KR20190020539A - A composition for improving alopecia containing novel compounds isolated from chestnut bur - Google Patents

Abstract

The present invention relates to a composition for reducing hair loss including a novel compound derived from a chestnut burr, which can minimize damage and irritation of hair and can promote the growth of hair. The composition comprises at least one selected from the group consisting of compounds represented by following chemical formulas 1 to 7, as an active ingredient.

Description

TECHNICAL FIELD [0001] The present invention relates to a composition for improving hair loss comprising a novel compound derived from chestnut tree,

The present invention relates to a composition for improving hair loss derived from natural materials, which can minimize damage and stimulation of hair and promote hair growth.

The animals have a molting period in which the hairs are totally replaced by the seasons, but in humans, some of the whole hairs are constantly replaced every day, so that a similar number is always maintained.

The hair cycle can be divided into three periods of growth period, regenerative period and pausing period. Among them, anagen is a period when active division of cells occurs in the dermal papilla and new hair growth is accelerated. During this period, hair grows .

The period of hair appearance is approximately 3 to 5 years for males and 4 to 6 years for females, and about 80 to 85% of hair as a whole is the growth period. The catagen is about 3 to 4 weeks when cell division is gradually stopped.

Finally, the taloge is a period when the hair is separated from the capillaries by the atrophy of the papillary hair and is simply put on the scalp. It is about 3 months. The hair in the pauses is easily separated from the fur by physical stimulation.

In general, hair loss refers to the shortening of hair growth rate in the growing period and the increase of hair in the retrograde period or rest period in such a cycle, resulting in abnormal abundance of hair.

Although human hair is irrelevant to life, it has a decisive influence on human impressions and appearances, so much attention has been socially attracted, and in recent years, the awareness that the hair loss has been recognized as a symptom is increasing.

Especially, as the recent upsurge and industrialization accelerate, excessive stress and lifestyle habits of socio-cultural factors are causing the hair loss population to increase rapidly. In recent years, hair loss has increased not only in middle-aged men but also in the elderly, and various studies for analyzing the various causes of hair loss have been actively conducted.

Meanwhile, in the cosmetics industry, many products using natural products have been developed to reduce skin irritation caused by various chemical substances. In addition to low adverse effects on skin, natural materials have recently become increasingly appreciated as a cosmetic raw material as consumers' response to cosmetics using natural materials has increased.

Accordingly, there is an increasing demand for cosmetics using natural materials with high consumer acceptance, and various researches on the development of multi-functional cosmetics having excellent biosafety and skin-improving effects have been actively conducted.

The inventors of the present invention have found that a new compound isolated from Bombyx mori effectively promotes the growth of dermal papilla cells and keratinocytes as a result of efforts to find a substance having a hair growth promoting activity and alopecia improving activity derived from natural materials as a part of the above technical problem. Thereby completing the present invention.

Disclosure of Invention Technical Problem [8] Accordingly, the present invention has been made in an effort to solve the problems of the prior art described above, and it is an object of the present invention to provide a composition for improving hair loss, which has excellent human safety and is excellent in hair loss prevention and hair growth promoting ability.

According to an aspect of the present invention, there is provided a composition for improving depilation comprising at least one selected from the group consisting of compounds represented by the following formulas (1) to (7) as an active ingredient.

[Chemical Formula 1]

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In one embodiment, the compounds of Formulas 1 to 7 may be isolated in chestnuts.

In one embodiment, the composition for alleviating hair loss may promote growth of dermal papilla cells or keratinocytes.

According to another aspect of the present invention, there is provided a cosmetic composition comprising the composition for alleviating hair loss as an active ingredient.

In one embodiment, the cosmetic composition is selected from the group consisting of hair toners, hair lotions, hair creams, hair sprays, hair mousses, hair gels, hair soaps, hair shampoos, hair rinses, hair packs, Or more.

According to another aspect of the present invention, there is provided an external preparation for skin comprising the composition for improving depilation hair loss as an active ingredient.

According to another aspect of the present invention, there is provided a pharmaceutical composition for preventing or treating hair loss comprising the composition for improving depilation hair loss as an active ingredient.

According to another aspect of the present invention, there is provided a health functional food for alleviating hair loss comprising the composition for improving alleviating hair loss as an active ingredient.

