KR20180003920A - Composition for skin improvement containing liriopesides B - Google Patents

Abstract

The present invention relates to a cosmetic composition containing liriopesides B. More specifically, the present invention relates to a cosmetic composition ensuring outstanding effects such as skin-whitening effects, skin elasticity improvement effects, wrinkle amelioration effects, or moisturizing effects. The composition of the present invention excellently reduces total amounts of melanin even in low concentration, and also exhibits effects of promoting collagen synthesis and inhibiting activities of collagenase and elastase while having anti-saccharification and antioxidant functions, thereby being used as cosmetic compositions for skin moisturization, wrinkle amelioration, elasticity improvement, and skin-whitening. In addition, the composition containing liriopesides B can be used as food compositions and quasi-drug compositions.

Description

[0001] The present invention relates to a cosmetic composition comprising a lilyopiside ratio,

More particularly, the present invention relates to a cosmetic composition having excellent effects such as skin whitening, skin elasticity enhancement, wrinkle improvement, moisturizing, and the like, and more particularly, to a cosmetic composition containing liriopeseides B. The present invention also relates to a food composition and a quasi-drug composition comprising a lyriopapeide ratio.

Commonly known whitening ingredients include substances inhibiting tyrosinase enzyme activity such as kojic acid or arbutin, hydroquinone, vitamin C (L-ascorbic acid) or derivatives thereof, various plant extracts . By inhibiting the synthesis of melanin pigment, they can brighten the skin tone to realize skin whitening, and it is possible to improve skin hypercholesterolemia such as stain or freckles due to ultraviolet rays, hormones or heredity. However, when applied to skin, there is a problem that the use amount is limited due to safety problems such as irritation and redness, or the effect is insignificant, so that a practical effect can not be expected.

Collagen is a major substrate protein produced in the fibroblasts of the skin and exists in extracellular epilepsy. Its important functions are mechanical durability of the skin, resistance of connective tissues and binding force of tissues, support of cell adhesion, cell division and differentiation (Induction of growth of an organism or wound healing) are known. Such collagen is reduced by photoaging by age and ultraviolet irradiation, and collagenase activity, which degrades collagen, promotes collagen reduction. This is known to be closely related to the formation of wrinkles in the skin.

In addition, Elastin fiber forms crosslinks with collagen and is a skin constituent important for wrinkle formation involved in skin elasticity. The deficiency and aggregation of elastin fibers and the dramatic increase in the activity of the elastin degrading enzyme Elastase have been found to be one of the causes of skin wrinkles. Elastase is the only enzyme capable of degrading elastin, and inhibition of it is known to be able to radically reduce wrinkles.

In addition, collagen and elastin fibers are substrate proteins that play an important role in moisture retention in the dermal layer. These protein proteins adsorb moisture and increase the water holding capacity inside the structure to maintain the skin's proper moisture content. And it is known to be involved in maintaining the elasticity of the skin.

At present, retinoids, adenosine, animal placenta-derived proteins, chlorella extract, and the like are known as cosmetics for improving skin elasticity and improving wrinkles. The best known retinol promotes collagen synthesis and is a substance that inhibits elastase enzyme, but it is unstable. When applied to the skin, there is a limitation in usage due to safety problems such as irritation and redness, and chlorella extract has little effect, It is known that it is difficult to expect the effect of improving elasticity and wrinkle.

Glycation generally refers to a reaction in which a simple sugar such as glucose or fructose forms a covalent bond to a protein or fat that occurs without involvement of the enzyme. The accumulation of the final glycation product converts the protein into a harder and more brittle state, and the glycated collagen prevents the collagen from forming a proper structure in the extracellular matrix of the dermal layer, thereby losing skin elasticity and promoting wrinkle formation Dyer, DG et al, The Journal of Clinical Investigation, 9, p. 2463, 1993). In addition, the final saccharification product produced by the saccharification is a brownish substance, which is considered to be a cause of yellowing of the face gradually as the skin ages, and as the specific final saccharification product accumulates, the reflection light reflected from the skin is reduced (Hiroshi, O. et al., Skin Research and Technology, 15, p. 496, 2009). Aminoguanidine, pyridoxamine, and aspirin are known to inhibit glycosylation. However, these substances are limited in their use due to the safety of the skin, There is a problem that can not be expected.

