Novel compound and use thereof

Abstract

The present invention addresses the problem of providing: a novel compound; and a use of the compound.　The features of the present invention for solving the problem are as follows. 1. A compound represented by chemical formula (1). 2. A compound represented by chemical formula (2). 3. A transepidermal water loss reducing agent containing the compound mentioned in 1 or 2 as an active ingredient. 4. A moisturizing agent containing the compound mentioned in 1 or 2 as an active ingredient. 5. An agent for promoting the production of interleukin-6 in dendritic cells, which contains the compound mentioned in 1 or 2 as an active ingredient. 6. An immunostimulant containing the compound mentioned in 1 or 2 as an active ingredient. 7. A method for producing the compound mentioned in 1 or 2, the method being characterized by including a step for isolating the compound from an extract from rice bran.

Description

New compounds and their uses

[0001] The present invention relates to a novel compound and its use, which can be widely used in pharmaceuticals, quasi-drugs, foods (including health foods, functional foods, and foods for specified health uses), cosmetics, topical skin preparations, etc.

[0002] The rice-derived ceramide composition contains β-sitosterol-3-O-glucoside (BSG) and elasticamide as active ingredients. BSG is known to have physiological activities such as immunomodulatory effects, and elasticamide is known to have physiological activities such as moisturizing effects.

[0003] Meanwhile, skin has a barrier function that prevents the intrusion of foreign substances from the outside world and suppresses moisture loss to the outside of the body. However, it is known that the skin's barrier function and moisture retention function can be impaired by external factors such as ultraviolet rays, changes in temperature and humidity, irritation from friction and pressure, and chemicals, as well as internal factors such as a weakened immune system due to various stresses and diseases, and a decline in physiological functions due to aging. Transepidermal water loss (TEWL) is used as an index reflecting such moisture retention and skin barrier function. Therefore, significantly suppressing the increase in transepidermal water loss is expected to suppress the decline in moisture retention and skin barrier function (Patent Document 1).

[0004] When pathogens or bacteria enter the body through cuts or mucous membranes, dendritic cells, which are distributed throughout the body, recognize and phagocytose the antigens, and present them to white blood cells and lymphocytes. Neutrophils, macrophages, and natural killer cells then phagocytose and kill the pathogens that have invaded the body (innate immunity). These cells are used to evaluate immunostimulatory effects.

[0005] There are two types of defense responses against foreign substances: innate immunity and adaptive immunity. In the innate immune response, immune cells such as neutrophils, dendritic cells, and macrophages produce cytokines in response to innate immune activators derived from bacteria or viruses, which then triggers an immune response. The innate immune system is an infection defense mechanism shared by all living organisms, and is generally nonspecific, allowing for a rapid response and effective function against many sources of infection.

[0006] Furthermore, dendritic cells, which are one type of innate immune cell, have phagocytic ability and release IL-6. When dendritic cells mature, they have superior antigen presentation ability compared to other cells and release cytokines. Various cytokines are released, including IL-6 (interleukin 6), which is produced in response to LPS stimulation. Mature dendritic cells also activate naive T cells into effector T cells, activating other immune cells. Examples include promoting the migration of neutrophils toward pathogens and the phagocytic ability of macrophages. Furthermore, mature dendritic cells induce the differentiation of naive T cells into Th17 cells by IL-6 and promote neutrophil migration (Patent Document 2).

[0007] Japanese Patent Application Publication No. 2022-096780 Japanese Patent Application Publication No. 2023-147196

[0008] Against this background, the present inventors discovered that rice bran extract contains a novel compound and that this compound has the effect of reducing transepidermal water loss (TEWL), thereby providing moisturizing and inhibiting a decline in skin barrier function, leading to the completion of the present invention. Furthermore, they discovered that the novel compound has the effect of promoting the production of interleukin-6 (IL-6) in dendritic cells, leading to the completion of the present invention. In other words, the present invention provides a novel compound and its uses.

[0009] The features of the present invention for solving the above problems are as follows: 1. A compound represented by the following chemical formula (1): 2. A compound represented by the following chemical formula (2): 3. A transepidermal water loss reducer comprising as an active ingredient the compound set forth in 1. or 2. above. 4. A moisturizer comprising as an active ingredient the compound set forth in 1. or 2. above. 5. An interleukin-6 production promoter in dendritic cells comprising as an active ingredient the compound set forth in 1. or 2. above. 6. An immunostimulant comprising as an active ingredient the compound set forth in 1. or 2. above. 7. A method for producing the compound set forth in 1. or 2. above, comprising a step of isolating the compound from a rice bran extract. 8. A moisturizing food or drink composition comprising as an active ingredient the compound set forth in 1. or 2. above. 9. A moisturizing pharmaceutical composition comprising as an active ingredient the compound set forth in 1. or 2. above. 10. A moisturizing cosmetic composition comprising as an active ingredient the compound set forth in 1. or 2. above. 11. A food or drink composition for immunostimulation comprising as an active ingredient the compound set forth in 1. or 2. above. 12. or 2. above. 13. An immunostimulating pharmaceutical composition having as an active ingredient the compound set forth in 1. or 2. above. 14. A method for moisturizing human skin, comprising the steps of: (a) isolating the compound set forth in 1. or 2. above from a rice bran extract; and (b) administering to a human an appropriate amount of the compound set forth in 1. or 2. above by oral or parenteral administration, thereby reducing transepidermal water loss in the human. 15. A method for stimulating human immunity, comprising the steps of: (a) isolating the compound set forth in 1. or 2. above from a rice bran extract; and (b) administering to a human an appropriate amount of the compound set forth in 1. or 2. above by oral or parenteral administration, thereby promoting interleukin-6 production in dendritic cells in the human.

[0010] The compound represented by chemical formula (1) (hereinafter referred to as "Compound A") and the compound represented by chemical formula (2) (hereinafter referred to as "Compound B") of the present invention have a TEWL-reducing effect, as described below. As a result, Compound A and Compound B are useful as moisturizing agents. Therefore, they can be used in pharmaceuticals, quasi-drugs, foods (including health foods, functional foods, and foods for specified health uses), cosmetics, and topical skin preparations. Furthermore, Compound A and Compound B promote the production of interleukin-6 in dendritic cells, thereby aiding neutrophil migration and enhancing the phagocytic activity of macrophages. This activates other immune cells and enhances the immune response. Therefore, Compound A and Compound B are useful as immunostimulants. Furthermore, Compounds A and B have been found to be contained in rice bran, and can be obtained by isolating Compounds A and B from a rice bran extract.

[0011] FIG. 1 is a diagram showing the proton-carbon correlation (arrow) and proton-proton correlation (bold line) of compound A. FIG. 2 is a diagram showing the proton-carbon correlation (arrow) and proton-proton correlation (bold line) of compound B. FIG. 3 is a graph showing the effects of compounds A and B on the TEWL of a 3D human epidermis model. FIG. 4 is a graph showing the evaluation results of the immunostimulatory effect of compounds A and B on dendritic cells.

[0012] The present invention is described in detail below. The present invention is a compound A represented by the following chemical formula (1). The present invention also relates to compound B represented by the following chemical formula (2):

[0013] The method for obtaining compounds A and B is not particularly limited, but for example, a method for isolating compounds A and B from a rice bran extract is preferred because it contains compounds A and B at high concentrations. The "rice bran extract" is not particularly limited as long as it is produced in the process of producing rice bran oil. For example, a rice bran extract can be obtained by extracting rice bran with an organic solvent and then precipitating the extract, but this method is not limited to this. In addition, the rice bran extract may also be a by-product produced in the production process of rice bran oil.

