KR20160081195A - SKIN EXTERNAL COMPOSITION FOR MOISTURING SKIN OR WHITENING SKIN CONTAINING ISOFLAVONE AND (2S)-1-O-LINOLENOYL-3-O-β-D-GALACTOPYRANOSYL-SN-GLYCEROL - Google Patents

Abstract

The present invention relates to a skin composition comprising isoflavone and (2S)-1-O-linolenoyl-3-O-β-D-galactopyranosyl-sn-glycerol for moisturizing or whitening skin and, more particularly, to a skin composition using a synergic effect of isoflavone and (2S)-1-O-linolenoyl-3-O-β-D-galactopyranosyl-sn-glycerol for external applications for enhancing skin barrier functions, and improving complexion and skin tone. According to the present invention, the skin composition for external uses enhances skin barrier functions, suppresses generation of melanin, and improves complexion and skin tone, thereby exhibiting a skin moisturizing effect, and a skin whitening effect.

Description

(SKIN EXTERNAL COMPOSITION FOR MOISTURING SKIN OR (2S) -1-O-LINOLENOYL-3-O- [beta] -D- Galactopyranosyl-sn- WHITENING SKIN CONTAINING ISOFLAVONE AND (2S) -1-O-linolenoyl-3-0-? -D-galactopyranosyl-sn-glycerol}

The present invention relates to a composition for external application for moisturizing or whitening skin containing isoflavone and (2S) -1-O-linolenol-3-O-? -D-galactopyranosyl-sn-glycerol, Specifically, it is used for enhancing skin barrier function, synergistic effect of isoflavone and (2S) -1-O-linolenoyl-3-O-? -D-galactopyranosyl-sn-glycerol Skin external composition.

Skin plays a very important role as a barrier function to protect individuals from the outside. The barrier function is a protection function for protecting against various stimuli (chemicals, air pollutants, dry environment, ultraviolet rays, etc.) from the outside and excessive divergence of water in the body through the skin. Such protection function is a function of protecting the stratum corneum The function can be maintained only when it is normally formed.

The outermost stratum corneum (horney layer) of the epidermis is formed from keratinocytes, and consists of keratinocytes with complete differentiation and a surrounding lipid layer (Marcelo CL et al . , J. Invest . Dermatol . 80 , pp 37-44, 1983).

The keratinocyte is a characteristic cell in which basal cells continuously proliferating in the lowest epidermis undergo a stepwise change in morphology and function and are elevated to the surface of the skin. After a certain period of time, And the new keratinocyte replaces its function. This repetitive sequence of changes is called "epidermal cell differentiation" or "keratinization".

In addition, during keratinization, keratinocytes form natural moisturizing factors (NMF) and intercellular lipids (ceramides, cholesterol, fatty acids) and form stratum corneum, which gives firmness and flexibility to the stratum corneum, barrier function.

Such stratum corneum can easily lose its function due to environmental factors such as excessive washing, bathing and other lifestyle factors, dry air pollutants, and endogenous diseases such as atopic skin and senile skin. In fact, Due to the increasing number of factors, dry skin symptoms and their complaints have been increasing recently.

Therefore, in order to maintain proper skin moisture, various studies have been made to supply water from the outside or to prevent water loss from the body. Various moisturizers having moisture retention ability have been developed. As a skin moisturizing agent, it is common to use a substance capable of increasing water retention in the stratum corneum such as ceramide and essential fatty acid and lipid complex (Rawlings AV et al . , J. Invest . Dermatol . , 5, pp731- 741, 1994).

However, recently, the risk factors for skin are increasing, and changes in dietary patterns slow down the generation and decline of the stratum corneum, and the function of the keratinocyte is reduced, so that the amount of the moisturizing factor and lipid in the stratum corneum is decreased, There is an increasing trend in people with skin that can not function as a skin barrier. Such breakdown of the skin barrier function causes various skin diseases such as dry skin, atopic dermatitis, contact dermatitis and psoriasis. Such diseases can be expected to be alleviated by moisturizing agents having a conventional moisture retention function but it is difficult to achieve fundamental healing.

