Flavor composition comprising triterpenoid and sweetness modifier

Abstract

A flavor composition is provided. The composition includes at least one triterpenoid compound selected from the group consisting of pterocaryoside B, pterocaryoside A, cyclocarioside K and combinations thereof; and at least one sweetness modifier selected from the group consisting of steviol glycosides, mogrosides, dihydrochalcones, sweet proteins and combinations thereof.

Description

[0001] COMPOSITIONS

[0002] TECHNICAL FIELD

[0003] The present disclosure relates to compositions and methods which use triterpenoids in combination with sweetness modifiers in flavor compositions and consumables, to improve the taste quality and / or the mouthfeel of sweet-tasting substances.

[0004] BACKGROUND

[0005] Compounds for modifying the taste of consumable products, that is, products taken orally either for ingestion or spitting out, such as foodstuffs, beverages, confectionery, oral care products and the like are widely used. They do not themselves add flavor to the consumable, but they provide desirable ancillary benefits, such as enhanced mouthfeel and / or sweetness, or masking undesirable characteristics of other ingredients, such as the distinctive tastes and textures perceived as unappealing of products containing sugar replacers.

[0006] In the case of sugar replacers, the tastes they impart can present different temporal profiles, flavor-profiles or adaptation behaviors compared with the sugars which they replace, in whole or in part. For example, the sweet taste of natural and synthetic high-intensity sweeteners (HIS), is generally slower in onset and longer in duration than the sweet taste produced by sugar (sweet, short-chain, soluble carbohydrates, including glucose, fructose, sucrose, maltose and lactose) or high fructose corn syrups (HFCS) which is known as a replacement for sugar, and this can change the taste balance of an edible composition containing them. This can create unbalanced temporal taste profiles. In addition to the difference in temporal profile, high- intensity sweeteners generally exhibit lower maximal response than sugar; off-tastes including bitter, metallic, cooling, astringent, licorice-like taste and / or sweetness, which diminishes on iterative tasting.

[0007] However, all high-intensity sweeteners have undesirable after-taste in the form of off- notes, such as liquorice-like after-taste, and / or lingering sweetness. In the particular case of Reb A, this takes the form of a combination of an undesirable lingering sweetness and a liquorice-like after-taste. This after-taste detracts from the desired sugar-like sweetness. Thus, effectively masking undesirable tastes or off-tastes in edible compositions is key to consumer acceptance of many edible compositions. Additionally, flavor solutions for sugar reduction are typically limited to stevia derived solutions that may be restricted by regulations, are too expensive, and lack sugar-like mouthfeel. Accordingly, there remains a need to provide flavor compositions in order to improve the the sweetness intensity and modulate the sweet quality of sweet-tasting substances by reducing bitterness, reducing lingering sweetness and increasing sugar-like mouthfeel.

[0008] SUMMARY

[0009] In one illustrative embodiment, a flavor composition comprises at least one triterpenoid compound selected from the group consisting of pterocaryoside B, pterocaryoside A, cyclocarioside K and combinations thereof, and at least one sweetness modifier selected from the group consisting of steviol glycosides, mogrosides, dihydrochalcones, sweet proteins and combinations thereof.

[0010] In yet another illustrative embodiment, a consumable is provided. The consumable includes at least one sweetener and a flavor composition according to the present disclosure comprising at least one triterpenoid compound selected from the group consisting of pterocaryoside B, pterocaryoside A, cyclocarioside K and combinations thereof. The consumable may also comprise a sweetness modifier and / or a taste modifier. The at least one sweetener is present in a sweetening amount.

[0011] In yet another illustrative embodiment, a method is disclosed for imparting a more sugar- like temporal profile, flavor profile and / or taste profile to a consumable by adding the flavor compositions disclosed herein to the consumable, thereby providing a consumable having a more sugar-like temporal profile, flavor profile and / or taste profile.

[0012] In another embodiment, the more sugar-like temporal profile is a reduced sweetness linger compared to a consumable to which the flavor composition disclosed herein had not been added.

[0013] In a further embodiment, the more sugar-like flavor profile is an improved mouthfeel (for example, increased body or fullness) compared to a consumable to which the flavor composition disclosed herein had not been added.

[0014] Certain embodiments of any aspect of the present disclosure may provide one or more of the following advantages:

[0015] - increased sweetness in a composition; enhanced sweetness in a composition including at least one sweetener; decrease in the amount of caloric sweetener required to obtain desired sweetness;

[0016] - improvement of one or more sweetness characteristics to make sweet taste more similar to sugar (sucrose); - weakening of lingering sweetness (e.g., decreasing the length of time the sweet taste remains and / or decreasing the intensity of the sweet taste more rapidly);

[0017] - weakening of bitter taste and / or liquorice taste and / or metallic taste;

[0018] - weakening of the sensory perceptions of dryness and / or astringent mouthfeel;

[0019] - improvement in sweetness impact (e.g., increasing the maximum intensity of the sweet taste and / or decreases the length of time for the sweet taste to be detected) (e.g., decreasing the lingering sweetness).

[0020] These and other features, aspects and advantages of specific embodiments will become evident to those skilled in the art from a reading of the present disclosure.

[0021] DETAILED DESCRIPTION

[0022] The following text sets forth a broad description of numerous different embodiments of the present disclosure. The description is to be construed as exemplary only and does not describe every possible embodiment since describing every possible embodiment would be impractical, if not impossible. It will be understood that any feature, characteristic, component, composition, ingredient, product, step or methodology described herein can be deleted, combined with or substituted for, in whole or part, any other feature, characteristic, component, composition, ingredient, product, step or methodology described herein. Numerous alternative embodiments could be implemented, using either current technology or technology developed after the filing date of this patent, which would still fall within the scope of the claims. All publications and patents cited herein are incorporated herein by reference.

