KR20160081174A - Skin external composition for anti-anging comprising catechins and monogalactopyranosylglycerol - Google Patents

Abstract

The present invention relates to a skin composition for external applications. By comprising low concentrations of catechin and monogalactosyldiacylglycerol at optimal concentrations, the skin composition for external applications exhibits excellent skin anti-aging effects, particularly, an antioxidant effect, an effect of promoting collagen synthesis, an effect of alleviating skin elasticity, and an effect of alleviating skin wrinkles.

Description

(SKIN EXTERNAL COMPOSITION FOR ANTI-ANGING COMPRISING CATECHINS AND MONOGALACTOPYRANOSYLGLYCEROL) <br> <br> <br> Patents - stay tuned to the technology SKIN EXTERNAL COMPOSITION FOR ANTI-ANGING COMPRISING CATECHINS AND MONOGALACTOPYRANOSYLGLYCEROL

The present invention relates to catechins and monogalactosyl diacyl glycerol, preferably (2S) -1-O-linoleoyl-2-O-linoleoyl-3-0- beta -D- galactopyranosyl- glycerol and (2S) -1-O-linolenol-2-O-linolenol-3-O- beta -D-galactopyranosyl-sn- The present invention relates to a composition for external application for skin excellent in anti-aging effect.

Human skin is the primary protective membrane of the human body. It functions to protect the internal organs from external environmental stimuli such as changes in temperature and humidity, ultraviolet rays, and pollutants. Depending on various internal and external factors, It undergoes change. In other words, internally, secretion of various hormones that regulate metabolism is reduced, the function of immune cells and the activity of cells are lowered, and the biosynthesis of immune proteins and biocompatible proteins necessary for the living body is reduced, and ozone layer destruction As the content of ultraviolet rays reaching the surface of the sunlight increases and environmental pollution is further intensified, free radicals and active noxious oxygen are increased, so that the thickness of the skin decreases, the wrinkles increase, the elasticity decreases Skin color is grayish, skin troubles are frequent, spots, freckles and black spots are increased, bleeding is poor, skin tone is getting dark, and so on.

In order to prevent the change of the skin condition due to the intrinsic and extrinsic factors, and to maintain a healthy skin condition, physiologically active substances obtained from various known animals, plants, microorganisms and the like are added to cosmetics to improve the skin condition There has been effort for.

On the other hand, (2S) -1-O-linoleoyl-2-O-linoleoyl-3-O- beta -D-galactopyranosyl- -2-O-linolenol-3-O- beta -D-galactopyranosyl-sn-glycerol is a monogalactosyl diacyl glycerol compound and is known to have anticancer and anti-inflammatory effects (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), the above-mentioned compounds exhibit other effects in relation to skin condition improvement and synergistic effects with other ingredients, Has not been reported.

Korean Patent Laid-Open No. 10-2012-0083943 (published on July 27, 2012)

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

The present invention relates to a pharmaceutical composition comprising a low concentration of catechin and monogalactosyl diacyl glycerol, preferably (2S) -1-O-linolenol-2-O-linolenol-3-O- Glycerol or (2S) -1-O-linoleoyl-2-O-linoleoyl-3-O- beta -D-galactopyranosyl-sn- An anti-aging effect, specifically, an antioxidant effect, an effect of promoting collagen synthesis, an effect of improving skin elasticity, and an effect of improving skin wrinkles.

In order to achieve the above object, And (2S) -1-O-linolenoyl-2-O-linolenol-3-O-beta-D- galactopyranosyl- The present invention provides a composition for external application for skin for anti-aging comprising as an active ingredient at least one of monogalactosyldiacyl glycerol in 2-O-linoleoyl-3-O-? -D-galactopyranosyl-sn- Specifically, the composition for external application for skin comprises 0.001 to 0.2% by weight of the catechin based on the total weight of the composition, 1.0 to 10% by weight of the monogalactosyl diacyl glycerol based on the total weight of the composition, : The content ratio of monogalactosyl diacyl glycerol is 1: 25 to 1: 50 in molar ratio.