In addition, human skin color is determined by various factors such as the activity of melanocyte making melanocyte, the distribution of blood vessels, the thickness of skin, and the presence or absence of pigment inside and outside the body, such as carotenoids and bilirubin. In particular, melanin, which is produced by the action of various enzymes such as tyrosinase in melanocytes, is the most important factor. The formation of melanin pigment is affected by environmental factors such as genetic factors, hormonal secretion, physiological factors such as stress, and ultraviolet irradiation. Melanin is present in the skin and protects the body from ultraviolet rays, but it is known that melanin is overproduced, thereby promoting pigmentation and aging of the skin and leading to skin cancer induction. (Ascorbic acid), kojic acid, arbutin, hydroquinone, and so on to treat or relieve excessive melanin pigmentation caused by skin pigmentation abnormalities and ultraviolet exposure. Glutathione or a derivative thereof and a substance having inhibitory activity against tyrosinase have been used in cosmetics or medicines in combination with insufficient whitening effect, safety problems to the skin, Its use is restricted due to stability problems and so on.

The isoflavones used in the present invention are mainly vegetable compounds contained in soybean, and isoflavones include genistein glycoside, daidzein glycoside, glycitein glycoside, It is composed of glycosides and derivatives, most of which are glycoside forms such as genistin and daidzin. They are hydrolyzed by enzymes such as microbial fermentation or glucosidase to change sugar residues into genistein, an aglycone which has a high uptake rate in the body (Korean Patent No. 10-0500641). Isoflavones have been reported to be effective against antioxidants, antimicrobials and metal chelating agents (Middleton et al., 1992; Dixon et al., 2002), and are known to have anti-aging and skin wrinkle benefits.

On the other hand, it is known that the known compounds of (2S) -1-O-linolenoyl-3-O- beta -D-galactopyranosyl-sn-glycerol of the present invention have anti-cancer and anti- BJ et al., Glycosyl glycerides from hydrophobic Panax ginseng inhibited NO production in LPS-stimulated RAW 264.7 cells, Journal of Ginseng Research (2014), doi: 10.1016 / j.jgr.2014.10.005) It is not known whether it is.

In view of the properties of the isoflavone and (2S) -1-O-linolenol-3-O- beta -D-galactopyranosyl-sn-glycerol, the present inventors promoted the function of keratinocyte (2S) -1-O-linolenol-3-O- beta -D-galactose (2S) -1-O-β-D-galactosyltransferase was found to enhance the skin barrier function and inhibit the production of melanin pigment in melanocytes. Glycopyranosylpyranosyl-sn-glycerol was used in combination, skin moisturizing and whitening effects were excellent, and the present invention was completed.

Korean Patent No. 10-0500641

Cha BJ et al., Glycosyl glycerides from hydrophobic Panax ginseng inhibited NO production in LPS-stimulated RAW 264.7 cells, Journal of Ginseng Research (2014), doi: 10.1016 / j.jr.2014.10.005

It is an object of the present invention to provide a cosmetic composition containing isoflavone and (2S) -1-O-linolenol-3-O-? -D-galactopyranosyl-sn-glycerol as an active ingredient, And an excellent external skin application composition for moisturizing.

In order to achieve the above-mentioned object, the present invention provides a method for moisturizing a composition containing isoflavone and (2S) -1-O-linolenoyl-3-0-? -D-galactopyranosyl-sn- Or whitening dermatologic external composition.

INDUSTRIAL APPLICABILITY The composition for external application for skin according to the present invention exhibits skin moisturizing effect and skin whitening effect by enhancing skin barrier function, inhibiting melanin production, improving color and skin tone.

Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In general, the nomenclature used herein is well known and commonly used in the art.

The present invention relates to a composition for external application for moisturizing or whitening skin containing isoflavone and (2S) -1-O-linolenoyl-3-0-? -D-galactopyranosyl-sn-glycerol as an active ingredient will be.

Hereinafter, the present invention will be described in more detail.

The soybean germ isoflavone used in the present invention is a substance which is abundant in plants, especially soybean plants, and may be referred to as bioisogen.

Specific examples of the soybean embryo isoflavones include sugar-linked forms such as genistin, daidzin, glycitin; Sugar-removed forms such as genistein, daidzein, gristitene, or mixtures thereof. On the other hand, soybean embryo isoflavones contain more than 50% of the aglycone form in which the sugar is removed by using an enzyme, and the sugar-removed form has a much better absorption capacity than the natural isoflavone, (Korean Patent Nos. 99020416 and 99039042).

Genistein, which is known to have the highest anticancer activity among soy isoflavones, has been extensively studied through diestylstilbestrol (DES) or estradiol at a concentration of 1 × 10 ^{-3 to} 1 × 10 ^-5 estrogen , And in the examples of the present invention, genistein is used as the isoflavone, but the present invention is not limited thereto.

