WO2014171279A1 - 1,5-アンヒドロ-d-グルシトール含有コラーゲン産生促進剤 - Google Patents
1,5-アンヒドロ-d-グルシトール含有コラーゲン産生促進剤 Download PDFInfo
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- WO2014171279A1 WO2014171279A1 PCT/JP2014/058542 JP2014058542W WO2014171279A1 WO 2014171279 A1 WO2014171279 A1 WO 2014171279A1 JP 2014058542 W JP2014058542 W JP 2014058542W WO 2014171279 A1 WO2014171279 A1 WO 2014171279A1
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- WIPO (PCT)
- Prior art keywords
- derivatives
- anhydro
- collagen production
- glucitol
- acid
- Prior art date
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Definitions
- the present invention relates to a collagen production promoter containing 1,5-anhydro-D-glucitol (sometimes abbreviated as “1,5-AG” in the present specification) or a derivative thereof, and a composition containing the same. .
- the skin is roughly composed of three types of layered structures of epidermis, dermis and subcutaneous tissue.
- the epidermis consists of a stratum corneum in contact with the outside world and a basal layer that creates new skin cells, and the dermis plays a role in supporting the basal layer.
- Typical components of the dermis include collagen, elastin, and hyaluronic acid. Among them, collagen accounts for 70%, and collagen production plays an important role in preventing and improving wrinkles.
- Patent Document 1 discloses a plant containing soybean seed, soybean germ, soybean embryo, soybean bud, wheat seed, wheat germ, wheat germ, wheat germ, soy milk, okara and the like.
- a cosmetic composition containing the extract is disclosed.
- Patent Document 2 discloses a humectant containing acyl oligopeptide, proline, hydroxyproline and the like.
- Patent Document 3 discloses an external composition containing sorbitol, mannitol, xylitol, and glycerin.
- Patent Document 4 discloses a cosmetic containing sorbitol, maltitol, xylitol, and erythritol.
- An object of the present invention is to provide a collagen production promoter having good biocompatibility and usability, and a composition containing the same.
- 1,5-AG is a non-reducing sugar in which the 1-position of D-glucose is reduced. Therefore, 1,5-AG is less reactive than reducing sugar and is chemically stable under conditions such as acidic, alkaline, and high temperature. is there. In addition, 1,5-AG is a saccharide that is present in the body next to D-glucose, and has excellent characteristics such as high biocompatibility and no safety problem.
- 1,5-AG can be used as a novel material having the ability to promote collagen production, thereby completing the present invention. It came.
- the present invention relates to the following [1] to [10].
- [1] A collagen production promoter in cells, comprising at least one selected from the group consisting of 1,5-anhydro-D-glucitol and its derivatives.
- [2] A composition comprising the collagen production promoter according to [1].
- [3] Collagen in a cell, comprising a step of administering at least one selected from the group consisting of 1,5-anhydro-D-glucitol and a derivative thereof to an individual in need of promoting collagen production in the cell. How to promote production.
- [4] including a step of administering an effective amount of at least one selected from the group consisting of 1,5-anhydro-D-glucitol and derivatives thereof to an individual in need of prevention and / or improvement of skin wrinkles
- a method for preventing and / or improving skin wrinkles [5] At least one compound selected from the group consisting of 1,5-anhydro-D-glucitol and derivatives thereof for promoting collagen production in cells.
- [8] Use of at least one compound selected from the group consisting of 1,5-anhydro-D-glucitol and derivatives thereof for preventing and / or improving skin wrinkles.
- [9] Use of at least one compound selected from the group consisting of 1,5-anhydro-D-glucitol and derivatives thereof in the preparation of a composition for promoting collagen production in cells.
- [10] Use of at least one compound selected from the group consisting of 1,5-anhydro-D-glucitol and its derivatives in the preparation of a composition for preventing and / or improving skin wrinkles.
- the collagen production promoter of the present invention has an excellent effect of not only having a collagen production promoting function but also having a moisturizing effect.
- FIG. 1 is a diagram showing the amount of collagen production in human fibroblasts.
