KR20100066125A - Cosmetic composition for anit-aging comprising flavonoid as active ingredients - Google Patents

Abstract

PURPOSE: A cosmetic composition for anti-aging containing flavonoid compounds is provided to suppress MMP-1(Matrix Metalloprotease-1) generation and to improve anti-wrinkle effect. CONSTITUTION: A cosmetic composition for anti-aging contains flavonoid compounds of chemical formula 1 as an active ingredient. In chemical formula 1, R1, R2, and R3 are independently hydrogy group, alkyl group of C1-C4, or alkoxy group of C1-C4. A cosmetic composition for anti-wrinkle also contains 0.000001-15.0 weight% of flavonoid compounds of chemical formula 1. The cosmetic composition is used in the form of solution, suspension, emulsion, paste, gel, cream, lotion, powder, soap, surfactant-containing cleansing, oil, power foundation, or spray.

Description

Anti-aging cosmetic composition containing a flavonoid compound as an active ingredient {Cosmetic Composition for Anit-Aging Comprising Flavonoid as Active Ingredients}

The present invention relates to an anti-aging cosmetic composition containing a flavonoid compound as an active ingredient. More specifically, the present invention relates to a cosmetic composition for preventing skin aging and improving skin wrinkles containing a flavonoid compound as an active ingredient.

Human skin undergoes various physical and chemical changes during the aging process. The causes are largely divided into internal aging and photo-aging, and research on this has been actively conducted. Free radicals may be activated by UV rays, stress, disease conditions, environmental factors, wounds, and age. If this condition is exacerbated, it destroys antioxidant defenses in vivo and damages cells and tissues. And aging. More specifically, lipids, proteins, polysaccharides, and nucleic acids, which are major constituents of the skin, are oxidized to destroy skin cells and tissues, resulting in skin aging. In particular, the oxidation of proteins is caused by severe cuts in the skin's connective tissues such as collagen, hyaluronic acid, elastin, proteoglycan, and fibronectin, resulting in severe over-inflammatory reaction and skin elasticity. If this becomes worse, mutations in the DNA can lead to mutations, cancer, and reduced immune function.

Therefore, it protects the cell membrane by eliminating free radicals caused by metabolic processes of the body, irradiation by ultraviolet rays, and inflammatory reactions.Also, damaged cells should be regenerated by active metabolism to proliferate the cells. You can recover quickly and maintain healthy skin. Aging involves not only free radicals, but also an enzyme called matrix metalloprotease (MMP) .In vivo, the synthesis and degradation of extracellular substrates such as collagen are properly regulated, but their synthesis decreases as aging progresses. Expression of matrix metalloproteinase (MMP), which is an enzyme that degrades, is promoted, thereby decreasing the elasticity of the skin and forming wrinkles. Ultraviolet irradiation also activates these degrading enzymes. Therefore, there is a need for the development of a substance capable of regulating MMP expression that inhibits activation or inhibiting its activity in cells. Until now, most of the raw materials used as materials for cosmetics simply inhibited enzyme activity. Therefore, we tried to regulate the expression and activity of MMP expression induced by intracellular natural aging and photoaging.

The present inventors have diligently researched to improve the skin aging phenomenon by promoting the synthesis of skin proteins damaged by ultraviolet rays, etc., the composition containing the flavonoid compound is excellent in the antioxidant effect, inhibiting the production of MMP-1 and skin wrinkle improvement The present invention has been completed by finding an effect.

Accordingly, an object of the present invention to provide a cosmetic composition for preventing skin aging comprising a flavonoid compound as an active ingredient.

Another object of the present invention to provide a cosmetic composition for improving skin wrinkles containing a flavonoid compound as an active ingredient.

Another object of the present invention is to provide a cosmetic method comprising the effect of preventing the skin aging by applying a cosmetic composition containing the flavonoid-based compound to the human skin.

Other objects and advantages of the present invention will become apparent from the following examples and claims.

The same purpose as above. It is achieved by a cosmetic composition for preventing skin aging containing a flavonoid compound represented by the following formula (1) as an active ingredient:

[Formula 1]

In the formula,

R ₁ , R ₂ and R ₃ are each independently a hydroxy group, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.

Another object of the present invention is achieved by a cosmetic composition for improving skin wrinkles containing a flavonoid compound represented by the following formula (1) as an active ingredient:

[Formula 1]

In the formula,

R ₁ , R ₂ and R ₃ are each independently a hydroxy group, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.

Preferably, the flavonoid compound is characterized in that it comprises 0.000001-15.0% by weight relative to the total weight of the cosmetic composition.

Also preferably, the cosmetic composition is a group consisting of a solution, a suspension, an emulsion, a paste, a gel, a cream, a lotion, a powder, a soap, a surfactant-containing cleansing, an oil, a powder foundation, an emulsion foundation, a wax foundation and a spray It is characterized by having the formulation selected from.

Another object of the present invention is achieved by a cosmetic method characterized in that the cosmetic composition is applied to human skin.

As described above, the present invention relates to a cosmetic composition for preventing skin aging and improving skin wrinkles containing a flavonoid compound as an active ingredient, wherein the composition containing a flavonoid compound of the present invention has an MMP-1 production inhibitory effect, Excellent antioxidant and skin wrinkle improvement.