The composition according to the present invention may contain isoflavone in an amount of 0.01 to 20% by weight, preferably 0.1 to 10% by weight, based on the total weight of the composition. If the content of the isoflavone is less than 0.01% by weight, the effect or effect of the ingredient is insufficient, and if it exceeds 20% by weight, skin safety or shape problems may occur.

(2S) -1-O-linolenoyl-3-O- beta -D-galactopyranosyl-sn-glycerol (molecular weight: 514) used in the present invention has the structure represented by the following formula (1).

[Chemical Formula 1]

The (2S) -1-O-linolenoyl-3-O- beta -D-galactopyranosyl-sn-glycerol of the present invention may be extracted from plants or synthesized according to methods known in the art And commercially available ones may be used.

The composition according to the present invention comprises 0.01 to 20% by weight of (2S) -1-O-linolenoyl-3-O-? -D-galactopyranosyl-sn-glycerol, By weight to 10% by weight. If the content of (2S) -1-O-linolenoyl-3-O- beta -D-galactopyranosyl-sn-glycerol is less than 0.01% by weight, %, There is a problem of skin safety or shape.

The composition for external application for skin according to the present invention is characterized in that isoflavones and (2S) -1-O-linolenol-3-O-? -D-galactopyranosyl-sn- Can be effectively improved overall.

The composition for external application for skin according to the present invention can be used for enhancing skin barrier function and inducing differentiation of dermal keratinocyte. Therefore, it is possible to prevent or ameliorate skin dryness, atopic dermatitis, contact dermatitis or psoriasis caused by imperfections of epidermal differentiation Can be usefully used as an external composition for skin.

In addition, the composition for external application for skin according to the present invention has excellent ability to recover damaged skin barrier and increase skin moisture content, and can be used as a composition for skin regeneration.

In addition, the composition for external application for skin according to the present invention is excellent in the ability to inhibit the melanin formation of melanocytes and improve the color and skin tone, and can be used as a composition for skin whitening.

The above composition for external application for skin of the present invention can be formulated as a cosmetic composition, and can be formulated containing a cosmetically or dermatologically acceptable medium or base. These are all formulations suitable for topical application, for example as a solution, a gel, a solid, a paste anhydrous product, an emulsion obtained by dispersing an oil phase in water, a suspension, a microemulsion, a microcapsule, a microgranule or an ionic form (liposome) In the form of ionic fibrin dispersions, or in the form of creams, skins, lotions, powders, ointments, sprays or conical sticks. It can also be used in the form of a foam or in the form of an aerosol composition further containing a compressed propellant. These compositions may be prepared according to conventional methods in the art.

The cosmetic composition according to the present invention can be applied to cosmetics such as softening agents, convergent lotion, nutritional lotion, nutritional cream, massage cream, essence, eye cream, eye essence, cleansing cream, cleansing foam, cleansing water, pack, powder, body lotion, body cream, And body essence.

In addition, the composition according to the present invention may further comprise at least one selected from the group consisting of fatty substances, organic solvents, solubilizers, thickening agents, gelling agents, softening agents, antioxidants, suspending agents, stabilizing agents, Such as fillers, emulsifiers, emulsifiers, fillers, sequestering agents, chelating agents, preservatives, vitamins, blockers, moisturizers, essential oils, dyes, pigments, hydrophilic or lipophilic active agents, lipid vesicles or any other ingredient commonly used in cosmetics May contain adjuvants commonly used in the field of cosmetics or dermatology. Such adjuvants are introduced in amounts commonly used in the cosmetics or dermatological fields.

In addition, the composition of the present invention may contain a skin absorption promoting substance to increase the skin improving effect.

Hereinafter, the present invention will be described in more detail with reference to examples and test examples, but the present invention is not limited to these examples.

[Referential Example 1]

Isoflavones (genistein) for testing the efficacy of the compositions of the present invention were prepared in the form of concentrated powders as described below.

Step 1. Production of soybean extract

6 ℓ of hexane was added to 2 ㎏ of soybeans, and the mixture was degreased with stirring at room temperature for 3 times. Then, 4 kg of 80% methanol was added to 1 kg of defatted soybeans, refluxed three times, and then immersed at 15 ° C for 1 day. Thereafter, the residue and the filtrate were separated by filtration through a filter cloth and centrifugation. The separated filtrate was concentrated under reduced pressure, and the resulting extract was suspended in water. The filtrate was extracted 5 times with 1 L of ether to remove the pigment. And extracted three times with 500 ml of butanol. The total 1-butanol layer thus obtained was concentrated under reduced pressure to obtain a 1-butanol extract. The extract was dissolved in a small amount of methanol and then added to a large amount of ethyl acetate. The resultant precipitate was dried to obtain 300 g of a soybean extract.

