CN111132656A - Cosmetic composition for protecting skin from active oxygen, ultraviolet rays or fine dusts comprising 3, 4-dicaffeoylquinic acid - Google Patents
Cosmetic composition for protecting skin from active oxygen, ultraviolet rays or fine dusts comprising 3, 4-dicaffeoylquinic acid Download PDFInfo
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- CN111132656A CN111132656A CN201880062138.0A CN201880062138A CN111132656A CN 111132656 A CN111132656 A CN 111132656A CN 201880062138 A CN201880062138 A CN 201880062138A CN 111132656 A CN111132656 A CN 111132656A
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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
- A61K8/37—Esters of carboxylic acids
- A61K8/375—Esters of carboxylic acids the alcohol moiety 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
- A61K8/37—Esters of carboxylic acids
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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 from active oxygen, ultraviolet rays or fine dusts, which contains 3, 4-dicaffeoylquinic acid or a cosmetically acceptable salt thereof as an active ingredient, and can be used as a cosmetic composition for protecting skin from active oxygen, ultraviolet rays or fine dusts.
Description
Technical Field
The present invention relates to a cosmetic composition, a quasi-pharmaceutical composition, and a skin external preparation composition, which contain 3, 4-dicaffeoylquinic acid or a cosmetically acceptable salt thereof as an active ingredient and protect the skin from active oxygen, ultraviolet rays, or fine dust.
Background
The skin is a body part directly exposed to the external environment, and serves not only as a protective film for protecting important organs of the human body, but also as an effect of regulating moisture evaporation and protecting the human body from external infection. However, although the skin prevents penetration of viruses from the outside, excessive ultraviolet rays, contaminated environments, and the like, all cause skin irritation, and eventually skin aging.
Ultraviolet B (UVB radiation) at a wavelength of 280-320nm is one of the major environmental factors responsible for the deleterious effects on the skin, such as skin cancer (skinner), immune system suppression and photo-aging. Reactive Oxygen Species (ROS) generated from such UVB causes oxidative damage (oxidative damage) to cellular components such as lipids (lipids), proteins (proteins), and DNA, and further, promotes skin aging, causing various skin disorders.
The active oxygen is oxygen in an unstable state, and is caused by excessive oxygen generation due to environmental pollution and chemical substances, ultraviolet rays, blood circulation disorder, stress, and the like. Such excessively generated active oxygen is oxidized together in the human body, and thus, cell membranes, DNA and all other cell structures are damaged, and according to the damaged range, cells are lost functions or deteriorated. In addition, in skin cells, active oxygen induces oxidative stress, promoting skin aging.
Many antioxidants have been proposed to protect the skin from cell damage caused by Reactive Oxygen Species (ROS), and for example, epigallocatechin gallate ((-) -epigallocatechin-3-gallate) and resveratrol (resveratrol) and the like are known to inhibit UVB damage to the skin. In addition, it is known that various marine algae (marine algae) and seaweeds (seaweed) containing compounds such as carotenoids (carotenoids), phenolic compounds (phenolics), and antioxidant vitamins (antioxidant vitamins) also alleviate oxidative stress (oxidative stress) in skin cells by a biological antioxidant system and direct scavenging of free radicals (fungi).
In addition, fine dust, sand dust, and smoke containing harmful substances such as heavy metals, which have been generated in recent years by industrialization of china, are considered to be the main causes of skin aging and skin problems.
Mote is a minute substance invisible to our eyes, is a particulate substance 10 μm or less in diameter, and floats or disperses in the air for a long time. Is an air pollutant which is discharged when fossil fuels such as coal and petroleum are burned or in exhaust gas of manufacturing industry and automobiles, and is adsorbed to lung through a bronchus to cause various lung diseases. According to the data of the ministry of environment of korea, terms for fine dusts used in 2017, 3, korea and internationally are different and confusing, respectively, fine dusts (PM10) having a diameter of 10 μm or less are defined as floating dusts, and ultra fine dusts (PM2.5) having a diameter of 2.5 μm or less are defined as fine dusts.
Pollutants such as dust and sand can generate pressure on the skin, which is generated by the active oxygen. Active oxygen acts as an intracellular signaling agent, playing an important role in maintaining normal cellular functions (e.g., activating electron carriers and protein cells in mitochondria). However, active oxygen is unstable and highly oxidizing, and easily reacts with biological materials, and therefore, if not eliminated from the body, it causes oxidative stress.
Disclosure of Invention
Technical problem
Accordingly, an object of the present invention is to develop a cosmetic composition having an effect of protecting skin from active oxygen, ultraviolet rays or fine dusts.
Means for solving the problems
The present invention provides a cosmetic composition for protecting skin from active oxygen, ultraviolet rays or fine dusts, which contains 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid) or a cosmetically acceptable salt thereof as an active ingredient.
Another object of the present invention is to provide a quasi-pharmaceutical composition for protecting skin from active oxygen, ultraviolet rays or fine dusts, which comprises 3, 4-dicaffeoylquinic acid or a physiologically acceptable salt thereof as an active ingredient.
