WO2006061915A1 - Skin remedy composition - Google Patents
Skin remedy composition Download PDFInfo
- Publication number
- WO2006061915A1 WO2006061915A1 PCT/JP2004/018777 JP2004018777W WO2006061915A1 WO 2006061915 A1 WO2006061915 A1 WO 2006061915A1 JP 2004018777 W JP2004018777 W JP 2004018777W WO 2006061915 A1 WO2006061915 A1 WO 2006061915A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- skin
- weight
- proanthocyanidins
- pine bark
- component
- Prior art date
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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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid, pantothenic acid
- A61K31/198—Alpha-aminoacids, e.g. alanine, edetic acids [EDTA]
-
- 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
- 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
- A61K31/365—Lactones
- A61K31/375—Ascorbic acid, i.e. vitamin C; Salts thereof
Definitions
- the present invention relates to a skin improvement composition.
- Collagen is the main component of skin or blood vessels, and is a flexible fibrous protein that occupies 25-30% of the human body. If the production of collagen is normal, it can maintain tension and smooth skin. Furthermore, in blood vessels, elastic blood vessels are formed, and arteriosclerosis is unlikely to occur. 'However, collagen production ability (synthesis ability) decreases due to aging, uneven nutrition due to unbalanced diets, etc., and this decrease in collagen production causes skin itchiness and sagging.
- the objective of this invention is providing the skin improvement composition which has the outstanding skin quality improvement effect.
- the present inventors surprisingly have a pine bark extract and a collagen production promoting effect. It was found that the combination with an amino acid exerted an excellent collagen production enhancing effect both in the oral administration and the transdermal administration, and as a result, the skin quality was improved, and the present invention was completed. It was.
- the skin improvement and synthesis product of the present invention contains proanthocyanidins and amino acids having an effect of promoting collagen production.
- ascorbic acid or a derivative thereof is further contained.
- the proanthocyanin is derived from pine bark.
- the skin improvement composition of the present invention contains proanthocyanidins (hereinafter sometimes referred to as “A component”) and amino acids having an effect of promoting collagen production (hereinafter sometimes referred to as “amino acid component” and “B component”). Preferably, it may further contain ascorbic acid or a derivative thereof (hereinafter sometimes referred to as “C component”).
- a component proanthocyanidins
- amino acid component amino acids having an effect of promoting collagen production
- ascorbic acid or a derivative thereof hereinafter sometimes referred to as “C component”.
- This skin improvement composition may contain other components as required.
- each component will be described.
- proanthocyanidins are those having a degree of polymerization of flavan 1-3-ol and Z or flavan 1 3,4-diol as a structural unit of 2 or more.
- a condensation polymer having a low polymerization degree particularly a condensation polymer having a polymerization degree of 2 to 4 (2 to 4 mer) is preferably used.
- a polycondensation polymer having a degree of polymerization of 2 to 4 is referred to as oligomeric proanthocyanidin (hereinafter OPC).
- OPC oligomeric proanthocyanidin
- Allo / intanidin is a kind of polyphenols, a powerful anti-acid substance produced by plants, concentrated in plant leaves, bark, fruit peel or seed parts.
- Proanthocyanin especially OPC, specifically, the bark of plants such as pine, persimmon, and yam; grapes, blueberries, strawberries, apogado, green tea, berries or seeds of barley; wheat; soybeans; black soybeans Cocoa; beans; tochi nut shells; peanut skins; Also in West African cola nuts, Peruvian Latania roots, Japanese green tea,
- OPC is included. 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 compared to the case of using proanthocyanidins with a high degree of polymerization (low OPC content).
- OPC can contribute not only to a direct skin quality improvement effect but also to an indirect skin quality improvement effect.
- proanthocyanidins used in the skin improving thread and adult product of the present invention food ingredients such as the above-mentioned bark, fruit or seed meal, or extracts thereof can be used.
- an extract derived from pine bark is preferable to use.
- pine bark is rich in OPC, and is therefore preferably used as a raw material for proanthocyanidins.
- an example of using pine bark rich in OPC as a raw material plant will be described as a method for preparing an extract containing puffer anthocyanin as a main component.
