WO2024007104A1 - 用于增强甜味的新型吡喃葡萄糖苷组合物 - Google Patents

用于增强甜味的新型吡喃葡萄糖苷组合物 Download PDF

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WO2024007104A1
WO2024007104A1 PCT/CN2022/103589 CN2022103589W WO2024007104A1 WO 2024007104 A1 WO2024007104 A1 WO 2024007104A1 CN 2022103589 W CN2022103589 W CN 2022103589W WO 2024007104 A1 WO2024007104 A1 WO 2024007104A1
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rebaudioside
lipedoside
group
sweetness
composition
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PCT/CN2022/103589
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English (en)
French (fr)
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尚志春
郑美梅
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国际香料和香精公司
尚志春
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Application filed by 国际香料和香精公司, 尚志春 filed Critical 国际香料和香精公司
Priority to PCT/CN2022/103589 priority Critical patent/WO2024007104A1/zh
Priority to PCT/US2023/069353 priority patent/WO2024011059A1/en
Publication of WO2024007104A1 publication Critical patent/WO2024007104A1/zh

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/33—Artificial sweetening agents containing sugars or derivatives
    • A23L27/36—Terpene glycosides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/88—Taste or flavour enhancing agents

Definitions

  • Reducing sugar content in food and beverages has become a necessity for the food industry.
  • Food and beverage manufacturers often use non-caloric, high-intensity sweetness modifiers (such as rebaudioside A (RebA), aspartame, saccharin, glycosylated steviol glycosides, etc.) to partially or completely replace sugar.
  • these sweetness modifiers may exhibit undesirable taste attributes such as delayed sweetness onset, bitter and astringent aftertaste, and lack of body and mouthfeel. Therefore, sweetness enhancers have become valuable tools that reduce the use of sugar and/or sweetness modifiers to achieve desired sweetness intensity and mouthfeel and reduce off-flavors.
  • Sweetness enhancers have been described in the prior art.
  • WO 2013/143822 teaches the use of adenosine as a sweetness enhancer for certain sugars
  • EP 2606747 describes the use of deoxycholic acid or its derivatives for enhancing the sweetness of consumables
  • WO 2013/077668 describes Sweetness enhancing effect of polysaccharides or glycopeptides derived from soy sauce
  • WO 2012/107203 teaches the use of nobiletin or its derivatives or hydrates as sweeteners or sweetness enhancers
  • WO 2009/023975 describes the use of nobiletin or its derivatives or hydrates as sweeteners or sweetness enhancers
  • WO 2009/023975 describes The use of mogroside V as a sweetener and sweetness enhancer
  • US 2008/0242740 teaches aromatic compositions of alkylamides with hesperetin and/or 4-hydroxydihydrochalcone for enhancing the sensory impression of sweetness
  • R1 and R2 represents hydrogen, and the other of which represents Ra and Rb are independently selected from the group consisting of hydrogen and hydroxyl; and wherein R represents a C alkenyl group.
  • the present invention relates to a method for enhancing the sweetness of a sweetness modifier, the method comprising the step of adding an olfactory effective amount of the above-mentioned glucopyranoside compound to the sweetness modifier, wherein
  • the glucopyranoside compound is provided in the form of Ligustrum robustum (Roxb.) Blume leaf extract.
  • the present invention relates to a composition
  • a composition comprising a sweetness modifier and an olfactory effective amount of the above-described glucopyranoside compound.
  • the invention in another embodiment, relates to a composition
  • a composition comprising a sweetness modifier and an olfactory effective amount of Ligustrum lucidum leaf extract.
  • the present invention relates to a consumable product comprising a sweetness modifier and an olfactory effective amount of the above-described glucopyranoside compound.
  • the present invention relates to a consumable product comprising a sweetness modifier and an olfactory effective amount of Ligustrum lucidum leaf extract.
  • Formula I can be illustrated by, for example but not limited to, the following structures.
  • alkenyl means a straight or branched chain unsaturated aliphatic hydrocarbon containing at least one carbon-carbon double bond.
  • a/an should be understood to mean one/an or a plurality/an.
  • a compound is understood to mean one or more glucopyranoside compounds represented by formula I.
  • structure 1 represents, for example, lipedoside B-IIa (CAS No. 156979-57-6); lipedoside B-IIb (CAS No. 157085-47-7); lipedoside B-IIIa (CAS No. 157085-44- 4); lipedoside B-IIIb (CAS No.
  • Structure 2 represents, for example, ligurobustoside E (CAS No. 189276-30-0).
  • Structure 3 represents, for example, Ligustilin C (CAS No. 176703-94-9) and Ligustin D (CAS No. 176779-11-6).
  • Structure 4 represents, for example, Ligustilin B (CAS No. 176703-93-8).
  • glucopyranoside compounds of formula I have unexpected and advantageous uses in food products. Specifically, these compounds have been found to enhance the sweetness of sweetness modifiers without undesirable off-flavors.
  • lipedoside B-IIIb, lipedoside C, lipedoside E, salts thereof or mixtures thereof have been found to enhance the sweetness of sweetness modifiers without undesirable off-flavors. Accordingly, the present invention provides a method for enhancing the sweetness of sweetness modifiers and reducing sweetness modifiers used in consumables using lipedoside B-IIIb, steguridin C, steguridin E, salts thereof, or mixtures thereof dosage method.
  • the compounds of the present invention are commercially available (e.g., Biopurify Phytochemicals Ltd., China), and can also be isolated and purified from plant extracts, such as Ligustrum robustum ( Roxb.) Blume) (also known as Ligustrum robustum), Phillyrea robusta Roxb., Olea robusta (Roxb.) Sweet), Visiania robusta (Roxb.) DC., Ligustrum purpurascens, Ligustrum expansum, holly tea or broad-leaf holly. Ligustrum lucidum is widely cultivated in the southeastern region of China and has long been used as a traditional health tea, named Kudingcha.
  • Ligustrum lucidum leaf extract contains from about 0.01% to about 95%, from about 0.05% to about 50%, or from about 0.1% to about 10% lipedoside B-IIIb, Ligustrum lucidum C, and Ligustrum lucidum C.
  • Ligustrum lucidum leaf extract contains from about 0.01% to about 95%, from about 0.05% to about 50%, or from about 0.1% to about 10% lipedoside B-IIIb, Ligustrum lucidum C, and Ligustrum lucidum C.
  • percentages (%) are by weight.
  • natural sweeteners include, but are not limited to, sucrose, fructose, glucose, high fructose corn syrup, Stevia rebaudiana compositions including RebA, stevioside, and rebaudioside D (Reb D). Pure component), xylose, arabinose, or rhamnose, and sugar alcohols such as erythritol, xylitol, mannitol, sorbitol, inositol, and combinations thereof.