Another object of the present invention is to provide a skin external preparation composition for protecting skin from active oxygen, ultraviolet rays or fine dusts, which comprises 3, 4-dicaffeoylquinic acid or a physiologically acceptable salt thereof as an active ingredient.
It is still another object of the present invention to provide a use of 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid) or a cosmetically acceptable salt thereof for preparing a cosmetic composition for protecting skin from active oxygen, ultraviolet rays or fine dusts.
It is still another object of the present invention to provide a use of 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid) or a physiologically acceptable salt thereof for preparing a quasi-pharmaceutical composition for protecting skin from active oxygen, ultraviolet rays or fine dusts.
It is still another object of the present invention to provide a use of 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid) or a physiologically acceptable salt thereof for preparing a composition for external preparation for skin for protecting skin from active oxygen, ultraviolet rays or fine dusts.
It is still another object of the present invention to provide a method for protecting skin from active oxygen, ultraviolet rays or fine dusts, which comprises the step of administering 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid) or a physiologically acceptable salt thereof to a subject.
ADVANTAGEOUS EFFECTS OF INVENTION
The present invention relates to a cosmetic composition for protecting skin from active oxygen, ultraviolet rays or fine dusts, which comprises 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid) or a cosmetically acceptable salt thereof as an active ingredient, and can protect skin from active oxygen, ultraviolet rays or fine dusts.
Drawings
Fig. 1 to 6 show the effect of DQA (3, 4-dicaffeoylquinic acid) on cytotoxicity and ROS scavenging. (FIG. 1) cells were treated with 1. mu.M, 2.5. mu.M, 5. mu.M, 10. mu.M and 20. mu.M DQA (3, 4-dicaffeoylquinic acid) for 24 hours. Cell viability was judged using the cell viability assay (MTT) method. Indicates a significant difference from untreated cells (P)<0.05). (FIG. 2) cells were pretreated with 1. mu.M, 2.5. mu.M, 5. mu.M, 10. mu.M and 20. mu.M DQA (3, 4-dicaffeoylquinic acid). After 30 minutes, 1mM of H2O2Or 30mJ/cm2To the panel. After 30 minutes, the intracellular ROS produced were detected by fluorescence spectroscopy after treatment with DCF-DA. The antioxidant NAC was used in the positive control group. Is represented by2O2Significant differences in treated cells (P)<0.05). # indicates a significant difference from UVB-treated cells (P)<0.05). (FIG. 3) DMPO-. OOH produced by superoxide anion and DMPO was detected by Enhanced Specular Reflectance (ESR) spectroscopy. Indicates significant difference from the control group (P)<0.05). # denotes a significant difference from the superoxide anion (P)<0.05). (FIG. 4) DMPO-. OH generated by hydroxyl radical and DMPO was detected by ESR spectrometer. Indicates significant difference from the control group (P)<0.05). # denotes a significant difference from the hydroxyl radical (P)<0.05). (FIG. 5) detection of the intracellular ROS generated after DCF-DA staining using confocal microscopy, (FIG. 6) detection by fluorescence spectroscopy after DCF-DA treatment. Indicates significant difference from control cells (P)<0.05), # indicates a significant difference (P) from UVB treated cells<0.05)。
Fig. 7 and 8 show the effect of DQA (3, 4-dicaffeoylquinic acid) on lipid peroxidation and DNA damage induced by UVB. (FIG. 7) lipid peroxidation was detected by confocal microscopy after DPPP staining. Indicates significant difference from control cells (P <0.05) and # indicates significant difference from UVB treated cells (P < 0.05). (FIG. 8) A representative graph was obtained, and the degree of DNA damage was judged by comet analysis. Indicates significant difference from control cells (P <0.05) and # indicates significant difference from UVB treated cells (P < 0.05).
Fig. 9 and 10 show the effect of apoptosis on DQA (3, 4-dicaffeoylquinic acid). (FIG. 9) cell viability was judged by MTT assay. Indicates a significant difference from untreated cells (P <0.05) and # indicates a significant difference from UVB treated cells (P < 0.05). (FIG. 10) after Hoechst 33342 staining, the formation of apoptotic bodies was observed with a fluorescence microscope. Apoptotic bodies are indicated by arrows. (FIG. 11) after staining the cells with JC-1, the mitochondrial membrane potential was assessed by flow cytometry analysis. Indicates a significant difference from control cells (P <0.05) and # indicates a significant difference from UVB treated cells (P < 0.05)).
Fig. 12 and 13 show the effect of DQA (3, 4-dicaffeoylquinic acid) on mote (PM) and UVB-induced ROS and apoptosis. (FIG. 12) detection of the intracellular ROS generated after DCF-DA staining with confocal microscopy. (FIG. 13) apoptotic bodies were observed with a fluorescence microscope after Hoechst 33342 staining. Apoptotic bodies are indicated by arrows.
