TW201717903A - Ginsenoside fatty acid ester compounds, preparation method thereof, and cosmetic composition comprising the same - Google Patents

Abstract

The invention relates to a ginsenoside fatty acid ester compound, a method of preparing the same, and a cosmetics composition including the same. More particularly, the invention relates to a ginsenoside fatty acid ester compound modified to be a fatty acid ester compound having a hydrophobic property and a method of preparing the same. The penetration of the compound into the horny layer is excellent, and the compound effectively inhibits the production of melanin and MMP-1 such that the compound preferably applies to cosmetics compositions for skin whitening and a reduction in wrinkles.

Description

Ginsenoside fatty acid ester compound, preparation method thereof and cosmetic composition containing same

The present invention relates to a novel ginsenoside fatty acid ester compound having skin whitening and anti-oxidation effects, a process for preparing the same, and a cosmetic composition containing the same.

Panax ginseng C.A. Meyer is a plant belonging to the genus Panax ginseng. It is used as a crude drug used in Korea, China, Japan and other countries since 2000 years ago. It is used for the purpose of preventing disease and prolonging life. The effects and effects of ginseng known to date have effects on the central nervous system, anticancer effects and anticancer activities, immune function regulation, antidiabetic effects, hyperfunction of liver function, improvement of cardiovascular disorders and anti-atherosclerosis, Blood pressure regulation, improvement of menopausal disorders and effects on osteoporosis, anti-stress and anti-fatigue effects, antioxidant activity and inhibition of aging.

The various effects and effects of the above ginseng are derived from "ginsenoside" (Ginsenoside, a glycoside contained in ginseng, also known as "saponin") which is one kind of saponin. Ginsenoside is a structure in which a sugar is bonded to a steroid skeleton, and the structure changes due to heat. When cooked in steam, the steroid-sugar bond is broken and the sugar is reduced, and different effects are exhibited depending on which sugar remains at the position. Further, since the water-soluble sugar is reduced, it exhibits fat solubility, and ginsenoside which easily passes through the cell membrane is formed.

There are more than 30 kinds of ginsenosides, which have different compositions and effects. Among them, as an active ingredient of a cosmetic composition, ginsenoside F1 and ginsenoside compound K are proposed. These compounds have a structure in which a sugar (glucose) is bonded to the protopanaxadiol in the saponin component of ginseng.

It is known that ginsenoside F1 down-regulates the expression of Bcl-2 and Brn-3a by inhibiting allergy and apoptosis by irradiation of ultraviolet B, thereby protecting human HaCaT keratinocytes (Lee EH, et al., J. Invest. Dermatol. 121: 607-13, 2003). In Korean Cosmetics Patent No. 2014-0013796, it is disclosed that the ginsenoside F1 has an effect of reducing sebum, improving acne and allergic dermatitis, and can be used for cosmetics for improving skin inflammatory diseases. In No. 095949, it is proposed that ginsenoside F1 has an antioxidant, anti-inflammatory effect and an effect of improving skin moisturizing power, and can be used as an external preparation for skin.

Further, in the Korean Patent Publication No. 10-0485326 and No. 10-1427572, it is disclosed that the ginsenoside compound K promotes the formation of hyaluronic acid and can be used as a composition for external use of the skin, and the Korean Patent Publication No. 2015-0083290 Among them, it has the effect of whitening and improving wrinkles.

Further, in Korean Patent No. 10-1140039, it is disclosed that ginsenoside F1 or compound K protects the boundary between the epidermis and the dermis of the skin and has an effect of preventing skin aging and improving wrinkles, and thus can be used as a composition for external use of skin.

As described above, when ginsenoside F1 or compound K is applied to a cosmetic composition, various effects including skin whitening effect and anti-oxidation effect (prevention of aging, improvement of wrinkles) can be obtained.

