KR101657557B1 - Cosmetic composition comprising luteolin-6-c-fucopyranoside having skin whitening and anti-aging activity - Google Patents

Abstract

The present invention relates to a cosmetic composition containing luteolin-6-C-fucopyranoside having a skin whitening and anti-aging effect, which comprises a skin whitening agent containing luteolin-6-C-fucopyranoside as an active ingredient And an anti-aging cosmetic composition.
The luteolin-6-C-fucopyranoside of the present invention has a free radical scavenging activity, an inhibitory effect on elastase activity and a tyrosinase activity inhibiting effect, and the active ingredient of the cosmetic composition for improving wrinkle, . ≪ / RTI >

Description

TECHNICAL FIELD The present invention relates to a cosmetic composition containing luteolin-6-C-fucopyranoside having skin whitening and anti-aging effect,

The present invention relates to a cosmetic composition, more particularly to a cosmetic composition having a skin whitening and anti-aging effect.

In order to solve the fundamental cause of human aging, modern science is conducting research in various ways. Especially as the life becomes rich, there is an increasing interest in preventing the aging of the body as well as the internal aging. The best study of external aging is skin, and many studies using skin have played a major role in identifying human aging [GJ Fisher, The pathophysiology of photoaging of the skin. Cutis., 75, pp5-8, 2005]. Skin aging can be divided into two types: chronologic aging, which is accompanied by the progressive deterioration of the structure and function of the skin as time elapses, and the other is the exogenous aging (photoaging) And changes in skin texture due to long-term exposure to sunlight. This aging process causes the skin to become dry, wrinkled and lose its elasticity. Free radicals and reactive oxygen species are the most important treatments in skin aging research. They are naturally produced in vivo, but they are caused by exposure to sunlight or by contact with various chemicals [BA Jurkiewicz and GR Buettner, Ultraviolet light-induced free radicals in skin: an electron paramagnetic resonance study. Photochem. Photobiol., 59, pp 1-4, 1994). The free electrons and reactive oxygen species that are generated cause oxidative stress to the skin cells, and the substances generated during this process are considered to be the causative agents of melanin and wrinkle formation [Tomita, Y. and Seiji, M. Inactivation mechanism of tyrosinase in mouse melanoma. J. Dermatol., 4, pp. 245-249, 1977]. It has been shown that by exposing active oxygen to polymeric substrates (collagen, hyaluronic acid, elastin) that maintain skin elasticity, these substrates are sequentially cleaved [M. Yaar and BA Gilchrest, Aging versus photoaging: postulated mechanisms and effectors, J. Investig. Dermatol. Symp. Proc., 3, pp47-51, 1998]. On the other hand, pigmentation in the skin is caused by melanin production or melanocyte proliferation, and such pigmentation can be inhibited by various methods. Commonly used methods include various methods such as suppression of tyrosinase activity, an important enzyme of melanin synthesis, reduction of melanocyte function, reduction of melanin production through inhibition of autoxidation reaction, and suppression of inflammatory reaction such as erythema have. As a result, in order to prevent skin aging, it is necessary to inhibit the production of excess reactive oxygen species and to efficiently remove the generated active oxygen, and to inhibit enzymes that cause skin wrinkles, It is necessary to have an associated system [Goihman-Yahr, M., Skin aging and photoaging: an outlook. Clin. Dermatol. 14, pp 153-160, 1996].

Therefore, in order to find a component for blocking the oxidative action, delaying the aging action caused by the oxidative action, and inhibiting pigmentation of the skin, it has been found that an excellent antioxidative effect in ruteolin-6-C-fucopyranoside, The inventors of the present invention have confirmed that it is possible to solve the allergy and side effects, safety and stability caused by the synthetic materials obtained from natural plants, and to accomplish the present invention Respectively.

The following describes prior art techniques for cosmetic compositions having skin whitening and antiaging effects.

Korean Patent Publication No. 2011-0036299 (Applicant: AMOREPACIFIC Co., Ltd.) relates to a composition exhibiting an anti-aging effect and a whitening effect such as collagen decomposition.

Korean Utility Model No. 2011-0117376 (Applicant: AmorePacific Co., Ltd.) discloses a composition containing red soybean extract as an active ingredient. It contains collagen and inhibits the production of melanin by containing red soybean extract To a cosmetic composition and a health food composition which exhibit excellent anti-aging effect and skin whitening effect.

Korean Patent Registration No. 10-0731613 (Applicant: Cosmax Co., Ltd.) relates to a cosmetic composition having excellent whitening and antioxidative effect by using a stem extract of a mulberry tree native to Jeju Island.

