some embodiments, the consumable product is a personal care product and personal care product comprises the one or more components in an amount of 0.01-5000 ppm.
  • In a more particular embodiment, the consumable product containing the above described sweetener or flavor composition is an oral hygiene product selected from the group consisting of toothpaste, tooth polish, tooth whitening agent, mouthwash, mouth rinse, mouth spray, breath fresheners, and dentifrice. In some embodiment, the oral hygiene product comprises a sweetener composition comprising (1) one or more components selected from the group consisting ofRU, GRU, STEs, GSTEs, STCs, GSTCs, MGs, GMGs, MFCs, GMFCs, SEs, GSEs, SCs, GSCs, SGs and GSGs of the present application, and (2) sugar donors or residues thereof in an amount that is greater than zero, but is less than 15%, less than 10%, less than 5%, less than 4%, less than 3%, less than 2%, less than 1%, less than 0.5%, less than 0.1%, less than 0.05%, or less than 0.01% (wt/wt) of the sweetener composition.
  • In some embodiments, the present application provides a consumable product comprising one or more components selected from the group consisting of RU, GRU, SGs, GSGs, SEs, GSEs, STEs, GSTEs, STCs and GSTCs of the present application. In certain particular embodiments, the one or more components are present in the consumable product in a concentration ranging from 0.0001 wt %to 99.9999 wt %, 0.0001 wt %to 75 wt %, 0.0001 wt % to 50 wt %, 0.0001 wt %to 25 wt %, 0.0001 wt %to 10 wt %, 0.0001 wt %to 5 wt %, 0.0001 wt %to 1 wt %, 0.0001 wt %to 0.5 wt %, 0.0001 wt %to 0.2 wt %, 0.0001 wt %to 0.05 wt %, 0.0001 wt %to 0.01 wt %, 0.0001 wt %to 0.005 wt %, or any range derived from any two of these values.
  • In certain particular embodiments, the consumable product is a beverage product in which the one or more components are present in a final concentration range of 1-15,000 ppm.
  • In another aspect, the present application provides a method for modifying a consumable product, comprising adding to the consumable product (e.g., beverage, food, oral hygiene or personal care product) one or more components selected from the group consisting of RU, GRU, STEs, GSTEs, STCs, GSTCs, MGs, GMGs, MFCs, GMFCs, SEs, GSEs, SCs, GSCs, SGs, and GSGs of the present application. In certain particular embodiments, the one or more components are added to the consumable product at a final concentration ranging from 0.0001 wt %to 99.9999 wt %, 0.0001 wt %to 75 wt %, 0.0001 wt %to 50 wt %, 0.0001 wt %to 25 wt %, 0.0001 wt %to 10 wt %, 0.0001 wt %to 5 wt %, 0.0001 wt %to 1 wt %, 0.0001 wt %to 0.5 wt %, 0.0001 wt %to 0.2 wt %, 0.0001 wt %to 0.05 wt %, 0.0001 wt %to 0.01 wt %, 0.0001 wt %to 0.005 wt %, or any range derived from any two of these values. In a more particular embodiment, the consumable product is a beverage product, wherein the one or more components are added in a final concentration range of 1-15,000 ppm.
    • BRIEF DESCRIPTION OF THE DRAWINGS
  • FIG. 1 is a representative time-intensity curve showing a relative appearance-time profile associated with taste tasting, including onset, maximum sweetness, lingering on and lingering off phases.
  • FIGS. 2A and 2B show the sugar equivalence (SugarE) as a function of concentration (ppm) in Example 3 for RU20 and GRU20, respectively, including the SugarE at which bitterness can be perceived
  • FIG. 3A shows the relationship between the sensory evaluation results and the ratio of sucralose to GTRU20 in Example 7. FIG. 3B shows the relationship between the overall likability results as a function of the ratio of sucralose to GTRU20 in Example 7.
  • FIG. 4A shows the relationship between the sensory evaluation results and the ratio of RA97 to GTRU20 in Example 8. FIG. 4B shows the relationship between the overall likability results as a function of the ratio of RA97 to GTRU20 in Example 8.
  • FIGS. 5A and 5B show the sugar equivalence (SugarE) as a function of concentration (ppm) in Example 9 for RU90 and GRU90, respectively.
  • FIG. 6A shows the relationship between the sensory evaluation results and the ratio of acesulfame-K to GRU90 in Example 10. FIG. 6B shows the relationship between the overall likability results in Example 10 as a function of the ratio of acesulfame-K to GRU90.
  • FIG. 7A-7F show sweetness profiles as a function of time corresponding to samples containing different rubusoside (RU) compositions containing 15 ppm thaumatin compared to 15 ppm thaumatin alone in Example 13. FIG. 7A: control containing 15 ppm thaumatin only; FIG. 7B: 50 ppm RU20 + 15 ppm thaumatin; FIG. 7C: 50 ppm RU90 + 15 ppm thaumatin; FIG. 7D: 50 ppm GRU20 + 15 ppm thaumatin; FIG. 7E: 50 ppm GRU90 + 15 ppm thaumatin; FIG. 7F: 50 ppm TRU20 + 15 ppm thaumatin.
  • FIGS. 8A and 8B show GC/MS chromatograms of RU90 and GRU90 samples in Example 14, respectively. Unknown 1 shows an MS spectrum indicative for Suavioside B. Unknown 2 shows an MS spectrum indicative for Suavioside H. Unknown 3 shows an MS spectrum tentative for 9-Hydroxy-Suavioside J. Unknown 4 shows an MS spectrum indicative for Suavioside K. m/z..... (+x Glc) indicates glucosylated rubusoside and the number of added glucose units. In most cases the peak shape indicates co-elution of compounds with the same m/z value but different glucosylation patterns.
  • FIGS. 9A and 9B show GC/MS chromatograms of RU20 and GRU20 samples in Example 14, respectively. Unknown 1 shows an MS spectrum indicative for Suavioside B. Unknown 2 shows an MS spectrum indicative for Suavioside H. Unknown 3 shows an MS spectrum tentative for 9-Hydroxy-Suavioside J. Unknown 4 shows an MS spectrum indicative for Suavioside K. m/z..... (+x Glc) indicates glucosylated rubusoside and the number of added  glucose units. In most cases the peak shape indicates co-elution of compounds with the same m/z value but different glucosylation patterns.
  • FIG. 10 shows a chromatogram (MS-Trace) depicting spectra indicative of a molar mass 966 or less in the GRU20 sample in Example 14 showing Rub-lGlc (2 isomers) and Rub-2Glc (2 isomers) .
  • FIG. 11 shows a two chromatograms, including an upper trace for RU20 at a wavelength (UV) of 254 nm, and a lower trace for GRU20 indicative of phenolic acids and polyphenols as described in Example 14.
  • FIGs. 12A-12C show representative chromatograms of RU20 as described in Example 14.
  • FIGs. 13A-13D show representative chromatograms of GRU20 in Example 14.
  • FIGs. 14A-14C show representative chromatograms of RU90 as described in Example 14.
  • FIGs. 15A-15D show representative chromatograms of GRU90 as described in Example 14.
  • FIG. 16 shows representative chromatograms of RU20 SIM neg as described in Example 14. MS 497, 335, and 317 peaks are indicative of suaviosides with an isosteviol skeleton.
  • FIG. 17 shows representative chromatograms of TRU20, SIM neg as described in Example 14. MS 497, 335, and 317 peaks are indicative of suaviosides with an isosteviol skeleton.
  • FIG. 18 shows representative chromatograms of GRU20, SIM neg as described in Example 14. MS 497, 335, and 317 peaks are indicative of suaviosides with an isosteviol skeleton.
  • FIG. 19 shows representative chromatograms of GTRU20, SIM neg as described in Example 14. MS 497, 335, and 317 peaks are indicative for suaviosides with an isosteviol skeleton.
  • FIG. 20 shows representative chromatograms of RU20 as described in Example 14, including a positive MS 439 peak.
  • FIG. 21 shows the different phases in the time intensity profiles in Example 15, including phase 1 reflecting the time of onset and increasing intensity of sweetness/acidity as a joint measure; phase 2 reflects the balanced sweetness/acidity phase; and phase 3 reflects the decay of acidity and sweetness lingering. The combined phases provide an estimate for the overall sweetness/acidity perception.
  • [Rectified under Rule 91, 08.02.2021]
    FIG. 22A shows time-intensity profiles for sweetness/acidity perception in the TRU20-and GTRU20-1emonade samples in Example 15. FIG. 22B shows time-intensity profiles for sweetness/acidity perception in RU 90-and GRU90-1emonade samples in Example 15.
  • FIG. 23A shows time-intensity profiles for sweetness/acidity perception in the TRU20-and GTRU20-Fanta Zero samples in Example 15. FIG. 23B shows time-intensity profiles for sweetness/acidity perception in RU 90-and GRU90-Fanta Zero samples in Example 15.
  • FIG. 24A shows the results from sensory evaluations of product compositions containing mixtures of GSTV85 and GRU90 in different ratios. FIG. 24B shows the overall likability of the product compositions in FIG. 24A.
  • FIG. 25 shows the results from sensory evaluations on adding glycosylated steviol glycosides (GSG) product 22-02 in Example 22 in Cherry Blossom whitening Lion toothpaste.
  • FIG. 26 shows the results from sensory evaluations on adding glycosylated steviol glycosides (GSG) product 22-03 in Example 22 in White &White Lion toothpaste.
  • FIG. 27 shows the results from sensory evaluations on adding glycosylated steviol glycosides (GSG) product 22-03 in Example 22 in toothpaste.
  • FIG. 28A shows the HPLC chromatograms of maltodextin standard and glucose standard. FIG. 28B shows the HPLC chromatogram of samples from Example 22.
  • FIG. 29 shows a combined water steam distillation and solvent extraction/concentration device.
    • DETAILED DESCRIPTION
  • I. Definitions
  • Unless defined otherwise, all technical and scientific terms used herein have the same meanings as commonly understood by one of ordinary skill in the art to which this application belongs. All publications and patents specifically mentioned herein are incorporated by reference in their entirety for all purposes including describing and disclosing the chemicals, instruments, statistical analyses and methodologies which are reported in the publications which might be used in connection with the application. All references cited in this specification are to be taken as indicative of the level of skill in the art. Nothing herein is to be construed as an admission that the application is not entitled to antedate such disclosure by virtue of prior invention.
  • In the specification and in the claims, the terms "including" and "comprising" are open-ended terms and should be interpreted to mean "including, but not limited to...." These terms encompass the more restrictive terms “consisting essentially of” and “consisting of. ”
  • It must be noted that as used herein and in the appended claims, the singular forms "a, " "an, " and "the" include plural reference unless the context clearly dictates otherwise. Further, the terms "a" (or "an" ) , "one or more" and "at least one" can be used interchangeably herein. It is also to be noted that the terms "comprising, " "including, " “characterized by” and "having" can be used interchangeably. Further, any reactant concentrations described herein should be considered as being described on a weight to weight (w/w) basis, unless otherwise specified to the contrary (e.g., mole to mole, weight to volume (w/v) , etc. ) .
  • The term “ST plant” , “Chinese sweet tea plant” , “sweet tea plant” , and “Rubus suavissimus plant” are used interchangeably with reference to a Rubus suavissimus plant.
  • The term “sweet tea extract (STE) ” refers to extract prepared from the whole ST plant, in the aerial part of an ST plant, in the leaves of an ST plant, in the flowers of an ST plant, in the fruit of an ST plant, in the seeds of an ST plant, in the roots of an ST plant, branches of an  ST plant, and/or any other portions of an ST plant. It should also be understood that a sweet tea extract (STE) can be purified and/or separated into one or more sweet tea components (STC) .
  • The term “sweet tea component (STC) ” , refers to a component of a STE. A STC, such as rubusoside, may be purified from a natural source, produced by a chemical or enzymatic process (e.g., converted from stevioside with glycosyl hydrolase) , or produced by fermentation. Examples of STC include, but are not limited to, rubusoside (RU) , suaviosides (SUs) , steviolmonoside, rebaudioside A, 13-O-β-D-glucosyl-steviol, isomers of rebaudioside B, isomers of stevioside, panicloside IV, sugeroside, ent-16α, 17-dihydroxy-kaurane-19-oic acid, ent-13-hydroxy-kaurane-16-en-19-oic acid, ent-kaurane-16-en-19-oic-13-O-β-D-glucoside, ent-16β, 17-dihydroxy-kaurane-3-one, ent-16α, 17-dihydroxy-kaurane-19-oic acid, ent-kaurane-16β, 17-diol-3-one-17-O-β-D-glucoside, ent-16α, 17-dihydroxy-kaurane-3-one, ent-kaurane-3α, 16β, 17-3-triol, ent-13, 17-dihydroxy-kaurane-15-en-19-oic acid, ellagic acid, gallic acid, oleanolic acid, ursolic acid, rutin, quercetin, and isoquercitrin. Examples of suavosides (SUs) include, but are not limited to, SU-A, SU-B, SU-C1, SU-D1, SU-D2, SU-E, SU-F, SU-G, SU-H, SU-I, and SU-J.
  • The term “non-Stevia sweet tea component” or “NS-STC” refers to a STC that is not present in detectable amount in a naturally growing Stevia plant. Examples of NS-STC include, but are not limited to, sauviosides.
  • The term “sauviosides” refers to a group of kaurane-type diterpene glycosides that can can be isolated from the leaves of Rubus suavissimus. Examples of suaviosides include, but are not limited to, SU-A, SU-B, SU-C1, SU-D1, SU-D2, SU-E, SU-F, SU-G, SU-H, SU-I, and SU-J. The chemical structure of some suaviosides are shown in Table 14-7.
  • The term “non-Stevia sweet tea extract” or “NS-STE” refers to a STE that comprises a NS-STC.
  • The term “glycosylated sweet tea extract (GSTE) ” refers to a glycosylation product of a STE.
  • The term “glycosylated sweet tea component (GSTC) ” refers to a glycosylation product of a STC.
  • The term “glycosylated non-stevia sweet tea component (GNS-STC) ” refers to a glycosylation product of a NS-STC.
  • The terms “rubusoside” or “RU” are used interchangeably with reference to a steviol glycoside that is steviol in which both the carboxy group and the tertiary allylic hydroxy group have been converted to their corresponding beta-D-glucosides. Rubusoside may be extracted from a natural source, e.g., leaves from Rubus suavissimus, produced by a chemical or enzymatic process, or produced by fermentation.
  • The terms “steviol glycoside, ” “steviol glycoside, ” and “SG” are used interchangeably with reference to a glycoside of steviol, a diterpene compound found in Stevia leaves. Non-limiting examples of steviol glycosides are shown in Tables A or B below. The steviol glycosides for use in the present application are not limited by source or origin. Steviol glycosides may be extracted from Stevia leaves, synthesized by enzymatic processes or chemical syntheses, or produced by fermentation.
  • The terms “rebaudioside A, ” “Reb A, ” and “RA” are equivalent terms referring to the same molecule. The same condition applies to all lettered rebaudiosides.
  • The term “Stevia extract (SE) ” as used herein, refers to a plant extract from Stevia that contains varying percentages of SGs.
  • The term “Stevia component (SC) ” , refers to a component of a SE.
  • The term “glycosylated Stevia component (GSC) ” refers to a glycosylation product of a SC.
  • The terms “glycosylated steviol glycoside” and “GSG” are used interchangeably with reference to an SG containing one or more additional glucose residues added relative to the parental SGs (including partially glycosylated steviol glycosides) present in e.g., Stevia leaves. A “GSG” may be produced from any known or unknown SG by enzymatic synthesis, chemical synthesis or fermentation. It should be understood that GSG (s) essentially contain a glycosylated steviol glycoside (s) , but may also contain unreacted steviol glycosides, dextrins and other non-steviol glycoside substances when using extracts in the starting materials.  It should also be understood that the GSG (s) can be purified and/or separated into purified/isolated components.
  • An acronym of the type "YYxx" refers to a composition, where YY refers to a given (such as RA) or collection of compounds (e.g., SGs) , where "xx" is typically a percent by weight number between 1 and 100 denoting the level of purity of a given compound (such as RA) or collection of compounds, where the weight percentage of YY in the dried product is equal to or greater than xx. The acronym “YYxx+WWzz” refers to a composition, where each one of “YY” and “WW” refers to a given compound (such as RA) or collection of compounds (e.g., SGs) , and where each of "xx" and “zz” refers to a percent by weight number between 1 and 100 denoting the level of purity of a given compound (such as RA) or collection of compounds, where the weight percentage of YY in the dried product is equal to or greater than xx, and where the weight percentage of WW in the dried product is equal to or greater than zz.
  • The acronym “YYx” refers to a Stevia composition containing YY in amount of ≥ x%and ＜ (x+10) %with the following exceptions: the acronym “RA100” specifically refers to pure RA; the acronym “RA99.5” specifically refers to a composition where the amount of RA is ≥99.5 wt %, but ＜100 wt %; the acronym “RA99” specifically refers to a composition where the amount of RA is ≥99 wt %, but ＜100 wt %; the acronym “RA98” specifically refers to a composition where the amount of RA is ≥98 wt %, but ＜99 wt %; the acronym “RA97” specifically refers to a composition where the amount of RA is ≥97 wt %, but ＜98 wt %; the acronym “RA95” specifically refers to a composition where the amount of RA is ≥95 wt %, but ＜97 wt %; the acronym “RA85” specifically refers to a composition where the amount of RA is ≥85 wt %, but ＜90 wt %; the acronym “RA75” specifically refers to a composition where the amount of RA is ≥75 wt %, but ＜80 wt %; the acronym “RA65” specifically refers to a composition where the amount of RA is ≥65 wt %, but ＜70 wt %; the acronym “RA20” specifically refers to a composition where the amount of RA is ≥15 wt %, but ＜30 wt %. Stevia extracts include, but are not limited to, including, but are not limited to RA20, RA40, RA50, RA60, RA80, RA 90, RA95, RA97, RA98, RA99, RA99.5, RB8, RB10, RB15, RC15, RD6, and combinations thereof.
  • As used herein, the acronym “RUx” is used with reference to a sweet tea extract (ST-E) that is defined by its concentration of RU. More particularly, the acronym “RUx” refers  to a sweet tea extract (ST-E) containing rubusoside (RU) in amount of ≥ x%and ＜ (x+10) %, except as otherwise noted, where e.g., the acronym “RU100” specifically refers to pure RU; the acronym “RU99.5” specifically refers to a composition where the amount of RA is ≥99.5 wt %, but ＜100 wt %; the acronym “RU99” specifically refers to a composition where the amount of RU is ≥99 wt %, but ＜100 wt %; the acronym “RU98” specifically refers to a composition where the amount of RU is ≥98 wt %, but ＜99 wt %; the acronym “RU97” specifically refers to a composition where the amount of RU is ≥97 wt %, but ＜98 wt %; the acronym “RAU95” specifically refers to a composition where the amount of RU is ≥95 wt %, but ＜97 wt %; the acronym “RU85” specifically refers to a composition where the amount of RU is ≥85 wt %, but ＜90 wt %; the acronym “RU75” specifically refers to a composition where the amount of RU is ≥75 wt %, but ＜80 wt %; the acronym “RU65” specifically refers to a composition where the amount of RU is ≥65 wt %, but ＜70 wt %; the acronym “RU20” specifically refers to a composition where the amount of RU is ≥15 wt %, but ＜30 wt %. Sweet tea extracts include, but are not limited to, RU 10, RU20, RU30, RU40, RU50, RU60, RU80, RU90, RU95, RU97, RU98, RU99, RU99.5, or any integer defining a lower limit of RU wt %.
  • The acronym “GSG-RAxx” refers to a GSG composition prepared in an enzymatically catalyzed glycosylation process with RAxx as the starting SG material. More generally, acronyms of the type “GSG-YYxx” refer to a composition of the present application where YY refers to a compound (such as RA, RB, RC or RD) , or a composition (e.g., RA20) , or a mixture of compositions (e.g., RA40+RB8) . For example, GSG-RA20 refers to the glycosylation products formed from RA20.
  • The acronym “GYYxx” refers to a glycosylated product of YYxx. For example, GRU20 refers to the glycosylation products formed from RU20.
  • The abbreviation “GX” refers to a glycosyl group “G” where “X” is a value from 1 to 20 and refers to the number of glycosyl groups present in the molecule. For example, Stevioside G1 (ST-G1) has one (1) glycosyl group (G) , thus “Gl, ” Stevioside G2 (ST-G2) has two (2) glycosyl groups present, Stevioside G3 (ST-G3) has three (3) glycosyl groups present, Stevioside G4 (ST-G4) has four (4) glycosyl groups present, Stevioside G5 (ST-G5) has five (5) glycosyl groups present, Stevioside G6 (ST-G6) has six (6) glycosyl groups present, Stevioside G7 (ST-G7) has seven (7) groups present, Stevioside G8 (ST-G8) has eight (8) glycosyl groups  present, Stevioside G9 (ST-G9) has nine (9) glycosyl groups present, etc. The glycosylation of the molecule can be determined by HPLC-MS.
  • The term “purified RU” refers to a RU preparation that contains at least 50%RU by weight. Purified RU may be prepared from a natural source, such a Stevia extract or a sweet tea extract, or produced by a chemical or enzymatic process, or fermentation. In some embodiments, the term “purified RU” refers to a RU prepration that contains at least 60%, 70%, 80%, 85%, 90%, 95%, 96%, 97%, 98%, or 99%RU by weight.
  • The term “enriched RU” refers to a RU preparation that contains at least 5%RU by weight. Enriched RU may be prepared from a natural source, such a Stevia extract or a sweet tea extract, or produced by a chemical or enzymatic process, or fermentation. In some embodiments, the term “enriched RU” refers to a RU prepration that contains at least 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%or 45%RU by weight.
  • The term “enriched stevioside” composition refers to a
  • The terms “non-RU STC” refers to a sweet tea component that is not RU. A non-RU STC may be purified from a natural source, or produced by a chemical or enzymatic process, or fermentation. The non-RU STC can be a volatile compound or a non-volatile compound.
  • The term “glycosylated RU” refers to molecules having a RU backbone (as shown in Table 1 with a molecular weight of 641) and additional sugar units added in a glycosylation reaction under man-made conditions. Glycosylated RUs include, but are not limited to, molecules having a RU backbone and 1-50 additional sugar units. As used herein, the term “sugar unit” refers to a monosaccharide unit.
  • As used herein, the term “glycoside” refers to a molecule in which a sugar (the "glycone" part or "glycone component" of the glycoside) is bonded to a non-sugar (the "aglycone" part or "aglycone component" ) via a glycosidic bond.
  • The term “terpene” is used with reference to a large and diverse class of organic hydrocarbon molecules classified according to the number of isoprene units in the molecule. Although terpenoids are sometimes used interchangeably with "terpenes" , terpenoids (or  isoprenoids) are modified terpenes as they contain additional functional groups, usually oxygen-containing. The term “terpene” includes hemiterpenes (isoprene, single isoprene unit) , monoterpenes (two isoprene units) , sesquiterpenes (three isoprene units) , diterpenes (four isoprene units) , sesterterpenes (five isoprene units) , triterpenes (six isoprene units) , sesquarterpenes (seven isoprene units) , tetraterpenes (eight isoprene units) and polyterpenes (long chains of many isoprene units) .
  • The term “terpenoid” is used with reference to a large and diverse class of organic molecules derived from terpenes, more specifically five-carbon isoprenoid units assembled and modified in a variety of ways and classified in groups based on the number of isoprenoid units used in group members. Although terpenoids are sometimes used interchangeably with “terpenes” , terpenoids (or isoprenoids) are modified terpenes as they contain additional functional groups, usually oxygen-containing. Similar to the nomenclature for terpenes, the term “terpenoids” includes hemiterpenoids, monoterpenoids, sesquiterpenoids, diterpenoids, sesterterpenoids, triterpenoids, tetraterpenoids and polyterpenoids.
  • The terms “terpene glycoside” and “terpene sweetener” refer to a compound having a terpene aglycone linked by a glycosidic bond to a glycone. Terpene glycosides include, but are not limited to, diterpene glycosides, such as steviol glycosides and suaviosides, and triterpene compounds, such as mogrosides.
  • Exemplary diterpene glycosides from Rubus suavissimus (and extracts thereof) , include steviol glycosides, such as rubusoside, steviol monoside, rebaudioside A, isomers of rebaudioside B, isomers of stevioside, as well as kaurane-type diterpene glycosides found in sweet tea plants, such as the sweet tasting suaviosides B (SU-B) , SU-G, SU-H, SU-I and SU-J, respectively. Additional SUs include bitter suaviosides, such as SU-C1, SU-D2, SU-F and tasteless suaviosides, such as SU-D1 and SU-E.
  • Exemplary triterpene glycosides from plants or extracts derived from Siraitia grosvenorii (also referred to Luo Han Guo or swingle) include mogrol glycosides, mogrosides, mogroside II, mogroside II B, mogroside II E, mogroside III, mogroside III A2, mogroside IV, mogroside V, mogroside VI, neomogroside, grosmomoside siamenoside I, 7-oxo-mogroside II E, 11-oxo-mogroside A1, 11-deoxy-mogroside III, -oxomogroside IV A, 7-oxo-mogroside V, 11-oxo-mogroside V and others.
  • The terms “steviol glycoside, ” and “SG” are used interchangeably with reference to a glycoside of steviol, a diterpene compound shown in Formula I, wherein one or more sugar residues are attached to the compound of Formula I. In the steviol skeleton structure depicted in Formula (I) , the carbonyl oxygen at C 19 forms a glycoside ester bond with a sugar (-C (O) -sugar) ; a hydroxyl group linked to C19 at position 17 can form an O-glycoside linkage with a sugar (-CH2-O-sugar) ; and the C1, C2, C3, C6, C7, C11, C12, C15 CH2 groups can directly form C-glycoside linkages with a sugar (-CH2-sugar) . C-glycosides can alos be formed at the two methyl groups.
  • Steviol glycosides also include glycosides of isomers of steviol (isosteviol) and derivatives of steviol, such as 12α-hydroxy-steviol and 15α-hydroxy-steviol. The chemical structure of isosteviol is shown in Formula II.
  • Formulas III and IV show the possible conformations of a typical sugar molecule exemplified by glucose that can form glycosidic bonds.
  • Pos 1: α-or β-conformation
  • A glycosidic bond involves the hydroxyl-group at the sugar carbon atom numbered 1 (so-called anomeric carbon atom) and either a hydroxyl-group at the steviol/isosteviol molecule building up a so-called O-glycoside or glycosidic ester. Linkage at the carbon atoms given in Table A yields C-glycosides.
  • The sugar part can be selected from any sugar with 3-7 carbon atoms, derived for either dihydroxy-acetone (ketoses) or glycerin-aldehyde (aldoses) . The sugars can occur in open chain or in cyclic form, as D-or L-enantiomers and in α-or β-conformation.
  • Table A, Possible positions of sugar (Sug) molecules linked to steviol/isosteviol
  • Examples of steviol glycosides include, but are not limited to, compounds listed in Table B and isomers thereof. The steviol glycosides for use in the present application are not limited by source or origin. Steviol glycosides may be extracted from Stevia plants, Sweet tea leaves, synthesized by enzymatic processes or chemical syntheses, or produced by fermentation.
  • Table B. Exemplary steviol glycosides
  • Legend: SG-1 to 16: SGs without a specific name; SG-Unk1-6: SGs without detailed structural proof; Glc: Glucose; Rha: Rhamnose; Xyl: Xylose; Ara: Arabinose.
  • As used herein, the terms “rebaudioside A, ” “Reb A, ” and “RA” are equivalent terms referring to the same molecule. The same condition applies to all lettered rebaudiosides.
  • The terms “steviol glycoside composition” and “SG composition” are used interchangeably with reference to a composition comprising one or more SGs.
  • The terms “non-sweet tea steviol glycosides” or “NST-SG” are used interchangeably with reference to steviol glycosides that are not present in sweet tea plant.
  • The term “monosaccharide” as used herein refers to a single unit of a polyhydroxyaldehyde forming an intramolecular hemiacetal the structure of which including a six-membered ring of five carbon atoms and one oxygen atom. Monosaccharides may be present in different diasteromeric forms, such as α or β anomers, and D or L isomers. An “oligosaccharide” consists of short chains of covalently linked monosaccharide units. Oligosaccharides comprise disaccharides which include two monosaccharide units, as well as trisaccharides which include three monosaccharide units. A “polysaccharide” consists of long chains of covalently linked monosaccharide units.
  • The term “glycosidic bond” and “glycosidic linkage” refer to a type of chemical bond or linkage formed between the anomeric hydroxyl group of a saccharide or saccharide derivative (glycone) and the hydroxyl group of another saccharide or a non-saccharide organic compound (aglycone) such as an alcohol. The reducing end of the di-or polysaccharide lies towards the last anomeric carbon of the structure, and the terminal end is in the opposite direction.
  • As used herein, the term “enzymatically catalyzed” refers to a method that is performed under the catalytic action of an enzyme, in particular of a glycosidase or a glycosyltransferase. The method can be performed in the presence of said glycosidase or glycosyltransferase in isolated (purified, enriched) or crude form.
  • The term “glycosyltransferase” (GT) refers to an enzyme that catalyzes the formation of a glycosidic linkage to form a glycoside. A GT catalyzes the transfer of saccharide moieties from an activated nucleotide sugar (also known as the “glycosyl donor or “sugar donor” ) to a nucleophilic glycosyl acceptor molecule, the nucleophile of which can be oxygen-carbon-, nitrogen-, or sulfur-based.
  • The result of glycosyl transfer can be a carbohydrate, glycoside, oligosaccharide, or polysaccharide. As used herein, the term “glycosyltransferase” also includes variants, mutants and enzymatically active portions of glycosyltransferases. Likewise, the term “glycosidase” also includes variants, mutants and enzymatically active portions of glycosidases.
  • The terms “sugar donor” or “glycosyl donor” refer to a compound or substance from natural or synthetic sources comprising one or more saccharide moieties for transfer to a an oxygen-carbon-, nitrogen-, or sulfur-based nucleophilic glycosyl acceptor molecule in a glycosylation reaction.
  • The term “dextrin” refers to a linear low-molecular weight water-soluble glucose polymer which is produced by the hydrolysis of starch that can serve as a sugar donor in a glycosylation reaction. Dextrins are mixtures of polymers of D-glucose units linked primarily by α- (1-4) glycosidic bonds and to a lesser extent α- (1-6) glycosidic bonds. Dextrins are typically produced by enzymatic hydrolysis of starch or application of heat under acid conditions, resulting in a mixture of polyglucose molecules of different chain lengths. “Maltodextrins” are the product of the dextrinization of starch using enzymes coupled with acid hydrolysis or heating; “pyrodextrins” are the product of dextrinization of starch using heat and acid. As used herein, the term “dextrin” includes maltodextrins, pyrodextrins and water-soluble glucose polymers having 3 or more glucose units. Dextrins can be obtained from various natural products, such as wheat, rice, maize and tapioca.
  • The terms “glycosylated steviol glycoside” and “GSG” are used interchangeably with reference to molecules that (1) contain a SG backbone and one or more additional sugar residues, and (2) are artificially produced by enzymatic synthesis, chemical synthesis or fermentation.
  • The terms “glycosylated steviol glycoside composition” and “GSG composition” are used interchangeably with reference to a composition comprising one or more GSGs.
  • It should be understood that a glycosylation product of X may contain unreacted starting materials. For example, a glycosylation product of a sweet tea extract may contain glycosylated sweet tea components, unreacted sweet tea components, and unreacted sugar donors such as maltodextrins. A suitable method for measuring the amount of unreacted sugar donors,  including dextrins and maltodextrins are described in the section entitled “Assay for determining residual maltodextrin and TSG (9) content in Example 22. Suitable methods for removing unreacted sugar donors, including dextrins and maltodextrins are described in the section entitled “Process for preparing reduced maltodextrin GSG product compositions” and subsequent modification thereto in Example 22.
  • The terms “sweet tea glycoside” or “STG” are used interchangeably with reference to a glycoside derived from sweet tea plants or known to be present in sweet tea plants. Examples of STG include, but are not limited to, rubusoside, suaviosides such as SU-A, SU-B, SU-C1, SU-D1, SU-D2, SU-E, SU-F, SU-G, SU-H, SU-I, and SU-J, steviolmonoside, rebaudioside A, 13-O-β-D-glucosyl-steviol, isomers of rebaudioside B, isomers of stevioside, panicloside IV and sugeroside.
  • The term “non-stevia sweet tea glycoside” or “NS-STG” refers to STGs that are not present in Stevia plant or stevia extracts. Examples of NS-STG include, but are not limited to, sauviosides.
  • The terms “glycosylated sweet tea glycoside” and “GSTG” are used interchangeably with reference to molecules that (1) contain a NS-STG backbone and one or more additional sugar residues, and (2) are artificially produced by enzymatic conversion, fermentation or chemical synthesis.
  • The terms “glycosylated non-stevia sweet tea glycoside” and “GNS-STG” are used interchangeably with reference to molecules that (1) contain a NS-STG backbone and one or more additional sugar residues, and (2) are artificially produced by enzymatic synthesis, chemical synthesis or fermentation.
  • The terms “glycosylated rubusoside” “glycosylated RU” and “GRU” are used interchangeably with reference to an exogenously glycosylated rubusoside, while the terms “glycosylated suavioside, ” “glycosylated SU’ and “GSU” are used interchangeably with reference to an exogenously glycosylated suavioside. Rubusoside may be mono-glucosylated or di-glucosylated. A chemical structure of mono-glucosylated rubusoside is shown in Formula (V) below. Table C shows various types of linkages that can occur in a mono-glucosylated rubusoside according to the present application.
  • Table C. Linkages in mono-glucosylated rubusoside.
  • The term "mogroside” ( “MG” ) refers to a triterpene-glycoside and is recognized in the art and is intended to include the major and minor constituents of mogroside extracts.
  • Extracts from the fruits of Siraitia grosvenorii (Swingle) , also known as Momordica grosvenori (Swingle) , Luo Han Guo or monk fruit etc. provide a family of triterpene-glycosides and are referred to as mogroside (s) ( “MGs” ) . The extracts include, for example, mogroside V, mogroside IV, siamenoside I, and 11-oxomogroside V. Constituents of the mogroside extracts are referred to by the designation “MG” followed by symbol, such as “V” ,  therefore mogroside V is “MGV” . Siamenoside I would be “SSI” , 11-oxomogroside V would be “OGV” .
  • Monk fruit extracts (MFEs; or “swingle extracts” ) can contain, for example, a mogroside such as MGV, in an amount of 3%by weight, 5%by weight, 20%by weight, 40%by weight, 50%by weight, 60%by weight or higher but containing other mogrosides or non-mogrosides in the extracts. For example, other components include other mogrosides such as mogroside II, mogroside IIIA, mogroside IIIE, mogroside IVA, mogroside IVE, siamenoside I, and 11-oxomogroside V. In addition, some other polysaccharides or flavonoids may be present.
  • The mogroside (s) of interest can be purified before use.
  • The term “glycosylated mogroside (s) ” ( “GMG” , “GMGs” ) , refers to a mogroside that is glycosylated at least at one or more positions in addition to those positions glycosylated in native form, obtained, for example, by synthetic manipulation or by enzymatic processes.
  • The terms “glycosylated monk fruit extract” and “GMFE” refers to extracts obtained by transglycosylating a monk fruit extract containing mogrosides, or transglycosylating purified mogrosides so as to add glucose units, for example, one, two, three, four, five or more than five glucose units, to the native mogrosides by glycosyltransferase, preferably, CGTase enzyme (cyclodextringlycosyltransferase) . GMGs or GMFEs containing glycosylated mogroside (s) contain short chain compounds obtained by hydrolyzation of glycosylated product and also comprises non-glycosylated ingredients which are the residue of non-reacted mogrosides, or unreacted components other than mogrosides contained in the monk fruit extract.
  • A suitable procedure to prepare glycosylated mogrosides (GMGs) or glycosylated monk fruit extracts (MFEs) includes i) dissolving dextrin in water (e.g., reverse osmosis) , ii) adding the mogrosides or extract to the solubilized dextrin to obtain a mixture, wherein the ratio of dextrin to mogrosides/extract is optimized in a ratio of between 100∶1 to 1∶100 with suitable ranges including 3∶1, 2∶1, 1.5∶1 and 1∶1, iii) adding CGTase enzyme to the mixture followed by incubating the mixture at 60℃ for a desired length of reaction time to glycosylate mogrosides with glucose molecules derived from dextrin.
  • It should be understood that GMG (s) essentially contains glycosylated mogroside (s) , but also contains unreacted mogrosides, dextrin and other non-mogroside substances found in extracts. It should also be understood that the GMG (s) can be purified and/or separated into purified/isolated components before use.
  • The acronym “G-X” refers to a glycosylation product of composition X, i.e., a product prepared in an enzymatically catalyzed glycosylation process with X and one or more sugar donors as the starting materials. For example, G-RU20 refers to the glycosylation products formed from RU20 and G- (RU20+RB8) refers to the glycosylation products formed from RU20+RB8.
  • The term “thaumatin” , as used herein, is used generically with reference to thaumatin I, II, III, a, b, c, etc. and/or combinations thereof.
  • The term “non-volatile” , as used herein, refers to a compound having a negligible vapor pressure at room temperature, and/or exhibits a vapor pressure of less than about 2 mm of mercury at 20 ℃.
  • The term “volatile” , as used herein, refers to a compound having a measurable vapor pressure at room temperature, and/or exhibits a vapor pressure of, or greater than, about 2 mm of mercury at 20 ℃.
  • As used herein, the term "sweetener" generally refers to a consumable product, which produces a sweet taste when consumed alone. Examples of sweeteners include, but are not limited to, high-intensity sweeteners, bulk sweeteners, sweetening agents, and low sweetness products produced by synthesis, fermentation or enzymatic conversion methods.
  • As used herein the term "high-intensity sweetener, " refers to any synthetic or semi-synthetic sweetener or sweetener found in nature. High-intensity sweeteners are compounds or mixtures of compounds which are sweeter than sucrose. High-intensity sweeteners are typically many times (e.g., 20 times and more, 30 times and more, 50 times and more or 100 times sweeter than sucrose) . For example, sucralose is about 600 times sweeter than sucrose, sodium cyclamate is about 30 times sweeter, Aspartame is about 160-200 times sweeter, and thaumatin is about 2000 times sweeter then sucrose (the sweeteness depends on the tested concentration compared with sucrose) .
  • High-intensity sweeteners are commonly used as sugar substitutes or sugar alternatives because they are many times sweeter than sugar but contribute only a few to no calories when added to foods. High-intensity sweeteners may also be used to enhance the flavor of foods. High-intensity sweeteners generally will not raise blood sugar levels.
  • As used herein, the term “high intensity natural sweetener, ” refers to sweeteners found in nature, typically in plants, which may be in raw, extracted, purified, refined, or any other form, singularly or in combination thereof. High intensity natural sweeteners characteristically have higher sweetness potency, but fewer calories than sucrose, fructose, or glucose. Examples of high intensity natural sweetener include, but are not limited to, sweet tea extracts, stevia extracts, swingle extracts, steviol glycosides, suaviosides, morgosides, mixtures, salts and derivatives thereof.
  • As used herein, the term “high intensity synthetic sweetener” or “high intensity artificial sweetener” refers to high intensity sweeteners that are not found in nature. High intensity synthetic sweeteners include “high intensity semi-synthetic sweeteners" or "high intensity semi-artificial sweeteners” , which are synthesized from, artificially modified from, or derived from, high intensity natural sweeteners. Examples of high intensity synthetic sweeteners include, but are not limited to, sucralose, aspartame, acesulfame-K, neotame, saccharin and aspartame, glycyrrhizic acid ammonium salt, sodium cyclamate, saccharin, advantame, neohesperidin dihydrochalcone (NHDC) and mixtures, salts and derivatives thereof.
  • As used herein, the term "sweetening agent” refers to a high intensity sweetener.
  • As used herein, the term “bulk sweetener” refers to a sweetener, which typically adds both bulk and sweetness to a confectionery composition and includes, but is not limited to, sugars, sugar alcohols, sucrose, commonly referred to as “table sugar, ” fructose, commonly referred to as “fruit sugar, ” honey, unrefined sweeteners, syrups, such as agave syrup or agave nectar, maple syrup, com syrup and high fructose com syrup (or HFCS) .
  • As used herein, the term "sweetener enhancer” refers to a compound (or composition) capable of enhancing or intensifying sensitivity of the sweet taste. The term "sweetener enhancer” is synonymous with a “sweetness enhancer, ” “sweet taste potentiator, ” “sweetness potentiator, ” and/or “sweetness intensifier. ” A sweetener enhancer enhances the  sweet taste, flavor, mouth feel and/or the taste profile of a sweetener without giving a detectable sweet taste by the sweetener enhancer itself at an acceptable use concentration. In some embodiments, the sweetener enhancer provided herein may provide a sweet taste at a higher concentration by itself. Certain sweetener enhancers provided herein may also be used as sweetening agents.
  • Sweetener enhancers can be used as food additives or flavors to reduce the amounts of sweeteners in foods while maintaining the same level of sweetness. Sweetener enhancers work by interacting with sweet receptors on the tongue, helping the receptor to stay switched “on” once activated by the sweetener, so that the receptors respond to a lower concentration of sweetener. These ingredients could be used to reduce the calorie content of foods and beverages, as well as save money by using less sugar and/or less othersweeteners. Examples of sweetener enhancers include, but are not limited to, brazzein, miraculin, curculin, pentadin, mabinlin, thaumatin, and mixtures thereof.
  • In some cases, sweetening agents or sweeteners can be used as sweetener enhancers or flavors when their dosages in food and beverage are low. In some cases, sweetener enhancers can be utilized as sweeteners where their dosages in foods and beverages are higher than dosages regulated by FEMA, EFSA or other related authorities.
  • As used herein, the phrase “low sweetness products” , including those produced by synthesis, fermentation or enzymatic conversion refer to products that have less sweetness or similar sweetness than sucrose. Examples of low sweetness products produced by extraction, synthesis, fermentation or enzymatic conversion method include, but are not limited to, sorbitol, xylitol, mannitol, erythritol, trehalose, raffmose, cellobiose, tagatose, DOLCIA PRIMA TM allulose, inulin, N-- [N- [3- (3-hydroxy-4-methoxyphenyl) propyl] -alpha-aspartyl] -L-phenylalanine 1-methyl ester, glycyrrhizin, and mixtures thereof.
  • For example, “sugar alcohols” or “polyols” are sweetening and bulking ingredients used in manufacturing of foods and beverages. As sugar substitutes, they supply fewer calories (about a halfto one-third fewer calories) than sugar, are converted to glucose slowly, and are not characterized as causing spiked increases in blood glucose levels.
  • Sorbitol, xylitol, and lactitol are exemplary sugar alcohols (or polyols) . These are generally less sweet than sucrose, but have similar bulk properties and can be used in a wide range of food and beverage products. In some case, their sweetness profile can be fine-tuned by being mixed together with high-intensity sweeteners.
  • The terms “flavor” and “flavor characteristic” are used interchangeably with reference to the combined sensory perception of one or more components of taste, odor, and/or texture.
  • The terms “flavoring agent” , “flavoring” and “flavorant” are used interchangeably with reference to a product added to food or beverage products to impart, modify, or enhance the flavor of food. As used herein, these terms do not include substances having an exclusively sweet, sour, or salty taste (e.g., sugar, vinegar, and table salt) . In some embodiments, a sweetener, such as a SG and or GSG containing composition, can be used as a flavoring agent at concentrations that are below the sweetness recognition threshold of the sweetener.
  • The term “natural flavoring substance” refers to a flavoring substance obtained by physical processes that may result in unavoidable but unintentional changes in the chemical structure of the components of the flavoring (e.g., distillation and solvent extraction) , or by enzymatic or microbiological processes, from material of plant or animal origin.
  • The term “synthetic flavoring substance” refers to a flavoring substance formed by chemical synthesis.
  • The term “enhance, ” as used herein, includes augmenting, intensifying, accentuating, magnifying, and potentiating the sensory perception of a flavor characteristic without changing the nature or quality thereof.
