Compositions and methods for taste modulation

Abstract

Provided herein are compositions comprising a flavor providing substance and at least one nor-diterpene of Formula (I), (I) wherein R1, R2, and R3 are each independently selected from hydrogen, hydroxyl, or oxo; wherein R4 is selected from methyl, hydroxymethyl, aldehyde, carboxylic acid, or an ester having C 1‑6 alkyl; wherein R5 is selected from hydrogen, C 1‑6 alkyl, a furanose moiety, a pyranose moiety, or an oligosaccharide moiety having two to six saccharide moieties; and wherein R6 is selected from hydrogen, hydroxyl, or C 1‑6 alkyl.

Description

Technical Field

[0001] This disclosure relates to compositions containing norditerpenoids. This disclosure further extends to consumer products containing sweeteners and at least one norditerpenoid to improve the sweetness, improve the mouthfeel, and / or mask off-flavors of the consumer product.

[0002] background

[0003] Compounds used to improve the taste of consumer products (i.e., products taken orally or vomited, such as food, beverages, sugars, oral care products, etc.) are widely used. They do not add flavor to consumer products on their own, but they provide desired auxiliary benefits, such as enhanced mouthfeel and / or sweetness or masking undesirable characteristics of other ingredients, such as unique tastes and textures that are not considered attractive to products containing sugar substitutes.

[0004] In the case of sugar substitutes, the flavors they impart can exhibit different temporal characteristics, flavor characteristics, or adaptive behaviors compared to the sugars they wholly or partially replace. For example, the sweetness of natural and synthetic high-intensity sweeteners (HIS) typically takes effect more slowly and lasts longer than the sweetness produced by sugars (sweet, short-chain, soluble carbohydrates, including glucose, fructose, sucrose, maltose, and lactose) or high-fructose corn syrup (HFCS) (which are known as sugar substitutes), and this can alter the flavor balance of edible compositions containing them. This can create unbalanced temporal flavor characteristics. In addition to differences in temporal characteristics, high-intensity sweeteners typically exhibit a lower maximum response than sugars; off-flavors, including bitterness, metallic taste, coolness, astringency, licorice-like taste, and / or a diminishing sweetness upon repeated tasting.

[0005] However, all high-sweetness sweeteners have an undesirable aftertaste in the form of off-flavors, such as a licorice-like aftertaste and / or a persistent sweetness. In the specific case of Reb A (“Reb A”), this manifests as a combination of an undesirable persistent sweetness and a licorice-like aftertaste. This aftertaste diminishes the desired sugary sweetness and thus effectively masks undesirable flavors or off-flavors in edible compositions, which is key to consumer acceptance of many edible compositions.

[0006] Therefore, there is still a need to provide natural and / or vegan (i.e., "cleaner label") flavor modifiers, extracts, or fractions that improve the taste of consumer products, mask off-flavors, and / or improve the sweetness of consumer products.

[0007] Overview

[0008] In one illustrative embodiment, the composition comprises a flavor-providing substance and at least one diterpene of formula I:

[0009] I

[0010] R1, R2, and R3 are each independently selected from hydrogen, hydroxyl, or oxo;

[0011] R4 is selected from methyl, hydroxymethyl, aldehyde, carboxylic acid, or substances containing C. 1-6 Alkyl esters; wherein R5 is selected from hydrogen, C 1-6 An alkyl, furanose, pyranose, or oligosaccharide moiety having two to six sugar moieties; wherein R6 is selected from hydrogen, hydroxyl, or C. 1-6 alkyl.

[0012] In another illustrative embodiment, the consumer product comprises (a) at least one sweetener, and (b) a sweetness improver comprising at least one diterpene of formula I:

[0013] I

[0014] R1, R2, and R3 are each independently selected from hydrogen, hydroxyl, or oxo;

[0015] R4 is selected from methyl, hydroxymethyl, aldehyde, carboxylic acid, or substances containing C. 1-6 Alkyl esters; wherein R5 is selected from hydrogen, C 1-6 An alkyl, furanose, pyranose, or oligosaccharide moiety having two to six sugar moieties; wherein R6 is selected from hydrogen, hydroxyl, or C. 1-6 Alkyl group; and wherein the at least one sweetener is present in a sweetening amount.

[0016] These and other features, aspects, and advantages of the specific embodiments will become apparent to those skilled in the art upon reading this disclosure.

[0017] Detailed Explanation

[0018] The following provides a broad description of many different embodiments of this disclosure. The description should be interpreted as exemplary only and does not describe every possible embodiment, as it would be impractical to describe every possible embodiment, if not impossible. It should be understood that any feature, characteristic, component, composition, ingredient, product, step, or method described herein can be removed, combined, or substituted, in whole or in part, with any other feature, characteristic, component, composition, ingredient, product, step, or method described herein. Many alternative embodiments can be implemented using current technology or technology developed after the filing date of this patent, which will still fall within the scope of the claims. All publications and patents cited herein are incorporated herein by reference.

[0019] This disclosure relates to the unexpected discovery that certain norditerpenes and extracts or fractions containing these compounds exhibit sweetness-modifying and mouth-improving properties without introducing unpleasant off-flavors. Specifically, this disclosure relates to the unexpected discovery that certain norditerpenes and extracts or fractions containing these compounds can be used to enhance the sweetness of certain sweeteners, particularly low-sugar or calorie-free sweeteners in consumer products such as beverages, and / or modify their flavor. In one embodiment, the norditerpenes of the formula disclosed herein enhance sweetness. In another embodiment, the norditerpenes of the formula disclosed herein are flavor modifiers / improvers, enhancing sweetness simultaneously or not simultaneously.