INDUSTRIAL APPLICABILITY The composition for external application for skin according to the present invention has an excellent anti-aging effect by optimally containing catechin and monogalactosyldiacyl glycerol at a low concentration, increases collagen biosynthesis in the dermis to maintain a resilient and healthy skin condition, And resilience recovery effect.

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

The catechins used in the present invention were extracted from green tea and mainly composed of EGCG, GCG, ECG and CG, but not limited to the above catechins.

Camellia sinensis ) is an evergreen tree of Camelliaceae. It is generally called green tea because its shoots or leaves are processed without fermentation during the manufacturing process. It has been reported that green tea was drunk from the new agriculture of China in 2700 BC, and it is said that Korea drank tea from the time of Silla Dynasty. In addition, green tea contains catechin, flavonoid, theanine, GABA, caffeine, tannin, and various vitamins, which are used for anticancer, antioxidant, antibacterial, deodorant, blood pressure Depression, and immune function are known to have a variety of effects, such as recently reported to be effective in dieting. Particularly, catechin is a major functional ingredient of green tea which exhibits various pharmacological actions ranging from antioxidant, anticancer, antibacterial, and prevention of heart disease.

The catechins contained in green tea were catechin (CA), epicatechin (EC), epigallocatechin (EGC), EGCG, and epigallocatechin (EGC) have.

In the present invention, the catechin is selected from the group consisting of EGCG (epigallocatechin gallate), GCG (gallocatechin gallate), ECG (epicatechin gallate), CG (catechin gallate), EGC (epigallocatechin) ), (-) EC (epicatechin), (+) EC (epicatechin), (-) CA (catechin) and (+) CA. The green tea extract is preferably extracted from green tea leaves, ) EGCG.

The content of catechin in the composition is 0.001 to 0.2% by weight based on the total weight of the composition, based on in vitro and in vivo experiments. If the content is less than 0.001% by weight, acting as an active ingredient is difficult to expect. If the content exceeds 0.2% by weight, the symptom improvement effect is rather reduced.

(2S) -1-O-linolenol-2-O-linolenol-3-O- beta -D-galactopyranosyl-sn-glycerol in the monogalactosyl diacyl glycerol used in the present invention is Can be represented by the following formula (1).

[Chemical Formula 1]

(2S) -1-O-linoleoyl-2-O-linoleoyl-3-O- beta -D-galactopyranosyl-sn-glycerol in the monogalactosyl diacyl glycerol used in the present invention is Can be represented by the following formula (2).

(2)

(2S) -1-O-linolenol-2-O-linolenol-3-O- beta -D- galactopyranosyl- Linoleoyl-2-O-linoleoyl-3-O- beta -D-galactopyranosyl-sn-glycerol has been reported in the literature on glycosyl glycerides (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), but the present invention is not limited thereto. May be extracted from plants, synthesized according to methods known in the art, and commercially available ones may be used.

The content of the monogalactosyl diacyl glycerol is 1.0-10% by weight based on the total weight of the composition based on in vitro and in vivo experiments. If the content is less than 1.0% by weight, it is difficult to expect the action as an active ingredient. If the content is more than 10% by weight, the symptom improvement effect is weak.

The composition for external application for skin according to the present invention can improve overall symptoms such as wrinkles and elasticity by using catechin and monogalactosyl diacyl glycerol.

The composition for external application for skin according to the present invention is characterized in that low concentration catechin and monogalactosyl diacyl glycerol are contained at a constant component ratio, that is, catechin is 0.001 to 0.2 wt%, catechin: monogalactosyl diacyl glycerol is 1: 25 ~ 1:50, the effect of skin aging is better.

The composition for external application for skin for anti-aging according to the present invention is characterized by being anti-aging.

The composition for external application for skin for anti-aging according to the present invention is characterized in that it is for promoting collagen synthesis.

Further, the composition for external application for skin for anti-aging according to the present invention is characterized by being for improving skin elasticity.

Further, the composition for external application for skin for anti-aging according to the present invention is characterized in that it is for improving skin wrinkles.

