CN111093607A - Cosmetic composition for protecting skin against active oxygen species, ultraviolet rays or fine dusts comprising red gallol - Google Patents
Cosmetic composition for protecting skin against active oxygen species, ultraviolet rays or fine dusts comprising red gallol Download PDFInfo
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- CN111093607A CN111093607A CN201880057443.0A CN201880057443A CN111093607A CN 111093607 A CN111093607 A CN 111093607A CN 201880057443 A CN201880057443 A CN 201880057443A CN 111093607 A CN111093607 A CN 111093607A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/345—Alcohols containing more than one hydroxy group
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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Abstract
The present invention relates to a cosmetic composition for protecting skin against reactive oxygen species, ultraviolet rays or fine dusts, comprising red gallol (purpurogenin) or a cosmetically acceptable salt thereof as an active ingredient, which is useful as a cosmetic composition for protecting skin against reactive oxygen species, ultraviolet rays or fine dusts.
Description
Technical Field
The present invention relates to a skin-protecting cosmetic composition quasi-drug composition and a skin external preparation composition containing red gallol (purpurogenin) or a cosmetically acceptable salt thereof as an active ingredient against active oxygen clusters, ultraviolet rays or fine dusts.
Background
The skin is a body part directly exposed to the external environment, and not only functions as a protective film for protecting vital organs of our body, but also protects the body from external infection by regulating moisture evaporation. However, even if the skin prevents penetration of viruses from the outside, external stress from excessive ultraviolet rays, polluted environments, and the like causes skin irritation, and eventually, skin aging.
Ultraviolet B (UVB radiation) with a wavelength of 280-320 nm is one of the major environmental factors that have a harmful effect on the skin, such as skin cancer (skin), immune system suppression and photo-aging. Reactive Oxygen Species (ROS) caused by such ultraviolet B cause oxidative damage (oxidative damage) to cell components such as lipids (lipids), proteins (proteins), and deoxyribonucleic acid (DNA), thereby promoting skin aging and causing various skin disorders.
The reactive oxygen species are oxygen in an unstable state, and generate excessive oxygen due to environmental pollution and chemicals, ultraviolet rays, blood circulation disorder, stress, and the like. Such excessive generation of active oxygen causes oxidation in the human body, damages cell membranes, deoxyribonucleic acid, all cell structures except for them, and loses cell functions or suffers deterioration according to the extent of damage. Also, reactive oxygen species in skin cells cause oxidative stress and promote skin aging.
Many antioxidant substances have been proposed to protect the skin from cell damage caused by reactive oxygen species, for example, (-) -epigallocatechin-3-gallate and resveratrol (resveratrol) and the like are known to inhibit skin damage caused by ultraviolet B. Various types of marine algae (marine algae) or seaweeds (seaweed) containing compounds such as carotenoids (carotenoids), phenolic compounds (phenols), and antioxidant vitamins (antioxidants) are known to relieve oxidative stress (oxidative stress) in skin cells by a biological antioxidant system and direct radical scavenging (free radicals).
On the other hand, in recent years, fine dust, sand dust, and haze mixed with harmful substances such as heavy metals due to industrialization of china are considered to be main causes of skin aging and skin problems.
The fine dust is a very small substance invisible to the human eye, and is a substance in the form of particles having a diameter of 10 μm or less that float in the atmosphere or fly down for a long time. When fossil fuels such as coal and petroleum are burned, or when exhaust gas such as soot from manufacturing industry and automobiles is exhausted, air pollutants that are adsorbed to the lungs through the bronchi and cause various lung diseases are generated. According to the difference in terms of fine dust used in korea and internationally, which was pointed out by the ministry of environment in 2017 in 3 months, fine dust (PM10) having a diameter of 10 μm or less was defined as fly dust, and fine particulate matter (PM2.5) having a diameter of 2.5 μm or less was defined as fine dust.
Pollutants such as dust and sand cause stress in the skin, which is caused by active oxygen. The reactive oxygen species act as intracellular signaling substances that play an important role in maintaining normal cellular functions, such as the activation of electron transporters and leukocytes within the mitochondria. However, active oxygen is unstable and has a strong oxidizing ability, and easily reacts with biological materials, and if it cannot be eliminated in the human body, it causes oxidative stress (oxidative stress).
Disclosure of Invention
Technical problem
In the present invention, it is attempted to develop a cosmetic composition having a skin-protecting effect against active oxygen clusters, ultraviolet rays or fine dusts.
Means for solving the problems
The present invention aims to provide a cosmetic composition for protecting skin against active oxygen clusters, ultraviolet rays or fine dusts, which contains red gallol or a cosmetically acceptable salt thereof as an active ingredient.
It is still another object of the present invention to provide a quasi-pharmaceutical composition for protecting skin against active oxygen clusters, ultraviolet rays or fine dusts, which comprises red gallol or a physiologically acceptable salt thereof as an active ingredient.
Another object of the present invention is to provide a skin external composition for protecting skin, which contains red gallol or a physiologically acceptable salt thereof as an active ingredient against active oxygen clusters, ultraviolet rays or fine dusts.
It is a further object of the present invention to provide the use of red gallol or its cosmetically acceptable salts for the preparation of a cosmetic composition for the protection of the skin against reactive oxygen species, ultraviolet light or fine dust.
It is a further object of the present invention to provide the use of red gallol or its physiologically acceptable salts for the preparation of a quasi-pharmaceutical composition for the protection of the skin against reactive oxygen species, ultraviolet light or fine dust.
