KR101874467B1 - Cosmetic composition for improving skin wrinkle or skin moisturing comprising Protaetia brevitarsis extract or compound isolated therefrom as effective component - Google Patents

Abstract

The present invention relates to a composition for improving skin wrinkles or moisturizing skin, containing a Protaetia brevitarsis extract or a compound divided from the Protaetia brevitarsis extract as an effective component. Specifically, the composition is to improve the content of hyaluronic acid capable of improving skin moisture and remarkably suppressing a manifestation of MMP-1 increased by radiation of ultraviolet rays. The composition of chemical formulas 1-5 and the Protaetia brevitarsis extract rarely have cytotoxicity. Therefore, according to the present invention, the composition can be used as a cosmetic composition for improving skin wrinkles, a chemical composition for preventing or curing skin wrinkles, or an anti-aging health functional food composition for improving skin wrinkles.

Description

[0001] The present invention relates to a cosmetic composition for improving skin wrinkles or skin moisturizing, comprising extracts of phytopathogenic fungus or a compound isolated therefrom as an active ingredient,

The present invention relates to a cosmetic composition for improving skin wrinkles or skin moisturizing, comprising as an active ingredient a flower bud extract or a compound isolated therefrom.

Skin is an organ that is always in contact with the outside environment. It protects the body from external physical damage and chemical substances, prevents bacteria, fungi, viruses from invading the skin, and acts as a protection barrier against moisture loss. Skin structure consists of three layers: epidermis, dermis, and subcutaneous fat. The epidermis is the thinnest of the three layers, which plays an important role in moisturizing and protecting the skin. In particular, the skin is elastic and softened by the water present in the stratum corneum of the epidermis, and it is known that the water content of 10% or more is essential for the elasticity of the stratum corneum to be maintained (OK Jacobi, Proc. , 22).

Recently, exposure to strong ultraviolet rays has become more frequent due to environmental pollution, skin aging has accelerated due to increase in moisture loss of the skin, and as the incidence of related diseases caused by skin damage has increased, exposure to ultraviolet There is an increasing demand for a composition that maintains the moisturizing maintenance and wrinkle-reducing effect of the skin for a long time.

On the other hand, the flower is a larva of white spotted flower, the white spotted flower is 17 ~ 22mm in length, and the body has green, brown or red light with strong gloss, and there are variations such as green, indigo, . The hair on the inside of the posterior medulla was grayish brown, the tip of the barycic auricle was bank shaped, and the tip of the scab wing protruded sharply. The abdomen of the male was decapitated in length. The mating hole is thin straight, the inner plate is narrow and long, and there is a part protruding round at the end.

One example of the technique related to the white spotted flowers known so far is the 'in vitro antioxidative physiology related to the white spotted flower free drink' in the Korean Journal of Food Science and Nutrition (J Korean Soc Food Sci Nutr 41 (1), 41-48,2012) Active ingredient and its safety has been disclosed in Korean Patent Publication No. 0414187. However, the present invention is not limited to the use of the extract of the present invention or the compound isolated therefrom as an active ingredient, No cosmetic composition for improving wrinkles or moisturizing skin has been disclosed.

The present invention provides a cosmetic composition for skin wrinkle improvement or skin moisturizing which comprises as an active ingredient at least one compound selected from Formulas 1 to 5, And the amount of hyaluronic acid to prevent skin damaging function and skin barrier damage is reduced by decreasing the expression amount of MMP-1, which is matrix metalloproteinases (MMPs) involved in degradation of extracellular matrix and basement membrane, , Thereby completing the present invention.

In order to achieve the above object, the present invention provides a cosmetic composition for improving skin wrinkles or skin moisturizing, comprising as an active ingredient a flower bud extract or at least one compound selected from the following formulas (1) to (5) isolated therefrom.

The present invention relates to a composition for improving skin wrinkles or skin moisturizing composition containing a flower bud extract or a compound isolated therefrom as an active ingredient. The effective ingredient of the present invention has little cytotoxicity, and is effective for improving skin wrinkles and skin moisturizing . Therefore, the composition of the present invention can be applied to a cosmetic for improving skin wrinkles or skin moisturizing.

