KR101921903B1 - Composition for antioxidation or whitening containing 21-O-angeloyltheasapogenol E3 from green tea seed - Google Patents

Abstract

The present invention relates to an antioxidative or whitening composition containing 21-O-angeloyldisasporinol E3 component derived from green tea seeds as an active ingredient, and more particularly to a composition for antioxidant or whitening comprising an acid, a base, an enzyme, O-angeloyldisasporin E3 derived from a green tea seed obtained from a seed-seed extract through a decomposition reaction using an enzyme of the present invention as an active ingredient.

Description

[0002] Composition for antioxidation or whitening containing 21-O-angeloyltasapogenol E3 from green tea seed containing 21-O-

The present invention relates to an antioxidative or whitening composition containing 21-O-angeloyldisasporinol E3 component derived from green tea seeds as an active ingredient, and more particularly to a composition for antioxidant or whitening comprising an acid, a base, an enzyme, O-angeloyldisasporin E3 derived from a green tea seed obtained from a seed-seed extract through a decomposition reaction using an enzyme of the present invention as an active ingredient.

The human skin undergoes changes due to various internal and external factors as it gets older. 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 The amount of ultraviolet rays reaching the surface of the sunlight increases, and as the environmental pollution is further intensified, free radicals and active harmful oxygen are increased, thereby causing various problems to the skin. Oxygen, which is present in a stable state, is oxidized by superoxide anion radical (O ₂ ^- ), hydroxyl radical (O ₂ ^- ) due to environmental and biochemical factors such as enzymes, reductive metabolites, chemicals, pollutants, , Reactive oxygen species (ROS), such as hydrogen peroxide (H ₂ O ₂ ), singlet oxygen ( ¹ O ₂ ), and the like, Proteins, lipids, DNA, etc. can be irreversibly destroyed. The action of these reactive oxygen species is the antioxidant enzymes such as superoxide dismutase (SOD), catalase, peroxidase, and glutathione, and vitamin C (ascorbic acid, vitamin E (tocopherol), and the like. However, when such bio-defense is abnormal or excessive oxygen is exposed to the active oxygen, residual or excess active oxygen causes deadly oxygen toxicity to the living body, and non-selective, irreversible reaction to lipid, protein, It is known that aging induces various diseases such as cancer, brain diseases such as stroke, Parkinson's disease, heart disease, ischemia, arteriosclerosis, skin disease, gastrointestinal disease, inflammation, rheumatism and autoimmune disease (Cross et al., Ann. Intern. Med., 1987, 107, 526; Alderson et al., Proc. Natl. Acad. Sci. USA, 1988, 85, 2706).

For the development of natural antioxidants, many raw materials derived from natural materials have been studied. Most raw materials derived from natural materials have been used as simple extracts, and it is not known what kind of substances the efficacy of the extracts is due to. It is a reality that it is used for cosmetics by word of mouth.

On the other hand, various factors are involved in determination of human skin color. Among them, activity of melanocyte which makes melanin pigment, distribution of blood vessels, thickness of skin, presence of pigment inside and outside of human body such as carotinoid and bilirubin The factors of importance are.

Especially, the most important factor is melanin, a melanin pigment produced by the action of various enzymes such as tyrosinase in melanocytes in the human body. The formation of melanin pigment affects genetic factors, hormonal secretion, physiological factors such as stress, and environmental factors such as ultraviolet irradiation.

The melanin pigment produced in the melanocytes of the body skin is a phenolic polymer substance having a complex form of black pigment and protein. It protects skin organs below the dermis by blocking ultraviolet rays irradiated from the sun, and at the same time, free radicals And protects proteins and genes in the skin.

Melanin, which is produced by stress stimuli inside and outside of the skin, is a stable substance that does not disappear until the skin is excreted through skin keratinization even if the stress disappears. However, when melanin is produced more than necessary, it induces hypercholesterolemia such as spots, freckles, and dots, resulting in poor cosmetic results.

In addition, as the number of people enjoying outdoor activities increased due to the increase in the leisure population, the demand for preventing melanin pigmentation due to ultraviolet rays increased.

In response to such demands, substances having ascorbic acid, kojic acid, arbutin, hydroquinone, glutathione, derivatives thereof, or thyrocinase inhibiting activity have been conventionally used in cosmetics or pharmaceuticals, The use thereof is limited due to insufficient whitening effect, safety problem to skin, formulation and stability of formulation in cosmetics, and the like.

