KR102152932B1 - Composition for improving skin conditions comprising catechin glycoside and method for improving skin conditions using the same - Google Patents

Abstract

The present invention relates to a composition for improving skin conditions containing a catechin glycoside as an active ingredient and a method for improving skin conditions using the same. Specifically, the present invention relates to a cosmetic composition, a quasi-drug composition, or a food composition for preventing or improving skin wrinkles, for preventing or improving skin aging, for improving skin elasticity or for improving skin moisturization, containing catechin glycosides as an active ingredient. In addition, the present invention relates to a pharmaceutical composition for preventing or treating skin aging or dry skin, containing a catechin glycoside as an active ingredient. In addition, the present invention relates to a method of improving a skin condition or preventing or treating skin aging or dry skin by using the above compositions.

Description

A composition for improving skin condition containing catechin glycoside as an active ingredient, and a method for improving skin condition using the same {COMPOSITION FOR IMPROVING SKIN CONDITIONS COMPRISING CATECHIN GLYCOSIDE AND METHOD FOR IMPROVING SKIN CONDITIONS USING THE SAME}

The present invention relates to a composition for improving skin conditions containing a catechin glycoside as an active ingredient and a method for improving skin conditions using the same.

Specifically, the present invention relates to a cosmetic composition, a quasi-drug composition, or a food composition for preventing or improving skin wrinkles, for preventing or improving skin aging, for improving skin elasticity or for improving skin moisturization, containing catechin glycosides as an active ingredient.

In addition, the present invention relates to a pharmaceutical composition for preventing or treating skin aging or dry skin, containing a catechin glycoside as an active ingredient.

In addition, the present invention relates to a method of improving a skin condition or preventing or treating skin aging or dry skin by using the above compositions.

The skin is largely composed of the epidermal layer, the dermis layer, and the subcutaneous fat layer, and the most basic role of such skin is to prevent the invasion of harmful ingredients from the outside and to block the evaporation of moisture from our body. In particular, in recent years, the phenomenon of relating physical health or human beauty to the beauty of the skin has become remarkable, and interest in the skin is increasing, and related products are being developed.

Human skin generally contains 15% to 20% of moisture, and such moisture in the skin functions to protect the skin from the outside together with oil. In particular, natural moisturizing factors and sebum components are present in the outermost stratum corneum of the skin's epidermis, and these play an important role in the elasticity and flexibility of the skin by properly maintaining moisture. However, in addition to factors such as natural aging progress in recent years, as the moisture in the stratum corneum decreases due to factors such as artificial temperature control and various stresses, the skin becomes dry and rough, preventing transepidermal water loss (TEWL) or There is increasing interest in the development of products that maintain skin moisturization by increasing the stratum corneum hydration (SC hydration) of the stratum corneum.

Wrinkles, a typical symptom of skin aging, are known to be caused by damage to matrix proteins such as collagen and elastic fibers that form a matrix in the dermis of the skin. Collagen in the skin is degraded through various signaling pathways during the aging process, and collagen decomposition is promoted by external stimuli such as ultraviolet rays, leading to increased wrinkle formation.

In order to prevent skin aging, studies have been made on substances that promote collagen synthesis in the past, and as substances that promote collagen synthesis, retinoid (US RE36068), protein derived from animal placenta (JP Hei 08-2312709), and betul Prior art related to phosphoric acid (JP Hei 08-208424), chlorella extract (JP Hei 09-0405239, JP Hei 10-0362839) and the like are known. However, in the case of retinoids, the amount of retinoids is limited due to stability problems such as unstable substances, severe irritation and redness when applied to the skin, and chlorella extracts are insignificant and substantially improve the skin condition by promoting collagen synthesis in the skin. There are limitations that are difficult to expect.

In addition, ultrasound treatment, skin scaling, laser dermabrasion, botulinum toxin injection, and restylane injection are being performed as newly emerging wrinkle treatments, but they are not showing great effects in terms of cost and persistence. .

On the other hand, MMP (Matrix metallo proteinase) is a calcium- and zinc-dependent endopeptidase secreted from cells such as polymorphonuclear neutrophils, macrophages, and fibroblasts, which degrade collagen. It is an enzyme.

As a method of inhibiting the formation of wrinkles, a method of promoting collagen synthesis or inhibiting collagen degradation can be used, so research on substances that inhibit collagen degradation in order to develop a more effective, easy and safe cosmetic for wrinkle improvement Needs to be done. In particular, in recent years, interest in the efficacy of natural substances having relatively superior skin stability compared to compounds has increased.