It is still another object of the present invention to provide the use of red gallol or a physiologically acceptable salt thereof for preparing a skin external composition for protecting skin against active oxygen clusters, ultraviolet rays or fine dusts.
It is still another object of the present invention to provide a method for skin protection against reactive oxygen species, ultraviolet rays or fine dusts comprising the step of administering red gallol or a physiologically acceptable salt thereof to a subject.
ADVANTAGEOUS EFFECTS OF INVENTION
The present invention relates to a cosmetic composition for protecting skin against reactive oxygen species, ultraviolet rays or fine dusts, comprising red gallol or a cosmetically acceptable salt thereof as an active ingredient, which is useful as a cosmetic composition for protecting skin against reactive oxygen species, ultraviolet rays or fine dusts.
Drawings
Fig. 1 to 3 show the active oxygen cluster formation inhibitory effect of red gallol (PG). FIG. 1: HaCaT cells were treated with red gallol (0. mu.M, 2.5. mu.M, 5. mu.M, 10. mu.M) for 24 hours and cell viability was determined by 3- (4, 5-dimethylthiazol-2) -2, 5-diphenyltetrazolium bromide salt (MTT) assay. FIG. 2: detection by H assay Using 2', 7' -Dihydrofluorescein diacetate (DCF-DA)2O2The produced red gallic acid (2.5. mu.M, 5. mu.M, 10. mu.M) had an intracellular active oxygen cluster removing ability. Means with H2O2Has significant difference (p) in the control group cells<0.05). FIG. 3: the hydroxyl group removing ability of 10. mu.M of red gallol was predicted by Fenton reaction. Means significant difference from control group; # means a significant difference from the UV group B.
FIGS. 4 to 7 are graphs showing the inhibitory effect of red gallol (10. mu.M) on UV-B-induced cell damage. Confocal microscopy was used for detection of intracellular reactive oxygen species (fig. 4) and lipid peroxidation (fig. 5) after staining with 2', 7' -dihydrofluorescein diacetate (green) and diphenyl-1-pyrenyl phosphine (DPPP) (blue). FIG. 6: deoxyribonucleic acid lesions were analyzed by comet analysis. FIG. 7: protein oxidation was analyzed by measuring the amount of carbonyl formation. Indicates significant difference from control cells (p <0.05) and # indicates significant difference from uv B-irradiated cells (p < 0.05).
FIGS. 8 to 10 are graphs showing the protective effect of UV B-induced apoptosis on red gallol (10. mu.M). FIG. 8: after the irradiation of ultraviolet B, 3- (4, 5-dimethylthiazole-2) -2, 5-diphenyl tetrazole bromide salt analysis is carried out on the activity of HaCaT cells. Means significant difference from control group; # means a significant difference from the UV group B. FIG. 9: after staining the cells with JC-1, the mitochondrial membrane potential (. DELTA.. psi.m) was assessed by flow cell analysis. Means significant difference from control cells (p < 0.05); # means a significant difference from UV B-irradiated cells (p < 0.05). FIG. 10: apoptotic cells stained with Hoechst 33342 were detected using fluorescence microscopy (arrow). Means significant difference from control cells (p < 0.05); # means a significant difference from UV B-irradiated cells (p < 0.05).
FIG. 11 shows the staining of cells with 2', 7' -dihydrofluorescein diacetate (green) and the detection of intracellular reactive oxygen species by Particulate Matter (PM) using confocal microscopy. FIG. 12 shows apoptotic cells stained with Hoechst 33342 detected by fluorescence microscopy (arrow). Means significant difference from control cells (p < 0.05); # means a significant difference from mote cells (p < 0.05).
Fig. 13 shows the fluorescence intensity (green) of DCF formed by reactive oxygen species in the ultraviolet B irradiation group and the fine dust treatment group. FIG. 14 shows apoptotic cells stained with Hoechst 33342 detected by fluorescence microscopy (arrow). Means significant difference from control cells (p < 0.05); # means a significant difference from UV B-irradiated cells (p < 0.05).
Detailed Description
Best mode for carrying out the invention
In one embodiment for achieving the above objects, the present invention provides a cosmetic composition for protecting skin against active oxygen clusters, ultraviolet rays or fine dusts, comprising red gallol or a cosmetically acceptable salt thereof as an active ingredient.
The cosmetic composition of the present invention comprises red gallol or a cosmetically acceptable salt thereof as an active ingredient.
The cosmetic composition comprising said red gallol has a skin protective effect against reactive oxygen species, ultraviolet light or fine dust.
In the present invention, "red gallol" has the following chemical formula.
Chemical formula 1:
in one embodiment of the present invention, it was confirmed that red gallol has no cytotoxicity in an experiment using human keratinocyte cell line (HaCaT), but has hydrogen peroxide (H)2O2) Induced scavenging effect of reactive oxygen species such as reactive oxygen species and hydroxyl radicals in cells, and can be used for scavenging reactive oxygen speciesActive ingredients of cosmetic compositions for protecting skin of clusters.
Also, in the present invention, the reactive oxygen species may be hydrogen peroxide (H)2O2) Or a hydroxyl group (hydroxyl).
In addition, in one embodiment of the present invention, it was confirmed that red gallol has an ultraviolet B-induced intracellular reactive oxygen species scavenging effect, and dna damage, protein damage, and lipid peroxidation increased by ultraviolet B stimulation were significantly reduced.
