WO2006067864A1 - Composition contenant de la proanthocyanidine - Google Patents

Composition contenant de la proanthocyanidine Download PDF

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Publication number
WO2006067864A1
WO2006067864A1 PCT/JP2004/019788 JP2004019788W WO2006067864A1 WO 2006067864 A1 WO2006067864 A1 WO 2006067864A1 JP 2004019788 W JP2004019788 W JP 2004019788W WO 2006067864 A1 WO2006067864 A1 WO 2006067864A1
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WO
WIPO (PCT)
Prior art keywords
proanthocyanidins
group
catechins
weight
extract
Prior art date
Application number
PCT/JP2004/019788
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English (en)
Japanese (ja)
Inventor
Kinya Takagaki
Takeshi Mitsui
Original Assignee
Toyo Shinyaku Co., Ltd.
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 Toyo Shinyaku Co., Ltd. filed Critical Toyo Shinyaku Co., Ltd.
Priority to PCT/JP2004/019788 priority Critical patent/WO2006067864A1/fr
Publication of WO2006067864A1 publication Critical patent/WO2006067864A1/fr

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Classifications

    • 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
    • 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 
    • A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics

Definitions

  • the present invention relates to a composition for enhancing the bioactive action of proanthocyanidins.
  • Proanthocyanidins are condensed or polymerized tannins (hereinafter referred to as polycondensation) present in various plants, and are a group of compounds obtained by polycondensation using flavan 1-ol or flavan 1,3-diol as a constituent unit. is there. These are given their names because they produce anthocyanidins such as cyanidin, delphinidin, and pelargonidin by acid treatment.
  • oligomeric proanthocyanidin hereinafter referred to as OPC.
  • Proanthocyanidins are a kind of polyphenols and have a strong antioxidant action (Japanese Patent Laid-Open No. Sho 61-16982), and further improve blood lipids; antihypertensive effects; Effect of suppressing blood sugar level rise; Effect of restoring blood vessel elasticity
  • Anti-vascular effect It is known to have an effect of increasing the utilization efficiency of vitamin C; and an effect of improving blood fluidity.
  • An object of the present invention is to provide a novel composition that can further enhance various physiologically active actions of proanthocyanidins.
  • composition of the present invention is characterized by containing proanthocyanidins and catechins having a 3,4,5-trihydroxyphenyl group.
  • composition of the present invention contains proanthocyanidins and catechins having a 3,4,5-trihydroxyphenyl group.
  • the 3, 4, 5_trihydroxyphenino group is a galloyl group.
  • compositions containing the above-mentioned proanthocyanidins and trihydroxenyl group-containing power textiles to improve the blood lipids and lipid metabolism of proanthocyanidins It can remarkably enhance physiological activities such as blood glucose level rise inhibitory effect, antihypertensive effect, blood flow improving effect, and skin beautifying effect. These effects are excellent effects that cannot be obtained by single administration of catechins having a proanthocyanidin and a trihydroxyphenyl group, respectively.
  • the composition of the present invention can be effectively used for foods, pharmaceuticals, quasi drugs, cosmetics and the like. Brief Description of Drawings
  • Figure 1 shows a rat with a pine bark extract and a category with trihydroxyphenyl groups. Feeds containing quinine, pine bark extract and catechin not containing trihydroxyphenyl group, and feed containing only pine bark extract 2 It is a graph which shows transition of the blood pressure increase rate.
  • composition of the present invention contains proanthocyanidins and catechins having a 3, 4, 5_trihydroxyphenyl group, and optionally contains other components.
  • proanthocyanidins and catechins having a 3, 4, 5_trihydroxyphenyl group and optionally contains other components.
  • each component will be described.
  • proanthocyanidins used in the present invention those containing a large amount of a condensation polymer having a low degree of polymerization are suitable.
  • a condensation polymer having a low degree of polymerization a condensation polymer having a degree of polymerization of 2 to 30 (a 2 to 30 mer) is preferable, and a condensation polymer having a degree of polymerization of 2 to 10 (a 2 to 10 mer).