The present inventors have researched a substance showing superior antioxidative and whitening effect and found that the extract obtained from the green tea seed extract by using an acid, a base, an enzyme or a microorganism producing the enzyme -O- Angelo deasaphorogen E3 component has excellent antioxidative and whitening effect, thus completing the present invention.

Accordingly, it is an object of the present invention to provide an antioxidant or skin whitening composition containing 21-O-angeloyldisasporin E3 component obtained from green tea seed extract.

In order to solve the above-mentioned object, the present invention provides an antioxidant skin external composition composition containing 21-O-angeloyldisasporin E3 as an active ingredient.

The present invention also provides a whitening dermatological external preparation composition containing 21-O-angeloyl deasaphorogen E3 as an active ingredient.

In the present invention, 21-O-angeloyl deasaphorogen E3 inhibits melanin formation and improves pigmentation caused by ultraviolet rays (UV), as well as antioxidative effects with DPPH and ROS formation inhibitory effects And thus the 21-O-angeloyldisasporin E3 according to the present invention can be very usefully used as a composition for skin external application such as antioxidant, whitening cosmetic composition or pharmaceutical composition, or as a food composition .

The present invention provides a composition comprising 21-O-angeloyltheasaponenol E3 represented by the following formula (1) as an active ingredient.

The 21-O-angeloyl deasaphorogen E3 is preferably derived from green tea seeds.

The 21-O-angeloyl deasaphorogen E3 used in the present invention is a first step for obtaining a saponin crude extract from plants using water or an organic solvent; And a second step of hydrolyzing the extract using an acid, a base, an enzyme or a microorganism producing the enzyme to isolate 21-O-angeloyl deasaphorogen E3.

Step 1: Obtaining saponin crude extract

Saponin crude extract is obtained from plants, especially green tea seeds. At this time, water or an organic solvent can be used as the extraction solvent. As the organic solvent, one or more organic solvents selected from the group consisting of ethanol, methanol, butanol, ether, ethyl acetate and chloroform or a mixture thereof with water, preferably 50 % Ethanol can be used.

In order to obtain a saponin crude extract from plants using water or an organic solvent, water or an organic solvent is added to the plant in an amount of about 1 to 6 times, preferably about 3 times, and extracted with stirring at room temperature for 1 to 5 times, . Water or organic solvent of about 1 to 8 times, preferably about 4 times, is added to the degreased plant, subjected to reflux extraction 1 to 5 times, and then immersed at 10 to 20 DEG C for 1 to 3 days. Then, the residue and the filtrate are separated through filtration and centrifugation, the separated filtrate is concentrated under reduced pressure, and the resulting extract is suspended in water, and then the pigment is removed using ether or the like. After the aqueous layer is extracted 1 to 5 times with an organic solvent, the obtained organic solvent layer is concentrated under reduced pressure to obtain an organic solvent extract, which is then dissolved in a small amount of methanol, ethanol, propanol, butanol and the like. Then, a large amount of ethyl acetate, acetonitrile or the like is added to the resulting precipitate to dry the saponin crude extract of the present invention.

Step 2: 21-O- Angeloides deasapogen E3 Separation of

The saponin crude extract obtained in the first step may be hydrolyzed to isolate 21-O-Angeloyldialesazool E3. The hydrolysis may be carried out using an acid, a base, an enzyme or a microorganism producing the enzyme have.

The acid is preferably at least one acid selected from the group consisting of hydrochloric acid, sulfuric acid and nitric acid, or a mixture thereof with at least one alcohol selected from the group consisting of ethanol, methanol and butanol, preferably with 50% ethanol A solvent may be used.

When the hydrolysis is carried out using an acid, a saponin crude extract is added to the saponin crude extract in an amount of 0.1 to 2 N, preferably 1 N, of an acid or a mixed solvent of an acid and an alcohol in an amount of 1 to 10% Is heated and refluxed in a water bath at 80 캜 for 0.5 to 8 hours, preferably 1 hour.

The base may be at least one selected from the group consisting of sodium hydroxide and potassium hydroxide, or a mixture thereof with at least one alcohol selected from the group consisting of ethanol, methanol and butanol, preferably with 50% butanol A solvent may be used.

In the case of hydrolysis using a base, the saponin crude extract is dissolved in water or a mixed solvent of water and ethanol, and then a 0.1 to 2N, preferably 1N, base or a mixed solvent of base and alcohol is added in an amount of 1 to 10% The mixture is heated to reflux in a water bath at 50 to 100 ° C, preferably 100 ° C for 0.5 to 24 hours, preferably 12 hours.

