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WO2025186080A1 - Compositions et procédés de modulation du goût - Google Patents

Compositions et procédés de modulation du goût

Info

Publication number
WO2025186080A1
WO2025186080A1 PCT/EP2025/055232 EP2025055232W WO2025186080A1 WO 2025186080 A1 WO2025186080 A1 WO 2025186080A1 EP 2025055232 W EP2025055232 W EP 2025055232W WO 2025186080 A1 WO2025186080 A1 WO 2025186080A1
Authority
WO
WIPO (PCT)
Prior art keywords
rebaudioside
consumable
mogroside
norditerpenoid
flavor
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/EP2025/055232
Other languages
English (en)
Other versions
WO2025186080A8 (fr
Inventor
Qingyao SHOU
Yosuke ONUMA
Feng Shi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Givaudan SA
Original Assignee
Givaudan SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Givaudan SA filed Critical Givaudan SA
Publication of WO2025186080A1 publication Critical patent/WO2025186080A1/fr
Publication of WO2025186080A8 publication Critical patent/WO2025186080A8/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/33—Artificial sweetening agents containing sugars or derivatives
    • A23L27/36—Terpene glycosides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/205—Heterocyclic compounds
    • A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms

Definitions

  • the present disclosure relates to compositions containing norditerpenoids.
  • the present disclosure further extends to consumables containing sweeteners and at least one nor diterpenoid to improve sweetness, improve mouthfeel and/or mask off-notes of consumables.
  • 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.
  • the sweet taste of natural and synthetic high-intensity sweeteners 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.
  • sugar sweet, short-chain, soluble carbohydrates, including glucose, fructose, sucrose, maltose and lactose
  • HFCS high fructose corn syrups
  • This can create unbalanced temporal taste profiles.
  • 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.
  • a composition comprises a flavor-providing substance and at least one norditerpenoid of Formula I: wherein Ri, R2 and R3 are each independently selected from hydrogen, hydroxyl or oxo; wherein R4 is selected from methyl, hydroxymethyl, aldehyde, carboxylic acid or ester with Ci-6 alkyl; wherein R5 is selected from hydrogen, C1-6 alkyl, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to six saccharide moieties; and wherein Re is selected from hydrogen, hydroxyl or C1-6 alkyl.
  • a consumable comprises (a) at least one sweetener, and (b) a sweetness modifier including at least one nor diterpenoid of Formula I: wherein Ri, R2 and R3 are each independently selected from hydrogen, hydroxyl or oxo; wherein R4 is selected from methyl, hydroxymethyl, aldehyde, carboxylic acid or ester with Ci-6 alkyl; wherein R5 is selected from hydrogen, C1-6 alkyl, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to six saccharide moieties; wherein Re is selected from hydrogen, hydroxyl or Ci-6 alkyl; and wherein the at least one sweetener is present in a sweetening amount.
  • Ri, R2 and R3 are each independently selected from hydrogen, hydroxyl or oxo; wherein R4 is selected from methyl, hydroxymethyl, aldehyde, carboxylic acid or ester with Ci-6 alkyl; wherein R5 is selected from hydrogen
  • the present disclosure relates to the surprising finding that certain norditerpenoids and the extracts or fractions containing these compounds exhibit a sweet modifying effect as well as mouthfeel modifying properties without introducing unpleasant off-notes.
  • the present disclosure relates to the surprising finding that certain norditerpenoids 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.
  • norditerpenoid compounds of the formulae disclosed herein enhance sweetness.
  • norditerpenoid compounds of the formulae disclosed herein are taste modulators/modifiers, with or without simultaneously enhancing sweetness.
  • certain norditerpenoids of the formulae disclosed herein may be isolated from the root barks of Jasminum gircildii. Jasminum giraldii Diels (Oleaceae), is an endemic plant found in China’s Shaanxi Province. Its dried root barks, named as “quan pi” in Chinese, are used as a traditional Chinese medicine for the treatment of various diseases such as fever, rheumatic pain and irregular menstruation. Certain norditerpenoids of the formulae disclosed herein can be derived from an extract, or can be synthetic, or can be a combination of extract and synthetic.
  • the root barks of Jasminum giraldii are dried prior to extraction. In some embodiments, the root barks are optionally milled prior to extraction.
  • the root barks of Jasminum giraldii 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.
  • 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.
  • the solvent comprises water and one or more alcohols.
