KR20080018855A - Novel use of panduratin a or derivatives thereof - Google Patents

Abstract

A Panduratin A isolated from the extract of Kaempferia pandurata or its derivative is provided to inhibit growth of bacteria including acne-causing bacteria in the skin without side effects, so that it is useful for treatment of acnes effectively. An antibacterial composition comprises a Panduratin A compound isolated from the extract of Kaempferia pandurata, represented by the formula(1) or the formula(2), or its derivative, and inhibits growth of Propionibacterium acnes, Staphylococcus epidermis, Micrococcus luteus, Staphylococcus aureus, Staphylococcus warneri, Staphylococcus haemolyticus, Staphylococcus xylosus, Staphylococcus hominis and Staphylococcus saprophyticus, wherein the extract of Kaempferia pandurata is prepared by extracting Kaempferia pandurata with water or a C1-C6 organic solvent selected from alcohol, acetone, ether, benzene, chloroform, ethyl acetate, methylene chloride, hexane, cyclohexane and petroleum ether.

Description

Novel use of Panduratin A or derivatives

The present invention relates to a novel use of panduratin A compounds, derivatives thereof, and more particularly to panduratin A compounds represented by the following formula (1), panduratin A represented by the following formula (2) and antimicrobial and acne therapeutic uses of derivatives of panduratin A.

<Formula 1>

<Formula 2>

　　　　　　　　

　　　　　　　　

There are many microorganisms in the human skin. Among the microorganisms causing the skin diseases are Propionibacterium acnes, Staphylococcus epidermidis, Micrococcus luteus, Staphylococcus aureus, Staphylococcus aureus. , Staphylococcus warneri, Staphylococcus haemolyticus, Staphylococcus xylosus, Staphylococcus hominis, Staphylococcus hominis Phyticus (Staphylococcus saprophyticus), and especially the microorganisms causing acne and inflammation, such as Propionibacterium acnes, Staphylococcus epidermidis and Micrococcus luteus (Raman A. et al., Lett. Appl. Microbiol., 21: 242-245, 1995). They are also present in normal skin, and Propionibacterium acnes is a major cause of acne. The microorganism first penetrates into the hair follicles through the hair follicle tube, and deeply inoculates the hair follicles while decomposing sebum to produce free fatty acid, and when staphylococcal bacteria are secondaryly infected, reddened swells and pus is formed.

The acne is caused by an inflammatory disease of the fur branch and is a very common skin disease that causes inflammation of facial hair follicles of puberty and young age. However, these days, acne is widening due to air pollution, sex hormone imbalance, drug abuse, stress, and visceral diseases. At puberty, both male and female sex hormones become active, stimulating the sebaceous glands attached to the hair follicles, and as a result, the sebaceous glands become larger and secrete more sebum. At the same time, the stratum corneum of the hair follicles, or pores inlet, becomes thick and the adhesion increases, resulting in narrowing or clogging the pores. As a result, sebum accumulates in the hair follicles, and bacteria living in the hair follicles multiply and develop into inflammation.

So far, benzoyl peroxide, salicylic acid, benzalkonium chloride, phenol, tetracycline, or erythro The use of antibiotics, such as erythromycin, is used. However, it is known that tetracycline and other antibiotics are effective for skin treatment, but are highly likely to cause side effects such as the emergence of strains resistant to propionibacterium and photosensitivity (Gollnick, H. et al. , Dermatology., 196: 119-125, 1998). In addition, salicylic acid preparations, whose main effect is the removal of keratin, cannot be used for purulent dermatitis and may cause skin redness and erythema, while benzoyl peroxide preparations that suppress purulent bacteria may cause allergic dermatitis and erythema. It is reported and does not cure acne in terms of efficacy.

In recent years, acne has been treated using natural products, such as tee tree oil, royal jelly extract, and ginseng extract, but most of these natural products are not a single substance. Due to the addition of other substances in the formulation, the antimicrobial activity may be drastically reduced, and there is a problem in that the antimicrobial activity spectrum is not wide and the antimicrobial activity is not effectively exhibited against acne-inducing bacteria. In particular, natural-derived antimicrobial material has a problem that it is difficult to formulate because a large portion of the active ingredient is lost by evaporation or weak thermal stability when heated, the antibacterial activity tends to drop sharply (Higaki, S. et al., J. Dermatology., 23: 310-314, 1996).

The present inventors have searched for a long time to find a natural-derived compound having strong antimicrobial activity against skin microorganisms, and as a result, a panduratin A compound, a derivative thereof, or a caemperia pandurata isolated from Kaempferia pandurata (Kaempferia pandurata) extract confirmed the excellent antimicrobial activity against skin microorganisms and completed the present invention.

The present invention provides a natural compound or a natural extract showing an excellent antimicrobial activity to skin microorganisms and a composition for treating antibacterial or acne containing the same, and a method for inhibiting the growth of skin microorganisms using the compound or extract or treating acne It provides a method for providing a new use for the production of antimicrobial or acne treatment of the compound or extract.

In order to achieve the above technical problem, the present invention is Propionibacterium Acnes, Staphylococcus epidermis, Micrococcus Luteus, Staphylococcus aureus, Staphylococcus warneri, Staphylococcus haemora Panduratin A compound represented by the following Chemical Formula 1 exhibiting antimicrobial activity to a microorganism selected from the group consisting of eticus, Staphylococcus xylose, Staphylococcus hominis and Staphylococcus sapropiticus, Provided is an antimicrobial composition containing a derivative of panduratin A represented by Formula 2 or a pharmaceutically acceptable salt thereof as an active ingredient.

<Formula 1>

<Formula 2>

　　　　　　　　

　　　　　　　　

In addition, the present invention is propionibacterium acnes, staphylococcus epidermis, micrococcus lutheus, staphylococcus aureus, staphylococcus warneri, staphylococcus haemoraiticus, staphylococcus xyl The present invention provides an antimicrobial composition containing an extract of Kaempferia pandurata, which exhibits antimicrobial activity against microorganisms selected from the group consisting of Rothus, Staphylococcus hominis, and Staphylococcus saprophyticus.

In addition, the present invention is an acne containing a panduratin A compound represented by Formula 1, a derivative of panduratin A represented by Formula 2, or a pharmaceutically acceptable salt thereof as an active ingredient A therapeutic composition is provided.

In another aspect, the present invention provides a composition for treating acne containing Kaempferia pandurata extract as an active ingredient.

Hereinafter, the present invention will be described in detail.

