KR102149057B1 - Apoptosis inhibitor comprising 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone and use thereof - Google Patents

Abstract

The present invention includes 2-carbomrthoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone (2-carbomrthoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone) It relates to an apoptosis (apoptosis) inhibitor, a pharmaceutical composition and a cosmetic composition for preventing, treating or improving cell damage caused by ultraviolet (UV) including the same. The 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone of the present invention can effectively inhibit cell damage, particularly apoptosis, caused by cytotoxic substances and ultraviolet rays. Since it exhibits an effect, it can be applied as an agent capable of inhibiting apoptosis, in particular, a pharmaceutical composition capable of effectively blocking cell damage and a cosmetic composition.

Description

Apoptosis inhibitors containing 2-carbomethoxy-2, 3-epoxy-3-prenyl-1, 4-naphthoquinone and uses thereof {APOPTOSIS INHIBITOR COMPRISING 2-CARBOMETHOXY-2,3-EPOXY-3-PRENYL -1,4-NAPHTHOQUINONE AND USE THEREOF}

The present invention includes 2-carbomrthoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone (2-carbomrthoxy-2, 3-epoxy-3-prenyl-1,4-naphthoquinone) It relates to an apoptosis (apoptosis) inhibitor, a pharmaceutical composition and a cosmetic composition for preventing, treating or improving cell damage caused by ultraviolet (UV) including the same.

Apoptosis refers to suicide of cells, and is a function of cells to maintain homeostasis of an individual, including regulation of normal ontogeny and removal of abnormal cells. Apoptosis occurs in response to stimuli inside and outside cells, and is accompanied by characteristic changes such as cytoplasmic destruction, cell membrane bubble formation, cytoskeleton changes, cell contraction, chromosome condensation, and DNA fragmentation.

Such apoptosis is a very important physiological phenomenon and is precisely regulated by complex mechanisms in vivo, and induction of inappropriate apoptosis due to abnormal regulation is associated with various diseases. Specifically, excessive cell death may cause destruction of specific cells and loss of in vivo functions mediated by this, and examples include central nervous system diseases, cardiovascular diseases, and autoimmune diseases.

On the other hand, damage to cells due to ultraviolet rays, especially damage to skin cells, is a major cause of aging, sunburn, and skin cancer, and is mainly related to the death of skin cells. Mainly used as a means to prevent such damage to the skin is the use of a sunscreen agent that prevents the penetration of ultraviolet rays into the skin.

However, by applying these sunscreens to the skin, they can only partially block the penetration of UV rays into the skin, and it has not been a fundamental solution to prevent or inhibit damage to the skin cells themselves, that is, the death of skin cells. There was a problem.

KR 10-2010-0081627 A

Park Jong-hee, Herbal Medicine Encyclopedia (bottom), Book Publishing Shinil Sangsa, p. 796-797, 2002 Jun DY, et al., Apoptogenic activity of Zanthoxylum schinifolium toward human acute leukemia Jurkat T cells is ssociated with ER stress-mediated caspase-8 activation that stimulates mitochondria-dependent or -independent caspase cascade, Carcinogenesis, 28, pp. 1303-1313, 2007 Jun DY, et al., Anti-adipogenic activity of 2-carbomrthoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone from Rubia cordifolia L., Journal of medicinal food 14(5), pp. 454-461, 2011

The present invention has been conceived to solve the problems of the prior art as described above, and the problem to be solved in the present invention is an apoptosis inhibitor capable of inhibiting apoptosis of cells exposed to harmful environments such as cytotoxic substances or ultraviolet rays. Is to provide. In addition, the problem to be solved in the present invention is to provide a pharmaceutical composition and a cosmetic composition for preventing, inhibiting, treating, and improving damage to cells exposed to ultraviolet rays.

In order to solve the above problems, the present invention is 2-carbomrthoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone (2-carbomrthoxy-2,3-epoxy-3-prenyl -1,4-naphthoquinone) containing apoptosis inhibitors.

The apoptosis may be induced by microtubule damage.

The cell death may be induced by DNA damage.

The cell death may be induced by UV irradiation.

