KR20200127661A - Composition for improving skin wrinkels or enhancing skin elasticity comprising dehydro-trametenolic acid and compound k - Google Patents

Abstract

The present specification discloses a composition for improving skin wrinkles or enhancing skin elasticity, comprising dehydrogenated tramethenolic acid and compound K as active ingredients. Specifically, by containing a mixture of dehydrogenated tramethenolic acid and Compound K as an active ingredient, skin cell proliferation, promotion of collagen production, and lipofuscin accumulation inhibiting effect without causing skin side effects are excellent for skin wrinkle improvement or skin A composition for enhancing elasticity is disclosed.

Description

A composition for improving skin wrinkles or enhancing skin elasticity containing dehydrogenated tramethenolic acid and compound K {COMPOSITION FOR IMPROVING SKIN WRINKELS OR ENHANCING SKIN ELASTICITY COMPRISING DEHYDRO-TRAMETENOLIC ACID AND COMPOUND K}

The present invention relates to a composition for improving skin wrinkles or enhancing skin elasticity comprising dehydrogenated tramethenolic acid and compound K as active ingredients.

The skin is the primary barrier of the human body, and it protects the internal organs from changes in temperature and humidity, and from external stimuli such as ultraviolet rays and pollutants, and plays an important role in maintaining biological homeostasis such as body temperature control. However, excessive physical and chemical stimuli, stress, and nutritional deficiencies received from the outside deteriorate the normal function of the skin and promote skin aging such as loss of elasticity, keratinization, and wrinkle formation. In order to maintain a healthy skin, efforts have been made to effectively suppress skin aging by maintaining the skin's intrinsic function and activating skin cells by using cosmetic products enhanced with physiologically active substances obtained from various plants and microorganisms.

However, most of the existing cosmetic ingredients have various problems, such as poor efficacy or causing skin side effects.

International Publication Patent No. 2018-045943 Korean Patent Publication No. 10-2014-0003198

In order to solve the above problems, the present invention contains a mixture of dehydrogenated tramethenolic acid and compound K as an active ingredient, thereby promoting skin cell proliferation, collagen production, and inhibiting lipofuscin accumulation without causing skin side effects. It is an object of the present invention to provide a composition for improving skin wrinkles or improving skin elasticity.

In order to achieve the above object, one aspect of the present invention, dehydrogenated tramethenolic acid, a stereoisomer thereof, a salt thereof, a hydrate or a solvate thereof; And

Compound K, its stereoisomer, its salt, its hydrate or its solvate; provides a composition for improving skin wrinkles or enhancing skin elasticity, comprising as an active ingredient.

The composition according to an aspect of the present invention may exhibit excellent skin wrinkle improvement or skin elasticity enhancement effect.

The composition according to an aspect of the present invention may exhibit an excellent effect of improving skin wrinkles or enhancing skin elasticity without causing skin side effects.

The composition according to an aspect of the present invention may exhibit excellent skin cell or fibroblast proliferation effect without causing skin side effects.

The composition according to an aspect of the present invention may exhibit excellent collagen biosynthesis promoting effect without causing skin side effects.

The composition according to an aspect of the present invention may exhibit excellent lipofuscin accumulation inhibitory effect without causing skin side effects.

The composition according to an aspect of the present invention may exhibit a remarkably superior effect of improving skin wrinkles or enhancing skin elasticity compared to each of dehydrogenated tramethenolic acid and compound K.

Hereinafter, the present invention will be described in detail.

One aspect of the present invention comprises a mixture of dehydro trametenolic acid and Compound K as an active ingredient, thereby promoting skin cell proliferation, collagen production, and lipofuscin ( It is an object of the present invention to provide a composition for improving skin wrinkles or enhancing skin elasticity, which has an excellent effect of inhibiting accumulation of Lipofuscin). In order to achieve the above object, an aspect of the present invention provides a composition for skin anti-aging comprising dehydrogenated tramethenolic acid represented by Formula 1 and Compound K represented by Formula 2 as an active ingredient.

In the present specification, dehydrogenated tramethenolic acid may be represented by the following formula (1).

[Formula 1]

In the present specification, compound K may be represented by the following formula (2).