On the other hand, liriopesides B is a steroid-based compound having molecular formula C ₃₉ H ₆₂ O ₁₂ , molecular weight of 722.9, and lirioprolioside B or 25 ( S ) -Lucosianin- -O- [beta] -D-fucopyranoside-3-O- alpha -L-raminopyranosyl. Liriopep latyphylla or Liriope spicata and is known to dissolve in solvents such as pyridine, methanol and ethanol.

Under these circumstances, the inventors of the present invention conducted studies on a substance having excellent whitening skin whitening, skin elasticity enhancement, wrinkle improvement and moisturizing effect, and the composition containing the lilyophenate ratio as an effective ingredient was found to be effective for reducing total melanin, , Elastase and collagenase activity, antihalation and antioxidative effects, and has completed the cosmetic composition, food composition and quasi-drug composition utilizing the same.

Korean Patent Publication No. 10-2012-0037202

An object of the present invention is to provide a cosmetic composition comprising the lyriophosphate ratio represented by the general formula (1) or a cosmetically acceptable salt thereof as an active ingredient.

Specifically, it is an object of the present invention to provide a cosmetic composition for skin whitening comprising a lilyopiside ratio represented by the general formula (1) or a cosmetically acceptable salt thereof as an active ingredient.

More specifically, the object of the present invention is to provide a cosmetic composition for skin elasticity enhancement or wrinkle improvement comprising the lyriophosphate ratio represented by the formula (1) or a cosmetically acceptable salt thereof as an active ingredient.

More specifically, the object of the present invention is to provide a cosmetic composition for moisturizing the skin comprising the lyriophosphate ratio represented by the general formula (1) or a cosmetically acceptable salt thereof as an active ingredient.

Another object of the present invention is to provide a food composition containing the lyriophosphate ratio represented by the general formula (1) or a pharmaceutically acceptable salt thereof as an active ingredient.

Another object of the present invention is to provide a quasi-drug composition comprising the lyriophosphate ratio represented by the general formula (1) or a pharmaceutically acceptable salt thereof as an active ingredient.

The present invention provides cosmetic compositions comprising the compound represented by the formula (I) or a cosmetically acceptable salt thereof in order to solve the above-mentioned problems and to achieve the object of the present invention.

Specifically, as one embodiment of the present invention, there is provided a cosmetic composition for skin whitening comprising, as an active ingredient, a lyriophosphate ratio represented by the general formula (1) or a cosmetically acceptable salt thereof.

As another aspect of the present invention, there is provided a cosmetic composition for skin elasticity enhancement or wrinkle improvement comprising the lyriophosphate ratio represented by the formula (1) or a cosmetically acceptable salt thereof as an active ingredient.

As another embodiment of the present invention, there is provided a cosmetic composition for moisturizing the skin comprising the lyriophosphate ratio represented by the general formula (1) or a cosmetically acceptable salt thereof as an active ingredient.

In another aspect of the present invention, there is provided a food composition comprising as an active ingredient a lyriophosphate ratio or a pharmaceutically acceptable salt thereof.

As another embodiment of the present invention, there is provided a quasi-drug composition comprising as an active ingredient a lyriophosphate ratio or a pharmaceutically acceptable salt thereof.

The present invention provides a composition comprising a non-lyophilate compound represented by the following general formula (I) or a salt thereof.

 [Chemical Formula 1]

In the present invention, " liriopesides B " is a compound represented by the above formula (1) and having the molecular formula C ₃₉ H ₆₂ O ₁₂ , a molecular weight of 722.9 and containing liriopesides B, ratio (B lirioprolioside) or 25 (S) - loose nose Janine -1-O-β-D- Foucault-pyrano side -3-O-α-L- ramno pyrazol-shi (25 (S) -ruscogenin-1 -O -β-Dfucopyranoside-3-O-α-L- rhamnopyranosy , which is an organic compound classified as a steroid contained in Liriopep latyphylla or Liriope spicata .

The maekmundong is Liriope platyphylla , Liriopep It is widely distributed throughout the world as a perennial plant species of the family Liliaceae, also called latyphylla or Liriope spicata . Leaves gather from short, coarse rootstocks to form an abandon, and often the root ends grow like peanuts. Stems stand straight and 20 to 50 cm high. Leaves are straw-green, linear, 30-40 cm in length, 8-12 mm in butterflies, and the bottom is like a leaflet. It is known to contain components such as beta-sitosterol, stigmasterol, steroid saponin, and amino acids.

