KR102029040B1 - Ginsenoside fatty acid ester compounds, preparation method thereof, and cosmetic composition comprising the same - Google Patents

Abstract

The present invention relates to a ginsenoside fatty acid ester compound, a method for preparing the same, and a cosmetic composition containing the same, and more particularly, to a ginsenoside fatty acid ester compound modified with a fatty acid ester compound to have hydrophobicity, and a method for preparing the same. The compound is excellent in penetration through keratin skin, effectively suppresses the expression of melanin and MMP-1, and is preferably applied as a cosmetic composition for skin whitening and wrinkle improvement.

Description

Ginsenoside fatty acid ester compound, a manufacturing method thereof, and a cosmetic composition comprising the same {GINSENOSIDE FATTY ACID ESTER COMPOUNDS, PREPARATION METHOD THEREOF, AND COSMETIC COMPOSITION COMPRISING THE SAME}

The present invention relates to a novel ginsenoside fatty acid ester compound having a skin whitening and antioxidant effect, a preparation method thereof, and a cosmetic composition containing the same.

Panax ginseng CA Meyer is a plant belonging to the genus Ogapiaceae ginseng and has been used in Korea, China and Japan for more than 2,000 years. It has been used to prevent disease and extend life. Ginseng's known effects and effects on the central nervous system, anticarcinogenic and anticancer activity, immune function regulation, antidiabetic activity, hepatic antifungal effect, cardiovascular disorder improvement and anti-arteriosclerosis, blood pressure control, menopause Effects on improving disorders and osteoporosis, antistress and anti-fatigue, antioxidant activity and anti-aging effects are known.

Various effects and effects of the above ginseng is due to a component called 'ginsenoside' (Ginsenoside, a glycoside in ginseng, aka saponin) which is a kind of saponin. Ginsenosides have a structure in which sugar is attached to a steroid skeleton, which is changed by heat. Steaming breaks the steroid-glucose bond, resulting in a drop in sugar and a different effect depending on what sugar remains in the position. As the water-soluble sugars fall, they become fat-soluble and produce ginsenosides that are easy to pass through the cell membrane.

There are more than 30 kinds of ginsenosides, and they do not all have the same ingredients and efficacy. Among them, ginsenoside F1 and ginsenoside compound K have been proposed as active ingredients of the cosmetic composition. These compounds have a structure in which one sugar (glucose) is attached to protopanaxadiol in the saponin component of ginseng.

Ginsenoside F1 is known to protect human HaCaT keratinocytes by down-regulating the expression of Bcl-2 and Brn-3a from allergy inhibition and apoptosis by irradiation of ultraviolet B. Lee EH, et al ., J. Invest. Dermatol . 121: 607-13, 2003. Korean Patent Publication No. 2014-0013796 discloses that ginsenoside F1 can be used in cosmetic compositions for improving skin inflammatory diseases by reducing sebum content and improving acne and atopic dermatitis, and Korean Patent Publication No. 2013-0095949 Ginsenoside F1 has been suggested to improve the antioxidant, anti-inflammatory and skin moisturizing properties, and is useful as a skin external preparation.

In addition, Korean Patent Registration Nos. 10-0485326 and 10-1427572 disclose that ginsenoside compound K can be applied as an external composition for skin by promoting the production of hyaluronic acid, and Korean Patent Publication No. 2015-0083290 is whitening. And the effect on wrinkle improvement.

In addition, Korean Patent Registration No. 10-1140039 discloses that ginsenoside F1 or Compound K protects the epidermal dermal boundary of the skin, thereby preventing skin aging and improving wrinkles, thereby being used as an external preparation for skin.

As such, ginsenoside F1 or compound K may have various effects including skin whitening and antioxidant effects (anti-aging, wrinkle improvement) when applied to cosmetic compositions.

On the other hand, the skin is structurally composed of lipids, the cell gap and the outermost stratum corneum, the skin surface is covered with sebum (oil component) secreted by the cells. Unfortunately, it is difficult for a hydrophilic material to penetrate through the skin, and to increase the concentration of the hydrophilic substance or give an electric shock such as ion foresis.