The present invention relates to a cosmetic composition for skin aging and skin wrinkle improvement comprising a flavonoid compound as an active ingredient.

Flavonoid compounds included as an active ingredient of the present invention is a compound having a structure of formula (1).

In the formula,

R ₁ , R ₂ and R ₃ are each independently a hydroxy group, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.

In Formula 1, R ₁ , R _2, and R ₃ are all methoxy groups, and the compound is 2,3-dihydrocyadophyticin and is represented by the following Formula 2.

In Chemical Formula 1, R ₁ is hydroxy, R ₂ and R ₃ is a methoxy group is 2,3-dihydroisozingettin, and is represented by the following formula (3).

In Formula 1, R ₁ and R ₂ is a hydroxy group, R ₃ is a methoxy group is a compound 2 ^// , 3 ^// -dihydro-4 ^/// , 5,5 ^// , 7,7 ^// -pentahydrate Roxy-4 ^/ -methoxy-3 ^/// , 8-biflavone (2 ^// , 3 ^// -dihydro-4 ^/// , 5,5 ^// , 7,7 ^// -pentahydroxy-4 ^/ - methoxy-3 ^/// , 8-biflavone), and is represented by the following formula (4).

In Formula 1, R ₁ and R ₃ is a hydroxy group, R ₂ is a methoxy group is 2 ^// , 3 ^// -dihydro-4 ^/ , 5,5 ^// , 7,7 ^// -pentahydroxy- 4 ^/// -methoxy-3 ^/// , 8-biflavone (2 ^// , 3 ^// -dihydro-4 ^/ , 5,5 ^// , 7,7 ^// -pentahydroxy-4 ^/// - methoxy-3 ^/// , 8-biflavone), and is represented by the following formula (5).

In Formula 1, R ₂ and R ₃ is a hydroxy group, R ₁ is a methoxy group is 2 ^// , 3 ^// -dihydro-4,4 ^/// , 5,5 ^// , 7-pentahydroxy- 7 ^// -methoxy-3 ^/// , 8-biflavone (2 ^// , 3 ^// -dihydro-4,4 ^/// , 5,5 ^// , 7-pentahydroxy-7 ^// -methoxy- 3 ^/// , 8-biflavone), and is represented by the following formula (6).

In Formula 1, R ₁ and R ₂ are a methoxy group and R ₃ is a hydroxy group. The compound is 2 ^// , 3 ^// -dihydro-4 ^/ , 5,5 ^// , 7-tetrahydroxy-4 ^/// , 7 ^// -dimethoxy-3 ^/// , 8-biflavone (2 ^// , 3 ^// -dihydro-4 ^/ , 5,5 ^// , 7-tetrahydroxy-4 ^/// , 7 ^// - dimethoxy-3 ^/// , 8-biflavone), and is represented by the following formula (7).

In Formula 1, R ₁ and R ₃ is a methoxy group, R ₂ is a hydroxy group compound is 2 ^// , 3 ^// -dihydro-4 ^/// , 5,5 ^// , 7-tetrahydroxy-4 ^/ , 7 ^// -dimethoxy-3 ^/// , 8-biflavone (2 ^// , 3 ^// -dihydro-4 ^/// .5,5 ^// , 7-tetrahydroxy-4 ^/ , 7 ^// - dimethoxy-3 ^/// , 8-biflavone), and is represented by the following formula (8).

In Formula 1, R _1, R _2, and R ₃ are hydroxy groups, and the compound is 2 ^// , 3 ^// -dihydro-4 ^/ , 4 ^/// , 5,5 ^// , 7,7 ^// -hexahydrate ^/// hydroxy -3, 8-by-flavone ^{(2 //, 3 // -dihydro-} 4 /, 4 ///, 5,5 //, 7,7 // -hexahydroxy-3 ///, 8 -biflavone), represented by the following formula (9).

Such a compound is an example of the flavonoid compound represented by the formula (1) used in the cosmetic composition of the present invention, but is not limited thereto.

2,3-dihydrocysadophyticin, 2,3-dihydroisozingettin used in the present invention can be isolated from natural sources such as leaves of Metasequoia glyptostroboides, Podocarpus macrophyllus var. And can be synthesized chemically.

Also, the above 2 ^// , 3 ^// -dehydro-4 ^/ , 4 ^/// , 5,5 ^// , 7,7 ^// -hexahydroxy-3 ^/// , 8-biflavone, 2 ^// , 3 ^// -dehydro-4 ^/ , 5,5 ^// , 7,7 ^// -pentahydroxy-4 ^/// -methoxy-3 ^/// , 8-biflavone, 2 ^// , 3 ^// -dehydro-4 ^/// , 5,5 ^// , 7,7 ^// -pentahydroxy-4 ^/ -methoxy-3 ^/// , 8-biflavone, 2 ^// , 3 ^// -dihydro-4,4 ^/// , 5,5 ^// , 7-pentahydroxy-7 ^// -methoxy-3 ^/// , 8-biflavones, 2 ^// , 3 ^// - Dihydro-4 ^/ , 5,5 ^// , 7-tetrahydroxy-4 ^/// , 7 ^// -dimethoxy-3 ^/// , 8-biflavone, 2 ^// , 3 ^// -dihydro -4 ^/// , 5,5 ^// , 7-tetrahydroxy-4 ^/ , 7 ^// -dimethoxy-3 ^/// , 8-biflavone and the like can be synthesized chemically.