The present invention is not particularly limited to the method for obtaining the lyopiazide ratio, and may be chemically synthesized by a method known in the art, or a commercially available material may be used.

The ratios of the lyophores of formula (I) of the present invention may be present in unsolvated form as well as solvated form including form of hydrate, ethanol and the like. The lyophopside ratios of the present invention may exist in crystalline or amorphous form, and all such physical forms are included within the scope of the present invention.

In the composition according to the present invention, it is preferable that the content of the lyriophosphate is 0.0001 to 10% by weight based on the total weight of the composition.

The present invention provides a cosmetic composition comprising the compound represented by Formula 1 or a cosmetically acceptable salt thereof.

Specifically, the present invention can provide a cosmetic composition for skin whitening, skin elasticity enhancement, wrinkle improvement, or skin moisturizing comprising the compound represented by the above formula (1) or a cosmetically acceptable salt thereof.

In the present invention, " skin whitening " refers to not only brightening the skin tone by inhibiting the synthesis of melanin pigment but also improving skin hypercholesterolemia due to ultraviolet rays, hormones or heredity, such as spots or freckles. In one embodiment of the present invention, the compound of Formula 1 was added to mouse melanoma cells (B-16 mouse melanoma cells) and the total amount of melanin was measured. As a result, in the test group to which the compound was added, And the composition containing the compound represented by the formula (1) can be used for skin whitening purposes (Experimental Example 1).

In the present invention, " skin elasticity enhancement " is intended to alleviate the degree to which the skin is stuck or stretched. Elastic fibers composed of elastin are present together with collagen fibers called collagen. Skin elasticity is maintained. In the present invention, " wrinkle improvement " refers to inhibiting or inhibiting the generation of wrinkles on the skin, or alleviating already formed wrinkles.

In one embodiment of the present invention, the compound represented by the formula (1) was added to a culture solution of human fibroblasts and then the collagen synthesis promoting effect was examined. As a result, in the test group to which the compound was added, And showed similar collagen synthesis effect (Experimental Example 2). In addition, in an embodiment of the present invention, it was found that the compounds of formula (1) inhibited the elastase activity and the collagenase activity, and as a result, in the test group supplemented with the lyriophosphate ratio, (Example 3 and 4). ≪ tb > < TABLE > Thus, it was confirmed that the composition containing the compound represented by Chemical Formula 1 can be used for skin elasticity enhancement or wrinkle improvement.

In the present invention, " skin moisturizing " means increasing moisture in the skin and maintaining a moist state. Skin moisturizing effect can help to improve wrinkles and elasticity of skin. In one embodiment of the present invention, the compound represented by the formula (1) exhibited excellent collagen synthesis, elastase and collagenase activity inhibition, and the composition containing the compound represented by the formula (1) (Experimental Examples 2 to 4).

The cosmetic composition according to the present invention can be used as a cosmetic composition in the form of a solution, an ointment for external use, a cream, a foam, a nutritional lotion, a softening water, a pack, a soft water, an emulsion, a makeup base, But are not limited to, emulsions, emulsions, pastes, gels, lotions, powders, soaps, surfactant-containing cleansing, oils, powder foundations, emulsion foundations, wax foundations, patches and sprays It is not.

In addition, the cosmetic composition of the present invention may further comprise at least one cosmetically acceptable carrier to be incorporated in a general skin cosmetic composition, and examples thereof include oil, water, a surfactant, a moisturizer, A thickening agent, a chelating agent, a coloring matter, an antiseptic, a perfume, and the like may be appropriately compounded, but the present invention is not limited thereto.

The cosmetically acceptable carrier to be contained in the cosmetic composition of the present invention varies depending on the formulations.

When the formulation of the present invention is an ointment, a paste, a cream or a gel, the carrier component may be an animal oil, a vegetable oil, a wax, a paraffin, a starch, a tracer, a cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc, zinc oxide Mixtures of these may be used.