  • a condensation polymer having a degree of polymerization of 2 to 4 (2 to 4 mer: OPC) is more preferred.
  • OPC is a particularly powerful antioxidant.
  • Proanthocyanidins are concentrated in plant leaves, bark, fruit peels or seeds.
  • Proanthocyanidins are specifically the bark of plants such as pine, straw, and yamatake; grapes, blueberries, strawberries, avocados, false acacia, berries or seeds of barley; wheat; soybeans; black It is contained in soybeans, cacao, red beans, tochi nut shells, peanut skins, ichiyo leaves, etc. Also, West African cola nuts, Peruvian Latania roots. Japanese green tea is known to contain OPC. OPC is a substance that cannot be produced in the human body.
  • proanthocyanidins with a high OPC content or proanthocyanidins with a high OPc content are used.
  • proanthocyanidins with a high degree of polymerization are used.
  • excellent lipid metabolism improvement effect, antihypertensive effect, blood glucose level rise suppression effect, etc. are obtained.
  • materials such as the bark of the above-mentioned plant, pulverized fruits or seeds, or extracts thereof can be used.
  • an extract derived from a plant because it contains abundant proanthocyanidins, and it is particularly preferable to use an extract derived from pine bark.
  • pine bark is rich in OPC, so it is preferably used as a raw material for proanthocyanidins.
  • the extract is preferably one from which impurities have been removed.
  • pine bark rich in OPC as a raw material plant will be described as a method for preparing an extract containing puffer anthocyanidin as a main component.
  • Pinus martima Pinus martima, larch, black pine, waka pine, Japanese pine, pine pine, Korean pine, high pine, Ryuyuki pine, Utsushima pine, Daiyu pine, white pine, Quebec in Canada
  • An extract of a bark of a plant belonging to the order of pine is preferably used. Above all, the bark extract of French coastal pine (Pinus Martima) is preferred.
  • French coastal pine is a marine pine that grows on the Atlantic coast of southern France.
  • This French coastal pine bark contains proanthocyanidins, organic acids, and other physiologically active ingredients.
  • Proanthocyanidins which are the main ingredients, have strong antioxidative effects to remove active oxygen. It is known that there is.
  • the pine bark extract is obtained by extracting the above pine bark with water or an organic solvent. When water is used, it is preferable to use warm water or hot water. To improve the extraction efficiency, salt such as sodium chloride is added to these waters. And are preferred.
  • organic solvent used for extraction organic solvents that are acceptable for the production of foods or pharmaceuticals are used.
  • water and organic solvents may be used alone or in combination.
  • water, hot water, ethanol, water-containing ethanol, and water-containing propylene glycol are preferable, and water, hot water, ethanol, and water-containing ethanol are more preferable from the viewpoint of safety when used in foods and pharmaceuticals.
  • the method for extracting proanthocyanidins from pine bark is not particularly limited. For example, by extracting 1 to 50 parts by weight of hot water of 50 to 120 ° C., preferably 70 to 100 ° C. with respect to 1 part by weight of pine bark dry, A pine bark extract having a high bioactivity and high water solubility can be obtained. A warm extraction method, a supercritical fluid extraction method, or the like may be used.
  • supercritical fluid extraction may be performed by an entrainer addition method.
  • ethanol, propanol, n-hexane, acetone, toluene, other aliphatic lower alcohols, aliphatic hydrocarbons, aromatic hydrocarbons, or ketones are added to a supercritical fluid.
  • it is a method for enhancing the selectivity of separation, and a method for efficiently obtaining a pine bark extract.
  • pine bark extracts For extraction from pine bark, you can combine several extraction methods. It is possible to obtain pine bark extracts with various compositions by combining multiple extraction methods. It becomes ability.
  • the pine bark extract obtained by the above extraction may be purified for the purpose of increasing the content of proanthocyanidins.
  • a solvent such as ethyl acetate is usually used, but from the viewpoint of safety as a food or pharmaceutical, a method that does not use a solvent, such as ultrafiltration or Diaion HP-2O, Sephadex It is preferable to purify by a column method or a batch method using an adsorbent carrier such as LH 20 or chitin.