  • the solvent comprises water and an alcohol selected from methanol, ethanol, n-propanol, 2-propanol, 1 butanol, 2-butanol and mixtures thereof.
  • 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.
  • alcohol comprises from about 80% to about 100% of the solvent, with the remainder being water.
  • 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 of about 100°C.
  • 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.”
  • Insoluble plant material may be separated from the extracted mixture by, e.g., filtration.
  • 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.
  • various filtration aids such as diatomaceous earth, bentonite, zeolite, etc., may be used in this process.
  • the crude extract is then subjected to one or more chromatographic separations to provide a solution of one or more norditerpenoid 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.
  • 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.
  • 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.
  • norditerpenoid compounds of Formula I are useful for enhancing and/or modifying/modulating sweetness of a consumable containing a sweetener:
  • Ri, R2 and R3 are each independently selected from hydrogen, hydroxyl or oxo; wherein R4 is selected from methyl, hydroxymethyl, aldehyde, carboxylic acid or ester with C1-6 alkyl; wherein R5 is selected from hydrogen, Ci-6 alkyl, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to six saccharide moieties; and wherein Re is selected from hydrogen, hydroxyl or Ci-6 alkyl.
  • saccharide refers to monosaccharides, disaccharides, oligosaccharides and polysaccharides.
  • a saccharide comprises at least one carbohydrate.
  • Exemplary carbohydrates include, but are not limited to, sucrose, glyceraldehyde, dihydroxyacetone, erythrose, threose, erythrulose, arabinose, lyxose, ribose, xylose, ribulose, xylulose, allose, altrose, galactose, glucose, gulose, idose, mannose, talose, fructose, psicose, sorbose, tagatose, mannoheptulose, sedoheltulose, octolose, fucose, rhamnose, arabinose, turanose and sialose.
  • nor di terpenoid compounds of Formula I according to the present disclosure are sweetness modifiers.
  • sweetness modifier 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).
  • sweetness recognition threshold concentration is the lowest known concentration of a compound that is perceivable by the human sense of taste as sweet.
  • the sweetness recognition threshold concentration is specific for a particular compound, and can vary based on temperature, matrix, ingredients and/or flavor system.
  • new norditerpenoid compounds of Formula I according to the present disclosure are taste modulators, with or without simultaneously acting as sweetness modifiers. That is, in some embodiments, the norditerpenoid compounds of Formula I modify sweetness and modulate one or more taste attributes of a sweetener. In other embodiments, the norditerpenoid compounds of Formula I modify the sweetness of a sweetener without modulating one or more taste attributes of the sweetener. In still other embodiments, the norditerpenoid compounds of Formula I modulate one or more taste attributes of a sweetener without modifying the sweetness of the sweetener.
  • the norditerpenoid compound is a compound of Formula 1(a):
  • the norditerpenoid compound is a compound of Formula 1(b):
  • the norditerpenoid compound is a compound of Formula 1(c):
  • new norditerpenoid compounds of Formula II according to the present disclosure are taste modulators, with or without simultaneously acting as sweetness modifiers. That is, in some embodiments, the norditerpenoid compounds of Formula II modify sweetness and modulate one or more taste attributes of a sweetener. In other embodiments, the norditerpenoid compounds of Formula II modify the sweetness of a sweetener without modulating one or more taste attributes of the sweetener. In still other embodiments, the norditerpenoid compounds of Formula II modulate one or more taste attributes of a sweetener without modifying the sweetness of the sweetener.
  • norditerpenoid compounds of Formula II are useful for enhancing and/or modifying/modulating sweetness of a consumable containing a sweetener: wherein Ri, R2 and R3 are each independently selected from hydrogen, hydroxyl or oxo; wherein R4 is selected from methyl, hydroxymethyl, aldehyde, carboxylic acid or ester with Ci-6 alkyl; wherein R5 is selected from hydrogen, Ci-6 alkyl, a furanose moiety, a pyranose moiety or an oligosaccharide moiety having two to six saccharide moieties; and wherein Re is selected from hydrogen, hydroxyl or Ci-6 alkyl.
  • new norditerpenoid compounds of Formula III are taste modulators, with or without simultaneously acting as sweetness modifiers. That is, in some embodiments, the norditerpenoid compounds of Formula III modify sweetness and modulate one or more taste attributes of a sweetener. In other embodiments, the norditerpenoid compounds of Formula III modify the sweetness of a sweetener without modulating one or more taste attributes of the sweetener. In still other embodiments, the norditerpenoid compounds of Formula III modulate one or more taste attributes of a sweetener without modifying the sweetness of the sweetener.
