KR20180061663A - Composition for skin improvement containing dehydroevodiamine - Google Patents

Abstract

The present invention relates to a cosmetic composition comprising dihydroevodiamine, and more particularly to a cosmetic composition having excellent effects such as skin whitening, skin elasticity enhancement, wrinkle improvement, moisturizing or skin trouble improvement. The composition of the present invention exhibits excellent melanin total amount reduction effect even at a low concentration and is excellent in collagen synthesis promoting effect, elastase activity inhibiting effect and anti-inflammatory effect, and is useful for skin whitening, elasticity enhancement or wrinkle improvement, skin moisturizing, It can be used as a cosmetic composition for improvement. In addition, the composition containing the dihydro-eo-biodiamine of the present invention can be used as a food composition and a quasi-drug composition.

Description

[0001] The present invention relates to a cosmetic composition containing dihydro-

The present invention relates to a cosmetic composition comprising dihydroevodiamine, and more particularly to a cosmetic composition having excellent effects such as skin whitening, skin elasticity improvement, wrinkle improvement, moisturizing or skin trouble improvement. The present invention also relates to a food composition and a quasi-drug composition comprising dihydro-eo-biodiamine.

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.

Cosmetics are products used to protect the skin and beautify and clean the skin, but the composition thereof inevitably includes ingredients that are different from the purpose of skin protection. These ingredients include surfactants, preservatives, fragrances, sunscreens, pigments, as well as various ingredients for imparting other efficacy and effects. These ingredients are generally known to cause skin irritation, rashes, swelling and other problems (Maibach, H., I. Contact Dermatitis, 6. 369-404, 1980). In addition, sebum and sweat discharged from the body, fatty acids in cosmetic ingredients, higher alcohols, protein components and the like may be decomposed into substances having high toxicity by the skin-on-ground bacteria existing on the skin, It is well known that skin inflammation is caused by ultraviolet rays from the sun.

Inflammation reactions are manifested in five phenomena, such as feeling of redness, pricking feeling, burning hotness, swelling, and tissue changes, which may be caused by harmful environmental conditions, It is a physiological reaction to protect a living body from intrusion and mechanical damage. These inflammatory phenomena lead to a large number of polymorphonuclear leukocytes (PMNs) and immune substances, and these increased cells secrete a variety of inflammatory cell products, proteases and cytokines. I can do it. However, this action may cause harmful damage to adjacent tissue cells and non-cellular components. Therefore, under proper conditions, the normal function is restored after the initial state of inflammation. However, if irritant stimulating agents are not eliminated or continuously produced, chronic inflammation occurs as a result, resulting in more serious tissue damage.

On the other hand, dehydroevodiamine is an alkaloid-based compound having a molecular formula C ₁₉ H ₁₅ N ₃ O and a molecular weight of 301.4. When dehydroevodiamine or hydrochloride is used, indole (2 ' 3 ': 3,4) pyrido (2,1-b) quinazolinium, 5,7,8,13-tetrahydro-14-methyl-5-oxochloride. It is known to dissociate from oyster oil ( Evodia rutaecarpa) and dissolve in solvents such as chloroform, dichloromethane, ethyl acetate, DMSO, and acetone.

Under these circumstances, the inventors of the present invention have conducted studies on a substance having excellent skin whitening, skin elasticity enhancement, wrinkle improvement, moisturizing and skin trouble improving effects, and a composition containing dihydrolobodiamine as an effective ingredient has been found to reduce the total amount of melanin, Collagen synthesis, inhibition of elastase activity and antiinflammatory effect. Thus, cosmetic composition, food composition and quasi-drug composition using the same were completed.

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

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

More specifically, it is an object of the present invention to provide a cosmetic composition for enhancing skin elasticity or wrinkle comprising dihydro-eo-bodiamine 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 dihydro-ebodiamine 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 improving skin trouble comprising dihydro-eo-bodiamine represented by the formula (1) or a cosmetically acceptable salt thereof as an active ingredient.