[0014] Here, the method for isolating compounds A and B from the extract is not particularly limited, but they can be isolated, for example, by chromatography using activated clay, activated carbon, silica gel, alumina, diatomaceous earth, synthetic adsorbents, ion exchange resins, or the like, or by a method of removing components other than compound A by adsorption, decomposition, precipitation, filtration, dissolution, distillation, or the like. Furthermore, subsequent purification may be carried out appropriately by HPLC or the like. Specifically, they can be produced according to the examples of the present specification.

[0015] The above compounds A and B of the present invention can be used as TEWL-reducing agents.

[0016] Compounds A and B of the present invention can be used as ingredients in various foods and beverages (including health foods, functional foods, and foods with specified health uses). Examples of foods and beverages include general foods such as confectioneries (gum, candy, caramel, chocolate, cookies, snacks, jellies, gummies, and tablets), noodles (soba, udon, ramen, and the like), dairy products (milk, ice cream, and yogurt), seasonings (miso, soy sauce, and the like), soups, and beverages (juice, coffee, black tea, green tea, carbonated drinks, and sports drinks), as well as health foods (tablets, capsules, and the like), nutritional supplements (nutrition drinks, and the like), foods with specified health uses, and foods with specified health uses. The agent of the present invention can be appropriately incorporated into these foods and beverages. Compounds A and B may be added directly or in the form of a composition, such as a plant extract, preferably a rice bran extract, containing sufficient amounts of compounds A and B to be used as active ingredients. In this case, the content of compounds A and B contained in the rice bran extract is not particularly limited as long as it is an amount that is contained as an active ingredient, but it is preferable to use one that contains, for example, 0.01 to 1 wt %, or even 0.05 to 0.5 wt %.

[0017] These foods and beverages can contain various ingredients depending on the type, and the following food ingredients can be used: glucose, fructose, sucrose, maltose, sorbitol, stevioside, corn syrup, lactose, citric acid, tartaric acid, malic acid, succinic acid, lactic acid, L-ascorbic acid, dl-α-tocopherol, sodium erythorbate, glycerin, propylene glycol, glycerin fatty acid esters, polyglycerin fatty acid esters, sucrose fatty acid esters, sorbitan fatty acid esters, propylene glycol fatty acid esters, gum arabic, carrageenan, casein, gelatin, pectin, agar, B vitamins, nicotinamide, calcium pantothenate, amino acids, calcium salts, colorings, flavorings, and preservatives.

[0018] As a specific manufacturing method, the agent of the present invention is spray-dried or freeze-dried together with powdered cellulose, and then formed into a powder, granules, tablets, or solution, which can be easily incorporated into foods and beverages (instant foods, etc.). The agent of the present invention can also be dissolved in, for example, fats and oils, ethanol, glycerin, or a mixture thereof to form a liquid, which can then be added to beverages or solid foods. If necessary, it can also be mixed with a binder such as gum arabic or dextrin to form a powder or granules, which can then be added to beverages or solid foods.

[0019] The compounds A and B of the present invention may be used as materials for pharmaceuticals (including pharmaceuticals and quasi-drugs). Pharmaceutical preparations can be produced by appropriately blending the agent of the present invention with raw materials for pharmaceutical preparations. Examples of pharmaceutical raw materials that can be incorporated into the agent of the present invention include excipients (glucose, lactose, sucrose, sodium chloride, starch, calcium carbonate, kaolin, crystalline cellulose, cocoa butter, hardened vegetable oil, kaolin, talc, etc.), binders (distilled water, saline, ethanol water, simple syrup, glucose solution, starch solution, gelatin solution, carboxymethylcellulose, potassium phosphate, polyvinylpyrrolidone, etc.), disintegrants (sodium alginate, agar, sodium bicarbonate, calcium carbonate, sodium lauryl sulfate, stearate monoglyceride, starch, lactose, powdered gum arabic, gelatin, ethanol, etc.), disintegration inhibitors (sucrose, stearin, cocoa butter, hydrogenated oil, etc.), absorption enhancers (quaternary ammonium base, sodium lauryl sulfate, etc.), adsorbents (glycerin, starch, lactose, kaolin, bentonite, silicic acid, etc.), and lubricants (purified talc, stearates, polyethylene glycol, etc.). Compounds A and B may be added as they are, or may be used as a composition, such as a plant extract, particularly preferably a rice bran extract, containing sufficient amounts of compounds A and B to enable them to be used as active ingredients. In this case, the content of compounds A and B in the rice bran extract is not particularly limited as long as they are contained in the amounts required for their active ingredients, but it is preferable to use one containing 0.01 to 1 wt %, and more preferably 0.05 to 0.5 wt %.

[0020] Compounds A and B of the present invention can generally be administered orally in the form of tablets, pills, soft or hard capsules, fine granules, powders, granules, or liquids, but can also be administered parenterally. When administered parenterally, they can be administered in the form of a solution or with the addition of a dispersant, suspending agent, stabilizer, or the like, by local tissue administration, intradermal, subcutaneous, intramuscular, or intravenous injection. They may also be administered in the form of suppositories or other formulations. Furthermore, they can be administered as eye drops. Compounds A and B may be added directly or in the form of a composition containing sufficient amounts of compounds A and B to be used as active ingredients, such as a plant extract, particularly preferably a rice bran extract. The content of compounds A and B in the rice bran extract is not particularly limited as long as they are present as active ingredients, but it is preferable to use one containing 0.01 to 1 wt %, or even 0.05 to 0.5 wt %.

[0021] The dosage may vary depending on factors such as the administration method, disease condition, and patient age. For adults, the typical daily dosage is 0.5 to 5,000 mg of active ingredient, while for children, it is typically 0.5 to 3,000 mg. The compounding ratio of Compounds A and B can be adjusted depending on the dosage form. Oral or mucosal administration typically involves approximately 0.001 to 1.0 wt% and parenteral administration involves approximately 0.0001 to 1.0 wt%. Since the dosage varies depending on various conditions, a smaller amount than the above may be sufficient, or an amount exceeding the range may be necessary. Compounds A and B may be added directly or as a composition containing sufficient amounts of Compounds A and B to be used as active ingredients, such as a plant extract, particularly preferably a rice bran extract. In this case, the content of compounds A and B contained in the rice bran extract is not particularly limited as long as it is an amount that is contained as an active ingredient, but it is preferable to use one that contains, for example, 0.01 to 1 wt %, or even 0.05 to 0.5 wt %.

[0022] Compounds A and B of the present invention can be used as ingredients for external skin preparations (including cosmetics, pharmaceuticals, and quasi-drugs). Examples of the present invention include emulsions, soaps, facial cleansers, bath additives, creams, emulsions, skin lotions, colognes, shaving creams, shaving lotions, cosmetic oils, sunscreen lotions, face powders, foundations, perfumes, face masks, nail creams, enamel, enamel removers, eyebrow pencils, blushers, eye creams, eye shadows, mascaras, eyeliners, lipsticks, lip balms, shampoos, rinses, hair dyes, dispersions, and cleansers. Pharmaceuticals and quasi-drugs that can incorporate the present invention include ointments, creams, and external liquids. Compounds A and B may be added directly or in the form of a composition containing sufficient amounts of compounds A and B to be used as active ingredients, such as a plant extract, particularly preferably a rice bran extract. In this case, the content of compounds A and B contained in the rice bran extract is not particularly limited as long as it is an amount that is contained as an active ingredient, but it is preferable to use one that contains, for example, 0.01 to 1 wt %, or even 0.05 to 0.5 wt %.

