KR20170078216A - Composition for improving skin conditions comprising Dehydrotumulosic acid - Google Patents

Abstract

The present invention relates to a cosmetic composition, a pharmaceutical composition, and a health food which have excellent effects on skin antiheration, blackening, wrinkle improvement, elasticity improvement, skin moisturization or anti-inflammation. The composition of the present invention exhibits excellent effects on skin or hair blackening, skin elasticity enhancement, skin wrinkle improvement, skin moisturization or skin anti-inflammation. The compound of Chemical Formula (1), which is an active ingredient of the composition of the present invention, can be used as a cosmetic raw material, a pharmaceutical ingredient or a health food raw material which is safe for skin and has excellent skin condition improving effect.

Description

[0001] The present invention relates to a composition for improving skin condition comprising dehydrofolate reductase (dehydrofolate reductase)

More particularly, the present invention relates to a cosmetic composition, a pharmaceutical composition, and a health composition having excellent effects on skin antiglycolysis, blackening, wrinkle improvement, elasticity improvement, skin moisturization or anti-inflammation It is about food.

Due to the economic growth, the interest in the appearance as well as the health is increasing, and the desire to keep skin and keep healthy is also increasing. In recent years, not only healthy skin maintenance but also self-tanning products have been increasingly used to make skin look healthier. Self-tanning can avoid photo-aging due to overexposure to ultraviolet light, and it is possible to produce a tanning effect even in a season when sunlight does not shine. Recently used self-tanning products have been combined with keratin in the stratum corneum, such as Erythrulose and Dihydroxyacetone, to temporarily dye the skin and dye it. However, in the case of dihydroxyacetone, the skin tone is often not uniform according to the usage method, and there is a problem that the skin is smudged due to peeling of the keratin, and the erythrulose is colored with a more uniform skin tone, . In addition, it has been reported that exposure to ultraviolet light within 24 hours after application to the skin promotes active oxygen production of the skin.

In addition, gray hair generally occurs when the age is higher, giving the feeling of old age, and gray hair, especially at a young age, causes stress. White moths are more prominent in Oriental populations with black hair than white ones with bright hair color, and are being studied in health and beauty and psychology. Melanin is divided into red-yellow Pheomelanin and black-brown Eumelanin. Melanin in hair is an important factor that determines the color of hair. Melanin produced in the melanocyte present in the hair, After being transferred to the cortical cell keratinocytes, the hair moves upward with the growth of the hair. The gray hair, recognized as a phenomenon of physiological aging, is caused by a decrease in the number of hair melanocytes and a decrease in the production of melanin due to a decrease in function of melanocytes. Dyeing is currently used as a solution to white moth, but dyeing must be re-pigmented by growth of gray hair in a temporary manner, and the ingredients contained in the dye of the hair dyes become irritants and cause contact dermatitis or skin allergy It is becoming a problem.

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 marked increase in the activity of the elastin degrading enzyme Elastase have been found to be one of the causes of skin wrinkles. It is known that Elastase is the only enzyme capable of degrading elastin, and its inhibition can fundamentally reduce the wrinkles of the skin.

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

In addition, the elastic fiber produced in the fibroblast of the skin forms a cross-link with collagen, and is a skin constituent important for wrinkle formation which is involved in skin elasticity. Deficiency and decomposition of elastic fibers were found to be one of the main factors of skin wrinkle formation and elasticity reduction.

Presently, retinoids, adenosine, animal placenta-derived proteins, chlorella extract, and the like are known to improve wrinkles. The best known retinol promotes collagen synthesis and inhibits elastase enzymes, but it is unstable. When applied to the skin, it has a limited use due to safety problems such as irritation and redness, and chlorella extract has little effect, It is known that it is difficult to expect a wrinkle-improving effect.

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. Saccharification takes place through a series of complex chemical reactions known as Amadori rearrangement, Maillard reaction, which results in the formation of advanced glycation endproducts (AGEs).

On the other hand, the glycation process of the protein does not involve the enzymatic action, so it occurs slowly, and as a result, the protein having a longer half-life such as collagen has more influence. Analysis of the final glycation products revealed that the more aged the glycated collagen was accumulated, the accumulation of the final glycated product changed the protein to a harder and more brittle state, and the glycated collagen was found in the extracellular matrix of the dermal layer (Dyer, DG et al. , The Journal of Clinical Investigation, 9, p. 2463, 1993), by inhibiting collagen from forming a proper structure and thereby reducing skin elasticity and promoting wrinkle formation.