Another object of the present invention is to provide a food composition comprising the dihydro ebodiamine 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 dihydro-ebodiamine 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 dihydro-ebodiamine 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 cosmetic composition for enhancing skin elasticity or improving wrinkles comprising dihydroisoindiamine 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 skin moisturizing comprising dihydro-eo-bodiamine represented by the general 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 improving skin trouble comprising dihydro ebodiamine 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 dihydro-eo-bodiamine or a pharmaceutically acceptable salt thereof as an active ingredient.

In another aspect of the present invention, there is provided a quasi-drug composition comprising dihydro ebodiamine or a pharmaceutically acceptable salt thereof as an active ingredient.

The present invention provides a composition comprising a dihydro ebodiamine compound represented by the following formula (1) or a salt thereof.

 [Chemical Formula 1]

In the present invention, " dehydroevodiamine " is represented by the above formula (1) and has a molecular formula C ₁₉ H ₁₅ N ₃ O and a molecular weight of 301.4. When the compound is a dehydroevodiamine or a hydrochloride, (2 ', 3': 3,4) pyrido (2,1-b) quinazolinium, 5,7,8,13-tetrahydro-14-methyl-5-oxochloride, It is an organic compound classified as an alkaloid contained in Evodia rutaecarpa .

The present invention is not particularly limited to the method for obtaining dihydro-e < ' > biodiamine, but may be chemically synthesized by a method known in the art, or a commercially available material may be used.

The dihydro-ebodiamine represented by formula (1) of the present invention may exist in solvated as well as unsolvated form. The dihydro-ebodiamines 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, the content of the dihydro-eo-bodiamine is preferably 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 provides a cosmetic composition for skin whitening, skin elasticity enhancement or wrinkle improvement, skin moisturizing or skin trouble improvement comprising the compound represented by Formula 1 or a cosmetically acceptable salt thereof can do.

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, The total amount of melanin was decreased to a level corresponding to that of the positive control at the lower concentration, and it was confirmed that the composition containing the compound represented by the formula (1) could be used for skin whitening purposes (Table 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, Showed similar collagen synthesis effects (Table 2). In addition, in an embodiment of the present invention, it was found that the compounds of formula (I) inhibited the elastase activity and the collagenase activity, and as a result, in the test group supplemented with dihydro-ebodiamine, (Table 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) has excellent collagen synthesis and elastase activity inhibitory effect, so that the composition containing the compound represented by the formula (1) can be used for skin moisturizing (Tables 2 to 4).

In the present invention, " skin trouble " means a skin disease that can be caused by inflammation caused by excessive nitric oxide production in macrophages. The skin trouble includes all kinds of skin diseases related to inflammation regardless of the type thereof. Non-limiting examples of the skin diseases related to the inflammation include inflammatory diseases caused by atopic dermatitis, psoriasis, radiation, chemical substances, Inflammatory hair loss such as acid burns, watery skin diseases, psoriasis type diseases, allergic itching, seborrheic eczema, rose acne, pemphigus vulgaris, polymorphic exudative erythema, erythema nodosum, Cell lymphoma, and the like. Specific examples include skin rash, acne, rash, injection (red nose), but are not limited thereto. The term "improvement of trouble" as used in the present invention refers to inhibiting or inhibiting the generation of troubles in the skin or alleviating troubles already generated.

In the present invention, " anti-inflammation " refers to inhibition of inflammation. The inflammation is a defense reaction of biological tissue against a certain stimulus, and includes complicated lesions involving tissue degeneration, circulatory disorder and exudation, and tissue proliferation. It says. More specifically, inflammation is part of congenital immunity and, like in other animals, human congenital immunity recognizes a pattern of cell surfaces that are specifically present in a pathogen. Phagocytes recognize cells with such surfaces as non-magnetic and attack pathogens. If pathogens break through the physical barriers of the body, an inflammatory reaction occurs. Inflammation is a nonspecific defense that creates hostile environments for microorganisms entering the wound. In the inflammatory response, white blood cells that are responsible for the early stage of immune response, when wounded or infected, enter the body to express cytokines. Therefore, the expression level of intracellular cytokine is an index of inflammatory response activation. The antiinflammation of the present invention may be to suppress inflammation caused in the skin.