  • artificial sweeteners include, but are not limited to, aspartame, sucralose, neotame, acesulfame potassium, saccharin, and combinations thereof.
  • Flavoring agents are agents that provide a special taste and/or smell to consumable products. Flavoring agents with modifying properties are a subset of flavoring agents. Add it to consumables to reduce odor and/or improve overall characteristics.
  • flavoring agents with modifying properties of the present invention include, but are not limited to, stevia compositions including steviol glycosides, steviol diglycosides, Reb A, rebaudioside B (Reb B), rebaudioside C (Reb C), Reb D, rebaudioside E (Reb E), rebaudioside F (Reb F), ducoside A, ducoside B, sweet tea glycoside, ⁇ -glucosyl stevia, fructosyl Stevia, galactosyl stevia, beta-glucosyl stevia, simonin, mogroside IV, mogroside V, Luo Han Guo, monatin, glycyrrhizic acid, thaumatin, Its salts, its glycosylated
  • glycosylated derivatives can be prepared by transglycosylation reactions with: but not limited to, glucose, fructose, galactose, rhamnose, ribose, mannose, arabinose, fucose, maltose, lactose, Sucrose, rutinose, sorbose, xylulose, ribulose, rhammulose and xylose.
  • the flavoring agents with modifying properties of the present invention include RebA, Reb C, sweet tea glycoside, Reb D, mogroside V, Luo Han Guo, monatin acid, salts thereof, glycosylated derivatives thereof, and the like. combination.
  • the flavoring agent with modifying properties of the present invention exhibits a weak inherent sweetness.
  • some other flavoring agents of the present invention include, but are not limited to, curculin, acrosin, capersin, brazzein, hernandulcin, phyllosin, sarsaparilla Glycyphyllin, phlorizin, trilobtain, baiyunoside, osladin, polypodosideA, pterocaryoside A, pterocaryoside B, soapberry sesquiterpene glycoside ( mukurozioside), phlomisoside I, periandrin I, abrusoside A, cyclocarioside I and combinations thereof.
  • sweetness modifier refers to sweeteners including natural sweeteners and artificial sweeteners or flavoring agents with modifying properties listed above.
  • sweetness or “sweetness intensity” is understood to mean the relative intensity of the sensation of sweetness as observed or experienced by an individual (e.g., a human), or the degree or amount of sweetness as detected by a taster, e.g., according to the U.S.
  • olfactory effective amount should be understood as meaning the amount of lipedoside B-IIIb, lutruzide C, lustin E, salts thereof or mixtures thereof used in combination with a sweetness modifier, wherein lipedoside B-IIIb, Ligustilin C, Ligustin E, their salts or mixtures thereof enhance the sweetness of the sweetness modifier.
  • the olfactory effective amount may vary depending on many factors including the other ingredients, their relative amounts and the desired olfactory effect. Any amount of lipedoside B-IIIb, lipedoside C, lipedoside E, salts thereof, or mixtures thereof that provides the desired degree of sweetness enhancement without exhibiting off-flavors may be used.
  • the olfactory effective amount ranges from about 1 ppb to about 1000 ppm by weight, preferably from about 2 ppb to about 100 ppm by weight, and more preferably from about 5 ppb to about 10 ppm by weight.
  • the olfactory effective amount ranges from about 100 ppb to about 5000 ppm by weight, preferably from about 1 to about 2000 ppm by weight and more preferably from about 10 to About 1000ppm.
  • consumable products include food products (eg, beverages), sweeteners such as natural or artificial sweeteners, pharmaceutical compositions, dietary supplements, nutraceuticals, dental hygiene compositions, and cosmetic products.
  • the consumables may further contain flavoring agents.
  • the consumables are food products, including, for example, but not limited to, fruits, vegetables, juices, meat products (such as ham, bacon, and sausages), egg products, juice concentrates, gelatin, and gelatin-like products (such as jam, jelly, preserves, etc.), dairy products (such as yogurt, ice cream, sour cream) and sherbet, icing, syrup (including molasses, corn, wheat, rye, soybean, oat, rice and barley products), Nuts and nut products, cakes, biscuits, confectionery (such as candy, chewing gum (gum), fruity Dettol and chocolate), chewing gum (chewing gum), mints, cream, pies and bread.
  • food products including, for example, but not limited to, fruits, vegetables, juices, meat products (such as ham, bacon, and sausages), egg products, juice concentrates, gelatin, and gelatin-like products (such as jam, jelly, preserves, etc.), dairy products (such as yogurt, ice cream, sour
  • the food product is a beverage, which includes, for example, but is not limited to, coffee, tea, carbonated soft drinks (such as Coca-Cola (COKE) and Pepsi-Cola (PEPSI)), non-carbonated soft drinks and other fruit drinks, Sports drinks (such as Gatorade) and alcoholic beverages (such as beer, wine and liquor).
  • Consumables also include prepared packaged products such as granular flavor mixes reconstituted with water to provide non-carbonated beverages, instant pudding mixes, instant coffee and tea, coffee mates, malted milk mixes, pet foods, livestock feed, tobacco, and materials for baking applications such as powdered baking mixes for the preparation of breads, biscuits, cakes, pancakes, donuts, etc.
  • Consumables also include low-fat or low-calorie foods and beverages that contain little to no sucrose.
  • Preferred consumables include carbonated beverages.
  • Consumables further include flavorings such as herbs, spices and seasonings, flavor enhancers (eg monosodium glutamate), dietary sweeteners and liquid sweeteners.
  • the consumable product is a pharmaceutical composition, dietary supplement, nutraceutical, dental hygiene composition, or cosmetic product.
  • Preferred compositions are pharmaceutical compositions containing lipedoside B-IIIb, ligustilin C, ligustilin E, salts thereof or mixtures thereof, one or more pharmaceutically acceptable excipients, and a One or more active agents that exert biological effects other than sweetness enhancement.
  • active agents include pharmaceuticals and biological agents that have activities other than taste enhancement.
  • Such active agents are well known in the art (see, e.g., The Physician's Desk Reference).
  • Such compositions may be prepared according to procedures known in the art, for example, as described in Remington's Pharmaceutical Sciences, Mack Publishing Co., Easton, Pa. .
  • such active agents include bronchodilators, anorexics, antihistamines, nutritional supplements, laxatives, analgesics, narcotics, antacids, H2-receptor antagonists, anticholinergics Energetic, antidiarrheal, demulcent, antitussive, antinausea, antimicrobial, antibacterial, antifungal, antiviral, expectorant, anti-inflammatory, antipyretic, and mixtures thereof.