  • Unless otherwise specified, the terms “modify” or “modified” as used herein, includes altering, varying, suppressing, depressing, fortifying and supplementing the sensory perception of a flavor characteristic where the quality or duration of such characteristic was deficient.
  • The phrase “sensory profile” or “taste profile” is defmed as the temporal profile of all basic tastes of a sweetener. The onset and decay of sweetness when a sweetener is consumed, as perceived by trained human tasters and measured in seconds from first contact with a taster′s tongue ( “onset” ) to a cutoff point (typically 180 seconds after onset) , is called the “temporal profile of sweetness. ” A plurality of such human tasters is called a “sensory panel” . In addition to sweetness, sensory panels can also judge the temporal profile of the other “basic tastes” : bitterness, saltiness, sourness, piquance (aka spiciness) , and umami (aka savoriness or meatiness) . The onset and decay of bitterness when a sweetener is consumed, as perceived by trained human tasters and measured in seconds from first perceived taste to the last perceived aftertaste at the cutoff point, is called the “temporal profile of bitterness” .
  • The phrase “sucrose equivalence” or “SugarE” is the amount of non-sucrose sweetener required to provide the sweetness of a given percentage of sucrose in the same food, beverage, or solution. For instance, a non-diet soft drink typically contains 12 grams of sucrose per 100 ml of water, i.e., 12%sucrose. This means that to be commercially accepted, diet soft drinks must generally have the same sweetness as a 12%sucrose soft drink, i.e., a diet soft drink must have a 12%SugarE. Soft drink dispensing equipment assumes a SugarE of 12%, since such equipment is set up for use with sucrose-based syrups.
  • As used herein, the term “off-tast” refers to an amount or degree of taste that is not characteristically or usually found in a beverage product or a consumable product of the present disclosure. For example, an off-taste is an undesirable taste of a sweetened consumable to consumers, such as, a bitter taste, a licorice-like taste, a metallic taste, an aversive taste, an astringent taste, a delayed sweetness onset, a lingering sweet aftertaste, and the like, etc.
  • As used herein, the term “personal care product” refers to a medicinal, oral hygiene, or cosmetic product comprising a composition in accordance with the present application.
  • The term “orally consumable product” refers to a composition that can be drunk, eaten, swallowed, inhaled, ingested or otherwise in contact with the mouth or nose of man or animal, including compositions which are taken into and subsequently ejected from the mouth or nose. Orally consumable products are safe for human or animal consumption when used in a generally acceptable range. Orally consumable products include, but are not limited to  mouthwashes, mouth rinses, breath fresheners, toothpastes, tooth polishes, dentifrices, mouth sprays, teeth whitening agents, soaps, perfumes, and the like. Food, feed, pharmaceuticals are also included.
  • Unless otherwise noted, the term “ppm” (parts per million) means parts per million on a w/w or wt/wt basis.
  • II. Sweetening or flavoring compositions
  • One aspect of the present application provides sweetening and flavoring compositions that comprise one or more products selected from the group consisting of rubusosides (RU) , sweet tea components (STCs) , sweet tea extracts (STEs) , morgrosides (MGs) , monk fruit components (MFCs) , monk fruit extracts (MFEs) , steviol glycosides (SGs) , Stevia components (SCs) , Stevia extracts (SEs) , glycosylated rubusoside (GRU) , glycosylated sweet tea components (GSTCs) , glycosylated sweet tea extracts (GSTEs) , glycosylated morgrosides (GMGs) , glycosylated monk fruit components (GMFCs) , glycosylated monk fruit extracts (GMFEs) , glycosylated stevia glycosides (GSGs) , glycosylated Stevia components (GSCs) and glycosylated stevia extracts (GSEs) , wherein the one or more products are present in the composition in a total amount of 0.1-99.9 wt%, and wherein the composition is a sweetener composition, a flavoring composition, or both, as well as methods of making and using such compositions to improve the taste and/or flavor of a consumable product.
  • In some embodiments, the present application provides stevia-based sweetening and flavoring compositions that comprise (A) a SG, SE and/or SC, (B) a GSG, GSE and/or GSC, or any combinations of (A) and (B) .
  • In some embodiments, the present application provides stevia-based sweetening and flavoring compositions that comprise (A) a MG, MFC and/or MFE, (B) a GMG, GMFC and/or GMFE, or any combinations of (A) and (B) .
  • In some embodiments, the present application provides sweet tea-based sweetening and flavoring compositions that comprise (A) a sweet tea extract (STE) or at least one sweet tea component (STC) , (B) a glycosylated STE or at least one glycosylated STC, or any combinations of (A) - (B) .
  • In some embodiments, the STE described above is a NS-STE. In some embodiments, the STC described above is a NS-STC.
  • Sweet tea plants and extracts therefrom include a wide variety of biochemically active STCs, including steviol glycosides, non-steviol glycosides substances, diterpenes, diterpenoids, triterpenes, triterpenoids, carotenoids (tetraterpenoids) , flavonoids, isoflavonoids, polyphenols, tannins, carotenoids, free amino acids, vitamins, and the like.
  • A. Sweet tea extracts (STEs) , sweet tea components (STCs) , steviol glycosides (SGs) , Stevia extracts (SEs) , Stevia components (SCs) , Mogrosides (MGs) , Monk fruit extracts (MFEs) and Monk fruit components (MFCs)
  • In some embodiments, a sweetener or flavoring composition comprises one or more STEs, one or more STCs, one or more SEs, one or more SGs, one or more SCs, one or more MFEs, one or more MGs, and/or or one or more MFCs in an amount of 000.1-99.9 wt%of the composition.
  • In some embodiments, one or more STEs, one or more STCs, one or more SEs, one or more SGs, one or more SCs, one or more MFEs, one or more MGs, and/or or one or more MFCs, are present in an amount of 0.001-99 wt %, 0.001-75 wt %, 0.001-50 wt%, 0.001-25 wt%, 0.001-10 wt %, 0.001-5 wt %, 0.001-2 wt %, 0.001-1 wt %, 0.001-0.1 wt %, 0.001-0.01 wt %, 0.01-99 wt %, 0.01-75 wt %, 0.01-50 wt%, 0.01-25 wt%., 0.01-10 wt %, 0.01-5 wt %, 0.01-2 wt %, 0.01-1 wt %, 0.1-99 wt %, 0.1-75 wt %, 0.1 wt-50 wt%, 0.1-25 wt%, 0.1-10 wt %, 0.1-5 wt %, 0.1-2 wt %, 0.1-1 wt %, 0.1-0.5 wt %, 1-99 wt %, 1-75 wt %, 1-50 wt%, 1-25 wt%, 1-10 wt %, 1-5 wt %, 5-99 wt %, 5-75 wt %, 5-50 wt%, 5-25 wt%, 5-10 wt %, 10-99 wt %, 10-75 wt %, 10-50 wt%, 10-25 wt%, 10-15 wt %, 20-99 wt %, 20-75 wt %, 20-50 wt%, 30-99 wt %, 30-75 wt %, 30-50 wt%, 40-99 wt %, 40-75 wt %, 40-50 wt%, 50-99 wt %, 50-75 wt %, 60-99 wt %, 60-75 wt %, 70-99 wt %, 70-75 wt %, 80-99 wt %, 80-90 wt %, or 90-99 wt%of the composition.
  • In some embodiments, the sweetener or flavoring composition comprises a STE that contains enriched RU.
  • In some embodiments, the sweetener or flavoring composition comprises a STE that contains an enriched diterpene glycoside.
  • In some embodiments, the sweetener or flavoring composition comprises one or more STCs selected from the group consisting of RU, SU, steviolmonoside, rebaudioside A, 13-O-β-D-glucosyl-steviol, isomers of rebaudioside B, isomers of stevioside, panicloside IV, sugeroside, ent-16α, 17-dihydroxy-kaurane-19-oic acid, ent-13 -hydroxy-kaurane-16-en-19-oic acid, ent-kaurane-16-en-19-oic-13-O-β-D-glucoside, ent-16β, 17-dihydroxy-kaurane-3-one, ent-16α, 17-dihydroxy-kaurane-19-oic acid, ent-kaurane-16β, 17-diol-3-one-17-O-β-D-glucoside, ent-16α, 17-dihydroxy-kaurane-3-one, ent-kaurane-3α, 16β, 17-3-triol, ent-13, 17-dihydroxy-kaurane-15-en-19-oic acid, ellagic acid, gallic acid, oleanolic acid, ursolic acid, rutin, quercetin, and isoquercitrin.
  • In some embodiments, the sweetener or flavoring composition comprises one or more suavosides slected from the group consisting of SU-A, SU-B, SU-C1, SU-D1, SU-D2, SU-E, SU-F, SU-G, SU-H, SU-I, and SU-J.
  • In some embodiments, the sweetener or flavoring composition comprises purified RU.
  • In some embodiments, the sweetener or flavoring composition comprises a STE having a RU content of 1-99 wt%, 1-95 wt%, 1-90 wt%, 1-80 wt%, 1-70 wt%, 1-60 wt%, 1-50 wt%, 1-40 wt%, 1-30 wt%, 1-20 wt%, 1-10 wt%, 1-5 wt%, 5-99 wt%, 5-95 wt%, 5-90 wt%, 5-80 wt%, 5-70 wt%, 5-60 wt%, 5-50 wt%, 5-40 wt%, 5-30 wt%, 5-20 wt%, 5-10 wt%, 10-99 wt%, 10-95 wt%, 10-90 wt%, 10-80 wt%, 10-70 wt%, 10-60 wt%, 10-50 wt%, 10-40 wt%, 10-30 wt%, 10-20 wt%, 20-99 wt%, 20-95 wt%, 20-90 wt%, 20-80 wt%, 20-70 wt%, 20-60 wt%, 20-50 wt%, 20-40 wt%, 20-30 wt%, 30-99 wt%, 30-95 wt%, 30-90 wt%, 30-80 wt%, 30-70 wt%, 30-60 wt%, 30-50 wt%, 30-40 wt%, 40-99 wt%, 40-95 wt%, 40-90 wt%, 40-80 wt%, 40-70 wt%, 40-60 wt%, 40-50 wt%, 50-99 wt%, 50-95 wt%, 50-90 wt%, 50-80 wt%, 50-70 wt%, 50-60 wt%, 60-99 wt%, 60-95 wt%, 60-90 wt%, 60-80 wt%, 60-70 wt%, 70-99 wt%, 70-95 wt%, 70-90 wt%, 70-80 wt%, 80-99 wt%, 80-95 wt%, 80-90 wt%, 90-99 wt%, 90-95 wt%, or 95-99 wt%of the STE.
  • In some embodiments, the sweetener or flavoring composition comprises a STE having a RU content of at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70  wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or any range defined by any pair of these integers.
  • In some embodiments, the the sweetener or flavoring composition comprises one or more flavonoid glycosides, isoflavone glycosides, saponin glycosides, phenol glycosides, cynophore glycosides, anthraquinone glycosides, cardiac glycosides, bitter glycosides, coumarin glycosides, or sulfur glycosides.
  • Exemplary flavonoids include, but are not limited to, anthocyanidins; anthoxanthins, including flavones, such as luteolin, apigenin, tangeritin; and flavonols, such as quercetin, kaempferol, myricetin, fisetin, galangin, isorhamnetin, pachypodol, rhamnazin, pyranoflavonols, furanoflavonols; flavanones, such as hesperetin, naringenin, eriodictyol, and homoeriodictyol; flavanonols, such as taxifolin (or dihydroquercetin) and dihydrokaempferol; and flavans, including flavanols, such as catechin, gallocatechin, catechin 3-gallate, gallocatechin 3-gallate, epicatechin, epigallocatechin (EGC) , epicatechin 3-gallate, epigallocatechin 3-gallate, theaflavin, theaflavin-3’-gallate, theaflavin-3, 3’-digallate, thearubigin, and proanthocyanidins, which are dimers, trimers, oligomers, or polymers of the flavanols, and glycosides thereof.
  • Exemplary isoflavonoids include isoflavones, such as genistein, daidzein, glycitein, isoflavanes, isoflavandiols, isoflavenes, coumestans, pterocarpans, and glycosides thereof.
  • Exemplary polyphenols include gallic acid, ellagic acid, quercetin, isoquercitrin, rutin, citrus flavonoids, catechins, proanthocyanidins, procyanidins, anthocyanins, reservatrol, isoflavones, curcumin, hesperidin, naringin, and chlorogenic acid, and and glycosides thereof.
  • Exemplary tannins include gallic acid esters, ellagic acid esters, ellagitannins, including rubusuaviins A, B, C, D, -E, and -F; punicalagins, such as pedunculagin and 1 (β) -O-galloyl pedunculagin; strictinin, sanguiin H-5, sanguiin H-6, 1-desgalloyl sanguiin H-6. lambertianin A, castalagins, vescalagins, castalins, casuarictins, grandimins, punicalins, roburin A, tellimagrandin II, terflavin B; gallotannins, including digalloyl glucose and 1, 3, 6-trigalloyl glucose; flavan-3-ols, oligostilbenoids, proanthocyanidins, polyflavonoid tannins, catechol-type tannins, pyrocatecollic type tannins, flavolans, and glycosides thereof.
  • Exemplary carotenoids include carotenes, including α-, β-, γ-, δ-, and ε-carotenes, lycopene, neurosporene, phytofluene, phytoene; and xanthophylls, including canthaxanthin, cryptoxanthin, zeaxanthin, astaxanthin, lutein, rubixanthin, and glycosides thereof.
  • In some embodiments, the sweetener or flavoring composition comprises one or more diterpenes, diterpenoids, triterpenes and/or triterpenoids. Exemplary diterpenes and diterpenoids include steviol, ent-16α, 17-dihydroxy-kaurane-19-oic acid, ent-13 -hydroxy-kaurane-16-en-19-oic acid, ent-16β, 17-dihydroxy-kaurane-3-one, ent-16α, 17-dihydroxy-kaurane-19-oic acid, ent-16α, 17-dihydroxy-kaurane-3-one, ent-kaurane-3α, 16β, 17-3-triol, ent-13, 17-dihydroxy-kaurane-15-en-19-oic acid, and glycosides thereof. Exemplary triterpenes and triterpenoids, include oleanolic acid, ursolic acid, saponin, and glycoside thereof.
  • In some embodiments, the STE/STC containing sweetener or flavoring composition further comprises a stevia extract. In some embodiments, the STE/STC containing sweetener or flavoring composition further comprises a one or more non-sweet tea steviol glycosides. In some embodiments, the STE/STC containing sweetener or flavoring composition further comprises thaumatin.
  • B. Glycosylated STEs, glycosylated STCs, glycosylated SEs, glycosylated SGs, glycosylated SCs, glycosylated MGs, glycosylated MFEs and glycosylated MFCs
  • In some embodiments, the sweetener or flavoring composition of the present application comprises one or more glycosylated STEs (GSTEs) , one or more glycosylated STCs (GSTCs) , one or more glycosylated SEs (GSEs) , one or more glycosylated SGs (GSGs) , one or more glycosylated SCs (GSCs) , one or more glycosylated MGs (GMGs) , one or more glycosylated MFEs (GMFEs) , and/or one or more glycosylated glycosylated MFCs (GMFCs) , where the glycosylated components are present in the sweetener or flavor composition in an amount of 000.1-99.9 wt%.
  • In some embodiments, the one or more GSTEs, one or more GSTCs, one or more GSEs, one or more GSGs, one or more GSCs, one or more GMGs, one or more GMFEs, and/or one or more GMFCs are present in the sweetener or flavoring composition in an amount of 0.001-99 wt %, 0.001-75 wt %, 0.001-50 wt%, 0.001-25 wt%, 0.001-10 wt %, 0.001-5 wt %, 0.001-2 wt %, 0.001-1 wt %, 0.001-0.1 wt %, 0.001-0.01 wt %, 0.01-99 wt %, 0.01-75 wt %,  0.01-50 wt%, 0.01-25 wt%., 0.01-10 wt %, 0.01-5 wt %, 0.01-2 wt %, 0.01-1 wt %, 0.1-99 wt %, 0.1-75 wt %, 0.1 wt-50 wt%, 0.1-25 wt%, 0.1-10 wt %, 0.1-5 wt %, 0.1-2 wt %, 0.1-1 wt %, 0.1-0.5 wt %, 1-99 wt %, 1-75 wt %, 1-50 wt%, 1-25 wt%, 1-10 wt %, 1-5 wt %, 5-99 wt %, 5-75 wt %, 5-50 wt%, 5-25 wt%, 5-10 wt %, 10-99 wt %, 10-75 wt %, 10-50 wt%, 10-25 wt%, 10-15 wt %, 20-99 wt %, 20-75 wt %, 20-50 wt%, 30-99 wt %, 30-75 wt %, 30-50 wt%, 40-99 wt %, 40-75 wt %, 40-50 wt%, 50-99 wt %, 50-75 wt %, 60-99 wt %, 60-75 wt %, 70-99 wt %, 70-75 wt %, 80-99 wt %, 80-90 wt %, or 90-99 wt%.
  • In some embodiments, the glycosylated STE is prepared from a STE that contains enriched RU.
  • In some embodiments, the glycosylated STE is prepared from a STE that contains an enriched diterpene glycoside.
  • In some embodiments, the one or more glycosylated STCs are selected from the glycosylation products ofRU, SU, steviolmonoside, rebaudioside A, 13-O-β-D-glucosyl-steviol, isomers of rebaudioside B, isomers of stevioside, panicloside IV, sugeroside, ent-16α, 17-dihydroxy-kaurane-19-oic acid, ent-13-hydroxy-kaurane-16-en-19-oic acid, ent-kaurane-16-en-19-oic-13-O-β-D-glucoside, ent-16β, 17-dihydroxy-kaurane-3-one, ent-16α, 17-dihydroxy-kaurane-19-oic acid, ent-kaurane-16β, 17-diol-3-one-17-O-β-D-glucoside, ent-16α, 17-dihydroxy-kaurane-3-one, ent-kaurane-3α, 16β, 17-3-triol, ent-13, 17-dihydroxy-kaurane-15-en-19-oic acid, ellagic acid, gallic acid, oleanolic acid, ursolic acid, rutin, quercetin, and isoquercitrin.
  • In some embodiments, the one or more glycosylated STCs comprise one or more of the glycosylation products of SU-A, SU-B, SU-C1, SU-D1, SU-D2, SU-E, SU-F, SU-G, SU-H, SU-I, and SU-J.
  • In some embodiments, the one or more glycosylated STCs comprise glycosylation product of purified RU.
  • In some embodiments, the sweetener or flavoring composition comprises the glycosylation product of a STE having a RU content of 1-99 wt%, 1-95 wt%, 1-90 wt%, 1-80 wt%, 1-70 wt%, 1-60 wt%, 1-50 wt%, 1-40 wt%, 1-30 wt%, 1-20 wt%, 1-10 wt%, 1-5 wt%, 5-99 wt%, 5-95 wt%, 5-90 wt%, 5-80 wt%, 5-70 wt%, 5-60 wt%, 5-50 wt%, 5-40 wt%, 5-30 wt%, 5-20 wt%, 5-10 wt%, 10-99 wt%, 10-95 wt%, 10-90 wt%, 10-80 wt%, 10-70 wt%, 10-60 wt%, 10- 50 wt%, 10-40 wt%, 10-30 wt%, 10-20 wt%, 20-99 wt%, 20-95 wt%, 20-90 wt%, 20-80 wt%, 20-70 wt%, 20-60 wt%, 20-50 wt%, 20-40 wt%, 20-30 wt%, 30-99 wt%, 30-95 wt%, 30-90 wt%, 30-80 wt%, 30-70 wt%, 30-60 wt%, 30-50 wt%, 30-40 wt%, 40-99 wt%, 40-95 wt%, 40-90 wt%, 40-80 wt%, 40-70 wt%, 40-60 wt%, 40-50 wt%, 50-99 wt%, 50-95 wt%, 50-90 wt%, 50-80 wt%, 50-70 wt%, 50-60 wt%, 60-99 wt%, 60-95 wt%, 60-90 wt%, 60-80 wt%, 60-70 wt%, 70-99 wt%, 70-95 wt%, 70-90 wt%, 70-80 wt%, 80-99 wt%, 80-95 wt%, 80-90 wt%, 90-99 wt%, 90-95 wt%, or 95-99 wt%of the STE.
  • In certain preferred embodiments, the sweetener or flavoring composition comprises the glycosylation product of a STE having a RU content of at least 1%, at least 2%, at least 5%, at least 10%, at least 15%, at least 20%, at least 25%, at least 30%, at least 35%, at least 40%, at least 45%, at least 50%, at least 55%, at least 60%, at least 65%, at least 70%, at least 75%, at least 80%, at least 85%, at least 90%, at least 95%, at least 90%, or any range defined by any pair of these integers.
  • In some embodiments, the sweetener or flavoring composition comprises one or more glycosylated flavonoid glycosides, glycosylated isoflavone glycosides, glycosylated saponin glycosides, glycosylated phenol glycosides, glycosylated cynophore glycosides, glycosylated anthraquinone glycosides, glycosylated cardiac glycosides, glycosylated bitter glycosides, glycosylated coumarin glycosides, or glycosylated sulfur glycosides.
  • In some embodiments, the GSTE/GSTC containing sweetener or flavoring composition further comprises a glycosylated stevia extract. In some embodiments, the the GSTE/GSTC containing sweetener or flavoring composition further comprises a one or more glycosylated non-sweet tea steviol glycosides. In some embodiments, the the GSTE/GSTC containing sweetener or flavoring composition further comprises thaumatin.
  • (1) Preparation of glycosylated products
  • Glycosyltransferases, Glycosyl Hydrolases and Transglycosidases
  • The glycosylated products described in the present application, such as GSTEs, GSTCs, GSEs, GSGs, GSCs, GMGs, GMFEs and GMFCs can be formed by exogenous glycosylation reactions in the presence of a glycosyltransferase.
  • As used herein, a “glycosyltransferase” refers to an enzyme that catalyzes the formation of a glycosidic linkage to form a glycoside. A glycoside is any molecule in which a sugar group is bonded through its anomeric carbon to another group via a glycosidic bond. Glycosides can be linked by an O- (an O-glycoside) , N- (a glycosylamine) , S- (a thioglycoside) , or C- (a C-glycoside) glycosidic bond. The sugar group is known as the glycone and the non-sugar group is known as the aglycone. The glycone can be part of a single sugar group (monosaccharide) or several sugar groups (oligosaccharide) . A glycosyltransferase according to the present application further embraces “glycosyltransferase variants” engineered for enhanced activities.
  • Glycosyltransferases utilize “activated” sugar phosphates as glycosyl donors, and catalyze glycosyl group transfer to an acceptor molecule comprising a nucleophilic group, usually an alcohol. A retaining glycosyltransferases is one which transfers a sugar residue with the retention of anomeric configuration. Retaining glycosyltransferase enzymes retain the stereochemistry of the donor glycosidic linkage after transfer to an acceptor molecule. An inverting glycosyltransferase, on the other hand, is one which transfers a sugar residue with the inversion of anomeric configuration. Glycosyltransferases are classified based on amino acid sequence similarities. Glycosyltransferases are classified by the Nomenclature Committee of the International Union of Biochemistry and Molecular Biology (NC-IUBMB) in the enzyme class of EC 2.4.1 on the basis of the reaction catalyzed and the specificity.
  • Glycosyltransferases can utilize a range of donor substrates. Based on the type of donor sugar transferred, these enzymes are grouped into families based on sequence similarities. Exemplary glyosyltransferases include glucanotransferases, N-acetylglucosaminyltransferases, N-acetylgalactosaminyltransferases, fucosyltransferases, mannosyltransferases, galactosyltransferases, sialyltransferases sialyltransferases, galactosyltransferases, fucosyltransferase, Leloir glycosyltransferases, non-Leloir glycosyltransferases, and other glycosyltransferases in the enzyme class of EC 2.4.1. The Carbohydrate-Active Enzymes database (CAZy) provides a continuously updated list of the glycosyltransferase families.
  • In some embodiments, the glycosylation products described in the present application, such as GSTEs, GSTCs, are formed from a reaction mixture comprising an  exogenous glycosyltransferase classified as an EC 2.4.1 enzyme, including but not limited to members selected from the group consisting of cyclomaltodextrin glucanotransferase (CGTase; EC 2.4.1.19) , amylosucrase (EC 2.4.1.4) , dextransucrase (EC 2.4.1.5) , amylomaltase, sucrose: sucrose fructosyltransferase (EC 2.4.1.99) , 4-α-glucanotransferase (EC 2.4.1.25) , lactose synthase (EC 2.4.1.22) , sucrose-1, 6-α-glucan 3 (6) -α-glucosyltransferase, maltose synthase (EC 2.4.1.139) , alternasucrase (EC 2.4.1.140) , including variants thereof.
  • Cyclomaltodextrin glucanotransferase, also known as CGTase, is an enzyme assigned with enzyme classification number EC 2.4.1.19, which is capable of catalyzing the hydrolysis and formation of (1→4) -α-D-glucosidic bonds, and in particular the formation of cyclic maltodextrins from polysaccharides as well as the disproportionation of linear oligosaccharides.
  • Dextransucrase is an enzyme assigned with enzyme classification number EC 2.4.1.5, and is also known as sucrose 6-glucosyltransferase, SGE, CEP, sucrose-1, 6-α-glucan glucosyltransferase or sucrose: 1, 6-α-D-glucan 6-α-D-glucosyltransferase. Dextransucrases are capable of catalyzing the reaction: sucrose + [ (1→6) -α-D-glucosyl]  n = D-fructose + [ (1→6) -α-D-glucosyl]  n+1. In addition, a glucosyltransferase (DsrE) from Leuconostoc mesenteroides, NRRL B-1299 has a second catalytic domain ( "CD2" ) capable of adding alpha-1, 2 branching to dextrans (U.S. Pat. Nos. 7,439,049 and 5,141,858; U.S. Patent Appl. Publ. No. 2009-0123448; Bozonnet et al., J. Bacteria 184: 5753-5761, 2002) .
  • Glycosyltransferases and other glycosylating enzymes for use in the present application may be derived from any source and may be used in a purified form, in an enriched concentrate or as a crude enzyme preparation.
  • In some embodiments, the glycosylation reaction is carried out by glycosylating an aglycone or glycoside substrate using e.g., a nucleotide sugar donor (e.g., sugar mono-or diphosphonucleotide) or “Leloir donor” in conjunction with a “Leloir glycosyltransferase” (after Nobel prize winner, Luis Leloir) that catalyzes the transfer of a monosaccharide unit from the nucleotide-sugar ( “glycosyl donor’ ) to a “glycosyl acceptor” , typically a hydroxyl group in an aglycone or glycoside substrate.
  • Accordingly, in some embodiments the glycosylation product of the present application is formed from a reaction mixture comprising a nucleotide sugar.
  • In certain embodiments, the glycosylation reactions may involve the use of a specific Leloir glycosyltransferase in conjunction with a wide range of sugar nucleotides donors, including e.g., UDP-glucose, GDP-glucose, ADP-glucose, CDP-glucose, TDP-glucose or IDT-glucose in combination with a glucose-dependent glycosyltransferase (GDP-glycosyltransferases; GGTs) , ADP-glucose-dependent glycosyltransferase (ADP-glycosyltransferases; AGTs) , CDP-glucose-dependent glycosyltransferase (CDP-glycosyltransferases; CGTs) , TDP-glucose-dependent glycosyltransferase (TDP-glycosyltransferases; TGTs) or IDP-glucose-dependent glycosyltransferase (IDP-glycosyltransferases; IGTs) , respectively.
  • In particular embodiments, the exogenous glycosylation reaction is carried out using an exogenous Leloir-type UDP-glycosyltransferase enzyme of the classification EC 2.4.1.17, which catalyzes the transfer of glucose from UDP-α-D-glucuronate (also known as UDP-glucose) to an acceptor, releasing UDP and forming acceptor β-D-glucuronoside. In some embodiments, the glycosyltransferases include, but are not limited to, enzymes classified in the GT1 family. In certain preferred embodiment, the glycosylation reaction is catalyzed by an exogenous UDP-glucose-dependent glycosyltransferase. In some embodiments, the glycosylaton reaction is catalyzed by a glycosyltransferase capable of transferring a non-glucose nonosaccharide, such as fructose, galactose, ribose, arabinose, xylose, mannose, psicose, fucose and rhamnose, and derivative thereof, to the receipient.
  • U.S. Patent No. 9,567,619 describes several UDP-dependent glycosyltransferases that can be used to transfer monosaccharides to rubusoside, including UGT76G1 UDP glycosyltransferase, HV1 UDP-glycosyltransferase, and EUGT11, a UDP glycosyltransferase-sucrose synthase fusion enzyme. The EUGT11 fusion enzyme contains a uridine diphospho glycosyltransferase domain coupled to a sucrose synthase domain and can exhibit 1, 2-β glycosidic linkage and 1, 6-β glycosidic linkage enzymatic activities, as well as sucrose synthase activity. Of the foregoing enzymes, UGT76G1 UDP glycosyltransferase contains a 1, 3-O-glucose glycosylation activity which can transfer a second glucose moiety to the C-3′ of 13-O-glucose ofrubusoside to produce rebaudioside G ( “Reb G” ) ; HV1 UDP-glycosyltransferase contains a 1, 2-O-glucose glycosylation activity which can transfer a second  glucoside moiety to the C-2′ of 19-O-glucose of rubusoside to produce rebaudioside KA ( “Reb KA”) ; and the EUGT11 fusion enzyme contains a 1, 2-O-glucose glycosylation activity which transfers a second glucose moiety to the C-2′ of 19-O-glucose ofrubusoside to produce rebaudioside KA or transfer a second glucose moiety to the C-2′ of 13-O-glucose ofrubusoside to produce stevioside. In addition, HV1 and EUGT11 can transfer a second sugar moiety to the C-2′ of 19-O-glucose of rebaudioside G to produce rebaudioside V ( “Reb V" ) and can additionally transfer a second glucose moiety to the C-2′ of 13-O-glucose of rebaudioside KA to produce rebaudioside E ( “Reb E” ) . Furthermore, when used singly or in combination, these enzymes can be used to generate a variety of steviol glycosides known to be present in Stevia rebaudiana, including rebaudioisde D ( “Reb D” ) and rebaudioside M ( “Reb M” ) .
  • In some embodiments, Monosaccharides that can be transferred to a saccharide or nonsaccharide acceptor include, but are not limited to glucose, fructose, galactose, ribose, arabinose, xylose, mannose, psicose, fucose and rhamnose, and derivative thereof, as well as acidic sugars, such as sialic acid, glucuronic acid and galacturonic acid.
  • In some embodiments, glycosylation of RU and/or other STCs is driven by an exogenous glycosyl hydrolase or glycosidase from the enzyme class of EC 3.2.1. GHs normally cleave a glycosidic bond. However, they can be used to form glycosides by selecting conditions that favor synthesis via reverse hydrolysis. Reverse hydrolysis is frequently applied e.g., in the synthesis of aliphatic alkylmonoglucosides.
  • Glycosyl hydrolases have a wide range of donor substrates employing usually monosaccharides, oligosaccharides or/and engineered substrates (i.e., substrates carrying various functional groups) . They often display activity towards a large variety of carbohydrate and non-carbohydrate acceptors. Glycosidases usually catalyze the hydrolysis of glycosidic linkages with either retention or inversion of stereochemical configuration in the product.
  • In some embodiments, the glycosylation products of the present application, such as GSTEs, GSTCs, are formed from a reaction mixture comprising an exogenous glycosyl hydrolase classified as an EC 3.2.1 enzyme, including but not limited to alpha-glucosidase, beta-glucosidase and beta-fructofuranosidase.
  • Exemplary glycosyl hydrolases for use in the present application include, but are not limited to a-amylases (EC 3.2.1.1) , α-glucosidases (EC 3.2.1.20) , β-glucosidases (EC 3.2.1.21) , α-galactosidases (EC 3.2.1.22) , β-galactosidases (EC 3.2.1.23) , α-mannosidase (EC 3.2.1.24) , β-mannosidase (EC 3.2.1.25) , β-fructofuranosidase (EC 3.2.1.26) , amylo-1, 6-glucosidases (EC 3.2.1.33) , β-D-fucosidases (EC 3.2.1.38) , α-L-rhamnosidases (EC 3.21.40) , glucan 1, 6-α-glucosidases (EC 3.2.70) , and variants thereof.
  • In some embodiments, the glycosylation products of the present application are formed using a class of glycoside hydrolases or glycosyltransferases known as “transglycosylases. ” As used herein, the term “transglycosylase” and “transglycosidase” (TG) are used interchangeably with reference to a glycoside hydrolase (GH) or glycosyltransferase (GT) enzyme capable of transferring a monosaccharide moiety from one molecule to another. Thus, a GH can catalyse the formation of a new glycosidic bond either by transglycosylation or by reverse hydrolysis (i.e., condensation) .
  • The acceptor for transglycosylase reaction acceptor can be saccharide acceptor or a nonsaccharide acceptor. Thus, a transglycosidase can transfer a monosaccharide moiety to a diverse set of aglycones, including e.g., nonsaccharide acceptors, such as aromatic and aliphatic alcohols. Transglycosidases can transfer a wide variety of monosaccharides (D-or L-configurations) to saccharide acceptors, including glycosides, as well as nonsaccharide acceptors, including a wide variety of flavonoid aglycones, such as naringenin, quercetin, hesperetin.
  • Monosaccharides that can be transferred to a saccharide or nonsaccharide acceptor include, but are not limited to glucose, fructose, galactose, ribose, arabinose, xylose, mannose, psicose, fucose and rhamnose, and derivative thereof, as well as acidic sugars, such as sialic acid, glucuronic acid and galacturonic acid. The term “transglucosidase” is used when the monosaccharide moiety is a glucose moiety.
  • Transglycosidases include GHs or GTs from the enzyme classes of EC 3.2.1 or 2.4.1, respectively. In spite of the inclusion of certain glycosyltransferases as transglycosidases, TGs are classified into various GH families on the basis of sequence similarity. A large number of retaining glycosidases catalyze both hydrolysis and transglycosylation reactions. In particular, these enzymes catalyze the intra-or intermolecular substitution of the anomeric position of a glycoside. Under kinetically controlled reactions, retaining glycosidases can be used to form  glycosidic linkages using a glycosyl donor activated by a good anomeric leaving group (e.g., nitrophenyl glycoside) . In contrast, the thermodynamically controlled reverse hydrolysis uses high concentrations of free sugars.
  • Transglycosidases corresponding to any of the GH families with notable transglycosylase activity may be used in the present application, and may include the use of e.g., members of the GH2 family, including LacZ β-galactosidase, which converts lactose to allolactose; GH13 family, which includes cyclodextran glucanotransferases that convert linear amylose to cyclodextrins, glycogen debranching enzyme, which transfers three glucose residues from the four-residue glycogen branch to a nearby branch, and trehalose synthase, which catalyzes the interconversion of maltose and trehalose; GH16 family, including xyloglucan endotransglycosylases, which cuts and rejoins xyloglucan chains in the plant cell wall; GH31, for example α-transglucosidases, which catalyze the transfer of individual glucosyl residues between α- (1→4) -glucans; GH70 family, for example glucansucrases, which catalyse the synthesis of high molecular weight glucans, from sucrose; GH77 family, for examples amylomaltase, which catalyzes the synthesis of maltodextrins from maltose; and the GH23, GH102, GH103, and GH104 families, which include lytic transglycosylases that convert peptidoglycan to 1, 6-anhydrosugars.
  • In one embodiment, the glycosyltransferase is a transglucosylase from the glycoside hydrolase 70 (GH70) family. GH70 enzymes are transglucosylases produced by lactic acid bacteria from, e.g., Streptococcus, Leuconostoc, Weisella or Lactobacillus genera. Together with the families GH13 and GH77 enzymes, they form the clan GH-H. Most of the enzymes classified in this family use sucrose as the D-glucopyranosyl donor to synthesize α-D-glucans of high molecular mass (＞10 6 Da) with the concomitant release of D-fructose. They are also referred to as glucosyltransferases or glucansucrases.
  • A wide range of α-D-glucans, varying in size, structure, degree of branching and spatial arrangements can thus be produced by GH70 family members. For example, GH70 glucansucrases can transfer D-glucosyl units from sucrose onto hydroxyl acceptor groups. Glucansucrases catalyze the formation of linear as well as branched α-D-glucan chains with various types of glycosidic linkages, namely α-1, 2; α-1, 3; α-1, 4; and/or α-1, 6.
  • In addition, sucrose analogues such as α-D-glucopyranosyl fluoride, p-nitrophenyl α-D-glucopyranoside, α-D-glucopyranosyl α-L-sorofuranoside and lactulosucrose can be utilized as D-glucopyranosyl donors. A large variety of acceptors may be recognized by glucansucrases, including carbohydrates, alcohols, polyols or flavonoids to yield oligosaccharides or gluco-conjugates.
  • Exemplary glucansucrases for use in the present application include e.g., dextransucrase (sucrose: 1, 6-α-D-glucosyltransferase; EC 2.4.1.5) , altemansucrase (sucrose: 1, 6 (1, 3) -α-D-glucan-6 (3) -α-D-glucosyltransferase, EC 2.4.1.140) , mutansucrase (sucrose: 1, 3-α-D-glucan-3-α-D-glucosyltransferase; EC 2.4.1.125) , and reuteransucrase (sucrose: 1, 4 (6-α-D-glucan-4 (6) -α-D-glucosyltransferase; EC 2.4.1. -) . The structure of the resultant glucosylated product is dependent upon the enzyme specificity.
  • In some embodiments, a fructosyltransferase may be used to catalyze the transfer of one or more fructose units, optionally comprising terminal glucose, of the following sequence: (Fru) n-Glc consisting of one or more of: β 2, 1, β 2, 6, α 1, 2 and β-1, 2 glycosidic bonds, wherein n typically is 3-10. Variants include Inulin type β-1, 2 and Levan type β-2, 6 linkages between fructosyl units in the main chain. Exemplary fructosytransferase for use in the present application include e.g., β-fructofuranosidase (EC 3.2.1.26) , inulosucrase (EC 2.4.1.9) levansucrase (EC 2.4.1.10) , or endoinulinase.
  • In some embodiments, a galactosyltransferase or β-galactosidase may be used to catalyze the transfer of multiple saccharide units, in which one of the units is a terminal glucose and the remaining units are galactose and disaccharides comprising two units of galactose. In certain embodiments, the resulting structure includes a mixture of galactopyranosyl oligomers (DP=3-8) linked mostly by β- (1, 4) or β- (1, 6) bonds, although low proportions of β- (1, 2) or β- (1, 3) linkages may also be present. Terminal glucosyl residues are linked by β- (1, 4) bonds to galactosyl units. These structures may be synthesized by the reverse action of β-galactosidases (EC 3.2.1.23) on lactose at relatively high concentrations of lactose.
  • In some embodiments, the transglycosidase is an enzyme having trans-fucosidase, trans-sialidase, trans-lacto-N-biosidase and/or trans-N-acetyllactosaminidase activity.
  • In some embodiments, the glycosylation reactions may utilize a combination of any of glycosyltransferases described herein in combination with any one of the glycosyl  hydrolases or transglycosidases described herein. In these reactions, the transglycosylase and the glycosyl hydrolase or translygosidase may be present in a range of ratios (w/w) , wherein the transglycosylase/glycosyl hydrolase ratio (w/w) ranges from 100∶1, 80∶1, 60∶1, 40∶1, 30∶1, 25∶1, 20∶1, 15∶1, 10∶1, 9∶1, 8∶1, 7∶1, 6∶1, 5∶1, 4∶1, 3∶1, 2∶1, 1∶1, 1∶2, 1∶3, 1∶4, 1∶5, 1∶6, 1∶7, 1∶8, 1∶9, 1∶10, 1∶15, 1∶20, 1∶25, 1∶30, 1∶40, 1∶50, 1∶60, 1∶80, 1∶100, or any ratio derived from any two of the aforementioned integers.
  • (2) Dextrins
  • In embodiments comprising GSGs, the composition typically comprises one or more dextrins remaining after the glycosylation reaction. Dextrins are hydrolysate products of starch that provide a substrate for glycosylation so as to produce a more cost-effective SG/GSG composition having improved solubility and/or an improved taste profile.
  • In some embodiments, the dextrins are produced from a starch. The starches used may be the naturally occurring starches, such as potato starch, waxy potato starch, corn starch, rice starch, pea starch, banana starch, horse chestnut starch, wheat starch, amylose, amylomaize, amylopectin, pullulan, lactose, and combinations thereof. However, it is also possible to use modified starches, for example pregelatinized starch, thin-boiling starch, oxidized starch, citrate starch, high-fructose corn syrup, hydrogenated starch hydrosylate, hydroxyethyl starch, hydroxypropyl distarch phosphate, maltitol, acetate starch, acetylated distarch adipate, starch ethers, starch esters, starch phosphates, phosphated distarch phosphate, and pentastarch. There is in principle no restriction in the selection of the starch. The starch may have, for example, low viscosity, moderate viscosity or high viscosity, and be cationic or anionic, and cold water-soluble or hot water-soluble.
  • Dextrins may be linear or circular. The dextrin may be selected from the group of tapioca dextrin, potato dextrin, corn dextrin, yellow dextrin, white dextrin, borax dextrin, maltodextrin and cyclodextrins (CD) , such as alpha, beta, and/or gamma cyclodextrin. In certain preferred embodiments, the dextrin is a CD or tapioca dextrin. CDs are a family of compounds made up of sugar molecules bound together in a ring, cyclic oligosaccharides. They are composed of 5 or more alpha-D-glucopyranoside units linked 1-＞4, as in amylose. CDs are also referred to as cycloamyloses.
  • Dextrins can make up 1 wt %, 2 wt %, 3 wt %, 4 wt %, 5 wt %, 6 wt %, 7 wt %, 8wt %, 9wt %, 10wt %, 11 wt %, 12 wt %, 13 wt %, 14 wt %, 15 wt %, 16 wt %, 17 wt %, 18 wt %, 19 wt %, 20 wt %, 21 wt %, 22 wt %, 23 wt %, 24 wt %, 25 wt %, 26 wt %, 27 wt %, 28 wt %, 29 wt %, 30 wt %, 31 wt %, 32 wt %, 33 wt %, 34 wt %, 35 wt %, 36 wt %, 37 wt %, 38 wt %, 39 wt %, 40 wt %, 41 wt %, 42 wt %, 43 wt %, 44 wt %, 45 wt %, 46 wt %, 47 wt %, 48 wt %, 49 wt %, 50 wt %, 51 wt %, 52 wt %, 53 wt %, 54 wt %, 55 wt %, 56 wt %, 57 wt %, 58 wt %, 59 wt %, 60 wt %, 61 wt %, 62 wt %, 63 wt %, 64 wt %, 65 wt %, 66 wt %, 67 wt %, 68 wt %, 69 wt %, 70 wt %, 71 wt %, 72 wt %, 73 wt %, 74 wt %, 75 wt %, 76 wt %, 77 wt %, 78 wt %, 79 wt %, 80 wt %, 81 wt %, 82 wt %, 83 wt %, 84 wt %, 85 wt %, 86 wt %, 87 wt %, 88 wt %, 89 wt %, 90 wt %, 91 wt %, 92 wt %, 93 wt %, 94 wt %, 95 wt %, 96 wt %, 97 wt %, 98 wt %or 99 wt %, and all ranges between 1 and 99 wt %, for example from about 1 wt %to about 99 wt %, from about 1 wt %to about 98 wt %, from about 1 wt %to about 97 wt %, from about 1 wt %to about 95 wt %, from about 1 wt %to about 90 wt %, from about 1 wt %to about 80 wt %, from about 1 wt %to about 70 wt %, from about 1 wt %to about 60 wt %, from about 1 wt %to about 50 wt %, from about 1 wt %to about 40 wt %, from about 1 wt %to about 30 wt %, from about 1 wt %to about 20 wt %, from about 1 wt %to about 10 wt %, from about 1 wt %to about 5 wt %, from about 2 wt %to about 99 wt %, from about 2 wt %to about 98 wt %, from about 2 wt %to about 97 wt %, from about 2 wt %to about 95 wt %, from about 2 wt %to about 90 wt %, from about 2 wt %to about 80 wt %, from about 2 wt %to about 70 wt %, from about 2 wt %to about 60 wt %, from about 2 wt %to about 50 wt %, from about 2 wt %to about 40 wt %, from about 2 wt %to about 30 wt %, from about 2 wt %to about 20 wt %, from about 2 wt %to about 10 wt %, from about 2 wt %to about 5 wt %, from about 3 wt %to about 99 wt %, from about 3 wt %to about 98 wt %, from about 3 wt %to about 97 wt %, from about 3 wt %to about 95 wt %, from about 3 wt %to about 90 wt %, from about 3 wt %to about 80 wt %, from about 3 wt %to about 70 wt %, from about 3 wt %to about 60 wt %, from about 3 wt %to about 50 wt %, from about 3 wt %to about 40 wt %, from about 3 wt %to about 30 wt %, from about 3 wt %to about 20 wt %, from about 3 wt %to about 10 wt %, from about 3 wt %to about 5 wt %, from about 5 wt %to about 99 wt %, from about 5 wt %to about 98 wt %, from about 5 wt %to about 97 wt %, from about 5 wt %to about 95 wt %, from about 5 wt %to about 90 wt %, from about 5 wt %to about 80 wt %, from about 5 wt %to about 70 wt %, from about 5 wt %to about 60 wt %, from about 5 wt %to about 50 wt %, from about 5 wt %to about  40 wt %, from about 5 wt %to about 30 wt %, from about 5 wt %to about 20 wt %, from about 5 wt %to about 10 wt %, from about 10 wt %to about 99 wt %, from about 10 wt %to about 98 wt %, from about 10 wt %to about 97 wt %, from about 10 wt %to about 95 wt %, from about 10 wt %to about 90 wt %, from about 10 wt %to about 80 wt %, from about 10 wt %to about 70 wt %, from about 10 wt %to about 60 wt %, from about 10 wt %to about 50 wt %, from about 10 wt %to about 40%w/wt, from about 10 wt %to about 30 wt %, and from about 10 wt %to about 20 wt %, of the composition.
