WO2022246313A1 - Renforcement de sucré et modulation de goût à l'aide d'analogues de digupigan a - Google Patents

Renforcement de sucré et modulation de goût à l'aide d'analogues de digupigan a Download PDF

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Publication number
WO2022246313A1
WO2022246313A1 PCT/US2022/030525 US2022030525W WO2022246313A1 WO 2022246313 A1 WO2022246313 A1 WO 2022246313A1 US 2022030525 W US2022030525 W US 2022030525W WO 2022246313 A1 WO2022246313 A1 WO 2022246313A1
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Prior art keywords
beverage
rebaudioside
ppm
mogroside
formula
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PCT/US2022/030525
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English (en)
Inventor
Bin Wang
Gil Ma
Juvenal Higiro
Indra Prakash
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The Coca-Cola Company
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Publication of WO2022246313A1 publication Critical patent/WO2022246313A1/fr

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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
    • 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
    • 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
    • A23L27/86—Addition of bitterness inhibitors

Definitions

  • Natural caloric sugars such as sucrose, fructose and glucose, are used to provide a pleasant taste to beverages, foods, pharmaceuticals, and oral hygienic/cosmetic products.
  • Sucrose in particular, imparts a taste preferred by consumers.
  • sucrose provides superior sweetness characteristics, it is disadvantageously caloric.
  • Consumers increasingly prefer non-caloric or low caloric sweeteners have been introduced to satisfy consumer demand.
  • non-caloric or low caloric sweeteners differ from natural caloric sugars in ways that frustrate consumers.
  • non-caloric or low caloric sweeteners exhibit a temporal profile, maximal response, flavor profile, mouth feel, and/or adaptation behavior that differ from sugar.
  • non-caloric or low caloric sweeteners exhibit delayed sweetness onset, lingering sweet aftertaste, bitter taste, metallic taste, astringent taste, cooling taste and/or licorice-like taste.
  • many non-caloric or low caloric sweeteners are synthetic chemicals. Consumer desire remains high for natural non- caloric or low caloric sweeteners that tastes like sucrose.
  • Stevia rebaudiana Bertoni is a perennial shrub of the Asteraceae (Compositae) family native to certain regions of South America. Its leaves have been used for hundreds of years in Paraguay and Brazil to sweeten local teas and medicines.
  • the plant is commercially cultivated in Japan, Singapore, Malaysia, South Korea, China, Israel, India, Brazil, Australia and Paraguay.
  • the leaves of the plant contain a mixture containing diterpene glycosides in an amount ranging from about 10% to 15% of the total dry weight.
  • These diterpene glycosides are about 30 to 450 times sweeter than sugar.
  • the diterpene glycosides are characterized by a single base, steviol, and differ by the presence of carbohydrate residues at positions C13 and C19.
  • the four major steviol glycosides found in the leaves of Stevia are dulcoside A (0.3%), rebaudioside C (0.6-1.0%), rebaudioside A (3.8%) and stevioside (9.1%).
  • Other glycosides identified in Stevia extract include rebaudioside B, D, E, and F, steviolbioside and rubusoside.
  • stevioside and rebaudioside A are available on a commercial scale.
  • Mogrosides are derived from Luo han guo, the common name for the sweet extract made from the fruit of Siraitia grosvenorii, a herbaceous perennial vine of the Cucurbitaceae family native to Southern China and Northern Thailand.
  • Luo han guo extracts are nearly 250 times sweeter than sugar and non-caloric.
  • the sweetness of Luo han guo is generally attributed to mogrosides.
  • Use of steviol glycosides and mogrosides has been limited to date by certain undesirable taste properties, including licorice taste, bitterness, astringency, sweet aftertaste, bitter aftertaste and licorice aftertaste, which become more prominent at increased concentrations and impart a taste distinct from sucrose to consumables (e.g., beverages) to which they are added.
  • maximal sweetness of most steviol glycoside and mogrosides is generally less than what is acceptable for traditional beverage formulations in sweetened consumables (e.g., beverages).
  • the present invention provides at least one sweetener and at least one compound of Formula I:
  • each R 1 is independently chosen from hydrogen, hydroxy, OR 4 , C 1 -C 6 alkyl and substituted C 1 -C 6 alkyl; each R 2 and R 3 is independently chosen from hydrogen, monosaccharide, disaccharide, and oligosaccharide; and R 4 is selected from C 1 -C 6 alkyl, substituted C 1 -C 6 alkyl, monosaccharide, and disaccharide.
  • the at least one compound of Formula I is selected from the group consisting of digupigan A, CC-00592, CC-00593, CC-00594, CC-00595, CC-00596, CC-00634, CC-00597, CC-00598, CC-00606, CC-00608, CC-00629, CC-00655, CC-00667, CC-00599, CC-00637, CC-00641, CC-00642, CC-00643, CC-00617, CC-00600, CC-00644, CC-00639, CC-00618, CC-00690, CC-00673, CC-00601, CC-00671, CC-00658 and CC- 00659.
  • the compound of Formula I is present in the beverage in a concentration from about 1 ppm to about 200 ppm, e.g., at least 25 ppm, at least 50 ppm or at least 100 ppm.
  • the sweetener is selected from a steviol glycoside or steviol glycoside mixture, a mogroside or mogroside mixture, a carbohydrate sweetener, a protein sweetener, a synthetic sweetener, a sugar alcohol sweetener or combinations thereof.
  • the concentration of at least one sweetener varies depending on the identity of the sweetener.
  • the present invention provides a method of enhancing the sweetness of a beverage comprising (i) providing a beverage comprising at least one sweetener described herein and (ii) adding at least one compound of Formula I described herein to the beverage to provide a beverage with enhanced sweetness compared to the beverage in the absence of the at least one compound of Formula I.
  • the present invention provides a method of making a beverage taste more like a sucrose-sweetened beverage comprising (i) providing a beverage comprising at least one sweetener described herein and (ii) adding at least one compound of Formula I described herein in an amount effective to modulate one or more taste attributes of the beverage to make the beverage taste more like a sucrose-sweetened beverage compared to the beverage in the absence of the at least one compound of Formula I.
  • the present invention provides a method of preparing a sweetened beverage comprising (i) providing a beverage comprising at least one sweetener described hereinabove and (ii) adding at least one compound of Formula I described herein to the beverage.
  • Alkyl generally refers to a noncyclic, cyclic, linear or branched, unsaturated or saturated hydrocarbon such as those containing from 1 to 22 carbon atoms, and specifically includes methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, isobutyl, t-butyl, pentyl, cyclopentyl, isopentyl, neopentyl, hexyl, isohexyl, cyclohexyl, cyclohexylmethyl, 3- methylpentyl, 2,2-dimethylbutyl, and 2,3-dimethylbutyl.
  • Alkyl groups can be optionally substituted with one or more moieties selected from, for example, hydroxyl, amino, halo, deutero, alkylamino, arylamino, alkoxy, aryloxy, nitro, cyano, sulfonic acid, sulfate, phosphonic acid, phosphate, or phosphonate, or any other viable functional group, either unprotected, or protected, as necessary, as known to those skilled in the art, for example, as taught in T. W. Greene and P. G. M.
  • “Beverage product”, as used herein, is a ready-to-drink beverage, a beverage concentrate, a beverage syrup, or a 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, beverage containing milk components (e.g. milk beverages, coffee containing milk components, café au lait, milk tea, fruit milk beverages), beverages containing cereal extracts and smoothies.
  • “Sweetening amount”, as used herein, refers to the concentration of a substance sufficient to perceptibly sweeten the beverage.
  • “Sweetness enhancer”, as used herein, refers to a compound that enhances, amplifies or potentiates the perception of sweetness of a consumable (e.g. a beverage) when said compound is present in the consumable in a concentration at or below the compound’s sweetener recognition threshold, i.e. a concentration at which the compound does not contribute any noticeable sweet taste in the absence of additional sweetener(s).
  • “Sweetness recognition threshold concentration,” as used herein, is the lowest known concentration of a compound that is perceivable by the human sense of taste as sweet. The sweetness recognition threshold concentration is specific for a particular compound, and can vary based on temperature, matrix, ingredients and/or flavor system.
  • a 1.5% (w/v) sucrose solution is generally considered the minimum perceivable sweet taste to humans. Accordingly, it is routine for compounds evaluated for their isosweetness with a 1.5% (w/v) sucrose solution.
  • the concentration at which the compound is isosweet with a 1.5% (w/v) sucrose solution is considered the compounds’ sweetness recognition threshold concentration.
  • sweetness enhancer is synonymous with the terms “sweet taste potentiator,” “sweetness potentiator,” “sweetness amplifier,” and “sweetness intensifier.”
  • Total mogroside content refers to the sum of the relative weight contributions of each mogroside in a sample.
  • Total steviol glycoside content refers to the sum of the relative weight contributions of each steviol glycoside in a sample.
  • Beverages The present invention provides beverages and beverage products comprising at least one sweetener and at least one compound of Formula I.
  • the at least one sweetener is present in the beverage in a sweetening amount, the precise concentration of which will depend on the sweetener.
  • the compound of Formula I is present in the beverage in concentrations at or below the compound’s sweetness recognition threshold concentration.
  • the at least one compound of Formula I enhances the sweetness of the at least one sweetener and/or modulates one or more taste attributes of the beverage to make the beverage taste more like a sucrose-sweetened beverage.
  • the at least one compound of Formula I enhances the sucrose equivalence (SE) of the beverage by at least 1.0 SE when compared to the SE of the beverage in the absence of the at least one compound of Formula I, such as for example, at least about 1.5 SE, at least about 2.0 SE, or at least about 2.5 SE.
  • the at least one compound of Formula I modulates one or more taste attributes of the beverage to make the beverage taste more like a sucrose-sweetened beverage.
  • Exemplary taste attribute modulations include decreasing or eliminating bitterness, decreasing or eliminating bitter linger, decreasing or eliminating sourness, decreasing or eliminating astringency, decreasing or eliminating saltiness, decreasing or eliminating metallic notes, improving mouthfeel, decreasing or eliminating sweetness linger, and increasing sweetness onset.
  • Multiple taste attributes of the sweetener can be modulated simultaneously, such that the beverage, overall, has more sucrose-sweetened characteristics.
  • Methods of quantifying improvement in sucrose-sweetened characteristics are known in the art and includes taste testing and histogram mapping with isosweet sucrose-sweetened beverage controls. A.
  • Digupigan A and Analogs Beverages of the present invention comprise at least one compound of Formula I (digupigan A and analogs): Formula I wherein each R 1 is independently chosen from hydrogen, hydroxy, OR 4 , C 1 -C 6 alkyl and substituted C 1 -C 6 alkyl; each R 2 and R 3 is independently chosen from hydrogen, monosaccharide, disaccharide, and oligosaccharide; and R 4 is selected from C 1 -C 6 alkyl, substituted C 1 -C 6 alkyl, monosaccharide, and disaccharide.
  • Formula I wherein each R 1 is independently chosen from hydrogen, hydroxy, OR 4 , C 1 -C 6 alkyl and substituted C 1 -C 6 alkyl; each R 2 and R 3 is independently chosen from hydrogen, monosaccharide, disaccharide, and oligosaccharide; and R 4 is selected from C 1 -C 6 alkyl, substituted C 1 -C 6 alkyl, monosacc
  • Monosaccharide substituents include, but are not limited to, glucose, xylose, rhamnose, arabinose, ribose, gentibiose, apio-furanose, glyceraldehyde, dihydroxyacetone, erythrose, threose, erythrulose, arabinose, lyxose, ribulose, xylulose, allose, altrose, galactose, gulose, idose, mannose, talose, fructose, psicose, sorbose, tagatose, mannoheptulose, sedoheltulose, octolose, fucose, arabinose, turanose, and sialose.
  • Disaccharides contain two same or different monosaccharides. Oligosaccharides includes from three to five same or different monosaccharides.
  • R 2 or R 3 is glucose, xylose, rhamnose, arabinose, ribose, apio-furanose, and fructose.
  • R 2 or R 3 is a disaccharide comprising glucose, xylose, rhamnose, arabinose, ribose, apio-furanose, fructose, or a combination thereof.
  • the compound has at least two R 1 groups selected from hydroxy, OR 4 , C 1 -C 6 alkyl and substituted C 1 -C 6 alkyl.
  • the compound has two R 1 groups selected from OH and OCH3, and one R 1 group that is hydrogen.
  • the compound belongs to Formula Ia: , Formula Ia wherein R 1 and R 3 are defined as above for Formula I.
  • R 3 is selected from monosaccharide, disaccharide, and oligosaccharide.
  • R 3 is a monosaccharide that is a 5-membered ring saccharide.
  • R 3 is a monosaccharide that is a 6-membered ring saccharide.
  • R 3 is hydrogen.
  • the compound belongs to Formula Ib: , Formula Ib wherein R 2 and R 3 are defined as above for Formula I.
  • R 3 is selected from monosaccharide, disaccharide, and oligosaccharide.
  • R 3 is a monosaccharide that is a 5-membered ring saccharide.
  • R 3 is a monosaccharide that is a 6-membered ring saccharide.
  • R 3 is hydrogen.
  • the compound belongs to Formula Ic: , wherein R 3 is defined as above for Formula I.
  • R 3 is selected from monosaccharide, disaccharide, and oligosaccharide.
  • R 3 is a monosaccharide that is a 5-membered ring saccharide. In other embodiments, R 3 is a monosaccharide that is a 6-membered ring saccharide. In other embodiments, R 3 is hydrogen. In another embodiment, the compound belongs to Formula Id: , Formula Id wherein R 2 and R 3 are defined as above for Formula I. In certain embodiments, R 3 is selected from monosaccharide, disaccharide, and oligosaccharide. In some embodiments, R 3 isa monosaccharide is a 5-membered ring saccharide. In other embodiments, R 3 is a monosaccharide that is a 6-membered ring saccharide.