The above anti-aging dermatological composition 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]

The (-) epigallocatechin (EGCG) for testing the efficacy of the composition of the present invention was purchased from Sigma-Aldrich.

[Reference Example 2]

(2S) -1-O-linolenol-2-O-linolenol-3-O- beta -D-galactopyranosyl-sn-glycerol for the test of the efficacy of the composition of the present invention is described in [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].

[Referential Example 3]

(2S) -1-O-linoleoyl-2-O-linoleoyl-3-O- beta -D-galactopyranosyl-sn-glycerol for the test of the efficacy of the composition of the present invention is described in [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].

[Reference Example 4]

4.56 ug of (-) EGCG of Reference Example 1 and 5 mL of distilled water were mixed to prepare 6 (2) standard solutions of (-) EGCG 2uM. 0.5 uM, 0.4 uM, 0.2 uM, 0.1 uM and 0.01 uM (-) EGCG standard solutions were prepared by adding 15 mL, 20 mL, 45 mL, 95 mL and 995 mL of distilled water to 5 of the prepared 2 uM standard solutions, respectively.

 [Reference Example 5]

389.25 ug of (2S) -1-O-linolenoyl-2-O-linolenol-3-O-? -D-galactopyranosyl-sn-glycerol of Reference Example 2 and 5 mL of distilled water were mixed to prepare ) -1-O-linolenol-2-O-linolenol-3-O- beta -D-galactopyranosyl-sn-glycerol. (2S) -1-O-linolenol-2-O-linolenol-3-O- [beta] -D-glucopyranosyl chloride was prepared by adding 45 mL and 495 mL of distilled water to two of the prepared 100 uM standard solutions, Galactopyranosyl-sn-glycerol standard solution.

[Referential Example 6]

387.25 ug of the (2S) -1-O-linoleoyl-2-O-linoleoyl-3-O-? -D-galactopyranosyl-sn-glycerol of Reference Example 3 and 5 mL of distilled water were mixed to prepare ) -1-O-linoleoyl-2-O-linoleoyl-3-O- beta -D-galactopyranosyl-sn-glycerol. (2S) -1-O-linoleoyl-2-O-linoleoyl-3-O- [beta] -D-glucopyranosyl chloride was prepared by adding 45 mL and 495 mL of distilled water to two of the prepared 100 [ Galactopyranosyl-sn-glycerol standard solution.

 [Test Example 1] Inhibitory effect on reactive oxygen species (ROS) production

5 × 10 ⁴ keratinocytes (cell line: HaCaT; available from ATCC) were added to each well of a 24-well plate containing keratinocyte growth media (Clonetics, BioWhittacker, MD, USA) And adhered for 24 hours. After 16 hours, (-) EGCG was treated with 0.001 uM. For comparison, the control group was not treated with (-) EGCG and paracodisol. After 2 hours, the culture solution was removed, and 100 μl of phosphate buffered saline (PBS) was added to each well. This keratinocyte was irradiated with ultraviolet rays of 30 mJ / cm 2 using an ultraviolet B (UVB) lamp (Model: F15T8, UVB 15 W, Sankyo Dennki, Japan), and then PBS was removed. Was added. The (-) EGCG was treated again and the amount of reactive oxygen species increased by ultraviolet stimulation was determined at certain time intervals. The amount of ROS was determined by reference to Tan's method of measuring the fluorescence of DCF-DA (dichlorofluorescin diacetate) oxidized by ROS (Tan et al., 1998, J. Cell Biol. Vol. 141, pp1423-1432).

At this time, for comparison, the amounts of active oxygen species were measured without treatment of the test substance (untreated), with no ultraviolet stimulation, and with ultraviolet stimulation without treatment of the test substance.

 The above procedures were carried out using the standard solutions of Reference Example 4 (concentrations 2 uM, 0.5 uM, 0.4 uM, 0.2 uM, 0.1 uM and 0.01 uM) as the above test materials. (Concentration 1, 10, and 100 uM), respectively, and the above procedures were performed with the standard solutions of Reference Example 6 (concentrations 1, 10, and 100 uM). These results are shown in the following Table 1 as a ratio to the ROS of the untreated group not treated with the test substance and not irradiated with ultraviolet light.