Ginsenoside F1 or compound K has a structure in which saccharides are connected by ether linkage with alcoholic OH groups, thus having high hydrophilicity and high molecular weight. Therefore, the skin penetrating power of ginsenoside F1 or compound K is very low, and even if a cosmetic composition contains these components, the amount which penetrates or is absorbed by the skin is small, and the effect obtained substantially is inadequate.

Republic of Korea Patent Publication No. 2014-0013796, "Cosmetic composition for improving skin inflammatory diseases comprising ginsenoside F1 as an active ingredient" Republic of Korea Patent Publication No. 2013-0095949, "External skin composition containing ginsenoside F1" Republic of Korea Patent No. 10-0485326, "Hyaluronic acid production promoter consisting of ginsenoside compound K" Republic of Korea Patent No. 10-1427572, "External skin composition for promoting hyaluronic acid production containing ginsenoside Re and ginsenoside compound 사이드" Republic of Korea Patent Publication No. 2015-0083290, "Manufacturing method of ginsenoside derivatives and the composition for whitening and wrinkle improvement comprising the ginsenoside derivatives prepared as an active ingredient" Republic of Korea Patent No. 10-1140039, "External skin composition containing ginsenoside F1 or Compound K"

Lee E H, et al, F1 significantly reduced ultraviolet-B-induced cell death and protected HaCaT cells from apoptosis caused by ultraviolet B irradiation. 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).

In order to solve the above problems, the present inventors reacted with these compounds and fatty acid vinyl ester compounds to increase the hydrophobicity of ginsenoside F1 or compound K, thereby preparing novel compounds. The present invention was completed by inhibiting the production of melanin pigment, having a skin whitening effect, and significantly inhibiting the collagen degrading enzyme MMP-1.

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

Another object of the present invention is to provide a method for preparing a ginsenoside fatty acid ester compound.

Still another object of the present invention is to provide a use of the ginsenoside fatty acid ester compound as a cosmetic composition.

In order to achieve the above object, the present invention provides a ginsenoside fatty acid ester compound represented by the following formula (1):

[Formula 1]

(In Formula 1, R ₁ to R ₃ are as described in the specification)

In addition, the present invention is represented by the following Scheme 1,

Provided is a method for preparing a ginsenoside fatty acid ester compound of Formula 1 prepared by enzymatic conversion of a compound of Formula 6 and a saturated or unsaturated fatty acid vinyl ester of C12 to C22:

Scheme 1

(In Reaction Scheme 1, R ₁ to R ₃ are as described in the specification)

The present invention also provides a cosmetic composition comprising the ginsenoside fatty acid ester compound represented by Formula 1 as an active ingredient.

The ginsenoside fatty acid ester compound according to the present invention has a whitening effect and an anti-wrinkle effect that the existing ginsenoside F1 or compound K has, and hydrophobicity is improved to have excellent skin penetration to the skin keratin.

Specifically, the compound acts on tyrosinase, an enzyme that produces melanin pigments causing freckles and blemishes, inhibits the production of melanin pigments, exerts skin whitening effects, and retinophosphate expression of MMP-1, an enzyme that degrades collagen. It can be more significantly suppressed to obtain a wrinkle improvement effect, it is formulated into a variety of cosmetic products to improve the consumer satisfaction.

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

Hereinafter, the present invention will be described in detail.

The present invention proposes a novel compound modified to have hydrophobicity in order to increase the skin absorbency of ginsenoside F1 or compound K. Preferably, the novel compound is a ginsenoside fatty acid ester compound represented by Formula 1:

[Formula 1]

(In Formula 1,

R ₁ is a C12-C22 saturated or unsaturated fatty acid group,

R ₂ is OH or a C12-C22 saturated or unsaturated fatty acid group,

R ₃ is H or OH)

Saturated fatty acid groups of C12 to C22 referred to herein are lauryl group (C12: 0, lauryl), tridecyl group (C13: 0, tridecyl), myristyl group (C14: 0, myristil), pentadecyl group (C15 : 0, pentadecyl), palmityl (C16: 0, palmityl). Margaryl group (C17: 0, margaryl), stearin group (C18: 0, stearyl), nonadecyl group (C19: 0, nonadecyl), arykidyl group (C20: 0, arachidyl), heneicosyl group (C21: 0 , heneixosylyl), or behenyl group C22: 0, behenyl).