When the formulation of the present invention is a powder or a spray, lactose, talc, silica, aluminum hydroxide, calcium silicate, polyamide powder or a mixture thereof may be used as the carrier component, Propellants such as fluorohydrocarbons, propane / butane or dimethyl ether.

When the formulation of the present invention is a solution or emulsion, a solvent, a dissolving agent or an emulsifying agent 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 may be used, in particular fatty acid esters of cottonseed oil, peanut oil, corn oil, olive oil, castor oil and sesame oil, glycerol aliphatic esters, polyethylene glycols or sorbitan may be used have.

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, Crystalline cellulose, aluminum metahydroxide, bentonite, agar or tracant, etc. may be used.

When the formulation of the present invention is a soap, an alkali metal salt of a fatty acid, a fatty acid hemiester salt, a fatty acid protein hydrolizate, isethionate, a lanolin derivative, an aliphatic alcohol, a vegetable oil, glycerol, .

The present invention also provides a food composition comprising the compound represented by the above-mentioned formula (1) or a pharmaceutically acceptable salt thereof.

Specifically, the present invention can provide a skin-whitening, skin elasticity-improving or wrinkle-improving or skin moisturizing food composition containing the compound represented by the above-mentioned formula (1) or a pharmaceutically acceptable salt thereof. The non-lyophilic compounds represented by Formula 1, skin whitening, skin elasticity enhancement, wrinkle improvement, and skin moisturization are as described above. The food composition may be used in the form of a health functional food, but is not limited thereto.

The compound represented by the formula (1) or a pharmaceutically acceptable salt thereof contained in the food composition of the present invention may be contained in the form of an animal or plant including the compound represented by the formula (1), an extract thereof, a fraction thereof or a processed product thereof. The composition may also include a food-acceptable food-aid additive in addition to the active ingredient.

In the present invention, the term "food-aid additive " means a component that can be added to foods in a supplementary manner, and is appropriately selected and used by those skilled in the art as added to produce health functional foods of each formulation. Examples of food-aid additives include flavors such as various nutrients, vitamins, minerals (electrolytes), synthetic flavors and natural flavors, colorants and fillers, pectic acid and its salts, alginic acid and its salts, organic acids, , a pH adjusting agent, a stabilizer, a preservative, a glycerin, an alcohol, and a carbonating agent used in a carbonated drink. However, the types of the food auxiliary additives of the present invention are not limited by these examples.

A health functional food may be included in the food composition of the present invention. In the present invention, the term "health functional food" refers to a food prepared and processed in the form of tablets, capsules, powders, granules, liquids and rings using raw materials and components having useful functions in the human body. The term "functional" as used herein means that the structure and function of the human body have a beneficial effect on health uses such as controlling nutrients or physiological actions. The health functional food of the present invention can be prepared by a method commonly used in the art and can be prepared by adding raw materials and ingredients that are conventionally added in the art. In addition, the formulations of the above health functional foods may also be manufactured without limitations as long as they are acceptable as health functional foods. The food composition of the present invention can be manufactured in various formulations, and unlike general pharmaceuticals, it has an advantage of being free from side effects that may occur when a food is used as a raw material for a long period of time, and is excellent in portability. Health functional foods can be ingested as an adjunct to improve skin whitening, skin elasticity or wrinkle improvement, or skin moisturizing effect.

The form of the health functional food of the present invention is not limited, and may include all foods in the conventional meaning, and may be used in combination with terms known in the art such as functional foods. In addition, the health functional food of the present invention can be prepared by mixing other suitable auxiliary ingredients, which may be included in food, according to the selection of a person skilled in the art, and known additives. Examples of foods that can be added include dairy products, such as meat, sausage, bread, chocolates, candies, snacks, confectionery, pizza, ramen, other noodles, gums, ice cream, various soups, drinks, tea, Vitamin complex, and the like, and can be prepared by adding to juice, tea, jelly, juice and the like prepared by using the compound represented by the formula (1) according to the present invention as a main component. It also includes foods used as feed for animals.

The present invention also provides a quasi-drug composition comprising the compound represented by Formula 1 or a pharmaceutically acceptable salt thereof.

In particular, the present invention can provide a quasi-skin composition for skin whitening, skin elasticity enhancement or wrinkle improvement, or skin moisturizing composition comprising the compound represented by the above-mentioned formula (1) or a pharmaceutically acceptable salt thereof. The non-lyophilic compounds represented by Formula 1, skin whitening, skin elasticity enhancement, wrinkle improvement, and skin moisturization are as described above.