In addition, the present invention provides a pharmaceutical composition for preventing or treating cell damage caused by ultraviolet rays comprising 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone.

The cell damage caused by ultraviolet rays is preferably a skin disease caused by ultraviolet rays.

The skin disease caused by ultraviolet rays is preferably selected from the group consisting of photoaging, spots, freckles, blemishes, dry skin, skin wrinkles, sunburn, photokeratosis, photoallergies, and skin cancer.

In addition, the present invention provides a cosmetic composition for preventing or improving cell damage caused by ultraviolet rays comprising 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone.

The cell damage caused by ultraviolet rays is preferably a skin disease caused by ultraviolet rays.

The skin disease caused by ultraviolet rays is preferably selected from the group consisting of photoaging, spots, freckles, blemishes, dry skin, skin wrinkles, sunburn, photokeratosis, photoallergies, and skin cancer.

The 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone of the present invention can effectively inhibit cell damage, particularly apoptosis, caused by cytotoxic substances and ultraviolet rays. Since it exhibits an effect, it can be applied as an agent capable of inhibiting apoptosis, in particular, a pharmaceutical composition capable of effectively blocking cell damage and a cosmetic composition.

Figure 1 shows apoptotic sub-G1 peak (A), mitochondrial membrane potential loss (B), caspase activation and PARP cleavage induced by treatment with nocodazole (0.3 μM), 2-methoxyestradiol (0.1 μM) or camptothecin (0.05 μM). (C) showing the inhibitory activity of 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone (expressed as'CMEP-NQ') (10 μM) of the present invention on (C) It is the result.
Figure 2 is a 2-carbomethoxy-2,3 of the present invention on apoptotic DNA fragmentation of human Jurkat T cells induced by treatment with Nocodazole (0.3 μM), 2-methoxyestradiol (0.1 μM) or camptothecin (0.05 μM). Results showing the inhibitory activity of -epoxy-3-prenyl-1,4-naphthoquinone (expressed as'CMEP-NQ') (10 μM).
Figure 3 is a 2-carbomethoxy-2,3-epoxy-3-prenyl- of the present invention on apoptosis (A) and mitochondrial membrane potential loss (B) of human keratinocytes (HaCaT) caused by UV irradiation. Results showing the inhibitory activity of 1,4-naphthoquinone (expressed as'CMEP-NQ') (10 μM).

Hereinafter, the present invention will be described in detail.

The inventors of the present invention are 2-carbomethoxy-2 isolated from the extract of Rubiae Radix , as disclosed in Korean Patent Registration No. 10-1072663, which has been patented and registered by the inventors of the present invention. Cytotoxicity of ,3-epoxy-3-prenyl-1,4-naphthoquinone, such as nocodazole, 2-methoxyestradiol and campotothecin The effect of inhibiting cell death by the substance or ultraviolet irradiation was assayed, and as a result, the compound isolated by the inventors of the present invention can effectively inhibit apoptosis induced by the aforementioned cytotoxic substances or ultraviolet irradiation. By confirming the present invention was completed.

Thus, the present invention is 2-carbomrthoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone (2-carbomrthoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone) It provides a cell death inhibitor comprising a.

The compound of the present invention, as disclosed in Korean Patent Registration No. 10-1072663 by the inventors of the present invention, Cheonchogeun ( Rubiae Radix ) as separated from the detailed separation and purification process is described in detail in the above registered patent. In addition, it is obvious to a person skilled in the art that the compound of the present invention may be prepared through a certain chemical synthesis process in addition to the case obtained according to the separation method described in the registered patent.

'Apoptosis' referred to in the present invention should be understood to mean the natural death of cells, that is, apoptotic cell death.

Therefore, the cell death may be induced by microtubule daage. Representative cytotoxic substances that can cause microtubule damage include nocodazole and 2-methoxyestradiol, but are not limited thereto.

In addition, the cell death may be induced by DNA damage. Representative cytotoxic substances that can cause DNA damage include camptothecin, but are not limited thereto.