[0020] According to this disclosure, certain diterpenes of the formula disclosed herein can be obtained from Forsythia suspensa (… Jasmine burned Separated from the root bark of ) . Forsythia ( Jasmine burned *Diels* (family Oleaceae) is a native plant distributed in Shaanxi Province, China. Its dried root bark, known in Chinese as "quanpi," is used as a traditional Chinese medicine to treat various ailments such as fever, rheumatic pain, and irregular menstruation. Some of the diterpenes disclosed herein may be derived from extracts, or may be synthetic compounds, or a combination of extracts and synthetic compounds.

[0021] In one embodiment, the root bark of *Forsythia suspensa* is dried prior to extraction. In some embodiments, the root bark is optionally ground prior to extraction.

[0022] The root bark of Forsythia suspensa can be extracted using any suitable extraction process, such as, for example, continuous or batch reflux extraction, supercritical fluid extraction, enzyme-assisted extraction, microbial-assisted extraction, ultrasound-assisted extraction, microwave-assisted extraction, etc. These methods can be deployed on any scale.

[0023] The solvent used for extraction can be any suitable solvent, such as, for example, polar organic solvents (degassed, vacuumed, pressurized, or distilled), nonpolar organic solvents, water (degassed, vacuumed, pressurized, deionized, distilled, carbonized, or reverse osmosis), or mixtures thereof. In a specific embodiment, the solvent includes water and one or more alcohols. In a specific embodiment, the solvent includes water and an alcohol selected from methanol, ethanol, n-propanol, 2-propanol, 1-butanol, 2-butanol, and mixtures thereof.

[0024] 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 therebetween). In a specific embodiment, alcohol constitutes about 80% to about 100% of the solvent, with the remainder being water.

[0025] In some embodiments, the extraction process occurs at elevated temperatures (e.g., from about 50°C to about 100°C). In more specific embodiments, the extraction process occurs at a temperature of about 100°C.

[0026] Those skilled in the art will understand that the duration of extraction will vary based on the solvent used and the amount of plant material. In some embodiments, extraction takes place from about 10 minutes to about 24 hours. Water and / or any insoluble material may be removed from the extraction mixture to provide a “crude extract”.

[0027] Insoluble plant material can be separated from the extracted mixture by means of, for example, filtration. Other suitable separation methods include, but are not limited to, gravity filtration, plate and frame filter presses, cross-flow filters, sieve filters, Nutsche filters, belt filters, ceramic filters, membrane filters, microfilters, nanofilters, ultrafiltration, or centrifugation. Optionally, various filter aids, such as diatomaceous earth, bentonite, zeolite, etc., can be used in this process.

[0028] The crude extract is then subjected to one or more chromatographic separations to provide a solution of one or more diterpenoid compounds described herein. The crude extract is passed through one or more columns, such as those packed with polymer adsorption resin. The one or more columns are eluted with an aqueous methanol solution to provide a solution containing fractions of the plant extract. In one embodiment, 10% ethanol is first applied to the column and the eluent is collected. Fractions may be collected based on the percentage of methanol used for elution, for example, 0% methanol, 30% methanol, 50% methanol, 70% methanol, and 100% methanol. Typically, the product of the chromatographic step is collected in multiple fractions, which can then be analyzed using any suitable technique, such as thin-layer chromatography or mass spectrometry.

[0029] In one embodiment, the diterpenoid compound of formula I can be used to enhance and / or alter / improve the sweetness of consumer products containing sweeteners:

[0030] I

[0031] R1, R2, and R3 are each independently selected from hydrogen, hydroxyl, or oxo; R4 is selected from methyl, hydroxymethyl, aldehyde, carboxylic acid, or having a C-type derivative. 1-6 Alkyl esters; wherein R5 is selected from hydrogen, C 1-6 An alkyl, furanose, pyranose, or oligosaccharide moiety having two to six sugar moieties; wherein R6 is selected from hydrogen, hydroxyl, or C. 1-6 alkyl.

[0032] As used herein, “sugar” refers to monosaccharides, disaccharides, oligosaccharides, and polysaccharides. Sugars include at least one carbohydrate. Exemplary carbohydrates include, but are not limited to, sucrose, glyceraldehyde, dihydroxyacetone, erythrose, threose, erythulose, arabinose, lysolose, ribose, xylose, ribulose, xylulose, allose, arabinose, galactose, glucose, gulose, idole, mannose, tarose, fructose, allulose, sorbose, tagatose, mannoheptulose, sedoheltulose, octolose, fucose, rhamnose, arabinose, menobiose, and sialose.

[0033] In one embodiment, the diterpenoid compound of formula I according to this disclosure is a sweetness improver. As used herein, the term "sweetness improver" refers to a compound that improves, enhances, amplifies, or strengthens the perceived sweetness of a consumer product when the compound is present in the product at a concentration equal to or below the sweetness recognition threshold of the compound (i.e., a concentration at which the compound does not contribute any noticeable sweetness in the absence of one or more other sweeteners).

[0034] As used herein, the term "sweetness recognition threshold concentration" is the lowest known concentration of a compound that is perceptible to human taste as sweet. Sweetness recognition threshold concentrations are specific to particular compounds and can vary based on temperature, matrix, composition, and / or flavor system.

[0035] In another embodiment, the novel diterpenoid compound of Formula I according to this disclosure is a flavor modifier, acting simultaneously or separately as a sweetness improver. That is, in some embodiments, the diterpenoid compound of Formula I improves sweetness and modulates one or more flavor properties of the sweetener. In other embodiments, the diterpenoid compound of Formula I improves the sweetness of the sweetener without modulating one or more flavor properties of the sweetener. In other embodiments, the diterpenoid compound of Formula I modulates one or more flavor properties of the sweetener without improving the sweetness of the sweetener.