FIG. 1 shows the results of analysis of the cell viability (%) according to the treatment of the concentration of the flower bud extract (A) of the present invention and the compound (B) of the formula 1 to 5 isolated therefrom.
FIG. 2 shows the results of analysis of changes in the expression level of MMP-1 protein according to the UV irradiation and treatment of the extract of the present invention (A) and the compound (B) of the formula 1 to 5 separated therefrom. Control is a negative control group that does nothing and UVB is a control group in which the present flower ear extract of the present invention and compounds 1 to 5 isolated therefrom are not treated but irradiated only with ultraviolet rays.
FIG. 3 shows the results of analysis of hyaluronic acid (HA) changes according to UV irradiation and treatment of the concentration of the compound (B) of the present invention (A) and the compound (B) isolated therefrom. Control is a negative control group that does nothing and UVB is a control group in which the present flower ear extract of the present invention and compounds 1 to 5 isolated therefrom are not treated but irradiated only with ultraviolet rays.

The present invention relates to a cosmetic composition for improving skin wrinkles or skin moisturizing, comprising as an active ingredient a flower bud extract or at least one compound selected from the following formulas (1) to (5) isolated therefrom.

The flower bud extract can be prepared by a method including, but not limited to, the following steps:

(1) extracting a dry powder of a flower bud by adding an extraction solvent;

(2) filtering the extract of step (1); And

(3) The step of extracting the filtered extract of step (2) by concentration under reduced pressure and drying.

In step (1), the extraction solvent is preferably selected from water, a C ₁ -C ₄ lower alcohol or a mixture thereof, more preferably ethanol, even more preferably 70% (v / v) ethanol But is not limited thereto.

In the above production method, any conventional method known in the art such as filtration, hot water extraction, immersion extraction, reflux cooling extraction, and ultrasonic extraction may be used. The extraction solvent is preferably added by 1 to 20 times the weight of the dried flower bud, more preferably 5 to 15 times the weight of the dried flower bud. The extraction temperature is preferably 4 to 50 DEG C, but is not limited thereto. The extraction time is preferably 0.5 to 10 hours, more preferably 0.5 to 5 hours, most preferably 1 hour, but not always limited thereto. In the above method, it is preferable to use a vacuum decompression concentrator or a vacuum rotary evaporator for the decompression concentration in the step (3), but it is not limited thereto. The drying is preferably performed under reduced pressure, vacuum drying, boiling, spray drying or freeze drying, but not always limited thereto.

In the present invention, wrinkle formation is caused by reduction of collagen, and reduction of the collagen may be caused by excessive oxidative stress or ultraviolet irradiation.

The above-mentioned flower bud extract or at least one compound selected from the above-mentioned formulas (1) to (5) from which the extract is isolated may reduce the expression amount of MMP-1 protein and increase the content of hyaluronic acid.

The cosmetic composition according to one embodiment of the present invention may be used as an external ointment for skin, a cream, a softening agent, a nutritional lotion, a pack, an essence, a hair tonic, a shampoo, a rinse, a hair conditioner, a hair treatment, a gel, a skin lotion, Toner, Astringent, Lotion, Milk Lotion, Moisture Lotion, Nutrition Lotion, Massage Cream, Nourishing Cream, Moisture Cream, Hand Cream, Foundation, Nutrition Essence, Sunscreen, Soap, Cleansing Foam, Cleansing Lotion, Cleansing Cream, Body Lotion and Body And a cleanser. However, the present invention is not limited thereto. The cosmetic composition comprising each of these formulations may contain various bases and additives necessary for formulation of the formulation, and the kinds and amounts of these ingredients can be easily selected by those skilled in the art.

When the formulation of the cosmetic composition of the present invention is a paste, a cream or a gel, an animal fiber, a plant fiber, a wax, a paraffin, a starch, a tragacanth, a cellulose derivative, a polyethylene glycol, a silicone, a bentonite, Etc. may be used.

When the formulation of the cosmetic composition 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, Propellants such as hydrocarbons, propane-butanes or dimethyl ethers.

