KR102503110B1 - Composition for improving skin conditions comprising genipin-1-b-D-gentiobioside - Google Patents

Abstract

The present invention relates to a cosmetic composition, a pharmaceutical composition, and a health food having excellent effects on antiglycation, whitening, wrinkle improvement, elasticity improvement or anti-inflammatory in the skin. The composition of the present invention shows excellent effects on skin whitening, skin elasticity enhancement, skin wrinkle improvement, skin moisturizing or skin anti-inflammatory. The compound of 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 genipin-1-beta-D-gentiobioside

The present invention relates to a composition having excellent effects in improving skin conditions, and more particularly, to a cosmetic composition, pharmaceutical composition, and health food having excellent effects in antiglycation, whitening, wrinkle improvement, elasticity improvement, or anti-inflammatory of the skin. will be.

It is a common desire to have white and fair skin. Skin color or brightness is genetically determined according to the concentration and distribution of melanin in human skin, but is also influenced by environmental or physiological conditions such as solar ultraviolet rays, fatigue or stress. Melanin is produced through a non-enzymatic oxidation reaction after sequentially converting tyrosine, a kind of amino acid, into DOPA and dopaquinone by an enzyme called tyrosinase acting as a catalyst. Although the pathway by which melanin is produced is known, the cause of triggering tyrosinase in the mechanism inducing melanin synthesis has not yet been clarified in detail.

On the other hand, commonly known whitening ingredients include substances that inhibit tyrosinase enzyme activity, such as Kojic acid or arbutin, and also hydroquinone, vitamin C (L-Ascorbic acid) or derivatives thereof. and various plant extracts are known to have whitening effects. By inhibiting the synthesis of melanin pigment, they can realize skin whitening by brightening the skin tone, and can improve skin hyperpigmentation such as spots and freckles caused by ultraviolet rays, hormones, or heredity. However, when applied to the skin, there is a problem in that the amount of use is limited due to safety problems such as irritation and redness, or a practical effect cannot be expected because the effect is insignificant.

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).

In addition, the final glycation product produced by glycation is a brownish substance and is known to accumulate in the upper dermal layer as skin aging progresses. It is thought to be a causative substance that gradually turns yellow as skin aging progresses, and it is known that as specific final saccharification products accumulate, reflected light from the skin decreases. While the amount of melanin pigment in the skin has a weak relationship with skin aging, the amount of advanced glycation end products accumulated in the dermal layer of the skin gradually increases as skin aging progresses and can make the complexion dull (Hiroshi, O. et al ., Skin Research and Technology, 15, p. 496, 2009).

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, whitening, anti-wrinkle effects are superior to substances previously known to have anti-glycation, whitening, wrinkle improvement, elasticity improvement or anti-inflammatory effects 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, to solve the above problems, and to have a new active ingredient that is safe to the human body and has excellent antiglycation, whitening, wrinkle improvement, elasticity improvement or anti-inflammatory effect of the skin, that is, 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 contains Genipin-1-beta-D-gentiobioside as an active ingredient for skin whitening, skin elasticity enhancement, and skin wrinkle improvement. It provides a composition for skin moisturizing or skin anti-inflammatory, preferably a cosmetic composition, pharmaceutical composition or health food.

That is, the present invention relates to the use of genipin-1-beta-D-gentiobioside as a cosmetic composition or pharmaceutical composition and for skin whitening, skin elasticity enhancement, skin wrinkle improvement, skin moisturizing or skin anti-inflammatory use provides a new use for

The inventors of the present invention found that genipin-1-beta-D-gentiobioside promotes collagen production in the skin and inhibits the activity of elastase, thereby improving wrinkles and elasticity of the skin. has completed In addition, it was confirmed that the genipin-1-beta-D-gentiobioside exhibits a skin whitening effect by reducing the total amount of melanin and exhibits an anti-inflammatory effect by inhibiting NO production. In addition, the genipin-1-beta-D-gentiobioside exhibits an anti-glycation effect, so it can act as an auxiliary role in improving skin whitening, skin wrinkles and skin elasticity, resulting in a synergistic effect.