According to another aspect of the present invention, there is provided a method for preventing or treating hair loss, comprising the step of administering the composition for improving hair loss to a non-human individual.

According to the present invention, the composition contains a naturally-occurring compound as an active ingredient, has low toxicity to human body, and has excellent hair growth promoting activity, so that it can be widely used as an application for improvement and prevention of hair loss.

It should be understood that the effects of the present invention are not limited to the above effects and include all effects that can be deduced from the detailed description of the present invention or the configuration of the invention described in the claims.

Figures 1 and 2 show the results of treating the compound according to one embodiment of the present invention with I-DPC and measuring the degree of cell proliferation for 72 hours.
Figures 3 and 4 are the results of treating the compound according to one embodiment of the present invention with DPC and measuring the degree of cell proliferation for 72 hours.
FIG. 5 shows the results of measuring the degree of cell proliferation for 72 hours in HaCaT treated with a compound according to an embodiment of the present invention.
Figures 6 and 7 are the results of hair removal after 7-week-old rats were depilated and treated with the compound according to one embodiment of the present invention (Example 3).
Figures 8 and 9 are the results of hair removal after 7-week-old rats were depilated and treated with the compound according to one embodiment of the present invention (Example 7).

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, the present invention will be described with reference to the accompanying drawings. The present invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. When an element is referred to as "comprising ", it means that it can include other elements, not excluding other elements unless specifically stated otherwise.

Unless otherwise defined, can be performed by molecular biology, microbiology, protein purification, protein engineering, and DNA sequencing and routine techniques commonly used in the art of recombinant DNA within the skill of those skilled in the art. These techniques are known to those skilled in the art and are described in many standardized textbooks and references.

Unless otherwise defined herein, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art.

Various scientific dictionaries, including the terms contained herein, are well known and available in the art. Although any methods and materials similar or equivalent to those described herein are found to be used in the practice or testing of the present application, some methods and materials have been described. It is not intended that the invention be limited to the particular methodology, protocols, and reagents, as they may be used in various ways in accordance with the context in which those skilled in the art use them. Hereinafter, the present invention will be described in more detail.

One aspect of the present invention provides a composition for improving depilation comprising at least one selected from the group consisting of compounds represented by the following formulas (1) to (7) as an active ingredient.

[Chemical Formula 1]

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

The term " hair loss " refers to a state in which hair is normally broken at a site where hair should be present, and generally means that the hair of the scalp is missing. Unlike colorless and thick skin, the Virgin Mary can cause cosmetic problems when it is missing.

The above-mentioned "improvement" refers to all the actions of alleviating the alopecia and symptoms of the alopecia using the composition and improving the symptoms of the alopecia. The composition for improving alopecia suppresses the growth of the papillary cells and keratinocytes, Do.

The hair loss can be classified into two types, that is, a case where the hair is clinically formed and a case where the hair is not formed. The hair loss (scarring) in which a scar is formed can not be regenerated due to the destruction of the hair follicle, Scarring) maintains the hair follicles so that the hair can be regenerated after the symptoms disappear.

The hair loss may include, without limitation, alopecia areata, alopecia totalis, alopecia totalis, hair loss, hair loss, hair loss, hair loss, but are not limited to, alopecia universalis, androgenic alopecia, telogen effluvium, anagen effluvium, or chemotherapy-induced alopecia.

The effect of improving hair loss may include the effect of promoting hair growth. The composition for improving hair loss has an excellent effect of preventing hair loss before hair loss begins.

The above-mentioned " comprising as an active ingredient " may mean an amount effective to prevent hair loss, to promote hair growth, for example, to promote the growth promotion activity of dermal papilla cells or keratinocytes related to hair growth efficacy.

