KR20230021049A - Composition for improving skin conditions comprising Ethyl ferulate - Google Patents

Abstract

The present invention relates to a cosmetic composition, a pharmaceutical composition, and health food having excellent effects on antiglycation, blackening, wrinkle reduction, elasticity improvement, skin moisturizing or anti-inflammation in the skin. The composition of the present invention shows excellent effects on skin or hair blackening, skin elasticity enhancement, skin wrinkle reduction, skin moisturizing or skin anti-inflammation. A compound represented by 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 that is safe for the skin and has excellent skin condition improvement effects.

Description

Composition for improving skin conditions comprising ethyl ferulate

The present invention relates to a composition having an excellent effect on improving skin conditions, and more specifically, a cosmetic composition, a pharmaceutical composition, and a health care composition having excellent effects on skin antiglycation, darkening, wrinkle improvement, elasticity improvement, skin moisturizing or anti-inflammatory. It's about food.

As the level of culture improves along with economic growth, interest in appearance as well as health is increasing, and the desire to care for and maintain healthy skin is also increasing. In recent years, the use of self-tanning products not only for maintaining healthy skin but also for making the skin look healthy is increasing. Self-tanning can avoid photoaging due to overexposure to ultraviolet rays and can produce a tanning effect even in seasons when sunlight is not shining, so interest is increasing. Recently used self-tanning products use methods such as erythrulose or dihydroxyacetone that combine with keratin in the stratum corneum of the skin to temporarily color the skin and dye it. However, in the case of dihydroxyacetone, the skin tone is often not uniform depending on the method of use, and there is a problem that the skin looks mottled as the dead skin cells are peeled off, and erythrulose develops a more uniform skin tone, but the color development is too weak. there is In addition, it has been reported that the production of active oxygen in the skin is accelerated when exposed to ultraviolet rays within 24 hours after application to the skin.

In addition, gray hair generally occurs with increasing age, giving a feeling of old age, and especially gray hair at a young age causes stress. White hair appears more clearly in Asians with black hair than Caucasians with light hair color, and is a research subject in terms of health and beauty and psychology. Melanin is divided into reddish-yellow pheomelanin and dark brown eumelanin. Melanin in hair is an important factor in determining the color of hair. After being delivered to cortical cell keratinocytes, it moves upward with hair growth. Gray hair, recognized as a phenomenon of physiological aging, is caused by a decrease in melanin production due to a decrease in the number of hair melanocytes and a decrease in the function of melanocytes. Currently, dyeing is used as a solution to gray hair, but dyeing is a temporary method and must be dyed again due to the growth of gray hair. is becoming a problem.

Collagen is a major matrix protein produced by fibroblasts of the skin and is present in the extracellular matrix. Its important functions include mechanical robustness of the skin, resistance and cohesiveness of connective tissue, support of cell adhesion, cell division and differentiation. (in the growth of organisms or wound healing), etc. are known. Such collagen is reduced by age and photoaging caused by ultraviolet irradiation, and collagen reduction is promoted by the activity of collagenase enzyme that decomposes collagen. It is known that it is closely related to the formation of wrinkles in the skin.

In addition, elastin fibers form cross-linked bonds with collagen and are an important skin component for wrinkle formation involved in skin elasticity. Deficiency and aggregation of elastin fibers and marked increase in the activity of elastase, an elastin degrading enzyme, have been found to be one of the causes of skin wrinkles. Elastase is the only enzyme capable of decomposing elastin, and inhibition of it is known to fundamentally reduce skin wrinkle improvement.

On the other hand, collagen and elastin fibers are matrix proteins that play an important role in retaining moisture in the dermal layer, and these matrix proteins adsorb moisture and increase the moisture retention within the structure they form so that the skin can maintain an appropriate moisture state. It is known to be involved in maintaining skin elasticity.

In addition, elastic fibers generated from fibroblasts of the skin form cross-linked bonds with collagen and are an important skin component for wrinkle formation involved in skin elasticity. Deficiency and decomposition of elastic fibers have been found to be one of the main causes of wrinkle formation and deterioration of skin elasticity.

Fibrillin-1 protein, which makes up elastic fibers, is a type of microfibril that exists on the outside of cells and is known to play a role in forming a scaffold when elastic fibers are formed. Fibrillin acts like an adhesive and helps each part of our body to be combined and maintained. known to be the cause. Recently, it has been found that fibrillin-1 acts as a TGF-beta reservoir.

