WO2020196484A1 - 皮膚バリア機能促進剤 - Google Patents

皮膚バリア機能促進剤 Download PDF

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WO2020196484A1
WO2020196484A1 PCT/JP2020/012913 JP2020012913W WO2020196484A1 WO 2020196484 A1 WO2020196484 A1 WO 2020196484A1 JP 2020012913 W JP2020012913 W JP 2020012913W WO 2020196484 A1 WO2020196484 A1 WO 2020196484A1
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Prior art keywords
barrier function
skin barrier
skin
function promoter
glyceryl glucoside
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PCT/JP2020/012913
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English (en)
French (fr)
Japanese (ja)
Inventor
鈴木　卓弥
伊世 鈴木
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Toyo Sugar Refining Co Ltd
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Toyo Sugar Refining Co Ltd
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Priority to JP2021509436A priority Critical patent/JPWO2020196484A1/ja
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations

Definitions

  • the present invention relates to a skin barrier function promoter.
  • the skin has a skin barrier function such as preventing the evaporation of water inside the skin and preventing the invasion of foreign substances such as allergens and microorganisms from the outside world.
  • the skin barrier function is mainly carried out by the tight junctions of the stratum corneum and the stratum granulosum in the epidermis.
  • Tight junctions are also called tight junctions, and play the role of a fence that adheres cells to each other, closes intercellular spaces, and partitions cell membranes. Tight junctions of the skin are known to exist only between the cells of SG2 cells when the cells existing in the stratum granulosum inside the stratum corneum are named SG1 cells to SG3 cells from the surface, and pass between the cells. It forms a barrier that limits the movement of substances.
  • Tight junctions are formed so as to close the gaps between adjacent cell membranes by adhering them with a transmembrane protein that crosses the gaps.
  • the transmembrane protein includes claudin, occludin, tricellulin and the like, which are called adhesive proteins.
  • Claudin is the major transmembrane protein for tight junction formation
  • occludin limits the permeability of binding sites
  • torcerin closes the cell membrane at the contact points of three cells, causing leakage of water and cell secretory components from the epithelium. Is being prevented.
  • Patent Document 1 discloses a skin barrier function improving agent containing a glycerin skeleton-containing group and a modified hyaluronic acid skeleton, in which the hyaluronic acid skeleton is in the water layer of the stratum corneum and the glycerin skeleton is in the lipid layer. It is reported that the placement modifies the lamellar structure and improves the skin barrier structure.
  • Patent Document 2 discloses an external preparation for promoting skin barrier function containing glyceride and astaxanthin. Further, Patent Document 3 discloses a cosmetic containing a glycerin compound having a predetermined molecular weight, and reports that the compound can sufficiently express the skin barrier function of ceramide.
  • Non-Patent Document 1 states that a single administration of a glycerol solution to the testis disrupts actin, occludin, and tubulin associated with tight junctions, which loosens Sertoli cells and improves the permeability of the blood-testis barrier. It discloses that.
  • Patent Documents 1 to 3 are all aimed at improving or promoting the skin barrier function by the glycerin compound, but do not have the effect of promoting the skin barrier function by the tight junction. Therefore, there is still room for improvement in promoting the skin barrier function.
  • the present invention includes the following [1] to [7].
  • [1] A skin barrier function promoter containing glyceryl glucoside.
  • [2] The skin barrier function promoter according to [1], which promotes the formation of tight junctions.
  • [3] The skin barrier function promoter according to [1] or [2], which enhances the expression of tight junction adhesive proteins.
  • [4] The skin barrier function promoter according to [3], wherein the adhesive protein is occludin.
  • [6] A quasi-drug containing the skin barrier function promoter according to any one of [1] to [4].
  • [7] An external preparation for skin containing the skin barrier function promoter according to any one of [1] to [4].
  • the skin barrier function of the epidermis can be promoted by promoting the formation of tight junctions.
  • the present invention can provide cosmetics, quasi-drugs, and external preparations for skin that can promote the skin barrier function.
  • FIG. 1 is a fluorescence micrograph of normal human epidermal keratinocytes treated with glyceryl glucoside when fluorescent immunostaining with an anti-occludin antibody.
  • the present invention is a skin barrier function promoter containing glyceryl glucoside.
  • Glyceryl glucoside also referred to as GG, is a compound in which glycerin and one or more molecules of glucose have an ⁇ - or ⁇ -glucoside bond.