On the other hand, in terms of the structure of the skin, the cell gap and the stratum corneum which is the outermost layer are mostly composed of lipids, and the surface of the skin is covered by sebum (oil component) secreted by the cells. Unfortunately, hydrophilic substances are difficult to penetrate through the skin, and for penetration, it is necessary to increase the concentration of use or apply an electric shock such as ion electrophoresis.

Ginsenoside F1 or compound K has a structure in which a saccharide is linked to an alcoholic OH group by an ether bond, and thus has high hydrophilicity and a large molecular weight. Therefore, the skin penetration of ginsenoside F1 or compound K is very low, so that even if the cosmetic composition includes these components, the amount of penetration or absorption into the skin is small and the effect actually obtained is small.

[Patent Document 1] (Patent Document 1) Korean Laid-Open Patent No. 2014-0013796, "Cosmetic Composition for Improving Skin Inflammatory Diseases Containing Ginsenoside F1 as an Active Component" (Patent Document 2) Korean Patent Publication Japanese Patent Publication No. 2013-0095949, "A composition for external use of skin containing ginsenoside F1" (Patent Document 3) Korean Patent No. 10-0485326, "Hybric acid production promoter composed of ginsenoside compound K" (Patent Literature) 4) Korean Patent No. 10-1427572, "Composition of a skin external preparation for promoting hyaluronic acid production containing ginsenoside Re and ginsenoside compound K" (Patent Document 5) Korean Patent Publication No. 2015-0083290, "Ginseng A method for preparing a saponin derivative and a ginsenoside derivative prepared thereby comprising a composition for whitening and wrinkle improvement as an active ingredient" (Patent Document 6) Korean Patent No. 10-1140039, "containing ginsenoside F1 or a compound K skin external preparation composition" [Non-Patent Document] (Non-Patent Document 1) Lee EH, et al, F1 significantly reduces the ultraviolet B induced fine Cell death and protection of HaCaT cells from apoptosis caused by UVB irradiation. Ultraviolet B-induced apoptosis and ginsenoside-F1 regulation inhibits the expression of Bcl-2 and Brn-3a induced by ultraviolet light B (F1) (Ultraviolet-B-induced apoptosis is related with ginsenoside-F1-mediated inhibition of ultraviolet-B-induced down-regulation of Bcl-2 and Brn-3a expression) J. Invest. Dermatol, 121:607-13, 2003 .

[Problems to be Solved by the Invention] In order to solve the above problems, the inventors of the present invention have prepared a novel compound by reacting these compounds with a fatty acid vinyl ester compound in order to improve the hydrophobicity of ginsenoside F1 or compound K, thereby confirming the following situation. The present invention has been completed: the compound obtained in this manner is excellent in the penetration into the stratum corneum of the skin, inhibits the formation of melanin and has a skin whitening effect, and significantly inhibits the collagen degrading enzyme, Matrix M metalloproteinase-1. , MMP-1) and excellent wrinkle improvement effect.

Accordingly, it is an object of the present invention to provide a novel ginsenoside fatty acid ester compound.

Further, another object of the present invention is to provide a process for producing a ginsenoside fatty acid ester compound.

Further, another object of the present invention is to provide a use of a ginsenoside fatty acid ester compound as a cosmetic composition. [Means for solving the problem]

In order to achieve the above object, the present invention provides a ginsenoside fatty acid ester compound represented by the following Chemical Formula 1: [Chemical Formula 1] (In the above Chemical Formula 1, R ₁ to R ₃ are the same as those in the specification).

Further, the present invention provides a process for producing a ginsenoside fatty acid ester compound of Chemical Formula 1, which is represented by the following Reaction Formula 1, and a compound of the following Chemical Formula 6 and a C12 to C22 saturated or unsaturated fatty acid vinyl ester compound (fatty acid) Vinyl ester) is prepared by enzymatic conversion reaction: [Reaction formula 1] (In the above Reaction Formula 1, R ₁ to R ₃ are the same as those in the specification).

