KR102633917B1 - Composition for reinforcing skin elasticity - Google Patents

Abstract

The present invention relates to a composition for enhancing skin elasticity, wherein the composition for enhancing skin elasticity contains 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl) as an active ingredient. ) Prop-2-enoethite compound is included in an appropriate content range and can exhibit anti-aging effects by strengthening skin elasticity by increasing the secretion of extracellular matrix.

Description

Composition for enhancing skin elasticity {COMPOSITION FOR REINFORCING SKIN ELASTICITY}

The present invention relates to a composition for enhancing skin elasticity that exhibits anti-aging effects by strengthening skin elasticity.

Recently, as the average lifespan has been extended due to the development of medical technology, the quality of life has improved, and the desire for a healthy and beautiful life has increased, interest in skin care and health is expanding. Accordingly, various beauty functional cosmetics have been developed for the purpose of maintaining healthy skin, and in particular, research on preventing, alleviating, and improving the formation of skin wrinkles is actively underway. In addition, there are recent limitations in the ability of cosmetic ingredients to reach the skin dermis and provide nutrients, and as there is a change in perception that ingestion of food can provide nutrients or functional ingredients to the skin to improve skin beauty, inner beauty foods Research to discover materials is also actively underway.

The skin is largely composed of three layers: the epidermis, dermis, and hypodermis. The epidermis, especially the stratum corneum, the outermost layer of the epidermis, acts as a skin barrier, preventing moisture and electrolytes from being lost from the skin. Meanwhile, the dermal layer plays a role in maintaining skin elasticity and supporting structure through collagen and elastin synthesis. In other words, collagen and elastin are major proteins produced in fibroblasts and are involved in the mechanical rigidity of the skin, tissue cohesion and elasticity (Moskowit, R. W. et al, Role of collagen hydroiysate in bone and joint disease, Semin Arthritis Rheu, 30: 87, 2000). Collagen consists of various isoforms depending on its shape and structural characteristics. There are a total of 28 collagen isotypes in human tissue, of which the collagen present in skin tissue is types 1, 3, and 4. 6. 7. 13, 14, 17, etc. are known. Collagen types 1 and 3 form interstitial components of the dermal layer, and collagen type 7 becomes the main component of the dermal and epidermal junction between the epidermis and dermis.

In skin connective tissue, type I collagen is present in the largest amount among extracellular matrix proteins, and other proteins such as elastin, fibronectin, integrin, fibrillin, and proteoglycan are present. Newly synthesized procollagen undergoes an enzymatic reaction and is secreted into the extracellular space of skin cells to form microfibrils with a triple helix configuration, and the microfibrils are leucine-rich small proteoglycans. It combines with -rich small proteoglycans to form fibrils. As a result, these fibrils come together to form collagen fibers that provide cohesion and elasticity to the skin (Bateman, J.F. et al., Collagen superfamily. Extracellular matrix, Harwood, New York, 2, 22-26, 1996).

In this way, the amount of extracellular matrix protein is important in order to improve the cohesion and elasticity of the skin and exhibit anti-aging functions, so there is an urgent need to develop functional substances that can increase the amount of extracellular matrix protein.

Korean Patent No. 457949

The present inventors conducted research from various angles to solve the above problems, and as a result, 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trime, which was previously recognized only as a whitening functional material. The aim is to provide a composition for strengthening skin elasticity that exhibits an anti-aging effect by strengthening skin elasticity using a toxyphenyl)prop-2-enoethite compound.

Therefore, the object of the present invention is to include 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite compound as an active ingredient. To provide a composition for enhancing skin elasticity.

In order to achieve the above object, the present invention provides 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2 represented by the following formula (I) -Provides a composition for enhancing skin elasticity, comprising an enoethite compound as an active ingredient:

<Formula I>

R ₁ , R ₂ and R ₃ are each independently H, methyl, ethyl, propyl or butyl, and X is CO or CH ₂ =CH ₂ CO.

According to the present invention, 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethyte compound, which was previously recognized only as a whitening functional material. A composition for enhancing skin elasticity containing an appropriate amount of as an active ingredient can increase the secretion amount of extracellular matrix.

In addition, the composition for enhancing skin elasticity is effective in anti-aging by enhancing skin elasticity by increasing the secretion amount of type 1 procollagen and fibronectin among the extracellular matrix.

Figure 1 shows fibroblasts treated with 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite compound of Example 1. This is a SEM (Scanning Electron Microscope) photo.
Figure 2 shows Type 1 Pro using the 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite compound of Example 1. This is a graph showing the results of measuring collagen secretion.
Figure 3 shows the measurement of fibronectin secretion by the 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite compound of Example 1. This is a graph showing the results.
Figure 4 shows MMP-1 prepared by the 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite compound of Example 1. This is a graph showing the results of measuring the secretion amount of (matrix metalloproteinase-1).
Figure 5 is a cytotoxicity test using the 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite compound of Example 1. The result is the graph shown.