  • R 3 is hydrogen.
  • the compound belongs to Formula Ie: , wherein R 3 is defined as above for Formula I.
  • R 3 is selected from monosaccharide, disaccharide, and oligosaccharide.
  • R 3 is a monosaccharide that is a 5-membered ring saccharide.
  • R 3 is a monosaccharide that is a 6-membered ring saccharide.
  • R 3 is hydrogen.
  • the compound belongs to Formula If:
  • R 3 is selected from monosaccharide, disaccharide, and oligosaccharide.
  • R 3 is a monosaccharide that is a 5-membered ring saccharide.
  • R 3 is a monosaccharide that is a 6-membered ring saccharide.
  • R 3 is hydrogen.
  • the compound belongs to Formula Ig: , Formula Ig wherein R 3 is defined as above for Formula I.
  • R 3 is selected from monosaccharide, disaccharide, and oligosaccharide.
  • R 3 is a monosaccharide that is a 5-membered ring saccharide. In other embodiments, R 3 is a monosaccharide that is a 6-membered ring saccharide. In other embodiments, R 3 is hydrogen. In a more particular embodiment, the compound belongs to Formula Ih:
  • R 3 is selected from monosaccharide, disaccharide, and oligosaccharide.
  • R 3 is a monosaccharide that is a 5-membered ring saccharide.
  • R 3 is a monosaccharide that is a 6-membered ring saccharide.
  • R 3 is hydrogen.
  • the compound belongs to Formula Ii: , Formula Ii wherein R 3 is defined as above for Formula I and R 1 is OR 4 , wherein R 4 is a disaccharide.
  • R 3 is selected from monosaccharide, disaccharide, and oligosaccharide. In some embodiments, R 3 is a monosaccharide that is a 5-membered ring saccharide. In other embodiments, R 3 is a monosaccharide that is a 6-membered ring saccharide. In other embodiments, R 3 is hydrogen. In another embodiment, the compound belongs to Formula Ij: , Formula Ij wherein R 2 is defined as above for Formula I and R 1 is OR 4 , wherein R 4 is a disaccharide. In certain embodiments, R 2 is selected from monosaccharide, disaccharide, and oligosaccharide.
  • R 2 is a monosaccharide that is a 5-membered ring saccharide. In other embodiments, R 2 is a monosaccharide that is a 6-membered ring saccharide. In other embodiments, R 2 is hydrogen. In another embodiment, the compound belongs to Formula Ik: , Formula Ik wherein R 2 and R 3 are defined as above for Formula I. In certain embodiments, R 2 and R 3 are each independently selected from monosaccharide, disaccharide, and oligosaccharide. In some embodiments, R 2 and/or R 3 is a monosaccharide that is a 5-membered ring saccharide.
  • R 2 and/or R 3 is a monosaccharide that is a 6-membered ring saccharide. In other embodiments, R 2 and/or R 3 is hydrogen. In another embodiment, the compound belongs to Formula Il: , Formula Il wherein R 2 is defined as above for Formula I. In certain embodiments, R 2 is selected from monosaccharide, disaccharide, and oligosaccharide. In some embodiments, R 2 is a monosaccharide that is a 5-membered ring saccharide. In other embodiments, R 2 is a monosaccharide that is a 6-membered ring saccharide. In other embodiments, R 2 is hydrogen.
  • the compound belongs to Formula Im: wherein R 2 is defined as above for Formula I.
  • R 2 is selected from monosaccharide, disaccharide, and oligosaccharide.
  • R 2 is a monosaccharide that is a 5-membered ring saccharide.
  • R 2 is a monosaccharide that is a 6-membered ring saccharide.
  • R 2 is hydrogen.
  • the compound belongs to Formula In: , Formula In wherein R 2 is defined as above for Formula I.
  • R 2 is selected from monosaccharide, disaccharide, and oligosaccharide.
  • R 2 is a monosaccharide that is a 5-membered ring saccharide. In other embodiments, R 2 is a monosaccharide that is a 6-membered ring saccharide. In other embodiments, R 2 is hydrogen.
  • the compound of Formula I is digupigan A: .
  • Digupigan A (CC-00529) was originally isolated from the root bark of Lycium chinense (goji berry, 1.5 – 4 mg/kg in yield). It was later found in many other plants, such as the bark of Fraxinus spp.(15 mg/kg in yield ) and the fruits of Sambucus williamsii (red elder). It can be easily acquired from several plant species, bioconversion, or synthesis.
  • the at least one compound of Formula I is a digupigan A analog is selected from the following:
  • the compounds described above can be prepared chemically or biochemically or isolated from natural sources. Exemplary synthetic methods for some of the compounds are provided in the Examples infra. Methods of obtaining digupigan A (CC-00529) are also provided in Wei, X.; Liang, J. “Chemical studies on root bark of Lycium chinense.” Zhongcaoyao, 2003, 34, 580-581. Methods of obtaining rhyncoside A (CC-00593) are provided in Bao, S.; Ding, Y.; Deng, Z.; et al. “Rhyncosides A-F, phenolic constituents from the Chinese mangrove plant Bruguiera sexangula var.
  • CC-00594 and CC-00596 are provided in Zhokhov, S. S.; Jastrebova, J. A.; Kenne, L.; et al. “Antioxidant Hydroquinones Substituted by ⁇ -1,6-Linked Oligosaccharides in Wheat Germ,” Journal of Natural Products, 2009, 72, 656-661.
  • Methods of obtaining CC- 00595 are provided in Bouvier, Edouard; Horvath, Csaba. Isolation of glucosides of methoxyhydroquinones from wheat germ.
  • Methods of obtaining CC-00599 are provided in Arevalo, C.; Ruiz, I.; Piccinelli, A. L.; “Phenolic derivatives from the leaves of Martinella obovata (Bignoniaceae),” Natural Product Communications, 2011, 6, 957-960.
  • Methods of obtaining CC-00600 are provided in Xu, M.; Zhang, M.; Wang, D.; “Phenolic Compounds from the Whole Plants of Gentiana rhodantha (Gentianaceae),” Chemistry & Biodiversity, 2011, 8, 1891-1900.
  • capparoside A (CC-00601) are provided in Luecha, P.; Umehara, K.; Miyase, T.; et al. “Antiestrogenic Constituents of the Thai Medicinal Plants Capparis flavicans and Vitex glabrata,” Journal of Natural Products, 2009, 72, 1954-1959.
  • Methods of obtaining tachioside (CC-00634) are provided in Masataka, S.; Masao. K. Phenolic glycosides from Osmanthus asiaticus. Phytochemistry 1991, 30(9), 3147-9.
  • Methods of obtaining CC-00673 are provided in Sergei S. Z.; Jelena A.
  • the concentration of the at least one compound of Formula I in the beverage can vary from 1 ppm to about 200 ppm, such as, for example, from 1 ppm to 150 ppm, from 1 ppm to 100 ppm, from 1 ppm to 50 ppm, from 25 ppm to 200 ppm, from 25 ppm to 150 ppm, from 25 ppm to 100 ppm, from 25 ppm to 50 ppm, from 50 ppm to 200 ppm, from 50 ppm to 150 ppm, from 50 ppm to 100 ppm, from 100 ppm to 200 ppm, from 100 pm to 150 ppm or from 150 ppm to 200 ppm.
  • the concentration of the at least one compound of Formula I can be 10 ppm, 20 ppm, 30 ppm, 40 ppm, 50 ppm, 60 ppm, 70 ppm, 80 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 or any range between these values.
  • the compounds of Formula I act as sweetness enhancers and/or taste modulators in the present beverages.
  • the beverage of the present invention comprises at least one sweetener in a sweetening amount.
  • the sweetener is a steviol glycoside or steviol glycoside mixture.
  • the steviol glycoside can be natural or synthetic.
  • the steviol glycoside can be provided in pure form or as part of a mixture.
  • Exemplary steviol glycosides include, but are not limited to, rebaudioside M, rebaudioside D, rebaudioside A, rebaudioside N, rebaudioside O, rebaudioside E, steviolmonoside, steviolbioside, rubusoside, dulcoside B, dulcoside A, rebaudioside B, rebaudioside G, stevioside, rebaudioside C, rebaudioside F, rebaudioside I, rebaudioside H, rebaudioside L, rebaudioside K, rebaudioside J, rebaudioside M2, rebaudioside D2, rebaudioside S, rebaudioside T, rebaudioside U, rebaudio
  • the steviol glycoside mixture sweetener typically has a total steviol glycoside content of about 95% by weight or greater on a dry basis. The remaining 5% comprises other non-steviol glycoside compounds, e.g. by-products from extraction or purification processes.
  • the steviol glycoside blend sweetener has a total steviol glycoside content of about 96% or greater, about 97% or greater, about 98% or greater or about 99% or greater.
  • a steviol glycoside mixture comprises at least about 5% of a particular steviol glycoside by weight, such as, for example, at least about 10%, at least about 20%, at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, at least about 80%, at least about 90%, at least about 95% or at least about 97%.
  • the steviol glycoside mixture comprises at least about 50% of a particular steviol glycoside by weight, such as, for example, from about 50% to about 90%, from about 50% to about 80%, from about 50% to about 70%, from about 50% to about 60%, from about 60% to about 90%, from about 60% to about 80%, from about 60% to about 70%, from about 70% to about 90%, from about 70% to about 80% and from about 80% to about 90%.
  • the sweetener is a steviol glycoside mixture comprising rebaudioside A.
  • the steviol glycoside mixture may comprise at least about 5% rebaudioside A by weight, such as, for example, at least about 10%, at least about 20%, at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, at least about 80%, at least about 90%, at least about 95% or at least about 97%.
  • the steviol glycoside mixture may comprise at least about 50% rebaudioside A by weight, such as, for example, from about 50% to about 90%, from about 50% to about 80%, from about 50% to about 70%, from about 50% to about 60%, from about 60% to about 90%, from about 60% to about 80%, from about 60% to about 70%, from about 70% to about 90%, from about 70% to about 80% and from about 80% to about 90%.
  • the steviol glycoside mixture may comprise from 70% to about 99% rebaudioside A by weight, such as, for example, from about 70% to about 95%, from about 70% to about 90%, from about 80% to about 99%, from about 80% to about 95%, from about 80% to about 90%, from about 90% to about 99% or from about 90% to about 95% by weight.
  • the sweetener is a steviol glycoside mixture comprising rebaudioside M.
  • the steviol glycoside blend mixture may comprise at least about 5% rebaudioside M by weight, such as, for example, at least about 10%, at least about 20%, at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, at least about 80%, at least about 90%, at least about 95% or at least about 97%.
  • the steviol glycoside mixture may comprise at least about 50% rebaudioside M by weight, such as, for example, from about 50% to about 90%, from about 50% to about 80%, from about 50% to about 70%, from about 50% to about 60%, from about 60% to about 90%, from about 60% to about 80%, from about 60% to about 70%, from about 70% to about 90%, from about 70% to about 80% and from about 80% to about 90%.
  • the steviol glycoside mixture may comprise from about 70% to about 99% rebaudioside M by weight, such as, for example, from about 70% to about 95%, from about 70% to about 90%, from about 80% to about 99%, from about 80% to about 95%, from about 80% to about 90%, from about 90% to about 99% or from about 90% to about 95% by weight.
  • the sweetener is a steviol glycoside mixture comprising rebaudioside D.
  • the steviol glycoside mixture may comprise at least about 5% rebaudioside D by weight, such as, for example, at least about 10%, at least about 20%, at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, at least about 80%, at least about 90%, at least about 95% or at least about 97%.
  • the steviol glycoside mixture may comprise at least about 50% rebaudioside D by weight, such as, for example, from about 50% to about 90%, from about 50% to about 80%, from about 50% to about 70%, from about 50% to about 60%, from about 60% to about 90%, from about 60% to about 80%, from about 60% to about 70%, from about 70% to about 90%, from about 70% to about 80% and from about 80% to about 90%.
  • the steviol glycoside mixture may comprise from about 70% to about 99% rebaudioside D by weight, such as, for example, from about 70% to about 95%, from about 70% to about 90%, from about 80% to about 99%, from about 80% to about 95%, from about 80% to about 90%, from about 90% to about 99% or from about 90% to about 95%.
  • the steviol glycoside mixture comprises rebaudioside M and a rebaudioside D.
  • the steviol glycoside mixture is A95, a specific blend of rebaudiosides D, M, A, N, O and, optionally, E. described in WO 2017/059414.
  • A95 comprises rebaudiosides D, M, A, N, O and, optionally, E, wherein the total steviol glycoside content is about 95% or greater by weight, wherein rebaudioside D accounts for from about 55% to about 70% of the total steviol glycoside content by weight, rebaudioside M accounts for from about 18% to about 30% total steviol glycoside content by weight, rebaudioside A accounts for from about 0.5% to about 4% of the steviol glycoside content by weight, rebaudioside N accounts for from about 0.5% to about 5% of the steviol glycoside content by weight, rebaudioside O accounts for from about 0.5% to about 5% of the total steviol glycoside content by weight and, optionally, rebaudioside E accounts for from about 0.2% to about 2% total steviol glycoside content by weight.