  • Examples of the glyceryl glucoside include compounds represented by the following formulas (1) to (5).
  • the compound represented by the formula (1) is 1-O- ( ⁇ - or ⁇ -) D- (mono or poly) glucopyranosylglycerol.
  • the compound is sometimes referred to as 1-O- ( ⁇ - or ⁇ -) D-dihydroxypropyl (mono or poly) glucopyranoside.
  • the carbon atom at the 2-position marked with * in the formula (1) is an asymmetric carbon atom, and there are optical isomers, that is, (2R) and (2S) isomers.
  • N in the formulas (1) and (2) is the degree of sugar condensation, and represents an integer of 1 or more.
  • Commercially available glyceryl glucosides produced by known methods such as an enzymatic method and an organic synthesis method usually have n as an integer of 1 to 6 and most of them as an integer of 1 to 3, especially compounds having n of 1. There are many.
  • the compound represented by the formula (2) is 2-O- ( ⁇ - or ⁇ -) D- (mono or poly) glucopyranosylglycerol.
  • the compound is sometimes referred to as 2-O- ( ⁇ - or ⁇ -) D-dihydroxypropyl (mono or poly) glucopyranoside.
  • M and n in the formula (3), n and l in the formula (4), and l, m and n in the formula (5) are the degree of sugar condensation, and each independently represents an integer of 1 or more, and is usually used. Is an integer of 1 to 6, most of which is an integer of 1 to 3, and there are many compounds in which n, m, and l are 1, in particular.
  • the glucopyranosyl groups are ⁇ 1-4 bond, ⁇ 1-4 bond, ⁇ 1-6 bond, ⁇ 1-6 bond. It may be connected by such as.
  • the glyceryl glucoside in the present invention is represented by the formula (1) or the formula (2), and at least of 1-OD-glucopyranosylglycerol and 2-OD-glucopyranosylglycerol in which n is 1. It is preferable that one of them is contained, and 1-O- ⁇ -D-glucopyranosylglycerol (formula (1A)) and 1-O- ⁇ -D-glucopyranosylglycerol (formula (formula)) are preferably contained.
  • 1-O- ⁇ -D-glucopyranosylglycerol 1-O- ⁇ -D-glucopyranosylglycerol, 2-O- ⁇ -D-glucopyranosylglycerol, and 2-O- ⁇ .
  • the glyceryl glucoside of -D-glucopyranosylglycerol is a combination of glycerin and one molecule of glucose, but in the present invention, the glyceryl glucoside is further bound with glucose, that is, n is 2 or more. It may be a mixture of a compound having n of 1 and a compound having n of 2 or more.
  • the bonding mode between the glucopyranosyl groups is not particularly limited.
  • the wavy lines in the formulas (1) to (5) may be independently bonded by reacting the hydroxyl group of glycerin with the hydroxyl group at the 1-position of the ⁇ -D-glucopyranosyl group ( ⁇ bond). ), It means that it may react with the hydroxyl group at the 1-position of the ⁇ -D-glucopyranosyl group and bond ( ⁇ bond).
  • 1-O- ⁇ -D-glucopyranosylglycerol is the main component, more preferably 40 to 50% in 100% by mass of glyceryl glucoside.
  • the form of glyceryl glucoside used as a skin barrier function promoter is not particularly limited.
  • Examples of the form of glyceryl glucoside include an aqueous solution and a starch syrup-like high-viscosity solution in which the aqueous solution is concentrated.
  • Glyceryl glucoside can be produced by a known method. For example, a method of reacting a fungal ⁇ -glucosidase or cyclomaltodexstring lucosyl transferase on a saccharide substrate in a glycerol solution; a method of extracting and purifying from a brewed product such as sake, miso, or mirin; isomaltose, maltose, etc.
  • COSARTE-2G registered trademark
  • Toyo Refinery Co., Ltd. is a glyceryl glucoside (1-O- ⁇ -D-glucopyranosylglycerol, 1-O- ⁇ -D-glucopyranosylglycerol).
  • 2-O- ⁇ -D-glucopyranosylglycerol and 2-O- ⁇ -D-glucopyranosylglycerol mixture water and glycerin-containing composition (water and glycerin in this composition).
  • the content of glyceryl glucoside excluding glyceryl glucoside is about 70 to 78%, average 73.5%), and the commercially available product can be used to add glyceryl glucoside to the skin barrier function promoter of the present invention. it can.