[0023] The present disclosure relates to the surprising finding that flavor compositions including certain triterpenoids and the extracts or fractions containing these compounds, in combination with sweetness modifiers improve the sweetness intensity and modulate the sweet quality of sweet-tasting substances by reducing bitterness, reducing lingering sweetness and increasing sugar-like mouthfeel. In particular, the present disclosure relates to the surprising finding that certain triterpenoids and the extracts or fractions containing these compounds are useful for enhancing the sweetness and / or modulating the taste of certain sweeteners, particularly reduced sugar or non-caloric sweeteners in consumables such as beverages. In one embodiment, triterpenoid compounds such as pterocaryoside B, pterocaryoside A and cyclocarioside K enhance sweetness. In another embodiment, triterpenoid compounds such as pterocaryoside B, pterocaryoside A and cyclocarioside K are taste modulators / modifiers, with or without simultaneously enhancing sweetness. According to the present disclosure, certain triterpenoid compounds of the formulae disclosed herein may be isolated from the leaves of Cyclocarya paliurus. commonly called “sweet tea tree”. The leaves of Cyclocarya paliurus are found in China’s Jiangxi province and have been used in traditional Chinese medicine for the treatment of obesity and diabetes.

[0024] In one embodiment, the leaves of Cyclocarya paliurus are dried prior to extraction. In some embodiments, the leaves are optionally milled prior to extraction.

[0025] The leaves of Cyclocarya paliurus may be extracted by any suitable extraction process, such as, for example, continuous or batch reflux extraction, supercritical fluid extraction, enzyme-assisted extraction, microorganism-assisted extraction, ultrasound-assisted extraction, microwave- assisted extraction, etc. The methods may be deployed at any scale.

[0026] The solvent used for the extraction can be any suitable solvent, such as for example, polar organic solvents (degassed, vacuumed, pressurized or distilled), non-polar organic solvents, water (degassed, vacuumed, pressurized, deionized, distilled, carbon-treated or reverse osmosis) or a mixture thereof. In a particular embodiment, the solvent comprises water and one or more alcohols. In a particular embodiment, the solvent comprises water and an alcohol selected from methanol, ethanol, n-propanol, 2 -propanol, 1 -butanol, 2 -butanol and mixtures thereof.

[0027] The amount of alcohol in the solvent can vary from about 10% to about 100%, such as, for example, about 20%, about 30%, about 40%, about 50%, about 60%, about 70%, about 80%, about 90% or any range between. In a particular embodiment, alcohol comprises from about 80% to about 100% of the solvent, with the remainder being water.

[0028] In some embodiments, the extraction process takes place at elevated temperatures, such as, for example, from about 50 °C to about 100 °C. In a more particular embodiment, the extraction process takes place at a temperature at about 100°C.

[0029] Those skilled in the art will understand that the duration of the extraction will vary based on the amount of solvent and plant material used. In some embodiments, the extraction is carried out for about 10 minutes to about 24 hours. Water and / or any insoluble material can be removed from the extraction mixture to provide a “crude extract.”

[0030] Insoluble plant material may be separated from the extracted mixture by, e.g., filtration. Other suitable separation methods include, but are not limited to, gravity filtration, a plate-and- frame filter press, cross flow filters, screen filters, Nutsche filters, belt filters, ceramic filters, membrane filters, microfilters, nanofilters, ultrafilters or centrifugation. Optionally, various filtration aids such as diatomaceous earth, bentonite, zeolite, etc., may be used in this process.

[0031] The crude extract is then subjected to one or more chromatographic separations to provide a solution of one or more triterpenoid compounds described herein. The crude extract is passed over one or more columns, e.g. those packed with polymeric adsorbent resins. Elution of the one or more columns with aqueous methanol provides a solution containing fractions of the plant extract. In one embodiment, 10% ethanol is first applied to the column and the eluent collected. Fractions can be collected based on % methanol used for elution, e.g., 0% methanol, 30% methanol, 50% methanol, 70% methanol and 100% methanol. Typically, the product of the chromatographic step is collected in multiple fractions, which may then be analyzed using any suitable technique, for example, thin layer chromatography or mass spectrometry.

[0032] In one embodiment according to the present disclosure, the triterpenoid compound is Pterocaryoside B. Its chemical structure (I) is given below:

[0033] In another embodiment, the triterpenoid compound is Pterocaryoside A. Its chemical structure (II) is given below:

[0034] In yet another embodiment, the triterpenoind compound is Cyclocarioside K. Its chemical structure (III) is given below:

[0035]

[0036] According to certain illustrative embodiments, a flavor composition may comprise triterpenoid compounds such as pterocaryoside B, pterocaryoside A and cyclocarioside K in combination with sweetness modifiers and / or taste modifiers. According to certain embodiments, the amount of triterpenoid compounds present in the flavor composition may be in a concentration of from about 100 ppm to about 70,000 ppm, in another embodiment from about 100 ppm to about 50,000 ppm, such as, for example, from about 100 ppm to about 30,000 ppm, from about 100 ppm to about 25,000 ppm, from about 100 ppm to about 20,000 ppm, from about 100 ppm to about 15,000 ppm, from about 100 ppm to about 10,000 ppm, and from about 500 ppm to about 10,000 ppm.

[0037] The sweetness modifiers may comprise one or more of a wide variety of compounds. According to certain illustrative embodiments, the sweetness modifiers are selected from the group consisting of steviol glycosides, mogrosides, dihydrochalcones, sweet proteins and combinations thereof. The term “sweetness modifier”, as used herein, refers to a compound that modifies, enhances, amplifies or potentiates the perception of sweetness of a consumable when the compound is present in the consumable in a concentration at or below the compound’s sweetness recognition threshold, i.e., a concentration at which the compound does not contribute any noticeable sweet taste in the absence of additional sweetener(s).

[0038] According to certain embodiments, the amount of sweetness modifiers present in the flavor composition may be in a concentration of from about 1,000 ppm to about 200,000 ppm, in another embodiment from about 2,000 ppm to about 100,000 ppm, and in another embodiment from about 5,000 ppm to about 100,000 ppm.

[0039] The term “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. In one embodiment, the sweetness modifier is a steviol glycoside(s). Examples of steviol glycosides include, for example, stevioside (CAS: 57817-89-7), rebaudioside A (CAS: 58543- 16-1), rebaudioside B (CAS: 58543-17-2), rebaudioside C (CAS: 63550-99-2), rebaudioside D (CAS: 63279-13-0), rebaudioside E (CAS: 63279-14-1), rebaudioside F (CAS: 438045-89-7), rebaudioside G (CAS: 127345-21-5), rebaudioside H, rebaudioside I (CAS: 1220616-34-1), rebaudioside J, rebaudioside K, rebaudioside L, rebaudioside M (CAS: 1220616-44-3), rebaudioside N (CAS: 1220616-46-5), rebaudioside O (CAS: 1220616-48-7), dulcoside A (CAS: 64432-06-0), dulcoside B (CAS: 63550-99-2) and rubusoside (CAS: 64849-39-4).