Test substance UVB 30 mJ / cm ² Time elapsed after investigation 0hr 2 hr 3hr No treatment 100 245 289 UVB + no treatment 100 327 383 UVB + (-) EGCG 0.01 uM 100 323 378 UVB + (-) EGCG 0.1 uM 100 321 372 UVB + (-) EGCG 0.2uM 100 318 364 UVB + (-) EGCG 0.4 uM 100 311 359 UVB + (-) EGCG 0.5 uM 100 310 354 UVB + (-) EGCG 2uM 100 295 342 UVB + (2S) -1-O-linolenoyl-2-O-linolenoyl-3-O- beta -D- galactopyranosyl- 100 321 380 UVB + (2S) -1-O-linolenoyl-2-O-linolenoyl-3-O- beta -D- galactopyranosyl- 100 311 357 UVB + (2S) -1-O-linolenoyl-2-O-linolenoyl-3-O- beta -D-galactopyranosyl-sn- 100 307 333 UVB + (2S) -1-O-linoleoyl-2-O-linoleoyl-3-O- beta -D-galactopyranosyl-sn- 100 323 379 UVB + (2S) -1-O-linoleoyl-2-O-linoleoyl-3-O- beta -D-galactopyranosyl-sn- 100 313 358 UVB + (2S) -1-O-linoleoyl-2-O-linoleoyl-3-O- beta -D-galactopyranosyl-sn- 100 305 331

(2S) -1-O-linolenol-2-O-linolenol-3-O- beta -D-galactopyranosyl-sn-glycerol and (2S) - 1-O-linoleoyl-2-O-linoleoyl-3-O- beta -D-galactopyranosyl-sn-glycerol inhibited the production of ROS, which is known to cause skin cell damage by UV radiation at low concentrations . However, the antioxidant effect of the untreated group is almost the same as that of ROS after ultraviolet stimulation.

In order to examine the synergistic effect on the sulfation activity of monogalactosyl diacyl glycerol, the standard solutions of Reference Example 4 (concentration 1 uM, 0.5 uM, 0.4 uM, 0.2 uM, 0.1 uM and 0.01 uM) were each mixed with the standard solution (concentration 10 uM) of Reference Example 5, and the standard solutions of Reference Example 4 (concentration 1 uM, 0.5 uM, 0.4 uM, 0.2 uM, 0.1 uM and 0.01 uM) were mixed with the standard solution of Reference Example 6 (concentration 10 uM), respectively.

These results are shown in the following Table 2 as a ratio to the ROS of the untreated group not treated with the test substance and not irradiated with ultraviolet light.

(-) EGCG concentration UVB 30 mJ / cm ² Time elapsed after investigation 0hr 2 hr 3hr (-) EGCG + (2S) -1-O-linolenol-2-O-linolenol-3-O- beta -D-galactopyranosyl-sn- 0.01 uM 100 319 361 0.1 uM 100 309 350 0.2 uM 100 318 364 0.4 uM 100 259 302 0.5 uM 100 258 300 1uM 100 257 298 (-) EGCG + (2S) -1-O-linoleoyl-2-O-linoleoyl-3-O- beta -D- galactopyranosyl- 0.01 uM 100 318 357 0.1 uM 100 304 345 0.2 uM 100 275 319 0.4 uM 100 261 302 0.5 uM 100 259 301 1uM 100 258 300

(2S) -1-O-linolenoyl-2-O-linolenol-3-O- beta -D-galactopyranosyl-sn- glycerol and (2S) -1- For 10 uM of each of leuyl-2-O-linoleoyl-3-O- beta -D-galactopyranosyl-sn-glycerol, when the concentration of catechin was less than 0.2 uM, the ROS inhibitory effect was weak, The optimum concentration of catechin: monogalactosyl diacyl glycerol is in the range of 1: 25 ~ 1: 50, and the optimum ratio of catechin: monogalactosyl diacyl glycerol is 1: 25 ~ 1: 50, And monogalactosyldiacylglycerol were superior to antioxidant synergistic effect in the case of using monogalactosyldiacylglycerol alone.

