WO2015156328A1 - 皮膚老化防止剤、及びレスベラトロール3-O-α-グルコシドの濃縮液 - Google Patents
皮膚老化防止剤、及びレスベラトロール3-O-α-グルコシドの濃縮液 Download PDFInfo
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- WO2015156328A1 WO2015156328A1 PCT/JP2015/061013 JP2015061013W WO2015156328A1 WO 2015156328 A1 WO2015156328 A1 WO 2015156328A1 JP 2015061013 W JP2015061013 W JP 2015061013W WO 2015156328 A1 WO2015156328 A1 WO 2015156328A1
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- Prior art keywords
- resveratrol
- glucoside
- skin
- extract
- skin aging
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- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
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- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
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Definitions
- the present invention relates to a skin aging preventive agent that prevents skin aging by the action of melanin production inhibition, hyaluronidase inhibition, antioxidant, cell activation, sirtuin gene activation, matrix metalloproteinase inhibition, anti-inflammatory and the like. Furthermore, the present invention relates to a concentrated solution obtained by concentrating resveratrol 3-O- ⁇ -glucoside and used by adding to foods, cosmetics, medicines and the like.
- Resveratrol is a kind of polyphenol contained in grape skins and is known as an antioxidant component.
- life extension action with regard to the physiological function of resveratrol, life extension action, anticancer action, antibacterial action and the like in various organisms have been reported.
- resveratrol has a melanin production inhibitory effect and has been proposed for use in whitening cosmetics (Patent Document 1, Non-Patent Documents 1 and 2, etc.).
- Patent Document 1 Non-Patent Documents 1 and 2, etc.
- resveratrol has various functionalities and is currently being used not only for cosmetics and foods but also for pharmaceuticals.
- Patent Document 3 discloses that the instability of resveratrol can be improved by using resveratrol ether such as resveratrol glucoside.
- Patent Document 3 shows that resveratrol glucoside can be obtained by extraction from tissue ( polygonum cuspidatum ) or in vitro culture of vitis vinifera cells, and resveratrol obtained by these techniques. All of the glucosides are resveratrol 3-O- ⁇ -glucoside. Therefore, even the resveratrol glucoside disclosed in Patent Document 3 is not satisfactory in terms of water solubility and functionality as described above.
- Non-Patent Document 4 discloses that resveratrol 3-O- ⁇ -glucoside can be obtained by allowing Streptococus mutans to act on a solution of resveratrol and sucrose. It is disclosed. However, Non-Patent Document 4 does not discuss any physical properties or characteristics of resveratrol 3-O- ⁇ -glucoside. In general, glycosides are known to be greatly affected by the physical properties and functions of aglycone itself depending on the binding position and mode of sugar, and the physical properties and properties of resveratrol 3-O- ⁇ -glucoside are disclosed. Non-patent document 4 that has not been disclosed does not indicate the availability of resveratrol 3-O- ⁇ -glucoside.
- JP-A-1-38009 JP 2002-80372 A Special table 2010-535221 gazette
- resveratrol 3-O- ⁇ -glucoside contains melanin production suppression, hyaluronidase inhibition, antioxidant, cell activation, sirtuin gene activation, It has been found that skin aging prevention effects such as matrix metalloprotease inhibition and anti-inflammatory are excellent and can be used as a skin aging inhibitor. Furthermore, resveratrol 3-O- ⁇ -glucoside can be concentrated at a high concentration in a dissolved state by mixing resveratrol 3-O- ⁇ -glucoside with a 1 to 4 carbon alcohol having 1 to 6 carbon atoms. I found. The present invention has been completed by further studies based on these findings.
- Item 1 A skin aging inhibitor comprising resveratrol 3-O- ⁇ -glucoside as an active ingredient.
- Item 2. Item 2. The skin aging inhibitor according to Item 1, which is used as a melanin production inhibitor or a whitening agent.
- Item 3. Item 2. The skin aging inhibitor according to Item 1, which is used as a hyaluronidase inhibitor.
- Item 4. Item 2. The skin aging inhibitor according to Item 1, which is used as an agent for reducing oxidative stress in skin tissue.
- Item 5. Item 2. The skin aging inhibitor according to Item 1, which is used as a matrix metalloproteinase expression inhibitor.
- Item 6. Item 2.
- the skin aging inhibitor according to Item 1 which is used as a cell activator for skin cells.
- Item 7. Item 2.
- Item 8. Item 2.
- Item 9. Item 11.
- An external preparation for skin comprising the skin antiaging agent according to any one of Items 1 to 8.
- An oral preparation comprising the skin antiaging agent according to any one of Items 1 to 8.
- Item 11. Item 9.
- a food or drink comprising the skin antiaging agent according to any one of Items 1 to 8.
- Item 12. Item 9.
- a pharmaceutical product for systemic administration comprising the skin antiaging agent according to any one of Items 1 to 8.
- Item 13. Use of resveratrol 3-O- ⁇ -glucoside for the manufacture of a skin anti-aging agent.
- Item 14. Resveratrol 3-O- ⁇ -glucoside used in the treatment for prevention of skin aging.
- Item 15. A method for preventing skin aging, comprising a step of transdermally or orally administering resveratrol 3-O- ⁇ -glucoside to a human who is required to prevent skin aging.
- resveratrol 3-O- ⁇ -glucoside which is an active ingredient of the skin antiaging agent of the present invention, has high water solubility, so it can be blended at a high content regardless of the type or form of the product. It is possible. Therefore, the skin aging inhibitor of the present invention can impart a skin aging prevention function to various products such as cosmetics, foods, and medicines.
- resveratrol 3-O- ⁇ -glucoside has excellent stability and can suppress browning over time. Therefore, a product containing the skin antiaging agent of the present invention has quality such as appearance. The effect can be maintained over a long period of time without loss.
- the concentrated solution of the present invention is concentrated to a high concentration in a state where resveratrol 3-O- ⁇ -glucoside is dissolved, and a small amount is added to various products such as cosmetics, foods, and pharmaceuticals. However, since it can be contained in an amount effective for the expression of the skin aging prevention function, it is useful as an additive material for various products containing resveratrol 3-O- ⁇ -glucoside.
- resveratrol 3-O- ⁇ -glucoside used as an active ingredient, the hydroxyl group at the 3-position of resveratrol and the hydroxyl group at the 1-position of ⁇ -glucose ( ⁇ -pyranose) are linked by a glucoside bond.
- Resveratrol derivative used as an active ingredient, the hydroxyl group at the 3-position of resveratrol and the hydroxyl group at the 1-position of ⁇ -glucose ( ⁇ -pyranose) are linked by a glucoside bond.
- the glucose constituting resveratrol 3-O- ⁇ -glucoside may be either D-form or L-form, and preferably D-form.
- resveratrol constituting resveratrol 3-O- ⁇ -glucoside may be either cis type or trans type, preferably trans type.
- the resveratrol 3-O- ⁇ -glucoside used may be a purified product or a crude product.
- Resveratrol 3-O- ⁇ -glucoside used in the present invention can be obtained by a known production method such as an enzymatic method or an organic synthesis method.
- sucrose phosphorylase and glucoamylase are added and subjected to an enzymatic reaction in the presence of revesulatrol and sucrose.
- sucrose phosphorylase used in the production method is not particularly limited.