The quasi-drug composition of the present invention may further contain a pharmaceutically acceptable carrier, excipient or diluent as necessary in addition to the above components. The pharmaceutically acceptable carrier, excipient or diluent is not limited as long as the effect of the present invention is not impaired, and examples thereof include fillers, extenders, binders, wetting agents, disintegrants, surfactants, lubricants, sweeteners, .

Representative examples of the pharmaceutically acceptable carrier, excipient or diluent of the present invention include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, maltitol, starch, gelatin, glycerin, acacia rubber, alginate, calcium phosphate, calcium Methyl cellulose, polyvinyl pyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate, mineral oil, propylene glycol, polyethylene glycol, vegetable oils such as sodium carboxymethylcellulose, , Injectable ester, witepsol, macrogol, tween 61, cacao paper, and laurie paper.

When the compound represented by the formula (1) of the present invention is used as a quasi-drug, it may further contain one or more active ingredients exhibiting the same or similar functions. For example, it may contain known skin whitening, elasticity enhancement, wrinkle improvement, and moisturizing ingredients. The addition of skin whitening, elasticity enhancement, wrinkle improvement, and moisturizing ingredients may further enhance skin whitening, elasticity enhancement, wrinkle enhancement and moisturizing effect of the composition of the present invention. When the above ingredients are added, skin safety, easiness of formulation, and stability of effective ingredients can be considered according to the combined use. The quasi-drug composition may be a whitening ingredient known in the art, such as a substance inhibiting tyrosinase enzyme activity such as kojic acid, arbutin, hydroquinone, L-ascorbic acid; Retinoic acid, TGF, proteins from animal placenta, betulinic acid and chlorella extract, as skin elasticity, wrinkle or moisturizing ingredients known in the art; And derivatives thereof, and various plant extracts. ≪ Desc / Clms Page number 2 > The additional ingredient may be contained in an amount of 0.0001% by weight to 10% by weight based on the total weight of the composition, and the content may be adjusted according to requirements such as skin safety, ease of formulation of the compound represented by Formula 1 will be.

The quasi-drug composition of the present invention can be exemplified by a disinfectant cleaner, a shower foam, a softener solution, a wet tissue, a coating agent, and the like. The formulation method, dosage, usage method, And the like.

In addition, the compound represented by Formula 1 of the present invention can be used for skin whitening, skin elasticity enhancement or wrinkle improvement, or skin moisturizing method including a step of applying the composition to the individual's skin. The subject includes, without limitation, mammals including rats, livestock, humans, and the like.

The cosmetic composition comprising the lilyopheneside ratio of the present invention or a cosmetically acceptable salt thereof as an active ingredient is excellent in skin whitening, improving elasticity or wrinkle, and skin moisturizing effect. Specifically, the composition of the present invention is excellent in anti-glycation and antioxidative effect, exhibits an excellent melanin total amount reduction effect even at a low concentration, has excellent collagen synthesis promoting effect, elastase and collagenase activity inhibiting effect, Or as a cosmetic composition for improving wrinkles and skin moisturizing. Further, the composition containing the lyopoideptide ratio of the present invention can be used as a food composition and a quasi-drug composition.

Hereinafter, the constitution and effects of the present invention will be described in more detail through examples. These embodiments are only for illustrating the present invention, and the scope of the present invention is not limited by these embodiments.

Reference Example 1: liriopesides B Substance Information

[Chemical Formula 1]

Material name: Liriopesides B

CAS No. : 87425-34-1

Molecular formula: C ₃₉ H ₆₂ O ₁₂

Molecular weight: 722.9

Where to buy: Chengdu Herbpurify CO., LTD

Experimental Example 1: Whitening effect according to the effect of decreasing total amount of melanin at the cell level

The compound of Chemical Formula 1 was added to the culture solution of mouse B-16 mouse melanoma cells to determine the whitening effect by measuring the total amount of melanin at the cellular level (Lotan R., Lotan D. Cancer Res . 40: 3345-3350, 1980). To evaluate the toxicity of melanoma cells in rats before the experiment, whitening evaluation was performed by selecting a concentration that is not toxic.