[Formula 2]

In one aspect, the present invention provides, in one aspect, dehydrogenated tramethenolic acid, a stereoisomer thereof, a salt thereof, a hydrate thereof, or a solvate thereof; And Compound K, its stereoisomer, its salt, its hydrate or its solvate; as an active ingredient, it may relate to a composition for improving skin wrinkles or improving skin elasticity.

In the present specification, "stereoisomers" are isomers having the same molecular formula and order of connection, but different arrangements of atoms in a three-dimensional space, and may be diastereomers and optical isomers. In addition, the diastereomer may be a geometric isomer and a diastereomer other than the geometric isomer.

In the present specification, "salt" refers to a salt that is acceptable as a pharmaceutical or cosmetic, and the term "acceptable as a pharmaceutical or cosmetic" is generally safe and non-toxic, and is useful for preparing a biologically or otherwise desirable pharmaceutical composition. And, it means that it is useful not only for veterinary use, but also for pharmaceutical and cosmetic uses for humans. The term "pharmaceutically or cosmetically acceptable" refers to a salt which is pharmaceutically or cosmetically acceptable and has a desired pharmacological activity as defined above. Such salts include (1) inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, or the like, or organic acids such as acetic acid, propionic acid, hexanoic acid, cyclopentanpropionic acid, glycolic acid, pyruvic acid, lactic acid, malonic acid, and stone. Sinic acid, malic acid, maleic acid, fumaric acid, tartaric acid, citric acid, benzoic acid, 3-(4-hydroxybenzoyl)benzoic acid, cinnamic acid, mandelic acid, methanesulfonic acid, ethanesulfonic acid, 1,2-ethane-disulfonic acid, 2-hydroxyethanesulfonic acid, benzene sulfonic acid, 4-chlorobenzenesulfonic acid, 2-naphthalenesulfonic acid, 4-toluenesulfonic acid, camphorsulfonic acid, 4-methylbicyclo[2.2.2]-oct-2- Formed by en-1-carboxylic acid, glucoheptonic acid, 3-phenylpropionic acid, trimethylacetic acid, tert-butylacetic acid, lauryl sulfuric acid, gluconic acid, glutamic acid, hydroxynaphtic acid, salicylic acid, stearic acid, muconic acid, etc. Acid addition salts; Or (2) a salt formed when an acidic proton present in the parent compound is replaced.

In the present specification, the "hydrate" means "a pharmaceutically or cosmetically acceptable hydrate". The "hydrate" exists when the compound of the present invention contains water. Hydrates may contain one or more water molecules per molecule of the compound of the present invention. Examples include, but are not limited to, monohydrate, dihydrate, trihydrate, and tetrahydrate. Hydrates may contain more than one molecule of a compound of the present invention per molecule of water. Examples include, but are not limited to, semi-hydrate. In one embodiment, water can be retained in the crystal in a variety of ways, so that water molecules can occupy a lattice position in the crystal, or form bonds with salts of the compounds described above. Baggage must be "acceptable" in the sense that it is not harmful to its accommodation.

In the present specification, "solvate" means "a pharmaceutically or cosmetically acceptable solvate", and the "solvate" refers to one or more pharmaceutically or cosmetically acceptable solvents of the present invention. Means to contain. The solvate may contain one or more solvent molecules per molecule of the compound of the present invention, or may contain one molecule of the compound of the present invention per molecule of solvent. In one embodiment, the solvent may be retained in the crystal in a variety of ways, so that water molecules may occupy a lattice position within the crystal, or form bonds with salts of the compounds described above.

In one embodiment of the present invention, the dehydrogenated tramethenolic acid, its stereoisomer, its salt, its hydrate or its solvate; And Compound K, a stereoisomer thereof, a salt thereof, a hydrate thereof, or a solvate thereof; the weight ratio of 1: 1 to 15 may be included. Specifically, the weight ratio may be 1: 1 or more, 1: 2 or more, 1: 3 or more, 1: 4 or more, 1: 5 or more, 1: 5.5 or more, 1: 6 or more, or 1: 6.5 or more weight ratio, In addition, the weight ratio may be 1: 15 or less, 1: 14 or less, 1: 13 or less, 1: 12 or less, 1: 11 or less, 1: 10 or less, 1: 9 or less, 1: 8 or less, or 1: 7.5 or less. have. Preferably, the dehydrogenated tramethenolic acid and compound K may be included in a weight ratio of 1:5 to 10. When the weight ratio of dehydrogenated tramethenolic acid and compound K is within the above range, the effect of proliferation of skin cells or fibroblasts, the effect of promoting collagen biosynthesis, and the effect of inhibiting the accumulation of lipofuscin in skin cells may be remarkably excellent.