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.

Inflammation is the immune response of the body in response to a wound or disease. Oxidative stresses such as ultraviolet rays, active oxygen, and free radicals activate inflammatory factors and cause aging of various diseases and skin. The vasoactive polypeptides Kinin, Plasmin and Complement have vasodilatation, contraction and chemotaxis, and also include lymphokines such as interleukin-6 (IL-6) Phosphorus and arachidonic acid are responsible for inflammation. Arachidonic acid is metabolized through the two pathways of cyclooxygenase or lipoxygenase and is metabolized to inflammation mediator Prostaglandin or Lukotriene to mediate various inflammatory responses.

On the other hand, in order to eliminate inflammation, elimination of inflammation source, reduction of vital reaction and symptoms is called anti-inflammatory. Flutenamic acid, Ibuprofen, Benzydamine, Indomethacin, and Prednisolone have been used for antiinflammatory purposes to date. Nonsteroidal antiinflammatory agents include fluthenic acid, , And dexamethasone. It is also known that allantoin, azene, hydrocortisone, etc. are effective in improving inflammation. However, these substances have problems in that their use is limited due to the safety of the skin, or the effects thereof are insignificant, have.

Accordingly, it is possible to provide a composition which is safe and biologically safe, effective for skin, safe and stable, and has anticalcification, blackening, wrinkle improvement, elasticity improvement, Improvement of elasticity, or development of a component for anti-inflammation is strongly desired.

Accordingly, a problem to be solved by the present invention is to solve the above-mentioned problems, and to provide a new active ingredient which is safe for human body and has little side effects and is excellent in antihalation, blackening, wrinkle improvement, elasticity improvement or anti- To provide useful applications.

In other words, a problem to be solved by the present invention is to provide a composition comprising an active ingredient having excellent efficacy as an active ingredient.

In order to solve the above-mentioned problems, the present invention provides a cosmetic composition or a pharmaceutical composition comprising a dehydrotest inhibitory compound or a pharmaceutically or cosmetically acceptable salt thereof as an active ingredient.

The present invention also relates to a method for improving the skin elasticity, skin wrinkle improvement, skin moisturizing effect, and the like for skin or hair, which comprises dehydrotumulosic acid or a pharmaceutically or cosmetically acceptable salt thereof as an active ingredient, Or a skin anti-inflammatory composition, preferably a cosmetic composition, a pharmaceutical composition or a health food.

That is, the present invention relates to a use of a dehydrotoxime-type excipient or a pharmaceutically or cosmetically acceptable salt thereof as a cosmetic composition or a pharmaceutical composition for blackening of skin or hair, for improving skin elasticity, for improving skin wrinkles, Or for skin anti-inflammation.

The inventors of the present invention have discovered that dehydrothioglycolic acid accelerates the production of collagen in the skin and inhibits the activity of the elastase, thereby improving wrinkles and elasticity of the skin, thus completing the present invention. Further, it was confirmed that the dehydrothioglycolic acid increased the total amount of melanin to exhibit the blackening effect of skin or hair, and inhibited the NO production and also showed an anti-inflammatory effect. In addition, the dehydrothioglycolic acid exerts an antihyperglycosylation effect and acts as an auxiliary for improving wrinkles and skin elasticity of the skin, thereby exhibiting a synergistic effect.

In the present invention, the term 'blackening effect' means that the coloring matter of the skin or hair is increased, and in particular, the amount of the melanin pigment is increased, which means that the skin or hair shows a dark color. The invention is not limited by this mechanism.

In the present invention, the term 'improving elasticity or skin elasticity' means reducing the degree to which the skin is stuck or stretched. In addition, the elasticity means that elasticity of the skin is maintained in a state where elastin and collagen are sufficiently present.

In the present invention, "improving wrinkles" refers to preventing, suppressing or inhibiting the generation of wrinkles on the skin, or alleviating wrinkles that have already been formed.

In the present invention, the term 'moisturizing or skin moisturizing' means increasing the skin moisture and maintaining a moist state. Skin moisturizing effect can help to improve wrinkles and elasticity of skin.