[0036] In another specific embodiment, the diterpene compound is a compound of formula I(a):

[0037] I(a)

[0038] In yet another specific embodiment, the diterpene compound is a compound of formula I(b):

[0039] I(b)

[0040] In yet another specific embodiment, the diterpene compound is a compound of formula I(c):

[0041] I(c)

[0042] In another embodiment, the novel norditerpenoid compound of Formula II according to this disclosure is a flavor modifier, acting simultaneously or separately as a sweetness improver. That is, in some embodiments, the norditerpenoid compound of Formula II improves sweetness and modulates one or more flavor properties of the sweetener. In other embodiments, the norditerpenoid compound of Formula II improves the sweetness of the sweetener without modifying one or more flavor properties of the sweetener. In other embodiments, the norditerpenoid compound of Formula II modulates one or more flavor properties of the sweetener without improving the sweetness of the sweetener.

[0043] In one embodiment, the diterpenoid compound of formula II can be used to enhance and / or improve / modify the sweetness of consumer products containing sweeteners:

[0044] II

[0045] R1, R2, and R3 are each independently selected from hydrogen, hydroxyl, or oxo; R4 is selected from methyl, hydroxymethyl, aldehyde, carboxylic acid, or having a C-type derivative. 1-6 Alkyl esters; wherein R5 is selected from hydrogen, C 1-6 An alkyl, furanose, pyranose, or oligosaccharide moiety having two to six sugar moieties; wherein R6 is selected from hydrogen, hydroxyl, or C. 1-6 alkyl.

[0046] In another embodiment, the novel norditerpenoid compound of Formula III according to this disclosure is a flavor modifier, acting simultaneously or separately as a sweetness improver. That is, in some embodiments, the norditerpenoid compound of Formula III improves sweetness and modulates one or more flavor properties of the sweetener. In other embodiments, the norditerpenoid compound of Formula III improves the sweetness of the sweetener without modifying one or more flavor properties of the sweetener. In other embodiments, the norditerpenoid compound of Formula III modulates one or more flavor properties of the sweetener without improving the sweetness of the sweetener.

[0047] In one embodiment, the diterpenoid compound of formula III can be used to enhance and / or improve / modify the sweetness of consumer products containing sweeteners:

[0048] III

[0049] R1, R2, R3, R9, R10, and R11 are independently selected from hydrogen, hydroxyl, or oxo groups; R4 is selected from methyl, hydroxymethyl, aldehyde, carboxylic acid, or having a C group. 1-6 Alkyl esters; R5 is independently selected from hydrogen, C 1-6 Alkyl, furanose, pyranose, or oligosaccharide moieties having two to six sugar moieties; R6, R7, and R8 are selected from hydrogen, hydroxyl, or C.1-6 alkyl.

[0050] In another embodiment, the novel norditerpenoid compound of formula IV according to this disclosure is a flavor modifier, acting simultaneously or separately as a sweetness improver. That is, in some embodiments, the norditerpenoid compound of formula IV improves sweetness and modulates one or more flavor properties of the sweetener. In other embodiments, the norditerpenoid compound of formula IV improves the sweetness of the sweetener without modifying one or more flavor properties of the sweetener. In other embodiments, the norditerpenoid compound of formula IV modulates one or more flavor properties of the sweetener without improving the sweetness of the sweetener.

[0051] In one embodiment, the diterpenoid compound of formula IV can be used to enhance and / or improve / modify the sweetness of consumer products containing sweeteners:

[0052] IV

[0053] R1, R2, R3, R9, R10, and R11 are independently selected from hydrogen, hydroxyl, or oxo groups; R4 is selected from methyl, hydroxymethyl, aldehyde, carboxylic acid, or groups having a C group. 1-6 Alkyl esters; R5 is independently selected from hydrogen, C 1-6 Alkyl, furanose, pyranose, or oligosaccharide moieties having two to six sugar moieties; R6, R7, and R8 are selected from hydrogen, hydroxyl, or C. 1-6 alkyl.

[0054] In another embodiment, the flavoring composition according to this disclosure may further comprise additional sweetness modifiers. According to certain illustrative embodiments, the additional sweetness modifiers are selected from steviol glycosides, mogrosides, dihydrochalcone, and combinations thereof. According to certain embodiments, the amount of these sweetness modifiers present in the flavoring composition may be a concentration of about 1,000 ppm to about 200,000 ppm, in another embodiment a concentration of 2,000 ppm to about 100,000 ppm, and in yet another embodiment a concentration of about 5,000 ppm to about 50,000 ppm.

[0055] In one embodiment, the flavoring composition according to this disclosure may further comprise a flavor-providing substance. For the purposes of "flavor-providing substance," it means a composition created by a flavorist using methods known to those skilled in the art, which is a mixture of flavor enhancers, aromatic compounds, and sensates. Examples of suitable flavoring agents include natural flavoring agents, artificial flavoring agents, spices, seasonings, etc. Exemplary flavor-providing substances include synthetic flavoring oils and flavoring aromatics and / or oils, oleoresins, fragrances, and distillates, as well as combinations comprising at least one of the foregoing.