Detailed Description
Next, as one embodiment for achieving the object of the present invention, the present invention provides a cosmetic composition for protecting skin from active oxygen, ultraviolet rays or fine dusts, which comprises 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid) or a cosmetically acceptable salt thereof as an active ingredient.
The cosmetic composition of the present invention contains 3, 4-dicaffeoylquinic acid or a cosmetically acceptable salt thereof as an active ingredient.
The cosmetic composition comprising the 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid) has skin protecting effect from active oxygen, ultraviolet rays or fine dusts.
In the present invention, the chemical formula of "3, 4-dicaffeoylquinic acid" is as follows.
[ chemical formula 1]
In one embodiment of the present invention, 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid, DQA) was confirmed to have no cytotoxicity in experiments with human keratinocyte cell line (HaCaT), and was confirmed to have no cytotoxicity against hydrogen peroxide (H)2O2) The induced scavenging effect of Reactive Oxygen Species (ROS) and reactive oxygen species such as superoxide anion and hydroxyl radical can be used as an effective ingredient of a cosmetic composition for protecting skin from reactive oxygen species.
In the present invention, the active oxygen may be selected from the group consisting of hydrogen peroxide (H)2O2) One or more selected from the group consisting of superoxide anion (superoxide anion) and hydroxyl radical (hydroxyl radical).
In addition, in one example of the present invention, 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid, DQA) was confirmed to have a scavenging effect on intracellular Reactive Oxygen Species (ROS) induced by UVB, and to significantly reduce DNA damage and lipid peroxidation increased by UVB stimulation.
Furthermore, it was confirmed that there is a protective effect on UVB-induced apoptosis by reducing apoptotic bodies (apoptotic bodies) increased in HaCaT cells by UVB irradiation.
Therefore, the 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid, DQA) can be used as an effective ingredient of a cosmetic composition for protecting skin from ultraviolet rays.
In the present invention, the ultraviolet ray may be ultraviolet ray B (UV B).
In addition, in the present invention, the 3, 4-dicaffeoylquinic acid (DQA) may exhibit skin-protective activity by scavenging Reactive Oxygen Species (ROS) generated by ultraviolet B.
In addition, in the present invention, the 3, 4-dicaffeoylquinic acid (DQA) may exhibit skin-protective activity by reducing the effect of intracellular lipid peroxidation or DNA damage caused by ultraviolet B.
In addition, in one example of the present invention, it was confirmed that 3, 4-dicaffeoylquinic acid (DQA) inhibits ROS and apoptotic bodies induced by UVB or UVB and Particulate Matter (PM) treatment in human keratinocyte cell lines, and the effect of protecting skin from uv light and particulate matter was confirmed. Therefore, the 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid, DQA) can be used as an effective ingredient of a cosmetic composition for protecting skin from ultraviolet rays or fine dusts.
In addition, in the present invention, the 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid, DQA) may exhibit skin-protective activity by inhibiting the action of apoptotic bodies (aptamers) of cells exposed to ultraviolet B or mote.
As the active ingredient of the cosmetic composition of the present invention, 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid, DQA) or a cosmetically acceptable salt form thereof may be used. Useful as an acid addition salt of a salt formed from a cosmetically acceptable free acid (free acid). Acid addition salts may be prepared by conventional methods, for example by dissolving the compound in an excess of aqueous acid and precipitating the resulting salt with a water-miscible organic solvent, for example methanol, ethanol, acetone or acetonitrile. The same molar amount of compound and aqueous acid or alcohol (e.g., ethylene glycol monomethyl ether) can be heated, and the mixture can then be evaporated to dryness or the precipitated salt can be suction filtered. In this case, the free acid may be an organic acid or an inorganic acid, the inorganic acid may be hydrochloric acid, phosphoric acid, sulfuric acid, nitric acid, tartaric acid, or the like, and the organic acid may be methanesulfonic acid, p-toluenesulfonic acid, acetic acid, trifluoroacetic acid, maleic acid, succinic acid, oxalic acid, benzoic acid, tartaric acid, fumaric acid (fumeric 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 (glucuronic acid), aspartic acid, ascorbic acid, carbonic acid, vanillic acid, hydroiodic acid, or the like, but not limited thereto.
Also, a cosmetically acceptable metal salt can be prepared using alkali. Alkali metal or alkaline earth metal salts are obtained, for example, by dissolving the compound in an excess of alkali metal hydroxide or alkaline earth metal hydroxide solution, filtering the undissolved compound salt, and then evaporating and drying it. And, the silver salt corresponding thereto can be obtained by reacting an alkali metal or alkaline earth metal salt with a suitable silver salt (e.g., silver nitrate).
The cosmetic composition for protecting skin from active oxygen, ultraviolet rays or fine dusts of the present invention may include 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid) or a cosmetically acceptable salt thereof in an amount of 0.001 to 100 weight percent, specifically, may include 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid) or a cosmetically acceptable salt thereof in an amount of 0.01 to 50 weight percent, relative to the total weight of the composition, but is not limited thereto.