The invention of Korean Patent Registration No. 10-0715485 (Applicant: Bioland Co., Ltd.) relates to a cosmetic composition containing a Nymphaea tetragona extract having wrinkle improvement, elasticity enhancement, antioxidant and whitening effect, more specifically, An antioxidant and whitening cosmetic composition comprising a water extract of Root seedlings having radical scavenging activity, elastase activity inhibiting activity and tyrosinase activity inhibiting activity as active ingredients.

It is an object of the present invention to provide a cosmetic composition for skin whitening and antiaging which contains a compound having an effect of improving wrinkles, improving elasticity, antioxidation and whitening effect.

In order to achieve the above object, the present invention provides a cosmetic composition for skin whitening and anti-aging comprising luteolin-6-C-fucopyranoside as an active ingredient.

The luteolin-6-C-fucopyranoside of the present invention has a free radical scavenging activity, an inhibitory effect on elastase activity and a tyrosinase activity inhibiting effect, and is effective for improving wrinkles, improving elasticity, antioxidant and whitening cosmetic composition . ≪ / RTI >

BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 shows a reaction scheme for obtaining the luteolin-6-C-fucopyranoside of the present invention.

Hereinafter, the present invention will be described in detail.

The present invention provides a skin whitening and anti-aging cosmetic composition containing, as an active ingredient, luteolin-6-C-fucopyranoside having the following formula:

[Chemical Formula 1]

The above-mentioned luteolin-6-C-fucopyranoside may be synthetically prepared by a synthetic method and starting materials and / or intermediates known in the art of organic chemistry, or may be extracted from natural products.

Figure 1 shows a reaction scheme for obtaining luteolin-6-C-fucopyranoside from natural products, especially Kummerowia striata.

The EtOAc fractions are obtained from the following steps:

1) extracting the knot grass by adding an extraction solvent, preferably an alcohol or a mixture of water and alcohol;

2) filtering the extract of step 1);

3) concentrating the filtered extract of step 2) under reduced pressure and drying;

4) suspending the extract of step 3) in water, and then sequentially extracting with hexane, methylene chloride, ethyl acetate, and butanol to obtain respective fractions; And

5) Concentrating the ethyl acetate (EtOAc) fraction obtained from step 4) under reduced pressure and drying.

In this method, the knot grass of step 1) may be used without limitation such as cultivated or commercially available.

The extraction solvent is preferably an alcohol or a mixture of water and alcohol. As the alcohol, C ₁ to C ₄ lower alcohol is preferably used, more preferably methanol and ethanol, and most preferably ethanol. As the extraction method, any extraction known in the art can be used, but preferably by cold extraction. It is preferable to add the extraction solvent to the dry knot full amount by 1 to 20 times and extract. The extraction time is preferably 1 hour to 30 days, preferably 1 to 15 days, more preferably 15 to 30 hours, but is not limited thereto. In addition, the extraction number is preferably 3 to 5 times, more preferably 3 times, but is not limited thereto. Alternatively, the extract of the present invention can be prepared using a heat extraction method. More specifically, the extract can be prepared by heating at 40 to 100 DEG C for 2 to 20 hours.

In the above method, it is preferable to use a vacuum decompression concentrator or a vacuum rotary evaporator for the decompression concentration in step 3), but it is not limited thereto. The drying is preferably performed under reduced pressure, vacuum drying, boiling, spray drying or freeze drying, but is not limited thereto.

The EtOAc fractions thus obtained can be separated and purified by chromatography. It is preferred that the chromatography is carried out at least once on reversed phase or silica gel column chromatography. Dichloromethane / methanol (50: 1 to 1: 1) or methanol / water (20% MeOH to 100% MeOH) may be used as the mobile phase. At this time, the solvent is eluted and separated by gradient elution using a gradient method in which the solvent to be used is sequentially raised from non-polar to polar or polar to non-polar, and the inhibitory effect of the thiocinase enzyme activity of the collected separates is measured, Fraction can be obtained. The active fractions showing inhibitory effect on thyrosinase activity can be further purified by chromatography to separate and purify and determine the structure of luteolin-6-C-fucopyranoside, which shows an inhibitory effect on thyrosinase enzyme activity .