Currently, retinoids, adenosine, animal placenta-derived proteins, chlorella extracts, and the like are known as wrinkle-improving cosmetics. Retinol, the most well-known, is a substance that promotes collagen synthesis and inhibits the elastase enzyme, but is unstable and has limitations in usage due to safety issues such as irritation and redness when applied to the skin. It is known that it is difficult to expect wrinkle improvement effects.

Glycation generally refers to a reaction in which a simple sugar such as glucose or fructose forms a covalent bond with a protein or fat that occurs without the involvement of enzymes. Glycation occurs through a series of complex chemical reactions known as Amadori-rearrangements and Maillard-reactions, resulting in advanced glycation endproducts (AGEs).

On the other hand, the glycosylation process of protein occurs slowly because enzyme action is not involved, and as a result, it has more effect on proteins with a long half-life such as collagen. As a result of the analysis of advanced glycation end products, it was shown that as the age increases, glycated collagen accumulates. By preventing collagen from forming its proper structure, it loses skin elasticity and promotes wrinkle formation (Dyer, DG et al. , The Journal of Clinical Investigation, 9, p. 2463, 1993).

Aminoguanidine, Pyridoxamine, and Aspirin are known as substances that inhibit glycation, but these substances have limitations in usage due to safety issues on the skin, or are ineffective due to insignificant effects. There are problems that cannot be expected.

Inflammation is an immune response of the human body in response to wounds or diseases, and oxidative stress such as ultraviolet rays, active oxygen, and free radicals activate inflammatory factors to cause various diseases and aging of the skin. Vasoactive polypeptides, such as Kinin, Plasmin, and Complement, act on vasodilation, contraction, and chemotaxis, and other lymphocytes such as interleukin-6 (IL-6) Phosphorus and arachidonic acid are responsible for the inflammatory response. Arachidonic acid is metabolized into prostaglandin or leukotrienes, which are inflammatory mediators, through two pathways, cyclooxygenase and lipooxygenase, to mediate various inflammatory reactions.

On the other hand, in order to disappear inflammation, it is called an anti-inflammatory agent that acts to remove the inflammatory source and reduce the physiological response and symptoms. Substances that have been used for the purpose of anti-inflammation so far include flufenamic acid, ibuprofen, benzydamine, and indomethacin as nonsteroids and prednisolone as steroids. , Dexamethasone, and the like. In addition, allantoin, Azene, hydrocortisone, etc. are known to be effective in improving inflammation, but these substances have a problem in that the amount of use is limited due to safety problems on the skin, or the effect is insignificant, so that the anti-inflammatory effect cannot be expected. there is.

Therefore, it is safe for the body, active ingredients are safe and stable for the skin, and above all, anti-glycation, darkening, wrinkle improvement, elasticity improvement, or anti-wrinkle effect are superior to previously known substances on the skin. Improvement, elasticity improvement, or development of an anti-inflammatory component is desperately desired.

Therefore, the problem to be solved by the present invention is to solve the above problems, and to solve the above problems, and while being safe to the human body, anti-glycation, blackening, wrinkle improvement, elasticity improvement or anti-inflammatory effect of the new active ingredient, that is, the active ingredient It serves a useful purpose.

In other words, the 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 problems, the present invention provides a cosmetic composition or pharmaceutical composition containing ethyl ferulate or a pharmaceutically or cosmetically acceptable salt thereof as an active ingredient.

In addition, the present invention is for blackening of skin or hair, for enhancing skin elasticity, for improving skin wrinkles, for moisturizing skin or for skin containing ethyl ferulate or a pharmaceutically or cosmetically acceptable salt thereof as an active ingredient An anti-inflammatory composition, preferably a cosmetic composition, pharmaceutical composition or health food is provided.

That is, the present invention relates to the use of ethyl ferulate or a pharmaceutically or cosmetically acceptable salt thereof as a cosmetic composition or pharmaceutical composition, and for darkening skin or hair, enhancing skin elasticity, improving skin wrinkles, moisturizing skin or skin It provides a new use called anti-inflammatory.