In addition, the unsaturated fatty acid group of C12 to C22 referred to in the present specification is palmitoleyl group (C16: 1, palmitoleyl), oleyl group (C18: 1, oleyl), myrioleyl group (C14: 1 myristoleyl), linoleyl group (C18: 2 linoleyl) or arachidyl group (C20: 3, arachidonyl).

Preferably, R ₁ is a palmityl group. It is a stearin group or an oleyl group, More preferably, it is a palmityl group.

Also preferably, R ₂ is OH, palmityl group. It is a stearin group or an oleyl group, More preferably, it is an OH or palmityl group.

In particular, the compounds of formula 1 of the present invention include all isomers unless otherwise specified. The isomers can be seen due to all stereoisomers, such as those which may exist due to asymmetric carbons on various R and Z substituents (including enantiomers (which may be present even when no asymmetric carbon is present) and diastereomers) Are considered within the scope of the invention. Each stereoisomer of a compound of the invention can be, for example, substantially free of other isomers, or mixed, for example, with racemates or with all stereoisomers or selected stereoisomers.

For example, it may be represented by an isomer of Formula 1a:

[Formula 1a]

(In Formula 1, R ₁ to R ₃ are as described above)

Examples of the compound represented by Formula 1 include the following compounds:

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In addition, the present invention is represented by the following Scheme 1,

A method for preparing a ginsenoside fatty acid ester compound of Formula 1 by enzymatic conversion of a compound of Formula 6 to a saturated or unsaturated fatty acid vinyl ester of C12 to C22 is provided:

Scheme 1

(In Reaction Scheme 1, R ₁ to R ₃ are as mentioned above)

The compound of Chemical Formula 6, which is a starting material in Scheme 1, is a ginsenoside compound, preferably ginsenoside F1 (R ₃ = OH) represented by Formula 7 or ginsenoside compound K represented by Formula 8 (R ₃ = H) or derivatives thereof.

[Formula 7]

[Formula 8]

Such starting materials may be obtained from ginseng, red ginseng, white ginseng, ginseng, rice ginseng, ginseng leaves, or ginseng fruit, or directly manufactured or purchased commercially available.

For example, ginseng tablet saponin may be hydrolyzed with acid, alkali or enzyme to remove sugar from ginseng saponin, and then the reaction solution may be prepared by passing through a silica column. Enzymes that can be used here include beta-glucosidase, alpha, and beta-arabinosidase, alpha and beta-rhamnose, which break down saponin sugar bonds. and exo-glucose degrading enzymes such as β-rhamnosidase, and complex enzymes containing them.

In addition, in Scheme 1, the fatty acid vinyl ester compound is a compound that introduces R ₁ and R ₂ into the chemical structure of Chemical Formula 1, and may be a C12 to C22 saturated or unsaturated fatty acid vinyl ester compound.

Preferably, the C12 to C22 saturated fatty acid vinyl ester compound is a vinyl lauryl ester (C12: 0, lauryl), tridecyl acid vinyl ester (C13: 0, tridecylic acid vinyl ester), myristyl vinyl ester ( C14: 0, myristic acid vinyl ester), pentadecyl acid vinyl ester (C15: 0, pentadecylic acid vinyl ester), palmitic acid vinyl ester (C16: 0). Margaric acid vinyl ester (C17: 0, margaric acid vinyl ester), stearic acid vinyl ester (C18: 0, stearic acid vinyl ester), nonadecylic acid vinyl ester (C19: 0, nonadecylic acid vinyl ester), arycydyl acid vinyl ester (C20: 0, arachidyl), heneixosylic acid vinyl ester (C21: 0, hehenixosylic acid vinyl ester), or behenylic acid vinyl ester (C22: 0, behenylic acid vinyl ester).