  • the pine bark extract containing proanthocyanidin as a main component is specifically prepared by the following method, but this is an example and is not limited to this method.
  • the washing step is repeated twice, in which the precipitate is added again to 1 L of chloroform and precipitated.
  • this method for example, about 5 g of pine bark extract containing 20% by weight or more of OPC and 5% by weight or more of strong techins can be obtained.
  • Extracts derived from raw material plants such as the above pine husks contain 40% by weight or more of pro It is preferable to contain anthocyanidin. Further, the extract derived from the raw material plant preferably contains 20% by weight or more of OPC, more preferably 30% by weight or more. As described above, a pine bark extract is preferably used as a raw material containing proanthocyanidins in a high proportion.
  • OPC is an antioxidant, it has the effect of reducing the risk rate of adult diseases such as cancer, heart disease, and cerebral thrombosis, and has the effect of improving the allergy in nature such as arthritis, atopic dermatitis, and hay fever.
  • it suppresses bacterial growth in the oral cavity and reduces plaque (dental glands); restores the elasticity of blood vessels; prevents lipoproteins in the blood from being damaged by active oxygen; It also has the effect of preventing cholesterol from adhering to the inner wall of blood vessels and adhering cholesterol; the effect of regenerating vitamin E decomposed by active oxygen; and the effect of enhancing vitamin E.
  • composition of the present invention contains catechins having a 3,4,5-trihydroxyphenyl group (hereinafter sometimes referred to as THP catechins).
  • Catechin is a generic name for polyhydroxyflavan 1-ol, (+) — force techin (referred to as catechin in a narrow sense), gallocatechin, afuzerekin, (+) 3-galloyl derivative of The 3-galloyl derivative of yopi gallocatechin is common.
  • THP catechins examples include (+)-gallocatechin, (1) one-epigalocatechin, force-techin gallate, epicatechin gallate, gallocatechin gallate, and epigallocatechin gallate.
  • catechins in which the trihydroxyphenyl group is a galloyl group are preferred.
  • Such catechins having a galloyl group include force techin gallate, epicatechin gallate, gallocatechin gallate, and epigallocatechin gallate.
  • THP catechins are contained in plants such as camellias (for example, tea leaves such as green tea, black tea, and ulong tea) and mao. These plants or their meals or extracts may be used as THP catechins. Preferably, it is a camellia plant, or a pulverized product thereof or an extract thereof.
  • green tea leaves contain about 10-15% catechins, of which about 80% or more are THP catechins and about 50% or more are TH P catechins. Since it is a catechin having one galloyl group, it is preferable.
  • THP catechins together with proanthocyanidins, can remarkably enhance various bioactive effects of proanthocyanidins.
  • THP catechins are materials that efficiently enhance the multiple bioactive effects of proanthocyanidins.
  • catechins having a galloyl group not only have high antioxidant activity, but also have excellent effects such as an inhibitory effect on blood glucose level increase, antihypertensive effect, anti-lipaemia, and the like, so proanthocyanidins It is possible to remarkably enhance various physiologically active actions possessed by.
  • THP catechins are other anti-carcinogenic effects, arteriosclerosis-preventing effects, fat-metabolism-suppressing effects, blood pressure rise-inhibiting effects, platelet aggregation-inhibiting effects, anti-allergic effects, anti-viral effects, anti-bacterial effects, caries-preventing effects, bad breath It is known to have an inhibitory action, an intestinal microbiota normalizing action, an active oxygen and free radical scavenging action, and an antioxidant action.
  • composition of the present invention contains the above-mentioned proanthocyanidins and THP catechins, and may contain various components as necessary.
  • normal food and medicine Ingredients that can be added as excipients (excipients, extenders, binders, thickeners, emulsifiers, colorants, fragrances, nutritional ingredients, food additives, etc.); and usually as external preparations for skin of cosmetics, quasi drugs Ingredients used (whitening agent, moisturizer, antioxidant, UV absorber, UV scattering agent, antiseptic, fragrance, gelling agent, polymer, oil component, surfactant, thickener, alcohol, Powder components, colorants, aqueous components, various skin nutrients, etc.).