- FIG. 2 is a diagram showing changes in the amount of moisture on the human skin surface.
- the collagen production promoter in the cell of the present invention (sometimes simply referred to as the collagen production promoter of the present invention) is a group consisting of 1,5-anhydro-D-glucitol (1,5-AG) and its derivatives. It contains at least one selected from the above.
- “promoting collagen production in cells” means that when 1,5-AG and its derivatives are allowed to act on cells, the amount of collagen produced in the cells is increased compared to the case where they are not acted on. Means. For example, it means that the amount of collagen production in the cells preferably reaches about 110% or more, more preferably about 120% or more, and even more preferably about 130% or more.
- the cell is not particularly limited as long as it has a collagen-producing ability, and examples thereof include fibroblasts and keratinocytes.
- 1,5-Anhydro-D-glucitol (1,5-AG) is a structure in which the 1-position of D-glucose is reduced, and is one of the most abundant polyols in the body.
- 1,5-AG derivatives are converted to 1,5-AG on the skin and in the body, and the effects of the present invention are exhibited.
- 1,5-AG derivatives include, for example, formula (I):
- R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom, a saccharide, an amino acid, a vitamin, a vitamin-like substance or a fatty acid, provided that R 1 , R 2 , R 3 and R 4 are not simultaneously hydrogen atoms
- a preferred example is a compound represented by the formula:
- R 1 , R 2 , R 3 and R 4 in formula (I) each independently represent a hydrogen atom, a saccharide, an amino acid, a vitamin, a vitamin-like substance or a fatty acid, provided that R 1 , R 2 , R 3 and R 4 are not simultaneously hydrogen atoms.
- saccharide examples include compounds having 3 to 7 carbon atoms such as aldose, ketose, alditol, deoxy sugar, anhydro sugar, amino sugar, inositol, aldonic acid, uronic acid, aldaric acid, carb sugar, thio sugar, imino sugar, aza sugar and the like.
- disaccharides and polysaccharides comprising them as constituents may be either cyclic
- monosaccharides such as glucose, galactose, mannose, and glucuronic acid, and maltose, isomaltose, and lactose containing them from the viewpoints of safety, biocompatibility, and types of enzymes present in the digestive tract.
- Disaccharides and polysaccharides such as trehalose are preferred.
- the derivatives having these saccharides are hydrolyzed by a series of enzymes such as amylase, glucosidase, mannosidase, galactosidase, fucosidase, glucuronidase existing in the digestive tract, or the physiological acidity in the skin surface or digestive tract. It is hydrolyzed and converted to 1,5-AG when exposed to alkaline conditions.
- the amino acids may be any of L-type amino acid residues, D-type amino acid residues, mixtures thereof, or derivatives thereof.
- the amino acid may be any of ⁇ -amino acid, ⁇ -amino acid, ⁇ -amino acid and ⁇ -amino acid, with ⁇ -amino acid being preferred. Specific examples include glycine, alanine, valine, leucine, isoleucine, serine, threonine, aspartic acid, glutamic acid, asparagine, glutamine, lysine, arginine, cystine, methionine, phenylalanine, tyrosine, tryptophan, histidine, proline and the like. . Derivatives having these amino acids are hydrolyzed by peptidase or esterase in the skin or digestive tract, or hydrolyzed by exposure to physiological acidic or alkaline conditions on the skin surface or digestive tract. -Converted to AG.
- Vitamins and vitamin-like active substances include vitamin A, vitamin B1 (thyamine, thiamine), vitamin B2 (riboflavin), vitamin B5 (pantothenic acid), vitamin B6 (pyridoxine), vitamin B12 (cobalamin), vitamin C ( Examples include ascorbic acid), vitamin D, vitamin E, vitamin K, folic acid, niacin (vitamin B3, nicotinic acid), vitamin B17 (leitolyl, amygdalin), inositol, choline, vitamin F, flavonoids, and the like. Derivatives containing these vitamins and vitamin-like active substances are hydrolyzed by peptidases, esterases, etc. in the skin and digestive tract, or hydrolyzed by exposure to physiological acidic or alkaline conditions on the skin surface or digestive tract. And converted to 1,5-AG.