The present inventors have confirmed that luteolin-6-C-fucopyranoside has a free radical scavenging activity, an inhibitory effect on elastase activity, and an inhibitory activity on tyrosinase activity. Accordingly, the present invention can be applied to cosmetics and facial cleansers for wrinkle improvement, elasticity enhancement, antioxidative and whitening effects, and the like. The luteolin-6-C-fucopyranoside The ranoside can be used in an amount of 0.001 to 90% by weight, preferably 0.01 to 10% by weight, more preferably 0.01 to 5% by weight based on the total weight of the cosmetic composition.

Examples of products to which the present composition can be added include cosmetics such as various creams, lotions, and skins, and cleansing, cleansing agents, soaps, treatments, and essences.

The cosmetic composition of the present invention comprises a composition selected from the group consisting of water-soluble vitamins, oil-soluble vitamins, high molecular weight peptides, polymeric polysaccharides, sphingolipids and seaweed extracts.

The water-soluble vitamin is not particularly limited as long as it can be compounded in cosmetics. Preferably, vitamin B, vitamin B2, vitamin B6, pyridoxine, pyridoxine hydrochloride, vitamin B12, pantothenic acid, nicotinic acid, nicotinic acid amide, folic acid, vitamin C, (Sodium thiamine hydrochloride, sodium ascorbic acid salt, etc.) or derivatives thereof (sodium ascorbic acid-2-phosphate salt, ascorbic acid-2-phosphate magnesium salt, etc.) can also be added to water-soluble vitamins . The water-soluble vitamin can be obtained by a conventional method such as a microorganism conversion method, a purification method from a culture of a microorganism, an enzymatic method, or a chemical synthesis method.

Usable vitamins include vitamins such as vitamin A, carotene, vitamin D2, vitamin D3, vitamin E (d1-alpha tocopherol, d-alpha tocopherol, d-alpha tocopherol) Alpha-tocopherol vitamin E, DL-pantothenyl alcohol, D-pantothenyl alcohol, pantothenyl ethyl laurate, and the derivatives thereof (palmitic acid ascorbin, stearic acid ascorbic acid, dipalmitic acid ascorbin, dl-alpha tocopherol acetate, Ether, etc.) are also included in the usable vitamins used in the present invention. Usability The vitamins can be obtained by a conventional method such as a microorganism conversion method, a purification method from a culture of a microorganism, an enzyme or a chemical synthesis method.

The polymeric peptide may be any compound as long as it can be compounded in cosmetics, and examples thereof include collagen, hydrolyzed collagen, gelatin, elastin, hydrolyzed elastin, and keratin. The polymeric peptide can be obtained by a conventional method such as purification from a culture broth of a microorganism, an enzymatic method, or a chemical synthesis method, or it can be purified from natural products such as ducks such as pigs and cows and silk fiber of silkworms.

The polymeric polysaccharide may be any compound as long as it can be incorporated in cosmetics, and examples thereof include hydroxyethyl cellulose, xanthan gum, sodium hyaluronate, chondroitin sulfate or a salt thereof (sodium salt, etc.). For example, chondroitin sulfate or a salt thereof can be usually purified from mammals or fish.

Sphingo lipids may be any as long as they can be incorporated into cosmetics, and preferable examples thereof include ceramides, phytosphingosine and sphingoglycolipids. Sphingoid lipids can be purified from ordinary mammals, fish, shellfish, yeast or plants by conventional methods or can be obtained by chemical synthesis.

Seaweed extract may be any compound that can be incorporated into cosmetics. Preferably, the seaweed extract may be a grape extract, a red mildew extract, or a green algae extract, or may be a color guanine, arginic acid, sodium alginate, Potassium sulfate and the like are also included in the seaweed extract used in the present invention. Seaweed extract can be obtained from seaweed by a conventional method.