- Pine pine bark extracts include Pinus Martima, larch, black pine, waka pine, himekomatsu, pine pine, Korean pine, pine, Ryuyuki pine, luck pine, pine pine, white pine, and 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 pine is a marine pine that grows on the Atlantic coast of southern France. This French coastal pine bark contains proanthocyanidin, organic acids, and other physiologically active ingredients, and removes the active oxygen from the main ingredients, the proanthocyanidins of the flavonoids. It is known to have a strong antioxidant effect.
- the pine bark extract is obtained by extracting the pine bark with water or an organic solvent.
- water it is preferable to use warm water or hot water.
- a salt such as sodium chloride to these waters.
- the organic solvent used for extraction an organic solvent that is acceptable for the production of foods or drugs is used.
- aqueous organic solvents may be used alone or in combination.
- hot water, hydrous ethanol, and hydrous propylene glycol are preferably used.
- the method for extracting proanthocyanidins from pine bark is not particularly limited, For example, a warm extraction method or a supercritical fluid extraction method is used.
- Supercritical fluid extraction is a method that uses a supercritical fluid, which is a fluid that exceeds the critical point (critical temperature, critical pressure) of a substance's gas-liquid.
- a supercritical fluid which is a fluid that exceeds the critical point (critical temperature, critical pressure) of a substance's gas-liquid.
- the supercritical fluid carbon dioxide, ethylene, propane, nitrous oxide (laughing gas) and the like are used, and carbon dioxide is preferably used.
- the supercritical fluid extraction method performs an extraction process of extracting a target component with a supercritical fluid and a separation process of separating the target component and the supercritical fluid.
- the separation step any of extraction separation by pressure change, extraction separation by temperature change, or extraction separation using an adsorbent / absorbent may be performed.
- 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.
- the solubility of the target extract such as OPC and catechins (described later) in the extraction solvent is dramatically increased.
- it is a method for enhancing the selectivity of separation, and a method for efficiently obtaining a pine bark extract.
- the supercritical fluid extraction method can be operated at a relatively low temperature, so it can be applied to substances that are altered and decomposed at high temperatures; the advantage is that the extraction fluid does not remain; and the recycling of the solvent is possible. There is an advantage that the solvent process can be omitted and the process becomes simple.
- Extraction from pine bark may be performed by a liquid carbon dioxide batch method, a liquid carbon dioxide reflux method, a supercritical carbon dioxide reflux method, or the like in addition to the above method.
- a plurality of extraction methods may be combined. It is edible to obtain pine bark extracts with various compositions by combining multiple extraction methods.
- the pine bark extract obtained by the above extraction may be purified for the purpose of increasing the proanthocyanidin content.
- a solvent such as ethyl acetate is usually used.
- a method that does not use a solvent is required to facilitate the application to skin cosmetics and quasi drugs as external preparations.
- it is preferable to purify by ultrafiltration or a column method or a batch method using an adsorbent biocarrier such as Diaion HP — 20, Cefadex-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 precipitate is dissolved in 100 ml of ethyl acetate, and then added to 1 L of black mouth form again for precipitation, and then a washing step is repeated twice.
- a washing step is repeated twice.
- the extract derived from the raw material plant such as pine bark preferably contains 40% by weight or more of proanthocyanidins.
- this source plant derived preferably contains 20% by weight or more of OPC, more preferably 30% by weight or more.
- a pine bark extract is preferably used as a raw material containing proanthocyanidins in a high proportion.
- plant extracts such as the above-mentioned pine bark extract further contain catechins together with proanthocyanidins, particularly ⁇ PC.
- Strength Tekins is a general term for polyhydroxyflavan 1-3-ol.
- (+)-catechin referred to as catechin in the narrow sense
- (1) one-catecatechin, (+)-gallocatechin, (_)-epigalocatechin, epigalocatechin gallate, epicatechin gallate Affzerekin is known.
- the catechins are preferably contained in the raw material plant extract in an amount of 5% by weight or more. More preferably, the extract contains 20% by weight or more of OPC and 5% by weight or more of catechins. For example, if the extract contains less than 5% by weight of strength techins, the strength may be adjusted so that the final content is 5% by weight or more. It is most preferable to use a pine bark extract containing 20% by weight or more of OPC and 5% by weight or more of catechins.
