JP6075025B2 - New compounds and their uses - Google Patents

Description

  The present invention relates to a novel compound and use using the same.

  Junsai is a perennial aquatic plant widely distributed from the temperate to the tropics. In Japan, it is eaten with sprouts and vinegar. As for Junsai extract, antioxidant and antibacterial action (see Patent Document 1), anti-inflammatory action (see Patent Document 2) and the like are disclosed. However, research on anti-aging effects on skin such as wrinkles, stains, sagging, etc. has not been made for Junsai and the compounds contained in them, and many of the substances contained in Junsai have not yet been isolated and identified. Is the current situation. From this, it is considered that Junsai may contain useful new compounds.

On the other hand, the composition of the skin is roughly classified into three, which are formed from the outer layer to the epidermis, dermis, and subcutaneous tissue, each of which plays various roles such as maintaining the body's regularity and protecting it from the outside world. The function of the skin dermis serves as a cushion that absorbs impacts from the outside world. If the effect of this cushion, that is, the thickness of the dermis and the flexibility are lost, wrinkles and sagging occur.

On the other hand, the components of the dermis are mainly collagen, elastin, and fibroblasts, and aging symptoms such as disappearance of wrinkles, wrinkles and sagging due to deterioration, reduction or degeneration of collagen and elastin. Appears. In the healthy dermis, old collagen and elastin are absorbed and excreted, while new collagen and elastin are produced from fibroblasts, maintaining a constant qualitative and quantitative homeostasis. However, with increasing age, the homeostasis of external and internal factors is lost, and elastase derived from fibroblasts degrades elastin more than necessary, and the chemical bond between the elastin protein and sugar that constitutes the dermal matrix. Due to abnormal cross-linking reaction (saccharification reaction) by elastin, elastin is reduced and denaturation is promoted.

Collagen is the main component of the skin and is an elastic fibrous protein. If the amount of collagen production is normal, the skin becomes rich and firm and smooth, and a flexible capillary is formed, so that nutrients and waste products can be exchanged smoothly. However, collagen is degraded in the body by the action of collagenase. Therefore, in order to suppress collagen degradation and prevent skin aging, various substances that can be collagenase activity inhibitors have been studied. To date, representative examples of collagenase activity inhibitors include caffeic acid or a salt thereof (Patent Document 3), guava leaf (Patent Document 4), Hamameris extract (Patent Document 5), cowberry, birch, hamasuge, Bodaiju, green tea (patent document 6), spruce, mistletoe, jojoba leaf, lotus leaf, red clover (patent document 7), pine bark extract (patent document 8), kale (patent document 9), camcam seed extract (patent) Document 10), an extract of acerola seed (Patent Document 11) and the like are known.

Hyaluronic acid retains moisture in the interstitial space, retains cells based on the formation of a jelly-like matrix in the tissue, retains tissue lubricity and flexibility, resists external forces such as mechanical failure, and It has many functions such as prevention of bacterial infection.

On the other hand, it has been reported that the hyaluronic acid staining intensity between epidermal cells decreases due to aging, and that almost no hyaluronic acid is detected in the part where photoelastic fibrosis has occurred due to ultraviolet irradiation. It is thought to cause a decrease in elasticity. In order to improve such a state, a method of keeping the skin surface moisturized by applying a cosmetic containing hyaluronic acid has been taken, but since hyaluronic acid, which is a polymer, does not penetrate the skin, it is fundamentally Improvement cannot be expected. Therefore, it is expected to develop a substance that fundamentally improves skin function by inhibiting hyaluronidase, which is a hyaluronic acid degrading enzyme, to enhance the hyaluronic acid synthesizing ability inherent in the cell itself.

Furthermore, factors such as slimming, skin beautification, and whitening are known in beauty, and pigmentation after inflammation such as spots, freckles, darkness, senile plaques, wounds and burns is regarded as a cosmetic problem. There is a growing awareness of whitening, especially among women. In the pigmentation, stimuli such as ultraviolet rays and inflammation activate melanoma cells in the dermal tissue, and tyrosinase, an enzyme contained in melanoma cells, oxidatively polymerizes tyrosine, a biological component, producing melanin, a dark brown pigment. The mechanism to do this has been clarified. Therefore, beauty foods and beverages and cosmetics containing various animal and plant extracts have been proposed for the purpose of obtaining a whitening effect by inhibiting the activity of tyrosinase.

Japanese Patent Laid-Open No. 1-138288 JP-A-2-286622 JP-A-5-117145 JP-A-7-291873 JP-A-8-283133 JP 2003-12531 A JP 2003-48846 A JP 2003-238426 A JP 2003-238426 A Japanese Patent No. 3635081 JP 2007-314552 A

Under such circumstances, the present inventors have found that the novel compound contained in Junsai has skin beautifying effects such as elastase inhibitory action, collagenase inhibitory action, hyaluronidase inhibitory action, tyrosinase inhibitory action, etc., and has completed the present invention. I let you.
An object of this invention is to isolate the useful novel compound contained in Junsai, and to provide the skin beautifying agent etc. containing this compound.

The features of the present invention for solving the above-described problems are as follows.
1. A compound represented by the following chemical formula (1).
2. Above 1. Junsai extract containing the compound described in 1.
3. Above 1. Or 2. A skin-beautifying agent comprising the substance described in 1.
4). A skin beautifying agent containing Junsai and / or an extract thereof as an active ingredient.
5. 3. above. Or 4. A composition for beautifying skin for oral consumption containing the beautifying agent described in 1.
6). 3. above. Or 4. Cosmetics containing the skin beautifier described in 1.
7). 3. above. Or 4. A pharmaceutical comprising the skin beautifying agent described in 1.
8). 3. above. Or 4. A skin external preparation containing the skin beautifying agent described in 1.

It is a figure which shows the main HMBC correlations of a compound (1). It is a graph which shows the elastase inhibitory effect of a novel compound (1). It is a graph which shows the elastase inhibitory effect of Junsai extract. It is a graph which shows the collagenase inhibitory effect of a novel compound (1). It is a graph which shows the collagenase inhibitory effect of Junsai extract. It is a graph which shows the tyrosinase inhibitory effect of a novel compound (1) (Junsainoside A). It is a graph which shows the tyrosinase inhibitory effect of Junsai extract. It is a graph which shows the hyaluronidase inhibitory effect of the novel compound (1) (Junsainoside A). It is a graph which shows the hyaluronidase inhibitory effect of Junsai extract.

Hereinafter, the present invention will be described in detail.
The compound of the present invention (hereinafter sometimes referred to as compound (1)) is represented by the following chemical formula (1).

Compound (1) is tamarixetin in the IUPAC nomenclature.
3-O- (6 "-OE-caffeoyl) -bD-glucopyranosid, and the present inventor named the compound (1) as JunsainosideA.
Compound (1) can be isolated by extracting Junsai with a solvent.