The compounds of formulas (1) to (6) are novel triterpene compounds of the cycloartane series isolated from Bombyx mori. These compounds are 3β, 7β, 24-trihydroxy-4,14-dimethyl-9,19-cyclo-5α, 9β-lanost- 3?, 7? -dihydroxy-4,14-dimethyl-9,19-cyclo-5 ?, 9? -lanost-28-oic acid (Formula 2) -dimethyl-9,19-cyclo-5 ?, 9? -lanost-24,28-oic acid (3), 3?, 7 ?, 24? -trihydroxy-4,14-dimethyl- lanost-25-en-28-oic acid (Formula 4), 3?, 7 ?, 24? -trihydroxy-4,14-dimethyl-9,19-cyclo-5 ?, 9? (5), 3?, 7?, 23?, 24 ?, 25-pentahydroxy-4,14-dimethyl-9,19-cyclo-5 ?, 9? -Lanost-28-oic acid.

The compound of formula (7) can be named as 3,3'-di-methylellagic acid as tannin compound isolated from chestnut tree.

The type of the chestnut is not particularly limited. Examples of the chestnut are Castanea crenata , Castanea mollissima , Castanea davidii , China , Castanea henryi , and Castanea seguinii ; Castanea dentata , Castanea pumila), kaseutaneah polyamic alni (Castanea alnifolia), kaseutaneah shaving her (Castanea ashei , Castanea floridana , Castanea paupispina ); Castanea sativa , and so on.

The chestnut extract can be obtained by hot extraction with a lower alcohol solvent such as methanol or ethanol or a mixed solvent thereof, followed by concentration under reduced pressure. In order to more effectively separate the compound, the chestnut can be pulverized by a pin mill or a ball mill pulverizer to 100 to 200 mesh, and can be pulverized at room temperature at a low temperature of less than 40 DEG C or at a high temperature of 60 DEG C or higher Of water as a solvent, or may be extracted with alcohol as a solvent.

The alcohol may be an aliphatic alcohol having 1 to 6 carbon atoms, and specifically, methanol, ethanol, isopropanol, butanol, hexane and the like may be used, but the present invention is not limited thereto.

The alcohol extract may be dispensed into an organic solvent and water. The organic solvent may be selected from aliphatic hydrocarbons having 1 to 10 carbon atoms, aliphatic halogenated hydrocarbons having 1 to 10 carbon atoms, and esters having 2 to 10 carbon atoms.

The extracted hot water can be separated into a water insoluble layer and a water soluble layer by filtration to dissolve in distilled water, and the water soluble layer can be degreased with a nonpolar organic solvent such as chloroform, ether or methylene chloride have.

Since the water-soluble layer may contain a large amount of hydrophilic or hydrophobic impurities as well as the compound, the water-soluble layer may be degreased with a nonpolar organic solvent to remove hydrophobic impurities. Preferably, the degreasing process is performed three times .

In addition, the compound contained in the chestnut extract can be isolated by chromatographic methods well known in the art.

The degreased water-soluble layer may be adsorbed to the nonionic resin for column chromatography after removing the nonpolar organic solvent. The column chromatography can be carried out by a conventional method well known in the art.

The compound may be isolated by further chromatography, such as silica gel column chromatography, and various known methodologies for separating a single compound may be applied.

Another aspect of the present invention provides a cosmetic composition or composition for external application for skin comprising the composition for alleviating hair loss as an active ingredient.

The external preparation for skin or the cosmetic composition may be formulated by a conventional method. In the formulation of the external preparation for skin, Remington's Pharmaceutical Science, Mack Publishing Company, Easton PA can refer to, and in the formulation of the cosmetic composition, International cosmetic ingredient dictionary, 6th ed., The cosmetic, Toiletry and Fragrance Association, Inc., Washington, 1995, which is incorporated herein by reference.

The external preparation for skin or the composition for cosmetics may contain a conventional acceptable carrier such as oil, water, a surfactant, a moisturizer, a lower alcohol, a thickener, a chelating agent, a pigment, a preservative and a flavoring agent. But is not limited thereto.

The composition may further include a base component that can be compounded with general external scalp and hair treatment agents. Specifically, the composition may contain a dissolution aid, a surfactant, a moisturizer, an agitator, a pH adjuster, an antiseptic, an antioxidant, a sequestering agent, , An anti-inflammatory agent, an antimicrobial agent, a solvent, a coloring agent, or a flavoring agent.

The composition may be formulated as a composition for treating hair, such as an emulsion, a cream, a paste, a gel, a lotion, a pack, a lotion, a powder, a spray or a soap, , A hair mousse, a hair gel, a hair soap, a hair shampoo, a hair rinse, a hair pack, and a hair treatment, and may be specifically formulated into a liquid hair shampoo.