- the content of proanthocyanidins contained in the skin improvement and composition of the present invention is not particularly limited. It is preferably contained in the skin improvement composition so that the daily intake of proanthocyanidins is preferably 5 mg to 100 mg, more preferably 10 mg to 50 O mg.
- the skin improvement composition When used as an external preparation, it is locally administered.
- the din is preferably contained in an amount of 0.001 to 10% by weight, more preferably 0.01 to 5% by weight. If the amount is less than 0. 5% by weight, the skin quality improving action is not sufficiently exerted, and if it exceeds 10% by weight, formulation may be difficult.
- Proanthocyanidins used in the present invention have an effect of enhancing collagen production, and therefore can improve skin quality.
- the amino acid having an effect of promoting collagen production contained in the skin improvement composition of the present invention is an important amino acid that is a constituent component of collagen, and preferably from proline, glycine, arginine, and alanine. And at least one amino acid selected from the group consisting of:
- These amino acids are the components of collagen that contain an average of 2% proline, an average of 21% glycine, an average of 8.1% of alanine, and an average of 6.9% of arginine. Contained. These are amino acids that are normally synthesized in vivo but are difficult to ingest sufficient amounts from a normal diet.
- the above amino acids have better absorption efficiency in both transdermal administration and oral administration than collagen, so they are more effectively absorbed and easily converted into collagen in the body than in the case of administering collagen itself. Is done. Therefore, the above-mentioned amino acid can have a higher skin quality improving effect when combined with proanthocyanidins than collagen.
- Proline is particularly important for improving skin because the collagen that makes up the skin is an essential amino acid for the helix structure. That is, collagen is formed by three polypeptide chains having a helix structure.
- proline in the collagen is reduced using vitamin C as a coenzyme. This is because it becomes hydroxyproline, and the three polypeptide chains form a hydrogen bond with the hydroxyl group of the hydroxyproline to form a helix.
- the amino acid is preferably contained in the skin improvement composition of the present invention so that the daily intake is 50 mg to 20 g, preferably 100 mg to 10 g.
- the amount of amino acid may be appropriately adjusted so that it can be administered topically.
- 0.001 to 5% by weight in the skin improvement composition is more preferable.
- Ascorbic acid (vitamin C) and its derivatives are important for collagen synthesis.
- the collagen production enhancing effect can be further enhanced. This effect is particularly effective when the composition of the present invention is orally administered. If you transdermal administration, in order to facilitate the percutaneous absorption of Asukorubin acid, it is not preferable to use a Asukorubin acid lipophile 'I 1 production is enhanced in palmitic Sana Sukorubiru.
- Ascorbic acid and its derivatives may be contained in the skin-improving composition preferably in an amount of 0.0001 to 30% by weight, more preferably 0.001 to 10% by weight.
- the skin improvement composition of the present invention may contain various components in addition to the above components depending on the application.
- ingredients that can be added as normal foods and pharmaceuticals antioxidants, excipients, fillers, binders, thickeners, emulsifiers, lubricants, wetting agents, suspending agents, coloring agents, flavoring agents, Nutritional ingredients, food additives, etc.
- ingredients normally used as skin preparations for cosmetics, pharmaceuticals, etc. whitening agents, moisturizers, antioxidants, oily ingredients, surfactants, thickeners, alcohols
- Powder components colorants, aqueous components, various skin nutrients, etc.
- the antioxidant may be contained for the purpose of preventing rough skin due to oxidation and aging.
- examples of such antioxidants include SOD, mannitol, carotenoids (eg, wastaxanthin), hydroquinone, ubiquinone, bilbiline, cholesterol, tryptophan, histidine, vitamin P-like substances (rutin, quercetin, hesperidin, etc.) Gallic acid, vitamins B, vitamin D or its derivatives, vitamin E, dartathione, BTH, B HA, plant extracts (eg, argon and rosemary).
- Such an antioxidant is preferably from 0.01 to 40% by weight in the skin-improving composition. It can be contained in a ratio of / 0 .
- the skin improvement composition When ingesting the skin improvement composition as a food, medicine, etc., preferably at a rate of 0.01% to 20% by weight, more preferably 0.01% to 10% by weight.
- it may be contained preferably in a proportion of 0.01 to 40% by weight, more preferably 0.01 to 20% by weight.