- fatty acids having 2 to 20 carbon atoms such as octanoic acid, decanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanoic acid, icosanoic acid and palmitic acid are preferable, and fatty acids having 8 to 20 carbon atoms are more preferable.
- Derivatives containing these fatty acids are hydrolyzed by various esterases including lipases in the skin and digestive tract, or hydrolyzed by exposure to physiological acidic or alkaline conditions on the skin surface or digestive tract. Converted to 1,5-AG.
- saccharides, amino acids, vitamins, vitamin-like substances or fatty acids can be converted into 1,5-AG in the living body, preferably on the skin surface. Vitamin-like substances or fatty acids themselves or their salts may be used.
- saccharides, amino acids, vitamins, vitamin-like substances or fatty acids as R 1 , R 2 , R 3 and R 4 mean residues bonded to 1,5-AG. .
- 1,5-AG and its derivatives are commercially available products, but any method known in the art, for example, JP-A-2008-54531, JP-A-2010-082661, J. ⁇ Am. Chem. Soc., 72, 4547 (1950), J. Chem. Soc., 214 (1956) may be used.
- Examples of commercially available products include 1,5-anhydro-D-glucitol (manufactured by Wako Pure Chemical Industries).
- the structure of the synthesized product can be confirmed according to known methods such as NMR, IR, optical rotation, MS, and melting point measurement.
- 1,5-AG and derivatives thereof of the present invention can be used to promote the production of collagen, for example, type I collagen, in cells.
- 1,5-AG and its derivatives can be used alone or in combination of two or more, and the total content in the collagen production promoter of the present invention is not particularly limited, and is usually about 0.1 to 100% by weight. is there.
- the form of the collagen production promoter of the present invention is not particularly limited as long as at least one selected from the group consisting of 1,5-AG and derivatives thereof can be applied to the surface of the target substance or taken into the body.
- a powder agent, a liquid agent, a cream agent, etc. are illustrated.
- the present invention also provides a composition containing the collagen production promoter of the present invention.
- the form of the composition is not particularly limited as long as at least one selected from the group consisting of 1,5-AG and derivatives thereof can be taken into cells.
- the form as an external preparation composition is demonstrated from a viewpoint of exhibiting an effect, and the form as an internal use composition from a viewpoint which can be ingested easily, Preferably it can be used as an external preparation.
- an external preparation composition it can be provided as a pharmaceutical composition, a quasi-drug composition, and a cosmetic composition.
- the form of the external preparation composition examples include solid, semi-solid or liquid preparations for transdermal administration or transmucosal (intraoral or intranasal) administration. Suppositories are also included. For example, emulsions such as emulsions and lotions, tinctures for external use, liquid preparations such as liquids for transmucosal administration, ointments such as oily ointments and hydrophilic ointments, transdermal administration such as films, tapes, and poultices Or for transmucosal administration, aerosols, sprays such as sprays, bathing agents and the like.
- emulsions such as emulsions and lotions, tinctures for external use
- liquid preparations such as liquids for transmucosal administration
- ointments such as oily ointments and hydrophilic ointments
- transdermal administration such as films, tapes, and poultices Or for transmuco
- a cosmetic composition for example, basic cosmetics such as lotions, emulsions, creams, oils, packs, gels, makeup cosmetics such as foundations, blushers, lipsticks, waxes, hair artnics, It can be used in any form such as soaps, shampoos, facial cleansing foams, cleansing agents such as body cleansing agents, skin perfumes such as eau de cologne, deodorant and perfume, bathing agents.
- an internal use composition it can be provided as a pharmaceutical composition, a quasi-drug composition, a food composition, or a cosmetic composition.
- the form include forms that can be easily blended (for example, powder form and granule form) and tablet forms and liquid forms from the viewpoint of easy intake.
- liquids, extracts, elixirs, capsules hard capsules, soft capsules, etc.