In addition, it was confirmed that red gallol inhibited apoptosis in HaCaT cells increased by uv B irradiation, reduced apoptotic bodies (apoptotic bodies), and had a protective effect against uv B-induced cells.
Therefore, the red gallol can be used as an effective ingredient of a cosmetic composition for protecting skin against ultraviolet rays.
In the present invention, the ultraviolet ray may be ultraviolet ray B (UV B).
Also, in the present invention, the red gallol may exhibit skin protective activity by scavenging (scavenging) of active oxygen clusters generated by ultraviolet B.
In the present invention, the red gallol exhibits skin protective activity by reducing intracellular lipid peroxidation, deoxyribonucleic acid damage, or protein damage caused by uv B.
In addition, in one embodiment of the present invention, it was confirmed that active oxygen clusters and apoptotic bodies caused by the treatment of fine dust in the red gallol human keratinocyte system were inhibited, and that the skin protective effect against fine dust was exhibited. Therefore, the red gallol can be used as an effective ingredient of a cosmetic composition for protecting skin against fine dusts.
In one embodiment of the present invention, it was confirmed that red gallol inhibits active oxygen clusters and apoptotic bodies induced by ultraviolet B irradiation, mote, or treatment with ultraviolet B and mote in the human keratinocyte system, and has a skin protective effect against mote and ultraviolet. Therefore, the red gallol can be used as an effective ingredient of a cosmetic composition for protecting skin against fine dust or ultraviolet rays.
Also, in the present invention, the red gallol may exhibit skin protective activity by the scavenging action of active oxygen clusters generated from the fine dusts.
Also, in the present invention, the red gallol may exhibit skin protective activity by inhibiting (inhibition) the apoptotic (apoptosis) effect of exposure to ultraviolet B or mote.
The active ingredient of the cosmetic composition of the present invention may be used in the form of the above-mentioned red gallic acid or a cosmetically acceptable salt thereof. As the salt, an acid addition salt formed from a cosmetically acceptable free acid (free acid) is used. Acid addition salts can be prepared by conventional methods, for example, by dissolving the compound in an excess of aqueous acid and precipitating the salt using an aqueous mixed organic solvent such as methanol, ethanol, acetone, or acetonitrile. Equimolar amounts of the compound and aqueous acid or alcohol (e.g., ethylene glycol monomethyl ether) are heated, and the mixture is evaporated and dried, or the precipitated salt is filtered off with suction. In this case, as the free acid, an organic acid and an inorganic acid may be used, and as the inorganic acid, hydrochloric acid, phosphoric acid, sulfuric acid, nitric acid, tartaric acid, and the like may be used, and as the organic acid, methanesulfonic acid, p-toluenesulfonic acid, acetic acid, trifluoroacetic acid, maleic acid (maleic acid), succinic acid, oxalic acid, benzoic acid, tartaric acid, fumaric acid (fumaric acid), mandelic acid, propionic acid (propionic acid), citric acid (citric acid), lactic acid (lactic acid), glycolic acid (glycolic acid), gluconic acid (gluconic acid), galacturonic acid, glutamic acid, glutaric acid (glutaric acid), glucuronic acid (glucoronic acid), aspartic acid, ascorbic acid, carbonic acid, vanillic acid, hydroiodic acid, and the like may be used, but not limited thereto.
Also, a cosmetically acceptable metal salt can be prepared by using the basic group. For example, the alkali metal or alkaline earth metal salt is obtained by dissolving the compound in an excess alkali metal hydroxide or alkaline earth metal hydroxide solution, filtering the undissolved compound salt, evaporating the filtrate, and drying. And, a silver salt corresponding thereto can be obtained by reacting an alkali metal or alkaline earth metal salt with an appropriate silver salt (e.g., silver nitrate).
The cosmetic composition for protecting skin comprising the active oxygen cluster, uv light or fine dust of the present invention may comprise 0.001 to 100 weight percent of red gallol or its cosmetically acceptable salt, specifically may comprise 0.01 to 50 weight percent of red gallol or its cosmetically acceptable salt, with respect to the total weight composition, but is not limited thereto.
Also, the cosmetic composition of the present invention may contain, in addition to the effective ingredients, generally accepted ingredients without limitation, for example, conventional adjuvants and carriers such as antioxidants, stabilizers, solubilizers, vitamins, pigments and perfumes.
The cosmetic composition according to the present invention may be prepared in one or more dosage forms selected from the group consisting of a solution, a topical ointment, a skin cream, a face lotion, a nutritional lotion, a skin softening lotion, a pack, a skin softening lotion, an emulsion, a foundation cream, a essence, a soap, a liquid cleansing liquid, a bathing agent, a sunscreen cream, a sunscreen oil, a suspension, an emulsion, an ointment, a gel, a skin care liquid, a pressed powder, a soap, a surfactant-containing face cleansing cream, an oil, a loose powder, an emulsion foundation, a wax foundation, a patch, and a spray, but is not limited thereto.
The cosmetic composition of the present invention may further comprise one or more cosmetically acceptable carriers for formulating general skin cosmetics, as conventional ingredients, for example, but not limited thereto, oil, water, surfactants, moisturizers, lower alcohols, thickeners, chelating agents, colorants, preservatives, perfumes, and the like may be appropriately formulated. The cosmetically acceptable carrier contained in the cosmetic composition of the present invention varies depending on the dosage form.