In the present invention, the 'whitening effect' refers to not only brightening the skin tone, but also improving skin hyperpigmentation such as spots or freckles caused by ultraviolet rays, hormones, or heredity. This whitening effect can be achieved, for example, by reducing the total amount of melanin pigment, but the present invention is not limited by this mechanism.

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 can help skin whitening by suppressing the production of advanced glycation end products accumulated in the upper dermal layer according to skin aging. Therefore, in the present invention, the antiglycation effect can generate a synergistic effect on skin whitening as well as skin elasticity enhancement and wrinkle improvement.

The present invention provides a composition containing a compound represented by Formula 1 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 of C ₂₃ H ₃₄ O ₁₅ , a molecular weight of 550.507, and is named Genipin-1-bD-gentiobioside.

The present invention is not particularly limited to the method for obtaining the genipin-1-beta-D-gentiobioside, and it may be 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 the genipin-1-beta-D-gentiobioside 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

Genipin-1-beta-D-gentiobioside of the present invention may exist in unsolvated form as well as solvated form including hydrate, ethanolate and the like. Genipin-1-beta-D-gentiobioside of the present invention may exist in crystalline or amorphous form, and all such physical forms are included in the scope of the present invention.

The composition for skin whitening, enhancing skin elasticity, improving skin wrinkles, moisturizing skin or 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, an emulsion, and a make-up. 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 It may be prepared as a formulation selected from the group consisting of foundation, patch and spray, 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 especially 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 provides a method for skin whitening, enhancing skin elasticity, improving skin wrinkles, moisturizing skin or anti-inflammatory skin, comprising applying a compound represented by Formula 1 to the skin of a subject. The subject includes, without limitation, mammals including mice, livestock, humans, and the like.

According to another embodiment of the present invention, the present invention provides a pharmaceutical composition for skin whitening, skin elasticity enhancement, skin wrinkle improvement, skin moisturizing or skin anti-inflammatory, containing the compound of Formula 1 as an active ingredient. to provide.

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 may also be provided in the form of an external skin preparation for skin whitening, skin elasticity enhancement, skin wrinkle improvement, skin moisturizing, or skin anti-inflammatory containing the compound of Formula 1 as an active ingredient.

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

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

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 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 skin whitening, skin elasticity enhancement, skin wrinkle improvement, skin moisturizing, or skin anti-inflammatory. When an additional skin whitening, skin elasticity enhancement, skin wrinkle improvement, skin moisturizing or skin anti-inflammatory component is included, the composition of the present invention can be used for skin whitening, skin elasticity enhancement, skin wrinkle improvement, skin moisturizing or skin anti-inflammatory The effect could 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; As a whitening ingredient known in the art, substances that inhibit tyrosinase enzyme activity such as Kojic acid and arbutin, hydroquinone, vitamin-C (L-Ascorbic acid); 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.

When the pharmaceutical composition of the present invention contains an effective amount of the compound of Formula 1, it can provide desirable skin whitening, skin elasticity enhancement, skin wrinkle improvement, skin moisturizing or skin anti-inflammatory effects. In the present invention, the term 'effective amount' means an amount of a compound capable of sufficiently exhibiting skin whitening, skin elasticity enhancement, skin wrinkle improvement, skin moisturizing or skin anti-inflammatory effects.

The effective amount of the compound of Formula 1 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 the compound 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 provides a health food for skin whitening, skin elasticity enhancement, skin wrinkle improvement, skin moisturizing or skin anti-inflammatory containing the compound of Formula 1.

In the present specification, 'health food' refers to a food prepared by adding the compound of Formula 1 to food materials such as beverages, teas, spices, chewing gum, confectionery, etc., or encapsulated, powdered, or suspended. It means that it brings about a specific effect, but unlike general drugs, it has the advantage of not having side effects that may occur when taking drugs for a long time 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 in skin whitening, skin elasticity enhancement, skin wrinkle improvement, skin moisturizing, or skin anti-inflammatory, and are very useful.

When the compound of Formula 1 is used as a food additive, the compound of Formula 1 may be added as it is or used together with other foods or food ingredients, and may be appropriately used according to conventional methods. 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 in an amount of 0.00001% to 10% by weight based on the total weight of the composition.