Examples of the extraction solvent include alcohols such as methanol, ethanol, propanol and butanol; glycols such as 1,3-butylene glycol, glycerin and propylene glycol; esters such as ethyl acetate and butyl acetate; ethyl ether and propyl ether Ethers such as isopropyl ether, tetrahydrofuran and dioxane; halogenated hydrocarbons such as dichloromethane and chloroform; ketones such as acetone, methyl ethyl ketone, diethyl ketone and cyclohexanone; hexane, cyclohexane, petroleum ether, water and the like. Of these, ethanol, 1,3-butylene glycol, water, acetone, dichloromethane and the like are preferably used. These solvents can be used alone or in admixture of two or more. When mixing and using a solvent, what is necessary is just to adjust the mixing ratio of each solvent suitably according to the kind of solvent.

The extraction method is not particularly limited, and after adding a solvent (for example, ethanol) to Junsai, it is heated and heated to an extent that does not deactivate the activity of the active ingredient contained in the extract, A critical extraction method or the like can be applied as appropriate. Moreover, various well-known extraction methods, such as the immersion extraction method which immerses the bark of Junsai in a fixed amount of solvent and performs batch processing, and the continuous extraction method which continues sending a solvent continuously, are applicable.

An example of a specific extraction method is, for example, about 5 to 50 times the dry weight of Junsai, preferably about 10 to 40 times the extraction solvent, and dipped and heated (for example) The active ingredient can be extracted by stirring the solvent for about 1 to 6 hours. Of course, the type of solvent, the amount of solvent, the heating temperature, the heating time, etc. may be appropriately adjusted so that the active ingredient can be extracted efficiently.

After obtaining an extract from Junsai by the method described above, the extract can be obtained by solid-liquid separation from the residue, usually by conventional methods such as filtration and centrifugation. In the present invention, the obtained extract can be used as it is as a skin-beautifying agent, but since the activity may be low, it may be used as an extract or powder by appropriately concentrating or distilling off the solvent. . Furthermore, activity is obtained from the extract obtained by solvent fractionation operation using one or more organic solvents such as methanol, ethanol, propanol, butanol, dichloromethane, chloroform, ethyl acetate, toluene, hexane, benzene, and acetone. Fractions can be collected. Furthermore, if necessary, one or more suitable separation and purification means such as alumina column chromatography, silica gel chromatography, gel filtration chromatography, ion exchange chromatography, hydrophobic chromatography, and high performance liquid chromatography may be combined. It can also be purified.

In addition, isolation and identification of compound (1) from Junsai can be performed specifically as described in Example 1.

As described above, the compound (1) of the present invention can be isolated and purified from a natural product, but the production method of the compound is not limited to this, and is based on a known chemical synthesis method. The compound may be synthesized or produced by subjecting a substance obtained from a natural product to a raw material as a raw material.

Further, the compound (1) of the present invention has an action of inhibiting elastase activity and collagenase activity, as shown in the test examples described later, so that the disappearance of the beam due to deterioration, reduction or denaturation of collagen and elastin, wrinkles, Since it suppresses aging symptoms such as sagging, it can be used as a skin beautifying agent that can prevent skin aging.

In the skin beautifying agent of the present invention, at least one of compound (1) and Junsai extract can be used.

The ratio of the compound (1) contained in the skin beautifying agent of the present invention is not particularly limited as long as the skin beautifying agent exhibits a skin beautifying effect. Moreover, it may consist only of the extract of compound (1) or Junsai. Specific examples of the content of compound (1) include a proportion of 0.005% by weight or more in terms of the total amount in terms of dry weight. In the case of using an extract, the amount of the compound (1) contained in the extract may be used.

The shape of the skin beautifying agent of the present invention is not particularly limited. Examples thereof include powder, granule, tablet, pill, emulsion, liquid, suspension, concentrated extract, and dry extract.

The compound (1) of the present invention can be applied to various uses for the purpose of the above-mentioned effects. Applications include pharmaceuticals, reagents (for research and test kits), cosmetics, and skin care compositions for oral consumption (eg, foods, health foods, functional foods, supplements, foods for specific uses, foods for specific health use, pets) Food, and food compositions such as pet supplements).

The pharmaceutical composition containing the compound (1) of the present invention may contain an excipient, a carrier or an additive. The excipient, carrier and additive are not particularly limited as long as they are usually used and pharmaceutically acceptable, and the type and composition thereof can be appropriately changed.

Examples of the excipient include sodium chloride and sodium citrate, and examples of the carrier include sterilized water, physiological saline, and various buffers. Examples of additives include thickeners, buffer materials, preservatives, preservatives, and the like.

The dosage form of the pharmaceutical composition is not particularly limited and may be appropriately selected as necessary. For example, oral preparations such as tablets, capsules, granules, fine granules, powders; injections And parenterals such as suppositories and coating agents.

Oral preparations such as tablets, capsules, granules, fine granules, powders and the like are produced according to a conventional method using, for example, starch, lactose, sucrose, trehalose, mannitol, carboxymethylcellulose, corn starch, inorganic salts, The compounding quantity of the compound of this invention in these formulations is not specifically limited, It can set suitably. In this type of preparation, binders, disintegrants, surfactants, lubricants, fluidity promoters, corrigents, colorants, fragrances and the like can be used as appropriate.

In the case of a parenteral preparation, the dose is adjusted according to the age, weight, disease level, etc. of the patient, and for example, intravenous administration, intravenous infusion, subcutaneous injection, intramuscular injection or the like is used. This parenteral preparation is produced according to a conventional method, and distilled water for injection, physiological saline and the like can be generally used as a diluent. Furthermore, you may add a bactericidal agent, antiseptic | preservative, a stabilizer, etc. as needed. In addition, from the viewpoint of stability, this parenteral preparation can be frozen after filling into a vial or the like, the water can be removed by ordinary freeze-drying treatment, and the liquid preparation can be re-prepared from the freeze-dried product immediately before use. Further, if necessary, an isotonic agent, a stabilizer, an antiseptic, a soothing agent and the like may be added. Examples of other parenteral agents include liquid preparations for external use, coating agents such as ointments, suppositories for rectal administration, etc., and these are also produced according to conventional methods.

When the compound of the present invention is used in a cosmetic (cosmetic composition), the compound is generally used as a cosmetic ingredient, for example, a surfactant, an oil, a moisturizer, a film-forming agent, a pigment, and a fragrance. It can prepare by mix | blending in arbitrary combinations with. The form in particular is not restrict | limited, For example, it can be set as a lotion, a cream, a milky lotion, a gel agent, an aerosol, an essence, a pack, a washing | cleaning agent, a foundation, powdering, various makeup agents (lipstick, teak etc.).

The blending ratio of the compound blended in the cosmetic is not particularly limited as long as the expected effect of the compound can be obtained, but is usually about 0.0001 to 10% by weight. In the case of using an extract, it is sufficient to set an amount such that the compound (1) contained therein has the above ratio.

In addition to the compound (1) of the present invention and the Junsai extract containing the same, the cosmetics contain ingredients, oils, higher alcohols, fatty acids, and UV absorbers that are blended in cosmetics as long as the skin-beautifying effect is not impaired. , Powders, pigments, surfactants, polyhydric alcohols / sugars, polymers, physiologically active ingredients, solvents, antioxidants, fragrances, preservatives, and the like.
Examples are listed below, but the present invention is not limited to these examples.