  • norditerpenoid compounds of Formula III are useful for enhancing and/or modifying/modulating sweetness of a consumable containing a sweetener: wherein Rl, R2, R3, R9, RIO and Rl l are independently selected from hydrogen, hydroxyl or oxo groups; R4 is selected from methyl group, hydroxymethyl group, aldehyde, carboxylic acid, or ester with Ci-6 alky; R5 is independently selected from hydrogen, Ci-6 alkyl, a furanose moiety, a pyranose moiety, or an oligosaccharide moiety having two to six saccharide moieties; R6, R7 and R8 are selected from hydrogen, hydroxyl or Ci-6 alkyl.
  • new norditerpenoid compounds of Formula IV are taste modulators, with or without simultaneously acting as sweetness modifiers. That is, in some embodiments, the norditerpenoid compounds of Formula IV modify sweetness and modulate one or more taste attributes of a sweetener. In other embodiments, the norditerpenoid compounds of Formula IV modify the sweetness of a sweetener without modulating one or more taste attributes of the sweetener. In still other embodiments, the norditerpenoid compounds of Formula IV modulate one or more taste attributes of a sweetener without modifying the sweetness of the sweetener.
  • norditerpenoid compounds of Formula IV are useful for enhancing and/or modifying/modulating sweetness of a consumable containing a sweetener: wherein Rl, R2, R3, R9, RIO and Rl l are independently selected from hydrogen, hydroxyl or oxo groups; R4 is selected from methyl group, hydroxymethyl group, aldehyde, carboxylic acid or ester with Ci-6 alky; R5 is independently selected from hydrogen, Ci-6 alkyl, a furanose moiety, a pyranose moiety, or an oligosaccharide moiety having two to six saccharide moieties; R6, R7 and R8 are selected from hydrogen, hydroxyl or Ci-6 alkyl.
  • the flavor composition according to the present disclosure may also comprise additional sweetness modifiers.
  • the additional sweetness modifiers are selected from the group consisting of steviol glycosides, mogrosides, dihydrochalcones and combinations thereof.
  • the amount of these 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 2,000 ppm to about 100,000 ppm, and in another embodiment from about 5,000 ppm to about 50,000 ppm.
  • the flavor composition according to the present disclosure may also comprise a flavor-providing substance.
  • flavor-providing substance it is meant a composition created by a flavorist using methods known to the skilled person that is a mixture of tastants, aroma compounds and sensates.
  • suitable flavorants include natural flavors, artificial flavors, spices, seasonings, and the like.
  • Exemplary flavor-providing substances include synthetic flavor oils and flavoring aromatics and/or oils, oleoresins, essences, and distillates, and a combination comprising at least one of the foregoing.
  • Flavor oils include spearmint oil, cinnamon oil, oil of wintergreen (methyl salicylate), peppermint oil, Japanese mint oil, clove oil, bay oil, anise oil, eucalyptus oil, thyme oil, cedar leaf oil, oil of nutmeg, allspice, oil of sage, mace, oil of bitter almonds, and cassia oil; useful flavoring agents include artificial, natural and synthetic fruit flavors such as vanilla, and citrus oils including lemon, orange, lime, grapefruit, yuzu, sudachi, and fruit essences including apple, pear, peach, grape, raspberry, blackberry, gooseberry, blueberry, strawberry, cherry, plum, prune, raisin, cola, guarana, neroli, pineapple, apricot, banana, melon, apricot, cherry, tropical fruit, mango, mangosteen, pomegranate, papaya, and so forth.
  • useful flavoring agents include artificial, natural and synthetic fruit flavors such as vanilla, and citrus oils including lemon, orange,
  • Additional exemplary flavors imparted by a flavor-providing substance include a milk flavor, a butter flavor, a cheese flavor, a cream flavor, and a yogurt flavor, a vanilla flavor, tea or coffee flavors, such as a green tea flavor, an oolong tea flavor, a tea flavor, a cocoa flavor, a chocolate flavor, and a coffee flavor; mint flavors, such as a peppermint flavor, a spearmint flavor, and a Japanese mint flavor; spicy flavors, such as an asafetida flavor, an ajowan flavor, an anise flavor, an angelica flavor, a fennel flavor, an allspice flavor, a cinnamon flavor, a chamomile flavor, a mustard flavor, a cardamom flavor, a caraway flavor, a cumin flavor, a clove flavor, a pepper flavor, a coriander flavor, a sassafras flavor, a savory flavor, a Zanthoxyli Fructus flavor, a
  • flavor-providing substances may also include aldehydes and esters such as cinnamyl acetate, cinnamaldehyde, citral diethylacetal, dihydrocarvyl acetate, eugenyl 49 formate, p-methylamisol, and so forth can be used.