In addition, the cosmetic composition of the present invention may include conventional acceptable ingredients in addition to the effective ingredients, but is not limited thereto, and for example, may include conventional adjuvants such as antioxidants, stabilizers, solubilizers, vitamins, pigments and perfumes, and carriers.
The cosmetic composition according to the present invention may be prepared into one or more dosage forms selected from the group consisting of a solution, an external ointment, a cream, a foam, a nutrient solution, a soft lotion, a pack, a soft water, an emulsion, a sun-screen cream, a essence, a soap, a liquid cleanser, a bathing agent, a sunscreen cream, a sunscreen oil, a suspension, an emulsion, a paste, a gel, a lotion, a powder, a soap, a surfactant-containing face wash, an oil, a powder foundation, 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 formulated in general skin cosmetics, and as conventional ingredients, for example, oils, water, surfactants, moisturizers, lower alcohols, thickeners, chelating agents, colorants, preservatives, perfumes, and the like may be appropriately blended, but not limited thereto. The cosmetically acceptable carrier contained in the cosmetic composition of the present invention is widely varied depending on the formulation.
When the dosage form of the present invention is an ointment, paste, cream or gel, animal oil, vegetable oil, wax, paraffin, starch, tragacanth, cellulose derivative, polyethylene glycol, silicon, bentonite, silica, talc, zinc oxide or a mixture thereof may be used as a carrier component.
When the formulation of the present invention is a powder or a spray, lactose, talc, silicon dioxide, aluminum hydroxide, calcium silicate, polyamide powder, or a mixture thereof can be used as a carrier component, and particularly in the case of a spray, an accelerator such as chlorofluorocarbon, propane/butane, or dimethyl ether can be further included.
When the dosage form of the present invention is a solution or emulsion, a solvent, a solubilizer or an emulsifier is used as a carrier component, and for example, water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1, 3-butyl glycol oil, and particularly, cottonseed oil, peanut oil, corn germ oil, olive oil, castor oil, sesame oil, glycerol aliphatic ester, polyethylene glycol or fatty acid ester of sorbitan can be used.
When the formulation of the present invention is a suspension, a liquid diluent such as water, ethanol or propylene glycol may be used as a carrier component; suspending agents such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester; microcrystalline cellulose, aluminum metahydroxide, bentonite, agar-agar or tragacanth, and the like.
When the formulation of the present invention is a soap, an alkali metal salt of a fatty acid, a fatty acid half ester salt, a fatty acid protein hydrolysate, an isethionate salt, a lanolin derivative, an aliphatic alcohol, a vegetable oil, glycerin, a sugar, or the like can be used as a carrier component.
When the formulation of the present invention is a surfactant-containing detergent, aliphatic alcohol sulfate, aliphatic alcohol ether sulfate, sulfosuccinic acid monoester, isethionate, imidazolinium 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 another embodiment, the present invention provides a quasi-pharmaceutical composition for protecting skin from active oxygen, ultraviolet rays or fine dusts, which comprises 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid) or a physiologically acceptable salt thereof as an active ingredient.
The protection of the skin from active oxygen, ultraviolet light or fine dust by the 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid) is as described above.
The term "physiologically acceptable" in the present invention means physiologically acceptable and does not generally cause allergic reactions such as gastrointestinal disorders, dizziness or the like when administered to an organism, and the compound used is a commonly used compound which can exert a desired effect.
The term "quasi-drug" as used in the present invention means a drug which has weaker action than a pharmaceutical in an article used for the purpose of diagnosis, treatment, amelioration, alleviation, treatment or prevention of human or animal diseases, and for example, according to the pharmaceutical law, the quasi-drug is an article which is used for purposes other than pharmaceutical, and includes fibers, rubber products, which have slight or no direct action on the human body, which are not instruments, machines or the like, for the purpose of treatment or prevention of human or animal diseases, and sterilization, pesticides or the like for the purpose of prevention of 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, shower foam, mouthwash, wet wipe, laundry soap, hand sanitizer, humidifier filler, mask, ointment, filter filler, or the like.
When the composition of the present invention is contained in a quasi-drug for the purpose of protecting the skin from active oxygen, ultraviolet rays or fine dusts, the composition may be used as it is or together with other quasi-drug ingredients, and may be suitably used according to a conventional method. The mixing amount of the effective ingredients may be appropriately determined depending on the purpose of use, and the quasi-pharmaceutical composition of the present invention may contain 0.01 weight percent to 20 weight percent of the 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid) or a physiologically acceptable salt thereof, relative to the total weight of the composition.
As another embodiment, the present invention provides a skin external preparation composition for protecting skin from active oxygen, ultraviolet rays or fine dusts, comprising 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid) or a physiologically acceptable salt thereof as an active ingredient.
The 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid), physiologically acceptable salts for protecting skin from active oxygen, ultraviolet rays or fine dusts are as described above.