The composition containing genipin-1-beta-D-gentiobioside of the present invention shows excellent effects on skin whitening, skin elasticity promotion, skin wrinkle improvement, skin moisturizing or skin anti-inflammatory.

The composition containing Genipin-1-beta-D-gentiobioside 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 One: Jenny Finn -1-beta-D- Gentiobioside ( Genipin -1-b-D- gentiobioside ) substance information

[Formula 1]

Substance name: Genipin-1-b-D-gentiobioside

CAS No. : 29307-60-6

Molecular formula: C ₂₃ H ₃₄ O ₁₅

Molecular Weight: 550.507

Where to buy: Shanghai Tauto 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 Amount of type 1 collagen synthesis (ng/ml) Increase (%) negative control group 150.2 - Positive control group (Vitamin C, 52.85ppm) 246.8 64.3 Compound of Formula 1 (1 ppm) 192.4 28.1 Compound of Formula 1 (10 ppm) 219 45.8

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 active 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) 5.4 48.08 Compound of Formula 1 (10 ppm) 9.3 31.58 Positive control group (Quercetin, 10ppm) 3.5 66.35 Control (DMSO, 20 ppm) 10.4 -

As can be seen from the results of Table 2, 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. Glycosylation inhibitory activity can be obtained by the following formula.

Anti-glycation effect of the compound of Formula 1

sample Inhibition rate (%) Control (DMSO, 50 ppm) - Positive control group (Aminoguanidine, 55ppm) 54.8 Compound of Formula 1 (50 ppm) 41.7 Compound of Formula 1 (25 ppm) 25.6

As can be seen from the results in Table 3, the compound of Formula 1 exhibits an excellent antiglycation effect, so that the antiglycation effect plays a secondary role in skin whitening or skin wrinkles and elasticity improvement, and synergistic effects can be expected.

Experimental example 4: Whitening effect - melanin total amount reduction effect

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

The compound of Formula 1 was added to the culture medium to a final concentration of 1 ppm or 10 ppm, and arbutin, a control, was added to the medium to be 100 ppm, and each B-16 melanoma cell was treated 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 in 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 was calculated as an inhibition rate (%), and the results are summarized in Table 4 below.

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

sample Amount of melanin produced (abs) Inhibition rate (%) Control (DMSO, 10 ppm) 0.33 - Positive control group (Arbutin, 100ppm) 0.228 31.06 Compound of Formula 1 (10 ppm) 0.171 48.22 Compound of Formula 1 (1 ppm) 0.242 26.57

As can be seen from the results of Table 4, the compound of Formula 1 showed a significantly superior effect of reducing the total amount of melanin even at 10 ppm, compared to arbutin, a positive control group, and it was found that it could be used for whitening purposes.

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

In order to confirm the anti-inflammatory effect and skin trouble alleviation 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 in which the compound of formula 1 was diluted at final concentrations of 1, 10, and 100 ppm was replaced. 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) 20.33 Compound of Formula 1 (10 ppm) 26.12 Compound of Formula 1 (100 ppm) 37.29

As can be seen from the results of Table 5, it was confirmed that the compound of 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 skin whitening or wrinkle improvement.

Claims (10)

A composition for skin whitening comprising a compound represented by Formula 1 below as an active ingredient.
[Formula 1]

A composition for enhancing skin elasticity comprising a compound represented by Formula 1 as an active ingredient.
[Formula 1]

A composition for improving skin wrinkles comprising a compound represented by Formula 1 as an active ingredient.
[Formula 1]

A composition for moisturizing skin comprising a compound represented by Formula 1 as an active ingredient.
[Formula 1]

delete The composition according to any one of claims 1 to 4, wherein the composition is used as a cosmetic composition or a health food. The composition according to any one of claims 1 to 4, wherein the compound represented by Formula 1 is contained in an amount of 0.00001 to 10% by weight based on the total weight of the composition. The composition according to any one of claims 1 to 4, wherein the compound represented by Formula 1 contained in the composition also exhibits an anti-glycation effect.
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