[0056] Spice oils include spearmint oil, cinnamon oil, wintergreen oil (methyl salicylate), peppermint oil, Japanese peppermint oil, clove oil, laurel oil, fennel oil, eucalyptus oil, thyme oil, cypress leaf oil, nutmeg oil, allspice oil, sage oil, mace oil, bitter almond oil, and cinnamon oil; available flavorings include artificial, natural, and synthetic fruit flavorings such as vanilla, and citrus oils including lemon, orange, lime, grapefruit, pomelo, and saffron, and fruit flavorings including apple, pear, peach, grape, raspberry, blackberry, currant, blueberry, strawberry, cherry, plum, prune, raisin, kola nut, guarana, orange blossom, pineapple, apricot, banana, melon, cherry, tropical fruits, mango, mangosteen, pomegranate, papaya, and so on.

[0057] Other exemplary flavors imparted by flavor-providing substances include milk flavor, butter flavor, cheese flavor, cream flavor and yogurt flavor, vanilla flavor, tea or coffee flavor (such as green tea flavor, oolong tea flavor, tea flavor, cocoa flavor, chocolate flavor and coffee flavor); mint flavor, such as peppermint flavor, spearmint flavor and Japanese mint flavor; spicy flavor, such as asafoetida flavor, ajowan flavor, fennel flavor, angelica flavor, cumin flavor, allspice flavor, cinnamon flavor, chamomile flavor, mustard flavor, cardamom flavor, caraway flavor, cumin flavor, clove flavor, pepper flavor, coriander flavor, sassafras flavor, mint flavor, and Zanthoxylum bungeanum flavor. Fructus flavor, perilla flavor, juniper flavor, ginger flavor, star anise flavor, horseradish flavor, thyme flavor, tarragon flavor, dill flavor, chili flavor, nutmeg flavor, basil flavor, marjoram flavor, rosemary flavor, bay leaf flavor, and horseradish (Japanese horseradish) flavor; nut flavor, such as almond flavor, hazelnut flavor, macadamia nut flavor, peanut flavor, pecan flavor, pistachio fruit flavor, and walnut flavor; floral flavor; and vegetable flavor, such as onion flavor, garlic flavor, cabbage flavor, carrot flavor, celery flavor, mushroom flavor, and tomato flavor.

[0058] According to some implementation schemes, flavor-providing substances may also include aldehydes and esters, such as cinnamyl acetate, cinnamaldehyde, citral diethyl acetal, dihydrocarboxyl acetate, eugenol formate 49, p-methylamisol, etc. Other examples of aldehyde flavoring agents include acetaldehyde (apple), benzaldehyde (cherry, almond), anisaldehyde (licorice, fennel), cinnamaldehyde (cinnamon), citral (i.e., α-citral) (lemon, lime), neraldehyde (i.e., β-citral) (lemon, lime), decanal (orange, lemon), ethyl vanillin (vanilla, cream), heliotrope (i.e., piperaldehyde) (vanilla, cream), vanillin (vanilla, cream), α-pentylcinnamaldehyde (spicy fruit flavor), butyraldehyde (butter, cheese), and pentanal (butter, dry...). Citronellol (modified forms, many types), decanal (citrus fruits), aldehyde C-8 (citrus fruits), aldehyde C-9 (citrus fruits), aldehyde C-12 (citrus fruits), 2-ethylbutanal (berry fruits), hexenal (i.e., trans-2) (berry fruits), tolualdehyde (cherries, almonds), veratral (vanilla), 2,6-dimethyl-5-heptenal (i.e., melon aldehyde) (melon), 2,6-dimethyloctanal (green fruits), and 2-dodecenal (citrus fruits, oranges), etc.

[0059] Generally, any flavor-providing substance or food additive, such as those described by the National Academy of Sciences in "Chemicals Used in Food Processing," Publication No. 1274, pp. 63-258, is acceptable. That publication is incorporated herein by reference.

[0060] In some embodiments, the at least one flavor-providing substance is present in an amount of about 1 wt.% to about 95 wt.% based on the total weight of the flavor composition. In some embodiments, the at least one flavor-providing substance is present in an amount of about 1 wt.% to about 70 wt.% based on the total weight of the flavor composition. In some embodiments, the at least one flavor-providing substance is present in an amount of about 5 wt.% to about 60 wt.% based on the total weight of the flavor composition. In some embodiments, the at least one flavor-providing substance is present in an amount of about 10 wt.% to about 50 wt.% based on the total weight of the flavor composition.

[0061] Flavor compositions may also contain one or more adjuvants. Adjuvants are components that do not affect the flavor or other sensory properties of the flavor composition, but may otherwise affect its quality. Adjuvants may include colorants, which can add a desired color or compensate for color loss during processing; pH buffers; preservatives; antioxidants, etc. Unrestrictedly, adjuvants may also include solvents, emulsifiers, disintegrants, and lubricants. Other examples of adjuvants used in fragrance compositions can be found, for example, in "Perfume and Flavour Materials of Natural Origin", edited by S. Arctander, Elizabeth, NJ, 1960; "Perfume and Flavour Chemicals", edited by S. Arctander, Volumes I & II, Allured Publishing Corporation, Carol Stream, USA, 1994; "Flavourings", edited by E. Ziegler and H. Ziegler, Wiley-VCH Weinheim, 1998; and "CTFA Cosmetic Ingredient Handbook", edited by JM Nikitakis, 1st edition, The Cosmetic, Toiletry and Fragrance Association, Inc., Washington, 1988.

[0062] The diterpenoids described herein may be provided in pure form or as part of a mixture. The mixture may be an extract or fraction prepared from a plant or a part of a plant, as described herein.

[0063] The diterpenoid compounds described herein modify and / or modulate the flavor of at least one sweetener. This at least one sweetener can be any known sweetener, such as a natural sweetener, a natural high-efficiency sweetener, or a synthetic sweetener.