[0023] In addition to the present invention, the above-mentioned external skin preparations can contain ingredients that are incorporated into external skin preparations such as cosmetics and quasi-drugs, as long as the ingredients do not impair the functions of the present invention, such as oils, higher alcohols, fatty acids, ultraviolet absorbers, powders, pigments, surfactants, polyhydric alcohols / sugars, polymers, physiologically active ingredients, solvents, antioxidants, fragrances, preservatives, etc. Examples are listed below, but the present invention is not limited to these examples.

[0024] (1) Examples of oils Ester-based oil phase components: glyceryl tri-2-ethylhexanoate, cetyl 2-ethylhexanoate, isopropyl myristate, butyl myristate, isopropyl palmitate, ethyl stearate, octyl palmitate, isocetyl isostearate, butyl stearate, butyl myristate, ethyl linoleate, isopropyl linoleate, ethyl oleate, isocetyl myristate, isostearyl myristate, isostearyl palmitate, octyldodecyl myristate, isocetyl isostearate, diethyl sebacate, adipic acid Diisopropyl, isoarachyl neopentanoate, caprylic / capric triglyceride, trimethylolpropane tri-2-ethylhexanoate, trimethylolpropane triisostearate, pentaerythritol tetra-2-ethylhexanoate, cetyl caprylate, decyl laurate, hexyl laurate, decyl myristate, myristyl myristate, cetyl myristate, stearyl stearate, decyl oleate, cetyl ricinoleate, isostearyl laurate, isotridecyl myristate, isocetyl myristate, myristyl Isostearyl Palmitate, Isocetyl Palmitate, Isostearyl Palmitate, Octyl Stearate, Isocetyl Stearate, Isodecyl Oleate, Octyldodecyl Oleate, Octyldodecyl Linoleate, Isopropyl Isostearate, Cetostearyl 2-Ethylhexanoate, Stearyl 2-Ethylhexanoate, Hexyl Isostearate, Ethylene Glycol Dioctanoate, Ethylene Glycol Dioleate, Propylene Glycol Dicaprate, Propylene Glycol Dicaprylate, Propylene Glycol Dicaprylate , Neopentyl glycol dicaprate, Neopentyl glycol dioctanoate, Glyceryl tricaprylate, Glyceryl triundecylate, Glyceryl triisopalmitate, Glyceryl triisostearate, Octyldodecyl neopentanoate, Isostearyl octanoate, Octyl isononanoate, Hexyldecyl neodecanoate, Octyldodecyl neodecanoate, Isocetyl isostearate, Isostearyl isostearate, Octyldecyl isostearate, Polyglycerin oleate, Polyglycerin isostearate,Dipropyl carbonate, dialkyl carbonate (C12-18), triisocetyl citrate, triisoarachidyl citrate, triisooctyl citrate, lauryl lactate, myristyl lactate, cetyl lactate, octyldecyl lactate, triethyl citrate, acetyltriethyl citrate, acetyltributyl citrate, trioctyl citrate, diisostearyl malate, 2-ethylhexyl hydroxystearate, di-2-ethylhexyl succinate, diisobutyl adipate, sebacic acid Diisopropyl, dioctyl sebacate, cholesteryl stearate, cholesteryl isostearate, cholesteryl hydroxystearate, cholesteryl oleate, dihydrocholesteryl oleate, phytosteryl isostearate, phytosteryl oleate, isocetyl 12-stearoylhydroxystearate, stearyl 12-stearoylhydroxystearate, isostearyl 12-stearoylhydroxystearate, etc. Hydrocarbon oil phase components include squalane, liquid paraffin, α-olefin oligomer, isoparaffin, ceresin, paraffin, liquid isoparaffin, polybutene, microcrystalline wax, petrolatum, etc. Animal and vegetable oils and their hydrogenated oils, and naturally derived waxes: beef tallow, hydrogenated beef tallow, lard, hydrogenated lard, horse oil, hydrogenated horse oil, mink oil, orange roughy oil, fish oil, hydrogenated fish oil, egg yolk oil and other animal oils and their hydrogenated oils, avocado oil, almond oil, olive oil, cocoa butter, kiwi seed oil, apricot kernel oil, kukui nut oil, sesame oil, wheat germ oil, rice germ oil, rice bran oil, safflower oil, shea butter, soybean oil, evening primrose oil, perilla oil, tea seed oil, camellia oil, corn oil, rapeseed oil, Examples of suitable oils include vegetable oils and their hydrogenated oils, such as hydrogenated rapeseed oil, palm kernel oil, hydrogenated palm kernel oil, palm oil, hydrogenated palm oil, peanut oil, hydrogenated peanut oil, castor oil, hydrogenated castor oil, sunflower oil, grape seed oil, jojoba oil, hydrogenated jojoba oil, macadamia nut oil, medlar oil, cottonseed oil, hydrogenated cottonseed oil, coconut oil, and hydrogenated coconut oil, as well as waxes such as beeswax, high acid value beeswax, lanolin, reduced lanolin, hydrogenated lanolin, liquid lanolin, carnauba wax, and montan wax. Silicone-based oil phase components: dimethylpolysiloxane, methylphenylpolysiloxane, methylcyclopolysiloxane, octamethylpolysiloxane,Examples of suitable oil phase components include decamethylpolysiloxane, dodecamethylcyclosiloxane, methylhydrogenpolysiloxane, polyether-modified organopolysiloxane, dimethylsiloxane-methylcetyloxysiloxane copolymer, dimethylsiloxane-methylstearoxysiloxane copolymer, alkyl-modified organopolysiloxane, terminal-modified organopolysiloxane, amino-modified silicone oil, amino-modified organopolysiloxane, dimethiconol, silicone gel, acrylic silicone, trimethylsiloxysilicate, and silicone RTV rubber. Fluorine-based oil phase components include perfluoropolyether, fluorine-modified organopolysiloxane, fluorinated pitch, fluorocarbon, fluoroalcohol, and fluoroalkyl-polyoxyalkylene-co-modified organopolysiloxane.

[0025] (2) Examples of higher alcohols include lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, behenyl alcohol, 2-ethylhexanol, hexadecyl alcohol, and octyldodecanol.

[0026] (3) Examples of fatty acids include caprylic acid, capric acid, undecylenic acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, linoleic acid, linolenic acid, arachidonic acid, behenic acid, erucic acid, and 2-ethylhexanoic acid.