- Streptococus mutans Leuconostoc mesenteroides
- Lactobacillus acidophilus Lactobacillus acidophilus
- Bifidobacterium adolescentis Bifidobacterium adolescentis
- Pseudomonas saccharophila and the like.
- the enzyme reaction is carried out with an organic solvent such as dimethyl sulfoxide, dimethylformamide, isopropyl alcohol, sec-butyl alcohol, acetonitrile, ethanol, and water. It is preferable to carry out in the mixed solution.
- resveratrol 3-O- ⁇ -glucoside has a melanin production-inhibiting action and can suppress pigmentation such as sunburn, blotches and dullness. It can be used as a melanin production inhibitor or a whitening agent. Furthermore, since resveratrol 3-O- ⁇ -glucoside has an antioxidant action, the skin antiaging agent of the present invention is not only for suppressing the above-mentioned pigmentation but also for reducing oxidative stress in skin tissue. Can also be used.
- Resveratrol 3-O- ⁇ -glucoside has a hyaluronidase inhibitory action and a matrix metalloprotease expression inhibitory action, and can suppress the degradation of hyaluronic acid, collagen, etc. present in the dermis layer. Furthermore, resveratrol 3-O- ⁇ -glucoside suppresses inflammation, which is known as an accelerating factor of aging, a cell activating effect, an effect of promoting the expression of a sirtuin gene also called an anti-aging gene Since it has an action, it is possible to effectively suppress erythema and skin cell function deterioration and aging associated with aging.
- the form of application of the skin antiaging agent of the present invention to the body is not particularly limited, and is used in any application form such as transdermal, transmucosal, oral, enteral, intravenous, transarterial, subcutaneous, intramuscular and the like. it can. From the viewpoint of more effectively exerting the skin aging prevention action, preferably, transdermal application, transmucosal application, or oral application, and more preferably transdermal application.
- the skin anti-aging agent of the present invention is used by blending into a product that is required to have a skin anti-aging function.
- the form of the product in which the skin antiaging agent of the present invention is blended may be any of solid, semi-solid, liquid, etc., and is appropriately set according to the type and use of the product.
- the product containing the skin antiaging agent of the present invention is not particularly limited as long as it is required to have a skin antiaging function.
- Resveratrol 3-O- ⁇ -glucoside exhibits excellent absorbability regardless of whether it is used transdermally or orally. Therefore, a product formulated with the skin antiaging agent of the present invention is, for example, for external use on the skin. Any of agents, oral preparations, foods and drinks, pharmaceuticals for systemic administration (including quasi-drugs for internal use) and the like may be used. Among these, Preferably, a skin external preparation is mentioned.
- the product in which the skin antiaging agent of the present invention is blended will be described.
- the skin external preparation containing the skin antiaging agent of the present invention is provided as a skin external preparation for preventing skin aging.
- the external preparation for skin is prepared by combining a pharmaceutically or cosmetically acceptable carrier or additive in addition to the skin antiaging agent of the present invention and formulating it into a desired dosage form.
- a pharmaceutically or cosmetically acceptable carrier and additive known ones used for external preparations for skin can be used. Specific examples of such carriers and additives include aqueous bases such as water and alcohols; oily base materials; cooling agents, pH adjusters, thickeners, antioxidants, metal sequestering agents, and surface active agents. Agents, emulsifiers, solubilizers, solubilizers, dyes (dyes, pigments), fragrances, preservatives and the like.
- monohydric to tetrahydric alcohols having 1 to 6 carbon atoms which will be described later, have the effect of further improving the solubility of resveratrol 3-O- ⁇ -glucoside.
- the agent preferably contains a mono- to tetrahydric alcohol having 1 to 6 carbon atoms.
- the content of the monohydric to tetrahydric alcohol having 1 to 6 carbon atoms in the external preparation for skin is not particularly limited, but for example 0.01 to 30% by weight, preferably 1 to 20% by weight, and more preferably 5 to 20%. % By weight.
- various pharmacological components used for the external preparation for skin can be blended with the external preparation for skin, if necessary.
- pharmacological components include humectants, antioxidants, cell activators, whitening agents, UV inhibitors, active oxygen scavengers, blood circulation promoters, anti-inflammatory agents, antihistamines, vitamins, plant extracts, skin Examples include astringents, skin function enhancers, bactericides, and antibacterial agents.
- the type of each pharmacological component is not particularly limited, and examples thereof include the following components.
- humectants include glycerin, 1,3-butylene glycol, proteins or derivatives or hydrolysates thereof, and salts thereof (collagen, elastin, keratin, etc.), mucopolysaccharides and derivatives thereof (hyaluronic acid, hydrolyzed hyaluronic acid) , Chondroitin sulfate, etc.), amino acids and derivatives thereof (histidine, serine, glycine, theanine, aspartic acid, arginine, lysine, pyrrolidone carboxylic acid, N-methyl-L-serine, etc.), saccharides (sorbitol, erythritol, trehalose, inositol, Glucose, xylitol, N-acetylglucosamine, raffinose, sucrose and derivatives thereof, dextrin and derivatives thereof, honey, etc.), phosphorylated oligosacchari
- Antioxidants include, for example, vitamin E and its derivatives (dl- ⁇ ( ⁇ , ⁇ ) -tocopherol, dl- ⁇ -tocopherol acetate, nicotinic acid-dl- ⁇ -tocopherol, linoleic acid-dl- ⁇ -tocopherol, Tocopherols such as dl- ⁇ -tocopherol succinate and derivatives thereof, ubiquinones and the like, vitamin A and derivatives thereof (retinol and retinol palmitate, derivatives such as retinol acetate, retinal such as dehydroretinal and derivatives thereof), carotenoids ( Carotene, lycopene, astaxanthin, capsanthin, etc.), vitamin B and its derivatives (thiamine hydrochloride, thiamine sulfate, riboflavin, riboflavin acetate, pyridoxine hydrochloride, pyridoxine dioctanoate, flavin
- the cell activator examples include vitamin A and derivatives thereof (derivatives such as retinol and retinol palmitate, retinol acetate; derivatives such as retinal and dehydroretinal), vitamin C and derivatives thereof (L-ascorbic acid phosphate, L-ascorbic acid sulfate, L-ascorbyl dipalmitate, L-ascorbyl tetraisopalmitate, ascorbyl glucoside, etc.), vitamin B and its derivatives (thiamine hydrochloride, thiamine sulfate, riboflavin, riboflavin acetate, pyridoxine hydrochloride, Pyridoxine dioctanoate, flavin adenine nucleotide, cyanocobalamin, diisopropylamine dichloroacetic acid, folic acid, nicotinic acid amide, nicotinic acid benzyl and other nicot
- whitening agents include vitamin C and its derivatives (L-ascorbic acid phosphate, L-ascorbic acid sulfate, dipalmitic acid L-ascorbyl, tetraisopalmitic acid L-ascorbyl, ascorbic acid glucoside, etc.), placenta Extract, dipotassium glycyrrhizinate, grabrizine, glabrene, liquiritin, isoliquiritin and licorice extract containing these, yokuinin (barley) extract, koganebana (ogon) extract, seaweed extract (comb, macombu, wakame, hijiki, hibamata , Sugime, Trollocombu, Kajime, Tsuruarame, Chigaiso, Hyundai Rawa, Giant Kelp, etc .; Brown algae; Japanese plover, Tsunomatsu, Suginori, Usubanori, Asakusanori, Mats
- UV inhibitors include 2-methoxyhexyl paramethoxycinnamate, 4-tert-butyl-4′-methoxydibenzoylmethane, oxybenzone and derivatives thereof (2-hydroxy-4-methoxybenzophenone, 2-hydroxy- 4-methoxybenzophenone-5-sulfonic acid, sodium 2-hydroxy-4-methoxybenzophenone-5-sulfonate, etc.), titanium oxide, fine particle titanium oxide, zinc oxide, barium sulfate and the like.