(1) Examples of oil components Ester-based oil phase components: glyceryl tri-2-ethylhexanoate, cetyl 2-ethylhexanoate, isopropyl myristate, butyl myristate, isopropyl palmitate, ethyl stearate, octyl palmitate, isostearic acid Isocetyl, butyl stearate, butyl myristate, ethyl linoleate, isopropyl linoleate, ethyl oleate, isocetyl myristate, isostearyl myristate, isostearyl palmitate, octyldodecyl myristate, isocetyl isostearate, diethyl sebacate, adipine Diisopropyl acid, isoaralkyl neopentanoate, glyceryl tri (capryl / caprate), trimethylolpropane tri-2-ethylhexanoate, trimethylol triisostearate Propane, pentaerythritol tetra-2-ethylhexanoate, cetyl caprylate, decyl laurate, hexyl laurate, decyl myristate, myristyl myristate, cetyl myristate, stearyl stearate, decyl oleate, cetyl ricinoleate, isolaurate Stearyl, isotridecyl myristate, isocetyl myristate, isostearyl myristate, isocetyl palmitate, isostearyl palmitate, octyl stearate, isocetyl stearate, isodecyl oleate, octyldodecyl linoleate, octyldodecyl isoleate, isopropyl isostearate Cetostearyl 2-ethylhexanoate, stearyl 2-ethylhexanoate, hexyl isostearate, ethyleneglycol dioctanoate , Ethylene glycol dioleate, propylene glycol dicaprate, propylene glycol di (capryl / capric acid), propylene glycol dicaprylate, neopentyl glycol dicaprate, neopentyl glycol dioctanoate, glyceryl tricaprylate, glyceryl triundecylate, triisopalmitine Glyceryl acid, glyceryl triisostearate, octyldodecyl neopentanoate, isostearyl octanoate, octyl isononanoate, hexyl decyl neodecanoate, octyldodecyl neodecanoate, isocetyl isostearate, isostearyl isostearate, octyldecyl isostearate, polyglycerin oleic acid Ester, polyglycerol isostearate, dipropyl carbonate, charcoal Dialkyl (C12-18), triisocetyl citrate, triisoaralkyl citrate, triisooctyl citrate, lauryl lactate, myristyl lactate, cetyl lactate, octyl decyl lactate, triethyl citrate, acetyl triethyl citrate, acetyl tributyl citrate, Trioctyl citrate, diisostearyl malate, 2-ethylhexyl hydroxystearate, di-2-ethylhexyl succinate, diisobutyl adipate, diisopropyl sebacate, dioctyl sebacate, cholesteryl stearate, cholesteryl isostearate, cholesteryl hydroxystearate, olein Cholesteryl acid, dihydrocholesteryl oleate, phytosteryl isostearate, phytosteryl oleate, 12-stearoyl hydroxystearate Cetyl, 12-stearoyl-hydroxystearic acid stearyl 12-stearoyl-hydroxystearic acid isostearate, and the like.
Hydrocarbon oil phase components: squalane, liquid paraffin, α-olefin oligomer, isoparaffin, ceresin, paraffin, liquid isoparaffin, polybutene, microcrystalline wax, petrolatum and the like.
Animal and vegetable oils and their hydrogenated oils, and naturally occurring waxes: beef tallow, hydrogenated beef tallow, lard, hydrogenated tallow, horse oil, hydrogenated horse oil, mink oil, orange luffy oil, fish oil, hydrogenated fish oil, egg yolk oil and other animal oils and Its hardened oil, avocado oil, almond oil, olive oil, cacao butter, apricot 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, hardened rapeseed oil, palm kernel oil, hardened palm kernel oil, palm oil, hardened palm oil, peanut oil, hardened peanut oil, castor oil, hardened castor oil, sunflower oil, Vegetable oil such as grape seed oil, jojoba oil, hardened jojoba oil, macadamia nut oil, medhome oil, cottonseed oil, hardened cottonseed oil, coconut oil, hardened coconut oil and its hardened oil, beeswax, Acid number beeswax, lanolin, reduced lanolin, hydrogenated lanolin, liquid lanolin, carnauba wax and montan wax.
Silicone oil phase components: dimethylpolysiloxane, methylphenylpolysiloxane, methylcyclopolysiloxane, octamethylpolysiloxane, decamethylpolysiloxane, dodecamethylcyclosiloxane, methylhydrogenpolysiloxane, polyether-modified organopolysiloxane, dimethyl Siloxane / methylcetyloxysiloxane copolymer, dimethylsiloxane / methylstearoxysiloxane copolymer, alkyl-modified organopolysiloxane, terminal-modified organopolysiloxane, amino-modified silicone oil, amino-modified organopolysiloxane, dimethiconol, silicone gel, acrylic Examples include silicone, trimethylsiloxysilicic acid, and silicone RTV rubber.
Fluorine oil phase components: perfluoropolyether, fluorine-modified organopolysiloxane, fluorinated pitch, fluorocarbon, fluoroalcohol, fluoroalkyl / polyoxyalkylene co-modified organopolysiloxane, and the like.

(2) Examples of higher alcohols Lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, behenyl alcohol, 2-ethylhexanol, hexadecyl alcohol, octyldodecanol and the like can be mentioned.

(3) Examples of fatty acids Caprylic acid, capric acid, undecylenic acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, linoleic acid, linolenic acid, arachidic acid, arachidonic acid, behenic acid , Erucic acid, 2-ethylhexanoic acid and the like.

(4) Examples of UV absorbers Paraaminobenzoic acid, amyl paraaminobenzoate, ethyldihydroxypropyl paraaminobenzoate, glyceryl paraaminobenzoate, ethyl paraaminobenzoate, octyl paraaminobenzoate, octyldimethyl paraaminobenzoate, ethylene glycol salicylate, salicylic acid Octyl, triethanolamine salicylate, phenyl salicylate, butylphenyl salicylate, benzyl salicylate, homomenthyl salicylate, benzyl cinnamate, octyl paramethoxycinnamate, 2-ethylhexyl paramethoxycinnamate, mono-2-diparamethoxycinnamate Glyceryl ethylhexanoate, isopropyl paramethoxycinnamate, diethanolamine salt of paramethoxyhydrocinnamic acid, diisopropyl diisopropylcinnamic acid Stealth mixture, urocanic acid, ethyl urocanate, hydroxymethoxybenzophenone, hydroxymethoxybenzophenone sulfonic acid and its salts, dihydroxymethoxybenzophenone, 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-diphenyl acrylate, phenylbenzimidazole sulfate, 3- (4-methylbenzylidene) can Examples include full, isopropyldibenzoylmethane, 4- (3,4-dimethoxyphenylmethylene) -2, 5-dioxo-1-imidazolidinepropionate 2-ethylhexyl, and the like, polymer derivatives, silane derivatives, and the like.