The unsaturated fatty acid vinyl ester compounds of C12 to C22 may be palmitoleic acid vinyl ester (C16: 1, palmitoleylic acid vinyl ester), oleic acid vinyl ester (C18: 1, oleylic acid vinyl ester), myrioleic acid vinyl ester (C14: 1 , myristoleylic acid vinyl ester), linoleylic acid vinyl ester (C18: 2), or arachidonylic acid vinyl ester (C20: 3).

More preferably, the fatty acid vinyl ester compound is palmitic acid vinyl ester. Stearic acid vinyl esters, or oleic acid vinyl esters, most preferably vinyl palmitate.

The reaction proceeds with an enzyme conversion reaction.

The enzyme is a protease (protease) or lipase can be characterized by using a hydrolase, such as (lipase), as the hydrolase is let Plastic Im (flavourzyme), protease A (protease A), Alcala the ( alcalase), Sabina claim (savinase), Pro other Mex (protamex), Esper cyclase (esperase), Novozymes (novozyme), esterase (esterlase), acylase (acylase) and, but to use a mixture thereof, It is not limited to this. In addition, a microorganism containing the hydrolase may be used as the enzyme source. Preferably, in the embodiment of the present invention was used novozyme 435 ( novozyme 435, Novozyme).

These strains Bacillus strains (Bacillus sp), Aspergillus duck claim (Aspergillus oryzae ), Aspergillus niger , Candida antarctica and mixtures thereof, and the like, but may be used without limitation as long as the strain or microorganism contains a hydrolase.

Kinds and administration methods of enzymes added in Scheme 1 are not particularly limited as long as they do not cause inactivation of enzymes, and methods commonly used in the art may be used.

The reaction temperature is reacted while stirring for 1 to 120 hours, preferably 36 to 72 hours in the range of 20 ~ 60 ℃ in the case of novozyme temperature, that is, enzyme inactivation does not occur.

The solvent used here is lower alcohols such as water, methanol, ethanol and propanol and acetone, dimethylformamide (DMF), methylene chloride (MC), diisopropyl ether, diethyl ether and tetrahydrofuran (THF) as organic solvents. ), Dimethylacetamide (DMA), dimethyl sulfoxide (DMSO), chlorobenzene, toluene, benzene and the like can be used alone or in combination, preferably acetone is used.

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

That is, the ginsenoside fatty acid ester compound of Formula 1 exhibits hydrophobicity while maintaining the whitening effect and wrinkle improvement effect of the ginsenoside compound, especially the ginsenoside F1 and the compound K, and is excellent in penetrating power to the stratum corneum.

In addition, as the ginsenoside fatty acid ester compound of the present invention exhibits hydrophobicity, the reactivity with tyrosinase, an enzyme that produces melanin pigments causing freckles and blemishes, is improved. For this reason, as shown in the test example 1, the whitening effect excellent compared with the koji-acid or rucinol which was excellent in the conventional whitening effect was secured.

In addition, as a result of measuring the expression inhibitory effect of MMP-1, an enzyme that degrades collagen (see Test Example 2), the ginsenoside fatty acid ester compound of the present invention was significantly inhibited than retinoic acid, thereby ensuring a wrinkle improvement effect. It can be seen that.

Thus, the ginsenoside fatty acid ester compound of Formula 1 may be used as an active ingredient of the cosmetic composition, the content of which varies depending on the formulation, it may be used in 0.001 to 99% by weight. When the active ingredient is contained in the above range, it is not only suitable to exhibit the intended effect of the present invention, but also satisfies both the stability and solubility of the composition, and may be appropriate to include in the above range in terms of cost-effectiveness.

Cosmetic compositions can be prepared in any formulations conventionally prepared in the art, including, for example, solution suspensions, emulsions, pastes, gels, creams, lotions, powders, oils, powder foundations, emulsion foundations, wax foundations And it may be formulated in a spray or the like, but is not limited thereto. More specifically, it may be prepared in the form of a sun cream, a flexible lotion, a convergent lotion, a nourishing lotion, a nourishing cream, a massage cream, an essence, an eye cream, a pack, a spray or a powder.