In the above-mentioned formulations, components other than the above-mentioned essential ingredients can be appropriately selected and blended by those skilled in the art depending on the use or purpose of the other external preparation.

For example, when the composition of the composition is a paste, cream or gel, an animal fiber, a plant fiber, a wax, a paraffin, a starch, a tracer, a cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc, Can be used.

When the formulation of the composition is a powder or a spray, lactose, talc, silica, aluminum hydroxide, calcium silicate or polyamide powder may be used as the carrier component. In particular, chlorofluorohydrocarbons, propane, And may further include propellants such as dimethyl ether.

When the formulation of the composition is a solution or an emulsion, a solvent, a solvent or an emulsifier may be used as the carrier component. Examples of the solvent include water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, 1,3-butyl glycol oil, glycerol aliphatic ester, polyethylene glycol or fatty acid esters of sorbitan can be used.

When the formulation of the composition is in the form of a suspension, the carrier component may be a liquid diluent such as water, ethanol or propylene glycol, a suspending agent such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester, Cellulose, aluminum metahydroxide, bentonite, agar or tracant, and the like.

However, the auxiliary agent and the mixing ratio thereof can be appropriately selected so as not to affect the desirable properties of the product according to the present invention.

There is provided a pharmaceutical composition for preventing or treating hair loss comprising the above composition for improving depilation hair loss as an active ingredient.

The " prevention " means any action that reduces the frequency or extent of the pathological event. Prevention can be complete or partial. In this case, hair loss symptoms in the subject may be reduced as compared with the case where the composition is not used.

The term " treatment " means any clinical intervention to alter the natural course of a subject or cell to be treated, and may be performed during or during the course of a clinical pathology. The desired therapeutic effect may be to prevent the occurrence or recurrence of the disease, to alleviate the symptoms, to reduce all direct or indirect pathological consequences of the disease, to prevent metastasis, to reduce the rate of disease progression, Relieving or temporarily alleviating the condition, or improving the prognosis.

The compositions can be administered in the form of oral delivery, parenteral delivery. The composition may be administered systemically or topically, and the administration may include oral administration and parenteral administration. The composition may be formulated with a suitable amount of a pharmaceutically acceptable vehicle or carrier to provide a suitable dosage form.

The composition may further comprise a carrier, an excipient and a diluent used in the preparation of the pharmaceutical composition. Examples of the carrier, excipient and diluent include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, acacia rubber, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methylcellulose, But are not limited to, cellulose, polyvinylpyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate or mineral oil.

In addition, the composition may be formulated in the form of oral, granule, tablet, capsule, suspension, emulsion, syrup, aerosol or the like, external preparation, suppository and sterilized injection solution.

The solid preparation for oral administration may be a tablet, a pill, a powder, a granule, a capsule, etc. The solid preparation may be prepared by adding to the compound and its fractions at least one or more excipients such as starch, calcium carbonate, sucrose, lactose , Or gelatin. In addition to the above excipients, lubricants such as magnesium stearate and talc may be used.

The liquid preparation for oral administration may be a suspension, a solution, an emulsion, a syrup, etc. In addition to water and liquid paraffin which are simple diluents, various excipients such as wetting agents, sweeteners, fragrances and preservatives may be used.

The preparation for parenteral administration may be a sterilized aqueous solution, a non-aqueous solvent, a suspension, an emulsion, a lyophilized preparation, or a suppository. Examples of the non-aqueous solutions and suspensions may include injectable esters such as propylene glycol, polyethylene glycol, vegetable oil such as olive oil, and ethyl oleate. Examples of the suppository base include witepsol, macrogol, tween 61, cacao butter, laurin, and glycerogelatin.

The composition may be administered in a pharmaceutically effective amount sufficient to treat the disease at a reasonable benefit / risk ratio applicable to medical treatment, and the effective dose level will depend on the species and severity, age, sex, disease type, Activity, sensitivity to the drug, time of administration, route of administration and rate of release, duration of treatment, factors including co-administered drugs, and other factors well known in the medical arts.