(5) Examples of powders and pigments Red 104, Red 201, Yellow 4, Blue 1, Black 401 and other dyes, Yellow 4 AL lake, Yellow 203 BA lake and other lake dyes, nylon powder , Silk powder, urethane powder, Teflon (registered trademark) powder, silicone powder, polymethyl methacrylate powder, cellulose powder, starch, silicone elastomer spherical powder, polyethylene powder, yellow iron oxide, red iron oxide, black Colored pigments such as iron oxide, chromium oxide, carbon black, ultramarine and bitumen, white pigments such as zinc oxide, titanium oxide and cerium oxide, extender pigments such as talc, mica, sericite, kaolin and barium sulfate plate, titanium mica Pearl pigments such as barium sulfate, calcium carbonate, magnesium carbonate, aluminum silicate, metal salts such as magnesium silicate, Inorganic powders such as Rica and alumina, metal soaps such as aluminum stearate, magnesium stearate, zinc palmitate, zinc myristate, magnesium myristate, zinc laurate, zinc undecylenate, bentonite, smectite, boron nitride, etc. It is done. There are no particular restrictions on the shape of these powders (spherical, rod-like, needle-like, plate-like, irregular shape, flake-like, spindle-like, etc.) and particle diameter. These powders are 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 agent treatment, N-acylated lysine treatment, The surface treatment may or may not be performed in advance by polyacrylic acid treatment, metal soap treatment, amino acid treatment, lecithin treatment, inorganic compound treatment, plasma treatment, mechanochemical treatment or the like.

(6) Examples of surfactants Anionic surfactants: fatty acid soap, α-acyl sulfonate, alkyl sulfonate, alkyl allyl sulfonate, alkyl naphthalene sulfonate, alkyl sulfate, POE alkyl ether sulfate , Alkylamide sulfate, alkyl phosphate, POE alkyl phosphate, alkylamide phosphate, alkyloylalkyl taurine salt, N-acyl amino acid salt, POE alkyl ether carboxylate, alkyl sulfosuccinate, alkyl sulfoacetic acid Sodium, acylated hydrolyzed collagen peptide salt, perfluoroalkyl phosphate, etc. are mentioned.
Cationic surfactant: 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, and the like.
Amphoteric surfactants: carboxybetaine type, amide betaine type, sulfobetaine type, hydroxysulfobetaine type, amide sulfobetaine type, phosphobetaine type, aminocarboxylate type, imidazoline derivative type, amidoamine type and the like.
Nonionic surfactant: propylene glycol fatty acid ester, glycerin fatty acid ester, polyglycerin fatty acid ester, sorbitan fatty acid ester, POE sorbitan fatty acid ester, POE sorbitol fatty acid ester, POE glycerin fatty acid ester, POE alkyl ether, POE fatty acid ester, POE cured castor Oil, POE castor oil, POE / POP copolymer, POE / POP alkyl ether, polyether-modified silicone lauric acid alkanolamide, alkylamine oxide, hydrogenated soybean phospholipid, and the like.
Natural surfactant: lecithin, saponin, sugar surfactant and the like.

(7) Examples of polyhydric alcohols and sugars 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 sugar, sulfated trehalose, pullulan and the like. These chemically modified compounds can also be used.

(8) Examples of polymers Acrylic ester / methacrylic acid ester copolymer (plus size, manufactured by Kyoyo Chemical), vinyl acetate / crotonic acid copolymer (resin 28-1310, manufactured by NSC), vinyl acetate / croton Acid / vinyl neodecanate copolymer (28-2930, manufactured by NSC), methyl vinyl ether maleic acid half ester (Gantrez ES, manufactured by ISP), T-butyl acrylate / ethyl acrylate / methacrylic acid copolymer (rubymer) , BASF), vinyl pyrrolidone / vinyl acetate / vinyl propionate copolymer (Rubicol VAP, BASF), vinyl acetate / crotonic acid copolymer (Rubiset CA, BASF), vinyl acetate / croton Acid / vinyl pyrrolidone copolymer (Rubiset CAP, manufactured by BASF), vinyl pyrrolidone / acrylate copolymer (Rubiflex, BA SF), acrylate / acrylamide copolymer (Ultrahold, BASF), vinyl acetate / butyl maleate / isobornyl acrylate copolymer (Advantage, ISP), carboxy vinyl polymer (Carbopol, BF Goodrich), anionic polymer compounds such as acrylic acid / alkyl methacrylate copolymer (Pemulene, BF Goodrich), and acetic acid amphoteric products of dialkylaminoethyl methacrylate polymers (Yukaformer, Mitsubishi Chemical) Amphoteric polymer compounds such as octyl acrylate acrylate / hydroxypropyl acrylate / butylaminoethyl methacrylate copolymer (AMPHOMER, NSC), quaternized vinylpyrrolidone / dimethylaminoethyl methacrylate (GAFQUAT, ISP) , Methyl vinyl imidazolium chloride Cationic polymer compounds such as vinyl / vinylpyrrolidone copolymer (rubicoat, manufactured by BASF), polyvinylpyrrolidone (rubiscol K, manufactured by BASF), vinylpyrrolidone / vinyl acetate copolymer (rubiscol VA, manufactured by BASF) ), Nonionic polymer compounds such as vinylpyrrolidone / dimethylaminoethyl methacrylate copolymer (copolymer 937, manufactured by ISP), vinylcaprolactam / vinylpyrrolidone / dimethylaminoethyl methacrylate copolymer (copolymer VC713, manufactured by ISP), etc. There is. Cellulose or derivatives thereof, keratin and collagen or derivatives thereof, calcium alginate, pullulan, agar, gelatin, tamarind seed polysaccharide, xanthan gum, carrageenan, high methoxyl pectin, low methoxyl pectin, guar gum, gum arabic, crystalline cellulose, arabino Naturally derived polymer compounds such as galactan, gum karaya, gum tragacanth, alginic acid, albumin, casein, curdlan, gellan gum and dextran can also be suitably used.

