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WO2006068212A1 - Inhibiteur de lipase et medicament prophylactique / remede pour maladies cutanees - Google Patents

Inhibiteur de lipase et medicament prophylactique / remede pour maladies cutanees Download PDF

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Publication number
WO2006068212A1
WO2006068212A1 PCT/JP2005/023575 JP2005023575W WO2006068212A1 WO 2006068212 A1 WO2006068212 A1 WO 2006068212A1 JP 2005023575 W JP2005023575 W JP 2005023575W WO 2006068212 A1 WO2006068212 A1 WO 2006068212A1
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WIPO (PCT)
Prior art keywords
lipase
proanthocyanidin
proanthocyanin
skin diseases
lipase inhibitor
Prior art date
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PCT/JP2005/023575
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English (en)
Japanese (ja)
Inventor
Makoto Saito
Kouichi Kasai
Tomoko Kanamori
Masayuki Arii
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Kikkoman Corporation
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Priority to JP2006549052A priority Critical patent/JPWO2006068212A1/ja
Publication of WO2006068212A1 publication Critical patent/WO2006068212A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/45—Ericaceae or Vacciniaceae (Heath or Blueberry family), e.g. blueberry, cranberry or bilberry
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/04—Antipruritics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/10—Anti-acne agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
    • C07D311/62—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2 with oxygen atoms directly attached in position 3, e.g. anthocyanidins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
    • A61K2800/782—Enzyme inhibitors; Enzyme antagonists
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/006—Antidandruff preparations