The cosmetic of the present invention may be blended with other essential ingredients, if necessary, in combination with the essential ingredients. Examples of the compounding ingredients that may be added include organic solvents such as a preservative component, a moisturizer, an emollient, a surfactant, an organic and inorganic pigment, an organic powder, an ultraviolet absorbent, a preservative, a bactericide, an antioxidant, a plant extract, a pH adjuster, A blood circulation accelerator, a cold agent, an antiperspirant agent, and purified water. Examples of the oil retaining component include ester-based oil retaining, hydrocarbon-based oil retaining, silicone-based oil retaining, fluoric oil retaining, animal retention and plant retention. Examples of ester-based fats include glyceryl tri-2-ethylhexanoate, cetyl 2-ethylhexanoate, isopropyl myristate, butyl myristate, isopropyl palmitate, ethyl stearate, octyl palmitate, isostearyl isostearate, Butyl isopropyl myristate, isopropyl myristate, isopropyl myristate, isopropyl myristate, isopropyl myristate, isopropyl myristate, butyl, ethyl linoleate, isopropyl linoleate, ethyl oleate, isosilyl myristate, isostearic acid isostearyl, isostearyl palmitate, octyldodecyl myristate, Trimethylol propane, triisostearic acid trimethylol propane, tetra 2-ethylhexanoic acid pentaerythritol tetra (2-ethylhexanoate) , Decyl caprylate, decyl laurate, hexyl laurate, decyl myristate, myristyl myristate, myristine acid stearate, stearyl stearate, decyl oleate, ricinoleic acid Isopropyl palmitate, isostearyl stearate, isostearyl stearate, isodecyl oleate, octyldodecyl oleate, octyldodecyl linoleate, isopropyl stearate, isopropyl stearate, isopropyl stearate, Ethylhexanoate, stearyl 2-ethylhexanoate, stearyl 2-ethylhexanoate, hexyl isostearate, ethylene glycol dioctanoate, ethylene glycol dioleate, propylene glycol dicaprate, di (capryl, capric acid) propylene glycol, Propylene glycol dicaprylate, propylene glycol dicaprylate, neopentyl glycol dicaprate, neopentyl glycol dioctanoate, glyceryl tricarboxylate, glyceryl triunsaturated acid, glyceryl triisopalmitate, glyceryl triisostearate, octyl dodecanoate Silane, octanoic acid, octanoic acid, octanoic acid, octanoic acid octanoate, octanoic acid octanoate, octanoic acid octanoate, octanoic acid octanoate, octanoic acid octanoate, octanoic acid octanoate, Octyldecyl lactate, octyldecyl lactate, polyglycerin isostearic acid ester, triisocetyl citrate, triisocylic citrate, triisooctyl citrate, lauryl lactate, myristyl lactate, octyldecyl lactate, citric acid tri Ethylhexyl stearate, diethyl stearate, ethyl stearate, ethyl stearate, ethyl stearate, ethyl stearate, ethyl stearate, ethyl stearate, But are not limited to, dioctyl sebacate, cholesteryl stearate, cholesteryl isostearate, cholesteryl hydroxystearate, cholesteryl oleate, dihydrocholestearyl oleate, pitostearyl isostearate, Stearoyl hydroxystearic acid isostearyl, 12-stearoyl hydroxystearic acid stearyl, Stearoyl hydroxystearic acid, and esters such as 12-stearoyl hydroxystearic acid and saxate.

 Examples of the hydrocarbon hydrocarbon-based fats include hydrocarbon fats and oils such as squalene, liquid paraffin, alpha-olefin oligomer, isoparaffin, ceresin, paraffin, floating isoparaffin, polybutene, microcrystalline wax and vaseline.

Examples of silicone based oils include polymethyl silicone, methylphenyl silicone, methyl cyclopolysiloxane, octamethylpolysiloxane, decamethylpolysiloxane, dodecamethylcyclosiloxane, dimethylsiloxane-methylcetyloxysiloxane copolymer, dimethylsiloxane-methylstarchoxysiloxane copolymer, alkyl Modified silicone oils, and amino-modified silicone oils.

Examples of the fluorine-based oil include perfluoropolyether and the like. Examples of animal or vegetable oils include avocado oil, almond oil, olive oil, sesame oil, rice bran oil, new flower oil, soybean oil, corn oil, rape oil, apricot kernel oil, palm kernel oil, palm oil, castor oil, , Corn oil, palm oil, palm oil, cucumber nut oil, wheat germ oil, rice germ oil, shea butter, coltsfoot colostrum, marker daisy nut oil, mead home oil, egg oil, , Canned wax, carnauba wax, liquid lanolin, hardened castor oil, and the like.

Examples of the moisturizing agent include water-soluble low-molecular moisturizing agents, oil-soluble molecular moisturizing agents, water-soluble polymers, and oil-soluble polymers. Examples of the water-soluble low-molecular moisturizing agent include serine, glutamine, sorbitol, mannitol, sodium pyrrolidone-carboxylate, glycerin, propylene glycol, 1,3-butylene glycol, ethylene glycol, polyethylene glycol B Glycol (polymerization degree n = 2 or more), polyglycerin B (polymerization degree n = 2 or more), lactic acid, lactic acid salt and the like.

Examples of the lipid-soluble low-molecular moisturizing agent include cholesterol and cholesterol ester.