  • aldehydes and esters such as cinnamyl acetate, cinnamaldehyde, citral diethylacetal, dihydrocarvyl acetate, eugenyl 49 formate, p-methylamisol, and so forth can be used.
  • aldehyde flavourings include acetaldehyde (apple), benzaldehyde (cherry, almond), anisic aldehyde (licorice, anise), cinnamic aldehyde (cinnamon), citral, i.e., alpha-citral (lemon, lime), neral, i.e., beta-citral (lemon, lime), decanal (orange, lemon), ethyl vanillin (vanilla, cream), heliotrope, i.e., piperonal (vanilla, cream), vanillin (vanilla, cream), alpha-amyl cinnamaldehyde (spicy fruity flavours), butyraldehyde (butter, cheese), valeraldehyde (butter, cheese), citronellal (modifies, many types), decanal (citrus fruits), aldehyde C-8 (citrus fruits), aldehyde (
  • the at least one flavor-providing substance is present in an amount of about 1 to about 95 wt.%, based on the total weight of the flavor composition. In certain embodiments, the at least one flavor-providing substance is present in an amount of about 1 to about 70 wt.%, based on the total weight of the flavor composition. In certain embodiments, the at least one flavor-providing substance is present in an amount of about 5 to about 60 wt.%, based on the total weight of the flavor composition. In certain embodiments, the at least one flavor-providing substance is present in an amount of about 10 to about 50 wt.%, based on the total weight of the flavor composition.
  • the flavor composition may also contain one or more adjuvants.
  • Adjuvants are ingredients that do not influence the flavor or other organoleptic properties of flavor composition, but which can affect its quality in other ways.
  • Adjuvants may include colorants, which can add desirable color or replace color lost through processing; pH buffers; preservatives; anti-oxidants, and the like.
  • adjuvants may also include solvents, emulsifiers, disintegrating agents and lubricants.
  • Other examples of adjuvants for flavor compositions may be found in for example, “Perfume and Flavour Materials of Natural Origin”, S. Arctander, Ed., Elizabeth, N.J., 1960; in “Perfume and Flavour Chemicals”, S. Arctander, Ed., Vol.
  • the norditerpenoid compounds described herein can be provided in pure form or as part of a mixture.
  • the mixture can be an extract or fraction prepared from the plant or portion of a plant, as described herein.
  • the norditerpenoid compounds described herein 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • the at least one sweetener does not comprise a carbohydrate sweetener.
  • 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 and combinations thereof.
  • sweeteners include siamenoside I, monatin and its salts (monatin SS, RR, RS, SR), curculin, glycyrrhizic acid and its salts, thaumatin, monellin, mabinlin, brazzein, tamatin, hemandulcin, phyllodulcin, glycyphyllin, trilobatin, baiyunoside, osladin, polypodoside A, pterocaryoside A, pterocaryoside B, mukurozioside, phlomisoside I, periandrin I, abrusoside A, steviolbioside and cyclocarioside I, sugar alcohols such as erythritol, sucralose, potassium acesulfame, acesulfame acid and salts thereof, aspartame, alitame, saccharin and salts thereof, hesperidin dihydrochalcone
  • the sweetener is a caloric sweetener or mixture of caloric sweeteners.
  • the caloric sweetener is selected from sucrose, fructose, glucose, high fructose com/starch syrup, a beet sugar, a cane sugar and combinations thereof.
  • the sweetener comprises at least one steviol glycoside, wherein the at least one steviol glycoside is present in a sweetening amount.
  • the steviol glycoside can be natural, synthetic or a combination of natural and synthetic.
  • the steviol glycoside can 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, 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.
  • the steviol glycoside blend sweetener typically has a total steviol glycoside content of about 95% by weight or greater on a dry basis. The remaining 5% comprises other non-steviol glycoside compounds, e.g. by-products from extraction or purification processes. In some embodiments, the steviol glycoside blend sweetener has a total steviol glycoside content of about 96% or greater, about 97% or greater, about 98% or greater or about 99% or greater. “Total steviol glycoside content”, as used herein, refers to the sum of the relative weight contributions of each steviol glycoside in a sample.