In the present invention, 'skin microorganism' is propionibacterium acnes, staphylococcus epidermis, micrococos luteus, staphylococcus aureus, staphylococcus warneri, staphylococcus haemoraiticus , Microorganisms selected from the group consisting of Staphylococcus xylose, Staphylococcus hominis and Staphylococcus sapropiticus.

The present invention is characterized by providing a novel use of a panduratin A compound represented by the following formula (1) or a derivative of panduratin A represented by the following formula (2).

<Formula 1>

<Formula 2>

　　　　　　　　

　　　　　　　　

In another aspect, the present invention Kaempferia ( Kempferia) pandurata ) is characterized by providing a novel use of the extract.

The compounds according to the invention can be used in the form of salts, preferably pharmaceutically acceptable salts. As the salt, an acid addition salt formed by a pharmaceutically acceptable free acid is preferable. Organic acids and inorganic acids may be used as the free acid. The organic acid is not limited thereto, 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. In addition, the inorganic acid includes, but is not limited to, hydrochloric acid, bromic acid, sulfuric acid and phosphoric acid.

The panduratin A compound represented by the general formula (1) of the present invention or a derivative thereof represented by the general formula (2) may be obtained from a plant or a part of a plant using a method of extracting and separating conventional substances, and preferably It can be obtained from Kaempferia pandurata Roxb. And most preferably from the rhizome of Kaemferia pandurata. Stems, roots or leaves are properly dehydrated and macerated or only dehydrated to obtain the desired extracts, and the desired extracts are purified using purification methods known to those skilled in the art to which this invention pertains. In addition, a synthetic compound or a derivative thereof corresponding to a panduratin A compound represented by plant-derived formula (1) or a derivative thereof represented by formula (2) is generally a commercially available material, or is prepared using a known synthesis method. Can be. Specifically, it may be extracted from herbal resources such as Kaemperia pandurata, and may be synthesized by conventional chemical synthesis.

In addition, as a preferred compound of the present invention, the panduratin A compound represented by the formula (1) or a derivative thereof represented by the formula (2) may be selected from the water of the caemperia pandurata or the organic solvent extract of the C1-C6 or the camperia pandurata. It can be separated and purified from the oil obtained by compression.

Kaempferia pandurata Roxb. Is a plant belonging to the zingiberaceae family. The root is widely used for colds, enteritis, skin diseases and urethral pain. Kaemperia pandurata contains pinocembrin chalcone, cardamonin, pinocempin, pinostrobin, 4-hydropanduratin A, etc. These ingredients have been reported to show anticancer effects (Trakoontivakorn, G., et al ., J. Agric . Food Chem ., 49, 3046-3050, 2001), and dihydrochalcone of the flavonoid family compounds have been reported to exhibit an insecticidal effect (see: Pandji, C., such as, phytochemistry, 34, 415-419, 1993 ). However, the antimicrobial activity of the panduratin A compound represented by the formula (1) or its derivative represented by the formula (2) to the skin microorganisms, especially acne-inducing bacteria has not been reported so far.

The panduratin A compound of the present invention or a derivative thereof represented by Chemical Formula 2 may be separated and purified from rhizome water of Kaemperia pandurata, or an oil obtained by compressing an organic solvent extract of C1-C6 or Kaemperia pandurata. have. Extraction solvents include purified water, methanol, ethanol, propanol, isopropanol, butanol, butanol, acetone, ether, benzene, chloroform Various solvents such as chloroform, ethyl acetate, methylene chloride, hexane, cyclohexane and petroleum ether may be used alone or in combination. . Separation and purification of panduratin A compounds or derivatives thereof from the extracts of Kaemperia pandurata is characterized by column chromatography and high performance liquid chromatography filled with various synthetic resins such as silica gel or activated alumina. HPLC) and the like can be used alone or in combination. However, the extraction and separation and purification method of the active ingredient is not necessarily limited to the above method.

The panduratin A compound represented by Formula 1 of the present invention or a derivative thereof represented by Formula 2 exhibits excellent antibacterial activity against acne-producing bacteria such as propionibacterium acnes, and is excellent in thermal stability, The antimicrobial activity is also maintained.

The panduratin A compound represented by Chemical Formula 1 or the derivative of panduratin A represented by Chemical Formula 2 may have a minimum inhibitory concentration for propionibacterium acnes as 2 μg / ml and 4 μg / ml, respectively. Much lower than the minimum benzoyl peroxide minimum inhibitor concentration of 500-1000 μg / ml (Decker, LC. Et al., Antimicro.Agents. Chemother., 33 (3): 326-330, 1989) Minimum inhibitory concentration of benzalkonium chloride, 200-300 ㎍ / ml (Gloor, M. et al., Arch. Dermatol. Res., 265 (2): 207-212, 1979) or terpinen-4, an oil component of tea tree It exhibits excellent antimicrobial activity by about 150 times lower than the minimum inhibitory concentration of -ol (300-500 ㎍ / mL (Raman, A. et al., Lett. Appl. Microbiol., 21 (4): 242-245, 1995)). . Therefore, the panduratin A compound represented by Formula 1 or the derivative of panduratin A represented by Formula 2 of the present invention may be effectively used as a composition for treating acne.

In addition, the panduratin A compound represented by the formula (1) or the derivative of panduratin A (panduratin A) represented by the formula (2), in addition to the microorganisms Staphylococcus epidermis, micrococos Luteus, Staphylococcus aureus, Minimum inhibitory concentrations for microorganisms selected from the group consisting of Staphylococcus warneri, Staphylococcus haemoraiticus, Staphylococcus xylose, Staphylococcus hominis and Staphylococcus sapropiticus It shows strong antimicrobial activity at μg / ml. Therefore, the panduratin A compound represented by Formula 1 or the derivative of panduratin A represented by Formula 2 of the present invention may be effectively used as an antimicrobial composition.

Caemperia pandurata extract of the present invention may be prepared using extraction methods known to those skilled in the art, and may be prepared by water or an organic solvent of C1 to C6. The organic solvent is C1 ~ C6 alcohol, acetone (acetone), ether (ether), benzene (benzene), chloroform (chloroform), ethyl acetate (ethyl acetate), methylene chloride (hexane), hexane (hexane), Various solvents, such as cyclohexane and a petroleum ether, can be used individually or in mixture. Preferably, the extract of Kaemperia pandurata may be extracted with ethanol to prepare an ethanol extract, and the extract may be fractionated with ethyl acetate to prepare an ethyl acetate extract.

In one embodiment of the present invention, the Kaemperia pandurata ethanol and ethyl acetate extracts were confirmed to exhibit excellent antimicrobial activity with a minimum inhibitory concentration of 39, 19.5 ㎍ / ㎖ for Propionibacterium acnes, respectively. Therefore, the extract Kaemperia pandurata of the present invention can be effectively used as a composition for treating acne and an antimicrobial composition.