[0040] In another embodiment, the steviol glycoside may be a glucosylated steviol glycoside. The glucosylated steviol glycoside included in the composition may be selected from any one or more steviol glycosides capable of having one or more glucose units added to the molecule by a glucosylation reaction. By way of example, but not in limitation, the glucosylated steviol glycoside included in the sweetness modifying composition may be selected from glucosylated stevioside, glucosylated rebaudioside A, glucosylated rebaudioside B, glucosylated rebaudioside C, glucosylated rebaudioside D, glucosylated rebaudioside E, glucosylated rebaudioside F, glucosylated rebaudioside G, glucosylated rebaudioside H, glucosylated rebaudioside I, glucosylated rebaudioside J, glucosylated rebaudioside K, glucosylated rebaudioside L, glucosylated rebaudioside M, glucosylated rebaudioside N, glucosylated rebaudioside O, glucosylated dulcoside A, glucosylated dulcoside B, glucosylated rubusoside, any other glucosylated steviol glycosides derived from an extract of Stevia rebaudiana, and mixtures thereof.

[0041] The glucosylated steviol glycosides may have different degrees of glucosylation. The glucosylated steviol glycoside of the composition may therefore comprise a blend of the same type of glucosylated steviol glycoside and having different or varying degrees of glucosylation. The glucosylated steviol glycoside of the composition may also comprise a blend of one or more different types of glucosylated steviol glycoside having the same degree of glucosylation. The glucosylated steviol glycoside of the composition may further comprise a blend of one or more of different types of glucosylated steviol glycoside with each type having different or varying degrees of glucosylation.

[0042] The glucosylated steviol glycosides may comprise a blend of at least one glucosylated steviol glycoside and at least one residual steviol glycoside. A residual steviol glycoside refers to an unreacted steviol glycoside that has not been glucosylated. The residual steviol glycoside may include residual stevioside, residual rebaudioside A, residual rebaudioside B, residual rebaudioside C, residual rebaudioside D, residual rebaudioside E, residual rebaudioside F, residual rebaudioside G, residual rebaudioside H, residual rebaudioside I, residual rebaudioside J, residual rebaudioside K, residual rebaudioside L, residual rebaudioside M, residual rebaudioside N, residual rebaudioside O, residual dulcoside A, residual dulcoside B, residual rubusoside, any other residual steviol glycosides derived from an extract of Stevia rebaudiana, and mixtures thereof. The blend of the at least one glucosylated steviol glycoside and the at least one residual steviol glycoside may comprise about 1 percent and 15 percent of the at least one residual steviol glycoside. According to certain embodiments, the blend of the at least one glucosylated steviol glycoside and the at least one residual steviol glycoside may comprise between about 1 percent and 10 percent, or about 1 percent to about 8 percent, or about 1 percent to about 6 percent, or about 1 percent to about 4 percent, or about 1 percent to about 2 percent, of the at least one residual steviol glycoside.

[0043] The glucosylated steviol glycosides may be prepared by preparing a reaction mixture of one or more steviol glycosides, a source of glucose units to be added to the steviol glycoside molecules, an enzyme to catalyze the glucosylation reaction, and a suitable solvent. According to certain embodiments, the glucosylated steviol glycosides are prepared by preparing a reaction mixture of one or more steviol glycosides, a starch as the source of glucose units to be added to the steviol glycoside molecules, CGTase (cyclodextrin glucano-transferase) to catalyze the glucosylation reaction, and water as the solvent. The glucosylation reaction is carried out on the reaction mixture, and the resulting product is purified and dried. By way of example, the glucosylated steviol glycosides may be prepared in accordance with the disclosure of JP2001- 120218 A, which is incorporated by reference. The alpha-glycosyl steviol glycosides (alpha-GS) are prepared by the alpha-addition of glucose by means of cyclodextrin glucosyl-transferase to a stevia extract that contains at least 1.5 times as much RebA as stevioside.

[0044] In another embodiment, the sweetness modifier may be one or more mogroside(s). Mogrosides are a group of triterpene glycosides and may be obtained from the fruit Luo Han Guo (Siraitia grosvenorii), also known as arhat fruit or longevity fruit or swingle fruit. Mogrosides make up approximately 1% of the flesh of the fresh fruit. Through extraction, an extract in the form of a powder containing up to 80% mogrosides can be obtained. Examples of mogrosides include, for example, grosvenorine II, grosvenorine I, 11-O-mogroside II (I), 11-O-mogroside II (II), 11-O-mogroside II (III), mogroside II (I), mogroside II (II), mogroside II (III), 11- dehydroxy-mogroside III, 11-O-mogroside III, mogroside III (I), mogroside III (II), mogroside Ille, mogroside IIIx, mogroside IV (I) (siamenoside), mogroside IV (II), mogroside IV (III), mogroside IV (IV), deoxymogroside V (I), deoxymogroside V (II), 11-O-mogroside V (I), mogroside V isomer, mogroside V, iso-mogroside V, iso-mogroside VI, 7-O-mogroside V, 11-O- mogroside VI, 11-epi-mogroside, mogroside VI (I), mogroside VI (II), mogroside VI (III) (neomogroside) and mogroside VI (IV). The mogroside(s) may, for example, be obtained or obtainable from Luo Han Guo extracts. In one embodiment, the sweetness modifier may be one or more dihydrochalcones. Examples of dihydrochalcones include, for example, trilobatin (l-[4-(beta-D- glucopyranosyloxy)-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-l -propanone; phloretin; hesperetin dihydrochalcone 4”-beta-D-glucoside (HDG); naringin dihydrochalcone (NarDHC), neohesperidin dihydrochalcone (NHDC, E959); and hesperetin dihydrochalcone (HDC).