Red bean is an annual herbaceous plant belonging to the legume family and has been widely used as an edible and medicinal plant since ancient times. So far, domestic and foreign studies on red beans have known the effects of red beans on reducing cholesterol and lowering blood sugar in the serum of diabetic mice. In addition, antibacterial, anti-tumor, and anti-allergic effects are known. However, no studies have been conducted on the effects of red beans in improving skin moisturization, wrinkles, or anti-aging, and in particular, the efficacy of catechin compounds contained in red beans on skin aging is unknown.

Under this background, the inventors of the present invention were conducting research on a substance that is not toxic from natural resources and has excellent skin condition improvement effect, while red beans ( Vigna angularis ) extract, especially catechin glycosides contained in red bean extract, has the effect of inhibiting collagen decomposition, blocking transdermal moisture loss, and enhancing the degree of hydration of the stratum corneum, thus finding out that it is effective in preventing skin aging and improving skin moisture. A composition for improving skin condition using glycosides has been completed.

An object of the present invention is to provide a composition for improving skin condition containing catechin glycosides and a method for improving skin condition using the same.

Specifically, one object of the present invention is to provide a cosmetic composition, quasi-drug composition or food composition for preventing or improving skin wrinkles, for preventing or improving skin aging, for improving skin elasticity or for improving skin moisturization, containing catechin glycosides. .

Another object of the present invention is to provide a pharmaceutical composition for the prevention or treatment of skin aging or dry skin, containing a catechin glycoside as an active ingredient.

Another object of the present invention is to provide a method for improving a skin condition or preventing or treating skin aging or dry skin by using the above compositions.

In order to solve the above problems, the present invention provides a cosmetic composition for improving skin condition, containing a catechin glycoside as an active ingredient as an embodiment.

The term "catechin" used in the present invention belongs to flavan-3-ols of the flavonoid group and refers to a kind of polyphenol.

The term used in the present invention, "Catechin Glycoside" refers to a glycoside produced through a glycosylation process of catechin. Specifically, the catechin sugar of the present invention is catechin-3-O-glucoside, catechin-3'-O-glucoside, catechin-4'-O-glucoside, catechin-5-O-glucoside, catechin-7 -O-glucoside, and the like, but are not limited thereto.

As an example of the catechin glycoside of the present invention, catechin-7-O-glucoside represented by the following Formula 1 may be used.

[Formula 1]

The present inventors have found that catechin glycosides have the effect of preventing skin aging, improving skin elasticity, and improving skin moisturization.In particular, catechin glycosides inhibit the expression of collagen-degrading enzyme MMP-1, and type 1 procollagen ( Type-1 Procollagen), elastin, and TGF-β1 (Transforming growth factor beta 1) were identified for the first time.

In a specific embodiment of the present invention, it was confirmed that when a catechin glycoside was treated in an albino hairless mouse induced photoaging by irradiation with UVB, the transdermal water loss of the mouse was reduced, the degree of stratum corneum hydration increased, and the wrinkle depth of the skin was decreased. (Test Examples 4 and 5).

In another example, it was also confirmed that when a catechin glycoside was treated in a mouse in which photoaging was induced, the expression of MMP-1 was reduced, and the expression of type 1 procollagen, elastin and TGF-β1 was increased (test Examples 3 and 7).

In the present invention, the catechin glycosides may be chemically synthesized or separated from natural substances, and may be purchased and used from domestic and foreign companies. In the case of separating the catechin glycoside of the present invention from a natural substance, as long as the catechin glycoside is included, it may be a concept including all extracts of natural substances or fractions thereof.

In the present invention, when the catechin glycoside is isolated from a plant, the type of plant is not particularly limited, but is preferably red beans ( Vigna angularis ) may be obtained by separation.

Red beans ( Vigna angularis ) is an annual herbaceous plant belonging to the legume family, generally 50 cm to 90 cm tall, and the stem is green or reddish purple. The leaves are alternate and consist of 3 small leaves, egg-shaped or rhombus-shaped, and flowers bloom in August, yellow raceme, hanging from 4 to 6 peduncles from the axils. Fruits are columnar, light brown, dark brown, and ripen with rounded ends.

In the present invention, the catechin glycoside may be isolated from an red bean extract or a fraction thereof, or may be used in a form contained in an red bean extract or a fraction thereof.

The term "extract" as used in the present invention refers to an extract obtained by extracting natural substances, a diluted or concentrated solution of the extract, a dried product obtained by drying the extract, a prepared product or purified product of the extract, or a mixture thereof. , The extract itself and all formulations that can be formed using the extract are included.

The extract may be extracted from various organs of natural products, hybrids or varieties thereof. For example, in the case of an extract of a plant, only the root, the upper part, the stem, the leaf, the flower, the body of the fruit, the skin of the fruit, the seed It can also be extracted from plant tissue culture. In the present invention, the red bean extract may preferably be an extract of red bean roe (fruit).