  • the active agent is selected from the group consisting of: an antipyretic analgesic (such as ibuprofen, acetaminophen, or aspirin), a laxative (such as dioctyl sodium phenolphthalein sulfosuccinate), Appetite suppressants (such as amphetamines, phenylpropanolamine, phenylpropanolamine hydrochloride or caffeine), antacids (such as calcium carbonate), antiasthmatics (such as theophylline), antidiarrheals (such as difenac noroxylate hydrochloride), anti-flatulence agents (e.g. simethecon), migraine agents (e.g.
  • an antipyretic analgesic such as ibuprofen, acetaminophen, or aspirin
  • a laxative such as dioctyl sodium phenolphthalein sulfosuccinate
  • Appetite suppressants such as amphe
  • ergotamine tartrate e.g. haloperidol
  • antispasmodics or sedatives such as phenobarbital
  • anti-hypertensive agents such as methyldopa or methylphenidate
  • sedatives such as benzodiazepine, hydroxyzine, meprobramate or phenothiazine
  • antihistamines Amine agents (such as astemizole, chlorpheniramine maleate, pyrilamine maleate, xylamine succinate, brompheniramine maleate, phenyltoloxamine citrate, chlorcyclizine hydrochloride, phenylamine maleate, or phenylindolamine tartrate), decongestants (such as phenylpropanolamine hydrochloride, phenylephrine hydrochloride, pseudoephedrine hydrochloride, pseudoephedrine sulfate, phenylpropanolamine bitart
  • propranolol alcohol withdrawal agents (e.g. disulfiram), antitussives (e.g. benzocaine, dextromethorphan, dextromethorphan hydrobromide, noscapine , chlorpheniramine and chlorbendarol hydrochloride), fluoride supplements (such as sodium fluoride), topical antibiotics (such as tetracycline or clindamycin), corticosteroid supplements (such as prednisone or prednisolone); anti-gout agents (e.g., colchicine or allopurinol), antiepileptic agents (e.g., phenytoin), antidehydration agents (e.g., electrolyte supplements), preservatives (e.g., cetylpyridinium chloride), NSAIDs (e.g., acetaminophen) phenol, ibuprofen, naproxen or its salts), gastrointestinal active agents (such as loperamide and
  • examples of dietary supplements or nutraceuticals include, but are not limited to, enteral nutritional products (used to treat nutritional deficiencies, trauma, surgery, Crohn's disease, kidney disease, hypertension, obesity, etc.), To improve athletic performance, muscle building or general health, or for inborn errors of metabolism such as phenylketonuria.
  • enteral nutritional products used to treat nutritional deficiencies, trauma, surgery, Crohn's disease, kidney disease, hypertension, obesity, etc.
  • such compositions may contain one or more amino acids with a bitter or metallic taste or aftertaste.
  • amino acids include, but are not limited to, essential amino acids such as leucine, isoleucine, histidine, lysine, methionine, phenylalanine, threonine, tryptophan, tyrosine acid, and the L isomer of valine.
  • dental hygiene compositions are known in the art and include, but are not limited to, toothpastes, mouthwashes, plaque rinses, dental floss, toothache relievers (such as ANBESOL), and the like.
  • the dental hygiene composition includes a natural sweetener.
  • the dental hygiene composition includes more than one natural sweetener.
  • a dental hygiene composition includes sucrose and corn syrup, or sucrose and aspartame.
  • beauty products include, but are not limited to, face creams, lipsticks, lip glosses, etc.
  • suitable cosmetic products for use in the present invention include lip balms such as CHAPSTICK or BURT'S BEESWAX lip balm.
  • the present invention also provides a method for enhancing the sweetness of flavoring agents with modifying properties and reducing their presence in Usage level methods in consumables.
  • the present invention provides a consumable product containing an olfactory effective amount of lipedoside B-IIIb, steatoside C, stegosteoside E, a salt thereof or a mixture thereof and a reduced amount of modified liposide B-IIIb. characteristics of the flavoring agent in order to achieve the same level of sweetness when the flavoring agent with modifying characteristics is used alone in conventional amounts.
  • the amount of flavoring agent with modifying properties used in the consumable product can be reduced by at least about 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or 95% %, from about 60% to about 99%, or from about 20% to about 50%.
  • lipedoside B-IIIb, lipedoside C, lipedoside E, salts thereof, or mixtures thereof may be used as sweetness enhancers in consumable products that retain the desired sweetness but contain a higher Low amounts of natural or artificial sweeteners.
  • lipedoside B-IIIb, lipedoside C, lipedoside E, salts thereof or mixtures thereof it is possible to produce modified carbonated drinks with the same sweetness as known carbonated soft drinks but with a lower sugar content. Soft drinks.
  • Additional materials may also be used in combination with lipedoside B-IIIb, steguridin C, steguridin E, salts thereof or mixtures thereof of the present invention to encapsulate and/or deliver residual aftertaste masking effects.
  • Some well-known materials are, for example, but not limited to, polymers, oligomers, other non-polymers such as surfactants, emulsifiers, lipids including fats, waxes and phospholipids, organic oils, mineral oils, petrolatum, Natural oils, perfume fixatives, fibers, starches, sugars and solid surface materials such as zeolites and silica.
  • Some preferred polymers include polyacrylates, polyureas, polyurethanes, polyacrylamides, polyesters, polyethers, polyamides, poly(acrylates-co-acrylamide), starch, silica, gelatin, and gum arabic, Alginate, chitosan, polylactide, poly(melamine-formaldehyde), poly(urea-formaldehyde), or combinations thereof.
  • Ligustrum lucidum leaf extract is prepared in water according to methods known to the skilled person. An extract containing lipedoside B-IIIb (0.3%), ligustilin C and ligustilin E (0.1%) was obtained.
  • lipedoside B-IIIb, lipedoside E and lipedoside K were each isolated and used in the following examples.
  • a sucrose solution (6%) was prepared in water and used as base solution.
  • lipedoside B-IIIb and stout ligustilin E were each prepared in base solutions of 1 and 0.3 ppm, respectively.
  • Ligustilin K (CAS No. 189276-67-3) was prepared in a base solution of 1.4 ppm and used as a control.
  • Lipedoside B-IIIb and Ligustilin E provide intense sweetness and sugary mouthfeel enhancement and are suitable for use in flavorings. Their close analogues, Ligustilin K, are less effective and are therefore not suitable for use in sweetening flavoring agents.