[0027] (4) Examples of ultraviolet absorbers: para-aminobenzoic acid, amyl para-aminobenzoate, dihydroxypropyl ethyl para-aminobenzoate, glyceryl para-aminobenzoate, ethyl para-aminobenzoate, octyl para-aminobenzoate, octyldimethyl para-aminobenzoate, ethylene glycol salicylate, octyl salicylate, triethanolamine salicylate, phenyl salicylate, butylphenyl salicylate, benzyl salicylate, homomenthyl salicylate, benzyl cinnamate, octyl para-methoxycinnamate, 2-ethylhexyl para-methoxycinnamate, glyceryl di-para-methoxycinnamate mono-2-ethylhexanoate, isopropyl para-methoxycinnamate, diethanolamine salt of para-methoxyhydrocinnamate, diisopropyl-diisopropylcinnamate mixture, urocanic acid, ethyl urocanate, hydroxymethoxybenzophenone, hydroxymethoxybenzophenone sulfonic acid and its salts, di Examples include hydroxymethoxybenzophenone, dihydroxymethoxybenzophenone sodium disulfonate, dihydroxybenzophenone, dihydroxydimethoxybenzophenone, hydroxyoctoxybenzophenone, tetrahydroxybenzophenone, butylmethoxydibenzoylmethane, 2,4,6-trianilino-p-(carbo-2-ethylhexyl-1-oxy)-1,3,5-triazine, 2-(2-hydroxy-5-methylphenyl)benzotriazole, methyl-O-aminobenzoate, 2-ethylhexyl-2-cyano-3,3-diphenylacrylate, phenylbenzimidazole sulfate, 3-(4-methylbenzylidene)camphor, isopropyldibenzoylmethane, 2-ethylhexyl 4-(3,4-dimethoxyphenylmethylene)-2,5-dioxo-1-imidazolidinepropionate, and their polymer and silane derivatives.

[0028] (5) Examples of powders and pigments: Dyes such as Red No. 104, Red No. 201, Yellow No. 4, Blue No. 1, Black No. 401, lake dyes such as Yellow No. 4 AL Lake and Yellow No. 203 BA Lake, nylon powder, silk powder, urethane powder, Teflon (registered trademark) powder, silicone powder, polymethyl methacrylate powder, cellulose powder, starch, silicone elastomer spherical powder, polymers such as polyethylene powder, yellow iron oxide, red iron oxide, black iron oxide, chromium oxide, carbon black, colored pigments such as ultramarine and iron blue, zinc oxide, titanium oxide, acid Examples of suitable pigments include white pigments such as cerium chloride, extender pigments such as talc, mica, sericite, kaolin, and plate-like barium sulfate, pearl pigments such as titanium dioxide, metal salts such as barium sulfate, calcium carbonate, magnesium carbonate, aluminum silicate, and magnesium silicate, inorganic powders such as silica and alumina, metal soaps such as aluminum stearate, magnesium stearate, zinc palmitate, zinc myristate, magnesium myristate, zinc laurate, and zinc undecylenate, bentonite, smectite, and boron nitride. There are no particular limitations on the shape (spherical, rod-like, needle-like, plate-like, irregular, flaky, spindle-like, etc.) and particle size of these powders. These powders may or may not have been previously surface-treated by conventionally known surface treatments, such as fluorine compound treatment, silicone treatment, silicone resin treatment, pendant treatment, silane coupling agent treatment, titanium coupling agent treatment, oil treatment, N-acylated lysine treatment, polyacrylic acid treatment, metal soap treatment, amino acid treatment, lecithin treatment, inorganic compound treatment, plasma treatment, mechanochemical treatment, etc.

[0029] (6) Examples of surfactants: Anionic surfactants include fatty acid soaps, α-acylsulfonates, alkylsulfonates, alkylarylsulfonates, alkylnaphthalenesulfonates, alkyl sulfates, POE alkyl ether sulfates, alkylamide sulfates, alkyl phosphates, POE alkyl phosphates, alkylamide phosphates, alkyloyl alkyl taurine salts, N-acylamino acid salts, POE alkyl ether carboxylates, alkyl sulfosuccinates, sodium alkylsulfoacetates, acylated hydrolyzed collagen peptide salts, perfluoroalkyl phosphate esters, etc. Cationic surfactants include alkyltrimethylammonium chloride, stearyltrimethylammonium chloride, stearyltrimethylammonium bromide, cetostearyltrimethylammonium chloride, distearyldimethylammonium chloride, stearyldimethylbenzylammonium chloride, behenyltrimethylammonium bromide, benzalkonium chloride, behenic acid amidopropyldimethylhydroxypropylammonium chloride, stearic acid diethylaminoethylamide, stearic acid dimethylaminopropylamide, lanolin derivative quaternary ammonium salts, etc. Amphoteric surfactants include carboxybetaine, amidobetaine, sulfobetaine, hydroxysulfobetaine, amidosulfobetaine, phosphobetaine, aminocarboxylate, imidazoline derivative, and amidoamine types. Nonionic surfactants include propylene glycol fatty acid esters, glycerin fatty acid esters, polyglycerin fatty acid esters, sorbitan fatty acid esters, POE sorbitan fatty acid esters, POE sorbitan fatty acid esters, POE glycerin fatty acid esters, POE alkyl ethers, POE fatty acid esters, POE hydrogenated castor oil, POE castor oil, POE-POP copolymer, POE-POP alkyl ether, polyether-modified silicone lauric acid alkanolamide, alkylamine oxide, and hydrogenated soybean phospholipids. Natural surfactants include lecithin, saponin, and sugar-based surfactants.

[0030] (7) Examples of polyhydric alcohols and sugars include ethylene glycol, diethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, glycerin, diglycerin, polyglycerin, 3-methyl-1,3-butanediol, 1,3-butylene glycol, sorbitol, mannitol, raffinose, erythritol, glucose, sucrose, fructose, xylitol, lactose, maltose, maltitol, trehalose, alkylated trehalose, mixed isomerized sugars, sulfated trehalose, pullulan, etc. Chemically modified versions of these can also be used.

[0031] (8) Examples of polymers: acrylic acid ester / methacrylic acid ester copolymer (Plassize, manufactured by GOO Chemical Co., Ltd.), vinyl acetate / crotonic acid copolymer (Resin 28-1310, manufactured by NSC Co., Ltd.), vinyl acetate / crotonic acid / vinyl neodecanoate copolymer (28-2930, manufactured by NSC Co., Ltd.), methyl vinyl ether maleic acid half ester (Gantrez ES, manufactured by ISP Co., Ltd.), t-butyl acrylate / ethyl acrylate / methacrylic acid copolymer (Ruvimer, manufactured by BASF Co., Ltd.), vinylpyrrolidone / vinyl acetate / vinyl propionate copolymer (Ruviscol VAP, manufactured by BASF Co., Ltd.), vinyl acetate Vinyl acetate / crotonic acid copolymer (Rubyset CA, BASF), vinyl acetate / crotonic acid / vinyl pyrrolidone copolymer (Rubyset CAP, BASF), vinyl pyrrolidone / acrylate copolymer (Rubyflex, BASF), acrylate / acrylamide copolymer (Ultrahold, BASF), vinyl acetate / butyl maleate / isobornyl acrylate copolymer (Advantage, ISP), carboxyvinyl polymer (Carbopol, BFGoodrich), acrylic acid / alkyl methacrylate copolymer (Pemulen, BF Examples of such polymers include anionic polymers such as acetic acid amphoteric dialkylaminoethyl methacrylate polymer (Yukaformer, Mitsubishi Chemical), and octylacrylamide acrylate / hydroxypropyl acrylate / butylaminoethyl methacrylate copolymer (AMPHOMER, NSC), cationic polymers such as quaternized vinylpyrrolidone / dimethylaminoethyl methacrylate (GAFQUAT, ISP), and methylvinylimidazolium chloride / vinylpyrrolidone copolymer (Rubycoat, BASF), and nonionic polymers such as polyvinylpyrrolidone (Ruviscol K, BASF), vinylpyrrolidone / vinyl acetate copolymer (Ruviscol VA, BASF), vinylpyrrolidone / dimethylaminoethyl methacrylate copolymer (Copolymer 937, ISP), and vinylcaprolactam / vinylpyrrolidone / dimethylaminoethyl methacrylate copolymer (Copolymer VC713, ISP).In addition, naturally occurring polymeric compounds such as cellulose or derivatives thereof, keratin and collagen or derivatives thereof, calcium alginate, pullulan, agar, gelatin, tamarind seed polysaccharides, xanthan gum, carrageenan, high methoxyl pectin, low methoxyl pectin, guar gum, gum arabic, crystalline cellulose, arabinogalactan, karaya gum, tragacanth gum, alginic acid, albumin, casein, curdlan, gellan gum, and dextran can also be suitably used.