[0045] Trilobatin is a natural dihydrochalcone type sweetener that occurs in the Chinese sweet tea plant Lithocarpus polystachyus, the leaves of which have been consumed as sweet tea in the south of China for centuries. The synthesis of HDG may be performed by reduction of hesperidin in dilute alkali which yields hesperidin dihydrochalcone, followed by partial hydrolysis, either by acid or by a dissolved or immobilized enzyme, to form HDG, for example as described in US 3,429,873.

[0046] In another embodiment, dihydrochlacones include a range of compounds of the formula: or a salt thereof, wherein Rj comprises wherein R2 comprises a heterocyclic moiety selected from pyridines, thiazoles, piperidines, pyrrolidines, furans and pyrans; and wherein R3 comprises H or OH.

[0047] According to another embodiment, the dihydrochalcone is l-(2-hydroxyphenyl)-3- (pyridine-4-yl)propan-l-one. Further dihydrochalcones are described in US 8,715,761, which is incorporated by reference in its entirety herein.

[0048] In another embodiment, the sweetness modifier may be a sweet protein, for example, brazzein. Brazzein is a sweet-tasting protein extracted from the West African fruit of the climbing plant Oubli (Pentadiplandr a brazzeana Baillori). It was first isolated by the University of Wisconsin-Madison in 1994. Brazzein is found in the extracellular region, in the pulp tissue surrounding the seeds. Like the other sweet proteins discovered in plants, it is extremely sweet compared to commonly used sweeteners (500 to 2000 times sweeter than sucrose). Other sweet proteins may include, thaumatin, monelin, curculin, mabinlin, miraculin and pentadin.

[0049] Other additional sweetness modifiers may include, glycyphyllin, mukurozioside lib, (+)- hernandulcin, 4P-hydroxyhernandulcin, baiyunoside, phlomisoside I, bryodulcoside, bryoside bryonoside, abrusosides A-E, cyclocarioside A, cyclocaryoside I, albiziasaponins A-E, glycyrrhizin, araboglycyrrhizin, periandrins I-V, pterocaryosides A and B, osladin, polypodosides A and B, telosmosideA8- 18, phyllodulcin, huangqioside E neoastilbin, monatin, 3-acetoxy-5,7- dihydroxy-4'-methoxyflavanone, 4'-trihydroxyflavanone, (2R,3R)- dihydroquercetin 3-0- acetate, dihydroquercetin 3-0-acetate 4'-methyl ether, hesepertin, neoculin, or combinations thereof.

[0050] In another embodiment, the sweetness modifier may be a positive allosteric modulators (also known in the art as “PAMs”) of the human sweet taste receptor are compounds that enhance the sweet receptor activity and sweetness taste perception, and have been used for reduced sugar / reduced calorie consumable applications. There are clear disadvantages to the use of PAMs in reduced sugar consumables, namely, the PAMs have a different temporal quality as compared to sugar and they lack a desired sugar-like mouthfeel.

[0051] Without limitation, and only by way of illustration, the positive allosteric modulator component of the flavor composition may be selected from any one or more compounds disclosed in WO 2008 / 154,221, U.S. Patent Application Publication No. U.S. 2014 / 0235624 Al, U.S. Patent Application Publication No. U.S. 2018 / 0086751 Al, and U.S. Patent Application Publication No. US 2017 / 0354175, each of which are incorporated by reference in their respective entireties.

[0052] According to certain illustrative embodiments, the positive allosteric modulator component of the flavor composition is selected from one or more of the following compounds:

[0053] 2,4-dihydroxyl Benzoic acid (CAS: 89-86-1), 3-[(4-amino-2, 2-dioxido-lH-2, 1, 3-benzothiadiazin-5-yl)oxy]-2, 2-dimethyl-N- propylpropanamide (CAS: 1093200-92-0), 3 -Quinolinecarboxylic acid, 4-amino-5-[2, 2-dimethyl-3-[(l-methylethyl)amino]-3-oxopropoxy]-

[0054] 2-methyl- (CAS: 1359963-68-0),

[0055] 3 -Piperidinecarboxamide, 3-[[(4-amino-2, 2-dioxido-lH-2, 1, 3 -benzothiadi azin- 5- yl)oxy]methyl]-N-cyclopentyl-2-oxo- (CAS: 1446687-20-2),

[0056] 1-Butanone, l-[(3S)-3-[[(4-amino-2, 2-dioxido-lH-2, 1, 3-benzothiadiazin-5-yl)oxy]methyl]-l- piperidinyl]-3-methyl- (CAS: 1469426-64-9),

[0057] 4-Pyridinecarboxamide, N-[2-[(4-amino-2,2-dioxido-lH-2,l,3-benzothiadiazin-5-yl)oxy]-l,l- dimethylethyl]-2,6-dimethyl- sulfamate salt (CAS:2079034-28-7),

[0058] 3 -Pyridinecarboxylic acid, 4-amino-5-[[3-[[(2S)-2-amino-2-cyclohexylacetyl]amino]-3-methyl- 1 -oxobutyl] amino]- (CAS:2242529-79-7),

[0059] 3 -Pyridinecarboxylic acid, 4-amino-5-[[3-[(2-cyclohexylacetyl)amino]-3-methyl-l- oxobutyl] amino]- (CAS: 2242529-82-2), and combinations thereof.

[0060] According to certain illustrative embodiments, the positive allosteric modulator component of the flavor composition is the following compound:

[0061] According to certain illustrative embodiments, the positive allosteric modulator component of the flavor composition is the following compound:

[0062]

[0063] According to certain illustrative embodiments, the positive allosteric modulator component of the flavor composition is the following compound:

[0064] According to certain embodiments, the positive allosteric modulator may be present in the flavor composition in an amount of about 10 ppm to about 20,000 ppm. According to other embodiments, the positive allosteric modulator may be present in an amount of about 20 ppm to about 18,000 ppm; in another embodiment from about 30 ppm to about 16,000 ppm; in another embodiment from about 40 ppm to about 14,000 ppm; in another embodiment from about 50 ppm to about 12,000 ppm; in another embodiment from about 60 ppm to about 10,000 ppm; in another embodiment from about 70 ppm to about 8,000 ppm; in another embodiment from about 80 ppm to about 6,000 ppm; in another embodiment from about 90 ppm to about 4, 000 ppm; and in another embodiment from about 100 ppm to about 2,000 ppm.