Abstract

提供了吡喃葡萄糖苷化合物用于增强甜味调节剂的甜味并且减少消耗品中使用的甜味调节剂的量的用途。

Description

用于增强甜味的新型吡喃葡萄糖苷组合物 背景技术
降低食品和饮料中的糖含量已成为食品工业的必要条件。食品和饮料制造商通常使用无热量、高强度的甜味调节剂(如莱鲍迪苷A(RebA)、阿斯巴甜、糖精、糖基化甜菊醇糖苷等)以部分或完全替代糖。然而，这些甜味调节剂可能表现出不希望的味道属性，如延迟的甜味起始、苦味和涩味的余味、以及缺乏醇厚感和口感。因此，甜味增强剂已成为有价值的工具，其减少糖和/或甜味调节剂的使用，以达到希望的甜味强度和口感并减少异味。
在现有技术中已经描述了甜味增强剂。例如，WO 2013/143822传授了腺苷作为某些糖的甜味增强剂的用途；EP 2606747描述了脱氧胆酸或其衍生物用于增强消耗品的甜味的用途；WO 2013/077668描述了源自酱油的聚糖或糖肽的甜味增强效果；WO 2012/107203传授了川陈皮素或其衍生物或水合物作为甜味剂或甜味增强剂的用途；WO 2009/023975描述了异罗汉果苷V作为甜味剂和甜味增强剂的用途；US 2008/0242740传授了用于增强甜味感官印象的烷酰胺与橙皮素和/或4-羟基二氢查耳酮的芳香组合物；并且WO 2007/014879和WO 2007/107596分别传授了橙皮素和4-羟基二氢查耳酮用于增强甜味物质的甜味或调味剂的甜味嗅觉印象的用途。
发明内容
本发明提供了一种通过将嗅觉有效量的由式I表示的吡喃葡萄糖苷化合物添加到甜味调节剂中来增强甜味调节剂的甜味的方法：
Figure PCTCN2022103589-appb-000001
其中R 1和R 2中的一个表示氢，并且其中另一个表示
Figure PCTCN2022103589-appb-000002
R a和R b独立地选自由氢和羟基组成的组；并且其中R表示C 4烯基。
在一个实施例中，本发明涉及一种增强甜味调节剂的甜味的方法，所述方法包括将嗅觉有效量的上述吡喃葡萄糖苷化合物添加到所述甜味调节剂中的步骤，其中所述吡喃葡萄糖苷化合物以粗壮女贞(Ligustrum robustum(Roxb.)Blume)叶提取物的形式提供。
在另一个实施例中，本发明涉及一种组合物，其包含甜味调节剂和嗅觉有效量的上述吡喃葡萄糖苷化合物。
在另一个实施例中，本发明涉及一种组合物，其包含甜味调节剂和嗅觉有效量的粗壮女贞叶提取物。
在另一个实施例中，本发明涉及一种消耗品，其包含甜味调节剂和嗅觉有效量的上述吡喃葡萄糖苷化合物。
在另一个实施例中，本发明涉及一种消耗品，其包含甜味调节剂和嗅觉有效量的粗壮女贞叶提取物。
通过阅读以下说明，本发明的这些和其他实施例将是显而易见的。
具体实施方式
在本发明中，式I可以通过例如但不限于以下结构来说明。
结构1：
Figure PCTCN2022103589-appb-000003
结构2：
Figure PCTCN2022103589-appb-000004
结构3：
Figure PCTCN2022103589-appb-000005
结构4：
Figure PCTCN2022103589-appb-000006
如本文所用，术语“烯基”意指含有至少一个碳-碳双键的直链或支链不饱和脂族烃。术语“一个/种(a/an)”应理解为意指一个/种或多个/种。术语“一种化合物”应理解为意指一种或多种由式I表示的吡喃葡萄糖苷化合物。
本文描述的化合物在本文中旨在包括此类化合物的异构体混合物以及可以使用本领域技术人员已知的技术分离的那些异构体。合适的技术包括色谱法，如高效液相色谱法(被称为HPLC)、特别是硅胶色谱法和被称为GC捕集的气相色谱法捕集。然而，此类产品的商业形式大多以混合物的形式提供。在本发明中，结构1表示，例如，lipedoside B-IIa(CAS号156979-57-6)；lipedoside B-IIb(CAS号157085-47-7)；lipedoside B-IIIa(CAS号157085-44-4)；lipedoside B-IIIb(CAS号157085-48-8)；β-D-吡喃葡萄糖苷、1-乙烯基-1,5-二甲基-4-己烯基3-O-(6-脱氧-α-L-吡喃甘露糖基)-,4-[(2E)-3-(4-羟基苯基)-2-丙烯酸酯](CAS号190896-33-4)；或其混合物。结构2表示，例如，粗壮女贞苷(ligurobustoside)E(CAS号189276-30-0)。结构3表示，例如，粗壮女贞苷C(CAS号176703-94-9)和粗壮女贞苷D(CAS号176779-11-6)。结构4表示，例如，粗壮女贞苷B(CAS号176703-93-8)。
在本发明中，已发现具有式I的吡喃葡萄糖苷化合物在食品中具有出乎意料且有利的用途。具体而言，已发现这些化合物增强了甜味调节剂的甜味，而没有不希望的异味。
特别地，已发现lipedoside B-IIIb、粗壮女贞苷C、粗壮女贞苷E、其盐或其混合物增强了甜味调节剂的甜味，而没有不希望的异味。因此，本发明提供了一种使用 lipedoside B-IIIb、粗壮女贞苷C、粗壮女贞苷E、其盐或其混合物来增强甜味调节剂的甜味并减少消耗品中使用的甜味调节剂的量的方法。
本发明的化合物是可商购的(例如，普瑞法科技开发有限公司(Biopurify Phytochemicals Ltd.)，中国)，并且还可从植物提取物中分离和纯化，例如像粗壮女贞(Ligustrum robustum(Roxb.)Blume)(也称为粗壮女贞(Ligustrum robustum))、粗壮连翘(Phillyrea robusta Roxb.)、粗壮木犀草(Olea robusta(Roxb.)Sweet)、Visiania robusta(Roxb.)DC.、紫叶女贞(Ligustrum purpurascens)、扩展女贞(Ligustrum expansum)、毛冬青茶或阔叶冬青。粗壮女贞在中国的西南区域广泛种植，并且长期以来被用作传统保健茶，命名为苦丁茶。据报道，其提取物具有对酰基辅酶A：胆固醇酰基转移(ACAT)酶的抑制效果，并且因此被认为可用于降低胆固醇水平(Fukuda等人,Chemical & Pharmaceutical Bulletin[化学与药物通报](1996),44(11):2173-2176)。据报道，粗壮女贞提取物还具有抗氧化活性(He等人,Journal of Natural Products[天然产物杂志](2003),66(6):851-854)。