  • Nutritional components include, for example, ascorbic acid, tocopherol, riboflavin, vitamins such as 3 -carotene, folic acid, and piotin; minerals such as calcium, magnesium, selenium, iron; included in taurine, garlic, etc.
  • Flavanoids such as hesperidin and quercetin; Flavonoids; Dietary fibers such as indigestible dextrin, alginic acid, chitin, chitosan and guagam; Proteins such as soy protein and collagen; Peptides; Amino acids; Milk Animal fats such as fat, lard, beef tallow and fish oil; vegetable oils such as soybean oil and rapeseed oil; fruits such as orange, lemon, grapefruit and strawberry and their juices; royal jelly and propolis.
  • food-added calories include honey, reduced maltose, lactose, sugar alcohol, liquid sugar, and seasonings.
  • the composition of the present invention contains proanthocyanidins and THP strength textiles and, if necessary, other ingredients.
  • proanthocyanidins and THP catechins may be any of isolated compounds, food materials containing them, and extracts of the food materials.
  • a plant extract containing THP strength is added to a plant extract containing proanthocyanidins.
  • it contains proanthocyanidins such as pine bark and cinnamon bark, and most of the catechins contained are trihydroxide.
  • a plant extract containing THP catechins is added to a plant extract that is a catechin that does not have a siphenyl group.
  • the plant extract contains both proanthocyanidins and THP catechins
  • add necessary ingredients for example, pine bark extract containing a large amount of proanthocyanidins
  • the amount ratio of each component in the composition can be adjusted as appropriate.
  • the content ratio of proanthocyanidins and THP catechins in the composition of the present invention is arbitrary.
  • the above-mentioned THP strength techins are 1 part by weight to 5000 parts by weight, more preferably 3 parts by weight to 2000 parts by weight, still more preferably 10 parts by weight to 1000 parts by weight, Most preferably, it can be contained in a proportion of 50 to 500 parts by weight.
  • proanthocyanidin in the composition of this invention is preferably contained so that the daily intake per adult is 1 to 1000 mg, more preferably 2 to 500 mg as proanthocyanidins.
  • transdermal administration since it is a topical administration, it is preferable to have a predetermined concentration.
  • proanthocyanidins are preferably contained in the composition in an amount of preferably 0.0001% to 20% by weight. More preferably, it may be contained in a proportion of 0.0001% to 10% by weight, more preferably 0.001% to 10% by weight, and most preferably 0.01% to 10% by weight.
  • THP catechins are preferably 0. 00001 wt% to 20 wt%, more preferably 0.001 wt% to 20 wt%, more preferably 0.001 wt% to 20 wt%, most preferably 0.01 wt% to 20 wt% May be contained.
  • the composition of the present invention can be prepared in various forms depending on the purpose, for example, as a food, a pharmaceutical, a quasi-drug, or a cosmetic.
  • composition of the present invention when the composition of the present invention is orally ingested (administered) as food, pharmaceuticals, quasi drugs, etc., there is no particular limitation on the form.
  • capsules such as hard capsules and soft capsules, tablets, pills, powder (powder), granules, tea bags, bowl-like viscous liquids, liquids, pastes, etc. are used in a form commonly used by those skilled in the art. .
  • these may be taken as they are, or may be taken by dissolving in water, hot water, milk, etc., or may be taken after leaching the ingredients.
  • composition of the present invention is applied to the skin as a quasi-drug, cosmetic, etc.
  • these forms are not particularly limited, such as ointments, creams, emulsions, lotions, packs, poultices, bath preparations, etc. Any form can be used as long as it is conventionally used for an external preparation for skin.
  • pine husk extract containing 40% by weight of proanthocyanidins as a material containing proanthocyanidins (containing 20% by weight of OPC in the material) (trade name: Flavandinol, Toyo Shinyaku Co., Ltd.) ) was used.
  • the THP catechins, catechin 8 0 weight 0/0 containing green tea-derived extract (trade name, containing these forces catechins having Garoi Le group 6 0 wt% or more: Porifuenon 7 0 S, Tokyo Food Techno Co., Ltd.) and an extract derived from green tea containing 93% by weight of Epigalocatechin Gallate (trade names: Theavigo, Roche “Vitamin” Japan Co., Ltd.) were used.