[0065] The flavor composition described herein may modify and / or modulate the taste of at least one sweetener. The at least one sweetener can be any known sweetener, for example, a natural sweetener, a natural high potency sweetener or a synthetic sweetener.

[0066] The at least one sweetener is present in a sweetening amount. “Sweetening amount”, as used herein, refers to the amount of compound required to provide detectable sweetness when present in a consumable, e.g., a beverage.

[0067] As used herein, the phrase “natural high potency sweetener” refers to any sweetener found naturally in nature and characteristically has a sweetness potency greater than sucrose, fructose, or glucose, yet has less calories. The natural high potency sweetener can be provided as a pure compound or, alternatively, as part of an extract. As used herein, the phrase “synthetic sweetener” refers to any composition which is not found naturally in nature and characteristically has a sweetness potency greater than sucrose, fructose, or glucose, yet has less calories.

[0068] In other embodiments, the at least one sweetener is a carbohydrate sweetener. Suitable carbohydrate sweeteners are selected from, but not limited to, the group consisting of 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, turanose, cellobiose, sialose and combinations thereof. In other embodiments, the at least one sweetener does not comprise a carbohydrate sweetener.

[0069] In another embodiment, the additional sweetener is a rare sugar selected from sorbose, lyxose, ribulose, xylose, xylulose, D-allose, L-ribose, D-tagatose, L-glucose, L-fucose, L- arabinose, turanose, D-allulose (D-Psicose), rhamnose and combinations thereof. Other sweeteners include Siamenoside I, monatin and its salts (monatin SS, RR, RS, SR), curculin, glycyrrhizic acid and its salts, thaumatin, monellin, mabinlin, tamatin, hemandulcin, phyllodulcin, glycyphyllin, trilobatin, baiyunoside, osladin, polypodoside A, pterocaryoside A, pterocaryoside B, mukurozioside, phlomisoside I, periandrin I, abrusoside A, steviolbioside and cyclocarioside I, sucralose, potassium acesulfame, acesulfame acid and salts thereof, aspartame, alitame, saccharin and salts thereof, hesperidin dihydrochalcone glucoside, neohesperidin dihydrochalcone, cyclamate, cyclamic acid and salts thereof, neotame, advantame, glucosylated steviol glycosides (GSGs) and combinations thereof.

[0070] In another embodiment, the additional sweetener is a sugar alcohol selected from allulose, erythritol, xylitol, maltitol, mannitol, isomalt, sorbitol, inositol, lactitol and combinations thereof.

[0071] In one embodiment, the sweetener is a caloric sweetener or mixture of caloric sweeteners. In another embodiment, the caloric sweetener is selected from sucrose, fructose, glucose, high fructose com / starch syrup, a beet sugar, a cane sugar and combinations thereof.

[0072] In other embodiments, the sweetener comprises at least one steviol glycoside or mogroside, wherein the at least one steviol glycoside or mogroside is present in a sweetening amount.

[0073] Products

[0074] According to the present disclosure, triterpenoid compounds such as pterocaryoside B, pterocaryoside A and cyclocarioside K may be added to a sweetened consumable (i.e., a consumable having at least one sweetener therein), or may be provided as part of a flavor composition for consumables. In one embodiment, triterpenoid compounds such as pterocaryoside B, pterocaryoside A and cyclocarioside K are present in the flavor composition in an amount such that, when the flavor composition is added to a sweetened consumable, the sucrose equivalence of the consumable is increased compared to the consumable in the absence of the triterpenoid compund.

[0075] When added to a consumable, triterpenoid compounds such as pterocaryoside B, pterocaryoside A and cyclocarioside K are included in an amount effective to modify the sweetness or mouthfeel of a sweetener without exhibiting any off-taste. According to certain embodiments, the amount of triterpenoid compounds such as pterocaryoside B, pterocaryoside A and cyclocarioside K present in the consumable may be in a concentration of from about 0.05 ppm to about 70 ppm, in another embodiment from about 0.05 ppm to about 50 ppm, such as, for example, from about 0.05 ppm to about 30 ppm, from about 0.05 ppm to about 25 ppm, from about 0.05 ppm to about 20 ppm, from about 0.05 ppm to about 15 ppm, from about 0.05 ppm to about 10 ppm, from about 0.1 ppm to about 10 ppm and from about 0.5 ppm to about 10 ppm.

[0076] In another embodiment, flavor compositions may include triterpenoid compounds such as pterocaryoside B, pterocaryoside A and cyclocarioside K in combination with aroma ingredients, sweetness modifiers to improve the taste quality and / or the mouthfeel of sweet-tasting substances. According to certain embodiments, the amount of sweetness modifiers present in the consumable may be in a concentration of from about 1 ppm to about 200 ppm, in another embodiment from about 2 ppm to about 100 ppm, and in another embodiment from about 5 ppm to about 50 ppm.

[0077] In one embodiment, the at least one sweetener described herein is present in the consumable in a concentration from about 50 ppm to about 600 ppm, such as, for example, about 50 ppm to about 500 ppm, from about 50 ppm to about 400 ppm, from about 50 ppm to about 300 ppm, from about 50 ppm to about 200 ppm, from about 50 ppm to about 100 ppm, about 100 ppm to about 600 ppm, about 100 ppm to about 500 ppm, about 100 ppm to about 400 ppm, about 100 ppm to about 300 ppm, about 100 ppm to about 200 ppm, about 200 ppm to about 600 ppm, about 200 ppm to about 500 ppm, about 200 ppm to about 400 ppm, about 200 ppm to about 300 ppm, about 300 ppm to about 600 ppm, about 300 ppm to about 500 ppm, about 300 ppm to about 400 ppm, about 400 ppm to about 600 ppm, about 400 ppm to about 500 ppm and about 500 ppm to about 600 ppm. In another embodiment, for full and reduced sugar applications, the at least one sweetener may be present in the consumable in a concentration up to 1,000 ppm.

[0078] When expressed as “ppm”, the concentration is parts per million by weight based on the total weight of the consumable. It should be understood that when a range of values is described in the present disclosure, it is intended that any and every value within the range, including the end points, is to be considered as having been disclosed. It is to be understood that the inventors appreciate and understand that any and all values within the range are to be considered to have been specified, and that the inventors have possession of the entire range and all the values within the range.