The method of preparing the extract is not particularly limited, and may be extracted according to a method commonly used in the art. Non-limiting examples of the extraction method include hot water extraction method, ultrasonic extraction method, filtration method, reflux extraction method, immersion extraction method, high temperature and high pressure steam extraction method, etc., which may be performed alone or in combination of two or more methods. have.

In the present invention, the kind of the extraction solvent used to extract natural substances is not particularly limited, and any solvent known in the art may be used. Non-limiting examples of the extraction solvent may include water, alcohol, or a mixed solvent thereof, and when alcohol is used as a solvent, preferably a C ₁ to C ₄ alcohol, more preferably C ₁ to C It can be extracted with ₂ lower alcohols.

In the present invention, the red bean extract is preferably washed red beans to remove foreign substances, and an extraction solvent of 2 to 10 times the weight of the red bean is added to the extraction temperature at room temperature (about 15°C to 25°C) to 100°C. It can be extracted for about 2 hours to 5 hours, but is not limited thereto. The number of extractions is not particularly limited, but may be preferably 1 to 3 times.

As used herein, the term "fraction" means a result obtained by performing fractionation in order to separate a specific component or a specific component group from a mixture containing several different constituents.

The fractionation method for obtaining the fraction in the present invention is not particularly limited, and may be performed according to a method commonly used in the art. Non-limiting examples of the fractionation method include a method of obtaining a fraction from the extract by treating an extract obtained by extracting a natural substance with a predetermined solvent.

In the present invention, the kind of the fractionation solvent used to obtain the fraction is not particularly limited, and any solvent known in the art may be used. Non-limiting examples of the fractionation solvent include polar solvents such as water and alcohol; Non-polar solvents, such as hexane, ethyl acetate, chloroform, and dichloromethane, etc. are mentioned. These may be used alone or in combination of two or more. In the case of using an alcohol in the fractionation solvent, preferably a C ₁ to C ₄ alcohol may be used.

The catechin glycosides of the present invention can be prepared by being separated from red beans by a manufacturing method comprising the following steps.

1) extracting red beans by adding an extraction solvent;

2) concentrating the extract of step 1) under reduced pressure;

3) separating the catechin glycoside from the concentrated extract of step 2);

4) Concentrating the separated catechin glycoside of step 3) under reduced pressure and drying and powdering.

In the present invention, a method of separating a catechin glycoside from an adzuki bean extract or a fraction thereof is not particularly limited, but may be preferably separated using a high speed counter current chromatogram (HSCCC).

As used herein, the term "improving skin condition" means preventing or improving skin wrinkles, preventing or improving skin aging, improving skin elasticity, or improving skin moisture.

As used herein, the term "improvement" refers to all actions of at least reducing the severity of a parameter related to the alleviation or treatment of a condition, for example, symptoms.

Based on the total weight of the cosmetic composition of the present invention, the catechin glycoside may preferably be contained in an amount of 0.01% to 50% by weight, more preferably 0.1% to 30% by weight, and more preferably It may be contained in an amount of 1% to 20% by weight. Within the above range, there is an advantage of showing excellent skin wrinkle prevention or improvement, skin aging prevention or improvement, skin elasticity improvement, and skin moisturizing improvement effect, and there is an advantage that the formulation of the composition is stabilized.

The cosmetic composition of the present invention is a solution, external ointment, cream, foam, nutritional lotion, flexible lotion, pack, softening water, emulsion, makeup base, essence, liquid detergent, bathing agent, sunscreen cream, sun oil, suspension, emulsion, Paste, gel, lotion, powder, soap, surfactant-containing cleansing, oil, powder foundation, emulsion foundation, wax foundation, can be prepared in a formulation selected from the group consisting of a patch and spray, but is not limited thereto.

The cosmetic composition of the present invention may additionally include one or more cosmetically acceptable carriers blended in general skin cosmetics, and as common ingredients, for example, oil, water, surfactants, moisturizers, lower alcohols, thickeners , A chelating agent, a colorant, a preservative, a fragrance, and the like may be appropriately blended, but are not limited thereto.

The cosmetically acceptable carrier included in the cosmetic composition of the present invention varies depending on the formulation of the cosmetic composition.

When the formulation of the present invention is an ointment, paste, cream or gel, animal oil, vegetable oil, wax, paraffin, starch, tragacanth, cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc, zinc oxide as carrier components Such as may be used, but is not limited thereto. These may be used alone or in combination of two or more.

When the formulation of the present invention is a powder or spray, lactose, talc, silica, aluminum hydroxide, calcium silicate, polyamide powder, etc. may be used as a carrier component. In particular, in the case of a spray, additional chlorofluorohydrocarbons , Propane/butane or a propellant such as dimethyl ether may be included, but is not limited thereto. These may be used alone or in combination of two or more.