  • In some embodiments, the composition of the present application comprises (1) glycosylated stevia glycosides or glycosylated sweet tea extract and (2) maltodextrin, wherein the total amount of oligosaccharides with 3-5 glucose units (DP 3-5) is less than 1 wt %, less than 0.8 wt %, less than 0.7 wt %, and wherein the total total amount of oligosaccharides with more than 5 glucose units (DP ＞5) is less than 0.5 wt %.
  • Testing methods for determination of dextrins may utilize any method well known in the art, such as HPLC. For example, an HPLC device manufactured by Shimadzu with a refractometric detector and a column recommended for assaying oligosaccharides (i.e., Luna 5 micrometer NH2 100A 250 x 4.60 mm; Phenomenex) may be used to assay maltodextrins. A 65∶35 acetonitrile-water system was used as an eluent, flow rate 3 ml/min, analysis time around 10 min, temperature 40℃. Maltodextrin contents (%) can be determined based on comparisons of the peak areas obtained in the examined samples with those from a reference solution (external standard method) .
  • In some embodiments, the compositions of the present application disclosed herein may be solubilized in an aqueous solution. The aqueous solution can include water and/or an alcohol, such as one or more of methanol, ethanol, propanol, isopropanol, n-butanol, isobutanol, sec-butanol, tert-butanol, n-pentanol, isopentanol, neopentanol, or combinations thereof.
  • The water alcohol solution can be less than 60%alcohol, less than 50%alcohol, less than 40%alcohol, less than 30%alcohol, less than 20%alcohol, less than 10%alcohol, less than 5%alcohol, less than 2%alcohol, or less than 1%alcohol by volume.
  • (3) Reaction Conditions
  • A glycosylating enzyme may be dissolved in the reaction mixture or immobilized on a solid support which is contacted with the reaction mixture. If the enzyme is immobilized, it may be attached to an inert carrier. Suitable carrier materials are known in the art. Examples for suitable carrier materials are clays, clay minerals such as kaolinite, diatomeceous earth, perlite, silica, alumina, sodium carbonate, calcium carbonate, cellulose powder, anion exchanger materials, synthetic polymers, such as polystyrene, acrylic resins, phenol formaldehyde resins, polyurethanes and polyolefins, such as polyethylene and polypropylene. For preparing carrier-bound enzymes the carrier materials usually are used in the form of fine powders, wherein porous forms are preferred. The particle size of the carrier material usually does not exceed 5 mm, in particular 2 mm. Further, suitable carrier materials are calcium alginate and carrageenan. Enzymes may directly be linked by glutaraldehyde. A wide range of immobilization methods are known in the art. Ratio of reactants can be adjusted based on the desired performance of the final product. The temperature of the glycosylation reaction can be in the range of 1-100℃, preferably 40-80℃, more preferably 50-70℃.
  • The enzymatically catalyzed reaction can be carried out batch wise, semi-batch wise or continuously. Reactants can be supplied at the start of reaction or can be supplied subsequently, either semi-continuously or continuously. The catalytic amount of glycosidase or glycosyltransferase required for the method of the invention depends on the reaction conditions, such as temperature, solvents and amount of substrate.
  • The reaction can be performed in aqueous media such as buffer. A buffer adjusts the pH of the reaction mixture to a value suitable for effective enzymatic catalysis. Typically the pH is in the range of about pH 4 to about pH 9, for example of about pH 5 to about pH 7. Suitable buffers comprise, but are not limited to, sodium acetate, tris (hydroxymethyl) aminomethane ( “Tris” ) and phosphate buffers.
  • Optionally, the reaction may take place in the presence of a solvent mixture of water and a water miscible organic solvent at a weight ratio of water to organic solvent of from 0.1∶1 to 9∶1, for example from 1∶1 to 3∶1. The organic solvent is no primary or secondary alcohol and, accordingly, is non-reactive towards the polysaccharide. Suitable organic solvents comprise alkanones, alkylnitriles, tertiary alcohols and cyclic ethers, and mixtures thereof, for  example acetone, acetonitrile, t-pentanol, t-butanol, 1, 4-dioxane and tetrahydrofuran, and mixtures thereof. Generally, the use of organic solvents is not preferred.
  • (4) Glycosylation Products
  • Glycosylation products, such as GSGs, GSEs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, may include both reacted and unreacted components from the starting materials (i.e., the mixture of materials before the initiation of the glycosylation reaction) .
  • In some embodiments, the glycosylated component (e.g., glycosylated RU) or components are present in the glycosylation product composition (or glycosylate) in a range between 0.00001-99.5 wt%, 0.0001-99.5 wt%, 0.001-99.5 wt%, 0.01-99.5 wt%, 0.01-0.02 wt%, 0.01-0.05 wt%, 0.01-0.07 wt%, 0.01-0.1 wt%, 0.01-0.2 wt%, 0.01-0.5 wt%, 0.01-0.7 wt%, 0.01-1 wt%, 0.01-2 wt%, 0.01-5 wt%, 0.01-7 wt%, 0.01-10 wt%, 0.01-20 wt%, 0.01-50 wt%, 0.01-70 wt%, 0.01-99 wt%, 0.02-0.05 wt%, 0.02-0.07 wt%, 0.02-0.1 wt%, 0.02-0.2 wt%, 0.02-0.5 wt%, 0.02-0.7 wt%, 0.02-1 wt%, 0.02-2 wt%, 0.02-5 wt%, 0.02-7 wt%, 0.02-10 wt%, 0.02-20 wt%, 0.02-50 wt%, 0.02-70 wt%, 0.02-99 wt%, 0.05-0.07 wt%, 0.05-0.1 wt%, 0.05-0.2 wt%, 0.05-0.5 wt%, 0.05-0.7 wt%, 0.05-1 wt%, 0.05-2 wt%, 0.05-5 wt%, 0.05-7 wt%, 0.05-10 wt%, 0.05-20 wt%, 0.05-50 wt%, 0.05-70 wt%, 0.05-99 wt%, 0.07-0.1 wt%, 0.07-0.2 wt%, 0.07-0.5 wt%, 0.07-0.7 wt%, 0.07-1 wt%, 0.07-2 wt%, 0.07-5 wt%, 0.07-7 wt%, 0.07-10 wt%, 0.07-20 wt%, 0.07-50 wt%, 0.07-70 wt%, 0.07-99 wt%, 0.1-0.2 wt%, 0.1-0.5 wt%, 0.1-0.7 wt%, 0.1-1 wt%, 0.1-2 wt%, 0.1-5 wt%, 0.1-7 wt%, 0.1-10 wt%, 0.1-20 wt%, 0.1-50 wt%, 0.1-70 wt%, 0.1-99 wt%, 0.2-0.5 wt%, 0.2-0.7 wt%, 0.2-1 wt%, 0.2-2 wt%, 0.2-5 wt%, 0.2-7 wt%, 0.2-10 wt%, 0.2-20 wt%, 0.2-50 wt%, 0.2-70 wt%, 0.2-99 wt%, 0.5-0.7 wt%, 0.5-1 wt%, 0.5-2 wt%, 0.5-5 wt%, 0.5-7 wt%, 0.5-10 wt%, 0.5-20 wt%, 0.5-50 wt%, 0.5-70 wt%, 0.5-99 wt%, 0.7-1 wt%, 0.7-2 wt%, 0.7-5 wt%, 0.7-7 wt%, 0.7-10 wt%, 0.7-20 wt%, 0.7-50 wt%, 0.7-70 wt%, 0.7-99 wt%, 1-2 wt%, 1-5 wt%, 1-7 wt%, 1-10 wt%, 1-20 wt%, 1-50 wt%, 1-70 wt%, 1-99 wt%, 2-5 wt%, 2-7 wt%, 2-10 wt%, 2-20 wt%, 2-50 wt%, 2-70 wt%, 2-99 wt%, 5-7 wt%, 5-10 wt%, 5-20 wt%, 5-50 wt%, 5-70 wt%, 5-99 wt%, 7-10 wt%, 7-20 wt%, 7-50 wt%, 7-70 wt%, 7-99 wt%, 10-20 wt%, 10-50 wt%, 10-70 wt%, 10-99 wt%, 20-50 wt%, 20-70 wt%, 20-99 wt%, 50-70 wt%, 50-99 wt%, or 70-99 wt%of the glycosylation product.
  • In some embodiments, the glycosylated components are present in the glycosylation product composition in an amount greater than 0.01 wt%, 0.1 wt%, 1 wt%, 2 wt%, 5 wt%, 10 wt%, 20 wt%, 30 wt%, 40 wt%, 50 wt%, 60 wt%, 70 wt%, 80 wt%, 90 wt%, 95 wt%, or 99 wt%.
  • In some embodiments, the glycosylation product composition comprise glycosylated RU in an amount ranging 1-5 wt%, 1-10 wt%, 1-15 wt%, 1-20 wt%, 1-30 wt %, 1-40 wt %, 1-50 wt%, 1-60 wt %, 1-70 wt%, 1-80 wt%, 1-90 wt%, 1-95 wt%, 1-99 wt%, 5-10 wt%, 5-15 wt%, 5-20 wt%, 5-30 wt %, 5-40 wt %, 5-50 wt%, 5-60 wt %, 5-70 wt%, 5-80 wt%, 5-90 wt%, 5-95 wt%, 5-99 wt%, 10-15 wt%, 10-20 wt%, 10-30 wt %, 10-40 wt %, 10-50 wt%, 10-60 wt %, 10-70 wt%, 10-80 wt%, 10-90 wt%, 10-95 wt%, 10-99 wt%, 15-20 wt%, 15-30 wt %, 15-40 wt %, 15-50 wt%, 15-60 wt %, 15-70 wt%, 15-80 wt%, 15-90 wt%, 15-95 wt%, 15-99 wt%, 20-30 wt %, 20-40 wt %, 20-50 wt%, 20-60 wt %, 20-70 wt%, 20-80 wt%, 20-90 wt%, 20-95 wt%, 20-99 wt%, 30-40 wt %, 30-50 wt%, 30-60 wt %, 30-70 wt%, 30-80 wt%, 30-90 wt%, 30-95 wt%, 30-99 wt%, 40-50 wt%, 40-60 wt %, 40-70 wt%, 40-80 wt%, 40-90 wt%, 40-95 wt%, 40-99 wt%, 50-60 wt %, 50-70 wt%, 50-80 wt%, 50-90 wt%, 50-95 wt%, 50-99 wt%, 60-70 wt%, 60-80 wt%, 60-90 wt%, 60-95 wt%, 60-99 wt%, 70-80 wt%, 70-90 wt%, 70-95 wt%, 70-99 wt%, 80-90 wt%, 80-95 wt%, 80-99 wt%, 90-95 wt%, 90-99 wt%or 95-99 wt%of the glycosylation products.
  • In some embodiments, the glycosylation product composition comprises unreacted sugar donors such as dextrins in an amount of greater than zero but less than 30%, 20%, 15%, 10%, 8%, 5%, 4%, 3%, 2%, 1%, 0.5%, 0.2%, 0.1%, 0.05%, 0.02%, 0.01%, 0.005%, 0.002%, or 0.001% (w/w) of the glycosylation product.
  • In a related aspect, the present application provides a method for preparing low dextrin glycosylation reaction products. In one embodiment, a methof for preparing low dextrin glycosylates includes the steps of: (a) dissolving glycosylated products; (b) adsorbing the glycosylated products to a suitable resin to the point of saturation; (c) washing the product-bound resin with an organic solvent and/or aqueous organic solvent at a concentration sufficient to elute the products (or desorb the resin therefrom) ; (d) collecting the desorbed glycosylation products, which can be further treated with resins or active carbon for discoloration and/or odor removal; and (e) drying the desorbed glycosylation products.
  • This method may be used for all types of glycosylates, including those containing GSGs, GSEs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs. Exemplary methods for preparing low dextrin glycosylation reaction products are further described in Example 22.
  • In some embodiments, the glycosylation products, such as GSGs, GSEs, GSTEs, GSTCs include glycosylated RU. The glycosylated RU may comprise RU molecules with different lavel of glycosylation, including but are not limited to, glycosylated RU molecules that contain a RU backbone (as described in Table 1 with a molecular weight of 641) with 1-50 additional monosaccharide units that are added to the RU backbone during a man-made glycosylation reaction. In some embodiments, the additional monosaccharide units are glucose units. In some embodiments, the additional monosaccharide units are non-glucose units, such as fructose, xylose and galactose units. In some embodiments, the additional monosaccharide units are a mixture of glucose units and non-glucose units.
  • In some embodiments, the composition of the present application comprises (1) glycosylated stevia glycosides or glycosylated sweet tea extract and (2) maltodextrin, wherein the total amount of oligosaccharides with 3-5 glucose units (DP 3-5) is less than 2 wt %, less than 1.5 wt %, less than 1.2 wt %, less than 1 wt %, less than 0.8 wt %, less than 0.7 wt %, less than 0.6 wt %, or less than 0.5 wt %, and wherein the total total amount of oligosaccharides with more than 5 glucose units (DP ＞5) is less than 0.5 wt %, less than 0.4 wt %, less than 0.3 wt %, less than 0.2 wt %, or less than 0.1 wt %.
  • In some embodiments, the the composition of the present application comprises (1) glycosylated stevia glycosides or glycosylated sweet tea extract and (2) maltodextrin, wherein the total amount of oligosaccharides with 3-5 glucose units (DP 3-5) is in the range of 0.0001-2 wt %, 0.0001-1.5 wt %, 0.0001-1.2 wt %, 0.0001-1 wt %, 0.0001-0.8 wt %, 0.0001-0.7 wt %, 0.0001-0.6 wt %, 0.0001-0.5 wt %, 0.01-2 wt %, 0.01-1.5 wt %, 0.01-1.2 wt %, 0.01-1 wt %, 0.01-0.8 wt %, 0.01-0.7 wt %, 0.01-0.6 wt %, 0.01-0.5 wt %, 0.1-2 wt %, 0.1-1.5 wt %, 0.1-1.2 wt %, 0.1-1 wt %, 0.1-0.8 wt %, 0.1-0.7 wt %, 0.1-0.6 wt %, or 0.1-0.5 wt %and wherein the total total amount of oligosaccharides with more than 5 glucose units (DP ＞5) is in the range of 0.0001-0.5 wt %, 0.0001-0.4 wt %, 0.0001-0.3 wt %, 0.0001-0.2 wt %, 0.0001-0.1 wt %, 0.01- 0.5 wt %, 0.01-0.4 wt %, 0.01-0.3 wt %, 0.01-0.2 wt %, 0.01-0.1 wt %, 0.1-0.5 wt %, 0.1-0.4 wt %, 0.1-0.3 wt %or 0.1-0.2 wt %.
  • In some embodiments, the glycosylation products, such as GSGs, GSEs, GSTEs, GSTCs comprise glycosylated RU in an amount of less than 80%, 75%, 70%, 65%, 60%, 55%, 50%, 45%, 40%, 35%, 30%, 25%, 20%, 15%or 10%by weight of the glycosylation products. In some embodiments, the glycosylation products, such as GSGs, GSEs, GSTEs, GSTCs, comprise glycosylated RU in an amount of greater than 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%or 95%by weight of the glycosylation products.
  • In some embodiments, the glycosylated RU comprises unreacted dextrins in an amount of greater than zero but less than 30%, 20%, 15%, 10%, 8%, 5%, 4%, 3%, 2%, 1%, 0.5%, 0.2%, 0.1%, 0.05%, 0.02%, 0.01%, 0.005%, 0.002%, or 0.001% (w/w) . In some embodiments, the glycosylated RU comprises mono-glucose RU (RU-1G) in an amount of greater than 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%or 90% (w/w) of the total GRU. In some embodiments, the glycosylated RU comprises di-glucose RU (RU-2G) in an amount of greater than 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%or 90% (w/w) of the total GRU. In some embodiments, the glycosylated RU comprises tri-glucose RU (RU-3G) in an amount of greater than 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%or 90% (w/w) of the total GRU. In some embodiments, the glycosylated RU comprises tetra-glucose RU (RU-4G) in an amount of greater than 10%, 20%, 30%, 40%, 50%60%, 70%, 80%or 90% (w/w) of the total GRU. In some embodiments, the glycosylated RU comprises penta-glucose RU (RU-5G) in an amount of greater than 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%or 90% (w/w) of the total GRU.
  • In some embodiments, the glycosylation product comprises unreacted RU residue in an amount of greater than zero but less than 30%, 20%, 15%, 10%, 8%, 5%, 4%, 3%, 2%, 1%, 0.5%, 0.2%, 0.1%, 0.05%, 0.02%, 0.01%, 0.005%, 0.002%, or 0.001% (w/w) of the glycosylation product.
  • In some embodiments, the glycosylation product comprises unreacted suaviosides in an amount of greater than zero but less than 20%, 15%, 10%, 8%, 5%, 4%, 3%, 2%, 1%, 0.5%, 0.2%, 0.1%, 0.05%, 0.02%, 0.01%, 0.005%, 0.002%, or 0.001% (w/w) of the glycosylation product.
  • In some embodiments, the glycosylation products, such as GSGs, GSEs, GSTEs, GSTCs, comprise steviol monoside in an amount of great than 6%, 8%, 10%, 12%, 15%, 20%25%or 30%by weight of the glycosylation products. In some embodiments, the glycosylation products, such as GSGs, GSEs, GSTEs, GSTCs, comprise steviol monoside in an amount of less than 60%, 55%, 50%, 45%, 40%, 35%, 30%, 25%, 20%, 15%, 10%or 5%by weight of the glycosylation products.
  • In some embodiments, the glycosylation products, such as GSGs, GSEs, GSTEs, GSTCs, comprise less than 50%, 30%, 10%, 8%, 6%, 4%or 2%mono-glycosylated RU (i.e., RU backbone with one added monosaccharide unit) by weight of the glycosylation products. In some embodiments, the glycosylation products, such as GSGs, GSEs, GSTEs, GSTCs, comprise greater than 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%or 60%mono-glycosylated RU by weight of the glycosylation products.
  • In some embodiments, the glycosylation products, such as GSGs, GSEs, GSTEs, GSTCs, comprise less than 50%, 40%, 15%, 12%, 10%, 8%, 6%, 4%or 2%bi-glycosylated RU (i.e., RU backbone with two added monosaccharide units) by weight of the glycosylation products. In some embodiments, the glycosylation products, such as GSGs, GSEs, GSTEs, GSTCs, comprise greater than 1%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%or 50%bi-glycosylated RU by weight of the glycosylation products.
  • In some embodiments, the glycosylation products, such as GSGs, GSEs, GSTEs, GSTCs, comprise less than 20%, 15%, 5%, 4%, 3%, 2%, 1%tri-glycosylated RU (i.e., RU backbone with three added monosaccharide units) by weight of the glycosylation products. In some embodiments, the glycosylation products, such as GSGs, GSEs, GSTEs, GSTCs, comprise greater than 5%, 10%, 15%, 20%, 25%, 30%, 35%or 40%tri-glycosylated RU by weight of the glycosylation products.
  • In some embodiments, the glycosylation products, such as GSGs, GSEs, GSTEs, GSTCs, comprise mono-glycosylated RU, bi-glycosylated RU and triglycosylated RU in a total amount of less than 30%, 25%, 20%, 15%or 10%by weight of the glycosylation products. In some embodiments, the glycosylation products, such as GSGs, GSEs, GSTEs, GSTCs, comprise mono-glycosylated RU, bi-glycosylated RU and triglycosylated RU in a total amount of greater  than 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%or 90%by weight of the glycosylation products.
  • In some embodiments, the glycosylation products, such as GSGs, GSEs, GSTEs, GSTCs, comprise RU in an amount of less than 30%, 25%, 20%, 15%, 10%, 5%, 4%, 3%, 2%or 1%by weight of the glycosylation products. In some embodiments, the glycosylation products, such as GSGs, GSEs, GSTEs, GSTCs, comprise RU in an amount of greated than 1%, 2%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%or 80%by weight of the glycosylation products.
  • In one aspect, in an exemplary composition having two different components, the components can have ratios of from 1∶99, 2∶98, 3∶97, 4∶96, 5∶95, 6∶94, 7∶93, 8∶92, 9∶91, 10∶90, 11∶89, 12∶88, 13∶87, 14∶86, 15∶85, 16∶84, 17∶83, 18∶82, 19∶81, 20∶80, 21∶79, 22∶78, 23∶77, 24∶76, 25∶75, 26∶74, 27∶73, 28∶72, 29∶71, 30∶70, 31∶69, 32∶68, 33∶67, 34∶66, 35∶65, 36∶64, 37∶63, 38∶62, 39∶61, 40∶60, 41∶59, 42∶58, 43∶57, 44∶56, 45∶55, 46∶54, 47∶53, 48∶52, 49∶51 and 50∶50, and all ranges therebetween wherein the ratios are from 1∶99 and vice versa, e.g., a ratio of from 1∶99 to 50∶50, from 30∶70 to 42∶58, etc.
  • It should be understood that the different components can be GSGs, GSEs, STEs, STCs, RU, G-STEs, G-STCs, G-SU, sweeteners, non-nutritive sweeteners, individual components of sweeteners, such as RA, RB, RD, RM, etc., components of stevia extracts, components of mogroside extracts, etc.
  • In another aspect, in an exemplary composition having three different components. The components can have ratios of from 1∶1∶98, 1∶2∶97, 1∶3∶96, 1∶4∶95, 1∶5∶94, 1∶6∶93, 1∶7∶92, 1∶8∶91, 1∶9∶90, 1∶10∶89, 1∶11∶88, 1∶12∶87, 1∶13∶86, 1∶14∶85, 1∶15∶84, 1∶16∶83, 1∶17∶82, 1∶18∶81, 1∶19∶80, 1∶20∶79, 1∶21∶78, 1∶22∶77, 1∶23∶76, 1∶24∶75, 1∶25∶74, 1∶26∶73, 1∶27∶72, 1∶28∶71, 1∶29∶70, 1∶30∶69, 1∶31∶68, 1∶32∶67, 2∶3∶95, 2∶4∶94, 2∶5∶93, 2∶6∶92, 2∶7∶91, 2∶8∶90, 2∶9∶89, 2∶10∶88, 2∶11∶87, 2∶12∶86, 2∶13∶85, 2∶14∶84, 2∶15∶83, 2∶16∶82, 2∶17∶81, 2∶18∶80, 2∶19∶79, 2∶20∶78, 2∶21∶77, 2∶22∶76, 2∶23∶75, 2∶24∶74, 2∶25∶73, 2∶26∶72, 2∶27∶71, 2∶28∶70, 2∶29∶69, 2∶30∶68, 2∶31∶67, 2∶32∶66, 2∶3∶95, 3∶3∶94, 3∶4∶93, 3∶5∶92, 3∶6∶91, 3∶7∶90, 3∶8∶89, 3∶9∶88, 3∶10∶87, 3∶11∶86, 3∶12∶85, 3∶13∶84, 3∶14∶83, 3∶15∶82, 3∶16∶81, 2∶17∶80, 3∶18∶79, 3∶19∶78, 3∶20∶77, 3∶21∶76, 3∶22∶75, 3∶23∶74, 3∶24∶73, 3∶25∶72, 3∶26∶71, 3∶27∶70, 3∶28∶69, 3∶29∶68, 3∶30∶67, 3∶31∶66, 3∶32∶65, 4∶4∶92, 4∶5∶91, 4∶6∶90, 4∶7∶89, 4∶8∶88, 4∶9∶87, 4∶10∶86, 4∶11∶85, 4∶12∶84, 4∶13∶83, 4∶14∶82, 4∶15∶81, 4∶16∶80,  4∶17∶79, 4∶18∶78, 4∶19∶77, 4∶20∶76, 4∶21∶75, 4∶22∶74, 4∶23∶73, 4∶24∶72, 4∶25∶71, 4∶26∶70, 4∶27∶69, 4∶28∶68, 4∶29∶67, 4∶30∶66, 4∶31∶65, 4∶32∶64, 5∶5∶90, 5∶6∶89, 5∶7∶88, 5∶8∶87, 5∶9∶86, 5∶10∶85, 5∶11∶84, 5∶12∶83, 5∶13∶82, 5∶14∶81, 5∶15∶80, 5∶16∶79, 5∶17∶78, 5∶18∶77, 5∶19∶76, 5∶20∶75, 5∶21∶74, 5∶22∶73, 5∶23∶72, 5∶24∶71, 5∶25∶70, 5∶26∶69, 5∶27∶68, 5∶28∶67, 5∶29∶66, 5∶30∶65, 5∶31∶64, 5∶32∶63, 6∶6∶88, 6∶7∶87, 6∶8∶86, 6∶9∶85, 6∶10∶84, 6∶11∶83, 6∶12∶82, 6∶13∶81, 6∶14∶80, 6∶15∶79, 6∶16∶78, 6∶17∶77, 6∶18∶76, 6∶19∶75, 6∶20∶74, 6∶21∶73, 6∶22∶72, 6∶23∶71, 6∶24∶70, 6∶25∶69, 6∶26∶68, 6∶27∶67, 6∶28∶66, 6∶29∶65, 6∶30∶64, 6∶31∶63, 6∶32∶62, 7∶7∶86, 7∶8∶85, 7∶9∶84, 7∶10∶83, 7∶11∶82, 7∶12∶81, 7∶13∶80, 7∶14∶79, 7∶15∶78, 7∶16∶77, 7∶17∶76, 7∶18∶75, 7∶19∶74, 7∶20∶73, 7∶21∶72, 7∶22∶71, 7∶23∶70, 7∶24∶69, 7∶25∶68, 7∶26∶67, 7∶27∶66, 7∶28∶65, 7∶29∶64, 7∶30∶63, 7∶31∶62, 7∶32∶61, 8∶8∶84, 8∶9∶83, 8∶10∶82, 8∶11∶81, 8∶12∶80, 8∶13∶79, 8∶14∶78, 8∶15∶77, 8∶16∶76, 8∶17∶75, 8∶18∶74, 8∶19∶73, 8∶20∶72, 8∶21∶71, 8∶22∶70, 8∶23∶69, 8∶24∶68, 8∶25∶67, 8∶26∶66, 8∶27∶65, 8∶28∶64, 8∶29∶63, 8∶30∶62, 8∶31∶61, 8∶32∶60, 9∶9∶82, 9∶10∶81, 9∶11∶80, 9∶12∶79, 9∶13∶78, 9∶14∶77, 9∶15∶76, 9∶16∶75, 9∶17∶74, 9∶18∶73, 9∶19∶72, 9∶20∶71, 9∶21∶70, 9∶22∶69, 9∶23∶68, 9∶24∶67, 9∶25∶66, 9∶26∶65, 9∶27∶64, 9∶28∶63, 9∶29∶62, 9∶30∶61, 9∶31∶60, 9∶32∶59, 10∶10∶80, 10∶11∶79, 10∶12∶78, 10∶13∶77, 10∶14∶76, 10∶15∶75, 10∶16∶74, 10∶17∶73, 10∶18∶72, 10∶19∶71, 10∶20∶70, 10∶21∶69, 10∶22∶68, 10∶23∶67, 10∶24∶66, 10∶25∶65, 10∶26∶64, 10∶27∶63, 10∶28∶62, 10∶29∶61, 10∶30∶60, 10∶31∶59, 10∶32∶58, 11∶11∶78, 11∶12∶77, 11∶13∶76, 11∶14∶75, 11∶15∶74, 11∶16∶73, 11∶17∶72, 11∶18∶71, 11∶19∶70, 11∶20∶69, 11∶21∶68, 11∶22∶67, 11∶23∶66, 11∶24∶65, 11∶25∶64, 11∶26∶63, 11∶27∶62, 11∶28∶61, 11∶29∶60, 11∶30∶59, 11∶31∶58, 11∶32∶57, 12∶12∶76, 12∶13∶75, 12∶14∶74, 12∶15∶73, 12∶16∶72, 12∶17∶71, 12∶18∶70, 12∶19∶69, 12∶20∶68, 12∶21∶67, 12∶22∶66, 12∶23∶65, 12∶24∶64, 12∶25∶63, 12∶26∶62, 12∶27∶61, 12∶28∶60, 12∶29∶59, 12∶30∶58, 12∶31∶57, 12∶32∶56, 13∶13∶74, 13∶14∶73, 13∶15∶72, 13∶16∶71, 13∶17∶70, 13∶18∶69, 13∶19∶68, 13∶20∶67, 13∶21∶66, 13∶22∶65, 13∶23∶64, 13∶24∶63, 13∶25∶62, 13∶26∶61, 13∶27∶60, 13∶28∶59, 13∶29∶58, 13∶30∶57, 13∶31∶56, 13∶32∶55, 14∶14∶72, 14∶15∶71, 14∶16∶70, 14∶17∶69, 14∶18∶68, 14∶19∶67, 14∶20∶66, 14∶21∶65, 14∶22∶64, 14∶23∶63, 14∶24∶62, 14∶25∶61, 14∶26∶60, 14∶27∶59, 14∶28∶58, 14∶29∶57, 14∶30∶56, 14∶31∶55, 14∶32∶54, 15∶15∶70, 15∶16∶69, 15∶17∶68, 15∶18∶67, 15∶19∶66, 15∶20∶65, 15∶21∶64, 15∶22∶63, 15∶23∶62, 15∶24∶61, 15∶25∶60, 15∶26∶59, 15∶27∶58, 17∶28∶57, 15∶29∶56, 15∶30∶55, 15∶31∶54, 15∶32∶53, 16∶16∶68, 16∶17∶67, 16∶18∶66, 16∶19∶65, 16∶20∶64, 16∶21∶63, 16∶22∶62, 16∶23∶61, 16∶24∶60, 16∶25∶59, 16∶26∶58, 16∶27∶57, 16∶28∶56, 16∶29∶55, 16∶30∶54, 16∶31∶53, 16∶32∶52, 17∶17∶66, 17∶18∶65, 17∶19∶64, 17∶20∶63, 17∶21∶62, 17∶22∶61, 17∶23∶60, 17∶24∶59, 17∶25∶58, 17∶26∶57, 17∶27∶56, 17∶28∶55, 17∶29∶54, 17∶30∶53, 17∶31∶52, 17∶32∶51, 18∶18∶64, 18∶19∶63, 18∶20∶62, 18∶21∶61,  18∶22∶60, 18∶23∶59, 18∶24∶58, 18∶25∶57, 18∶26∶56, 18∶27∶55, 18∶28∶54, 18∶29∶53, 18∶30∶52, 18∶31∶51, 18∶32∶50, 19∶19∶62, 19∶20∶61, 19∶21∶60, 19∶22∶59, 19∶23∶58, 19∶24∶57, 19∶25∶56, 19∶26∶55, 19∶27∶54, 19∶28∶53, 19∶29∶52, 19∶30∶51, 19∶31∶50, 19∶32∶49, 20∶20∶60, 20∶21∶59, 20∶22∶58, 20∶23∶57, 20∶24∶56, 20∶25∶55, 20∶26∶54, 20∶27∶53, 20∶28∶52, 20∶29∶51, 20∶30∶50, 20∶31∶49, 20∶32∶48, 21∶21∶58, 21∶22∶57, 21∶23∶56, 21∶24∶55, 21∶25∶54, 21∶26∶53, 21∶27∶52, 21∶28∶51, 21∶29∶50, 21∶30∶49, 21∶31∶48, 21∶32∶47, 22∶22∶56, 22∶23∶55, 22∶24∶54, 22∶25∶53, 22∶26∶52, 22∶27∶51, 22∶28∶50, 22∶29∶49, 22∶30∶48, 22∶31∶47, 22∶32∶46, 23∶23∶54, 23∶24∶53, 23∶25∶52, 23∶26∶51, 23∶27∶50, 23∶28∶49, 23∶29∶48, 23∶30∶47, 23∶31∶46, 23∶32∶45, 24∶24∶52, 24∶25∶51, 24∶26∶50, 24∶27∶49, 24∶28∶48, 24∶29∶47, 24∶30∶46, 24∶31∶45, 24∶32∶44, 25∶25∶50, 25∶26∶49, 25∶27∶48, 25∶28∶47, 25∶29∶46, 25∶30∶45, 25∶31∶44, 25∶32∶43, 26∶26∶48, 26∶27∶47, 26∶28∶46, 26∶29∶45, 26∶30∶44, 26∶31∶43, 26∶32∶42, 27∶27∶46, 27∶28∶45, 27∶29∶44, 27∶30∶43, 27∶31∶42, 27∶32∶41, 28∶28∶44, 28∶29∶43, 28∶30∶42, 28∶31∶41, 28∶32∶40, 29∶29∶42, 29∶30∶41, 29∶31∶40, 29∶32∶39, 30∶30∶40, 30∶31∶39, 30∶32∶38, 31∶31∶38, 31∶32∶37, 32∶32∶36, 32∶33∶35, and 33.3∶33.3∶33.3, and all ranges therebetween wherein the ratios are from 1∶1∶98 and vice versa, e.g., a ratio of from 1∶1∶98 to 33.3∶33.3∶33.3, from 10∶30∶70 to 15∶40∶45, etc.
  • It should be understood that the different components can be GSGs, GSEs, STEs, STCs, RU, G-STEs, G-STCs, G-SU, sweeteners, non-nutritive sweeteners, individual components of sweeteners, such as RA, RB, RD, RM, etc., components of stevia extracts, components of mogroside extracts, etc.
  • It is noted that the present disclosure is not limited to compositions having only two or three different components, and that the exemplary ratios are non-limiting. Rather, the same formula can be followed for establishing ratios of as many different components as are contained within a given composition. As a further example, in a composition that comprises 20 different components described herein, the components can have ratios of from 1∶1∶1∶1∶1∶1∶1∶1∶1∶1∶1∶1∶1∶1∶1∶1∶1∶1∶1∶81 to 5∶5∶5∶5∶5∶5∶5∶5∶5∶5∶5∶5∶5∶5∶5∶5∶5∶5∶5∶5, and all possible combinations of ratios therebetween. In some embodiments, a composition of the present disclosure may have up to and including a combination of all compounds.
  • The SGs, SEs, STEs, STCs and compositions derived therefrom contain volatile and unvolatile terpine and/or terpinoid substances that can be further purified in order to obtain substance providing a tasteful, sweet and/or aromatic profile. Treatment of SGs, SEs, GSGs,  GSEs, STEs, STCs, GSTEs, and GSTCs using column chromatography, separation resins, and/or other separation methods, such as distillation, can be employed to retain most of the tasteful aroma terpine and/or terpinoid substances containing oxygen in the structure, while removing other unpleasant taste substances.
  • High intensity sweeteners like natural sweeteners such as stevia extract, monk fruit extract etc, and synthetic sweeteners such as sucralose, acesulfame-K, aspartame, sodium saccharin etc. are characterized by their slow on-site, less high-peak sweetness, lower tongue heaviness, sweet aftertaste, less mouth coating, slipperiness, and high bitter aftertaste, metallic aftertaste. An extraordinary or good beverage must have synchronized or harmonized sweetness temporal profile, acidity temporal profile and aroma temporal profile. However, it is painful for food and beverage formulators when using these high intensity sweeteners to make these three dimensions synchronized, especially for sugar reduced, sugar free products.
  • Normally, the formulation sequence seeks to achieve balanced sweetness and sourness, followed by the addition of flavor. However, but it is difficult to achieve such a balance for sugar reduced, sugar free products. The deficiencies associated with high intensity sweeteners renders current diet products less palatable to consumers. In the currently prevailing market, flavor, acidity and sweetness are not sufficiently integrated in diet products; such non-synchronized products leave either an initial bad taste/flavor which makes them less prone to be swallowed, or they leave an undesirable aftertaste or after flavor. In most cases, the temporal profile of the flavor (s) is very short, or the flavor comes first before sweet or sour taste, or is associated with bitterness, lingering, and/or a metallic taste. All of so-called “good tasting” natural sweeteners, such as Reb D and Reb M, as well as synthetic sweeteners, such as Ac-K and sucralose, create metallic and lingering tastes, which are difficult for consumers to accept.
  • Oral acceptability constitues a big decision for consumers. For example, where a product or drink is bitter, a baby or child may use their mouth or tongue to repel the food or beverage therefrom. Mouth is the scout to identify the risk. Ideally, a food or beverage should create a synchronized aroma/taste leading one to relax and release their alertness and suspiciousness, and promote swallowing of the food or beverage.
  • An additional embodiment of a food or beverage comprises rubusoside and one or more components selected from GSGs, GSEs, G-STEs, G-STCs, and high intensity  sweeteners, 1) where rubusoside is less than 100 ppm; or 2) where total rubusoside and glycosylated rubusoside is less than 1,000 ppm, less than 800 ppm, 600 ppm, less than 500 ppm, less than 400 ppm, less than 200 ppm, less than 100 ppm, less than 50 ppm, less than 20 ppm or less than 10 ppm.
  • In another embodiment, the food or beverage comprising a GSE, GSG, G-STE, and/or G-STC comprises mono-glycosylated rubusoside and unconverted rubusoside, where the mono-glycosylated rubusoside in the total glycosylate rubusosides is more than 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%or 95%.
  • A further embodiment of a food or beverage comprises rubusoside and glycosylated rubusoside, where the mono-glycosylated rubusoside is more than 1 ppm, 10 ppm, 50 ppm, 100 ppm, 150 ppm, 200 ppm, 250 ppm, 300 ppm, 500 ppm, 1,000 ppm or 10,000 ppm.
  • A further embodiment of a food or beverage comprises glycosylated rubusoside, where the mono-glycosylated rubusoside is present but in an amount that is less than 10,000 ppm, 5,000 ppm, 1,000 ppm, 500 ppm, 300 ppm, 250 ppm, 100 ppm, 50 ppm, 10 ppm, 5 ppm or 1 ppm. In some embodiments, mono-glycosylated rubusoside is present in an amount of 0.01-10,000 ppm, 0.01-5,000 ppm, 0.01-1,000 ppm, 0.01-500 ppm, 0.01-300 ppm, 0.01-250 ppm, 0.01-100 ppm, 0.01-50 ppm, 0.01-10 ppm, 0.01-5 ppm, 0.01-1 ppm, 0.1-10,000 ppm, 0.1-5,000 ppm, 0.1-1,000 ppm, 0.1-500 ppm, 0.1-300 ppm, 0.1-250 ppm, 0.1-100 ppm, 0.1-50 ppm, 0.1-10 ppm, 0.1-5 ppm or 0.1-1 ppm, 1-10,000 ppm, 1-5,000 ppm, 1-1,000 ppm, 1-500 ppm, 1-300 ppm, 1-250 ppm, 1-100 ppm, 1-50 ppm, 1-10 ppm, 1-5 ppm, 100-10,000 ppm, 1-5,000 ppm, 10-1,000 ppm, 10-500 ppm, 10-300 ppm, 10-250 ppm, 10-100 ppm, 10-50 ppm, 50-10,000 ppm, 50-5,000 ppm, 50-1,000 ppm, 50-500 ppm, 50-300 ppm, 50-250 ppm, 50-100 ppm, 100-10,000 ppm, 100-5,000 ppm, 100-1,000 ppm, 100-500 ppm, 100-300 ppm, 300-10,000 ppm, 300-5,000 ppm, 300-1,000 ppm, 1,000-10,000 ppm or 1,000-5,000 ppm.
  • The nasal cavity has a large surface area and is a good approach for brain nutrition and medicines. Sublingual administration has certain advantages over oral administration. Being more direct, it is often faster and effective. The intranasal and sublingual route of drug administration has been used for a variety of medications. Current invention provide a solution to make intranasal and sublingual nutrition and medicines more palatable. An  embodiment of intranasal or sublingual composition comprises one or more ingredients selected from G-STEs and G-STCs.
  • Masking bitter tastes remains a primary goal for the food and beverage industry. Bitterness has been a challenge with a wide range of foodstuffs, including fruits, such as grapefruit, passionfruit, oranges; vegetables, including cucumbers and avocados; beverage products, including beer, coffee, and chocolate; and protein products, including dairy and soy products. The inventor of the present application has successfully developed compositions comprising one or more ingredients selected from G-STEs and G-STCs, which can mask the bitterness of food and beverage products.
  • The inventor also surprisingly found that SGs, GSGs, SE, GSE, STE, STC, GSTE and GSTC comprises rubusoside and or glycosylated rubusosides, could enhance the astringency, accelerate the quick acidity sensation. An embodiment of a consumable comprises one or more substances selected from SGs, SE, GSE, GSGs, STE, STC, GSTE and GSTC comprises rubusoside and or glycosylated rubusosides, which could enhance the astringency and quick acid onsite sensation. Preferably, the consumable is contains tea extract, tea concentrate, cranberry juice, cranberry flavor, cranberry concentrate, grapefruit juice, grapefruit concentrate, grapefruit flavor, lemon and or lime flavor/juice/concentrate. More preferably, a consumable contains one or more substances selected from STE, STC, GSTE, and GSTC, s and quinic acid, where the quinic acid is above 0.1ppm, 1ppm, 5ppm, 10ppm, 50ppm, 100ppm, 200ppm, 500ppm, 1,000ppm, 2,000ppm, 5,000ppm, 10,000ppm, 50,000ppm or 100,000ppm.
  • Once again, rubusoside is one of STC, it should be understandable in whole specification that STC includes rubusoside or other sweet tea components originated from other sources including but not limited to stevia extract, stevia glycosides, or fermentation, enzymatic conversion, synthetic method.
  • The inventor also surprisingly found that STE, STC, GSTE and GSTC could improve the solubility and enhance the sweetness of stevia glycosides. There is synergy effect when combined together. An embodiment of a consumable comprises one or more substances selected from STE, STC, GSTE and GSTC, and stevia extract comprises one or more stevia glycosides selected from Reb A, Reb B, Reb C, Reb D, Reb E, Reb I, Reb M, Reb O, which solubility and or sweetness of stevia extract is increased.
  • An embodiment of composition comprises GSG, GSE, GSTE or GSTC, where the ratio of one-added glucose to two added glucose to rubusoside is more than 1.
  • An embodiment of composition comprises SGs, SE, STE or STC, where the rubusoside content is less than 90%, less than 70%, less than 50%, less than 30%, less than 20%, less than 15%, less than 10%, less than 5%, the non-rubusoside substances originated from sweet tea plant are above 5%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%or 95%.