The inventors of the present invention found that ethyl ferulate promotes collagen production in the skin and inhibits the activity of elastase, thereby improving wrinkles and elasticity of the skin, and completed the present invention. In addition, it was confirmed that the ethyl ferulate increases the total amount of melanin to show a blackening effect of skin or hair, and also exhibits an anti-inflammatory effect by inhibiting NO production. In addition, the ethyl ferulate exhibits an anti-glycation effect and acts as an auxiliary role in improving skin wrinkles and skin elasticity, thereby exhibiting a synergistic effect.

In the present invention, the 'blackening effect' means that the color pigment of the skin or hair is increased, and in particular, it may mean a phenomenon in which the amount of melanin pigment is increased so that the skin or hair shows a dark color. The invention is not limited by these mechanisms.

In the present invention, 'improvement of elasticity or skin elasticity' means alleviating the degree of sagging or sagging of the skin. In addition, the elasticity means maintaining the elasticity of the skin in a state in which elastin and collagen are sufficiently present.

In the present invention, 'wrinkle improvement' refers to preventing, suppressing, or inhibiting the formation of wrinkles on the skin, or alleviating wrinkles that have already been created.

In the present invention, 'moisturizing or skin moisturizing' means to increase the feeling of moisture in the skin and to maintain a moist state. The skin moisturizing effect can help improve wrinkles and increase elasticity of the skin.

In the present invention, the term 'anti-inflammatory effect' refers to suppressing inflammation, and the inflammation is one of the defense reactions of living tissues to certain stimuli, which causes tissue deterioration, circulatory disorder and exudation, and tissue proliferation. refers to complex lesions. More specifically, inflammation is part of innate immunity, and as in other animals, innate immunity in humans recognizes cell surface patterns that are specific to pathogens. Phagocytes recognize cells with such surfaces as non-self and attack the pathogen. If a pathogen breaks through the body's physical barrier, an inflammatory response occurs. The inflammatory response is a non-specific defense action that creates a hostile environment for microorganisms invading the wound. In the inflammatory response, when a wound or an external infectious agent enters the body, white blood cells in charge of the early stage immune response flock to express cytokines. Therefore, the expression level of intracellular cytokines is an indicator of activation of the inflammatory response. Examples of skin diseases related to inflammation include atopic dermatitis, psoriasis, erythematous diseases triggered by radiation, chemicals, burns, etc., acid burns, bullous dermatosis, lichenoid type diseases, itching due to allergies, seborrheic eczema, rosacea, pemphigus vulgaris, exudative erythema multiforme, erythema nodosum, balanitis, vulvitis, inflammatory hair loss such as alopecia areata, cutaneous T-cell lymphoma, etc., but are not limited thereto.

In the present invention, the 'anti-glycation' effect refers to preventing collagen from being glycated in the extracellular matrix of the dermal layer, enhancing skin elasticity and preventing wrinkles. In addition, the anti-glycation effect suppresses the production of advanced glycation end products accumulated in the upper dermal layer according to skin aging. Therefore, in the present invention, the anti-glycation effect can generate a synergistic effect in enhancing skin elasticity and improving wrinkles.

The present invention provides a composition comprising a compound represented by Formula 1 or a pharmaceutically or cosmetically acceptable salt thereof in order to solve the above problems and achieve the object of the present invention.

[Formula 1]

The compound represented by Chemical Formula 1 has a molecular formula C ₁₂ H ₁₄ O ₄ , molecular weight: 222.24, and is ethyl ferulate; It is named Ethyl 3-(4-hydroxy-3-methoxyphenyl)acrylate.

The present invention is not particularly limited to the method for obtaining the ethyl ferulate, and chemically synthesized by a known method in the field to which the present invention belongs, or a commercially available material may be used.

In the cosmetic composition, pharmaceutical composition and health food according to the present invention, the content of ethyl ferulate or a pharmaceutically or cosmetically acceptable salt thereof is 0.00001 to 10% by weight relative to the total weight of the cosmetic composition, pharmaceutical composition and health food It is desirable to be

In the present invention, the ethyl ferulate used as an active ingredient may be used in the form of a "pharmaceutically or cosmetically acceptable salt". The “pharmaceutically or cosmetically acceptable salt” of ethyl ferulate may include salts prepared by adding a base to ethyl ferulate. 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 acids. .