When the formulation of the present invention is a solution or emulsion, a solvent, a solubilizing agent or an emulsifying agent may be used as a carrier component, such as water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, Propylene glycol, 1,3-butyl glycol oil, and the like may be used, and 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 May be used, but is not limited thereto. These may be used alone or in combination of two or more.

When the formulation of the present invention is a suspension, as a carrier component, a liquid diluent such as water, ethanol or propylene glycol, an ethoxylated isostearyl alcohol, a suspending agent such as polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester, micro Crystalline cellulose, aluminum metahydroxide, bentonite, agar, or tragacanth may be used, but is not limited thereto. These may be used alone or in combination of two or more.

When the formulation of the present invention is a soap, an alkali metal salt of a fatty acid, a fatty acid hemiester salt, a fatty acid protein hydrolyzate, isethionate, a lanolin derivative, an aliphatic alcohol, vegetable oil, glycerol, sugar, etc. are used as a carrier component. It may be, but is not limited thereto. These may be used alone or in combination of two or more.

According to another embodiment of the present invention, there is provided a quasi-drug composition for improving skin conditions containing catechin glycosides as an active ingredient.

The term "quasi-drug" as used in the present invention refers to items that are less effective than medicines among items used for the purpose of diagnosing, treating, improving, alleviating, treating or preventing diseases of humans or animals. According to this, quasi-drugs exclude items used for pharmaceutical purposes, and include products used for the treatment or prevention of diseases of humans and animals, and products that have mild or no direct action on the human body.

When the catechin glycoside of the present invention is used as a quasi-drug additive, it may be added as it is or used with other quasi-drug or quasi-drug components, and may be appropriately used according to a conventional method. The mixing ratio with other ingredients used together may be appropriately determined depending on the purpose of use (eg, prevention, improvement or therapeutic treatment).

Based on the total weight of the quasi-drug composition of the present invention, the catechin glycoside may preferably be contained in an amount of 0.01% to 50% by weight, more preferably 0.1% to 30% by weight, more preferably It may be contained in an amount of 1% to 20% by weight. Within the above range, there is an advantage of showing excellent skin wrinkle prevention or improvement, skin aging prevention or improvement, skin elasticity improvement, and skin moisturizing improvement effect, and there is an advantage that the formulation of the composition is stabilized.

The quasi-drug composition of the present invention may be prepared in a formulation selected from the group consisting of a body cleanser, foam, soap, mask, ointment, cream, lotion, essence, and spray, but is not limited thereto.

According to another embodiment of the present invention, there is provided a food composition for improving skin conditions containing catechin glycosides as an active ingredient.

The food composition of the present invention is not particularly limited, and includes a health functional food composition.

When using the health functional food composition of the present invention as a food additive, the composition may be added as it is or may be used with other foods or food ingredients, and may be appropriately used according to a conventional method.

The kind of the food is not particularly limited, and includes all foods in a conventional sense. Non-limiting examples of foods to which the above substances 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, alcoholic beverages, and vitamin complexes.

When the health functional food composition of the present invention is a beverage composition, it may contain various flavoring agents or natural carbohydrates as an additional component, like a normal beverage. Non-limiting examples of the natural carbohydrates include monosaccharides such as glucose and fructose; Disaccharides such as maltose and sucrose; Natural sweeteners such as dextrin and cyclodextrin; And synthetic sweeteners such as saccharin and aspartame. The proportion of the additional ingredients to be added may be appropriately determined by the choice of a person skilled in the art.

In addition to the above, the health functional food composition of the present invention includes various nutrients, vitamins, electrolytes, flavoring agents, coloring agents, pectic acid and salts thereof, alginic acid and salts thereof, organic acids, protective colloid thickeners, pH adjusters, stabilizers, preservatives, glycerin , Alcohol, carbonated beverages, and the like. In addition, the health functional food composition of the present invention may contain pulp for the production of natural fruit juice, fruit beverage or vegetable beverage. These components may be used independently or may be used in combination of two or more. The proportion of these additives can also be appropriately selected by those skilled in the art.

According to another embodiment of the present invention, there is provided a pharmaceutical composition for preventing or treating skin aging or dry skin, containing a catechin glycoside as an active ingredient.

In addition to containing a catechin glycoside as an active ingredient, the pharmaceutical composition of the present invention may further contain a pharmaceutically acceptable carrier.

In the present invention, the "pharmaceutically acceptable" means that it is commonly used in the field of pharmaceuticals, which does not stimulate an organism when administered, and does not inhibit the biological activity and properties of the administered compound.

In the present invention, the kind of the carrier is not particularly limited, and any carrier commonly used in the art may be used. Non-limiting examples of the carrier include saline, sterile water, Ringer's solution, buffered saline, albumin injection solution, lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, maltodextrin, glycerol, ethanol, and the like. I can. These may be used alone or in combination of two or more.