[0032] (9) Examples of physiologically active ingredients: Physiologically active ingredients include substances that impart some kind of physiological activity to the skin when applied to the skin, such as whitening ingredients, immunostimulants, anti-aging agents, UV protection agents, slimming agents, tightening agents, antioxidants, hair growth agents, hair restoration agents, moisturizing agents, blood circulation promoters, antibacterial agents, disinfectants, drying agents, cooling agents, warming agents, vitamins, amino acids, wound healing promoters, irritation soothing agents, analgesics, cell activators, and enzyme components. Examples of suitable ingredients include angelica extract, avocado extract, hydrangea extract, althaea extract, arnica extract, aloe extract, apricot extract, apricot kernel extract, ginkgo extract, fennel extract, turmeric extract, oolong tea extract, angelica tree extract, echinacea leaf extract, Scutellaria root extract, Phellodendron bark extract, Coptis japonica extract, barley extract, St. John's wort extract, dead nettle extract, watercress extract, orange extract, dried seawater, seaweed extract, hydrolyzed elastin, hydrolyzed wheat powder, hydrolyzed silk, chamomile extract, carrot extract, artemisia capillaris extract, licorice extract, kalkade extract, kakyoku extract, cinchona extract, cucumber extract, guanosine, gardenia extract, kumazasa extract, sophora flavescens extract, walnut extract, grapefruit extract, clematis extract, chlorella extract, mulberry extract, gentian extract, black tea extract, yeast extract, and burdock. extract, rice bran fermented extract, rice germ oil, comfrey extract, collagen, bilberry extract, Chinese radish extract, Bupleurum extract, umbilical cord extract, salvia extract, soapwort extract, bamboo extract, hawthorn extract, Japanese pepper extract, shiitake mushroom extract, rehmannia root extract, Lithospermum root extract, perilla extract, linden extract, meadowsweet extract, peony extract, calamus root extract, white birch extract, horsetail extract, ivy extract, European sage Zashi extract, elderberry extract, yarrow extract, peppermint extract, sage extract, mallow extract, cnidium extract, Swertia japonica extract, soybean extract, Chinese laurel extract, thyme extract, tea extract, clove extract, Imperata cylindrica extract, tangerine peel extract, Angelica acutiloba extract, calendula extract, peach kernel extract, spruce extract, Houttuynia cordata extract, tomato extract, natto extract, carrot extract, garlic extract, wild rose extract,Hibiscus extract, Bakumondo extract, Parsley extract, Honey, Hamamelis extract, Parietaria extract, Kochia extract, Bisabolol, Loquat extract, Coltsfoot extract, Butterbur extract, Poria columbine extract, Butcher's broom extract, Grape extract, Propolis, Luffa extract, Safflower extract, Peppermint extract, Tilia extract, Peony extract, Hop extract, Pine extract, Horse chestnut extract, Skunk cabbage extract, Soapberry extract, Melissa extract, Peach extract, Cornflower extract Examples of such extracts include kiss, eucalyptus extract, saxifrage extract, coix seed extract, mugwort extract, lavender extract, apple extract, lettuce extract, lemon extract, astragalus extract, rose extract, rosemary extract, Roman chamomile extract, royal jelly extract, placenta, yuzu seed extract, blueberry extract, lingonberry extract, Cistanche Tubulosa extract, black rice extract, green coffee bean extract, resveratrol, kiwi seed extract, strawberry seed extract, cherry blossom extract, and kudzu lactic acid bacteria. In addition, biopolymers such as deoxyribonucleic acid, mucopolysaccharides, sodium hyaluronate, sodium chondroitin sulfate, collagen, elastin, chitin, chitosan, and hydrolyzed eggshell membrane; moisturizing ingredients such as amino acids, hydrolyzed peptides, sodium lactate, urea, sodium pyrrolidone carboxylate, betaine, whey, and trimethylglycine; oily ingredients such as sphingolipids, ceramides, phytosphingosine, cholesterol, cholesterol derivatives, and phospholipids; immunostimulants such as ε-aminocaproic acid, glycyrrhizinic acid, β-glycyrrhetinic acid, lysozyme chloride, guaiazulene, and hydrocortisone; and vitamins. Vitamins such as A, vitamin B2, vitamin B6, vitamin C, vitamin D, vitamin E, calcium pantothenate, biotin, nicotinamide, vitamin C ester, active ingredients such as allantoin, diisopropylamine dichloroacetate, 4-aminomethylcyclohexanecarboxylic acid, antioxidants such as tocopherol, carotenoids, flavonoids, tannins, lignans, saponins, cell activators such as alpha-hydroxy acids and beta-hydroxy acids, blood circulation promoters such as gamma-oryzanol and vitamin E derivatives, wound healing agents such as retinol and retinol derivatives, arbutin, kojic acid, placenta extract, sulfur,Skin whitening agents such as ellagic acid, linoleic acid, tranexamic acid, and glutathione, cepharanthine, licorice extract, capsicum tincture, hinokitiol, iodized garlic extract, pyridoxine hydrochloride, DL-α-tocopherol, DL-α-tocopherol acetate, nicotinic acid, nicotinic acid derivatives, calcium pantothenate, D-pantothenyl alcohol, acetyl pantothenyl ethyl ether, biotin, allantoin, isopropyl methylphenol, estradiol, ethinyl estradiol, capronium chloride, benzalkonium chloride, diphenhydramine hydrochloride, tacanal, camphor, salicylic acid, vanillyl nonyl amide, and vanilla nonanoate. Hair growth agents such as methylparaben, piroctone olamine, glyceryl pentadecanoate, L-menthol, mononitroguaiacol, resorcinol, γ-aminobutyric acid, benzethonium chloride, mexiletine hydrochloride, auxin, female hormones, cantharides tincture, cyclosporine, zinc pyrithione, hydrocortisone, minoxidil, polyoxyethylene sorbitan monostearate, peppermint oil, Sasanishiki extract, placenta, yuzu seed extract, blueberry extract, lingonberry extract, Cistanche Tubulosa extract, black rice extract, green coffee bean extract, resveratrol, kiwi seed extract, strawberry seed extract, cherry blossom extract, and kudzu lactic acid bacteria are also included.

[0033] (10) Examples of antioxidants include sodium bisulfite, sodium sulfite, erythorbic acid, sodium erythorbate, dilauryl thiodipropionate, tocopherol, tolylbiguanide, nordihydroguaiaretic acid, parahydroxyanisole, butylhydroxyanisole, dibutylhydroxytoluene, ascorbyl stearate, ascorbyl palmitate, octyl gallate, propyl gallate, carotenoids, flavonoids, tannins, lignans, saponins, and plant extracts that are known to have antioxidant effects, such as apple extract and clove extract.

[0034] (11) Examples of solvents include purified water, ethanol, lower alcohols, ethers, LPG, fluorocarbons, N-methylpyrrolidone, fluoroalcohols, volatile linear silicones, and next-generation fluorocarbons.