In addition, the cosmetic composition according to the present invention may be a fatty substance, an organic solvent, a dissolving agent, a thickening agent, a gelling agent, a softening agent, an antioxidant, a suspending agent, a stabilizer, a foaming agent, a perfume, a surfactant, water, an ionic type Nonionic emulsifiers, fillers, metal ion sequestrants, chelating agents, preservatives, vitamins, blockers, wetting agents, essential oils, dyes, pigments, hydrophilic or lipophilic active agents, lipid vesicles or any other ingredients commonly used in cosmetics It may contain adjuvants conventionally used in the cosmetic or dermatology field. Such adjuvants are introduced in amounts generally used in the cosmetic or dermatological arts.

When the formulation is a paste, cream or gel, animal oil, vegetable oil, wax, paraffin, starch, tracant, cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc or zinc oxide may be used as a carrier component. .

If the formulation is a powder or a spray, lactose, talc, silica, aluminum hydroxide, calcium silicate or polyamide powder may be used, especially in the case of a spray, additionally chlorofluorohydrocarbon, propane / butane. Or propellants such as dimethyl ether.

When the formulation is a solution or emulsion, a solvent, solubilizer or emulsion is used as carrier component, such as water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1,3 Fatty acid esters of butylglycol oil, glycerol aliphatic ester, polyethylene glycol or sorbitan.

When the formulation is a suspension, a carrier diluent such as water, ethanol or propylene glycol, suspending agents such as ethoxylated isostearin alcohol, polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester, microcrystalline cellulose, Aluminum metahydroxide, bentonite, agar or tracant and the like can be used.

Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the following examples are merely to illustrate the present invention, but the content of the present invention is not limited by the following examples.

[ Example  1] Preparation of the Compound of Formula 2

Pressure tube (Compound K, 1eq), vinyl palmitate (2.5eq), 42.5 molecular sieve (100 wt%), novozyme 435, and anhydrous acetone (500 wt%, 5 to substrate) Pear) was injected and stirred at 45 ° C. for 3 days to proceed with the reaction.

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

¹ H NMR (300 MHz, CDCl ₃ ) 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 Formula 3

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

¹ H NMR (300 MHz, CDCl ₃ ) 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 Formula 4

A compound of Chemical Formula 4 (yield 89%) was prepared in the same manner as in Example 1, except that the compound of Chemical Formula 8 (Compound K, 2eq) was used as a starting material.

¹ H NMR (300 MHz, CDCl ₃ ) 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 Formula 5

A compound of Formula 5 was prepared (yield 88%) in the same manner as in Example 1, except that the compound of Formula 7 (ginsenoside F1, 2eq) was used as a starting material.

¹ H NMR (300 MHz, CDCl ₃ ) 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] Inhibitory effect of melanogenesis in melanocyte-producing cells

The melanin production inhibitory effect in melanocyte-producing cells to the compound prepared in Example 2 was measured by Dooley's method.

The cell line used mouse-derived B16 F10 (melanoma cells) purchased from Korea Cell Line Bank. DMEM (Cat No. 11995), FBS (Cat No. 16000-044) and antibiotic-antifungal reagents (Cat No. 15240-062) required for cell culture were purchased from Invitrogen (GIBCO).

Cell lines were incubated under 37 ° C., 5% CO ₂ . Cultured B16F10 cells were detached with 0.05% Trypsin-EDTA and seeded in 48-well plates again in the same number (1 × 10 ⁴ cells / well), followed by three consecutive days from the second day. Compounds were replaced with medium containing 10 ppm. In this case, kojic acid and rucinol were used as comparative examples.

After 5 days, 1N NaOH was treated and reacted at 60 ° C. for 2 hours to melt melanin contained in the cells, and the amount of melanin was measured by measuring absorbance at 405 nm. From this the concentration of Example (IC ₅₀ ) required to reduce melanin production in melanocytes by half is calculated and shown in the table below.