[0079] Flavor compositions may also contain one or more food grade excipient(s). Suitable excipients for flavor compositions are well known in the art and include, for example, without limitation, solvents (including water, alcohol, ethanol, oils, fats, vegetable oil, and miglyol), binders, diluents, disintegranting agents, lubricants, flavoring agents, colouring agents, preservatives, antioxidants, emulsifiers, stabilisers, flavor-enhancers, sweetening agents, anticaking agents, and the like. Examples of such carriers or diluents for flavors may be found e.g. in "Perfume and Flavour Materials of Natural Origin", S. Arctander, Ed., Elizabeth, N.J., 1960; in "Perfume and Flavor Chemicals", S. Arctander, Ed., Vol. I & II, Allured Publishing Corporation, Carol Stream, USA, 1994; in "Flavourings", E. Ziegler and H. Ziegler (ed.), Wiley-VCH Weinheim, 1998 , and "CTFA Cosmetic Ingredient Handbook", J.M. Nikitakis (ed.), 1st ed., The Cosmetic, Toiletry and Fragrance Association, Inc., Washington, 1988.

[0080] The flavor composition may have any suitable form, for example liquid or solid, wet or dried, or in encapsulated form bound to or coated onto carriers / particles or as a powder.

[0081] In the present disclosure, the term “about” used in connection with a value is inclusive of the stated value and has the meaning dictated by the context. For example, it includes at least the degree of error associated with the measurement of the particular value. One of ordinary skill in the art would understand the term “about” is used herein to mean that an amount of “about” of a recited value produces the desired degree of effectiveness in the compositions and / or methods of the present disclosure. One of ordinary skill in the art would further understand that the metes and bounds of “about” with respect to the value of a percentage, amount or quantity of any component in an embodiment can be determined by varying the value, determining the effectiveness of the compositions or methods for each value, and determining the range of values that produce compositions or methods with the desired degree of effectiveness in accordance with the present disclosure.

[0082] The consumable may include a base. As used herein, the term “base” refers to all the ingredients necessary for the consumable, apart from the flavor composition. These will naturally vary in both nature and proportion, depending on the nature and use of the consumable or additive, but they are all well known to the art and may be used in art-recognized proportions. The formulation of such a base for every conceivable purpose is therefore within the ordinary skill of the art. For example, the base for a beverage according to the present disclosure may include about 5% sucrose and about 0.05% citric acid in water.

[0083] Without limitation, and only by way of illustration, suitable bases may include, anticaking agents, anti-foaming agents, anti-oxidants, binders, colourants, diluents, disintegrants, emulsifiers, encapsulating agents or formulations, enzymes, fats, flavor-enhancers, flavoring agents, gums, polysaccharides, preservatives, proteins, solubilisers, solvents, stabilisers, sugarderivatives, surfactants, sweetening agents, vitamins, waxes, and the like. Solvents which may be used are known to those skilled in the art and include e.g., water, ethanol, ethylene glycol, propylene glycol, glycerine and triacetin. Encapsulants and gums include maltodextrin, gum arabic, alginates, gelatine, modified starch, other polysaccharides, and proteins.

[0084] Examples of excipients, carriers, diluents or solvents for flavor compounds may be found e.g. in “Perfume and Flavour Materials of Natural Origin”, S. Arctander, Ed., Elizabeth, N.J., 1960; in “Perfume and Flavour Chemicals”, S. Arctander, Ed., Vol. I & II, Allured Publishing Corporation, Carol Stream, USA, 1994; in “Flavourings”, E. Ziegler and H. Ziegler (ed.), Wiley- VCH Weinheim, 1998, and “CTFA Cosmetic Ingredient Handbook”, J. M. Nikitakis (ed.), 1st ed., The Cosmetic, Toiletry and Fragrance Association, Inc., Washington, 1988.

[0085] Non-limiting examples of suitable flavor-providing ingredients include natural flavors, artificial flavors, spices, seasonings, and the like. These include synthetic flavor oils and flavoring aromatics and / or oils, oleoresins, essences, and distillates, and combinations thereof.

[0086] Ancillary ingredients may be present to provide other benefits such as enhanced stability, ease of incorporation into a consumable or additive and enhanced nutritional value. Non-limiting typical examples of such ancillary ingredients include stabilizers, emulsifiers, preservatives, gums, starches, dextrins, vitamins and minerals, functional ingredients, salts, antioxidants, and polyunsaturated fatty acids. Particular examples are emulsifiers and carriers, useful in spray drying processes. Non-limiting examples of these are modified starches, such as CAPSUL™, and maltodextrin.

[0087] The additive may be a single ingredient or a blend of ingredients, or it may be encapsulated in any suitable encapsulant. The additive may be prepared by any suitable method, such as spray drying, extrusion and fluidized bed drying.

[0088] According to the present disclosure, the term “consumable” refers to products for consumption by a subject, typically via the oral cavity (although consumption may occur via non-oral means such as inhalation), for at least one of the purposes of enjoyment, nourishment, or health and wellness benefits. Consumables may be present in any form including, but not limited to, liquids, solids, semi-solids, tablets, capsules, lozenges, strips, powders, gels, gums, pastes, slurries, solutions, suspensions, syrups, aerosols and sprays. The term also refers to, for example, dietary and nutritional, and health and wellness supplements. Consumables include compositions that are placed within the oral cavity for a period of time before being discarded but not swallowed. It may be placed in the mouth before being consumed, or it may be held in the mouth for a period of time before being discarded.

[0089] Broadly, consumables include, but are not limited to, comestibles of all kinds, confectionery products, baked products, sweet products, savoury products, fermented products, dairy products, non-dairy products, beverages, nutraceuticals and pharmaceuticals.