The composition may be administered as an individual therapeutic agent or in combination with other therapeutic agents, and may be administered sequentially or simultaneously with conventional therapeutic agents. And can be administered singly or multiply. It is important to take into account all of the above factors and to administer the amount in which the maximum effect can be obtained in a minimal amount without adverse effect, and can be easily determined by those skilled in the art.

The preferred dosage of the composition may vary depending on the condition and the weight of the patient, the severity of the disease, the type of drug, the route of administration and the period of time, and the appropriate total daily dose may be determined by the treatment within the proper medical judgment range , Generally in an amount of 0.001 to 1000 mg / kg, preferably 0.05 to 200 mg / kg, more preferably 0.1 to 100 mg / kg, once or several times a day.

 Any object can be applied as long as it is an object for prevention or treatment of hair loss, without any particular limitation. For example, it can be applied to any individual such as a monkey, a dog, a cat, a rabbit, a guinea pig, a rat, a mouse, a cattle, a sheep, a pig, . For example, transdermal administration through topical application may be used, but is not limited thereto.

On the other hand, there is no particular limitation on the method of administering the composition, and the composition can be administered orally, and the composition can be administered in a form suitable for application to a hair loss site or in a region where hair loss progress is expected.

In addition, since there is no particular limitation on the method of administration, it is possible to inject directly into the site where the progress of hair loss or hair loss is predicted, or inject it by injection into the artery or vein.

Specifically, the pharmaceutical composition can be used for treatment of hair loss by transdermal dosage formulations.

The above-mentioned "percutaneous administration formulations" are formulations that show effects by administering drugs through the skin, and may be formulated in the form of drugs applied to the skin or drugs applied to the skin. In transdermal administration, the skin permeation of the active ingredient can be made through the intracellular, intracellular, or parenchyma, hairy orifices, etc. by simple diffusion according to the chemical potential, that is, the concentration gradient.

It is not easy to pass through uninjured skin. However, there are advantages in ease of use such as efficiency of drug, control of administration rate, possibility of direct application to affected part, maintenance of relatively constant blood concentration, minimization of side effects of substances showing gastrointestinal toxicity, And reducing the burden on the liver. In order to facilitate skin permeation of the active ingredient, a skin administration promoter may be additionally formulated.

The transdermal preparation can be used without limitation as long as it is a formulation capable of directly administering the active ingredient to the surface of the disease site of the skin. For example, it is formulated into preparations such as ointments, creams, gels, lotions, solutions, emulsions, suspensions, warnings (sticks), pastes, linings, papings, tapes, aerosols or external powders Can be used. To this end, it may further comprise suitable carriers, excipients and diluents conventionally used in the manufacture of conventional transdermal dosage forms.

Also, the dosage level selected from the composition can be controlled according to the activity of the compound, the route of administration, the severity of the hair loss to be treated, and the condition and previous history of the hair loss to be treated. It is, however, within the knowledge of the art to gradually increase the dose until the desired effect is achieved, starting with the dose of the compound at a level lower than that required for achieving the desired therapeutic effect, , Body shape, and body weight.

The composition may be further processed before being formulated into a pharmaceutically acceptable pharmaceutical formulation and may be preferably ground or ground into smaller particles.

Also, the composition will vary depending on the condition and the patient being treated, but it can be determined non-ingeniously.

According to another aspect of the present invention, there is provided a health functional food for alleviating hair loss comprising the composition for improving alleviating hair loss as an active ingredient.

The health functional food refers to a food prepared and processed by using raw materials or ingredients having useful functions in the human body according to the Act on Health Functional Foods. The functional properties include nutrients for the structure and function of the human body, ≪ / RTI > may be meant to be ingested for the purpose of obtaining a beneficial effect for a health use such as the action.

The above-mentioned health functional foods may contain conventional food additives, and the above-mentioned food additives may be added to the standards and standards of the relevant items in accordance with the General Rules and General Test Methods approved by the Food and Drug Administration, It can be judged whether it is suitable or not.

The food additives described in the above-mentioned Food Additives Code include chemical compounds such as ketones, glycine, potassium citrate, nicotinic acid, and cinnamic acid, natural additives such as persimmon extract, licorice extract, crystalline cellulose, high- A preservative formulation, a tar coloring agent, and the like.