The enzyme is an enzyme that degrades sugar chains and is characterized in that the sugar moiety of green tea saponin is removed to produce 21-O-angeloyldialcaspiol E3. These enzymes can be commercially available or can be prepared and used as needed, in particular from microorganisms that produce the enzyme.

Further, as the above-mentioned enzyme, more preferably, glucosidase, arabinosidase, rhamnosidase, xylosidase, cellulase, hesperidinase, one selected from the group consisting of hesperidinase, naringinase, glucuronidase, pectinase, galactosidase, and amyloglucosidase. Or more can be used.

In addition, the microorganisms producing the enzyme may be selected from the group consisting of aspergillus genus, bacillus genus, penicillium genus, rhizopus genus, rhizomucor genus, One or more members selected from the group consisting of the genus Corynebacterium, the genus Corynebacterium, the genus Corynebacterium, the genus Corynebacterium, the genus Corynebacterium, the genus Corynebacterium, the genus Corynebacterium, the genus Corynebacterium, the genus Corynebacterium, the genus Thaleromyces, the genus Bifidobacterium, the genus Mortierella, the genus Cryptococcus and the microbacterium genus.

When the enzyme is hydrolyzed, the saponin crude extract is dissolved in an acidic buffer solution at 5 to 20 times, preferably about 10 times, and then the enzyme is added in an amount of 0.001 to 10%. It is confirmed by the thin layer chromatography that the substrate is scraped off while stirring in a water bath at about 25 to 37 ° C for about 40 to 55 hours, preferably about 48 hours. When the substrate is completely lost, The reaction is terminated by heating for 15 minutes.

When the microorganism is hydrolyzed, the saponin crude extract is dissolved in ionized water at 5 to 10 times, preferably about 10 times, and then sterilized at 121 占 폚 for 30 minutes and cooled to 30 占 폚. Then, the pre-cultured microorganism is inoculated at 5 to 10% by weight with respect to the liquid amount, cultured at 20 to 30 ° C for 2 to 5 days, preferably 5 days, and then the substrate scavenging rate is confirmed by thin layer chromatography When the substrate is completely lost, the culture is centrifuged at 5,000 to 10,000 rpm, and the recovered precipitate is washed three times with distilled water and centrifuged to obtain a precipitate.

After hydrolysis using an acid, a base, an enzyme, or a microorganism producing the enzyme as described above, the reaction solution is concentrated under reduced pressure to remove the solvent, alcohol is added to the residue, and the mixture is stirred for 1 to 5 times. Then, the precipitated salts were removed by filtration, and the filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was separated by silica gel column chromatography (chloroform: methanol = 8: 1 to 4: 1) To obtain 21-O-angeloyl deasaphorogen E3.

The composition of the present invention contains, in an amount of (0.0001) to (10)% by weight, based on the total weight of the composition, 21-O-angioyldisasporin E3 which can be prepared by the above-mentioned method. When the content is less than 0.0001% by weight, antioxidative or whitening effect due to the above-mentioned ingredients can not be obtained. Even if the content exceeds 10% by weight,

The composition of the present invention can be used as an antioxidant composition, and has excellent DPPH and ROS production inhibitory effect.

In addition, the composition of the present invention can be used as a whitening composition, and has an excellent effect of inhibiting melanin production and improving pigment deposition caused by ultraviolet rays (UV).

The composition of the present invention may be formulated into a cosmetic or pharmaceutical composition 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 composition of the present invention may also be in the form of a solution or suspension of a fatty substance, an organic solvent, a solubilizer, a thickening agent, a gelling agent, a softening agent, an antioxidant, a suspending agent, a stabilizer, a foaming agent, a fragrance, Cosmetics such as emulsifying agents, fillers, sequestering agents, chelating agents, preservatives, vitamins, blocking agents, wetting agents, essential oils, dyes, pigments, hydrophilic or lipophilic active agents, lipid vesicles or any other ingredient commonly used in cosmetics Or adjuvants conventionally used in the field of 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 antioxidant or skin whitening effect.

In addition, the composition of the present invention can be formulated into a food composition, for example, in the form of various foods, beverages, gums, tea vitamin complexes, health functional foods, and various food additives.