  • the epidermis of the skin is composed of the stratum corneum, the stratum granulosum, the stratum spinosum, and the stratum basale from the outside, and has a skin barrier function to prevent the invasion of foreign substances such as allergens and bacteria and the evaporation of water from the body.
  • the skin barrier function promoter of the present invention is a skin barrier function promoter carried by a tight junction of the stratum granulosum, and is preferably a skin barrier function promoter that promotes the formation of tight junctions.
  • the skin barrier function promoter of the present invention is considered to have an effect of promoting the barrier function of the stratum corneum.
  • the skin barrier function of the stratum corneum includes, for example, the stratum corneum and the stratum corneum, which are filled with interkeratinocyte lipids around the epidermal keratinocytes covered with a cell membrane that is stable against physical and chemical stimuli.
  • the stratum corneum and the stratum corneum are filled with interkeratinocyte lipids around the epidermal keratinocytes covered with a cell membrane that is stable against physical and chemical stimuli.
  • the skin barrier function of the tight junction of the stratum granulosum includes, for example, the function of retaining water in the stratum granulosum and the prevention of foreign matter from entering by bringing the cells into close contact with each other by forming a tight junction between the cells of the stratum granulosum. Barrier function against target stimuli can be mentioned.
  • the skin barrier function promoter of the present invention preferably promotes the skin barrier function by enhancing the expression of adhesive proteins and promoting the formation of tight junctions, and more preferably by enhancing the expression of occludin, thereby promoting the skin barrier. Promote function.
  • Quantitative indicators for the evaluation of skin barrier function include, for example, the value of transepithelial electrical resistance (TER), the permeation rate of the skin, and the amount of transepidermal water evaporation (Trans-epidermal Water Loss: TEWL). Be done.
  • TER transepithelial electrical resistance
  • TEWL Trans-epidermal Water Loss
  • the transepithelial electrical resistance value (TER value) is widely adopted as a value for evaluating the skin barrier function by transwell, and the transepithelial electrical resistance caused by limiting the permeation of ions above and below the cell layer by tight junctions. It is obtained by measuring. In normal skin, the permeability of chemical substances in the cell layer is low, so the electrical resistance values ( ⁇ / cm 2 ) above and below the cell layer are high, but when the skin barrier function deteriorates, it penetrates the cell layer. This value decreases as the amount of chemicals increases.
  • the transepithelial electrical resistance value can be measured by a known method.
  • a predetermined device for example, a predetermined operating voltage (for example, 1 to 3 volts), a predetermined frequency (for example, 50 to 50).
  • the skin impedance is measured in a predetermined measurement range (for example, 0.1 to 30 k ⁇ ) at 1000 Hz) and divided by the skin surface area of the sample to calculate.
  • a predetermined measurement range for example, 0.1 to 30 k ⁇
  • the permeation rate of the skin is the rate per unit area when a substance diffuses or permeates through the skin according to a concentration gradient, and usually, a soluble fluorescent polymer is used as a tracer and the following formula (d) It can be calculated by quantitatively measuring from 1).
  • a soluble fluorescent polymer for example, Fluorescein isothiocyanate-dextran (FD) can be used.
  • D is the diffusion coefficient in the tracer's skin barrier
  • K is the tracer's skin barrier / base partition coefficient
  • Cd is the tracer. Concentration and L indicate skin barrier thickness
  • the tracer concentration can be determined by a known method. For example, the skin is sandwiched between horizontal diffusion cells, a tracer solution having a predetermined concentration is applied to the epidermis side, and the concentration of the tracer solution moved to the dermis side after a lapse of a predetermined time is measured with a fluorescence spectrophotometer or the like. Can be done. When the permeation rate of the skin is lower than that of the control, it can be judged that the skin barrier function is promoted.
  • the transepidermal water evaporation amount is the amount of water that evaporates through the stratum corneum, and is expressed by the unit area and the weight of water per unit time (for example, g / cm 2 / h). In normal skin, water evaporates only slightly, but when the skin barrier function is reduced, this value fluctuates relatively greatly.
  • the measurement can be performed by a known method. For example, a probe designed so that two humidity sensors can be placed on the skin surface at predetermined intervals is applied to the skin, the water content of the two sensors is measured, and TEWL is calculated from the water concentration gradient according to Fick's law. can do.
  • TEWL can be calculated from the water content of the recovered gas by applying a closed probe to the surface of the skin and refluxing dry air or the like to the surface of the skin in the probe. If the TEWL is significantly lower than the control, it can be determined that the skin barrier function is promoted.