Therefore, a panduratin A compound represented by Formula 1, a derivative of panduratin A represented by Formula 2, or a pharmaceutically acceptable salt thereof may be used as an antimicrobial composition or a composition for treating acne. The composition may be used, but is not limited thereto, and may be used in the preparation of pharmaceuticals.

In addition, the Kaemperia pandurata extract may be used as an antimicrobial composition or a composition for treating acne, and the composition may be used as a pharmaceutical preparation, although not limited thereto.

When formulated in the form of the drug, diluents or excipients such as fillers, extenders, binders, wetting agents, disintegrating agents, and surfactants are usually used. Solid preparations for oral administration include tablets, pills, powders, granules, capsules and the like, which solid preparations comprise at least one excipient such as at least one excipient, e.g. Starch, calcium carbonate, sucrose or lactose, gelatin and the like are mixed and prepared. In addition to simple excipients, lubricants such as magnesium styrate talc are also used. Liquid preparations for oral administration include suspensions, liquids, emulsions, and syrups. In addition to commonly used simple diluents such as water and liquid paraffin, various excipients such as wetting agents, sweeteners, fragrances, and preservatives may be included. have. Formulations for parenteral administration include sterile aqueous solutions, non-aqueous solvents, suspensions, emulsions, lyophilized preparations, ointments, creams. As the non-aqueous solvent and the suspension solvent, propylene glycol, polyethylene glycol, vegetable oil such as olive oil, injectable ester such as ethyl oleate, and the like can be used.

The parenteral administration is by subcutaneous injection, intravenous injection, intramuscular injection or intrathoracic injection injection. In order to formulate into a parenteral formulation, a panduratin A compound represented by Formula 1, a derivative thereof, or a kaemperia pandurata extract may be prepared as a solution or suspension by mixing in water with a stabilizer or a buffer. Formulated in unit dosage forms of ampoules or vials. Dosage units may contain, for example, one, two, three or four times, or 1/2, 1/3 or 1/4 times the individual dosage. The individual dosage preferably contains an amount in which the effective drug is administered at one time, which usually corresponds to all, 1/2, 1/3 or 1/4 times the daily dose.

The effective dose of the panduratin A compound, a derivative thereof, or the camemperia pandurata extract represented by Formula 1 of the present invention is a single dose of 0.1-50 mg / kg, preferably 1-10 mg / kg and may be administered 1-3 times a day. Dosage levels for a particular patient may vary depending on the patient's weight, age, sex, health condition, diet, time of administration, method of administration, rate of excretion, severity of the disease, and the like.

Toxicity of oral administration of a panduratin A compound, a derivative thereof, or a Kaemperia pandurata extract represented by Formula 1 of the present invention to a mouse was 50% lethal dose by oral toxicity test (LD ₅₀ ) was found to be at least 2,000 mg / kg.

In particular, the antimicrobial composition and acne treatment composition of the present invention may be formulated in the form of a medicament for skin application, ie, ointment, cream, and 0.001-10.0% by weight, preferably 0.001-5.0% by weight, based on the total weight of the formulation. It can be suitably formulated according to the formulation within the range of. If the amount is less than 0.001% by weight, the antimicrobial activity is lowered. When the amount is added more than 10.0% by weight, only the added amount is increased, and there is no significant difference in the antimicrobial activity.

In addition, the antimicrobial composition or the acne treatment composition of the present invention can be used in the form of cosmetic preparations for acne skin. The cosmetics include, but are not limited to, detergents, creams, lotions, essences and lotions. The composition of the present invention may be formulated in various forms such as cream, lotion, gel, water soluble liquid, essence, oil-in-water type and water-in-oil type, but it may be used in cosmetics, which formulation is used in the technical field to which the present invention belongs. It can be determined very easily by those skilled in the art. For example, in the case of preparing the detergent, in order to improve the acne treatment effect by adding the composition of the present invention to a conventional detergent base, salicylic acid, alpha-hydroxy acid, and beta-hydroxy acid (Keratolytic or Exfoliating agents) such as (β-hydroxy acid) or sulfur (Sulfur) can be added, fragrances, pigments, fungicides, antioxidants, preservatives, moisturizers, etc. can be used to improve the properties Thickeners, inorganic salts, synthetic polymers and the like can be used.

The antimicrobial composition and the acne treatment composition of the present invention may be suitably formulated in a range of 0.001-10.0% by weight, preferably 0.001-5.0% by weight, based on the total weight of the cosmetic preparation. If the amount is less than 0.001% by weight, the antimicrobial activity is lowered. When the amount is added more than 10.0% by weight, only the added amount is increased, and there is no significant difference in the antimicrobial activity.

The panduratin A compound represented by the formula (1) of the present invention, a derivative of panduratin A represented by the formula (2), or the extract of Kaempferia pandurata (Prophynibacterium acnes, Staphylococcus epi) Staphylococcus, Micrococcus Luteus, Staphylococcus aureus, Staphylococcus warneri, Staphylococcus haemoraiticus, Staphylococcus xylose, Staphylococcus hominis and Staphylococcus sapropiti Excellent antimicrobial activity that inhibits the growth of microorganisms selected from the group consisting of couss can be effectively used in antimicrobial composition or acne treatment composition against the microorganism.

Hereinafter, the present invention will be described in detail with reference to Examples and Experimental Examples. However, the following Examples and Experimental Examples illustrate the present invention and do not limit the scope of the present invention.

In addition, in the following Examples and Experimental examples, the% not specifically indicated as% by weight indicates weight%.

<Example 1>

Pandulatin  Isolation and Structure Determination of A-Compounds and Their Derivatives

<1-1> Kaemperia From Pandurata Isolation and Structural Determination of Panduratin A Compounds

To 100 g (dry weight) of dry pulverized Kaemperia pandurata, 400 ml of 100 vol% ethanol was added and allowed to stand at room temperature for two days, after which the solution was prepared using Whatman filter paper No. 2 Filtered. After repeating the above procedure twice, the ethanol filtrate was concentrated in vacuo and lyophilized, and then eluted with a solvent mixed with hexane, chloroform and ethyl acetate in a ratio of 15: 5: 2 by silica gel column chromatography, followed by vacuum rotation. The solvent was completely removed by a concentrator to prepare a crude extract of Caemperia pandurata.