When the formulation of the cosmetic composition of the present invention is a solution or an emulsion, a solvent, a solvent or an emulsifier is used as a carrier component, and examples thereof include water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, Glycol, 1,3-butyl glycol oil, glycerol aliphatic ester, polyethylene glycol or fatty acid esters of sorbitan.

When the formulation of the cosmetic composition of the present invention is a suspension, a carrier such as water, a liquid diluent such as ethanol or propylene glycol, a suspension such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester, Microcrystalline cellulose, aluminum metahydroxide, bentonite, agar or tracant, etc. may be used.

When the formulation of the cosmetic composition of the present invention is a cleansing agent containing an interfacial active agent, the carrier component may include aliphatic alcohol sulfate, aliphatic alcohol ether sulfate, sulfosuccinic acid monoester, acethionate, imidazolinium derivative, methyltaurate, sarcosinate , Fatty acid amide ether sulfate, alkylamidobetaine, aliphatic alcohol, fatty acid glyceride, fatty acid diethanolamide, vegetable oil, linolenic derivative or ethoxylated glycerol fatty acid ester.

The cosmetic composition of the present invention may further contain an excipient including a fluorescent substance, a fungicide, a hygroscopic substance, a moisturizer, a fragrance, a fragrance carrier, a protein, a solubilizer, a sugar derivative, a sunscreen, a vitamin, .

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 merely illustrative of the present invention and that the scope of the present invention is not limited thereto.

Example  One. Flower bud  Preparation of Extracts and Isolation of Five Compounds

The ethanol extract (5 L × 4) was extracted with ethanol containing 1% (v / v) acetic acid (5.17 kg) of a flower bud (white spotted flower larva), and the ethanol extract was distilled under reduced pressure to obtain brown ethanol 968.0 g of the extract was obtained.

The obtained ethanol extracts were suspended in water and sequentially fractionated with n -hexane, ethyl acetate and butanol. The n -hexane fraction (400 g, PBS-1), the ethyl acetate fraction (10.0 g, PBS-2) and the butanol fraction (47.3 g, PBS-3) and water residue fraction (510.0 g, PBS-4). The ethyl acetate fraction (PBS-2) was eluted with hexane / ethyl acetate 5: 1, 4: 1, 2: 1 and 1: 1 (v: v); Hexane / ethyl acetate / methanol 1/1 / 0.2 (v: v: v); Chloroform / methanol 7: 1 (v: v); Seven small fractions (PBS-2a to PBS-2g) were obtained by vacuum liquid chromatography (VLC) under chloroform / methanol 5: 1 (v: v) gradient elution and methanol washing conditions. The small fraction, PBS-2d (2 g), was purified by HPLC (hexane / ethyl acetate / methanol 1: 1: 0.2 (v: v)) using a Kinetex Biphenyl column under the condition of gradient of aqueous methanol solution of 30 to 70% (v / v) v) elution conditions) cyclo (L-Val-L -Pro) through _{(t R, 23min, 21 mg} ) ( compound of formula (4)) and _{N-acetyltyramine (t R, 28min} , 115mg) (compound of formula (5) ).

The butanol fraction (47.8 g, PBS-3) was eluted with VLC having elution conditions of 9: 1, 7: 1, 6: 1, 4: 1, 2: 1 (v: v) chloroform / methanol (v: And fractionated into six small fractions (PBS-3a to PBS-3-f). From the PBS-3f fraction (20 g), three small fractions were obtained by MPLC using a methanol aqueous solution elution condition having a concentration gradient of 20 to 50% (v / v) (PBS-3f-a to PBS -3f-c).

(1 R, 3 S) -1 -methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (t R, 58min, 15mg) ( compounds of formula (1));

(1 S, 3 S) -1 -methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (t R, 57min, 20mg) ( compound of formula (2));

(3 S) -1,2,3,4-tetrahydro- β-carboline-3-carboxylic acid (t R, 53min, 25mg) is 10 ~ 40% (v / v ) Kinetex Biphenyl having a concentration gradient of aqueous methanol solution The column was separated from the PBS-3f-b (2 g) fraction by HPLC. methyl 9 H -pyrido [3,4-β ] indole-1-carboxylate (t R, 45min, 10mg) in a condition having a concentration gradient of aqueous methanol solution (the compound of formula 3) is 50 ~ 70% (v / v ) Were separated from the PBS-3a (100 g) fraction by HPLC using a Kinetex Biphenyl column.