The food composition of the present invention is not limited to any other ingredients other than those containing 21-O-Angeloyldialesazool E3 as an essential ingredient in the indicated ratios, and may contain various flavors or natural carbohydrates As a component. Examples of the above-mentioned natural carbohydrates include monosaccharides such as glucose, fructose and the like; Disaccharides such as maltose, sucrose and the like; And polysaccharides, for example, conventional sugars such as dextrin, cyclodextrin and the like, and sugar alcohols such as xylitol, sorbitol and erythritol. As natural flavors other than those described above, natural flavors (such as tau martin, stevia extract (e.g., rebaudioside A, glycyrrhizin)) and synthetic flavors (saccharin, aspartame, etc.) have. The ratio of the natural carbohydrate is not limited thereto, but is generally about 1 to 20 g, preferably about 5 to 12 g per 100 ml of the composition of the present invention.

In addition, the food composition of the present invention may contain other components or the like which can give a synergistic effect to the main effect within a range not impairing the intended main effect of the present invention. For example, additives such as perfume, coloring agent, bactericide, antioxidant, preservative, moisturizing agent, thickening agent, inorganic salt, emulsifier and synthetic polymer substance may be further added for improvement of physical properties. In addition, it may further contain auxiliary components such as water-soluble vitamins, oil-soluble vitamins, polymer peptides, polymeric polysaccharides and seaweed extract. The above components may be mixed and selected without difficulty by those skilled in the art depending on the purpose of formulation or use, and the amount thereof may be selected within a range that does not impair the objects and effects of the present invention. For example, the addition amount of the above components may be in the range of 0.01 to 5% by weight, more specifically 0.01 to 3% by weight based on the total weight of the composition.

Hereinafter, the present invention will be described in more detail by way of Examples and Test Examples, but the present invention is not limited thereto.

[Example 1] Preparation of green tea seed extract

To 2 kg of green tea seed, 6 L of hexane was added, and the mixture was degreased with stirring at room temperature for 3 times. Then, 4 kg of 50% ethanol was added to 1 kg of the defatted green tea seeds, refluxed for 3 times, and immersed at 15 캜 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 five times with 1 liter of ether to remove the dye. The aqueous layer was washed with 1-butanol And extracted three times with 500 ml. The whole 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 resulting precipitate was dried to obtain a green tea seed extract (saponin crude extract) 300 g.

[Example 2] Production of 21-O-Angeloyldiaxaphenol E3 by acid hydrolysis method

A 1N HCl-50% methanol solution (v / v) 20 times (v / w) was added to 10 g of the green tea seed extract obtained in Example 1 and the mixture was heated and refluxed in a water bath at 80 ° C for 8 hours, The sugars bound to saponin were hydrolyzed. The reaction solution was concentrated under reduced pressure to remove the solvent. Ethanol (200 ml) was added to the residue and stirred three times, and the precipitated salts were removed by filtration. The filtrate was concentrated under reduced pressure to obtain a crude product. The crude product thus obtained was separated by silica gel column chromatography (chloroform: methanol = 7: 1 to 3: 1) to obtain 21-O-benzoyldialaphthalene E3 0.55 g.

[Example 3] Production of 21-O-angeloyldisasporin E3 by base hydrolysis

10 g of the green tea seed extract obtained in Example 1 was dissolved in 500 ml of dry pyridine and subjected to a reflux reaction in an oil bath for 8 hours by adding sodium methoxide (powder, 10 g) to the green tea seed saponin The bound sugars were hydrolyzed. The reaction solution was concentrated under reduced pressure to remove the solvent. Ethanol (200 ml) was added to the residue and stirred three times, and the precipitated salts were removed by filtration. The obtained filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was separated by silica gel column chromatography (chloroform: methanol = 8: 1 to 4: 1) to obtain 21-O-angeloyldisazaporol E3 g.

[Example 4] Production of 21-O-angeloyldisasporin E3 by enzyme degradation method

10 g of the green tea seed extract obtained in Example 1 was dissolved in 100 ml of 0.1 M acetic acid buffer solution (pH 4.5), and 2.5 g of the enzyme (0.5 g of hesperidinase, 0.5 g of Naringin, 0.5 g of cellulase 0.5 , 0.2 g of? -glucuronidase, 0.5 g of? -galactosidase, 0.3 g of amyloglucosidase, manufactured by Sigma Co.), and the mixture was stirred at 37 ° C. in a water bath for 48 hours, . When green tea saponin disappeared, the reaction was terminated by heating in hot water (80 to 100 ° C) for 10 minutes. The reaction solution was concentrated under reduced pressure to remove the solvent. Ethanol (200 ml) was added to the residue and stirred three times, and the precipitate was removed by filtration. The obtained filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was separated by silica gel column chromatography (chloroform: methanol = 8: 1 to 4: 1) to obtain 21-O-angeloyldialcaspiol E3 1.02 g.