Furthermore, the present invention provides a cosmetic composition comprising the ginsenoside fatty acid ester compound represented by the above Chemical Formula 1 as an active ingredient. [Effects of the Invention]

The ginsenoside fatty acid ester compound of the present invention has improved whitening effect and wrinkle-improving effect of the conventional ginsenoside F1 or compound K, and has excellent hydrophobicity and excellent skin penetration to skin keratin.

Specifically, the above-mentioned compound acts on tyrosinase which is an enzyme which produces melanin which is a cause of freckles and melasma, and suppresses the production of melanin to exhibit a skin whitening effect, which significantly inhibits collagen breakdown than retinoic acid. The enzyme, that is, the performance of MMP-1, obtains a wrinkle-improving effect, and thus is formulated into various cosmetic products to improve consumer satisfaction.

Hereinafter, the present invention will be described in detail.

In the present invention, a novel compound which is modified in a hydrophobic manner in order to improve the skin absorbency of ginsenoside F1 or compound K is proposed. The above novel compound is preferably a ginsenoside fatty acid ester compound represented by the following Chemical Formula 1: [Chemical Formula 1] (In the above Chemical Formula 1, R ₁ is a saturated or unsaturated fatty acid group of C12 to C22, R ₂ is OH, or a saturated or unsaturated fatty acid group of C12 to C22, and R ₃ is H or OH). The saturated fatty acid groups of C12 to C22 mentioned in the present specification are lauryl (C12:0, lauryl), tridecyl (C13:0, tridecyl), myristyl (C14:0, myristil), fifteen. Alkyl (C15:0, pentadecyl), soft lipid (C16:0, palmityl), pearlescent (C17:0, margaryl), stearyl (C18:0, stearyl), nonadecyl (C19: 0, nonadecyl), peanut base (C20:0, arachidyl), icosyl (C21:0, heneixosylyl) or behenyl (C22:0, behenyl).

Further, the C12 to C22 unsaturated fatty acid groups mentioned in the present specification are a lipid sulfonyl group (C16:1, palmitoleyl), an oleyl group (C18:1, oleyl), and a myristyl group (C14:1, Myristoleyl), linoleyl (C18: 2, linoleyl) or arachidonic acid (C20: 3, arachidyl).

The above R _{1 is} preferably a soft aliphatic group, a stearyl group or an oleyl group, and more preferably a soft lipid group.

Further, R _{2 is} preferably OH, a soft aliphatic group, a stearyl group or an oleyl group, more preferably an OH or a soft aliphatic group.

In particular, the compound of Chemical Formula 1 of the present invention includes all isomers unless otherwise specified. The above isomers are considered within the scope of the invention for all stereoisomers, for example, which may be present due to asymmetric carbons on various R and Z substituents (including mirror image isomers (in the absence of asymmetric carbon). It may also be present in the case of) and partial stereoisomers). Individual stereoisomers of the compounds of the invention, for example, are not substantially different isomers, or may, for example, be racemates or be mixed with all stereoisomers or selected stereoisomers.

As an example, it can be represented by the isomer of the following chemical formula 1a: [Chemical Formula 1a] (In the above Chemical Formula 1, R ₁ to R ₃ are the same as those described above).

Examples of the compound represented by the above Chemical Formula 1 include the following compounds: [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] .

Further, the present invention provides a process for producing a ginsenoside fatty acid ester compound of Chemical Formula 1, which is represented by the following Reaction Formula 1, and a compound of the following Chemical Formula 6 and a C12 to C22 saturated or unsaturated fatty acid vinyl ester compound (fatty acid) Vinyl ester) for enzymatic conversion reaction: [Reaction formula 1] (In the above Reaction Formula 1, R ₁ to R ₃ are the same as those described above).