In the case where the formulation of the present invention is an ointment, a cream, a skin cream or a gel, animal oil, vegetable oil, wax, paraffin, starch, amine yellow gum, cellulose derivative, polyethylene glycol, silicon, bentonite, silicon dioxide, talc, zinc oxide or a mixture thereof may be used as a carrier component.
In the case where the dosage form of the present invention is a compact or a spray, lactose, talc, silica, aluminum hydroxide, calcium silicate, polyamide powder or a mixture thereof may be used as a carrier ingredient, and particularly, in the case of a spray, a propellant such as chlorofluorocarbon, propane/butane or dimethyl ether may be further contained.
In the case where the dosage form of the present invention is a solution or emulsion, a solvent, a dissolving agent or a suspending agent may be used as a carrier component, and for example, water, ethanol, isopropyl alcohol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 11, 3-butylene glycol oil, and in particular, cottonseed oil, peanut oil, corn oil, olive oil, castor oil, and sesame oil, glycerol fatty acid ester, polyethylene glycol or fatty acid ester of sorbitan may be used.
In the case where the dosage form of the present invention is a suspension, a liquid phase diluent such as water, ethanol or propylene glycol; suspending agents such as ethoxylated isostearyl alcohols, polyoxyethylene sorbitol esters and polyoxyethylene sorbitan esters; microcrystalline cellulose, aluminum metahydroxide, bentonite, agar, or traganth, and the like.
In the case where the formulation of the present invention is a soap, as carrier components, alkali metal salts of fatty acids, fatty acid half ester salts, fatty acid protein hydrolysates, isethionate, lanolin derivatives, fatty alcohols, vegetable oils, glycerin, and sugars.
In the case where the formulation of the present invention is a surfactant-containing face cleanser, fatty alcohol sulfate, fatty alcohol ether sulfate, sulfosuccinic acid monoester, isethionate, imidazoline derivative, methyl taurate, sarcosinate, fatty acid amide ether sulfate, alkylamidobetaine, fatty alcohol, fatty acid glyceride, fatty acid diethanolamide, vegetable oil, lanolin derivative, ethoxylated glycerin fatty acid ester, or the like can be used as the carrier component.
As still another embodiment, the present invention provides a quasi-pharmaceutical composition for protecting skin against active oxygen clusters, ultraviolet rays or fine dusts comprising red gallol or a physiologically acceptable salt thereof as an active ingredient.
Skin protection against the red gallic phenol, reactive oxygen species, ultraviolet light or fine dust is as described above.
The term "physiologically acceptable" in the present invention means that the physiologically acceptable in general use does not cause allergic reactions such as gastrointestinal diseases, dizziness or the like or expect similar reactions when administered to an organism, and the administered compound can exert desired effects.
The term "quasi-drug" used in the present invention means an article having inferior effect to a drug in the articles for diagnosis, treatment, improvement, alleviation, treatment or prevention of diseases of human or animals, for example, according to korean "pharmacography", the quasi-drug excludes articles used as medicines, and may include fiber or rubber products for treating or preventing diseases of human or animals, bactericides or insecticides having little or no direct effect on the human body, similar to those of non-machines or machines, for preventing infectious diseases.
The quasi-pharmaceutical composition of the present invention is not particularly limited in kind or formulation, and preferably may be a disinfectant cleanser, a shower foam, a mouth wash, a wet wipe, a detergent soap, a hand sanitizer, a humidifier filler, a mask, an ointment, a filter filler, or the like.
In the case where the composition of the present invention is contained for the purpose of skin protection against reactive oxygen species, ultraviolet rays or fine dusts, the composition may be contained directly or used together with other quasi-pharmaceutical ingredients, and may be suitably used according to conventional methods. The mixing amount of the active ingredient may be suitably determined depending on the purpose of use, and the quasi-pharmaceutical composition according to the present invention may contain 0.01 to 20 weight percent of the above-mentioned red gallol or its physiologically acceptable salt, relative to the total weight of the composition.
As another embodiment, the present invention provides a skin external composition for protecting skin against active oxygen clusters, ultraviolet rays or fine dusts comprising red gallol or a physiologically acceptable salt thereof as an active ingredient.
The physiologically acceptable salts for skin protection against the red gallic phenol, active oxygen species, ultraviolet light or dust are as described above.
For example, the composition for external preparation for skin according to the present invention may be exemplified by ointment, lotion, soluble phase, suspension, emulsion, cream, gel, spray, cataplasm, coagulant, patch, or liquid medicine, but is not limited thereto, and may be formulated into any base known in the art. The composition for external use on skin according to the present invention comprises 0.01 to 20 weight percent of the red gallol or its physiologically acceptable salt, relative to the total weight of the composition.
As a further embodiment, the present invention provides the use of red gallol or a cosmetically acceptable salt thereof for the preparation of a cosmetic composition for the protection of the skin against reactive oxygen species, ultraviolet light or fine dust.
As a further embodiment, the present invention provides the use of red gallol or a physiologically acceptable salt thereof for the preparation of a quasi-pharmaceutical composition for the protection of the skin against reactive oxygen species, ultraviolet light or micro-dust.
As still another embodiment, the present invention provides the use of red gallol or a physiologically acceptable salt thereof for the preparation of a skin external composition for protecting skin against active oxygen clusters, ultraviolet rays or fine dusts.
In the present invention, the terms "red gallic phenol", "physiologically acceptable salt", "cosmetically acceptable salt", "active oxygen cluster", "ultraviolet ray", "fine dust", "cosmetic composition", "quasi-drug composition", "skin external composition", "skin protection" are explained as described above.