[0064] The at least one sweetener is present in a sweetening amount. As used herein, "sweetening amount" refers to the amount of compound required to provide detectable sweetness when present in a consumer product (e.g., a beverage).

[0065] As used herein, the phrase "natural high-potency sweetener" refers to any sweetener that is naturally occurring in nature and is characterized by having a sweetening potency greater than that of sucrose, fructose, or glucose, but with fewer calories. Natural high-potency sweeteners may be provided as pure compounds or alternatively as part of an extract. As used herein, the phrase "synthetic sweetener" refers to any composition that is not naturally occurring in nature and is characterized by having a sweetening potency greater than that of sucrose, fructose, or glucose, but with fewer calories.

[0066] In other embodiments, the at least one sweetener is a carbohydrate sweetener. Suitable carbohydrate sweeteners are selected from, but are not limited to, sucrose, glyceraldehyde, dihydroxyacetone, erythrose, threose, erythritol, arabinose, lysolose, ribose, xylose, ribulose, xylulose, allose, azoose, galactose, glucose, gulose, idole, mannose, tarose, fructose, allulose, sorbitol, tagatose, mannoheptulose, sedoheptulose, octanulose, fucose, rhamnose, menobiose, cellobiose, sialic acid, and combinations thereof. In other embodiments, the at least one sweetener does not include carbohydrate sweeteners.

[0067] In another embodiment, the additional sweetener is a rare sugar selected from sorbitol, lysoose, ribulose, xylose, xylulose, D-allose, L-ribose, D-tagatose, L-glucose, L-fucose, L-arabinose, menobiose, and combinations thereof. Other sweeteners include sarcomatin I, monatin and its salts (monatin SS, RR, RS, SR), curculigoside, glycyrrhizic acid and its salts, thaumatin, monalin, mabinlin, brazzein, tamatin, hemandulcin, folate, glycyphyllin, baiyunoside, osladin, polypodoside A, pterocaryoside A, pterocaryoside B, mukurozioside, phlomisoside I, and periandrin I. I), abrusoside A, stevioside and eucommia glycoside I, sugar alcohols such as erythritol, sucralose, acesulfame potassium, acesulfame acid and its salts, aspartame, alitame, saccharin and its salts, hesperidin dihydrochalcone glucoside, neohesperidin dihydrochalcone, cyclohexylsulfamic acid, cyclohexylsulfamic acid and its salts, neotame, adventitia, glucosylstevioside (GSGs) and combinations thereof.

[0068] In one embodiment, the sweetener is a caloric sweetener or a mixture of caloric sweeteners. In another embodiment, the caloric sweetener is selected from sucrose, fructose, glucose, high-fructose corn (com) / starch syrup, beet sugar, sucrose, and combinations thereof.

[0069] In other embodiments, the sweetener comprises at least one steviol glycoside, wherein the at least one steviol glycoside is present in a sweetening amount. The steviol glycoside may be natural, synthetic, or a combination of natural and synthetic. The steviol glycoside may be provided in pure form or as part of a mixture (i.e., a steviol glycoside blend). Exemplary steviol glycosides include, but are not limited to, riboboroside M, riboboroside D, riboboroside A, riboboroside N, riboboroside O, riboboroside E, steviol monosaccharide glycoside, steviol disaccharide glycoside, stevioside, durcuroside B, durcuroside A, riboboroside B, riboboroside G, steviol glycoside, riboboroside C, riboboroside F, riboboroside I, riboboroside H, riboboroside L, riboboroside K, riboboroside J, riboboroside M2, riboboroside D2, riboboroside S, riboboroside T, riboboroside U, riboboroside V, riboboroside W, riboboroside Z1, riboboroside Z2, riboboroside IX, enzymatically glucosylated steviol glycosides, and combinations thereof.

[0070] Steviol glycoside blend sweeteners typically have a total steviol glycoside content of about 95% by weight or more on a dry basis. The remaining 5% comprises other non-steviol glycoside compounds, such as byproducts from extraction or purification processes. In some embodiments, the steviol glycoside blend sweetener has a total steviol glycoside content of about 96% or more, about 97% or more, about 98% or more, or about 99% or more. As used herein, "total steviol glycoside content" refers to the sum of the relative weight contributions of each steviol glycoside in the sample.

[0071] In one embodiment, the sweetener comprises at least one mogroside, wherein the at least one mogroside is present in a sweetening amount. Mogroside can be natural, synthetic, or a combination of natural and synthetic. Mogroside can be provided in pure form or as part of a mixture (i.e., a mogroside blend). Exemplary mogrosides include, but are not limited to, any one of the following: grosmogroside I, mogroside IA, mogroside IE, 11-oxomogroside IA, mogroside II, mogroside IIA, mogroside IIB, mogroside IIE, 7-oxomogroside IIE, mogroside III, mogroside HIE, 11-oxomogroside HIE, 11-deoxymogroside III, mogroside IV, mogroside IVA, 11-oxomogroside IV, 11-oxomogroside IVA, mogroside V, isomogroside V, 11-deoxymogroside V, 7-oxomogroside V, 11-oxomogroside V, isomogroside V, mogroside VI, mogroside alcohol, 11-oxomogroside alcohol, symbioside I, and combinations thereof.

[0072] In one embodiment, the weight ratio of the at least one sweetener to the diterpenoid compound described herein can vary.

[0073] product

[0074] According to this disclosure, diterpenoid compounds can be added to sweetened consumer products (i.e., consumer products having at least one sweetener) or can be provided as part of a flavoring composition for use in consumer products.