Step 2. Genistein using microorganisms ( genistein , 4 ', 5,7- Trihydroxy  Isoflavone)

10 g of the soybean extract obtained in the above (1) was dissolved in 100 ml of ionized water, sterilized at 121 캜 for 30 minutes, cooled to 30 캜, and pre-cultured Aspergillus niger (KCCM 11885) And incubated at 30 ° C for 7 days. Substrate clearance was confirmed by thin layer chromatography and the reaction was terminated when the substrate completely disappeared. The culture solution was centrifuged at 5,000 to 10,000 rpm. The collected precipitate was washed three times with distilled water and centrifuged to obtain a reaction solution. The precipitate was added with ethanol (200 ml) and stirred (3 times) The precipitated salts were removed by filtration. The filtered filtrate was then concentrated under reduced pressure to give a crude product. Then, the obtained crude product was separated by silica gel column chromatography (chloroform: methanol = 8: 1 to 4: 1) to obtain 0.12 g of genistein.

[Reference Example 2]

(2S) -1-O-linolenol-3-O- beta -D-galactopyranosyl-sn-glycerol for the purpose of testing the efficacy of the composition of the present invention is described in the prior art (Cha BJ et al., Glycosyl glycerides from hydrophobic Panax ginseng inhibited NO production in LPS-stimulated RAW264.7 cells, Journal of Ginseng Research (2014), doi: 10.1016 / j.jgr.2014.10.005).

[Test Example 1] Measurement of promoting effect of keratinocyte differentiation

In order to examine the differentiation promoting effect of the composition for external application for skin according to the present invention, the amount of corned envelope (CE) produced upon differentiation of keratinocytes was measured by absorbance as described below.

First, keratinocytes (HEK; Lonza Co., NHEK-Neonatal Normal Human Epidermal Keratinocytes, Pooled) isolated from epidermis of a newborn baby were placed in a culture flask and adhered to the bottom. (2 ppm concentration) - 2 mg of genistein in Reference Example 1 or (2S) -1-O-linolenol-3-O-? -D-galactopyranosyl-sn-glycerol in Reference Example 2 was dissolved in distilled water Diluted to 1 L, 2.5 ppm concentration - 2.5 mg of genistein of Reference Example 1 or (2S) -1-O-linolenol-3-O- beta -D-galactopyranosyl-sn-glycerol of Reference Example 2 3-O-beta-D-galactopyranosyl-sn-glycerol (2S) -1-O-beta-D-galactopyranosyl- 3 mg was diluted with 1 L of distilled water), and then cultured for 5 days until the cells were grown to 70-80% of the floor area.

At this time, the treated group of low calcium (0.03 mM) and the treated group of high calcium (1.2 mM) were used as a negative control and a positive control group, respectively. The genistein (5 ppm concentration of the reference example 1-diluted with 1 L of distilled water) (2S) -1-O-linolenol-3-O- beta -D-galactopyranosyl-sn-glycerol (5 ppm concentration- (2S) -1- O-beta -D-galactopyranosyl-sn-glycerol (5 mg) was diluted with 1 L of distilled water).

Then, the cultured cells were harvested, washed with PBS (Phosphate buffered saline), and then suspended in 10 mM Tris-HCl buffer (Tris-HCl buffer containing 2% SDS (sodium dodecyl sulfate) and 20 mM DTT (Dithiothreitol) , pH 7.4) was added, sonication, boiling, and centrifugation. The precipitate was suspended again in 1 ml of PBS and the absorbance at 340 nm was measured. Separately, a part of the solution after the sonication was taken to measure the protein content and used as a standard in evaluating the degree of cell differentiation. The results are shown in Table 1 below.

Test substance The ability to differentiate in keratinocytes (%) Low calcium (0.03 mM) solution
(Negative control) 100 High calcium (1.2 mM) solution
(Positive control group) 210 Genistein (2.5 ppm) +
(2S) -1-O-linolenol-3-O- beta -D-galactopyranosyl-sn-glycerol (2.5 ppm) 288 Genistein (3ppm) +
(2S) -1-O-linolenol-3-O- beta -D-galactopyranosyl-sn-glycerol (2ppm) 300 Genistein (2ppm) +
(2S) -1-O-linolenol-3-O- beta -D-galactopyranosyl-sn-glycerol (3 ppm) 313 Genistein (5ppm) 256 (2S) -1-O-linolenol-3-O- beta -D-galactopyranosyl-sn-glycerol (5 ppm) 230

As shown in Table 1 above, when isoflavone (genistein) or (2S) -1-O-linolenol-3-O- beta -D-galactopyranosyl- (2S) -1-O-linolenol-3-O- beta -D-galactopyranosyl-sn-glycerol were treated with synergist It was confirmed that the effect of promoting differentiation of keratinocytes was excellent.