- granules, pills, suspensions, emulsions, suppositories powders, spirits, tablets, syrups , Soaking agent, decoction, tincture, troche, fragrance, limonade, flow extract, etc., quasi-drug composition, boiled food (boiled, boiled, meat potato, etc.) White salad, salad, etc.), vinegared food, fried food (tempura, fried chicken, fried food, etc.), steamed food (shumai, steamed rice bowl, etc.), konpeira, gyoza, confectionery (boiled, large-format, rice bowl, grass bowl, dumpling, manju, Rice crackers, sheep crab, Uiro, red rice, cake, crepe, cookies, pudding, jelly, steamed bread, chocolate, caramel, raw caramel, salmon, etc.), bread (sandwich etc.), sake, fruit sake, mirin,
- composition of the present invention having the above-mentioned form contains at least one selected from the group consisting of 1,5-AG and derivatives thereof, it is used in the pharmaceutical field, cosmetic field, food field, etc. according to a conventional method.
- Usually used carriers, bases, and / or additives can be appropriately blended and prepared within the scope of achieving the object of the present invention.
- Carriers, bases, and / or additives used in the pharmaceutical field include excipients (glucose, lactose, sucrose, sodium chloride, starch, calcium carbonate, kaolin, crystalline cellulose, cocoa butter, hydrogenated vegetable oil, talc, etc.
- Binder distilled water, physiological saline, ethanol water, simple syrup, glucose solution, starch solution, gelatin solution, carboxymethylcellulose, potassium phosphate, polyvinylpyrrolidone, etc.
- disintegrator sodium alginate, agar, sodium bicarbonate, Calcium carbonate, sodium lauryl sulfate, stearic acid monoglyceride, starch, lactose, gum arabic powder, gelatin, ethanol, etc.
- disintegration inhibitors sodium lauryl sulfate, stearic acid monoglyceride, starch, lactose, gum arabic powder, gelatin, ethanol, etc.
- disintegration inhibitors sodium lauryl sulfate, stearic acid monoglyceride, starch, lactose, gum arabic powder, gelatin, ethanol, etc.
- disintegration inhibitors sodium lauryl sulfate, stearic acid monoglyceride, starch, lactose, gum arabic
- Carriers, bases, and / or additives used in the cosmetics field include oils (butyl myristate, isobutyl myristate, butyl palmitate, isobutyl palmitate, butyl stearate, isobutyl stearate, butyl isostearate, myristine Cetyl acid, isostearyl laurate, isostearyl myristate, propylene glycol dicaprate, isostearyl adipate, squalane, liquid paraffin, isoparaffin, beef tallow, lard, mink oil, fish oil, corn oil, cocoa butter, almond oil, beeswax Lanolin, reduced lanolin, liquid lanolin, etc.), higher alcohols (lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, oleyl alcohol, behenyl alcohol, hexyl) Decyl alcohol, etc.), fatty acids (caprylic acid, capric acid, unde
- Carriers, bases and / or additives used in the food field include edible oil (salad oil), glucose, fructose, sucrose, maltose, sorbitol, stevioside, corn syrup, lactose, citric acid, tartaric acid, malic acid , Succinic acid, lactic acid, L-ascorbic acid, dl- ⁇ -tocopherol, sodium erythorbate, glycerin, propylene glycol, glycerin fatty acid ester, propylene glycol fatty acid ester, gum arabic, sucrose fatty acid ester, sorbitan, casein, gelatin, pectin And agar, vitamin Bs, nicotinic acid amide, calcium pantothenate, amino acids, calcium salts, pigments, fragrances, preservatives and the like. These contents are not particularly limited, and can be used according to a known technique.