Examples of the water-soluble polymer include carboxyvinyl polymer, polyaspartic acid, tragacanth, xanthan gum, methylcellulose, hydroxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, carboxymethylcellulose, water-soluble chitin, chitosan, dextrin have. Examples of the oil-soluble polymer include polyvinylpyrrolidone / eicosene copolymer, polyvinylpyrrolidone / hexadecene copolymer, nitrocellulose, dextrin fatty acid ester, and polymer silicone.

Examples of the emollients include long chain acyl glutamic acid cholesteryl ester, hydroxystearic acid cholesteryl, 12-hydroxystearic acid, stearic acid, rosin acid, and lanolin fatty acid cholesteryl ester.

Examples of the surfactant include nonionic surfactants, anionic surfactants, cationic surfactants, and amphoteric surfactants. Examples of the nonionic surfactant include self emulsifying monostearic acid glycerin, propylene glycol fatty acid ester, glycerin fatty acid ester, polyglycerin fatty acid ester, sorbitan fatty acid ester, POE (polyoxyethylene) sorbitan fatty acid ester, POE sorbit fatty acid ester, POE-POP fatty acid ester, POE alkyl ether, POE fatty acid ester, POE hardened castor oil, POE castor oil, POE.POP (polyoxyethylene.polyoxypropylene) copolymer, POE.POP alkyl ether, polyether- Acid alkanolamides, alkylamine oxides, hydrogenated soybean phospholipids, and the like. Examples of the anionic surfactant include fatty acid soap, alpha-acylsulfonate, alkylsulfonate, alkylarylsulfonate, alkylnaphthalenesulfonate, alkylsulfate, POE alkyl ether sulfate, alkylamide sulfate, alkyl phosphate, POE alkyl ginseng salt, Alkylsulfosuccinates, sodium alkylsulfoacetates, acylated hydrolyzed collagen peptide salts, perfluoroalkyl phosphate esters, and the like can be given. have. Examples of the cationic surfactant include alkyl trimethyl ammonium chloride, stearyl trimethyl ammonium chloride, stearyl trimethyl ammonium bromide, cetostearyl trimethyl ammonium chloride, distearyl dimethyl ammonium chloride, stearyl dimethyl benzyl ammonium chloride, behenyl trimethyl ammonium chloride, Benzalkonium, diethylaminoethylamide stearate, dimethylaminopropylamide stearate, quaternary ammonium salts of lanolin derivatives, and the like. Examples of the amphoteric surfactant include carboxybetaine, amidebetaine, sulfobetaine, hydroxysulfobetaine, amidosulfobetaine, phosphobetaine, aminocarboxylate, imidazoline derivative, amideamine Amphoteric surfactants and the like. Examples of the organic and inorganic pigments include inorganic pigments such as silicic acid, silicic anhydride, magnesium silicate, talc, sericite, mica, kaolin, Bengala, clay, bentonite, titanium mica, titanium oxide, bismuth chloride, zirconium oxide, magnesium oxide, Inorganic pigments such as calcium sulfate, barium sulfate, magnesium sulfate, calcium carbonate, magnesium carbonate, iron oxide, chromium oxide, chromium oxide, chromium hydroxide, But are not limited to, polyamide, polyester, polypropylene, polystyrene, polyurethane, vinyl resin, urea resin, phenol resin, fluororesin, silicon resin, acrylic resin, melamine resin, epoxy resin, polycarbonate resin, Silk powder, cellulose, CI Pigment Yellow, CI Pigment Orange, and composite pigments of inorganic pigments and organic pigments thereof.