如果以粗壮女贞提取物、特别是叶提取物的形式提供，则其富含lipedoside B-IIIb、粗壮女贞苷C和/或粗壮女贞苷E，以分别达到约0.01％和更高的含量。例如，粗壮女贞提取物叶提取物含有从约0.01％至约95％、从约0.05％至约50％或从约0.1％至约10％的lipedoside B-IIIb、粗壮女贞苷C和粗壮女贞苷E中的每一种。除非另外指明，否则百分比(％)是重量百分比。
例如，天然甜味剂包括，但不限于，蔗糖、果糖、葡萄糖、高果糖玉米糖浆、甜叶菊(Stevia rebaudiana)组合物(其包括RebA、甜菊苷、和莱鲍迪苷D(Reb D)的纯组分)、木糖、阿拉伯糖、或鼠李糖，以及糖醇如赤藓糖醇、木糖醇、甘露糖醇、山梨糖醇、肌醇及其组合。例如，人造甜味剂包括，但不限于，阿斯巴甜、三氯蔗糖、纽甜、乙酰磺胺酸钾、糖精及其组合。
调味剂是为消耗品提供特别味道和/或气味的制剂。具有改性特性的调味剂是调味剂的子集。将其添加到消耗品中以减少异味和/或改善总体特征。例如，本发明的具有改性特性的调味剂包括，但不限于，甜叶菊组合物，其包括甜菊苷、甜菊双糖苷、Reb A、莱鲍迪苷B(Reb B)、莱鲍迪苷C(Reb C)、Reb D、莱鲍迪苷E(Reb E)、莱鲍迪苷F(Reb F)、杜克苷A、杜克苷B、甜茶苷、α-葡萄糖基甜叶菊、果糖基甜 叶菊、半乳糖基甜叶菊、β-葡萄糖基甜叶菊，赛门苷，罗汉果苷IV，罗汉果苷V，罗汉果(Luo Han Guo)，莫纳甜(monatin)，甘草酸，奇异果甜蛋白，其盐，其糖基化衍生物及其组合。例如，糖基化衍生物可以通过与以下的转糖基化反应制备：但不限于，葡萄糖、果糖、半乳糖、鼠李糖、核糖、甘露糖、阿拉伯糖、岩藻糖、麦芽糖、乳糖、蔗糖、芦丁糖、山梨糖、木酮糖、核酮糖、rhammulose和木糖。在一个实施例中，本发明的具有改性特性的调味剂包括RebA、Reb C、甜茶苷、Reb D、罗汉果苷V、罗汉果、莫纳甜酸、其盐、其糖基化衍生物及其组合。本发明的具有改性特性的调味剂表现出弱的固有甜味。例如，本发明的一些其他调味剂包括，但不限于，仙茅甜蛋白、应乐果甜蛋白、马槟榔甜蛋白、巴西甜(brazzein)、荷南度辛(hernandulcin)、叶甜素、菝葜苷(glycyphyllin)、根皮苷、trilobtain、白云参苷(baiyunoside)、欧亚水龙骨甜素(osladin)、polypodosideA、蝶核苷(pterocaryoside)A、蝶核苷B、无患子倍半萜甙(mukurozioside)、糙苏苷(phlomisoside)I、巴西甘草甜素(periandrin)I、相思子苷(abrusoside)A、青钱柳苷(cyclocarioside)I及其组合。
因此，本发明的术语“甜味调节剂”是指包括天然甜味剂和人造甜味剂的甜味剂或以上列出的具有改性特性的调味剂。
术语“甜味”或“甜味强度”应理解为意指如个体(例如人)观察或体验到的甜蜜感觉的相对强度，或品尝者检测到的甜味的程度或量，例如，根据美国材料试验学会，特别技术出版物-434：“感官测试方法手册(Manual on Sensory Testing Methods)”，ASTM国际，西康舍霍肯，宾夕法尼亚州(1996)中描述的程序，在感官评价中使用的从0(无)至8(非常强)的等级。
术语“嗅觉有效量”应理解为意指与甜味调节剂组合使用的lipedoside B-IIIb、粗壮女贞苷C、粗壮女贞苷E、其盐或其混合物的量，其中lipedoside B-IIIb、粗壮女贞苷C、粗壮女贞苷E、其盐或其混合物增强了甜味调节剂的甜味。其嗅觉有效量可以取决于许多因素(包括其他成分、它们的相对量和希望的嗅觉效果)而改变。可以使用任何量的提供希望程度的甜味增强而不表现出异味的lipedoside B-IIIb、粗壮女贞苷C、粗壮女贞苷E、其盐或其混合物。在某些实施例中，嗅觉有效量的范围为按重量计从约1ppb至约1000ppm、优选按重量计从约2ppb至约100ppm并且更优选按重量计从约5ppb至约10ppm。当以植物提取物如粗壮女贞叶提取物的形式使用时，嗅 觉有效量的范围为按重量计从约100ppb至约5000ppm、优选按重量计从约1至约2000ppm并且更优选从约10至约1000ppm。
例如，消耗品包括食物产品(例如饮料)、甜味剂如天然甜味剂或人造甜味剂、药物组合物、膳食补充剂、保健营养品、牙齿卫生组合物和美容产品。消耗品可以进一步含有调味剂。
在一些实施例中，消耗品是食物产品，例如，其包括，但不限于，水果、蔬菜、果汁、肉制品(如火腿、培根和香肠)、蛋制品、浓缩果汁、明胶和类似明胶的产品(如果酱、果冻、蜜饯等)、奶制品(如酸奶、冰淇淋、酸性稀奶油)和果子露、糖衣、糖浆(包括糖蜜、玉米、小麦、黑麦、大豆、燕麦、大米和大麦制品)、坚果仁和坚果制品、蛋糕、饼干、糖食(如糖果、口香糖(gum)、果味滴露和巧克力)、口香糖(chewing gum)、薄荷糖、奶油、馅饼和面包。在某一实施例中，食物产品是饮料，例如，其包括，但不限于，咖啡、茶、碳酸软饮品(如可口可乐(COKE)和百事可乐(PEPSI))、非碳酸软饮品和其他果汁饮品、运动饮品(如佳得乐(GATORADE))和酒精饮料(如啤酒、葡萄酒和白酒)。消耗品还包括制备的包装产品，如颗粒状香精混合物，所述颗粒状香料混合物用水重构后提供非碳酸饮品、速溶布丁混合物、速溶咖啡和茶、咖啡伴侣、麦芽奶混合物，宠物食品，牲畜饲料，烟草，以及用于烘焙应用的材料，如用于制备面包、饼干、蛋糕、煎饼、甜甜圈等的粉末状烘焙混合物。消耗品还包括低脂或低卡食品和几乎不含蔗糖的饮料。优选的消耗品包括碳酸饮料。消耗品进一步包括调味品，如香草、香辛料和调味料、增味剂(例如谷氨酸一钠)、饮食甜味剂和液体甜味剂。