The compound of formula (1) was added to the culture solution to a final concentration of 1 ppm or 10 ppm, and the control group, arbutin, was added to 100 ppm, and the mixture was treated with B-16 melanoma cells and cultured for 3 days.

Cells were then trypsinized, detached from the culture, centrifuged, and then melanin was extracted. The removed cells were incubated with 1 ml of sodium hydroxide solution (1N concentration), boiled for 10 minutes to dissolve melanin, and the amount of melanin produced was measured by measuring the absorbance at 400 nm using a spectrophotometer.

The amount of melanin was measured by the absorbance of 1 × 10 ⁶ cells per unit cell, and the total amount of melanin relative to the control group was calculated as the inhibition rate (%). The results are summarized in Table 1 below.

Reduction effect of the total amount of melanin at the cellular level according to the concentration (number of repeats = 3) sample Melanin production (abs) Inhibition rate (%) Control group (DMSO, 10 ppm) 0.33 - Positive control (arbutin, 100 ppm) 0.228 31.06 The compound of formula (1) (10 ppm) 0.273 17.34 The compound of formula (1) (1 ppm) 0.301 8.65

As can be seen from the results in Table 1, the compound of Chemical Formula 1 shows a significantly lower total amount of melanin even at a low concentration of 10 ppm as compared with the positive control arbutin, and can be used for skin whitening purposes And it was found.

Experimental Example  2: promoting the synthesis of type I collagen in human fibroblasts

The compound of Chemical Formula 1 was added to the culture medium of human-derived fibroblasts to confirm the promoting effect of type I collagen synthesis at the cellular level. The collagen synthesis was quantitated using a PICP EIA kit (Procollagen Type I C-Peptide Enzyme Immuno Assay Kit). To measure the amount of collagen synthesis, the compound of formula (I) was added to a culture medium of fibroblasts (DMEM medium) and cultured for 48 hours. The culture broth was taken and the degree of type 1 collagen synthesis was measured at low concentration using a PICP EIA kit using a spectrophotometer And measured at 450 nm.

For the comparison of the effects, the degree of collagen synthesis was measured in the same manner for the samples in which the culture medium of the untreated fibroblasts (negative control) and vitamin C (positive control) were added to a final concentration of 52.85 μg / ml. The increase rate of collagen production was calculated as a ratio of relative collagen production to the control group, and the results are shown in Table 2 below.

Promoting collagen synthesis of the compound of formula (1) (number of repeats = 4) sample Type 1 collagen production (ng / ml) Growth rate (%) Negative control group 150.2 - The positive control (vitamin C, 50 ppm) 200.01 33.16 The compound of formula (1) (1 ppm) 179.4 12.40 The compound of formula (1) (10 ppm) 218.5 38.52

As can be seen from the results in Table 2, when the compound of Chemical Formula 1 was treated, collagen synthesis was increased in a concentration-dependent manner, and similar collagen was produced at a lower concentration than vitamin C, which is generally known to induce collagen synthesis Synthesis effect. Thus, it has been found that the compound of formula (I) can be used for skin elasticity enhancement, wrinkle improvement or skin moisturizing.

Experimental Example 3: Elastase activity inhibitory effect (number of repeats = 3)

The activity inhibition effect of elastase, an enzyme that degrades elastin, was confirmed as follows.

Elastase was derived from human leukocyte cells and MeOSuc-Ala-Ala-Pro-Val-pNA, a synthetic substrate for elastase, was used. The buffer solution used was 100 mM Tris (pH 7.5) solution. Elastase was finally used at 0.2 mU using a buffer solution. The synthetic substrate of elastase was diluted with buffer to make a final concentration of 0.5 mM after making 100 mM solution using DMSO. At this time, the positive control group was set to contain 10 ppm of quercetin, which is known as an ELASASTE inhibitor. Elastase inhibition candidates were added to give a final concentration of 10, 20 ppm. The reaction was carried out in a 96-well plate and allowed to react at room temperature for 20 minutes. The absorbance was measured at 405 nm using a spectrophotometer at intervals of 1 minute, and the slope of the absorbance versus time was measured to determine the activity of the enzyme. Elastase inhibition rates were calculated as follows, and the results are shown in Table 3 below.