- Nutritional ingredients include, for example, royal jelly, vitamins, protein, strong rumum-containing materials (eg eggshell calcium), lecithin, chlorella powder, ashtaba powder, and moroheiya powder.
- food additives include stevia powder, matcha powder, lemon powder, honey, reduced maltose, lactose, sugar solution, and seasonings.
- the skin improvement composition of the present invention contains proanthocyanidins and amino acids having an effect of promoting collagen production, and the ratio thereof is arbitrary.
- the amino acid is preferably contained in an amount of 50 to 500 parts by weight, more preferably 10 to 500 parts by weight with respect to 100 parts by weight of proanthocyanidins. Can do.
- the skin improvement composition of the present invention may further contain ascorbic acid or a derivative thereof and other components in addition to the above essential components.
- This skin improvement composition can be prepared in various forms as, for example, foods, pharmaceuticals, quasi-drugs, cosmetics, etc. for the purpose of obtaining a skin quality improvement effect.
- the skin improvement composition of the present invention when orally ingested 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, 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.
- the skin improvement composition of the present invention is applied to the skin as a quasi-drug, cosmetics, etc.
- these forms are not particularly limited, and are for ointments, creams, emulsions, mouth lotions, packs, poultices, baths. Any form may be used as long as it is a form used in conventional skin external preparations such as a preparation.
- mouthwash such as mouthwash, toothpaste, eye drops, etc. J3 may be in a form suitable for application to the mucous membrane in the air or eyes, and these can obtain mucosal strengthening and protective action by the same action .
- the skin improvement composition of the present invention contains a proanthocyanin and an amino acid having an effect of promoting collagen production, and takes in foods, pharmaceuticals, etc. comprising the composition, or applies cosmetics or the like to the skin. Increases the amount and exhibits an excellent skin quality improvement effect. This effect can be obtained even when the ability to produce collagen is reduced.
- the composition of the present invention can be used as a food, a pharmaceutical product, a quasi-drug, a cosmetic product, etc. excellent in improving skin firmness and preventing wrinkles.
- the composition of the present invention is useful as a topical skin preparation or health food that has an effect of improving skin quality (beauty effect) indirectly because proanthocyanidins, especially OPC, have an excellent anti-stress effect. It is.
- Purified water (7.2 L) was added to 900 g of pine bark, and the mixture was broken with a blender (Waring Blender) and heated at 100 ° C. for 10 minutes. Then, it was immediately filtered to obtain a filtrate. The residue after filtration was washed with 1.8 L of purified water, and the filtrate and the washing solution were combined to obtain 9 L of a crude pine bark extract.
- the crude extract was allowed to cool to 25 ° C., sodium chloride was added to 100% saturated concentration and stirred well, and then allowed to stand at 4 ° C. for 24 hours. After standing, this solution was filtered to obtain a filtrate. 1 L of the above filtrate was further purified by the steps shown below. First, the filtrate was passed through a 30 x 300 mm force ram filled with 100 ml of an aromatic synthetic resin swollen with water (Diaion HP—20: manufactured by Mitsubishi Chemical Corporation). And further washed with 1 L of purified water. Subsequently, the column was eluted with 15% (V / V) ethanol mixed solvent in ethanol to obtain 200 mL of purified pine bark extract.
- the purified pine bark extract obtained was freeze-dried and powdered. Repeat this procedure to dry the purified pine bark extract from 9 L pine bark hot water extract. A dry powder of 7.21 g was obtained. Dry powder of the purified pine bark extract, a Puroanto Shianijin 40 wt% (20 wt 0/0 as OPC) contained.
- proanthocyanidins were administered dermally (application) or orally (orally ingested) to test guinea pigs whose skin collagen content had been reduced in advance. After the administration, hydroxyproline (hyp amount) specifically present in collagen constituting the skin was measured.
- test guinea pigs Of the five groups of test guinea pigs, three groups of test guinea pigs (groups a to c) were used. First, the hair of the site of the three groups of guinea pigs to be administered transdermally was removed using a clipper. The aqueous solution to a dry powder of the obtained pine bark extract in Preparation containing 0.3 by weight%, a group of guinea pigs site hair was removed the (a group) 5 00 ⁇ L / 5 00 cm 2 And then dried with cold air. This coating and drying operation was performed once a day for 2 weeks. During the application period, mol Kis were given low vitamin C diet ad libitum.