In addition, the pharmaceutical composition of the present invention may be used by adding other pharmaceutically acceptable additives such as excipients, diluents, antioxidants, buffers or bacteriostatic agents, if necessary, and fillers, extenders, wetting agents, disintegrants, dispersants, surfactants , A binder or a lubricant may be additionally added and used.

In the pharmaceutical composition of the present invention, the catechin glycoside may be contained in an amount of 0.00001% to 99.99% by weight based on the total weight of the pharmaceutical composition, preferably 1% to 99.99% by weight, more preferably 10 It may be included in an amount of from 50% to 99.99% by weight, more preferably from 50% to 99.99% by weight, and may also be included in the total amount of the pharmaceutical composition.

The pharmaceutical composition of the present invention may be formulated and used in various formulations suitable for oral administration or parenteral administration.

Non-limiting examples of formulations for oral administration include troches, lozenges, tablets, aqueous suspensions, oily suspensions, powders, granules, emulsions, hard capsules, soft capsules, syrups or elixirs, etc. Can be mentioned.

In order to formulate the pharmaceutical composition of the present invention for oral administration, a binder such as lactose, saccharose, sorbitol, mannitol, starch, amylopectin, cellulose or gelatin; Excipients such as dicalcium phosphate and the like; Disintegrants such as corn starch or sweet potato starch; Lubricating oils such as magnesium stearate, calcium stearate, sodium stearyl fumarate or polyethylene glycol wax may be used, and sweeteners, fragrances, syrups, and the like may also be used.

Furthermore, in the case of capsules, in addition to the above-mentioned substances, a liquid carrier such as fatty oil may be additionally used.

Non-limiting examples of the parenteral preparation include injection solutions, suppositories, respiratory inhalation powders, spray aerosols, ointments, coating powders, oils, creams, and the like.

In order to formulate the pharmaceutical composition of the present invention for parenteral administration, sterilized aqueous solutions, non-aqueous solvents, suspensions, emulsions, freeze-dried preparations, external preparations, etc. may be used. As the non-aqueous solvents and suspensions, propylene glycol, polyethylene Glycols, vegetable oils such as olive oil, injectable esters such as ethyloleate, and the like may be used.

In addition, more specifically, when the pharmaceutical composition of the present invention is formulated as an injection solution, the composition of the present invention is prepared as a solution or suspension by mixing in water with a stabilizer or a buffer, and this is used in an ampoule or vial. It can be formulated for unit administration. In addition, when the pharmaceutical composition of the present invention is formulated with an aerosol, a propellant or the like may be blended with an additive so that the aqueous concentrated or wet powder is dispersed.

In addition, when the pharmaceutical composition of the present invention is formulated as an ointment, cream, etc., animal oil, vegetable oil, wax, paraffin, starch, tracant, cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc, zinc oxide It can be formulated using the like as a carrier.

The pharmaceutically effective amount and effective dosage of the pharmaceutical composition of the present invention may vary depending on the formulation method, the mode of administration, the administration time and/or the route of administration of the pharmaceutical composition, and the response to be achieved by the administration of the pharmaceutical composition Including the type and degree, the type of the subject to be administered, the age, weight, general health condition, the symptom or degree of the disease, sex, diet, excretion, drugs used concurrently with the subject or at the same time, and other components of the composition. It may vary depending on various factors and similar factors well known in the medical field, and a person of ordinary skill in the art can easily determine and prescribe an effective dosage for a desired treatment.

The administration of the pharmaceutical composition of the present invention may be administered once a day, or may be divided several times. The pharmaceutical composition of the present invention may be administered as an individual therapeutic agent or administered in combination with other therapeutic agents, and may be administered sequentially or simultaneously with a conventional therapeutic agent. It is important to administer an amount capable of obtaining the maximum effect in a minimum amount without side effects in consideration of all the above factors, and can be easily determined by a person skilled in the art.

When the pharmaceutical composition of the present invention is administered orally, for a more preferable effect, it can be administered once to several times in an amount of 0.0001 mg to 500 mg per 1 kg of body weight per day, and 0.001 mg/1 It is preferable to administer in an amount of kg/1 day to 100 mg/1 kg/1 day.

The route of administration and the method of administration of the pharmaceutical composition of the present invention may each be independent, and the method is not particularly limited, and any route of administration and administration method may be applied as long as the pharmaceutical composition can reach the desired site. You can follow. The pharmaceutical composition may be administered orally or parenterally.

As the parenteral administration method, for example, intravenous administration, intraperitoneal administration, intramuscular administration, transdermal administration or subcutaneous administration, etc. can be used, and a method of applying, spraying, or inhaling the composition to a diseased site may also be used. Can be, but is not limited to these.