In addition, it was found that when genistein 3 ppm + (2S) - (2S) -glucosidase was used as compared with 2.5 ppm of genistein 2.5 ppm + (2S) -1-O-linolenol- 2-ppm of 1-O-linolenol-3-O- beta -D-galactopyranosyl-sn-glycerol was more effective in promoting the differentiation of keratinocytes, -1-O-linolenol-3-O- beta -D-galactopyranosyl-sn-glycerol at a concentration of 3 ppm resulted in the best promotion of keratinocyte differentiation.

[Test Example 2] Measurement of skin barrier function recovery effect

In order to measure the effect of the composition for external application for skin according to the present invention on the recovery of damaged skin barrier function due to skin damage, the following experiment was conducted. The tops of 10 adult males and females were damaged by damaging the skin barrier using a tape stripping method and applied to the six groups of Formulation Examples 1 to 3 and Comparative Formulation Examples 1 to 3, (TWEL) was measured and compared with the Vapometer (Delfin, Finland) once a day for 7 days. Comparative Formulation Example 1 is a vehicle as a negative control, Comparative Formulation Example 2 is a comparative control containing only isoflavone of Reference Example 1, and Comparative Formulation Example 3 is (2S) -1 -O-linolenol-3-O-? -D-galactopyranosyl-sn-glycerol alone. The experimental results are shown in Table 3 below. The results in Table 3 were compared before treatment before barrier damage and after treatment before barrier damage on the basis of 100%.

(Unit: wt%) Compounding ingredient Formulation Example 1 Formulation Example 2 Formulation Example 3 Comparative Formulation Example 1 Comparative Formulation Example 2 Comparative Formulation Example 3 Purified water 69 69 69 70 69 69 Propylene glycol 30 30 30 30 30 30 Genistein 0.5 0.6 0.4 - One - (2S) -1-O-linolenol-3-O- beta -D-galactopyranosyl-sn-glycerol 0.5 0.4 0.6 - - One

Test group TWEL Change (%) Before processing 1 day 2 days 3 days 4 days 5 days 6 days Formulation Example 1 100 123 121 117 110 110 108 Formulation Example 2 100 123 122 120 118 113 111 Formulation Example 3 100 123 125 124 123 119 116 Comparative Formulation Example 1 100 122 110 97 77 68 44 Comparative Formulation Example 2 100 124 119 113 112 109 106 Comparative Formulation Example 3 100 123 116 111 109 104 102

As can be seen from the above Table 3, when the isoflavones and (2S) -1-O-linolenol-3-O-? -D-galactopyranosyl-sn-glycerol were treated together, The amount of transdermal water loss returned to normal at a higher rate than when isoflavone or (2S) -1-O-linolenol-3-O- beta -D-galactopyranosyl-sn- It can be confirmed that the damage is recovered.

[Reference Example 3] Formulation examples 4 to 6 and comparative formulations 4 to 6

Nutritive creams were prepared according to the composition of Table 4 below in a conventional manner (unit: wt%).

Compounding ingredient Formulation Example 4 Formulation Example 5 Formulation Example 6 Comparative Formulation Example 4 Comparative Formulation Example 5 Comparative Formulation Example 6 Purified water To 100 To 100 To 100 To 100 To 100 To 100 Genistein 0.25 0.3 0.2 - 0.5 - (2S) -1-O-linolenol-3-O- beta -D-galactopyranosyl-sn-glycerol 0.25 0.2 0.3 - - 0.5 Vegetable hydrogenated oil 1.50 1.50 1.50 1.50 1.50 1.50 Stearic acid 0.60 0.60 0.60 0.60 0.60 0.60 Glycerol stearate 1.00 1.00 1.00 1.00 1.00 1.00 Stearyl alcohol 2.00 2.00 2.00 2.00 2.00 2.00 Polyglyceryl-10pentastearate and behenyl alcohol and sodium stearoyl lactylate 1.00 1.00 1.00 1.00 1.00 1.00 Arachidyl behenyl alcohol & arachidyl glucoside 1.00 1.00 1.00 1.00 1.00 1.00 Cetylaryl Alcohol and Cetearyl Glucoside 2.00 2.00 2.00 2.00 2.00 2.00 PEG-100 Stearate & Glycerololate & Propylene Glycol 1.50 1.50 1.50 1.50 1.50 1.50 Caprylic / Carrick Triglyceride 11.00 11.00 11.00 11.00 11.00 11.00 Cyclomedicone 6.00 6.00 6.00 6.00 6.00 6.00 Preservative, incense Suitable amount Suitable amount Suitable amount Suitable amount Suitable amount Suitable amount Triethanolamine 0.1 0.1 0.1 0.1 0.1 0.1