Inhibitory effect of the compound of formula (1) on elastase activity (number of repeats = 3) sample Enzyme activity Inhibition rate (%) The compound of formula (1) (20 ppm) 3.2 70.64 The compound of formula (1) (10 ppm) 3.8 65.14 The positive control (Quercetin, 10 ppm) 3.5 67.89 The control (DMSO, 20 ppm) 10.9 -

As can be seen from the results of Table 3, the compound of Chemical Formula 1 showed a high level of inhibition of elastase activity at a concentration of 10 ppm, corresponding to quercetin as a positive control, and at a concentration of 20 ppm, And the compound of formula (1) was found to be excellent in the effect of inhibiting elastase activity. Thus, it has been found that the compound of formula (I) can be used for skin elasticity enhancement, wrinkle improvement or skin moisturizing.

Experimental Example 4: Inhibitory effect on collagenase activity (number of repeats = 3)

The inhibitory effect of Collagenase, an enzyme that degrades collagen, was confirmed as follows.

Collagenase used collagenase derived from rat's interest, and N- (3- [2-Furyl] acryloyl) -Leu-Gly-Pro-Ala was used as a substrate for collagenase. Buffer solution was used as a solution with _{50mM Tricine, 10mM CaC l2 · H} 2O, 400mM NaCl (pH 7.5) to melt. The synthetic substrate was dissolved in a buffer solution at a concentration of 10 mM and finally diluted to 75 μM. The collagenase was dissolved at a concentration of 1 unit / ml using cold distilled water at 4 ° C, and then diluted with buffer solution to a final concentration of 0.05 unit / ml. Collagenase inhibition candidates were tested at final concentrations of 10, 20 ppm. At this time, the positive control group was set to have a final concentration of 10 ppm of epigallocatechin gallate (EGCG) whose collagenase inhibitory effect is known. The reaction was carried out in a 96-well plate and allowed to react at room temperature for 10 minutes. Absorbance was measured at 345 nm using a spectrophotometer at intervals of 1 minute, and the maximum slope of absorbance versus time was determined to determine the activity of the enzyme. The inhibition rates of collagenase were calculated as follows, and the results are shown in Table 4 below.

Inhibition of collagenase activity of the compound of formula (1) (number of repeats = 3) sample Enzyme activity Inhibition rate (%) The compound of formula (1) (20 ppm) 1.9 44.12 The compound of formula (1) (10 ppm) 2.8 17.65 The positive control (EGCG, 10 ppm) 2.1 38.24 The control (DMSO, 20 ppm) 3.4 -

As shown in the results of Table 4, the compound of Chemical Formula 1 showed a collagenase activity inhibitory effect at a concentration of 20 ppm, which is superior to the positive control, EGCG, and the compound of Chemical Formula 1 was found to be excellent in collagenase effect. Thus, it has been found that the compound of formula (I) can be used for skin elasticity enhancement, wrinkle improvement or skin moisturizing.

Experimental Example 5: Anti-glycation effect

In order to confirm anti-glycation efficacy, anti-glycation activity was measured using L-arginine and glucose.

First, 1 M L-arginine and 1 M glucose were dissolved in 1 M phosphate buffer (pH 7.4) and diluted to 25 and 50 ppm with 1M phosphate buffer solution. 1M L-arginine and 1M phosphate buffer solution were mixed at a ratio of 1: 4, and then 80 [mu] l each was added to a 96-well plate. To this was added 100 μl of 0.01 M aminoguanidine to be used as a positive control and a sample diluted to 25 and 50 ppm, respectively. These samples were mixed well and finally glucose diluted with 1M phosphate buffer solution was added to the final concentration of glucose to 0.1 M and reacted at 70 ° C for 4 hours. The degree of saccharification was measured by measuring the absorbance of the 96-well plate at 420 nm using a spectrophotometer.

In order to measure the absorbance of the sample itself, 1M L-arginine and the sample alone were added without glucose, and the absorbance at 420 nm was measured by adding 1M L-arginine and 1M glucose to the glycation test group. Respectively. The saccharide inhibitory activity was determined by the following equation, and the results are shown in Table 5 below.