The ethyl ferulate of the present invention may exist in unsolvated as well as solvated forms, including hydrates, ethanolates, and the like. The ethyl ferulate 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 blackening skin or hair, for enhancing skin elasticity, for improving skin wrinkles, for moisturizing skin, or for anti-inflammatory skin according to the present invention is a solution, an external ointment, a cream, a foam, a nutrient lotion, a softening lotion, a pack, softening water, and an emulsion. , makeup base, essence, soap, liquid cleanser, bath additive, sun screen cream, sun oil, suspension, emulsion, paste, gel, lotion, powder, soap, surfactant-containing cleanser, oil, powder foundation, emulsion foundation , wax foundation, it may be prepared as a formulation selected from the group consisting of patches and sprays, but is not limited thereto.

In addition, the cosmetic composition of the present invention may further include one or more cosmetically acceptable carriers formulated in general skin cosmetics, and as typical ingredients, for example, oil, water, surfactants, moisturizers, lower alcohols, A thickener, a chelating agent, a colorant, a preservative, a flavoring agent, and the like may be suitably blended, but are not limited thereto.

Cosmetically acceptable carriers included in the cosmetic composition of the present invention vary depending on the formulation. When the formulation of the present invention is an ointment, paste, cream or gel, animal oil, vegetable oil, wax, paraffin, starch, tracanth, cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc, zinc oxide or Mixtures of these may be used.

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

When the formulation of the present invention is a solution or emulsion, a solvent, solubilizing agent, or emulsifying agent is used as a carrier component, such as water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl benzoate, propylene glycol, 1,3 -There is butyl glycol oil, in particular cottonseed oil, peanut oil, corn germ oil, olive oil, castor oil and sesame oil, glycerol aliphatic ester, polyethylene glycol or fatty acid ester of sorbitan.

When the dosage form of the present invention is a suspension, a liquid diluent such as water, ethanol or propylene glycol, a suspending agent such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester, a micro Crystalline cellulose, aluminum metahydroxide, bentonite, agar or tracanth and the like may be used.

When the formulation of the present invention is a soap, alkali metal salts of fatty acids, fatty acid hemiester salts, fatty acid protein hydrolyzates, isethionates, lanolin derivatives, aliphatic alcohols, vegetable oils, glycerol, sugars, etc. may be used as carrier components. can

The present invention also relates to skin or hair blackening, skin elasticity enhancement, skin wrinkle improvement, skin moisturizing or Provides a skin anti-inflammatory method. The subject includes, without limitation, mammals including mice, livestock, humans, and the like.

According to another embodiment of the present invention, the present invention is for blackening skin or hair, enhancing skin elasticity, and improving skin wrinkles containing the compound of Formula 1 or a pharmaceutically or cosmetically acceptable salt thereof as an active ingredient. , It provides a pharmaceutical composition for skin moisturizing or skin anti-inflammatory.

A composition containing the compound of the present invention may be in various oral or parenteral formulations, but may preferably be a parenteral formulation. When formulated, it is prepared using diluents or excipients such as commonly used fillers, extenders, binders, wetting agents, disintegrants, and surfactants. Solid preparations for oral administration include tablets, pills, powders, granules, capsules, etc., and these solid preparations include at least one excipient in one or more compounds, for example, starch, calcium carbonate, sucrose or lactose ( lactose) and gelatin. In addition to simple excipients, lubricants such as magnesium stearate and talc are also used. Liquid preparations for oral administration include suspensions, solutions for oral administration, emulsions, syrups, etc. In addition to water and liquid paraffin, which are commonly used simple diluents, various excipients such as wetting agents, sweeteners, aromatics, and preservatives may be included. there is. Formulations for parenteral administration include sterilized aqueous solutions, non-aqueous solutions, suspensions, and emulsions. Propylene glycol, polyethylene glycol, vegetable oils such as olive oil, and injectable esters such as ethyl oleate may be used as non-aqueous solvents and suspending agents.

The present invention is also directed to skin or hair blackening, skin elasticity enhancement, skin wrinkle improvement, skin moisturizing, or skin anti-inflammatory, comprising the compound of Formula 1 or a pharmaceutically or cosmetically acceptable salt thereof as an active ingredient. It can be provided in the form of an external skin preparation.