Definitions

  • the present invention relates to a lipase inhibitor and a prophylactic / therapeutic agent for skin diseases caused by bacterial lipase.
  • Skin diseases caused by bacterial lipase include, for example, inflammatory cases caused by lipase produced by the microorganism Propionibacterium acnes (hereinafter referred to as P. acnes) present in the skin.
  • P. acnes Propionibacterium acnes
  • Inflammatory eczema such as acne, pimples, sardines, and comedones, dandruff caused by increased lipase activity of skin resident bacteria, and generation of body odor such as side odor.
  • plant extracts are effective for prevention and treatment of acne, for example, one or two selected from bilberry (Vaccinium vitis-idaea L.) extract and its extract fractions.
  • bilberry Vaccinium vitis-idaea L.
  • microbial lipase inhibitors containing more than one species
  • Patent Document 3 skin external preparations for preventing and treating millet
  • Patent Document 1 Japanese Patent Application Laid-Open No. 2004-244379
  • Patent Document 2 JP 2002-97147 A
  • Patent Document 3 Japanese Patent Application Laid-Open No. 2004-115466
  • An object of the present invention is to provide a novel lipase inhibitor and a prophylactic / therapeutic agent for skin diseases caused by bacterial lipase. Means for solving the problem
  • cranberry extract is useful as an agent for preventing and treating skin diseases caused by lipase inhibitors and bacterial lipases.
  • the present inventors fractioned the active ingredient in the Cranberry extract, confirmed that it was proanthocyanidin, and completed the present invention. That is, the present invention relates to the following.
  • a lipase inhibitor containing proanthocyanidin as an active ingredient 1.
  • a lipase inhibitor comprising cranberry extract containing proanthocyanidins as an active ingredient.
  • a food, beverage, pharmaceutical or cosmetic comprising the lipase inhibitor according to item 1.
  • a prophylactic and therapeutic agent for skin diseases caused by bacterial lipase containing proanthocyanidin as an active ingredient.
  • a prophylactic / therapeutic agent for skin diseases caused by bacterial lipase comprising a cranberry extract containing proanthocyanidins as an active ingredient.
  • the present invention is a lipase inhibitor containing proanthocyanidin as an active ingredient.
  • the lipase include bacterial lipases, specifically those derived from skin resident bacteria such as P. acnes.
  • Proanthocyanidins refer to a group of compounds in which flavan 3-ol or flavan 3,4-diol is a structural unit and bonded by condensation or polymerization at the 4-position to the 6-position or the 4-position to the 8-position.
  • the proanthocyanins of the present invention include proanthocyanates such as polymeric procyanidins, prodelphidins, and propellergodins composed of trimers, tetramers, and even 10-mers of structural units. Gin and their stereoisomers are also included.
  • one or more of the bonds between the structural units are a carbon-oxygen bond (ether bond) at the 2-position 7-position hydroxyl group in addition to the carbon-carbon bond at 4-position 6-position or 4-position 8-position.
  • ether bond a carbon-oxygen bond
  • A-type bond a structure in which structural units are bonded to each other via two bonds (A-type bond)
  • A-type proanthocyanines are also included.
  • a type proanthocyanin is abundant in cranberries and peanuts.
  • proanthocyanidins from the viewpoint of the effect as a lipase inhibitor, a mixture of proanthocyanidin pentamer to 9mer, or proanthocyanidin trimer to 7mer It is particularly preferred to use a multimer such as a mixture of
  • a type A proanthocyanin trimer is represented by the following formula.
  • the proanthocyanin of the present invention may be an isolated and purified pure product or a plant extract containing broanthocyanin.
  • the plant extract can be obtained by extracting plants containing proanthocyanines such as grapes, oysters, apples, pine, peanuts, chestnuts, azuki beans and cranberries with water or organic solvents.
  • the plant extract can be further subjected to distillation under reduced pressure, spray drying, freeze drying, or the like to remove the solvent and increase the proanthocyanin content.
  • Lipase inhibitors containing proanthocyanidins as active ingredients are food and drink, pharmaceuticals or It can be used orally or parenterally with cosmetics.
  • Proanthocyanin is preferably added in such a way that the weight is, for example, 1 mg to 10 gZ adult Z days, more preferably 10 mg to LgZ adult Z days.
  • a lipase inhibitor comprising a cranberry extract containing proanthocyanidins as an active ingredient:
  • the present invention also provides a lipase inhibitor comprising a cranberry extract containing proanthocyanidin as an active ingredient.
  • Lipases include bacterial lipases, specifically those derived from skin resident bacteria such as P. acnes.
  • Cranberries are small fruit pods that originate in both Europe and North America.
  • the original species and cultivars can be used.
  • the cultivar is a fruit tree of about 20cm in height of the Vaccinium macrocarpon species or Vaccinium oxycoccus species native to Winsconsin, USA. Examples include Stevens, Benlear, Pilgrim, Early black, and Bergman.
  • a "cranberry extract containing proanthocyanidin” (hereinafter simply referred to as “cranberry extract”) is a cranberry extract having lipase inhibitory activity and a yarn and composition containing proanthocyanin Say.
  • the proanthocyanidins include, as described above, proanthocyanates such as polymer procyanidins, prodelphidins, and propellagogins, which have a trimeric, tetrameric, or even 10-mer or more power unit. Gin and their stereoisomers.
  • the extract can be obtained by extracting a cranberry plant under conditions containing proanthocyanidin. Cranberry seeds, fruits, pulp, peels and other tissues can be used as raw materials for extraction. Cranberry juice or fruit juice concentrate is also included in the Cranberry extract of the present invention.