In addition, in the mixture of dehydrogenated tramethenolic acid and compound K, if the weight ratio of dehydrogenated tramethenolic acid: compound K is greater than or equal to 1:1, inhibition of accumulation of lipofuscin may be further increased compared to the case where the weight ratio is less than 1:1. In addition, when the weight ratio of dehydrogenated tramethenolic acid: compound K is 1:15 or less, the inhibition of accumulation of lipophosine may be further increased compared to the case where the weight ratio is more than 1:15.

In one embodiment of the present invention, the active ingredient may be included in 0.0001 to 1% by weight based on the total weight of the composition. Specifically, the active ingredient is 0.0001% by weight or more, 0.0005% by weight or more, 0.001% by weight or more, 0.005% by weight or more, 0.01% by weight or more, 0.05% by weight or more, 0.1% by weight or more, 0.3% by weight based on the total weight of the composition. It may be more than, 0.5% by weight or more, 0.7% by weight or more, or 0.9% by weight or more, and the active ingredient is 1% by weight or less, 0.9% by weight or less, 0.7% by weight or less, 0.5% by weight or less, based on the total weight of the composition, It may be 0.3 wt% or less, 0.1 wt% or less, 0.05 wt% or less, 0.01 wt% or less, or 0.001 wt% or less. If the content of the active ingredient is less than 0.0001% by weight, the effect of improving skin wrinkles and enhancing skin elasticity is weak, and if it exceeds 1% by weight, there is no significant increase in efficacy due to the increase in content, which is not economical.

In one embodiment of the present invention, the composition may improve skin wrinkles or improve skin elasticity through proliferation of skin cells or fibroblasts.

In one embodiment of the present invention, the composition may improve skin wrinkles or enhance skin elasticity by promoting collagen biosynthesis.

In one embodiment of the present invention, the composition may improve skin wrinkles or improve skin elasticity by inhibiting accumulation of lipofuscin in the skin. In another embodiment, the composition may improve skin tone by inhibiting the accumulation of lipofuscin in the skin. Lipofuscin interferes with DNA and RNA synthesis and protein synthesis, and is known to destroy cellular enzymes required for important chemical metabolic processes, and its inhibition is used to improve skin wrinkles, improve skin elasticity, or improve skin tone. It is an important factor in prevention.

In one embodiment of the present invention, the daily dosage of the active ingredient may be 1 to 100 mg/kg. Specifically, the daily dosage of the active ingredient is 1 mg/kg or more, 5 mg/kg or more, 10 mg/kg or more, 15 mg/kg or more, 20 mg/kg or more, 30 mg/kg or more, 40 mg /kg or more, 50 mg/kg or more, 60 mg/kg or more, 70 mg/kg or more, 80 mg/kg or more, or 90 mg/kg or more. In addition, the daily dose of the active ingredient is 100 mg/kg or less, 90 mg/kg or less, 80 mg/kg or less, 70 mg/kg or less, 60 mg/kg or less, 50 mg/kg or less, 40 mg/ It may be kg or less, 30 mg/kg or less, 20 mg/kg or less, 15 mg/kg or less, 10 mg/kg or less, or 5 mg/kg or less.

In one embodiment of the present invention, the daily dosage of the dehydrogenated tramethenolic acid, its stereoisomer, its salt, its hydrate or its solvate may be 0.125 to 12.5 mg/kg. Specifically, the daily dosage of the dehydrogenated tramethenolic acid, its stereoisomer, its salt, its hydrate or its solvate is 0.125 mg/kg or more, 0.3 mg/kg or more, 0.5 mg/kg or more, 1 mg/ kg or more, 1.2 mg/kg or more, 1.25 mg/kg or more, 1.5 mg/kg or more, 2 mg/kg or more, 3 mg/kg or more, 4 mg/kg or more, 6 mg/kg or more, 8 mg/kg or more Or 10 mg/kg or more, and 12.5 mg/kg or less, 10 mg/kg or less, 8 mg/kg or less, 6 mg/kg or less, 4 mg/kg or less, 3 mg/kg or less, 2 mg/ kg or less, 1.5 mg/kg or less, 1.25 mg/kg or less, 1.2 mg/kg or less, 1 mg/kg or less, 0.5 mg/kg or less, or 0.3 mg/kg or less.