In the present invention, the term 'anti-inflammatory effect' refers to inhibition of inflammation. The inflammation is one of defensive responses of biological tissues to certain stimuli, and involves three types of tissue degeneration, circulatory disorder, exudate, and tissue proliferation Complex lesions. 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. Examples of skin diseases associated with inflammation include atopic dermatitis, psoriasis, radiation, chemical substances, inflammatory diseases caused by burns, acid burns, vesicular dermatosis, visceral type diseases, itching due to allergies, seborrheic eczema, rose acne, Inflammatory hair loss such as pemphigus vulgaris, polymorphous exudative erythema, erythema nodosum, erythematosus, pharyngitis, alopecia areata, skin T-cell lymphoma, and the like.

In the present invention, the 'antagonism' effect means preventing the collagen from being saccharified in the extracellular matrix of the dermal layer, thereby enhancing elasticity of the skin and preventing wrinkle formation. In addition, the anti-glycation effect inhibits the production of a final glycation product accumulated on the dermal layer according to skin aging. Therefore, in the present invention, the anticarcinogenic effect can cause a synergistic effect on skin elasticity enhancement and wrinkle improvement.

In order to solve the above-mentioned problems and to achieve the object of the present invention, the present invention provides a composition comprising a compound represented by the following Chemical Formula 1, or a pharmaceutically or cosmetically acceptable salt thereof.

[Chemical Formula 1]

The compound represented by the formula (1) has the molecular formula C ₃₁ H ₄₈ O ₄ , the molecular weight is 484, and is named dehydrotumulosic acid.

The present invention is not particularly limited to the method for obtaining the dehydrohalogenated acid, and may be chemically synthesized by a method known in the field of the present invention, or a commercially available substance may be used.

In the cosmetic composition, the pharmaceutical composition and the health food according to the present invention, the content of the dehydrotensitized rosin or its pharmaceutically or cosmetically acceptable salt may be 0.00001 to 0.005% by weight based on the total weight of the cosmetic composition, 10% by weight.

In the present invention, the dehydrotoxime-based excipient used as an active ingredient can be used in the form of a "pharmaceutically or cosmetically acceptable salt ". A "pharmaceutically or cosmetically acceptable salt " of the dehydrotoxime excipient may include salts prepared by adding a base to the formula hydroxides. Additional salts that can be used to prepare the pharmaceutically or cosmetically acceptable salts include, but are not limited to, any one or more salts selected from the group consisting of sodium, potassium, calcium, ammonium, magnesium, and organic amino .

The dehydrohalogenated compounds of the present invention may exist in solvated as well as unsolvated forms including forms of hydrates, ethanolates and the like. The dehydrohalogenated compounds 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.

The composition for skin or hair blackening, skin elasticity enhancement, skin wrinkle improvement, skin moisturizing or skin anti-inflammation according to the present invention can be used as a solution, external ointment, cream, foam, nutritional lotion, softening water, , Makeup bases, essences, soaps, liquid cleansing agents, bath salts, sunscreen creams, sun oil, suspensions, emulsions, pastes, gels, lotions, powders, soaps, surfactant-containing cleansing oils, powder foundations, emulsion foundation , A wax foundation, a patch, and a spray, although the present invention is not limited thereto.

In addition, the cosmetic composition of the present invention may further comprise at least one cosmetically acceptable carrier compounded in a cosmetic composition for general skin, and examples thereof include oil, water, a surfactant, a moisturizer, a lower alcohol, 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 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, silicon, 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 an emulsion, a solvent, a solubilizing agent or an emulsifying agent is used as a carrier component, and examples thereof include water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl benzoate, -Butyl glycol oil, and 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.

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, alkali metal salts of fatty acids, fatty acid hemiesters, fatty acid protein hydrolizates, isethionates, lanolin derivatives, aliphatic alcohols, vegetable oils, glycerol, sugars and the like are used as carrier components .

The present invention also relates to the use of a compound represented by the general formula (I) or a pharmaceutically or cosmetically acceptable salt thereof as an active ingredient for skin or hair blackening, skin elasticity enhancement, skin wrinkle improvement, Thereby providing a skin anti-inflammatory method. The subject includes, without limitation, mammals including rats, livestock, humans, and the like.