(9) Examples of physiologically active ingredients Examples of physiologically active ingredients include substances that impart some physiological activity to the skin when applied to the skin. For example, whitening ingredients, anti-inflammatory agents, anti-aging agents, UV protection agents, slimming agents, tanning agents, antioxidants, moisturizers, blood circulation promoters, antibacterial agents, bactericides, desiccants, cooling agents, warming agents , Vitamins, amino acids, wound healing promoters, stimulation relieving agents, analgesics, cell activators, enzyme components, and the like. Examples of these suitable ingredients include, for example, ashitaba extract, avocado extract, amateur extract, altea extract, arnica extract, aloe extract, apricot extract, apricot kernel extract, ginkgo biloba extract, fennel extract, turmeric extract, oolong tea extract, ages Extract, Echinacea leaf extract, Ogon extract, Oat extract, Oen extract, Barley extract, Hypericum extract, Oyster extract, Dutch mustard extract, Orange extract, Seawater dried product, Seaweed extract, Hydrolyzed elastin, Hydrolyzed wheat powder, Hydrolyzed silk , Chamomile extract, Carrot extract, Kawara mugwort extract, Licorice extract, Calcade extract, Oyster extract, Kina extract, Cucumber extract, Guanosine, Gardenia extract, Kumazasa extract, Clarae Kiss, walnut extract, grapefruit extract, clematis extract, chlorella extract, mulberry extract, gentian extract, tea extract, yeast extract, burdock extract, fermented rice bran extract, rice germ oil, comfrey extract, collagen, bilberry extract, saicin extract, psycho extract Extract Kizuta extract, hawthorn extract, elderberry extract, yarrow extract, mint extract, sage extract, mallow extract, senki Sue extract, assembly extract, soybean extract, tiso extract, thyme extract, tea extract, clove extract, chigaya extract, chimpi extract, touki extract, toshinsen extract, tonin extract, spruce extract, dokudami extract, tomato extract, natto extract, carrot extract, garlic extract, Novara extract, hibiscus extract, bacmond extract, parsley extract, honey, hamamelis extract, parietalia extract, toad extract, bisabolol, loquat extract, dandelion extract, burdock extract, bukuro extract, butcher bloom extract, grape extract, propolis, loofah extract, Safflower extract, peppermint extract, bodaige extract, button extract, hop extract, pine extract, marronnier extract, mizubasho Kiss, Mukuroji extract, Melissa extract, Peach extract, Cornflower extract, Eucalyptus extract, Yukinoshita extract, Yokuinin extract, Artemisia extract, Lavender extract, Apple extract, Lettuce extract, Lemon extract, Lotus root extract, Rose extract, Rosemary extract, Roman chamomile extract And royal jelly extract.
Biopolymers such as deoxyribonucleic acid, mucopolysaccharide, sodium hyaluronate, sodium chondroitin sulfate, collagen, elastin, chitin, chitosan, hydrolyzed eggshell membranes, amino acids, hydrolyzed peptides, sodium lactate, urea, sodium pyrrolidonecarboxylate , Moisturizing ingredients such as betaine, whey, trimethylglycine, oily ingredients such as sphingolipid, ceramide, phytosphingosine, cholesterol, cholesterol derivatives, phospholipids, ε-aminocaproic acid, glycyrrhizic acid, β-glycyrrhetinic acid, lysozyme chloride, guaiazulene, Anti-inflammatory agents such as hydrocortisone, vitamin A, vitamin B2, vitamin B6, vitamin C, vitamin D, vitamin E, calcium pantothenate, biotin, nicotinamide, vitamin C ester, etc. Active ingredients such as vitamins, allantoin, diisopropylamine dichloroacetate, 4-aminomethylcyclohexanecarboxylic acid, antioxidants such as tocopherol, carotenoid, flavonoid, tannin, lignan, saponin, α-hydroxy acid, β-hydroxy acid, etc. Cell activators, blood circulation promoters such as γ-oryzanol and vitamin E derivatives, wound healing agents such as retinol and retinol derivatives, whitening such as arbutin, kojic acid, placenta extract, sulfur, ellagic acid, linoleic acid, tranexamic acid and glutathione Agents and the like.

(10) Examples of antioxidants Sodium bisulfite, sodium sulfite, erythorbic acid, sodium erythorbate, dilauryl thiodipropionate, tocopherol, tolyl biguanide, nordihydroguaiaretic acid, parahydroxyanisole, butylhydroxyanisole, dibutylhydroxy Examples include plant extracts having an antioxidant effect such as toluene, ascorbyl stearate, ascorbyl palmitate, octyl gallate, propyl gallate, carotenoid, flavonoid, tannin, lignan, saponin, apple extract and clove extract.

(11) Examples of solvents Purified water, ethanol, lower alcohol, ethers, LPG, fluorocarbon, N-methylpyrrolidone, fluoroalcohol, volatile linear silicone, next-generation chlorofluorocarbon and the like.

When the compound of the present invention is used in a food composition, the compound of the present invention is added to a food or drink as a raw material for various beverages or various processed products, or if necessary, excipients such as dextrin, lactose, starch, and flavorings, It can be processed into pellets, tablets, granules, etc. together with pigments, etc., or coated with gelatin and molded into capsules to produce food compositions such as health foods and health foods.

The blending ratio of the compound to be blended in the food composition is not particularly limited as long as the expected effect of the compound can be obtained, but the intake amount per time is usually about 0.0001 to 20 mg. In the case of using an extract, it is sufficient to set an amount such that the compound (1) contained therein has the above ratio.

These food compositions can be blended with various components depending on the type, for example, 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 ester, polyglycerin fatty acid ester, sucrose fatty acid ester, sorbitan fatty acid ester, propylene glycol fatty acid ester, Arabia Food materials such as gum, carrageenan, casein, gelatin, pectin, agar, vitamin Bs, nicotinic acid amide, calcium pantothenate, amino acids, calcium salts, pigments, fragrances and preservatives can be used. In addition, this skin-beautifying composition having a health maintenance function includes other antioxidants and health food ingredients such as antioxidants (reduced ascorbic acid (vitamin C), vitamin E, reduced glutatin). , Tocotrienol, vitamin A derivatives, lycopene, lutein, astaxanthin, zeaxanthin, fucoxanthin, uric acid, ubiquinone, coenzyme Q10, folic acid, garlic extract, allicin, sesamin, lignans, catechin, isoflavone, chalcone, tannins, flavonoids, coumarin , Isocoumarins, blueberry extract), health food ingredients (V. (vitamin) A, V.B1, V.B2, V.B6, V.B12, VC, VD, VE, VP, choline, niacin, pantothenic acid, Calcium folate, EPA, oligosaccharide, dietary fiber, squalene, soybean lecithin, taurine, donariella, pro Thein, octacosanol, DHA, egg yolk lecithin, linoleic acid, lactoferrin, magnesium, zinc, chromium, selenium, potassium, heme iron, oyster meat extract, chitosan, chitin oligosaccharides, collagen, chondroitin, turmeric, licorice, kokushi, keihi, hawthorn , Ginger, ganoderma, swordfish extract, suppon, licorice, kokushi, keihi, hawthorn, ginger, ganoderma, plantain, chamomile, chamomile, dandelion, hibiscus, honey, boren, royal jelly, lime, lavender, rosehip, rosemary, Sage, bifidobacteria, faecalis, lacris, wheat germ oil, sesame oil, perilla oil, soybean oil, medium chain fatty acid, agaricus, ginkgo biloba extract, turmeric, chondroitin, brown rice germ extract, litchi, onion, DHA, EPA, DPA甜 Tea, Cordyceps, Garlic, Bee, Papaya, Puaru, Propolis, Meguri Tree, Yabushitake, Royal Jelly, Saw Palmetto, Hyaluronic Acid, Collagen, Gabba, Harpseal Oil, Shark Cartilage, Glucosamine, Lecithin, Phosphatidylserine, Tabashi Carrot, mulberry leaf, soy extract, echinacea, sorghum, barley extract, olive leaf, olive fruit, gymnema, banaba, salacia, garcinia, chitosan, st jones wort, jujube, carrot, passion flower, broccoli, placenta, pearl barley, grape Seeds, peanut seed coat, bilberry, black cohosh, maria thistle, laurel, sage, rosemary, raffma, black vinegar, bitter gourd, maca, safflower, flax, oolong tea, flower spine, caffeine, capsaicin, xy Oligosaccharide, Glucosamine, Buckwheat, Citrus, Dietary fiber, Protein, Prunes, Spirulina, Barley young leaves, Nucleic acid, Yeast, Shiitake, Plum meat, Amino acid, Deep sea potato extract, Noni, Oyster meat, Suppon, Champignon, Psyllium, Acerola, Pineapple, banana, peach, apricot, melon, strawberry, raspberry, orange, fucoidan, mesimacob, cranberry, chondroitin sulfate, zinc, iron, ceramide, silk peptide, glycine, niacin, chesttree, L-cysteine, red wine leaf, millet, Horsetail, Biotin, Centella Asiatica, Lotus Cup, Pycnogenol, Japanese cypress, Rhubarb, Clove, Rosemary, Catechin, Pual, Citric Acid, Beer Yeast, Merirot, Black Zinger, Ginger, Gajutsu, Nattokina , Benikouji, Tocotrienol, Lactoferrin, Cinnamon, Persimmon Buckwheat, Cocoa, Yuzu Seed Extract, Perilla Seed Extract, Lychee Seed Extract, Evening Primrose Extract, Black Rice Extract, α-Lipoic Acid, Raw Coffee Bean Extract) .