In one embodiment of the present invention, the inhibitory potency of NO formation of the compound represented by Chemical Formula 1 was measured. As a result, the test group to which the compound was added exhibited anti-inflammatory effect to a degree equivalent to that of the positive control. It was confirmed that the composition containing the compound represented by Chemical Formula 1 can be used for improving skin troubles and can act as an auxiliary role in skin whitening, elasticity enhancement, wrinkle improvement, and skin moisturizing (Table 5) .

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 formulation.

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, vegetable oil, wax, paraffin, starch, tragacanth, 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, .

In another aspect of the present invention, there is provided a food composition comprising the compound represented by the above-mentioned formula (1) or a pharmaceutically acceptable salt thereof.

Specifically, the present invention provides a food composition for skin whitening, skin elasticity enhancement or wrinkle improvement, skin moisturizing or skin trouble improvement comprising the compound represented by the above formula (1) or a pharmaceutically acceptable salt thereof can do. The dihydro-ebodiamine compound represented by Formula 1, skin whitening, skin elasticity enhancement, wrinkle improvement, skin moisturization, and skin trouble improvement 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 supplemented as an adjunct to improve skin whitening, skin elasticity improvement or wrinkle improvement, skin moisturizing or skin trouble improving 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.

As another embodiment of the present invention, there is provided a quasi-drug composition comprising the compound represented by the above-mentioned formula (1) or a pharmaceutically acceptable salt thereof.

Specifically, the present invention provides a composition for skin whitening, skin elasticity enhancement or wrinkle improvement, skin moisturizing or skin trouble-improving composition comprising the compound represented by Formula 1 or a pharmaceutically acceptable salt thereof can do. The dihydro-ebodiamine compound represented by Formula 1, skin whitening, skin elasticity enhancement, wrinkle improvement, skin moisturization, and skin trouble improvement 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, moisturizing or anti-inflammatory ingredients. The skin whitening, elasticity enhancement, wrinkle enhancement, moisturizing or skin trouble improving effect of the composition of the present invention may be further increased by the addition of the additional skin whitening, elasticity enhancement, wrinkle improvement, moisturizing or anti-inflammatory component. 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 is a whitening ingredient known in the art, and includes 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; As anti-inflammatory ingredients known in the art, there are non-steroid based flufenamic acid, ibuprofen, benzydamine, indomethacin, prednisolone, dexamethasone, allantoin, azene, hydrocortisone; 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, skin moisturization, or skin trouble improving method including a step of applying to the individual's skin. The subject includes, without limitation, mammals including rats, livestock, humans, and the like.

The cosmetic composition comprising the dihydro-ebodiamine of the present invention or a cosmetically acceptable salt thereof as an active ingredient is excellent in skin whitening, improving elasticity or wrinkle, skin moisturizing, and improving skin troubles. Specifically, the composition of the present invention shows excellent total melanin reduction effect even at a low concentration and is excellent in collagen synthesis promoting effect, elastase activity inhibiting effect and anti-inflammatory effect, and is useful for skin whitening, elasticity enhancement or wrinkle improvement, skin moisturizing, And is highly utilized as a cosmetic composition for improving skin troubles. In addition, the composition containing the dihydro-eo-biodiamine 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: Dehydroevodiamine Material Information

[Chemical Formula 1]

Material name: Dehydroevodiamine

CAS No. : 67909-49-3

Molecular formula: C ₁₉ H ₁₅ N ₃ O

Molecular weight: 301.4

Where to Buy: CHENGDU MUST BIO-TECHNOLOGY CO., LTD

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

The compound of Formula 1 was added to the culture medium 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 negative control 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 (%) Negative control (DMSO, 10 ppm) 0.33 - Positive control (arbutin, 100 ppm) 0.228 30.91 The compound of formula (1) (10 ppm) 0.242 26.67 The compound of formula (1) (1 ppm) 0.289 12.42

As can be seen from the results of the above Table 1, the compound of the formula (1) shows an excellent melanin total reducing effect corresponding to the positive control even at a lower concentration of 10 ppm as compared with the positive control arbutin, .