  • a composition having a lipase inhibitory activity can be obtained by extracting the above extraction raw material under suitable conditions using water or an organic solvent.
  • Organic solvents include, for example, water-soluble alcohols such as methanol, ethanol, isopropanol, n-butanol, acetone, ethyl methyl ketone, acetonitrile, 1,4-dioxane, N, N-dimethylformamide (D MF), acetic acid and the like.
  • the water-soluble organic solvent may be used alone, or may be used by mixing with water at an arbitrary ratio.
  • the cranberry extract obtained above can also be used as an active ingredient of the present invention. Further, in order to further enhance the activity of the extract, a column chromatograph using Cefadettas, polyamide, silica gel, ODS, etc. Purification / separation operations such as membrane separation using cellulose membranes, liquid-liquid separation using ethyl acetate-water, etc., and decomposition of impurities by addition of microorganisms such as yeast may be performed. As shown in the Examples, since proanthocyanin in the cranberry extract has a lipase inhibitory activity, it is preferable to employ conditions for increasing the content of proanthocyanin in the purification and separation operation.
  • cranberry juice When concentrating cranberry juice, it can be concentrated by any of the following methods, such as liquid membrane flow-down method, TASTE method, ultrafiltration method, reverse osmosis membrane method, freeze-drying method, and concentration method under reduced pressure.
  • a lipase inhibitor containing cranberry extract containing proanthocyanidins as an active ingredient can be added to foods, drinks, pharmaceuticals or cosmetics and used orally or parenterally.
  • the cranberry extract may be added so that the dry weight of the extract is, for example, lOmg to: LOOgZ adult Z day, preferably 100 mg to 10 gZ adult Z day.
  • the present invention also relates to a preventive / therapeutic agent for skin diseases caused by bacterial lipase, comprising proanthocyanidin or cranberry extract as an active ingredient.
  • Proanthocyanin and cranberry extract can exert a preventive or therapeutic effect on skin diseases caused by bacterial lipase through lipase inhibitory activity.
  • the bacterial lipase is a lipase derived from a skin resident bacterium such as P. acnes.
  • Skin diseases include, for example, the generation of body odors such as millet, pimples, cooking, comedones, dandruff, side odors, etc. caused by lipases derived from skin resident bacteria such as P. acnes.
  • the weight is, for example, from lmg to 10gZ adult Z days, preferably from lOmg to: LgZ adult Z days. It can be taken orally.
  • the dry weight of the extract is, for example, 1 Omg ⁇ : LOOgZ adult Z day, preferably 100mg to 10gZ adult Z day, the dose may be taken orally or parenterally.
  • the above intake may be set appropriately according to the physical condition, gender, age, and purpose of intake (prevention, treatment or symptom reduction).
  • the present invention is a food, drink, pharmaceutical or cosmetic containing the above-mentioned preventive or therapeutic agent for skin diseases.
  • the agent of the present invention is used as a food or drink, the proanthocyanidin or cranberry extract may be added to an appropriate food or drink, such as a beverage, confectionery, seasoning, or side dish.
  • the agent of the present invention can also be used as a functional food of capsule, granule, fine granule, syrup or drink type.
  • proanthocyanidin or cranberry extract can be formulated as an oral preparation, an external preparation for skin or an injection with other components.
  • Oral preparations include tablets, capsules, granules, fine granules, syrups, and drinks, and parenteral preparations include sterile solutions, suspensions and other injections, ointments, creams, solutions, etc. And other external preparations.
  • Other ingredients used in the formulation include, for example, excipients, integration agents, lubricants, swelling agents, sweeteners, coating agents, fragrances, preservatives, antioxidants, buffering agents and the like.
  • a liquid carrier such as fats and oils can be contained in addition to the above materials.
  • the proanthocyanidin or cranberry extract may be prepared as a cosmetic together with a commonly used base material. Its usage is preferably applied to the skin.
  • cranberry extract was used as a sample to confirm bacterial lipase inhibitory activity and therapeutic effect against skin diseases (acne). Subsequently, the active ingredient in the cranberry extract was fractionated, and it was confirmed that it was proanthocyanin. In the examples, the unit of numerical values is% by weight unless otherwise specified.
  • the cells were cultured at 32 ° C for 48 hours to obtain a single colony of P. acnes.
  • the obtained colonies were cultured at 32 ° C. for 48 hours in an anaerobic GAM liquid medium (Nissi).
  • the bacterial cells are collected by centrifugation, then dispersed and washed twice with 50 mM Tris-HCl (pH 7.4), and sonicated in the same buffer under ice-cooling to give a crude enzyme solution containing lipase derived from P. acnes. Got. (2) Preparation of cranberry extract
  • the following extracts were prepared using cranberries mainly composed of Stevens species and used as test samples.
  • Fresh raw cranberry fruit lOOOOg was squeezed with a squeezer and then concentrated under reduced pressure. As a concentrated solution, 100 g was obtained.
  • the cranberry juice concentrate had a solid content of 50%, a total polyphenol content of 1.3%, a total proanthocyanin content of 0.5%, and a total anthocyanin content of 0.2%.
  • This cranberry juice concentrate had a solid content of 50%, a total polyphenol content of 4.8%, a total proanthocyanin content of 2.3%, and a total anthocyanin content of 0.6%.
  • Cranberry fruit juice concentrate (solid content 50%, total polyphenol content 1.3%) 50 g was purified by column chromatography using Sepa beads (200 g). In column chromatography, the juice concentrate was diluted with 250 ml of ion exchange water, adsorbed onto the column, washed with ion exchange water, and then eluted with 70% aqueous ethanol. Fractions containing polyphenol were collected, concentrated under reduced pressure, and then lyophilized to obtain 1.6 g of powder. This high purity cranberry extract has a total polyphenol content of 34.2% and a total proanthocyanin content. 12. 6%, total anthocyanin content 2.4%.