In addition, the cell death may be induced by ultraviolet irradiation. The ultraviolet rays include UVA having a wavelength of 320-400 nm, UVB having a wavelength of 280-320 nm, and UVC having a wavelength of 180-280 nm individually or entirely, and as a preferred embodiment, UVC as applied in the following examples of the present invention Can be

The term'apoptosis inhibitor' referred to in the present invention refers to a substance capable of inhibiting apoptosis of cells constituting an individual of a mammal, including humans, or cells separated from the individual and present.

Therefore, the'apoptosis inhibitor' is a medical use for the prevention or treatment of various diseases related to apoptosis, a use as a research reagent capable of inhibiting apoptosis in the study of various animal and plant cells including cell lines, or apoptosis. It may be applied to health functional foods and functional cosmetics for the prevention or improvement of various diseases caused by this.

As a preferred embodiment, the present invention provides a pharmaceutical composition for preventing or treating cell damage caused by ultraviolet rays comprising 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone do.

The cell damage caused by ultraviolet rays is preferably a skin disease caused by ultraviolet rays.

The skin disease caused by ultraviolet rays is preferably selected from the group consisting of photoaging, spots, freckles, blemishes, dry skin, skin wrinkles, sunburn, photokeratosis, photoallergies, and skin cancer.

The pharmaceutical composition containing 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone of the present invention is prepared in a powder, granule, or tablet according to a conventional method according to each purpose of use. , Capsules, suspensions, emulsions, syrup, oral formulations such as aerosols, and injections of sterile injectable solutions can be formulated and used. Orally or intravenously, intraperitoneally, subcutaneously, rectal, topical administration, etc. It can be administered through a variety of routes, including.

Such pharmaceutical compositions may further include a carrier, excipient, or diluent, and examples of suitable carriers, excipients or diluents that may be included include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, Starch, gum acacia, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methyl cellulose, amorphous cellulose, polyvinyl pyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and mineral oil And the like. In addition, the pharmaceutical composition of the present invention may further include a filler, an anti-aggregating agent, a lubricant, a wetting agent, a fragrance, an emulsifying agent, a preservative, and the like.

Solid preparations for oral administration include tablets, pills, powders, granules, capsules, and the like, and such solid preparations include at least one excipient, such as starch, calcium carbonate, sucrose, lactose, and gelatin, in the pharmaceutical composition. And the like are mixed and formulated. Further, in addition to simple excipients, lubricants such as magnesium stearate and talc may be used.

Examples of liquid formulations for oral use include suspensions, solvents, emulsions, syrups, etc., and various excipients, such as wetting agents, sweeteners, fragrances, and preservatives, in addition to water and liquid paraffin, which are simple diluents commonly used Can be included.

Formulations for parenteral administration include sterilized aqueous solutions, non-aqueous solutions, suspensions, emulsions, lyophilized agents, suppositories, and the like. Non-aqueous solvents and suspensions may include propylene glycol, polyethylene glycol, vegetable oils such as olive oil, and injectable esters such as ethyloleate. Injectables may contain conventional additives such as solubilizing agents, isotonic agents, suspending agents, emulsifying agents, stabilizing agents, and preservatives.

The 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone of the present invention is administered in a pharmaceutically effective amount. In the present invention, "pharmaceutically effective amount" refers to an amount sufficient to treat a disease at a reasonable benefit/risk ratio applicable to medical treatment, and the effective dose level is the type of disease, severity, drug activity, Sensitivity to drugs, time of administration, route of administration and rate of excretion, duration of treatment, factors including drugs used concurrently, and other factors well known in the medical field. The pharmaceutical composition of the present invention may be administered as an individual therapeutic agent or administered in combination with other therapeutic agents, may be administered sequentially or simultaneously with a conventional therapeutic agent, and may be administered single or multiple. It is important to administer an amount capable of obtaining the maximum effect in a minimum amount without side effects in consideration of all the above factors, which can be easily determined by a person skilled in the art.

The effective amount of 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone in the pharmaceutical composition of the present invention may vary depending on the patient's age, sex, and body weight, and generally 1 to 5,000 mg per kg, preferably 10 to 1,000 mg, may be administered daily or every other day, or divided into 1 to 3 times a day. However, since it may increase or decrease depending on the route of administration, the severity of the disease, sex, weight, age, etc., the dosage amount is not limited by any method.