As the organic powder, metallic soap such as calcium stearate; Metal alkyl phosphates such as zinc sodium cetylate, zinc laurylate and calcium lauryl laurate; Acylamino acid polyvalent metal salts such as N-lauroyl-beta-alanine calcium, N-lauroyl-beta-alanine zinc and N-lauroylglycine calcium; Amidosulfonic acid multivalent metal salts such as N-lauroyl-taurine calcium and N-palmitoyl-taurine calcium; Such as N-epsilon-lauroyl-L-lysine, N-epsilon-palmitoylidene, N-alpha-paratyylnitine, N-alpha-lauroyl arginine, Acyl basic amino acids; N-acylpolypeptides such as N-lauroylglycylglycine; Alpha-amino fatty acids such as alpha-aminocaprylic acid, alpha-aminoaurauric acid, and the like; Polyethylene, polypropylene, nylon, polymethylmethacrylate, polystyrene, divinylbenzene-styrene copolymer, ethylene tetrafluoride, and the like. Examples of ultraviolet absorbers include paraaminobenzoic acid, ethyl parnamobenzoate, amyl paranobenzoate, octyl paranobenzoate, ethyleneglycol salicylate, phenyl salicylate, benzyl salicylate, benzyl salicylate, butylphenyl salicylate, homomenthyl salicylate, benzyl cinnamate , Octyl methoxycinnamate, dioctyl methoxycinnamate, mono-2-ethylhexane glyceryl dipyrromethoxycinnamate, isopropyl paratumoxycinnamate, diisopropyl-diisopropyl cinnamate ester mixture, Carninoic acid, ethyl urocanoate, hydroxymethoxybenzophenone, hydroxymethoxybenzophenone sulfonic acid and salts thereof, dihydroxymethoxybenzophenone, sodium dihydroxymethoxybenzophenone disulfonate, dihydroxybenzophenone , 4-tert-butyl-4'-methoxydibenzoylmethane, 2,4,6-trianylino-p- (carbo-2'-ethylhexyl-1'-oxy) -1 , 3,5-tri There may be mentioned 2- (2-hydroxy-5-methylphenyl) benzotriazole. Examples of the bactericide include hinokitiol, trichloroacid, trichlorohydrodiphenyl ether, crohexidine gluconate, phenoxyethanol, resorcin, isopropylmethylphenol, azulene, salicylic acid, zinc filitione, benzalkonium chloride, No. 301, mononitro, eicosyl sodium, undecylenic acid, and the like. Examples of the antioxidant include butylhydroxy anisole, gallic acid propyl, and eicosorbic acid. Examples of the pH adjusting agent include citric acid, sodium citrate, malic acid, sodium malate, fumaric acid, sodium pyrophosphate, succinic acid, sodium succinate, sodium hydroxide, sodium monohydrogenphosphate and the like. Examples of the alcohol include higher alcohols such as cetyl alcohol. In addition, any of the above components may be blended within the range not to impair the objects and effects of the present invention, but is preferably 0.01 to 5% by weight, more preferably 0.01 to 5% Preferably 0.01 to 3% by weight.

The cosmetic of the present invention may take the form of a solution, an emulsion, a viscous mixture or the like. The ingredients contained in the cosmetic composition of the present invention may contain, in addition to the above-mentioned extracts, the components conventionally used in cosmetic compositions, such as stabilizers, solubilizers, vitamins, pigments and fragrances, And a carrier. The cosmetic composition of the present invention can be prepared in any formulations conventionally produced in the art, and examples thereof include emulsions, creams, lotions, packs, foundations, lotions, essences, and hair cosmetics. Specifically, the cosmetic composition of the present invention can be used as a skin lotion, a skin softener, a skin toner, an astringent, a lotion, a milk lotion, a moisturizing lotion, a nutrition lotion, a massage cream, a nutrition cream, a moisturizing cream, a hand cream, a foundation, , Packs, soaps, cleansing foams, cleansing lotions, cleansing creams, body lotions and body cleansers. When the formulation of the present invention is a paste, a cream or a gel, an animal fiber, a plant fiber, a wax, a paraffin, a starch, a tracer, a cellulose derivative, polyethylene glycol, silicon, bentonite, silica, talc or zinc oxide . When the formulation of the present invention is a powder or a spray, lactose, talc, silica, aluminum hydroxide, calcium silicate or polyamide powder may be used as a carrier component. In the case of a spray, in particular, chlorofluorohydrocarbons, Propane / butane or dimethyl ether. When the formulation of the present invention is a solution or emulsion, a solvent, a solvent or an emulsifier is used as a carrier component, and examples thereof include water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, 1,3-butyl glycol oil, glycerol aliphatic ester, polyethylene glycol or fatty acid esters of sorbitan. When the formulation of the present invention is a suspension, a carrier such as water, a liquid diluent such as ethanol or propylene glycol, a suspension such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester, Cellulose, aluminum metahydroxide, bentonite, agar or tracant, etc. may be used. When the formulation of the present invention is an interface-active agent-containing cleansing, it is preferable to use, as the carrier component, aliphatic alcohol sulfate, aliphatic alcohol ether sulfate, sulfosuccinic acid monoester, isethionate, imidazolinium derivative, methyltaurate, sarcosinate, Amide ether sulfate, alkylamidobetaine, aliphatic alcohol, fatty acid glyceride, fatty acid diethanolamide, vegetable oil, linolenic derivative or ethoxylated glycerol fatty acid ester.

Hereinafter, the present invention will be described in detail with reference to Examples, Experimental Examples and Production Examples.