When the compound of Formula 1 or a pharmaceutically or cosmetically acceptable salt thereof is used as an external skin preparation, additionally a fatty substance, an organic solvent, a solubilizing agent, a thickening agent and a gelling agent, a softening agent, an antioxidant, a suspending agent, and a stabilizer , foaming agents, fragrances, surfactants, water, ionic or nonionic emulsifiers, fillers, sequestering agents and chelating agents, preservatives, vitamins, blocking agents, wetting agents, essential oils, dyes, pigments, hydrophilic or It may contain adjuvants commonly used in the field of dermatology, such as lipophilic actives, lipid vesicles, or any other ingredients commonly used in external preparations for the skin. In addition, the components may be introduced in an amount generally used in the field of skin science.

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

The pharmaceutical composition of the present invention can be particularly preferably used as a parenteral preparation, and for example, the external skin preparation may include a suitable pharmaceutically acceptable base such as petrolatum and stearyl alcohol; suitable pharmaceutically acceptable surfactants such as polysorbate and sorbitan sesquioleate; suitable pharmaceutically acceptable moisturizers such as glycerin; suitable pharmaceutically acceptable solvents; and a flavoring agent, a colorant, a stabilizer, a viscosifying agent, and the like can be prepared by a conventional method for preparing an external preparation for skin.

In addition, when the compound represented by Formula 1 or a pharmaceutically or cosmetically acceptable salt thereof of the present invention is used as a pharmaceutical, it may additionally contain one or more active ingredients exhibiting the same or similar functions. For example, it may include known ingredients for blackening skin or hair, enhancing skin elasticity, improving skin wrinkles, moisturizing the skin, or anti-inflammatory skin. When additional skin or hair blackening, skin elasticity enhancement, skin wrinkle improvement, skin moisturizing or skin anti-inflammatory components are included, the composition of the present invention blackens skin or hair, enhances skin elasticity, improves skin wrinkles, and moisturizes the skin. Alternatively, the skin anti-inflammatory effect may be further enhanced. When adding the above components, skin safety according to combined use, ease of formulation, and stability of active ingredients may be considered.

In one embodiment of the present invention, the composition is a skin elasticity or wrinkle improvement component known in the art, retinoic acid, TGF, protein derived from animal placenta, betulinic acid and chlorella extract; Anti-inflammatory ingredients known in the art include COX-2 inhibitors, prednisolone and allantoin; As moisturizing ingredients known in the art, petrolatum (vaseline), mineral oil, silicone, neutral fat, essential fatty acids (eg gamma linolenic acid (evening primrose oil)), GGF, amino acids, provitamin B5, hyaluronic acid, poly- γ-glutamic acid, Lipidure PMB, ceramides, cholesterol, fatty acids; And it may further include one or two or more components selected from the group consisting of derivatives thereof and various plant extracts. The additional component may be included in an amount of 0.0001% to 10% by weight based on the total weight of the composition, and the content range may be adjusted according to requirements such as skin safety and ease of formulation of the compound of Formula 1.

The pharmaceutical composition of the present invention, when containing an effective amount of the compound of Formula 1 or a pharmaceutically or cosmetically acceptable salt thereof, has desirable effects of blackening skin or hair, enhancing skin elasticity, improving skin wrinkles, moisturizing skin or anti-inflammatory skin. can provide. In the present invention, the term 'effective amount' refers to 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 effects.

An effective amount of the compound of Formula 1 or a pharmaceutically or cosmetically acceptable salt thereof included in the composition of the present invention will vary depending on the form in which the composition is commercialized, how the compound is applied to the skin, and how long it stays on the skin. For example, when the composition is commercialized as a pharmaceutical product, it may contain the compound of Formula 1 at a higher concentration than when the composition is commercialized as a cosmetic product that is routinely applied to the skin. Therefore, the daily dose 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, and 1 to 100 mg/kg per day. 6 doses may be administered.

According to another embodiment of the present invention, the compound of Formula 1 or a pharmaceutically or cosmetically acceptable salt thereof is used for darkening skin or hair, enhancing skin elasticity, improving skin wrinkles, moisturizing skin, or treating skin problems. Provides health food for inflammation.