As yet another embodiment, the present invention provides a method for skin protection against reactive oxygen species, ultraviolet light or fine dust comprising the step of administering red gallol or a physiologically acceptable salt thereof to a subject.
In the present invention, the terms "red gallic phenol", "physiologically acceptable salt", "active oxygen cluster", "ultraviolet ray", "fine dust", "skin protection" are explained as mentioned above.
The individual to which the composition of the present invention is administered includes mammals including humans without limitation, and may be, for example, cows, pigs, horses, rabbits, mice, and humans.
The skin protection method using red gallol or a physiologically acceptable salt of the present invention can administer red gallol or a physiologically acceptable salt to a subject or the skin of a subject. In the present invention, the term "administration" means that red gallol or a physiologically acceptable salt is introduced by some appropriate method, and the administration route of the compound and salt of the present invention is not particularly limited, but administration can be carried out by various routes to achieve desired skin tissues.
Detailed description of the invention
Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings so that those skilled in the art to which the present invention pertains can easily carry out the embodiments. The present invention may, however, be embodied in many different forms and should not be construed as being limited to the embodiments set forth herein.
A. Materials and methods
Example 1 reagent
Red gallol, N-acetylcysteine (NAC), 1-diphenyl-2-picrylhydrazine (DPPH), 2', 7' -dihydrofluorescein diacetate (DCF-DA), 3- (4, 5-dimethylthiazol-2) -2, 5-diphenyltetrazolium bromide, Hoechst 33342, and 5, 5-dimethyl-1-pyrroline-N-oxide (DMPO) were purchased from sigma aldrich (st. louis, MO, USA). Diphenyl-1-pyrenylphosphine (DPPP) was purchased from Molecular Probes, Inc. (Eugene, OR, USA, Oregon, USA). All chemicals and reagents were of analytical grade.
Example 2 cell culture and ultraviolet B irradiation (UVB irradation)
Human keratinocyte cell line (HaCaT) was purchased from Amore pacific company (Yongin, Republic of Korea) and maintained at a temperature of 37 ℃ in a medium containing 5% carbon dioxide. The cell lines were grown in DMEM medium containing 10% bovine serum, streptomycin (100. mu.g/ml) and penicillin (100units/ml) heated at 56 ℃ for 30 minutes. As a source (source) of ultraviolet B having an ultraviolet B spectrum of 280nm to 320nm, a ultraviolet crosslinking agent (UVP, Calif., U.S.A.) of CL-1000M was usedEpaland (Upland, CA, USA)), in the present invention, the dose of ultraviolet B irradiation is 30mJ/cm2。
Example 3 Cell viability
At 0.8X 105Cells were seeded in 24-well plates at a density of cells/ml. After the cells were fully attached to the bottom of the plate, 2.5. mu.M, 5. mu.M and 10. mu.M of red gallol was added. To each well was added 3- (4, 5-dimethylthiazole-2) -2, 5-diphenyltetrazolium bromide stock solution (stock solution) (50. mu.l, 2mg/ml) and the total reaction volume was adjusted to 500. mu.l and incubated for 4 hours. Furthermore, the cells were treated with 1mM N-acetylcysteine or 20. mu.M red gallol and irradiated after 1 hour at 30mJ/cm2Ultraviolet rays B of (1). After culturing at 37 ℃ for 24 hours, 10. mu.l of 3- (4, 5-dimethylthiazole-2) -2, 5-diphenyltetrazolium bromide stock solution (2mg/ml) was added to each well and the total volume was adjusted to 500. mu.l, and the cells were cultured for 4 hours. Subsequently, the supernatant was withdrawn (asparated). The formazan crystals of each well were dissolved in 500. mu.l of dimethyl sulfoxide (DMSO) and the absorbance at 540nm was read using a scanning multi-well spectrophotometer (scanning multi-well spectrophotometer).
Example 4 detection of hydroxyl groups
By the Fenton (Fenton) reaction (H)2O2+FeSO4) The resulting hydroxyl group is reacted with 5, 5-dimethyl-1-pyrroline-N-oxide. The 5, 5-dimethyl-1-pyrroline-N-oxide/. OH addition product thus formed was detected using ESR spectroscopy. Phosphate buffer (pH 7.4) was mixed with 0.02ml of 0.3M 5, 5-dimethyl-1-pyrroline-N-oxide and 10mM FeSO410mM of H2O2And 10 μ M of 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid, DQA) were mixed and the ESR spectrum was recorded after 2.5 minutes. The ESR spectrometer parameters were set as follows: a central magnetic field: 336.8 mT; power: 1.00 mW; frequency: 9.4380 GHz; modulation width (modulation width), 0.2 mT; amplitude (amplitude): 600, preparing a mixture; sweep width (sweep width): 10 mT; scan time (sweep time): 0.5 minute; time constant (timestatus): 0.03 second; and temperature: at 25 ℃.