[0090] Non-limiting examples of consumables include: wet / liquid soups regardless of concentration or container, including frozen soups. For the purpose of this definition, soup(s) means a food prepared from meat, poultry, fish, vegetables, grains, fruit and other ingredients, cooked in a liquid which may include visible pieces of some or all of these ingredients. It may be clear (as a broth) or thick (as a chowder), smooth, pureed or chunky, ready-to-serve, semicondensed or condensed and may be served hot or cold, as a first course or as the main course of a meal or as a between meal snack (sipped like a beverage), soup may be used as an ingredient for preparing other meal components and may range from broths (consomme) to sauces (cream or cheese-based soups); dehydrated and culinary foods, including cooking aid products such as: powders, granules, pastes, concentrated liquid products, including concentrated bouillon, bouillon and bouillon like products in pressed cubes, tablets or powder or granulated form, which are sold separately as a finished product or as an ingredient within a product, sauces and recipe mixes (regardless of technology); meal solutions products such as: dehydrated and freeze dried soups, including dehydrated soup mixes, dehydrated instant soups, dehydrated ready-to-cook soups, dehydrated or ambient preparations of ready-made dishes, meals and single serve entrees including pasta, potato and rice dishes; meal embellishment products such as: condiments, marinades, salad dressings, salad toppings, dips, breading, batter mixes, shelf stable spreads, barbecue sauces, liquid recipe mixes, concentrates, sauces or sauce mixes, including recipe mixes for salad, sold as a finished product or as an ingredient within a product, whether dehydrated, liquid or frozen; beverages, including beverage mixes and concentrates, including but not limited to, alcoholic and non-alcoholic ready to drink and dry powdered beverages, carbonated and noncarbonated beverages, e.g., sodas, fruit or vegetable juices, alcoholic and non-alcoholic beverages, teas such as green tea and black tea, wine such as red wine; confectionery products, e.g., cakes, cookies, pies, candies, chewing gums, gelatins, ice creams, sorbets, puddings, jams, jellies, salad dressings, and other condiments, cereal, and other breakfast foods, canned fruits and fruit sauces and the like. Methods of enhancing the sweetness of a consumable and / or modulating one or more taste attributes of the sweetener to make the consumable taste more like a sucrose-sweetened consumable are provided.

[0091] The disclosure is further described with reference to the following non-limiting examples.

[0092] EXAMPLES

[0093] The following examples are given solely for the purpose of illustration and are not to be construed as limitations of the present invention, as many variations of the invention are possible without departing from the spirit and scope of the present disclosure.

[0094] While particular embodiments of the present invention have been illustrated and described, it would be obvious to those skilled in the art that various other changes and modifications can be made without departing from the spirit and scope of the invention. It is therefore intended to cover in the appended claims all such changes and modifications that are within the scope of this invention.

[0095] Extraction and isolation of pterocaryoside B

[0096] 160 g of the leaves of the plant Cyclocarya paliurus was extracted with 2 L of 85% ethanol / water. The extract was dried down to 200 mL and stored in a refrigerator at 4 °C overnight. Thereafter, the extract was centrifuged and the precipitate was dissolved in 200 mL 100% and mixed with 2 g of activated carbon and stirred for 30 mins. After filtration, 2 g of the extract was purified by preparative HPLC to give the compound pterocaryoside B (54 mg).

[0097] Extraction and isolation of pterocaryoside A

[0098] 250 g of the leaves of the plant Cyclocarya paliurus was extracted with 5 L of 100% MeOH, and dried down to give 40 g of the extract. The 40 g of the extract was suspended in 100 mL 50% MeOH / water and subjected on 500 g HP20 column, and eluted with 2 L 50% MeOH, 2 L 70% MeOH and 2 L 90% MeOH. The 90% methanol fraction was dried down to give 7.4 g of the fraction. The 7.4 g of the HP20 90% fraction was subjected on Sephadex LH20 followed by preparative HPLC to give the compound pterocaryoside A (125 mg). Extraction and isolation of Cyclocarioside K

[0099] 500 g of the leaves of the plant Cyclocarya paliurus was extracted with 4 L of 80% ethanol at room temperature overnight. Thereafter, the extraction solution was dried down with Rotovap to 500 mL, and stored overnight in a refrigerator at 4 °C. Next, the precipitate was filtered and re-dissolved in 500 mL of 200 proof ethanol, and treated with 50 g of activated carbon for 1 hour. After filtration, the solution was dried down to give 12.3 g of the extract. The extract was dissolved in DCM and subjected on flash system with silica gel column, and eluted with DCM / MeOH from 1% to 20% to give the fraction, and the fraction was further applied to preparative HPLC to give the compound Cyclocarioside K (180 mg).

[0100] A Base (5% sucrose and 0.05% citric acid in water) for use in beverages was prepared. The Base did not include triterpenoid compounds (pterocaryoside B, pterocaryoside A or cyclocarioside K). A Control was prepared by combining the Base with a stevia compound. Different combinations of the Control with a triterpenoid compound were prepared in accordance with the Examples (1-3) below and were evaluated by experienced flavorists for sweetness characteristics and sensory perceptions of mouthfeel.

[0101] Example A — Control (Base + 30 ppm Reb A)

[0102] Preparation of Cyclocarya paliurus extract and sensory evaluation.

[0103] Extract I: 10 g of the leaves of the plant Cyclocarya paliurus was extracted with 70% ethanol / water at 80 degree for 1 hour, the extract solution was dried down to give 1.624 g of Extract I. Extract I was analyzed by LC / MS and found to include pterocaryoside B, pterocaryoside A and cyclocarioside K. The extract was evaluated for its sweet enhancement and modifier properties, and the results of the evaluation as compared to the same application in the absence of C. paliurus extract are presented below.

[0104] A Base (5% sucrose and 0.05% citric acid in water) for use in beverages was prepared. The Base did not include C. paliurus extracts. A Control was prepared by combining the Base with a stevia compound. A combination of the Control with C. paliurus extract was prepared in accordance with the Example below and was evaluated by experienced flavorists for sweetness characteristics and sensory perceptions of mouthfeel.

[0105] Example B -- Control (Base + 30 ppm Reb A)

[0106] Preparation of enzymatic treated Cyclocarya paliurus extract and sensory evaluation.

[0107] The leaves of the plant Cyclocarya paliurus were ground into fine powder, 25 g of the powdered leaves was suspended in water, treated with enzyme (cellulose, Tannase, alkaline protease) mediated extraction at 50°C, nylon filtration was applied to keep the solid slurry, followed by 70% EtOH extraction for 1 hour at 60 °C. The extraction solvent was removed by 50 °C Rotor vapor followed by 60°C Vacuum dry to give 1.3 g of the extract. The C. paliurus extract was analyzed by LC / MS and found to include pterocaryoside B, pterocaryoside A and cyclocarioside K.