As used herein, the term "prevention" refers to any action that suppresses or delays skin aging or dry skin symptoms by administering the pharmaceutical composition of the present invention to an individual.

The term "treatment" used in the present invention refers to any action to improve or benefit from skin aging or dry skin symptoms by administering the pharmaceutical composition of the present invention to an individual.

According to another embodiment of the present invention, there is provided a method for improving skin conditions, comprising administering to an individual a cosmetic composition, quasi-drug composition, or food composition containing a catechin glycoside as an active ingredient.

According to another embodiment of the present invention, there is provided a method for preventing or treating skin aging or dry skin, comprising administering to an individual a pharmaceutical composition containing a catechin glycoside as an active ingredient.

The term "individual" as used in the present invention means all animals including mammals including mice, livestock, humans, and the like.

In the present invention, the description of the dosage of the composition, the route of administration, the mode of administration, etc. will be replaced with the contents described in relation to the pharmaceutical composition of the present invention.

The composition containing the catechin glycoside of the present invention has the effect of preventing transdermal moisture loss and enhancing the degree of hydration of the stratum corneum, so it can be usefully used for improving skin moisturization or preventing or treating dry skin, as well as excellent antioxidant effect. And it has an inhibitory activity against the activity of the collagen-degrading enzyme MMP-1, it can be usefully used for improving skin wrinkles, preventing or treating skin aging.

1 shows the cell viability for catechin glycosides in NHDF cells.
Figure 2 shows the effect of catechin glycosides on reactive oxygen species increased by UV-B in NHDF cells.
Figure 3 shows the effect of catechin glycosides on MMP-1 increased by UV-B in NHDF cells.
4 shows changes in the degree of hydration of the stratum corneum (a) and the degree of transdermal water loss (b) when catechin glycosides are treated in SKH:HR-1 mice.
Figure 5 shows the changes in the appearance of wrinkles (a) and wrinkle depth (b) of skin samples when catechin glycosides were treated in SKH:HR-1 mice.
Figure 6 shows the histological changes of skin when treated with catechin glycosides in SKH:HR-1 mice.
7 shows changes in the protein expression levels of MMP-1, type 1 procollagen, elastin and TGF-1 in SKH:HR-1 mice treated with catechin glycosides.
8 shows the chemical formula of a catechin glycoside isolated from red bean extract using HSCCC in an embodiment of the present invention.
In FIGS. 1 to 8, CG is a catechin glycoside, UVB is ultraviolet-B, Normal is a normal group, Cot (or UVBcont) is a negative control, and RP is a positive control treated with retinyl palmitate.

Hereinafter, the present invention will be described in more detail through examples. However, these examples are for illustrative purposes only, and thus the scope of the present invention should not be construed as being limited by these examples.

Example 1: Preparation of catechin glycoside

Commercially available red beans were obtained, 8 L of 80% by weight aqueous methanol solution was added to 800 g of red beans, followed by extraction at 25°C for 3 days. The extract was filtered under reduced pressure and concentrated to obtain 51.7 g of red bean extract. After separating 1 g of the extract using HSCCC, the catechin glycoside was concentrated and dried and powdered to obtain 23 mg of catechin glycoside (catechin-7-O-glucoside) in powder form (FIG. 8).

Test example One: In skin fibroblasts Verification of the effect of catechin glycosides on cell growth

In order to confirm the effect of the catechin glycoside obtained in Example 1 on the growth of skin fibroblasts (NHDF, normal human dermal fibroblasts), DMEM (Dulbeccos modified Eagles), a dedicated medium containing 10% FBS (fetal bovine serum, Cambrex ) medium) skin fibroblasts were seeded in a 40 mm dish at 1.2×10 ⁵ /dish, and then cultured for 24 hours at 37° C. and under 5% CO ₂ moist conditions. Thereafter, the medium was removed, 300 µl of PBS was added, UVB (UVB Peak range: 312 nm, UV dose: 144 mJ/cm ² ) was irradiated, and then the catechin glycosides diluted with serum-free DMEM medium were added at different concentrations (1, 10). , 25 µg/µl) and cultured for 72 hours. After 72 hours, 1 mg/mL of MTT was treated, and after 2 hours, formazan produced by the MTT treatment was dissolved in DMSO and absorbance was measured at 570 nm.

As a result of the above experiment, when each catechin glycoside was treated on NHDF cells, it was confirmed that the catechin glycoside did not significantly affect the cell viability (FIG. 1), and thus it was confirmed that the catechin glycoside did not show toxicity to the NHDF cells. .