According to another embodiment of the present invention, there is provided a composition for skin or hair blackening, skin elasticity enhancement, skin wrinkle improvement, or the like, which contains the compound of Chemical Formula 1 or a pharmaceutically or cosmetically acceptable salt thereof as an active ingredient , A skin moisturizing or skin anti-inflammatory composition.

The composition comprising the compound of the present invention may be various oral or parenteral formulations, but may preferably be a parenteral agent. In the case of formulation, a diluent or excipient such as a filler, an extender, a binder, a wetting agent, a disintegrant, or a surfactant is usually used. Solid formulations for oral administration include tablets, pills, powders, granules, capsules, and the like, which may contain one or more excipients such as starch, calcium carbonate, sucrose or lactose lactose, gelatin and the like. In addition to simple excipients, lubricants such as magnesium stearate, talc, and the like are also used. Liquid preparations for oral administration include suspensions, solutions, emulsions, syrups and the like. Various excipients such as wetting agents, sweeteners, fragrances, preservatives and the like may be included in addition to water and liquid paraffin, which are simple diluents commonly used. have. Formulations for parenteral administration include sterile aqueous solutions, non-aqueous solutions, suspensions, and emulsions. Propylene glycol, polyethylene glycol, vegetable oil such as olive oil, injectable ester such as ethyl oleate, and the like can be used as the non-aqueous solvent and suspension agent.

The present invention also relates to the use of a compound of formula (I) or a pharmaceutically or cosmetically acceptable salt thereof as an active ingredient for skin or hair blackening, skin elasticity enhancement, skin wrinkle improvement, skin moisturizing, And can be provided as a formulation of an external preparation for skin.

When the compound of Chemical Formula 1 or a pharmaceutically or cosmetically acceptable salt thereof is used as an external preparation for skin, it may further contain a fatty substance, an organic solvent, a solubilizing agent, a thickening agent and a gelling agent, a softening agent, an antioxidant, a suspending agent, A foaming agent, a fragrance, a surfactant, water, an ionic or nonionic emulsifier, a filler, a sequestering and chelating agent, a preservative, a vitamin, a barrier, a wetting agent, A lipophilic active agent, a lipid vesicle or any other ingredient conventionally used in external preparations for skin. The components can also be introduced in amounts commonly used in the field of dermatology.

When the compound of Formula 1, or a pharmaceutically or cosmetically acceptable salt thereof, is provided as an external dermal preparation, it may have a formulation such as, but not limited to, ointments, patches, gels, creams or sprays.

The pharmaceutical composition of the present invention is particularly preferably used as a parenteral preparation. For example, the external preparation for skin may be a pharmaceutically acceptable base such as vaseline or stearyl alcohol; Suitable pharmaceutically acceptable surfactants such as polysorbate, sorbitan sesquioleate, and the like; A suitable pharmaceutically acceptable humectant such as glycerin; A suitable pharmaceutically acceptable solvent; And a conventional external preparation for skin preparation in which a flavoring agent, a coloring agent, a stabilizer, a tackifier and the like are homogeneously mixed.

When the compound of Formula 1 of the present invention or its pharmaceutically or cosmetically acceptable salt is used as a medicament, it may further contain one or more active ingredients showing the same or similar functions. For example, it may contain known ingredients for skin or hair blackening, skin elasticity enhancement, skin wrinkle improvement, skin moisturizing or skin anti-inflammatory ingredients. The skin or hair of the composition of the present invention can be blackened, skin elasticity is improved, skin wrinkle is improved, skin moisturization is improved when the skin or hair for blackening, skin elasticity enhancement, skin wrinkle improvement, skin moisturizing or skin anti- Or the skin anti-inflammatory effect may be further enhanced. When the above ingredients are added, skin safety, easiness of formulation, and stability of effective ingredients can be considered according to the combined use.

In one embodiment of the invention, the composition is a skin elasticity or wrinkle improving ingredient known in the art and includes retinoic acid, TGF, animal placenta-derived proteins, betulinic acid and chlorella extract; Anti-inflammatory components known in the art include, but are not limited to, COX-2 inhibitors, prednisolone and allantoin; Examples of moisturizing ingredients known in the art include petrolatum, mineral oil, silicone, triglycerides, essential fatty acids such as gamma linolenic acid (evening primrose oil), GGF, amino acids, provitamin B5, hyaluronic acid, γ-glutamic acid, Lipidure PMB, ceramide, cholesterol, fatty acids; And derivatives thereof, and various plant extracts. ≪ Desc / Clms Page number 2 > The additional ingredients may be included in an amount of 0.0001 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 of Formula 1, and the like.