In one embodiment of the present invention, the daily dosage of Compound K, its stereoisomer, its salt, its hydrate or its solvate may be 0.875 to 87.5 mg/kg. Specifically, the daily dosage of Compound K, its stereoisomer, its salt, its hydrate or its solvate is 0.875 mg/kg or more, 1 mg/kg or more, 5 mg/kg or more, 7 mg/kg or more, 8.5 mg/kg or more, 8.75 mg/kg or more, 9 mg/kg or more, 10 mg/kg or more, 20 mg/kg or more, 30 mg/kg or more, 40 mg/kg or more, 60 mg/kg or more, or 80 mg /kg or more, and also, 87.5 mg/kg or less, 80 mg/kg or less, 60 mg/kg or less, 40 mg/kg or less, 30 mg/kg or less, 20 mg/kg or less, 10 mg/kg or less, It may be 9 mg/kg or less, 8.75 mg/kg or less, 8.5 mg/kg or less, 7 mg/kg or less, 5 mg/kg or less, or 1 mg/kg or less.

In one embodiment of the present invention, the composition may be a cosmetic composition. The formulation of the cosmetic composition is not particularly limited, and may be appropriately selected depending on the intended purpose. For example, skin lotion, skin softener, skin toner, astringent, lotion, milk lotion, moisture lotion, nutrition lotion, massage cream, nutrition cream, moisture cream, hand cream, foundation, essence, nutrition essence, pack, soap, cleansing Foam, cleansing lotion, cleansing cream, body lotion, and may be prepared in one or more formulations selected from the group consisting of a body cleanser, but is not limited thereto.

When the formulation of the cosmetic composition is a paste, cream or gel, animal fibers, plant fibers, wax, paraffin, starch, tracanth, cellulose derivatives, polyethylene glycol, silicone, bentonite, silica, talc, or zinc oxide are used as carrier components. Can be.

When the formulation of the cosmetic composition is a powder or spray, lactose, talc, silica, aluminum hydroxide, calcium silicate, or polyamide powder may be used as a carrier component. In particular, in the case of a spray, additional chlorofluorohydrocarbon, Propellants such as propane/butane or dimethyl ether.

When the formulation of the cosmetic composition is a solution or emulsion, a solvent, a solvating agent or an emulsifying agent is used as a carrier component, such as water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1,3-butylglycol oil, glycerol aliphatic ester, polyethylene glycol or fatty acid ester of sorbitan.

When the formulation of the cosmetic composition is a suspension, liquid diluents such as water, ethanol or propylene glycol as carrier components, ethoxylated isostearyl alcohol, suspending agents such as polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester, crystallites Sex cellulose, aluminum metahydroxide, bentonite, agar or tracant, and the like can be used.

When the formulation of the cosmetic composition is a surfactant containing cleansing, as a carrier component, aliphatic alcohol sulfate, aliphatic alcohol ether sulfate, sulfosuccinic acid monoester, isethionate, imidazolinium derivative, methyltaurate, sarcosinate, fatty acid Amide ether sulfates, alkylamidobetaines, aliphatic alcohols, fatty acid glycerides, fatty diethanolamides, vegetable oils, linoline derivatives, or ethoxylated glycerol fatty acid esters may be used.

In one embodiment of the present invention, the cosmetic composition may further include functional additives and components included in general cosmetic compositions in addition to the added active ingredient. The functional additive may include a component selected from the group consisting of water-soluble vitamins, oil-soluble vitamins, polymer peptides, polymer polysaccharides, sphingo lipids, and seaweed extract.

In one embodiment of the present invention, the cosmetic composition may further include the functional additives and, if necessary, ingredients included in a general cosmetic composition. Other ingredients included include fats and oils, moisturizers, emollients, surfactants, organic and inorganic pigments, organic powders, ultraviolet absorbers, preservatives, fungicides, antioxidants, plant extracts, pH adjusters, alcohols, pigments, fragrances, blood circulation Examples include accelerators, cooling agents, restrictors, and purified water.