[Test Example 2] Measurement of collagen biosynthesis efficiency of skin cells

Human fibroblast (cell line: KF-4109; available from Klebosaur) was added to a 48 well microtiter plate containing 2.5% fetal bovine serum-containing DMEM (Dulbecco's Modified Eagle's Media) after incubation for 10 into the ^four levels, it was replaced with medium containing the test substance. After 48 hours of incubation, the supernatant was harvested and the amount of procollagen produced was quantitated using the ELISA (Takara MK101) method.

The above procedures were carried out using the standard solutions of Reference Example 4 (concentrations 2 uM, 0.5 uM, 0.4 uM, 0.2 uM, 0.1 uM and 0.01 uM) as the above test materials. (Concentration 1, 10, and 100 uM), respectively. These results are shown in Table 3, where the control group without any treatment is designated as 100, and the comparative values are shown in Table 3 below.

density Amount of collagen production (-) EGCG 0.01 uM 125.7 0.1 uM 133.8 0.2 uM 147.4 0.4 uM 154.6 0.5 uM 155.8 2uM 156.7 (2S) -1- O - Reno Reno days -2- O - Reno Reno yl -3- O - β - D - galactosidase pyrazol nosil - sn - glycerol 1uM 100.6 10uM 129.5 100uM 157.4 (2S) -1- O - Reno Leo days -2- O - Reno Leo yl -3- O - β - D - galactosidase pyrazol nosil - sn - glycerol 1uM 100.7 10uM 129.5 100uM 157.5

From the above Table 3, it can be seen that catechin, (2S) -1-O-linolenoyl-2-O-linolenoyl-3-0-? -D- galactopyranosyl- O-linoleoyl-2-O-linoleoyl-3-O- beta -D-galactopyranosyl-sn-glycerol increased collagen biosynthesis even at low concentrations, respectively.

In addition, (2S) -1-O-linolenoyl-2-O-linolenol-3-O- beta -D- galactopyranosyl- -2-O-linoleoyl-3-O- beta -D-galactopyranosyl-sn-glycerol, the standard solutions of Reference Example 4 (concentration 1uM, 0.5uM, 0.4uM, 0.2uM, 0.1uM and 0.01uM) were mixed with the standard solution of Reference Example 5 (concentration 10uM), respectively. (Concentration of 1 uM, 0.5 uM, 0.4 uM, 0.2 uM, 0.1 uM and 0.01 uM) of the standard solution of Reference Example 6 (concentration of 10 uM), respectively.

These results are shown in the following Table 4 as a control group in which no treatment is performed.

(-) EGCG concentration Amount of collagen production (-) + EGCG (2S) -1- O - Reno Reno days -2- O - Reno Reno yl -3- O - β - D - galactosidase pyrazol nosil - sn - glycerol 10uM 0.01 uM 144.5 0.1 uM 151.8 0.2 uM 164.6 0.4 uM 167.4 0.5 uM 168.3 1uM 168.9 (-) + EGCG (2S) -1- O - Reno Leo days -2- O - Reno Leo yl -3- O - β - D - galactosidase pyrazol nosil - sn - glycerol 10uM 0.01 uM 147.2 0.1 uM 153.4 0.2 uM 161.4 0.4 uM 168.9 0.5 uM 169.1 1uM 169.9

From Table 4, it can be seen that (2S) -1-O-linolenoyl-2-O-linolenoyl-3-0-? -D- galactopyranosyl- For each 10 uM of leuyl-2-O-linoleoyl-3-O- beta -D-galactopyranosyl-sn-glycerol, when the concentration of catechin was less than 0.2 uM, the amount of collagen production was weak. The optimum concentration ratio of catechin: monogalactosyl diacyl glycerol is 1: 25 ~ 1: 50, and the optimum concentration ratio of catechin: monogalactosyl diacyl glycerol is 1: 25 ~ 1: It was confirmed that the synergistic effect of collagen biosynthesis was superior to the case of using galactosyldiacyl glycerol alone.