  • polyphenone 70 S contains 48% by weight or more of THP-powered tekins, Referred to as the “tea catechin 48", “Teabiko” is, the THP force catechins from that it contains 93 by weight 0/0 or more, Les as “tea catechin 93", to Ukoto.
  • Catechin (Sigma Aldrich Japan) was used as a catechin having no trihydroxyphenyl group.
  • a solid feed was prepared in the same manner as in Example 1 except that tea catechin 93 was used instead of tea catechin 48 (referred to as feed 2). (Comparative Example 1)
  • a solid feed was prepared in the same manner as in Example 1 except that catechin was used instead of tea catechin 48 (referred to as feed 3).
  • a solid feed was prepared in the same manner as in Example 1 except that tea catechin 48 was not mixed (referred to as feed 4). (Comparative Example 3)
  • a solid feed was prepared in the same manner as in Example 1 except that the pine bark extract was not mixed (referred to as feed 5).
  • Three-week-old male guinea pigs (Japan SLC Co., Ltd.) were given a commercial solid feed (RC4, Oriental Yeast Co., Ltd.) for one week to acclimate.
  • the guinea pigs were divided into groups of 7 by a total randomization method. Each group of guinea pigs was allowed free intake of the above feeds 1-5 for 28 days. Furthermore, as a control group, a group that freely ingested purified feed was established. After the intake period, the total cholesterol level, LDL cholesterol level, HDL cholesterol level, and triglyceride level in the blood of each group of guinea pigs were measured. The results are shown in Table 1. The measurement method is as follows.
  • Total cholesterol (mgZd L) was measured by enzymatic method using “Serotech” TCHO-L (manufactured by Serotech Co., Ltd.).
  • LDL cholesterol (mgZd L) was measured by an enzyme method using Cholestest LDL (Daiichi Chemical Co., Ltd.).
  • HDL cholesterol (mg / d L) was measured by enzymatic method using Choleest HDL (Daiichi Chemical Co., Ltd.).
  • Triglyceride (mgZd L) was measured by an enzymatic method using “Cellotech” TG-L (manufactured by Seguchi Tech Co., Ltd.). table 1
  • a solid feed was prepared in the same manner as in Example 4 except that catechin was used instead of tea catechin 48 (referred to as feed 7).
  • a solid feed was prepared in the same manner as in Example 4 except that tea catechin 48 was not mixed (referred to as feed 8).
  • the composition containing pine bark extract and THP catechins has an effect of improving blood lipids and suppressing an increase in blood glucose level. Is considered to be obtained.
  • SHR and other disease model joint study group Four-week-old male SHR rats (SHR and other disease model joint study group) were acclimated with a basic diet and water for one week. The rats were divided into 7 groups, so that the average fit of each group was almost uniform. The rats in each group were allowed to freely take the above diets 6-8 for 28 days. In addition, a group with free intake of basic feed was established as a control group. During the intake period, all groups received free drinking water containing 1% by weight of NaC1.
  • Pine bark extract, tea catechin 93, and excipients are mixed in the proportions (weight%) shown in Table 3 to produce tablets (about 200 mg per tablet). Yes.
  • the balance is purified water
  • the group to which the skin lotion (lotion 1) containing the pine bark extract of the example and the THP catechins was applied was either one of the pine bark extract of the comparative example and the THP strength techin. It can be seen that skin wrinkles, spots, and kusumi are improved compared to the group to which the skin lotion containing only the skin lotion (skin lotions 2 and 3) is applied. This indicates that the pine peel extract and trihydroxif 2 It shows that a composition containing a catechin having a ru group has a beautifying effect.
  • composition of the present invention can be administered orally (taken) or transdermally (applied) to improve the lipid metabolism of proanthocyanidins, improve blood lipids, suppress blood glucose elevation, and antihypertensive.
  • Physiologically active effects such as blood flow improvement effect and skin beautifying effect can be remarkably enhanced. These effects are excellent effects that cannot be obtained when proanthocyanidins and THP strength techins are administered alone.
  • the composition of the present invention can be used for foods, pharmaceuticals, quasi drugs, cosmetics and the like.