The composition for external preparation for skin according to the present invention may be exemplified by, but not limited to, ointment, lotion, solubilizer, suspension, emulsion, cream, gel, spray, puff, coagulant, patch, or analgesic, and may be formulated by any mechanism known in the art. The composition for external preparation for skin according to the present invention may comprise 0.01 weight percent to 20 weight percent of the 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid) or a physiologically acceptable salt thereof, relative to the total weight of the composition.
As another embodiment, the present invention provides a use of 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid), or a cosmetically acceptable salt thereof, for preparing a cosmetic composition for protecting skin from active oxygen, ultraviolet light, or fine dust.
As another embodiment, the present invention provides a use of 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid), or a physiologically acceptable salt thereof, for the preparation of a quasi-pharmaceutical composition for protecting skin from active oxygen, ultraviolet light, or fine dust.
As another embodiment, the present invention provides a use of 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid) or a physiologically acceptable salt thereof for preparing a composition for external preparation for skin for protecting skin from active oxygen, ultraviolet rays or fine dusts.
In the present invention, the terms "3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid", "physiologically acceptable salt", "cosmetically acceptable salt", "active oxygen", "ultraviolet ray", "fine dust", "cosmetic composition", "quasi-pharmaceutical composition", "composition for external preparation for skin", "skin protection" are explained as described above.
As another embodiment, the present invention provides a method for protecting skin from active oxygen, ultraviolet rays or fine dusts, which comprises the step of administering 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid) or a physiologically acceptable salt thereof to a subject.
In the present invention, the terms "3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid)," physiologically acceptable salt "," active oxygen "," ultraviolet "," fine dust "," skin protection "are explained as described above.
The subject to which the composition of the invention is administered is all mammals including humans, such as cows, pigs, horses, rabbits, mice, humans.
With the skin protection method of 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid) or a physiologically acceptable salt thereof according to the present invention, 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid) or a physiologically acceptable salt thereof may be administered to an individual or the skin of an individual.
The term "administration" in the present invention means introducing 3, 4-dicaffeoylquinic acid (3, 4-dicaffeoylquinic acid) of the present invention or a physiologically acceptable salt thereof by any suitable method, and the administration route of the compound and salt of the present invention is not particularly limited, and administration can be carried out by various routes to achieve the intended purpose of skin tissue.
Detailed description of the preferred embodiments
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 invention. However, the present invention may be embodied in various forms and is not limited to the embodiments described herein.
A. Materials and methods
Example 1 cell culture and UVB irradiation (UVB irradiation)
Human keratinocyte cell lines (HaCaT) were maintained at 37 ℃ in a medium containing 5% carbon dioxide. Cells were grown in DMEM medium containing 10% fetal bovine serum, 1% penicillin and 1% streptomycin. Exposing the cells to 30mJ/cm2UVB (CL-1000M UV Cross-linker, Aphan, Calif., USA).
Example 2 Cell viability (Cell viability)
The effect of DQA (3, 4-dicaffeoylquinic acid) on survival of HaCaT cells was evaluated by the following method. The cells were incubated at 0.8X 105cells/ml were seeded into 24-well plates and 1, 2.5, 5, 10, 20 μ M of DQA (3, 4-dicaffeoylquinic acid) was processed after 24 hours. Stock solution (50. mu.l, 2mg/ml) of MTT stock solution was added to each well plate separately to bring the total reaction volume to 500. mu.l. After 4 hours, the supernatant was aspirated (aspirated). The formazan crystals in each well were dissolved in dimethyl sulfoxide (DMSO), and the absorbance at 540nm was read by a scanning multi-well spectrophotometer (scanning multi-well spectrophotometer).
EXAMPLE 3 detection of superoxide anion
Superoxide anion generated from xanthine/xanthine oxidase was reacted with DMPO, and the resulting DMPO/-OH addition product was detected using ESR spectroscopy. Phosphate buffer (pH7.4) was mixed with 0.02ml of 3 MDMCPO, 5mM xanthine, 0.25U xanthine oxidase and 10. mu.M DQA (3, 4-dicaffeoylquinic acid), respectively, and ESR spectra were recorded after 2.5 minutes. The parameters of the ESR spectrometer were set as follows: central magnetic field, 336.8 mT; power, 5.00 mW; frequency, 9.4380 GHz; modulation width (modulation width), 0.2 mT; amplitude (amplitude), 1000; scan width (sweep width), 10 mT; scan time (sweep time), 0.5 minutes; time constant, 0.03 seconds; and temperature, 25 ℃.