  • An embodiment of composition comprises GSG, GSE, G-STE or G-STC, where total glycosylated rubusosides is less than 90%, less than 70%, less than 50%, less than 30%, less than 20%, less than 15%, less than 10%, less than 5%, the non-rubusoside substances or their glycosylated form originated from sweet tea plant are above 5%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%or 95%.
  • Poor aqueous solubility is not only an obstacle to extend their application for stevia glycosides, but also for many other pharmaceutical active substances, herb extract, for instance, carotenoids like lutein, zeaxanthin, lutein esters, epilutein, polyphenols like apple polyphenols, kiwi polyphenols, grape seed polyphenols, flavonoids such as flavonoids extracted from gingko biloba, alkaloids such as devil’s claw extract etc.. The inventor found high intensity sweetener extracts, such as stevia extract, sweet tea extract, monk fruit extract could improve the solubility of substances which have poor water solubility; preferably the crude extract comprises non-stevia glycosides or non-sweetening substances. An embodiment of composition comprising a) one or more ingredient selected from sweet tea extract, stevia extract, monk fruit extract, licorice extract, their glycosylated products; and b) one or more ingredient selected from herb extract or pharmaceutical active ingredients, where a) could improve the solubility and bioavailability of b) .
  • Flavors from edible products such as fruits, berries, herbs and species are useful to enhance the palatability of food and beverage. However, the prevailing mindset of flavor industry takes volatile substances to bring the olfactory smell as key factor to measure the quality of flavor. However, the inventor found flavors containing flavor substances from fruit juice, berries juice, fresh herb or species juices could have substantially positive impact on retronasal flavors when adding into a food or beverage. The flavor compositions comprises less volatile substances are important to influence the palatability of food and beverage. An embodiment of  composition comprising a) one or more ingredient selected from sweet tea extract, stevia extract, monk fruit extract and licorice extract, their glycosylated products; and b) one or more flavor extracted or concentrated ingredient selected from fruits juices, berries juices, herb and species fresh juices, where b) comprises less volatile or non-volatile substances from juices, and the composition could improve the palatability of food and beverage substantially. An additional embodiment of such composition comprises water soluble juicy substances, such as fruit concentration or juice concentrate or extract from water melon, bilberry, citrus, orange, lime, lemon, kiwi, apple etc.
  • In some embodiments, a SG, GSG, SE, GSE, STE, STC, GSTE or GSTC can be enriched for the presence of aromatic terpene substances containing oxygen in the structure. In some embodiments, a citrus or tangerine taste is enhanced by heat-treating a terpine-and/or terpinoid rich STE under acidic conditions comprising e.g., citric acid, tartaric acid, fumaric acid, lactic acid, malic acid etc., more preferably citric acid. In addition, substances such as linalool can react with citric acid. Vacuum distillation of fractions or column chromatography employing macroporous resins and/or silica gels, including ion exchange resins produced by Dow and Sunresin can be used for further purification.
  • In some embodiments, a SG, GSG, SE, GSE, STE, STC, GSTE or GSTC composition further includes flavor substances from the sweet tea plant or other natural sweetener plants described herein, including leaves, roots, seeds, etc. therefrom.
  • In another aspect, the present application provides a stevioside-enriched composition or extract. As used in this context, the term “stevioside-enriched” refers to a composition or Stevia extract containing or processed to contain more than 50%stevioside.
  • In another aspect, the present application provides a rubusoside-enriched composition originated from Stevia extract (RU-Stevia) . As used in this context, the term “rubusoside-enriched composition” refers to a composition or extract containing, or processed to contain, more than 50%rubusoside. In some embodiments, the RU-Stevia composition is obtained by bio-conversion of stevioside to rubusoside using a stevioside-enriched Stevia composition or extract (containing stevioside more than 40%) , including sweetener and flavor compositions thereof. The term “GRU-Stevia” composition is used with reference to a glycosylate composition formed from an RU-Stevia composition.
  • In some embodiments, a sweetener or flavor composition includes one or more components selected from the group consisting of 9-OH Suav J, suavioside A, Suavioside B, Suavioside E, uavioside F, Suavioside H, Suavioside K, Suavioside L, Suavioside O, Steviol, Reb A, and Rubososide.
  • In some emobodiment, an RU-Stevia sweetener or flavor composition comprises Stevia composition having a rubusoside content of at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or any range defined by any pair of these integers.
  • In some embodimenst, an RU-Stevia sweetener or flavor composition includes rubusoside and sauviosides, where the total content of sauviosides is at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or any range defined by any pair of these integers.
  • In some embodiment, an RU-Stevia sweetener or flavor composition comprises Reb A, rubusoside and one or more sauviosides, where the Reb A content is less than 50%, less than 40%, less than 30%, less than 20%, less than 10%, less than 5%, less than 1%.
  • In some embodiments, an RU-Stevia sweetener, flavor sweetener or flavor composition comprises one or more substances selected from 9-OH Suav J, suavioside A, Suavioside B, Suavioside E, Suavioside F, Suavioside H, Suavioside K, Suavioside L, Suavioside O, Steviol, Reb A, Rubososide, and stevioside, where the stevioside content is present but in an amount of less than 50 wt %, less than 40 wt %, less than 30 wt %, less than 20 wt %, less than 10 wt %, less than 5 wt %, less than 2 wt %, or less than 1 wt %of the composition.
  • In some embodiments, an RU-Stevia sweetener, flavor sweetener or flavor composition comprises one or more substances selected from 9-OH Suav J, suavioside A, Suavioside B, Suavioside E, Suavioside F, Suavioside H, Suavioside K, Suavioside L, Suavioside O, Steviol, Reb A, Rubososide, and stevioside, where the stevioside content is present but in an amount of 0.01-50 wt %, 0.01-40 wt %, 0.01-30 wt %, 0.01-20 wt %, 0.01-10 wt %, 0.01-5 wt %, 0.01-2 wt %, or 0.01-1 wt %of the composition.
  • In some embodiments, a GRU-Stevia composition is prepared from an RU-Stevia composition comprising one or more substances selected from 9-OH Suav J, suavioside A, Suavioside B, Suavioside E, Suavioside F, Suavioside H, Suavioside K, Suavioside L, Suavioside O, Steviol, Reb A, and Rubososide.
  • In some embodiments, the sweetener or flavor composition comprises GRU-Stevia and a sweetener composition, where the sweetener composition includes one or more substances selected from high intensity synthetic sweeteners, high intensity natural sweetners, bulk sweetners, and low sweetness products.
  • In some embodiement, the sweetener or flavor composition comprises glycosylated rubusosides and a sweetener, where the sweetener is selected from high intensity synthetic sweeteners, high intensity natural sweetners, bulk sweeteners, and low sweetness products, where the content of glycosylated rubusosides is at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or encompasses any range defined by any pair of these integers.
  • In some embodiments, a GRU-Stevia sweetener or flavor composition comprises GRU-Stevia, unreated RU-stevia, and unreacted sugar donors.
  • In some embodiments, the sweetner or flavor composition comprises: (a) GSGs; and (b) SGs, where (a) the GSGs are prepared from an SG composition comprising Reb A in an amount less than 20%, less than 10%, less than 5%, or less than 1%.
  • In some embodiments, the sweeetner or flavor composition comprises GSGs, where the total GSG content is at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or any range defined by any pair of these integers.
  • In some embodiments, the sweetener or flavor composition comprises GSGs, where the glycosylated Reb B content is at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or any range defined by any pair of these integers.
  • In some embodiments, the sweetener or flavor composition comprises GSGs, where the glycosylated Reb C content is at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or any range defined by any pair of these integers.
  • In some embodiments, the sweetener or flavor composition comprises GSGs, where the glycosylated Reb D content is at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or any range defined by any pair of these integers.
  • In some embodiments, the sweetener or flavor composition comprises GSGs, where the glycosylated Reb E content is at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or any range defined by any pair of these integers.
  • In some embodiments, the sweetener or flavor composition comprises GSGs, where the glycosylated Reb M content is at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or any range defined by any pair of these integers.
  • In some embodiments, the sweetener or flavor composition comprises GSGs, where the glycosylated steviolmonoside content is at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or any range defined by any pair of these integers.
  • In some embodiments, the sweetener or flavor composition comprises GSGs, where the glycosylated steviolbioside content is at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or any range defined by any pair of these integers.
  • In some embodiments, the sweetener or flavor composition comprises GSGs, where the glycosylated dulcoside A content is at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or any range defined by any pair of these integers.
  • In some embodiment, the sweetener or flavor composition comprises glycosylated sauviosides, where the total glycosylated sauvioside content is at least 1 wt %, at least 2 wt %, at least 5 wt %, at least 10 wt %, at least 15 wt %, at least 20 wt %, at least 25 wt %, at least 30 wt %, at least 35 wt %, at least 40 wt %, at least 45 wt %, at least 50 wt %, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at  least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or any range defined by any pair of these integers.
  • In some embodiment, the sweetener or flavor composition comprises (a) GSGs; and (b) stevia glycosides, where the GSGs are from SG compositions comprising stevioside in an amount greater than 30%wt%, greater than 40%wt%, greater than 50%wt%, greater than 60%wt%, greater than 70%wt%, greater than 80%wt%, greater than 90%wt%, or greater than 95%wt%, more preferably where the stevioside content is greater than 60 wt%, greater than 70 wt%, greater than 80 wt%, greater than 90 wt%, greater than 95 wt%, and most preferably where the rubusoside content is greater than 90 wt%or greater than 95 wt%. Typically, the SG composition will at least include some (or detectable) levels of stevioside.
  • In some embodiment, the sweetener or flavor composition comprises (a) GSGs and (b) SGs, where the GSGs are prepared from stevia glycoside compositions comprising rubusoside in an amount greater than 5 wt%, greater than 10 wt%, greater than 30 wt%, greater than 40 wt%, greater than 50 wt%, greater than 60 wt%, greater than 70 wt%, greater than 80 wt%, greater than 90 wt%, or greater than 95 wt%, more preferably where the rubusoside content is greater than 60 wt%, greater than 70 wt%, greater than 80 wt%, greater than 90 wt%, greater than 95 wt%, and most preferably where the rubusoside content is greater than 80 wt%, greater than 90 wt%, greater than 95 wt%; and where the SGs include one or more components selected from Reb A, Reb B, stevioside, Reb C, Reb D, Reb E, Reb F, Reb M, Reb N, and Reb O.
  • In some embodiments, a consumable product comprises GSGs as described in the present application, including GSGs present in the consumable product in a range from 0.1～1,5000 ppm.
  • III. Consumable products comprising the sweetener or flavoring compositions of the  present application
  • The compositions and methods described herein are useful in a wide range of consumable products. A non-limiting outline of products for application of the sweet tea-based sweetener or flavoring compositions described herein includes the following:
  • 1 Dairy Products
  • 1.1 Milk and dairy-based drinks
  • Milk and buttermilk
  • Buttermilk (plain)
  • Dairy based drinks, flavored and/or fermented
  • 1.2 Fermented, renneted milk products (excluding drinks)
  • 1.3 Condensed milk and analogues
  • Condensed milk (plain)
  • Beverage whiteners
  • 1.4 Cream (plain) and similar products
  • Pasteurized cream
  • Sterilized, UHT, whipping or whipped and reduced-fat creams
  • Clotted cream
  • Cream analogues
  • 1.5 Milk or cream powders
  • Milk or cream powders
  • Milk or cream powders analogues
  • 1.6 Cheese
  • Unripened cheese
  • Ripened cheese
  • Whey cheese
  • Processed cheese
  • Cheese analogues
  • 1.7 Dairy-based desserts (e.g., ice cream, ice milk, pudding, fruit or flavored yogurt)
  • 1.8 Whey and whey products, excluding whey cheese
  • 2 Fats and oils and fat emulsions (type water-in-oil)
  • 2.1 Fats and oils essentially free from water
  • 2.2 Fat emulsions, water-in-oil
  • 2.3 Fat emulsions other than 2.2, including mixed and/or flavored products based on fat emulsions.
  • 2.4 Fat-based desserts (excluding dairy-based desserts)
  • 3 Edible ices, including sherbet and sorbet
  • 4, Fruits and vegetables (including mushrooms and fungi, roots and tubers, pulses and legumes) and nuts and seeds
  • 4.1 Fruit
  • 4.1.1 Fresh fruit
  • Untreated fruit
  • Surface -treated fruit
  • Peeled or cut fruit
  • 4.1.2 Processed fruit
  • Frozen fruit
  • Dried fruit
  • Fruit in vinegar, oil or brine
  • Canned or bottled (pasteurized) fruit
  • Jams, jellies and marmalades
  • Fruit -based spread
  • Candied fruit
  • Fruit preparations, including pulp and fruit toppings
  • Fruit-based desserts, including fruit-flavored water-based desserts
  • Fermented fruit products
  • Fruit fillings for pastries
  • Cooked or fried fruits
  • 4.2 Vegetables (including mushrooms and fungi, roots and tubers, pulses and legumes) and nuts and seeds
  • 4.2.1 Fresh vegetables
  • Untreated vegetables
  • Surface treated vegetables
  • Peeled or cut vegetables
  • 4.2.2 Processed vegetable and nuts and seeds
  • Frozen vegetable
  • Dried vegetables
  • Vegetables in vinegar, oil or brine
  • Canned or bottled (pasteurized) vegetables
  • Vegetable, nut and seed purees and spreads
  • Vegetable, nut and seed pulps and preparations
  • Fermented vegetable products
  • Cooked or fried vegetables
  • 5 Confectionery
  • 5.1 Cocoa products and chocolate products, including imitations and chocolate substitutes
  • Cocoa mixes (powder and syrups)
  • Cocoa based spreads, including fillings
  • Cocoa and chocolate products (e.g., milk chocolate bars, chocolate flakes, white chocolate)
  • Imitation chocolate and chocolate substitute products
  • 5.2 Sugar-based confectionery other than 5.1, 5.3 and 5.4, including hard and soft candy and nougats
  • 5.3 Chewing gum
  • 5.4 Decorations (e.g., for fine bakery wares) , toppings (non-fruit) and sweet sauces
  • 6 Cereals and cereal products, including flours and starches from roots and tubers, and pulses and legumes, excluding bakery wares
  • Whole, broken or flaked grain, including rice
  • Flours and starches
  • Breakfast cereals, including rolled oats
  • Pastas and noodles
  • Cereals and starch-based desserts (e.g., rice pudding, tapioca pudding)
  • Batters (e.g., for fish or poultry)
  • 7 Bakery wares
  • 7.1 Bread and ordinary bakery wares
  • Breads and rolls
  • Crackers, excluding sweet crackers
  • Other ordinary bakery products (e.g., bagels, pitta, English muffins)
  • Bread-type products, including bread stuffing and breadcrumbs
  • 7.2 Fine bakery wares
  • Cakes, cookies and pies (e.g., fruit-filled or custard types)
  • Other fine bakery products (e.g., doughnuts, sweet rolls, scones and muffins)
  • Mixes for fine bakery wares (e.g., cakes, pancakes)
  • 8 Meat and meat products, including poultry and game
  • 8.1 Fresh meat, poultry and game
  • Fresh meat, poultry and game, whole pieces or cuts
  • Fresh meat, poultry and game, comminuted
  • 8.2 Processed meat, poultry and game products in whole pieces or cuts
  • 8.3 Processed comminuted meat, poultry and game products
  • 8.4 Edible casings (e.g., sausage casings)
  • 9, Fish and fish products, including mollusks, crustaceans and echinoderms
  • 9.1 Fish and fish products
  • 9.2 Processed fish and fish products
  • 9.3 Semi-preserved fish and fish products
  • 9.4 Fully preserved fish and fish products
  • 10 Eggs and egg products
  • 10.1 Fresh egg
  • 10.2 Egg products
  • 10.3 Preserved eggs
  • 10.4 Egg-baseddesserts
  • 11 Sweeteners, including honey
  • 11.1 White and semi-white sugar (sucrose or sacharose) , fructose, glucose (dextrose) , xylose, sugar solutions and syrups, and (partially) inverted sugars, including molasses, treacle and sugar toppings.
  • 11.2 Other sugar and syrups (e.g., brown sugar, maple syrup)
  • 11.3 Honey
  • 11.4 Table -top sweeteners, including those containing high-intensity sweeteners, other than 11.1-11.3
  • 12 Salt, spices, soups, sauces, salads, protein products, etc
  • 12.1 Salt
  • 12.2 Herbs, spices, seasonings (including salt substitutes) and condiments
  • 12.3 Vinegars
  • 12.4 Mustards
  • 12.5 Soups and broths
  • Ready-to-eat soups and broths, including canned, bottled and frozen
  • Mixes for soups and broths
  • 12.6 Sauces and similar products
  • Emulsified sauces (e.g., mayonnaise, salad dressing)
  • Non-emulsified sauces (e.g., ketchup, cheese sauce, cream sauce, brown gravy)
  • Mixes for sauces and gravies
  • 12.7 Salads (e.g., macaroni salad, potato salad) and sandwich spreads (excluding cocoa-and nut-based spreads)
  • 12.8 Yeast
  • 12.9 Protein products
  • 13 Foodstuffs intended for particular nutritional uses
  • 13.1 Infant formulae and follow-up formulae
  • 13.2 Foods for young children (weaning food)
  • 13.3 Diabetic foods intended for special medical purposes
  • 13.4 Diabetic formulae for slimming purposes and weight reduction
  • 13.5 Diabetic foods other than 13.1-13.4
  • 13.6 Food supplements
  • 14 Beverage excluding dairy products
  • 14.1 Non-alcoholic ( “soft” ) beverages
  • 14.1.1 Waters
  • Natural mineral waters and source waters
  • Table waters and soda waters
  • 14.1.2 Fruit and vegetable juices
  • Canned or bottled (pasteurized) fruit juice
  • Canned or bottled (pasteurized) vegetable juice
  • Concentrates (liquid or solid) for fruit juice
  • Concentrates (liquid or solid) for vegetable juice
  • 14.1.3 Fruit and vegetable nectars
  • Canned or bottled (pasteurized) fruit nectar
  • Canned or bottled (pasteurized) vegetable nectar
  • Concentrate (liquid or solid) for fruit nectar
  • Concentrate (liquid or solid) for vegetable nectar
  • 14.1.4 Water-based flavored drinks, including ‘sport’ or ‘electrolyte” drinks
  • Carbonated drinks
  • Non-carbonated drinks, including punches
  • Concentrates (liquid or solid) for drinks
  • 14.1.15 Coffee, coffee substitutes, tea, herbal infusions and other hot cereal beverages, excluding cocoa
  • 14.2 Alcoholic beverages, including alcohol-free and low-alcoholic counterparts
  • 14.2.1 Beer or malt beverage
  • 14.2.2 Cider and perry
  • 14.2.3 Wines
  • Still wine
  • Sparking and semi-sparkling wines
  • Fortified wine and liquor wine
  • Aromatized wine
  • 14.2.4 Fruit wine
  • 14.2.5 Mead
  • 14.2.6 Spirituous beverages
  • Spirituous beverage containing at least 15%alcohol
  • Spirituous beverage containing less than 15%alcohol
  • 15 Ready-to-eat savories
  • Snacks, potato-, cereal-, flour-, or starch-based (from roots and tubers, pulses and legumes)
  • Processed nuts, including coated nuts and nut mixtures (with e.g., dried fruit) 
  • 16 Composite foods (e.g., casseroles, meat pies, mincemeat) -foods that could not be placed in categories 1-15.
  • In one aspect, the present application provides an orally consumable product comprising one or more sweet tea-based sweetener or flavoring compositions of the present application described herein. The term “consumables” , as used herein, refers to substances which are contacted with the mouth of man or animal, including substances, which are taken into and subsequently ejected from the mouth, substances which are drunk, eaten, swallowed or otherwise ingested, and are safe for human or animal consumption when used in a generally acceptable range.
  • The sweetener or flavoring compositions of the present application can be added to an orally consumable product to provide a sweetened product or a flavored product. The sweetener or flavoring compositions of the present application can be incorporated into any oral consumable product, including but not limited to, for example, beverages and beverage products, food products or foodstuffs (e.g., confections, condiments, baked goods, cereal compositions, dairy products, chewing compositions, and tabletop sweetener compositions) , pharmaceutical compositions, smoking compositions, oral hygiene compositions, dental compositions, and the like. Consumables can be sweetened or unsweetened. Consumables employing the sweetener or flavoring compositions of the present application are also suitable for use in processed agricultural products, livestock products or seafood; processed meat products such as sausage and the like; retort food products, pickles, preserves boiled in soy sauce, delicacies, side dishes; soups; snacks, such as potato chips, cookies, or the like; as shredded filler, leaf, stem, stalk, homogenized leaf cured and animal feed.
  • A. Beverages and Beverage Products
  • In some embodiments, a beverage or beverage product comprises a composition of the present application, or a sweetener composition comprising the same. The beverage may be sweetened or unsweetened. The composition of the present application, or sweetener composition comprising the same, may be added to a beverage to sweeten the beverage or enhance its existing sweetness or flavor profile. In some embodiments, the composition of the present application comprises one or more substances selected from the group consisting of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs.
  • A “beverage” or “beverage product, ” is used herein with reference to a ready-to-drink beverage, beverage concentrate, beverage syrup, or powdered beverage. Suitable ready-to-drink beverages include carbonated and non-carbonated beverages. Carbonated beverages include, but are not limited to, frozen carbonated beverages, enhanced sparkling beverages, cola, fruit-flavored sparkling beverages (e.g., lemon-lime, orange, grape, strawberry and pineapple) , ginger-ale, soft drinks and root beer. Non-carbonated beverages include, but are not limited to, fruit juice, fruit-flavored juice, juice drinks, nectars, vegetable juice, vegetable-flavored juice, sports drinks, energy drinks, enhanced water drinks, enhanced water with vitamins, near water drinks (e.g., water with natural or synthetic flavorants) , coconut water, tea type drinks (e.g., black tea, green tea, red tea, oolong tea) , coffee, cocoa drink, broths, beverages comprising milk components (e.g., milk beverages, coffee comprising milk components, cafe au lair, milk tea, fruit milk beverages) , beverages comprising cereal extracts, and smoothies. Beverages may be frozen, semi-frozen ( “slush” ) , non-frozen, ready-to-drink, concentrated (powdered, frozen, or syrup) , dairy, non-dairy, probiotic, prebiotice, herbal, non-herbal, caffeinated, non-caffeinated, alcoholic, non-alcoholic, flavored, non-flavored, vegetable-based, fruit-based, root/tuber/corm-based, nut-based, other plant-based, cola-based, chocolate-based, meat-based, seafood-based, other animal-based, algae-based, calorie enhanced, calorie-reduced, and calorie-free.
  • The resulting beverages may be dispensed in open containers, cans, bottles or other packaging. Such beverages and beverage preparations can be in ready-to-drink, ready-to-cook, ready-to-mix, raw, or ingredient form and can use the composition as a sole sweetener or as a co-sweetener.
  • A significant challenge in the beverage industry is to preserve flavor in drinks. Normally, essential oils and their fractions are used as key flavors. They are prone to be oxidized to create unpleasant flavor (s) or the components easily evaporate to cause the food or beverage to lose their initial designed flavors as they sit on shelves. The embodiments herein provide new methods and compositions to overcome those disadvantages and provide new solutions to the food and flavor industry.
  • Compared with conventional flavors, which are mainly preserved in different oils or oil soluble solvents, the present embodiments provide new methods to provide water soluble solutions, syrups and powders for flavoring agents.
  • Compared to conventional isolated flavors, often as extracts from plant or animal sources, which are not always compatible for top note flavor and/or taste when sugar replacement sweeteners are added, the current embodiments provide new types of combined multi components which are compatible for a designed flavor.
  • The embodiments surprisingly create sugar reduced sweeteners which have better taste than sugar including, for example, sweetening agents such as Stevia extract, steviol glycosides, STE, monk fruit, licorice, etc. and synthetic sweetener such as sucralose.
  • Beverage concentrates and beverage syrups can be prepared with an initial volume of liquid matrix (e.g., water) and the desired beverage ingredients. Full strength beverages are then prepared by adding further volumes of water. Powdered beverages are prepared by dry-mixing all of the beverage ingredients in the absence of a liquid matrix. Full strength beverages are then prepared by adding the full volume of water.
  • Beverages comprise a matrix, i.e., the basic ingredient in which the ingredients -including the compositions of the present application -are dissolved. In one embodiment, a beverage comprises water of beverage quality as the matrix, such as, for example deionized water, distilled water, reverse osmosis water, carbon-treated water, purified water, demineralized water or combinations thereof, can be used. Additional suitable matrices include, but are not limited to phosphoric acid, phosphate buffer, citric acid, citrate buffer and carbon-treated water.
  • The beverage concentrations below can be provided by the composition of the present application or sweetener composition of the present application.
  • Traditionally, the use of regular guar gum and other thickeners have been limited to certain applications due to their notable “beany” or “grassy” off notes in both flavor and odor. These “off notes” are the result of volatile organic compounds such as hexanal and hexanoic acid etc. These compounds can influence the sensation of many delicate flavors in food and beverage applications. The STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs described herein, can modify the taste of thickeners, such as guar gum, caragum, xanthan gum etc. so that the taste is more pleasing to the consumer. The STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs described herein could also partially or totally replace thickeners used in the food and beverage industry. There is a synergy between the STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, and thickeners to obtain a balance of taste and cost.
  • The size of bubbles in a carbonated beverage can significantly affect the mouth feel and flavor of the beverage. It is desirable to manipulate one or more properties of the bubbles produced in a beverage. Such properties can include the size of bubbles produced, the shape of bubbles, the amount of bubbles generated, and the rate at which bubbles are released or otherwise generated. Taste tests revealed a preference for carbonated beverages containing bubbles of smaller size.
  • The inventors of the present application have surprisingly found that adding certain STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, especially, STEs, STCs, GSTEs and GSTCs, can minimiz the size of bubbles, thus improving the mouth feel and flavor of beverages. Accordingly, in some embodiments, compositions of STEs, STCs, GSTEs, and GSTCs, with or without other additives such as sweetening agents and/or thaumatin, can be used as additives to manipulate the size of bubbles, preferably for reducing the size of bubbles.
  • Additionally, the inventors surprisingly found that inclusion of thaumatin in combination of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, especially STEs, STCs, GSTEs and GSTCs can significantly improve the overall taste profile of food and beverages to have a better mouth feel, a creamy taste, a reduction of bitterness of other ingredients in food and beverage, such as  astringency of tea, protein, or their extracts, acidic nature and bitterness of coffee, etc. It can also reduce lingering, bitterness and metallic aftertaste of natural, synthetic high intensity sweeteners, or their combinations, their combination with other sweeteners, with other flavors much more than thaumatin itself. Thus, it plays a unique function in sugar reduction or sugar free products, and can be used as an additive for improving the taste performance of food and beverage products comprising one or more sweetening agents or sweeteners such as sucralose, acesulfame-K, aspartame, steviol glycosides, swingle extract, sweet tea extracts, allulose, sodium saccharin, sodium cyclamate or siratose.
  • A probiotic beverage normally is made by fermenting milk, or skimmed milk powder, sucrose and/or glucose with selected bacteria strains, by manufacturers such as Yakult or Weichuan. Normally, a large amount of sugar is added to the probiotic beverage to provide nutrients to the probiotics in order to keep them alive during shelf life. Actually, the main function of such a large amount of sugar is also needed to counteract the sourness of probiotic beverage and enhance its taste. Sweetness and the thickness are the two key attributes that are most affected for the acceptability of the beverage. It is a challenge for the manufacturers to produce tasteful probiotic beverages of reduced sugar versions.
  • In any of the embodiments described in the present application, the final concentration of any of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs in the beverage may be 0.0001 ppm, 0.001 ppm, 0.01 ppm, 0.1 ppm, 1 ppm, 2 ppm, 5 ppm, 10 ppm, 15 ppm, 20 ppm, 25 ppm, 30 ppm, 35 ppm, 40 ppm, 45 ppm, 50 ppm, 55 ppm, 60 ppm, 65 ppm, 70 ppm, 75 ppm, 80 ppm, 85 ppm, 90 ppm, 100 ppm, 110 ppm, 120, ppm, 130 ppm, 140 ppm, 150 ppm, 160 ppm, 170 ppm, 180 ppm, 190 ppm, 200 ppm, 220 ppm, 240 ppm, 260 ppm, 280 ppm, 300 ppm, 320 ppm, 340 ppm, 360 ppm 380 ppm, 400 ppm, 420 ppm, 440 ppm, 460 ppm, 480 ppm, 500 ppm, 525 ppm, 550 ppm, 575 ppm, 600 ppm, 625 ppm, 650 ppm, 675 ppm, 700 ppm, 725 ppm, 750 ppm, 775 ppm, 800 ppm, 825 ppm, 850 ppm, 875 ppm, 900 ppm, 925 ppm, 950 ppm, 975 ppm, 1,000 ppm, 1,200 ppm, 1,400 ppm, 1,600 ppm, 1,800 ppm, 2,000 ppm, 2,200 ppm, 2,400 ppm, 2,600 ppm, 2,800 ppm, 3,000 ppm, 3,200 ppm, 3,400 ppm, 3,600 ppm, 3,800 ppm, 4,000 ppm, 4,200 ppm, 4,400 ppm, 4,600 ppm, 4,800 ppm, 5,000 ppm, 5,500 ppm, 6,000 ppm, 6,500 ppm, 7,000 ppm, 7,500 ppm, 8,000 ppm, 8,500 ppm, 9,000 ppm, 9,500 ppm, 10,000 ppm, 11,000 ppm, 12,000 ppm, 13000  ppm, 14,000 ppm, 15,000 ppm, or a range defined by any pair of the aforementioned concentration values in this paragraph.
  • In more particular embodiments, any of the STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs may be present in the beverage at a final concentration ranging from 1 ppm to 15,000 ppm, from 1 ppm to 10,000 ppm, from 1 ppm to 5,000 ppm, from 10 ppm to 1,000 ppm, from 50 ppm to 900 ppm, from 50 ppm to 600 ppm, from 50 ppm to 500 ppm, from 50 ppm to 400 ppm, from 50 ppm to 300 ppm, from 50 ppm to 200 ppm, from 100 ppm to 600 ppm, from 100 ppm to 500 ppm, from 100 ppm to 400 ppm, from 100 ppm to 300 ppm, from 100 ppm to 200 ppm, from 125 ppm to 600 ppm, from 125 ppm to 500 ppm, from 125 ppm to 400 ppm, from 125 ppm to 300 ppm, from 125 ppm to 200 ppm, from 150 ppm to 600 ppm, from 150 ppm to 500 ppm, from 150 ppm to 500 ppm, from 150 ppm to 400 ppm, from 150 ppm to 300 ppm, from 150 ppm to 200 ppm, from 200 ppm to 600 ppm, from 200 ppm to 500 ppm, from 200 ppm to 400 ppm, from 200 ppm to 300 ppm, from 300 ppm to 600 ppm, from 300 ppm to 500 ppm, from 300 ppm to 400 ppm, from 400 ppm to 600 ppm, from 500 ppm to 600 ppm, from 20 ppm to 200 ppm, from 20 ppm to 180 ppm, from 20 ppm to 160 ppm, from 20 ppm to 140 ppm, from 20 ppm to 120 ppm, from 20 ppm to 100 ppm, from 20 ppm to 80 ppm, from 20 ppm to 60 ppm, from 20 ppm to 40 ppm, from 40 ppm to 150 ppm, from 40 ppm to 130 ppm, from 40 ppm to 100 ppm, from 40 ppm to 90 ppm, from 40 ppm to 70 ppm, from 40 ppm to 50 ppm, from 20 ppm to 100 ppm, from 40 ppm to 100 ppm, from 50 ppm to 100 ppm, from 60 ppm to 100 ppm, from 80 ppm to 100 ppm, from 5 ppm to 100 ppm, from 5 ppm to 95 ppm, from 5 ppm to 90 ppm, from 5 ppm to 85 ppm, from 5 ppm to 80 ppm, from 5 ppm to 75 ppm, from 5 ppm to 70 ppm, from 5 ppm to 65 ppm, from 5 ppm to 60 ppm, from 5 ppm to 55 ppm, from 5 ppm to 50 ppm, from 5 ppm to 45 ppm, from 5 ppm to 40 ppm, from 5 ppm to 35 ppm, from 5 ppm to 30 ppm, from 5 ppm to 25 ppm, from 5 ppm to 20 ppm, from 5 ppm to 15 ppm, from 5 ppm to 10 ppm, any aforementioned concentration value in this paragraph, or a range defined by any pair of the aforementioned concentration values in this paragraph. As used herein, ″final concentration″ refers to the concentration of, for example, any one of the aforementioned components present in any final composition or final orally consumable product (i.e., after all ingredients and/or compounds have been added to produce the composition or to produce the orally consumable product) .
  • B. Confections
  • In some embodiments, the consumable product comprising one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application is a confection. In some embodiments, a “confection” refers to a sweet, a lollipop, a confectionery, or similar term. The confection generally contains a base composition component and a sweetener component. A “base composition” refers to any composition which can be a food item and provides a matrix for carrying the sweetener component. The confection may be in the form of any food that is typically perceived to be rich in sugar or is typically sweet.
  • In other embodiments of the present application, the confection may be a bakery product, such as a pastry, Bavarian cream, blancmange, cake, brownie, cookie, mousse and the like; a dessert, such as yogurt, a jelly, a drinkable jelly, a pudding; a sweetened food product eaten at tea time or following meals; a frozen food; a cold confection, such as ice, ice milk, lacto-ice and the like (food products in which sweeteners and various other types of raw materials are added to milk products, and the resulting mixture is agitated and frozen) ; ice confections, such as sherbets, dessert ices and the like (food products in which various other types of raw materials are added to a sugary liquid, and the resulting mixture is agitated and frozen) ; general confections, e.g., baked confections or steamed confections such as crackers, biscuits, buns with bean-jam filling, halvah, alfajor, and the like; rice cakes and snacks; table top products; general sugar confections such as chewing gum (e.g., including compositions which comprise a substantially water-insoluble, chewable gum base, such as chicle or substitutes thereof, including jetulong, guttakay rubber or certain comestible natural synthetic resins or waxes) , hard candy, soft candy, mints, nougat candy, jelly beans, fudge, toffee, taffy, Swiss milk tablet, licorice candy, chocolates, gelatin candies, marshmallow, marzipan, divinity, cotton candy, and the like; sauces including fruit flavored sauces, chocolate sauces and the like; edible gels; cremes including butter cremes, flour pastes, whipped cream and the like; jams including strawberry jam, marmalade and the like; and breads including sweet breads and the like or other starch products, or combinations thereof.
  • Suitable base compositions for embodiments of this application may include flour, yeast, water, salt, butter, eggs, milk, milk powder, liquor, gelatin, nuts, chocolate, citric  acid, tartaric acid, fumaric acid, natural flavors, artificial flavors, colorings, polyols, sorbitol, isomalt, maltitol, lactitol, malic acid, magnesium stearate, lecithin, hydrogenated glucose syrup, glycerine, natural or synthetic gum, starch, and the like, or combinations thereof. Such components generally are recognized as safe (GRAS) and/or are U.S. Food and Drug Administration (FDA) -approved.
  • In any of the condiments described herein, the STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be present in the condiment at a final weight concentration of 0.0001 wt %, 0.001 wt %, 0.01 wt %, 0.1 wt %, 1 wt %, 2 wt %, 3 wt %, 4 wt %, 5 wt %, 6 wt %, 7 wt %, 8 wt %., 9wt %, 10wt %, 11 wt %, 12 wt %, 13 wt %, 14wt %, 15 wt %, 16wt %, 17 wt %, 18 wt %, 19 wt %, 20 wt %, 21 wt %, 22 wt %, 23 wt %, 24 wt %, 25 wt %, 26 wt %, 27 wt %, 28 wt %, 29 wt %, 30wt %, 31wt %, 32wt %, 33 wt %, 34wt %, 35 wt %, 36wt %, 37 wt %, 38 wt %, 39 wt %, 40 wt %, 41 wt %, 42 wt %, 43 wt %, 44 wt %, 45 wt %, 46 wt %, 47 wt %, 48 wt %, 49 wt %, 50 wt %, 51 wt %, 52 wt %, 53 wt %, 54 wt %, 55 wt %, 56 wt %, 57 wt %, 58 wt %, 59 wt %, 60 wt %, 61 wt %, 62 wt %, 63 wt %, 64 wt %, 65 wt %, 66 wt %, 67 wt %, 68 wt %, 69 wt %, 70 wt %, 71 wt %, 72 wt %, 73 wt %, 74 wt %, 75 wt %, 76 wt %, 77 wt %, 78 wt %, 79 wt %, 80 wt %, or a weight concentration range defined by any two of the aforementioned weight percentages in this paragraph.
  • In more particular embodiments, the STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be present in any of the condiments described herein at a final weight percentage range from 0.001 wt %to 99 wt %, 0.001 wt %to 75 wt %, 0.001 wt %to 50 wt%, 0.001 wt %to 25 wt%, 0.001 wt %to 10 wt %, 0.001 wt %to 5 wt %, 0.001 wt %to 2 wt %, 0.001 wt %to 1 wt %, 0.001 wt %to 0.1 wt %, 0.001 wt %to 0.01 wt %, 0.01 wt %to 99 wt %, 0.01 wt %to 75 wt %, 0.01 wt %to 50 wt%, 0.01 wt %to 25 wt%., 0.01 wt %to 10 wt %, 0.01 wt %to 5 wt %, 0.01 wt %to 2 wt %, 0.01 wt %to 1 wt %, 0.1 wt %to 99 wt %, 0.1 wt %to 75 wt %, 0.1 wt %to 50 wt%, 0.1 wt %to 25 wt%, 0.1 wt %to 10 wt %, 0.1 wt %to 5 wt %, 0.1 wt %to 2 wt %, 0.1 wt %to 1 wt %, 0.1 wt %to 0.5 wt %, 1 wt %to 99 wt %, 1 wt %to 75 wt %, 1 wt %to 50 wt%, 1 wt %to 25 wt%, 1 wt %to 10 wt %, 1 wt %to 5 wt %, 5 wt %to 99 wt %, 5 wt %to 75 wt %, 5 wt %to 50 wt%, 5 wt %to 25 wt%, 5 wt %to 10 wt %, 10 wt %to  99 wt %, 10 wt %to 75 wt %, 10 wt %to 50 wt%, 10 wt %to 25 wt%, 10 wt %to 15 wt %, 20 wt %to 99 wt %, 20 wt %to 75 wt %, 20 wt %to 50 wt%, 30 wt %to 99 wt %, 30 wt %to 75 wt %, 30 wt %to 50 wt%, 40 wt %to 99 wt %, 40 wt %to 75 wt %, 40 wt %to 50 wt%, 50 wt %to 99 wt %, 50 wt %to 75 wt %, 60 wt %to 99 wt %, 60 wt %to 75 wt %, 70 wt %to 99 wt %, 70 wt %to 75 wt %, 80 wt %to 99 wt %, 80 wt %to 90 wt %, 90 wt %to 99 wt%, or a weight concentration range defined by any two of the aforementioned weight percentages in this paragraph.
  • The base composition of the confection may optionally include other artificial or natural sweeteners, bulk sweeteners, or combinations thereof. Bulk sweeteners include both caloric and non-caloric compounds. Non-limiting examples of bulk sweeteners include sucrose, dextrose, maltose, dextrin, dried invert sugar, fructose or fruit sugar, levulose, honey, unrefined sweetener, galactose, syrups, such as agave syrup or agave nectar, maple syrup, corn syrup, including high fructose corn syrup (HFCS) ; solids, tagatose, polyols (e.g., sorbitol, mannitol, xylitol, lactitol, erythritol, and maltitol) , hydrogenated starch hydrolysates, isomalt, trehalose, or mixtures thereof. Generally, the amount of bulk sweetener present in the confection ranges widely depending on the particular embodiment of the confection and the desired degree of sweetness. Those of ordinary skill in the art will readily ascertain the appropriate amount of bulk sweetener.
  • C. Condiments
  • In some embodiments, the consumable product that contains STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application is a condiment. Condiments, as used herein, are compositions used to enhance or improve the flavor of a food or beverage. Non-limiting examples of condiments include ketchup (catsup) ; mustard; barbecue sauce; butter; chili sauce; chutney; cocktail sauce; curry; dips; fish sauce; horseradish; hot sauce; jellies, jams, marmalades, or preserves; mayonnaise; peanut butter; relish; remoulade; salad dressings (e.g., oil and vinegar, Caesar, French, ranch, bleu cheese, Russian, Thousand Island, Italian, and balsamic vinaigrette) , salsa; sauerkraut; soy sauce; steak sauce; syrups; tartar sauce; and Worcestershire sauce.
  • Condiment bases generally comprise a mixture of different ingredients, non-limiting examples of which include vehicles (e.g., water and vinegar) ; spices or seasonings (e.g.,  salt, pepper, garlic, mustard seed, onion, paprika, turmeric, or combinations thereof) ; fruits, vegetables, or their products (e.g., tomatoes or tomato-based products (paste, puree) , fruit juices, fruit juice peels, or combinations thereof) ; oils or oil emulsions, particularly vegetable oils; thickeners (e.g., xanthan gum, food starch, other hydrocolloids, or combinations thereof) ; and emulsifying agents (e.g., egg yolk solids, protein, gum arabic, carob bean gum, guar gum, gum karaya, gum tragacanth, carageenan, pectin, propylene glycol esters of alginic acid, sodium carboxymethyl-cellulose, polysorbates, or combinations thereof) . Recipes for condiment bases and methods of making condiment bases are well known to those of ordinary skill in the art.
  • Generally, condiments also comprise caloric sweeteners, such as sucrose, high fructose corn syrup, molasses, honey, or brown sugar. In exemplary embodiments of the condiments provided herein, an composition containing one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application is used instead of traditional caloric sweeteners.
  • The condiment composition optionally may include other natural and/or synthetic high-potency sweeteners, bulk sweeteners, pH modifying agents (e.g., lactic acid, citric acid, phosphoric acid, hydrochloric acid, acetic acid, or combinations thereof) , fillers, functional agents (e.g., pharmaceutical agents, nutrients, or components of a food or plant) , flavoring agents, colorings, or combinations thereof.
  • In any of the confections described herein, the STEs, STCs, SGs, SEs, SCs, MGs. MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be present in the confection at a final weight concentration of 0.0001 wt %, 0.001 wt %, 0.01 wt %, 0.1 wt %, 1 wt %, 2 wt %, 3 wt %, 4 wt %, 5 wt %, 6 wt %, 7 wt %, 8 wt %, 9wt %, 10wt %, 11 wt %, 12 wt %, 13 wt %, 14wt %, 15 wt %, 16 wt %, 17 wt %, 18 wt %, 19 wt %, 20 wt %, 21 wt %, 22 wt %, 23 wt %, 24 wt %, 25 wt %, 26 wt %, 27 wt %, 28 wt %, 29 wt %, 30 wt %, 31 wt %, 32 wt %, 33 wt %, 34 wt %, 35 wt %, 36 wt %, 37 wt %, 38 wt %, 39 wt %, 40 wt %, 41 wt %, 42 wt %, 43 wt %, 44 wt %, 45 wt %, 46 wt %, 47 wt %, 48 wt %, 49 wt %, 50 wt %, 51 wt %, 52 wt %, 53 wt %, 54 wt %, 55 wt %, 56 wt %, 57 wt %, 58 wt %, 59 wt %, 60 wt %, 61 wt %, 62 wt %, 63 wt %, 64 wt %, 65 wt %, 66 wt %, 67 wt %, 68 wt %, 69 wt %, 70 wt %, 71 wt %, 72 wt %, 73 wt %, 74 wt %, 75 wt %, 76 wt %, 77  wt %, 78 wt %, 79 wt %, 80 wt %, or a weight concentration range defined by any two of the aforementioned weight percentages in this paragraph.