[Test Example 3] Wrinkle improvement effect in human

The nutritional creams prepared in the compositions of Examples 1 to 8 in Table 5 and Comparative Examples 1 to 6 in the following Table 6 were evaluated as follows in order to confirm the wrinkle-improving effect. 140 women in their 30s were divided into 10 groups of 10 persons each in Comparative Examples 1 to 6 and Examples 1 to 8, and applied once a day for 8 weeks. Then, the replicas were removed using silicone and the wrinkles were measured with a visiometer, SV600, Courage + Khazaka electronic GmbH, Germany). The results are shown in Table 7 below. The values in Table 6 below are the average values obtained by subtracting the pre-application parameter values from the respective parameter values after 8 weeks of application.

Compounding ingredient
(Content:% by weight) Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Example 8 Purified water To 100 To 100 To 100 To 100 To 100 To 100 To 100 To 100 (-) EGCG 0.02 0.03 0.03 0.02 0.02 0.03 0.03 0.02 (2S) -1-O-linolenoyl-2-O-linolenoyl-3-O- beta -D-galactopyranosyl-sn- glycerol 1.48 1.47 1.47 1.48 - - - - (2S) -1-O-linoleoyl-2-O-linoleoyl-3-O- beta -D-galactopyranosyl-sn- glycerol - - - - 1.48 1.47 1.47 1.48 Vegetable hydrogenated oil 1.50 1.50 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 0.60 0.60 Glycerol stearate 1.00 1.00 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 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 1.00 1.00 Arachidyl behenyl alcohol and arachidyl glucoside 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 Cetylaryl Alcohol and Cetearyl Glucose Side 2.00 2.00 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 1.50 1.50 Caprylic / capric triglyceride 11.0 11.0 11.0 11.0 11.0 11.0 11.0 11.0 Cyclone methicone 6.0 6.0 6.0 6.0 6.0 6.0 6.0 6.0 Preservative, incense Suitable amount Suitable amount 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 0.1 0.1

Compounding ingredient
(Content:% by weight) Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Comparative Example 5 Comparative Example 6 Purified water To 100 To 100 To 100 To 100 To 100 To 100 (-) EGCG 0.02 0.03 - - - - (2S) -1-O-linolenoyl-2-O-linolenoyl-3-O- beta -D-galactopyranosyl-sn- glycerol - - 1.47 1.48 - - (2S) -1-O-linoleoyl-2-O-linoleoyl-3-O- beta -D-galactopyranosyl-sn- glycerol - - - - 1.47 1.48 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 and arachidyl glucoside 1.00 1.00 1.00 1.00 1.00 1.00 Cetylaryl Alcohol and Cetearyl Glucose Side 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 / capric triglyceride 11.0 11.0 11.0 11.0 11.0 11.0 Cyclone methicone 6.0 6.0 6.0 6.0 6.0 6.0 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

Clinical results after 8 weeks of use R1 R2 R3 R4 R5 Example 1 -0.22 -0.22 -0.18 -0.04 -0.04 Example 2 -0.23 -0.23 -0.19 -0.06 -0.05 Example 3 -0.23 -0.24 -0.18 -0.06 -0.04 Example 4 -0.24 -0.23 -0.18 -0.05 -0.03 Example 5 -0.22 -0.23 -0.18 -0.04 -0.04 Example 6 -0.23 -0.24 -0.19 -0.06 -0.05 Example 7 -0.24 -0.25 -0.18 -0.05 -0.04 Example 8 -0.26 -0.25 -0.18 -0.05 -0.03 Comparative Example 1 -0.16 -0.17 -0.13 -0.04 -0.03 Comparative Example 2 -0.16 -0.17 -0.12 -0.05 -0.03 Comparative Example 3 0.28 0.27 0.23 0.08 0.08 Comparative Example 4 0.26 0.26 0.22 0.07 0.08 Comparative Example 5 0.28 0.28 0.23 0.08 0.09 Comparative Example 6 0.27 0.26 0.22 0.08 0.08 * R1: Difference between the maximum value and the minimum value of the contour line
R2: The wrinkle contour line is arbitrarily divided into 5 squares, and the average of R1 values
R3: Maximum value of R1 divided by 5
R4: Mean value obtained by subtracting the value of the apex and valley of each angle from the baseline of the wrinkle contour line. R5: Difference value obtained by subtracting each wrinkle contour from the baseline of the wrinkle contour line.