The skin beautifying agent of the present invention comprises Junsai and / or an extract thereof as an active ingredient.
As the skin beautifying agent of the present invention, Junsai may be used as it is or as an extract. Furthermore, when using as it is, it is preferable to use what was grind | pulverized. Further, in some cases, dried Junsai can be used.

When the extract is used as the skin beautifying agent of the present invention, examples of the extraction solvent include alcohols such as methanol, ethanol, propanol and butanol; glycols such as 1,3-butylene glycol, glycerin and propylene glycol; ethyl acetate Esters such as butyl acetate; ethers such as ethyl ether, propyl ether, isopropyl ether, tetrahydrofuran and dioxane; halogenated hydrocarbons such as dichloromethane and chloroform; ketones such as acetone, methyl ethyl ketone, diethyl ketone and cyclohexanone; hexane, Cyclohexane, petroleum ether, water or the like can be used. Of these, ethanol, 1,3-butylene glycol, water, acetone, dichloromethane and the like are preferably used. These solvents can be used alone or in admixture of two or more. When mixing and using a solvent, what is necessary is just to adjust the mixing ratio of each solvent suitably according to the kind of solvent.

The extraction method is not particularly limited, and after adding a solvent (for example, ethanol) to Junsai, it is heated and heated to an extent that does not deactivate the activity of the active ingredient contained in the extract, A critical extraction method or the like can be applied as appropriate. Moreover, various well-known extraction methods, such as the immersion extraction method which immerses the bark of Junsai in a fixed amount of solvent and performs batch processing, and the continuous extraction method which continues sending a solvent continuously, are applicable.

The present invention can be applied to various purposes for the purpose described above. Applications include pharmaceuticals, reagents (for research and test kits), cosmetics, and skin care compositions for oral consumption (eg, foods, health foods, functional foods, supplements, foods for specific uses, foods for specific health use, pets) Food, and food compositions such as pet supplements). In addition, when using as these uses, the skin beautifying agent of the present invention can be made into a dosage form similar to the case where the above-mentioned compound (1) is used as a skin agent, and further, other compounding ingredients are skin beautifying agents. It can mix | blend similarly to the case where the said compound (1) is used.

Examples of the present invention will be described below.

Example 1: Isolation and structure determination of a new component (1) Isolation of a new component Extraction and isolation of a compound from Junsai were performed as follows.
That is, 50% w / w ethanol (20 kg) was added to dried Junsai (870 g), soaked overnight, and extracted at 80 ° C. for 3 hours. After filtration, the filtrate was concentrated to obtain Junsai extract (188 g, yield: 21.6%). The extract (100 g) was applied to a Diaion HP-20 (1 kg) column, and the resin was washed with 10% v / v methanol (6 L) and then with 30% methanol v / v (6 L). Elution was performed with 70% methanol (6 L), and the eluate was concentrated and dried to obtain a 70% methanol elution part (Fr. 70, 29 g) of HP-20. Fr. 70 (29 g) was subjected to ODS column chromatography (300 g), washed sequentially with 40% methanol (1.5 L) and 50% methanol (1 L), and eluted with 60% methanol (0.8 L). The eluate was concentrated and dried to obtain a 60% ethanol elution part (Fr. 70-60, 1.8 g) of ODS. Fr.70-60 (1 g) HPLC [Column: Inertosyl preparative ODS, 250 mm x 20 mm ID (GL Science), eluent: 60% methanol, detection: UV (220 nm), flow rate: 10 mL / min] And then purified by HPLC [column: RPAQUEOUS, 250 mm x inner diameter 20 mm (Nomura Chemical), eluent: 70% methanol, detection: UV (220 nm), flow rate: 10 mL / min] Pale yellow powder Fr. 70-60-3 (32 mg) was obtained.

(2) Determination of the structure of the new component Fr. 70-6-3 Fr. 70-6-3 obtained was measured for optical rotation, mass spectrometry, ultraviolet and infrared absorption spectra, ¹ H and ¹³ C-NMR spectra. went.
1) Physicochemical data Pale yellow powder. [A] _D ²¹ -52.0 ° (c = 0.1, MeOH). High resolution
MALDI-TOF-MS Calcd for C ₃₁ H ₂₈ O ₁₅ Na (M + Na) ⁺ :
663.1320; Found: 663.1327, UV [MeOH, nm, (loge)]: 255 (4.28), 329 (4.32).
IR (KBr, cm ^-1 ): 3400, 1689, 1655, 1605, 1514, 1016. ¹ H-NMR
(CD ₃ OD, 500 MHz) d: 3.35 (1H, m, 4``-H), 3.43 (1H, m, 3``-H), 3.45 (1H, m, 5``-H),
3.50 (1H, m, 2``-H), 3.88 (3H, s, 4'-OCH ₃ ), 4.28 (2H, m, 6``-H),
5.26 (1H, d, J = 7.3 Hz, 1``-H), 6.07 (1H, d, J = 2.0 Hz, 6-H), 6.12
(1H, d, J = 16.0 Hz, 8 '''-H), 6.25 (1H, d, J = 2.0, 8-H), 6.79 (1H,
d, J = 8.3 Hz, 5 '''-H), 6.80 (1H, d, J = 8.8 Hz, 5'-H), 6.91 (1H, dd,
J = 2.0, 8.3 Hz, 6 '''-H), 7.04 (1H, d, J = 2.0 Hz, 2'''-H), 7.39 (1H,
d, J = 16.0 Hz, 7 '''-H), 7.56 (1H, dd, J = 2.0, 8.8 Hz, 6'-H), 7.57
. (1H, d, J = 2.0 Hz, 2'-H) 13 C-NMR (CD 3 OD, 125 MHz) d c: 159.2 (C-2), 135.2 (C-3), 179.4 (C-4 ), 162.9 (C-5), 99.8 (C-6),
165.8 (C-7), 94.7 (C-8), 158.4 (C-9), 105.6 (C-10), 123.1 (C-1 '), 123.4 (C-2'),
115.9 (C-3 '), 149.8 (C-4'), 115.9 (C-5 '), 123.4 (C-6'), 56.5 (4'-OCH ₃ ),
103.8 (Glc-1 '), 75.6 (Glc-2'), 78.0 (Glc-3 '), 71.8 (Glc-4'), 75.9 (Glc-5 '),
64.3 (Glc-6``), 127.6 (C-1 "'), 146.8 (C-2"'), 149.3 (C-3 "'),
150.5 (C-4 "'), 116.4 (C-5"'), 124.2 (C-6 "'), 146.8 (C-7"'),
115.0 (C-8 "'), 168.8 (C-9"'). Positive-ion MALDI-TOF-MS: m / z
663 (M + Na) ⁺ .