Hereinafter, the present invention will be described in more detail to facilitate understanding of the present invention.

In this specification, “skin” refers to an organ that covers the outside of a living thing, and is composed of the epidermis, dermis, and subcutaneous fat layer, and is the broadest concept to include the scalp and hair as well as tissues covering the outside of the face or the entire body. am.

As used herein, “5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite compound” generally refers to Melasolv It is also called by the brand name (melasolve).

Composition for enhancing skin elasticity

The present invention uses 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethyl compound represented by the following formula (I) as an active ingredient: It relates to a composition for enhancing skin elasticity, comprising:

<Formula I>

R ₁ , R ₂ and R ₃ are each independently H, methyl, ethyl, propyl or butyl, and X is CO or CH ₂ =CH ₂ CO.

The 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite compound represented by the formula (I) is a substance that exhibits whitening function. However, in the present invention, 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethyl represented by the formula (I) A composition for enhancing skin elasticity can be provided by utilizing the compound's property of increasing the secretion of extracellular matrix. In particular, among the extracellular matrices, the secretion amount of type 1 procollagen and fibronectin is increased, making it effective in anti-aging by strengthening skin elasticity.

The “5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethyte compound” is commonly referred to as melasolve. It is also called a brand name.

In the present invention, the 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite compound represented by the formula (I) The content may be 0.01 to 3% by weight, preferably 0.05 to 2% by weight, and more preferably 0.05 to 1% by weight, based on the total weight of the composition.

The content of 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethyte compound represented by the formula (I) is 0.01% by weight. If it is less than 3% by weight, the increase in the expression level of the extracellular matrix is minimal, and if it is more than 3% by weight, the stability of the composition and formulation safety may decrease, and the manufacturing cost may increase.

In the present invention, the composition for enhancing skin elasticity can increase the secretion amount of extracellular matrix.

5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethyte compound represented by the formula (I) and skin elasticity strengthening function and The relationship was not yet known.

However, through research, the inventors of the present invention found that 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2- represented by the formula (I) It was found that the enoethite compound increases the secretion of extracellular matrix, especially type 1 procollagen and fibronectin, and is effective in anti-aging by strengthening skin elasticity.

In the present invention, the composition for enhancing skin elasticity may be a composition for external skin application.

5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethyte compound included as an active ingredient in the composition for enhancing skin elasticity When applied to the skin, it can prevent or delay aging by increasing the secretion of extracellular matrix such as type 1 procollagen and fibronectin, thereby improving skin elasticity and giving it shine.

In the present invention, the composition for enhancing skin elasticity may be a cosmetic composition.

The cosmetic composition can be provided in any formulation suitable for topical application. For example, it may be provided in the form of a liquid, an emulsion obtained by dispersing an oil phase in an aqueous phase, an emulsion obtained by dispersing an aqueous phase in an oil phase, a suspension, solid, gel, powder, paste, foam, or aerosol composition. Compositions of this dosage form can be prepared according to conventional methods in the art.

In addition to the above-mentioned substances, the cosmetic composition may contain other ingredients that can have a synergistic effect on the skin elasticity strengthening effect within the range that does not impair the skin elasticity strengthening effect. The cosmetic composition according to the present invention may contain a substance selected from the group consisting of vitamins, high molecular weight peptides, molecular polysaccharides, and sphingolipids. In addition, the cosmetic composition according to the present invention may include moisturizers, emollients, surfactants, ultraviolet absorbers, preservatives, disinfectants, antioxidants, pH adjusters, organic and inorganic pigments, fragrances, cooling agents, or antiperspirants. . The mixing amount of the above components can be easily selected by a person skilled in the art within a range that does not impair the purpose and effect of the present invention.

In the present invention, the composition for enhancing skin elasticity may be a pharmaceutical composition. The pharmaceutical composition may be a pharmaceutical composition for preventing or treating diseases caused by decreased skin elasticity, for example, for preventing or treating dry skin, etc.

The pharmaceutical composition can be formulated into an oral or parenteral dosage form in solid, semi-solid or liquid form by using the composition as an active ingredient and adding a commonly used inorganic or organic carrier.

Examples of the preparations for oral administration include tablets, pills, granules, tablets, hard capsules, powders, fine granules, powders, emulsions, syrups, pellets, etc. In addition, preparations for parenteral administration include injections, drops, ointments, lotions, sprays, suspensions, emulsions, suppositories, etc. In order to formulate the active ingredient of the present invention, it can be easily formulated by carrying out conventional methods, and surfactants, excipients, colorants, spices, preservatives, stabilizers, buffers, suspending agents, and other commonly used auxiliaries can be appropriately used.