[Test Example 3] Measurement of skin moisturizing effect

Formulations 4 to 6 and Comparative Formulations 4 to 6 were used to measure the effect of the composition of the present invention on the skin moisturizing effect, and were evaluated as follows.

Sixty male and female adult persons aged 40 to 50 classified as dry skin were divided into 6 groups of 10 persons for each of the six groups of Formulation Examples 4 to 6 and Comparative Formulation Examples 4 to 6, and the nutritional cream was applied twice daily for 4 weeks to the face . (24 ° C, relative humidity 40%) after 1 week, 2 weeks, and 4 weeks after application, and after 2 weeks (total 6 weeks) (Corneometer CM825, C + K Electronic Co., Germany). The results are shown in Table 5 below. The results in Table 5 are based on the skin moisture meter measured just before the start of the test, and the increase in the measured value after a certain period of treatment is expressed as a percentage.

Test group Moisture growth rate (%) 1 week Two weeks 4 weeks 6 weeks Formulation Example 4 49 44 42 40 Formulation Example 5 52 47 45 41 Formulation Example 6 59 56 52 50 Comparative Formulation Example 4 32 30 27 12 Comparative Formulation Example 5 32 35 34 32 Comparative Formulation Example 6 31 30 28 23

The results of Table 5 show that when Comparative Formulation Example 4 is applied, the moisture increase rate is about 30% until 4 weeks of application, but after the application is stopped (6 weeks) Comparative Formulation Example 6, which contained Comparative Formulation Example 5 alone containing genistein alone and (2S) -1-O-linolenol-3-O-? -D-galactopyranosyl-sn-glycerol alone , The skin moisture increase rate remained mostly in the 30% range. However, the skin moisture increase rate remained at about 30% in the case of using (2S) -1-O-linolenol-3-O-beta-D-galactopyranosyl- When Formulation Examples 4 to 6 were applied, it was confirmed that the skin moisture increase rate was 40% or more even after stopping the application due to the synergy effect. Thus, it can be seen that the composition of the present invention has excellent skin moisturizing effect.

[Test Example 4] Inhibitory effect on melanin formation by B16 / F10 melanoma cells

The B16 / F10 melanoma used in this test example is a mouse-derived cell line, and is a cancer cell caused by malignantization of a cell that secretes a melanin pigment called melanin. During the artificial incubation of these cells, the test material was treated to compare the degree of decrease in melanin production. The B16 / F10 melanoma used in this test was purchased from Korean Cell Line Bank (KCLB No: 8008).

Melanin biosynthesis inhibitory effect of B16 / F10 melanoma was measured as follows. B16 / F10 melanoma dries to a 6-well plate at ⁵ × 10 5 / well of frequency divider 37 ℃, 5% CO ₂ And cultured in DMEM (Dulbecco's Modified Eagle's Medium) containing 10% FBS (fetal bovine serum) for 24 hours in an incubator (MCO-20AIC, Sanyo). The test material was added to fresh DMEM medium without FBS and aged for 72 hours. The test materials used at this time are as shown in Table 6 below. After treatment with trypsin-EDTA, the cells were separated by centrifugation, and melanin was dissolved at 95 ° C in 1N NaOH containing DMSO. Absorbance was measured at 405 nm using an ELISA reader (DIbiotech, Korea). Cells to which the test substance was not added were used as a control group, and the melanin formation inhibition degree of each test substance was measured by comparing with the melanin content in the control group. The inhibition rate of melanin production was calculated according to Equation (1) and the results are shown in Table 6.

[Equation 1]

Test substance Melanin inhibition rate (%) Control group (no addition) 0 Kojic acid 53 (0.05 wt.%) + (2S) -1-O-linolenol-3-O- beta -D-galactopyranosyl- 51 (0.03 wt.%) + (2S) -1-O-linolenol-3-O -? - D-galactopyranosyl- 55 (0.03 wt.%) + (2S) -1-O-linolenol-3-O- beta -D- galactopyranosyl- 62 Genistein (0.1% by weight) 48 (0.1% by weight) of (2S) -1-O-linolenol-3-O- beta -D- galactopyranosyl- 42

In the results of Table 6 above, when the combination of genistein and (2S) -1-O-linolenol-3-O- beta -D-galactopyranosyl-sn-glycerol is used, the rate of melanin production inhibition is increased, (2S) -1-O-linolenol-3-O- beta -D-galactopyranosyl-sn-glycerol, .