  • the concentration of the steviol glycoside sweetener or steviol glycoside mixture sweetener can vary from about 25 ppm to about 600 ppm, such as, for example, from about 25 ppm to about 500 ppm, from about 25 ppm to about 400 ppm, from about 25 ppm to about 300 ppm, from about 25 ppm to about 200 ppm, from about 25 ppm to about 100 ppm, from about 100 ppm to about 600 ppm, from about 100 ppm to about 500 ppm, from about 100 ppm to about 400 ppm, from about 100 ppm to about 300 ppm, from about 100 ppm to about 200 ppm, from about 200 ppm to about 600 ppm, from about 200 ppm to about 500 ppm, from about 200 ppm to about 400 ppm, from about 200 ppm to about 300 ppm, from about 300 ppm to about 600 ppm, from about 300 ppm to about 500 ppm, from about 200
  • the sweetener is a mogroside or mogroside mixture.
  • the mogroside can be natural or synthetic.
  • the mogroside can be provided in pure form or as part of mixture.
  • Exemplary mogrosides include, but are not limited to, any of grosmogroside I, mogroside IA, mogroside IE, 11-oxomogroside IA, mogroside II, mogroside II A, mogroside II B, mogroside II E, 7- oxomogroside II E, mogroside III, Mogroside IIIe, 11- deoxymogroside III, Mogroside IV, 11- oxomogroside IV, 11-oxomogroside IV A, Mogroside V, Isomogroside V, 11-deoxymogroside V, 7-oxomogroside V, 11-oxomogroside V, Isomogroside V, Mogroside VI, Mogrol, 11- oxomogrol, Siamenoside I and combinations thereof.
  • mogrosides include those described in U.S. Patent Application Publication 2016039864.
  • the mogroside is selected from (3 ⁇ ,9 ⁇ ,10 ⁇ ,11 ⁇ ,24R)-3-[(4-O- ⁇ -D-glucospyranosyl-6-O- ⁇ -D-glucopyranosyl]-25-hydroxyl-9- methyl-19-norlanost-5-en-24-yl-[2-O- ⁇ -D-glucopyranosyl-6-O- ⁇ -D-glucopyranosyl]- ⁇ -D- glucopyranoside); (3 ⁇ , 9 ⁇ , 10 ⁇ , 11 ⁇ , 24R)-[(2-O- ⁇ -D-glucopyranosyl-6-O- ⁇ -D- glucopyranosyl- ⁇ -D- glucopyranosyl)oxy]-25-hydroxy-9-methyl-19-norlanost-5-en-24-yl-[2-O- ⁇ -D-glucopyrano
  • a mogroside mixture comprises at least about 5% of a particular mogroside by weight, such as, for example, at least about 10%, at least about 20%, at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, at least about 80%, at least about 90%, at least about 95% or at least about 97%.
  • the mogroside blend comprises at least about 50% of a particular mogroside by weight, such as, for example, from about 50% to about 90%, from about 50% to about 80%, from about 50% to about 70%, from about 50% to about 60%, from about 60% to about 90%, from about 60% to about 80%, from about 60% to about 70%, from about 70% to about 90%, from about 70% to about 80% and from about 80% to about 90%.
  • the mogroside blend has a total mogroside content of about 95% by weight or greater on a dry basis.
  • the mogroside blend sweetener has a total mogroside content of about 96% or greater, about 97% or greater, about 98% or greater or about 99% or greater.
  • the sweetener is a mogroside mixture comprising siamenoside I.
  • the mogroside mixture may comprise at least about 5% siamenoside I by weight, such as, for example, at least about 10%, at least about 20%, at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, at least about 80%, at least about 90%, at least about 95% or at least about 97%.
  • the mogroside mixture may comprise at least about 50% siamenoside I by weight, such as, for example, from about 50% to about 90%, from about 50% to about 80%, from about 50% to about 70%, from about 50% to about 60%, from about 60% to about 90%, from about 60% to about 80%, from about 60% to about 70%, from about 70% to about 90%, from about 70% to about 80% and from about 80% to about 90%.
  • the mogroside mixture may comprise from about 70% to about 99% siamenoside I by weight, such as, for example, from about 70% to about 95%, from about 70% to about 90%, from about 80% to about 99%, from about 80% to about 95%, from about 80% to about 90%, from about 90% to about 99% or from about 90% to about 95%.
  • the sweetener is a mogroside mixture comprising mogroside V.
  • the mogroside mixture may comprise at least about 5% Mogroside V by weight, such as, for example, at least about 10%, at least about 20%, at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, at least about 80%, at least about 90%, at least about 95% or at least about 97%.
  • the mogroside mixture may comprise at least about 50% mogroside V by weight, such as, for example, from about 50% to about 90%, from about 50% to about 80%, from about 50% to about 70%, from about 50% to about 60%, from about 60% to about 90%, from about 60% to about 80%, from about 60% to about 70%, from about 70% to about 90%, from about 70% to about 80% and from about 80% to about 90%.
  • the mogroside mixture may comprise from about 70% to about 99% mogroside V by weight, such as, for example, from about 70% to about 95%, from about 70% to about 90%, from about 80% to about 99%, from about 80% to about 95%, from about 80% to about 90%, from about 90% to about 99% or from about 90% to about 95%.
  • the concentration of the mogroside sweetener or mogroside mixture sweetener can vary from about 25 ppm to about 600 ppm, such as, for example, from about 25 ppm to about 500 ppm, from about 25 ppm to about 400 ppm, from about 25 ppm to about 300 ppm, from about 25 ppm to about 200 ppm, from about 25 ppm to about 100 ppm, from about 100 ppm to about 600 ppm, from about 100 ppm to about 500 ppm, from about 100 ppm to about 400 ppm, from about 100 ppm to about 300 ppm, from about 100 ppm to about 200 ppm, from about 200 ppm to about 600 ppm, from about 200 ppm to about 500 ppm, from about 200 ppm to about 400 ppm, from about 200 ppm to about 300 ppm, from about 300 ppm to about 600 ppm, from about 300 ppm to about 500 ppm, from about 200 ppm to
  • the sweetener is at least one carbohydrate sweetener.
  • suitable carbohydrate sweeteners include, but are not limited to, sucrose, glyceraldehyde, dihydroxyacetone, erythrose, threose, erythrulose, arabinose, lyxose, ribose, xylose, ribulose, xylulose, allose, altrose, galactose, glucose, gulose, idose, mannose, talose, fructose, psicose, sorbose, tagatose, mannoheptulose, sedoheltulose, octolose, fucose, rhamnose, arabinose, turanose, sialose, high fructose corn syrup and combinations thereof.
  • the concentration of the at least one carbohydrate sweetener can vary from about 1.5 wt% to about 12 wt%, such as, for example, from about 5 wt% to about 12 wt%, from about 5 wt% to about 11 wt% or from about 5 wt% to about 10 wt%.
  • the sweetener is at least one protein sweetener. Suitable protein sweeteners include, but are not limited to, brazzein, thaumatin, monellin, curclin, mabinlin, miraculin, pentadin, neoculin, lysozyme and combinations thereof.
  • the concentration of the at least one protein sweetener can vary from about 1 ppm to about 100 ppm, such as, for example, from about 10 ppm to about 100 ppm, from about 10 ppm to about 75 ppm, from about 10 ppm to about 50 ppm, from about 10 ppm to about 25 ppm, from about 25 ppm to about 100 ppm, from about 25 ppm to about 75 ppm, from about 25 ppm to about 50 ppm, from about 50 ppm to about 100 ppm, from about 50 ppm to about 75 ppm and from about 75 ppm to about 100 ppm.
  • the sweetener is at least one synthetic sweetener.
  • Suitable synthetic sweeteners include, but are not limited to, sucralose, potassium acesulfame, aspartame, alitame, saccharin, neohesperidin dihydrochalcone, cyclamate, neotame, N—[N-[3-(3-hydroxy-4- methoxyphenyl)propyl]-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester, N—[N-[3-(3-hydroxy-4- methoxyphenyl)-3-methylbutyl]-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester, N—[N-[3-(3- methoxy-4-hydroxyphenyl)propyl]-L- ⁇ -aspartyl]-L-phenylalanine 1-methyl ester, sucralose, glycyrrhizin, salts thereof and combinations thereof.
  • the concentration of the at least one synthetic sweetener can vary from about 1 ppm to about 500 ppm, such as, for example, from about 1 ppm to about 400 ppm, about 1 ppm to about 300 ppm, from about 1 ppm to about 200 ppm, from about 1 ppm to about 100 ppm, from about 1 ppm to about 50 ppm or from about 1 ppm to about 25 ppm.
  • the sweetener is at least one sugar alcohol. Suitable sugar alcohols include, but are not limited to, sorbitol, mannitol, lactitol, maltitol, xylitol, erythritol and combinations thereof.
  • the at least one sugar alcohol can be present in an amount from about 0.1% to about 3.5% of the finished beverage by weight, such as, for example, from about 0.5% to about 3.5%, from about 0.5% to about 3.0%, from about 0.5% to about 2.5%, from about 0.5% to about 2.0%, from about 0.5% to about 1.5%, from about 0.5% to about 1.0%, from about 1.0% to about 3.5%, from about 1.0% to about 3.0%, from about 1.0% to about 2.5%, from about 1.0% to about 2.0%, from about 1.0% to about 1.5%, from about 1.5% to about 3.5%, from about 1.5% to about 3.0%, from about 1.5% to about 2.5%, from about 1.5% to about 2.0%, from about 2.0% to about 3.5%, from about 2.0% to about 3.0%, from about 2.0% to about 2.5%, from about 2.5% to about 3.5%, from about 2.5% to about 3.0% or from about 3.0% to about 3.5%.
  • the sweetener comprises a mixture of two or more types of sweeteners discussed herein above.
  • the sweetener can contain at least one steviol glycoside or steviol glycoside mixture sweetener in combination with at least one mogroside or mogroside mixture sweetener, at least one carbohydrate sweetener, at least one protein sweetener, at least one synthetic sweetener and/or at least one sugar alcohol sweetener.
  • the sweetener can contain a mogroside or mogroside mixture in combination with at least one steviol glycoside or steviol glycoside mixture sweetener, at least one carbohydrate sweetener, at least one protein sweetener, at least one synthetic sweetener and/or at least one sugar alcohol sweetener.
  • the sweetener can contain at least one carbohydrate sweetener in combination with at least one steviol glycoside or steviol glycoside mixture sweetener, at least one mogroside or mogroside mixture sweetener, at least one carbohydrate sweetener, at least one protein sweetener, at least one synthetic sweetener and/or at least one sugar alcohol sweetener.
  • the sweetener can contain at least one protein sweetener in combination with at least one steviol glycoside or steviol glycoside mixture sweetener, at least one mogroside or mogroside mixture sweetener, at least one carbohydrate sweetener, at least one synthetic sweetener and/or at least one sugar alcohol sweetener.
  • the sweetener can contain at least one synthetic sweetener in combination with at least one steviol glycoside or steviol glycoside mixture sweetener, at least one mogroside or mogroside mixture sweetener, at least one carbohydrate sweetener, at least one protein sweetener and/or at least one sugar alcohol sweetener.
  • the sweetener can contain at least one sugar alcohol sweetener in combination with at least one steviol glycoside or steviol glycoside mixture sweetener, at least one mogroside or mogroside mixture sweetener, at least one carbohydrate sweetener, at least one protein sweetener and/or at least one synthetic sweetener.
  • the specific type of sweetener and concentration/amount in the beverage are described herein above. C.
  • Beverage Formulations The present invention provides a beverage or beverage product comprising at least one sweetener described hereinabove and at least one compound of Formula I.
  • Beverage concentrates and beverage syrups are prepared with an initial volume of liquid matrix (e.g. water) and the desired beverage ingredients. Full strength beverages are then prepared by adding further volumes of water. Powdered beverages are prepared by dry-mixing all of the beverage ingredients in the absence of a liquid matrix. Full strength beverages are then prepared by adding the full volume of water.
  • Beverages comprise a beverage matrix, i.e. the basic ingredient in which the ingredients - including the at least one sweetener and at least one compound of Formula I - 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 and combinations thereof, can be used.
  • Additional suitable beverage matrices include, but are not limited to phosphoric acid, phosphate buffer, citric acid, citrate buffer and carbon-treated water.
  • a non-limiting example of the pH range of the beverage may be from about 1.8 to about 10.
  • a further example includes a pH range from about 2 to about 5.
  • the pH of beverage can be from about 2.5 to about 4.2.
  • the pH of the beverage can vary based on the type of beverage.
  • Dairy beverages can have pHs greater than 4.2.
  • the titratable acidity of a beverage may, for example, range from about 0.01 to about 1.0% by weight of beverage.
  • the sparkling beverage product has an acidity from about 0.01 to about 1.0% by weight of the beverage, such as, for example, from about 0.05% to about 0.25% by weight of beverage.
  • the carbonation of a sparkling beverage product has 0 to about 2% (w/w) of carbon dioxide or its equivalent, for example, from about 0.1 to about 1.0% (w/w).
  • the beverage can be caffeinated or non-caffeinated.
  • the temperature of a beverage may, for example, range from about 4oC to about 100 oC, such as, for example, from about 4oC to about 25oC.
  • the beverage can be a full-calorie beverage that has up to about 120 calories per 8 oz serving.
  • the beverage can be a mid-calorie beverage that has up to about 60 calories per 8 oz. serving.
  • the beverage can be a low-calorie beverage that has up to about 40 calories per 8 oz. serving.
  • the beverage can be a zero-calorie that has less than about 5 calories per 8 oz. serving.
  • the beverage is a cola beverage.
  • the cola beverage can be a low-, mid- or zero-calorie beverage.
  • the cola beverage further comprises allulose and/or erythritol. In other embodiments, the cola beverage further comprises caffeine.
  • high potency sweeteners are more potent and therefore lower concentrations are required to achieve a particular sucrose equivalence (SE).
  • SE sucrose equivalence
  • the sweetness of a non-sucrose sweetener can be measured against a sucrose reference by determining the non-sucrose sweetener’s sucrose equivalence (SE).