Test substance IC ₅₀ Kojisan > 500 μM Rucinol 16 μM Compound of Example 1 7.8 μM Compound of Example 2 7.2 μM Compound of Example 3 7.5 μM Compound of Example 4 7.4 μM

Referring to Table 1, the ginsenoside fatty acid ester compound according to the present invention can inhibit melanin production in a small amount compared to koji acid and rucinol. Therefore, it can be seen that the ginsenoside fatty acid ester compounds according to the present invention have excellent skin whitening effect by inhibiting melanin production.

[ Test Example  2] MMP -1 expression inhibitory effect

To evaluate the inhibitory efficacy of MMP-1 expression of ginsenoside fatty acid ester compounds, fibroblasts were dispensed in ^four well plates at 1 × 10 ⁴ per well, containing 10% FBS until reaching about 80% confluency. Incubated for about 24 hours in the medium. Thereafter, the cells were exchanged with a medium without FBS for 24 hours.

After washing the cells once with PBS for UV irradiation, UVB 15 mJ / ㎠ was irradiated with 100 ml of PBS. After PBS was removed, the resultant was treated by diluting the final concentration of the ginsenoside fatty acid ester compound prepared in Example 2 to 0.01, 0.05, 0.1 and 0.5% in a fresh medium without FBS. Retinoic acid was used. After 48 hours of treatment with the test substance, the culture supernatant was collected and evaluated for expression of MMP-1 using ELISA kits (enzyme-linked immunosorbent assay kits; RPN 2610, Biotrak Amersham Pharmacia Biotech, UK). The amount of MMP-1 respectively measured was corrected by the total protein amount, and the results are shown in Table 2 and FIG. 1. 1 is a graph comparing the MMP-1 inhibition rate of the compound of Example 1 and Comparative Example 1

% Inhibition of MMP-1 expression density(%) Example 1 Example 2 Example 3 Example 4 Comparative Example 1 0 100 100 100 100 100 0.01 97.9 97 97.1 97.5 98.1 0.05 77.1 75.1 79.5 80.1 87.3 0.1 64.3 65.5 63.4 66.7 82.5 0.5 40.7 42.5 43.2 45.5 72.2

Referring to Table 2 and Figure 1, ginsenoside fatty acid ester compound according to the present invention is a retinoic acid than Comparative Example 1 It can be seen that it significantly inhibits the expression of MMP-1.

Through these results, the ginsenoside fatty acid ester compound presented in the present invention inhibits the biosynthesis of skin tissue degrading enzyme MMP-1 caused by internal aging or external environmental factors, thereby inhibiting skin aging and improving wrinkles. It can be seen.

Hereinafter, another formulation example of the present invention will be described, but the cosmetic formulation containing the ginsenoside fatty acid ester compound according to the present invention is not limited only to these examples.

[Formulation Example 1] Lotion

The lotion was prepared according to a conventional method with the composition described in the table below.

ingredient Content (% by weight) Compound of Example 1 0.1 glycerin 3.0 Butylene glycol 2.0 Propylene glycol 2.0 Carboxy Vinyl Polymer 0.1 PEG 12 nonylphenyl ether 0.2 Polysorbate 80 0.4 ethanol 10.0 Triethanolamine 0.1 Preservative, coloring, flavoring Quantity Purified water Remaining amount

Formulation Example 2 @ Nutritional Cream

A nutritious cream was prepared according to a conventional method with the composition described in the table below.

ingredient Content (% by weight) Compound of Example 1 2.0 Polysorbate 60 1.5 Solbitan Sesquioleate 0.5 PEG 60 Cured Castor Oil 2.0 Liquid paraffin 10. Squalane 5.0 Caprylic / Capric Triglycerides 5.0 glycerin 5.0 Butylene glycol 3.0 Propylene glycol 3.0 Triethanolamine 0.2 Preservative, coloring, flavoring Quantity Purified water Remaining amount