On the other hand, 2,3-dihydrocysidopycin and 2,3-dihydroisozingettin used in the present invention were isolated from the metasequoia (Metasequoia glyptostroboides) leaves.

According to a preferred embodiment of the present invention, the flavonoid compound is 0.000001-15.0% by weight relative to the total weight of the cosmetic composition of the present invention, preferably contained in an amount of 0.001-10% by weight.

In this case, when the content of the flavonoid compound included in the cosmetic composition of the present invention is less than the minimum content, the expected effect is less likely to occur, and when the content exceeds the maximum content, the effect does not increase any more and is likely to cause irritation to the skin. It also greatly affects the stabilization of the formulation.

According to the present invention, the flavonoid compound of Formula 1 is excellent in the inhibitory effect of MMP-1 production (Experimental Example 1) and the antioxidant effect (Experimental Example 2). In addition, the cosmetic composition containing the flavonoid-based compound is also excellent in the skin wrinkle improvement effect (Experimental Example 3).

Therefore, the cosmetic composition comprising a flavonoid compound having various functions as an active ingredient has an excellent effect on suppressing MMP-1 production, antioxidant effect and skin wrinkle improvement.

In addition, it is apparent to those skilled in the art in consideration of the technical level in the art that the compound of Formula 1 is also included in the scope of the present invention as a mixture with a derivative obtained by the addition or substitution reaction of a substituent commonly practiced in the art.

The cosmetic composition of the present invention can achieve the effect by topical application or spraying on the skin. Therefore, according to a preferred embodiment of the present invention, the composition of the present invention may be prepared in the form of cosmetic compositions such as creams, lotions and softening water or pharmaceutical compositions such as sprays and ointments.

Ingredients included in the cosmetic composition of the present invention as an active ingredient includes components conventionally used in cosmetic compositions in addition to the active ingredient, for example, conventional auxiliaries such as antioxidants, stabilizers, solubilizers, vitamins, pigments and flavors, And carriers.

The cosmetic composition of the present invention may be prepared in any formulation commonly prepared in the art, for example, solutions, suspensions, emulsions, pastes, gels, creams, lotions, powders, soaps, surfactant-containing cleansing , Oils, powder foundations, emulsion foundations, wax foundations and sprays, and the like can be formulated, but is not limited thereto. More specifically, it may be prepared in the form of a flexible lotion, nutrition lotion, nutrition cream, massage cream, essence, eye cream, cleansing cream, cleansing foam, cleansing water, pack, spray or powder.

When the formulation of the present invention is a paste, cream or gel, animal oils, vegetable oils, waxes, paraffins, starches, trachants, cellulose derivatives, polyethylene glycols, silicones, bentonites, silicas, talc or zinc oxide may be used as carrier components. Can be.

In the case where the formulation of the present invention is a powder or a spray, lactose, talc, silica, aluminum hydroxide, calcium silicate or polyamide powder may be used as a carrier component. Especially, in the case of a spray, a mixture of chlorofluorohydrocarbons, propane / Propane or dimethyl ether.

When the formulation of the present invention is a solution or an emulsion, a solvent, a dissolving agent or an emulsifying agent is used as a carrier component, and examples thereof include water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, , 3-butyl glycol oil, glycerol aliphatic ester, polyethylene glycol or sorbitan fatty acid esters.

When the formulation of the present invention is a suspension, liquid carrier diluents such as water, ethanol or propylene glycol, suspending agents such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol esters and polyoxyethylene sorbitan esters, and microcrystals are used as carrier components. Soluble cellulose, aluminum metahydroxy, bentonite, agar or tracant and the like can be used.

When the formulation of the present invention is a surfactant-containing cleansing, the carrier component is aliphatic alcohol sulfate, aliphatic alcohol ether sulfate, sulfosuccinic acid monoester, isethionate, imidazolinium derivative, methyltaurate, sarcosinate, fatty acid amide. Ether sulfates, alkylamidobetaines, aliphatic alcohols, fatty acid glycerides, fatty acid diethanolamides, vegetable oils, lanolin derivatives or ethoxylated glycerol fatty acid esters and the like can be used.

In addition, the present invention provides a cosmetic method characterized in that the cosmetic composition containing the flavonoid compound of the present invention is applied to human skin to exhibit an anti-aging effect of the skin.

The cosmetic method of the present invention refers to all cosmetic methods for applying the cosmetic composition of the present invention to human skin. That is, all the methods known in the art for applying the cosmetic composition to the skin belong to the cosmetic method of the present invention.

The cosmetic composition of the present invention may be used alone or in combination with other cosmetic compositions other than the cosmetic composition of the present invention. In addition, the cosmetic composition with excellent skin protection effect according to the present invention can be used according to a conventional method of use, the number of times of use can be varied according to the user's skin condition or taste.

When the cosmetic composition of the present invention is a soap, surfactant-containing cleansing or surfactant-free cleansing formulation, it may be wiped off, peeled off or washed with water after application to the skin. As a specific example, the soap is liquid soap, powdered soap, solid soap and oil soap, the surfactant-containing cleansing formulation is a cleansing foam, cleansing water, cleansing towels and cleansing pack, the surfactant-free cleansing formulation is a cleansing cream , Cleansing lotion, cleansing water and cleansing gel, but are not limited thereto.