  • taste panelists are trained to detect sweetness of reference sucrose solutions containing between 1- 15% sucrose (w/v).
  • non-sucrose sweeteners are then tasted at a series of dilutions to determine the concentration of the non-sucrose sweetener that is as sweet as a given percent sucrose reference. For example, if a 1% solution of a non-sucrose sweetener is as sweet as a 10% sucrose solution, then the sweetener is said to be 10 times as potent as sucrose, and has 10% sucrose equivalence.
  • a beverage has a sucrose equivalence of about 1% (w/v), such as, for example, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9%, about 10%, about 11%, about 12%, about 13%, about 14% or any range between these values.
  • a beverage has a SE from about 2% to about 14%, such as, for example, from about 2% to about 10%, from about 2% to about 5%, from about 5% to about 15%, from about 5% to about 10% or from about 10% to about 15%.
  • the amount of sucrose, and thus another measure of sweetness, in a reference solution may be described in degrees Brix (°Bx).
  • a beverage comprises at least one carbohydrate sweetener and at least one compound of Formula I.
  • the carbohydrate sweetener can be selected from sucrose, glyceraldehyde, dihydroxyacetone, erythrose, threose, erythrulose, arabinose, lyxose, ribose, xylose, ribulose, xylulose, allose, altrose, galactose, glucose, gulose, idose, mannose, talose, fructose, psicose, sorbose, tagatose, mannoheptulose, sedoheltulose, octolose, fucose, rhamnose, arabinose, turanose, sialose, high fructose corn syrup and combinations thereof.
  • the concentration of the at least one compound of Formula I can be any described hereinabove, e.g., from 1 ppm to about 200 ppm, from about 25 ppm to about 200 ppm, from about 50 ppm to about 200 ppm, or from about 100 ppm to about 200 ppm.
  • the amount of carbohydrate sweetener can be any described herein above, e.g., from about 1.5 wt% to about 12 wt%, or about 5 wt% to about 12 wt%, or about 5 wt% to about 10 wt%.
  • the at least one carbohydrate sweetener is selected from sucrose and high fructose corn syrup and the compound of Formula I is digupigan A.
  • the carbohydrate sweetener is sucrose and the compound of Formula I is selected from CC-00594, CC-00599, CC-00600, and CC-00596.
  • the carbohydrate sweetener is high fructose corn syrup and the compound of Formula I is selected from digupigan A and CC- 00600.
  • a beverage product comprises at least one carbohydrate sweetener and at least one compound of Formula I.
  • the carbohydrate sweetener can be selected from sucrose, glyceraldehyde, dihydroxyacetone, erythrose, threose, erythrulose, arabinose, lyxose, ribose, xylose, ribulose, xylulose, allose, altrose, galactose, glucose, gulose, idose, mannose, talose, fructose, psicose, sorbose, tagatose, mannoheptulose, sedoheltulose, octolose, fucose, rhamnose, arabinose, turanose, sialose, high fructose corn syrup and combinations thereof.
  • the at least one carbohydrate sweetener is selected from sucrose and high fructose corn syrup and the compound of Formula I is digupigan A.
  • the carbohydrate sweetener is sucrose and the compound of Formula I is selected from CC-00594, CC-00599, CC-00600, and CC-00596.
  • the carbohydrate sweetener is high fructose corn syrup and the compound of Formula I is selected from digupigan A and CC-00600.
  • a beverage comprises at least one steviol glycoside sweetener and at least one compound of Formula I.
  • the steviol glycoside sweetener can be selected from rebaudioside M, rebaudioside D, rebaudioside A, rebaudioside N, rebaudioside O, rebaudioside E, steviolmonoside, steviolbioside, rubusoside, dulcoside B, dulcoside A, rebaudioside B, rebaudioside G, stevioside, rebaudioside C, rebaudioside F, rebaudioside I, rebaudioside H, rebaudioside L, rebaudioside K, rebaudioside J, rebaudioside M2, rebaudioside D2, rebaudioside S, rebaudioside T, rebaudioside U, rebaudioside V, rebaudioside W, rebaudioside Z1, rebaudioside Z2, rebaudioside IX, enzymatically glucosylated steviol glycosides and combinations thereof.
  • the concentration of the at least one compound of Formula I can be any described hereinabove, e.g., from 1 ppm to about 200 ppm, from about 25 ppm to about 200 ppm, from about 50 ppm to about 200 ppm, or from about 100 ppm to about 200 ppm.
  • the concentration of the steviol glycoside sweetener can be any described hereinabove, e.g., from about 25 ppm to about 600 ppm or from about 100 ppm to about 600.
  • the steviol glycoside sweetener is rebaudioside M and the compound of Formula I is selected from digupigan A and CC-00600.
  • a beverage product comprises at least one steviol glycoside sweetener and at least one compound of Formula I.
  • the steviol glycoside sweetener can be selected from rebaudioside M, rebaudioside D, rebaudioside A, rebaudioside N, rebaudioside O, rebaudioside E, steviolmonoside, steviolbioside, rubusoside, dulcoside B, dulcoside A, rebaudioside B, rebaudioside G, stevioside, rebaudioside C, rebaudioside F, rebaudioside I, rebaudioside H, rebaudioside L, rebaudioside K, rebaudioside J, rebaudioside M2, rebaudioside D2, rebaudioside S, rebaudioside T, rebaudioside U, rebaudioside V, rebaudioside W, rebaudioside Z1, rebaudioside Z2, rebaudioside IX, en
  • the steviol glycoside sweetener is rebaudioside M and the compound of Formula I is selected from digupigan A and CC-00600.
  • a beverage comprises at least one mogroside sweetener and at least one compound of Formula I.
  • the mogroside sweetener can be selected from grosmogroside I, mogroside IA, mogroside IE, 11-oxomogroside IA, mogroside II, mogroside II A, mogroside II B, mogroside II E, 7-oxomogroside II E, mogroside III, Mogroside IIIe, 11- deoxymogroside III, Mogroside IV, 11-oxomogroside IV, 11-oxomogroside IV A, Mogroside V, Isomogroside V, 11-deoxymogroside V, 7-oxomogroside V, 11-oxomogroside V, Isomogroside V, Mogroside VI, Mogrol, 11-oxomogrol, siamenoside I and combinations thereof.
  • the concentration of the at least one compound of Formula I can be any described hereinabove, e.g., from 1 ppm to about 200 ppm, from about 25 ppm to about 200 ppm, from about 50 ppm to about 200 ppm, or from about 100 ppm to about 200 ppm.
  • the concentration of the mogroside sweetener can be any described hereinabove, e.g., from about 25 ppm to about 600 ppm.
  • the mogroside sweetener is mogroside V and the compound of Formula I is digupigan A.
  • the mogroside sweetener is siamenoside I and the compound of Formula I is digupigan A.
  • a beverage product comprises at least one mogroside sweetener and at least one compound of Formula I.
  • the mogroside sweetener can be selected from grosmogroside I, mogroside IA, mogroside IE, 11-oxomogroside IA, mogroside II, mogroside II A, mogroside II B, mogroside II E, 7-oxomogroside II E, mogroside III, Mogroside IIIe, 11- deoxymogroside III, Mogroside IV, 11-oxomogroside IV, 11-oxomogroside IV A, Mogroside V, Isomogroside V, 11- deoxymogroside V, 7-oxomogroside V, 11-oxomogroside V, Isomogroside V, Mogroside VI, Mogrol, 11-oxomogrol, siamenoside I and combinations thereof.
  • the mogroside sweetener is mogroside V and the compound of Formula I is digupigan A.
  • the mogroside sweetener is siamenoside I and the compound of Formula I is digupigan A.
  • the beverage or beverage product can optionally include additives, functional ingredients and combinations thereof, as described herein.
  • the beverage or beverage product may further comprise at least additive and/or at least one functional ingredient, detailed herein below.
  • Exemplary functional ingredients include, but are not limited to, saponins, antioxidants, dietary fiber sources, fatty acids, vitamins, glucosamine, minerals, preservatives, hydration agents, probiotics, prebiotics, weight management agents, osteoporosis management agents, phytoestrogens, long chain primary aliphatic saturated alcohols, phytosterols and combinations thereof.
  • the functional ingredient is at least one saponin.
  • the at least one saponin may comprise a single saponin or a plurality of saponins as a functional ingredient for the composition provided herein.
  • Saponins are glycosidic natural plant products comprising an aglycone ring structure and one or more sugar moieties.
  • Non-limiting examples of specific saponins for use in particular embodiments of the invention include group A acetyl saponin, group B acetyl saponin, and group E acetyl saponin.
  • group A acetyl saponin group B acetyl saponin
  • group E acetyl saponin group E acetyl saponin.
  • Several common sources of saponins include soybeans, which have approximately 5% saponin content by dry weight, soapwort plants (Saponaria), the root of which was used historically as soap, as well as alfalfa, aloe, asparagus, grapes, chickpeas, yucca, and various other beans and weeds.
  • Saponins may be obtained from these sources by using extraction techniques well known to those of ordinary skill in the art. A description of conventional extraction techniques can be found in U.S. Pat. Appl. No.2005/0123662.
  • the functional ingredient is at least one antioxidant.
  • antioxidant refers to any substance which inhibits, suppresses, or reduces oxidative damage to cells and biomolecules.
  • suitable antioxidants for embodiments of this invention include, but are not limited to, vitamins, vitamin cofactors, minerals, hormones, carotenoids, carotenoid terpenoids, non-carotenoid terpenoids, flavonoids, flavonoid polyphenolics (e.g., bioflavonoids), flavonols, flavones, phenols, polyphenols, esters of phenols, esters of polyphenols, nonflavonoid phenolics, isothiocyanates, and combinations thereof.
  • the antioxidant is vitamin A, vitamin C, vitamin E, ubiquinone, mineral selenium, manganese, melatonin, ⁇ -carotene, ⁇ - carotene, lycopene, lutein, zeanthin, crypoxanthin, reservatol, eugenol, quercetin, catechin, gossypol, hesperetin, curcumin, ferulic acid, thymol, hydroxytyrosol, tumeric, thyme, olive oil, lipoic acid, glutathinone, gutamine, oxalic acid, tocopherol-derived compounds, butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), ethylenediaminetetraacetic acid (EDTA), tert-butylhydroquinone, acetic acid, pectin, tocotrienol, tocopherol, coenzyme
  • the antioxidant is a synthetic antioxidant such as butylated hydroxytolune or butylated hydroxyanisole, for example.
  • suitable antioxidants for embodiments of this invention include, but are not limited to, fruits, vegetables, tea, cocoa, chocolate, spices, herbs, rice, organ meats from livestock, yeast, whole grains, or cereal grains.
  • Particular antioxidants belong to the class of phytonutrients called polyphenols (also known as “polyphenolics”), which are a group of chemical substances found in plants, characterized by the presence of more than one phenol group per molecule.
  • Suitable polyphenols for embodiments of this invention include catechins, proanthocyanidins, procyanidins, anthocyanins, quercerin, rutin, reservatrol, isoflavones, curcumin, punicalagin, ellagitannin, hesperidin, naringin, citrus flavonoids, chlorogenic acid, other similar materials, and combinations thereof.
  • the antioxidant is a catechin such as, for example, epigallocatechin gallate (EGCG).
  • the antioxidant is chosen from proanthocyanidins, procyanidins or combinations thereof.
  • the antioxidant is an anthocyanin.
  • the antioxidant is chosen from quercetin, rutin or combinations thereof. In one embodiment, the antioxidant is reservatrol. In another embodiment, the antioxidant is an isoflavone. In still another embodiment, the antioxidant is curcumin. In a yet further embodiment, the antioxidant is chosen from punicalagin, ellagitannin or combinations thereof. In a still further embodiment, the antioxidant is chlorogenic acid. In certain embodiments, the functional ingredient is at least one dietary fiber. Numerous polymeric carbohydrates having significantly different structures in both composition and linkages fall within the definition of dietary fiber.
  • Such compounds are well known to those skilled in the art, non-limiting examples of which include non-starch polysaccharides, lignin, cellulose, methylcellulose, the hemicelluloses, ⁇ -glucans, pectins, gums, mucilage, waxes, inulins, oligosaccharides, fructooligosaccharides, cyclodextrins, chitins, and combinations thereof.
  • dietary fiber generally is derived from plant sources, indigestible animal products such as chitins are also classified as dietary fiber.
  • Chitin is a polysaccharide composed of units of acetylglucosamine joined by ⁇ (1-4) linkages, similar to the linkages of cellulose.
  • the functional ingredient is at least one fatty acid.
  • fatty acid refers to any straight chain monocarboxylic acid and includes saturated fatty acids, unsaturated fatty acids, long chain fatty acids, medium chain fatty acids, short chain fatty acids, fatty acid precursors (including omega-9 fatty acid precursors), and esterified fatty acids.
  • long chain polyunsaturated fatty acid refers to any polyunsaturated carboxylic acid or organic acid with a long aliphatic tail.
  • omega-3 fatty acid refers to any polyunsaturated fatty acid having a first double bond as the third carbon-carbon bond from the terminal methyl end of its carbon chain.
  • the omega-3 fatty acid may comprise a long chain omega-3 fatty acid.
  • omega-3 fatty acid any polyunsaturated fatty acid having a first double bond as the sixth carbon-carbon bond from the terminal methyl end of its carbon chain.
  • suitable omega-3 fatty acids for use in embodiments of the present invention can be derived from algae, fish, animals, plants, or combinations thereof, for example.
  • suitable omega-3 fatty acids include, but are not limited to, linolenic acid, alpha-linolenic acid, eicosapentaenoic acid, docosahexaenoic acid, stearidonic acid, eicosatetraenoic acid and combinations thereof.