[0108] The enzymatic treated Cyclocarya paliurus extract was evaluated for its sweet enhancement and modifier properties, and the results of the evaluation as compared to the same application in the absence of C. paliurus extract are presented below.

[0109] A Base (5% sucrose and 0.05% citric acid in water) for use in beverages was prepared. The Base did not include the C. paliurus extract. A Control was prepared by combining the Base with a stevia compound. A combination of the Control with an enzyme treated C. paliurus extract was prepared in accordance with the Example below and was evaluated by experienced flavorists for sweetness characteristics and sensory perceptions of mouthfeel.

[0110] Example C - Control (Base + 30 ppm Reb A)

[0111] The compositions of the above Examples were taste tested by experienced flavorists and the combinations were compared to the Base. As is evident, the combinations of triterpenoid compounds and / or extracts with sweetness modifier(s) were found to have a sweeter and / or more sugar-like mouthfeel and / or less lingering sweetness and / or less licorice-like taste, as compared to the Controls which did not contain a triterpenoid compound.

[0112] Example D

[0113] Two Bases were prepared for use in beverages. These Bases were combined with various combinations of sweetness modifiers (Table 1) and were evaluated by experienced flavorists for sweetness characteristics and sensory perceptions of mouthfeel. Each attribute was described by rating the instensity on a scale of 1-10, with 1 being low intensity and 10 being high intensity.

[0114] Base 1 - (5% sucrose, 0.05% citric acid in water)

[0115] Base 1+- (5% sucrose, 0.05% citric acid, 5 ppm pterocaryoside B in water)

[0116] Table 1 (Sweetness Modifiers)

[0117] 13-[(4-amino-2, 2-dioxido-lH-2, 1, 3 -benzothiadiazin-5 -yl)oxy] -2, 2-dimethyl-N- propylpropanamide The following compositions (Base 1 / Base 1+), plus sweetness modifiers from Table 1

[0118] (Ingredients 1-8) were taste tested by experienced flavorists and were compared to the Base 1 control without pterocaryoside B.

[0119] Table 2

[0120] Overall, as evident from the above results, the combination of a triterpenoid compound with a sweetness modifier was found to be sweeter, more sugar-like mouthfeel and more body mouthfeel.

[0121] The dimensions and values disclosed herein are not to be understood as being strictly limited to the exact numerical values recited. Instead, unless otherwise specified, each such dimension is intended to mean both the recited value and a functionally equivalent range surrounding that value. For example, a dimension disclosed as “40 mm” is intended to mean “about 40 mm”.

[0122] While particular embodiments of the present invention have been illustrated and described, it would be obvious to those skilled in the art that various other changes and modifications can be made without departing from the spirit and scope of the invention. It is therefore intended to cover in the appended claims all such changes and modifications that are within the scope of this invention.

Claims

What is claimed is:

1. A flavor composition comprising: a. at least one triterpenoid compound selected from the group consisting of pterocaryoside B, pterocaryoside A, cyclocarioside K and combinations thereof; and b. at least one sweetness modifier selected from the group consisting of steviol glycosides, mogrosides, dihydrochalcones, sweet proteins, and combinations thereof.

2. The flavor composition of claim 1, wherein the steviol glycosides are selected from the group consisting of 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 Zl, rebaudioside Z2, rebaudioside IX, enzymatically glucosylated steviol glycosides, and combinations thereof.

3. The flavor composition of claim 1, wherein the mogrosides are selected from the group consisting of grosvenorine II, grosvenorine I, 11-O-mogroside II (I), 11-O-mogroside II (II), 11-O-mogroside II (III), mogroside II (I), mogroside II (II), mogroside II (III), 11- dehydroxy-mogroside III, 11-O-mogroside III, mogroside III (I), mogroside III (II), mogroside Ille, mogroside IIIx, mogroside IV (I) (siamenoside), mogroside IV (II), mogroside IV (III), mogroside IV (IV), deoxymogroside V (I), deoxymogroside V (II), 11-O-mogroside V (I), mogroside V isomer, mogroside V, iso-mogroside V, iso- mogroside VI, 7-O-mogroside V, 11-O-mogroside VI, 11-epi-mogroside, mogroside VI (I), mogroside VI (II), mogroside VI (III) (neomogroside), mogroside VI (IV), and combinations thereof.

4. The flavor composition of claim 1, wherein the dihydrochalcones are selected from the group consisting of trilobatin, phloretin, naringin dihydrochalcone, neohesperidin dihydrochalcone, hesperetin dihydrochalcone, hesperetin dihydrochalcone 4”-beta-D- glucoside, and combinations thereof.

5. The flavor composition of claim 1, wherein the at least one triterpenoid compound is present in the flavor composition in a concentration of from 100 ppm to 70,000 ppm.

6. A consumable comprising: a. at least one sweetener; and b. a flavor composition including at least one triterpenoid compound selected from the group consisting of pterocaryoside B, pterocaryoside A, cyclocarioside K and combinations thereof; and at least one sweetness modifier selected from the group consisting of steviol glycosides, mogrosides, dihydrochalcones, sweet proteins and combinations thereof; wherein the at least one sweetener is present in a sweetening amount.

7. The consumable of claim 6, wherein the at least one sweetener is selected from the group consisting of sucrose, fructose, glucose, xylose, arabinose, rhamnose, tagatose, allulose, trehalose, isomaltulose, steviol glycosides, mogrosides, stevia, trilobatin, rubusoside, aspartame, advantame, agave syrup, acesulfame potassium (AceK), high fructose corn syrup, neotame, saccharin, sucralose, high fructose com syrup, starch syrup, Luo Han Guo extract, neohespiridin dihydrochalcone, naringin dihydrochalcone, HDG, sugar alcohols, cellobiose, psicose, cyclamate, tamatin, molasses, rice syrup, and combinations thereof.

8. The consumable of claim 7, wherein the at least one sweetness modifier is present in a concentration of from 1 ppm to 200 ppm.

9. The consumable of claim 6, wherein the consumable is a beverage.

10. The consumable of claim 6, wherein the least one triterpenoid compound is present in the consumable in a concentration of from 0.05 ppm to 70 ppm.

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