As shown in Table 7, when catechin and (2S) -1-O-linolenol-2-O-linolenol-3-O- beta -D-galactopyranosyl-sn- (2S) -1-O-linoleoyl-2-O-linoleoyl-3-O- beta -D-galactopyranosyl-sn- It was found that the external-use composition of Examples 5 to 8 prepared by containing all the ingredients in the composition ratio was excellent in the skin wrinkle-improving effect.

 [Test Example 4] Measurement of skin elasticity improvement in human body

The skin elasticity improvement effect of the nutrition cream prepared with the composition of Table 5 was measured. 100 healthy women over 30 years old at a temperature of 24-26 캜 and a humidity of 75% were divided into 10 groups and the nutritional creams of Comparative Examples 1 to 4 and Examples 1 to 4 were applied to the face for 2 weeks for 12 weeks in each group The skin elasticity was measured using a skin elasticity meter Cutometer SEM 575, C + K Electronic Co., Germany). The results are shown in Table 6. The results in Table 8 are expressed as the value of ΔR8 of the skin elasticity meter Cutometer SEM 575, and the value of R8 indicates the property of viscoelasticity.

At the end of the test, subjects were asked to fill out questionnaires and perform subjective evaluation of efficacy at the same time. The results are shown in Table 9 below.

Application group Skin elasticity effect Example 1 0.37 Example 2 0.43 Example 3 0.41 Example 4 0.42 Example 5 0.39 Example 6 0.44 Example 7 0.43 Example 8 0.45 Comparative Example 1 0.29 Comparative Example 2 0.31 Comparative Example 3 0.27 Comparative Example 4 0.28 Comparative Example 5 0.28 Comparative Example 6 0.29

Application group Number of respondents (in) Very good Good usually Inadequate Example 1 4 3 2 One Example 2 4 4 One One Example 3 4 3 3 0 Example 4 3 5 One One Example 5 4 3 2 One Example 6 4 4 One One Example 7 4 3 3 0 Example 8 3 5 One One Comparative Example 1 One One 6 2 Comparative Example 2 One 2 4 3 Comparative Example 3 0 2 5 3 Comparative Example 4 One One 5 3 Comparative Example 5 0 One 6 3 Comparative Example 6 One One 6 2

As shown in Table 8, when catechin and (2S) -1-O-linolenol-2-O-linolenol-3-O- beta -D-galactopyranosyl-sn- (2S) -1-O-linoleoyl-2-O-linoleoyl-3-O- beta -D-galactopyranosyl-sn- The skin elasticity was further increased in the group to which the external preparation composition of Examples 5 to 8 was applied, as compared with the group to which the comparative example was applied.

In addition, as shown in Table 9, when catechin and (2S) -1-O-linolenol-2-O-linolenol-3-0-? -D- galactopyranosyl- (2S) -1-O-linoleoyl-2-O-linoleoyl-3-O- beta -D-galactopyranosyl-sn-glycerol Was contained in a certain ratio, the skin elasticity was improved in the group to which the external preparation composition of Examples 5 to 8 was applied, as compared with the group to which the Comparative Example was applied.

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 10 below.

Content (% by weight) (-) EGCG 0.04 (2S) -1-O-linoleoyl-2-O-linoleoyl-3-O- beta -D- galactopyranosyl- -O-linolenol-3-O-? -D-galactopyranosyl-sn-glycerol 2.46 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

Nutritive creams are prepared according to the usual methods with the compositions shown in Table 11 below.

Content (% by weight) (-) EGCG 0.04 (2S) -1-O-linoleoyl-2-O-linoleoyl-3-O- beta -D- galactopyranosyl- -O-linolenol-3-O-? -D-galactopyranosyl-sn-glycerol 2.46 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 12 below.