  • the skin barrier function can be qualitatively evaluated by morphological observation using a marker molecule of skin cells.
  • fluorescent immunostaining of the skin is performed using a fluorescently labeled antibody against an adhesive protein such as claudin, occludin, or torserin expressed at a tight junction, and the skin barrier is determined by the fluorescence intensity emitted from the cell membrane from microscopic observation.
  • the function can be evaluated qualitatively. When the fluorescence is stronger than that of the control, it means that the expression level of the adhesive protein is high and the formation of tight junctions is promoted, and it can be judged that the skin barrier function is promoted.
  • the skin barrier function promoter contains the above-mentioned glyceryl glucoside, and may contain glycerin, diglycerin, glucose, water, and other components, if necessary.
  • the content of glyceryl glucoside in the skin barrier function promoter is not particularly limited as long as it is sufficient to promote the skin barrier function, but is preferably 20% by mass to 100% by mass, preferably 60% by mass to 90%. By mass% is more preferable, and 70% by mass to 80% by mass is further preferable.
  • the other components are not particularly limited as long as they do not impair the effects of the present invention, and can be appropriately selected depending on the intended purpose.
  • ingredients include, for example, excipients, disintegrants, emulsifiers, diluents, binders, lubricants, stabilizers, solvents for injections, moisturizers, oily bases, surfactants, propellants, antioxidants.
  • pharmaceutically acceptable carriers such as agents, thickeners, gelling agents, antibacterial agents, powder components, pH adjusters, auxiliary agents, wetting agents, and solvents.
  • excipients examples include organic excipients including sugar derivatives such as lactose, cellulose derivatives such as crystalline cellulose, starch derivatives such as potato starch, and inorganic excipients including sulfates such as calcium sulfate. Excipients can be mentioned.
  • disintegrant examples include starch derivatives such as sodium carboxymethyl starch, cellulose derivatives such as croscarmellose sodium, crosslinked polyvinylpyrrolidone, and compounds used in the above excipients.
  • emulsifier examples include cationic surfactants such as benzalkonium chloride, anionic surfactants such as sodium lauryl sulfate, nonionic surfactants such as polyoxyethylene alkyl ether, and polyglyceryl fatty acids such as polyglyceryl stearate 10. Examples thereof include ester surfactants and colloidal clays such as bentonite.
  • Examples of the diluent include water, ethanol and the like.
  • Examples of the binder include polyethylene glycol, polyvinylpyrrolidone, gelatin, and compounds used in the above-mentioned excipients.
  • lubricant examples include sulfates such as sodium sulfate, lauryl sulfates such as sodium lauryl sulfate, waxes such as bead wax, and starch derivatives such as colloidal silica, stearic acid, and potato starch.
  • the stabilizer examples include parahydroxybenzoic acid esters such as methylparaben and propylparaben, and phenols such as phenol and cresol.
  • the solvent for injection examples include water, ethanol, glycerin and the like.
  • Moisturizers include polyhydric alcohols such as glycerin, polypropylene and polyethylene glycol; water-soluble polymers such as mucopolysaccharides, collagen and hyaluronic acid; sugars such as glucose, trehalose, arabinose, cycloglycerins, dextrin, dextran and pectin. And derivatives thereof; amino acids and the like.
  • polyhydric alcohols such as glycerin, polypropylene and polyethylene glycol
  • water-soluble polymers such as mucopolysaccharides, collagen and hyaluronic acid
  • sugars such as glucose, trehalose, arabinose, cycloglycerins, dextrin, dextran and pectin. And derivatives thereof; amino acids and the like.
  • Oily bases include, for example, higher fatty acids such as lauric acid, palmitic acid, stearic acid, docosahexaenoic acid, eikosapentaenoic acid, linoleic acid, oleic acid; kind; Waxes such as beeswax, paraffin wax, candelilla wax; Higher alcohols such as lauryl alcohol, oleyl alcohol, cetanol, stearyl alcohol, dodeca alcohol, jojoba alcohol; Plants such as palm oil, palm oil, olive oil, castor oil Fats and oils; lanolins such as lanolin acetate and polyoxylanolin; phospholipids such as lecithin, phosphatidylcholine and sphingomyelin; monoalcohol carboxylic acid esters such as ethyl oleate, isopropyl palmitate and diisopropyl adipate.
