KR20180099563A - Cosmetic composition for improving skin wrinkle comprising Oxya chinensis sinuosa extract or compound isolated from the extract as effective component - Google Patents

Abstract

The present invention relates to a cosmetic composition for preventing or reducing skin wrinkles comprising an Oxya chinensis sinuosa extract containing: a compound of chemical formula 1 or acceptable salt thereof; a compound of chemical formula 2 or acceptable salt thereof; a compound of chemical formula 3 or acceptable salt thereof; or at least one compound selected from compounds of chemical formula 1 to 3, as effective components, wherein the cosmetic composition inhibits cell damage due to ultraviolet irradiation, and remarkably inhibits the expression of MMP-1, thereby being used as cosmetics for reducing the skin wrinkles.

Description

[0001] The present invention relates to a cosmetic composition for improving skin wrinkles, which comprises an extract of a rice plant or a compound isolated therefrom as an active ingredient.

The present invention relates to a rice plant chinensis The present invention relates to a cosmetic composition for improving skin wrinkles containing an extract or a compound isolated therefrom as an active ingredient.

Skin protects the organs in the body from external stimuli and plays an important role in the maintenance of body homeostasis, such as body temperature control. Such skin is aged by various internal and external factors and is divided into endogenous aging by genetic cause and exogenous aging by environmental cause. Among them, photoaging refers to aging by ultraviolet (UV). Recently, the destruction of the ozone layer due to environmental pollution has increased the amount of ultraviolet rays, and accordingly, research on photoaging has been attracting attention (Wang SQ et al., 2010, Dermatol. Ther. 23 (1): 31-47). In the photoaged skin, appearance characteristics such as roughness, loss of elasticity, wrinkles and irregular pigmentation are observed. Among them, the main research field of photoaging is the change of the skin wrinkles. There have been many reports on the basic physiological metabolism changes such as synthesis, degradation, and moisture content of collagen, which is a major constituent of skin, in the formation of skin wrinkles by photoaging (Brenneisen et al., 2002, Ann. NY Acad. Sci., 973: 31-43). Particularly, ultraviolet rays increase the production of reactive oxygen species, collapse of enzymatic and non-enzymatic antioxidant defenses of skin, decrease collagen decomposition and biosynthesis, and decrease collagen in the dermis (Bickers DR , Athar M, 2006, J. Invest. Dermatol., 126 (12): 2565-2575). Important collagen degradation factors are matrix metalloproteinases (MMPs), which are involved in the degradation of extracellular matrix and basement membrane. Studies have been reported that the enzyme increases activity by ultraviolet rays and inhibits it, thereby increasing skin thickness and wrinkling induced by ultraviolet light (Inomata S et al., 2003, J. Invest. Dermatol., 120 (1): 128-134). Therefore, it is known that effective control of MMPs is required for prevention and treatment of photoaging.

On the other hand, the grasshopper is 30 ~ 38cm in length, body color is yellow-green, and head and chest are yellowish brown. The compound eyes are egg-shaped and lustrous grayish brown. There are three thin lateral grooves on the pronotum, with brown vertical stripes on both sides. The wing is yellowish brown and longer than the tip of the wing but does not fly much. Inhabits grassy areas near rice fields and cultivated areas. It occurs once a year, and it drifts with a bunch of ground in the ground. The alum is wrapped in a thin film of collagen. The larvae grow up to the fourth ventral wing and the body length is about 30mm. The use of pesticides as a major pest of rice has decreased, but it is gradually increasing. In 1930, it originated in Hwanghae Province and bought eggs from the government. It is distributed in Korea, Japan, and China.

Korean Patent No. 1648812 discloses a method for producing a diet food composition containing a rice-grasshopper ingredient, Korean Patent Publication No. 2010-0002661 discloses a functional complex containing hyaluronic acid and a method for producing the same, There has been no description of a cosmetic composition for improving skin wrinkles containing the rice grasshopper extract of the invention or a compound isolated therefrom as an active ingredient.