The health functional food may be used in various foods and beverages to prevent or ameliorate alopecia such as various foods, beverages, gums, tea, vitamin complex, health functional supplement, food additive and the like.

The health functional food may be manufactured and processed into any one form selected from the group consisting of tablets, granules, powders, capsules, liquid solutions and rings for the purpose of preventing or improving alopecia.

Specifically, the health functional food in the form of tablets can be prepared by granulating the compound, excipient, binder, disintegrant and other additives in a conventional manner, compression-molding the mixture with a lubricant or the like, . The health functional food of the tablet form may contain a mating agent and the like if necessary, and may be sieved to a suitable skin care agent if necessary.

The hard capsule of the above-mentioned capsule type health functional food can be prepared by filling a normal hard capsule with a mixture of the above compound and an additive such as an excipient, or a granular product thereof or a granular product obtained by soaking the product. And the like can be filled in a capsule base such as gelatin. The soft capsule may contain a plasticizer such as glycerin or sorbitol, a coloring agent, a preservative and the like, if necessary.

The above-mentioned ring-form health functional food can be prepared by molding a mixture of the above compound, excipient, binder, disintegrant and the like by an appropriate method. If necessary, the preparation may be mixed with white sugar or other suitable skin care agent or a starch, talc or a suitable substance It is possible that the

The granular health functional food may be prepared by granulating a mixture of the above compound, excipient, binder, disintegrant and the like by a suitable method, and if necessary, may contain a flavoring agent, a mating agent and the like.

Further, the definitions of the above excipients, binders, disintegrants, lubricants, mating agents, flavoring agents and the like are described in documents known in the art, and the functions and the like may be the same or similar.

The present invention will be further described with reference to the following examples, but it should be apparent that the present invention is not limited by the following examples.

Example

9.7 kg of chestnut dried balsam were extracted with 80% (w / w) ethanol to extract compounds having the structures of the above formulas (1) to (7) by ultrasonic extraction.

Specifically, the dried bryophytes were cleaned with distilled water, immersed in 5% w / v ethanol for 80% (w / w), and the ultrasonic extraction method was repeated 3 times for 2 hours to obtain a chestnut extract.

The extracts were dissolved in purified water and fractionated in the order of polarity from nonpolar solvent to polar fraction according to the polar fraction method. In this case, 5 fractions were obtained by sequentially using hexane, dichloromethane, ethyl acetate and butanol while increasing the solvent polarity .

Each fraction was fractionated by gradient conditions according to the ratio of chloroform and methanol.

Since the fraction 3 of dichloromethane and the fraction 1 and 2 of ethyl acetate were confirmed to have the same pattern as the result of TLC confirmation, the three fractions were combined and subjected to column chromatography using silica gel. In Examples 2 to 6 ≪ / RTI >

Ethyl acetate was subjected to column chromatography on fractions 3 and 4 to obtain the chemical of Example 1.

After the first gradient, a white powder was formed as a crystal at subfraction 3, filtered to obtain a residue, and the remaining solution and the fourth fraction were combined and finally the compound of Example 7 was separated using silica gel and Rpsilica gel.

The separated compounds were confirmed by NMR and MS.

division compound Example 1 Formula 1 Example 2 (2) Example 3 (3) Example 4 Formula 4 Example 5 Formula 5 Example 6 6 Example 7 Formula 7

Experimental Example  1: I- DPC Proliferative ability  Evaluation test

The immortalized dermal papilla cells were treated with the compounds of the examples and tested for cell proliferation to test for the effect of treating hair loss or promoting hair growth.

Figures 1 and 2 show the results of measuring the degree of cell proliferation for 72 hours after treatment of the compounds of the Examples with I-DPC.

Referring to Figures 1 and 2, the compounds of Examples 1 to 4 significantly promoted cell proliferation at certain concentrations.

In particular, the compound of Example 3 effectively promoted cell proliferation at a concentration of 1 μM as compared to the control, and the compound of Example 4 effectively promoted cell proliferation at a concentration of 10 μM.

Compared with the control group, the remaining compounds exhibited a relatively low ability to promote cell proliferation, and the compounds of Examples 5 and 6 inhibited cell proliferation at high concentrations.