In one embodiment of the present invention, the composition may be a composition for external application for skin.

In one embodiment of the present invention, the composition may be a pharmaceutical composition. The pharmaceutical composition may be in various oral or parenteral dosage forms. In the case of formulation, it can be 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, soft or hard capsules, and the like, and these solid preparations include at least one excipient, such as starch, calcium carbonate, and sucrose, in one or more compounds. Alternatively, it may be prepared by mixing lactose, gelatin, or the like. In addition, in addition to simple excipients, lubricants such as magnesium stearate and talc may be used. Liquid preparations for oral administration include suspensions, liquid solutions, emulsions, syrups, etc., and various excipients, such as humectants, sweeteners, fragrances, and preservatives, are included in addition to water and liquid paraffin, which are commonly used simple diluents. I can. Preparations for parenteral administration may include sterilized aqueous solutions, non-aqueous solutions, suspensions, emulsions, freeze-dried preparations, and suppositories. As the non-aqueous solvent and the suspension solvent, propylene glycol, polyethylene glycol, vegetable oil such as olive oil, and injectable ester such as ethyl oleate may be used. As a base for suppositories, witepsol, macrogol, tween 61, cacao butter, laurin, glycerogelatin, and the like may be used.

In one embodiment of the present invention, the pharmaceutical dosage form of the composition may be used in the form of a pharmaceutically acceptable salt thereof, and may be used alone or in combination with other pharmaceutically active compounds as well as in an appropriate set. have. The salt is not particularly limited as long as it is pharmaceutically acceptable, and for example, hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, hydrofluoric acid, hydrobromic acid, formic acid acetic acid, tartaric acid, lactic acid, citric acid, fumaric acid, maleic acid, succinic acid, methanesulfonic acid , Benzenesulfonic acid, toluenesulfonic acid, naphthalenesulfonic acid, and the like can be used.

In one embodiment of the present invention, the determination of the dosage of the active ingredient is within the level of those skilled in the art, and the daily dosage of the drug includes the degree of progression of obesity, the onset time, age, health condition, complications, etc. of the subject to be administered. Depends on various factors, but on an adult basis, the composition may be administered by dividing 1 μg/kg to 200 mg/kg, preferably 50 μg/kg to 50 mg/kg, 1 to 3 times a day. In addition, the dosage is not intended to limit the scope of the present invention in any way.

The pharmaceutical composition according to an embodiment of the present invention, respectively, according to a conventional method, oral dosage forms such as powders, granules, tablets, soft or hard capsules, suspensions, emulsions, syrups, aerosols, ointments, and skin such as creams. It can be formulated and used in any form suitable for pharmaceutical preparations, including external preparations, suppositories, injections, and sterile injectable solutions, and preferably can be formulated and used in the form of injections or skin external preparations.

The pharmaceutical composition according to an embodiment of the present invention may be administered to mammals such as rats, mice, livestock, humans, etc. by various routes such as parenteral or oral, and all modes of administration can be expected. For example, it can be administered by oral, transdermally, rectal or intravenous, intramuscular, subcutaneous, intrauterine dura mater or intracerebroventricular injection.

The pharmaceutical composition according to an embodiment of the present invention may be administered by various routes that can be easily applied by a person skilled in the art. In particular, the pharmaceutical composition according to an aspect of the present invention may be administered as an external preparation for skin by a route applied to the skin surface.