- the amount of skin hypops was measured as follows. The skin was removed from the guinea pig and dried overnight at 60 ° C. This dried product was pulverized, and 5 Omg of the powder frame was added to 5 mL of hydrochloric acid (6M), maintained at 110 ° C using a heating block, and hydrolyzed for 24 hours. Hy pi in this hydrolyzate was measured by the chloramine T method. The results are shown in Table 1. The higher the amount of hypo, the greater the amount of collagen in the skin, indicating that the skin is improved.
- test guinea pigs (groups b and c) from which the remaining two groups of hair had been removed contained an aqueous solution containing 0.3% by weight of grape seed extract (Kikkoman Corporation) containing 38% by weight of proanthocyanidin. Purified water was applied to each skin, and the amount of hypo in the skin was measured in the same manner as described above. The results are shown in Table 1.
- test guinea pigs Of the remaining two groups of test guinea pigs (groups d and e), one group of test guinea pigs (group d) was mixed with 0.3% by weight of the dry powder of the pine bark extract obtained in the above production example. The low-vitamin C diet contained was freely given for 2 weeks. After the intake period, the amount of Hyp was measured as described above. The remaining one group of test guinea pigs (e group) contains a low vitamin C diet containing 0.3% by weight of pudo seed extract (Kikko Isman Co., Ltd.) containing 38% by weight of proanthocyanidins. Ingested in the same manner and measured the amount of Hyp. These results are shown in Table 1.
- the Hyp amount increased, and the Hyp amount recovered to almost the same level as the healthy subject (control). I understand. In particular, it can be seen that the pine bark extract has an excellent skin improvement effect compared to other plant extracts.
- the dry powder (component A) and proline (component B) of the pine bark extract obtained in the above production example were mixed with the low vitamin C feed in the proportions shown in Table 2 to produce feed 1.
- Examples 2 to 4 Preparation of feed 2 to 4
- alanine, glycine, and arginine were used as other B components instead of proline (B component), and mixed in the proportions shown in Table 2, respectively. 2-4 were produced.
- Example 2 In addition to the composition of Example 1, A feed 5 was produced in the same manner as in Example 1 except that ascorbic acid was mixed as a component at a ratio shown in Table 2.
- Feeds were produced by mixing the ingredients listed in Table 2, and these were designated as feeds 6 and 7.
- Ingredients are in weight percent. Ingredients are low vitamin c feed.
- a lotion 2 was produced in the same manner as in Example 14 except that the dry powder of pine bark extract was not dissolved in the base at the ratio shown in Table 4.
- the number is the number of people who answered yes
- the group ingesting tablet 1 of Example 13 has an excellent skin improvement effect compared to the group ingesting tablet 2 of Comparative Example 5. It can be seen that the group to which the lotion 1 of Example 14 was applied had an excellent skin improvement effect as compared to the group to which the lotion 2 of Comparative Example 6 was applied. From the above, the skin improvement composition of the present invention has an excellent skin improvement effect in both oral administration and transdermal administration. It turns out that a fruit is obtained.
- a beverage was prepared by mixing the dry powder of the pine bark extract obtained in Production Example and the following ingredients:
- the dry powder of the pine bark extract obtained in the production example and the following components were uniformly stirred and mixed to obtain a gel-like product, which was then applied to a polyester film (50 / im thickness) with a gel thickness l After forming the film to a thickness of mm, it was bonded to a polyester nonwoven fabric (elongation 50%) and heated at 50 ° C. for 24 hours to obtain a sheet-like water-containing pack agent.
- This pack is expected to be extremely effective because it can be transdermally administered in large amounts locally on proanthocyanidins and amino acids:
- an excellent skin improvement effect can be obtained by ingesting or applying a skin improvement thread and composition containing p-Panthocyanidin and an amino acid having a collagen production promoting effect.
- the skin improvement composition of the present invention can be effectively used for foods, pharmaceuticals, quasi drugs, cosmetics and the like.