Experimental Example  2 : DPC Proliferative ability  Evaluation test

The compounds of the examples were treated with human dermal papilla cells (DPC) and cell proliferation was measured to examine the effect of alopecia treatment or hair growth stimulation.

FIGS. 3 and 4 are the results of measuring the degree of cell proliferation for 72 hours by treating the compounds of the Examples with different concentrations in primary DPC.

Referring to Figures 3 and 4, the compounds of Examples 1 to 6 significantly promoted cell proliferation at certain concentrations.

However, the compounds of Examples 1 to 4 promoted cell proliferation at all concentrations as compared with the control group, while the compounds of Examples 5 and 6 promoted cell proliferation at low concentration, but inhibited cell proliferation at high concentration.

Experimental Example  3: keratinocytes Proliferative ability  Evaluation test

HaCaT cells cultured for 48 hours were treated with the compounds of the examples and cell proliferation was measured with time.

The degree of proliferation of HaCaT cells treated with compounds of the Examples and HaCaT cells (control) without any treatment was compared, and the relative values thereof were shown in FIG.

Referring to Figure 5, the compounds of Examples 1 to 6 significantly promoted HaCaT cell proliferation at specific concentrations. However, the compounds of Examples 1 to 4 promoted cell proliferation at all concentrations, while the compounds of Examples 5 and 6 inhibited cell proliferation over time at a concentration of 10 μM.

These results suggest that the compounds of the Examples can be utilized for improving hair loss by controlling the concentration.

Experimental Example  4 : Amount of hair growth  Evaluation test

When C3H mice (7 weeks old) of Tologen group were depilated and the compound of Example 3 or Example 7 was treated, anagen was induced after 2 weeks, and the results of the experiment are shown in FIGS. 6 to 9.

6 and 7, the compound (10 μM) of Example 3 was superior to the negative control group treated with PBS, and exhibited superior hair growth promoting effect, as well as a comparable level of positive control compared to the positive control treated with rogaine Hair growth promoting activity.

Referring to FIGS. 8 and 9, the compound of Example 7 was remarkably superior in the hair growth promoting effect as compared with the control group.

In particular, the hair weight of the control group measured after 2 weeks did not reach 40 mg, but when the compound of Example 3 was applied at 10 μM, the hair growth increased by about 50%.

In addition, when the compound of Example 7 mixed with PBS was administered subcutaneously, the hair growth was increased by more than two times, and when applied to skin by mixing with petrolatum, hair growth increased by about 50% or more.

These results suggest that the compound of Example 3 or Example 7 can be effectively administered under the skin or when applied to the skin.

It will be understood by those skilled in the art that the foregoing description of the present invention is for illustrative purposes only and that those of ordinary skill in the art can readily understand that various changes and modifications may be made without departing from the spirit or essential characteristics of the present invention. will be. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive. For example, each component described as a single entity may be distributed and implemented, and components described as being distributed may also be implemented in a combined form.

The scope of the present invention is defined by the appended claims, and all changes or modifications derived from the meaning and scope of the claims and their equivalents should be construed as being included within the scope of the present invention.

Claims (9)

And at least one compound selected from the group consisting of compounds represented by the following formulas (1) to (7) as an active ingredient.
[Chemical Formula 1]

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

The method according to claim 1,
The compound of the above formulas (1) to (7) is isolated in Bombyx mori. The method according to claim 1,
A composition for improving hair loss, which promotes growth of dermal papilla cells or keratinocytes. A cosmetic composition comprising the composition of any one of claims 1 to 3 as an active ingredient. 5. The method of claim 4,
Wherein the cosmetic composition is at least one selected from the group consisting of hair toners, hair lotions, hair creams, hair sprays, hair mousses, hair gels, hair soaps, hair shampoos, hair rinses, hair packs, and hair treatments. A composition for external application for skin comprising the composition of any one of claims 1 to 3 as an active ingredient. A pharmaceutical composition for preventing or treating hair loss comprising the composition of any one of claims 1 to 3 as an active ingredient. A health functional food for improving hair loss comprising the composition of any one of claims 1 to 3 as an active ingredient. A method for preventing or treating hair loss, comprising the step of administering the composition of any one of claims 1 to 3 to a non-human subject.

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