In the above Reaction Formula 1, the compound of Chemical Formula 6 as a starting material is a ginsenoside compound, preferably a ginsenoside compound represented by the following Chemical Formula 7, ginsenoside F1 (R ₃ = OH), and a ginsenoside compound represented by Chemical Formula 8. K(R ₃ =H) or a derivative thereof.

[Chemical Formula 7]

[Chemical Formula 8]

Such starting materials can be obtained from extracts such as ginseng, red ginseng, white ginseng, ginseng, ginseng, ginseng leaves or ginseng fruits, directly prepared or purchased by a commercially available person.

As an example, it can be prepared by hydrolyzing ginseng refined saponin with an acid, a base, or an enzyme to remove sugar from ginseng saponin, and then passing the reaction liquid through a column. Examples of the enzyme which can be used herein include β-glucosidase which decomposes saponin-glycosidase, α,β-arabinosidase (α,β-arabinosidase), α,β. - an exo-glucose-decomposing enzyme such as a rhamnosidase-degrading enzyme (α, β-rhamnosidase), a complex enzyme agent containing the same, and the like.

Further, in the reaction formula 1, the fatty acid vinyl ester compound is a compound in which R ₁ and R ₂ are introduced into the chemical structure of Chemical Formula 1, and may be a C12 to C22 saturated or unsaturated fatty acid vinyl ester compound.

The above saturated fatty acid vinyl ester compound of C12 to C22 is preferably vinyl laurate (C12:0, lauryl), vinyl tridecylic acid ester (C13:0, tridecylic acid vinyl ester), vinyl myristate (C14: 0, myristic acid vinyl ester), pentadecylic acid vinyl ester (C15:0, pentadecylic acid vinyl ester), vinyl palmitate (C16:0, palmitic acid vinyl ester), vinyl phthalate (C17:0) ,margaric acid vinyl ester), vinyl stearate vinyl ester (C18:0, stearic acid vinyl ester), vinyl nonadecyl acid ester (C19:0, nonadecylic acid vinyl ester), vinyl arachidate (C20:0, arachidyl ), vinyl phthalate (C21: 0, heenixosylic acid vinyl ester) or vinyl phthalate (C22: 0, behenylic acid vinyl ester).

The above unsaturated fatty acid vinyl ester compounds of C12 to C22 are vinyl palmitate (C16:1, palmiticoleic acid vinyl ester), vinyl oleic acid vinyl ester (C18:1, oleylic acid vinyl ester), vinyl myristate ( C14:1, myristoleylic acid vinyl ester), linoleylic acid vinyl ester (C18:2, arachidonylic acid vinyl ester).

The above fatty acid vinyl ester compound is more preferably vinyl palmitate, vinyl stearate or vinyl oleate, and most preferably vinyl palmitate.

The above reaction is carried out by an enzymatic conversion reaction.

In this case, the enzyme may be characterized in that a hydrolase such as a protease or a lipase is used, and as the hydrolase, flavourzyme, protease A, or alcalase may be used. , a mixture of savinase, protamex, esperase, novozyme, esterlase, acylase, etc., but Not limited to this. Further, as the above enzyme source, a microorganism containing the above hydrolase can also be used. In an embodiment of the invention, Novozymes lipase 435 (novozyme 435, Novozymes) is preferably used.

Examples of such a strain include Bacillus sp., Aspergillus oryzae, Aspergillus niger, Candida antarctica, and the like, but are included as long as they are included. The strain or microorganism of the hydrolase can be used without limitation.

The type and method of the enzyme to be added to the reaction formula 1 are not particularly limited as long as they do not inactivate the enzyme, and can be used in a method generally used in the art.

The reaction temperature is a temperature which does not inactivate the enzyme, that is, in the case of Novozymes lipase, the reaction is carried out by stirring in the range of 20 ° C to 60 ° C for 1 hour to 120 hours, preferably for 36 hours. The reaction was carried out for 72 hours.