- Anti-inflammatory agents include, for example, glycyrrhizic acid derivatives, allantoin, tranexamic acid, bisabolol, turmeric extract, cucumber fruit extract, edelweiss extract, rosemary leaf extract, sage leaf extract, eel extract, yellowfin bark extract, licorice extract, chimney extract, Eucalyptus extract, lactoferrin, etc., such as perilla extract, aloe extract, aloin, aloe emodin, flavonoids (rutin and its glycoside, quercetin and its glycoside, hesperidin and its glycoside, hesperetin and its glycoside) .
- oral preparation The oral preparation containing the skin antiaging agent of the present invention is provided as an oral preparation for preventing skin aging.
- the type of oral preparation is not particularly limited.
- toothpastes such as toothpastes, powder dentifrices, liquid dentifrices; tooth creams; mouthwashes such as mouthwashes and mouthwashes; oral pasta preparations , Mouse spray, orally disintegrating film, gel, troche, tablet, chewable and the like.
- what is necessary is just to set suitably about the dosage form of a skin external preparation according to the kind.
- monohydric to tetrahydric alcohols having 1 to 6 carbon atoms which will be described later, have the effect of further improving the solubility of resveratrol 3-O- ⁇ -glucoside.
- the agent preferably contains a mono- to tetrahydric alcohol having 1 to 6 carbon atoms.
- the content of the monohydric to tetrahydric alcohol having 1 to 6 carbon atoms in the oral preparation is not particularly limited, but for example 0.01 to 99% by weight, preferably 1 to 50% by weight, more preferably 5 to 30%. % By weight.
- the food / beverage products containing the skin antiaging agent of this invention are provided as food / beverage products provided with the skin aging prevention function.
- the food and drink containing the skin antiaging agent of the present invention can be provided as a food for specified health use, a dietary supplement, a functional food, a food for the sick, etc. in addition to a general food and drink.
- sweets such as red bean paste, sheep crab, bun, chocolate, gum, jelly, gummy, agar, apricot tofu, cake, castella, cookie, rice cracker, tablet confectionery, etc .; bread; rice cake; Products; processed meat products such as sausages and ham; processed fruit products such as jam, marmalade and fruit sauce; seasonings such as mirin, cooking liquor, dressing, mayonnaise and miso; noodles such as udon and soba noodles; pickles; Bottles, canned fruits, etc .; capsules such as soft capsules and hard capsules; carbonated drinks such as energy drinks, cider and ramune Soft drinks, condiments beverages, alcohol-containing beverages, beverages such as powdered juice and the like.
- Resveratrol 3-O- ⁇ -glucoside exhibits very good solubility in a mixed solution of ethanol and water. Therefore, in view of such characteristics, a food / beverage product containing the antiaging agent of the present invention is preferable.
- An example is an alcohol-containing beverage.
- “alcohol-containing beverage” includes beer, shochu, wine, whiskey, sake, spirits, and other energy drinks including ethanol.
- the content of ethanol in the alcohol-containing beverage is not particularly limited, and examples thereof include 0.001 to 25% by weight, preferably 0.001 to 20% by weight, and more preferably 0.001 to 15% by weight.
- the food and drink are prepared by adjusting the skin aging inhibitor of the present invention to a desired form in combination with other food materials and additive ingredients, and processing and cooking according to the type of food and drink.
- the content of the skin antiaging agent of the present invention in the food and drink may be appropriately set according to the type and dosage form of the food and drink.
- resveratrol 3-O- ⁇ -glucoside is 0.
- the range is 001 to 90% by weight, preferably 0.01 to 50% by weight, more preferably 0.1 to 30% by weight.
- the content of the skin antiaging agent in the alcohol-containing beverage is, for example, 0.001 to 5% by weight, preferably Is 0.01 to 5% by weight, more preferably 0.05 to 5% by weight, and particularly preferably 0.12 to 5% by weight.
- the skin antiaging agent of the present invention when used in the field of food and drink, the skin antiaging agent of the present invention is provided alone or in combination with other ingredients as an additive for food and drink for preventing skin aging. You can also When the skin antiaging agent of the present invention is used as a food additive, the content of resveratrol 3-O- ⁇ -glucoside in the food additive, the amount of the food additive added to food and drink, etc. May be appropriately set so that resveratrol 3-O- ⁇ -glucoside can satisfy the above-described content in the food and drink to be added.
- Drugs for systemic administration including quasi-drugs for internal use) containing the skin aging inhibitor of the present invention are provided as drugs for preventing skin aging.
- the administration form of the pharmaceutical for systemic administration is not particularly limited as long as it is systemic administration, and examples thereof include oral administration, enteral administration, intravenous administration, transarterial administration, subcutaneous administration, and intramuscular administration. Among these systemic administrations, oral administration is preferable.
- the above-mentioned pharmaceutical for systemic administration is prepared by combining a pharmaceutically acceptable carrier or additive in addition to the skin aging inhibitor of the present invention and formulating it into a desired dosage form.
- a pharmaceutically acceptable carrier or additive include aqueous bases such as water and alcohol; oily base materials; abrasives, excipients, coating agents, binders, extenders, disintegrants, lubricants. , Cooling agents, pH adjusters, thickeners, antioxidants, sequestering agents, surfactants, emulsifiers, solubilizers, solubilizers, dyes (dyes, pigments), fragrances, preservatives, and the like. .
- monohydric to tetrahydric alcohols having 1 to 6 carbon atoms which will be described later, have the effect of further improving the solubility of resveratrol 3-O- ⁇ -glucoside.
- a monohydric to tetrahydric alcohol having 1 to 6 carbon atoms is contained.
- the content of the monohydric to tetrahydric alcohol having 1 to 6 carbon atoms in the pharmaceutical is not particularly limited, but for example 0.001 to 75% by weight, preferably 0.001 to 50% by weight, and more preferably 0.001. Up to 15% by weight.
- the pharmacological component for systemic administration can be blended with various pharmacological components that are medicinal products for systemic administration, if necessary.
- pharmacological components include humectants, antioxidants, cell activators, whitening agents, active oxygen scavengers, blood circulation promoters, anti-inflammatory agents, antihistamines, vitamins, plant extracts, blood circulation promoters, skin Examples include function enhancers, bactericides, and antibacterial agents.
- each of these pharmacological components is not particularly limited, but for example, specific examples of humectants, antioxidants, cell activators, whitening agents, active oxygen scavengers, blood circulation promoters, and anti-inflammatory agents, It is the same as what is mix
- the content of the skin antiaging agent of the present invention in the pharmaceutical for systemic administration may be appropriately set according to the type and dosage form of the pharmaceutical for systemic administration.