  • In more particular embodiments, STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be present in any of the confections described herein, at a final weight percentage range from 0.001 wt %to 99 wt %, 0.001 wt %to 75 wt %, 0.001 wt %to 50 wt%, 0.001 wt %to 25 wt%, 0.001 wt %to 10 wt %, 0.001 wt %to 5 wt %, 0.001 wt %to 2 wt %, 0.001 wt %to 1 wt %, 0.001 wt %to 0.1 wt %, 0.001 wt %to 0.01 wt %, 0.01 wt %to 99 wt %, 0.01 wt %to 75 wt %, 0.01 wt %to 50 wt%, 0.01 wt %to 25 wt%., 0.01 wt %to 10 wt %, 0.01 wt %to 5 wt %, 0.01 wt %to 2 wt %, 0.01 wt %to 1 wt %, 0.1 wt %to 99 wt %, 0.1 wt %to 75 wt %, 0.1 wt %to 50 wt%, 0.1 wt %to 25 wt%, 0.1 wt %to 10 wt %, 0.1 wt %to 5 wt %, 0.1 wt %to 2 wt %, 0.1 wt %to 1 wt %, 0.1 wt %to 0.5 wt %, 1 wt %to 99 wt %, 1 wt %to 75 wt %, 1 wt %to 50 wt%, 1 wt %to 25 wt%, 1 wt %to 10 wt %, 1 wt %to 5 wt %, 5 wt %to 99 wt %, 5 wt %to 75 wt %, 5 wt %to 50 wt%, 5 wt %to 25 wt%, 5 wt %to 10 wt %, 10 wt %to 99 wt %, 10 wt %to 75 wt %, 10 wt %to 50 wt%, 10 wt %to 25 wt%, 10 wt %to 15 wt %, 20 wt %to 99 wt %, 20 wt %to 75 wt %, 20 wt %to 50 wt%, 30 wt %to 99 wt %, 30 wt %to 75 wt %, 30 wt %to 50 wt%, 40 wt %to 99 wt %, 40 wt %to 75 wt %, 40 wt %to 50 wt%, 50 wt %to 99 wt %, 50 wt %to 75 wt %, 60 wt %to 99 wt %, 60 wt %to 75 wt %, 70 wt %to 99 wt %, 70 wt %to 75 wt %, 80 wt %to 99 wt %, 80 wt %to 90 wt %, 90 wt %to 99 wt%, or a weight concentration range defined by any two of the aforementioned weight percentages in this paragraph.
  • D. Dairy Products
  • A wide variety of dairy products can be made using the STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present invention. Such products include without limitation, milk, whole milk, buttermilk, skim milk, infant formula, condensed milk, dried milk, evaporated milk, fermented milk, butter, clarified butter, cottage cheese, cream cheese, and various types of cheese.
  • In any of the solid dairy compositions described herein, the STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be present in the solid dairy composition at a final weight  concentration of 0.0001 wt %, 0.001 wt %, 0.01 wt %, 0.1 wt %, 1 wt %, 2 wt %, 3 wt %, 4 wt %, 5 wt %, 6 wt %, 7 wt %, 8wt %, 9wt %, 10 wt %, 11 wt %, 12 wt %, 13 wt %, 14 wt %, 15 wt %, 16wt %, 17wt %, 18wt %, 19wt %, 20wt %, 21wt %, 22 wt %, 23 wt %, 24 wt %, 25 wt %, 26 wt %, 27 wt %, 28 wt %, 29 wt %, 30 wt %, 31 wt %, 32 wt %, 33 wt %, 34 wt %, 35 wt %, 36 wt %, 37 wt %, 38 wt %, 39 wt %, 40 wt %, 41 wt %, 42 wt %, 43 wt %, 44 wt %, 45 wt %, 46 wt %, 47 wt %, 48 wt %, 49 wt %, 50 wt %, 51 wt %, 52 wt %, 53 wt %, 54 wt %, 55 wt %, 56 wt %, 57 wt %, 58 wt %, 59 wt %, 60 wt %, 61 wt %, 62 wt %, 63 wt %, 64 wt %, 65 wt %, 66 wt %, 67 wt %, 68 wt %, 69 wt %, 70 wt %, 71 wt %, 72 wt %, 73 wt %, 74 wt %, 75 wt %, 76 wt %, 77 wt %, 78 wt %, 79 wt %, 80 wt %, or a weight concentration range defined by any two of the aforementioned weight percentages in this paragraph.
  • In more particular embodiments, the STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be present in any of the confections described herein, at a weight percentage range from 0.001 wt %to 99 wt %, 0.001 wt %to 75 wt %, 0.001 wt %to 50 wt%, 0.001 wt %to 25 wt%, 0.001 wt %to 10 wt %, 0.001 wt %to 5 wt %, 0.001 wt %to 2 wt %, 0.001 wt %to 1 wt %, 0.001 wt %to 0.1 wt %, 0.001 wt %to 0.01 wt %, 0.01 wt %to 99 wt %, 0.01 wt %to 75 wt %, 0.01 wt %to 50 wt%, 0.01 wt %to 25 wt%., 0.01 wt %to 10 wt %, 0.01 wt %to 5 wt %, 0.01 wt %to 2 wt %, 0.01 wt %to 1 wt %, 0.1 wt %to 99 wt %, 0.1 wt %to 75 wt %, 0.1 wt %to 50 wt%, 0.1 wt %to 25 wt%, 0.1 wt %to 10 wt %, 0.1 wt %to 5 wt %, 0.1 wt %to 2 wt %, 0.1 wt %to 1 wt %, 0.1 wt %to 0.5 wt %, 1 wt %to 99 wt %, 1 wt %to 75 wt %, 1 wt %to 50 wt%, 1 wt %to 25 wt%, 1 wt %to 10 wt %, 1 wt %to 5 wt %, 5 wt %to 99 wt %, 5 wt %to 75 wt %, 5 wt %to 50 wt%, 5 wt %to 25 wt%, 5 wt %to 10 wt %, 10 wt %to 99 wt %, 10 wt %to 75 wt %, 10 wt %to 50 wt%, 10 wt %to 25 wt%, 10 wt %to 15 wt %, 20 wt %to 99 wt %, 20 wt %to 75 wt %, 20 wt %to 50 wt%, 30 wt %to 99 wt %, 30 wt %to 75 wt %, 30 wt %to 50 wt%, 40 wt %to 99 wt %, 40 wt %to 75 wt %, 40 wt %to 50 wt%, 50 wt %to 99 wt %, 50 wt %to 75 wt %, 60 wt %to 99 wt %, 60 wt %to 75 wt %, 70 wt %to 99 wt %, 70 wt %to 75 wt %, 80 wt %to 99 wt %, 80 wt %to 90 wt %, 90 wt %to 99 wt%, or a weight concentration range defined by any two of the aforementioned weight percentages in this paragraph.
  • Alternatively, in any of the liquid dairy compositions described herein, the STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be present in the liquid dairy composition at a final concentration of 0.0001 ppm, 0.001 ppm, 0.01 ppm, 0.1 ppm, 1 ppm, 2 ppm, 5 ppm, 10 ppm, 15 ppm, 20 ppm, 25 ppm, 30 ppm, 35 ppm, 40 ppm, 45 ppm, 50 ppm, 55 ppm, 60 ppm, 65 ppm, 70 ppm, 75 ppm, 80 ppm, 85 ppm, 90 ppm, 100 ppm, 110 ppm, 120, ppm, 130 ppm, 140 ppm, 150 ppm, 160 ppm, 170 ppm, 180 ppm, 190 ppm, 200 ppm, 220 ppm, 240 ppm, 260 ppm, 280 ppm, 300 ppm, 320 ppm, 340 ppm, 360 ppm 380 ppm, 400 ppm, 420 ppm, 440 ppm, 460 ppm, 480 ppm, 500 ppm, 525 ppm, 550 ppm, 575 ppm,600 ppm, 625 ppm, 650 ppm, 675 ppm, 700 ppm, 725 ppm, 750 ppm, 775 ppm, 800 ppm, 825 ppm, 850 ppm, 875 ppm, 900 ppm, 925 ppm, 950 ppm, 975 ppm, 1,000 ppm, 1,200 ppm, 1,400 ppm, 1,600 ppm, 1,800 ppm, 2,000 ppm, 2,200 ppm, 2,400 ppm, 2,600 ppm, 2,800 ppm, 3,000 ppm, 3,200 ppm, 3,400 ppm, 3,600 ppm, 3,800 ppm, 4,000 ppm, 4,200 ppm, 4,400 ppm, 4,600 ppm, 4,800 ppm, 5,000 ppm, 5,500 ppm, 6,000 ppm, 6,500 ppm, 7,000 ppm, 7,500 ppm, 8,000 ppm, 8,500 ppm, 9,000 ppm, 9,500 ppm, 10,000 ppm, 11,000 ppm, 12,000 ppm, 13000 ppm, 14,000 ppm, 15,000 ppm, or a range defined by any pair of the aforementioned concentration values in this paragraph.
  • In more particular embodiments, the STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be present in the liquid dairy composition at a final concentration ranging from 1 ppm to 15,000 ppm, from 1 ppm to 10,000 ppm, from 1 ppm to 5,000 ppm, from 10 ppm to 1,000 ppm, from 50 ppm to 900 ppm, from 50 ppm to 600 ppm, from 50 ppm to 500 ppm, from 50 ppm to 400 ppm, from 50 ppm to 300 ppm, from 50 ppm to 200 ppm, from 100 ppm to 600 ppm, from 100 ppm to 500 ppm, from 100 ppm to 400 ppm, from 100 ppm to 300 ppm, from 100 ppm to 200 ppm, from 125 ppm to 600 ppm, from 125 ppm to 500 ppm, from 125 ppm to 400 ppm, from 125 ppm to 300 ppm, from 125 ppm to 200 ppm, from 150 ppm to 600 ppm, from 150 ppm to 500 ppm, from 150 ppm to 500 ppm, from 150 ppm to 400 ppm, from 150 ppm to 300 ppm, from 150 ppm to 200 ppm, from 200 ppm to 600 ppm, from 200 ppm to 500 ppm, from 200 ppm to 400 ppm, from 200 ppm to 300 ppm, from 300 ppm to 600 ppm, from 300 ppm to 500 ppm, from 300 ppm to 400 ppm, from 400 ppm to 600 ppm, from 500 ppm to 600 ppm, from 20 ppm to 200 ppm, from 20 ppm to 180 ppm, from 20 ppm to 160 ppm, from 20 ppm to 140 ppm, from 20 ppm to 120 ppm, from 20 ppm to 100 ppm, from 20 ppm to 80 ppm, from 20  ppm to 60 ppm, from 20 ppm to 40 ppm, from 40 ppm to 150 ppm, from 40 ppm to 130 ppm, from 40 ppm to 100 ppm, from 40 ppm to 90 ppm, from 40 ppm to 70 ppm, from 40 ppm to 50 ppm, from 20 ppm to 100 ppm, from 40 ppm to 100 ppm, from 50 ppm to 100 ppm, from 60 ppm to 100 ppm, from 80 ppm to 100 ppm, from 5 ppm to 100 ppm, from 5 ppm to 95 ppm, from 5 ppm to 90 ppm, from 5 ppm to 85 ppm, from 5 ppm to 80 ppm, from 5 ppm to 75 ppm, from 5 ppm to 70 ppm, from 5 ppm to 65 ppm, from 5 ppm to 60 ppm, from 5 ppm to 55 ppm, from 5 ppm to 50 ppm, from 5 ppm to 45 ppm, from 5 ppm to 40 ppm, from 5 ppm to 35 ppm, from 5 ppm to 30 ppm, from 5 ppm to 25 ppm, from 5 ppm to 20 ppm, from 5 ppm to 15 ppm, from 5 ppm to 10 ppm, any aforementioned concentration value in this paragraph, or a range defined by any pair of the aforementioned concentration values in this paragraph.
  • E. Cereal Compositions
  • In some embodiments, the consumable product comprising one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application is a cereal composition. Cereal compositions typically are eaten either as staple foods or as snacks. Non-limiting examples of cereal compositions for use in some embodiments include ready-to-eat cereals as well as hot cereals. Ready-to-eat cereals are cereals which may be eaten without further processing (i.e., cooking) by the consumer. Examples of ready-to-eat cereals include breakfast cereals and snack bars. Breakfast cereals typically are processed to produce a shredded, flaky, puffy, or extruded form. Breakfast cereals generally are eaten cold and are often mixed with milk and/or fruit. Snack bars include, for example, energy bars, rice cakes, granola bars, and nutritional bars. Hot cereals generally are cooked, usually in either milk or water, before being eaten. Non-limiting examples of hot cereals include grits, porridge, polenta, rice, oatmeal, and rolled oats.
  • Cereal compositions generally comprise at least one cereal ingredient. As used herein, the term “cereal ingredient” denotes materials such as whole or part grains, whole or part seeds, and whole or part grass. Non-limiting examples of cereal ingredients for use in some embodiments include maize, wheat, rice, barley, bran, bran endosperm, bulgur, sorghums, millets, oats, rye, triticale, buckwheat, fonio, quinoa, bean, soybean, amaranth, teff, spelt, and kaniwa.
  • The cereal composition comprises one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application and at least one cereal ingredient. The STEs, STCs, GSTEs and GSTCs of present application may be added to the cereal composition in a variety of ways, such as, for example, as a coating, as a frosting, as a glaze, or as a matrix blend (i.e., added as an ingredient to the cereal formulation prior to the preparation of the final cereal product) .
  • Accordingly, in some embodiments, one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application are added to the cereal composition as a matrix blend. In one embodiment, one or more STEs, STCs, GSTEs and GSTCs are blended with a hot cereal prior to cooking to provide a sweetened hot cereal product. In another embodiment, one or more STEs, STCs, GSTEs, and GSTCs are blended with the cereal matrix before the cereal is extruded.
  • In some embodiments, one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs are added to the cereal composition as a coating, such as, for example, in combination with food grade oil and applying the mixture onto the cereal. In a different embodiment, one or more STEs, STCs, SGs, SEs, SCs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMFEs and GMFCs, and the food grade oil are applied to the cereal separately, by applying either the oil or the sweetener first. Non-limiting examples of food grade oils for use some embodiments include vegetable oils such as corn oil, soybean oil, cottonseed oil, peanut oil, coconut oil, canola oil, olive oil, sesame seed oil, palm oil, palm kernel oil, or mixtures thereof. In yet another embodiment, food grade fats may be used in place of the oils, provided that the fat is melted prior to applying the fat onto the cereal.
  • In another embodiment, one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs are added to the cereal composition as a glaze. Non-limiting examples of glazing agents for use in some embodiments include corn syrup, honey syrups and honey syrup solids, maple syrups and maple syrup solids, sucrose, isomalt, polydextrose, polyols, hydrogenated starch hydrolysate, aqueous solutions thereof, or mixtures thereof. In another such embodiment, one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and  GMFCs are added as a glaze by combining with a glazing agent and a food grade oil or fat and applying the mixture to the cereal. In yet another embodiment, a gum system, such as, for example, gum acacia, carboxymethyl cellulose, or algin, may be added to the glaze to provide structural support. In addition, the glaze also may include a coloring agent, and also may include a flavor.
  • In another embodiment one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs are added to the cereal composition as a frosting. In one such embodiment, one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs are combined with water and a frosting agent and then applied to the cereal. Non-limiting examples of frosting agents for use in some embodiments include maltodextrin, sucrose, starch, polyols, or mixtures thereof. The frosting also may include a food grade oil, a food grade fat, a coloring agent, and/or a flavor.
  • In any of the cereal compositions described herein, the one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs are present in the cereal composition at a final weight concentration of 0.0001 wt %, 0.001 wt %, 0.01 wt %, 0.1 wt %, 1 wt %, 2wt %, 3 wt %, 4wt %, 5 wt %, 6wt %, 7wt %, 8 wt %, 9 wt %, 10wt %, 11 wt %, 12 wt %, 13 wt %, 14wt %, 15 wt %, 16wt %, 17 wt %, 18 wt %, 19 wt %, 20 wt %, 21 wt %, 22 wt %, 23 wt %, 24 wt %, 25 wt %, 26 wt %, 27 wt %, 28 wt %, 29 wt %, 30 wt %, 31 wt %, 32 wt %, 33 wt %, 34 wt %, 35 wt %, 36 wt %, 37 wt %, 38 wt %, 39 wt %, 40 wt %, 41 wt %, 42 wt %, 43 wt %, 44 wt %, 45 wt %, 46 wt %, 47 wt %, 48 wt %, 49 wt %, 50 wt %, 51 wt %, 52 wt %, 53 wt %, 54 wt %, 55 wt %, 56 wt %, 57 wt %, 58 wt %, 59 wt %, 60 wt %, 61 wt %, 62 wt %, 63 wt %, 64 wt %, 65 wt %, 66 wt %, 67 wt %, 68 wt %, 69 wt %, 70 wt %, 71 wt %, 72 wt %, 73 wt %, 74 wt %, 75 wt %, 76 wt %, 77 wt %, 78 wt %, 79 wt %, 80 wt %, or a weight concentration range defimed by any two of the aforementioned weight percentages in this paragraph.
  • In some embodiments, one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs may be present in any of the cereal compositions described herein, at a weight percentage range from 0.001 wt %to 99 wt %, 0.001 wt %to 75 wt %, 0.001 wt %to 50 wt%, 0.001 wt %to 25 wt%, 0.001 wt %to 10  wt %, 0.001 wt %to 5 wt %, 0.001 wt %to 2 wt %, 0.001 wt %to 1 wt %, 0.001 wt %to 0.1 wt %, 0.001 wt %to 0.01 wt %, 0.01 wt %to 99 wt %, 0.01 wt %to 75 wt %, 0.01 wt %to 50 wt%, 0.01 wt %to 25 wt%., 0.01 wt %to 10 wt %, 0.01 wt %to 5 wt %, 0.01 wt %to 2 wt %, 0.01 wt %to 1 wt %, 0.1 wt %to 99 wt %, 0.1 wt %to 75 wt %, 0.1 wt %to 50 wt%, 0.1 wt %to 25 wt%, 0.1 wt %to 10 wt %, 0.1 wt %to 5 wt %, 0.1 wt %to 2 wt %, 0.1 wt %to 1 wt %, 0.1 wt %to 0.5 wt %, 1 wt %to 99 wt %, 1 wt %to 75 wt %, 1 wt %to 50 wt%, 1 wt %to 25 wt%, 1 wt %to 10 wt %, 1 wt %to 5 wt %, 5 wt %to 99 wt %, 5 wt %to 75 wt %, 5 wt %to 50 wt%, 5 wt %to 25 wt%, 5 wt %to 10 wt %, 10 wt %to 99 wt %, 10 wt %to 75 wt %, 10 wt %to 50 wt%, 10 wt %to 25 wt%, 10 wt %to 15 wt %, 20 wt %to 99 wt %, 20 wt %to 75 wt %, 20 wt %to 50 wt%, 30 wt %to 99 wt %, 30 wt %to 75 wt %, 30 wt %to 50 wt%, 40 wt %to 99 wt %, 40 wt %to 75 wt %, 40 wt %to 50 wt%, 50 wt %to 99 wt %, 50 wt %to 75 wt %, 60 wt %to 99 wt %, 60 wt %to 75 wt %, 70 wt %to 99 wt %, 70 wt %to 75 wt %, 80 wt %to 99 wt %, 80 wt %to 90 wt %, 90 wt %to 99 wt%, or a weight concentration range defined by any two of the aforementioned weight percentages in this paragraph.
  • F. Chewing Compositions
  • In some embodiments, the consumable product comprising one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application is a chewing composition. The term “chewing compositions” include chewing gum compositions, chewing tobacco, smokeless tobacco, snuff, chewing gum and other compositions which are masticated and subsequently expectorated.
  • Chewing gum compositions generally comprise a water-soluble portion and a water-insoluble chewable gum base portion. The water soluble portion, which typically includes one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application, dissipates with a portion of the flavoring agent over a period of time during chewing while the insoluble gum base portion is retained in the mouth. The insoluble gum base generally determines whether a gum is considered chewing gum, bubble gum, or a functional gum.
  • The insoluble gum base, which is generally present in the chewing gum composition in an amount in the range of about 15 to about 35 weight percent of the chewing gum composition, generally comprises combinations of elastomers, softeners (plasticizers) ,  emulsifiers, resins, and fillers. Such components generally are considered food grade, recognized as safe (GRA) , and/or are U.S. Food and Drug Administration (FDA) -approved.
  • Elastomers, the primary component of the gum base, provide the rubbery, cohesive nature to gums and can include one or more natural rubbers (e.g., smoked latex, liquid latex, or guayule) ; natural gums (e.g., jelutong, perillo, sorva, massaranduba balata, massaranduba chocolate, nispero, rosindinha, chicle, and gutta hang kang) ; or synthetic elastomers (e.g., butadiene-styrene copolymers, isobutylene-isoprene copolymers, polybutadiene, polyisobutylene, and vinyl polymeric elastomers) . In a particular embodiment, the elastomer is present in the gum base in an amount in the range of about 3 to about 50 weight percent of the gum base.
  • Resins are used to vary the firmness of the gum base and aid in softening the elastomer component of the gum base. Non-limiting examples of suitable resins include a rosin ester, a terpene resin (e.g., a terpene resin from α-pinene, β-pinene and/or D-limonene) , polyvinyl acetate, polyvinyl alcohol, ethylene vinyl acetate, and vinyl acetate-vinyl laurate copolymers. Non-limiting examples of rosin esters include a glycerol ester of a partially hydrogenated rosin, a glycerol ester of a polymerized rosin, a glycerol ester of a partially dimerized rosin, a glycerol ester of rosin, a pentaerythritol ester of a partially hydrogenated rosin, a methyl ester of rosin, or a methyl ester of a partially hydrogenated rosin. In some embodiment, the resin is present in the gum base in an amount in the range of about 5 to about 75 weight percent of the gum base.
  • Softeners, which also are known as plasticizers, are used to modify the ease of chewing and/or mouth feel of the chewing gum composition. Generally, softeners comprise oils, fats, waxes, and emulsifiers. Non-limiting examples of oils and fats include tallow, hydrogenated tallow, large, hydrogenated or partially hydrogenated vegetable oils (e.g., soybean, canola, cottonseed, sunflower, palm, coconut, corn, safflower, or palm kernel oils) , cocoa butter, glycerol monostearate, glycerol triacetate, glycerol abietate, lecithin, monoglycerides, diglycerides, triglycerides acetylated monoglycerides, and free fatty acids. Non-limiting examples of waxes include polypropylene/polyethylene/Fisher-Tropsch waxes, paraffin, and microcrystalline and natural waxes (e.g., candelilla, beeswax and carnauba) . Microcrystalline waxes, especially those with a high degree of crystallinity and a high melting point, also may be  considered as bodying agents or textural modifiers. In some embodiments, the softeners are present in the gum base in an amount in the range of about 0.5 to about 25 weight percent of the gum base.
  • Emulsifiers are used to form a uniform dispersion of the insoluble and soluble phases of the chewing gum composition and also have plasticizing properties. Suitable emulsifiers include glycerol monostearate (GMS) , lecithin (phosphatidyl choline) , polyglycerol polyricinoleic acid (PPGR) , mono and diglycerides of fatty acids, glycerol distearate, tracetin, acetylated monoglyceride, glycerol triacetate, and magnesium stearate. In some embodiments, the emulsifiers are present in the gum base in an amount in the range of about 2 to about 30 weight percent of the gum base.
  • The chewing gum composition also may comprise adjuvants or fillers in either the gum base and/or the soluble portion of the chewing gum composition. Suitable adjuvants and fillers include lecithin, inulin, polydextrin, calcium carbonate, magnesium carbonate, magnesium silicate, ground limestone, aluminum hydroxide, aluminum silicate, talc, clay, alumina, titanium dioxide, and calcium phosphate. In some embodiments, lecithin can be used as an inert filler to decrease the stickiness of the chewing gum composition. In other some embodiments, lactic acid copolymers, proteins (e.g., gluten and/or zein) and/or guar can be used to create a gum that is more readily biodegradable. The adjuvants or fillers are generally present in the gum base in an amount up to about 20 weight percent of the gum base. Other optional ingredients include coloring agents, whiteners, preservatives, and flavors.
  • In some embodiments of the chewing gum composition, the gum base comprises about 5 to about 95 weight percent of the chewing gum composition, more desirably about 15 to about 50 weight percent of the chewing gum composition, and even more desirably from about 20 to about 30 weight percent of the chewing gum composition.
  • The soluble portion of the chewing gum composition may optionally include other artificial or natural sweeteners, bulk sweeteners, softeners, emulsifiers, flavoring agents, coloring agents, adjuvants, fillers, functional agents (e.g., pharmaceutical agents or nutrients) , or combinations thereof. Suitable examples of softeners and emulsifiers are described above.
  • Bulk sweeteners include both caloric and non-caloric compounds. Non-limiting examples of bulk sweeteners include sucrose, dextrose, maltose, dextrin, dried invert sugar, fructose, high fructose corn syrup, levulose, galactose, corn syrup solids, tagatose, polyols (e.g., sorbitol, mannitol, xylitol, lactitol, erythritol, and maltitol) , hydrogenated starch hydrolysates, isomalt, trehalose, or mixtures thereof. In some embodiments, the bulk sweetener is present in the chewing gum composition in an amount in the range of about 1 to about 75 weight percent of the chewing gum composition.
  • Flavoring agents may be used in either the insoluble gum base or soluble portion of the chewing gum composition. Such flavoring agents may be natural or artificial flavors. In some embodiments, the flavoring agent comprises an essential oil, such as an oil produced from a plant or a fruit, peppermint oil, spearmint oil, other mint oils, clove oil, cinnamon oil, oil of wintergreen, bay, thyme, cedar leaf, nutmeg, allspice, sage, mace, and almonds. In another embodiment, the flavoring agent comprises a plant extract or a fruit essence such as apple, banana, watermelon, pear, peach, grape, strawberry, raspberry, cherry, plum, pineapple, apricot, or mixtures thereof. In still another embodiment, the flavoring agent comprises a citrus flavor, such as an extract, essence, or oil of lemon, lime, orange, tangerine, grapefruit, citron, or kumquat.
  • In some embodiments, the chewing gum composition comprises one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application and a gum base.
  • In any of the chewing gum compositions described herein, the one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be present in the chewing gum composition at a final weight concentration of 0.0001 wt %, 0.001 wt %, 0.01 wt %, 0.1 wt %, 1 wt %, 2 wt %, 3 wt %, 4wt %, 5 wt %, 6wt %, 7wt %, 8 wt %, 9wt %, 10 wt %, 11 wt %, 12 wt %, 13 wt %, 14 wt %, 15 wt %, 16 wt %, 17 wt %, 18 wt %, 19 wt %, 20 wt %, 21 wt %, 22 wt %, 23 wt %, 24 wt %, 25 wt %, 26 wt %, 27 wt %, 28 wt %, 29 wt %, 30 wt %, 31 wt %, 32 wt %, 33 wt %, 34 wt %, 35 wt %, 36 wt %, 37 wt %, 38 wt %, 39 wt %, 40 wt %, 41 wt %, 42 wt %, 43 wt %, 44 wt %, 45 wt %, 46 wt %, 47 wt %, 48 wt %, 49 wt %, 50 wt %, 51 wt %, 52 wt %, 53 wt %, 54 wt %, 55 wt %, 56 wt %, 57 wt %, 58 wt %, 59 wt %, 60 wt %, 61 wt %, 62 wt %, 63 wt %,  64 wt %, 65 wt %, 66 wt %, 67 wt %, 68 wt %, 69 wt %, 70 wt %, 71 wt %, 72 wt %, 73 wt %, 74 wt %, 75 wt %, 76 wt %, 77 wt %, 78 wt %, 79 wt %, 80 wt %, or a weight concentration range defined by any two of the aforementioned weight percentages in this paragraph.
  • In more particular embodiments, the one or STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be present in any of the chewing gum compositions described herein, at a weight percentage range from 0.001 wt %to 99 wt %, 0.001 wt %to 75 wt %, 0.001 wt %to 50 wt%, 0.001 wt %to 25 wt%, 0.001 wt %to 10 wt %, 0.001 wt %to 5 wt %, 0.001 wt %to 2 wt %, 0.001 wt %to 1 wt %, 0.001 wt %to 0.1 wt %, 0.001 wt %to 0.01 wt %, 0.01 wt %to 99 wt %, 0.01 wt %to 75 wt %, 0.01 wt %to 50 wt%, 0.01 wt %to 25 wt%., 0.01 wt %to 10 wt %, 0.01 wt %to 5 wt %, 0.01 wt %to 2 wt %, 0.01 wt %to 1 wt %, 0.1 wt %to 99 wt %, 0.1 wt %to 75 wt %, 0.1 wt %to 50 wt%, 0.1 wt %to 25 wt%, 0.1 wt %to 10 wt %, 0.1 wt %to 5 wt %, 0.1 wt %to 2 wt %, 0.1 wt %to 1 wt %, 0.1 wt %to 0.5 wt %, 1 wt %to 99 wt %, 1 wt %to 75 wt %, 1 wt %to 50 wt%, 1 wt %to 25 wt%, 1 wt %to 10 wt %, 1 wt %to 5 wt %, 5 wt %to 99 wt %, 5 wt %to 75 wt %, 5 wt %to 50 wt%, 5 wt %to 25 wt%, 5 wt %to 10 wt %, 10 wt %to 99 wt %, 10 wt %to 75 wt %, 10 wt %to 50 wt%, 10 wt %to 25 wt%, 10 wt %to 15 wt %, 20 wt %to 99 wt %, 20 wt %to 75 wt %, 20 wt %to 50 wt%, 30 wt %to 99 wt %, 30 wt %to 75 wt %, 30 wt %to 50 wt%, 40 wt %to 99 wt %, 40 wt %to 75 wt %, 40 wt %to 50 wt%, 50 wt %to 99 wt %, 50 wt %to 75 wt %, 60 wt %to 99 wt %, 60 wt %to 75 wt %, 70 wt %to 99 wt %, 70 wt %to 75 wt %, 80 wt %to 99 wt %, 80 wt %to 90 wt %, 90 wt %to 99 wt%, or a weight concentration range defined by any two of the aforementioned weight percentages in this paragraph.
  • G. Tabletop Sweetener Compositions
  • In general, tabletop sugar replacements lack certain taste attributes associated with sugar, especially for solid tabletop sweeteners. In addressing this need, the inventor of the present application has developed more palatable tabletop sugar replacements than commonly known. Specifically, in some embodiments, the present application provides an orally consumable product comprising one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application in  the form of an orally consumable tabletop sweetener composition. In one embodiment, the orally consumable tabletop sweetener composition has a taste similar to molasses.
  • In some embodiments, the tabletop sweetener composition may further include at least one bulking agent, additive, anti-caking agent, functional ingredient or combination thereof.
  • Suitable “bulking agents” include, but are not limited to, maltodextrin (10 DE, 18 DE, or 5 DE) , corn syrup solids (20 or 36 DE) , sucrose, fructose, glucose, invert sugar, sorbitol, xylose, ribulose, mannose, xylitol, mannitol, galactitol, erythritol, maltitol, lactitol, isomalt, maltose, tagatose, lactose, inulin, glycerol, propylene glycol, polyols, polydextrose, fructooligosaccharides, cellulose and cellulose derivatives, and the like, or mixtures thereof. Additionally, in accordance with still other embodiments of the application, granulated sugar (sucrose) or other caloric sweeteners such as crystalline fructose, other carbohydrates, or sugar alcohol can be used as a bulking agent due to their provision of good content uniformity without the addition of significant calories.
  • As used herein, the phrase “anti-caking agent” and “flow agent” refers to any composition which assists in content uniformity and uniform dissolution. In some embodiments, non-limiting examples of anti-caking agents include cream of tartar, aluminium silicate (Kaolin) , calcium aluminium silicate, calcium carbonate, calcium silicate, magnesium carbonate, magnesium silicate, mono-, di-and tri-calcium orthophosphate, potassium aluminium silicate, silicon dioxide, soldium aluminium silicate, salts of stearic acid, microcrystalline cellulose (Avicel, FMC BioPolymer, Philadelphia, Pennsylvania) , and tricalcium phosphate. In one embodiment, the anti-caking agents are present in the tabletop sweetener composition in an amount from about 0.001 to about 3 %by weight of the tabletop sweetener composition.
  • The tabletop sweetener compositions can be packaged in any form known in the art. Non-limiting forms include, but are not limited to, powder form, granular form, packets, tablets, sachets, pellets, cubes, solids, and liquids.
  • In one embodiment, the tabletop sweetener composition is a single-serving (portion control) packet comprising a dry-blend. Dry-blend formulations generally may comprise powder or granules. Although the tabletop sweetener composition may be in a packet  of any size, an illustrative non-limiting example of conventional portion control tabletop sweetener packets are approximately 2.5 by 1.5 inches and hold approximately 1 gram of a sweetener composition having a sweetness equivalent to 2 teaspoons of granulated sugar (～ 8 g) . In some embodiments, a dry-blend tabletop sweetener formulation may comprise a Composition of the present application in an amount from about 1% (w/w) to about 10 % (w/w) of the tabletop sweetener composition.
  • Solid tabletop sweetener embodiments include cubes and tablets. A non-limiting example of conventional cubes is equivalent in size to a standard cube of granulated sugar, which is approximately 2.2 x 2.2 x 2.2 cm 3 and weighs approximately 8 g. In one embodiment, a solid tabletop sweetener is in the form of a tablet or any other form known to those skilled in the art.
  • A tabletop sweetener composition also may be embodied in the form of a liquid, wherein one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application are combined with a liquid carrier. Suitable non-limiting examples of carrier agents for liquid tabletop sweeteners include water, alcohol, polyol, glycerin base or citric acid base dissolved in water, or mixtures thereof. The sweetness equivalent of a tabletop sweetener composition for any of the forms described herein or known in the art may be varied to obtain a desired sweetness profile. For example, a tabletop sweetener composition may have a degree of sweetness comparable to that of an equivalent amount of standard sugar. In another embodiment, the tabletop sweetener composition may comprise a sweetness of up to 100 times that of an equivalent amount of sugar. In another embodiment, the tabletop sweetener composition may comprise a sweetness of up to 90 times, 80 times, 70 times, 60 times, 50 times, 40 times, 30 times, 20 times, 10 times, 9 times, 8 times, 7 times, 6 times, 5 times, 4 times, 3 times, and 2 times that of an equivalent amount of sugar.
  • In any of the tabletop sweetener compositions described herein, one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be present in the tabletop sweetener composition at a final weight concentration of 0.0001 wt %, 0.001 wt %, 0.01 wt %, 0.1 wt %, 1 wt %, 2 wt %, 3 wt %, 4 wt %, 5 wt %, 6 wt %, 7 wt %, 8 wt %, 9 wt %, 10 wt %, 11 wt %, 12  wt %, 13 wt %, 14 wt %, 15 wt %, 16 wt %, 17 wt %, 18 wt %, 19 wt %, 20 wt %, 21 wt %, 22 wt %, 23 wt %, 24 wt %, 25 wt %, 26 wt %, 27 wt %, 28 wt %, 29 wt %, 30 wt %, 31 wt %, 32 wt %, 33 wt %, 34 wt %, 35 wt %, 36 wt %, 37 wt %, 38 wt %, 39 wt %, 40 wt %, 41 wt %, 42 wt %, 43 wt %, 44 wt %, 45 wt %, 46 wt %, 47 wt %, 48 wt %, 49 wt %, 50 wt %, 51 wt %, 52 wt %, 53 wt %, 54 wt %, 55 wt %, 56 wt %, 57 wt %, 58 wt %, 59 wt %, 60 wt %, 61 wt %, 62 wt %, 63 wt %, 64 wt %, 65 wt %, 66 wt %, 67 wt %, 68 wt %, 69 wt %, 70 wt %, 71 wt %, 72 wt %, 73 wt %, 74 wt %, 75 wt %, 76 wt %, 77 wt %, 78 wt %, 79 wt %, 80 wt %, 81 wt %, 82 wt %, 83 wt %, 84 wt %, 85 wt %, 86 wt %, 87wt %, 88 wt %, 89 wt %, 90 wt %, 91 wt %, 92 wt %, 93 wt %, 94 wt %, 95 wt %, 96 wt %, 97 wt %, 98 wt %, 99 wt %, or 100 wt %, or a weight concentration range defined by any two of the aforementioned weight percentages in this paragraph.
  • In more particular embodiments, one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be present in any of the tabletop sweetener compositions described herein, at a weight percentage range from 0.001 wt %to 99 wt %, 0.001 wt %to 75 wt %, 0.001 wt %to 50 wt%, 0.001 wt %to 25 wt%, 0.001 wt %to 10 wt %, 0.001 wt %to 5 wt %, 0.001 wt %to 2 wt %, 0.001 wt %to 1 wt %, 0.001 wt %to 0.1 wt %, 0.001 wt %to 0.01 wt %, 0.01 wt %to 99 wt %, 0.01 wt %to 75 wt %, 0.01 wt %to 50 wt%, 0.01 wt %to 25 wt%., 0.01 wt %to 10 wt %, 0.01 wt %to 5 wt %, 0.01 wt %to 2 wt %, 0.01 wt %to 1 wt %, 0.1 wt %to 99 wt %, 0.1 wt %to 75 wt %, 0.1 wt %to 50 wt%, 0.1 wt %to 25 wt%, 0.1 wt %to 10 wt %, 0.1 wt %to 5 wt %, 0.1 wt %to 2wt %, 0.1 wt %to 1 wt %, 0.1 wt %to 0.5 wt %, 1 wt %to 99 wt %, 1 wt %to 75 wt %, 1 wt %to 50 wt%, 1 wt %to 25 wt%, 1 wt %to 10 wt %, 1 wt %to 5 wt %, 5 wt %to 99 wt %, 5 wt %to 75 wt %, 5 wt %to 50 wt%, 5 wt %to 25 wt%, 5 wt %to 10 wt %, 10 wt %to 99 wt %, 10 wt %to 75 wt %, 10 wt %to 50 wt%, 10 wt %to 25 wt%, 10 wt %to 15 wt %, 20 wt %to 99 wt %, 20 wt %to 75 wt %, 20 wt %to 50 wt%, 30 wt %to 99 wt %, 30 wt %to 75 wt %, 30 wt %to 50 wt%, 40 wt %to 99 wt %, 40 wt %to 75 wt %, 40 wt %to 50 wt%, 50 wt %to 99 wt %, 50 wt %to 75 wt %, 60 wt %to 99 wt %, 60 wt %to 75 wt %, 70 wt %to 99 wt %, 70 wt %to 75 wt %, 80 wt %to 99 wt %, 80 wt %to 90 wt %, 90 wt %to 99 wt%, or a weight concentration range defined by any two of the aforementioned weight percentages in this paragraph.
  • H. Medicinal Compositions
  • In certain embodiments, one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be used in medicinal compositions. As used herein, the term “medicinal composition” includes solids, gases and liquids which are ingestible materials having medicinal value, such as cough syrups, cough drops, medicinal sprays, vitamins, and chewable medicinal tablets that are administered orally or used in the oral cavity in the form of e.g., a pill, tablet, spray, capsule, syrup, drop, troche agent, powder, and the like.
  • I. Oral Hygiene Compositions
  • In some embodiments, one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be used in an oral hygiene composition. As used herein, the “oral hygiene composition” includes mouthwashes, mouth rinses, breath fresheners, toothpastes, tooth polishes, dentifrices, mouth sprays, teeth whitening agents, soaps, perfumes, and the like.
  • In some embodiment, the oral hygiene product comprises a sweetener composition comprising (1) one or more components selected from the group consisting of RU, GRU, STEs, GSTEs, STCs, GSTCs, MGs, GMGs, MFCs, GMFCs, SEs, GSEs, SCs, GSCs, SGs and GSGs of the present application, and (2) sugar donors or residues thereof in an amount that is greater than zero, but is less than 15%, less than 10%, less than 5%, less than 4%, less than 3%, less than 2%, less than 1%, less than 0.5%, less than 0.1%, less than 0.05%, or less than 0.01% (wt/wt) of the sweetener composition.
  • J. Cosmetic Compositions
  • In some embodiments, one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application is utilized in a cosmetic composition for enhancing the aroma of a cosmetic or skin-care product. As used herein, the term “cosmetic composition” means a composition that is formulated for topical application to skin, which has a pleasant colour, odour and feel, and which does not cause unacceptable discomfort (stinging, tautness or redness) liable to discourage the consumer from using it.
  • Cosmetic composition may be preferably formulated in the form of an emulsion, e.g., W/O (water-in-oil) , O/W (oil-in-water) , W/O/W (water-in-oil-in-water) , O/W/O (oil-in-water-in-oil) emulsion, PIT emulsion, Pickering emulsion, emulsion with a low oil content, micro-or nanoemulsion, a solution, e.g., in oil (fatty oils or fatty acid esters, in particular C 6-C 32 fatty acid C 2-C 30 esters) or silicone oil, dispersion, suspension, creme, lotion or milk, depending on the production method and ingredients, a gel (including hydrogel, hydrodispersion gel, oleogel) , spray (e.g., pump spray or spray with propellant) or a foam or an impregnating solution for cosmetic wipes, a detergent, e.g., soap, synthetic detergent, liquid washing, shower and bath preparation, bath product (capsule, oil, tablet, salt, bath salt, soap, etc. ) , effervescent preparation, a skin care product such as e.g., an emulsion (as described above) , ointment, paste, gel (as described above) , oil, balsam, serum, powder (e.g., face powder, body powder) , a mask, a pencil, stick, roll-on, pump, aerosol (foaming, non-foaming or post-foaming) , a deodorant and/or antiperspirant, mouthwash and mouth rinse, a foot care product (including keratolytic, deodorant) , an insect repellent, a sunscreen, aftersun preparation, a shaving product, aftershave balm, pre-and aftershave lotion, a depilatory agent, a hair care product such as e.g., shampoo (including 2-in-1 shampoo, anti-dandruff shampoo, baby shampoo, shampoo for dry scalps, concentrated shampoo) , conditioner, hair tonic, hair water, hair rinse, styling creme, pomade, perm and setting lotion, hair spray, styling aid (e.g., gel or wax) , hair smoothing agent (detangling agent, relaxer) , hair dye such as e.g., temporary direct-dyeing hair dye, semi-permanent hair dye, permanent hair dye, hair conditioner, hair mousse, eye care product, make-up, make-up remover or baby product.
  • K. Smokable Compositions
  • In some embodiments, one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be used in a smokable composition. The term “smokable composition, ” as used herein, includes any material that can be smoked or inhaled, such as tobacco and cannabis, as well as any smokable material that is burned to provide desirable aromas (e.g., charcoal briquettes for grilling foods, incense etc) . The smoking compositions may encompass cigarettes, electronic cigarettes (e-cigarettes) , cigars, pipe and cigar tobacco, chew tobacco, vaporizable liquids, and all forms of tobacco such as shredded filler, leaf, stem, stalk, homogenized leaf  cured, reconstituted binders, reconstituted tobacco from tobacco dust, fines, or other sources in sheet, pellet or other forms. “Smokable compositions” also include cannabis compositions (e.g., flower materials, leaf materials, extracts, oils, edible candies, vaporizable liquids, cannabis-infused beverages, etc. ) and tobacco substitutes formulated from non-tobacco materials.
  • IV. Taste Profiles and Taste Testing of Compositions containing one or more STEs, STCs,  SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs  and GMFCs
  • The one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, and methods described herein are useful for improved taste and aroma profiles of many comsumable products relative to control samples. The phrase “taste profile” , which is interchangeable with “sensory profile” and “sweetness profile” , may be defined as the temporal profile of all basic tastes of a sweetener. The “temporal profile” may be considered to represent the intensity of sweetness perceived over time in tasting of the composition by a human, especially a trained “taster” . Carbohydrate and polyol sweeteners typically exhibit a quick onset followed by a rapid decrease in sweetness, which disappers realtively quickly on swallowing a food or beverage containing the same. In contrast, high intensity natural sweeteners typically have a slower sweet taste onset reaching a maximal response more slowly, followed by a decline in intensity more slowly than with carbohydrate and polyol sweeteners. This decline in sweetness is often referred to as “sweetness linger” and is a major limitation associated with the use of high intensity natural sweeteners.