[0075] In one embodiment, the diterpenoid compound described herein is present in the flavoring composition in an amount such that when the flavoring composition is added to a sweetened consumer product, the sucrose equivalent of the consumer product is increased compared to the consumer product in the absence of the diterpenoid compound.

[0076] When added to consumer products, the norditerpenoid compound is used in an amount that effectively improves the sweetness or mouthfeel of the sweetener without exhibiting any off-flavor. According to some embodiments, the amount of the norditerpenoid compound present in the consumer product can be from a concentration of about 0.01 ppm to about 100 ppm, and in another embodiment from 0.01 ppm to about 50 ppm, such as, for example, from about 0.01 ppm to about 45 ppm, from about 0.01 ppm to about 40 ppm, from about 0.01 ppm to about 35 ppm, from about 0.01 ppm to about 30 ppm, from about 0.01 ppm to about 25 ppm, from about 0.01 ppm to about 20 ppm, from about 0.01 ppm to about 15 ppm, from about 0.01 ppm to about 10 ppm, and from about 0.01 ppm to about 5 ppm.

[0077] In one embodiment, the at least one sweetener described herein is present in concentrations of about 50 ppm to about 600 ppm, such as, for example, about 50 ppm to about 500 ppm, about 50 ppm to about 400 ppm, about 50 ppm to about 300 ppm, about 50 ppm to about 200 ppm, 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... The sweetener is present in the consumer product at concentrations of about 600 ppm, about 400 ppm to about 500 ppm, and about 500 ppm to about 600 ppm. In another embodiment, for full-sugar and low-sugar applications, the at least one sweetener may be present in the consumer product at a concentration of up to 100,000 ppm.

[0078] When expressed as "ppm", the concentration is a fraction of a million based on the total weight of the consumer product. It should be understood that when ranges of values ​​are described in this disclosure, it is intended that any and every value (including endpoints) within that range be considered as disclosed. For example, a "range of 0.01 ppm to 100 ppm" for the at least one diterpene will be interpreted as indicating every possible number along the continuous interval from 0.01 to 100. It should be understood that the inventors recognize and understand that any and all values ​​within this range are considered as specified, and that the inventors possess the entire range and all values ​​within that range.

[0079] In this disclosure, the term “about” used in conjunction with a value includes the value and has a meaning defined by the context. For example, it includes at least the degree of error associated with the measurement of a particular value. Those skilled in the art will understand that the term “about” used herein to refer to an amount of the value that produces the desired degree of effectiveness in the compositions and / or methods of this disclosure. Those skilled in the art will further understand that the boundaries and limits of the “about” value relating to the percentage, amount, or quantity of any component in the embodiments can be determined by changing the value, determining the effectiveness of the composition or method for each value, and determining the range of values ​​that produce compositions or methods with the desired degree of effectiveness according to this disclosure.

[0080] Consumer products may contain base materials. As used herein, the term "base material" refers to all ingredients necessary for a consumer product, except for diterpenoid compounds. These will naturally vary in both nature and proportion depending on the nature and use of the consumer product or additive, but they are all well known in the art and can be used in proportions generally accepted in the art. Therefore, such base materials are formulated within the ordinary techniques of the art for every conceivable purpose.

[0081] Unrestrictedly, and by way of illustration only, suitable base materials may include anti-caking agents, defoamers, antioxidants, binders, colorants, diluents, disintegrants, emulsifiers, encapsulating agents or formulations, enzymes, fats, flavor enhancers, seasonings, gums, polysaccharides, preservatives, proteins, solubilizers, solvents, stabilizers, sugar derivatives, surfactants, sweeteners, vitamins, waxes, etc. Solvents that may be used are known to those skilled in the art and include, for example, water, ethanol, ethylene glycol, propylene glycol, glycerol, and triacetin. Encapsulating agents and gums include maltodextrin, gum arabic, alginate, gelatin, modified starch, other polysaccharides, and proteins.

[0082] According to this disclosure, the term "consumer product" means a product intended for consumption by a subject for at least one purpose of enjoyment, nutrition, or health and wellness benefits, typically via the oral cavity (although consumption can also be made via non-oral means such as inhalation). Consumer products can be 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, diets and nutrition, as well as health and wellness supplements. Consumer products include compositions that remain in the mouth for a period of time before being discarded but are not swallowed. They may be placed in the mouth before consumption, or may remain in the mouth for a period of time before being discarded.

[0083] Broadly speaking, consumer goods include, but are not limited to, all types of food, confectionery, baked goods, sweetened products, flavored products, fermented products, dairy products, non-dairy products, beverages, nutritional supplements, and pharmaceuticals.

[0084] Non-limiting examples of consumer products include: wet / liquid soups, regardless of concentration or container, including frozen soups. For the purposes of this definition, one or more soups mean a food prepared from meat, poultry, fish, vegetables, grains, fruits, and other ingredients, cooked in a liquid, which may include some or all of the visible fragments of these ingredients. It can be clear (e.g., broth) or thick (e.g., stew), smooth, pureed or chunky, ready-to-eat, semi-concentrated or concentrated, and can be hot or cold, served as a first course or as a main course of a meal or as a snack between meals (sipped like a beverage). Soup can be used as an ingredient in the preparation of other dietary components and can range from broth (clear soup) to sauces (cream or cheese-based soups); dehydrated and cooked foods, including cooking aids such as: powders, granules, pastes, concentrated liquid products, including concentrated broths, broths and broth-like products in the form of compressed cubes, tablets or powders or granules, which are sold separately as finished products or as ingredients in products, sauces and formulation mixtures (regardless of the technology); dietary solution products such as: dehydrated and freeze-dried soups, including dehydrated soup mixtures, dehydrated instant soups, dehydrated ready-to-cook soups, dehydrated or environmentally prepared formulations of ready-made dishes, dietary and Main dishes for single servings, including pasta, potato, and rice dishes; food garnishes, such as: condiments, vinaigrettes, salad dressings, salad toppings, dips, breadcrumbs, batter mixtures, storage-stable spreads, barbecue sauces, liquid formulation mixtures, concentrates, sauces or sauce mixtures, including formulation mixtures for salads, sold as finished products or as ingredients within products, whether dehydrated, liquid, or frozen; beverages, including beverage mixtures and concentrates, including but not limited to alcoholic and non-alcoholic ready-to-drink beverages and powdered beverages, carbonated and non-carbonated beverages, such as soda water, fruit or vegetable juices, alcoholic and non-alcoholic beverages, teas such as green tea and black tea, wines such as red wine; confectionery products, such as cakes, cookies, pies, candies, chewing gum, gelatin, ice cream, fruit jelly, puddings, jams, jellies, salad dressings and other condiments, cereals and other breakfast foods, canned fruit and fruit jams, etc.