When the cosmetic method including the flavonoid compound of the present invention is applied to human skin, an excellent wrinkle improvement effect can be obtained.

(Example)

Hereinafter, the present invention will be described in more detail with reference to Examples. It is to be understood by those skilled in the art that these embodiments are only for describing the present invention in more detail and that the scope of the present invention is not limited by these embodiments in accordance with the gist of the present invention .

Preparation Example 1 Isolation and Identification of 2,3-Dihydrocythiadophyticin and 2,3-Dihydroisozingettin

2,3-Dihydrocysadophyticin and 2,3-dihydroisozingegetin used in the present invention were isolated and identified in the following manner.

About 1.0 Kg of dry metasequoia was added to 5 L of 80% ethanol, and the mixture was stirred under reflux, followed by filtration and drying of the filtrate under reduced pressure. This was repeated twice to obtain about 60 g of concentrate. This was dissolved in distilled water, and then fractionated into n-hex, EA (ethyl acetate), n-BuOH, and water layers to load the ethyl acetate layer into a column tube filled with silica of 230-400 mesh, and ethyl as a developing solvent. 20 mL fractions were added with acetate and methanol flowing in a 30: 1 to 1: 1 gradient. Fractions up to Rf = 0.43-5.0 were concentrated by qualitative analysis with a thin membrane chromatograph, and the fractions were fractionated with MeOH in a column filled with Sepadex20.

The structure was analyzed by NMR and mass by the fraction. As a result, the components were identified as 2,3-dihydrosciadopitysin and 2,3-dihydroisoginkgetin.

2,3-Dihydrocysadophyticin yellow powder. Melting point, 150-152 →. UV (MeOH) max nm: 278, 322. EI-MS m / z : 582 [M] < + >. 1 H - NMR (CD3COCD3, 400 MHz): 13.08 (1H, s, OH-5``), 12.12 (1H, s, OH-5), 7.68 (2H, d, J = 8.8 Hz, H-2 ''',6'''), 7.65 (1H, dd, J = 8.8, 2.0 Hz, H-6 '), 7.63 (1H, d, J = 2.0 Hz, H-2'), 7.24 (1H, d, J = 8.8 Hz, H-5 '), 6.99 (2H, d, J = 8.8 Hz, H-3''', 5 '''), 6.69 (1H, s, H-3''), 6.42 ( 1H, s, H-6 ''), 6.04 (1H, d, J = 2.0 Hz, H-8), 6.01 (1H, d, J = 2.0 Hz, H-6), 5.60 (1H, dd, J = 13.2, 2.8 Hz, H-2), 3.85 (3H, s, OCH3-4 '''), 3.81 (3H, s, OCH3-7), 3.79 (3H, s, OCH3-4'), 3.31 (1H, m, H-3a), 2.85 ( 1H, m, H-3b); 13C - NMR (CD3COCD3, 100 MHz): 80.1 (C-2), 43.9 (C-3), 197.5 (C-4), 164.2 (C-5), 95.6 (C-6), 168.9 (C-7 ), 94.7 (C-8), 163.6 (C-9), 103.8 (C-10), 132.1 (C-1 '), 132.5 (C-2'), 121.9 (C-3 '), 159.2 (C -4 '), 112.1 (C-5'), 129.0 (C-6 '), 165.0 (C-2''), 104.0 (C-3''), 183.5 (C-4''), 162.4 ( C-5``), 99.7 (C-6 ''), 162.4 (C-7 ''), 105.4 (C-8 ''), 155.7 (C-9 ''), 105.6 (C-10 '' ), 124.3 (C-1 '''), 129.0 (C-2'''), 115.4 (C-3 '''), 164.5 (C-4'''), 115.4 (C-5 ''' ), 129.0 (C-6 '''), 56.0 (OCH3-4'), 56.1 (OCH3-4 '''), 55.5 (OCH3-7).

2, 3-dihydroisozingegetin pale yellow powder. UV (MeOH) max nm: 280, 322. EI-MS m / z : 568 [M] < + >. 1 H - NMR (CD3COCD3, 400 MHz): 13.09 (1H, s, OH-5``), 12.17 (1H, s, OH-5), 7.68 (2H, d, J = 8.8 Hz, H-2 ''',6'''), 7.66 (1H, dd, J = 8.4, 1.6 Hz, H-6 '), 7.63 (1H, d, J = 1.6 Hz, H-2'), 7.24 (1H, d, J = 8.4 Hz, H-5 '), 6.99 (2H, d, J = 8.8 Hz, H-3''', 5 '''), 6.68 (1H, s, H-3''), 6.42 ( 1H, s, H-6 ''), 5.98 (1H, d, J = 2.0 Hz, H-8), 5.95 (1H, d, J = 2.0 Hz, H-6), 5.60 (1H, dd, J = 13.2, 2.8 Hz, H-2), 3.84 (3H, s, OCH3-4 '''), 3.79 (3H, s, OCH3-4'), 3.29 (1H, m, H-3a), 2.82 (1H, m, H-3b); 13C - NMR (CD3COCD3, 100 MHz): 80.0 (C-2), 43.9 (C-3), 197.2 (C-4), 164.5 (C-5), 97.0 (C-6), 167.4 (C-7 ), 96.0 (C-8), 163.7 (C-9), 103.3 (C-10), 132.2 (C-1 '), 132.5 (C-2'), 121.9 (C-3 '), 159.2 (C -4 '), 112.2 (C-5'), 129.0 (C-6 '), 165.1 (C-2``), 104.0 (C-3''), 183.5 (C-4''), 162.4 ( C-5``), 99.7 (C-6 ''), 162.1 (C-7 ''), 105.4 (C-8 ''), 155.8 (C-9``), 105.6 (C-10 '' ), 124.3 (C-1 '''), 129.0 (C-2'''), 115.4 (C-3 '''), 164.5 (C-4'''), 115.4 (C-5 ''' ), 129.0 (C-6 '''), 56.0 (OCH3-4'), 56.2 (OCH3-4 ''').