In the present specification, 'health food' means that the compound of Formula 1 or a pharmaceutically or cosmetically acceptable salt thereof is added to food materials such as beverages, teas, spices, chewing gum, confectionery, etc., or encapsulated, powdered, suspended, etc. It is a food manufactured with , which means that it brings a specific effect on health when ingested, but unlike general medicines, it has the advantage of not having side effects that can occur when taking medicines for a long time by using food as a raw material. Since the health food of the present invention obtained in this way can be consumed on a daily basis, excellent effects can be expected for blackening of the skin or hair, promotion of skin elasticity, improvement of skin wrinkles, skin moisturizing, or skin anti-inflammatory, and is very useful.

When the compound of Formula 1 or a pharmaceutically or cosmetically acceptable salt thereof is used as a food additive, the compound of Formula 1 or a pharmaceutically or cosmetically acceptable salt thereof is added as it is or mixed with other foods or food ingredients. can be used together, and can be used appropriately according to a conventional method. The mixing amount of the active ingredient may be appropriately determined depending on the purpose of use (prevention, health or therapeutic treatment). In general, when preparing food or beverage, the composition of the present invention is added in an amount of 15 parts by weight or less, preferably 10 parts by weight or less, based on the raw material. However, in the case of long-term intake for the purpose of health and hygiene or health control, 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 above the above range. . There is no particular limitation on the type of food. Examples of foods to which the substance can be added include meat, sausage, bread, chocolate, candy, snacks, confectionery, pizza, ramen, other noodles, gum, dairy products including ice cream, various soups, beverages, tea, drinks, There are alcoholic beverages and vitamin complexes, and includes all health foods in a conventional sense. The health beverage composition of the present invention may contain various flavoring agents or natural carbohydrates as additional components, like conventional beverages. The aforementioned natural carbohydrates include monosaccharides such as glucose and fructose, disaccharides such as maltose and sucrose, polysaccharides such as dextrin and cyclodextrin, and sugar alcohols such as xylitol, sorbitol, and erythritol. As the sweetener, natural sweeteners such as thaumatin and stevia extract, or synthetic sweeteners such as saccharin and aspartame may be used. The proportion 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 includes various nutrients, vitamins, electrolytes, flavors, colorants, pectic acid and its salts, alginic acid and its salts, organic acids, protective colloidal thickeners, pH adjusters, stabilizers, preservatives, glycerin, alcohol , carbonation agents used in carbonated beverages, and the like. In addition, the health food of the present invention may contain fruit flesh for the production of natural fruit juice, fruit juice beverages and vegetable beverages. These components may be used independently or in combination. The ratio of these additives is not very important, 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.

Although not limited thereto, in one embodiment of the present invention, the composition may include the compound of Formula 1 or a pharmaceutically or cosmetically acceptable salt thereof in an amount of 0.00001% to 10% by weight based on the total weight of the composition. there is.

The composition containing ethyl ferulate of the present invention shows excellent effects on skin or hair blackening, skin elasticity enhancement, skin wrinkle improvement, skin moisturizing or skin anti-inflammatory.

The composition containing ethyl ferulate of the present invention can be used as a cosmetic raw material, pharmaceutical ingredient, or health food raw material that is safe for the skin and has excellent skin condition improvement effects.

Hereinafter, the following examples and the like will be described in order to explain the present invention in more detail. However, embodiments according to the present invention can be modified in many different forms, and the scope of the present invention should not be construed as being limited to the embodiments described below. Embodiments of the present invention are provided by way of example to help a detailed understanding of the present invention.

reference example 1: ethyl ferule (Ethyl ferulate ) substance information

[Formula 1]

Substance Name : Ethyl ferulate; Ethyl 3-(4-hydroxy-3-methoxyphenyl)acrylate

CAS No. :4046-02-0

Molecular Formula: C ₁₂ H ₁₄ O ₄

Molecular Weight: 222.24

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

Experimental example 1: Effect of promoting synthesis of type I collagen in human-derived fibroblasts

The compound of Formula 1 was added to the culture medium of human-derived fibroblasts to confirm the effect of promoting type 1 collagen synthesis at the cellular level. The measurement of synthesized collagen was quantified using a PICP EIA kit (Procollagen Type I C-Peptide Enzyme Immuno Assay KIT). In order to measure the amount of collagen synthesis, the compound of Formula 1 was added to the culture medium (DMEM medium) of fibroblasts, cultured for 48 hours, and then the culture medium was taken and the degree of type 1 collagen synthesis at each concentration was measured using a PICP EIA kit using a spectrophotometer. and measured at 450 nm.