  • In the context of taste tasting, the terms “improve” , “improved” and “improvement” are used interchangeably with reference to a perceived advantageous change in a composition or consumable product upon introduction of one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application from the original taste profile of the composition or consumable product without the added one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs in any aspect, such as less bitterness, better sweetness, better sour taste, better aroma, better mouth feel, better flavor, less aftertaste, etc. The terms “improve” or “improvement” can refer to a slight change, a change, or a  significant change of the original taste profile, etc., which makes the composition more palatable to an individual.
  • In some embodiments, the one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application and methods described herein are useful for improving the taste and aroma profiles for other synthetic sweeteners, such as sucralose, ACE-K, aspartame, sodium saccharin, and mixtures thereof, and for natural high intensity sweeteners such as steviol glycosides, Stevia extracts, monk fruit extract, monk fruit components, licorice extract, licorice components.
  • In some embodiments, the one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application may be evaluated with reference to the degree of their sucrose equivalence. Accordingly, the STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs compositions of the present application may be diluted or modified with respect to its ingredients to conform this sucrose equivalence.
  • The onset and decay of sweetness when one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs of the present application are consumed can be perceived by trained human tasters and measured in seconds from first contact with a taster′s tongue ( ″onset″ ) to a cutoff point (typically 180 seconds after onset) to provide a ″temporal profile of sweetness″ . A plurality of such human tasters is called a ″sensory panel. ″ In addition to sweetness, sensory panels can also judge the temporal profile of the other ″basic tastes″ : bitterness, saltiness, sourness, piquance (aka spiciness) , and umami (aka savoriness or meatiness) . The onset and decay of bitterness when a sweetener is consumed, as perceived by trained human tasters and measured in seconds from first perceived taste to the last perceived aftertaste at the cutof fpoint, is called the ″temporal profile of bitterness. ″ Aromas from aroma producing substances are volatile compounds which are perceived by the odor receptor sites of the smell organ, i.e., the olfactory tissue of the nasal cavity. They reach the receptors when drawn in through the nose (orthonasal detection) and via the throat after being released by chewing (retronasal detection) . The concept of aroma substances, like the concept of taste substances, is to be used loosely, since a compound might contribute to the typical odor or taste of one food, while in another food it may cause a faulty  odor or taste, or both, resulting in an off-flavor. Thus, sensory profile may include evaluation of aroma as well.
  • The term “mouth feel” involves the physical and chemical interaction of a consumable in the mouth. More specifically, as used herein, the term “mouth feel” refers to the fullness sensation experienced in the mouth, which relates to the body and texture of the consumable such as its viscosity. Mouth feel is one of the most important organoleptic properties and the major criteria that consumers use to judge the quality and freshness of foods. Subtle changes in a food and beverage product’s formulation can change mouth feel significantly. Simply taking out sugar and adding a high intensity sweetener can cause noticeable alterations in mouth feel, making a formerly good product unacceptable to consumers. Sugar not only sweetens, it also builds body and viscosity in food and beverage products, and leaves a slight coating on the tongue. For example, reducing salt levels in soup changes not only taste, but can alter mouth feel as well. Primarily it is the mouth feel that is always the compliant with non-sugar sweeteners.
  • The phrase “sweetness detection threshold” refers to the minimum concentration at which panelists consisting of 1-10 persons are able to detect sweetness in a composition, liquid or solid. This is further defined as provided in the Examples herein and are conducted by the methods described in Sensory Testing for Flavorings with Modifying Properties by Christie L. Harman, John B. Hallagan, and the FEMA Science, Committee Sensory Data Task Force, November 2013, Volume 67, No. 11 and Appendix A attached thereto, the teachings of which are incorporated herein by reference.
  • “Threshold of sweetness” refers to a concentration of a material below which sweetness cannot be detected, but can still impart a flavor to a consumable (including water) . When half of a trained panel of testers determines something is “sweet” at a given concentration, then the sample meets the threshold. When less than half of a panel of testers cannot discern sweetness at a given concentration, then concentrations of the substance below the sweetness level are considered a flavoring agent.
  • It should be understood that the flavoring agents described herein, including STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, can be used in combination with other materials, including non-ST steviol  glycosides, to encapsulate and reduce or eliminate the unwanted off taste present in the composition. The processes described herein can be used to preserve flavors.
  • For example, to dissolve any flavor or flavor combination in a dissolved steviol glycosides solution, afterwards, the solution could be ready to use, or it could be further concentrated to syrup or powder form. For evaluating the taste profile of a given composition, a sample may be tested by e.g., a panel of 1-10 people. In some cases, a trained taster may independently taste the sample (s) first. The taster may be asked to describe the taste profile and score 0-5 according to the increasing sugar like, bitterness, aftertaste and lingering taste profiles. The taster may be allowed to re-taste, and then make notes for the sensory attributes perceived. Afterwards, another group of 1-10 tasters may similarly taste the sample (s) , record its taste attributes and discuss the samples openly to find a suitable description. Where more than 1 taster disagrees with the results, the tasting may be repeated. For example, a “5” for sugar like is the best score for having a taste that is sugar like and conversely a value of 0 or near zero is not sugar like. Similarly, a “5” for bitterness, aftertaste and lingering is not desired. A value of zero or near zero means that the bitterness, aftertaste and/or lingering is reduced or is removed. Other taste attributes may include astringency and overall likabilityability.
  • In some embodiments, vanilla, maltol or other flavor modifier product (s) “FMPs” can be added to the compositions described herein to further improve the taste. FMPs, such as maltol, ethyl-maltol, vanillin, ethyl vanillin, m-methylphenol, and m-n-propylphenol can further enhance the mouth feel, sweetness and aroma of the STC, STE compositions described herein. Such compositions may be used in any of the food or beverage products described herein.
  • Additionally, the flavor substances in the sweet tea plant should also contain any new possible flavor substances from new sweet tea varieties by hybridizing, grafting and other cultivating methods.
  • Flavor oils include spearmint oil, cinnamon oil, oil of wintergreen (methyl salicylate) , peppermint oil, Japanese mint oil, clove oil, bay oil, anise oil, eucalyptus oil, thyme oil, cedar leaf oil, oil of nutmeg, allspice, oil of sage, mace, oil of bitter almonds, and cassia oil; useful flavoring agents include artificial, natural and synthetic fruit flavors, such as vanilla, and citrus oils including lemon, orange, lime, grapefruit, yuzu, sudachi, and fruit essences including apple, pear, peach, grape, raspberry, blackberry, gooseberry, blueberry, strawberry, cherry, plum,  prune, raisin, cola, guarana, neroli, pineapple, apricot, banana, melon, apricot, cherry, tropical fruit, mango, mangosteen, pomegranate, papaya, and so forth.
  • Additional exemplary flavors imparted by a flavoring agent include a milk flavor, a butter flavor, a cheese flavor, a cream flavor, and a yogurt flavor; a vanilla flavor; tea or coffee flavors, such as a green tea flavor, an oolong tea flavor, a tea flavor, a cocoa flavor, a chocolate flavor, and a coffee flavor; mint flavors, such as a peppermint flavor, a spearmint flavor, and a Japanese mint flavor; spicy flavors, such as an asafetida flavor, an ajowan flavor, an anise flavor, an angelica flavor, a fennel flavor, an allspice flavor, a cinnamon flavor, a chamomile flavor, a mustard flavor, a cardamom flavor, a caraway flavor, a cumin flavor, a clove flavor, a pepper flavor, a coriander flavor, a sassafras flavor, a savory flavor, a Zanthoxyli Fructus flavor, a perilla flavor, a juniper berry flavor, a ginger flavor, a star anise flavor, a horseradish flavor, a thyme flavor, a tarragon flavor, a dill flavor, a capsicum flavor, a nutmeg flavor, a basil flavor, a marjoram flavor, a rosemary flavor, a bayleaf flavor, a wasabi (Japanese horseradish) flavor; a nut flavor, such as an almond flavor, a hazelnut flavor, a macadamia nut flavor, a peanut flavor, a pecan flavor, a pistachio flavor, and a walnut flavor; alcoholic flavors, such as a wine flavor, a whisky flavor, a brandy flavor, a rum flavor, a gin flavor, and a liqueur flavor; floral flavors; and vegetable flavors, such as an onion flavor, a garlic flavor, a cabbage flavor, a carrot flavor, a celery flavor, mushroom flavor, and a tomato flavor.
  • Generally any flavoring agent or food additive, such as those described in ″Chemicals Used in Food Processing″ , Publication No 1274, pages 63-258, by the National Academy of Sciences, can be used. This publication is incorporated herein by reference.
  • As used herein, a “flavoring agent” or “flavorant” herein refers to a compound or an ingestibly acceptable salt or solvate thereof that induces a flavor or taste in an animal or a human. The flavoring agent can be natural, semi-synthetic, or synthetic. Suitable flavorants and flavoring agentt additives for use in the compositions of the present application include, but are not limited to, vanillin, vanilla extract, mango extract, cinnamon, citrus, coconut, ginger, viridiflorol, almond, bay, thyme, cedar leaf, nutmeg, allspice, sage, mace, menthol (including menthol without mint) , an essential oil, such as an oil produced from a plant or a fruit, such as peppermint oil, spearmint oil, other mint oils, clove oil, cinnamon oil, oil of wintergreen, or an oil of almonds; a plant extract, fruit extract or fruit essence from grape skin extract, grape seed  extract, apple, banana, watermelon, pear, peach, grape, strawberry, raspberry, cherry, plum, pineapple, apricot, a flavoring agent comprising a citrus flavor, such as an extract, essence, or oil of lemon, lime, orange, tangerine, grapefruit, citron, kumquat, or combinations thereof. Flavorants for use in the present application include both natural and synthetic substances which are safe for humans or animals when used in a generally accepted range.
  • Non-limiting examples of proprietary flavorants include Dohler TM Natural Flavoring Sweetness Enhancer K14323 (Dohler TM, Darmstadt, Germany) , Symrise TM Natural Flavor Mask for Sweeteners 161453 and 164126 (Symrise TM, Holzminden, Germany) , Natural Advantage TM Bitterness Blockers 1, 2, 9 and 10 (Natural Advantage TM, Freehold, New Jersey, U.S.A. ) , and Sucramask TM (Creative Research Management, Stockton, California, U.S.A. ) .
  • In the any of the embodiments described in the present application, the flavoring agent is present in the sweetener or flavoring composition of the present application in an amount effective to provide a final concentration of about 0.1 ppm, 0.5 ppm, 1 ppm, 2 ppm, 5 ppm, 10 ppm, 15 ppm, 20 ppm, 25 ppm, 30 ppm, 35 ppm, 40 ppm, 45 ppm, 50 ppm, 55 ppm, 60 ppm, 65 ppm, 70 ppm, 75 ppm, 80 ppm, 85 ppm, 90 ppm, 100 ppm, 110 ppm, 120 ppm, 130 ppm, 140 ppm, 150 ppm, 160 ppm, 170 ppm, 180 ppm, 190 ppm, 200 ppm, 220 ppm, 240 ppm, 260 ppm, 280 ppm, 300 ppm, 320 ppm, 340 ppm, 360 ppm, 380 ppm, 400 ppm, 425 ppm, 450 ppm, 475 ppm,500 ppm, 550 ppm, 600 ppm, 650 ppm, 700 ppm, 750 ppm, 800 ppm, 850 ppm, 900 ppm, 950 ppm, 1000 ppm, 1500 ppm, 2000 ppm, 2500 ppm, 3000 ppm, 3500 ppm, 4000 ppm, 4500 ppm, 5000 ppm, 6000 ppm, 7000 ppm, 8000 ppm, 9000 ppm, 10,000 ppm, 11,000 ppm, 12,000 ppm, 13,000 ppm, 14,000 ppm, or 15,000 ppm; or to provide a final concentration corresponding to any one of the aforementioned values in this paragraph; or to provide a final concentration range corresponding to any pair of the aforementioned values in this paragraph.
  • In more particular embodiments, the flavoring agent is present in the composition of the present application in an amount effective to provide a final concentration ranging from 10 ppm to 1000 ppm, from 50 ppm to 900 ppm, from 50 ppm to 600 ppm, from 50 ppm to 500 ppm, from 50 ppm to 400 ppm, from 50 ppm to 300 ppm, from 50 ppm to 200 ppm, from 75 ppm to 600 ppm, from 75 ppm to 500 ppm, from 75 ppm to 400 ppm, from 75 ppm to 300 ppm, from 75 ppm to 200 ppm, from 75 ppm to 100 ppm, from 100 ppm to 600 ppm, from 100 ppm to 500 ppm, from 100 ppm to 400 ppm, from 100 ppm to 300 ppm, from 100 ppm to  200 ppm, from 125 ppm to 600 ppm, from 125 ppm to 500 ppm, from 125 ppm to 400 ppm, from 125 ppm to 300 ppm, from 125 ppm to 200 ppm, from 150 ppm to 600 ppm, from 150 ppm to 500 ppm, from 150 ppm to 500 ppm, from 150 ppm to 400 ppm, from 150 ppm to 300 ppm, from 150 ppm to 200 ppm, from 200 ppm to 600 ppm, from 200 ppm to 500 ppm, from 200 ppm to 400 ppm, from 200 ppm to 300 ppm, from 300 ppm to 600 ppm, from 300 ppm to 500 ppm, from 300 ppm to 400 ppm, from 400 ppm to 600 ppm, from 500 ppm to 600 ppm; or to provide a final concentration corresponding to any one of the aforementioned values in this paragraph; or to provide a final concentration range corresponding to any pair of the aforementioned values in this paragraph.
  • V. STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs,  GMGs, GMFEs and GMFCs as flavor enhancers
  • The inventors have surprisingly found that STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs can bind the volatiles of various flavors used in food, beverages, cosmetics, feeds and pharmaceuticals. STEs, STCs, GSTEs and GSTCs formed by the methods disclosed herein can be widely soluble in water, water/alcohol, alcohol, and other organic solvents used for the flavor industry at different temperatures. The sweet tea composition can naturally encapsulate the flavor produced during the processes described herein. Therefore, it is also an excellent carrier or encapsulation material for flavors, including but not limited to flavors and spices originated from plants such as bark, flowers, fruits, leaves, animals such as concentrated meat and sea food soups etc., and their extracts such as essential oils etc.
  • In one aspect, a processed flavor is added to solution containing one or more composition selected from STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, then dried into a powder by any method, including but not limited spray-drying, crystallization, tray-drying, freeze drying etc. Thus, volatile flavors could be preserved. The advantage of the present embodiments is that encapsulated flavors by STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs could be kept at room temperature or even  higher temperatures without much loss of flavor. In addition, depending on desired product, specially designed compositions can enhance a foam for a specific application such as foamed/frothy coffee. In addition, an anti-foaming agent could be added together or separately during the reaction processes descried herein, such that the product could be used to prevent foaming for beverage bottling applications.
  • Another advantage of the present embodiments is that flavors could be absorbed in or to the inner surface of pores of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs powders. Flavors are preserved and can be released when in solution. The present embodiments avoid the use of starch, or dextrin as a carrier which can bring wheat taste to the flavors.
  • Another advantage is that three or more molecules selected from rubusosides, or suaviosides bind one water molecule and act as a moisture preserver. An embodiment of composition comprises one more ingredient selected from STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs as a moisture preserver.
  • The inventor surprisingly found the sweetness synergy between the sweet tea derived products with other sweeteners. An embodiment comprises A) one or more ingredients selected from STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs; and B) one or more ingredients selected from following components:
  • (1) A GMG or mixtures of GMGs.
  • (2) A GMG in combination with a GSG.
  • (3) A GMG in combination with an SG.
  • (4) A GMG in combination with an MG.
  • (5) A GMG, a GSG and an SG.
  • (6) A GMG, a GSG and an MG.
  • (7) A GMG, an SG and an MG.
  • (8) A GMG, a GSG, an SG and an MG.
  • (9) An MG and a GSG.
  • (10) An MG, a GSG and an SG.
  • (11) A stevia extract.
  • (12) A steviol glycoside (SG) .
  • (13) A glycosylated steviol glycoside (GSG) .
  • (14) A swingle extract (mogroside extract) .
  • (15) A glycosylated swingle extract.
  • (16) A mogroside (MG) or a mixture of MGs.
  • (17) A glycosylated mogroside (GMG) .
  • (18) A steviol glycoside (SG) and a glycosylated steviol glycoside (GSG) .
  • (19) Any of the above 18 combinations further including one or more salts.
  • (20) Any of the above 19 further including a sweetener.
  • (21) Any of the above 20 combinations further including a sweetener enhancer.
  • It should be understood, that in the 21 combinations noted above, that where the singular is used, e.g., a glycosylated stevia glycoside, that the plural of such is included, e.g., glycosylated stevia glycosides.
  • An embodiment of composition comprises A) and B) , where the ratio of A) to B) is from 1∶ 99 to 99∶ 1. A further embodiment of food and beverage comprises A) and B) . An additional embodiment of food and beverage comprises A) and B) , where total amount of A) + B) is from 1ppm to 10,000 ppm.
  • Foods and beverages that contain tea powder or tea extract, or flavored tea have a bitter taste or astringent mouth feel. The inventors surprisingly found that adding the compositions of this invention could significantly mask the bitter taste and/or improve the mouth feel.
  • With the increase of obesity and a diabetic population, limiting sugar became a top concern for a healthy diet choices worldwide, with consumers preferring for low sugar foods and beverages but without a sacrifice in taste. High intensive natural sugar alternatives such as stevia extract, monk fruit extract and sweet tea extract, and artificial high intensive sweetener such as sucralose, ACE-K and aspartame, are applied in foods and beverages for reduced sugar product claims, each of these highly intensive sugar alternatives has a unique taste profile but none tastes exactly like sugar. Some bring bitter or metallic off notes which results in the low sugar food and beverage to have an unsatisfactory taste to consumers’ palate. A solution to improve the taste of low sugar foods and beverages is imperative in the promotion of a healthy diet.
  • In one aspect, a flavoring agent (s) in combination with one or more ingredient selected from STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs is provided. It has been found that substances including rubusoside surprisingly protects the flavoring agent. Not to be limited by any theory, there is a surprising protective effect exerted by the sweet tea or rubusoside-rich derived products on the flavoring agent (s) .
  • For example, unlike typical powdered flavoring agents which have a strong odor, the inventors have surprisingly found that the combination of one or more ingredient selected from STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs and flavoring agent (s) result in a composition with minimal smell. However, when one or more ingredient selected from STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, and flavoring agent (s) are dissolved in a solution (e.g., water, alcohol or mixtures thereof) , the odor of the flavoring is released resulting in a strong smell.
  • The above observations are not meant to be limited to powders. The one or more ingredient selected from STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, and the flavoring agent (s) can be part of a liquid composition, such as a syrup.
  • In one embodiment, the processes of the embodiments described herein are useful for improvement of taste and aroma profile for other natural sweeteners, including but not  limited to licorice, thaumatin etc., their mixtures, their mixtures with sweet tea or rubusoside-rich derived products, etc.
  • In another embodiment, the processes of the embodiments described herein are used for improvement of taste and aroma profile for other synthetic sweeteners, including but not limited to AC-K, aspartame, sodium saccharin, sucralose or their mixtures.
  • The embodiments described above are applicable for any synthetic sweetener, blends thereof and other natural sweeteners, blends thereof, or mixtures of synthetic and natural sweetener (s) , especially with sucralose.
  • Consumers are now open and willing to experiment with spices to experience new flavors like tamarind, lemongrass, ginger, kaffir lime, cinnamon and clove. From candy to beer to tea, everything with ginger is now fashionable. Ginger works well in alcoholic beverages as a mixer, in ginger beer itself, in confections, muffins and cookies.
  • Sodium metabisulfite, olive oil and ascorbic acid were found to be effective to stabilize the antibacterial activity. 1.5%CMC shows a good performance too. Ginseng is one of the top 10 best selling herbal dietary supplements in US, but ginseng-containing products have been mostly limited to beverages, despite a growing functional food market. The original ginseng flavors include bitterness and earthiness and must be minimized in order to establish potential success in the US market. The embodiments described herein can successfully solve this issue and make new ginseng food products such as cookies, snacks, cereals energy bars, chocolates and coffee with great taste.
  • In Asia, especially south-east Asia, Rose, Jasmine, Pandan, Lemon grass, yellow ginger, blue ginger, lime leaf, curry leave, Lilies, basil, coriander, coconut etc. are specific local flavors. In East Asia, many herbs are used in the cooking such as Artemisia argyi, dandelion, Codonopsis pilosula, Radix Salviae Miltiorrhizae, Membranous Milkvetch Root, rhizoma gastrodiae etc.. The inventors have found that adding STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs could significantly improve the taste profile of these flavors and their added products.
  • Flavonoids are an important and widespread group of plant natural products that possess many biological activities. These compounds are part of the wide range of substances  called “polyphenols” , which are widely known mainly by their antioxidant properties, and are present in human dietary sources showing great health benefits.
  • Neohesperidine and naringin, which are flavanone glycosides present in citrus fruits and grapefruit, are responsible for the bitterness of citrus juices. These substances and their derivates such as neohesperidine chalcone, naringin chalcone, phloracetophenone, neohesperidine dihydrochalcone, naringin dihydrochalcone etc. can be good candidates for bitterness or sweetener enhancers. The inventors surprisingly found adding these components in the compositions described herein could help the masking the bitterness or aftertaste of other ingredients and made the taste cleaner. One embodiment includes the compositions described herein and further comprises flavonoids, more preferably flavonoids containing flavonone glycosides. The ratio of flavonoids in the composition could be in range of from about 0.1 ppm to 99.9%.
  • Metal salts of dihydrochalcone having the following formula:
  • wherein R is selected from the group consisting of hydrogen and hydroxy, R′ is selected from the group consisting of hydroxy, methoxy, ethoxy and propoxy, and R″ is selected from the group consisting of neohesperidoxyl, B-rutinosyl and β-D-glucosyl, M is a mono-or divalent metal selected from the group consisting of an alkali metal and an alkaline earth metal, and n is an integer from 1 to 2 corresponding to the valence of the selected metal M.
  • Typical compounds of the above formula are the alkali or alkaline earth metal monosalts of the following:
  • Neohesperidin dihydrochalcone, having the formula:
  • 2′, 4′, 6′, 3-tetrahydroxy-4-n-propoxydihydrochalcone 4′-β neohesperidoside having the formula:
  • naringin dihydrochalcone of the formula:
  • prunin dihydrochalcone of the formula:
  • hesperidin dihydrochalcone having the formula:
  • and hesperitin dihydrochalcone glucoside having the formula:
  • The alkali metal includes sodium, potassium, lithium, rubidium, caesium, and ammonium, while the term alkaline earth metal includes calcium, strontium and barium. Other alkali amino acids can serve as as counterions. Thus embodiments of compositions described herein furhter comprises one or more salts of dihydrochalone.
  • The composition described herein can further comprise one or more products selected from Trilobatin, phyllodulcin, Osladin, Polypodoside A, Eriodictyol, Homoeriodicyol sodium salt, hesperidin or hesperetin, Neohesperidin dihydrochalcone, naringin dihydrocholcone, or advantame to provide additional flavors and products. Another embodiment comprises of the compositions described herein and one or more of the aforementioned products, wherein the ratio of one or more products selected in the composition can be in the range of from about 0.1%to about 99.9%.
  • Advantame is high potency synthetic sweetener and can be used as a flavor enhancer. The inventors found that adding advantame into the compositions described herein can boost the flavor and taste profile of a food or beverage. One embodiment provides compositions described herein which further comprise advantame, wherein the amount of advantame can be in the range of from about 0.01ppm to about 100 ppm.
  • Pigs, especially young pigs, appreciate good and pleasant tastes and aroma much the way young children do. Cats are notoriously fussy about the taste and smell of their feed. Feeds such as rapeseed meal, which has a bitter taste, are used as good protein sources for cattle, sheep, and horses. Even chickens are known for their taste discrimination, as chickens are selective to their feeds. Green, natural or organic farming of animals become more and more popular. Therefore, there is a need to find a solution to satisfy market requirements. An embodiment of feed or feed additives comprises the compositions described herein.
  • The intense sweetness and flavor/aroma enhancement properties of the compositions described herein provide useful applications in improving the palatability of medicines, traditional Chinese medicine, food supplements, beverage, food containing herbs, particularly those with unpleasant long-lasting active ingredients not easily masked by sugar or glucose syrups, let alone sweetening agents or synthetic high intensity sweeteners. The inventors surprisingly found the compositions described herein can mask the unpleasant taste and smell of the products containing these substances, for instance Goji berries juice, sea buckthorn juice, milk thistle extract, ginkgo biloba extract etc.. Thus traditional Chinese medicine, or food supplements can be combined with one or more of compositions described herein, especially when used as a masking agent.
  • Aquaplants and seafood cultivated from fresh water or sea water always have a fish smell or marine odor. Examples of odoriferous aquatic foodstuffs include spirulina powder or its enriched protein extract, protein extracted from duckweeds (lemnoideae family) , fish protein, fish meal etc. There is a need to minimize or cover the unpleasant odor to make the food product palatable. The inventors surprisingly found that compositions described herein could be added in these products to minimize the odors to make them more acceptable to consumers including feeds for animals. Embodiments of consumables comprise components from aquaplants and or seafood, and any of the compositions described herein.
  • Foods and beverages containing acids can irritate the tongue. For instance, products containing acetic acid can irritate the tongue and make that product unpalatable. The inventors surprisingly found that adding any of the compositions described herein could significantly balance the acid taste and make the products palatable.
  • Beverages containing vinegar, such as apple cider vinegar drink, shrub, switchel etc. have become popular in the market due to vinegar’s health attributes. The acetic acid can be naturally occurring, for instance it is originated from fermentation of fruits such as apple, pear, persimmon etc., grains such as rice, wheat etc. It could be also synthetic. However, the taste of acetic acid is strong and sour and tends to bum the throat. Therefore, there is a need to find a solution to harmonize it. The inventors surprisingly found that adding any of the compositions described herein can strongly harmonize the taste of beverages containing acetic acid and make them palatable. One embodiment provides a composition comprising acetic acid and any of the compositions described herein. Another embodiment provides a method to harmonize the taste of acetic acid by using any of the compositions described herein. Another embodiment provides a consumable that comprises acetic acid and any of the compositions described herein. Another embodiment provides the use of any the compositions described herein in beverages containing acetic acid, where the dosage of the composition (s) described herein is above 10 ( -9) ppb. Embodiments of the composition (s) described herein include, for example, one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, combinations of thaumatin and one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, combinations of one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs and high intensity sweeteners, combinations of thaumatin, STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs and high intensity sweetener.
  • Thermotreating STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, especially thermo-reaction treatment can result in improved taste of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs. Thermo-treatment is like caramelization of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs,  GMFEs and GMFCs. The temperature range can be from 0-1000℃, in particular from about 20 to about 200℃, more particularly from about 60 to about 120℃. The period of treatment can be from be from a few seconds to a few days, more particularly about one day and even more particularly from about 1 hour to about 5 hours.
  • The inventors surprisingly found that adding one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, combinations of thaumafin and one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, combinations of one or more of STE, STC, GSTE, GSTC and high intensity sweeteners, combinations of thaumatin, STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs and high intensity sweetener in food and beverages containing alcohol can enhance the strength of alcohol. Embodiments provide food and beverages containing alcohol comprising composition selected from one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs.
  • Flavor of beer, the size and the amount of bubbles are important factors in measuring the quality of beer. Compositions described herein can be used for enhancing the flavor of beer taste and to adjust the size and amount of bubbles. In one embodiment, beer or beer containing products can include one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs
  • Foods having high sugar content such as area catechu, spicy bar (or called spicy strip, hot strip, spicy glutein) , pickled vegetables, meat and fishes, or fermented foods always require large amounts of sugar in order to balance the total taste profile and make them more palatable. The inventors surprisingly found that adding thaumatin, one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, combinations of one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs and thaumatin, combinations of one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, high intensity sweetener and thaumatin, could significantly improve the taste profile and or palatability, especially when sugar reduction is  required for such foods. For example, embodiments of such compositions include area catechu, spicy bar, pickled food, or fermented foods with one of composition (s) described herein.
  • Vegetable burgers have become popular in recent years, but the taste is still not palatable to most consumers. Compositions described herein can be used for enhancing the flavor and taste of the vegetable burger. In one embodiment, a vegetable burger comprises thaumatin, one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, combinations of one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs and thaumatin, combinations of one or more of STE, STC, GSTE, GSTCand high intensity sweetener, or combinations of thaumatin, one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs and high intensity sweeteners.
  • Grilled foods often incorporate sugar to enhance the taste. However, sugar creates strong colors during grilling, and when the fried foods become cold, the sugar syrup becomes sticky. The inventors found that by adding the compositions described herein to the food to be grilled, these disadvantages can be overcome. For example, embodiments include grilled foods that include thaumatin, one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs, combinations of one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs and thaumatin, combinations of one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs and high intensity sweetener, or combinations of thaumatin, one or more of STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs and high intensity sweeteners.
  • An embodiment of composition comprises A) one or more ingredients selected from STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs and B) one or more substances selected from fibers such as polydextrose; inulin, Promitor produced by Tate&Lyle; monosaccharide-derived polyols such as erythritol, mannitol, xylitol, and sorbitol; disaccharide-derived alcohols such as isomalt, lactitol, and maltitol; and hydrogenated starch hydrolysates, synthetic high intensity sweeteners such as  sodium saccharin, sucralose, aspartame, acesulfame-K, N-- [N- [3- (3-hydroxy-4-methoxyphenyl) propyl] -alpha-aspartyl] -L-phenylalanine 1-methyl ester, sodium cyclamate, neotame; natural low intensity sweeteners such as trehalose, raffinose, cellobiose, tagatose, DOLCIA PRIMA TM allulose; Natural high intensity sweeteners such as Licorice extract, glycyrrhizin-derived substances, stevia extract, monk fruit extract, glycosylated stevia extract, glycosylated monk fruit extract; modified starch such as Rezista, Claria, Kolgauard etc. produced by Tate&Lyle; Oligosaccharides such as IMO (Isomalto-oligosaccharides) , MOS (Malto-oligosaccharides) , FOS (Fructooligosaccharide) , or mixtures thereof. A further embodiment of composition comprises A) and B) , where ratio of A) to B) is from 1∶99 to 99∶1. An additional embodiment of composition comprises A) and B) , where the final product is in powder or liquid form. A certain embodiment of a food and beverage syrup comprises A) and B) .
  • An embodiment of composition comprises A) one or more ingredients selected from GSGs, GSEs, STEs, STCs, GSTEs and GSTCs; and B) a stevia glycoside composition contains one or more stevia glycosides selected from Reb A, Reb B, Reb C, Reb D, Reb E, Reb I, Reb M, Reb N, Reb O, Stevioside. An additional embodiment of composition of A) and B) , where ratio of A) to B) is from 1∶99 to 99∶1. A further embodiment of food and beverage comprises A) and or B) , where the total concentration of A) is in range of 1ppm to 10,000 ppm; and or B) where the total concentration of B) is in range of 1ppm to 2,000 ppm. A certain embodiment of a food and beverage syrup comprises A) and B) .
  • The inventor surprisingly found that current invention could improve the solubility of stevia extract, stevia glycosides. An embodiment comprises A) one or more of GSGs, GSEs, STEs, STCs, GSTEs and GSTCs; and B) one or more stevia glycosides selected from Reb A, Reb B, Reb C, Reb D, Reb E, Reb I, Reb M, Reb N, Reb O, Stevioside, where A) could improve the solubility of B) .
  • Rubusoside could inhibit absorption of glucose and fructose in intestine. Without limiting the theory, stevia extract, stevia glycosides, sweet tea extract, and sweet tea component may block the absorption of lactose, gluten, absorption by humans in intestine and nasal cavity. An embodiment of a product comprising one or more ingredient selected from SGs, SEs, SCs, GSEs, GSGs, STEs, STCs, GSTEs and GSTCs is used to improve the tolerance of lactose, gluten. A further embodiment to use such consumable for weight management.
  • The volatile substances from sweet tea could form aerosol when formulated in food and beverage. These substances could inhibit the absorption of pollen or other substances which could bring the allergies to humans. A method to use one or more STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs s in anti-allergy products. The product could be consumable, or health supplement or medical formulation such as sprayer.
  • Another aspect of the present application relates to compositions comprising one or more terpenoid glycosides (TGs) . TGs include steviol glycosides and other high intensity natural sweetening agents from plants, including glycosides, which may serve as sugar substitutes, and which are further described below.
  • A glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. The sugar group is known as the glycone and the non-sugar group as the aglycone or genin part of the glycoside. Glycosides are prevalent in nature and represent a significant portion of all the pharmacologically active constituents of botanicals. As a class, aglycones are much less water-soluble than their glycoside counterparts.
  • Depending on whether the glycosidic bond lies "below" or "above" the plane of the cyclic sugar molecule, glycosides of the present application can be classified as α-glycosides or β-glycosides. Some enzymes such as can only hydrolyze α-linkages; others, such as emulsin, can only affect β-linkages. Further, there are four types of linkages present between glycone and aglycone: a C-linked glycosidic bond, which cannot be hydrolyzed by acids or enzymes" ; an O-linked glycosidic bond; an N-linked glycosidic bond; or an S-linked glycosidic bond.
  • The glycone can consist of a single sugar group (monosaccharide) or several sugar groups (oligosaccharide) . Exemplary glycones include glucose, galactose, fructose, mannose, rhamnose, rutinose, xylose, lactose, arabinose, glucuronic acid etc. An aglycone is the compound remaining after the glycosyl group on a glycoside is replaced by a hydrogen atom. When combining a glycone with an aglycone, a number of different glycosides may be formed, including steviol glycosides, terpenoid glycosides, alcoholic glycosides, anthraquinone glycosides, coumarin glycosides, chromone glycosides, cucurbitane glycosides, cyanogenic glycosides, flavonoid glycosides, phenolic glycosides, steroidal glycosides, iridoid glycosides, and thioglycosides.
  • For example, the term "flavonoid aglycone" refers to an unglycosylated flavonoid. Flavonoid aglycones include flavone aglycones, flavanol aglycones, flavanone aglycones, isoflavone aglycones and mixtures thereof. Thus, the terms "flavone aglycone" , "flavanol aglycone" , "flavanone aglycone" and "isoflavone aglycones" refer to unglycosylated flavones, flavanols, flavanones and isoflavones, respectively. More particularly, the flavonoid aglycone may be selected from the group consisting of apigenin, luteolin, quercetin, kaempferol, myricetin, naringenin, pinocembrin, hesperetin, genistein, and mixtures thereof.
  • Terpenoid glycosides (TGs) for use in the present application, include e.g., steviol glycosides, Stevia extracts , mogrosides (MGs) , Siraitia grosvenorii (luo han guo or monk fruit) plant extracts, rubusosides (RUs) , Rubus suavissimus (Chinese sweet tea) plant extracts; flavanoid glycosides, such as neohesperidin dihydrochalcone (NHDC) ; osladin, a sapogenin steroid glycoside from the rhizome of Polypodium vulgare; trilobatin, a dihydrochalcone glucoside from apple leaves; eriodictyol, a bitter-masking flavonoid glycoside extracted from yerba santa (Eriodictyon californicum) , one of the four flavanones extracted from this plant as having taste-modifying properties, along homoeriodictyol, its sodium salt, and sterubin; polypodoside A (from the rhizome of Polypodium glycyrrhiza) ; phyllodulcin, a coumarin glycoside found in Hydrangea macrophylla and Hydrangea serrata; swingle glycosides, such as mogroside V, mogroside IV, siamenoside I, and 11-oxomogroside V, which are cucurbitane glycosides; monatin, a naturally occurring, high intensity sweetener isolated from the plant Sclerochiton ilicifolius, and its salts (monatin SS, RR, RS, SR) ; hernandulcin, an intensely sweet chemical compound gained from the chiefly Mexican and South American plant Lippia dulcis; phlorizin, plant-derived dihydrochalcone that is a glucoside of phloretin, which is found primarily in unripe Malus (apple) and the root bark of apple; glycyphyllin, an alpha-L-rhamnoside derived from phloretin, the aglucone of phlorizin, a plant-derived dihydrochalcone; baiyunoside, a diterpene glycoside isolated from the Chinese drug Bai-Yun-Shen; pterocaryoside A and pterocaryoside B, secodammarane saponin glycosides isolated from Pterocarya paliurus Batal. (Juglandaceae) , which are native to China; mukuroziosides Ia, Ib, IIa and Iib, acyclic sesquiterpene oligoglycosides isolated from the pericarp of Sapindus mukurossi and Sapindus rarak; phlomisoside I, a furanolabdane-type diterpene glycoside isolated from the roots of the Chinese plant, Phlomis betonicoides Diels (Lamiaceae) ; periandrin I and V, two sweet-tasting triterpene-glycosides from Periandra dulcis; abrusoside A-D, four sweet tasting triterpine  glycosides from the leaves of Abrus precatorius; cyclocariosides I; II, and III, and synthetically glycosylated compositions thereof (e.g., GSGs, glycosylated Stevia extracts etc) . Lithocarpus litseifolius folium (latin name) is a kind of species of sweet tea. Phlorizin and trilobatin are the main ingredients. Phlorizin is a glucoside of phloretin, a dihydrochalcone. Phlorhizin is abundant in the leaves of another kind of Sweet Tea (Lithocarpus polystachyus Rehd) , too.
  • In some embodiments, the composition of the present application is a flavor composition comprises one or more glycosylated non-sweet terpenoids in STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs in an amount of above 0.01 ppm, 0.1 ppm, 1ppm, 10ppm, 100ppm, 1,000ppm, 1%, 5%, 10%, 20%, 50%or 90%by weight.
  • In some embodiments, the flavor composition comprises one or more glycosylated non-sweet terpenoids in GSGs, GSTEs and GSTCs in an amount of above 0.01 ppm, 0.1 ppm, 1ppm, 10ppm, 100ppm, 1,000ppm, 1%, 5%, 10%, 20%, 50%, 90%, where the content of glycosylated non-sweet terpenoids is higher than the natural sources or their natural extracts. For example, Glycosylated stevia glycosides or stevia extracts contains higher glycosylated non-sweet terpenoids than their feeding material of stevia glycosides and Stevia extract before glycosylation. GSTEs, GSTCs contain higher glycosylated non-sweet terpeonoids than their STEs and STCs before glycosylation.
  • In some embodiments, the consumable product is a beverage and the beverage comprises the one or more glycosylated non-sweet terpenoids in STEs, STCs, SGs, SEs, SCs, MGs, MFEs, MFCs, GSTEs, GSTCs, GSGs, GSEs, GSCs, GMGs, GMFEs and GMFCs in an amount of 0.01-5000 ppm.
  • It should be understood that throughout this specification, when reference is made to a specific terpenoid glycoside or high intensity natural sweetening agent, such as an SG, a Stevia extract, a mogroside, a swingle extract, a sweet tea extract, NHDC, or any glycosylated derivative thereof, that the example is meant to be inclusive and applicable to all of the other terpenoid glycosides or high intensity natural sweetening agents in these classes. The same principle applies to other sweeteners; when reference is made to a sweetening agent, such as a terpenoid glycoside sweetener, steviol glycoside sweetener, high intensity natural sweetener, sweetener enhancer, high intensity synthetic sweetener, reducing sugar, or non-reducing sugar,  that the example is meant to be inclusive and applicable to all of the other sweeteners or sweetening agents in any given class.
  • Plants contain aglycones, which normally are hydrophobic, water insoluble volatile substances. There are also glycosides in plants which are more water soluble. The inventor found that glycosylation process could make these hydrophobic compounds into water soluble and stable in water solution. The inventor surprisingly found that adding these substances in food and beverage could significantly improve the intensity of retronasal aroma. An embodiment of flavor composition comprises glycosylated treated ingredients to have content of glyocosides higher than their natural plant sources before glycosylation treatment, where the ingredients are originated from plant sources such as leaves, flowers, fruits, berries, barks, seeds etc. An embodiment of these composition further include one or more components selected from stevia extract, stevia glycosides, glycosylated stevia extract, glycosylated stevia glycosides, sweet tea extract, sweet tea components, glycosylated sweet tea extract, glycosylated sweet tea components, monk fruit extract, monk fruit component, glycosylated monk fruit extract, glycosylated monk fruit component, licorice root extract, licorice root component, glycosylated licorice root extract, glycosylated licorice root component. An embodiment of all these types of glycosylated treated plant ingredients are used in food and beverage.
  • Flavonoids are widely contained in citrus such as lemon, conferring the typical taste and biological activities to lemon. There are five main flavonoid glycosides, of which the aglycone are eriocitrin, narirutin, hesperidin, rutin, and diosmin, respectively. Citrus extract could be glycosylated. An embodiment of a flavor composition comprises glycosylated substances in citrus extracts higher than its original natural sources. A further embodiment of a consumable comprises lemon extract with enriched glycosylated substances in amount of higher than 0.01 ppm, 0.1ppm, 1ppm, 5ppm, 100ppm, 1,000ppm, 5,000ppm, 1%, 5%or 10%by weight.
  • Natural sources used to produce food and beverage, such as apple to produce apple juice, citrus peels to produce citrus flavor. During the concentration of juice, water soluble volatile substances could be collected and could be used in the formulation of retronasal aroma. An embodiment of retronasal aroma composition comprises water soluble volatile substances. In some embodiments, the consumable product is a beverage or food, and the beverage or food comprises a) the one or more Stevia extracts, SGs, glycosylated Stevia extract, GSGs, STEs,  GSTEs, STCs and GSTCs and b) water soluble volatile substances from fruit juices, berries, species, where the water soluble volatile substances in an amount of 0.01-5000 ppm.
  • The embodiments described above are applicable for any synthetic sweetener, blends thereof and other natural sweeteners, blends thereof, or mixtures of synthetic and natural sweetener (s) , especially sucralose.
  • EXAMPLES
  • Example 1. Purification treatment of Rubusoside 20% (RU20)
  • Materials: Rubusoside 20% (RU20, Guilin Layin Natural Ingredients Corp. The concent of RU is 20.68%Lot# STL02-151005) , CaO (Sinopharm Chemical Reagent Co., Ltd)
  • Process:
  • i) 20 g Rubusoside 20%was dissolved in 170 ml deionized water and stirred at 69 ℃. for 2 hours.
  • ii) 60 mL 0.1mol/L CaO was added to above i) solution and stirred at 69 ℃. for 30 min.
  • iii) the above ii) solution was incubated at room temperature for 30 min, followed by centrifugation at 4000 rpm for 10 min.
  • iv) the pH of the supernatant from iii) was adjusted to about 5.3 and followed by centrifugation at 4000 rpm for 10 min.
  • v) the solution from iv) was treated with cation exchange resin (Xi′an Lanxiao Technology New Material Co., Ltd) .
  • vi) the solution from (v) was spray dried, yielding 10g of treated-RU20 (TRU20) as a white powder.
  • Example 2. Preparation of glycosylated treated RU (GTRU20) from treated rubusoside 20% (TRU20)
  • A glycosylated reaction product composition was prepared using Rubusoside 20% (the product of Example 1, TRU20) according to the following method:
  • i) 15 g Tapioca dextrin (BAOLIBAO BIOLOGY Co., Ltd) was dissolved in 45 ml deionized water
  • ii) 15 g TRU20 (the product of Example 1) was added to liquefied dextrin to form a mixture.
  • iii) 0.75 ml CGTase enzyme (Amano Enzyme, Inc) and 15 ml deionized water were added to the mixture and incubated at 69℃ for 20 hours to glycosylate the TRU20 with glucose molecules derived from Tapioca dextrin.
  • iv) The reaction mixture in iii) was heated to 85℃ for 10 min to inactivate the CGTase, which was then removed by filtration.
  • v) The resulting solution of glycosylated rubusoside (GRU) , residual RU and dextrin were decolored and spray dried, thereby yielding 25 g of GTRU20 as a white powder (the residue RU is 1.15 wt%) .
  • Example 3. Sweetness and overall likability evaluation of RU20, GTRU20
  • The products in examples below are evaluated by the following method.
  • Sensory evaluation method:
  • Products were evaluated in terms of mouth feel, bitterness, bitterness lingering, sweet lingering, metallic aftertaste and overall likability.
  • A panel of 6 trained testers evaluated the samples and gave scores of 1-5 according to the followed standards. The average score of the panel members was taken as the score of each factor.