In one embodiment of the present invention, the composition may be a food composition. The food composition may include a health food composition. In one aspect, the present invention can provide various types of food additives or functional foods comprising the composition. The food composition may be formulated as fermented milk, cheese, yogurt, juice, probiotics, tablets, granules, drinks, caramels, diet bars, etc., including the composition, and may be formulated in the form of ordinary tea leaves, tea bags, and health supplements. It can be processed into, and can be used in the form of various other food additives. In one embodiment, the food composition may contain other ingredients that can give a synergistic effect to the main effect within a range that does not impair the main effect targeted by the present invention. For example, additives such as fragrances, pigments, disinfectants, antioxidants, preservatives, moisturizers, thickeners, inorganic salts, emulsifiers, and synthetic polymer substances may be further included in order to improve physical properties. In addition, auxiliary ingredients such as water-soluble vitamins, oil-soluble vitamins, polymer peptides, polymer polysaccharides, and seaweed extract may be further included. The above ingredients may be appropriately selected and blended by a person skilled in the art according to the formulation or purpose of use, and the amount added may be selected within a range not impairing the object and effect of the present invention. For example, the amount of the ingredients added may range from 0.01 to 5% by weight, more specifically from 0.01 to 3% by weight, based on the total weight of the composition. The food composition may be in various forms such as solutions, emulsions, viscous mixtures, tablets, and powders, which may be administered by various methods such as simple drinking, injection administration, spray method, or squeeze method.

Hereinafter, the content of the present invention will be described in more detail through Examples and Test Examples. However, these examples and test examples are only presented to understand the content of the present invention, and the scope of the present invention is not limited to these examples and test examples, and modifications and substitutions commonly known in the art And insertion and the like can be performed, and this is also included in the scope of the present invention.

[Example 1 and Comparative Examples 1 to 2]

The dehydrogenated tramethenolic acid of Formula 1 purchased from Chemfaces was used as Comparative Example 1, the compound K of Formula 2 purchased from Ambo Institute was used as Comparative Example 2, and the dehydrogenated tramethenolic acid and the compound K were used. A mixture mixed at a weight ratio of 1:7 was used as Example 1, and Comparative Examples 1 to 2 and Example 1 were used as samples, and the following Test Examples 1 to 3 were performed.

[Test Example 1] Skin cell proliferation effect

Human normal fibroblasts (Catalog #: CC-2509, Lonza) were used in 96-well microplates to see the effect of skin cell proliferation as a skin wrinkle improvement and skin elasticity enhancement effect. Each well was inoculated to 1×10 ⁴ cells and cultured in DMEM (Dulbecco's Modified Eagle's Medium) medium for 24 hours.

After incubation, dehydrogenated tramethenolic acid (Comparative Example 1), Compound K (Comparative Example 2), and a mixture of dehydrogenated tramethenolic acid and compound K (1:7 weight ratio mixture, Example 1) so that the final concentration of each was 10 ppm. It was replaced with DMEM medium without the adjusted serum and cultured for an additional 24 hours. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium (3-(4,5-dimdimeth-thiazol-2-yl)2,5-diphenyl tetrazolium; MTT: 5mg /ml) was added each 10 μl and left to stand for 4 hours, and then the medium portion was discarded. 100 μl of dimethyl sulfoxide solution was added to each well, and absorbance was measured at 570 nm with a microplate reader (SPECTRO star Nano, BGM LABTECH).

By carrying out the test of the above procedure, the cell proliferation effect was calculated from Equation 1 below, and the results are shown in Table 1 below.

[Equation 1]

Skin cell proliferation effect (%) =

Ingredient name (concentration) Absorbance (570 nm) Cell proliferation effect (%) Control (0ppm) 0.348 - Dehydrogenated tramethenolic acid (Comparative Example 1, 10 ppm) 0.537 54.3 Compound K (Comparative Example 2, 10 ppm) 0.516 48.3 Dehydrogenated tramethenolic acid and compound K mixture (1:7) (Example 1, 10 ppm) 0.652 87.4

From the results of Table 1, the mixture of dehydrogenated tramethenolic acid and compound K showed 1.61 times and 1.81 times higher skin cell proliferation effect than the skin cell proliferation efficacy of dehydrogenated tramethenolic acid and compound K treated with the same concentration. I could confirm.

[Test Example 2] Collagen biosynthesis promotion effect

In order to find out the effect of promoting collagen biosynthesis as an effect of improving skin wrinkles and enhancing skin elasticity, normal human fibroblasts were placed into 1×10 ⁴ cells in each well of a 96-well microplate. It was inoculated and cultured in DMEM (Dulbecco's Modified Eagle's Medium) medium for 24 hours.