[0035] Examples of the present invention will be described below. Note that the examples shown below are provided to confirm the various actions and effects of the agent of the present invention obtained by the present invention, and the scope of the present invention is not limited to these products and manufacturing methods.

[0036] Example: Preparation of Compounds A and B 1. Preparation of Compound A A glucosylceramide (GlcCer) enriched fraction (15.4 g) from a by-product obtained in the rice bran oil manufacturing process was subjected to medium-pressure silica gel chromatography (column: Universal Column Premium, 3 L, Yamazen Corporation), washed with ethyl acetate for 20 minutes, and then eluted with a chloroform:methanol gradient (95:5 → 50:50, v / v, 50 minutes). The fraction (580 mg) obtained by concentrating and drying the eluate from the 95:5→90:10 gradient was crudely purified by HPLC [column: CAPCELLPAK C18, 250 mm × 20 mm inner diameter (Shiseido), eluent: methanol:THF = 90:10, detection: RI, flow rate: 9 mL / min], and then further purified by HPLC [column: Sunrise C30, 250 mm × 20 mm inner diameter (Chromanik Technologies), eluent: methanol:THF = 90:10, detection: RI, flow rate: 9 mL / min] to obtain new compounds (compound A, 15.2 mg) and (compound B, 12.8 mg) as white powders.

[0037] 2. Identification of the structure of compound A The obtained component was analyzed by optical rotation, mass spectrometry, and infrared absorption spectrum. 1 H and 13 C-NMR spectrum was measured. 1) Physical and chemical data: White powder. [α] D 25 28.0° (c=0.2, MeOH). High resolution ESI-MS Calcd for C 62 H 115 NO 10 Na (M+Na) + ; Found: 1056.8419, IR (KBr, cm -1): 3379, 2920, 2851, 1740, 1624, 1516, 1467, 1080. 1H-NMR (C5D5N, 800 MHz) δ: 0.88 (3H×2, t, J=7.1 Hz 18, 20'-H), 0.89 (3H, t, J=7.1 Hz 18'''-H), 1.25 (2H×3, m, 16, 18', 16'''-H), 1.29 (2H×3, m, 17, 19', 17'''-H), 1.25-1.32 (m, 11-15, 6'-17', 4'''-7''', 12'''-15'''-H), 1.64 (2H, tt, J=7.6, 7.8 Hz, 3'''-H), 1.72 (1H, m, 4'a-H), 1.79 (1H, m, 4'b-H), 1.99 (1H, m, 3'a-H), 2.10 (2H, m, 10, 8''', 11'''-H), 2.20 (2H, m, 6-H), 2.20 (1H, m, 3'b-H), 2.22 (2H, m, 7-H), 2.35 (2H, m, 2'''-H), 3.98 (1H, ddd, J=2.1, 6.2, 9.4 Hz, 5''-H), 3.99 (1H, dd, J=7.8, 8.9 Hz, 2''-H), 4.03 (1H, dd, J=9.2, 9.2 Hz, 4''-H), 4.16 (1H, dd, J=8.9, 8.9 Hz, 3''-H), 4.25 (1H, dd, J=3.7, 10.5 Hz, 1a-H), 4.54 (1H, m, 2'-H), 4.70 (1H, m, 1b-H), 4.71 (1H, m, 3-H), 4.76 (1H, dd, J=6.0, 11.7 Hz, 6''a-H), 4.79 (1H, m, 2-H), 4.88 (1H, d, J=7.8 Hz, 1''-H), 4.96 (1H, dd, J=1.8, 11.7 Hz, 6''b-H), 5.50 (2H×2, m, 8,9; 9''', 10'''-H), 5.94 (1H, dd, J=5.7, 15.3 Hz, 5-H), 5.99 (1H, dd, J=5.7, 15.5 Hz, 4-H), 8.28 (1H, d, J=8.9 Hz, NH). 13 C-NMR (C5D5N, 200 MHz) δ C: 70.2 (C-1), 54.6 (C-2), 72.5 (C-3), 132.2 (C-4), 132.1 (C-5), 32.9 (C-6), 27.4 (C-7), 129.5 (C-8), 130.7 (C-9), 27.7 (C-10), 29.6, 29.9, 30.0, 30.1 (C-11-15), 32.1 (C-16), 22.9 (C-17), 14.3 (C-18), 175.7 (C-1'), 72.5 (C-2'), 35.7 (C-3'), 25.9 (C-4'), 30.1 (C-5'), 29.6, 29.9, 30.0, 30.1 (C-6'-17'), 32.1 (C-18'), 22.9 (C-19'), 14.3 (C-20'), 105.5 (C-1''), 75.4 (C-2''), 78.3 (C-3''), 71.5 (C-4''), 75.0 (C-5''), 64.6 (C-6''), 173.7 (C-1'''), 34.4 (C-2'''), 25.3 (C-3'''), 29.4 (C-4'''), 29.4 (C-5'''), 29.5 (C-6'''), 29.6 (C-7'''), 27.6 (C-8'''), 130.3 (C-9'''), 130.3 (C-10'''), 27.6 (C-11'''), 29.8 (C-12'''), 29.6 (C-3'''), 29.6 (C-14'''), 29.6 (C-15'''), 32.1 (C-16'''), 22.9 (C-17'''), 14.3 (C-18'''). Positive-ion ESI-MS: m / z 1030 (M+Na) + .

[0038] 2) Two-dimensional NMR HMQC ( 1 H-detected multiple quantum coherence spectrum), HMBC ( 1 H-detected multi-bond heteronuclear multiple quantum coherence spectrum) and 1 H- 1As a result of H COSY (Correlation Spectroscopy) analysis, the proton-carbon correlation shown by the arrows in Figure 1 and the proton-proton correlation shown by the thick line were confirmed.