Preparation Example 2 Synthesis of Derivatives of 2,3-Dihydrocysadophyticin and 2,3-Dihydroisozingettin

1 equivalent of 2,3-dihydrocysidopycin prepared in Preparation Example 1 is dissolved in a solution of 3: 1 mixed with methanol and water. This maintains the temperature of the reactor at 0 ° C. Then, slowly add 3 equivalents of lithium hydroxide and stir for 3 hours. After the reaction was terminated with dilute hydrochloric acid, the methanol solution was removed by an evaporator. Then, the mixture was extracted with methylene chloride solution to obtain a compound. This was separated by flowing normal hexane and ethyl acetate 1: 1 in a column filled with silica. After separating Sepadex LH 20 column packed column with methanol and chloroform solution 1: 1 in a column tube filled with 2 ^// , 3 ^// -dihydro-4 ^/// , 5,5 ^// , 7,7 ^// -pentahydroxy-4 ^/ -methoxy-3 ^/// , 8-biflavone, 2 ^// , 3 ^// -dihydro-4 ^/ , 5,5 ^{/ /} , 7,7 ^// -pentahydroxy-4 ^/// -methoxy-3 ^/// , 8-biflavone, 2 ^// , 3 ^// -dihydro-4,4 ^{/ //} , 5,5 ^// , 7-pentahydroxy-7 ^// -methoxy-3 ^/// , 8-biflavone, 2 ^// , 3 ^// -dihydro-4 ^/ , 5,5 ^// , 7-tetrahydroxy-4 ^/// , 7 ^// -dimethoxy-3 ^/// , 8-biflavone, 2 ^// , 3 ^// -dihydro -4 ^/// , 5,5 ^// , 7-tetrahydroxy-4 ^/ , 7 ^// -dimethoxy-3 ^/// , 8-biflavone and 2 ^// , 3 ^// as shown in Formula 9 above -Dihydro-4 ^/ , 4 ^/// , 5,5 ^// , 7,7 ^// -hexahydroxy-3 ^/// , 8-biflavones were obtained.

Experimental Example 1. Inhibitory effect of 2,3-dihydrocysidopitsine, 2,3-dihydroisozingegetin and derivatives thereof on MMP-1 production

Fibroblasts (Korean Cell Line Bank, Korea), which are human normal skin cells, were seeded in 48-well microplates (Nunc, Denmark) at 1 × 10 ⁶ cells per well, and treated with DMEM medium (Sigma, USA) and 37 ° C. After incubating for 24 hours at 2,3-dihydrocysadophyticin obtained in Preparation Example 1, 2,3-dihydroisozingettin was added to the final concentration of 5, 10, 50, 100 ㎍ / ㎖ , 2 ^// , 3 ^// -dihydro-4 ^/// , 5,5 ^// , 7,7 ^// -pentahydroxy-4 ^/ -methoxy-3 ^/ obtained in Preparation Example 2 as a derivative thereof ^// , 8-biflavone (Formula 4), 2 ^// , 3 ^// -dihydro-4 ^/ , 5,5 ^// , 7,7 ^// -pentahydroxy-4 ^/// -methoxy- 3 ^/// , 8-biflavone (Formula 5), 2 ^// , 3 ^// -dihydro-4,4 ^/// , 5,5 ^// , 7-pentahydroxy-7 ^// -methoxy -3 ^/// , 8-biflavone (Formula 6), 2 ^// , 3 ^// -dihydro-4 ^/ , 5,5 ^// , 7-tetrahydroxy-4 ^/// , 7 ^// - Dimethoxy-3 ^/// , 8-biflavone (Formula 7), 2 ^// , 3 ^// -dihydro-4 ^/// , 5,5 ^// , 7-tetrahydroxy-4 ^/ , 7 ^// -dimethoxy-3 ^/// , 8-biflavone (Formula 8), 2 ^// , 3 ^// -dehydro-4 ^/ , 4 ^/// , 5,5 ^// , 7,7 ^// -hexahydroxy-3 ^/// , 8-biflavone (Formula 9) Serum-free DMEM medium added at a concentration of 10 μg / ml and negative control group added for 48 hours in serum-free DMEM medium without 2,3-dihydrocysidopitsin and 2,3-dihydroisozinqetin Incubated with After incubation, the supernatants of each well were collected and the amount of ng / ml newly synthesized MMP-1 was measured using an MMP-1 assay kit (Amersham, USA), and MMP-1 production was performed according to Equation 1 below. The percent inhibition was calculated and the results are shown in Table 1. At this time, TGF-β (10 µg / ml, Roche, United States) was used as a positive control of MMP-1 production inhibition rate.