After incubation, dehydrogenated tramethenolic acid (Comparative Example 1), Compound K (Comparative Example 2), and a mixture of dehydrogenated tramethenolic acid and compound K (1:7 weight ratio mixture, Example 1) so that the final concentration of each was 10 ppm. It was replaced with DMEM medium without the adjusted serum and cultured for an additional 48 hours. Collagen synthesis was promoted by adding 10 μM of ascorbic acid as a positive control 24 hours before the end of the culture. After incubation, each well was washed, replaced with a DMEM medium containing no serum, and cultured for an additional 24 hours. After incubation, the supernatant of each well was collected and the amount of newly synthesized collagen was determined as the amount of procollagen type-I C-peptide (PICP, Procollagen Type-I C-peptide) using a kit (Kit, Takara, Kyoto, Japan). It was measured, and the amount of PCIP was converted to ng/2×10 ⁴ cells, and the collagen synthesis effect was shown in Table 2 below.

Ingredient name (concentration) Collagen synthesis amount (ng/2×10 ⁴ ) Control (0ppm) 127 Ascorbic acid (10 ppm) 179 Dehydrogenated tramethenolic acid (Comparative Example 1, 10 ppm) 168 Compound K (Comparative Example 2, 10 ppm) 160 Dehydrogenated tramethenolic acid and compound K mixture (1:7) (Example 1, 10 ppm) 276

From the results of Table 2, it was confirmed that the mixture of dehydrogenated tramethenolic acid and Compound K exhibited 1.64 times and 1.73 times the effect of promoting collagen biosynthesis than each of the dehydrogenated tramethenolic acid and compound K treated at the same concentration. Could

[Test Example 3] Effect of inhibiting accumulation of lipofuscin in skin cells

In order to investigate the effect of inhibiting lipofuscin accumulation, human normal fibroblasts were inoculated to 1×10 ⁴ cells in each well of a 96-well microplate, and DMEM (Dulbecco's Modified Eagle's Medium) cultured for 24 hours.

After incubation, dehydrogenated tramethenolic acid (Comparative Example 1), Compound K (Comparative Example 2), and a mixture of dehydrogenated tramethenolic acid and compound K (1:7 weight ratio mixture, Example 1) so that the final concentration of each was 10 ppm. After replacing with the adjusted serum-free DMEM medium, the culture was further cultured for 48 hours and subcultured with a new medium. After 10 passages were performed, the amount of the self-luminescent protein lipofuscin in the cells was excitation at 360 nm using a microplate reader, and the emission fluorescence intensity at 570 nm was measured.

By performing the test of the above process, the lipofuscin accumulation inhibitory effect was calculated from Equation 2 below, and the results are shown in Table 3 below.

[Equation 2]

] X 100Lipofucine accumulation inhibitory effect (%) = [

] X 100

Ingredient name (concentration) Absorbance (570 nm) Lipofucin accumulation inhibition rate (%) Control (0ppm) 0.678 - Dehydrogenated tramethenolic acid (Comparative Example 1, 10 ppm) 0.473 30.2 Compound K (Comparative Example 2, 10 ppm) 0.482 28.9 Dehydrogenated tramethenolic acid and compound K mixture (1:7) (Example 1, 10 ppm) 0.308 54.6

From the results of Table 3, the mixture of dehydrogenated tramethenolic acid and compound K exhibits a lipofuscin accumulation inhibitory effect that is 1.81 times and 1.89 times higher than the lipofuscin accumulation inhibitory effect of dehydrogenated tramethenolic acid and compound K treated with the same concentration I could confirm that.

Hereinafter, examples of the formulation of a cosmetic composition having an anti-aging effect on the skin according to one aspect of the present invention as described above will be described below, but it can be applied to various other formulations, which is not intended to limit the present invention, but only specifically It is intended to be explained.