- the resveratrol 3-O- ⁇ -glucoside is 0.05% by weight or more, preferably It can also be contained at a high concentration of 0.12 to 5% by weight.
- the concentrated liquid of the present invention is characterized in that resveratrol 3-O- ⁇ -glucoside is contained in a solvent containing a monohydric to tetrahydric alcohol having 1 to 6 carbon atoms.
- resveratrol 3-O- ⁇ -glucoside and a 1- to 4-hydric alcohol solvent having 1 to 6 carbon atoms coexist, so that resveratrol 3-O- ⁇ -glucoside is dissolved in a high concentration. It becomes possible to concentrate.
- Resveratrol 3-O- ⁇ -glucoside used in the concentrated solution of the present invention is as described in “1. Anti-aging agent for skin”.
- the content of resveratrol 3-O- ⁇ -glucoside contained in the concentrated solution of the present invention varies depending on the type and amount of 1 to 4 carbon alcohols having 1 to 6 carbon atoms to be used. 50 w / v%, preferably 8 to 40 w / v%, more preferably 10 to 30 w / v%.
- the monohydric to tetrahydric alcohol having 1 to 6 carbon atoms functions as a solvent for dissolving resveratrol 3-O- ⁇ -glucoside.
- the type of the monohydric to tetrahydric alcohol having 1 to 6 carbon atoms is not particularly limited, and is pharmaceutically or cosmetically acceptable or edible depending on the use of the concentrate of the present invention. Should be selected.
- the monohydric alcohol having 2 to 6 carbon atoms include ethanol; propanol such as 1-propanol and 2-propanol; 1-butanol, 2-methyl-2-propanol, 2-methyl-1-propanol, Butanol such as 2-butanol; pentanol such as 1-pentanol, 2-pentanol, 3-pentanol, isoamyl alcohol, tert-amyl alcohol, neopentyl alcohol; 1-hexanol, 2-hexanol, 3-hexanol, Examples include hexanol such as 2-methyl-1-pentanol, 3-methyl-1-pentanol, and 4-methyl-1-pentanol.
- dihydric alcohol having 2 to 6 carbon atoms examples include ethylene glycol, propylene glycol (1,2-propanediol), trimethylene glycol, 1,3-butylene glycol, 1,2-pentanediol, , 2-hexanediol, diethylene glycol, dipropylene glycol.
- trihydric alcohol having 2 to 6 carbon atoms examples include glycerin and the like.
- tetrahydric alcohol having 2 to 6 carbon atoms include diglycerin.
- a monohydric alcohol having 2 to 3 carbon atoms preferably a dihydric alcohol having 4 to 6 carbon atoms, a trihydric alcohol having 3 to 4 carbon atoms; more preferably ethanol, propylene glycol, 1,3-butylene glycol, Examples include dipropylene glycol, 1,2-pentanediol, 1,2-hexanediol, and glycerin.
- These 1 to 4 carbon alcohols having 1 to 6 carbon atoms may be used alone or in combination of two or more.
- the solvent may be composed of a monohydric alcohol having 1 to 6 carbon atoms alone, or an aqueous solvent other than the monohydric to tetrahydric alcohol having 1 to 6 carbon atoms (for example, water Etc.) may be included.
- the solubility of resveratrol 3-O- ⁇ -glucoside decreases as the content of aqueous solvents other than 1 to 4 carbon alcohols having 1 to 6 carbon atoms increases. Is appropriately set according to the amount of resveratrol 3-O- ⁇ -glucoside to be dissolved, the type of monohydric to tetrahydric alcohol having 1 to 6 carbon atoms, and the like.
- resveratrol 3-O- ⁇ -glucoside with respect to 100 parts by weight of the total amount of the solvent contained in the concentrated solution of the present invention (total amount of 1 to 4 carbon alcohol having 1 to 6 carbon atoms and other aqueous solvent) May be appropriately set within the range of 5 to 100 parts by weight, preferably 25 to 100 parts by weight, and more preferably 50 to 100 parts by weight. More specifically, the following ranges are exemplified as the ratio of the monohydric to tetrahydric alcohol having 1 to 6 carbon atoms with respect to the total amount of the solvent contained in the concentrated liquid of the present invention.
- ethanol is 25 to 100 parts by weight, preferably 50 to 100 parts by weight, more preferably 75 to 100 parts by weight per 100 parts by weight of the total amount of the solvent.
- propylene glycol is used as a monohydric to tetrahydric alcohol having 1 to 6 carbon atoms: 50 to 100 parts by weight, preferably 75 to 100 parts by weight, more preferably 90 to 100 parts by weight of propylene glycol per 100 parts by weight of the total amount of the solvent.
- 1,3-butylene glycol is used as a monohydric to tetrahydric alcohol having 1 to 6 carbon atoms: 25 to 100 parts by weight, preferably 50 to 100 parts by weight of 1,3-butylene glycol per 100 parts by weight of the total amount of the solvent Parts, more preferably 75 to 100 parts by weight
- dipropylene glycol is used as a monohydric to tetrahydric alcohol having 1 to 6 carbon atoms: 25 to 100 parts by weight, preferably 50 to 100 parts by weight, more preferably 75 parts by weight of dipropylene glycol per 100 parts by weight of the total amount of the solvent.
- 1,2-pentanediol is used as a monohydric to tetrahydric alcohol having 1 to 6 carbon atoms: 25 to 100 parts by weight, preferably 50 to 100 parts by weight of 1,2-pentanediol per 100 parts by weight of the total amount of the solvent Parts, more preferably 75 to 100 parts by weight
- 1,2-hexanediol is used as a monohydric to tetrahydric alcohol having 1 to 6 carbon atoms: 10 to 100 parts by weight, preferably 25 to 100 parts by weight of 1,2-hexanediol per 100 parts by weight of the total amount of the solvent Parts, more preferably 50 to 100 parts by weight
- glycerin is used as the monohydric to tetrahydric alcohol having 1 to 6 carbon atoms: 75 to 100 parts by weight, preferably 90 to 100 parts by weight, more preferably 95 to 100 parts by weight of glycerin per 100 parts by weight of the total amount of the solvent
- the concentrated liquid of the present invention is used as an additive in the manufacture of products such as external preparations for skin, oral preparations, foods and drinks, and pharmaceuticals for systemic administration. Since the concentrated solution of the present invention contains a high concentration of resveratrol 3-O- ⁇ -glucoside in a dissolved state, it can be added to the product by adding a small amount to the product. The functionality of ⁇ -glucoside can be provided.
- the products and the like to which the concentrated liquid of the present invention is added are as described in the column of “1. Anti-aging agent for skin”.
- Production Example 1 Production of resveratrol 3-O- ⁇ -glucoside 5 g of resveratrol (Tokyo Kasei Kogyo) and 250 g of sucrose (Wako Pure Chemical Industries, Ltd.) were added to 500 mL of a 30% by weight dimethyl sulfoxide aqueous solution, and stirred and dissolved at 45 ° C. did. Sucrose phosphorylase (derived from Streptococcus mutans, 40,000 units) was added to the above mixed solution and reacted at 45 ° C. for 42 hours. To this reaction solution, 250 mL of water and glucoamylase (derived from Aspergillus niger, 20 units) were further added and reacted for another 4 hours.