Example 5 intracellular reactive oxygen species determination
Measurement by irradiation of H by the 2', 7' -dihydrofluorescein diacetate method2O2(1mM) or ultraviolet B (30 mJ/cm)2) To induce intracellular reactive oxygen species levels. After 16 hours of smearing, the cells were treated with red gallol at concentrations of 2.5. mu.M, 5. mu.M and 10. mu.M for 1 hour. Treatment of cells with respective treatment H2O2Or ultraviolet B for 30 minutes and 8 hours. After adding 25. mu.M of 2', 7' -dihydrofluorescein diacetate for 10 minutes, 2', 7' -dichlorofluorescein fluorescence was detected using an LS-5B spectrofluorometer (PerkinElmer, Waltham, MA, USA). Removal effect of intracellular reactive oxygen species (%) [ (treatment alone H)2O2Or fluorescence value at ultraviolet B) - (treatment H2O2Or the fluorescence value of UV B cell treated erythrogallol)/(treatment H2O2Or fluorescence value at ultraviolet B]×100。
For image analysis of intracellular reactive oxygen species, 2X 105Cell/well density cells were seeded on 4-well chamber slides. After 16 hours, red gallol was treated at a concentration of 10. mu.M for 1 hour, and the slides were again exposed to UV-B (30 mJ/cm)2)6 hours and/or 18 hours at a temperature of 37 ℃ to a mote (50 ppM). 50 μ M of 2', 7' -dihydrofluorescein diacetate was added to each well at 37 ℃ for 30 minutes. After 3 washes with Phosphate Buffered Saline (PBS), the stained cells were mounted on chamber slides using a mounting agent (DAKO, Carpinteria, CA, USA). Images were obtained using a confocal Microscope equipped with Laser Scanning Microscope5 pascal software (Laser Scanning 5 pascal software) (Carl Zeiss, Oberkochen, Germany).
Example 6 cell gel electrophoresis (Comet analysis)
The degree of oxidative DNA damage was evaluated by Comet analysis. The cell suspension was mixed with 75. mu.l of 0.5% Low Melting Agarose (LMA) at a temperature of 39 ℃ and the mixture was smeared (spading) onto a fully frozen microscope slide pre-coated with 200. mu.l of 1% Normal Molten Agarose (NMA). After agarose curing, the slides were immersed in an additional 0.5% LMA 170X-100 and 10% dimethyl sulfoxide (pH10) at a temperature of 4 ℃ for 1 hour. Next, the slide glass was placed in a gel electrophoresis apparatus containing 300mM NaOH and 10mM Na-EDTA (pH10) and incubated for 40 minutes to induce unwinding (unwinding) of deoxyribonucleic acid and expression of alkali-labile lesion (alkali-labile damage). Subsequently, an electric field (300mA, 25V) was applied at a temperature of 25 ℃ for 30 minutes to attract the negatively charged deoxyribonucleic acid to the anode. The slides were washed 3 times in neutral buffer (0.4M Tris, pH 7.5) at a temperature of 4 ℃ and after 5 minutes each time, stained with 80. mu.l of 10. mu.g/mL ethidium bromide and visualized using a fluorescence microscope and image analyzer Komet 5.5(Andor Technology, Belfast, UK)). The tail length and percent total fluorescence of the comet tail were recorded in 50 cells per slide.
Example 7 lipid peroxidation assay
Lipid peroxidation was evaluated using diphenyl-1-pyrenylphosphine as a probe. Diphenyl-1-pyrenyl phosphine lipid hydroperoxides react to form diphenyl-1-pyrenyl phosphine oxide as a fluorescent substance, providing evidence of membrane damage. After treating the cells with 10. mu.M of red gallol for 1 hour, the cells were exposed to UV-B (30 mJ/cm)2). After 5 hours, 5mM of diphenyl-1-pyrenyl phosphine was added, and the diphenyl-1-pyrenyl phosphine fluorescent photographs were analyzed using a fluorescence microscope and image analyzer Komet 5.5(Andor Technology, Belfast, UK) for 30 minutes in a dark room.
Example 8 protein carbonyl formation
After inoculating the cells in a medium containing 10. mu.M of red gallol for 1 hour, the cells were cultured for 12 hours and exposed to ultraviolet B (30 mJ/cm)2). Using Oxiselect according to the manufacturer's instructionsTMProtein carbonyl enzyme-linked immunosorbent assay (ELISA) kits judge the amount of protein carbonyl formed (Cell Biolabs, San Diego, CA, USA).
Example 9 Nuclear staining Using Hoechst 33342
After treating the cells with 10. mu.M of red gallol for 1 hour,treatment of dust particles (50ppm) and/or UV B (30 mJ/cm)2) And cultured at 37 ℃ for 18 hours. Then, a fluorescent pigment specific for deoxyribonucleic acid, Hoechst 3334 (1.5. mu.l of stock solution of 10 mg/ml) was added to each well and the cells were cultured at a temperature of 37 ℃ for 10 minutes. Stained cells were observed with a fluorescence microscope equipped with a CoolSNAP-Pro color digital camera. Nuclear condensation was assessed and the number of apoptosis was determined. Apoptosis index ═ number of apoptosis of red-gallol-treated group/total number of cells of red-gallol-treated group)/(number of apoptosis of control group/total number of cells of control group).
Statistical analysis
All assays were performed 3 times and all values are expressed as mean ± standard error. The results were analyzed for mean difference by Tukey test analysis after analysis of variance. In all cases, a p-value <0.05 was considered statistically significant.