[0085] Methods are provided for enhancing the sweetness of consumer products and / or modulating one or more flavor properties of sweeteners to make the consumer products taste more like sucrose-sweetened consumer products.

[0086] In one embodiment, a method of enhancing the sweetness of a consumer product includes (i) providing a consumer product containing at least one sweetener and (ii) adding a sweetness improver containing at least one diterpenoid compound as disclosed herein to the consumer product to provide a consumer product with enhanced sweetness.

[0087] In another embodiment, a method for enhancing the sweetness of a consumer product includes (i) providing a base material for the consumer product and (ii) adding at least one sweetener and a sweetness modifier comprising at least one norditerpene compound as disclosed herein to the base material for the consumer product to provide a consumer product with enhanced sweetness. The at least one sweetener and the at least one norditerpene compound may be added together in the form of a flavoring agent or added separately.

[0088] This disclosure is further described with reference to the following non-limiting embodiments.

[0089] Example

[0090] The following examples are given for illustrative purposes only and should not be construed as limiting the invention, as many variations of the invention are possible without departing from the spirit and scope of this disclosure.

[0091] Example 1: Extraction and isolation of diterpenes from Forsythia suspensa

[0092] 100 g of *Paeonia lactiflora* powder was extracted with 80% methanol using an ASE extraction system to obtain 31.6 g of extract. The extract was then suspended in water and partitioned with hexane to obtain a fraction of 1.58 g. Subsequently, the extract was purified by preparative HPLC with a gradient from 60% acetonitrile to 100% acetonitrile to obtain three compounds: Formula I(a) (29 mg), Formula I(b) (112 mg), and Formula I(c) (36 mg).

[0093] Characterization of the chemical structure of compounds of formula I(a)

[0094]

[0095] A compound of formula I(a) was obtained as a pale yellow amorphous powder and had the molecular formula C confirmed by HRESIMS analysis. 19 H 26 O2([M+H)) + At m / z 287.1942, the calculated value is 287.1933). The structure of the compound of established formula I(a) is shown above, and based on... 1 H NMR, 13 C NMR, 1 H- 1 H COSY, HSQC, and HMBC spectra for all compounds of formula I(a) 1 H and 13 The C NMR spectrum signals were assigned (Table 1).

[0096] Table 1. Number of NMR spectra of compounds of formula I(a)

[0097]

[0098] Data on Bruker 300 in methanol - d 6 records, 1 H: 300 MHz 13 C: 75 MHz

[0099] Characterization of the chemical structure of compounds of formula I(b)

[0100] I(b)

[0101] Compound of formula I(b) was obtained as a pale yellow amorphous powder. Its HRESIMS values ​​are 303.1941 [M+H]. + The molecular ion peak at [value], calculated at 303.1960, is consistent with the molecular formula C. 19 H 26 O3 is consistent. The structure of the compound with established formula I(b) is shown above, and based on... 1 H NMR, 13 C NMR, 1 H- 1 H COSY, HSQC, and HMBC spectra for all compounds of formula I(b) 1 H and 13 The C NMR spectrum signals were assigned (Table 2).

[0102] Table 2. NMR spectral data of compounds of formula I(b)

[0103]

[0104] Data on Bruker 300 in methanol - d 6 records, 1 H: 300 MHz 13 C: 75 MHz

[0105] Characterization of the chemical structure of compounds of formula I(c)

[0106] I(c)

[0107] A compound of formula I(c) was obtained as a pale yellow amorphous powder, with the molecular formula C. 19 H 24 O4 is generated by HRESIMS in positive ion mode (m / z 317.1727 [M+H)). +The calculated value is 317.11753. The structure of the compound with established formula I(c) is shown above, and is based on... 1 H NMR, 13 C NMR, 1 H- 1 H COSY, HSQC, and HMBC spectra represent all compounds of formula I(c). 1 H and 13 The C NMR spectrum signals were assigned (Table 3).

[0108] Table 3. NMR spectral data of compounds of formula I(c)

[0109]

[0110] Data on Bruker 300 in methanol - d 6 records, 1 H: 300 MHz 13 C: 75 MHz

[0111] Example 2: Flavor adjustment using compounds derived from Forsythia fractions

[0112] Descriptive sensory evaluations were performed on the same substrate using varying amounts of compounds isolated from the Forsythia suspensa fraction. The results of this analysis, compared to the same substrate in which the compound was absent, are presented in Table 4.

[0113] Table 4

[0114]

[0115] The compounds in Table 4 show a positive overall contribution to the sweetness-modifying effect.