For comparison of the effect, the degree of collagen synthesis was measured in the same manner for the samples to which the culture medium of untreated fibroblasts (negative control) and vitamin C (positive control) were added to a final concentration of 52.85 μg/ml. The rate of increase in collagen production was calculated as the ratio of the amount of collagen production relative to the control group, and the results are shown in Table 1 below.

Collagen synthesis promoting effect of the compound of formula 1 (number of repetitions = 4)

sample Type 1 collagen production (ng/ml) Increase (%) negative control group 150.2 - Positive control group (vitamin C, 52.85 ppm) 246.8 64.3 Compound of Formula 1 (1 ppm) 185.4 23.4 Compound of Formula 1 (10 ppm) 217.4 44.7

As can be seen from the results of Table 1, when the compound of Formula 1 was treated, the amount of collagen synthesis was increased in a concentration-dependent manner, and in general, similar collagen at a lower concentration than when vitamin C, which is well known to induce collagen synthesis, was applied. synthetic effect was shown.

Experimental Example 2: Elastase activity inhibitory effect

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

Elastase derived from human leukocytes was used, and a synthetic substrate MeOSuc-Ala-Ala-Pro-Val-pNA was used as a substrate for the elastase. A 100 mM Tris (pH 7.5) solution was used as the buffer solution. Elastase was finally used at 0.2 mU using a buffer solution. In addition, the synthetic substrate of Elastase was diluted with a buffer solution to a final concentration of 0.5 mM after making a 100 mM solution using DMSO. At this time, as a positive control group, quercetin known as an elastase inhibitor was set at a concentration of 10 ppm. The elastase inhibitory candidate was added to a final concentration of 10 or 20 ppm. The reaction was carried out in a 96-well plate and reacted at room temperature for 20 minutes. The absorbance was measured at 405 nm at 1-minute intervals using a spectrophotometer, and the slope of the absorbance versus time was determined to determine the activity of the enzyme. The elastase inhibition rate was calculated as follows.

Elastase activity inhibitory effect of the compound of Formula 1 (number of repetitions = 3)

sample enzyme activity Inhibition rate (%) Compound of Formula 1 (20 ppm) 2.8 73.08 Compound of Formula 1 (10 ppm) 4.8 53.85 Positive control group (Quercetin, 10ppm) 3.5 66.35 Control (DMSO, 20 ppm) 10.4 -

As can be seen from the results in Table 2, the compound of Formula 1 showed an elastase activity inhibitory effect corresponding to that of the positive control, quercetin, at a concentration of 10 ppm, and at a concentration of 20 ppm, elastase superior to quercetin. As a result, it was confirmed that the compound of Formula 1 has an excellent elastase activity inhibitory effect. Accordingly, it was found that the compound of Formula 1 can be effectively used for improving skin elasticity and wrinkles.

Experimental example 3: glycosylation inhibition (anti- glycation ) effect

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

First, 1M L-arginine and 1M glucose were dissolved in 1M phosphate buffer (pH 7.4), and samples were diluted to 50 and 100 ppm using 1M phosphate buffer. 1M L-arginine and 1M phosphate buffer were mixed at a ratio of 1:4, and then 80 μl was dispensed into a 96-well plate. Samples diluted to 50 and 100 ppm, respectively, and 100 μl of 0.01 M aminoguanidine to be used as a positive control were added thereto. After mixing these samples well, finally, after adding glucose diluted with 1M phosphate buffer so that the final concentration of glucose is 0.1M, the mixture was reacted at 70°C for 4 hours. The degree of glycosylation was measured by measuring the absorbance at 420 nm of the 96-well plate using a spectrophotometer.

The Glycation experimental group of the following formula is an experimental group in which 1M L-arginine and 1M glucose are added to induce glycation. The glycosylation inhibitory activity can be obtained in the following way.