When the pharmaceutical composition of the present invention contains an effective amount of the compound of Chemical Formula 1 or a pharmaceutically or cosmetically acceptable salt thereof, it is preferable to use the composition of the present invention for skin or hair blackening, skin elasticity enhancement, skin wrinkle improvement, skin moisturizing, Can be provided. In the present invention, the term "effective amount" means an amount of a compound capable of sufficiently exhibiting skin or hair blackening, skin elasticity enhancement, skin wrinkle improvement, skin moisturizing or skin anti-inflammatory effect.

The effective amount of the compound of formula (I) or a pharmaceutically or cosmetically acceptable salt thereof contained in the composition of the present invention will vary depending on the form in which the composition is produced, the manner in which the compound is applied to the skin, and the time on the skin. For example, when the composition is commercialized as a pharmaceutical product, the compound of Formula 1 may be contained at a higher concentration than that of a cosmetic product that is routinely applied to skin. Accordingly, the daily dosage is 0.1 to 100 mg / kg, preferably 30 to 80 mg / kg, more preferably 50 to 60 mg / kg, based on the amount of the compound of formula (1) 6 times a day.

According to another embodiment of the present invention, there is provided a pharmaceutical composition for skin or hair for blackening, skin elasticity enhancement, skin wrinkle improvement, skin moisturizing, or skin antiaging agent containing the compound of Chemical Formula 1 or a pharmaceutically or cosmetically acceptable salt thereof Inflammatory health food.

In the present specification, the term 'health food' is intended to include a compound of the above formula (1) or a pharmaceutically or cosmetically acceptable salt thereof to a food material such as a beverage, a tea, a spice, a gum or a confectionery, or to encapsulate, , Which means that it has a certain health effect when ingested. However, unlike general medicines, there is an advantage that there is no side effect that may occur when a drug is taken for a long time by using a food as a raw material. Since the health food of the present invention thus obtained can be taken on a daily basis, it can be expected to exert excellent effects on blackening of skin or hair, skin elasticity enhancement, skin wrinkle improvement, skin moisturization or skin anti-inflammation.

When the compound of Chemical Formula 1, or a pharmaceutically or cosmetically acceptable salt thereof, is used as a food additive, the compound of Chemical Formula 1 or a pharmaceutically or cosmetically acceptable salt thereof may be directly added, Can be used together, and can be suitably used according to a conventional method. The amount of the active ingredient to be mixed can be suitably determined according to its intended use (prevention, health or therapeutic treatment). Generally, the composition of the present invention is added in an amount of not more than 15 parts by weight, preferably not more than 10 parts by weight, based on the raw material, when the food or beverage is produced. However, in the case of long-term consumption intended for health and hygiene purposes or for health control purposes, the amount may be less than the above range, and since there is no problem in terms of safety, the active ingredient may be used in an amount exceeding the above range . There is no particular limitation on the kind of the food. Examples of the food to which the above substance can be added include dairy products including meat, sausage, bread, chocolate, candy, snack, confectionery, pizza, ramen, other noodles, gums, ice cream, various soups, drinks, tea, Alcoholic beverages, and vitamin complexes, all of which include health foods in a conventional sense. The health beverage composition of the present invention may contain various flavors or natural carbohydrates as an additional ingredient such as ordinary beverages. The above-mentioned natural carbohydrates are sugar alcohols such as monosaccharides such as glucose and fructose, disaccharides such as maltose and sucrose, polysaccharides such as dextrin and cyclodextrin, and xylitol, sorbitol and erythritol. Examples of sweeteners include natural sweeteners such as tau martin and stevia extract, synthetic sweeteners such as saccharin and aspartame, and the like. The ratio of the natural carbohydrate is generally about 0.01 to 0.04 g, preferably about 0.02 to 0.03 g per 100 mL of the composition of the present invention. In addition to the above, the health food of the present invention may contain various nutrients, vitamins, electrolytes, flavors, colorants, pectic acids and salts thereof, alginic acid and its salts, organic acids, protective colloid thickeners, pH adjusters, stabilizers, preservatives, glycerin, , A carbonating agent used in carbonated drinks, and the like. In addition, the health food of the present invention may contain flesh for the production of natural fruit juice, fruit juice drink and vegetable drink. These components may be used independently or in combination. The proportion of such additives is not critical, but is generally selected in the range of 0.01 to 0.1 parts by weight per 100 parts by weight of the composition of the present invention.