  • suitable omega-3 fatty acids can be provided in fish oils, (e.g., menhaden oil, tuna oil, salmon oil, bonito oil, and cod oil), microalgae omega-3 oils or combinations thereof.
  • suitable omega-3 fatty acids may be derived from commercially available omega-3 fatty acid oils such as Microalgae DHA oil (from Martek, Columbia, MD), OmegaPure (from Omega Protein, Houston, TX), Marinol C-38 (from Lipid Nutrition, Channahon, IL), Bonito oil and MEG-3 (from Ocean Nutrition, Dartmouth, NS), Evogel (from Symrise, Holzminden, Germany), Marine Oil, from tuna or salmon (from Arista Wilton, CT), OmegaSource 2000, Marine Oil, from menhaden and Marine Oil, from cod (from OmegaSource, RTP, NC).
  • Suitable omega-6 fatty acids include, but are not limited to, linoleic acid, gamma- linolenic acid, dihommo-gamma-linolenic acid, arachidonic acid, eicosadienoic acid, docosadienoic acid, adrenic acid, docosapentaenoic acid and combinations thereof.
  • Suitable esterified fatty acids for embodiments of the present invention include, but are not limited to, monoacylgycerols containing omega-3 and/or omega-6 fatty acids, diacylgycerols containing omega-3 and/or omega-6 fatty acids, or triacylgycerols containing omega-3 and/or omega-6 fatty acids and combinations thereof.
  • the functional ingredient is at least one vitamin.
  • suitable vitamins include, vitamin A, vitamin D, vitamin E, vitamin K, vitamin B1, vitamin B2, vitamin B3, vitamin B5, vitamin B6, vitamin B7, vitamin B9, vitamin B12, and vitamin C.
  • Suitable vitamins include, vitamin A, vitamin D, vitamin E, vitamin K, vitamin B1, vitamin B2, vitamin B3, vitamin B5, vitamin B6, vitamin B7, vitamin B9, vitamin B12, and vitamin C.
  • Various other compounds have been classified as vitamins by some authorities. These compounds may be termed pseudo-vitamins and include, but are not limited to, compounds such as ubiquinone (coenzyme Q10), pangamic acid, dimethylglycine, taestrile, amygdaline, flavanoids, para-aminobenzoic acid, adenine, adenylic acid, and s-methylmethionine.
  • the term vitamin includes pseudo-vitamins.
  • the vitamin is a fat- soluble vitamin chosen from vitamin A, D, E, K and combinations thereof.
  • the vitamin is a water-soluble vitamin chosen from vitamin B1, vitamin B2, vitamin B3, vitamin B6, vitamin B12, folic acid, biotin, pantothenic acid, vitamin C and combinations thereof.
  • the functional ingredient is glucosamine, optionally further comprising chondroitin sulfate.
  • the functional ingredient is at least one mineral.
  • Minerals in accordance with the teachings of this invention, comprise inorganic chemical elements required by living organisms. Minerals are comprised of a broad range of compositions (e.g., elements, simple salts, and complex silicates) and also vary broadly in crystalline structure.
  • Minerals may naturally occur in foods and beverages, may be added as a supplement, or may be consumed or administered separately from foods or beverages.
  • Minerals may be categorized as either bulk minerals, which are required in relatively large amounts, or trace minerals, which are required in relatively small amounts. Bulk minerals generally are required in amounts greater than or equal to about 100 mg per day and trace minerals are those that are required in amounts less than about 100 mg per day. In one embodiment, the mineral is chosen from bulk minerals, trace minerals or combinations thereof.
  • Non-limiting examples of bulk minerals include calcium, chlorine, magnesium, phosphorous, potassium, sodium, and sulfur.
  • Non-limiting examples of trace minerals include chromium, cobalt, copper, fluorine, iron, manganese, molybdenum, selenium, zinc, and iodine.
  • the mineral is a trace mineral, believed to be necessary for human nutrition, non-limiting examples of which include bismuth, boron, lithium, nickel, rubidium, silicon, strontium, tellurium, tin, titanium, tungsten, and vanadium.
  • the minerals embodied herein may be in any form known to those of ordinary skill in the art.
  • the minerals may be in their ionic form, having either a positive or negative charge.
  • the minerals may be in their molecular form.
  • the functional ingredient is at least one preservative.
  • the preservative is chosen from antimicrobials, antioxidants, antienzymatics or combinations thereof.
  • antimicrobials include sulfites, propionates, benzoates, sorbates, nitrates, nitrites, bacteriocins, salts, sugars, acetic acid, dimethyl dicarbonate (DMDC), ethanol, and ozone.
  • the preservative is a sulfite.
  • Sulfites include, but are not limited to, sulfur dioxide, sodium bisulfite, and potassium hydrogen sulfite.
  • the preservative is a propionate. Propionates include, but are not limited to, propionic acid, calcium propionate, and sodium propionate.
  • the preservative is a benzoate. Benzoates include, but are not limited to, sodium benzoate and benzoic acid.
  • the preservative is a sorbate. Sorbates include, but are not limited to, potassium sorbate, sodium sorbate, calcium sorbate, and sorbic acid.
  • the preservative is a nitrate and/or a nitrite.
  • Nitrates and nitrites include, but are not limited to, sodium nitrate and sodium nitrite.
  • the at least one preservative is a bacteriocin, such as, for example, nisin.
  • the preservative is ethanol.
  • the preservative is ozone.
  • Non-limiting examples of antienzymatics suitable for use as preservatives in particular embodiments of the invention include ascorbic acid, citric acid, and metal chelating agents such as ethylenediaminetetraacetic acid (EDTA).
  • the functional ingredient is at least one hydration agent.
  • the hydration agent is a carbohydrate to supplement energy stores burned by muscles.
  • Suitable carbohydrates for use in particular embodiments of this invention are described in U.S. Patent Numbers 4,312,856, 4,853,237, 5,681,569, and 6,989,171.
  • suitable carbohydrates include monosaccharides, disaccharides, oligosaccharides, complex polysaccharides or combinations thereof.
  • suitable types of monosaccharides for use in particular embodiments include trioses, tetroses, pentoses, hexoses, heptoses, octoses, and nonoses.
  • Non-limiting examples of specific types of suitable monosaccharides include glyceraldehyde, dihydroxyacetone, erythrose, threose, erythrulose, arabinose, lyxose, ribose, xylose, ribulose, xylulose, allose, altrose, galactose, glucose, gulose, idose, mannose, talose, fructose, psicose, sorbose, tagatose, mannoheptulose, sedoheltulose, octolose, and sialose.
  • suitable disaccharides include sucrose, lactose, and maltose.
  • Non-limiting examples of suitable oligosaccharides include saccharose, maltotriose, and maltodextrin.
  • the carbohydrates are provided by a corn syrup, a beet sugar, a cane sugar, a juice, or a tea.
  • the hydration agent is a flavanol that provides cellular rehydration. Flavanols are a class of natural substances present in plants, and generally comprise a 2-phenylbenzopyrone molecular skeleton attached to one or more chemical moieties.
  • Non- limiting examples of suitable flavanols for use in particular embodiments of this invention include catechin, epicatechin, gallocatechin, epigallocatechin, epicatechin gallate, epigallocatechin 3-gallate, theaflavin, theaflavin 3-gallate, theaflavin 3’-gallate, theaflavin 3,3’ gallate, thearubigin or combinations thereof.
  • Several common sources of flavanols include tea plants, fruits, vegetables, and flowers.
  • the flavanol is extracted from green tea.
  • the hydration agent is a glycerol solution to enhance exercise endurance.
  • the functional ingredient is chosen from at least one probiotic, prebiotic and combination thereof.
  • the probiotic is a beneficial microorganism that affects the human body’s naturally-occurring gastrointestinal microflora.
  • probiotics include, but are not limited to, bacteria of the genus Lactobacilli, Bifidobacteria, Streptococci, or combinations thereof, that confer beneficial effects to humans.
  • the at least one probiotic is chosen from the genus Lactobacilli.
  • the probiotic is chosen from the genus Bifidobacteria.
  • the probiotic is chosen from the genus Streptococcus.
  • Probiotics that may be used in accordance with this invention are well-known to those of skill in the art.
  • Non-limiting examples of foodstuffs comprising probiotics include yogurt, sauerkraut, kefir, kimchi, fermented vegetables, and other foodstuffs containing a microbial element that beneficially affects the host animal by improving the intestinal microbalance.
  • Prebiotics include, without limitation, mucopolysaccharides, oligosaccharides, polysaccharides, amino acids, vitamins, nutrient precursors, proteins and combinations thereof.
  • the prebiotic is chosen from dietary fibers, including, without limitation, polysaccharides and oligosaccharides.
  • Non-limiting examples of oligosaccharides that are categorized as prebiotics in accordance with particular embodiments of this invention include fructooligosaccharides, inulins, isomalto-oligosaccharides, lactilol, lactosucrose, lactulose, pyrodextrins, soy oligosaccharides, transgalacto-oligosaccharides, and xylo-oligosaccharides.
  • the prebiotic is an amino acid. Although a number of known prebiotics break down to provide carbohydrates for probiotics, some probiotics also require amino acids for nourishment.
  • Prebiotics are found naturally in a variety of foods including, without limitation, bananas, berries, asparagus, garlic, wheat, oats, barley (and other whole grains), flaxseed, tomatoes, Jerusalem artichoke, onions and chicory, greens (e.g., dandelion greens, spinach, collard greens, chard, kale, mustard greens, turnip greens), and legumes (e.g., lentils, kidney beans, chickpeas, navy beans, white beans, black beans).
  • the functional ingredient is at least one weight management agent.
  • a weight management agent includes an appetite suppressant and/or a thermogenesis agent.
  • appetite suppressant describes macronutrients, herbal extracts, exogenous hormones, anorectics, anorexigenics, pharmaceutical drugs, and combinations thereof, that when delivered in an effective amount, suppress, inhibit, reduce, or otherwise curtail a person’s appetite.
  • thermogenesis agent describes macronutrients, herbal extracts, exogenous hormones, anorectics, anorexigenics, pharmaceutical drugs, and combinations thereof, that when delivered in an effective amount, activate or otherwise enhance a person’s thermogenesis or metabolism.
  • Suitable weight management agents include macronutrients selected from the group consisting of proteins, carbohydrates, dietary fats, and combinations thereof. Consumption of proteins, carbohydrates, and dietary fats stimulates the release of peptides with appetite- suppressing effects. For example, consumption of proteins and dietary fats stimulates the release of the gut hormone cholecytokinin (CCK), while consumption of carbohydrates and dietary fats stimulates release of Glucagon-like peptide 1 (GLP-1). Suitable macronutrient weight management agents also include carbohydrates. Carbohydrates generally comprise sugars, starches, cellulose and gums that the body converts into glucose for energy.
  • Carbohydrates often are classified into two categories, digestible carbohydrates (e.g., monosaccharides, disaccharides, and starch) and non-digestible carbohydrates (e.g., dietary fiber). Studies have shown that non-digestible carbohydrates and complex polymeric carbohydrates having reduced absorption and digestibility in the small intestine stimulate physiologic responses that inhibit food intake. Accordingly, the carbohydrates embodied herein desirably comprise non-digestible carbohydrates or carbohydrates with reduced digestibility.
  • Non-limiting examples of such carbohydrates include polydextrose; inulin; monosaccharide-derived polyols such as erythritol, mannitol, xylitol, and sorbitol; disaccharide- derived alcohols such as isomalt, lactitol, and maltitol; and hydrogenated starch hydrolysates.
  • Carbohydrates are described in more detail herein below.
  • the weight management agent is a dietary fat. Dietary fats are lipids comprising combinations of saturated and unsaturated fatty acids. Polyunsaturated fatty acids have been shown to have a greater satiating power than mono-unsaturated fatty acids.
  • the dietary fats embodied herein desirably comprise poly-unsaturated fatty acids, non-limiting examples of which include triacylglycerols.
  • the weight management agent is an herbal extract. Extracts from numerous types of plants have been identified as possessing appetite suppressant properties. Non-limiting examples of plants whose extracts have appetite suppressant properties include plants of the genus Hoodia, Trichocaulon, Caralluma, Stapelia, Orbea, Asclepias, and Camelia.
  • Other embodiments include extracts derived from Gymnema Sylvestre, Kola Nut, Citrus Auran tium, Yerba Mate, Griffonia Simplicifolia, Guarana, myrrh, guggul Lipid, and black current seed oil.
  • the herbal extracts may be prepared from any type of plant material or plant biomass. Non-limiting examples of plant material and biomass include the stems, roots, leaves, dried powder obtained from the plant material, and sap or dried sap.
  • the herbal extracts generally are prepared by extracting sap from the plant and then spray-drying the sap. Alternatively, solvent extraction procedures may be employed. Following the initial extraction, it may be desirable to further fractionate the initial extract (e.g., by column chromatography) in order to obtain an herbal extract with enhanced activity.
  • the herbal extract is derived from a plant of the genus Hoodia.
  • a sterol glycoside of Hoodia known as P57, is believed to be responsible for the appetite- suppressant effect of the Hoodia species.
  • the herbal extract is derived from a plant of the genus Caralluma, non-limiting examples of which include caratuberside A, caratuberside B, bouceroside I, bouceroside II, bouceroside III, bouceroside IV, bouceroside V, bouceroside VI, bouceroside VII, bouceroside VIII, bouceroside IX, and bouceroside X.
  • the at least one herbal extract is derived from a plant of the genus Trichocaulon.
  • Trichocaulon plants are succulents that generally are native to southern Africa, similar to Hoodia, and include the species T. piliferum and T. officinale.