Content (% by weight) (-) EGCG 0.04 (2S) -1-O-linoleoyl-2-O-linoleoyl-3-O- beta -D- galactopyranosyl- -O-linolenol-3-O-? -D-galactopyranosyl-sn-glycerol 2.46 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 13 below.

Content (% by weight) (-) EGCG 0.04 (2S) -1-O-linoleoyl-2-O-linoleoyl-3-O- beta -D- galactopyranosyl- -O-linolenol-3-O-? -D-galactopyranosyl-sn-glycerol 2.46 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 14 below.

Content (% by weight) (-) EGCG 0.02 (2S) -1-O-linoleoyl-2-O-linoleoyl-3-O- beta -D- galactopyranosyl- -O-linolenol-3-O-? -D-galactopyranosyl-sn-glycerol 1.48 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 in a conventional manner with the composition shown in Table 15 below.

Content (% by weight) (-) EGCG 0.02 (2S) -1-O-linoleoyl-2-O-linoleoyl-3-O- beta -D- galactopyranosyl- -O-linolenol-3-O-? -D-galactopyranosyl-sn-glycerol 1.48 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

(-) EGCG, (2S) -1-O-linoleoyl-2-O-linoleoyl-3-O- beta -D- galactopyranosyl-sn- glycerol and (2S) -1- 2-O-linolenoyl-3-O- beta -D-galactopyranosyl-sn-glycerol, 2.5 mg of vitamin C, 2 mg of palm oil, 8 mg of palm kernel oil, 4 mg and lecithin (6 mg) were mixed, and 400 mg / capsule was filled according to a conventional method to prepare a soft capsule.

[Formulation Example 8] Tablets

(-) EGCG, (2S) -1-O-linoleoyl-2-O-linoleoyl-3-O- beta -D- galactopyranosyl- O-beta-D-galactopyranosyl-sn-glycerol, 2.5 mg of vitamin C, 100 mg of glucose, 96 mg of starch and 1 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]

(2S) -1-O-linoleoyl-2-O-linoleoyl-3-O- beta -D- galactopyranosyl-sn- glycerol and 2.4 mg of ( 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 100 mg of 30% ethanol was added to form granules, followed by drying at 60 캜 to form granules, which were then filled in a capsule. The final weight of the contents was 1 g.

[Formulation Example 10]

(-) EGCG, 2.46 mg of (2S) -1-O-linolenol-3-O- beta -D-galactopyranosyl-sn- glycerol, 2.5 mg of vitamin C, 10 g of glucose, 2 g of citric acid, Were mixed and filled in a bottle. 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 (7)

In a composition for external application for skin containing catechin and monogalactosyldiacyl glycerol as an active ingredient,
Wherein the catechin is contained in an amount of 0.001 to 0.2% by weight based on the total weight of the composition, the monogalactosyl diacyl glycerol is contained in an amount of 1.0 to 10% by weight based on the total weight of the composition,
Wherein the content ratio of the catechin: monogalactosyl diacyl glycerol is from 1:25 to 1:50 by molar ratio. The method according to claim 1, wherein the monogalactosyl diacyl glycerol is (2S) -1-O-linolenoyl-2-O-linolenol-3-O- (2S) -1-O-linoleoyl-2-O-linoleoyl-3-O- beta -D-galactopyranosyl-sn-glycerol represented by the following formula , Wherein the composition is at least one selected from the group consisting of an anti-aging skin composition and an anti-aging skin composition.
[Chemical Formula 1]

(2)

The catechin according to claim 1, wherein the catechin is at least one selected from the group consisting of EGCG (epigallocatechin gallate), GCG (gallocatechin gallate), ECG (epicatechin gallate), and CG Wherein the composition is an external preparation for skin. The composition for external application for skin according to claim 1, wherein the composition is for antioxidation. The composition for external application for skin according to claim 1, wherein the composition is for promoting collagen synthesis. The composition for external application for skin according to claim 1, wherein the composition is for improving skin elasticity. The composition for external application for skin according to claim 1, wherein the composition is for improving skin wrinkles.