In one embodiment of the present invention, but not limited thereto, the composition may comprise 0.00001% to 10% by weight of the compound of Formula 1 or a pharmaceutically or cosmetically acceptable salt thereof, based on the total composition weight have.

The composition containing the dehydrothioglycoside of the present invention exhibits excellent effects on skin or hair blackening, skin elasticity enhancement, skin wrinkle improvement, skin moisturization or skin anti-inflammation.

The composition of the present invention containing a dihydrotreated formula can be used as a cosmetic raw material, a pharmaceutical ingredient, or a raw material for health food, which is safe for skin and has excellent skin condition improving effect.

Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the embodiments according to the present invention can be modified into various other forms, and the scope of the present invention should not be construed as being limited to the embodiments described below. The embodiments of the present invention are provided by way of example to facilitate a specific understanding of the present invention.

Reference Example  One: Dehydrotourism Exceed ( Dehydrotumulosic  acid) Material Information

[Chemical Formula 1]

Material name: Dehydrotumulosic acid

CAS No. : 6754-16-1

Molecular formula: C ₃₁ H ₄₈ O ₄

Molecular weight: 484

Where to buy: Shanghai Tauto Biotech Co., Ltd.

Experimental Example  1: 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 synthesized collagen 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 (1) 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 by 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 / / 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 1 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 140.3 - The positive control (vitamin C, 52.85 ppm) 215.1 53.3 The compound of formula (1) (1 ppm) 182.1 29.8 The compound of formula (1) (10 ppm) 209.9 49.6

As can be seen from the results of Table 1, when the compound of Chemical Formula 1 was treated, the amount of collagen synthesis was increased in a concentration-dependent manner. In the case of vitamin C, which is generally known to induce collagen synthesis, Synthesis effect.

Experimental Example 2: Elastase activity inhibitory effect

The activity inhibitory effect of Elastase, an enzyme that degrades elastin, was confirmed as follows.

Elastase used Elastase from human leukocyte cells and MeOSuc-Ala-Ala-Pro-Val-pNA as synthetic substrate for Elastase. The buffer solution used was 100 mM Tris (pH 7.5) solution. Finally, 0.2 mU was used for the ELASTASES using a buffer solution. In addition, the synthetic substrate of Elastase was diluted with buffer solution to make a final concentration of 0.5 mM by making a 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 ELASTIC inhibitor. Ella stase 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. Absorbance was measured at 405 nm using a spectrophotometer at intervals of 1 minute, and the slope of the absorbance versus time was determined as the activity of the enzyme. Ella stasis inhibition rates were calculated as follows.

Elastase activity inhibitory effect (number of repeats = 3) of the compound of formula (1)

sample Enzyme activity Inhibition rate (%) The compound of formula (1) (20 ppm) 3.9 62.5 The compound of formula (1) (10 ppm) 4.6 55.77 The positive control (Quercetin, 10 ppm) 4.9 53.19 The control (DMSO, 20 ppm) 10.4 -

As can be seen from the results of Table 2, the compound of Chemical Formula 1 showed an inhibitory effect on elasstase activity superior to that of quercetin at a concentration of 20 ppm, and the compound of Chemical 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 effectively used for skin elasticity and wrinkle improvement.

Experimental Example  3: Glycation  The anti- glycation ) effect

In order to confirm the anti-glycation effect, the saccharification inhibitory activity was measured using L-arginine and glucose.

First, 1 M L-arginine and 1 M glucose were prepared by dissolving 1 M phosphoric acid buffer (pH 7.4) and diluted to 50 ppm and 100 ppm using 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 each sample, 100 μl of 0.01 M aminoguanidine to be used as a positive control and a sample diluted to 50 ppm and 100 ppm, respectively, were added. 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.

Glycation group of the following formula was an experimental group in which 1M L-arginine and 1M glucose were added to induce glycation. Absorbance was measured at 420 nm by adding 1M L-arginine and sample alone without glucose to measure the absorbance of the sample itself. The saccharide inhibitory activity can be obtained by the following formula.