- Sucrose phosphorylase derived from Streptococcus mutans, 40,000 units
- Example 1 Evaluation of inhibitory action of resveratrol 3-O- ⁇ -glucoside on melanin production
- Resveratrol 3-O- ⁇ -glucoside, resveratrol (Tokyo Kasei Kogyo), or resveratrol 3-O- ⁇ -glucoside (Tokyo Kasei Kogyo) to become a 0.2 wt% solution or suspension PBS was added to prepare a test substance.
- a skin model (Mat-3MEL-312B)
- 50 ⁇ L of the test substance was added to the stratum corneum side, and cultured for 16 days at 37 ° C. in a special medium (EPI-100NMM-113 made by MatTek). On day 2, 4, 7, 9, 11, and 14, the medium and the test substance were changed.
- the same operation was performed using PBS instead of the test substance as a control group.
- Example 2 Evaluation of resveratrol 3-O- ⁇ -glucoside on melanin production inhibitory action (2) Resveratrol 3-O- ⁇ -glucoside was prepared by adding PBS to a 0.2 wt% solution, 0.1 wt% solution, and 0.01 wt% solution, and this was used as a test substance. In the same manner as in Example 1, the melanin production inhibitory effect was evaluated.
- Table 2 shows the results obtained. From this result, it was confirmed that resveratrol 3-O- ⁇ -glucoside exerts a melanin production inhibitory effect in a concentration-dependent manner.
- Example 3 Evaluation of melanin production inhibitory action of resveratrol 3-O- ⁇ -glucoside-containing skin lotion The fact that the skin lotion having the composition shown in Table 3 was used as the test substance, the test substance on the stratum corneum side The amount of melanin in the skin model was measured by the same method as in Example 1 except that the addition amount was changed to 25 ⁇ L and the culture period was changed to 14 days.
- the amount of melanin in the skin model administered with the skin lotion of Example 3 was 64% of the skin model administered with the skin lotion of Comparative Example 1. From the above, it was confirmed that resveratrol 3-O- ⁇ -glucoside can exert a melanin production inhibitory effect even in the formulation of a lotion.
- Example 4 Evaluation of melanin production inhibitory action of a cosmetic liquid containing resveratrol 3-O- ⁇ -glucoside
- the cosmetic liquid having the composition shown in Table 4 was used as a test substance, and the test substance on the stratum corneum side
- the amount of melanin in the skin model was measured by the same method as in Example 1 except that the addition amount was changed to 25 ⁇ L and the culture period was changed to 14 days.
- the amount of melanin in the skin model administered with the essence of Example 4 was 43% of the skin model administered with the essence of Comparative Example 2. From the above, it was confirmed that resveratrol 3-O- ⁇ -glucoside exerts a melanin production inhibitory effect even in the formulation of a cosmetic liquid.
- Example 5 Evaluation of melanin production inhibitory action of resveratrol 3-O- ⁇ -glucoside combination cream The use of a cream having the composition shown in Table 5 as a test substance, the amount of test substance added to the stratum corneum side The amount of melanin in the skin model was measured by the same method as in Example 1 except that the amount was changed to 25 ⁇ L and the culture period was changed to 14 days.
- the amount of melanin in the skin model administered with the creams of Examples 5-1 and 5-2 was 61% and 62% of the amount of melanin of the skin model administered with the cream of Comparative Example 3, respectively. From the above, it was confirmed that resveratrol 3-O- ⁇ -glucoside exerts an inhibitory effect on melanin production even during cream formulation.
- each sample was filtered with a 0.45 ⁇ m centrifugal filter, and the concentration of each component in the filtrate was analyzed by HPLC under the same conditions as in Production Example 1 to obtain the dissolution concentration (w / v%) at 25 ° C. Asked.
- Table 18 shows the obtained results. From these results, it was revealed that resveratrol 3-O- ⁇ -glucoside showed significantly higher solubility than resveratrol and resveratrol 3-O- ⁇ -glucoside in the presence of ethanol. . In particular, in a solvent of 50% by weight or more of ethanol, the concentration of resveratrol 3-O- ⁇ -glucoside dissolved exceeded 30 w / v% and could be concentrated to a very high concentration.
- Table 20 shows the obtained results. This result also confirmed that resveratrol 3-O- ⁇ -glucoside showed significantly higher solubility than resveratrol and resveratrol 3-O- ⁇ -glucoside in the presence of propylene glycol. . In particular, with a solvent of propylene glycol of 75% by weight or more, the dissolution concentration of resveratrol 3-O- ⁇ -glucoside exceeded 30 w / v% and could be concentrated to a very high concentration.
- Example 22 Evaluation of the solubility of resveratrol 3-O- ⁇ -glucoside in dipropylene glycol Example 18 except that a solvent (composition shown in Table 22) containing dipropylene glycol (Asahi Glass) was used. Under the same conditions, the solubility of resveratrol 3-O- ⁇ -glucoside was evaluated.
- Example 23 Evaluation of the solubility of resveratrol 3-O- ⁇ -glucoside in 1,2-pentanediol
- 1,2-pentanediol photosensitive company
- Table 23 shows the obtained results. Even in this result, it was confirmed that resveratrol 3-O- ⁇ -glucoside showed remarkably high solubility in the presence of 1,2-pentanediol. In particular, in the solvent of 25% by weight or more of 1,2-pentanediol, the dissolution concentration of resveratrol 3-O- ⁇ -glucoside exceeded 20 w / v% and could be concentrated to a very high concentration.
- Reference Test Example 1 Evaluation of water solubility of resveratrol 3-O- ⁇ -glucoside Resveratrol 3-O- ⁇ -glucoside, resveratrol (Tokyo Chemical Industry) or resveratrol 3-O- ⁇ - 5 mg each of glucoside (Tokyo Chemical Industry) was weighed, 1 mL of water was added, placed in a 25 ° C. water bath under light shielding, and incubated for 20 hours with occasional shaking. After 20 hours, each sample was filtered with a 0.45 ⁇ m centrifugal filter, and then the concentration of each component in the filtrate was analyzed by HPLC under the same conditions as in Production Example 1 and dissolved in water at 25 ° C. (w / v %).