[Test Example 5] Skin tone improvement effect

To examine the effect of the composition of the present invention on the improvement of skin tone, 60 male and female adults in the 20s to 50s were divided into 6 groups of 10 groups for each of the four groups of Formulations 4 to 6 and Comparative Formulations 4 to 6, (Morningx, Japan) was applied to each of the above Formulation Examples 4 to 6 and Comparative Formulation Examples 4 to 6 (once a day / once a day for a total of one week) . The improvement rate of the skin tone was determined by determining the brightness and color change value of the skin from the brightness and color measurement values of the skin, and the average value of the results was obtained and is shown in Table 7 below. The larger the change in brightness and color, the better the skin tone.

Test substance Skin tone improvement rate (%) brightness Color Formulation Example 4 27 26 Formulation Example 5 30 28 Formulation Example 6 36 33 Comparative Formulation Example 4 9 7 Comparative Formulation Example 5 13 11 Comparative Formulation Example 6 11 10

The results of Table 7 show that Comparative Formulation Example 4, which does not contain any of the genistein and (2S) -1-O-linolenol-3-O-? -D-galactopyranosyl-sn-glycerol, Comparative formulation No. 5 containing (2S) -1-O-linolenol-3-O-? -D-galactopyranosyl-sn-glycerol, which does not show skin tone improving efficacy, Example 6 shows improvement in skin tone before use, and in Formulations 4 to 6 which simultaneously contain these two components, skin tone is remarkably improved by synergy effect.

Hereinafter, formulation examples of the composition according to the present invention will be described. However, the pharmaceutical composition and the cosmetic composition can be applied to various formulations, and the present invention is not limited thereto but is specifically described.

[Formulation Example 1] Lotion

Lotions are prepared according to a conventional method with the composition shown in Table 8 below.

Content (% by weight) Genistein 1.0 (2S) -1-O-linolenol-3-O- beta -D-galactopyranosyl-sn-glycerol 1.0 glycerin 3.0 Butylene glycol 2.0 Propylene glycol 2.0 Carboxyvinyl polymer 0.1 PEG 12 nonyl phenyl ether 0.2 Polysorbate 80 0.4 ethanol 10.0 Triethanolamine 0.1 Preservative, coloring, fragrance Suitable amount Purified water Balance

[Formulation Example 2] Nourishing cream

Nutrition cream is prepared according to a conventional method with the composition shown in Table 9 below.

Content (% by weight) Genistein 1.0 (2S) -1-O-linolenol-3-O- beta -D-galactopyranosyl-sn-glycerol 1.0 Polysorbate 60 1.5 Sorbitan sesquioleate 0.5 PEG 60 hardened castor oil 2.0 Liquid paraffin 10.0 Squalane 5.0 Caprylic / caproic triglyceride 5.0 glycerin 5.0 Butylene glycol 3.0 Propylene glycol 3.0 Triethanolamine 0.2 Preservative, coloring, fragrance Suitable amount Purified water Balance

[Formulation Example 3] Massage cream

A massage cream is prepared according to a conventional method with the composition shown in Table 10 below.

Content (% by weight) Genistein 0.5 (2S) -1-O-linolenol-3-O- beta -D-galactopyranosyl-sn-glycerol 0.5 Wax 10.0 Polysorbate 60 1.5 PEG 60 hardened castor oil 2.0 Sorbitan sesquioleate 0.8 Liquid paraffin 40.0 Squalane 5.0 Caprylic / capric triglyceride 4.0 glycerin 5.0 Butylene glycol 3.0 Propylene glycol 3.0 Triethanolamine 0.2 Preservative, coloring, fragrance Suitable amount Purified water Balance

[Formulation Example 4] Pack

A pack is prepared according to a conventional method with the composition shown in Table 11 below.

Content (% by weight) Genistein 0.5 (2S) -1-O-linolenol-3-O- beta -D-galactopyranosyl-sn-glycerol 0.5 Polyvinyl alcohol 13.0 Sodium carboxymethylcellulose 0.2 glycerin 5.0 Allantoin 0.1 ethanol 6.0 PEG 12 nonyl phenyl ether 0.3 Polysorbate 60 0.3 Preservative, coloring, fragrance Suitable amount Purified water Balance

[Formulation Example 5] Gel

A gel is prepared according to a conventional method with the composition shown in Table 12 below.