[Example 5] Preparation of 21-O-angeloyldisasporin E3 using microorganisms

10 g of the green tea seed extract obtained in Example 1 was dissolved in 100 ml of ionized water, sterilized at 121 캜 for 30 minutes, cooled to 30 캜, and then pre-cultured Aspergillus niger KCCM 11885 was added to a liquid amount 5 to 10%, and cultured at 30 ° C for 5 days. After confirming that the substrate had completely disappeared by confirming the substrate scavenging rate by thin layer chromatography, the culture solution was centrifuged at 5,000 to 10,000 rpm, And then centrifuged to obtain a precipitate. Ethanol (200 ml) was added to the precipitate and stirred three times, and the precipitate was removed by filtration. The filtrate was concentrated under reduced pressure to obtain a crude product. The crude product thus obtained was separated by silica gel column chromatography (chloroform: methanol = 8: 1 to 4: 1) to obtain 21-O-benzoyldiazapol g.

[Test Example 1] DPPH generation inhibition test (DPPH test)

The antioxidant activity was evaluated by the change of the absorbance generated by the reduction of the organic radical, DPPH (1,1-diphenyl-2-picryl hydrazyl) (the antioxidant was oxidized). The antioxidant activity was evaluated by measuring the degree of decrease in the absorbance of DPPH compared with that of the control group, and the concentration (IC ₅₀ ) showing an absorbance of 50% or less of the absorbance of the control group as the effective antioxidant concentration.

190 μl of a 100 μM (in ethanol) DPPH solution was mixed with 10 μl of the green tea seed extract of Example 1, 21-O-angioyl deasaphorogen E 3 of Examples 2 to 5 and control samples, respectively, to prepare a reaction solution. The mixed reaction solution was reacted at 37 ° C for 30 minutes and absorbance was measured at 540 nm. As a control sample, Trolox, which is widely used as a synthetic antioxidant, was used. The DPPH analysis results for each case are shown in Table 1 below.

sample IC ₅₀ (ppm) Example 1 450.24 Example 2 7.73 Example 3 7.52 Example 4 7.47 Example 5 7.53 Trolox 8.64

From the results shown in the above Table 1, it can be seen that 21-O-angeloyldialczaphenol E3 has an excellent antioxidation ability and is more excellent in antioxidative capacity than Trolox, a known antioxidant.

[Test Example 2] Test for inhibiting the production of reactive oxygen species (ROS) using a fluorescent substance

The cell line used for the test was a human keratinocyte HaCaT cell line (human keratinocyte HaCaT cell line), which was dispensed into a 96-well black plate for fluorescence measurement at a density of 2.0 x 10 ⁴ cells per well and cultured in DMEM supplemented with penicillin / streptomycin (Dulbeccos Modification of Eagles Medium, FBS 10%) medium at 37 ° C, 5% CO ₂ Lt; RTI ID = 0.0 > 1 < / RTI > As a test sample, 50 ppm of green tea seed extract of Example 1, 21-O-Angeloyldialesazool E3 of Examples 2 to 5 and a control sample were used, and as a control sample, trolox Trolox) was used. Then, serum-free DMEM (FBS free) supplemented with penicillin / streptomycin as a culture medium was used and cultured at 37 ° C in 5% CO ₂ Lt; / RTI > for 1 day.

The test samples were incubated for 24 hours and then washed with HCSS (HEPES-buffered control salt solution) to remove the remaining medium. DCFH-DA (2 ', 7'-dichlorodihydro-fluorescein diacetate, Molecular Probes , Inc.) was added, and the mixture was incubated at 37 ° C in 5% CO ₂ For 20 min and washed with HCSS. Then, the fluorescence intensity of DCF (dichlorofluorescein) oxidized with ROS at the initial stage was measured with a fluorescent plate reader (Ex = 485 nm, Em = 530 nm) to measure the fluorescence intensity. Subsequently, the fluorescence intensity was measured with a fluorescent plate reader (Ex = 485 nm, Em = 530 nm) after the irradiation with UVB (30 mJ / cm ² ) and immediately after the treatment and three hours after the treatment.

DMSO was used as a control group. Based on this, the inhibitory activity of each test substance on ROS production was calculated (% of the control group), and the test results are shown in Table 2 below.