  • the herbal extract is derived from a plant of the genus Stapelia or Orbea.
  • saponins such as pregnane glycosides, which include stavarosides A, B, C, D, E, F, G, H, I, J, and K.
  • the herbal extract is derived from a plant of the genus Asclepias.
  • the extracts comprise steroidal compounds, such as pregnane glycosides and pregnane aglycone, having appetite suppressant effects.
  • the weight management agent is an exogenous hormone having a weight management effect.
  • hormones include CCK, peptide YY, ghrelin, bombesin and gastrin-releasing peptide (GRP), enterostatin, apolipoprotein A-IV, GLP-1, amylin, somastatin, and leptin.
  • the weight management agent is a pharmaceutical drug.
  • Non- limiting examples include phentenime, diethylpropion, phendimetrazine, sibutramine, rimonabant, oxyntomodulin, floxetine hydrochloride, ephedrine, phenethylamine, or other stimulants.
  • the functional ingredient is at least one osteoporosis management agent.
  • the osteoporosis management agent is at least one calcium source.
  • the calcium source is any compound containing calcium, including salt complexes, solubilized species, and other forms of calcium.
  • Non-limiting examples of calcium sources include amino acid chelated calcium, calcium carbonate, calcium oxide, calcium hydroxide, calcium sulfate, calcium chloride, calcium phosphate, calcium hydrogen phosphate, calcium dihydrogen phosphate, calcium citrate, calcium malate, calcium citrate malate, calcium gluconate, calcium tartrate, calcium lactate, solubilized species thereof, and combinations thereof.
  • the osteoporosis management agent is a magnesium soucrce.
  • the magnesium source is any compound containing magnesium, including salt complexes, solubilized species, and other forms of magnesium.
  • Non-limiting examples of magnesium sources include magnesium chloride, magnesium citrate, magnesium gluceptate, magnesium gluconate, magnesium lactate, magnesium hydroxide, magnesium picolate, magnesium sulfate, solubilized species thereof, and mixtures thereof.
  • the magnesium source comprises an amino acid chelated or creatine chelated magnesium.
  • the osteoporosis agent is chosen from vitamins D, C, K, their precursors and/or beta-carotene and combinations thereof. Numerous plants and plant extracts also have been identified as being effective in the prevention and treatment of osteoporosis.
  • suitable plants and plant extracts as osteoporosis management agents include species of the genus Taraxacum and Amelanchier, as disclosed in U.S.
  • Patent Publication No.2005/0106215 and species of the genus Lindera, Artemisia, Acorus, Carthamus, Carum, Cnidium, Curcuma, Cyperus, Juniperus, Prunus, Iris, Cichorium, Dodonaea, Epimedium, Erigonoum, Soya, Mentha, Ocimum, thymus, Tanacetum, Plantago, Spearmint, Bixa, Vitis, Rosemarinus, Rhus, and Anethum, as disclosed in U.S. Patent Publication No.2005/0079232.
  • the functional ingredient is at least one phytoestrogen.
  • Phytoestrogens are compounds found in plants which can typically be delivered into human bodies by ingestion of the plants or the plant parts having the phytoestrogens.
  • ''phytoestrogen'' refers to any substance which, when introduced into a body causes an estrogen- like effect of any degree.
  • a phytoestrogen may bind to estrogen receptors within the body and have a small estrogen-like effect.
  • suitable phytoestrogens for embodiments of this invention include, but are not limited to, isoflavones, stilbenes, lignans, resorcyclic acid lactones, coumestans, coumestroI, equol, and combinations thereof.
  • Sources of suitable phytoestrogens include, but are not limited to, whole grains, cereals, fibers, fruits, vegetables, black cohosh, agave root, black currant, black haw, chasteberries, cramp bark, dong quai root, devil's club root, false unicorn root, ginseng root, groundsel herb, licorice, liferoot herb, motherwort herb, peony root, raspberry leaves, rose family plants, sage leaves, sarsaparilla root, saw palmetto berried, wild yam root, yarrow blossoms, legumes, soybeans, soy products (e.g., miso, soy flour, soymilk, soy nuts, soy protein isolate, tempen, or tofu) chick peas, nuts, lentils, seeds, clover, red clover, dandelion leaves, dandelion roots, fenugreek seeds, green tea, hops, red wine, flaxseed, garlic, onions, linseed, bo
  • Isoflavones belong to the group of phytonutrients called polyphenols.
  • polyphenols also known as “polyphenolics”
  • Suitable phytoestrogen isoflavones in accordance with embodiments of this invention include genistein, daidzein, glycitein, biochanin A, formononetin, their respective naturally occurring glycosides and glycoside conjugates, matairesinol, secoisolariciresinol, enterolactone, enterodiol, textured vegetable protein, and combinations thereof.
  • Suitable sources of isoflavones for embodiments of this invention include, but are not limited to, soy beans, soy products, legumes, alfalfa sprouts, chickpeas, peanuts, and red clover.
  • the functional ingredient is at least one long chain primary aliphatic saturated alcohol.
  • Long-chain primary aliphatic saturated alcohols are a diverse group of organic compounds. The term alcohol refers to the fact these compounds feature a hydroxyl group (-OH) bound to a carbon atom.
  • Non-limiting examples of particular long-chain primary aliphatic saturated alcohols for use in particular embodiments of the invention include the 8 carbon atom 1-octanol, the 9 carbon 1-nonanol, the 10 carbon atom 1-decanol, the 12 carbon atom 1-dodecanol, the 14 carbon atom 1-tetradecanol, the 16 carbon atom 1-hexadecanol, the 18 carbon atom 1-octadecanol, the 20 carbon atom l-eicosanol, the 22 carbon 1-docosanol, the 24 carbon 1-tetracosanol, the 26 carbon 1-hexacosanol, the 27 carbon 1-heptacosanol, the 28 carbon 1-octanosol, the 29 carbon 1-nonacosanol, the 30 carbon 1-triacontanol, the 32 carbon 1- dotriacontanol, and the 34 carbon 1-tetracontanol.
  • the long-chain primary aliphatic saturated alcohol is a policosanol.
  • Policosanol is the term for a mixture of long-chain primary aliphatic saturated alcohols composed primarily of 28 carbon 1-octanosol and 30 carbon 1-triacontanol, as well as other alcohols in lower concentrations such as 22 carbon 1-docosanol, 24 carbon 1-tetracosanol, 26 carbon 1-hexacosanol, 27 carbon 1-heptacosanol, 29 carbon 1-nonacosanol, 32 carbon 1- dotriacontanol, and 34 carbon 1-tetracontanol.
  • the functional ingredient is at least one phytosterol, phytostanol or combination thereof.
  • stanol Plant stanol
  • stanol plant stanol
  • stanol plant stanol
  • stanol plant stanol
  • stanol plant stanol
  • stanol stanol
  • stanol stanol
  • stanol stanol
  • stanol stanol
  • Plant sterols and stanols are present naturally in small quantities in many fruits, vegetables, nuts, seeds, cereals, legumes, vegetable oils, bark of the trees and other plant sources.
  • Sterols are a subgroup of steroids with a hydroxyl group at C-3.
  • phytosterols have a double bond within the steroid nucleus, like cholesterol; however, phytosterols also may comprise a substituted side chain (R) at C-24, such as an ethyl or methyl group, or an additional double bond.
  • R substituted side
  • phytosterols are well known to those of skill in the art. At least 44 naturally-occurring phytosterols have been discovered, and generally are derived from plants, such as corn, soy, wheat, and wood oils; however, they also may be produced synthetically to form compositions identical to those in nature or having properties similar to those of naturally-occurring phytosterols.
  • Non-limiting suitable phytosterols include, but are not limited to, 4-desmethylsterols (e.g., ⁇ -sitosterol, campesterol, stigmasterol, brassicasterol, 22-dehydrobrassicasterol, and ⁇ 5-avenasterol), 4-monomethyl sterols, and 4,4- dimethyl sterols (triterpene alcohols) (e.g., cycloartol, 24-methylenecycloartanol, and cyclobranol).
  • 4-desmethylsterols e.g., ⁇ -sitosterol, campesterol, stigmasterol, brassicasterol, 22-dehydrobrassicasterol, and ⁇ 5-avenasterol
  • 4-monomethyl sterols e.g., cycloartol, 24-methylenecycloartanol, and cyclobranol
  • stanol “plant stanol” and “phytostanol” are synonymous.
  • Phytostanols are saturated sterol alcohols present in only trace amounts in nature and also may be synthetically produced, such as by hydrogenation of phytosterols. Suitable phytostanols include, but are not limited to, ⁇ -sitostanol, campestanol, cycloartanol, and saturated forms of other triterpene alcohols. Both phytosterols and phytostanols, as used herein, include the various isomers such as the ⁇ and ⁇ isomers. The phytosterols and phytostanols of the present invention also may be in their ester form. Suitable methods for deriving the esters of phytosterols and phytostanols are well known to those of ordinary skill in the art, and are disclosed in U.S.
  • Non- limiting examples of suitable phytosterol and phytostanol esters include sitosterol acetate, sitosterol oleate, stigmasterol oleate, and their corresponding phytostanol esters.
  • the phytosterols and phytostanols of the present invention also may include their derivatives.
  • Exemplary additives include, but not limited to, carbohydrates, polyols, amino acids and their corresponding salts, poly-amino acids and their corresponding salts, sugar acids and their corresponding salts, nucleotides, organic acids, inorganic acids, organic salts including organic acid salts and organic base salts, inorganic salts, bitter compounds, caffeine, flavorants and flavoring ingredients, astringent compounds, proteins or protein hydrolysates, surfactants, emulsifiers, plant extracts, flavonoids, alcohols, polymers and combinations thereof.
  • the composition further comprises one or more polyols.
  • polyol refers to a molecule that contains more than one hydroxyl group.
  • a polyol may be a diol, triol, or a tetraol which contains 2, 3, and 4 hydroxyl groups respectively.
  • a polyol also may contain more than 4 hydroxyl groups, such as a pentaol, hexaol, heptaol, or the like, which contain 5, 6, or 7 hydroxyl groups, respectively.
  • a polyol also may be a sugar alcohol, polyhydric alcohol, or polyalcohol which is a reduced form of carbohydrate, wherein the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.
  • Non-limiting examples of polyols in some embodiments include maltitol, mannitol, sorbitol, lactitol, xylitol, isomalt, propylene glycol, glycerol (glycerin), threitol, galactitol, palatinose, reduced isomalto-oligosaccharides, reduced xylo-oligosaccharides, reduced gentio-oligosaccharides, reduced maltose syrup, reduced glucose syrup, and sugar alcohols or any other carbohydrates capable of being reduced which do not adversely affect taste.
  • Suitable amino acid additives include, but are not limited to, aspartic acid, arginine, glycine, glutamic acid, proline, threonine, theanine, cysteine, cystine, alanine, valine, tyrosine, leucine, arabinose, trans-4-hydroxyproline, isoleucine, asparagine, serine, lysine, histidine, ornithine, methionine, carnitine, aminobutyric acid ( ⁇ , ⁇ , and/or ⁇ -isomers), glutamine, hydroxyproline, taurine, norvaline, sarcosine, and their salt forms such as sodium or potassium salts or acid salts.
  • the amino acid additives also may be in the D- or L-configuration and in the mono-, di-, or tri-form of the same or different amino acids. Additionally, the amino acids may be ⁇ -, ⁇ -, ⁇ - and/or ⁇ -isomers if appropriate. Combinations of the foregoing amino acids and their corresponding salts (e.g., sodium, potassium, calcium, magnesium salts or other alkali or alkaline earth metal salts thereof, or acid salts) also are suitable additives in some embodiments.
  • the amino acids may be natural or synthetic.
  • the amino acids also may be modified.
  • Modified amino acids refers to any amino acid wherein at least one atom has been added, removed, substituted, or combinations thereof (e.g., N-alkyl amino acid, N-acyl amino acid, or N-methyl amino acid).
  • modified amino acids include amino acid derivatives such as trimethyl glycine, N-methyl-glycine, and N-methyl-alanine.
  • modified amino acids encompass both modified and unmodified amino acids.
  • amino acids also encompass both peptides and polypeptides (e.g., dipeptides, tripeptides, tetrapeptides, and pentapeptides) such as glutathione and L-alanyl-L-glutamine.
  • Suitable polyamino acid additives include poly-L-aspartic acid, poly-L-lysine (e.g., poly-L- ⁇ -lysine or poly-L- ⁇ -lysine), poly-L- ornithine (e.g., poly-L- ⁇ -ornithine or poly-L- ⁇ -ornithine), poly-L-arginine, other polymeric forms of amino acids, and salt forms thereof (e.g., calcium, potassium, sodium, or magnesium salts such as L-glutamic acid mono sodium salt).
  • the poly-amino acid additives also may be in the D- or L-configuration.
  • poly-amino acids may be ⁇ -, ⁇ -, ⁇ -, ⁇ -, and ⁇ - isomers if appropriate.
  • Combinations of the foregoing poly-amino acids and their corresponding salts e.g., sodium, potassium, calcium, magnesium salts or other alkali or alkaline earth metal salts thereof or acid salts
  • the poly-amino acids described herein also may comprise co-polymers of different amino acids.
  • the poly-amino acids may be natural or synthetic.
  • poly-amino acids also may be modified, such that at least one atom has been added, removed, substituted, or combinations thereof (e.g., N-alkyl poly- amino acid or N-acyl poly-amino acid).
  • poly-amino acids encompass both modified and unmodified poly-amino acids.
  • modified poly-amino acids include, but are not limited to, poly-amino acids of various molecular weights (MW), such as poly-L- ⁇ - lysine with a MW of 1,500, MW of 6,000, MW of 25,200, MW of 63,000, MW of 83,000, or MW of 300,000.