Test example 2: Verification of the antioxidant effect of catechin glycosides

In order to confirm the inhibitory effect of catechin glycosides on the production of ROS (Reactive Oxygen Species) in NHDF cells, NHDF cells were irradiated with UVB (UVB Peak range: 312 nm, UV dose: 144 mJ/cm ² ), followed by serum-free DMEM medium. Diluted catechin glycosides were treated at different concentrations (10, 25 μg/µl) and incubated for 30 minutes, and then fluorescence was measured at 480 nm for excitation and 530 nm for emission, resulting in DCF fluorescence. intensity) was compared.

Statistical processing of the obtained results was performed using the GraphPad Prism program, and the significance of the average value was investigated with a limit of less than 5% using a one-way analysis of variance (ANOVA).

As a result of the above experiment, it was confirmed that the catechin glycoside has an effect of inhibiting ROS production at a concentration of 25 µg/µl compared to the control group (Fig. 2).

Test example 3: NHDF Of catechin glycosides in cells MMP -1 Inhibition effect verification

In order to confirm the effect of catechin glycosides on the enzyme activity of MMP-1 (Matrix Metallo Proteinase-1), skin fibroblasts were seeded in a 40 mm dish at 1.2×10 ⁵ /dish, cultured for 24 hours, and then removed. 300 µl of PBS was added, irradiated with UVB, and then catechin glycosides diluted with serum-free DMEM medium were treated at different concentrations (1, 10, 25 µg/µl) and cultured for 72 hours. Thereafter, the medium was collected and the amount of MMP-1 secreted in the medium was measured using the MMP-1 Kit (Amersham bioscience).

As a result of the above experiment, catechin glycosides showed a concentration-dependent inhibitory effect on the production of MMP-1, which is increased by UVB (FIG. 3). Therefore, it was confirmed that the catechin glycoside of the present invention has an effect of preventing wrinkles by inhibiting the production of MMP-1, a collagen-degrading enzyme.

Test example 4: processed catechin glycosides SKH : HR -1 Verification of skin moisturizing effect on mice

In order to confirm the skin moisturizing effect of the catechin glycosides, 7-week-old albino hairless mice (SKH:HR-1) were divided into 5 groups A to E each of 10 mice. Group A was a normal group and was not irradiated with UVB [Normal], and groups B to E were irradiated with UVB to induce aging. Thereafter, groups C to E were dissolved in a solution mixed with PG:EtOH=7:3 at a volume of 100 μl each, and applied to the back of SKH:HR-1 mice for 4 weeks. In the case of group B, only aging was induced as a negative control [Cont], and in group C, retinyl palmitate was applied as a positive control at a dose of 10 mg/g [RP]. Group D and Group E were test groups, and Group D was coated with the catechin glycoside prepared in Example 1 at a dose of 10 mg/g [CG 1%], and Group E was prepared in Example 1 Catechin glycosides were applied at a dose of 50 mg/g [CG 5%].

As a result of the above experiment, it was confirmed that in the group treated with the catechin glycoside, there was an effect of decreasing transdermal water loss and increasing the degree of stratum corneum hydration in a concentration-dependent manner (FIG. 4).

Test example 5: treated catechin glycosides SKH : HR -1 Verification of skin wrinkle improvement effect in mice

In order to confirm the skin wrinkle improvement effect of SKH:HR-1 mice treated with catechin glycosides, after killing the mice of each group of Test Example 4, a SILFLO impression material (Flexico, Colchester, UK) was used on the back skin. Thus, a skin sample was prepared. Thereafter, the skin specimen (Fig. 5(a)) was observed through a CCD video camera, and the wrinkle depth degree (Fig. 5(b)) was measured through the Viscometer SV 600 software (Courage & Khazaka, Cologne, Germany). .

In the x-axis of FIG. 5(b), R1 is the difference value between the highest peak value and the lowest valley value of the total wrinkle curve, and R3 is the average value of R1 values within each equal part divided after dividing the wrinkle contour line by five equal parts. R2 is the largest value among R1 values in each equal part divided by the corrugation contour line by 5 equal parts, R5 is the distance between the corrugation height intersecting the corrugated contour line by drawing two parallel lines and crossing the corrugated contour line, and R4 is A parallel line is drawn at the highest point of the wrinkle contour line, and the depth of the fine wrinkle is indicated by the distance of the wrinkle meeting the baseline line below it. The y-axis shows the values of R1 to R5 relatively, and the smaller the value, the smaller the depth of wrinkles, and the units of R1 to R5 are arbitrary units.

As a result of the above experiment, it was confirmed that the group treated with catechin glycosides had a concentration-dependent skin wrinkle improvement effect.

Test example 6: processed catechin glycosides SKH : HR -1 Measurement of histological changes in mouse skin

In order to observe changes in skin thickness and tissue of SKH:HR-1 mice treated with catechin glycosides, after killing the mice of each group of Test Example 4, the back skin tissue was collected and fixed with 4% formaldehyde solution I did. After fixation, water washing and dehydration were performed, and paraffin was embedded, and 4 µm sections were prepared, followed by Hematoxylin & Eosin (H&E) staining and Masson trichrome (MTC) staining.