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) 246.8 64.3 The compound of formula (1) (1 ppm) 190.4 21.1 The compound of formula (1) (10 ppm) 236.0 57.1

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, was used as a substrate for elastase. 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. The compound of formula (1), which is an inhibitor of elastase inhibition, was 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) 3.3 68.27 The compound of formula (1) (10 ppm) 3.9 62.50 The positive control (Quercetin, 10 ppm) 3.5 66.35 The control (DMSO, 20 ppm) 10.4 -

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 a final concentration of 100, 200 ppm. At this time, the positive control group was set to have a final concentration of 100 ppm of quercetin, which is known to have a collagenase inhibitory effect. 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 Compound (1) (Number of Repeats = 3) sample Enzyme activity Inhibition rate (%) The compound of Formula 1 (200 ppm) -2.12 38.73 The compound of formula (1) (100 ppm) -2.38 31.21 The positive control (Quercetin, 100 ppm) -2.42 30.06 Control group (DMSO, 1%) -3.46 -

As can be seen from the results of Table 4, the compound of Chemical Formula 1 showed an inhibitory effect on collagenase activity superior to quercetin, which is a positive control, at a concentration of 200 ppm, and the compound of Chemical Formula 1 was found to be excellent in inhibiting collagenase activity Respectively. 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-inflammatory effect - NO production inhibitory effect

In order to confirm the antiinflammatory effect and the skin trouble-improving effect of the compound of Chemical Formula 1, nitric oxide (NO) formation inhibition experiment was performed by the GRIESS method using RAW264.7 cell line (ATCC number: CRL-2278).

Specifically, RAW264.7 cells, macrophages of mice, were subcultured several times, and the cultured cells were put into 24-well plates so as to enter 3 × 10 ⁵ cells into one well, followed by culturing for 24 hours. Subsequently, the cell culture medium containing the compound of the formula (1) diluted to the concentration shown in the following Table 5 was replaced. At this time, L-NMMA (L-NG-monomethylarginine), a NO-production inhibitor, was treated together as a positive control and cultured for 30 minutes. Lipopolysaccharide (LPS) And cultured for 24 hours. 100 μl of the supernatant was transferred to a 96-well plate, and 100 μl of GRIESS solution was added thereto at room temperature for 10 minutes. Then, the absorbance at 540 nm was measured to determine the NO inhibitory effect of the compound of formula The results are shown in Table 5 below.

NO production inhibitory effect of the compound of formula (1) sample NO production inhibition rate (%) Control group (DMSO, 10 ppm) - The positive control (L-NMMA, 10 ppm) 41.02 The compound of formula (1) (1 ppm) 18.33 The compound of formula (1) (10 ppm) 29.01 The compound of formula (1) (100 ppm) 34.62

As can be seen from the results of Table 5, when the compound of Formula 1 was used in an amount of 100 ppm, the compound of Formula 1 showed a superior inhibitory rate of NO production as compared with that of the positive control, when compared with L-NMMA, It was found that there was a good anti-inflammatory effect. Therefore, the compound of Chemical Formula (1) can be used for improving skin troubles, and it can be expected that synergistic effect can be expected by acting as an auxiliary role in skin whitening, elasticity enhancement, wrinkle improvement and skin moisturization.

Claims (11)

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 cosmetic composition according to claim 1, wherein the cosmetic composition is for improving skin troubles.
6. The cosmetic composition according to any one of claims 1 to 5, wherein the composition has reduced total amount of melanin, promotion of collagen synthesis, inhibition of elastase activity or anti-inflammatory effect.
The composition according to any one of claims 1 to 5, wherein the composition is at least one selected from the group consisting of a solution, an ointment, a cream, a foam, a nutritional lotion, a softening longevity pack, a pack, a soft water, an emulsion, a makeup base, , 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]

9. The composition of claim 8, wherein the food composition is for skin whitening; For improving skin elasticity or improving wrinkles; For skin moisturizing; Or for improving skin troubles.
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]

11. The composition according to claim 10, wherein the quasi-drug composition is used for skin whitening; For improving skin elasticity or improving wrinkles; For skin moisturizing; Or for improving skin troubles.