  • the sweetener comprises at least one mogroside, wherein the at least one mogroside is present in a sweetening amount.
  • the mogroside can be natural, synthetic or a combination of natural and synthetic.
  • the mogroside can be provided in pure form or as part of mixture, i.e. a mogroside blend.
  • mogrosides include, but are not limited to, any of grosmogroside I, mogroside IA, mogroside IE, 1 1-oxomogroside IA, mogroside II, mogroside II A, mogroside II B, mogroside II E, 7-oxomogroside II E, mogroside III, Mogroside Hie, 1 1- oxomogroside HIE, 11- deoxymogroside III, mogroside IV, Mogroside IVA 1 1-oxomogroside IV, 1 1-oxomogroside IV A, mogroside V, isomogroside V, 1 1-deoxymogroside V, 7- oxomogroside V, 11- oxomogroside V, isomogroside V, mogroside VI, mogrol, 1 1-oxomogrol, siamenoside I, and combinations thereof.
  • the weight ratio of the at least one sweetener to the norditerpenoid compound described herein can vary.
  • the norditerpenoid compounds 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.
  • the norditerpenoid compounds described herein 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 norditerpenoid compound.
  • the norditerpenoid compounds When added to a consumable, the norditerpenoid compounds are used in an amount effective to modify the sweetness or mouthfeel of a sweetener without exhibiting any off-taste.
  • the amount of the norditerpenoid compound present in the consumable may be in a concentration of from about 0.01 ppm to about 100 ppm, 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.
  • 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
  • ppm concentration
  • 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. For example, “a range of from 0.01 ppm to 100 ppm” of the at least one norditerpenoid is to be read as indicating each and every possible number along the continuum between 0.01 and 100. 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.
  • 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.
  • 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.
  • 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.
  • the consumable may include a base.
  • base refers to all the ingredients necessary for the consumable, apart from the norditerpenoid compound. 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.
  • 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.
  • 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.
  • 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.
  • Non-limiting examples of consumables include: wet/liquid soups regardless of concentration or container, including frozen soups.
  • 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.
  • 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
  • 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.
  • a method of enhancing the sweetness of a consumable comprises (i) providing a consumable comprising at least one sweetener and (ii) adding a sweetness modifier including at least one norditerpenoid compound as disclosed herein to the consumable to provide a consumable with enhanced sweetness.
  • a method of enhancing the sweetness of a consumable comprises (i) providing a consumable base and (ii) adding at least one sweetener and a sweetness modifier including at least one norditerpenoid compound as disclosed herein to the consumable base to provide a consumable with enhanced sweetness.
  • the at least one sweetener and the at least one norditerpenoid compound can be added together in the form of a flavor, or separately.
  • Example 1 Extraction and Isolation of Norditerpenoids from Jastninum giraldii
  • Jasminum giraldii powder (100 g) was extracted with 80% methanol with ASE extraction system to give 31.6 g of extract, the extract was suspended in water and partitioned with hexane to give 1.58 g of a fraction. Thereafter, the extract was purified by preparative HPLC with a gradient from 60% acetonitrile to 100% acetonitrile to give three compounds Formula 1(a) (29 mg), Formula 1(b) (112 mg) and Formula 1(c) (36 mg). Characterization of chemical structure of compound of Formula 1(a)
  • the compound of Formula 1(a) was obtained as a yellowish amorphous powder and had a molecular formula C19H26O2 by HRESIMS analysis ([M+H] + at m/z 287.1942 calcd 287.1933).
  • the structure of the compound of Formula 1(a) was established as shown above and all the 'H and 13 C NMR spectroscopic signals of the compound of Formula 1(a) were assigned on the basis of the H NMR, 13 C NMR, ⁇ -’H COSY, HSQC, and HMBC spectra (Table 1).
  • the compound of Formula 1(b) was obtained as a yellowish amorphous powder. Its HRESIMS exhibited a molecular ion peak at m/z 303.1941 [M+H] + , calcd. 303.1960, which was compatible with the molecular formula C19H26O3.