As a result of the above experiment, it was confirmed that the thickness of the skin increased by UVB in the skin tissue of the mouse treated with the catechin glycoside was decreased in a concentration-dependent manner, and the synthesis was enhanced while the degradation of collagen was inhibited (FIG. 6).

Test example 7: processed catechin glycosides SKH : HR -1 of mouse MMP -1, type 1 procollagen, elastin and TGF -β1 protein expression level change measurement

In order to confirm the change in the expression levels of MMP-1, Type-1 Procollagen, elastin and TGF-β1 in the skin of SKH:HR-1 mice, mice of each group of Test Example 4 were After killing, the skin tissue on the back was collected. After collection, the protein was isolated from the skin tissue, and the expression levels of MMP-1, type 1 procollagen, elastin and TGF-β1 in the control group and the test group were confirmed using a general western blot method.

As a result of the above experiment, in the case of mice treated with catechin glycosides, it was confirmed that the expression levels of type 1 procollagen, elastin, and TGF-β1 were increased while suppressing the expression of the collagen-degrading enzyme MMP-1 in a concentration-dependent manner. The effect of improving skin wrinkles of catechin glycosides was confirmed (Fig. 7).

By combining the results of the above test examples, catechin glycosides have an effect of preventing transdermal moisture loss and enhancing the degree of hydration of the stratum corneum, and thus can be usefully used for improving skin moisturization or preventing or treating dry skin, as well as excellent It has an antioxidant effect, inhibits MMP-1 expression, and promotes expression of type 1 procollagen, elastin and TGF-β1, and thus it was confirmed that it can be usefully used for improving skin wrinkles, preventing or treating skin aging.

In the present specification, details that can be sufficiently recognized and inferred by those of ordinary skill in the technical field of the present invention have been omitted, and the technical spirit or essential configuration of the present invention other than the specific examples described in the present specification is changed. More various modifications are possible within the range that does not. Accordingly, the present invention may be implemented in a manner different from that specifically described and illustrated in the present specification, and this is a matter that can be understood by those of ordinary skill in the technical field of the present invention.

Claims (16)

A cosmetic composition for improving skin condition containing a catechin glycoside represented by the following Formula 1 as an active ingredient, wherein the improvement of the skin condition is at least one selected from the group consisting of preventing or improving skin wrinkles and improving skin elasticity. Composition.
[Formula 1]

A cosmetic composition for improving skin moisturization containing a catechin glycoside represented by the following formula (1) as an active ingredient.
[Formula 1]

The cosmetic composition according to claim 1 or 2, wherein the catechin glycoside is obtained from an red bean ( Vigna angularis ) extract or a fraction thereof.
The cosmetic composition according to claim 1 or 2, wherein the catechin glycoside inhibits the expression of a collagen-degrading enzyme.
The cosmetic composition of claim 4, wherein the collagen-degrading enzyme is MMP-1 (Matrix metallo proteinase-1).
The expression of one or more kinds of proteins according to claim 1 or 2, wherein the catechin glycoside is type 1 procollagen, elastin, and TGF-β1 (Transforming growth factor beta 1). To promote, cosmetic composition.
A quasi-drug composition for improving skin condition containing a catechin glycoside represented by the following Formula 1 as an active ingredient, wherein the improvement of the skin condition is at least one selected from the group consisting of preventing or improving skin wrinkles and improving skin elasticity. Composition.
[Formula 1]

A quasi-drug composition for improving skin moisturization containing a catechin glycoside represented by the following formula (1) as an active ingredient.
[Formula 1]

The quasi-drug composition according to claim 7 or 8, wherein the catechin glycoside is obtained from an red bean ( Vigna angularis ) extract or a fraction thereof.
A food composition for improving skin condition containing a catechin glycoside represented by the following Formula 1 as an active ingredient, wherein the improvement of the skin condition is at least one selected from the group consisting of preventing or improving skin wrinkles and improving skin elasticity. Composition.
[Formula 1]

A food composition for improving skin moisturization containing a catechin glycoside represented by the following formula (1) as an active ingredient.
[Formula 1]

The food composition of claim 10 or 11, wherein the catechin glycoside is obtained from red bean ( Vigna angularis ) extract or a fraction thereof.
delete A pharmaceutical composition for preventing or treating dry skin containing a catechin glycoside represented by the following formula (1) as an active ingredient.
[Formula 1]

The method of claim 14, wherein the catechin glycoside is red bean ( Vigna angularis ) extract or a fraction thereof, which is obtained from the pharmaceutical composition.
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