Content (% by weight) Genistein 0.25 (2S) -1-O-linolenol-3-O- beta -D-galactopyranosyl-sn-glycerol 0.25 Ethylenediamine sodium acetate 0.05 glycerin 5.0 Carboxyvinyl polymer 0.3 ethanol 5.0 PEG 60 hardened castor oil 0.5 Triethanolamine 0.3 Preservative, coloring, fragrance Suitable amount Purified water Balance

[Formulation Example 6] Ointment

Ointment was prepared by a conventional method with the composition shown in Table 13 below.

Content (% by weight) Genistein 0.5 (2S) -1-O-linolenol-3-O- beta -D-galactopyranosyl-sn-glycerol 0.5 glycerin 8.0 Butylene glycol 4.0 Liquid paraffin 15.0 Beta Glucan 7.0 Carbomer 0.1 Caprylic / capric triglyceride 3.0 Squalane 1.0 Cetearyl glucoside 1.5 Sorbitan stearate 0.4 Cetearyl alcohol 1.0 Wax 4.0 Preservative, coloring, fragrance Suitable amount Purified water Balance

[Formulation Example 7] Soft capsule

0.0025 g of genistein, 0.0025 g of (2S) -1-O-linolenoyl-3-O-? -D-galactopyranosyl-sn-glycerol, 0.0025 g of vitamin C, 2 mg of palm oil, 8 mg of palm kernel oil, 6 mg of lecithin were mixed, and 400 mg / capsule was filled in accordance with a conventional method to prepare a soft capsule.

[Formulation Example 8] Tablets

Galactopyranosyl-sn-glycerol, 0.0025 g of vitamin C, 100 mg of glucose, 96 mg of starch and 4 mg of magnesium stearate And 40 mg of 30% ethanol was added thereto to form granules. The granules were dried at 60 ° C and tableted by a tablet machine.

[Formulation Example 9]

150 mg of genistein, 150 mg of (2S) -1-O-linolenoyl-3-O- beta -D-galactopyranosyl-sn-glycerol, 150 mg of vitamin C, 100 mg of glucose and 600 mg of starch were mixed and 30% 100 mg was added to form granules, followed by drying at 60 DEG C to form granules, which were then filled in a capsule. The final weight of the contents was 1 g.

[Formulation Example 10]

Galactopyranosyl-sn-glycerol, 0.0025 g of vitamin C, 10 g of glucose, 2 g of citric acid and 187.8 g of purified water were added to a solution containing 0.0025 g of genistein, 0.0025 g of (2S) -1-O-linolenoyl- Mixed and filled in bottles. The final volume of the contents was adjusted to 200 ml.

While the present invention has been particularly shown and described with reference to specific embodiments thereof, those skilled in the art will readily appreciate that many modifications are possible in the exemplary embodiments without materially departing from the novel teachings and advantages of this invention. something to do. Accordingly, the actual scope of the present invention will be defined by the appended claims and their equivalents.

Claims (8)

(2S) -1-O-linolenol-3-O- beta -D-galactopyranosyl-sn-glycerol represented by the following formula (1) as an active ingredient, a moisturizing or whitening external preparation for skin Composition.
[Chemical Formula 1]

2. The composition of claim 1, wherein the isoflavone is selected from the group consisting of genistin, daidzin, glycitin, genistein, daidzein, and glycitein. Wherein the composition is at least one selected from the group consisting of the following. The composition for external application for skin according to claim 1, wherein the isoflavone content is 0.01 to 20% by weight based on the total weight of the composition. The method according to claim 1, wherein the content of (2S) -1-O-linolenoyl-3-O- beta -D-galactopyranosyl-sn-glycerol is 0.01 to 20% by weight Wherein the external preparation is a skin external preparation. The composition for external application for skin according to claim 1, wherein the composition is for inducing differentiation of dermal keratinocytes. The composition for external application for skin according to claim 1, wherein the composition is for enhancing skin barrier function. The composition for external application for skin according to claim 1, wherein the composition is for improving color and skin tone. 8. The composition according to any one of claims 1 to 7, wherein the composition is selected from the group consisting of softening agents, convergent lotion, nutritional lotion, nutritional cream, massage cream, essence, eye cream, eye essence, cleansing cream, cleansing foam, , A powder, a body lotion, a body cream, a body oil, and a body essence.