- antioxidants reduced ascorbic acid, vitamin E, reduced glutathione, vitamin A derivatives, lycopene, ⁇ -cryptoxanthin, astaxanthin, zeaxanthin, fucoxanthin, uric acid, ubiquinone, coenzyme Q10, folic acid, garlic extract , Allicin, sesamin, lignans, catechin, isoflavone, chalcone, tannins, flavonoids, coumarin, isocoumarins, blueberry extract, arbutin, anthocyanin, apple polyphenol, grape seed extract, ellagic acid, kojic acid, vitamin A, vitamin B1 , Vitamin B2, vitamin B6, vitamin B12, vitamin C, vitamin D, vitamin E, vitamin P, choline, niacin, pantothenic acid, calcium folate, EPA, DHA, oligosaccharide, food Fiber, squalene, soy lec
- At least one selected from the group consisting of 1,5-AG of the present invention and derivatives thereof is left as it is or as a mixture, dried, various solutions, pasty state, etc.
- Various additives, carriers, base materials and the like are added to this, and a powder, granule, tableting, dissolving or mixing can be used to prepare a preparation.
- the external preparation As a specific preparation example of the external preparation, at least one selected from the group consisting of 1,5-AG and its derivatives of the present invention is used as it is, or the mixture is a highly water-soluble solvent such as purified water, ethanol or glycerin.
- a cosmetic liquid and / or makeup by slowly mixing the mixture and the compound with the compound and a compound that has been previously mixed with a highly fat-soluble substance such as squalane, jojoba oil, or glycerin monostearate.
- a cream can be prepared.
- composition of the present invention contains 1,5-AG and its derivatives together with other components that can be used for the same applications, for example, components having a known collagen production promoting effect or a known moisturizing effect. Can do.
- the composition of the present invention is suitably used for promoting collagen production in cells.
- it can be used for diseases requiring an action of promoting collagen production for treatment or prevention.
- it can be used to improve scars caused by trauma such as burns, abrasions, wounds, split wounds, cut wounds, and stab wounds. it can.
- It can also be used as a preventive and / or therapeutic agent for skin wrinkles due to UV exposure, drying, aging, and the like.
- treatment in the present specification is intended to include “improvement”.
- the content of at least one selected from the group consisting of 1,5-AG and derivatives thereof takes into account its administration form, administration method, etc., and the desired effect of the present invention can be obtained.
- the amount is not particularly limited as long as it is an amount that can be obtained.
- the content of at least one selected from the group consisting of 1,5-AG and derivatives thereof is preferably 0.01 to 10% by weight, preferably 0.05 to 7% by weight. Is more preferable, and 0.1 to 5% by weight is more preferable.
- “at least one content selected from the group consisting of 1,5-AG and its derivatives” refers to 1,5-AG and its derivatives contained in the external preparation composition of the present invention. It means the total content.
- composition of the present invention is administered by an appropriate administration method according to the preparation form.
- administration method There is also no particular limitation on the administration method, and for example, it can be administered by internal use, external use or injection.
- administration is intended to include “intake” and “take”.
- the dose of the composition of the present invention is appropriately set according to the administration form, administration method, purpose of use and age, weight, and symptom of the patient to whom the composition is administered, and is not constant.
- it is usually preferably about 0.1 ⁇ g to 5 g / day per weight of about 50 kg per adult.
- Administration may be performed once or divided into several times within one day within a desired dose range.
- the administration period is also arbitrary.
- the administration subject of the present specification is preferably a human who needs an action of promoting collagen production in cells, but may be a pet animal or the like.
- the present invention also provides a humectant containing at least one selected from the group consisting of the 1,5-AG and derivatives thereof. Since 1,5-AG and its derivatives in the composition of the present invention are sugar alcohols, in addition to the collagen production promoting function, a moisturizing action is also exerted by sugar alcohols and can be suitably used as a moisturizing agent. it can.
- the surface of the target substance undergoes changes such as hydrolysis due to physical factors (acidic or alkaline, moisture, heat, light, etc.), resulting in 1,5-AG or two or more A 1,5-AG derivative having a hydroxyl group, or a 1,5-AG derivative of a polyol having a plurality of hydroxyl groups in the molecule (even if no chemical change occurs on the surface of the article)
- the moisturizing effect is exhibited even when used for an article other than a living body.