Example 4 detection of hydroxyl radicals
Will react by Fenton (Fenton) (H)2O2+FeSO4) The resulting hydroxyl radical reacts with DM PO. The resulting DMPO/-OH addition product was detected using ESR spectroscopy. Phosphate buffer (pH7.4) was mixed with 0.02ml of 0.3M DMPO, 10mM FeSO4、10mM H2O2And 10 μ MDQA (3, 4-dicaffeoylquinic acid) and ESR spectra were recorded after 2.5 minutes. The parameters of the ESR spectrometer were set as follows: central magnetic field, 336.8 mT; power, 1.00 mW; frequency, 9.4380 GHz; modulation width (modulation width), 0.2 mT; amplitude (amplitude), 600; scan width (sweepwidth), 10 mT; scan time (sweep time), 0.5 minutes; time constant, 0.03 seconds; and temperature, 25 ℃.
Example 5 measurement of intracellular ROS
To go through H2O2Or detecting Reactive Oxygen Species (ROS) in UVB-treated HaCaT cells, and treating the cells at 1.0 × 105cells/ml were seeded onto the well plate and 10. mu.M of DQA (3, 4-dicaffeoylquinic acid) was worked up after 20 hours. After incubation at 37 ℃ for 1 hour, cells were exposed to H2O2(1. mu.M) or PM (particulate matter)2.5(50ppm) and/or UVB (30 mj/cm)2). The UVB source (source) was a CL-1000MUV crosslinking instrument (UVP, Upland, CA, USA). After incubation at 37 ℃ for 30 minutes, DCF-DA solution (50. mu.M) was added. Then, 2 ', 7' -dichlorofluorescein fluorescence (dichlorfluoroscein fluorescence) was detected and quantified using LS-5B spectrofluorescence system (PerkinElmer, Waltham, MA, USA). DCF-DA fluorescence (excitation, 485nm, radiation (emission), 535nm) was detected using a Perkinelmer LS-5B spectrofluorometer and images were collected using a confocal microscope.
Example 6 lipid peroxidation assay
DPPP was evaluated for lipid peroxidation using probes. DPPP reacts with lipid hydroperoxides to produce DPPP oxide, a fluorescent substance, which provides a sign of membrane damage. After treating the cells with 10. mu.M DQA (3, 4-dicaffeoylquinic acid) for 24 hours, they were incubated with 20. mu.M DPPP for 30 minutes in the dark. DPPP fluorescence images were obtained with a Zeiss Axiovert 200 inverted microscope at an excitation wavelength of 351nm and an emission wavelength of 380 nm. Images were collected using a confocal microscope.
Example 7 Single cell gel electrophoresis (Comet analysis)
The degree of oxidative DNA damage was evaluated by Comet analysis. The cell suspension was mixed with 70. mu.l of 1% Low Melting Agarose (LMA) at 37 ℃ and the mixture was spread (spading) on a fully frozen microscope slide pre-coated with 200. mu.L of 1% Normal Melting Agarose (NMA). After the agarose solidified, the slides were covered with 170. mu.l of another 0.5% LMA and then soaked with a lysis solution (2.5M NaCl, 100mM Na-EDTA, 10mM Tris, 1% Triton X-100 and 10% DMSO, 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 (pH 10), and after incubation for 30 minutes, the expression of DNA unwinding (unwinding) and alkali-labile damage (a lkali-simple damage) was induced. Then, an electric field (300mA, 25V) was applied at a temperature of 25 ℃ for 30 minutes to attract the negatively charged DNA to the anode. The slides were washed 3 times in neutral buffer (0.4M Tris, pH 7.5) at 25 ℃ for 10 minutes, then 1 time 10 minutes at 25 ℃ with 100% ethanol. Then, the slide glass was stained with 80. mu.l of 10. mu.g/mL ethidium bromide, and observed using a fluorescence microscope and an image analyzer (Komet 5.5, Kinetic imaging Ltd, Wirral, UK). The tail length of 50 cells per slide and the percentage of total fluorescence in the comet tail were recorded.
Example 8 Nuclear staining Using Hoechst 33342
Cells were treated with 10. mu.M DQA (3, 4-dicaffeoylquinic acid), 1 hour later with PM (particulate matter)2.5(50ppm) and/or UVB (30 mJ/cm)2) And (6) processing. After incubation at 37 ℃ for 24 hours, the DNA-specific fluorescent dye Hoechst 33342 (1. mu.l of 20mM stock solution) was added to each well, and the cells were incubated at 37 ℃ for 10 minutes. Stained cells were visualized using a fluorescence microscope equipped with a CoolSNAP-Pro color digital camera. The degree of nuclear condensation was evaluated and the number of apoptotic cells was measured.
Example 9 mitochondrial Membrane potential analysis
The cells were cultured at 1X 105cells/mL were seeded in 6-well plates. After 16 hours of plating, the cells were treated with 10 μ M DQA (3, 4-dicaffeoylquinic acid) and further incubated for 24 hours at a temperature of 37 ℃. Mitochondrial membrane potential was analyzed using a lipophilic cationic fluorescent dye JC-1 entering mitochondria, which changed fluorescence from green to red as the membrane potential increased. Mitochondrial membrane potential was analyzed by flow cytometry.