  • For mouth feel, one factor, kokumi, was evaluated.
  • 1) Kokumi level
  • Evaluation standard: A 5%sucrose solution with neutral water was prepared. This solution was used as a standard solution to which the kokumi degree was set as 5.
  • A 250 ppm RA (available from Sweet Green Fields) solution was prepared with neutral water. This solution was used as a standard solution to which the kokumi degree was set as 1.
  • An appropriate amount of yeast extract (available from Leiber, 44400P-145) was dissolved in a 250 ppm aqueous solution of RA97 such that the degree of kokumi of the resulting solution was consistent with the standard solution of kokumi degree of 5 (5%sucrose) . After evaluation by a panel of 6 testers, it was determined that a solution of 100 ppm the yeast extract dissolved in 250 ppm RA97 was substantially identical to the degree of kokumi of the 5%sucrose solution. Thus, the criteria for determining the degree of kokumi are as follows.
  • Table 3-1. Kokumi evaluation test standard
  • Evaluation method:
  • The sample to be evaluated was dissolved in neutral deionized water. The tester placed 20-30 mL of the evaluation solution in their mouth. After 5 seconds the solution was spit out. After a mouthwash step with water, the standard solution was taken. If the degree of Kokumi was similar, the Kokumi degree of the sample solution could be determined as the Kokumi degree value of the standard solution. Otherwise it was necessary to take additional standard solutions and try again until the Kokumi degree value was determined.
  • 2) Bitterness
  • Quinine (99%purity) concentration of 10 -8-10 -4 mol/L was the bitterness standard, and the specific bitterness scoring standards are shown in the following table.
  • Table 3-2. Bitterness evaluation test standard
  • Range of quinine concentrations ＜8×10 -7 8×10 -7～3×10 -6 7×10 -6～2×10 -5 2×10 -5～1×10 -4 ＞1×10 -4
  • (mol/L)          
    Bitterness score 1 2 3 4 5
  • The sample to be evaluated was dissolved in neutral deionized water. The tester placed 20-30 mL of the evaluation solution in their mouth. After 5 seconds the sample was spit out. After a rinse step with water, the standard solution was tasted. If the bitter taste was similar, the bitterness of the sample could be determined as the bitterness value of the standard solution. Otherwise it was necessary to take additional standard solution (s) and try again until the bitterness value was determined.
  • 3) Bitterness lingering
  • The sample to be evaluated was dissolved in neutral deionized water. The tester placed 20-30 mL of the evaluation solution in their mouth, and timing was started to record the bitterness start time and peak time. The test solution was then spit out. Recording of time continued for the time when the bitterness disappeared completely. The time at which the bitterness completely disappeared was compared to the time in the table below to determine the value of bitterness lingering.
  • Table 3-3. Bitterness lingering evaluation test standard
  • 4) Sweet lingering
  • The sample to be evaluated was dissolved in neutral deionized water. The tester placed 20-30 mL of the evaluation solution in their mouth, and timing was started to record the sweetness start time and peak time. The test solution was then spit out. Recording of time continued for the time when the sweetness disappeared completely. The time at which the sweetness completely disappeared was compared to the time in the table below to determine the value of sweet lingering.
  • Table 3-4. Sweet lingering evaluation test standard
  • 5) Metallic aftertaste
  • Sucralose (available from Anhui Jinhe Industrial Co., Ltd and Lot# is 201810013) was used as a standard reference. The specific metallic aftertaste scoring standards are shown in the table below.
  • Table 3-5. Metallic aftertaste evaluation test standard
  • Range of sucralose concentrations ＜50ppm 50-100ppm 100-150ppm 150-200ppm ＞200ppm
    Metallic aftertaste score 1 2 3 4 5
  • The sample to be evaluated was dissolved in neutral deionized water. The tester placed 20-30 mL of the evaluation solution in their mouth. After 5 seconds, the solution was spit out. After a rinse step with water the standard solution was tasted. If the metallic aftertaste was similar, the metallic aftertaste of the sample was determined as the metallic aftertaste score of the standard liquid, otherwise it was necessary to take additional standard liquid samples and taste it again until the metallic aftertaste score was determined.
  • 6) Overall likability
  • Overall likability is the general impact of the sample. The sample to be evaluated was dissolved in neutral deionized water. The tester places 20-30 mL of the evaluation solution in their mouth and evaluate the general impact based on its kokumi, bitterness, bitterness lingering, sweet lingering, and metallic aftertaste. The test solution was then spit out. A score of 1-5 indicates a strong dislike, dislike, average, like, and strong like, respectively.
  • 7) Sucrose equivalence or SugarE
  • The phrase “sucrose equivalence” or SugarE is the amount of non-sucrose sweetener required to provide the sweetness of a given percentage of sucrose in the same solution.
  • Table 3-6. SugarE evaluation standard:
  • Evaluation method: The sample to be evaluated was dissolved in neutral deionized water. The tester placed 20-30 mL of the evaluation solution in their mouth. After 5 seconds the solution was spit out. After a mouthwash step with water, the standard solution was taken. If the degree of SugarE was similar, the SugarE degree of the sample solution can be determined as the SugarE degree value of the standard solution. Otherwise it was necessary to take additional standard solutions and try again until the SugarE degree value was determined.
  • 8) Time-intensity curves
  • Evaluation method: Each person of the test panel had to drink sample solutions with defined concentrations. During the test, all persons had a time clock. They had to note the appearance-time for four specific points of a time-intensity curves (onset, maximum sweetness, lingering on and lingering off) . The results were recorded and make a graph, mean values were calculated from at least 6 individual test persons. FIG. 1 shows a schematic diagram of the time-intensity curve.
  • 9) Starch taste
  • Maltodextrin (available from BAOLIBAO BIOLOGY Co., Ltd) was used as a standard reference. The specific starch taste scoring standards are shown in the table below.
  • Table 3-7. Starch taste evaluation test standard
  • Range of maltodextrin concentrations ＜0.5% 0.5%-1% 1%-2% 2%-3% ＞3%
    Score of starch taste 1 2 3 4 5
  • The sample to be evaluated was dissolved in neutral deionized water. The tester placed 20-30 mL of the evaluation solution in their mouth. After 5 seconds, the solution was spit out. After a rinse step with water the standard solution was tasted. If the starch taste was similar, the starch taste of the sample was determined as the starch taste score of the standard liquid, otherwise it was necessary to take additional standard liquid samples and taste it again until the starch taste score was determined.
  • Preparation of sample solutions:
  • RU20, GTRU20, from Examples 1 to 2 were weighed and uniformly mixed according to the weights shown in Tables 3-8 and 3-9; dissolved in 100ml pure water; and subjected to a sweetness and overall likability evaluation test.
  • Table 3-8. RU20 sample composition
  • Table 3-9. GTRU20 sample composition
  • The sugar equivalence and overall likability (an overall likebility score of 4 or above means very good taste, an overall likebility score of 3 or above means palabable taste) of above solutions were evaluated by the above method.
  • The results are shown in Tables 3-10 and 3-11.
  • Table 3-10. SugarE and overall likability evaluation of RU20
  • Table 3-11. SugarE and overall likability evaluation of GTRU20
  • NO. Concentration of Sugar equivalence Overall likability
  •   GTRU20 (ppm)  (SugarE)  
    3-2-01 200 0.3 3.65
    3-2-02 400 1 3.1
    3-2-03 800 2 2.5
    3-2-04 1600 2.8 2
    3-2-05 2400 4 1
    3-2-06 4000 5 1
    3-2-07 5000 5 1
  • Data analysis: The SugarE of different concentrations of RU20, GTRU20 in this Example are shown in FIGs. 2A and 2B, respectively.
  • Conclusion: As shown in FIG. 2A, the taste of RU20 was unpalatable even at low SugarE level. However, when modified by glycosylation, the taste was improved, as shown in FIG. 2B. The SugarE at which the taste can be palatable increased to 1%SugarE. This example demonstrates that the overall likability of RU20 can be modified, such as by glycosylation.
  • Example 4. Evaluation of the taste profiles of RU20, GTRU20 in a 40%sugar reduction system
  • Materials: RU20, Guilin Layin Natural Ingredients Corp. The concent of RU is 20.68%; Lot#: STL02-151005; GTRU20, the product of Example 2.
  • Preparation of sample solutions: RU20, GTRU20, and 6%sugar solution were mixed according to the weights shown in Table 4-1 below.
  • The samples in example below were evaluated by the method in Example 3. Each panelist was asked to evaluate by his preference on six aspects -flavor, sweet lingering, mouth feel, bitterness, bitterness lingering and overall likability. It should be noted that according to the sensory evaluation method, the evaluation of the mouth feel, sweet lingering, bitterness, bitterness lingering and overall likability is based on the iso-sweetness, 10%SugarE. The evaluation results are shown in Table 4-2.
  • Table 4-1. Test sample composition
  • Evaluation: Table 4-2. RU20, GTRU20 in 6%sugar solution
  • Conclusion: In a 40%sugar reduction system, compared to RU20, the bitterness and bitterness lingering of the GTRU20 were remarkably decreased. The results further showed that the mouth feel of RU20 can be significantly improved by purification and then glycosylation.
  • Example 5. Preparation of glycosylated Rubusoside 90% (GRU90) from Rubusoside 90%
  • Glycosylated reaction products from Rubusoside 90%were prepared according to the following method.
  • Rubusoside 90% (available from EPC Natural Products Co., Ltd. The content of RU is 92.8%Lot# EPC-238-34-03)
  • i) 15 g tapioca dextrin was dissolved in 45 ml deionized water.
  • ii) 15 g Rubusoside 90%was added to liquefied dextrin.
  • iii) 0.75 ml CGTase enzyme and 15ml deionized water were added to the mixture of ii) and incubated at 69℃ for 20 hours to glycosylate the RU90 composition via glucose molecules derived from tapioca dextrin.
  • iv) The reaction mixture was heated to 85℃ for 10 min to inactivate the CGTase, which was then removed by filtration.
  • v) The resulting solution of GRU90, residual RU and dextrin were decolored and spray dried yielding 25 g of GRU90 as a white powder (the content of residue RU is 12.16%) .
  • Example 6. Evaluation of the taste profile of RU90 and GRU90 in 60%sugar reduction system
  • Materials: RU90, available from EPC Natural Products Co., Ltd. The content of RU is 92.8%; GRU90, the product of Example 5.
  • Method: RU90, GRU90 and 4%SugaE sugar solution were mixed according to the weight shown in Table 6-1 in this example. Each sample was evaluated according to the aforementioned sensory evaluation method in Example 3. It should be noted that according to the sensory evaluation method, the evaluation of the mouth feel and the taste profile were based on the iso-sweetness, 10%SugarE. The evaluation results are shown in Tables 6-2 and 6-3.
  • Table 6-1. Test sample composition
  • Evaluation: Table 6-2. RU90, GRU90 in 4%sugar solution
  • Conclusion: In a 60%sugar reduction system, GRU90 showed significantly decreased bitterness and bitterness lingering compared to RU90. In addition, GRU90 provided a significantly pleasant flavor that served to improve their full body mouth feel. In summary,  GRU90 a significantly more pleasant taste, as well as remarkably improved overall likability compared to RU20.
  • Example 7. GTRU20 improves the taste and mouth feel of sucralose
  • Process: GTRU20 and sucralose (available from Anhui Jinhe Industrial Co., Ltd and Lot# is 201810013) were weighed and uniformly mixed according to the weight shown in Table 7-1, dissolved in 100 ml pure water, and subjected to a sensory evaluation test.
  • Table 7-1. Test sample composition
  • Evaluation: Several mixtures of GTRU20 and sucralose were mixed in this example. Each sample was evaluated according to the aforementioned sensory evaluation method in example 5, and the average score of the panel was taken as the evaluation result data. The taste profile of the mixture is as follows. It should be noted that according to the sensory evaluation method, in these evaluations, the concentration of sucralose in the sample solution was the same, 150 ppm. The results are shown in Table 7-2.
  • Table 7-2. Sensory evaluation results
  • Data analysis: The relationship between the sensory evaluation results to the ratio of sucralose to GTRU20 in this example is shown in FIG. 3A. The relationship between the overall likability results to the ratio of sucralose to GTRU20 in this example is shown in FIG. 3B.
  • Conclusion: The results showed that GTRU20 significantly improved the mouth feel, cut the sweet lingering and decrease the metallic aftertaste of sucralose. This effect was observed in all the tested sucralose-to-GTRU20 ratios (from 10∶1 to 10∶100) . The effect can be extended to a sucralose-to-GTRU20 ratio range of 99∶1 to 1∶99. This example demonstrates that GTRU20 could improve taste profile, flavor intensity and mouth feel of artificial sweetener such as sucralose. Such effect can be extended to all artificial sweeteners.
  • Example 8. GTRU20 improves the taste and mouth feel of RA97
  • Process: GTRU20 and RA97 (available from Sweet Green Fields. The content is 97.15%. Lot# 3050123) were weighed and uniformly mixed according to the weight shown in Table 8-1, dissolved in 100ml pure water, and subjected to a sensory evaluation test.
  • Table 8-1. Test sample composition
  • Experiment: Several mixtures of RA97 and GTRU20 were mixed in this example. Each sample was evaluated according to the aforementioned sensory evaluation method in Example 3, and the average score of the panel was taken as the evaluation result data. The taste profile of the mixture is as follows. It should be noted that according to the sensory evaluation method, in these evaluations, the concentration of RA97 in the sample solution was the same, 200 ppm. The results are shown in Table 8-2.
  • Table 8-2. Sensory evaluation results
  • Data analysis: The relationship between the sensory evaluation results to the ratio of RA97 to GTRU20 in this example is shown in FIG. 4A. The relationship between the overall likability results to the ratio of RA97 to GTRU20 in this example is shown in FIG. 4B.
  • Conclusion: The result showed that GTRU20 significantly improve the mouth feel, cut the sweet lingering and decrease the bitterness of RA97. This effect was observed in all the tested RA97-to-GTRU20 ratios (from 10∶1 to 10∶100) . The effect can be extended to the RA97-to-GTRU20 ratio range of 99∶1 to 1∶99. This example demonstrates that GTRU20 can improve taste and mouth feel of natural sweetener such as RA97. Such effect can be extended to all natural sweeteners.
  • Example 9. Sweetness and overall likability evaluation of RU90 and GRU90
  • RU90 and GRU90 from Examples 5-6 were weighed and uniformly mixed according to the weights shown in Table 9-1 and 9-2 dissolved in 100ml pure water; and subjected to a sweetness and overall likability evaluation test.
  • Table 9-1. RU90 sample composition
  • Table 9-2. GRU90 sample composition
  • The sugar equivalence and overall likability of above solutions were evaluated by the above method in Example 3.
  • The results are shown in Tables 9-3 and 9-4.
  • Table 9-3. SugarE and overall likability evaluation of RU90
  • Table 9-4. SugarE and overall likability evaluation of GRU90
  • Data analysis: The SugarE evaluation of different concentrations of RU90 and GRU90 in this Example is shown in FIGs. 5A and 5B.
  • Conclusion: As shown in FIG. 5A, the acceptable taste of RU90 is low to 2%SugarE. However, the good taste perception of GRU90 was improved to 4%SugarE, as shown in  FIG. 5B. This example demonstrates that the overall likability of RU90 can be modified by further modification, such as glycosylation.
  • Example 10. GRU90 improves the taste and mouth feel of acesulfame-K
  • Process: GRU90 and acesulfame-K (available from JINGDA PERFUME) were weighed and uniformly mixed according to the weight shown in Table 10-1, dissolved in 100 ml pure water, and subjected to a mouth feel evaluation test.
  • Table 10-1. Test sample composition
  • Experiments: Several mixtures of GRU90 and acesulfame-K were mixed in this example. Each sample was evaluated according to the aforementioned sensory evaluation method in Example 3, and the average score of the panel was taken as the evaluation result data. The taste profile of the mixture is as follows. It should be noted that according to the sensory evaluation method, in these evaluations, the concentration of acesulfame-K in the sample solution was the same, 200 ppm. The results are shown in Table 10-2.
  • Table 10-2. Sensory evaluation results
  • Data analysis: The relationship between the sensory evaluation results to the ratio of acesulfame-K to GRU90 in this example is shown in FIG. 6A. The relationship between the overall likability results to the ratio of acesulfame-K to GRU90 in this example is shown in FIG. 6B.
  • Conclusion: The result showed that GRU90 significantly improved the mouth feel, cut the sweet lingering, decrease the metallic aftertaste and bitterness of acesulfame-K. This effect was observed in all the tested acesulfame-K-to-GRU90 ratios (from 10∶1 to 10∶100) . The effect can be extended to the acesulfame-K-to-GRU90 ratio range of 99∶1 to 1∶99. This example demonstrates that GRU90 can improve taste, flavor intensity and mouth feel of artificial sweetener such as acesulfame-K. Such effects can be extended to all artificial sweeteners.
  • Example 11. Formation of rubusoside from steviol glycoside compositions
  • Materials: Steviol glycosides: RA20/TSG (9) 95, Lot No. EPC-309-1-0, Reb A 28.98%, Stevioside 60.36%, available from Sweet Green Fields. β-galactosidase: Lactase DS 100, Lot No. LAMR0351901K, 111000ALU/g, available from AmanoEnzyme Inc.
  • Process: 100 mL steviol glycosides solution (80g/L) and β-galactosidase (0.8 kU/g stevioside) were mixed in a 250 mL flask, stirred at 60℃ for 8 h. The reaction mixture was then boiled for 3 min to deactivate the enzyme and the precipitated enzyme was removed by centrifugation. The supernatant was spray-dried to produce 7.5 g white powder, which contained 27.4%Reb A, 42.8%rubusoside and almost no stevioside.
  • Conclusion: Stevioside can be converted to rubusoside by the effect of β-galactosidase. Under certain conditions, the conversion ratio is close to 100%. The converted product (in solution or powder form) can be used as raw material for glycosylation, or it can be further purified into 95%total stevia glycosides. The rubusoside can be enriched by crystallization etc. to any desired purity. For instance, rubusosides can be prepared from a Stevia extract to a purity of more than 40%, 90%or 95%. Any type of these compositioins can be used as sweetener or flavor ingredient in food and beverage products. Any type of these composition can be further subjected to a glycosylation reaction to produce a glycosylated product.
  • Some embodiments of the present application relate to a Stevia extract comprising rubusoside and Reb A, wherein the Reb A content is less than 50%, 40%, 30%, 20%, 10%, 5%by weight of the Stevia extract. A further embodiment of the Stevia extract comprises rubusoside and Reb A, wherein the total amount of rubusoside and Reb A is above 50%by weight of the Stevia extract, where ratio of rubusoside to Reb A is greater than 1∶2 or 1∶1.
  • Some embodiments of the present application relate to a Stevia extract comprising rubusoside, Reb A, and one or more other stevia glycosides selected from the group consisting of stevioside, Reb B, Reb C, Reb D, Reb E, Reb I, Reb M, Reb N and Reb O, wherein the total amount of the one or more other stevia glycosides is less than 50%, 40%, 30%, 20%, 10%, 5%, 2%, 1%, 0.5%by weight of the Stevia extract. In some embodiments, the Stevia extract comprises stevioside in an amount that is less than 50%, 40%, 30%, 20%, 10%, 5%, 2%, 1%, 0.5%by weight of the Stevia extract.
  • Some embodiments of the present application relate to a glycosylated Stevia extract composition that comprises glycosylated Reb A and glycosylated rubusoside, unreacted Reb A and unreacted rubusoside. In some embodiments, the the total content of glycosylated rubusoside and glycosylated Reb A is above 1%, 5%, 10%, 40%, 50%, 60%, 70%, 80%, 85%, 90%, 95%by weight of the composition.
  • Some embodiments of the present application relate to a composition that comprises (1) glycosylated rubusoside originated from a Stevia extract, and/or (2) glycosylated rubusoside enzymatic converted from stevisoide. In some embodiments, the glycosylated rubuososide is present in an amount of greater than 1%, 5%, 10%, 20%, 30%, 40%, 50%, 60%, 80%, 90%or 95%by weight of the composition. In some embodiments, the composition further comprises unreacted rubusoside and sugar donors, such as starch or dextrins. In some embodiments, the dextrins is present in an amount of less than 30%, 20%, 15%, 10%, or 5%by weight of the composition.
  • Example 12. Sensory evaluation of steviol glycoside samples
  • Materials: RU20, Lot # STL02-151005, EPC Lab; GRU20, Lot # EPC-303-89-03, EPC Lab; TRU20, Lot # EPC-303-74-01, EPC Lab; GTRU20, Lot # EPC-303-73-01, EPC Lab; RU90, Lot # EPC-238-34-03, EPC Lab; GRU90, Lot # EPC-303-89-02, EPC Lab.
  • Sample preparation: To perform the tests, a 100 ppm water solution of each sample was prepared and sensory evaluated. The test results are summarized in Table 12-1.
  • Table 12-1. Sensory evaluation results
  • Conclusion: Compared to rubusoside and/or sweet tea extract, G-STE, G-STC, showed significantly improved palatability. The unique characters of these products, such as  colorless, neutral odor and less lingering, provide advantage in their use in food and beverage applications.
  • Example 13. Sweetness profile of thaumatin with/without Ru samples
  • Materials: GRU20, Lot # EPC-303-89-03, EPC Lab; GRU90, Lot # EPC-303-89-02, EPC Lab; RU20, Lot # STL02-151005, EPC Lab; TRU20, Lot # EPC-303-74-01, EPC Lab; RU90, Lot # EPC-238-34-03, EPC Lab; Thaumatin 93%, Part Number T93001, Lot # 20190601.
  • Experimental design and results:
  • The following samples were prepared and evaluated:
  • I. 15 ppm thaumatin
  • II. 15 ppm thaumatin + 50 ppm RU20
  • III. 15 ppm thaumatin + 50 ppm RU90
  • IV. 15 ppm thaumatin + 50 ppm GRU20
  • V. 15 ppm thaumatin + 50 ppm GRU90
  • VI. 15 ppm thaumatin + 50 ppm TRU20
  • The test results are shown in Table 13-1 and FIGS. 7A-7F.
  • Table 13-1. Sensory test results
  • Conclusion: As shown in FIG. 7B, RU20 reduced lingering by 7 seconds. RU90, GRU20 and GRU90 were able to reduce lingering by 20 and 19 seconds respectively (FIG. 7C to 7E) . Effect of TRU20 was presented by reduce lingering by 14 seconds (FIG. 7F) .
  • Example 14. Analytical investigations with Sweet Tea Leaf extracts
  • Sample descriptions:
  • 1. Product Name: RU20 (Guilin Layin Natural Ingredients Corp. ) , Lot#: STL02-151005
  • Process: This sample is sweet tea extract Rubusoside 20%
  • 2. Product Name: GRU20, Lot#: EPC-303-89-03.
  • Process: This sample is enzymatic transglucosylated RU20.
  • 3. Product Name: TRU20, Lot#: EPC-303-74-01.
  • Process: This sample is treated sweet tea extract RU20.
  • 4. Product Name: GTRU20-Treated, Lot#: EPC-303-73-01.
  • Process: This sample is enzymatic transglucosylated TRU20.
  • 5. Product Name: RU90, Lot#: EPC-238-34-03.
  • Process: This sample is sweet tea extract Rubusoside 92%.
  • 6. Product Name: GRU90, Lot#: EPC-303-89-02.
  • Process: This sample is enzymatic transglucosylated RU90.
  • Methods and Materials
  • Reference standards (to qualify the analytical method) for steviolglycosides (Reb A, Reb B, Reb C, Reb D, Reb E, Reb F, Reb G, Reb I, Reb M, Reb N, Reb O, Stevioside, Isoreb A, Isostevioside) were obtained from Chromadex (LGC Germany) . Solvents and reagents (HPLC grade) were obtained from VWR (Vienna) or Sigma-Aldrich (Vienna) . Davisil Grade 633 (high-purity grade silica gel, pore size  200-425 mesh particle size was obtained from Sigma-Aldrich (Vienna) .
  • Sample Preparation (HPLC/DAD/MS) :
  • All samples were fractionated over a glass column (100 x 5 mm) filled with Davisil Grade 633. The column was equilibrated with ethlyacetate/Acetic acid/H 2O = 8/3/2 (v/v/v) . 100 mg sample, dissolved in 2 ml H 2O, were loaded on the column and eluted with ethlyacetate/Acetic acid/H 2O = 8/3/2 at a flow rate of 2 ml/min. The first 6 ml of the eluate were discarded and the next 30 ml containing unreacted steviol-glycosides were collected. Enzymatically reacted steviol-glycosides eluted in the range of 36-70 ml and were again collected.
  • After fractionation of 3 samples, the pooled eluates were evaporated to dryness and reconstituted in 20 ml Acetonitrile/H 2O=9/1 (v/v) corresponding to an equivalent sample concentration of 150 mg sample/10 ml.
  • The method was qualified by fractionation of steviolglycoside standards and enzymatically reacted steviol-glycosides. An elution yield of ＞97 %of steviol-glycosides and of ＞95 %enzymatically reacted steviol-glycosides was observed, the carry over between the fraction was calculated to less than 3 %.
  • The pooled, evaporated samples were used for analysis of steviol-related compounds as well as for non-volatile non-steviol-related compounds.
  • HPLC-Method:
  • The HPLC system consisted of an Agilent 1100 system (autosampler, ternary gradient pump, column thermostat, VWD-UV/VIS detector, DAD-UV/VIS detector) connected in-line to an Agilent mass spectrometer (ESI-MS quadrupole G1956A VL) . For HPLC analysis 150 mg of the corresponding sample was dissolved in Acetonitrile (1 ml) and filled up to 10 ml with H 2O.
  • The samples were separated at 0.8 ml/min on a Phenomenex Synergi Hydro-RP (150 x 3 mm) followed by a Macherey-Nagel Nucleosil 100-7 C18 (250 x 4.6 mm) at 45 ℃ by gradient elution. Mobile Phase A consisted of a 0.01 molar NH 4-Acetate buffer (native pH) with 0.1%acetic acid, 0.05 %trimethylamine and 0.001%dichloromethane. Mobile Phase B consisted of 0.01 molar NH 4-Acetate buffer (native pH) and Acetonitrile (1/9 v/v) with 0.1%acetic acid, 0.05 %trimethylamine and 0.001%dichloromethane. The gradient started with 22 % B, was increased linearly in 20 minutes to 45 %B and kept at this condition for another 15 minutes. Injection volume was set to 10 μl.
  • The detectors were set to 210 nm (VWD) , to 205 and 254 nm (DAD with spectra collection between 200-600 nm) and to ESI negative mode TIC m/z 300-1500, Fragmentor 200, Gain 2 (MS, 300 ℃, nitrogen 12 l/min, nebulizer setting 50 psig. Capillary voltage 4500 V) .
  • Detection at 205 and 210 nm were used to quantify the chromatograms, the MS-spectra were used to determine the molar mass and structural information of individual peaks. Detection at 254 nm was used to identify non-steviolglycoside peaks.
  • Samples were quantified by external standardization against reference compounds of Reb A or stevioside, in case where no authentic reference standard was available, the peak area was quantified against the reference standard with the most similar mass and corrected for the molar mass differences. The calibration range of reference standards was in a range 1-75 mg/10 ml (dissolved in Acetonitrile/H 2O=9/1 (v/v) ) .
  • Identification and Quantification
  • Steviol-glycosides and enzymatically reacted steviol-glycosides were identified by comparison of retention times to authentic reference standards and/or by evaluation of the mass spectra obtained (including interpretation of the fragmentation pattern and double charged ions triggered by the presence of dichloromethane) .
  • Steviol-glycosides were quantified against external standards. In case that no reference standard was available quantification was performed against the reference standard with the most similar molar mass.
  • Sample preparation (GC/MS) :
  • 1g of the sample was dissolved in 100 ml water and transferred in a round flask used for water steam distillation. The sample was submitted to a combined water steam distillation and solvent extraction/concentration process as shown in FIG. 29. One ml of the organic solvent used was ethyl acetate placed between the bubbles HJ and L.
  • The steam distillation was performed for 120 minutes. The ethyl acetate was collected and injected onto the GC/MS system.
  • Results:
  • [Rectified under Rule 91, 08.02.2021]
    Tables 14-1 to 14-3 show the test results for steviol-glycosides and glucosylated steviol-glycosides. Tables 14-4 and 14-5 show the suavioside related compounds detected in the samples. Table 14-6 shows volatile compounds observed in the samples. FIGS. 8-11 show chromatograms of exemplifying samples. Table 14-7 shows representative structures of suaviosides. FIGS. 12-20 show chromatograms of various samples.
  • [Rectified under Rule 91, 08.02.2021]
    The screening for gallic acid, rutin and ellagic acid (described in the literature as marker compounds for Rubus suavissimus S. leaves) failed to show any of these compounds in the samples. The screening consisted of comparison of retention times to authentic standards, comparison of online DAD-UV spectra and tracing of m/z values in ESI-MS detection. FIG. 11 shows a chromatographic evaluation at 254 nm. As seen there, there are no discernable signals observed in the RU20 and GRU20 samples. These two samples should contain the maximum amount of compounds from this class.
  • As seen in Tables 14-1 to 14-3, the base samples with 20 %rubusoside (whether or not treated) contains mainly rubusoside and steviol-monoside in a ratio of around 10∶1 together with traces of suaviosides. The base sample with 92 %rubusoside contains mainly  rubusoside and traces of suaviosides (see Table 14-4) . It is therefore acceptable to allocate glucosylated steviol-glycosides as stemming mostly from rubusoside. Steviol-monoside with one added glucose can be determined due to chromatographic separation from Rubusoside, in all other glycosylation patterns it can only be differentiated between different molar masses, but not the basic molecule (rubusoside or steviol-monoside) . As shown in Tables 14-1 to 14-3, the glycosylated samples show for most molar masses 2 peaks which are interpreted as rubusoside isomers.
  • Further tracing of minor steviol-related compounds tentatively present in sweet tea leaf extracts (i.e. suaviosides) was performed by detailed evaluation of the ESI-MS trace. FIGS. 8A and 8B present comparative fingerprints and Tables 14-4 and 14-5 provide quantitative estimates for steviol-related compounds, tentatively from the group of suaviosides. Table 14-6 shows the qualitative results for the volatile compounds detected in the RU20, RU90, TRU20, GRU20 and GRU90 samples.
  • Table 14-1. Steviolglycosides detected in the RU20 sample and the GRU20 sample therefrom.
  • Tentative structure m/z RU20 GRU20
    Related (as Ru)   1.24 1.26
    Ru-5Glc A 1452 n.d.  2) 0.31
    Ru-5Glc B 1452 n.d. 0.62
    Ru-4Glc A 1289 n.d. 0.98
    Ru-4Glc B 1289 n.d. 1.78
    Ru-3Glc A 1127 n.d. 0.41
    Ru-3Glc B 1127 n.d. 0.52
    Ru-2Glc A 965 n.d. 1.47
    Ru-2Glc B 965 n.d. 2.65
  • Ru-1Glc A/B 803 n.d. 4.86
    Ru 641 23.4 4.01
    Stev-Mono 479 3.58 1.44
  • 1) ... Quantification was performed by peak area at 210 nm against Reb A as external standard with molar mass correction where applicable;
  • 2) ... n.d.: not detected
  • Table 14-2. Steviolglycosides detected in the TRU20 sample and the GTRU20 sample therefrom.
  • Tentative structure m/z TRU20 GTRU20
    Related (as Ru)   1.07 1.952
    Ru-5Glc A 1452 n.d. 0.36
    Ru-5Glc B 1452 n.d. 0.66
    Ru-4Glc A 1289 n.d. 1.08
    Ru-4Glc B 1289 n.d. 1.61
    Ru-3Glc A 1127 n.d. 0.36
    Ru-3Glc B 1127 n.d. 0.53
    Ru-2Glc A 965 n.d. 1.34
    Ru-2Glc B 965 n.d. 2.36
    Ru-1Glc A/B 803 n.d. 4.51
    Ru 641 25.5 1.37
    Stev-Mono 479 2.04 0.0748
  • 1) ... Quantification was performed by peak area at 210 nm against Reb A as external standard with molar mass correction where applicable;
  • 2) ... n.d.: not detected
  • Table 14-3. Steviolglycosides detected in the RU90 sample and the GRU90 sample therefrom.
  • Tentative structure m/z RU90 GRU90
    Related (as Ru)   n.d.  2) 3.71
    Ru-5Glc A 1452 n.d. 1.28
    Ru-5Glc B 1452 n.d. 2.61
    Ru-4Glc A 1289 n.d. 4.24
    Ru-4Glc B 1289 n.d. 7.14
    Ru-3Glc A 1127 n.d. 1.62
    Ru-3Glc B 1127 n.d. 2.02
    Ru-2Glc A 965 n.d. 5.67
    Ru-2Glc B 965 n.d. 10.9
    Ru-1Glc A/B 803 n.d. 18.3
    Ru 641 92.8 12.7
    Stev-Mono 479 n.d. n.d.
  • 1) ... Quantification was performed by peak area at 210 nm against Reb A as external standard with molar mass correction where applicable;
  • 2) ... n.d.: not detected
  • Table 14-4. Suavioside related compounds in samples derived from RU 92 %.
  • 1) ... Calculated as Rubusoside on basis of peak area at 210 nm, compound identification is tentative on basis of mass spectra.
  • 2) ... 9-Hydroxy-Suavioside J
  • Table 14-5. Suavioside related compounds in the RU20 sample and the GRU20, TRU20 and GTRU samples derived therefrom.
  • 1) ... Calculated as Rubusoide on basis of peak area at 210 nm, compound identification is tentative on basis of mass spectra.
  • 2) ... 9-Hydroxy-Suavioside J
  • Table 14-6. Volatile compounds detected in the RU20, RU90, GRU20 and GRU90 samples.
  • Table 14-7. Suavioside-Structures
  • Table 14-7. Suavioside structures (cont. )
  • Table 14-7. Suavioside structures (cont. )
  • Table 14-7. Suavioside structures (cont. )
  • Table 14-7. Suavioside structures (cont. )
  • Table 14-7. Suavioside structures (cont. )
  • FIGs. 8A-8B show chromatograms (MS-TIC Mode) corresponding to the volatile compounds detected in the RU90 and GRU90 samples, respectively. In FIGs. 8A-8B, Unknown 1 shows an MS peak indicative of Suavioside B; Unknown 2 shows an MS peak indicative of Suavioside H; Unknown 3 shows an MS peak tentatively indicative of 9-Hydroxy-Suavioside J; Unknown 4 shows an MS peak indicative of Suavioside K. In addition, m/z.....  (+x Glc) indicates glucosylated rubusoside and the number of added glucose units. In most cases the peak shape indicates co-elution of compounds with the same m/z value but different glucosylation patterns.
  • FIGs. 9A-9B show chromatograms (MS-TIC Mode) corresponding to the volatile compounds detected in the RU20 and GRU20 samples, respectively.
  • FIG. 10 shows a chromatogram (MS-Trace) depicting spectra indicative of a molar mass 966 or less in the GRU20 sample showing Rub-1Glc (2 isomers) and Rub-2Glc (2 isomers) .
  • FIG. 11 shows a two chromatograms, including an upper trace for RU20 at a wavelength (UV) of 254 nm, and a lower trace for GRU20 indicative of phenolic acids and polyphenols.
  • FIGs. 12A-12C show representative chromatograms of RU20.
  • FIGs. 13A-13D show representative chromatograms of GRU20.
  • FIGs. 14A-14C show representative chromatograms of RU90.
  • FIGs. 15A-15D show representative chromatograms of GRU90.
  • FIG. 16 shows representative chromatograms of RU20 SIM neg. MS 497, 335, 317 (indicative for suaviosides with isosteviol as skeleton. SIM means single ion monitoring (only one mass/charge ratio) and “neg” means that the SIM was chosen on basis of the molar mass -1 (because of the loss of one hydrogen) . For example: RA has a molar mass of 966 and a SIM neg. mass/charge of 965.
  • FIG. 17 shows representative chromatograms of TRU20, SIM neg. MS 497, 335, 317 (indicative for suaviosides with isosteviol as skeleton) .
  • FIG. 18 shows representative chromatograms of GRU20, SIM neg. MS 497, 335, 317 (indicative for suaviosides with isosteviol as skeleton) .
  • FIG. 19 shows representative chromatograms of TRU20, SIM neg. MS 497, 335, 317 (indicative for suaviosides with isosteviol as skeleton) .
  • FIG. 20 shows representative chromatograms of RU20, Positive MS 439.
  • Example 15. Perception of acidity and sweetness in soft drinks.
  • Test 1: Lemonade
  • The aim of this study was to analyze the effectiveness of different sweeteners or flavors to maintain a balance between sweetness and acidity in lemonade.
  • Materials: TRU20, Lot #EPC-303-74-01, EPC Lab; GTRU20, Lot #EPC-303-73-01, EPC Lab; RU90, Lot #EPC-238-34-03, EPC Lab; GRU90, Lot #EPC-303-89-03, EPC Lab; Lemon juice, 100%, Alnatura, VL80311, 20.01.2021 09: 33.
  • Experimental procedure: To perform the tests, a lemonade drink was selected. The 100 %direct lemon juice “Alnatura” was diluted 1∶5 with water. Sugar was then added at a concentration of 4% (w/v) . A lemonade sample without the addition of rubusosides or glycosylated rubusosides was used as a control. For the test samples, 75 ppm of rubusosides or glycosylated rubusosides were added to the diluted lemonade samples containing 4%sugar. Each sample was sensory evaluated to determine comparable sweetness, flavor and acidity intensity (each test sample compared to control) .
  • Description of sensory testing: The sensory tests were performed by 5 tasters. To evaluate the acidity/sweetness perception, the time intensity profiling was separated into 3 phases as shown in FIG. 21.
  • In FIG. 21, phase 1 reflects the time of onset and increasing intensity of sweetness/acidity as a joint measure; phase 2 reflects the balanced sweetness/acidity phase; and phase 3 reflects the decay of acidity and sweetness lingering. The combined phases provide a very good estimate for the overall sweetness/acidity perception.
  • The sensory evaluation results are shown in Table 15-1.
  • Table 15-1. Sensory evaluation results
  • FIG. 22A shows time-intensity profiles for sweetness/acidity perception in the TRU20-and GTRU20-lemonade samples. FIG. 23B shows time-intensity profiles for sweetness/acidity perception in the RU 90-and GRU90-lemonade samples.
  • Conclusion: STE, STC, GSTE and GSTC can improve or change the taste and flavor profile of lemonade juice. Preferably RU90 or GRU90 are used, due to their substantial improvement in overall flavor, taste and preference rating among all tasters. Any type of these compositions, such as STE, STC, GSTE, GSTC or any combination thereof could be used in a beverage. The added amount could be from 0.1 ppm to 99.9%, preferably from 0.1ppm to 20,000 ppm.
  • Test 2: Fanta Orange zero added sugar
  • The aim of this study was to analyze the effectiveness of different sweeteners to maintain a balance between sweetness and acidity in the soft drink Fanta Orange zero added sugar.
  • Materials: TRU20, Lot #EPC-303-74-01, EPC Lab; GTRU20, Lot #EPC-303-73-01, EPC Lab; RU90, Lot #EPC-238-34-03, EPC Lab; GRU90, Lot #EPC-303-89-03, EPC Lab; Fanta Orange zero added sugar, L05Z 05: 44 RA, 05.06.2020.
  • Experimental procedure: Fanta Orange zero added sugar is a calorie-free orange flavored soft drink sweetened with sodium cyclamate, Ace-K, sucralose, steviol glycoside and NHDC. Citric acid and malic acid were present as acidifiers. A Fanta Orange zero added sugar without the addition of rubusoside or glycosylated rubusosides served as a control sample. Fanta Orange zero added sugar with the addition of 75 ppm (w/v) of rubusosides or glycosylated  rubusosides served as the test samples. Each test sample was sensory evaluated (and compared to control) to determine comparable sweetness and flavor. Table 15-2 shows the sensory evaluation results.
  • Table 15-2, Sensory evaluation results.
  • FIG. 23A shows time-intensity profiles for sweetness/acidity perception in the TRU20-and GTRU20-Fanta Zero samples. FIG. 23B shows time-intensity profiles for sweetness/acidity perception in the RU 90-and GRU90-Fanta Zero samples.
  • Conclusion: STE, STC, GSTE and GSTC could improve or change the taste and flavor profile of sugar free or sugar reduced beverage. Preferably RU90 or GRU90 are used, due to their substantial improvement of the overall flavor, taste and preference rating among all tasters. Any type of these sweeteners, such as STE, STC, GSTE, GSTC or any combination thereof could be used in beverage. The added amount could be from 0.1 ppm to 99.9%by weight, preferably from 0.1 ppm to 20,000 ppm.
  • Example 16. Applications with RU samples.
  • In the following applications the following RU samples were used: RU20, Lot #STL02-151005, EPC Lab; GRU20, Lot #EPC-303-89-03, EPC Lab; RU90, Lot #EPC-238-34-03, EPC Lab; GRU90, Lot #EPC-303-89-03, EPC Lab.
  • Sensory evaluation: Before tasting the tasters are discussing the upcoming series of samples and taste regular samples (without added flavour) to find a common sense of the description. Thereafter the flavored samples were tasted at the use level to find a common sense on how to describe the flavors (taste, smell, intensity) . Five trained tasters were tasting blinded and independently all samples of a series. They were allowed to re-taste and are making notes for the sensory attributes perceived. In the last step the attributes noted were discussed openly to find a compromise description. In case that more than 1 taster disagrees with the compromise, the tasting was repeated.
  • Application 1: Sugar free energy drink (commercial sample)
  • Materials: RedBull sugar free, M23C5, PR: 02.02.2020/23: 35 N0, EX: 02.02.21/1803976.
  • Test design: To evaluate the taste profile of RU samples a commercial sugar free energy drink (250 ml can, Brand: Red Bull, sweetened with acesulfame K and aspartame) was used. As control sample, a RedBull sugar free without the addition of RU samples, and as test sample, a RedBull sugar free with RU samples were used.
  • Results: The sensory evaluation results from this analysis are shown in Table 16-1.
  • Table 16-1. Sensory evaluation results.
  • Application 2: Flavored milk beverage (commercial sample)
  • Materials: Vanille Kurkuma Drink, 30%less sugar, without sweeteners, S9170 23.03.20 14: 41, 
  • Test design: To evaluate the taste profile of RU samples a commercial flavored vanilla curcuma drink (500 g bottle, Brand:  30 %less sugar, sweetened with sugar, without artificial sweeteners) was used. As reference sample, a vanilla curcuma drink without the addition of RU samples, and as test sample, a vanilla curcuma drink with RU samples were used.
  • Results: The sensory evaluation results from this analysis are shown in Table 16-2.
  • Table 16.2. Sensory evaluation results.
  • Conclusion: Compared to RU20 and GRU20, RU90 and GRU90 showed substantial improvement of the overall smell and taste.
  • Application 3: Flavored milk beverage (commercial sample)
  • Materials: Chocolate drink, 30%less sugar, without sweeteners, S9148 12.04.2020, 07: 27, 
  • Test design: To evaluate the taste profile of RU samples a commercial flavored chocolate milk drink (500 g bottle, Brand:  30 %less sugar, sweetened with sugar, without artificial sweeteners) was used. As reference sample, a chocolate drink without the addition of RU samples, and as test sample, a chocolate drink with RU samples were used.
  • Results: The sensory evaluation results from this analysis are shown in Table 16-3.
  • Table 16-3. Sensory evaluation results.
  • Compared to RU20 and GRU20, RU90 and GRU90 showed substantial improvement of the overall smell and taste.
  • Application 4: Reduced sugar ice tea with peach flavor (laboratory sample)
  • Materials: Black tea extract, kwl, Ref. Nr: K245856; 27102 Citric acid monohydrates gritty, puriss, Lot 60960, Riedel-de 01602636 Peach Aroma, Akras Flavours GmbH. The reference and test samples were prepared as shown in Table 16-4.
  • Table 16-4. Preparation of reduced sugar ice tea samples.
  • Results: The sensory evaluation results from this analysis are shown in Table 16-5.