[Formulation Example 1] Lotion

A lotion was prepared according to a conventional method with the composition shown in Table 4 below.

ingredient Content (% by weight) Example 1 0.1 glycerin 3.0 Butylene glycol 2.0 Propylene glycol 2.0 Carboxyvinyl polymer 0.1 PEG 12 nonylphenyl ether 0.2 Polysorbate 80 0.4 ethanol 10.0 Triethanolamine 0.1 Preservatives, colors, flavors Appropriate amount Purified water Balance

[Formulation Example 2] 　nutrition cream

A nourishing cream was prepared according to a conventional method with the composition shown in Table 5 below.

ingredient Content (% by weight) Example 1 0.5 Polysorbate 60 1.5 Solbitansesuquioleate 0.5 PEG 60 hydrogenated castor oil 2.0 Floating paraffin 10.0 Squalane 5.0 Caprylic/Capractriglyceride 5.0 glycerin 5.0 Butylene glycol 3.0 Propylene glycol 3.0 Triethanolamine 0.2 Preservatives, colors, flavors Appropriate amount Purified water Balance

[Formulation Example 3] Massage Cream

A massage cream was prepared according to a conventional method with the composition shown in Table 6 below.

ingredient Content (% by weight) Example 1 1.0 Beeswax 10.0 Polysorbate 60 1.5 PEG 60 hydrogenated castor oil 2.0 Sorbitansquioleate 0.8 Floating paraffin 40.0 Squalane 5.0 Caprylic/Capric Triglyceride 4.0 glycerin 5.0

[Formulation Example 4] Pack

A pack was prepared according to a conventional method with the composition shown in Table 7 below.

ingredient Content (% by weight) Example 1 0.5 Polyvinyl alcohol 13.00 L-ascorbic acid-2-phosphate magnesium salt 1.00 Lauroylhydroxyproline 1.00 Water-soluble collagen (1% aqueous solution) 2.00 1,3-butylene glycol 3.00 ethanol 5.00 Purified water Balance

[Formulation Example 5] Tablet

Tablets were prepared according to a conventional method with the composition shown in Table 8 below.

ingredient Content(mg) Example 1 100 Corn starch 100 Lactose 100 Magnesium stearate 2

As described above, specific parts of the present invention have been described in detail, and it is obvious that these specific techniques are only preferred embodiments for those of ordinary skill in the art, and the scope of the present invention is not limited thereby. something to do. Therefore, it will be said that the substantial scope of the present invention is defined by the appended claims and their equivalents.

Claims (12)

Dehydrogenated tramethenolic acid, its stereoisomer, its salt, its hydrate or its solvate; And
A composition for improving skin wrinkles or improving skin elasticity comprising Compound K represented by the following Formula 2, its stereoisomer, its salt, its hydrate or its solvate; as an active ingredient
[Formula 2]

. The method of claim 1,
The dehydrogenated tramethenolic acid, its stereoisomer, its salt, its hydrate or its solvate; And the compound K, its stereoisomer, its salt, its hydrate or its solvate; 1: 1 to 15, characterized in that it is included in a weight ratio of, skin wrinkle improvement or skin elasticity improvement composition. The method of claim 2,
The weight ratio is 1: 5 to 10, characterized in that the weight ratio, skin wrinkle improvement or skin elasticity improvement composition. The method of claim 1,
The active ingredient is characterized in that contained in 0.0001 to 1% by weight based on the total weight of the composition, a composition for improving skin wrinkles or improving skin elasticity. The method of claim 1,
The composition is characterized in that to proliferate fibroblasts, for improving skin wrinkles or for improving skin elasticity. The method of claim 1,
The composition is characterized in that to promote the biosynthesis of collagen, a composition for improving skin wrinkles or improving skin elasticity. The method of claim 1,
The composition is characterized in that to inhibit the accumulation of lipofuscin (lipofuscin) in the skin, a composition for improving skin wrinkles or enhancing skin elasticity. The method of claim 1,
The daily dosage of the active ingredient is 1 to 100 mg/kg, a composition for improving skin wrinkles or improving skin elasticity. The method of claim 1,
The daily dosage of the dehydrogenated tramethenolic acid, its stereoisomer, its salt, its hydrate or its solvate is 0.125 to 12.5 mg/kg, a composition for improving skin wrinkles or enhancing skin elasticity. The method of claim 1,
The compound K, a stereoisomer thereof, a salt thereof, a hydrate thereof or a solvate thereof daily dose of 0.875 to 87.5 mg / kg, a composition for improving skin wrinkles or enhancing skin elasticity. The method according to any one of claims 1 to 7,
The composition is a cosmetic composition, characterized in that, for improving skin wrinkles or improving skin elasticity. The method according to any one of claims 1 to 7,
The composition is a food composition, characterized in that, skin wrinkle improvement or skin elasticity improvement composition.