The solvent used at this time may be used singly or in combination with a lower alcohol such as water, methanol, ethanol or propanol, acetone as an organic solvent, dimethylformamide (DMF), dichloromethane (MC), diisopropyl ether. And diethyl ether, tetrahydrofuran (THF), dimethylacetamide (DMA), dimethyl hydrazine (DMSO), chlorobenzene, toluene, benzene, etc., preferably acetone.

The ginsenoside fatty acid ester compound of Chemical Formula 1 of the present invention can be applied to various fields, and is preferably used as an active ingredient of a cosmetic composition.

In other words, the ginsenoside fatty acid ester compound of Chemical Formula 1 retains the whitening effect and wrinkle-improving effect of the ginsenoside compound, particularly ginsenoside F1 and compound K, and has hydrophobicity and is excellent in penetration into the stratum corneum of the skin.

Further, the ginsenoside fatty acid ester compound of the present invention exhibits hydrophobicity and is more reactive with tyrosinase which is an enzyme which produces melanin which is a cause of freckles and chloasma. Therefore, as shown in Test Example 1, the whitening effect of kojic acid or resveratrol superior to the previous whitening effect can be ensured.

Furthermore, the effect of inhibiting the expression of MMP-1, which is an enzyme which decomposes collagen, was measured (see Test Example 2). As a result, it was found that the ginsenoside fatty acid ester compound of the present invention can more significantly inhibit the above MMP-1 than retinoic acid. Performance to ensure wrinkle improvement.

Therefore, the ginsenoside fatty acid ester compound of Chemical Formula 1 can be used as an active ingredient of a cosmetic composition, and the content thereof at this time varies depending on the dosage form, and may be 0.001% by weight to 99% by weight. When the active ingredient is contained in the above range, it is not only suitable for exhibiting the intended effect of the present invention, but also satisfies the stability and solubility of the composition at the same time, and in terms of cost performance, it is preferable to include the case according to the above range. .

The cosmetic composition can be prepared in any dosage form usually prepared in the technical field, for example, can be formulated into a solution suspension, an emulsion, a paste, a gel, a cream, a lotion, a powder, an oil, a powder foundation, and an opacity. Liquid foundation, wax foundation, spray, etc., but are not limited thereto. More specifically, it can be prepared into a sunscreen, a soft lotion, a shrinking lotion, a nutritional lotion, a nutrient cream, a massage cream, a serum, an eye cream, a mask, a spray or a powder.

Furthermore, the cosmetic composition of the present invention may contain a fatty substance, an organic solvent, a solvent, a concentrate, a gel, a softener, an antioxidant, a suspending agent, a stabilizer, a foaming agent, a fragrance, and an interface. Active agent, water, ionic or nonionic emulsifier, filler, metal ion blocker, chelating agent, preservative, vitamin, blocker, wetting agent, essential oil, dye, pigment, hydrophilic or An adjuvant which is commonly used in the field of cosmetics or dermatology, a lipophilic active agent, a lipoprotein or other optional ingredients commonly used in cosmetics. The above adjuvants are introduced in amounts generally used in the field of cosmetic or dermatological science.

When the above dosage form is a paste, a cream or a gel, as the carrier component, animal oil, vegetable oil, wax, paraffin, starch, tragacanth, cellulose derivative, polyethylene glycol, hydrazine can be used. , bentonite, cerium oxide, talc or zinc oxide.

When the above dosage form is powder or spray, as a carrier component, lactose, talc, cerium oxide, aluminum hydroxide, calcium citrate or polyamidamine powder may be used, especially in the case of spraying, which may further include chlorofluorocarbon. Propellants such as hydrocarbons, propane/butane or dimethyl ether.

When the above dosage form is a solution or an emulsion, as a carrier component, a solvent, a solvent or an opacifying agent such as water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol or benzoic acid is used. A fatty acid ester of benzyl ester, propylene glycol, 1,3-ethylene glycol butyl ether oil, glycerol fatty ester, polyethylene glycol or sorbitan.