  • higher fatty acids such as lauric acid, palm
  • surfactant examples include nonionic surfactants such as sorbitan fatty acid ester, polyol fatty acid ester and polyoxyethylene sorbitan fatty acid ester; lauryl sulfate, alkylbenzene sulfonate, polyoxyethylene alkyl ether sulfate and the like.
  • Anionic surfactants cationic surfactants such as benzethonium chloride and stearyltrimethylammonium chloride
  • amphoteric surfactants such as betaine lauryldimethylaminoacetate and alkyldiaminoethylglycine hydrochloride.
  • propellant examples include propylene carbonate, carbon dioxide gas, LPG, and next-generation chlorofluorocarbons.
  • examples of the antioxidant include ascorbic acid derivatives containing ascorbic acid, tocopherol derivatives containing tocopherols, dibutylhydroxytoluene, butylhydroxyanisole and the like.
  • thickener and gelling agent examples include cellulose derivatives such as carboxylmethyl cellulose and hydroxyethyl cellulose; algae-derived components such as carrageenan, agar and alginic acid; polysaccharides such as pectin; gums such as xanthan gum and guar gum. ..
  • antibacterial agent examples include benzalkonium chloride, phenoxyethanol, dichlorophene, chlorhexidyl hydrochloride, methyl paraoxybenzoate, ethyl paraoxybenzoate and the like.
  • Examples of the powder component include magnesium carbonate, calcium carbonate, aluminum silicate, mica, mica, kaolin, kaolinite, vermiculite, hydroxyapatite and the like.
  • pH adjuster examples include sodium hydroxide, potassium hydroxide, calcium hydroxide, magnesium hydroxide, ammonia, trisodium phosphate, disodium hydrogen phosphate, citric acid, sodium citrate and the like.
  • auxiliary agent examples include ethyl alcohol, isopropyl alcohol, butanol, 1,3-butanediol, propylene glycol, menthol, limonene, urea and the like.
  • wetting agent examples include sorbitol, glycerin, propylene glycol, 1,3-butylene glycol, sodium lactate and the like.
  • the solvent examples include alcohols such as ethanol, butanol and benzyl alcohol; ketones such as acetone and methyl ethyl ketone; glycol ether esters such as ethylene glycol monoethyl ether acetate and propylene glycol monoethyl ether acetate.
  • alcohols such as ethanol, butanol and benzyl alcohol
  • ketones such as acetone and methyl ethyl ketone
  • glycol ether esters such as ethylene glycol monoethyl ether acetate and propylene glycol monoethyl ether acetate.
  • the skin barrier function promoter has the effect of promoting the barrier function of the tight junction, it is suitable for use in the cosmetics, quasi-drugs, and skin external preparations of the present invention described later.
  • Other embodiments of the present invention are cosmetics, quasi-drugs, and external preparations for skin containing skin barrier function promoters.
  • Quasi-drugs are products that have specific indications and effects and have mild effects on the human body.
  • the content of the skin barrier function promoting agent in the cosmetics, quasi-drugs and external preparations for skin is adjusted so as to exhibit the skin barrier function promoting effect in the final product.
  • the content of the skin barrier function promoter in cosmetics, quasi-drugs and external preparations for skin is preferably 0.5% by mass to 15% by mass, more preferably 1% by mass to 10% by mass.
  • the content of glyceryl glucoside in the cosmetics, quasi-drugs, and external preparations for skin is preferably 0.1% by mass to 15% by mass, more preferably 0.7% by mass to 7% by mass.
  • glyceryl glucoside in the skin barrier function promoter promotes the skin barrier function at tight junctions. Suitable.
  • the dose of the quasi-drug or the external preparation for skin containing the skin barrier function promoter may be appropriately adjusted according to the symptoms, application method, application mode, and the like.
  • the cosmetics, quasi-drugs, and skin external preparations of the present invention include the above ⁇ skin barrier function promoters as long as the effects of the present invention are not impaired. > May contain other ingredients, such as those described in.
  • Cosmetics, quasi-drugs and external preparations for skin are not particularly limited as long as they can be applied to the skin, and the dosage forms include, for example, cream, liquid, gel, semi-solid, solid, stick, etc. Examples include powder.
  • the cosmetics, quasi-drugs and external preparations for skin may be water-in-oil type, oil-in-water type, microemulsion, multiple emulsification or the like, and can be appropriately selected depending on the purpose and application.
  • Examples of cosmetics include milky lotions, lotions, beauty essences, facial cleansers, facial cleansers, body cosmetics, and massage cosmetics.