The pharmaceutical composition according to the present invention has an excellent effect in strengthening skin elasticity and can be usefully used in the treatment and prevention of skin diseases caused by damage to skin elasticity. Skin diseases caused by decreased skin elasticity include, but are not limited to, xeroderma, psoriasis, and ichthyosis.

The pharmaceutical composition may be administered orally, parenterally, rectally, topically, transdermally, intravenously, intramuscularly, intraperitoneally, subcutaneously, etc.

In addition, the dosage of the active ingredient will vary depending on the age, gender, and weight of the subject to be treated, the specific disease or pathological state to be treated, the severity of the disease or pathological state, the route of administration, and the judgment of the prescriber. Dosage determinations based on these factors are within the level of one skilled in the art. A typical dosage is 0.001 mg/kg/day to 2000 mg/kg/day, specifically 0.5 mg/kg/day to 1500 mg/kg/day.

Preferred examples are presented below to aid understanding of the present invention. However, the following examples are merely illustrative of the present invention, and it is clear to those skilled in the art that various changes and modifications can be made within the scope and spirit of the present invention. It is natural that changes and modifications fall within the scope of the attached patent claims.

Example One

The compound 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite was used.

Experiment example 1: Type 1 procollagen , fibronectin and MMP -1 analysis

Amount of extracellular matrix secretion by 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite compound according to Example 1 An experiment was conducted to confirm the increase effect.

Fibroblasts isolated from human skin were seeded in 6 holes (5×10 ⁵ cells per hole) and cultured until they grew to about 90%. The 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite compound of Example 1 was dissolved in serum-free medium, respectively. The results of observing fibroblasts after treatment with concentrations of 0, 1, 5, and 10 ppm, respectively, and culturing in a CO ₂ incubator for 24 hours are shown in Figure 1.

In the following experiment, the 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethyl compound contained in the composition for strengthening the skin barrier was used. The experiment was conducted by diluting 100 times the content. That is, the following treatment groups (1 ppm, 5 ppm, 10 ppm) contain the 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-tri) in the skin barrier strengthening composition. This means that the methoxyphenyl)prop-2-enoethite compound is included in an amount of 0.01% by weight, 0.05% by weight, and 0.1% by weight, respectively.

Figure 1 shows fibroblasts treated with 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite compound of Example 1. This is an optical microscope photo.

Referring to Figure 1, it can be seen that the cell tissue of the treated group (1 ppm, 10 ppm) is more dense than the untreated group (0 ppm).

In addition, the supernatant of the cultured medium was taken out and the increase or decrease of procollagen, fibronectin, and MMP-1 (matrix metalloproteinase-1) was examined by western blotting assay. The test was conducted at a concentration considering cytotoxicity, and the results are shown in Figures 2, 3, and 4.

Figure 2 shows Type 1 Pro using the 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite compound of Example 1. This is a graph showing the results of measuring collagen secretion. At this time, the type 1 procollagen secretion amount represents the relative secretion amount when the secretion amount in the untreated group (0 ppm) is set to 1.

Referring to Figure 2, the 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite compound of Example 1 was treated. In the case of one fibroblast, the extracellular secretion amount of type 1 procollagen was found to be increased compared to the untreated group (0 ppm).

Figure 3 shows the measurement of fibronectin secretion by the 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite compound of Example 1. This is a graph showing the results.

Referring to Figure 3, the 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite compound of Example 1 was treated. In the case of one fibroblast, the extracellular secretion amount of fibronectin was found to be increased compared to the untreated group (0 ppm).

In addition, among the 1, 5, and 10 ppm treatment groups, it was confirmed that the 5 and 10 ppm treatment groups showed a significant difference in the amount of fibronectin secretion compared to the untreated group (0 ppm).

Figure 4 shows MMP-1 prepared by the 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite compound of Example 1. This is a graph showing the results of measuring the secretion amount of (matrix metalloproteinase-1).

Referring to Figure 4, the 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite compound of Example 1 was treated. In the case of one fibroblast, MMP-1 secretion was found to be increased compared to the untreated group (0 ppm), but it was confirmed that there was no significant difference compared to the untreated group (0 ppm).

Experiment example 2: Cytotoxicity experiment

Confirming the cytotoxicity of the 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite compound according to Example 1 An experiment was conducted for this purpose.