When the above dosage form is a suspension, as a carrier component, a liquid diluent such as water, ethanol or propylene glycol, ethoxylated isostearyl alcohol, polyoxyethylene sorbitan ester and polyoxyethylene sorbitan ester can be used. Suspending agent, microcrystalline cellulose, aluminum metahydroxide, bentonite, agar or tragacanth.

Hereinafter, the present invention will be described in more detail based on the following examples. However, the following examples are merely illustrative of the invention, and the contents of the invention are not limited to the following examples.

[Example 1] Preparation of Compound of Chemical Formula 2 A compound of Chemical Formula 8 (Compound K, 1 eq), vinyl palmitate (2.5 eq), and 4 Å molecule (100 wt%) were injected into a Pressure Tube (Pressure Tube). Novozyme lipase 435 and anhydrous acetone (500 wt%, 5 times relative to the substrate) were stirred at 45 ° C for 3 days to carry out a reaction.

After the completion of the reaction, the obtained product was purified by silica gel column chromatography (ethyl acetate:methanol = 10:1) to give the compound of the formula 2 (white solid, yield: 75%).

¹ H-NMR (300MHz, CDCl3) d 7.27(1H), 5.78(1H), 5.28(2H), 5.16(1H), 5.02(1H), 4.77(1H), 4.42(1H), 4.15(1H), 4.04(1H), 3.93(1H), 3.83(1H), 3.56-3.47(3H), 2.44(2H), 2.35(3H), 2.21(1H), 2.15(1H), 2.06(1H), 1.90-1.87 (3H), 1.80-1.78(2H), 1.72-1.61(13H), 1.57-1.41(5H), 1.31-1.25(14H), 1.16(4H), 1.07-1.00(4H), 0.93-0.88(12H)

[Example 2] Preparation of compound of Chemical Formula 3 A compound of Chemical Formula 3 (yield 85%) was prepared in the same manner as in the above Example 1 except that the compound of the formula 7 (ginsenoside F1, 1 eq) was used as a starting material.

¹ H-NMR (300MHz, CDCl3) d 7.27(1H), 5.74(1H), 5.26-5.16(4H), 5.02(1H), 4.77(1H), 4.42(1H), 4.27-4.15(2H), 4.02 (2H), 3.83(1H), 3.56(1H), 3.51(1H), 3.37(1H), 2.43(2H), 2.34(3H), 2.21-2.06(3H), 1.92(1H), 1.79-1.61( 17H), 1.57(3H), 1.41-1.35(8H), 1.31-1.27(23H), 1.2-1.12(2H), 1.04-0.74(13H)

[Example 3] Preparation of compound of Chemical Formula 4 A compound of Chemical Formula 4 (yield 89%) was obtained in the same manner as in the above Example 1 except that the compound of the formula 8 (Compound K, 2 eq) was used as the starting material.

¹ H-NMR (300MHz, CDCl3) d 7.27(1H), 5.74(1H), 5.26-5.16(4H), 5.02(1H), 4.77(1H), 4.42(1H), 4.27-4.15(2H), 4.02 (2H), 3.83(1H), 3.56(1H), 3.51(1H), 3.37(1H), 2.43(2H), 2.34(3H), 2.21-2.06(3H), 1.92(1H), 1.79-1.61( 17H), 1.57(3H), 1.41-1.35(8H), 1.31-1.27(23H), 1.2-1.12(2H), 1.04-0.74(13H)

[Example 4] Preparation of compound of Chemical Formula 5 A compound of Chemical Formula 5 (yield 88%) was obtained in the same manner as in the above Example 1 except that the compound of Chemical Formula 7 (ginsenoside F1, 2 eq) was used as a starting material.