在其他实施例中，消耗品是药物组合物、膳食补充剂、保健营养品、牙齿卫生组合物、或美容产品。优选的组合物是药物组合物，其含有lipedoside B-IIIb、粗壮女贞苷C、粗壮女贞苷E、其盐或其混合物、一种或多种药学上可接受的赋形剂、以及一种或多种发挥除甜味增强外的生物效应的活性剂。此类活性剂包括有除味道增强外的活性的药物和生物试剂。此类活性剂是本领域众所周知的(参见，例如，The Physician's Desk Reference[医生案头参考])。可以根据本领域已知的步骤制备此类组合物，例如，如以下文献中描述：Remington's Pharmaceutical Sciences[雷明顿的医药科学],Mack Publishing Co.[马克出版公司],宾夕法尼亚州伊斯顿市。在一个实施例中，这种活性 剂包括支气管扩张剂、厌食剂、抗组胺剂、营养补充剂、缓泻剂、镇痛剂、麻醉剂、抗酸剂、H2-受体拮抗剂、抗胆碱能剂、止泻剂、缓和剂、镇咳剂、防恶心剂、抗微生物剂、抗细菌剂、抗真菌剂、抗病毒剂、祛痰剂、抗炎剂、解热剂、及其混合物。在另一个实施例中，活性剂选自由以下组成的组：解热镇痛剂(例如布洛芬、对乙酰氨基酚或阿司匹林)、缓泻剂(例如酚酞二辛基磺基琥珀酸钠)、食欲抑制剂(例如安非他明、苯丙醇胺、盐酸苯丙醇胺或咖啡因)、抗酸剂(例如碳酸钙)、镇喘剂(例如茶碱)、止泻剂(例如地芬诺酯盐酸盐)、抗肠胃气胀剂(例如二甲基硅油(simethecon))、偏头痛剂(例如酒石酸麦角胺)、精神药理学剂(例如氟哌啶醇)、解痉剂或镇静剂(例如苯巴比妥)、抗亢进剂(例如甲基多巴或哌醋甲酯)、镇静剂(例如苯二氮卓、羟嗪、甲丙氨酯(meprobramate)或吩噻嗪)、抗组胺剂(例如阿司咪唑、马来酸氯苯那敏、马来酸吡拉明、琥珀酸西拉敏、马来酸溴苯那敏、柠檬酸苯托沙敏、盐酸氯环利嗪、马来酸非尼拉敏、或酒石酸苯茚胺)、减充血剂(例如盐酸苯丙醇胺、盐酸去氧肾上腺素、盐酸伪麻黄碱、硫酸伪麻黄碱、重酒石酸苯丙醇胺或麻黄碱)、β-受体阻滞剂(例如普萘洛尔)、酒精戒断剂(例如双硫仑)、镇咳剂(例如苯佐卡因、右美沙芬、氢溴酸右美沙芬、诺司卡品、咳必清和盐酸氯苯达诺)、氟补充剂(例如氟化钠)、局部抗生素(例如四环素或克林霉素)、皮质类固醇补充剂(例如强的松或泼尼松龙)；抗痛风剂(例如秋水仙碱或别嘌醇)、抗癫痫剂(例如苯妥英钠)、抗脱水剂(例如电解质补充剂)、防腐剂(例如氯化十六烷基吡啶)、NSAID(例如对乙酰氨基酚、布洛芬、萘普生或其盐)、胃肠活性剂(例如洛哌丁胺和法莫替丁)、生物碱(例如磷酸可待因、硫酸可待因或吗啡)、微量元素补充剂(例如氯化钠、氯化锌、碳酸钙、氧化镁和其他碱金属盐和碱土金属盐)；维生素、离子交换树脂(例如消胆胺)、降胆固醇和降脂物质、抗心律失常药(例如N-乙酰普鲁卡因胺)和祛痰剂(例如愈创甘油醚)。例如，膳食补充剂或保健营养品的实例包括，但不限于，肠道营养产品(用于治疗营养不足、创伤、外科手术、克罗恩氏病、肾脏疾病、高血压、肥胖症等)，以改善运动表现、肌肉增强或一般健康、或如苯酮尿症的先天性代谢缺陷。特别地，此类组合物可以含有一种或多种具有苦味或金属味或余味的氨基酸。例如，此类氨基酸包括但不限于必需氨基酸，如亮氨酸、异亮氨酸、组氨酸、赖氨酸、甲硫氨酸、苯丙氨酸、苏氨酸、色氨酸、酪氨酸、和缬氨酸的L异构体。例如，牙齿卫生组合物在本领域是 已知的，并且包括，但不限于，牙膏、漱口剂、牙菌斑冲洗液、牙线、牙痛缓解剂(如ANBESOL)等。在一个实施例中，牙齿卫生组合物包括一种天然甜味剂。在另一个实施例中，牙齿卫生组合物包括多于一种天然甜味剂。在又另一个实施例中，牙齿卫生组合物包括蔗糖和玉米糖浆、或蔗糖和阿斯巴甜。例如，美容产品包括，但不限于，面霜、唇膏、唇彩等。在本发明中使用的其他合适的美容产品包括润唇膏，如防裂唇膏(CHAPSTICK)或BURT'S BEESWAX润唇膏。
此外，本发明还提供了用于通过掺入lipedoside B-IIIb、粗壮女贞苷C、粗壮女贞苷E、其盐或其混合物来增强具有改性特性的调味剂的甜味并降低其在消耗品中的使用水平的方法。在一个实施例中，本发明提供了一种消耗品，其含有嗅觉有效量的lipedoside B-IIIb、粗壮女贞苷C、粗壮女贞苷E、其盐或其混合物以及减少量的具有改性特性的调味剂，以便达到当所述具有改性特性的调味剂以传统量单独使用时的同一甜味水平。在这个方面，消耗品中使用的具有改性特性的调味剂的量可以减少至少约10％、20％、30％、40％、50％、60％、70％、80％、90％或95％、从约60％至约99％或从约20％至约50％。
如所指出的，lipedoside B-IIIb、粗壮女贞苷C、粗壮女贞苷E、其盐或其混合物可在消耗品中用作甜味增强剂，其保留了希望的甜味，但含有较低量的天然甜味剂或人造甜味剂。例如，通过添加lipedoside B-IIIb、粗壮女贞苷C、粗壮女贞苷E、其盐或其混合物，可以生产具有与已知碳酸软饮品相同甜味但具有更低的糖含量的改良的碳酸软饮品。
还可与本发明的lipedoside B-IIIb、粗壮女贞苷C、粗壮女贞苷E、其盐或其混合物结合使用额外的材料，以包封和/或传递残留余味掩蔽效应。一些众所周知的材料是，例如，但不限于，聚合物，低聚物，其他非聚合物如表面活性剂、乳化剂，脂质包括脂肪、蜡和磷脂质，有机油，矿物油，矿脂，天然油，固香剂(perfume fixative)，纤维，淀粉，糖和固体表面材料如沸石和二氧化硅。一些优选的聚合物包括聚丙烯酸酯、聚脲、聚氨酯、聚丙烯酰胺、聚酯、聚醚、聚酰胺、聚(丙烯酸酯-共-丙烯酰胺)、淀粉、二氧化硅、明胶和阿拉伯树胶、藻酸盐、壳聚糖、聚交酯、聚(三聚氰胺-甲醛)、聚(脲-甲醛)、或其组合。