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Abstract
Description
項1. レスベラトロール3-O-α-グルコシドを有効成分とすることを特徴とする、皮膚老化防止剤。
項2. メラニン生成抑制剤又は美白剤として使用される、項1に記載の皮膚老化防止剤。
項3. ヒアルロニダーゼ阻害剤として使用される、項1に記載の皮膚老化防止剤。
項4. 皮膚組織における酸化ストレス低減剤として使用される、項1に記載の皮膚老化防止剤。
項5. マトリックスメタロプロテアーゼ発現抑制剤として使用される、項1に記載の皮膚老化防止剤。
項6. 皮膚細胞に対する細胞賦活剤として使用される、項1に記載の皮膚老化防止剤。
項7. サーチュイン遺伝子発現促進剤として使用される、項1に記載の皮膚老化防止剤。
項8. 皮膚老化を抑制するための抗炎症剤として使用される、項1に記載の皮膚老化防止剤。
項9. 項1~8のいずれかに記載の皮膚老化防止剤を含む、皮膚外用剤。
項10. 項1~8のいずれかに記載の皮膚老化防止剤を含む、口腔用剤。
項11. 項1~8のいずれかに記載の皮膚老化防止剤を含む、飲食品。
項12. 項1~8のいずれかに記載の皮膚老化防止剤を含む、全身投与用の医薬品。
項13. レスベラトロール3-O-α-グルコシドの、皮膚老化防止剤の製造のための使用。
項14. 皮膚老化の防止のための処置に使用されるレスベラトロール3-O-α-グルコシド。
項15. 皮膚老化防止が求められているヒトに、レスベラトロール3-O-α-グルコシドを経皮又は経口投与する工程を含む、皮膚老化防止方法。
項16. レスベラトロール3-O-α-グルコシドが、炭素数1~6の1~4価アルコールを含む溶媒に含有されてなる、レスベラトロール3-O-α-グルコシドの濃縮液。
項17. 炭素数1~6の1~4価アルコールが、エタノール、プロピレングリコール、1,3-ブチレングリコール、ジプロピレングリコール、1,2-ペンタンジオール、1,2-ヘキサンジオール、及びグリセリンよりなる群から選択される少なくとも1種である、項16に記載の濃縮液。
項18. 溶媒の総量100重量部当たり、炭素数1~6の1~4価アルコールが5~100重量部含まれる、項16又は17に記載の濃縮液。
項19. レスベラトロール3-O-α-グルコシドが5~50w/v%含まれる、項16~18のいずれかに記載の濃縮液。
本発明の皮膚老化防止剤は、レスベラトロール3-O-α-グルコシドを有効成分とすることを特徴とする。以下、本発明の皮膚老化防止剤について詳述する。
有効成分として使用されるレスベラトロール3-O-α-グルコシドは、レスベラトロールの3位の水酸基部分とα-グルコース(α-ピラノース)の1位の水酸基部分がグルコシド結合によって結合しているレスベラトロール誘導体である。
本発明の皮膚老化防止剤は、紫外線曝露等の外的ストレスや加齢によって生じる皮膚の老化を防止するために使用される。
本発明の皮膚老化防止剤を含む皮膚外用剤は、皮膚老化防止用の皮膚外用剤として提供される。
本発明の皮膚老化防止剤を含む口腔用剤は、皮膚老化防止用の口腔用剤として提供される。
本発明の皮膚老化防止剤を含む飲食品は、皮膚老化防止機能を備えた飲食品として提供される。本発明の皮膚老化防止剤を含む飲食品は、一般の飲食品の他、特定保健用食品、栄養補助食品、機能性食品、病者用食品等として提供することができる。
本発明の皮膚老化防止剤を含む全身投与用の医薬品(内服用の医薬部外品を含む)は、皮膚老化防止用の医薬品として提供される。
本発明の濃縮液は、レスベラトロール3-O-α-グルコシドが、炭素数1~6の1~4価アルコールを含む溶媒に含有されていることを特徴とする。このように、レスベラトロール3-O-α-グルコシドと炭素数1~6の1~4価アルコール溶媒を共存させることによって、レスベラトロール3-O-α-グルコシドが溶解した状態で高濃度に濃縮することが可能になる。
炭素数1~6の1~4価アルコールとしてエタノールを使用する場合:溶媒の総量100重量部当たり、エタノールが25~100重量部、好ましくは50~100重量部、更に好ましくは75~100重量部、
炭素数1~6の1~4価アルコールとしてプロピレングリコールを使用する場合:溶媒の総量100重量部当たり、プロピレングリコールが50~100重量部、好ましくは75~100重量部、更に好ましくは90~100重量部、
炭素数1~6の1~4価アルコールとして1,3-ブチレングリコールを使用する場合:溶媒の総量100重量部当たり、1,3-ブチレングリコールが25~100重量部、好ましくは50~100重量部、更に好ましくは75~100重量部、
炭素数1~6の1~4価アルコールとしてジプロピレングリコールを使用する場合:溶媒の総量100重量部当たり、ジプロピレングリコールが25~100重量部、好ましくは50~100重量部、更に好ましくは75~100重量部、
炭素数1~6の1~4価アルコールとして1,2-ペンタンジオールを使用する場合:溶媒の総量100重量部当たり、1,2-ペンタンジオールが25~100重量部、好ましくは50~100重量部、更に好ましくは75~100重量部、
炭素数1~6の1~4価アルコールとして1,2-ヘキサンジオールを使用する場合:溶媒の総量100重量部当たり、1,2-ヘキサンジオールが10~100重量部、好ましくは25~100重量部、更に好ましくは50~100重量部、
炭素数1~6の1~4価アルコールとしてグリセリンを使用する場合:溶媒の総量100重量部当たり、グリセリンが75~100重量部、好ましくは90~100重量部、更に好ましくは95~100重量部。
レスベラトロール(東京化成工業)5g及びスクロース(和光純薬)250gを30重量%ジメチルスルホキシド水溶液500mLに加え、45℃で攪拌、溶解した。上記混合液にスクロースホスホリラーゼ(ストレプトコッカス・ミュータンス由来、40000単位)を加え、45℃で42時間反応させた。この反応液に更に水250mL及びグルコアミラーゼ(アスペルギルス・ニガー由来、20単位)を加え更に4時間反応させた。得られた反応終了液を下記の条件でHPLC分析したところ、レスベラトロール3-O-α-グルコシドが約480mg、レスベラトロール4'-O-α-グルコシドが40mg生成していた。
<HPLC分析条件>
カラム:LiChrospher RP-18(5μm)充填LiChroCART 250-4(メルク社製)
移動相:アセトニトリル-0.2%リン酸水溶液(45:55,v:v)混液
カラム温度:40℃
流速:0.7mL/分
検出波長:310nm
レスベラトロール3-O-α-グルコシド、レスベラトロール(東京化成工業)、又はレスベラトロール3-O-β-グルコシド(東京化成工業)を0.2重量%溶液又は懸濁液となるようにPBSを添加して調製し、これを被検物質とした。皮膚モデル(MatTek製MEL-312B)を用い、この角層側に被検物質を50μL添加し、専用培地(MatTek製EPI-100NMM-113)で、37℃で16日間培養した。2、4、7、9、11、及び14日目に培地及び被検物質を交換した。なお、対照群として被検物質の代わりにPBSを用いて同様の操作を行なった。
レスベラトロール3-O-α-グルコシドを0.2重量%溶液、0.1重量%溶液、0.01重量%溶液となるようにPBSを添加して調製し、これを被検物質として用いて、前記実施例1と同様の方法で、メラニン生成抑制効果を評価した。
