WO2021232750A1 - Sweetener and flavor compositions - Google Patents

Sweetener and flavor compositions Download PDF

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Publication number
WO2021232750A1
WO2021232750A1 PCT/CN2020/134014 CN2020134014W WO2021232750A1 WO 2021232750 A1 WO2021232750 A1 WO 2021232750A1 CN 2020134014 W CN2020134014 W CN 2020134014W WO 2021232750 A1 WO2021232750 A1 WO 2021232750A1
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composition
less
ppm
glycosylated
extract
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PCT/CN2020/134014
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English (en)
French (fr)
Inventor
Jingang Shi
Hansheng Wang
Thomas Eidenberger
Xiaorui ZHANG
Weiyao Shi
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Epc Natural Products Co., Ltd.
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Priority to CN202080100967.0A priority Critical patent/CN115835784A/zh
Priority to EP20936550.1A priority patent/EP4152954A4/en
Publication of WO2021232750A1 publication Critical patent/WO2021232750A1/en

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    • 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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CN117965500A (zh) * 2024-03-28 2024-05-03 北京理工大学 一种α-L鼠李糖苷酶AfRhase及其产品、应用和生产工艺
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