MMP-1 Production Inhibition Rate (%) Experimental substance MMP-1
% Production inhibition Negative Control 0 5 μg / ml 2,3-dihydrocydapidocin 77.5 10 μg / ml of 2,3-dihydrocythiadophyticin 86.7 50 μg / ml 2,3-dihydrocydapidocin 91.5 100 μg / ml 2,3-dihydrocydadophyticin 100.6 2,3-dihydroisozingettin 5 ug / ml 75.3 2,3-dihydroisozingegetin 10 ug / ml 81.4 2,3-dihydroisozingegetin 50 ug / ml 100.3 2,3-dihydroisozingegetin 100 ug / ml 110.2 2 ^// , 3 ^// -dehydro-4 ^/ , 4 ^/// , 5,5 ^// , 7,7 ^// -hexahydroxy
-3 ^/// , 8 μg / ml 10 μg / ml 82.3 2 ^// , 3 ^// -dehydro-4 ^/ , 5,5 ^// , 7,7 ^// -pentahydroxy
-4 ^/// -methoxy-3 ^/// , 8-biflavone 10 μg / ml 89.2 2 ^// , 3 ^// -dehydro-4 ^/// , 5,5 ^// , 7,7 ^// -pentahydroxy
-4 ^/ -methoxy-3 ^/// , 8-biflavone 10 μg / ml 84.5 2 ^// , 3 ^// -dehydro-4,4 ^/// , 5,5 ^// , 7-pentahydroxy
-7 ^// -methoxy-3 ^/// , 8-biflavone 10 μg / ml 85.3 2 ^// , 3 ^// -dihydro-4 ^/ , 5,5 ^// , 7-tetrahydroxy
-4 ^/// , 7 ^// -dimethoxy-3 ^/// , 8-biflavone 10 μg / ml 84.2 2 ^// , 3 ^// -dehydro-4 ^/// , 5,5 ^// , 7-tetrahydroxy
-4 ^/ , 7 ^// -dimethoxy-3 ^/// , 8-biflavone 10 μg / ml 84.2 Positive Control (TGF-b) 79.5

As shown in Table 1, it can be seen that the MMP-1 production inhibition rate is significantly increased in the experimental group to which the 2,3-dihydrocysidopitsin, 2,3-dihydroisozingettin or derivatives thereof of the present invention are added. have. In addition, even better results were obtained when compared with 100 μg / ml TGF-b used as a positive control.

Experimental Example 2: Free radical scavenging action of 2,3-dihydrocysidopitsin, 2,3-dihydroisozingettin and derivatives thereof

The free radical scavenging activity of 2,3-dihydrocysidopitsin, 2,3-dihydroisozingettin and derivatives thereof was measured as follows.

In other words, each 2,3-dihydrocysadophyticin in 2 ml of 100 μM 1,1-diphenyl-2-picryl-2-hydrazyl (1,1-diphenyl-2-picryl hydrazyl, DPPH) ethanol solution , 250%, 100, 50, 25, 10 ㎍ / ml of sciadophytosine and isosinkgetin were added, and their derivatives were added at 25 ㎍ / ml, respectively, and reacted at room temperature for 30 minutes, followed by absorbance at 520 nm. Measured. Vitamin C was used as a positive control. Free radical scavenging activity (%) was calculated by the following equation (2), the results are shown in Table 2 below.

Experimental substance Free radical
% Scavenging Activity Negative Control 0 250 μg / ml of 2,3-dihydrocysidopycin 88.9% 100 μg / ml 2,3-dihydrocydadophyticin 88.8% 50 μg / ml 2,3-dihydrocydapidocin 87.8% 25 μg / ml of 2,3-dihydrocyadodophyticin 82.4% 10 μg / ml of 2,3-dihydrocythiadophyticin 72.7% 250 μg / ml 2,3-dihydroisozingegetin 89.4% 2,3-dihydroisozingegetin 100 ug / ml 80.2% 2,3-dihydroisozingegetin 50 ug / ml 75.3% 2,3-dihydroisozingegetin 25 ug / ml 73.2% 2,3-dihydroisozingegetin 10 ug / ml 69.7% 2 ^// , 3 ^// -dehydro-4 ^/ , 4 ^/// , 5,5 ^// , 7,7 ^// -hexahydroxy
-3 ^/// , 25 μg / ml of 8-biflavone 67.2% 2 ^// , 3 ^// -dehydro-4 ^/ , 5,5 ^// , 7,7 ^// -pentahydroxy
-4 ^/// -methoxy-3 ^/// , 8-biflavone 25 μg / ml 64.2% 2 ^// , 3 ^// -dehydro-4 ^/// , 5,5 ^// , 7,7 ^// -pentahydroxy
-4 ^/ -methoxy-3 ^/// , 8-biflavone 25 μg / ml 59.9% 2 ^// , 3 ^// -dehydro-4,4 ^/// , 5,5 ^// , 7-pentahydroxy
-7 ^// -methoxy-3 ^/// , 8-biflavone 25 μg / ml 63.5% 2 ^// , 3 ^// -dihydro-4 ^/ , 5,5 ^// , 7-tetrahydroxy
-4 ^/// , 7 ^// -dimethoxy-3 ^/// , 8-biflavone 25 μg / ml 61.8% 2 ^// , 3 ^// -dehydro-4 ^/// , 5,5 ^// , 7-tetrahydroxy
-4 ^/ , 7 ^// -dimethoxy-3 ^/// , 8-biflavone 25 μg / ml 60.8% 250 μg / ml of vitamin C 91.2% 100 μg / ml of vitamin C 90.8% 50 μg / ml of vitamin C 87.1% 25 μg / ml of vitamin C 75.8% 10 μg / ml of vitamin C 71.3%

Hereinafter, in the formulation example, 2,3-dihydrocysidopycin and 2,3-dihydroisozinqetine obtained from Preparation Example 1 of the present invention were used, but are not necessarily limited thereto.