  • MW molecular weights
  • Suitable sugar acid additives include, but are not limited to, aldonic, uronic, aldaric, alginic, gluconic, glucuronic, glucaric, galactaric, galacturonic, and salts thereof (e.g., sodium, potassium, calcium, magnesium salts or other physiologically acceptable salts), and combinations thereof.
  • Suitable nucleotide additives include, but are not limited to, inosine monophosphate ("IMP”), guanosine monophosphate (“GMP”), adenosine monophosphate (“AMP”), cytosine monophosphate (CMP), uracil monophosphate (UMP), inosine diphosphate, guanosine diphosphate, adenosine diphosphate, cytosine diphosphate, uracil diphosphate, inosine triphosphate, guanosine triphosphate, adenosine triphosphate, cytosine triphosphate, uracil triphosphate, alkali or alkaline earth metal salts thereof, and combinations thereof.
  • IMP inosine monophosphate
  • GMP guanosine monophosphate
  • AMP adenosine monophosphate
  • CMP cytosine monophosphate
  • UMP uracil monophosphate
  • inosine diphosphate guanosine diphosphate
  • nucleotides described herein also may comprise nucleotide-related additives, such as nucleosides or nucleic acid bases (e.g., guanine, cytosine, adenine, thymine, uracil).
  • nucleosides or nucleic acid bases e.g., guanine, cytosine, adenine, thymine, uracil.
  • Suitable organic acid additives include any compound which comprises a -COOH moiety, such as, for example, C2-C30 carboxylic acids, substituted hydroxyl C2-C30 carboxylic acids, butyric acid (ethyl esters), substituted butyric acid (ethyl esters), benzoic acid, substituted benzoic acids (e.g., 2,4-dihydroxybenzoic acid), substituted cinnamic acids, hydroxyacids, substituted hydroxybenzoic acids, anisic acid substituted cyclohexyl carboxylic acids, tannic acid, aconitic acid, lactic acid, tartaric acid, citric acid, isocitric acid, gluconic acid, glucoheptonic acids, adipic acid, hydroxycitric acid, malic acid, fruitaric acid (a blend of malic, fumaric, and tartaric acids), fumaric acid, maleic acid, succinic acid, chlorogenic acid, salicylic acid, creat
  • organic acid additives also may be in either the D- or L-configuration.
  • Suitable organic acid additive salts include, but are not limited to, sodium, calcium, potassium, and magnesium salts of all organic acids, such as salts of citric acid, malic acid, tartaric acid, fumaric acid, lactic acid (e.g., sodium lactate), alginic acid (e.g., sodium alginate), ascorbic acid (e.g., sodium ascorbate), benzoic acid (e.g., sodium benzoate or potassium benzoate), sorbic acid and adipic acid.
  • organic acid additives described optionally may be substituted with at least one group chosen from hydrogen, alkyl, alkenyl, alkynyl, halo, haloalkyl, carboxyl, acyl, acyloxy, amino, amido, carboxyl derivatives, alkylamino, dialkylamino, arylamino, alkoxy, aryloxy, nitro, cyano, sulfo, thiol, imine, sulfonyl, sulfenyl, sulfinyl, sulfamyl, carboxalkoxy, carboxamido, phosphonyl, phosphinyl, phosphoryl, phosphino, thioester, thioether, anhydride, oximino, hydrazino, carbamyl, phosphor or phosphonato.
  • the organic acid additive is present in the sweetener composition in an amount effective to provide a concentration from about 10 ppm to about 5,000 ppm when present in a consumable, such as, for example, a beverage.
  • Suitable inorganic acid additives include, but are not limited to, phosphoric acid, phosphorous acid, polyphosphoric acid, hydrochloric acid, sulfuric acid, carbonic acid, sodium dihydrogen phosphate, and alkali or alkaline earth metal salts thereof (e.g., inositol hexaphosphate Mg/Ca).
  • Suitable bitter compound additives include, but are not limited to, caffeine, quinine, urea, bitter orange oil, naringin, quassia, and salts thereof.
  • Suitable flavorants and flavoring ingredient additives include, but are not limited to, vanillin, vanilla extract, mango extract, cinnamon, citrus, coconut, ginger, viridiflorol, almond, menthol (including menthol without mint), grape skin extract, and grape seed extract.
  • “Flavorant” and “flavoring ingredient” are synonymous and can include natural or synthetic substances or combinations thereof. Flavorants also include any other substance which imparts flavor and may include natural or non-natural (synthetic) substances which are safe for human or animals when used in a generally accepted range.
  • Non-limiting examples of proprietary flavorants include DöhlerTM Natural Flavoring Sweetness Enhancer K14323 (DöhlerTM, Darmstadt, Germany), SymriseTM Natural Flavor Mask for Sweeteners 161453 and 164126 (SymriseTM, Holzminden, Germany), Natural AdvantageTM Bitterness Blockers 1, 2, 9 and 10 (Natural AdvantageTM, Freehold, New Jersey, U.S.A.), and SucramaskTM (Creative Research Management, Stockton, California, U.S.A.).
  • Suitable polymer additives include, but are not limited to, chitosan, pectin, pectic, pectinic, polyuronic, polygalacturonic acid, starch, food hydrocolloid or crude extracts thereof (e.g., gum acacia senegal (FibergumTM), gum acacia seyal, carageenan), poly-L-lysine (e.g., poly-L- ⁇ -lysine or poly-L- ⁇ -lysine), poly-L-ornithine (e.g., poly-L- ⁇ -ornithine or poly-L- ⁇ - ornithine), polypropylene glycol, polyethylene glycol, poly(ethylene glycol methyl ether), polyarginine, polyaspartic acid, polyglutamic acid, polyethylene imine, alginic acid, sodium alginate, propylene glycol alginate, and sodium polyethyleneglycolalginate, sodium hexametaphosphate and its salt
  • Suitable protein or protein hydrolysate additives include, but are not limited to, bovine serum albumin (BSA), whey protein (including fractions or concentrates thereof such as 90% instant whey protein isolate, 34% whey protein, 50% hydrolyzed whey protein, and 80% whey protein concentrate), soluble rice protein, soy protein, protein isolates, protein hydrolysates, reaction products of protein hydrolysates, glycoproteins, and/or proteoglycans containing amino acids (e.g., glycine, alanine, serine, threonine, asparagine, glutamine, arginine, valine, isoleucine, leucine, norvaline, methionine, proline, tyrosine, hydroxyproline, and the like), collagen (e.g., gelatin), partially hydrolyzed collagen (e.g., hydrolyzed fish collagen), and collagen hydrolysates (e.g., porcine collagen hydrolysate).
  • BSA bovine
  • Suitable surfactant additives include, but are not limited to, polysorbates (e.g., polyoxyethylene sorbitan monooleate (polysorbate 80), polysorbate 20, polysorbate 60), sodium dodecylbenzenesulfonate, dioctyl sulfosuccinate or dioctyl sulfosuccinate sodium, sodium dodecyl sulfate, cetylpyridinium chloride (hexadecylpyridinium chloride), hexadecyltrimethylammonium bromide, sodium cholate, carbamoyl, choline chloride, sodium glycocholate, sodium taurodeoxycholate, lauric arginate, sodium stearoyl lactylate, sodium taurocholate, lecithins, sucrose oleate esters, sucrose stearate esters, sucrose palmitate esters, sucrose laurate esters, and other emulsifiers, and the
  • Suitable flavonoid additives are classified as flavonols, flavones, flavanones, flavan-3- ols, isoflavones, or anthocyanidins.
  • flavonoid additives include, but are not limited to, catechins (e.g., green tea extracts such as PolyphenonTM 60, PolyphenonTM 30, and PolyphenonTM 25 (Mitsui Norin Co., Ltd., Japan), polyphenols, rutins (e.g., enzyme modified rutin SanmelinTM AO (San-fi Gen F.F.I., Inc., Osaka, Japan)), neohesperidin, naringin, neohesperidin dihydrochalcone, and the like.
  • catechins e.g., green tea extracts such as PolyphenonTM 60, PolyphenonTM 30, and PolyphenonTM 25 (Mitsui Norin Co., Ltd., Japan
  • polyphenols e
  • Suitable alcohol additives include, but are not limited to, ethanol.
  • Suitable astringent compound additives include, but are not limited to, tannic acid, europium chloride (EuCl 3 ), gadolinium chloride (GdCl 3 ), terbium chloride (TbCl 3 ), alum, tannic acid, and polyphenols (e.g., tea polyphenols).
  • EuCl 3 europium chloride
  • GdCl 3 gadolinium chloride
  • TbCl 3 terbium chloride
  • alum tannic acid
  • polyphenols e.g., tea polyphenols
  • a method of enhancing the sweetness of a beverage comprises (i) providing a beverage comprising at least one sweetener described hereinabove and (ii) adding at least one compound of Formula I described herein to the beverage to provide a beverage with enhanced sweetness compared to the beverage in the absence of the at least one compound of Formula I.
  • a method of enhancing the sweetness of a beverage comprises (i) providing a beverage matrix and (ii) adding at least one sweetener described hereinabove and at least one compound of Formula I described herein to the beverage matrix to provide a beverage with enhanced sweetness.
  • the at least one sweetener and at least one compound of Formula I can be added together, i.e. in the form of a composition, or separately.
  • a method of making a beverage taste more like a sucrose- sweetened beverage comprises (i) providing a beverage comprising at least one sweetener described hereinabove and (ii) adding at least one compound of Formula I described herein in an amount effective to modulate one or more taste attributes of the beverage to make the beverage taste more like a sucrose-sweetened beverage compared to the beverage in the absence of the at least one compound of Formula I.
  • a method of making a beverage taste more like a sucrose- sweetened beverage comprises (i) providing a beverage matrix and (ii) adding at least one sweetener described hereinabove and at least one compound of Formula I described herein to the beverage to provide a beverage that tastes more like a sucrose-sweetened beverage, wherein the at least one compound of Formula I is present in an amount effective to modulate one or more taste attributes of the beverage to make the beverage taste more like a sucrose-sweetened beverage compared to the beverage in the absence of the at least one compound of Formula I.
  • the at least one sweetener and at least one compound of Formula I can be added together, i.e. in the form of a composition, or separately.
  • a method of preparing a sweetened beverage comprises (i) providing a beverage comprising at least one sweetener described hereinabove and (ii) adding at least one compound of Formula I described herein to the beverage.
  • a method of preparing a sweetened beverage comprises (i) providing a beverage matrix and (ii) adding at least one sweetener described hereinabove and at least one compound of Formula I described herein to the beverage matrix. The at least one sweetener and at least one compound of Formula I can be added together, i.e.
  • a method of preparing a sweetened beverage comprises (i) providing an unsweetened beverage and (ii) adding at least one sweetener described hereinabove and at least one compound of Formula I described herein to the unsweetened beverage to provide a sweetened beverage.
  • the at least one sweetener and at least one compound of Formula I can be added together, i.e. in the form of a composition, or separately.
  • High-resolution electrospray ionization mass spectrometry was performed in the negative and positive ion mode with a Sciex Triple TOF 4600 spectrometer.
  • GC-MS were performed on an Aglient 7890A/5977A GC/MSD System using an Aglient HP-5MS column (30 m ⁇ 0.25 mm ⁇ 0.25 ⁇ m).
  • Preparative HPLC was carried out on a Shimadzu LC-20AP system using a YMC-Triart ODS column (50 ⁇ 250 mm, 7 ⁇ m). Column chromatography (CC) was performed using AB-8 resin (Sunresin New Materials Co. Ltd., China).
  • the identification of the botanical origin was performed according to the China pharmacopoeia.
  • Extraction The dried stem bark of F. chinensis Roxb (10 kg) was extracted with 80% ethanol (200 L) at 70°C for 4h. After evaporation of the ethanol, the solution was concentrated to 7 L.
  • LC-MS guided isolation An overall isolation scheme is provided in FIG. 1. The concentrated solution was subjected to an AB-8 resin column and eluted with water (90 L), 30% ethanol (90 L), 60% ethanol (90 L) and 95% ethanol (60 L).
  • the water eluates were applied to a Flash ODS chromatography using methanol-water at 300 mL/min (water 25 L ⁇ 2, totally 50 L;20% MeOH, 5 L ⁇ 16, totally 80 L; 40% MeOH, 5 L ⁇ 10, totally 50 L; 60% MeOH, 5 L ⁇ 10, totally 50 L; 90% MeOH, 5 L ⁇ 10, totally 50 L) as a mobile phase.
  • the elute was combined as follow: the water eluate as Fraction 1; the foregoing 30 L from 20% MeOH as Fraction 2; the last 50 L eluate from 20% MeOH and the whole 40% MeOH eluates as Fraction 3; the whole 60% MeOH eluates as Fraction 4; the whole 90% MeOH eluates as Fraction 5.
  • Fraction 2 50 g was dissolved in 150 mL methanol-water (3:7) and chromatographied on a Sephadex LH-20 column and eluted with methanol-water (3:7) to give 22 eluates, each with 300 mL.
  • Fraction 2.3 (10 g) was dissolved in water (120 mL) and purified on preparative HPLC (YMC Triart C18, 50 ⁇ 250 mm, 7 ⁇ m) eluting with acetonitrile-water (0-100 min, 2%; 100-150 min, 5%; 150-200 min, 8%; 200-220 min, 90% MeCN) at 55 mL/min.
  • Flash column chromatography was carried out using a Teledyne Isco combiflash companion unit with redisep Rf silica gel columns.