Statistical analysis
All measurements were performed 3 times and all values are expressed as mean ± sd. As a result, the difference in average was analyzed by performing Tukey experiment after the dispersion analysis. In all cases, p values less than 0.05 were considered statistically significant.
B. Results of the experiment
Experimental example 1 Effect of DQA on cytotoxicity and ROS scavenging
DQA (3, 4-dicaffeoylquinic acid) is not cytotoxic at up to 20. mu.M (FIG. 1). DQA (3, 4-dicaffeoylquinic acid) pair is composed of H2O2The induced scavenging effect of Reactive Oxygen Species (ROS) in cells is increased in a concentration-dependent manner in the concentration range of 1-20 μ M. In addition, DQA (3, 4-dicaffeoylquinic acid) has a scavenging effect on intracellular Reactive Oxygen Species (ROS) induced by UVB (fig. 2). Therefore, in all subsequent experiments, it was decided to use 10 μ M of DQA (3, 4-dicaffeoylquinic acid). This is because DQA (3, 4-dicaffeoylquinic acid) shows similar scavenging effect and cytotoxicity at 10 μ M and 20 μ M.
Next, the ability of DQA (3, 4-dicaffeoylquinic acid) to scavenge superoxide anions and hydroxyl radicals was measured using ESR spectroscopy. In the absence of D QA (3, 4-dicaffeoylquinic acid) in the superoxide anion signal (signal), a 1922 signal was present, and in the presence of DQA (3, 4-dicaffeoylquinic acid), a 1390 signal was present (fig. 3). In addition, 3375 signal appeared in the absence of DQA (3, 4-dicaffeoylquinic acid) and 2278 signal appeared in the presence of DQA (3, 4-dicaffeoylquinic acid) (fig. 4). It is thus found that DQA (3, 4-dicaffeoylquinic acid) has a scavenging effect on superoxide anions and hydroxyl radicals.
After DCF-DA staining, UVB-induced intracellular ROS production was detected using confocal microscopy and fluorescence spectrometer (FIGS. 5 and 6). As a result, it was confirmed that UVB-induced intracellular ROS were eliminated by DQA (3, 4-dicaffeoylquinic acid).
In conclusion, DQA (3, 4-dicaffeoylquinic acid) is not cytotoxic and has a protective effect against the inflammatory response of H2O2Induced intracellular ROS, UVB-induced intracellular ROS scavenging, and confirming the scavenging ability for superoxide anion and hydroxyl radical.
Experimental example 2 Effect of DQA on UVB-induced lipid peroxidation and DNA Damage
UVB radiation initiates lipid peroxidation and cell damage. First, lipid peroxidation was detected in HaCaT cells using confocal microscopy after DPPP treatment. Figure 7 shows that UVB-induced lipid peroxidation was generated in UVB-treated cells, while it was reduced in DQA (3, 4-dicaffeoylquinic acid) -pretreated cells. Then, it was confirmed by comet analysis whether DQA (3, 4-dicaffeoylquinic acid) reduced DNA damage induced by UVB. As a result, it was confirmed that the amount of DNA decomposition was increased by UVB stimulation and DQA (3, 4-dicaffeoylquinic acid) significantly decreased the amount of DNA decomposition (FIG. 8). From this, it was found that DQA (3, 4-dicaffeoylquinic acid) inhibits lipid peroxidation induced by UVB and inhibits DNA damage.
EXAMPLE 3 Effect of DQA on apoptosis
UVB radiation triggers apoptosis in HaCaT cells. Fig. 9 shows the effect of DQA (3, 4-dicaffeoylquinic acid) on apoptosis induced by UVB (fig. 9). Apoptotic bodies were confirmed by UVB irradiation in HaCaT cells. DQA (3, 4-dicaffeoylquinic acid) significantly reduced apoptotic bodies induced by UVB irradiation (figure 10).
Apoptosis results in changes in mitochondrial membrane potential. Therefore, mitochondrial membrane potential was detected by staining with the fluorescent dye JC-1. As a result, the cells irradiated with UVB showed an increase in fluorescence more than the control cells. However, DQA (3, 4-dicaffeoylquinic acid) reduced fluorescence compared to UVB-irradiated cells (fig. 11).
In conclusion, it is known that DQA (3, 4-dicaffeoylquinic acid) has a protective effect on apoptosis induced by UVB.
EXAMPLE 4 Effect of DQA on PM and UVB induced ROS and apoptosis
The combination of mote (PM) and UVB induces intracellular ROS and cell damage. Therefore, ROS levels and apoptotic bodies were irradiated under treated PM2.5 and UVB. Figures 12 and 13 show that the group treated PM2.5 with UVB produced more ROS and apoptotic bodies than the group treated UVB alone. In addition, it was confirmed that DQA (3, 4-dicaffeoylquinic acid) significantly reduced intracellular ROS levels and apoptotic bodies in the group treated with PM2.5 together with UVB and the group treated with UVB alone.