The pharmaceutical composition of the present invention can be administered to a subject through various routes. All modes of administration can be expected and can be administered, for example, by oral, rectal or intravenous, intramuscular, subcutaneous, intrauterine dural or cerebrovascular injection.

In the present invention, "administration" means providing a predetermined substance to a patient by any suitable method, and the route of administration of the pharmaceutical composition of the present invention is oral or parenteral through all general routes as long as it can reach the target tissue. It can be administered orally. In addition, the composition of the present invention may be administered using any device capable of delivering an active ingredient to target cells.

In the present invention, the "object" is not particularly limited, but includes, for example, human, monkey, cow, horse, sheep, pig, chicken, turkey, quail, cat, dog, mouse, mouse, rabbit, or guinea pig And, preferably, a mammal, more preferably a human.

In a preferred embodiment, the present invention provides a research reagent for effectively inhibiting apoptosis, including 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone.

The reagent may further contain an appropriate preservative to secure the stability of the compound, and the type and amount of the preservative are obvious to those skilled in the art.

The reagents of the present invention may be treated at various concentrations depending on the purpose of the study, the type of cells used, and the number of cells, but it is preferable to treat them at a concentration of 0.1 to 15 μg/ml in consideration of cytotoxicity. It is more preferable to treat at a concentration of 10 μg/ml.

The treatment time may also vary depending on the purpose of the study, the type of cells to be used, and the number of cells, but, for example, it is preferable to treat the compound of the above concentration for 0.5 to 3 hours.

As a preferred embodiment, the present invention provides a health functional food for preventing or improving cell damage caused by ultraviolet rays containing 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone do.

The cell damage caused by ultraviolet rays is preferably a skin disease caused by ultraviolet rays.

The skin disease caused by ultraviolet rays is preferably selected from the group consisting of photoaging, spots, freckles, blemishes, dry skin, skin wrinkles, sunburn, photokeratosis, photoallergies, and skin cancer.

The health functional food of the present invention can be used in various ways such as foods and beverages that are effective in preventing or improving cell damage caused by ultraviolet rays. Foods containing 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone of the present invention include, for example, various foods, beverages, gum, tea, vitamin complexes, There are health supplement foods, and can be used in the form of powder, granule, tablet, capsule or beverage.

The 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone of the present invention can be generally added in an amount of 0.01 to 15% by weight of the total food weight, and the health beverage composition is 100 ml It can be added in a ratio of 0.02 to 10 g, preferably 0.3 to 1 g, based on.

The health functional food of the present invention may contain the compound as an essential component in the indicated ratio as an additional component, as well as food supplementary additives acceptable for food, such as natural carbohydrates and various flavoring agents.

Examples of the natural carbohydrates include monosaccharides such as glucose and fructose, disaccharides such as maltose and sucrose, and conventional sugars such as polysaccharides such as dextrin and cyclodextrin, and sugar alcohols such as xylitol, sorbitol, and erythritol.

Taumatin as the flavoring agent; Natural flavoring agents such as stevia, such as rebaudioside A or glycyrrhizin, and synthetic flavoring agents such as saccharin and aspartame, may be used. The ratio of the natural carbohydrate is generally about 1 to 20 g, preferably about 5 to 12 g per 100 ml of the health functional food of the present invention. In addition to the above, the health functional food of the present invention includes various nutrients, vitamins, minerals, synthetic flavoring agents and natural flavoring agents, and other flavoring agents, coloring agents and thickeners, pectic acid and salts thereof, alginic acid and salts thereof, organic acids, protective colloids. It may contain thickeners, pH adjusters, stabilizers, preservatives, glycerin, alcohols, carbonation agents used in carbonated beverages, and the like. In addition, the health functional food of the present invention may contain pulp for the production of natural fruit juices, fruit juice drinks, and vegetable drinks. These components may be used independently or in combination. The proportion of these additives is generally selected from 0.01 to about 20 parts by weight per 100 parts by weight of 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone of the present invention.