The crude extract of Caemperia pandurata was separated on a TLC plate using a solvent system in which hexane, chloroform and ethyl acetate were mixed at 15: 5: 2 and confirmed by TLC plate analysis. Using a solvent system in which the antimicrobial activity of the extract identified by TLC plate analysis was mixed with hexane, chloroform, and ethyl acetate at 15: 5: 2, the ratio of the distance of solvent development and the distance of antimicrobial activity was 0.2 Rf = 0.2, and the panduratin A compound, which is a single substance having a strong absorption band in ultraviolet (254, 365 nm, VL-6-LC, Vilber lourmat), was isolated.

¹ H-NMR spectra and ¹³ C-NMR spectra were measured at 500 MHz and 125 MHz (solvent: DMSO), respectively, to determine the structure of the separated single material, and are shown in FIGS. 1 and 2, respectively. ¹³ C-NMR spectrum and the ^{1 H-NMR 1 H- 1 H} COSY spectrum and ¹ H- ¹³ to measure the correlation of the correlation of the ¹ H- ¹ H, based on the result of the spectrum related to the ¹ H- ¹³ C C COSY Spectra were measured and the results are shown in FIGS. 3 and 4.

In addition, the results of FAS / MS measured for mass spectrometry of the separated single material are shown in FIG. 5. The compound had a molecular weight of 406 with [M + H ⁺ ] observed at m / z 407 in FAS / MS and a molecular formula of C ₂₆ H ₃₀ O ₄ .

Results of the above ¹ H-NMR, ¹³ C-NMR, ¹ H- ¹ H COZY, ¹ H- ¹³ C HMBC and EI / MS and previously published research reports (Woo, WS et al., Phytochemistry , 26: 1542-1543, 1987) as a result of comparative analysis and identified, the single substance isolated in Example 1-1 was (2,6-dihydroxy-4-methoxylphenyl)-[3'-methyl-2 '-(3 "- Methylbut-2 ″ enyl) -6′-phenylcyclohex-3′-enyl] methanone was identified as panduratin A compound represented by the formula (1).

<Formula 1>

<1-2> Kaemperia From Pandurata Pandulatin Of panduratin A Isolation and Determination of Derivatives

The crude extract of Caemperia pandurata extracted in Example <1-1> was eluted with a solvent in which methanol and water were mixed at a ratio of 9: 1 using RP-18 gel 60F ₂₅₄ and Merck, followed by a silica gel column. Chromatography was used again to elute the chloroform and methanol in a solvent mixture of 10: 0.2 ratio, and finally eluted with a solvent in which hexane and ethyl acetate were mixed in a ratio of 10: 3. Using a solvent system in which the antimicrobial active material of the extract identified by TLC plate analysis was mixed with hexane, chloroform and ethyl acetate in a ratio of 15: 5: 1.5, the ratio of the distance between the solvent developed and the antimicrobial active developed was 0.2. The derivative of panduratin A, which is a single substance having a value of Rf = 0.2 and having a strong absorption band in ultraviolet rays (254, 365 nm, VL-6-LC and Vilber lourmat), was isolated.

For the structure determination of the isolated single material, ¹³ C-NMR spectra and ¹ H-NMR spectra were measured at 500 MHz and 125 MHz (solvent: DMSO), respectively, and are shown in FIGS. 6 and 7, respectively. ¹³ C-NMR to measure the correlation between the spectrum and ¹ H-NMR correlation of the ¹ H- ¹ H on the basis of the result of the spectrum related to the ¹ H- ¹³ C by measuring the DEPT spectrum is shown in Figure 8 the results.

In addition, the results of EI-MASS measured for mass spectrometry of the separated single material are shown in FIG. 9. The compound had a molecular weight of 406 with [M ⁺ ] observed at m / z 406 in EI / MS and a molecular formula of C ₂₆ H ₃₀ O ₄ .

The results of ¹³ C-NMR, ¹ H-NMR, DEPT, and EI / MS and previously published research reports (Woo, WS et al., Phytochemistry , 26: 1542-1543, 1987) were identified and compared. As a result, the single substance isolated in Example 1-2 was (2-methoxy-4,6-dihydroxyphenyl)-[3'-methyl-2 '-(3 "-methylbut-2" -enyl) -6'-phenylcyclohex. -3'-enyl] methanon was identified as a derivative of panduratin A represented by the formula (2).

<Formula 2>

　　　　　　　　

　　　　　　　　

<Example 2>

Pandulatin  Evaluation of antimicrobial activity against microorganisms of A compound and its derivatives

<2-1> Bactericidal Activity of Panduratin A Compounds

The panduratin A compound prepared in Example <1-1> was dissolved in dimethyl sulfoxide to prepare a sample having a concentration of 0.0004%. After diluting Propionibacterium acnes to 2 × 10 ⁵ CFU / mL in the prepared sample, 100 μl was added to each test tube and 4 hours, 8 hours, 12 hours, 16 hours, and 20 hours at 37 ° C., respectively. After reacting for 24 hours and 28 hours, the viable cell number of propionibacterium acnes, a representative acne-inducing bacterium, was measured at an absorbance of 625 nm for each sample.

As can be seen in the graph of FIG. 10, when 4 μg / ml panduratin A compound was added, the bacteria were almost killed in all sections of the measurement time. In Fig. 10, panduratin A compound exhibits almost the same effect as erythromycin currently used as an acne antibiotic. The result is that the drug is usually used once every 8 hours, and the ointment or application is used for about 2-4 hours. In this case, it represents a very effective bactericidal activity against propionibacterium acnes, a representative acne causing bacterium.

Staphylococcus epidermis, Micrococcus luteus, Staphylococcus aureus, Staphylococcus waneri, Staphylococcus haemoraiticus, Staphylococcus xylose, Minimum concentrations showing bactericidal activity against Staphylococcus hominis and Staphylococcus sapropiticus were measured, and the results are shown in Table 1.

Minimum concentration showing the bactericidal activity of panduratin A against microorganisms (ug / ml) Concentrations of Pandoratin A Compounds Propionibacterium Acnes 4 Staphylococcus Epidermis 4 Micrococos Luteus 4 Staphylococcus aureus 4 Staphylococcus Warneri 4 Staphylococcus Haemoraiticus 4 Staphylococcus Xylose 8 Staphylococcus Hominis 2 Staphylococcus sapropicus 4

As a result, it can be seen that panduratin A exhibits a very effective bactericidal activity against the microorganisms as well as propionibacterium acnes, which is an acne-causing bacterium, and can be used as a useful antimicrobial composition.

<2-2> pandulatin Bactericidal Activity of Derivatives of A

The bactericidal activity of the derivative of panduratin A by dissolving the derivative of panduratin A prepared in Example <1-2> in dimethyl sulfoxide to a sample having a concentration of 0.0008%, in the same manner as in Example <2-1>. Was measured.