作为本发明的具体实施例提供以下内容。本发明的其他修改对本领域技术人员将是显而易见的。此类修改应理解为在本发明的范围内。除非另行说明，否则材料购自奥德里奇化工公司(Aldrich Chemical Company)。除非另行说明，否则如本文所使用的所有百分比是重量百分比，ppm应理解为代表份数/百万份，L应理解为升，mL应解为毫升，g应理解为克，Kg应理解为千克，mol应理解为摩尔，mmol应理解为毫摩尔，psig应理解为磅力/平方英寸的表压，并且mmHg应理解为汞(Hg)的毫米数(mm)。如实例中使用的IFF应理解为意指美国纽约州纽约市的国际香精香料公司(International Flavors & Fragrances Inc.)。
实例I：测试样品的制备
根据技术人员已知的方法在水中制备粗壮女贞叶提取物。获得含有lipedoside B-IIIb(0.3％)、粗壮女贞苷C和粗壮女贞苷E(0.1％)的提取物。
此外，lipedoside B-IIIb、粗壮女贞苷E和粗壮女贞苷K各自被分离并用于以下实例中。
实例II：增强蔗糖甜味
在水中制备蔗糖溶液(6％)并用作底液。lipedoside B-IIIb和粗壮女贞苷E各自分别在1和0.3ppm的底液中制备。类似地，在1.4ppm的底液中制备粗壮女贞苷K(CAS号189276-67-3)并用作对照。
添加有lipedoside B-IIIb和粗壮女贞苷E的蔗糖溶液的风味特征报告如下：
Figure PCTCN2022103589-appb-000007
lipedoside B-IIIb和粗壮女贞苷E提供强烈的甜味和糖状口感增强，并且适合用于调味剂。它们的近似类似物粗壮女贞苷K效果较差，并且因此不适合用于增强甜味的调味剂。

Claims (20)

  1. 一种增强甜味调节剂的甜味的方法，所述方法包括将嗅觉有效量的由式I表示的化合物添加到所述甜味调节剂中的步骤：
    Figure PCTCN2022103589-appb-100001
    其中R 1和R 2中的一个表示氢，并且其中另一个表示
    Figure PCTCN2022103589-appb-100002
    R a和R b独立地选自由氢和羟基组成的组；并且其中R表示C 4烯基。
  2. 如权利要求1所述的方法，其中，所述甜味调节剂是甜味剂。
  3. 如权利要求2所述的方法，其中，所述甜味剂是选自由以下组成的组的天然甜味剂：蔗糖、果糖、葡萄糖、高果糖玉米糖浆、莱鲍迪苷A、甜菊苷、莱鲍迪苷D、木糖、阿拉伯糖、鼠李糖、赤藓糖醇、木糖醇、甘露糖醇、山梨糖醇、肌醇及其组合。
  4. 如权利要求2所述的方法，其中，所述甜味剂是选自由以下组成的组的人造甜味剂：阿斯巴甜、三氯蔗糖、纽甜、乙酰磺胺酸钾、糖精及其组合。
  5. 如权利要求1所述的方法，其中，所述甜味调节剂是选自由以下组成的组的具有改性特性的调味剂：甜菊苷、甜菊双糖苷、莱鲍迪苷A、莱鲍迪苷B、莱鲍迪苷C、莱鲍迪苷D、莱鲍迪苷E、莱鲍迪苷F、杜克苷A、杜克苷B、甜茶苷、α-葡萄糖基甜叶菊、果糖基甜叶菊、半乳糖基甜叶菊、β-葡萄糖基甜叶菊、赛门苷、罗汉果苷 IV、罗汉果苷V、罗汉果、莫纳甜、甘草酸、奇异果甜蛋白、其盐、其糖基化衍生物及其组合。
  6. 如权利要求1所述的方法，其中，所述嗅觉有效量为从约1ppb至约1000ppm。
  7. 如权利要求1所述的方法，其中，所述化合物选自由以下组成的组：lipedoside B-IIa；lipedoside B-IIb；lipedoside B-IIIa；lipedoside B-IIIb；β-D-吡喃葡萄糖苷、1-乙烯基-1,5-二甲基-4-己烯基3-O-(6-脱氧-α-L-吡喃甘露糖基)-,4-[(2E)-3-(4-羟基苯基)-2-丙烯酸酯]；粗壮女贞苷E；粗壮女贞苷C；粗壮女贞苷D；粗壮女贞苷B；及其混合物。
  8. 如权利要求7所述的方法，其中，所述化合物是lipedoside B-IIIb和粗壮女贞苷E的混合物。
  9. 如权利要求8所述的方法，其中，所述化合物以粗壮女贞(Ligustrum robustum(Roxb.)Blume)叶提取物的形式提供；并且其中所述嗅觉有效量为从约100ppb至约5000ppm。
  10. 一种组合物，其包含甜味调节剂和嗅觉有效量的由式I表示的化合物：
    Figure PCTCN2022103589-appb-100003
    其中R 1和R 2中的一个表示氢，并且其中另一个表示
    Figure PCTCN2022103589-appb-100004
    R a和R b独立地选自由氢和羟基组成的组；并且其中R表示C 4烯基。
  11. 如权利要求10所述的组合物，其中，所述甜味调节剂是甜味剂。
  12. 如权利要求11所述的组合物，其中，所述甜味剂是选自由以下组成的组的天然甜味剂：蔗糖、果糖、葡萄糖、高果糖玉米糖浆、莱鲍迪苷A、甜菊苷、莱鲍迪苷D、木糖、阿拉伯糖、鼠李糖、赤藓糖醇、木糖醇、甘露糖醇、山梨糖醇、肌醇及其组合。
  13. 如权利要求11所述的组合物，其中，所述甜味剂是选自由以下组成的组的人造甜味剂：阿斯巴甜、三氯蔗糖、纽甜、乙酰磺胺酸钾、糖精及其组合。
  14. 如权利要求10所述的组合物，其中，所述甜味调节剂是选自由以下组成的组的具有改性特性的调味剂：甜菊苷、甜菊双糖苷、莱鲍迪苷A、莱鲍迪苷B、莱鲍迪苷C、莱鲍迪苷D、莱鲍迪苷E、莱鲍迪苷F、杜克苷A、杜克苷B、甜茶苷、α-葡萄糖基甜叶菊、果糖基甜叶菊、半乳糖基甜叶菊、β-葡萄糖基甜叶菊、赛门苷、罗汉果苷IV、罗汉果苷V、罗汉果、莫纳甜、甘草酸、奇异果甜蛋白、其盐、其糖基化衍生物及其组合。.