However, the following Examples, Experimental Examples and Preparation Examples are merely illustrative of the present invention, and the contents of the present invention are not limited by Examples, Experimental Examples and Production Examples.

Example 1 Preparation of Luteolin-6-C-fucopyranoside of the Present Invention

5 kg of knot grass was weighed, powdered and then extracted with ethanol.

Ethanol solvent (70% EtOH), 5 times the volume of the sample, was added and extracted three times at 75 ° C. The obtained extract was filtered, concentrated by using a vacuum concentrator, and then lyophilized (FDU-2100, EYELA, Japan).

The obtained concentrated concentrate was fractionated into a water (H ₂ O) layer and a hexane (HX, H) layer, and then the water layer was fractionated into a dichloromethane (CH ₂ Cl ₂ , C) , And then the remaining water layer was separated again into a layer of ethyl acetate (EtOAc, E) and a layer of water. The remaining water layer was further fractionated into a n-butanol (n-BuOH, B) layer and an aqueous layer, and the ethyl acetate layer thus obtained was concentrated under reduced pressure.

Subsequently, the concentrated ethyl acetate layer was chromatographed on a mobile phase using a gradient gradient of 50: 1 to 1: 1 dichloromethane / methanol and methanol / water in 20% methanol to 100% methanol to give luteolin- 6-C-fucopyranoside was obtained.

Compound ^{1 - 1 H-NMR (700} MHz, CD 3 OD): 7.38 (1H, dd, J = 1.4 & 8.6, H-1 '), 7.37 (1H, d, J = 1.4Hz, H-6') , 6.90 (1H, d, J = 8.6 Hz, H-2), 6.57 (1H, s, H- Glc-1), 4.21-3.30 (6H, m, Glc-2-6); ^{13 C-NMR (175 MHz,} CDCl 3): 166.3 (C-2), 103.9 (C-3), 184.0 (C-4), 162.0 (C-5), 109.2 (C-6), 164.8 (C (C-1), 114.1 (C-2), 147.0 (C-3), 151.0 2), 75.2 (Glc-3), 72.5 (Glc-4), 116.7 (C-5 '), 120.3 , 71.7 (Glc-5), 20.7 (Glc-6).

The fractionation process of luteolin-6-C-fucopyranoside is shown in Fig.

<Experimental Example 1> Determination of whitening effect of luteolin-6-C-fucopyranoside by measuring in vitro tyrosinase inhibitory activity

Mushroom tyrosinase inhibition assay was used to confirm the tyrosinase enzyme activity inhibitory effect of the luteolin-6-C-fucopyranoside obtained in Example 1. 10 μl of the sample and 20 μl of the sample were added to 170 μl of a reaction mixture of 1 mM L-tyrosine, 50 mM potassium phosphate buffer (pH 6.5), and distilled water at a ratio of 10: 10: 9 The reaction solution containing Mushroom Tyrosinase aqueous solution (1000 units / mL) was incubated at 25 ° C for 30 minutes. Then, the amount of dopachrome generated at 490 nm using a microplate reader was measured by absorbance. As a positive control, kojic acid, which is known as inhibitor of tyrosinase enzyme activity, was used. The percentage formula of inhibition of tyrosinase enzyme activity was as follows.

[Equation 1]

Tyrosinase activity inhibitory effect (%) = {1- (A-B) / C} 100

(A: sample absorbance, B: color control absorbance, C: control absorbance)

The inhibitory activity of tyrosinase enzyme activity of luteolin-6-C-fucopyranoside calculated by the above formula is shown in Table 1 below.

sample IC ₅₀ (ug / ml) Luteolin-6-C-fucopyranoside 96.68 Arbutin 629.3 Kojic acid 35.3

As can be seen from the above Table 1, the IC ₅₀ value was 96.68 ㎍ / mL for luteolin-6-C-fucopyranoside, which was significantly higher than arbutin (629.3 ㎍ / mL) used as a positive control And showed high enzyme activity inhibition.

These results demonstrate that the ruteolin-6-C-fucopyranoside of the present invention effectively inhibits tyrosinase expression, and consequently inhibits melanin synthesis, thereby preventing whitening as well as treating diseases caused by melanin deposition .