As can be seen in the graph of Figure 11, when the addition of the derivative of 8 ㎍ / ml panduratin A bacterium almost appeared to be killed at all intervals of the measurement time as a drug or a treatment for acne based on the derivative of panduratin A as a material When used, it was found that the bactericidal activity was very effective against propionibacterium acnes, which is a representative acne causing bacterium.

Staphylococcus epidermis, Micrococcus luteus, Staphylococcus aureus, Staphylococcus waneri, Staphylococcus haemoraiticus, Staphylococcus xylose The minimum concentrations showing bactericidal activity against, Staphylococcus hominis and Staphylococcus saprophyticus were measured, and the results are shown in Table 2.

Minimum concentration of bactericidal activity of panduratin A derivative against microorganism (unit: ㎍ / mL) Concentrations of Pandoratin A Derivatives Propionibacterium Acnes 8 Staphylococcus Epidermis 8 Micrococos Luteus 8 Staphylococcus aureus 4 Staphylococcus Warneri 4 Staphylococcus Haemoraiticus 8 Staphylococcus Xylose 4 Staphylococcus Hominis 4 Staphylococcus sapropicus 4

As a result, it can be seen that panduratin A derivative also shows a very effective bactericidal activity against the microorganisms as well as propionibacterium acnes, which is an acne-causing bacterium, and thus can be used as a useful antimicrobial composition.

<2-3> Minimum Concentration of Pandulatin A Compound Inhibitory Concentration ( MIC ) measurement

The panduratin A compound prepared in Example <1-1> was dissolved in 0.5% methanol, and 100 ul of blood plate medium was placed in a prepared 96-well plate, and the panduratin A compound was added at a concentration of 0.1% only in the first well. 100 ul each was added, and then diluted 2 times sequentially. 100 μl of Propionibacterium acnes was added to each test tube so as to be 2 × 10 ⁵ CFU / mL in this dilution solution, and after culturing at 37 ° C. for 24 hours or more, the minimum concentration without turbidity was measured. Also in the same manner as above, Staphylococcus epidermis, Micrococcus lutheus, Staphylococcus aureus, Staphylococcus warneri, Staphylococcus haemoraiticus, Staphylococcus xylose The minimum inhibitory concentrations for, Staphylococcus hominis and Staphylococcus saprophyticus were measured, and the results are shown in Table 3.

Minimum Inhibitory Concentration of Microorganisms of Panduratin A (unit: ㎍ / mL) Concentrations of Pandoratin A Compounds Propionibacterium Acnes 2 Staphylococcus Epidermis 2 Micrococos Luteus 2 Staphylococcus aureus 2 Staphylococcus Warneri 2 Staphylococcus Haemoraiticus 2 Staphylococcus Xylose 4 Staphylococcus Hominis 2 Staphylococcus sapropicus 2

<2-4> pandulatin Minimum concentration of derivatives of A Inhibitory Concentration ( MIC ) measurement

The minimum inhibitory concentration of the derivative of panduratin A was measured in the same manner as in Example <2-3>, and the results are shown in Table 4 below.

Minimum Inhibitory Concentration of Microorganisms of Panduratin-A Derivative (Unit: ㎍ / ㎖) Concentrations of Pandoratin A Derivatives Propionibacterium Acnes 4 Staphylococcus Epidermis 4 Micrococos Luteus 4 Staphylococcus aureus 4 Staphylococcus Warneri 2 Staphylococcus Haemoraiticus 8 Staphylococcus Xylose 4 Staphylococcus Hominis 2 Staphylococcus sapropicus 2

<Example 3>

Pandulatin  Confirmation of acne treatment effect using A compound and its derivatives

Clinical trials for acne prevention and treatment were performed using pandulatin A prepared in Example <1-1>. The test subjects were selected from 30 men and women in their mid teens to mid 30's who suffered from acne, and then administered 600 mg twice a day for 4 weeks and the results are shown in Table 5. The number of lesions decreased significantly after 4 weeks compared to the number of lesions before the start of the study, which was statistically significant (p-value <0.05).

Determination of the number of acne lesions when orally administered pandulatin A Average number before the start of the study Average number after 4 weeks of study P-value Cotton cloth 19.12 6.82 0.0065 papule 13.86 5.57 0.011 pustule 5.78 2.41 0.033 nodule 0.84 0.21 0.0208

On the other hand, using the derivative of panduratin A prepared in Example <1-2> and carried out a clinical experiment on the prevention and treatment of acne in the same manner as shown in Table 6 the results. The number of lesions decreased significantly after 4 weeks compared to the number of lesions before the start of the study, which was statistically significant (p-value <0.05).

Determination of Acne Lesions after Oral Administration of Pandoratin A Average number before the start of the study Average number after 4 weeks of study P-value Cotton cloth 18.52 5.78 0.0057 papule 14.25 6.23 0.013 pustule 6.27 3.24 0.035 nodule 0.93 0.32 0.0318

<Example 4>

Pandulatin  Of these compounds and derivatives thereof Thermal stability

<4-1> Thermal Stability of Panduratin A Compounds

The panduratin A compound prepared in Example <1-1> was dissolved in dimethyl sulfoxide to prepare a sample having a concentration of 0.1%, and then 60 ° C, 70 ° C, 80 ° C, 90 ° C, 100 ° C, and 121 ° C, respectively. After the heat treatment for 30 minutes at 30, the results of measuring the antimicrobial activity by the well diffusion analysis method are shown in Table 7 below.

Results of Determination of Antimicrobial Activity According to Temperature of Panduratin A Compound Treatment temperature (℃) 60 70 80 90 100 121 Diameter of low ring of plate which added pandulatina (mm) 17 16 17 17 18 17

As can be seen from the results of Table 7, almost no reduction of the antimicrobial activity occurred after the heat treatment from 60 ℃ to 121 ℃. Therefore, it was confirmed that the panduratin A compound of the present invention is stable even at high temperature.

<4-2> pandulatin Thermal Stability of Derivatives of A

The derivative of panduratin A prepared in Example <1-2> was measured in the same manner as in Example <4-1>, and the results are shown in Table 8 below.

Determination of Antimicrobial Activity According to Temperature of Derivatives of Panduratin A Treatment temperature (℃) 60 70 80 90 100 121 Diameter of low ring of plate which added derivative of panduratin A (mm) 16 17 17 16 18 17

As can be seen from the results of Table 8, the panduratin-A derivative of the present invention was confirmed that even after the heat treatment from 60 ℃ to 121 ℃ hardly decrease in antibacterial activity is stable even at high temperature treatment process.