Anti-glycation effect of the compound of Formula 1

sample Inhibition rate (%) Control (DMSO, 50 ppm) - Positive control group (Aminoguanidine, 55ppm) 54.89 Compound of Formula 1 (50 ppm) 69.98 Compound of Formula 1 (25 ppm) 42.11

As can be seen from the results in Table 3, it was found that the compound of Formula 1 has a more excellent anti-glycation effect than aminoguanidine known as an anti-glycation substance. That is, the compound of Formula 1 exhibits an excellent antiglycation effect, and in improving skin wrinkles and elasticity, the antiglycation effect acts as an auxiliary role, and a synergistic effect can be expected.

Experimental example 4: blackening Effect - the effect of increasing the total amount of melanin

The compound of Chemical Formula 1 was added to the culture medium of mouse melanoma cells (B-16 mouse melanoma cells), and the blackening effect was confirmed by measuring the total amount of melanin at the cellular level (Lotan R., Lotan D. Cancer Res . 40: 3345-3350, 1980). Before the experiment, toxicity was evaluated for melanoma cells of mice, and blackening was evaluated by selecting a non-toxic concentration.

The compound of Formula 1 was added to the culture medium to a final concentration of 1 ppm and 10 ppm, and Forskolin, a control, was added to the medium to be 10 ppm, treated with B-16 melanoma cells, respectively, and cultured for 3 days.

Thereafter, the cells were treated with trypsin, detached from the culture vessel, centrifuged, and then melanin was extracted. The detached cells were boiled for 10 minutes by adding 1 ml of sodium hydroxide solution (1N concentration) 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 a method of expressing absorbance per unit cell number (1×10 ⁶ cell), and the total amount of melanin relative to the control group was calculated as an increase rate (%), and the results are summarized in Table 4 below.

The effect of increasing the total amount of melanin at the cellular level according to the concentration

sample Amount of melanin produced (abs) Increase (%) Control (DMSO, 10 ppm) 0.33 - Positive control group (Forskolin, 10ppm) 0.792 140 Compound of Formula 1 (10 ppm) 0.515 56 Compound of Formula 1 (1 ppm) 0.427 29.4

As can be seen from the results in Table 4, it can be seen that the compound of Formula 1 exhibits a significantly superior effect of increasing the total amount of melanin even at 10 ppm, compared to the positive control, forskolin, and can be used for blackening of skin or hair. there was.

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

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

Specifically, RAW264.7 cells, which are mouse macrophages, were subcultured several times, placed in a 24-well plate so that 3×10 ⁵ per well, and cultured for 24 hours. Subsequently, the cell medium was replaced with a diluted compound of Formula 1 at final concentrations of 1, 10, and 100 ppm. At this time, L-NMMA (L-NG-Monomethylarginine), an NO-production inhibitor, was treated as a positive control and cultured for 30 minutes, and LPS (Lipopolysaccharide) was treated as a stimulus at 1 μg each and cultured for 24 hours. . 100 μl of the supernatant was transferred to a 96-well plate, 100 μl of the GRIESS solution was added and reacted 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, and the result are shown in Table 5 below.

sample NO production inhibition rate (%) Control (DMSO, 10 ppm) - L-NMMA (positive control, 10 ppm) 41.02 Compound of Formula 1 (1 ppm) 14.62 Compound of Formula 1 (10 ppm) 18.83 Compound of Formula 1 (100 ppm) 56.05

As can be seen from the results of Table 5, the compound of Formula 1 exhibited a significant NO production inhibition rate as a natural substance compared to L-NMMA, a representative anti-inflammatory drug. Therefore, it was confirmed that Formula 1 can be effectively used for skin anti-inflammatory and skin trouble improvement purposes. In addition, the anti-inflammatory effect can be expected to have a synergistic effect by acting as an auxiliary role in improving skin elasticity or wrinkles.

Claims (6)

A composition for blackening skin or hair comprising a compound represented by Formula 1 below or a pharmaceutically or cosmetically acceptable salt thereof as an active ingredient.
[Formula 1]

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

An anti-inflammatory composition for skin comprising a compound represented by Formula 1 below or a pharmaceutically or cosmetically acceptable salt thereof as an active ingredient.
[Formula 1]

The composition according to any one of claims 1 to 3, 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 3, wherein the compound represented by 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 method according to any one of claims 1 to 3, wherein the compound of Formula 1 or a pharmaceutically or cosmetically acceptable salt thereof contained in the composition exhibits an anti-glycation effect as well. composition to be.