[0116] Example 3: Flavor adjustment using Forsythia suspensa fraction

[0117] The root bark of *Forsythia suspensa* (10 g) was extracted with 200 mL of 25%, 50%, and 75% ethanol / water at room temperature or at temperatures ranging from 20°C to 100°C to obtain three ethanol / water extracts. The extracts were then filtered and dried under reduced pressure using a rotary evaporator (Rotovap) to obtain the three extracts. Analysis of *Forsythia suspensa* root bark (10 g) by LC / MS was performed. J. Giraldii Extracts were obtained and compounds containing formulas I(a), I(b), and I(c) were identified. Sensory evaluation was performed using the extracts. The results of this analysis are presented in Table 5 compared to the same application without the Forsythia fraction.

[0118] Table 5

[0119]

[0120] The compounds in Table 5 show a positive overall contribution to the sweetness-modifying effect.

[0121] While specific embodiments of the invention have been described and illustrated, it will be apparent 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. Therefore, all such changes and modifications falling within the scope of the invention are intended to be covered in the appended claims.

Claims

1. A composition comprising, Flavor provides substances; and At least one diterpene of formula I: (I) R1, R2, and R3 are each independently selected from hydrogen, hydroxyl, or oxo; R4 is selected from methyl, hydroxymethyl, aldehyde, carboxylic acid, or substances containing C. 1-6 Alkyl esters; R5 is selected from hydrogen and C. 1-6 Alkyl, furanose, pyranose, or oligosaccharide moieties having two to six sugar moieties; and R6 is selected from hydrogen, hydroxyl group, or C. 1-6 alkyl.

2. The composition according to claim 1, wherein the at least one diterpene has the structure of formula I(a): I(a)。 3. The composition according to claim 1, wherein the at least one diterpene has the structure of formula I(b): I(b)。 4. The composition according to claim 1, wherein the at least one diterpene has the structure of formula I(c). I(c)。 5. The composition according to claim 1, wherein it is in the form of an emulsion.

6. The composition according to claim 1, wherein it is in powder form.

7. The composition according to claim 1, further comprising at least one sweetness improver selected from steviol glycosides, mogrosides, dihydrochalcone, and combinations thereof.

8. Consumer goods, which include, (a) at least one sweetener, and (b) A sweetness improver comprising at least one diterpene of formula I: (I) R1, R2, and R3 are each independently selected from hydrogen, hydroxyl, or oxo; R4 is selected from methyl, hydroxymethyl, aldehyde, carboxylic acid, or substances containing C. 1-6 Alkyl esters; R5 is selected from hydrogen and C. 1-6 Alkyl, furanose, pyranose, or oligosaccharide moieties having two to six sugar moieties; R6 is selected from hydrogen, hydroxyl group, or C. 1-6 Alkyl groups; and The at least one sweetener is present in a sweetening amount.

9. The consumer product according to claim 8, wherein the at least one diterpene has the structure of formula I(a): I(a)。 10. The consumer product according to claim 8, wherein the at least one diterpene has the structure of formula I(b): I(b)。 11. The consumer product according to claim 8, wherein the at least one diterpene has the structure of formula I(c). I(c)。 12. The consumer product according to claim 8, wherein the at least one sweetener is selected from sucrose, fructose, glucose, xylose, arabinose, rhamnose, tagatose, allusion, trehalose, isomaltulose, steviol glycosides, mogrosides, stevia, trifolin, stevia glycosides, aspartame, advans, agave syrup, acesulfame potassium (AceK), high fructose corn syrup, neotame, saccharin, sucralose, high fructose corn syrup, starch syrup, mogroside extract, neomethyl hesperidin dihydrochalcone, naringin dihydrochalcone, HDG, sugar alcohol cellobiose, allulose, cyclohexylsulfamic acid, carbapenem, tamartin, molasses, rice syrup, and combinations thereof.

13. The consumer product according to claim 12, wherein the steviol glycoside is selected from riboboroside M, riboboroside D, riboboroside A, riboboroside N, riboboroside O, riboboroside E, steviol monosaccharide glycoside, steviol disaccharide glycoside, stevioside, durcuroside B, durcuroside A, riboboroside B, riboboroside G, steviol glycoside, riboboroside C, riboboroside F, riboboroside I, riboboroside H, riboboroside L, riboboroside K, riboboroside J, riboboroside M2, riboboroside D2, riboboroside S, riboboroside T, riboboroside U, riboboroside V, riboboroside W, riboboroside Z1, riboboroside Z2, riboboroside IX, enzymatically glucosylated steviol glycosides, and combinations thereof.

14. The consumer product according to claim 12, wherein the mogroside is selected from grosmogroside I, mogroside IA, mogroside IE, 11-oxomogroside IA, mogroside II, mogroside IIA, mogroside IIB, mogroside IIE, 7-oxomogroside IIE, mogroside III, mogroside HIE, 11-oxomogroside HIE, 11-deoxymogroside III, mogroside IV, mogroside IVA, 11-oxomogroside IV, 11-oxomogroside IVA, mogroside V, isomogroside V, 11-deoxymogroside V, 7-oxomogroside V, 11-oxomogroside V, isomogroside V, mogroside VI, mogroside alcohol, 11-oxomogroside alcohol, symmonoside I, and combinations thereof.

15. The consumer product of claim 8, wherein the sweetness improver is present at a concentration of 0.01 ppm to 100 ppm.

16. The consumer product of claim 8, wherein the consumer product is a beverage.

17. The consumer product of claim 8, wherein the sweetness improver further comprises a compound selected from steviol glycosides, mogrosides, dihydrochalcone, and combinations thereof.

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