¹ H-NMR (300MHz, CDCl3) d 7.27(1H), 5.74(1H), 5.26-5.16(4H), 5.02(1H), 4.77(1H), 4.42(1H), 4.27-4.15(2H), 4.02 (2H), 3.83(1H), 3.56(1H), 3.51(1H), 3.37(1H), 2.43(2H), 2.34(3H), 2.21-2.06(3H), 1.92(1H), 1.79-1.61( 17H), 1.57(3H), 1.41-1.35(8H), 1.31-1.27(23H), 1.2-1.12(2H), 1.04-0.74(13H)

[Test Example 1] Melanin production inhibitory effect in melanin-producing cells The melanin production-inhibiting effect in melanin-producing cells was measured by the method of Dooley on the compound prepared in the above Example 2.

The cell strain used was mouse-derived B16 F10 (black seed cell) purchased from Bank of Korea Cell Bank. The cell culture medium (Dulbecco's Modified Eagle Medium, DMEM) (Cat No. 11995), fetal calf serum (Fetal Calf Serum, FBS) (Cat No. 16000-044) and the desired cell culture are purchased from Invitrogen (GIBCO). Antibiotic-antimycotic agent (Cat No. 15240-062).

The cell strain was cultured at 37 ° C under 5% CO ₂ . The cultured B16F10 cells were removed by 0.05% trypsin-Ethylene Diamine Tetraacetic Acid (EDTA) and again in the same amount in a 48-culture vessel (well plate). 1 × 10 ⁴ cells / well) were inoculated, after three consecutive days from the next day medium was replaced with a compound comprising 10 ppm of the various embodiments. At this time, as a comparative example, kojic acid and rucinol were used.

After the fifth day, treatment with 1 N NaOH was carried out for 2 hours at 60 ° C to melt the melanin contained in the cells, and the amount of melanin was measured by measuring the absorbance at 405 nm. The concentration (IC ₅₀ ) of the Example required to halve the melanin produced by the black cells was thereby shown in the following table.

[Table 1]

With reference to the above Table 1, the ginsenoside fatty acid ester compound of the present invention can inhibit the formation of melanin even in an amount less than that of kojic acid and resveratrol. Therefore, it is understood that the ginsenoside fatty acid ester compound of the present invention has an excellent skin whitening effect by suppressing the formation of melanin.

[Test Example 2] MMP-1 expression inhibitory effect In order to evaluate the inhibitory effect of the ginsenoside fatty acid ester compound on MMP-1 expression, fibroblasts were dispensed into a 24-well plate in units of 1 × 10 ⁴ per well. The culture was carried out for about 24 hours in a medium containing 10% FBS until a confluency of about 80% was reached. Thereafter, the medium was replaced with FBS-free medium and cultured for 24 hours.

To irradiate ultraviolet rays (Ultraviolet, UV), the cells were washed once with Phosphate Buffered Saline (PBS), and then irradiated with UVB 15 mJ/cm ² with the addition of 100 ml of PBS. After removing the PBS, the dilution treatment was carried out in a new medium without FBS so that the final concentrations of the ginsenoside fatty acid ester compounds prepared in Example 2 were 0.01%, 0.05%, 0.1%, and 0.5% as a comparison. Example 1, using retinoic acid. After 48 hours of treatment of the test substance, the culture supernatant was recovered and subjected to enzyme-linked immunosorbent assay (ELISA) kits (RPN 2610, Biotrak Amersham Pharmacia Biotech, UK). The performance of MMP-1 was assessed. The amount of MMP-1 measured by the total amount of the protein was corrected, and the results are shown in Table 2 below and FIG. At this time, FIG. 1 is a graph comparing the inhibition ratio of the compound of Example 1 and MMP-1 of Comparative Example 1.

[Table 2] MMP-1 performance inhibition rate (%)

Referring to Table 2 and Figure 1, the ginsenoside fatty acid ester compound of the present invention significantly inhibited the expression of MMP-1 compared to the retinoic acid of Comparative Example 1.