2) Two-dimensional NMR
HMQC ( ¹ H-detected multiple quantum coherence spectrum) and HMBC
( ¹ H-detected multi-bond heteronuclear multiple quantum coherence
As a result of the analysis of the spectrum), a HMBC correlation was observed between the proton and carbon indicated by the arrow in FIG.

3) Identification of constituent sugars Sugars were identified by acid hydrolysis as follows.
Fr. 70-60-3 (2.0 mg) was dissolved in 5% sulfuric acid / 1,4-dioxane mixture (1: 1, v / v, 1.0 mL) according to the following literature 1) and reacted at 90 ° C for 3 hours. I let you. The reaction mixture was washed 3 times with ethyl acetate, and the aqueous layer was washed with Amberlite IRA-400 (OH-
form). After drying under reduced pressure, the residue was dissolved in pyridine (0.1 mL) containing L-cysteine methyl ester hydrochloride (0.5 mg) and heated at 60 ° C for 1 hour. A pyridine solution (0.1 mL) containing o-torylisothiocyanate (0.5 mg) was added to the reaction solution, and the mixture was further heated at 60 ° C for 1 hour. Reverse reaction HPLC of the reaction solution [Column: COSMOSIL 5C18-AR-II (Nacalai Tesque), 250 x 4.6 mm (5 mm) ID; Eluent: Acetonitrile-1% acetic acid (18:82, v / v); Detection: UV (250 nm); flow rate: 0.8 mL / min; column temperature: 35 ° C], the retention time of the monosaccharide of the derivative is the retention time of the standard product (D-glucose) (t _R :
D-glucose; 47.0 min, L-glucose; 42.7
min) and identified as D-glucose.
1) Tanaka, T .; Nakashima, T .; Ueda, T .; Tomii, K .; Kouno, I. Chem. Pharm. Bull. 2007, 55, 899-901.
Based on the above physicochemical data, Fr. 70-60-3 obtained from Junsai is JunsainosideA, which has D-glucose bonded to the 3rd position of the flavonoid tamarixetin and caffeic acid bonded to the 6 "position. It was found to be the compound (1)) represented by (1).

Example 2: Preparation of Junsai extract 30% w / w ethanol (20 kg) was added to dried Junsai (870 g) and immersed overnight, followed by extraction at 80 ° C for 3 hours. After filtration, the filtrate was concentrated to obtain Junsai extract of Example 2 (188 g, yield: 21.6%). The Junsai extract of Example 2 was confirmed to contain 0.12% (wt / wt) of compound (1) by HPLC.

Test Example 1: Evaluation of Elastase Inhibitory Action The samples of Example 1 were prepared in 1% DMSO so as to have final reaction concentrations of 10, 30, and 100 μg / mL, and 50 μL each was added to a 96-well plate. Next, 50 μL of DQ elastin (100 μg / mL) was added, and then 100 μL of elastase (0.2 U / mL) was added. Then, it measured using the fluorimeter (after 30 minutes, excitation wavelength 485nm, measurement wavelength 530nm). The result is shown in FIG. Further, the Junsai extract of Example 2 was similarly evaluated. The result is shown in FIG.

Results and Effects of Examples in Test Example 1
In the range of 30-100 μg / mL, compound (1) (Example 1) and Junsai extract containing it (Example 2) showed a significant elastase inhibitory effect (FIGS. 2 and 3). As described above, compound (1) and Junsai extract containing the same can effectively suppress the overexpression of elastase, and therefore, elastin is hardly denatured and gives elasticity and elasticity to the skin. It was confirmed that skin aging can be prevented.

Test Example 2: Evaluation of Collagenase Inhibitory Action Collagenase (0.25 mg / ml) dissolved in Tris-HCl buffer (0.1 M), the sample solution of Example 1 (concentration 10, 30, 100 μg / ml) and PZ-peptide ( 0.5
mg / ml) and mixed at 37 ° C. for 30 minutes. To this was added 25 mM citric acid as an enzyme reaction stop solution, and then the supernatant containing collagen decomposed by ethyl acetate was recovered. The absorbance (320 nm) of the supernatant was measured using a spectrophotometer, and the collagenase inhibition rate was calculated. The result is shown in FIG.
A similar test was performed on the Junsai extract of Example 2 (concentrations 10, 30, 100, 300, 1000 μg / ml). The result is shown in FIG.

Results and Effect of Example in Test Example 2 As shown in FIGS. 4 and 5, it was confirmed that the novel compound (1) and Junsai extract inhibit the collagenase enzyme in a concentration-dependent manner. Thus, it can be seen that the novel compound and Junsai extract containing the same can suppress the degradation of collagen, and therefore can give elasticity and elasticity to the skin and prevent skin aging.

Test Example 3: Evaluation of Hyaluronidase Inhibitory Action Activator solution (0.5 mg / mL Compound48 / 80 (SIGMA)) 100 μL and 4000NF / mL hyaluronidase (SIGMA) were added and incubated at 37 ° C. for 20 minutes. The sample solution of Example 1 (concentration 10, 30, 100 μg / ml) was added and incubated at 37 ° C. for 20 minutes. Subsequently, 0.8 mg / mL sodium hyaluronate (SIGMA) was added and incubated at 37 ° C. for 40 minutes, and then 100 μL of 0.4N sodium hydroxide solution was added and ice-cooled. Further, 100 μL of borate buffer (pH 9.1) was added, boiled for 3 minutes, and then ice-cooled. After ice cooling, 49 μL was dispensed into an Eppendorf tube, 210 μL of p-DAB reagent was added, and the mixture was incubated at 37 ° C. for 20 minutes. Thereafter, the absorbance at 585 nm was measured. The result is shown in FIG. A similar test was conducted on the Junsai extract of Example 2. The result is shown in FIG.