  • Examples of quasi-drugs and external preparations for skin include sprays, ointments, creams, gelling agents, patches, tapes, external solid preparations, and external liquid preparations.
  • COSARTE-2G 0.73% by mass and 1.46% by mass as the final concentration of glyceryl glucoside
  • ultrapure water as a control were added to each well for culturing.
  • the TER values at 0, 3, 6 and 12 hours after culturing were measured using a Millicell-ERS system (manufactured by Millipore). The relative values of the measured values to the control were calculated and the results are shown in Table 1. From this, it was shown that the TER value was significantly increased in the group treated with the skin barrier function promoter containing glyceryl glucoside, and the barrier function of the excellent tight junction was promoted.
  • glyceryl glucoside (GG) concentration was 0.73% by mass, 1.46% by mass, and 3.66% by mass.
  • TER value transepithelial electrical resistance value
  • Table 2 shows the results of calculating the relative values of the measured values with respect to the control. From this, it was shown that the barrier function of the tight junction improves as the concentration of glyceryl glucoside increases.
  • Example 2 Evaluation test of permeation rate of intracellular tight junction Normal human epidermal keratinocytes (NHEK) (purchased from Kurashiki Spinning Co., Ltd.) were seeded in Transwell System, and used as a skin barrier function promoter containing glyceryl glucoside.
  • COSARTE-2G (0.73% by mass and 1.46% by mass as the final concentration of glyceryl glucoside) and ultrapure water as a control were added to each well and cultured for 12 hours.
  • FITC-Conjugated dextran (“FD-4”: average molecular weight 4000, manufactured by Sigma) was added to each well and reacted for 12 hours.
  • the absorbance of FD-4 was measured using a fluorescent plate reader (“ARVO X4”, manufactured by Perkin Elmer Japan), the permeation rate of FD-4 was calculated from the obtained values, and the results are shown in Table 3. It was. From this, it was shown that in the group treated with the skin barrier function promoter containing glyceryl glucoside, the permeation rate of FD-4 was suppressed and the barrier function of tight junction was promoted.
  • Example 3 Tight junction formation evaluation test using anti-occludin antibody Normal human epidermal keratinocytes (NHEK) (purchased from Kurashiki Spinning Co., Ltd.) were seeded in Transwell System to promote skin barrier function containing glyceryl glucoside.
  • COSARTE-2G (3.66% by mass as the final concentration of glyceryl glucoside) as an agent and ultrapure water as a control were added to each well and cultured for 6 hours.
  • the cultured cells were fixed with methanol at 0 ° C. for 5 minutes and subjected to permeation treatment with 0.2% Triton-X100 for 5 minutes.
  • the cells after the clearing treatment were blocked with 10% goat serum and cultured at 4 ° C.

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Cited By (2)

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Publication number Priority date Publication date Assignee Title
JP2023091784A (ja) * 2021-12-20 2023-06-30 大関株式会社 肌の弾力の維持又は向上用組成物
WO2024262189A1 (ja) * 2023-06-20 2024-12-26 東洋精糖株式会社 細菌の増殖抑制剤、それを含む化粧品、医薬部外品、及び医薬組成物、並びに細菌の増殖抑制方法

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JPH11222496A (ja) * 1998-02-02 1999-08-17 Tatsuuma Honke Brewing Co Ltd α−Ｄ−グルコピラノシルグリセロール類及びその製 造方法及びその用途
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JP2012500781A (ja) * 2008-08-22 2012-01-12 ビトップ アーゲー グルコシルグリセロールの使用
JP2015166340A (ja) * 2014-02-14 2015-09-24 東洋精糖株式会社 フィラグリン遺伝子およびカスパーゼ−１４遺伝子の発現促進剤ならびに幹細胞因子の産生抑制剤
US20190038689A1 (en) * 2017-08-07 2019-02-07 Mary Kay Inc. Topical skin compositions for treating erythema or skin inflammation
WO2019078370A1 (ja) * 2017-10-20 2019-04-25 ロート製薬株式会社 皮膚障害改善用組成物

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JP2023091784A (ja) * 2021-12-20 2023-06-30 大関株式会社 肌の弾力の維持又は向上用組成物
WO2024262189A1 (ja) * 2023-06-20 2024-12-26 東洋精糖株式会社 細菌の増殖抑制剤、それを含む化粧品、医薬部外品、及び医薬組成物、並びに細菌の増殖抑制方法

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