The antagonism effect (number of repeats = 3) of the compound of formula (1) sample Inhibition rate (%) The control (DMSO, 50 ppm) - The positive control (Aminoguanidine, 55 ppm) 54.89 The compound of formula (1) (50 ppm) 62.23 The compound of formula (1) (25 ppm) 42.11

As can be seen from the results shown in Table 5, the compound of Chemical Formula 1 was found to be more excellent in antagonism effect as compared with amino guanidine, which is known as an anticarious substance. Therefore, the compound of the formula (1) shows an excellent antagonism effect, and it can be expected that a synergistic effect can be expected by acting as an auxiliary role in skin whitening, elasticity enhancement, wrinkle improvement and skin moisturization.

Experimental Example 6: Antioxidant effect - Free radical scavenging rate

The free radical scavenging activity was measured to confirm the antioxidative activity of the substance of the formula (1). Free radical scavenging activity was measured using DPPH. DPPH was purchased from Sigma Co. (Sigma Co., Ltd, USA) and used. First, a standard DPPH ethanol solution of 1.5 mM (0.06 mg / ml) was prepared. Then, a 1000 μg / ml vitamin C solution was prepared using the third distilled water, and then serially diluted with 1/2 of the diluted solution to obtain 1000, 500, 250, 125, 62.5, 31.25, 15.625, 7.8125, 3.90625, 1.953125, 0.9765625, 0.48828125 μg / ml of vitamin C sample. In addition, a diluted solution of formula (1) was prepared at the same concentration as vitamin C. Then, the sample and standard DPPH solution were added at the same ratio, stirred well, reacted at 37 ° C for 30 minutes, and absorbance was measured at 520 nm. At this time, ethanol was added instead of the sample to give a control group. The free radical scavenging activity was determined by IC ₅₀ , the half maximal inhibitory concentration (inhibition median), and the results are shown in Table 6 below. IC ₅₀ is a common method for expressing free radical scavenging activity with the concentration of vitamin C and the compound of formula 1 required to remove 50% of the free radicals of the no-added control group.

Free radical scavenging rate (IC ₅₀ ) (number of repeats = 3) sample IC ₅₀ Positive control (vitamin C) 7.1 The compound of formula (1) 5.2

As can be seen from the results in Table 6, the compound of Chemical Formula 1 has a lower IC ₅₀ value than that of vitamin C, which is generally known as an antioxidant. Therefore, the compound of the formula (1) shows excellent antioxidative effect, and it can be expected that a synergistic effect can be expected by acting as an auxiliary role in skin whitening, elasticity enhancement, wrinkle improvement and skin moisturization similarly to the anticarcinogenic effect.

Claims (10)

1. A cosmetic composition comprising a compound represented by the following formula (1) or a cosmetically acceptable salt thereof as an active ingredient.
[Chemical Formula 1]

The cosmetic composition according to claim 1, wherein the cosmetic composition is for skin whitening.
The cosmetic composition according to claim 1, wherein the cosmetic composition is for enhancing skin elasticity or improving wrinkles.
The cosmetic composition according to claim 1, wherein the cosmetic composition is for skin moisturizing.
The composition according to any one of claims 1 to 4, wherein the composition has a total amount of melanin, promotion of collagen synthesis, inhibition of elastase activity, inhibition of collagenase activity, antagonism or antioxidation effect Composition.
The composition according to any one of claims 1 to 4, wherein the composition is a solution, an external ointment, a cream, a foam, a nutritional lotion, a softening longevity pack, a pack, a soft water, a latex, a makeup base, an essence, Formulations selected from the group consisting of sunscreen creams, sun oil, suspensions, emulsions, pastes, gels, lotions, powders, soaps, surfactant-containing cleansing, oils, powder foundations, emulsion foundations, wax foundations, patches and sprays ≪ / RTI >
1. A food composition comprising a compound represented by the following formula (1) or a pharmaceutically acceptable salt thereof as an active ingredient.
[Chemical Formula 1]

The food composition according to claim 7, wherein the food composition is for skin whitening, skin elasticity enhancement or wrinkle improvement, or skin moisturizing.
A quasi-drug composition comprising a compound represented by the following formula (1) or a pharmaceutically acceptable salt thereof as an active ingredient.
[Chemical Formula 1]

The quasi-drug composition according to claim 9, wherein the quasi-drug composition is for skin whitening, skin elasticity enhancement or wrinkle improvement, or skin moisturization.