As a preferred embodiment, the present invention provides a cosmetic composition for preventing or improving cell damage caused by ultraviolet rays comprising 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone. .

The cell damage caused by ultraviolet rays is preferably a skin disease caused by ultraviolet rays.

The skin disease caused by ultraviolet rays is preferably selected from the group consisting of photoaging, spots, freckles, blemishes, dry skin, skin wrinkles, sunburn, photokeratosis, photoallergies, and skin cancer.

The cosmetic composition of the present invention may contain the 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone of the present invention by itself or in the form of a salt. The salt is preferably an acid addition salt formed by free acid. Organic acids and inorganic acids may be used as the free acid. The organic acids are, for example, citric acid, acetic acid, lactic acid, tartaric acid, maleic acid, fumaric acid, formic acid, propionic acid, oxalic acid, trifluoroacetic acid, benzoic acid, gluconic acid, metasulfonic acid, glycolic acid, succinic acid, 4-toluenesulfonic acid, glutamic acid and aspartic acid. And the like, but are not limited thereto. In addition, examples of the inorganic acid include hydrochloric acid, bromic acid, sulfuric acid, and phosphoric acid, but are not limited thereto.

The cosmetic composition may be prepared in a liquid or solid form using a base, auxiliaries and additives such as water, alcohol, propylene glycol, stearic acid, glycerol, cetyl alcohol and liquid paraffin, which are commonly used in the cosmetic field. . Cosmetics in liquid or solid form may include lotions, creams, lotions, gelling agents, sprays, etc., but are not limited thereto.

More specifically, the cosmetic composition of the present invention comprises the 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone of the present invention, and is based on a dermatologically acceptable excipient. Cosmetic composition (toilet, cream, essence, cleansing foam, cleansing water, pack, body oil), color cosmetic composition (foundation, lipstick, mascara, maker-up base), hair product composition (shampoo, conditioner, hair conditioner, hair gel), It can be prepared in the form of a functional cosmetic composition (sunscreen agent, wrinkle improvement agent) and soap. The excipients may include, for example, emollients, skin penetration enhancers, colorants, fragrances, emulsifiers, thickeners, and solvents, but are not limited thereto. In addition, fragrances, colorants, disinfectants, antioxidants, preservatives, moisturizing agents, etc. may be additionally included, and thickeners, inorganic salts, synthetic polymer materials, etc. may be further included for the purpose of improving physical properties.

For example, when preparing a face wash and soap containing 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone of the present invention, 2 -Can be easily prepared by adding carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone. In addition, when preparing a cream, it can be prepared by adding 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone to a general oil-in-water cream base. Synthetic or natural materials such as amino acids, minerals, vitamins, etc. for the purpose of improving physical properties such as fragrances, chelating agents, coloring agents, antioxidants, preservatives, and the like may be additionally added.

The content of 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone contained in the cosmetic composition of the present invention is 0.0001 to 50% by weight, preferably based on the total weight of the cosmetic composition. It may be contained in the range of 0.01 to 10% by weight.

Hereinafter, the present invention will be described in more detail through examples. The following examples are only one preferred specific example of the present invention, and the scope of the present invention is not limited to the scope of the following examples.

[ Example ]

One. Microtubule - damaging agents ( nocodazole , 2- methoxyestradiol )Wow DNA -damaging agent ( campotothecin ) On apoptosis induced by 2- Carbomethok Si-2,3-epoxy-3- Prenyl -1,4- Naphthoquinone Cytoprotective activity

In order to investigate the cytotoxic effect of 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone on the apoptosis of human cells by cytotoxic substances, various microtubule-damaging agents ( nocodazole, 2-methoxyestradiol) or DNA-damaging agent (campotothecin) in human Jurkat T cells to induce apoptosis and affect 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4 -The cytoprotective effect of naphthoquinone was investigated.

First, human Jurkat T cells were pretreated with 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone (10 μM) for 1 hour, followed by nocodazole (0.3 μM). , 2-methoxyestradiol (0.1 μM) or camptothecin (0.05 μM) was incubated for 20 hours, respectively.