The sample (50 ppm) Production inhibition (%) Control group
(DMSO) 00 Example 1 25 Example 2 61.7 Example 3 61.5 Example 4 61.2 Example 5 62.1 Trolox 51.7

From the results shown in Table 2, it can be seen that 21-O-angeloyl deasaphorogen E3 is superior in inhibiting ROS formation, and is superior to Trolox, a known antioxidant, in inhibiting ROS production.

[Test Example 3] Measurement of inhibitory effect on melanin production using mouse pigment cells

(Dooley, TP et al, Skin pharmacol, 7, pp 188-200) in mouse derived from C57BL / 6 mice were cultured in DMEM supplemented with 10% fetal bovine serum, 100 nM 2-O-tetradecanoyl And cultured in a medium supplemented with tetradecanoyphorbol-13-acetate and 1 nM cholera toxin at 37 ° C and 5% CO ₂ . The cells were cultured in a concentration of 10 ⁵ cells / well in a 24-well plate, and each test sample was continuously cultured for 10 days at 10 ppm / RTI > As the test samples, the green tea seed extract of Example 1, 21-O-Angeloyldialesazool E3 of Examples 2 to 5, and the control sample were used. As a control sample, hyclocquinone, a known whitening agent, As a negative control, the test sample was not treated. After the addition of the test sample, 5% CO ₂ The cells were washed with PBS, and the cells were dissolved in 1 N sodium hydroxide. The absorbance at 400 nm was measured. The inhibition rate of melanin production was calculated according to the following equation (1), and the results are shown in Table 3 below (Dooley's method).

Test substance Melanin production inhibition rate (%) Untreated group (negative control group) 00.0 Example 1 75.3 Example 2 75.2 Example 3 75.7 Example 4 74.9 Example 5 75.1 Hydroquinone (positive control) 41.1

From the results shown in Table 3, it can be confirmed that 21-O-angeloyl deasaphorogen E3 exhibits a superior melanin production inhibitory rate and shows a better melanin production inhibitory rate than the known whitening agent hydroquinone.

[Test Example 4] Test for whitening effect on human skin

The following experiment was conducted to examine the whitening effect of 21-O-Angeloyldialesazool E3 of Example 4 on human skin.

First, 12 healthy boys were exposed to a 1.5 cm diameter opaque tape at the upper part of the subject's body, and then they were exposed to ultraviolet rays (UVB) of about 1.5 to 2 times the minimum erythema dose of each subject. To induce blackening of the skin.

After irradiating with ultraviolet rays, 21% of 21-O-benzoyldiazaspol E3 of Example 4 (1% of solvent: 1,3-butyleneglycol: ethanol = 7: 3), 1% of hydroquinone, And 1% of the control group), and one of the conditions was observed for 10 weeks in a state where nothing was applied. The color of skin was measured with a colorimeter CR2002 (Minolta Co., Japan) every 1 week.

Then, the difference (ΔL *) between the start time of the application of the respective test substances and the completion time of the application of the test substances was calculated according to the following equation (2). On the other hand, the whitening effect is judged by comparison of DELTA L * between the sample application region and the control region. When the DELTA L * value is 2, it is determined that whitening of the deposited pigment is noticeable. .

Test substance The degree of skin color brightness (DELTA L *) Example 4 1.80 0.21 Hydroquinone (positive control) 1.90 + 0.11 Vehicle (negative control) 0.50 ± 0.15

From the results shown in Table 4, it can be confirmed that 21-O-angeloyl deasaphorogen E3 brightens skin color and shows a degree of skin color brightness similar to that of hydroquinone, which is a known whitening agent. This can be attributed to the fact that 21-O-angeloyl deasaphorogen E3 used in the present invention improves pigmentation caused by ultraviolet rays to brighten skin color.

Claims (5)

delete A composition for external skin application for skin whitening comprising 21-O-Angeloyldialesazool E3 represented by the following formula (1) as an active ingredient.
[Chemical Formula 1]

3. The composition for external application for skin according to claim 2, wherein the content of 21-O-angeloyldisasporin E3 is 0.0001 to 10% by weight based on the total weight of the composition. 3. The composition for external application for skin according to claim 2, wherein the 21-O-angeloyl deasaphorogen E3 is derived from green tea seeds. The method according to claim 4, wherein the 21-O-angioyl deasaphorogen E3 is obtained by decomposing an extract derived from green tea seeds with an acid, a base, an enzyme, or a microorganism producing the enzyme. ≪ / RTI >