The antagonism effect of the compound of formula (1)

sample Inhibition rate (%) The control (DMSO, 50 ppm) - The positive control (Aminoguanidine, 55 ppm) 56.21 The compound of formula (1) (50 ppm) 71.34 The compound of formula (1) (25 ppm) 40.97

As can be seen from the results shown in Table 3, the compound of Chemical Formula 1 was found to be more excellent in antagonism effect as compared with aminoguanidine known as an antagonist. That is, the compound of the formula (1) exhibits an excellent antihyperglycosylating effect, and antiherating effect plays an auxiliary role in improving the wrinkles and elasticity of the skin, and a synergistic effect can be expected.

Experimental Example  4: Blackening  Effect - Increase in the total amount of melanin

The compound of the formula (1) was added to the culture solution of mouse B-16 mouse melanoma cells to determine the blackening 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 and to determine the concentration without toxicity, blackening evaluation was performed.

The compound of formula (1) was added to the culture medium to a final concentration of 1 ppm and 10 ppm, and the control group, Forskolin, was added to the medium so as to be 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 absorbance was measured at 400 nm using a spectrophotometer to measure the amount of melanin produced.

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 an increase rate (%). The results are summarized in Table 4 below.

 Increased effect of total melanin level at cell level according to concentration

sample Melanin production
(abs) Growth rate (%) Control group (DMSO, 10 ppm) 0.321 - The positive control (Forskolin, 10 ppm) 0.413 28.6 Formula 1 (10 ppm) 0.475 48.0 (1 ppm) 0.398 24.0

As can be seen from the results in Table 4, the compound of Chemical Formula 1 shows a remarkably superior total amount of melanin even at 10 ppm as compared with the positive control phosholin, and can be used for blackening of skin or hair there was.

Experimental Example 5: Anti-inflammatory effect -NO formation inhibitory effect

In order to confirm the anti-inflammatory effect and the skin trouble relieving effect of the compound of formula (1), nitrite oxide (NO) formation inhibition test was carried out by the GRIESS method using RAW264.7 cell line (ATCC number: CRL-2278).

Specifically, RAW264.7 cells, macrophages of mice, were subcultured several times, placed in 24-well plates at 3 × 10 ⁵ per well, and cultured for 24 hours. Subsequently, the compound of formula (1) was replaced with a diluted cell culture medium at a final concentration of 1, 10 and 100 ppm. At this time, L-NMMA (L-NG-Monomethylarginine), which is an inhibitor of NO production, was treated together as a positive control, and cultured for 30 minutes. Lipopolysaccharide (LPS) . 100 μl of the supernatant was transferred to a 96-well plate, and 100 μl of the GRIESS solution was added thereto at room temperature for 10 minutes, and the absorbance at 540 nm was measured to determine the NO inhibitory effect of the compound of formula (1) Are shown in Table 5 below.

sample NO production inhibition rate (%) Control group (DMSO, 10 ppm) - L-NMMA (positive control, 10 ppm) 49.36 The compound of formula (1) (1 ppm) 11.79 The compound of formula (1) (10 ppm) 17.31 The compound of formula (1) (100 ppm) 47.98

As can be seen from the results of Table 5, the compound of Chemical Formula 1 showed a significant inhibition of NO production as a natural substance when compared with L-NMMA which is a representative anti-inflammatory drug substance. Accordingly, it has been confirmed that the compound of formula (1) can be effectively used for improving skin inflammation and skin troubles. In addition, the anti-inflammatory effect acts as an auxiliary function to the skin elasticity or wrinkle improvement, so that a synergistic effect can be expected.

Claims (10)

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

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

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

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

1. A composition for skin inflammation comprising a compound represented by the following formula 1 or a pharmaceutically or cosmetically acceptable salt thereof as an active ingredient.
[Chemical Formula 1]

6. The composition according to any one of claims 1 to 5, wherein the composition is used as a cosmetic composition, a pharmaceutical composition or a health food. The composition according to any one of claims 1 to 5, wherein the compound represented by the formula (1) or a pharmaceutically or cosmetically acceptable salt thereof is contained in an amount of 0.00001 to 10% by weight based on the total weight of the composition . The composition according to any one of claims 1 to 5, wherein the compound of formula (I) or a pharmaceutically or cosmetically acceptable salt thereof contained in the composition exhibits an anti-glycation effect . 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]

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