表3に示す組成の化粧水を被検物質として使用したこと、角層側への被検物質の添加量を25μLに変更したこと、培養期間を14日間に変更したこと以外は、前記実施例1と同様の方法で、皮膚モデル中のメラニン量の測定を行った。
表4に示す組成の美容液を被検物質として使用したこと、角層側への被検物質の添加量を25μLに変更したこと、培養期間を14日間に変更したこと以外は、前記実施例1と同様の方法で、皮膚モデル中のメラニン量の測定を行った。
表5に示す組成のクリームを被検物質として使用したこと、角層側への被検物質の添加量を25μLに変更したこと、培養期間を14日間に変更したこと以外は、前記実施例1と同様の方法で、皮膚モデル中のメラニン量の測定を行った。
以下の試料溶液、酵素溶液、及びヒアルロン酸溶液を準備した。
(試料溶液)
レスベラトロール3-O-α-グルコシドを0.025又は0.1重量%となるように0.2M酢酸緩衝液(pH4.0)に溶解させ、これを試料溶液とした。
(酵素溶液)
ヒアルロニダーゼ(ウシ精巣由来、SIGMA社製)7400単位を0.2M酢酸緩衝液(pH4.0)1.5mLに溶解させ、これを酵素溶液とした。
(ヒアルロン酸溶液)
ヒアルロン酸ナトリウム(鶏冠由来、和光純薬社製)10mgを0.2M酢酸緩衝液(pH4.0)12.5mLに溶解させ、これをヒアルロン酸溶液とした。
以下の試料溶液、DPPH溶液を準備した。
(試料溶液)
レスベラトロール3-O-α-グルコシドを100、250、500および1000μmol/Lとなるように水に溶解させ、これを試料溶液とした。
(DPPH溶液)
2,2-Diphenyl-1-picrylhydrazyl(和光純薬製)2mgをエタノール10mLに溶解させ、これをDPPH溶液とした。
以下の試料溶液を準備した。
(試料溶液)
レスベラトロール3-O-α-グルコシドを5、10および20mmol/Lとなるように15%エタノール液に溶解させ、これを試料溶液とした。
ヒト皮膚三次元モデルを用いて、レスベラトロール3-O-α-グルコシドの皮膚細胞賦活効果について検討した。
正常ヒト表皮ケラチノサイトを1ウェル当たり5×104個となるように12ウェル培養プレートに播種した。培地としてインスリン、ヒト上皮細胞成長因子(hEGF)、ハイドロコーチゾン、抗菌剤、ウシ下垂体抽出液(BPE)を添加したEpiLife KG‐2培地(基本培地)を用いて37℃、5%CO2中にて48時間プレインキュベートした。更に基本培地のうちハイドロコーチゾンのみ無添加とした培地(アッセイ培地)中で更に48時間インキュベートした。次に、上記アッセイ培地に1μg/mLとなるようにPoly I:C(イノシンリボヌクレオチド鎖とシチジンリボヌクレオチド鎖の二重鎖)を添加した炎症誘導培地に培地を交換し、9時間培養し、炎症モデルとした。次いで、培地を除去し、PBS(Phosphate buffered saline)で洗浄後、アッセイ培地にレスベラトロール3-O-α-グルコシド0.001重量%となるよう添加したサンプル培地に交換し、更に37℃、5%CO2下で15時間培養した。培養後、細胞から全RNAを抽出しリアルタイムPCRによって炎症性サイトカインであるIL-1β遺伝子の発現量の定量を行った。対照区としてはPoly I:C及びレスベラトロール3-O-α-グルコシドを添加せずに培養を行った細胞から回収した全RNAを用いた。比較区としてPoly I:Cによる炎症誘導は行ったがレスベラトロール3-O-α-グルコシドを添加せずに培養を行った細胞から回収した全RNAを用いた。
正常ヒト表皮ケラチノサイトを1ウェル当たり5×104個となるように12ウェル培養プレートに播種した。培地としてインスリン、hEGF、ハイドロコーチゾン、抗菌剤、BPEを添加したEpiLife KG‐2培地(基本培地)を用いて37℃、5%CO2中にて48時間プレインキュベートした。更に基本培地のうちハイドロコーチゾンのみ無添加とした培地(アッセイ培地)中で更に24時間インキュベートした。次に、上記アッセイ培地にレスベラトロール3-O-α-グルコシド0.001重量%となるよう添加したサンプル培地に交換し、37℃、5%CO2下で24時間培養し、レスベラトロール3-O-α-グルコシドによるプレトリートメントを施した。24時間後の培養プレートに、1μg/mLとなるようにPoly I:C(イノシンリボヌクレオチド鎖とシチジンリボヌクレオチド鎖の二重鎖)を添加し、9時間培養して炎症誘導を行なった。培地を除去し、PBSで洗浄後、細胞から全RNAを抽出し、リアルタイムPCRによって炎症性サイトカインであるIL-1β遺伝子の発現量の定量を行った。対照区としてはPoly I:C及びレスベラトロール3-O-α-グルコシドを添加せずに同様に培養を行った細胞から回収したtotal RNAを用いた。比較区として、レスベラトロール3-O-α-グルコシドによるプレトリートメントを行なわずにPoly I:Cによる炎症誘導を同様に行なった細胞から回収した全RNAを用いた。
正常ヒト表皮ケラチノサイトを1ウェル当たり7.5×104個となるように12ウェル培養プレートに播種した。培地としてインスリン、hEGF、ハイドロコーチゾン、抗菌剤、BPEを添加したEpiLife KG‐2培地(基本培地)を用いて37℃、5%CO2中にて72時間プレインキュベートした。培地を除去した後、レスベラトロール3-O-α-グルコシド0.02重量%となるよう添加したサンプル培地に交換し37℃、5%CO2下で培養した。72時間後、細胞から全RNAを抽出しリアルタイムPCRによってサーチュイン1遺伝子の発現量の定量を行った。対照区としてはレスベラトロール3-O-α-グルコシドを添加せずに培養を行った細胞から回収した全RNAを用いた。
正常ヒト表皮ケラチノサイトを1ウェル当たり5×104個となるように12ウェル培養プレートに播種した。培地としてインスリン、hEGF、ハイドロコーチゾン、抗菌剤、BPEを添加したEpiLife KG‐2培地(基本培地)を用いて37℃、5%CO2中にて48時間プレインキュベートした。培地を除去した後、上記基本培地のうちハイドロコーチゾンを無添加にし、且つレスベラトロール3-O-α-グルコシド0.001重量%となるよう添加したサンプル培地に交換し37℃、5%CO2下で培養した。また、比較のために、サンプル培地におけるレスベラトロール3-O-α-グルコシドをレスベラトロール3-O-β-グルコシドに代えて、前記と同条件で培養を行った。培養を33時間行った後に、細胞から全RNAを抽出しリアルタイムPCRによってサーチュイン1遺伝子の発現量の定量を行った。対照区としてはレスベラトロール3-O-α-グルコシド及びレスベラトロール3-O-β-グルコシドを添加せずに培養を行った細胞から回収した全RNAを用いた。
対照区のサーチュイン1遺伝子発現量を100%とし、レスベラトロール3-O-α-グルコシド又はレスベラトロール3-O-β-グルコシド添加区のサーチュイン1遺伝子発現量の相対比(SIRT1遺伝子発現率、%)を求めた。なお、サーチュイン1遺伝子発現量の測定において、内部標準補正にはPPIAを使用した。
ヒト皮膚三次元モデルを用いて、レスベラトロール3-O-α-グルコシドの表皮中マトリックスメタルプロテアーゼ9(MMP9)遺伝子発現への効果について検討した。
正常ヒト真皮線維芽細胞を用いて、レスベラトロール3-O-α-グルコシドの真皮中マトリックスメタルプロテアーゼ1(MMP1)及び9(MMP9)遺伝子発現への効果について検討した。
ヒト皮膚三次元モデルを用いて、皮膚表面側から投与した際のレスベラトロール3-O-α-グルコシド及びレスベラトロールの皮膚モデルへの浸透性について比較した。