B. Results of the experiment
Experimental example 1 Effect of inhibiting active oxygen Cluster formation of Red Gallol
The 3- (4, 5-dimethylthiazole-2) -2, 5-diphenyltetrazolium bromide salt assay showed no cytotoxicity to HaCaT cells regardless of the concentration of red gallol used. The cell viability of each sample-treated group was higher than 96% relative to the control group (fig. 1). And, treatment of H using 2', 7' -dihydrofluorescein diacetate assay2O2Then, the intracellular reactive oxygen species-removing activity of red gallol was judged (FIG. 2). From the fluorescence spectroscopy data, it was confirmed that red gallol had H in a concentration-dependent manner2O2The intracellular reactive oxygen species removing effect of the treated cells was 11% at 2.5. mu.M, 23% at 5. mu.M and 42% at 10. mu.M, respectively, as compared with the control group (FIG. 2). In order to evaluate the hydroxyl group removing ability of red gallol (10. mu.M), ESR spectroscopy was performed. In FeSO4+H2O2In this system, the 5, 5-dimethyl-1-pyrroline-N-oxide/. OH addition product had a signal of about 3366 in the control group and was reduced to about 2090 in the red gallol group (FIG. 3). This result demonstrates that red gallol effectively inhibits the reactive oxygen species.
Finally, it was confirmed that red gallol was presentNo cytotoxicity, H2O2The induced intracellular active oxygen cluster and hydroxyl radical scavenging effect is excellent.
EXAMPLE 2 UV-B-induced cell injury preventing Effect of Red Gallol
First, 10 μ M of red gallol obtained by confocal microscopy attenuated the intensity (green) caused by UV B radiation (FIG. 4). This indicates that red gallol has active oxygen cluster removal properties.
And, lipid peroxidation was confirmed by examining the fluorescent product diphenyl-1-pyrenyl phosphine oxide generated from diphenyl-1-pyrenyl phosphine. The diphenyl-1-pyrenylphosphine oxide intensity was higher in uv B exposed cells than in uv B exposed cells treated with red gallol (blue) (fig. 5). Thus, it is known that red gallic acid inhibits lipid peroxidation.
Then, comet analysis was used to evaluate the protective effects of uv B-induced dna damage and red gallol. Representative micrographs show the comet tail length and the proportion of fluorescence of the tail (FIG. 6). As a result, it was confirmed that the red gallol pretreatment significantly reduced the fluorescence of the tail, and the tail length induced by the uv B treatment was reduced from 65% to 22%.
Finally, carbonyl groups are detected during protein oxidation by protein carbonylation analysis. As a result, it was confirmed that irradiation with ultraviolet B increased the concentration of carbonyl residues, but when red gallol was pretreated in the ultraviolet B exposure group, formation of protein carbonyl groups was suppressed (fig. 7).
Briefly, these results indicate that red gallol inhibits deoxyribonucleic acid damage, lipid peroxidation, and protein damage from oxidative damage induced by ultraviolet B irradiation, and effectively protects deoxyribonucleic acid, lipid, and protein.
EXAMPLE 3 apoptosis-suppressing Effect induced by ultraviolet B irradiation of Red Gallol
The viability of HaCaT cells was assessed using 3- (4, 5-dimethylthiazole-2) -2, 5-diphenyltetrazolium bromide assay (fig. 8). Uv B-irradiated cells were as low as 59% viable relative to control cells. However, the viability of the red-gallic-phenol-pretreated group was up to 77%, indicating that the red-gallic-phenol cells are protected from UV-B induced apoptosis.
Flow cell analysis was then used to determine the number of apoptotic bodies (figure 9). Apoptosis induces changes in mitochondrial membrane permeability and displacement, and mitochondrial dysfunction in inducing apoptosis can be detected by JC-1 staining. As a result, the uv B-irradiated cells contained the largest number of apoptotic cells and had a fluorescence intensity of 180, but the red gallol pretreatment reduced the number of apoptotic cells and had a fluorescence intensity of 154. Therefore, it was found that red gallol had a protective effect against UV-B-induced apoptosis.
Furthermore, cells were stained with Hoechst 33342, and the degree of nuclear condensation and the formation of apoptotic bodies, which are characteristics of apoptosis, were visualized. Normal nuclei were observed in the control and red-gallol treated cells, but significant nuclear condensation was observed in the uv B-irradiated cells (fig. 10).
Therefore, it is known that red gallol has a protective effect on skin apoptosis induced by ultraviolet B.
EXAMPLE 4 dust-induced active oxygen Cluster formation and apoptosis-inhibiting Effect of Red Gallol
Images obtained with a confocal microscope showed that 10 μ M of red gallic phenol reduced the intensity (green) based on mote (fig. 11). This indicates that red gallol inhibits the formation of reactive oxygen species.
Further, it was confirmed that apoptosis was the most in the mote-treated cells and that the red-gallol pretreatment protected the cells from apoptosis by showing an image of apoptosis body formation based on nuclear condensation and Hoechst 33342 staining (fig. 12).
Finally, it was found that red gallol had a protective effect on the removal of reactive oxygen species induced by mote and apoptosis of skin cells.
EXAMPLE 5 protective Effect against micronic dust and UV-B-induced oxidative damage and apoptosis of Red Gallol
It was confirmed from the image obtained by confocal microscopy that the generation of reactive oxygen species in the cells was promoted by the irradiation of the fine dust or ultraviolet B. Further, it was confirmed that red gallol (10 μ M) decreased the intensity (green) due to ultraviolet B irradiation, mote or mote + ultraviolet B irradiation (fig. 13). This indicates that red gallol inhibits the generation of reactive oxygen species caused by mote or ultraviolet B irradiation.
Further, it was confirmed from the results of nuclear staining with Hoechst 33342 that the ultraviolet B-induced apoptosis was further increased by the motes, but the red-gallol pretreatment group inhibited the apoptosis increased by the motes or the irradiation with ultraviolet B (fig. 14).