&Lt; Formulation Example 1 >

Nutrition lotion was prepared by a conventional method according to the composition shown in Table 2 below.

ingredient Content (% by weight) The compound of Example 1 5.0 Squalane 5.0 Wax 4.0 Polysorbate 60 1.5 Sorbitan sesquioleate 1.5 Liquid paraffin 0.5 Caprylic / capric triglyceride 5.0 glycerin 3.0 Butylene glycol 3.0 Propylene glycol 3.0 Carboxyvinyl polymer 0.1 Triethanolamine 0.2 Preservative, coloring, fragrance Suitable amount Purified water Suitable amount Sum 100

&Lt; Formulation Example 2 >

Nutrition creams were prepared according to the compositions shown in Table 3 below in a conventional manner.

ingredient Content (% by weight) The compound of Example 1 5.0 Polysorbate 60 1.5 Sorbitan sesquioleate 0.5 PEG60 hardened castor oil 2.0 Liquid paraffin 10.0 Squalane 5.0 Caprylic / capric triglyceride 5.0 glycerin 5.0 Butylene glycol 3.0 Propylene glycol 3.0 Triethanolamine 0.2 Preservative, coloring, fragrance Suitable amount Purified water Suitable amount Sum 100

&Lt; Formulation Example 3 >

Packs were prepared in a conventional manner according to the composition shown in Table 4 below.

ingredient Content (% by weight) The compound of Example 1 5.0 Polyvinyl alcohol 13.0 Sodium carboxymethyl cellulose 0.2 glycerin 5.0 Alatoin 0.1 ethanol 6.0 PEG12 nonyl phenyl ether 0.3 Polysorbate 60 0.3 Preservative, coloring, fragrance Suitable amount Purified water Suitable amount Sum 100

&Lt; Formulation Example 4 > Lotion

Lotions were prepared in a conventional manner according to the composition shown in Table 5 below.

ingredient Content (% by weight) The compound of Example 1 10.0 Squalane 3.50 Cetyl alcohol 3.00 glycerin 3.00 Glyceryl stearate 2.50 Cetyl octanoate 6.00 Sorbitan sesquioleate 1.50 PEG-100 stearate 1.00 Sheer butter 0.50 Carbomer 0.30 Triethanolamine 0.30 Methyl paraben 0.20 Imidazolidinyl urea 0.15 Propylparaben 0.10 Combination fragrance 0.10 Purified water Suitable amount (up to 100)

Claims (10)

A cosmetic composition for skin whitening and anti-aging comprising luteolin-6-C-fucopyranoside represented by the following formula (1) as an active ingredient:
[Chemical Formula 1]

The method of claim 1, wherein the luteolin -6-C- Foucault-pyrano side it is a knot grass hexane C ₁ ~ C ₄ alcohols, or C ₁ ~ C ₄ after extraction with alcohol and water mixture, water, dichloromethane, Ethyl acetate and butanol to obtain an ethyl acetate fraction which is successively extracted with ethyl acetate and butanol. The process according to claim 2, wherein after obtaining the extracted ethyl acetate fractions, the mobile phase is eluted with a concentration gradient elution method using dichloromethane / methanol of 50: 1 to 1: 1 and methanol / water of 20% methanol to 100% The composition for skin whitening and anti-aging according to claim 1, The cosmetic composition for skin whitening and anti-aging according to claim 1, wherein the luteolin-6-C-fucopyranoside is contained in an amount of 0.01 to 10% by weight based on the total weight of the composition. The cosmetic composition for skin whitening and antiaging according to claim 1, wherein the composition is in the form of a skin. The cosmetic composition for skin whitening and antiaging according to claim 1, wherein the composition is in the form of a nutritional lotion. The cosmetic composition for skin whitening and antiaging according to claim 1, wherein the composition is in the form of a nutritional cream. The method of claim 1, wherein the luteolin -6-C- Foucault-pyrano side knot pull the C ₁ ~ C ₄ alcohols, or C ₁ ~ C ₄ alcohol and water mixture is extracted with hexane after this, and extracted sequentially with butanol Ethylacetate fractions are obtained in a cosmetic composition for skin whitening and anti-aging. The method of claim 1, wherein the luteolin -6-C- Foucault-pyrano side knot pull the C ₁ ~ C ₄ alcohols, or C ₁ ~ C ₄ alcohol and water mixture was then extracted with this, dichloromethane, ethyl acetate and butanol To obtain an ethyl acetate fraction which is successively extracted with water. The method of claim 1, wherein the luteolin -6-C- Foucault-pyrano side knot pull the C ₁ ~ C ₄ alcohols, or C ₁ ~ C then extracted with ₄ alcohol and water mixture it hexane, dichloromethane, ethyl acetate And ethyl acetate fractions sequentially extracted with butanol are obtained.

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