  • the cranberry extract prepared in (2) was added as a test sample to the lipase-containing crude enzyme solution of (1) at various concentrations, and the lipase inhibitory activity of the cranberry extract was evaluated.
  • the ribose activity was measured by a fluorescence measurement method using 4-methylumbelliferyoleate (4-MU-oleate; Sigma).
  • Example 1 demonstrates that cranberry extract is useful as a lipase inhibitor.
  • test drinks containing cranberry extract on skin diseases was evaluated by the following method.
  • Fructose, acidulant, etc. were mixed with cranberry juice mainly composed of Stevens seeds to prepare a beverage (125 ml) having the following composition.
  • Composition Energy 68kcal, Protein Og, Lipid Og, Carbohydrate 17g, Sodium 86mg, Vitamin C 37.5mg, Cranberry-derived compound (800mg quinic acid, Total positive phenol content 21 lmg, Total proanthocyanin content 41mg, Total Anthocyanin content
  • the subjects were healthy adult women in their 30s who were aware of rough skin, breakouts, and acne.
  • the purpose and contents of the test were fully explained in advance and written consent was obtained.
  • Test group (12 women, 35.5 ⁇ 0.6) who took the test subjects' skin after taking the skin measurements in consideration of attributes such as age, physique, skin quality, constitution, etc. (2 years old) or a control group (12 females, 35. 1 ⁇ 0. 5 years old) for seasonal variation measurement that does not specify drink intake in particular, so that the prior skin condition is as even as possible It was.
  • the test group received two test drinks daily, one in the morning and one in the evening.
  • the test period was 4 weeks, and each test item was measured three times before intake, 2 weeks after intake, and 4 weeks after intake. Life during the test period was not particularly limited except for the intake of the test drink.
  • the skin diagnosis by a beauty specialist was performed by visual inspection and palpation to diagnose the skin condition.
  • Diagnosis items by visual inspection are ⁇ Finger millet breakout '', ⁇ Transparency '', ⁇ Blemish '', ⁇ Redness '', ⁇ Smoothness '', and Diagnostic items by palpation are ⁇ Moistness '', ⁇
  • the three items were “smoothness” and “total skin condition”.
  • the criteria for diagnostic items are very bad (1 point), poor power (2 points), slightly bad (3 points), neither (4 points), slightly good (5 points), and quite good (6 points) ), Very good (7 points), 7 grades, replaced with scores.
  • the specialists who performed the visual inspection and palpation considered not to divide the group to which the test subject belongs. The results are shown in Table 2.
  • the growth inhibition test of P. acnes was conducted by the following method.
  • Example 2 A single colony of P. acnes obtained in Example 1 was inoculated into 10 mL of GAM liquid medium for anaerobic bacteria, and the bacterial solution that had been allowed to stand at 32 ° C for 48 hours was then boiled and degassed with physiological saline. 10-fold diluted, the out lmL to solidified anaerobes for GAM agar 10 cm 2 dish it was uniformly coated by Konra di bars.
  • a sample aqueous solution having a predetermined concentration was infiltrated into a sterilized filter paper having a diameter of 18 mm, and was allowed to stand in the center of an agar medium coated with bacterial cells. The bacteriostatic action was evaluated by comparing the diameters of circles formed by inhibiting the growth of the fungi after culturing at 32 ° C for 48 hours. As a positive control, salt benzalcoum was used. The results are shown in Table 3.
  • Non-polyphenol fraction 10. Og powder was obtained. The total polyphenol content in the powder was 0.1%, the total proanthocyanin content was 0.0%, and the total anthocyanin content was 0.0%.
  • the fraction eluted with 100 ml of 70% aqueous ethanol solution was concentrated under reduced pressure from the column after elution of the “non-polyphenol fraction”, and then freeze-dried to give 0.5 g of “polyphenol fraction” powder.
  • the total polyphenol content in the powder was 59.0%, the total proanthocyanin content was 33.1%, and the total anthocyanin content was 7.3%.
  • the above-mentioned "polyphenol fraction” was fractionated by the method described in Journal of the Science Food and Agriculture (81: 1306-1313, 2001). Specifically, 2 g of the “polyphenol fraction” was subjected to column chromatography using Sephadex LH20 (300 ml), ion-exchanged water, 50% aqueous ethanol solution, ethanol, a 1: 1 mixture of ethanol and methanol, methanol, 80 Elution was sequentially performed with 6 kinds of aqueous solutions of 800% acetone (800 ml each), and each fraction was concentrated under reduced pressure and then lyophilized to obtain the following 6 kinds of fractions.
  • Example 1 Using the cranberry extract obtained in Example 1 as an active ingredient, it is possible to prepare foods, drinks, pharmaceuticals or cosmetics containing a prophylactic / therapeutic agent for skin diseases caused by bacterial lipase.
  • This tablet can be used as an internal medicine or functional food.
  • Capsules containing 50 mg of cranberry extract, 6 mg of potato starch, 4 mg of light anhydrous keyed acid, 1 mg of calcium stearate, 80 mg of lactose as a tablet are obtained by conventional methods.
  • a solution in which the following components (1) to (6) are mixed and dissolved and a solution in which the components (7) to (10) are mixed and dissolved are mixed and made uniform to obtain a lotion.
  • a novel lipase inhibitor derived from cranberry extract containing proanthocyanidin as an active ingredient and a prophylactic / therapeutic agent for skin diseases caused by bacterial lipase containing the same as an active ingredient
  • foods and drinks, pharmaceuticals or cosmetics containing the same can be provided.