Example 2. Cell survival analysis according to the treatment of the compounds of the formulas 1 to 5 isolated from the flower bud extract or the extract

HaCaT cells (human keratinocyte cell line) is 37 ℃, the CO ₂ conditions of 5%, 10% of FBS (Fetal bovine serum) and 1% penicillin-streptomycin (PS, Gibco) Dulbecco (this contained DMEM's Modified Eagle Medium).

Each sample was diluted by concentration for 24 hours in the cultured HaCaT cells (human keratinocyte line), and the cells were treated with MTS assay (CellTiter Aqueous One Solution Cell proliferation assay kit 3- (4,5-dimethylthiazol-2-yl) Cell viability was measured at 490 nm using a microplate reader (Molecular Devices, Sunnyvale, Calif.) At 490 nm by the method of MTS, Promega Co., Madison, Wis., USA) , CA, USA).

As a result, as shown in Fig. 1, even when the flower bud extract of the present invention and the compounds of the general formulas 1 to 5 isolated therefrom were treated, the cell survival rate (%) showed almost no change on the basis of the control group It was confirmed that there was almost no toxicity.

Example  3. MMP -1 and hyaluronic acid ( Hyaluronic  Acid; HA)

Each sample was treated with HaCaT cells (human keratinocyte line) for 24 hours, irradiated with ultraviolet light (UV Crosslinker, Ultra Lum) at 20 mJ / cm ² for 30 minutes, and then the supernatant of the culture was collected and the MMP-1 ELISA kit (R & D Systems, Inc., Minneapolis, MN, USA), and the content of HA was measured using a Hyaluronic acid ELISA kit (R & D Systems, Respectively. The reactants were subjected to an absorbance assay.

As a result, as shown in FIG. 2 and FIG. 3, the amount of MMP-1 expression increased sharply and the content of hyaluronic acid decreased by ultraviolet irradiation. However, when irradiated with ultraviolet rays, 5, the expression level of MMP-1 was remarkably decreased (FIG. 2) in a concentration-dependent manner, and it was confirmed that the amount of MMP-1 was increased compared with the content of hyaluronic acid in the ultraviolet irradiation group (FIG. 3) .

Claims (5)

A cosmetic composition for improving skin wrinkles or skin moisturizing, comprising as an active ingredient at least one compound selected from the following Formulas (1) to (5), wherein the extract is:
[Chemical Formula 1]

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

The cosmetic composition for improving skin wrinkles or skin moisturizing according to claim 1, wherein the solvent of the flower extract is water, a C ₁ -C ₄ lower alcohol or a mixture thereof. The cosmetic composition for improving skin wrinkles or skin moisturizing according to claim 1, wherein the flower bud extract or at least one compound selected from the above-mentioned formulas (1) to (5) isolated therefrom reduces the expression amount of MMP-1 protein. The cosmetic composition for improving skin wrinkles or skin moisturizing according to claim 1, wherein the flower bud extract or at least one compound selected from the above-mentioned formulas (1) to (5) from which the extract is isolated increases the content of hyaluronic acid. The cosmetic composition according to claim 1, wherein the cosmetic composition is at least one selected from the group consisting of an ointment for external use, a cream, a softening agent, a nutritional lotion, a pack, an essence, a hair tonic, a shampoo, a rinse, a hair conditioner, a hair treatment, a gel, a skin lotion, Lotion, milk lotion, moisturizing lotion, nutrition lotion, massage cream, nutritional cream, moisturizing cream, hand cream, foundation, nutrition essence, sunscreen, soap, cleansing foam, cleansing lotion, cleansing cream, body lotion and body cleanser Wherein the composition is at least one selected from the group consisting of a composition for improving skin wrinkles and a composition for skin moisturizing.

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