  15. 如权利要求10所述的组合物，其中，所述嗅觉有效量为从约1ppb至约1000ppm。
  16. 如权利要求10所述的组合物，其中，所述化合物选自由以下组成的组：lipedoside B-IIa；lipedoside B-IIb；lipedoside B-IIIa；lipedoside B-IIIb；β-D-吡喃葡萄糖苷、1-乙烯基-1,5-二甲基-4-己烯基3-O-(6-脱氧-α-L-吡喃甘露糖基)-,4-[(2E)-3-(4- 羟基苯基)-2-丙烯酸酯]；粗壮女贞苷E；粗壮女贞苷C；粗壮女贞苷D；粗壮女贞苷B；及其混合物。
  17. 如权利要求16所述的组合物，其中，所述化合物是lipedoside B-IIIb和粗壮女贞苷E的混合物。
  18. 如权利要求17所述的组合物，其中，所述化合物以粗壮女贞叶提取物的形式提供；并且其中所述嗅觉有效量为从约100ppb至约5000ppm。
  19. 一种消耗品，其包含甜味调节剂和嗅觉有效量的由式I表示的化合物：
    Figure PCTCN2022103589-appb-100005
    其中R 1和R 2中的一个表示氢，并且其中另一个表示
    Figure PCTCN2022103589-appb-100006
    R a和R b独立地选自由氢和羟基组成的组；并且其中R表示C 4烯基。
  20. 如权利要求19所述的消耗品，其中，所述消耗品是食物产品；所述化合物以粗壮女贞叶提取物的形式提供；并且其中所述嗅觉有效量为从约100ppb至约5000ppm。
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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09104630A (ja) * 1995-10-11 1997-04-22 Pola Chem Ind Inc コレステロールアシルトランスフェラーゼ活性阻害剤及び組成物
AU2009241274A1 (en) * 2008-05-01 2009-11-05 Afexa Life Sciences Inc. Pharmaceutical composition comprising extracts of huanglian and Ku Ding Cha effective for lowering blood lipid levels
CN107485615A (zh) * 2017-08-11 2017-12-19 中国医学科学院药用植物研究所 粗壮女贞苷c及其组合物在制备治疗高脂血症及减肥药物中的用途
CN112384076A (zh) * 2018-07-12 2021-02-19 国际香料和香精公司 用于增强甜度的女贞甙酸及其衍生物
US20210177023A1 (en) * 2019-12-11 2021-06-17 International Flavors & Fragrances Inc. Compounds for sweetness enhancement
US20220046970A1 (en) * 2018-07-12 2022-02-17 International Flavors & Fragrances Inc. Verbascoside and related compounds for sweetness enhancement

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2368442B1 (en) 2005-07-27 2014-12-17 Symrise AG Use of hesperetin for enhancing the sweet taste
CA2613722A1 (en) 2005-07-27 2007-02-08 Symrise Gmbh & Co. Kg Use of hesperetin for enhancing the sweet taste
EP1977655B1 (de) 2007-03-29 2011-05-18 Symrise AG Aromakompositionen von Alkamiden mit Hesperetin und/oder 4-Hydroxydihydrochalkonen und deren Salzen zur Verstärkung süßer sensorischer Eindrücke
EP2188300B1 (en) 2007-08-17 2013-01-30 Givaudan SA Novel sweetener iso-mogroside v
WO2012107203A1 (en) 2011-02-08 2012-08-16 Nutrinova Nutrition Specialties & Food Ingredients Gmbh Sweetener and/or sweetness enhancer, sweetener composition, methods of making the same and consumables containing the same
JP5860542B2 (ja) 2011-11-23 2016-02-16 コリア フード リサーチ インスティテュート 甘味増強剤
EP2606747A1 (en) 2011-12-22 2013-06-26 Nutrinova Nutrition Specialties & Food Ingredients GmbH Sweetness enhancer, sweetener compositions, and consumables containing the same
WO2013143822A1 (en) 2012-03-26 2013-10-03 Imax Discovery Gmbh Adenosine as sweetness enhancer for certain sugars
CN102846720B (zh) * 2012-09-29 2013-11-13 广西梧州制药（集团）股份有限公司 一种降血脂、提高缺氧耐受力的组合物
CN104824759A (zh) * 2015-04-30 2015-08-12 安徽徽王食品有限公司 一种解渴蓝莓饮料及其制备方法
CN105919107A (zh) * 2016-05-31 2016-09-07 马鞍山市牛魔王科技发展有限公司 一种高蛋白含量罗汉果润肺当归陈皮咀嚼片及其制备方法
CN109007082A (zh) * 2018-07-25 2018-12-18 兴义市绿缘中药材种植农民专业合作社 一种能够降低小叶苦丁茶苦味的加工方法
WO2020118002A1 (en) 2018-12-06 2020-06-11 International Flavors & Fragrances Inc. Boehmeria nivea compositions and methods for taste modulation
CN111838369A (zh) * 2020-07-21 2020-10-30 余庆乌江泉小叶苦丁茶业有限公司 一种余庆小叶苦丁茶代用茶配方工艺

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09104630A (ja) * 1995-10-11 1997-04-22 Pola Chem Ind Inc コレステロールアシルトランスフェラーゼ活性阻害剤及び組成物
AU2009241274A1 (en) * 2008-05-01 2009-11-05 Afexa Life Sciences Inc. Pharmaceutical composition comprising extracts of huanglian and Ku Ding Cha effective for lowering blood lipid levels
CN107485615A (zh) * 2017-08-11 2017-12-19 中国医学科学院药用植物研究所 粗壮女贞苷c及其组合物在制备治疗高脂血症及减肥药物中的用途
CN112384076A (zh) * 2018-07-12 2021-02-19 国际香料和香精公司 用于增强甜度的女贞甙酸及其衍生物
US20220046970A1 (en) * 2018-07-12 2022-02-17 International Flavors & Fragrances Inc. Verbascoside and related compounds for sweetness enhancement
US20210177023A1 (en) * 2019-12-11 2021-06-17 International Flavors & Fragrances Inc. Compounds for sweetness enhancement

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