In order to investigate the extent of cell damage and apoptosis caused by these cytotoxic substances after culture, the distribution of the cell cycle and mitochondrial membrane potential loss (Δψm) were analyzed by flow cytometry. In addition, apoptosis-related caspase-9 activation and the presence of PARP cleavage were analyzed and assayed by Western blotting.

As a result, as shown in Figure 1, 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone is a microtubule-damaging agent (nocadazole or 2-methoxyestradiol) or DNA-damaging It was confirmed that it has a cytoprotective activity that effectively blocks apoptosis by the agent (camptothecin).

In particular, since it has a protective effect against mitochondrial damage, it was confirmed that it has excellent efficacy in inhibiting the activation of the apoptotic caspase cascade, which is induced dependently on mitochondrial damage.

In addition, the cytoprotective activity of 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone, which effectively inhibits apoptosis induced by Nocodazole, 2-methoxyestradiol, or camptothecin treatment, Apoptotic DNA fragmentation used as a marker for apoptosis to determine whether it is due to the inhibitory effect of 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone on drug-induced apoptosis. The inhibitory activity of 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone against

As a result, as shown in Figure 2, 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone (10 μM) is nocodazole (0.3 μM), 2-methoxyestradiol (0.1 μM) or camptothecin (0.05 μM) treatment-induced apoptotic DNA fragmentation was significantly inhibited.

These results show that 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone protects cells from the cytotoxic effects of various cytotoxic drugs through induction of apoptosis. This suggests that it is a material with excellent utility with efficacy.

2. UV irradiation 2- affecting apoptosis induced by Carbomethoxy -2,3-epoxy-3- Prenyl -1,4- Naphthoquinone Skin cell protection activity

To investigate the effect of 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone on apoptosis caused by irradiation of human skin cells with ultraviolet (UV) light. , After pretreatment of 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone (10 μM) to HaCaT cells, a human keratinocyte cell line, for 1 hour , UVC was irradiated at a dose of 25 Joule/m ² . Thereafter, the cells were cultured for 24 hours, and then the presence or absence of the cells, the distribution of the cell cycle, and the extent of mitochondrial membrane potential loss were confirmed by flow cytometery.

As a result, as shown in FIG. 3, 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone almost reduced apoptosis caused by skin cell damage caused by UVC irradiation. It was confirmed that it has excellent cell protection activity that blocks most. In addition, 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone has the effect of remarkably inhibiting intracellular mitochondrial membrane potential loss (Δψm) caused by UVC irradiation. Confirmed.

The above study results show that 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone protects cells from cell damage that may be caused to human skin cells by UVC irradiation. It confirms that there is, and also suggests that it can be used as a material that protects the health of the skin from UV.

3. 2- Carbomethoxy -2,3-epoxy-3- Prenyl -1,4- Naphthoquinone Toxicity test

When 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone was treated with normal human peripheral blood cells, it was confirmed that the cytotoxicity was very low and there was no liver toxicity [Korea Conducted on the new drug platform of the Chemical Research Institute].

Claims (8)

Apoptosis containing 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone (2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone) Reagent composition for inhibition. The reagent composition for inhibiting apoptosis according to claim 1, wherein the cell death is induced by microtubule damage, DNA damage, or ultraviolet irradiation. UV light containing 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone A pharmaceutical composition for preventing or treating cell damage caused by. The pharmaceutical composition of claim 3, wherein the cell damage caused by ultraviolet rays is a skin disease caused by ultraviolet rays. The pharmaceutical composition according to claim 4, wherein the skin disease caused by ultraviolet rays is selected from the group consisting of sunburn, photokeratosis, photoallergy, and skin cancer. UV light containing 2-carbomethoxy-2,3-epoxy-3-prenyl-1,4-naphthoquinone A cosmetic composition for preventing or improving cell damage caused by. The cosmetic composition of claim 6, wherein the cell damage caused by ultraviolet rays is a skin disease caused by ultraviolet rays. The cosmetic composition according to claim 7, wherein the skin disease caused by ultraviolet rays is selected from the group consisting of photoaging, melasma, freckles, blemishes, dry skin, skin wrinkles, sunburn, photokeratosis, photoallergies, and skin cancer.

Images