- moisturizing agents include cosmetic wetting agents, anti-drying agents, food wetting agents, and anti-drying agents, and the form is not limited. Since the humectant of the present invention contains 1,5-AG and its derivatives as in-vivo substances, it has high biological safety.
- the content of the moisturizing agent in cosmetics and foods is not particularly limited as long as the desired effect of the present invention can be obtained.
- the present invention further provides a method for promoting collagen production in cells, characterized by using at least one selected from the group consisting of 1,5-AG and derivatives thereof, or the composition. Further, based on the collagen production promoting function, at least one selected from the group consisting of the 1,5-AG and derivatives thereof, or the composition is used, and / or skin wrinkles are prevented and / or Provide a way to improve.
- At least one selected from the group consisting of 1,5-AG and derivatives thereof, or the above composition may be used in an effective amount or more that can obtain the effect of promoting collagen production.
- Test example 1 To evaluate the effect of 1,5-AG on type I collagen synthesis in dermal fibroblasts. Specifically, normal human fibroblasts were seeded in a 96-well microplate using Dulbecco's modified Eagle medium (DMEM) containing 0.5% fetal bovine serum (FBS). After culturing at 37 ° C. for 24 hours, the medium was exchanged with DMEM containing 0.5% FBS containing a sample of a predetermined concentration. The same treatment was performed using magnesium ascorbate phosphate as a positive control (PC). After culturing in the sample-containing medium for 24 hours, the culture supernatant was recovered and subjected to ELISA. The amount of protein was measured using PIERCE (Pierce Biotechnology Inc.) according to the bicinchoninic acid (BCA) method.
- DMEM Dulbecco's modified Eagle medium
- FBS fetal bovine serum
- the culture supernatant and the collagen solution for calibration curve were placed in each well of the high-adsorption ELISA plate, coated overnight at 4 ° C., and then blocked at 37 ° C. for 1 hour using 1% bovine serum albumin (BSA) solution.
- BSA bovine serum albumin
- For the primary antibody reaction Anti-Human Collagen Type I antibody (Bio-Rad Laboratories, Inc., Rabbit) was diluted with a 0.3% BSA solution, added to each well, and reacted at 37 ° C. for 1 hour.
- histophan MAX-PO (R) manufactured by Nichirei, Rabbit
- was diluted with a phosphate buffer added to each well, and reacted at 37 ° C. for 1 hour.
- a phosphoric acid-citrate buffer (0. 0,3) containing 0.3 mg / mL 2,2′-Azinobis (3-ethylbenzothiazole-6-sulfonic acid) diammonium salt (ABTS) and 0.03% hydrogen peroxide. 1M, pH 4.0) was added to each well and reacted for 20 minutes, and the absorbance at 405 nm was measured with a microplate reader.
- ABTS 2,2′-Azinobis (3-ethylbenzothiazole-6-sulfonic acid) diammonium salt
- the amount of collagen in the culture supernatant was calculated from a calibration curve prepared with commercially available collagen.
- the amount of collagen synthesized per unit protein was calculated by dividing the amount of collagen in the medium by the amount of protein in all cells.
- the amount of collagen synthesis at each concentration was tested for significance using the Student-t test, and the difference from the untreated control was evaluated. The results are shown in Table 1 and FIG.
- 1,5-AG significantly increased the amount of type I collagen synthesized in normal human fibroblasts.
- Test example 2 The moisturizing effect of 1,5-AG is evaluated by a short-term use test of human volunteers. Specifically, 5 males aged 26 to 34 years old were subjects, and an aqueous solution of a predetermined concentration of the sample shown in Table 2 was applied to the inner side of the forearm at 2.5 ⁇ L / cm 2, and the moisture on the skin surface according to the following method. The amount was measured.
- the change in the amount of water at each test site was expressed as a relative value with an initial value of 100%.
- the difference in the amount of moisture on the skin surface before and after the test sample was used in each subject was tested for significant difference by Student-t test.
- Table 2 and FIG. 2 show the results obtained by rejecting the data of the subject whose skin surface water content in the non-application site increased with time as an abnormal value and calculating using the measured values of four people.