From this, it is known that DQA (3, 4-dicaffeoylquinic acid) inhibits ROS and apoptotic bodies induced by UVB or UVB and Particulate Matter (PM) treatment in human keratinocyte cell lines, and has an effect of protecting skin from ultraviolet rays and particulate matter.
Although the preferred embodiments of the present invention have been described in detail, the scope of the present invention is not limited thereto, and various modifications and improvements that can be performed by those skilled in the art using the basic concept of the present invention defined in the claims should also fall within the scope of the present invention.
Claims (9)
1. A cosmetic composition for protecting skin from active oxygen, ultraviolet rays or fine dusts, which comprises 3, 4-dicaffeoylquinic acid or a cosmetically acceptable salt thereof as an active ingredient.
2. The cosmetic composition according to claim 1, wherein the active oxygen is one or more selected from the group consisting of hydrogen peroxide, superoxide anion, and hydroxyl radical.
3. The cosmetic composition of claim 1, wherein the ultraviolet light is ultraviolet B.
4. The cosmetic composition according to claim 1, wherein the 3, 4-dicaffeoylquinic acid exhibits skin-protective activity through scavenging of active oxygen due to ultraviolet B.
5. The cosmetic composition of claim 1, wherein said 3, 4-dicaffeoylquinic acid exhibits skin protective activity by reducing intracellular lipid peroxidation or DNA damage effects due to ultraviolet B.
6. The cosmetic composition of claim 1, wherein said 3, 4-dicaffeoylquinic acid exhibits skin protective activity by hindering the effects of apoptosis of cells exposed by ultraviolet B or mote.
7. The cosmetic composition according to claim 1, wherein the cosmetic composition is one or more selected from the group consisting of a solution, an ointment for external use, a cream, a foam, a nutrient solution, a soft lotion, a pack, a soft water, an emulsion, a makeup cream, an essence, a soap, a liquid cleanser, a bathing agent, a sunscreen cream, a suntan oil, a suspension, an emulsion, a paste, a gel, an emollient, a powder, a soap, a surfactant-containing face wash, an oil, a powder foundation, an emulsion foundation, a wax foundation, a patch, and a spray.
8. A quasi-pharmaceutical composition for protecting skin from active oxygen, ultraviolet rays or fine dusts, which comprises 3, 4-dicaffeoylquinic acid or a physiologically acceptable salt thereof as an active ingredient.
9. A skin external preparation composition for protecting skin from active oxygen, ultraviolet rays or fine dusts, which comprises 3, 4-dicaffeoylquinic acid or a physiologically acceptable salt thereof as an active ingredient.
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| PCT/KR2018/008346 WO2019059511A2 (en) | 2017-09-25 | 2018-07-24 | Cosmetic composition containing 3,4-dicaffeoylquinic acid for skin protection against reactive oxygen species, ultraviolet radiation, or fine dust |
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| KR20230130479A (en) * | 2022-03-03 | 2023-09-12 | 서울대학교병원 | Compositions for preventing, alleviating, or treating dry eye disease or meibomian gland dysfunction |
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| KR20110000356A (en) * | 2009-06-26 | 2011-01-03 | 이화여자대학교 산학협력단 | Cosmetic composition comprising an extract of aster ageratoides turcz. var. ageratoides having whitening activities |
| KR20160030626A (en) * | 2014-09-11 | 2016-03-21 | 주식회사 사임당화장품 | Cosmetic composition for prevention or amelioration of skin photodamage containing extracts of Cornus walteri leaves as an active ingredient |
| US20160228394A1 (en) * | 2013-09-30 | 2016-08-11 | Calscience International Ltd | Compositions Comprising A Conjugate of Quinic Acid Wth Caffeic Acid, Cosmetic And Therapeutic Uses |
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| KR20120071841A (en) * | 2010-12-23 | 2012-07-03 | 중앙대학교 산학협력단 | Composition for treating or preventing atopic dermatitis comprising extract from ilex rotunda leaf or caffeoyl derivatives |
| CN103415299B (en) * | 2011-01-03 | 2017-02-08 | 株式会社爱茉莉太平洋 | Composition for combating oxidation and alleviating detrimental effects on skin caused by Asian Dust |
| CN104546819A (en) * | 2013-10-09 | 2015-04-29 | 中国医学科学院药物研究所 | Use of dicaffeoylquinic acid in treatment of systemic autoimmune disease |
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| US20160228394A1 (en) * | 2013-09-30 | 2016-08-11 | Calscience International Ltd | Compositions Comprising A Conjugate of Quinic Acid Wth Caffeic Acid, Cosmetic And Therapeutic Uses |
| KR20160030626A (en) * | 2014-09-11 | 2016-03-21 | 주식회사 사임당화장품 | Cosmetic composition for prevention or amelioration of skin photodamage containing extracts of Cornus walteri leaves as an active ingredient |
Non-Patent Citations (1)
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| NINGJIAN LIANG，等: ""Role of Chlorogenic Acids in Controlling Oxidative and Inflammatory Stress Conditions"", 《NUTRIENTS》 * |
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