Example 5

Caemperia Pandurata  Evaluation of Antimicrobial Activity against Microorganisms of Extracts

Propionibacterium arc, which is an acne-inducing bacterium of 100% ethanol crude extract of Kaemperia pandurata prepared in the process of separating panduratin A or a derivative thereof in Example <1-1> or Example <1-2> The bactericidal activity against nes was measured in the same manner as in Example <2-1>. As a result, it was found that the acne-causing bacteria were almost killed when 78 μg / ml of the extract was added. In addition, the minimum inhibitory concentrations of the acne-inducing bacteria of the extract, Propionibacterium acnes, Staphylococcus epidermidis and Micrococcus luteus, were measured in the same manner as in Example <2-3>, respectively, 39 ㎍. / Ml, 156 µg / ml, 39 µg / ml.

In addition, Propionibacterium acnes, which is an acne-inducing bacterium of ethyl acetate extract of Kaemperia pandurata, prepared in the process of separating panduratin A or its derivatives in Example <1-1> or Example <1-2>. As a result of measuring the bactericidal activity against Example <2-1>, it was found that the acne-causing bacteria were almost killed when 39 µg / ml of the extract was added. In addition, as a result of measuring the minimum inhibitory concentration for the propionibacterium acnes, acne-inducing bacteria of the extract in the same manner as in Example <2-3> was confirmed to 19.5 ㎍ / ㎖.

Therefore, it was found that the extract of Kaemperia pandurata can be used as a very effective antimicrobial composition because it has excellent bactericidal activity against the microorganism in a relatively small amount.

<Manufacture example 1-4>

Pandulatin  Preparation of lotion containing this compound

Using a panduratin A compound of the present invention, a lotion having the following composition was prepared. The panduratin A compound isolated in Example <1-1> was dissolved in a predetermined amount of water at four concentrations of 1.0, 0.1, 0.01, and 0.001%, and then mixed with an aqueous solution of phosphoric acid. Ethanol, glycerin, and propylene glycol were mixed and mixed into the mixture prepared above, flavoring and preservatives were added, the weight was adjusted with purified water, and mixed evenly.

Preparation Example 1 Preparation Example 2 Preparation Example 3 Preparation Example 4 Main Needs Pandora Latin A 1.0% Pandora Latin A 0.1% Pandora Latin A 0.01% Pandora Latin A 0.001% Glycerin 2.0% Glycerin 2.0% Glycerin 2.0% Glycerin 2.0% Propylene Glycol 2.0% Propylene Glycol 2.0% Propylene Glycol 2.0% Propylene Glycol 2.0% Potassium Phosphate 0.1% Potassium Phosphate 0.1% Potassium Phosphate 0.1% Potassium Phosphate 0.1% Sodium Diphosphate 0.05% Sodium Diphosphate 0.05% Sodium Diphosphate 0.05% Sodium Diphosphate 0.05% Fragrance 0.02% Fragrance 0.02% Fragrance 0.02% Fragrance 0.02% Ethanol (96%) 50% Ethanol (96%) 50% Ethanol (96%) 50% Ethanol (96%) 50% Purified water balance Purified water balance Purified water balance Purified water balance 0.1% preservative 0.1% preservative 0.1% preservative 0.1% preservative

Experimental Example 1

Pandulatin  Determination of antimicrobial activity of lotion containing A compound

To the test tube containing 4 ml of each of the concentrations of the panduratin A prepared in each concentration, 1 ml of acetic acid-inducing bacteria such as propionibacterium acnes were added to the test tube, followed by culturing while shaking the tube. The antimicrobial activity was measured by measuring the number, and the results are shown in Table 9 below.

Acne pathogenic bacteria Test solution Viable cell count (microbial count / ml) 0 hours 24 hours Propionibacterium Acnes Preparation Example 1 2.0 × 10 ⁵ <One Preparation Example 2 2.0 × 10 ⁵ <One Preparation Example 3 2.0 × 10 ⁵ <2 Preparation Example 4 2.0 × 10 ⁵ 2.1 × 10 ² Lotion Lotion 2.0 × 10 ⁵ 4.2 × 10 ³ Staphylococcus Epidermis Preparation Example 1 5.4 × 10 ⁵ <One Preparation Example 2 5.4 × 10 ⁵ <One Preparation Example 3 5.4 × 10 ⁵ <2 Preparation Example 4 5.4 × 10 ⁵ 1.8 × 10 ² Lotion Lotion 5.4 × 10 ⁵ 3.8 × 10 ³ Microcaucus Luteus Preparation Example 1 6.0 × 10 ⁵ <One Preparation Example 2 6.0 × 10 ⁵ <One Preparation Example 3 6.0 × 10 ⁵ 〈3 Preparation Example 4 6.0 × 10 ⁵ 2.5 × 10 ² Lotion Lotion 6.0 × 10 ⁵ 6.2 × 10 ³

As can be seen from the results of Table 9, medicinal cosmetics according to the present invention had a very high antibacterial activity against acne-inducing bacteria, such as propionibacterium Acnes compared to the components except panduratin A compound.

<Manufacture example 5-8>

Pandulatin A  Preparation of lotion containing derivative

Using a derivative of panduratin A of the present invention, a lotion having the following composition was prepared in the same manner as in <Preparation Example 1-4>.

Preparation Example 5 Preparation Example 6 Preparation Example 7 Preparation Example 8 Main Components Derivatives of Panduratin A 1.0% Derivatives of Panduratin A 0.1% Derivatives of Panduratin A 0.01% Derivative of Panduratin A 0.001% Glycerin 2.0% Glycerin 2.0% Glycerin 2.0% Glycerin 2.0% Propylene Glycol 2.0% Propylene Glycol 2.0% Propylene Glycol 2.0% Propylene Glycol 2.0% Potassium Phosphate 0.1% Potassium Phosphate 0.1% Potassium Phosphate 0.1% Potassium Phosphate 0.1% Sodium Diphosphate 0.05% Sodium Diphosphate 0.05% Sodium Diphosphate 0.05% Sodium Diphosphate 0.05% Fragrance 0.02% Fragrance 0.02% Fragrance 0.02% Fragrance 0.02% Ethanol (96%) 50% Ethanol (96%) 50% Ethanol (96%) 50% Ethanol (96%) 50% Purified water balance Purified water balance Purified water balance Purified water balance 0.1% preservative 0.1% preservative 0.1% preservative 0.1% preservative

Experimental Example 2

Pandulatin A  Determination of antimicrobial activity of lotion containing derivatives

The antimicrobial activity was measured in the same manner as in <Experimental Example 1> using the lotion containing the derivative of panduratin A. The results are shown in Table 10 below.