- each formulation example means weight% of each component.
- Formulation Example 1 Emulsion The following 1-4 oil components are heated and mixed at 70-80 ° C. Next, when the following 5 to 11 water-soluble components were heated and mixed at 70 to 80 ° C, the mixture of the oily components was slowly stirred and mixed so that the temperature does not fall below 70 ° C. After stirring at temperature for 12-24 hours, the desired emulsion is produced by slowly cooling to room temperature.
- the collagen production promoter containing 1,5-AG or a derivative thereof of the present invention is preferably used for preventing and / or improving skin wrinkles, for example, to promote collagen production in cells.
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Abstract
Description
〔1〕 1,5-アンヒドロ-D-グルシトール及びその誘導体からなる群より選ばれる少なくとも1つを含有してなる、細胞におけるコラーゲン産生促進剤。
〔2〕 前記〔1〕記載のコラーゲン産生促進剤を含有してなる組成物。
〔3〕 1,5-アンヒドロ-D-グルシトール及びその誘導体からなる群より選ばれる少なくとも1つを、その有効量を細胞におけるコラーゲン産生促進を必要とする個体に投与する工程を含む、細胞におけるコラーゲン産生の促進方法。
〔4〕 1,5-アンヒドロ-D-グルシトール及びその誘導体からなる群より選ばれる少なくとも1つを、その有効量を皮膚のシワの予防及び/又は改善を必要とする個体に投与する工程を含む、皮膚のシワの予防及び/又は改善方法。
〔5〕 細胞におけるコラーゲン産生を促進するための、1,5-アンヒドロ-D-グルシトール及びその誘導体からなる群より選ばれる少なくとも1つの化合物。
〔6〕 皮膚のシワを予防及び/又は改善するための、1,5-アンヒドロ-D-グルシトール及びその誘導体からなる群より選ばれる少なくとも1つの化合物。
〔7〕 細胞におけるコラーゲン産生を促進するための、1,5-アンヒドロ-D-グルシトール及びその誘導体からなる群より選ばれる少なくとも1つの化合物の使用。
〔8〕 皮膚のシワを予防及び/又は改善するための、1,5-アンヒドロ-D-グルシトール及びその誘導体からなる群より選ばれる少なくとも1つの化合物の使用。
〔9〕 細胞におけるコラーゲン産生を促進するための組成物の調製における、1,5-アンヒドロ-D-グルシトール及びその誘導体からなる群より選ばれる少なくとも1つの化合物の使用。
〔10〕 皮膚のシワを予防及び/又は改善するための組成物の調製における、1,5-アンヒドロ-D-グルシトール及びその誘導体からなる群より選ばれる少なくとも1つの化合物の使用。
で表わされる化合物が好適例として挙げられる。
1,5-AGの真皮線維芽細胞のI型コラーゲン合成に対する作用を評価する。具体的には、正常ヒト線維芽細胞を、0.5%ウシ胎仔血清(FBS) 含有ダルベッコ変法イーグル培地(DMEM)を用いて96穴マイクロプレートに播種した。37℃で24時間培養後に所定濃度の試料を含有した0.5%FBS含有DMEMと交換した。陽性コントロール(P.C.)としてアスコルビン酸リン酸マグネシウムを用い、同様の処理を行った。試料含有培地で24時間培養したのち、培養上清を回収してELISAに供した。また、タンパク量をビシンコニン酸(BCA)法に従って、PIERCE(Pierce Biotechnology Inc.社製)を用いて測定した。
1,5-AGの保湿効果をヒトボランティアの短期使用試験により評価する。具体的には、26歳から34歳の男性5名を被験者として、表2に示す試料の所定濃度の水溶液を、前腕内側部に2.5μL/cm2塗布し、以下の方法に従って皮膚表面水分量を測定した。
各被検者は、前腕内側を所定の洗浄料にて洗浄後、恒温恒湿室(室温22℃、湿度45%)にて15分馴化した。その後、SKICON200(I.B.S株式会社製 皮表角層水分測定装置)を用いて皮膚表面水分量の初期値を測定した。次いで各試験試料及び精製水を塗布方法に従い塗布した。さらに、無塗布部位を設定した。試料塗布直後、15分後、30分後、45分後に水分量を測定した。無塗布部位の水分量は試料塗布部位の測定時間に合わせて測定した。各被検部位の水分量の変化は、初期値を100%とした相対値で表した。各被験者における試験試料使用前後の皮膚表面水分量の差異は、Student-t検定にて有意差検定を行った。無塗布部位の皮膚表面水分量が経時的に増加した被験者のデータを異常値として棄却し、4名の測定値を用いて演算した結果を表2及び図2に示す。