[0039] 3. Structural determination of compound B The obtained component was analyzed by optical rotation, mass spectrometry, and infrared absorption spectrum. 1 H and 13 C-NMR spectrum was measured. 1) Physical and chemical data: White powder. [α] D 25 27.9° (c=0.17, MeOH). High resolution ESI-MS Calcd for C 62 H 113 NO 10 Na (M+Na) + : ; Found: 1054.8246, IR (KBr, cm -1 ): 3374, 2957, 2891, 1740, 1628, 1522, 1468, 1080. 1H-NMR (C5D5N, 800 MHz) δ: 0.87 (3H, t, J=7.0 Hz 18 or 20'-H), δ: 0.88 (3H, t, J=7.0 Hz 18 or 20'-H), 0.89 (3H, t, J=6.9 Hz 16'''-H), 1.25 (2H×2, m, 16, 18', 16'''-H), 1.29 (2H×3, m, 17, 19', 17'''-H), 1.26-1.32 (m, 11-15, 5'-17', 4'''-7''', 15'''-H), 1.64 (2H, tt, J=7.3, 7.6 Hz, 3'''-H), 1.72 (1H, m, 4'a-H), 1.79 (1H, m, 4'b-H), 2.01 (1H, m, 3'a-H), 2.11 (2H×3, m, 10, 8''', 14'''-H), 2.20 (2H, m, 6-H), 2.20 (1H, m, 3'b-H), 2.22 (2H, m, 7-H), 2.35 (2H, m, 2'''-H), 2.92 (2H, dd, J=5.7, 6.0 Hz, 11'''-H), 3.98 (1H, ddd, J=2.1, 6.0, 9.2 Hz, 5''-H), 4.00 (1H, dd, J=7.8, 8.9 Hz, 2''-H), 4.04 (1H, dd, J=8.9, 9.2 Hz, 4''-H), 4.16 (1H, dd, J=8.9, 8.9 Hz, 3''-H), 4.25 (1H, dd, J=3.7, 10.5 Hz, 1a-H), 4.55 (1H, m, 2'-H), 4.71 (1H, dd, J=6.2, 10.5 Hz, 1b-H), 4.73 (1H, m, 3-H), 4.76 (1H, dd, J=6.0, 11.7 Hz, 6''a-H), 4.79 (1H, m, 2-H), 4.89 (1H, d, J=7.8 Hz, 1''-H), 4.96 (1H, dd, J=2.1, 11.7 Hz, 6''b-H), 5.50 (2H×3, m, 8,9; 9''', 10'''; 12''', 13''' -H), 5.95 (1H, dt, J=15.6, 6.0 Hz, 5-H), 5.99 (1H, dd, J=6.2, 15.6 Hz, 4-H), 8.29 (1H, d, J=8.9 Hz, NH). . 13 C-NMR (C5D5N, 200 MHz) δ C : 70.2 (C-1), 54.6 (C-2), 72.5 (C-3), 132.2 (C-4), 132.1 (C-5), 33.0 (C-6), 27.4 (C-7), 129.5 (C-8), 130.7 (C-9), 27.6 (C-10), 29.6, 29.9, 30.0, 30.1 (C-11-15), 32.1 (C-16), 22.9 (C-17), 14.3 (C-18), 175.7 (C-1'), 72.5 (C-2'), 35.7 (C-3'), 25.9 (C-4'), 30.1 (C-5'), 29.6, 29.9, 30.0, 30.1 (C-6'-17'), 32.1 (C-18'), 22.9 (C-19'), 14.3 (C-20'), 105.5 (C-1''), 75.4 (C-2''), 78.3 (C-3''), 71.5 (C-4''), 75.0 (C-5''), 64.6 (C-6''), 173.7 (C-1'''), 34.4 (C-2'''), 25.3 (C-3'''), 29.4 (C-4'''), 29.4 (C-5'''), 29.5 (C-6'''), 29.6 (C-7'''), 27.6 (C-8'''), 128.5 (C-9'''), 128.5 (C-10'''), 26.1 (C-11'''), 130.5 (C-12'''), 130.5 (C-3'''), 27.5 (C-14'''), 29.9 (C-15'''), 31.7 (C-1 6'''), 22.8 (C-17'''), 14.2 (C-18'''). Positive-ion ESI-MS: m / z 1054 (M+Na) + .

[0040] 2) Two-dimensional NMR HMQC ( 1 H-detected multiple quantum coherence spectrum), HMBC ( 1H-detected multi-bond heteronuclear multiple quantum coherence spectrum) and 1 H- 1 As a result of H COSY (Correlation Spectroscopy) analysis, the proton-carbon correlation shown by the arrows in Figure 2 and the proton-proton correlation shown by the thick line were confirmed.

[0041] 4. Identification of acyl groups and GlcCer molecular species Identification of acyl groups by solvolysis was performed as follows. The new compound (compound A, 2.1 mg) or (compound B, 2.0 mg) was dissolved in 0.5% sodium methoxide / methanol solution (500 μL) and reacted on ice for 3 hours. After that, 1% acetic acid / methanol solution (500 μL) was added to the reaction mixture. To identify the acyl groups, the reaction mixture was subjected to reversed-phase HPLC [column: CAPCELLPAK C18 SG-120, 250 mm × 4.6 mm inner diameter (Shiseido)], eluent: acetonitrile:methanol:water = 75:11:14, detection: CAD, flow rate: 1 mL / min; column temperature: 40 °C]. The retention times of the fatty acid methyl esters of the derivatives were compared with the retention times of the standards (t R The acyl group of new component (2) was identified as oleic acid, and the acyl group of new component (3) as linoleic acid by comparing with the retention times of the standard (t : methyl palmitate; 25.4 min, methyl oleate; 26.3 min, methyl linoleate; 13.8 min). The GlcCer molecular species were identified by subjecting the reaction mixture to a column (CAPCELLPAK C18 SG-120, 250 mm × 4.6 mm inner diameter (Shiseido) column, eluent: methanol, detection: CAD, flow rate: 1 mL / min; column temperature: 40 °C). The retention time of the derivative GlcCer was compared with that of the standard (t RThe GlcCer molecular species was identified as GlcCer[d18:2(4E,8Z / 20:0)] by comparing with the GlcCer[d18:2(4E,8Z / 20:0)]; 7.1 min, GlcCer[d18:2(4E,8E / 20:0)]; 7.3 min. From the above physicochemical data, it was determined that the new component (compound A) is 6"-O-oleoyl-GlcCer[d18:2(4E,8Z / 20:0)], in which oleic acid is ester-linked to the 6" position of the glucose of GlcCer[d18:2(4E,8Z / 20:0)], and the new component (compound B) is 6"-O-linoleoyl-GlcCer[d18:2(4E,8Z / 20:0)], in which linoleic acid is ester-linked to the 6" position of the glucose of GlcCer[d18:2(4E,8Z / 20:0)].

[0042] Test Example 1: Effect of Compounds A and B on Transepidermal Water Loss in a 3D Human Epidermis Model 1. Test Method A LabCyte EPI-MODEL (24-well) from J-Tec was used for the 3D human epidermis model. Compounds A and B were added to the culture medium to final concentrations of 1, 3, and 10 μM, and TEWL was measured before and after culture. TEWL measurements were performed using Integral's Tewitro24, and evaluated as the amount of change from before culture. The results are shown in Figure 3.

[0043] 2. Measurement Results and Effects of Examples in Test Example 1 Figure 3 shows the changes in TEWL of a human epidermis 3D model cultured with compounds A and B. As a result of the experiment, compounds A and B significantly reduced TEWL. This confirmed that compounds A and B are useful as TEWL improvers.

[0044] Test Example 2: Evaluation of immunostimulatory activity using iPS cell-derived dendritic cells (iMylc®) In this experiment, iMylc® cells (immature myeloid cells obtained by inducing differentiation from iPS cells) purchased from Mican Technology, Inc. were used. These cells were cultured and evaluated using iMylc® dedicated maintenance medium provided by Mican Technologies. iMylc® cells were seeded (1.0 × 10) in a 96-well plate. 4 After adding medium containing the test substance (100 μL / well) to the cells (100 μL / well), the cells were cultured for 20 hours at 37°C in the presence of 5% CO2. The final DMSO concentration was adjusted to 0.1% (v / v). After culture, the amount of IL-6 produced in the culture supernatant was measured using a commercially available kit (Human IL-6 ELISA MAX™ Deluxe Set (Biolegend)) according to the standard method. The results are shown in Figure 4.

[0045] Results and Effects of Examples in Test Example 2 Three types of acylated GlcCer, which are novel compounds, were evaluated for their immunostimulatory activity in dendritic cells. As a result, 6"-O-linoleoyl-GlcCer[d18:2(4E,8Z) / 20:0] (compound B) and 6"-O-oleoyl-GlcCer[d18:2(4E,8Z) / 20:0] (compound A) were found to have a significant effect of increasing IL-6 production. The results suggest that the type of fatty acid bound to GlcCer[d18:2(4E,8Z) / 20:0] affects activity. This confirms that compounds A and B activate dendritic cells and increase cytokine production, and therefore have immunostimulatory activity. In other words, compounds A and B were confirmed to be useful as immunostimulants.