According to the results, the ginsenoside fatty acid ester compound proposed in the present invention has an effect of inhibiting skin aging by inhibiting biosynthesis of skin tissue decomposing enzyme, MMP-1, which is caused by internal aging or external environmental factors. Improve wrinkles.

Hereinafter, another dosage form of the present invention will be described, but the cosmetic dosage form containing the ginsenoside fatty acid ester compound of the present invention is not limited thereto.

[Formulation Example 1] lotion The lotion was prepared by a usual method according to the composition described in the following table.

[table 3]

[Formulation Example 2] Nutrient Cream A nutrient cream was prepared by a usual method according to the composition described in the following table.

[Table 4]

[Formulation Example 3] Massage Cream A massage cream was prepared by a usual method according to the composition described in the following table.

[table 5]

[Formulation Example 4] Mask The mask was prepared by a usual method according to the composition described in the following table.

[Table 6]

Fig. 1 is a graph showing the inhibitory effects of the compound of Example 1 and MMP-1 of Comparative Example 1.

Claims (7)

A ginsenoside fatty acid ester compound represented by the following Chemical Formula 1: [Chemical Formula 1] In the above Chemical Formula 1, R ₁ is a saturated or unsaturated fatty acid group of C12 to C22, R ₂ is an OH or a saturated or unsaturated fatty acid group of C12 to C22, and R ₃ is H or OH. The ginsenoside fatty acid ester compound according to claim ₁ , wherein the R ₁ is lauryl, tridecyl, myristyl, pentadecyl, soft lipid, pearlescent, hard fat a base, a nonadecyl group, a peanut base, a behenyl group, a behenyl group, a decyl oleyl group, an oleyl group, a myristyl group, a linoleyl group or an arachidonic acid group, wherein the R ₂ is OH, lauryl, tridecyl, myristyl, pentadecyl, palmitoyl, pearlescent, stearyl, pentadecyl, arachidyl, icosyl, hawthorn, soft A lipid sulfhydryl group, an oleyl group, a myristyl group, a linoleyl group or an arachidonic acid group, and R ₃ is H or OH. The ginsenoside fatty acid ester compound according to the above aspect of the invention, wherein the ginsenoside fatty acid ester compound is any one of the compounds represented by the following Chemical Formula 2 to Chemical Formula 5: [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] . A method for producing a ginsenoside fatty acid ester compound of Chemical Formula 1, which is represented by the following Reaction Formula 1, which is prepared by subjecting a compound of the following Chemical Formula 6 to a C12 to C22 saturated or unsaturated fatty acid vinyl ester compound by enzymatic conversion reaction: Reaction formula 1] In the above Reaction Scheme 1, R ₁ is a C12 to C22 saturated or unsaturated fatty acid group, R ₂ is H or a C12 to C22 saturated or unsaturated fatty acid group, and R ₃ is H or OH. The method for producing a ginsenoside fatty acid ester compound according to claim 4, wherein the R ₁ is lauryl, tridecyl, myristyl, pentadecyl, soft lipid, pearlescent , stearyl, nonadecyl, arachidyl, behenyl, behenyl, leucoyl, oleyl, myristyl, linoleyl or arachidonic acid, said R ₂ is OH, lauryl, tridecyl, myristyl, pentadecyl, palmitoyl, pearlescent, stearyl, nonadecyl, arachidyl, icosyl, hawthorn a base, a lipid sulfhydryl group, an oleyl group, a myristyl group, a linoleyl group or an arachidonic acid group, and the R ₃ is H or OH. The method for preparing a ginsenoside fatty acid ester compound according to claim 4, wherein the enzyme conversion reaction is selected from the group consisting of a flavor protease, a protease A, an alkaline protease, a siazyme, a complex protease, and a proteinase. One or more enzymes in the group consisting of Novozymes lipase, esterase and thiol transferase. A cosmetic composition comprising the ginsenoside fatty acid ester compound according to any one of claims 1 to 3 as an active ingredient.