Fibroblasts isolated from human skin were seeded in 6 holes (5×10 ⁵ cells per hole) and cultured until they grew to about 90%. The 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite compound of Example 1 was dissolved in serum-free medium, respectively. The results of observing fibroblasts after treatment with concentrations of 0, 1, 5, and 10 ppm, respectively, and culturing in a CO ₂ incubator for 24 hours are shown in Figure 1.

These supernatants were taken out and the increase or decrease in cell number was checked using CCK8 (Cell Counting Kit8, Dojindo, CK04-11), and the results are shown in Figure 4.

Figure 5 is a cytotoxicity test using the 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite compound of Example 1. The result is the graph shown.

Referring to Figure 5, treatment of 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite compound of Example 1 There was no significant difference in the number of cells depending on the presence or absence and treatment amount, indicating that there was no cytotoxicity.

A formulation example of a composition according to an embodiment of the present invention will be described below, but it can be applied to various other formulations, and this is not intended to limit the present invention, but is only intended to provide a detailed explanation.

Formulation example 1. Nourishing lotion

Nutritional lotion was prepared in a conventional manner according to the composition shown in Table 1 below.

Raw material name Content (% by weight) glycerin 3 Butylene glycol 3 propylene glycol 3 Carboxy vinyl polymer 0.1 5-Methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite compound of Example 1 One beeswax 4 Polysorbate 60 1.5 Caprylic/Capric Liglyceride 5 squalane 5 Sorvitasequiolate 1.5 cetearyl alcohol One Triethanolamine 0.2 Preservatives, flavorings Appropriate amount Purified water remaining amount total 100

Formulation example 2. Nourishing lotion

A nutritional lotion was prepared by a conventional method according to the composition shown in Table 2 below.

Raw material name Content (% by weight) Purified water remaining amount glycerin 3 Butylene glycol 3 liquid paraffin 5 beta glucan 7 5-Methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite compound of Example 1 One carbomer 0.1 Caprylic/Capric Triglyceride 3 squalane 5 Cetearyl Glucoside 1.5 Sorbitan Stearate 0.4 Polysorbate 60 1.5 antiseptic Appropriate amount incense Appropriate amount pigment Appropriate amount Triethanolamine 0.1 total 100

Formulation example 3. Nourishing cream

A nutritional cream was prepared by a conventional method according to the composition shown in Table 3 below.

Raw material name Content (% by weight) glycerin 3.5 liquid paraffin 3 beta glucan 7 carbomer 7 5-Methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite compound of Example 1 One Caprylic/Capric Triglyceride One squalane 3 Cetaaryl Glucoside 5 Sorbitan Stearate 1.5 Polysorbate 60 0.4 Triethanolamine 1.2 Preservatives, flavorings Appropriate amount Purified water remaining amount total 100

Formulation example 4. Drugs for topical administration ( patch )Manufacture of

A medication (patch) for topical administration was prepared by a conventional method according to the composition shown in Table 4 below.

Raw material name Content (% by weight) 5-Methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite compound of Example 1 One Beta-1,3-glucan 3 Diethylamine 0.7 sodium sulfite 0.1 Polyoxyethylene lauryl ether (E.O=9) One Polyhydroxyethylenecetylstearyl ether (Cetomacrogol 1000) One viscous paraffin oil 2.5 Caprylic acid ester/Capric acid ester (Cetiol LC) 2.5 Polyethylene glycol 400 3 Polyacrylic acid (Carbopol 934P) One Purified water remaining amount total 100

Although the present invention has been described above with limited examples and drawings, the present invention is not limited thereto, and the technical idea of the present invention and the following description will be provided by those skilled in the art in the technical field to which the present invention pertains. Of course, various modifications and variations are possible within the scope of equivalence of the patent claims.

Claims (7)

5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethyl (5-methyl-2-) represented by the following formula (I) A composition for enhancing skin elasticity comprising (methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate) compound as an active ingredient:
<Formula I>

R ₁ , R ₂ and R ₃ are each independently H, methyl, ethyl, propyl or butyl, and X is CO or CH ₂ =CH ₂ CO. According to paragraph 1,
The content of the 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoethite compound represented by the formula (I) is the total amount of the composition. 0.01 to 3% by weight of a composition for enhancing skin elasticity. According to paragraph 1,
The composition is a composition for enhancing skin elasticity, which increases the secretion amount of extracellular matrix. According to paragraph 3,
A composition for enhancing skin elasticity, wherein the extracellular matrix is at least one selected from type 1 procollagen and fibronectin. According to paragraph 1,
The composition is a composition for strengthening skin elasticity, which is a composition for external application to the skin. According to paragraph 1,
The composition is a cosmetic composition, a composition for enhancing skin elasticity. According to paragraph 1,
The composition is a pharmaceutical composition, a composition for enhancing skin elasticity.