SUMMARY OF THE INVENTION The present invention has been achieved by the above-mentioned needs, and the present invention provides a compound of the formula 1 or an acceptable salt thereof; A compound of formula 2 or an acceptable salt thereof; A compound of formula (III) or an acceptable salt thereof; Or byeomettugi (Oxya comprising at least one compound selected from compounds of formula 1-3 chinensis The present invention relates to a cosmetic composition for improving the skin wrinkles containing an extract of the present invention as an active ingredient. The compounds of the general formulas (1) to (3) and the rice grasshopper extract have no cytotoxicity and remarkably reduce the expression amount of MMP- Thereby completing the present invention.

In order to accomplish the above object, the present invention provides a compound of formula 1 or an acceptable salt thereof; A compound of formula 2 or an acceptable salt thereof; A compound of formula (III) or an acceptable salt thereof; Or byeomettugi (Oxya comprising at least one compound selected from compounds of formula 1-3 chinensis The present invention provides a cosmetic composition for preventing or ameliorating skin wrinkles containing an extract of Aspergillus sinuosa as an active ingredient.

The present invention relates to a compound of formula (I) or an acceptable salt thereof; A compound of formula 2 or an acceptable salt thereof; A compound of formula (III) or an acceptable salt thereof; The present invention relates to a cosmetic composition for preventing or improving skin wrinkles containing, as an active ingredient, an extract of a rice plant ( Oxya chinensis sinuosa ) comprising at least one compound selected from the group consisting of compounds of the following formulas (1) to (3) Since the effect of suppressing the expression of MMP-1 is remarkable, it can be usefully used in cosmetics for improving skin wrinkles.

FIG. 1 shows the results of confirming cell viability (%) after treatment of rice plant extracts of the present invention by concentration.
2 shows the results of confirming the cell viability (%) after treating the compounds derived from the rice-grasshopper extract of the present invention (Compound A (Formula 1), Compound B (Formula 2) and Compound C (Formula 3)) by concentration.
FIG. 3 shows the results of confirming changes in the expression level of MMP-1 after treatment of the rice-grasshopper extract of the present invention at various concentrations.
4 is a result of examining changes in the expression level of MMP-1 after treatment of the compounds (Compound A (Formula 1), Compound B (Formula 2) and Compound C (Formula 3)) derived from the rice grasshopper extract of the present invention by concentration .

The present invention relates to compounds of the general formula (I) or acceptable salts thereof; Claims 1. A compound of formula (2) or an acceptable salt thereof; Claims 1. A compound of formula (3): The present invention also relates to a cosmetic composition for preventing or improving skin wrinkles containing, as an active ingredient, an extract of a rice plant ( Oxya chinensis sinuosa ) comprising at least one compound selected from the group consisting of compounds represented by formulas (1) to (3)

The compounds of the above formulas (1) to (3) are characterized in that they are extracted from rice hermit, but the present invention is not limited thereto, and it is possible to extract or synthesize from other natural products.

The rice grasshopper extract may be produced by a method including, but not limited to, the following steps:

(1) extracting the rice seedlings with 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 rice hogger, more preferably 5 to 15 times. 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.

The cosmetic composition is characterized by inhibiting the expression of MMP-1.

In the cosmetic composition according to one embodiment of the present invention, the cosmetic composition for improving skin wrinkles may be at least one selected from the group consisting of ointment for external use, cream, softening longevity, nutrition lotion, pack, essence, hair tonic, shampoo, rinse, hair conditioner, Lotion, milk lotion, moisturizing lotion, nutrition lotion, massage cream, nutritional cream, moisturizing cream, hand cream, foundation, nutrition essence, sunscreen, soap, cleansing foam, skin lotion, skin softener, skin toner, astringent, But are not limited to, any one form selected from the group consisting of cleansing lotion, cleansing cream, body lotion and body cleanser. 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. Especially, in the case of a spray, Propellants such as carbon, propane-butane or dimethyl ether.

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.

[ Materials and Methods]

1. Manufacture of rice-grasshopper extract

The rice seedlings (4.87 kg) were extracted with ethanol containing 1% (v / v) acetic acid and then distilled under reduced pressure to obtain 421.8 g of a brown rice seed extract ethanol extract.

2. Isolation and Structure Determination of Compounds of Formulas 1 to 3

Ethanol extract (421.8 g) was purified by vacuum liquid chromatography (VLC) using hexane / ethyl acetate (6 L), 80:20 (6 L), 60:40 (6 L), 40:60 ) And 20: 80 (6 L) (v: v); The concentration gradient of chloroform / methanol 100: 0 (6 L), 80:20 (6 L), 60:40 (6 L), 40:60 (6 L) and 20:80 (6 L) Six small fractions were obtained (A to F) through elution and methanol washing conditions.