  • Proton NMR spectra were obtained on a 300 MHz and 400 MHz Bruker Nuclear Magnetic Resonance Spectrometer. Chemical shifts ( ⁇ ) are reported in parts per million (ppm) and coupling constants (J) values are given in Hz, with the following spectral pattern designations: singlet (s), doublet (d), triplet (t), quartet (q), doublet of doublet (dd), multiplet (m), broad singlet (brs). Tetramethylsilane was used as an internal reference.
  • CC-00629 To a solution of 6 (400 mg, 0.38 mmol) in MeOH (10.0 mL) was added Et 3 N (0.50 mL) under N2 atmosphere at room temperature. The reaction mixture was stirred at 70 °C for 16 h. Upon completion of the reaction, the reaction mixture was concentrated under reduced pressure to obtain the crude product. The crude product was purified by C-18 column chromotography using 20% H 2 O and CH 3 CN to afford CC-00629 [120 mg, with HPLC (>99%)]. The product was further purified by preparative HPLC to afford CC-00629 (85.0 mg, 35% yield) as an off- white solid.
  • reaction stirred at room temperature for 16 h under N2 atmosphere. Upon completion of the reaction, the reaction mixture was diluted with CH2Cl2 (30.0 mL) and filtered through celite. The filtrate was quenched with aqueous saturated NaHCO 3 solution (40.0 mL) and extracted with CH2Cl2 (2 ⁇ 70 mL). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to obtain the crude product, which was purified by silica-gel column chromatography using 50-55%EtOAc-hexanes to afford 3 (110 mg, 13% yield) as an off-white solid.
  • reaction mixture was stirred at room temperature under H 2 atmosphere for 1 h. Upon completion of the reaction, the reaction mixture was filtered through celite. The filtrate was concentrated under reduced pressure to obtain crude product, which was further purified by silica-gel column chromatography using (70-75% EtOAc- hexanes to afford 2 (150 mg, 83% yield) as an off-white solid.
  • CC-00641 was prepared by the following scheme: Synthesis of 3: To a solution of 1 (2.00 g, 8.69 mmol) and 2 (5.30 g, 13.04 mmol) in a mixture of CHCl3 (20.0 mL) and water (4.00 mL) was added TBAB (270 mg, 0.86 mmol) followed by K2CO3 (3.60 g, 26.07 mmol) at room temperature under N 2 atmosphere. The reaction mixture was stirred at 65 °C for 16 h. Upon completion of the reaction, the reaction mixture was diluted with CH2Cl2 and filtered through celite. The filtrate was washed with H2O (2 ⁇ 100 mL).
  • CC-00642 To a solution of 4 (250 mg, 0.32 mmol) in CH 3 OH (5.00 mL) was added Et 3 N (0.5 mL, 3.76 mmol) and stirred at 80 °C under N2 atmosphere for 16 h. Upon completion of the reaction, the reaction mixture was concentrated under reduced pressure and the obtained crude was purified by C-18 column chromatography using 20% of H 2 O inCH 3 CN to afford CC-00642 (75.0 mg, with 97.2% HPLC purity). The material was further purified preparative HPLC to afford CC-00642 (60.1 mg, 39% yield) as an off-white solid.
  • EXAMPLE 12 Synthesis of CC-00643 CC-00643 was prepared by the following scheme: Synthesis of 3: To a solution of 1 (470 mg, 0.90 mmol) and 2 (458 mg, 1.08 mmol) in CH2Cl2 (20.0 mL) was added powder dried 4 ⁇ MS (500 mg) followed by BF3 ⁇ Et2O (0.23 mL, 1.81 mmol) at 0 °C and allowed to stir at room temperature under N 2 atmosphere for 16 h. Upon completion of the reaction, the mixture was diluted with CH2Cl2 and filtered through celite.
  • CC-00643 To a solution of 4 (285 mg, 0.41 mmol) in CH3OH (10.0 mL) was added Et3N (0.57 mL, 4.15 mmol) and stirred at 75 °C under N 2 atmosphere for 16 h. Upon completion of the reaction, the reaction mixture was concentrated under reduced pressure to obtain crude product, which was purified by C-18 column chromatography using 10% of H2O in CH3CN to afford CC-00643 (105 mg with HPLC-77.3% purity). The compound was further purified by preparative HPLC to afford CC-00643 (58.3 mg, 32% yield) as an off-white solid.
  • EXAMPLE 13 Synthesis of CC-00617 CC-00617 was prepared by the following scheme: Synthesis of 3: To a solution of 1 (400 mg, 0.77 mmol) and 2 (402 mg, 0.92 mmol) in CH2Cl2 (20.0 mL) was added powder dried 4 ⁇ MS (500 mg) followed by BF3 ⁇ Et2O (0.19 mL, 1.54 mmol) at 0 °C and allowed to stir at room temperature for 16 h under N 2 atmosphere. Upon completion of the reaction, the mixture was diluted with CH2Cl2 and filtered through celite.
  • EXAMPLE 15 Synthesis of CC-00639 CC-00639 was prepared by the following scheme: Synthesis of 3: To a solution of 1 (300 mg, 0.579 mmol) and 2 (542 mg, 0.694 mmol) in CH 2 Cl 2 (20.0 mL) was added powder dried 4 ⁇ MS (150 mg) followed by BF 3 ⁇ Et 2 O (0.147 mL, 1.157 mmol) at 0 °C and allowed to stir at room temperature for 16 h under N2 atmosphere. Upon completion of the reaction, the reaction mixture was diluted with CH 2 Cl 2 (25.0 mL) and filtered through celite.
  • CC-00618 was prepared by the following scheme: Synthesis of 3: To a solution of 1 (110 mg, 0.478 mmol) and 2 (448 mg, 0.573 mmol) in CH2Cl2 (20.0 mL) was added powder dried 4 ⁇ MS (1.00 g) followed by BF 3 •Et 2 O (0.091 mL, 0.717 mmol) at 0 °C and allowed to stir at room temperature for 16 h under N2 atmosphere.
  • reaction mixture was diluted with CH2Cl2 (20.0 mL) and filtered through celite. The filtrate was quenched with aqueous saturated NaHCO 3 solution and extracted with CH 2 Cl 2 (2 ⁇ 15.0 mL). The combined organic layers were dried over Na 2 SO 4 and concentrated under reduced pressure to obtain the crude product, which was purified by silica-gel column chromatography using 30% EtOAc-hexanes to afford 3 (380 mg, 0.448 mmol, 93% yield) as a white solid.
  • reaction mixture was diluted with CH 2 Cl 2 (10 mL), cooled to 0 °C, quenched with triethyl amine (1 mL), then filtered through celite. The filtrate was concentrated under reduced pressure to obtain the crude product, which was purified by silica-gel column chromatography using 60-65% EtOAc-hexanes to afford 3 (300 mg, 61%) as an off- white solid.
  • CC-00690 To a solution of 4 (300 mg, 0.39 mmol) in CH 3 OH (10.0 mL) was added Et 3 N (0.42 mL, 3.12 mmol) and stirred at 75 °C under N2 atmosphere for 12 h. Upon completion of the reaction, the reaction mixture was concentrated under reduced pressure to obtained crude product, which purified by C-18 column chromatography using 10% of H2O in CH3CN to afford CC-00690 (220 mg, with HPLC-84.0% purity). The material was further purified by preparative HPLC to afford CC-00690 (72.1 mg, 41% yield) as an off- white solid.
  • EXAMPLE 18 Synthesis of CC-00671 CC-00671 was prepared by the following scheme: Synthesis of 3: To a solution of 1 (300 mg, 1.30 mmol) and 2 (1.21 g, 1.56 mmol) in CH 2 Cl 2 (20.0 mL) was added powder dried 4 ⁇ MS (300 mg) followed by BF3 ⁇ Et2O (0.32 mL, 1.73 mmol) at 0 °C. The mixture was stirred at room temperature for 16 h under N 2 atmosphere. Upon completion of the reaction, the reaction mixture was diluted with CH 2 Cl 2 and filtered through celite. The filtrate was quenched with sat. NaHCO3 solution and extracted with CH2Cl2 (2 ⁇ 20 mL).
  • CC-00671 To a solution of 4 (400 mg, 0.52 mmol) in CH3OH (10.0 mL) was added Et3N (0.5 mL) and stirred at 80 °C under N2 atmosphere for 16 h. Upon completion of the reaction, the reaction mixture was concentrated under reduced pressure and the obtained crude was purified by C-18 column chromatography using 20% H2O in CH3CN to afford CC-00671 (120 mg, 50% yield) as an off-white solid.
  • reaction mixture was diluted with CH2Cl2 and filtered through celite. The filtrate was quenched with sat. NaHCO3 solution and extracted with CH2Cl2 (2 ⁇ 20 mL). The combined organic layers were dried over Na 2 SO 4 and concentrated under reduced pressure to obtain the crude product, which was purified by silica-gel column chromatography using 60% EtOAc-hexanes to afford 3 as an off-white solid (150 mg, 55%).
  • CC-00658 To a solution of 5 (150 mg, 0.10 mmol) in CH3OH (10.0 mL) was added Et3N (0.30 mL) and stirred at 70 °C under N2 atmosphere for 16 h. Upon completion of the reaction, the reaction mixture was concentrated to obtain crude compound (80.0 mg). The crude compound was purified by C-18 column chromatography using 20% H2O in CH 3 CN (70.0 mg, with 81.7% HPLC purity). The product was further purified by preparative HPLC to afford CC-00658 (25.0 mg, 28% yield) as an off-white solid.
  • reaction mixture was diluted with CH 2 Cl 2 and filtered through celite. The filtrate was quenched with aqueous sat. NaHCO 3 solution and extracted with CH 2 Cl 2 (2 ⁇ 20 mL). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to obtain the crude product, which was purified by silica-gel column chromatography using 50% EtOAc-hexanes to afford 3 as a pale-yellow solid (210 mg, 38%).
  • EXAMPLE 21 Sweetness Enhancement of Samples Containing Digupigan A with Sweetener Sample Preparation Each substrate is added into filtered water while stirring. The sample was tested within 24 hours at room temperature. Taste Evaluation Taste tests were carried out with two panelists. Bottles or vials were removed from the refrigerator and warmed up to room temperature. Due to small amount of allowed sample size, panelist used pipet to drop the sample on their tongue and were requested to spit the sample after 5 seconds. Panelist was given mineral water to rinse their mouth before tasting and between tasting different samples. Unsalted crackers were also given to panelist to eat followed by rinsing their mouth with mineral water before tasting the next sample. Results Table 1. Sweetness of 100 ppm of digupigan A in water Table 2. Examples of Sweetness Enhancement with 100 ppm of digupigan A
  • EXAMPLE 23 Assessment of Compounds for Sweetness Enhancement Taste Evaluation 0.5ml of the test solution (targeting to 200 ppm but fully dissolved) placed into a sterile plastic syringe, and was compared with two references, A and B.
  • Reference A was a 1% Sucrose solution and reference B was a 2% sucrose solution.
  • Panelists were asked to rank the test in terms of sweetness compared to both references and decide where the test fell on this sweetness ‘scale’. N.B. where panelist comments have a number in bracket next to them, this denotes the number of panelists in agreement. Table 6. Result

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Abstract

La présente invention concerne des boissons et des produits de boisson comprenant certains édulcorants et au moins un composé de la formule I. Les composés de la formule I sont des analogues de digupigan A qui agissent pour renforcer le sucré de certaines boissons et/ou moduler un ou plusieurs attributs de goût de la boisson pour fournir une boisson présentant des caractéristiques d'un goût plus sucré au saccharose. Des procédés de préparation de boissons et des procédés de renforcement du sucré et/ou d'un ou de plusieurs attributs de goût de boissons sont également détaillés dans la présente invention.
PCT/US2022/030525 2021-05-21 2022-05-23 Renforcement de sucré et modulation de goût à l'aide d'analogues de digupigan a WO2022246313A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2816725B2 (ja) * 1989-10-31 1998-10-27 万田発酵株式会社 糖類吸収抑制剤
US20130102554A1 (en) * 2009-12-30 2013-04-25 Hai Soo LEE Composition for treatment of obesity using wheat bran extract or active ingredient isolated therefrom
KR101431008B1 (ko) * 2012-06-25 2014-08-20 재단법인 경기과학기술진흥원 밀겨 추출물에서 분리된 타치오시드를 이용한 알러지성 질환의 개선제 조성물
US20200178574A1 (en) * 2017-05-31 2020-06-11 The Coca-Cola Company Sweetness and Taste Improvement of Steviol Glycoside and Mogroside Sweeteners with Cyclamate
JP2020147527A (ja) * 2019-03-13 2020-09-17 国立大学法人九州大学 ヒアルロン酸産生促進剤および保湿剤、コラーゲン産生促進剤および抗シワ剤、細胞賦活化剤、ならびに、メラニン産生抑制剤および美白剤

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2816725B2 (ja) * 1989-10-31 1998-10-27 万田発酵株式会社 糖類吸収抑制剤
US20130102554A1 (en) * 2009-12-30 2013-04-25 Hai Soo LEE Composition for treatment of obesity using wheat bran extract or active ingredient isolated therefrom
KR101431008B1 (ko) * 2012-06-25 2014-08-20 재단법인 경기과학기술진흥원 밀겨 추출물에서 분리된 타치오시드를 이용한 알러지성 질환의 개선제 조성물
US20200178574A1 (en) * 2017-05-31 2020-06-11 The Coca-Cola Company Sweetness and Taste Improvement of Steviol Glycoside and Mogroside Sweeteners with Cyclamate
JP2020147527A (ja) * 2019-03-13 2020-09-17 国立大学法人九州大学 ヒアルロン酸産生促進剤および保湿剤、コラーゲン産生促進剤および抗シワ剤、細胞賦活化剤、ならびに、メラニン産生抑制剤および美白剤

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