Acne pathogenic bacteria Test solution Viable cell count (microbial count / ml) 0 hours 24 hours Propionibacterium Acnes Preparation Example 5 2.0 × 10 ⁵ <One Preparation Example 6 2.0 × 10 ⁵ <One Preparation Example 7 2.0 × 10 ⁵ 〈3 Preparation Example 8 2.0 × 10 ⁵ 1.7 × 10 ² Lotion without derivative of panduratin A 2.0 × 10 ⁵ 4.8 × 10 ³ Staphylococcus Epidermis Preparation Example 5 5.4 × 10 ⁵ <One Preparation Example 6 5.4 × 10 ⁵ <One Preparation Example 7 5.4 × 10 ⁵ <2 Preparation Example 8 5.4 × 10 ⁵ 2.3 × 10 ² Lotion without derivative of panduratin A 5.4 × 10 ⁵ 5.7 × 10 ³ Microcaucus Luteus Preparation Example 5 6.0 × 10 ⁵ <One Preparation Example 6 6.0 × 10 ⁵ <One Preparation Example 7 6.0 × 10 ⁵ <2 Preparation Example 8 6.0 × 10 ⁵ 2.1 × 10 ² Lotion without derivative of panduratin A 6.0 × 10 ⁵ 5.2 × 10 ³

As can be seen from the results of Table 10, the medicinal cosmetics according to the present invention had a very high antibacterial activity against acne-inducing bacteria such as propionibacterium acnes compared to the component except the derivative of panduratin A.

<Manufacture Example 9-12>

Pandulatin  Preparation of a Cream Containing A Compound

Using the panduratin A compound of the present invention, a cream having the following composition was prepared. First, substances labeled B were dissolved at 75 to 80 ° C., and cetyl alcohol and preservatives were dissolved at the same temperature. C was emulsified in B and then mixed with the panduratin A compound represented by A at concentrations of 3.0, 0.1, 0.01, and 0.001%, respectively.

Preparation Example 9 Preparation Example 10 Preparation Example 11 Preparation Example 12 Main Needs A Pandora Latin A 3.0% Pandora Latin A 0.1% Pandora Latin A 0.01% Pandora Latin A 0.001% B Glycerin 2.0% Glycerin 2.0% Glycerin 2.0% Glycerin 2.0% Propylene Glycol 2.0% Propylene Glycol 2.0% Propylene Glycol 2.0% Propylene Glycol 2.0% Lauryl chloride sulfide 8.0% Lauryl chloride sulfide 8.0% Lauryl chloride sulfide 8.0% Lauryl chloride sulfide 8.0% Stearin 5.4% Stearin 5.4% Stearin 5.4% Stearin 5.4% Mineral oil 4.5% Mineral oil 4.5% Mineral oil 4.5% Mineral oil 4.5% C Fragrance 0.02% Fragrance 0.02% Fragrance 0.02% Fragrance 0.02% Cetyl alcohol 6.5% Cetyl alcohol 6.5% Cetyl alcohol 6.5% Cetyl alcohol 6.5% Purified water balance Purified water balance Purified water balance Purified water balance 0.1% preservative 0.1% preservative 0.1% preservative 0.1% preservative

Experimental Example 3

Pandulatin  Determination of antimicrobial activity of creams containing A compound

To the test tube containing 4 ml of each concentration of the pandoratin A compound prepared above, 1 ml of a solution containing acne-producing bacteria such as propionibacterium acnes was added and cultured by shaking the tube. After measuring the number of viable cells to measure the antimicrobial activity is shown in Table 11 below.

Acne pathogenic bacteria Test solution Viable cell count (microbial count / ml) 0 hours 24 hours Propionibacterium Acnes Preparation Example 9 2.0 × 10 ⁵ <One Preparation Example 10 2.0 × 10 ⁵ <One Preparation Example 11 2.0 × 10 ⁵ 〈6 Preparation Example 12 2.0 × 10 ⁵ 8.4 × 10 ² Pandulatin Minus Cream 2.0 × 10 ⁵ 4.1 × 10 ³ Staphylococcus Epidermis Preparation Example 9 5.4 × 10 ⁵ <One Preparation Example 10 5.4 × 10 ⁵ <One Preparation Example 11 5.4 × 10 ⁵ <8 Preparation Example 12 5.4 × 10 ⁵ 4.3 × 10 ² Pandulatin Minus Cream 5.4 × 10 ⁵ 7.0 × 10 ³ Microcaucus Luteus Preparation Example 9 6.0 × 10 ⁵ <One Preparation Example 10 6.0 × 10 ⁵ <One Preparation Example 11 6.0 × 10 ⁵ <4 Preparation Example 12 6.0 × 10 ⁵ 2.3 × 10 ² Pandulatin Minus Cream 6.0 × 10 ⁵ 2.1 × 10 ³

As can be seen from the results of Table 11, the cream of the embodiment according to the present invention had a very high antimicrobial activity against acne-inducing bacteria such as propionibacterium acnes compared to the ingredients minus panduratin.

Production Example 13-16

Pandulatin A  Preparation of Creams Containing Derivatives

Using the derivative of panduratin A of the present invention, a cream having the following composition was prepared in the same manner as in <Preparation Example 9-12>.

Preparation Example 13 Preparation Example 14 Preparation Example 15 Preparation Example 16 Main Components A Derivatives of Panduratin A 3.0% Derivatives of Panduratin A 0.1% Derivatives of Panduratin A 0.01% Derivative of Panduratin A 0.001% Glycerin 2.0% Glycerin 2.0% Glycerin 2.0% Glycerin 2.0% Propylene Glycol 2.0% Propylene Glycol 2.0% Propylene Glycol 2.0% Propylene Glycol 2.0% B Lauryl chloride sulfide 8.0% Lauryl chloride sulfide 8.0% Lauryl chloride sulfide 8.0% Lauryl chloride sulfide 8.0% Stearin 5.4% Stearin 5.4% Stearin 5.4% Stearin 5.4% Mineral oil 4.5% Mineral oil 4.5% Mineral oil 4.5% Mineral oil 4.5% Fragrance 0.02% Fragrance 0.02% Fragrance 0.02% Fragrance 0.02% C Cetyl alcohol 6.5% Cetyl alcohol 6.5% Cetyl alcohol 6.5% Cetyl alcohol 6.5% Purified water balance Purified water balance Purified water balance Purified water balance 0.1% preservative 0.1% preservative 0.1% preservative 0.1% preservative

Experimental Example 4

Pandulatin A  Determination of antimicrobial activity of creams containing derivatives

The antimicrobial activity was measured in the same manner as in <Experimental Example 3> using the cream containing the derivative of panduratin A, and the results are shown in Table 12 below.