下記1~4の油状成分を70~80℃において加熱混合する。次に、下記5~11の水溶性成分を70~80℃において加熱混合したところに、前記油状成分の混合物を、温度が70℃を下回らないように注意しながら、ゆっくりと攪混合し、同温度にて12~24時間攪拌した後、ゆっくりと室温まで冷却することで目的の乳液を製造する。
Claims (15)
Priority Applications (6)
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CA2907968A CA2907968A1 (en) | 2013-04-15 | 2014-03-26 | 1,5-anhydro-d-glucitol-containing collagen production accelerator |
EP14786113.2A EP2990035B1 (en) | 2013-04-15 | 2014-03-26 | 1,5-anhydro-d-glucitol-containing collagen production accelerator |
KR1020157032593A KR20150143738A (ko) | 2013-04-15 | 2014-03-26 | 1,5-안하이드로-d-글루시톨 함유 콜라겐 산생 촉진제 |
CN201480021322.2A CN105120861B (zh) | 2013-04-15 | 2014-03-26 | 含有1,5‑脱水‑d‑葡糖醇的胶原产生促进剂 |
US14/782,006 US20160022556A1 (en) | 2013-04-15 | 2014-03-26 | 1,5-anhydro-d-glucitol-containing collagen production accelerator |
JP2015512381A JP6045688B2 (ja) | 2013-04-15 | 2014-03-26 | 1,5−アンヒドロ−d−グルシトール含有コラーゲン産生促進剤 |
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US (1) | US20160022556A1 (ja) |
EP (1) | EP2990035B1 (ja) |
JP (1) | JP6045688B2 (ja) |
KR (1) | KR20150143738A (ja) |
CN (1) | CN105120861B (ja) |
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WO2017122495A1 (ja) * | 2016-01-13 | 2017-07-20 | 国立大学法人富山大学 | セラミド含量増加剤 |
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CN109528554A (zh) * | 2018-12-10 | 2019-03-29 | 珀莱雅化妆品股份有限公司 | 一种抗皱组合物及其巴布剂的制备方法 |
CN114457136A (zh) * | 2022-01-27 | 2022-05-10 | 美尔健(深圳)生物科技有限公司 | 一种基于玫瑰花发酵重组胶原蛋白的发酵液及其应用 |
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- 2014-03-26 US US14/782,006 patent/US20160022556A1/en not_active Abandoned
- 2014-03-26 WO PCT/JP2014/058542 patent/WO2014171279A1/ja active Application Filing
- 2014-03-26 CN CN201480021322.2A patent/CN105120861B/zh active Active
- 2014-03-26 JP JP2015512381A patent/JP6045688B2/ja active Active
- 2014-03-26 CA CA2907968A patent/CA2907968A1/en not_active Abandoned
- 2014-03-26 KR KR1020157032593A patent/KR20150143738A/ko not_active Application Discontinuation
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JP6045688B2 (ja) | 2016-12-14 |
US20160022556A1 (en) | 2016-01-28 |
JPWO2014171279A1 (ja) | 2017-02-23 |
EP2990035B1 (en) | 2018-03-07 |
EP2990035A1 (en) | 2016-03-02 |
CA2907968A1 (en) | 2014-10-23 |
KR20150143738A (ko) | 2015-12-23 |
EP2990035A4 (en) | 2016-10-12 |
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