[0046] The following are formulation examples of the rice bran extract containing compounds A and B of the present invention (compounds A and B 0.05 to 0.5%). Note that the following formulation examples do not limit the present invention. Formulation Example 1: Chewing gum Sugar 53.0 wt% Gum base 20.0 Glucose 10.0 Starch syrup 16.0 Flavoring 0.5 Rice bran extract 0.5 100.0 wt%

[0047] Formulation Example 2: Gummy Reduced starch syrup 40.0 wt% Granulated sugar 20.0 Glucose 20.0 Gelatin 4.7 Water 9.68 Yuzu juice 4.0 Yuzu flavor 0.6 Coloring 0.02 Rice bran extract 1.0 100.0 wt%

[0048] Formulation Example 3: Candy Sugar 50.0 wt% Starch syrup 33.0 Water 14.4 Organic acid 2.0 Flavoring 0.2 Rice bran extract 0.4 100.0 wt%

[0049] Formulation example 4: Yogurt (hard / soft) Milk 41.5 wt% Skim milk powder 5.8 Sugar 8.0 Agar 0.15 Gelatin 0.1 Lactic acid bacteria 0.005 Rice bran extract 0.4 Flavoring trace Water balance 100.0 wt%

[0050] Formulation example 5: Soft drink Fructose glucose syrup 30.0 wt% Emulsifier 0.5 Rice bran extract 0.3 Flavoring appropriate amount Purified water Remaining 100.0 wt%

[0051] Formulation Example 6: Tablets Sugar 76.4 wt% Glucose 19.0 Sucrose fatty acid ester 0.2 Rice bran extract 0.5 Purified water 3.9 100.0 wt%

[0052] Formulation Example 7: Soft capsule Brown rice germ oil 47.0 wt% Yuzu seed oil 40.0 Emulsifier 12.0 Rice bran extract 1.0 100.0 wt%

[0053] Formulation Example 8: Tablet Lactose 54.0 wt% Microcrystalline cellulose 30.0 Starch hydrolysate 10.0 Glycerin fatty acid ester 5.0 Rice bran extract 1.0 100.0 wt%

[0054] Formulation Example 9: Cosmetic Cream Squalane 20.0 wt% Beeswax 5.0 Refined Jojoba Oil 5.0 Glycerin 5.0 Glycerin Monostearate 2.0 Polyoxyethylene (20) Sorbitan Monostearate 2.0 Strawberry Seed Extract 0.1 Glucosylceramide 0.1 Rice Bran Extract 1.0 Preservative Appropriate Quantity Fragrance Appropriate Quantity Purified Water Remaining 100.0 wt%

[0055] Formulation Example 10: Lotion Ethanol 5.0 wt% Glycerin 2.0 1,3-butylene glycol 2.0 Polyethylene oleyl ether 0.5 Sodium citrate 0.1 Citric acid 0.1 Strawberry seed extract 0.1 Glucosylceramide 0.1 Rice bran extract 0.1 Purified water Remaining 100.0 wt%

[0056] Formulation Example 11: Body Gel Macadamia nut oil 2.0 wt% Octyldodecyl myristate 10.0 Methylphenylpolysiloxane 5.0 Behenyl alcohol 3.0 Stearic acid 3.0 Batyl alcohol 1.0 Glyceryl monostearate 1.0 Polyoxyethylene sorbitol tetraoleate 2.0 Hydrogenated soybean phospholipid 1.0 Ceramide 0.1 Retinol palmitate 0.1 Preservative (as needed) Centella asiatica extract 1.0 Strawberry seed extract 0.1 Glucosylceramide 0.1 Rice bran extract 1.0 1,3-butylene glycol 5.0 Purified water Balance 100.0 wt%

[0057] Formulation Example 12: Emulsion Squalane 4.0 wt% Vaseline 2.5 Cetyl alcohol 2.0 Glycerin 2.0 Lipophilic glyceryl monostearate 1.0 Stearic acid 1.0 L-arginine 1.0 Strawberry seed extract 0.1 Glucosylceramide 0.1 Rice bran extract 0.5 Potassium hydroxide 0.1 Fragrance Trace amount Purified water Balance 100.0 wt%

[0058] Formulation example 13: Bath additive (liquid) Propylene glycol 49.8 wt% Ethanol 20.0 Sodium sulfate 5.0 Strawberry seed extract 0.1 Glucosylceramide 0.1 Rice bran extract 0.5 Lanolin 0.5 Avocado oil 0.5 Coloring 1.5 Fragrance 22.0 100.0 wt% Formulation example 14: Shampoo Sodium polyoxyethylene alkyl ether sulfate (E.O 2 moles) 15.0 Coconut oil fatty diethanolamide 5.0 Glycerin 3.0 Strawberry seed extract 0.1 Glucosylceramide 0.1 Rice bran extract 0.4 Ethanol 5.0 Fragrance and preservative appropriate amount Ion-exchanged water Rest Total 100 wt%

[0059] Formulation Example 15: Hair Cream Liquid paraffin 20.0 wt% Solid paraffin 3.0 Polyoxyethylene cetyl ether (E.O. 15 moles) 2.0 Sorbitan sesquioleate 1.0 Strawberry seed extract 0.1 Glucosylceramide 0.1 Rice bran extract 0.2 Ethanol 10.0 Potassium hydroxide 0.1 Glycerin 3.0 Fragrance and preservatives appropriate amount Purified water Rest Total 100 wt%

[0060] Formulation Example 16: Ointment White beeswax 5.0 wt% Purified lanolin 5.0 Strawberry seed extract 0.1 Glucosylceramide 0.1 Rice bran extract 1.0 Fragrance 0.1 Vaseline Remainder Total 100 wt%

[0061] As described above, the present invention can provide a novel compound and its use.

Claims

1. A compound represented by the following chemical formula (1).

2. A compound represented by the following chemical formula (2).

3. A transepidermal water loss reducer comprising the compound according to claim 1 or 2 as an active ingredient.

4. A moisturizing agent comprising the compound according to claim 1 or 2 as an active ingredient.

5. An agent for promoting interleukin 6 production in dendritic cells, comprising the compound according to claim 1 or 2 as an active ingredient.

6. An immunostimulant comprising the compound according to claim 1 or 2 as an active ingredient.

7. A method for producing the compound according to claim 1 or 2, characterized in that it comprises a step of isolating the compound from an extract of rice bran.

8. A moisturizing food or drink composition containing the compound shown in 1. or 2. above as an active ingredient.

9. A pharmaceutical composition for moisturizing comprising the compound shown in 1. or 2. above as an active ingredient.

10. A moisturizing cosmetic composition comprising the compound described in 1. or 2. above as an active ingredient.

11. An immunostimulating food or drink composition containing the compound described in 1. or 2. above as an active ingredient.

12. An immunostimulating pharmaceutical composition containing the compound described in 1. or 2. above as an active ingredient.

13. An immunostimulating cosmetic composition containing the compound described in 1. or 2. above as an active ingredient.

14. A method for moisturizing human skin, comprising: (a) isolating the compound described in 1. or 2. above from an extract of rice bran; and (b) orally or parenterally administering an appropriate amount of the compound described in 1. or 2. above to a human, thereby reducing transepidermal water loss in the human.

15. A method for stimulating human immunity, comprising: (a) isolating the compound described in 1. or 2. above from an extract of rice bran; and (b) administering an appropriate amount of the compound described in 1. or 2. above to a human by oral or parenteral administration, thereby promoting interleukin 6 production in dendritic cells of the human.

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