Results and Effects of Examples in Test Example 3 As shown in FIGS. 6 and 7, the novel compound (1) (Junsainoside A) and Junsai extract can inhibit the hyalonidase enzyme in a concentration-dependent manner. confirmed. Thus, it can be seen that the novel compound and Junsai extract containing the same can suppress the degradation of hyaluronic acid, and thus can prevent the skin from aging by suppressing the drying of the skin and the reduction of elasticity and elasticity. .

Test Example 4: Evaluation of tyrosinase inhibitory action
136 μL of 0.1 M phosphate buffer (pH: 6.8), 50 μL of 0.4 mg / mLL-DOPA (SIGMA) and 4 μL of the sample solution of Example 1 (concentration 10, 30, 100 μg / ml) dissolved in DMSO were mixed. To this, 10 μL (250 units / mL) of tyrosinase (derived from SIGMA, Mashrum) was added and allowed to react at room temperature for 5 minutes. Thereafter, the absorbance at 490 nm was measured. A similar test was conducted on the Junsai extract of Example 2.

Results and Effects of Examples in Test Example 4 As shown in FIGS. 8 and 9, it was confirmed that the novel compound (1) (Junsainoside A) and Junsai extract inhibit tyrosinase in a concentration-dependent manner. It was done. As a result, it was confirmed that the novel compound and Junsai extract containing the same suppress the oxidative polymerization reaction of tyrosine, suppress the degradation of the production of melanin, a dark brown pigment, and thereby have a whitening effect. .

Formulation examples of the skin beautifying agent (novel compound (1)) according to the present invention are shown. In addition, the following compounding examples do not limit the present invention.
Formulation Example 1: Cosmetic cream
Squalane 20.0wt%
Beeswax 5.0
Refined jojoba oil 5.0
Glycerin 5.0
Glycerol monostearate 2.0
Polyoxyethylene (20) sorbitan-
Monostearate 2.0
Skin care 2.0
Preservative appropriate amount
Perfume
Purified water residue
100.0wt%

Formulation Example 2: Lotion
Ethanol 5.0wt%
Glycerin 2.0
1,3-butylene glycol 2.0
Polyethylene oleyl ether 0.5
Sodium citrate 0.1
Citric acid 0.1
Skin care 0.1
Purified water residue
100.0wt%

Formulation Example 3: Body Gel
Macadamia nut oil 2.0wt%
Octyldodecyl myristate 10.0
Methylphenylpolysiloxane 5.0
Behenyl alcohol 3.0
Stearic acid 3.0
Batyl alcohol 1.0
Glyceryl monostearate 1.0
Tetraoleic acid polyoxyethylene sorbit 2.0
Hydrogenated soybean phospholipid 1.0
Ceramide 0.1
Retinol palmitate 0.1
Preservative appropriate amount
Centella extract 1.0
Skin care 1.0
1,3-butylene glycol 5.0
Purified water residue
100.0wt%

Formulation Example 4: Latex
Squalane 4.0wt%
Vaseline 2.5
Cetanol 2.0
Glycerin 2.0
Lipophilic glyceryl monostearate 1.0
Stearic acid 1.0
L-Arginine 1.0
Skin softener 0.5
Potassium hydroxide 0.1
Perfume
Purified water residue
100.0wt%

Formulation Example 5: Bath agent (liquid)
Propylene glycol 50.0wt%
Ethanol 20.0
Sodium sulfate 5.0
Skin softener 0.5
Lanolin 0.5
Avocado oil 0.5
Dye 1.5
Fragrance 22.0
100.0wt%
Formulation Example 6: Shampoo Polyoxyethylene alkyl ether sodium sulfate
(E.O2 mol) 15.0
Palm oil aliphatic diethanolamide 5.0
Glycerin 3.0
Skin care 0.4
Ethanol 5.0
Perfume and preservatives
Ion exchange water
Total 100wt%

Formulation Example 7: Hair Cream
Liquid paraffin 20.0wt%
Solid paraffin 3.0
Polyoxyethylene cetyl ether
(E.O15 mol) 2.0
Sorbitan sesquioleate 1.0
Skin softener 0.2
Ethanol 10.0
Potassium hydroxide 0.1
Glycerin 3.0
Perfume and preservatives
Total 100wt%

Formulation Example 8: Ointment
White beeswax 5.0wt%
Purified lanolin 5.0
Skin care 1.0
Fragrance 0.1
Vaseline residue
Total 100wt%

Formulation Example 9: Chewing gum
53.0wt% sugar
Gum base 20.0
Glucose 10.0
Minamata 16.0
Fragrance 0.5
Skin softener 0.5
100.0wt%

Formulation Example 10: Gummy
Reduced water tank 40.0wt%
Granulated sugar 20.0
Buto sugar 20.0
Gelatin 4.7
Water 9.68
Yuzu fruit juice 4.0
Yuzu Flavor 0.6
Dye 0.02
Skin care 1.0
100.0wt%

Formulation Example 11: Candy
50.0 wt% sugar
Minamata 33.0
Water 14.4
Organic acid 2.0
Fragrance 0.2
Skin care 0.4
100.0wt%

Formulation Example 12: Yogurt (hard / soft)
Milk 41.5wt%
Nonfat dry milk 5.8
Sugar 8.0
Agar 0.15
Gelatin 0.1
Lactic acid bacteria 0.005
Skin care 0.4
Perfume
Water residue
100.0wt%

Formulation Example 13: Soft drink
Fructose glucose liquid sugar 30.0wt%
Emulsifier 0.5
Skin softener 0.3
Perfume
Purified water residue
100.0wt%

Formulation Example 14: Tablet
76.4 wt% sugar
Glucose 19.0
Sucrose fatty acid ester 0.2
Skin softener 0.5
Purified water 3.9
100.0wt%

Formulation Example 15: Soft capsule
Brown rice germ oil 47.0wt%
Yuzu seed oil 40.0
Emulsifier 12.0
Skin care 1.0
100.0wt%

Formulation Example 16: Tablet
Lactose 54.0wt%
Crystalline cellulose 30.0
Starch degradation product 10.0
Glycerin fatty acid ester 5.0
Skin care 1.0
100.0wt%

  As described above, since the compound represented by the chemical formula (1) is novel and has high elastase and collagenase inhibitory activity, it is useful as a skin-beautifying agent containing this as an active ingredient, such as pharmaceuticals, cosmetics, and food compositions. Can be used.

Claims (8)

A compound represented by the following chemical formula (1).
An elastase inhibitor comprising the compound according to claim 1 as an active ingredient . A collagenase inhibitor comprising the compound according to claim 1 as an active ingredient . A hyaluronidase inhibitor comprising the compound according to claim 1 as an active ingredient . An elastase inhibitor containing Junsai extract as an active ingredient . A collagenase inhibitor comprising Junsai extract as an active ingredient . The hyaluronidase inhibitor which uses Junsai extract containing the compound of Claim 1 as an active ingredient . A composition for beautifying skin for oral intake containing the agent according to any one of claims 2 to 7 .