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Abstract

L’invention concerne un inhibiteur de lipase contenant, comme ingrédient actif, de la « proanthocyanidine » ou un « extrait d’airelles rouges contenant de la proanthocyanidine » ; un médicament prophylactique / remède pour les maladies cutanées causées par la lipase bactérienne ; et des aliments, boissons, médicaments ou produits cosmétiques contenant cette même substance.
PCT/JP2005/023575 2004-12-22 2005-12-22 Inhibiteur de lipase et medicament prophylactique / remede pour maladies cutanees WO2006068212A1 (fr)

Priority Applications (1)

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JP2006549052A JPWO2006068212A1 (ja) 2004-12-22 2005-12-22 リパーゼ阻害剤及び皮膚疾患の予防・治療剤

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008018638A1 (fr) * 2006-08-11 2008-02-14 Kracie Foods, Ltd. Inhibiteur d'absorption de graisse et aliment et boisson utilisant celui-ci
JP2008239620A (ja) * 2007-03-01 2008-10-09 Kazuko Hirai クランベリー果汁を有効成分とする抗アレルギー剤
EP2133121A1 (fr) * 2008-06-11 2009-12-16 Laboratoires SANTINOV Additifs nutritionnels comprenant d'extrait de canneberge destinés au système digestif et leurs utilisations
JP2010227002A (ja) * 2009-03-27 2010-10-14 Kikkoman Corp クランベリー抽出物及びその製造方法
CN101525327B (zh) * 2008-03-06 2011-12-14 陕西嘉禾植物化工有限责任公司 一种从越橘中提取花青素的方法
WO2014092175A1 (fr) * 2012-12-14 2014-06-19 株式会社 明治 Polyphénol spécifique utilisé dans des produits alimentaires et de boisson, des compléments, des produits pharmaceutiques, et similaires et procédé de fabrication dudit polyphénol spécifique
EP4062901A1 (fr) * 2021-03-26 2022-09-28 Lumene Oy Utilisation cosmétique d'ingrédients de baies nordiques pour soutenir un microbiome de peau sain

Citations (8)

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JPH09291039A (ja) * 1995-12-26 1997-11-11 Suntory Ltd プロシアニジンを有効成分とする抗肥満剤
JP2001335499A (ja) * 2000-05-29 2001-12-04 Ichimaru Pharcos Co Ltd 化粧料組成物
JP2002000230A (ja) * 2000-06-28 2002-01-08 Kikkoman Corp 飲食用粉末組成物
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EP4062901A1 (fr) * 2021-03-26 2022-09-28 Lumene Oy Utilisation cosmétique d'ingrédients de baies nordiques pour soutenir un microbiome de peau sain

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