Therefore, it is known that red gallol inhibits active oxygen clusters and apoptotic bodies caused by ultraviolet B irradiation or ultraviolet B irradiation and fine dust treatment in the human keratinocyte cell line, and has a skin-protecting effect by ultraviolet light and fine dust.
Although the preferred embodiments of the present invention have been described in detail, the scope of the invention is not limited thereto, and various modifications and improvements by those skilled in the art are possible within the scope of the present invention by using the basic concept of the present invention defined in the above-described scope of the invention.
Claims (9)
1. A cosmetic composition for protecting skin against active oxygen clusters, ultraviolet rays or fine dusts, characterized by comprising red gallol or a cosmetically acceptable salt thereof as an active ingredient.
2. The cosmetic composition for protecting skin against reactive oxygen species, ultraviolet rays or fine dusts according to claim 1, wherein the reactive oxygen species is hydrogen peroxide or hydroxyl group.
3. The cosmetic composition for protecting skin against reactive oxygen species, ultraviolet rays or fine dusts according to claim 1, wherein the ultraviolet rays are ultraviolet rays B.
4. The cosmetic composition for protecting skin against reactive oxygen species, ultraviolet rays or fine dusts according to claim 1, wherein the red gallol exhibits the skin protective activity by the scavenging action of the reactive oxygen species by the ultraviolet B or the fine dusts.
5. The cosmetic composition for protecting skin against reactive oxygen species, ultraviolet rays or fine dusts according to claim 1, wherein the red gallol exhibits the skin protecting activity by reducing the effect of intracellular lipid peroxidation, deoxyribonucleic acid damage or protein damage caused by ultraviolet B.
6. The cosmetic composition for protecting skin against reactive oxygen species, ultraviolet rays or fine dusts according to claim 1, wherein the red gallol exhibits skin protective activity by inhibiting the action of apoptosis of cells exposed to ultraviolet B or fine dusts.
7. The cosmetic composition for protecting skin against reactive oxygen species, ultraviolet rays or fine dusts according to claim 1, wherein the cosmetic composition is in one or more dosage forms selected from the group consisting of a solution, a topical ointment, a skin cream, a face lotion, a nourishing lotion, a skin softening lotion, a pack, a skin softening lotion, an emulsion, a makeup base, a essence, a soap, a liquid cleansing liquid, a bathing agent, a sun cream, a sunscreen, a suspension, an emulsion, a cream, a gel, a skin care lotion, a cake, a soap, a surfactant-containing face cleanser, an oil, a loose powder, an emulsion foundation, a wax foundation, a patch and a spray.
8. A quasi-pharmaceutical composition for protecting skin against active oxygen clusters, ultraviolet rays or fine dusts, characterized by comprising red gallol or a physiologically acceptable salt thereof as an active ingredient.
9. A skin external composition for protecting skin against active oxygen clusters, ultraviolet rays or fine dusts, which comprises red gallol or a physiologically acceptable salt thereof as an active ingredient.
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| PCT/KR2018/008350 WO2019059512A2 (en) | 2017-09-25 | 2018-07-24 | Cosmetic composition containing purpurogallin for skin protection against reactive oxygen species, ultraviolet radiation, or fine dust |
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| US5650439A (en) * | 1994-05-02 | 1997-07-22 | Hoffmann-La Roche Inc. | Purpurogallin derivatives |
| CN102238983A (en) * | 2008-06-25 | 2011-11-09 | 巴斯夫欧洲公司 | Use of benzotropolone derivatives as uv absorbers and antioxidants and their use in sunscreens and/or cosmetic compositions |
| KR20130132508A (en) * | 2011-01-03 | 2013-12-04 | (주)아모레퍼시픽 | Composition for combating oxidation and alleviating detrimental effects on skin caused by asian dust |
| KR101748806B1 (en) * | 2016-02-29 | 2017-06-19 | 대구대학교 산학협력단 | Anti-melanogenic cosmetic composition of Purpurogallin as an efficient component and preparation method of the same |
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| JPH06507610A (en) * | 1991-05-16 | 1994-09-01 | ウー，タイ−ウィン | Pharmaceutical compositions containing purprogalin useful as antioxidants and cytoprotective agents |
| JP2004359576A (en) * | 2003-06-03 | 2004-12-24 | Fumio Hashimoto | Apoptosis-inducing agent |
| KR100865022B1 (en) | 2007-03-20 | 2008-10-23 | 이월자 | The Cosmetic composition for preventing the skin aging |
| KR101736714B1 (en) * | 2016-12-12 | 2017-05-17 | 박지영 | Cosmetic composition for improvement of skin function comprising natural extract |
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| US5650439A (en) * | 1994-05-02 | 1997-07-22 | Hoffmann-La Roche Inc. | Purpurogallin derivatives |
| CN102238983A (en) * | 2008-06-25 | 2011-11-09 | 巴斯夫欧洲公司 | Use of benzotropolone derivatives as uv absorbers and antioxidants and their use in sunscreens and/or cosmetic compositions |
| KR20130132508A (en) * | 2011-01-03 | 2013-12-04 | (주)아모레퍼시픽 | Composition for combating oxidation and alleviating detrimental effects on skin caused by asian dust |
| KR101748806B1 (en) * | 2016-02-29 | 2017-06-19 | 대구대학교 산학협력단 | Anti-melanogenic cosmetic composition of Purpurogallin as an efficient component and preparation method of the same |
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