Formulation Example 1. Softening Longevity

Formulation examples of the flexible longevity was prepared as follows according to a conventional method.

ingredient Content (unit: weight%) 2,3-dihydrocysadophyticin
glycerin
1.3-butylene glycol
PEG 1500
Allantoin
DL-panthenol
E.T.A.-2NA
Benzophenone-9
Sodium hyaluronate
ethanol
Octicdodeceth-16
Polysorbate 20
Preservative, fragrance, coloring
Distilled water 3.0
5.0
3.0
1.0
0.1
0.3
0.02
0.04
5.0
10.0
0.2
0.1
a very small amount
Remaining amount      Sum 100

Formulation Example 2. Converging Cosmetic Water

Formulation examples of convergent longevity were prepared as follows according to a conventional method.

ingredient Content (unit: weight%) 2,3-dihydrocysadophyticin
glycerin
1.3-butylene glycol
Allantoin
DL-panthenol
E.T.A.-2NA
Benzophenone-9
Sodium hyaluronate
ethanol
Polysorbate 20
Witch hazel extract
Citric acid
Preservative, fragrance, coloring
Distilled water 1.5
2.0
2.0
0.2
0.2
0.02
0.04
3.0
15.0
0.3
2.0
a very small amount
a very small amount
Remaining amount      Sum 100

Formulation Example 3. Nutrients

Formulation examples of nutrient cosmetics was prepared as follows in a conventional manner.

ingredient Content (unit: weight%) 2,3-dihydrocysadophyticin
Stearyl alcohol
lanolin
Polysorbate 60
Sorbitan stearate
Cured Vegetable Oil
Mineral oil
Squalane
Trioctanoine
Dimethicone
Tocopherol Acetate
Carboxy Vinyl Polymer
glycerin
1.3-butylene glycol
Sodium hyaluronate
Tri ethanolamine
Preservative, fragrance, coloring
Distilled water 1.5
1.5
1.5
1.3
0.5
1.0
5.0
3.0
2.0
0.8
0.5
0.12
5.0
3.0
5.0
0.12
a very small amount
Remaining amount Sum 100

Formulation Example 4. Nutrition Cream

Formulation of nutrition cream was prepared as follows according to a conventional method.

ingredient Formulation Example 4-1 Formulation Example 4-2 2,3-dihydroiso zinc gettin
2,3-dihydrocysadophyticin
Lipophilic monostearate
Cetearyl Alcohol
Stearic acid
Beeswax
Polysorbate 60
Sorbitan stearate
Cured Vegetable Oil
Squalane
Mineral oil
Trioctanoine
Dimethicone
Sodium magnesium silicate
glycerin
Betaine
Triethanolamine
Sodium hyaluronate
Preservative, fragrance, coloring
Distilled water 3.0
-
1.0
2.0
2.2
1.5
1.0
1.5
0.6
1.0
3.0
5.0
5.0
1.0
0.1
5.0
3.0
1.0
a very small amount
Remaining amount -
3.0
1.0
2.0
2.2
1.5
1.0
1.5
0.6
1.0
3.0
5.0
5.0
1.0
0.1
5.0
3.0
1.0
a very small amount
Remaining amount Sum 100

Formulation Example 5. Massage Cream

Formulation example of the massage cream was prepared as follows according to a conventional method.

ingredient Content (unit: weight%) 2,3-dihydroiso zinc gettin
Lipophilic monostearic acid glycerin
Stearyl alcohol
Stearic acid
Polysorbate 60
Sorbitan stearate
Isostearyl Isosterate
Squalane
Mineral oil
Dimethicone
Hydroxyethyl Cellulose
glycerin
Triethanolamine
Preservative, fragrance, coloring
Distilled water 3.0
1.5
1.5
1.0
1.5
0.6
5.0
5.0
35.0
0.5
0.12
6.0
0.7
a very small amount
Remaining amount Sum 100

Formulation Example 6. Essence

Formulation examples of the essence was prepared as follows in a conventional manner.

ingredient Content (unit: weight%) 2,3-dihydroiso zinc gettin
glycerin
Betaine
Fiji 1500
Allantoin
DL-panthenol
E.T.A.-2Na
Benzophenone-9
Hydroxyethyl cellulose
Sodium hyaluronate
Carboxy Vinyl Polymer
Triethanolamine
Octyldodecanol
Octyldodeceth -16
ethanol
Preservative, fragrance, coloring
Distilled water 5.0
10.0
5.0
2.0
0.1
0.3
0.02
0.04
0.1
8.0
0.2
0.18
0.3
0.4
6.0
a very small amount
Remaining amount Sum 100