  • the structure of the compound of Formula 1(b) was established as shown above and all the 'H and 13 C NMR spectroscopic signals of the compound of Formula 1(b) were assigned on the basis of the 'H NMR, 13 C NMR, ⁇ - ⁇ H COSY, HSQC, and
  • the compound of Formula 1(c) was obtained as a yellowish amorphous powder, the molecular formula C19H24O4 was deduced from the positive-ion mode HRESIMS (m/z 317.1727 [M+H] + , calcd. 317.11753).
  • the structure of the compound of Formula 1(c) was established as shown above, and all the J H and 13 C NMR spectroscopic signals of the compound of Formula 1(c) were assigned on the basis of the J H NMR, 13 C COSY, HSQC, and HMBC spectra (Table 3). Table 3. NMR Spectroscopic Data of Compound of Formula 1(c)*
  • the root barks of Jasminum giraldii (10 g) were extracted with 200 mL of 25%, 50% and 75% ethanol/water to give three ethanol/water extracts at room temperature or at a temperature from 20 to 100 °C, the extract was then filtered and dried down with Rotovap at reduced pressure to give three extracts.
  • the J. giraldii extracts were analyzed by LC/MS and found to include compounds of Formulas 1(a), 1(b) and 1(c). Sensory evaluations were carried out using the extracts. The results of this analysis, as compared to the same applications in the absence of the J. giraldii fraction, are presented in Table 5.

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Abstract

L'invention concerne une composition comprenant une substance fournissant un arôme et au moins un norditerpénoïde de formule (I), (I) dans laquelle R1, R2 et R3 sont chacun indépendamment choisis parmi hydrogène, hydroxyle ou oxo ; R4 étant choisi parmi méthyle, hydroxyméthyle, aldéhyde, acide carboxylique ou ester avec C1-6 alkyle ; R5 étant choisi parmi hydrogène, C1-6 alkyle, une fraction furanose, une fraction pyranose ou une fraction oligosaccharide ayant deux à six fractions saccharides ; et R6 étant choisi parmi hydrogène, hydroxyle ou C1-6 alkyle.
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102652819A (zh) * 2012-03-06 2012-09-05 深圳市国源药业有限公司 一种妇炎康分散片及其制备方法
CN104087476A (zh) * 2014-07-15 2014-10-08 寿建卫 白酒酒曲和制备工艺及其酿造白酒后所得酒糟的应用
CN104135871B (zh) * 2012-03-13 2018-01-02 奇华顿股份有限公司 用于生产包含具有皂树皂苷的纳米乳的澄清饮料的组合物和方法
WO2019150388A1 (fr) * 2018-01-31 2019-08-08 Veganutritech LLP Nouvelles compositions de glucose oxydase

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102652819A (zh) * 2012-03-06 2012-09-05 深圳市国源药业有限公司 一种妇炎康分散片及其制备方法
CN104135871B (zh) * 2012-03-13 2018-01-02 奇华顿股份有限公司 用于生产包含具有皂树皂苷的纳米乳的澄清饮料的组合物和方法
CN104087476A (zh) * 2014-07-15 2014-10-08 寿建卫 白酒酒曲和制备工艺及其酿造白酒后所得酒糟的应用
WO2019150388A1 (fr) * 2018-01-31 2019-08-08 Veganutritech LLP Nouvelles compositions de glucose oxydase

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
"CTFA Cosmetic Ingredient Handbook", 1988, THE COSMETIC, TOILETRY AND FRAGRANCE ASSOCIATION, INC.
"Flavourings", 1998, WILEY-VCH
"Perfume and Flavour Chemicals", vol. 1, 2, 1994, ALLURED PUBLISHING CORPORATION
"Publication No 1274", NATIONAL ACADEMY OF SCIENCES, article "Chemicals Used in Food Processing", pages: 63 - 258
ARA IFFAT ET AL: "Structurally Novel Diterpenoid Constituents from the Stem Bark of Azadirachta indica (Meliaceae)", J. CHEM. SOC. PERKIN TRANS, 1 January 1989 (1989-01-01), pages 1 - 3, XP093272991 *
ELIZABETH, N.J.: "Perfume and Flavour Materials of Natural Origin", 1960
JESS: "Pear Bowl With Vegan Yogurt & Neem Bark Powder Recipe - House of Tomorrow", 31 May 2022 (2022-05-31), pages 1 - 6, XP093273010, Retrieved from the Internet <URL:https://houseoftomorrow.net/pear-bowl-with-vegan-yogurt-neem-bark-powder-recipe/> *

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