Acne pathogenic bacteria Test solution Viable cell count (microbial count / ml) 0 hours 24 hours Propionibacterium Acnes Preparation Example 13 2.0 × 10 ⁵ <One Preparation Example 14 2.0 × 10 ⁵ <One Preparation Example 15 2.0 × 10 ⁵ 〈7 Preparation Example 16 2.0 × 10 ⁵ 7.8 × 10 ² Cream without derivative of panduratin A 2.0 × 10 ⁵ 4.5 × 10 ³ Staphylococcus epidermis Preparation Example 13 5.4 × 10 ⁵ <One Preparation Example 14 5.4 × 10 ⁵ <One Preparation Example 15 5.4 × 10 ⁵ 〈6 Preparation Example 16 5.4 × 10 ⁵ 3.9 × 10 ² Cream without derivative of panduratin A 5.4 × 10 ⁵ 6.8 × 10 ³ Microcaucus Luteus Preparation Example 13 6.0 × 10 ⁵ <One Preparation Example 14 6.0 × 10 ⁵ <One Preparation Example 15 6.0 × 10 ⁵ 〈7 Preparation Example 16 6.0 × 10 ⁵ 2.5 × 10 ² Cream without derivative of panduratin A 6.0 × 10 ⁵ 2.3 × 10 ³

As can be seen from the results of Table 12, the cream of the embodiment according to the present invention had a very high antibacterial activity against acne-inducing bacteria such as propionibacterium acnes compared to the component except the derivative of panduratin A.

Experimental Example 5

Pandulatin  Skin application of creams containing A compound or derivatives thereof

A clinical trial of acne prevention and treatment was performed using panduratin A-containing cream prepared in <Production Example 9>. Subjects were 30 males and females in their mid teens to mid thirties who suffered from acne. The number of lesions decreased significantly after 4 weeks compared to the number of lesions before the start of the study, which was statistically significant (p-value <0.05).

Determination of the number of acne lesions when applying pandulatin A Average number before study Average number after 4 weeks of study P-value Cotton cloth 19.43 5.19 0.0081 papule 17.90 6.05 0.0027 pustule 5.81 2.05 0.0225 nodule 0.75 0.22 0.031

On the other hand, using the cream containing the derivative of panduratin A prepared in <Production Example 13> was carried out a clinical experiment on the prevention and treatment of acne in the same manner as above and the results are shown in Table 14. The number of lesions decreased significantly after 4 weeks compared to the number of lesions before the start of the study, which was statistically significant (p-value <0.05).

Determination of the number of acne lesions when applied to the skin Average number before study Average number after 4 weeks of study P-value Cotton cloth 18.92 4.97 0.0075 papule 18.82 7.04 0.0031 pustule 6.53 3.02 0.0232 nodule 0.58 0.18 0.025

1 is a ¹³ C-NMR spectrum of isolated purified panduratin A of the present invention.

2 is a ¹ H-NMR spectrum of the isolated purified panduratin A of the present invention.

Figure 3 is a ¹ H- ¹ H COSY spectrum of the isolated purified panduratin A of the present invention.

4 is a ¹ H- ¹³ C HMBC spectrum of the isolated purified panduratin A of the present invention.

5 is a FAB-Mass spectrum of isolated purified panduratin A of the present invention.

Figure 6 is an isolated purified purified panduratin A of the present invention ¹³ C-NMR spectrum of the derivative.

Figure 7 is isolated purified purified panduratin A of the present invention ¹ H-NMR spectrum of the derivative.

8 is isolated and purified of panduratin A of the present invention DEPT spectrum of the derivative.

9 is isolated and purified of panduratin A of the present invention EI / MS spectrum of the derivative.

10 is a graph showing the results of measuring the antimicrobial activity of propionibacterium acnes of isolated purified panduratin A by viable cell count method.

◆: dimethyl sulfoxide, a control

Panduratin A sample at 0.0004% concentration

▲: erythromycin sample at 0.0004% concentration

Figure 11 shows isolated purified panduratin A of the present invention. It is a graph showing the results of measuring the antimicrobial activity of the derivatives propionibacterium acnes by viable cell count method.

◆: dimethyl sulfoxide, a control

■: Pandoratin A of 0.0008% concentration Sample of derivative

▲: erythromycin sample at 0.0008% concentration

Claims (8)

Contains as an active ingredient a panduratin A compound represented by Formula 1, a derivative of panduratin A represented by Formula 2, and a pharmaceutically acceptable salt thereof Antimicrobial composition. <Formula 1>

<Formula 2>

　　　　　　　　 According to claim 1, wherein the composition is Propionibacterium Acnes, Staphylococcus epidermis, Micrococos Luteus, Staphylococcus aureus, Staphylococcus warneri, Staphylococcus haemoraiticus, An antimicrobial composition comprising an antimicrobial activity against a microorganism selected from the group consisting of Staphylococcus xylose, Staphylococcus hominis, and Staphylococcus sapropiticus. An antimicrobial composition comprising an extract of water of Kaempferia pandurata or an organic solvent of C1 to C6 as an active ingredient. According to claim 3, wherein the C1 ~ C6 organic solvent is C1 ~ C6 alcohol, acetone (acetone), ether (ether), benzene (benzene), chloroform (chloroform), ethyl acetate (ethyl acetate), methylene chloride ( methylene chloride), hexane (hexane), cyclohexane (cyclohexane), petroleum ether (petroleum ether) composition for antibacterial, characterized in that selected from the group consisting of. The composition according to claim 3 or 4, wherein the composition is selected from propionibacterium acnes, staphylococcus epidermis, micrococos luteus, staphylococcus aureus, staphylococcus warneri, and staphylococcus. An antimicrobial composition comprising an antimicrobial activity against one or more microorganisms selected from the group consisting of Moraticus, Staphylococcus xylose, Staphylococcus hominis and Staphylococcus sapropiticus. Contains as an active ingredient a panduratin A compound represented by Formula 1, a derivative of panduratin A represented by Formula 2, and a pharmaceutically acceptable salt thereof Acne treatment composition. A composition for treating acne, comprising an extract of water of Kaempferia pandurata or an organic solvent of C1 to C6 as an active ingredient. The method of claim 7, wherein the C1 ~ C6 organic solvent is C1 ~ C6 alcohol, acetone (acetone), ether (ether), benzene (benzene), chloroform (chloroform), ethyl acetate (ethyl acetate), methylene Chloride (methylene chloride), hexane (hexane), cyclohexane (cyclohexane), petroleum ether (petroleum ether) composition for treating acne, characterized in that selected from the group consisting of.

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