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  • Health & Medical Sciences (AREA)
  • Diabetes (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Endocrinology (AREA)
  • Emergency Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L’invention concerne une composition comprenant une proanthocyanidine et une catéchine possédant un groupement trihydroxyphényle. Ladite composition renforce de manière remarquable les diverses activités physiologiques de la proanthocyanidine.
PCT/JP2004/019788 2004-12-24 2004-12-24 Composition contenant de la proanthocyanidine WO2006067864A1 (fr)

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PCT/JP2004/019788 WO2006067864A1 (fr) 2004-12-24 2004-12-24 Composition contenant de la proanthocyanidine

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Application Number Priority Date Filing Date Title
PCT/JP2004/019788 WO2006067864A1 (fr) 2004-12-24 2004-12-24 Composition contenant de la proanthocyanidine

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002275076A (ja) * 2001-03-15 2002-09-25 Toyo Shinyaku:Kk 血糖上昇抑制剤および健康食品
JP2003095964A (ja) * 2001-09-21 2003-04-03 Toyo Shinyaku:Kk 抗ストレス剤
JP2003095965A (ja) * 2001-09-27 2003-04-03 Toyo Shinyaku:Kk 高血圧症の予防・治療剤
JP2003146898A (ja) * 2001-11-09 2003-05-21 Toyo Shinyaku:Kk 高脂血症改善剤
JP2003238428A (ja) * 2002-02-18 2003-08-27 Toyo Shinyaku:Kk 冷え症改善剤および健康食品
WO2003090673A2 (fr) * 2002-04-22 2003-11-06 Rtc Research & Development, Llc. Compositions et methodes pour favoriser la perte de poids, la thermogenese, la diminution de la faim, une masse musculaire maigre, augmenter le metabolisme et amplifier les niveaux energetiques et utilisation en tant que complement alimentaire chez des mammiferes
JP2004346132A (ja) * 2003-05-20 2004-12-09 Toyo Shinyaku:Kk フラバン化合物含有組成物

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002275076A (ja) * 2001-03-15 2002-09-25 Toyo Shinyaku:Kk 血糖上昇抑制剤および健康食品
JP2003095964A (ja) * 2001-09-21 2003-04-03 Toyo Shinyaku:Kk 抗ストレス剤
JP2003095965A (ja) * 2001-09-27 2003-04-03 Toyo Shinyaku:Kk 高血圧症の予防・治療剤
JP2003146898A (ja) * 2001-11-09 2003-05-21 Toyo Shinyaku:Kk 高脂血症改善剤
JP2003238428A (ja) * 2002-02-18 2003-08-27 Toyo Shinyaku:Kk 冷え症改善剤および健康食品
WO2003090673A2 (fr) * 2002-04-22 2003-11-06 Rtc Research & Development, Llc. Compositions et methodes pour favoriser la perte de poids, la thermogenese, la diminution de la faim, une masse musculaire maigre, augmenter le metabolisme et amplifier les niveaux energetiques et utilisation en tant que complement alimentaire chez des mammiferes
JP2004346132A (ja) * 2003-05-20 2004-12-09 Toyo Shinyaku:Kk フラバン化合物含有組成物

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