Formulation Example 7 Pack

Formulation examples of the pack were prepared as follows in a conventional manner.

ingredient Content (unit: weight%) 2,3-dihydrocysadophyticin
Polyvinyl alcohol
Cellulose gum
glycerin
Fiji 1500
Cyclodextrin
DL-Panthenol
Allantoin
Monomethylammonium Glycyric Acid
Nicotinamide
ethanol
Fiji 40 Cured Castor Oil
Incense, pigment, preservative
Distilled water 3.0
15.0
0.15
3.0
2.0
0.15
0.4
0.1
0.3
0.5
6.0
0.3
a very small amount
Remaining amount Sum 100

Experimental Example 3. Skin Wrinkle Improvement Effect

A clinical trial was conducted on the skin antiwrinkle effect of the cream cosmetic containing 2,3-dihydrosciadopitysin and 2,3-dihydroisozingegetin of the present invention. Clinical trials were evaluated through the actual use test of each cosmetic.

The experiments were carried out using 3% of each of the above ingredients in Formulations 4-1 and 4-2, and Formulation Examples 4-1 and 4-2 containing 2,3-dihydrosocadophyticin, 2,3-dihydroisozingettin. The nutrition cream of the control example which does not contain was evaluated. Each subject was used together on one cheek. Among 40 30-40 year old females, women who had a lot of external activities were randomly divided into 4 groups, and the creams of Formulation Examples 4-1 and 4-2 and Control were washed twice each morning and evening, and then the appropriate amount was centered around the eyes. It was corrected continuously for two months. The eye area of the subject was observed, and the degree of damage by light was quantified according to the photodamage score of Table 10 below, and the experimental results are shown in Table 11.

Photodamage score near the subject 0 none One none / mild 2 mild 3 mild / moderate 4 moderate 5 moderate / severe 6 severe 7 Verysevere Arch Dermatol vol. 137 (8): 1043-1051, 2001

Wrinkle improvement effect (visual evaluation) of the cosmetics of the present invention Week 0 4 Weeks 8 Weeks 4-1 3.86 ± 0.60 3.60 ± 0.60 3.49 ± 0.5 4-2 3.98 ± 0.60 3.71 ± 0.40 3.55 ± 0.50 Control 3.88 ± 0.60 3.84 ± 0.50 3.89 ± 0.60

   As can be seen from the results in Table 11, the cream of Formulation Examples (4-1, 4-2) each containing 2,3-dihydrocyadophyticin and 2,3-dihydroisozingettin is none. It also showed a higher antiwrinkle effect than the cream of the non-added control.

Having described the specific part of the present invention in detail, it is apparent to those skilled in the art that such a specific technology is only a preferred embodiment, and the scope of the present invention is not limited thereto. Therefore, the substantial scope of the present invention will be defined by the appended claims and equivalents thereof.

Claims (6)

A cosmetic composition for preventing skin aging containing a flavonoid compound represented by Formula 1 as an active ingredient. [Formula 1]

In the formula, R ₁ , R ₂ and R ₃ are each independently a hydroxy group, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms. Cosmetic composition for improving skin wrinkles containing a flavonoid compound represented by the formula (1) as an active ingredient. [Formula 1]

In the formula, R ₁ , R ₂ and R ₃ are each independently a hydroxy group, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms. The flavonoid compound of claim 1, wherein the flavonoid compound of Formula 1 is 2,3-dihydrocysidopitsin, 2,3-dihydroisozingettin, 2 ^// , 3 ^// -dihydro -4 ^/// , 5,5 ^// , 7,7 ^// -pentahydroxy-4 ^/ -methoxy-3 ^/// , 8-biflavone, 2 ^// , 3 ^// -dihydro-4 ^/ , 5,5 ^// , 7,7 ^// -pentahydroxy-4 ^/// -methoxy-3 ^/// , 8-biflavones, 2 ^// , 3 ^// -dihydro-4,4 ^/// , 5,5 ^// , 7-pentahydroxy-7 ^// -methoxy-3 ^/// , 8-biflavones, 2 ^// , 3 ^// -dihydro-4 ^/ , 5,5 ^// , 7-tetrahydroxy-4 ^/// , 7 ^// -dimethoxy-3 ^/// , 8-biflavones, 2 ^// , 3 ^// -dihydro-4 ^/// , 5,5 ^// , 7-tetrahydroxy-4 ^/ , 7 ^// -dimethoxy-3 ^/// , 8-biflavones and 2 ^// , 3 ^// -dihydro-4 ^/ , 4 ^/// , 5, 5 ^// , 7,7 ^// -hexahydroxy-3 ^/// , a cosmetic composition, characterized in that it is selected from the group consisting of 8-biflavones. The cosmetic composition according to claim 1 or 2, wherein the flavonoid compound of Formula 1 is contained in an amount of 0.000001-15.0% by weight based on the total weight of the cosmetic composition.  3. The cosmetic composition according to claim 1 or 2, wherein the cosmetic composition is a solution, suspension, emulsion, paste, gel, cream, lotion, powder, soap, surfactant-containing cleansing, oil, powder foundation, emulsion foundation, wax foundation And a formulation selected from the group consisting of sprays. A cosmetic method according to claim 1 or 2, wherein the cosmetic composition is applied to human skin to exhibit an anti-aging effect on the skin.