レスベラトロール3-O-α-グルコシド及びレスベラトロール3-O-β-グルコシドを経口摂取した際の、血中レスベラトロール代謝物濃度を調べ、吸収性を比較した。
<HPLC分析条件>
カラム:LiChrospher RP-18(5μm)充填LiChroCART 250-4(メルク社製)
移動相:アセトニトリル-0.2%リン酸水溶液(45:55,v:v)混液
カラム温度:40℃
流速:0.7mL/分
検出波長:310nm
注入量:50μL
レスベラトロール3-O-α-グルコシド、レスベラトロール(東京化成工業)又はレスベラトロール3-O-β-グルコシド(東京化成工業)を、それぞれ約40mgずつ量り取り、エタノール(和光純薬工業)を含む溶媒(組成は表8に示す)約70mgを加え、遮光下、25℃の水浴につけて、時々振とう撹拌しながら15時間インキュベートした。15時間後に各試料を0.45μm遠心フィルターでろ過後、ろ液中の各成分の濃度を前記製造例1と同条件でHPLCにて分析し、25℃における溶解濃度(w/v%)を求めた。
グリセリン(和光純薬工業)を含む溶媒(組成は表19に示す)を使用したこと以外は、前記実施例18と同条件で、レスベラトロール3-O-α-グルコシドの溶解度を評価した。
プロピレングリコール(和光純薬工業)を含む溶媒(組成は表20に示す)を使用したこと以外は、前記実施例18と同条件で、レスベラトロール3-O-α-グルコシドの溶解度を評価した。
1,3-ブチレングリコール(和光純薬工業)を含む溶媒(組成は表21に示す)を使用したこと以外は、前記実施例18と同条件で、レスベラトロール3-O-α-グルコシドの溶解度を評価した。
レスベラトロール3-O-α-グルコシドは、格段に高い溶解度を示すことが確認された。特に、1,3-ブチレングリコール50重量%以上の溶媒では、レスベラトロール3-O-α-グルコシドの溶解濃度は20w/v%を超えており、極めて高濃度に濃縮できていた。
ジプロピレングリコール(旭硝子)を含む溶媒(組成は表22に示す)を使用したこと以外は、前記実施例18と同条件で、レスベラトロール3-O-α-グルコシドの溶解度を評価した。
1,2-ペンタンジオール(感光社)を含む溶媒(組成は表23に示す)を使用したこと以外は、前記実施例18と同条件で、レスベラトロール3-O-α-グルコシドの溶解度を評価した。
1,2-ヘキサンジオール(感光社)を含む溶媒(組成は表24に示す)を使用したこと以外は、前記実施例18と同条件で、レスベラトロール3-O-α-グルコシドの溶解度を評価した。
レスベラトロール3-O-α-グルコシド、レスベラトロール(東京化成工業)又はレスベラトロール3-O-β-グルコシド(東京化成工業)を、それぞれ5mgずつ量り取り、水1mLを加え、遮光下、25℃の水浴につけて、時々振とう撹拌しながら20時間インキュベートした。20時間後に各試料を0.45μm遠心フィルターでろ過後、ろ液中の各成分の濃度を前記製造例1と同条件でHPLCにて分析し、25℃における水への溶解濃度(w/v%)を求めた。
レスベラトロール3‐O‐α‐グルコシド(製造例1で製造したもの)、レスベラトロール(東京化成工業)、及びレスベラトロール4’‐O‐α‐グルコシド(製造例1で製造したもの)をそれぞれ2mMとなるよう30容量%エタノール水溶液に溶解し、遮光下、40℃で保存した。保存6ヶ月後の溶液の着色を目視にて確認した。更に、保存前後の溶液について、430nmの吸光度測定により確認すると共に、溶液中の各成分の残存量をHPLCで分析した。HPLCは製造例1と同条件で実施した。
Claims (19)
- レスベラトロール3-O-α-グルコシドを有効成分とすることを特徴とする、皮膚老化防止剤。
- メラニン生成抑制剤又は美白剤として使用される、請求項1に記載の皮膚老化防止剤。
- ヒアルロニダーゼ阻害剤として使用される、請求項1に記載の皮膚老化防止剤。
- 皮膚組織における酸化ストレス低減剤として使用される、請求項1に記載の皮膚老化防止剤。
- マトリックスメタロプロテアーゼ発現抑制剤として使用される、請求項1に記載の皮膚老化防止剤。
- 皮膚細胞に対する細胞賦活剤として使用される、請求項1に記載の皮膚老化防止剤。
- サーチュイン遺伝子発現促進剤として使用される、請求項1に記載の皮膚老化防止剤。
- 皮膚老化を抑制するための抗炎症剤として使用される、請求項1に記載の皮膚老化防止剤。
- 請求項1~8のいずれかに記載の皮膚老化防止剤を含む、皮膚外用剤。
- 請求項1~8のいずれかに記載の皮膚老化防止剤を含む、口腔用剤。
- 請求項1~8のいずれかに記載の皮膚老化防止剤を含む、飲食品。
- 請求項1~8のいずれかに記載の皮膚老化防止剤を含む、全身投与用の医薬品。
- レスベラトロール3-O-α-グルコシドの、皮膚老化防止剤の製造のための使用。
- 皮膚老化の防止のための処置に使用されるレスベラトロール3-O-α-グルコシド。
- 皮膚老化防止が求められているヒトに、レスベラトロール3-O-α-グルコシドを経皮又は経口投与する工程を含む、皮膚老化防止方法。
- レスベラトロール3-O-α-グルコシドが、炭素数1~6の1~4価アルコールを含む溶媒に含有されてなる、レスベラトロール3-O-α-グルコシドの濃縮液。
- 炭素数1~6の1~4価アルコールが、エタノール、プロピレングリコール、1,3-ブチレングリコール、ジプロピレングリコール、1,2-ペンタンジオール、1,2-ヘキサンジオール、及びグリセリンよりなる群から選択される少なくとも1種である、請求項16に記載の濃縮液。
- 溶媒の総量100重量部当たり、炭素数1~6の1~4価アルコールが5~100重量部含まれる、請求項16又は17に記載の濃縮液。
- レスベラトロール3-O-α-グルコシドが5~50w/v%含まれる、請求項16~18のいずれかに記載の濃縮液。
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JP2019055932A (ja) * | 2017-09-20 | 2019-04-11 | 学校法人同志社 | Dj−1タンパク質産生促進用組成物 |
JP7061766B2 (ja) | 2017-09-20 | 2022-05-02 | 学校法人同志社 | Dj-1タンパク質産生促進用組成物 |
JP2021507905A (ja) * | 2017-12-21 | 2021-02-25 | ロレアル | 化粧品に使用するためのレスベラトロールのキシロシド誘導体 |
WO2023008218A1 (ja) * | 2021-07-28 | 2023-02-02 | 池田食研株式会社 | レスベラトロールグルクロニドの新たな用途 |
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EP3130331B1 (en) | 2021-05-26 |
JPWO2015156328A1 (ja) | 2017-04-13 |
US20170035674A1 (en) | 2017-02-09 |
US10149809B2 (en) | 2018-12-11 |
JP6664319B2 (ja) | 2020-03-13 |
ES2879955T3 (es) | 2021-11-23 |
EP3130331A4 (en) | 2017-11-15 |
EP3130331A1 (en) | 2017-02-15 |
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