Formulation Example 3 Massage Cream

Massage creams were prepared according to a conventional method with the compositions described in the table below.

ingredient Content (% by weight) Compound of Example 1 1.0 Beeswax 10.0 Polysorbate 60 1.5 PEG 60 Cured Castor Oil 2.0 Sorbitan sesquioleate 0.8 Liquid paraffin 40.0 Squalane 5.0 Caprylic / Capric Triglycerides 4.0 glycerin 5.0 Butylene glycol 3.0 Propylene glycol 3.0 Triethanolamine 0.2 Preservative, coloring, flavoring Quantity Purified water Remaining amount

[Formulation Example 4] Pack

Packs were prepared according to conventional methods with the compositions described in the table below.

ingredient Content (% by weight) Compound of Example 1 0.2 Polyvinyl alcohol 13.0 Sodium Carboxymethyl Cellulose 0.2 glycerin 5.0 Allantoin 0.1 ethanol 6.0 PEG 12 nonylphenyl ether 0.3 Polysorbate 60 0.3 Preservative, coloring, flavoring Quantity Purified water Remaining amount

Claims (7)

Ginsenoside fatty acid ester compound represented by Formula 1 below:
[Formula 1]

(In Formula 1,
R ₁ is a C12-C22 saturated or unsaturated fatty acid group,
R ₂ is a C12-C22 saturated or unsaturated fatty acid group,
R ₃ is H or OH) The method of claim 1,
R ₁ is a lauryl group, tridecyl group, myristyl group, pentadecyl group, palmityl group, margaryl group, stearin group, nonadecyl group, arkydyl group, heneicosyl group, behenyl group, palmitoleyl group, Oleyl group, mylesoleyl group, linoleyl group, or arachidyl group,
R ₂ is a lauryl group, tridecyl group, myristyl group, pentadecyl group, palmityl group, margaryl group, stearyl group, nonadecyl group, arkydyl group, heneicosyl group, behenyl group, palmitoleyl group , An oleyl group, mylesoleyl group, a linoleyl group, or an arachidyl group,
R ₃ is H or OH ginsenoside fatty acid ester compound. The method of claim 1,
The ginsenoside fatty acid ester compound is any one of the compounds represented by the following formulas (4) and (5) ginsenoside fatty acid ester compound:
[Formula 4]

[Formula 5]

Represented by Scheme 1 below,
A method for preparing a ginsenoside fatty acid ester compound of Formula 1 prepared by enzymatic conversion of a compound of Formula 6 to a saturated or unsaturated fatty acid vinyl ester of C12 to C22:
Scheme 1

(In Scheme 1,
R ₁ is a C12-C22 saturated or unsaturated fatty acid group,
R ₂ is a C12-C22 saturated or unsaturated fatty acid group,
R ₃ is H or OH) The method of claim 4, wherein
R ₁ is a lauryl group, tridecyl group, myristyl group, pentadecyl group, palmityl group, margaryl group, stearin group, nonadecyl group, arkydyl group, heneicosyl group, behenyl group, palmitoleyl group, Oleyl group, mylesoleyl group, linoleyl group, or arachidyl group,
R ₂ is a lauryl group, tridecyl group, myristyl group, pentadecyl group, palmityl group, margaryl group, stearyl group, nonadecyl group, arkydyl group, heneicosyl group, behenyl group, palmitoleyl group , An oleyl group, mylesoleyl group, a linoleyl group, or an arachidyl group,
R ₃ is H or OH, the method for producing a ginsenoside fatty acid ester compound. The method of claim 4, wherein
The enzyme conversion reaction is flavozyme ( flavourzyme ), protease A ( protease A), alcalase ( sacalase ), savinase ( savinase ), protamex ( protamex ), esperase ( nosperzyme ), novozyme ( novozyme ) Method for producing a ginsenoside fatty acid ester compound, characterized in that using one enzyme selected from the group consisting of esterase , acylase and mixtures thereof. Cosmetic composition comprising the ginsenoside fatty acid ester compound according to any one of claims 1 to 3 as an active ingredient.

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