  • Table 16-5. Sensory evaluation results.
  • Compared to RU20 and GRU20, RU90 and GRU90 showed substantial improvement of the overall smell and taste. -Please confirm the conclusion, the sensory evaluation results above did not mention smell.
  • Application 5: Peach-flavored sugar free ice tea (laboratory sample)
  • Materials: Black tea extract, kwl, Ref. Nr: K245856; 27102 Citric acid monohydrate gritty, puriss, Lot 60960, Riedel-de 01602636 Peach Aroma, Akras Flavours GmbH; Acesulfame K, Lot #LRAA9064, Sigma Aldrich; Aspartame, Lot #LRAAB3060, Sigma Aldrich. The reference and test samples were prepared as shown in Table 16-6.
  • Table 16-6. Preparation of peach-flavored sugar-free ice tea samples.
  • Results: The sensory evaluation results from this analysis are shown in Table 16-7.
  • Table 16-7. Sensory evaluation results.
  • The results from the tasters in Table 16-7 showed that the addition of GRU90 substantially improved the overall taste and preference rating of the peach-flavored sugar-free ice tea.
  • Application 6: Reduced-sugar iced cappuccino (laboratory sample)
  • Materials: Dried skimmed milk powder, Artikel Nr.: 2230049/PZN: 09090890, 219300491, 30.05.2020; Instant Coffee Nescafe Typ Espresso, 100%Arabica, 43876240-100143829, 02 2021 17: 04 90440814C3. The reference and test samples were prepared as shown in Table 16-8.
  • Table 16-8. Preparation of reduced-sugar iced cappuccino samples.
  • Results: The sensory evaluation results from this analysis are shown in Table 16-9.
  • Table 16-9. Sensory evaluation results.
  • The results from the tasters in Table 16-9 showed that the addition of RU90 or GRU90 substantially improved the overall taste and preference rating of the reduced-sugar iced cappuccino.
  • Application 7: Sugar free iced cappuccino (laboratory sample)
  • Materials: Dried skimmed milk powder, Artikel Nr.: 2230049/PZN: 09090890, 219300491, 30.05.2020; Instant Coffee Nescafe Typ Espresso, 100%Arabica, 43876240-100143829, 02 2021 17: 04 90440814C3. The reference and test samples were prepared as shown in Table 16-10.
  • Table 16-10. Preparation of sugar-free iced cappuccino samples.
  • Results: The sensory evaluation results from this analysis are shown in Table 16-11.
  • Table 16-11. Sensory evaluation results.
  • The results from the tasters in Table 16-11 showed that the addition of RU90 or GRU90 substantially improved the overall taste and preference rating of the sugar-free iced cappuccino.
  • Overall conclusions: Different composition of sweet tea extract has different taste and flavor effect on beverage such as energy drinks, flavored milk beverages, flavored teas, flavored coffee drinks. G-STE and GSTC could significantly improve the taste profile and palatability of beverage. The added amount calculated based on pure rubusoside content in food and beverage could be in extended to the range of 1-10,000 ppm, preferably in the range of 5-5,000 ppm, more preferably in the range of 5-3,000 ppm. In some embodiments, G-STE or GSTC, are added at a final concentration of 10-2,000 ppm, 10-1,000 ppm, 10-500 ppm, 10-200 ppm, 10-100 ppm, 10-50 ppm, 20-2,000 ppm, 20-1,000 ppm, 20-500 ppm, 20-200 ppm, 20-100 ppm, 20-50 ppm, 50-2,000 ppm, 50-1,000 ppm, 50-500 ppm, 50-200 ppm, 50-100 ppm, 100-2,000 ppm, 100-1,000 ppm, 100-500 ppm, 100-200 ppm, 200-2,000 ppm, 200-1,000 ppm, 200-500 ppm, 500-2,000 ppm, 500-1,000 ppm or 1000-2000 ppm.
  • Example 17. Preparation of glycosylated Rubusoside 10% (GRU10) .
  • Materials: Rubusoside 10% (Name of producer: Guilin Layin Natural Ingredients Corp., content of Ru: 11.66%, Lot#STL12-20011602) .
  • A glycosylated reaction product was prepared using Rubusoside 10% (RU10) by the followed method:
  • i) 10 g dextrin (BAOLINGBAO BIOLOGY Co., Ltd., Lot#16052872) was dissolved in 100 ml deionized water
  • ii) 10g RU10 was added to liquefied dextrin.
  • iii) 0.5 ml CGTase enzyme (Amano Enzyme, Inc, Lot#CGTN0450202SLK activity: 476u/mL) was added to mixture and incubated at 69℃. for 20 hours to glycosylate the RU10 with glucose molecules derived from Tapioca dextrin.
  • v) The reaction mixture was heated to 85℃. for 10 min to inactivate the CGTase, which was then removed by filtration.
  • vi) The resulted solution comprises glycosylated Rubusoside, residual RU and dextrin, and was decolored and spray dried, thereby yielding 17 g of GRU10 as a white powder. The final product contains glycosylated rubusoside, glycosylated non-sweet glycosides, residues of unreacted sweet tea extract components, and residues of unreacted dextrin.
  • Example 18. Conversion of rubusoside from steviol glycoside (STV95)
  • Materials: steviol glycosides, available from Sweet Green Fields, Lot#: STV95-YCJ20200618. The content of steviol glycosides is as follows.
  • Table 18-1. Contents of steviol glycosides (m/m %)
  • Note: TSG refers to the content of total Steviol glycosides (TSG (9) ) , which includes Rebaudioside A, Rebaudioside B, Rebaudioside C, Rebaudioside D, Rebaudioside F, stevioside, steviolbioside, rubusoside, and dulcoside A.
  • Process:
  • A 1-L steviol glycoside (Lot#STV95-YCJ20200618) solution (100 g/L) was mixed with 1.5g β-galactosidase (0.8 kU/g stevioside) , and stirred at 60℃ for 12h. The reaction mixture was then boiled for 3 min to deactivate the enzyme and the precipitated enzyme was removed by centrifugation. The resulting glycoside solution was then passed through an 800 mL T-28 macroporous resin (Sunrise) column and washed with 1600 mL of water. The column was then washed with 1600 mL ethanol, and the solution was collected and vacuum concentrated.
  • The ethanol was removed and the solution was spray-dried, resulting in a RU product composition (Product No. 18-01) as a powder. Table 18-2 shows the contents of steviol glycosides in the resulting powder obtained following conversion.
  • Table 18-2. Contents of steviol glycosides (m/m %) after conversion
  • Conclusion: Stevioside can be converted to rubusoside with β-galactosidase. Under certain conditions, the conversion rate can be close to 100%.
  • Example 19. Conversion of rubusoside from steviol glycosides (STV85)
  • Materials: Steviol glycosides, available from Sweet Green Fields, Lot #: STV85-20170802. The steviol glycoside contents are shown in Table 19-1.
  • Table 19-1. Steviol glycoside contents (m/m %)
  • Lot# RD RA STV RC RB Others TSG (9)
    STV85-20170802 0.34 10.88 85.67 0.32 0.08 1.48 98.77
  • Note: TSG (9) refers to the total steviol glycoside contents pertaining to the following 9 species: Rebaudioside A, Rebaudioside B, Rebaudioside C, Rebaudioside D, Rebaudioside F, stevioside, steviolbioside, rubusoside, and dulcoside A.
  • Process:
  • A 1-L steviol glycosides (Lot#STV85-201-70802) solution (100g/L) was mixed with 1.5g β-galactosidase (0.8 kU/g stevioside) and stirred at 60℃ for 5h. The reaction mixture was then boiled for 3 min to deactivate the enzyme and the precipitated enzyme was removed by centrifugation. The resulting glycoside solution was then passed through an 800 mL T-28 macroporous resin (Sunrise) column and washed with 2 column volumes of water (1600 mL water) . The column was then washed with 1600 mL ethanol, and the solution was collected and  vacuum concentrated. The ethanol was removed and the solution was spray-dried, resulting in a RU product composition (Product No. 19-01) as a powder with steviol glycoside contents as shown in Table 19-1.
  • Table 19-1. Contents of steviol glycosides (m/m %) following conversion (5 hr enzymatic reaction)
  • The above-described conversion process was repeated, except that the length of the enzymatic reaction was increased to 8 hours (from 5 hours in the preceding experiment) . The resulting RU product composition (Product No. 19-02) was obtained as a powder containing steviol glycoside contents as shown in Table 19-2.
  • Table 19-2. Steviol glycoside contents (m/m %) following conversion
  • Conclusion: Stevioside can be converted to rubusoside in the presence of β-galactosidase. Increasing the time of the enzymatic conversion reaction can increase the conversion of rubuoside from stevioside. Under certain conditions, the conversion rate can be close to 100%. Surprisingly, certain amounts of suaviosides are produced during this conversion process. An embodiment of stevia glycosides composition originated from stevia comprises suaviosides.
  • Example 20. Conversion of rubusoside from steviol glycosides (STV60)
  • Materials: Steviol glycosides (RA20/TSG90) , available from Sweet Green Fields, Lot#: 20191122-23. The steviol glycoside contents are shown in Table 20-1.
  • Table 20-1. Steviol glycoside contents (m/m %)
  • Lot# RD RA STV RC RB Others TSG (9)
    20191122-23 0.83 27.82 60.22 2.42 0.51 1.38 93.18
  • Process: A 1L steviol glycosides (Lot#20191122-23) solution (100g/L) and 2.4g β-galactosidase (0.8 kU/g stevioside) were mixed, stirred at 60℃ for 8h. The reaction mixture was then boiled for 3 min to deactivate the enzyme and the precipitated enzyme was removed by centrifugation. The resulting glycoside solution was then passed through an 800 mL T-28 macroporous resin (Sunrise) column and washed with 2 column volumes of water (1600 mL water) . The column was then washed with 1600 mL ethanol, and the solution was collected, decompressed and concentrated. The ethanol was later removed and the solution was spray-dried, resulting in a RU product composition (Product 20-01) as a powder with steviol glycoside contents as shown in Table 20-2.
  • Table 20-2. Contents of RU and TSG (9) (m/m %)
  • Example 21. Preparation of glycosylated rubusoside derived from steviol glycosides conversion
  • A glycosylated reaction product composition was prepared by a steviol glycoside conversion process using the rubusoside Product Nos. (18-01, 19-01 and 19-02 from Examples 18 and 19) according to the following method:
  • i) 15 g maltodextrin (BAOLINGBAO BIOLOGY Co., Ltd) was dissolved in 45 mL deionized water
  • ii) 15 g rubusoside derived from steviol glycosides conversion (18-01, 19-01 and 19-02 Product Nos. from Examples 18 and 19) was added to the dissolved dextrin solution to form a mixture.
  • iii) 0.75 mL CGTase enzyme (Amano Enzyme, Inc. ) and 15 mL deionized water were added to the mixture and incubated at 69℃ for 20 hours to glycosylate the rubusoside from the steviol glycosides conversion with glucose molecules derived from maltodextrin.
  • iv) The reaction mixture of iii) was heated to 85℃ for 10 min to inactivate the CGTase, which was then removed by filtration.
  • v) The resulting solution of glycosylated rubusoside (GRU) , residual RU and dextrin were decolored and spray dried, thereby yielding 25 g glycosylated rubusoside derived from steviol glycosides (GRUds) product compositions shown in Table 21-1, each in the form of a white powder. An analysis of the glyocosylated products formed is shown in Table 21-2.
  • Table 21-1. GRUds Product Nos and their raw material product numbers.
  • GRUds Product No. Raw material Product No.
    21-01 19-01
    21-02 20-01
    21-03 20-02
  • Table 21-2. Summary of glycosylated rubusoside derived from steviol glycosides (GRUds) contents
  • Table 21-3. Statistical Summary of glycosylated rubusoside derived from steviol glycosides (GRUds) contents
  • Conclusion: Glycosylated rubososide derived from steviol glycosides originating in stevia leaves comprises mono-glucose, di-glucose, tri-glucose, tetra-glucose and penta-glucose added rubusoside. The products can be used as flavors or sweeteners. An embodiment of a sweetener or flavor composition comprises one or more substances selected from mno-glucose, di-glucose, tri-glucose, tetra-glucose and penta-glucose added rubusoside.
  • Example 22. Preparation of glycosylated steviol glycoside (GSGs) composition with reduced maltodextrin content.
  • Materials: GSGs (Lot #: 20200474) , available from Sweet Green Fields. The contents of steviol glycosides in Lot #20200474 are shown in Table 22-1. Its contents are calculated according to the macroporous adsorption resin method below.
  • Table 22-1. Contents of steviol glycosides (m/m %)
  • *Residual dextrin content was assayed by macroporous adsorption resin method described below:
  • Assay for determining residual maltodextrin and TSG (9) content: 5 g GSG composition is dissolved in 250mL of water and added to a glass column containing 200mL of macroporous resin (inner diameter 25mm) at a ratio below 15 mL/min, and washed with 1000 mL water. Adsorbed stevioside is eluted by adding 1000 mL 50% (by volume) ethanol at a ratio of 15mL/min or lower. The aqueous ethanol collected is evaporated by placement in a vacuum oven and dried at 105℃ for two hours. The dry weight of each component is weighed and recorded. TSG (9) (total steviol glycosides (9) including unreacted steviol glycosides and glycosylated steviol glycosides) and residue dextrin contents (%) are calculated according to the following formulas.
  • The TSG mass fraction (w1) content is calculated according to formula A. 1 below:
  • where
  • m1-Total amount of the ethanol component after drying, in grams (g) ;
  • m2-Wet weight of the original sample, in grams (g) ; and
  • wh-Moisture content (%) .
  • The dextrin residue mass fraction (w2) content is calculated according to formula A. 2 below:
  • where
  • m3-Total amount of the water component after drying, in grams (g) ;
  • m2-Wet weight of the original sample, in grams (g) ;
  • wh-Moisture content (%) ;
  • Acceptance Criteria: The sample recovery ratio must be within the range of 98.0%-102.0%. The sample recovery ratio (w3) is calculated according to formula A. 3 below:
  • w 3 = w 1 + w 2............................(A. 3)
  • where
  • w1-Mass fraction of total TSG content (%) ; and
  • w2-Mass fraction of RD content (%) .
  • Process for preparing reduced maltodextrin GSG product composition: A GSG sample (as described above) is dissolved in deionized water to form a solution with a GSG content of 1-3%. In the first experiment, the GSG composition in Table 22-1 (Lot#20200474) was diluted and then passed through the macroporous resin (T-28) adsorption column until the sweetness of the effluent liquid can be detected by the panelists. The resin-bound products are then washed with water (at 2x the column volume) . The resin-bound products are first eluted from the column with 20%ethanol (at 2x the column volume) to wash more bound dextrins, and  then eluted with 60-70%ethanol solution (at 2x the column volume) , collect the elution. The effluent liquids are collected and decolored with 3-5%active carbon at 60-70℃ for 30-60 min. The final solution is then sprayed dried, resulting in a product (Product No. 22-01) as an off-white powder. The contents of Product No. 22-01 obtained from further processing of the GSG composition (Lot #20200474) are shown in Table 22-2.
  • Table 22-2. Composition of final product after adsorption treatment
  • To further develop and refine this methodology, three additional GSG compositions from Lot#20200474) were processed for maltodextrin removal in accordance with the above-described maltodextrin removal process, with the following modifications. Specifically, the above method was modified so that the resin-bound components were first washed with water (at 3x the column volume) , followed by a first elution with 20%ethanol (at 3x the column volume) , and then followed by the second elution with 60-70%ethanol (at 3x the column volume) . The composition of the final products are shown in Table 22-3 below.
  • Table 22-3. Composition of the final products
  • Conclusion: A new sweetener or flavor with low residual maltodextrin content can be obtained from further processing standard glycosylated stevia glycoside compositions according to the above process. The treated GSG sample prepared by above process achieved final products with a residual maltodextrin content of no more than 1%. Products prepared by the described process are especially suited for use in oral care products where reduced sugar content is desirable.
  • Example 23. Preparation of glycosylated stevioside 85% (GSTV85)
  • Material: Stevioside 85% (STV85) , available from Sweet Green Fields (Lot#: STV85-20170802) . The steviol glycoside contents in this composition are shown in Table 23-1.
  • Table 23-1. Contents of stevioside 85% (m/m %)
  • Lot# RD RA STV RC RB Others TSG (9)
    STV85-20170802 0.34 10.88 85.67 0.32 0.08 1.48 98.77
  • A glycosylated product composition was prepared from STV85 according to the following method:
  • i) 15 g maltodextrin (BAOLINGBAO BIOLOGY Co., Ltd) was dissolved in 45 mL deionized water
  • ii) 15 g stevioside 85% (STV85) was added to the dissolved dextrin solution to form a mixture.
  • iii) 0.75 mL CGTase enzyme (Amano Enzyme, Inc. ) and 15 mL deionized water were added to the mixture and incubated at 69℃ for 20 hours to glycosylate the stevioside 85% (STV85) with glucose molecules derived from maltodextrin.
  • iv) The reaction mixture of iii) was heated to 85℃ for 10 min to inactivate the CGTase, which was then removed by filtration.
  • v) The resulting solution of glycosylated steviol glycosides, residual steviol glycosides and dextrin were decolored and spray dried, thereby yielding 25 g GSTV85 as a white powder.
  • Example 24. GSTV85 improves the taste profile of glycosylated rubusoside 90% (GRU90)
  • Materials: GSTV85, the product of Example 23. GRU90 prepared by the procedure in Example 23, except that the glycosylated product composition was prepared by glycosylating RU90 instead of STV85.
  • Sample preparation: GSTV85 and GRU90 were weighed and uniformly mixed according to Table 24-1, dissolved in 100 ml pure water, and subjected to a sensory evaluation test.
  • Table 24-1. Glycosylated product compositions
  • Experiment: Several mixtures of GRU90 and GSTV85 were prepared and evaluated according to the aforementioned sensory evaluation method, where average scores for each evaluation criteria were determined and recorded in the evaluation results shown in Table 24-2. It should be noted that in these evaluations, the concentration of GRU90 in each product sample solution was the same (i.e. 200 ppm) .
  • Table 24-2. Sensory evaluation results
  • Data analysis: The relationship between the sensory evaluation results to the ratio of GRU90 to GSTV85 in this Example is shown in FIG. 24A. The relationship between the overall likability results to the ratio of GRU90 to GSTV85 in this Example is shown in FIG. 24B.
  • Conclusion: The results show that GSTV85 significantly improves the mouth feel and decreases the bitterness and metallic aftertaste of GRU90. This effect was observed in all the tested GRU90-to-GSTV85 ratios (from 10∶1 to 10∶100) . This effect can be further extended to GRU90-to-GTRU20 ratio ranges of 99∶1 to 1∶99. This example demonstrates that GSTV85 can improve taste and mouth feel of natural sweeteners, such as GRU90. Such effects can be extended to all natural sweeteners.
  • Example 25. Analysis of stevia glycosides enriched in rubusosides by hydrolysis of stevia glycosides rich in stevioside.
  • Materials: Lot numbers: EPC-308-50-03, EPC-311-02-02, EPC-308-76-03. )
  • An analysis of the steviol glycosides in the above samples is shown in Table 25-1.
  • Table 25-1. Stevia glycosides identified in hydrolyzed, rubusoside-enriched stevia samples.
  • The enriched rubusosides from hydrolysis of stevia glycosides could be further purified to obtain products such as rubusosides above 85%, 90%, 95%, 99%. All products including rubusosides originated from such method such as 5%, 10%, 20%, 30%, 50%, 60%, 70%, 80%, 90%, 95%, 99%rubusoside could be used as raw material for glycosylation. An embodiment of glycosylated rubusosides by using raw material from hydrolysis of stevioside from stevia glycosides, where the stevioside content is above 5%, 10%, 20%, 30%, 50%, 60%, 70%, 80%, 85%, 90%, 95%, 99%. An embodiment of glycosylated stevia glycosides contain glycosylated rubusosides, where the glycosylated rubusosides are above 1%, 5%, 10%, 20%, 30%, 50%, 70%, 85%, 90%, 95%, 99%. An embodiment of glycosylated stevia glycosides contain glycosylated rubusosides and glycosylated Reb A, where glycosylated Reb A content is less than 99%, 80%, 50%, 30%, 20%, 10%, 5%, 1%. An embodiment of glycosylated stevia glycosides contain glycosylated rubusosides and glycosylated suaviosides, where glycosylated suaviosides is less than 50%, 30%, 10%, 5%, 1%. An embodiment of glycosylated stevia glycosides contain glycosylated rubusosides and glycosylated suaviosides, where glycosylated suaviosides is higher than 1%, 10%, 30%, 50%. An embodiment of glycosylated stevia glycosides contain glycosylated rubusosides, unreacted stevia glycosides selected from one or more of Reb A, stevioside, rubusoside, sauviosides, where unreacted rubusoside is less than 50%, 30%, 20%, 10%, 5%, 1%.
  • Example 26. GSG product 22-02 in Example 22 improved the taste profile of Cherry Blossom Whitening Lion toothpaste
  • Commercial Cherry Blossom Whitening Lion toothpaste: available from Lion Specialty Chemicals Co., Ltd, Lot#: 20190102.
  • Ingredients: sorbitol, water, hydrated silica, polyethylene glycol-8-1auryl sulfate, Xanthan gum, essence, tetrasodium pyrophosphate, sodium polyacrylate, polyethylene glycol-5M, PEG-20 hydrogenated castor oil, Coco-amide propyl betaine, saccharin sodium salt, sodium monofluorophosphate (0.10%fluorine) , sodium benzoate, mica.
  • Process: Dissolve a certain amount of GSG product 22-02 in Example 22 powder into the Cherry Blossom whitening Lion toothpaste solution (1g/100mL) . The details are as follows.
  • Table 26-1. Sample composition
  • Experiment: Each sample was evaluated according to the aforementioned sensory evaluation method in Example 3, and the average score of the panel was taken as the evaluation result data. The taste profile of the mixture is shown in Table 26-2 and FIG. 25.
  • Table 26-2. Sensory evaluation results.
  • Conclusion: GSG product 22-02 with low maltodextrin in Example 22 significantly reduced the unpleasant bitterness in Cherry Blossom whitening Lion toothpaste. In addition, GSG product 22-02 provided significant enhancements in both flavor, and refreshing, resulting in an improved overall likability of the product. The result showed that GSG products with low sugar contenct can improve the taste profile of toothpaste.
  • Example 27. GSG product 22-03 in Example 22 improved the taste profile of White &White Lion toothpaste
  • Commercial White &White Lion toothpaste: available from Lion Specialty Chemicals Co., Ltd, Lot#: 200525W7.
  • Ingredients: calcium carbonate, water, propylene glycol, Sodium lauryl sulfate, cellulose gum, essence, monofiuorophosphate, saccharin sodium, sodium polyacrylate, methylparaben, butylparabenbutyl hydroxybenzoate.
  • Process: Dissolve a certain amount of GSG product 22-03 in Example 22 powder into the White &White Lion toothpaste (1g/100mL) . The details are as follows.
  • Table 27-1. Sample composition
  • Experiment: Each sample was evaluated according to the aforementioned sensory evaluation method in Example 3, and the average score of the panel was taken as the evaluation result data. The taste profile of the mixture is shown in Table 27-2 and FIG. 26.
  • Table 27-2. Sensory evaluation results.
  • Conclusion: GSG product 22-03 with low maltodextrin content in Example 22 significantly reduced the unpleasant bitterness in White &White Lion toothpaste. In addition,  GSG product 22-03 provided significant enhancements in both flavor, and refreshing, resulting in an improved overall likability of the product. The result showed that GSG products with low sugar content can improve the taste profile of toothpaste.
  • Example 28. GSG product 22-03 in Example 22 improved the taste profile of toothpaste
  • A mixture of toothpaste was prepared as follows: sodium Saccharin 0.2% (weight ratio) , sodium monofluorophosphate 0.75%, sodium benzoate 0.5%, carrageenan 0.2%, sorbitol (70%) 21.82%, dicalcium phosphate 51.4%, peppermint Oil 0.79%, water 22.62%, sodium dodecyl sulfonate 1.49%are mixed into a white paste.
  • Process: mix a certain amount of GSG product 22-03 in Example 22 powder into the sample above (1g/100mL) . The details are as follows.
  • Table 28-1. Sample composition
  • Experiment: Each sample was evaluated according to the aforementioned sensory evaluation method in Example 3, and the average score of the panel was taken as the evaluation result data. The taste profile of the mixture is shown in Table 28-02 and FIG. 27.
  • Table 28-2. Sensory evaluation results.
  • Conclusion: GSG product 22-03 with low maltodextrin content in Example 22 significantly reduced the unpleasant bitterness in toothpaste. In addition, GSG product 22-03 provided significant enhancements in both flavor and refreshing, resulting in an improved overall likability of the product. The result showed that GSG products with low sugar content can improve the taste profile of toothpaste.
  • Example 29. Determination of maltodextrin by HPLC Method
  • Method: Samples from example 22 were dissolved in water, syringe-fitrated (0.2 μm) and injected onto the HPLC system. An Agilent 1100 chromatographic system was equipped with a degasser, ternary gradient pump, autosampler, column thermostat, VWD-Detector and Agilent G1362A refractive index (RI) detector. The samples were analyzed using a MetaCarb 87C Column (Agilent Technologies) under isocratic condition. Mobile Phase was a deionized water. The column temperature was maintained at 70℃ and the RI detector at 45℃. Injection volume was set to 10 μl, flow rate 0.6 ml/min. Data evaluation was performed with the Agilent LC ChemStation (B. 04.03-SP2) using the RI trace. Quantification was performed by external calibration using Maltodextrin (Sigma-Aldrich 419699, dextrin equivalent 16.5-19.5) and glucose (Sigma-Aldrich 47829) .
  • Chromatograms: The standard chromatograms are shown in FIG. 28A and the sample chromatogram (Arrow indicates retention time of glucose)
  • Test results: Test results are shown in Table 29-1. The results are given as sum of maltodextrins and the fractions DP 3-5 (oligomers with 3-5 glucose units) and DP＞5 (oligomers with more than 5 glucose units)
  • Table 29-1.
  • Unless defined otherwise, all technical and scientific terms used herein have the same meanings as commonly understood by one of ordinary skill in the art to which this invention belongs. All publications and patents specifically mentioned herein are incorporated by reference in their entirety for all purposes including describing and disclosing the chemicals, instruments, statistical analyses and methodologies which are reported in the publications which might be used in connection with the invention. All references cited in this specification are to be taken as indicative of the level of skill in the art. Nothing herein is to be construed as an admission that the invention is not entitled to antedate such disclosure by virtue of prior invention.

Claims (64)

  1. A composition comprising one or more products selected from the group consisting of rubusoside (RU) , one or more sweet tea components (STCs) , sweet tea extracts (STEs) , one or more monk fruit components (MFCs) , monk fruit extracts (MFEs) , one or more Stevia glycosides (SGs) , Stevia extracts (SEs) , glycosylated rubusoside (GRU) , glycosylated sweet tea components (GSTCs) , glycosylated sweet tea extracts (GSTEs) , glycosylated monk fruit components (GMFCs) , glycosylated monk fruit extracts (GMFEs) , glycosylated stevia glycosides (GSGs) , and/or glycosylated stevia extracts (GSEs) , wherein the one or more products are present in the composition in a total amount of 0.1-99.9 wt%, and wherein the composition is a sweetener composition, a flavoring composition, or both.
  2. The composition of claim 1, wherein the composition is a sweetener composition.
  3. The composition of claim 1, wherein the composition is a flavoring composition
  4. The composition of claim 1, wherein the composition is a sweetener composition and a flavoring composition.
  5. The composition of any one of claims 1-4, wherein the one or more products comprise an STE.
  6. The composition of claim 5, wherein the STE comprises a diterpene glycoside.
  7. The composition of claim 6, wherein the diterpene glycoside is RU.
  8. The composition of claims 7, wherein the composition comprises rubusoside in an amount (w/w) greater than zero, but less than 95%, less than 80%, less than 70%, less than 50%, less than 30%, less than 20%, less than 10%, less than 5%, less than 1%, less than 0.5%, or less than 0.1%.
  9. The composition of claim 6, wherein the STE comprises an enriched diterpene glycoside in an amount of 50-99 wt%of the STE.
  10. The composition of claim 9, wherein the enriched diterpene glycoside is RU.
  11. The composition of any one of claims 5-10, wherein the STE comprises one or more one or more sweet tea derived components (STCs) selected from the group consisting of rubusoside (RU) , suavioside (SU) , steviolmonoside, rebaudioside A, 13-O-β-D-glucosyl-steviol, isomers of rebaudioside B, isomers of stevioside, panicloside IV, sugeroside, ent-16α, 17-dihydroxy-kaurane-19-oic acid, ent-13-hydroxy-kaurane-16-en-19-oic acid, ent-kaurane-16-en-19-oic-13-O-β-D-glucoside, ent-16β, 17-dihydroxy-kaurane-3-one, ent-16α, 17-dihydroxy-kaurane-19-oic acid, ent-kaurane-16β, 17-diol-3-one-17-O-β-D-glucoside, ent-16α, 17-dihydroxy-kaurane-3-one, ent-kaurane-3α, 16β, 17-3-triol, ent-13, 17-dihydroxy-kaurane-15-en-19-oic acid, ellagic acid, gallic acid, oleanolic acid, ursolic acid, rutin, quercetin, and isoquercitrin.
  12. The composition of claim 11, comprising one or more suaviosides slected from the group consisting of SU-A, SU-B, SU-C1, SU-D1, SU-D2, SU-E, SU-F, SU-G, SU-H, SU-I, and SU-J.
  13. The composition of claim 11 or claim 12, comprising purified RU.
  14. The composition of any one of claims 11-13, comprising at least one GSTE.
  15. The composition of claim 14, wherein the at least one GSTE comprises glycosylated RU (GRU) .
  16. The composition of claim 15, wherein the composition comprises mono-glucosylated rubusosides in a total amount (w/w) of at least 0.1%, at least 0.5%, at least 1%, at least 5%, at least 10%, at least 20%, at least 30%, at least 50%, at least 70%, at least 90%, or at least 95%.
  17. The composition of claim 15, wherein the composition comprises mono and di-glucosylated rubusosides in a total amount (w/w) of at least 0.1%, at least 0.5%, at least 1%, at least 5%, at least 10%, at least 20%, at least 30%, at least 50%, at least 70%, at least 90%, or at least 95%.
  18. The composition of claim 15, wherein the composition comprises mono, di, and tri-glyocosylated rubusosides in a total amount (w/w) of at least 0.1%, at least 0.5%, at least 1%, at least 5%, at least 10%, at least 20%, at least 30%, at least 50%, at least 70%, at least 90%, or at least 95%.
  19. The composition of claim 15, wherein the composition comprises mono, di, tri-and tetra glycosyslated rubusosides in a total amount (w/w) of at least 0.1%, at least 0.5%, at least 1%, at least 5%, at least 10%, at least 20%, at least 30%, at least 50%, at least 70%, at least 90%, or at least 95%.
  20. The composition of claim 15, wherein the composition comprises mono, di, tri-, tetra and penta glycosylated rubusosides in a total amount (w/w) of at least 0.1%, at least 0.5%, at least 1%, at least 5%, at least 10%, at least 20%, at least 30%, at least 50%, at least 70%, at least 90%, or at least 95%.
  21. The composition of claims 15, wherein the composition comprises penta glycosylated rubusosides in a total amount (w/w) that is greater than zero, but less than 95%, less than 80%, less than 70%, less than 50%, less than 30%, less than 20%, less than 10%, less than 5%, less than 1%, less than 0.5%, or less than 0.1%.
  22. The composition of claim 15, wherein the composition comprises tetra and penta glycosylated rubusosides in a total amount (w/w) that is greater than zero, but less than 95%, less than 80%, less than 70%, less than 50%, less than 30%, less than 20%, less than 10%, less than 5%, less than 1%, less than 0.5%, or less than 0.1%.
  23. The composition of claim 15, wherein the composition comprises tri, tetra and penta glycosylsated rubusosides in a total amount (w/w) that is greater than zero, but less than 95%, less than 80%, less than 70%, less than 50%, less than 30%, less than 20%, less than 10%, less than 5%, less than 1%, less than 0.5%, or less than 0.1%.
  24. The composition of claim 15, wherein the composition comprises di, tri, tetra and penta glycosylated rubusosides in a total amount (w/w) that is greater than zero, but less than 95%, less than 80%, less than 70%, less than 50%, less than 30%, less than 20%, less than 10%, less than 5%, less than 1%, less than 0.5%, or less than 0.1%.
  25. The composition of claim 15, wherein the GRU is present in the composition in a total amount (w/w) that is greater than zero, but less than 95%, less than 80%, less than 70%, less than 50%, less than 30%, less than 20%, less than 10%, less than 5%, less than 1%, less than 0.5%, or less than 0.1%.
  26. The composition of any one of claims 14-25, wherein the composition comprises an enriched glycosylated diterpene in an amount (w/w) of 40-90 %of the composition.
  27. The composition of claim 26, wherein the enriched diterpene glycoside is glycosylated RU (GRU) .
  28. The composition of any one of claims 1-27, wherein the composition further comprises one or more flavors selected from the group consisting of oil phase flavors, water phase flavors, juice concentrated aromas, fraction of oil phase flavors, crude extracts, flavors or flavor derivatives from plant sources, and flavors or flavor derivatives from animal sources.
  29. The composition of claim 28, wherein the one or more flavors are selected from the group consisting of lemon juice concentrate aroma, orange juice volatiles concentrate extract, mandarin orange juice volatiles concentrate extract, bitter orange volatiles concentrate extract, lemon volatiles concentrate extract, cucumber juice volatiles concentrated aroma, blood orange volatiles concentrate extract, blood orange juice concentrate aroma, lime juice concentrated aroma, bilberry or blueberry juice volatile concentrate extract, cranberry juice volatile concentrate extract, pineapple juice volatile concentrate extract, peach juice volatile concentrate extract, mongo juice volatile concentrate extract, banana paste volatile concentrate extract, coconut juice volatile concentrate extract, Litchi juice volatile concentrate extract, grape volatile concentrate extract, grapefruit volatile concentrate extract, ginger juice volatile concentrate extract, ginseng juice volatile concentrate juice extract, pear juice volatile concentrate extract, pomegranate juice volatile concentrate extract, jasmine water extracted volatile concentrate, cocoa juice volatile concentrate extract, tea volatile concentrate extract, coffee volatile concentrate extract, and mint juice volatile concentrate extract.
  30. The composition of claim 28 or claim 29, wherein the one or more flavors are extracted from a fruit or berry juice.
  31. The composition of any one of claims 28-30, wherein the one or more flavors are selected from Massoia lactone Mossoia bark extract, hydrolyzed products from cheese, butter, milk fat, casein or salts thereof, and vanilla extract.
  32. The composition of any one of claims 28-31, wherein the one or more flavors in the composition comprise one or more substances selected from limonene, linalool, citronellol, citral,  geraniol, bergaptene, terpineol, decanal, linalyl acetate, caryophyllene, neryl acetate, perillaldehyde, thymol, methyl N-methylanthranilate, apha-sinensal, gamma-terpinene, and octanal.
  33. The composition of any one of claims 28-32, wherein the one or more flavors in the composition are present in an amount of at least 0.1%, at least 0.5%, at least 1%, at least 2%, at least 2.5%, at least 5%, or at least 10%on w/w basis, optionally wherein the one or more flavors comprise one or more volatile substances.
  34. The composition of any one of claims 1-19, wherein the composition further comprises one or more high intensity sweeteners.
  35. The composition of claim 34, wherein the one or more high intensity sweeteners are selected from acesulfame K, sucralose, saccharine, aspartame, stevia extract, stevia glycosides, monk fruit extract, mongrosides, sweet tea extract, enriched rubusoside from sweet tea or stevia, and licorice extract.
  36. The composition of any one of claims 1-35, wherein the composition further comprises one or more sweeteners or fibers selected from allulose, inulin, polydextrins, modified starch, erythritol.
  37. The composition of any one of claims 1-36, wherein the composition further comprises one or compounds listed in Tables 19-1 to 19-12.
  38. The composition of any one of claims 1-37, wherein the composition comprises:
    (a) a glycosylated component selected from the group consisting of glycosylated sweet tea extract, a glycosylated rubusoside, a glycosylated suavioside, a glycosylated stevia glycoside, a glycosylated stevia extract, a glycosylated monk fruit extract, or a glycosylated mogroside;
    (b) a sweet tea extract, a rubusoside, a suavioside, a stevia extract, a stevia glycoside, a monk fruit extract, or a mogroside corresponding to the glycosylated component in (a) ; and
    (c) an unreacted sugar donor or residue thereof,
    whereing the unreacted sugar donor or residue therefrom is derived from a dextrin and is present in the composition in an amount greater than zero, but less than 15%, less than 10%, less  than 5%, less than 4%, less than 3%, less than 2%, less than 1%, less than 0.5%, less than 0.1%, less than 0.05%, less than 0.01%, less than 100 ppm, less than 10 ppm, or less than 1 ppm (wt/wt) .
  39. The composition of claim 38, wherein the unreacted sugar donor or residue therefrom comprises dextrin, maltodextrin or a hydrolysis product thereof.
  40. A consumable product comprising the composition in any one of claims 1-39.
  41. The consumable product of claim 40, wherein the concentration (w/w) of the composition in the consumable is greater than zero, but less than 10,000 ppm, less than 5,000 ppm, less than 1,000 ppm, less than 500 ppm, less than 100 ppm, less than 50 ppm, less than 10 ppm, or less than 1 ppm.
  42. The consumable product of claim 40 or claim 41, wherein the consumable product is a beverage, food product, or personal care product.
  43. The consumable product of any one of claims 40-42, wherein the consumable product is a beverage.
  44. The consumable product of any one of claims 40-42, wherein the consumable product is a food product.
  45. The consumable product of any one of claims 40-42, wherein the consumable product is a personal care product.
  46. The consumable product of claim 45, wherein the personal care product is an oral hygiene product selected from the group consisting of toothpaste, tooth polish, tooth whitening agent, mouthwash, mouth rinse, mouth spray, breath freshener, and dentifrice.
  47. The consumable product of any one or claims 40-46, wherein the composition comprises one or more flavors selected from the group consisting of lemon juice concentrate aroma, orange juice volatiles concentrate extract, mandarin orange juice volatiles concentrate extract, bitter orange volatiles concentrate extract, lemon volatiles concentrate extract, cucumber juice volatiles concentrated aroma, blood orange volatile concentrate extract, blood orange juice concentrate aroma, lime juice concentrated aroma, bilberry or blueberry juice volatile concentrate extract, cranberry juice volatile concentrate extract, pineapple juice volatile  concentrate extract, peach juice volatile concentrate extract, mongo juice volatile concentrate extract, banana paste volatile concentrate extract, coconut juice volatile concentrate extract, Litchi juice volatile concentrate extract, grape volatile concentrate extract, grapefruit volatile concentrate extract, ginger juice volatile concentrate extract, ginseng juice volatile concentrate juice extract, pear juice volatile concentrate extract, pomegranate juice volatile concentrate extract, jasmine water extracted volatile concentrate, cocoa juice volatile concentrate extract, tea volatile concentrate extract, coffee volatile concentrate extract, and mint juice volatile concentrate extract, and
    wherein the one or more flavors are present in the consumable product in an amount greater than zero, but less than 1000 ppm, less than 100 ppm, less than 50 ppm, less than 10 ppm, less than 5 ppm, less than, 1 ppm, less than 0.5 ppm, or less than 0.1 ppm.
  48. The consumable product of any one of claims 40-47, wherein the one or more flavors in the composition further comprise one or more substances selected from the group consisting of limonene, linalool, citronellol, citral, geraniol, bergaptene, terpineol, decanal, linalyl acetate, caryophyllene, neryl acetate, perillaldehyde, thymol, methyl N-methylanthranilate, apha-sinensal, gamma-terpinene, octanal, and combinations thereof.
  49. The product of any one of claims 40-48, wherein the composition comprises at least one high intensity sweetener, wherein the concentration of the at least one high intensity sweeteners in the consumable product is at least 1 ppm, at least 10 ppm, at least 100 ppm, at least 200 ppm, at least 300 ppm, at least 500 ppm, at least 1,000 ppm, or at least 10,000 ppm.
  50. A method to improve the freshness of flavor in a consumable product comprising adding to the consumable product the composition of any one of claims 1-39.
  51. A method to modify the sweetness profile of a high intensity sweetener comprising adding to the high intensity sweetener the composition of any one of claims 1-39 in an amount sufficient to reduce lingering, reduce metallic and/or synthetic aftertaste, or synergistically increase sweetness of the high intensity sweetener.
  52. A method to accelerate the recognition of flavor in a consumable product by adding to the consumable product the composition of any one of claims 1-39.
  53. A method to reduce astringency, sourness, and/or bitterness of a consumable product comprising the step of adding to the consumable product the composition of any one of claims 1-39, wherein the composition further comprises one or more fruit/berry juices or flavors selected from the group consisting of Orange Volatiles Conc. Extract, Mandarin Volatiles Conc. Extract, Lemon Volatiles Conc. Extract, Bitter Orange Volatiles Conc. Extract, Blood Orange Volatiles Conc. Extract and Mandarin Juice Volatiles Conc. Extract.
  54. A method to increase solubility and bioavailability of insoluble substances by adding to a consumable product the composition of any one of claims 1-39.
  55. A method to reduce the off-note of a plant vegetable byadding to the plant vegetable the composition of any one of claims 1-39.
  56. The method of any one of claims 50-55, wherein the composition added to the consumable product comprises one or more flavors that are present in the composition in an amount (w/w) of at least 0.1%, at least 0.5%, at least 1%, at least 2%, at least 2.5%, at least 5%, or at least 10%on w/w basis, optionally wherein the one or more flavors comprise one or more volatile substances.
  57. The method of any one of claims 50-55, wherein the composition added to the consumable product comprises one or more flavors that are present in the composition in an amount (w/w) greater than zero, but less than 100 ppm, less than 50 ppm, less than 20 ppm, less than 10 ppm, less than 5 ppm, less than 2 ppm, less than 1 ppm, or less than 0.1ppm.
  58. A rubososide (RU) -enriched composition, wherein the rubusoside is present in the composition in an amount (w/w) of at least 50 wt%, at least 55 wt %, at least 60 wt %, at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, at least 95 wt %, at least 99 wt %, or any range defined by any pair of these integers.
  59. A method for preparing an RU-enriched composition according to Claim 58, wherein the method comprises the steps of:
    (a) forming a glycosylate from a stevioside-enriched composition;
    (b) passing the glycosylate through a macroporous affinity resin to bind glycosylated steviol glycosides (GSGs) , including glycosylated RU (GRU) ;
    (c) washing the bound fraction with water;
    (d) eluting the bound GRU with ethanol; and
    (e) drying the eluate to form a RU-enriched composition in the form of a powder.
  60. The method of Claim 59, wherein the stevioside-enriched composition comprises stevioside in an amount greater or equal to: 60 wt%, 70wt%, 75 wt%, 85 wt%or 95 wt%.
  61. A method for preparing a low dextrin glycosylated steviol glycoside composition comprising the steps of:
    (a) preparing a glycosylated steviol glycoside (GSG) composition;
    (b) dissolving the GSG composition in water to form a solution with a GSG content between 1-10 wt%;
    (c) passing the solution through a macroporous resin adsorption column for binding the GSGs;
    (d) washing the column comprising resin-bound GSGs with water;
    (e) eluting resin-bound GSGs with one or more aqueous solvents;
    (f) drying the eluate (s) to form a low dextrin GSG composition in the form of a powder.
  62. The method of Claim 61, wherein the the GSG composition is dissolved in water to form a solution with a GSG content between 1-3 wt%/
  63. The method of Claim 61 or Claim 62, wherein the resin-bound GSGS are eluted with an aqueous solution of 20%ethanol, 60-70%ethanol or a combination thereof.
  64. The method of any one of Claims 61-63, wherein the powder comprises dextrin or maltodextrin in an amount less than or equal to 1 wt%.
EP20936550.1A 2020-05-19 2020-12-04 Sweetener and flavor compositions Pending EP4152954A4 (en)

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