D fraction (35.7 g) was purified by VLC (vacuum liquid chromatography) using hexane / ethyl acetate 100: 0 (6 L), 85:15 (6 L), 75:25 (6 L) and 50:50 (6 L) v); The concentration gradient elution conditions and the methanol washing conditions of chloroform / methanol 85:15 (6 L), 80:20 (6 L), 67:33 (6 L) and 50:50 (6 L) (D-1 to D-7).

D-5 fraction (18.3 g) was purified by gradient elution of acetonitrile / water (10:90 to 60:40, 8160 ml) using MPLC (medium pressure liquid chromatography) and acetonitrile (D-5-1 to D-5-6).

With respect to D-5-2 fraction (1.9g) prep HPLC (Phenomenex Kinetex C 18 250 × 21 mm, 5μm, Kinetex Biphenyl 250 × 21mm, 5μm) proceeds to the compound A _(R t bun 52: 331.2mg), compound B (t _R, 47 bun: 389.2mg), compound C (t _R 64 bun: 37.2mg) was obtained.

3. Cell culture

HaCaT cells were cultured in Dulbecco's Modified Eagle Medium (DMEM, Gibco) supplemented with 10% fetal bovine serum (FBS, Gibco) and 1% penicillin-streptomycin And cultured in medium containing penicillin-streptomycin (PS, Gibco) at 37 ° C and 5% CO ₂ .

Example  One. Cell survival rate  analysis

The HaCaT cells were cultured for 24 hours in a concentration-dependent manner, 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 by a microplate reader (Molecular Devices, Sunnyvale, Calif., USA) at 490 nm by the method of MTS, Promega Co. Madison, WI, ).

As a result, the cell survival rate in the UVB irradiated group was lower than that in the control group treated with nothing, and the relative cell survival rate (%) after treatment with the samples of the present invention (the rice grasshopper extract and the compounds of Formulas 1 to 3) ) Were slightly increased or remained in Fig. 1 and Fig. 2, respectively. Therefore, it was found that the rice plant extract of the present invention and the compounds of the formulas (1) to (3) had little cytotoxicity.

Example  2. MMP -1 expression level

Each sample was treated with HaCaT cells for 24 hours and irradiated with ultraviolet light (UV Crosslinker, Ultra Lum) at 20 mJ / cm ^{2. Then} , using an MMP-1 ELISA kit (R & D Systems, Inc., Minneapolis, The expression level of MMP-1 was measured.

Specifically, HaCaT cells were plated on a 96-well plate, and then the rice-grasshopper extract of the present invention and the compounds of Formulas 1 to 3 were treated at respective concentrations. Then, ultraviolet (UV) irradiation was performed, and the supernatant of the culture was collected and centrifuged at 13,000 rpm for 5 minutes. The supernatant was then subjected to fluorescent assay using an ELISA kit to quantitatively analyze the expression level of MMP-1.

As a result, it was confirmed that the expression level of MMP-1 remarkably increased in the group irradiated with ultraviolet light as compared with the negative control group not irradiated with ultraviolet light as disclosed in Figs. 3 and 4, and the sample of the present invention 1 to 3) of MMP-1 was remarkably decreased compared with that of ultraviolet irradiation group.

Claims (4)

Claims 1. Compounds of the general formula (I) or acceptable salts thereof; Claims 1. A compound of formula (2) or an acceptable salt thereof; Claims 1. A compound of formula (3): Or one or more compounds selected from the group consisting of compounds represented by the following formulas (1) to (3): Oxya chinensis The present invention relates to a cosmetic composition for preventing or ameliorating skin wrinkles containing an extract of Aspergillus sinuosa as an active ingredient.
[Chemical Formula 1]

(2)

(3)

2. The cosmetic composition according to claim 1, wherein the rice plant extract is extracted using at least one solvent selected from the group consisting of water, C ₁ -C ₄ lower alcohols and mixtures thereof. The cosmetic composition according to claim 1, wherein the cosmetic composition inhibits the expression of MMP-1. 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 . The cosmetic composition for prevention or improvement of wrinkles of skin.

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