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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PCT/JP2004/018777 WO2006061915A1 (en) | 2004-12-09 | 2004-12-09 | Skin remedy composition |
Applications Claiming Priority (1)
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PCT/JP2004/018777 WO2006061915A1 (en) | 2004-12-09 | 2004-12-09 | Skin remedy composition |
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WO2006061915A1 true WO2006061915A1 (en) | 2006-06-15 |
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PCT/JP2004/018777 WO2006061915A1 (en) | 2004-12-09 | 2004-12-09 | Skin remedy composition |
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Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02134309A (en) * | 1988-11-16 | 1990-05-23 | Kikkoman Corp | Beautifying and whitening cosmetic |
JPH07194375A (en) * | 1993-12-28 | 1995-08-01 | Kanebo Ltd | Promoter for synthesizing collagen and collagen metabolism activator |
US5804594A (en) * | 1997-01-22 | 1998-09-08 | Murad; Howard | Pharmaceutical compositions and methods for improving wrinkles and other skin conditions |
JPH1149628A (en) * | 1997-07-31 | 1999-02-23 | Shiseido Co Ltd | Cosmetic for improving wrinkle |
WO2000051561A1 (en) * | 1999-03-02 | 2000-09-08 | Kyowa Hakko Kogyo Co., Ltd. | Cosmetics |
JP2002119210A (en) * | 2000-10-13 | 2002-04-23 | Riken Vitamin Co Ltd | Method for producing coffee beverage |
JP2003530410A (en) * | 2000-04-14 | 2003-10-14 | マーズ インコーポレイテッド | Compositions and methods for improving vascular health |
JP2004149441A (en) * | 2002-10-30 | 2004-05-27 | Toyo Shinyaku:Kk | External preparation for skin |
JP2004210675A (en) * | 2002-12-27 | 2004-07-29 | Toyo Shinyaku:Kk | Bone quantity amelioration composition |
JP2004307370A (en) * | 2003-04-04 | 2004-11-04 | Kyowa Hakko Kogyo Co Ltd | Composition containing proanthocyanidin |
JP3595816B2 (en) * | 2002-04-24 | 2004-12-02 | 株式会社東洋新薬 | Method for producing proanthocyanidin-containing material |
JP2005029486A (en) * | 2003-07-09 | 2005-02-03 | Toyo Shinyaku:Kk | Skin-improving composition |
-
2004
- 2004-12-09 WO PCT/JP2004/018777 patent/WO2006061915A1/en not_active Application Discontinuation
Patent Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02134309A (en) * | 1988-11-16 | 1990-05-23 | Kikkoman Corp | Beautifying and whitening cosmetic |
JPH07194375A (en) * | 1993-12-28 | 1995-08-01 | Kanebo Ltd | Promoter for synthesizing collagen and collagen metabolism activator |
US5804594A (en) * | 1997-01-22 | 1998-09-08 | Murad; Howard | Pharmaceutical compositions and methods for improving wrinkles and other skin conditions |
JPH1149628A (en) * | 1997-07-31 | 1999-02-23 | Shiseido Co Ltd | Cosmetic for improving wrinkle |
WO2000051561A1 (en) * | 1999-03-02 | 2000-09-08 | Kyowa Hakko Kogyo Co., Ltd. | Cosmetics |
JP2003530410A (en) * | 2000-04-14 | 2003-10-14 | マーズ インコーポレイテッド | Compositions and methods for improving vascular health |
JP2002119210A (en) * | 2000-10-13 | 2002-04-23 | Riken Vitamin Co Ltd | Method for producing coffee beverage |
JP3595816B2 (en) * | 2002-04-24 | 2004-12-02 | 株式会社東洋新薬 | Method for producing proanthocyanidin-containing material |
JP2004149441A (en) * | 2002-10-30 | 2004-05-27 | Toyo Shinyaku:Kk | External preparation for skin |
JP2004210675A (en) * | 2002-12-27 | 2004-07-29 | Toyo Shinyaku:Kk | Bone quantity amelioration composition |
JP2004307370A (en) * | 2003-04-04 | 2004-11-04 | Kyowa Hakko Kogyo Co Ltd | Composition containing proanthocyanidin |
JP2005029486A (en) * | 2003-07-09 | 2005-02-03 | Toyo Shinyaku:Kk | Skin-improving composition |
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