WO2005084613A1 - Skin preparation for external use - Google Patents

Abstract

It is intended to provide a skin preparation for external use whereby sunburn due to ultraviolet light irradiation and spots and freckles accompanying aging can be relieved, decolored or eliminated to give whitened and beautiful skin. Namely, a skin preparation for external use containing at least one member selected from the group consisting of curdione, curcumol, neocurdione and curcumenone having activity of highly inhibiting melanogenesis. It may contain a turmeric leaf extract as a substitute for the above active ingredient(s).

Description

 Description Skin external preparation Technical field

 The present invention percutaneously penetrates into the skin by applying, soaking, rubbing, or contacting the skin, reducing the amount of stains and freckles already formed, The present invention relates to an external preparation for skin used to regain the color of the skin, and to a basic external preparation such as cosmetic water and cosmetic cream, and a skin external preparation used as a bath and medical soap. Background art

 Its purpose is to protect the skin from the ultraviolet rays that increase due to the recent stratospheric ozone depletion, prevent skin aging and darkening, and restore skin's original beauty by eliminating spots, sonogas, and dullness. Demand for basic whitening cosmetics has increased. In particular, women who had been tanned by irradiating ultraviolet light for the blackheads that were prevalent in the 1990s began to shift to the whitening trend, and the stains that remained after the sunburn had subsided. There is a strong demand for removing freckles.

 Cosmetic products for whitening include those that try to improve the dullness due to aging of the skin by suppressing the production of pigments due to active oxygen generated by ultraviolet irradiation, and the melanin-forming reaction that causes spots. Some try to reduce spots by inhibiting the activity of the chin mouth synase, which partially catalyzes. As the former chemical products, cosmetics containing antioxidants such as vitamin C, tocopherol (vitamin E), and superoxide dismutase (SOD) are being sold. Vitamins such as vitamins C and E generally have poor stability, and oxidized vitamin A and oxidized vitamin E generated after being oxidized with active oxygen have a negative effect, so they are satisfactory in terms of whitening. It cannot be done. Synthetic antioxidants with good stability tend to be shunned in recent years by consumers for safety, nature and health.

In order to meet the demands of consumers who prefer natural cosmetics, natural whitening cosmetics using herbal extracts or herbal extracts have been proposed as useful ingredients for skin and whitening. Yes.

 For example, Japanese Patent Application Laid-Open No. 6-227960 discloses a skin cosmetic containing a crude drug extract such as coconut and cypress as an inhibitor of melanin production based on tyrosinase f tongue inhibition. The radish extract used here is an extract obtained by extracting the rhizome of ゥ = r with a hydrophilic organic solvent such as water, methanol or ethanol.

 Japanese Patent Application Laid-Open No. 2002-121144 discloses that crude drug extracts such as bread corn, cowpea, and radish are excellent in preventing the oxidation of unsaturated fatty acids and eliminating active oxygen, and the external preparation for skin containing these is effective in improving dullness. Is superior to vitamin E. The extract of van radish used here is a hot water extract of the rhizome, an ethanol extract of the whole plant, and an extract of 1,3-butylene recall of the rhizome, and the excellent antioxidant effect of the extract It is intended to improve skin, firmness, and even dullness of the skin.

 Japanese Patent Application Laid-Open No. 2002-212052 discloses water-soluble thickeners such as glycerin hyaluronate Na, antibacterial alcohols such as ethanol, antioxidant vitamins such as tocofunicole, mefenamic acid and tranexam. There is disclosed a cosmetic composition containing an anti-inflammatory agent such as an acid and a plant extract such as ozone, button, aloe, carrot, and corn as a whitening component. This patent document shows that the pigmentation induced by ultraviolet light disappears, but the role of the fit substance on its action and effect is not evident.

 On the other hand, it is known that talcumin contained in the root rhizome extract of konkon has an antioxidant effect. (Supervised by Hideharu Itokawa, "The great effect of konkon," Sora Publishing, June 22, 2001, 10th printing, 20-34 JP-A-2001-139466 and JP-A-2002-80338 disclose cosmetics utilizing a salt or derivative of talcumin which acts as an inhibitor of the activity of matritus proteases (collagenase, gelatinase, etc.). Proposed. The cosmetics disclosed herein are intended to prevent degradation of fiber proteins such as elastin related to aging of the skin, and to improve skin, tarmi, and dullness of the skin.

The scavenging of active oxygen by the antioxidant component is intended to suppress the formation of spots and freckles due to ultraviolet irradiation, and further reduces the whitening effect of reducing, eliminating, and fading stains and freckles already formed. Improvement is desired. On the other hand, as described above, various cosmetics utilizing the effect of konkon extract on the skin and skin have been disclosed, but the mechanism of the effect is still unclear, and the effect varies depending on the extraction method and the composition of the extract. There is. Disclosure of the invention

 The present invention has been made as a result of detecting the active ingredients for whitening and the method for extracting whitening, and the object of the present invention is to reduce sunburn due to ultraviolet irradiation, stains and freckles due to aging, fading, and erasing. An object of the present invention is to provide a skin external preparation that restores the original color and shine of the skin to achieve whitening and beautiful skin.

 The external preparation for skin of the present invention contains, as an active ingredient, at least one selected from the group consisting of curdion, krugmole, neognoresion, and curcumenone. A skin external preparation according to another aspect of the present invention contains konkon (Curuc ui mae R hizoma) leaf extract, and particularly preferably contains an extract obtained by extracting konkon leaf with a hydrophobic organic solvent. . In addition, it is preferable that at least one selected from the group consisting of a hydrophobic organic solvent f, hexane, dimethyl ether and ethyl acetate is used.

 In yet another aspect of the present invention, a whitening agent for skin, containing 0.5 to 5% by mass of culdione and 0.5 to 5% by mass of talcumol, for example, extracted with a mixture of water and ethanol. Is contained in an amount of 1 to 20% by mass.

 The present invention further provides a cosmetic containing the above-mentioned external preparation for skin or a skin whitening agent of the present invention as a cosmetic capable of achieving skin whitening and skin whitening.

 In addition, the present invention provides an extraction method including a step of extracting a whitening component from a powdered coconut leaf, and a step of extracting the coconut leaf with a hydrophobic organic solvent.

The external preparation for skin of the present invention is transdermally taken into the skin, inhibits the activity of tyrosinase in the reaction pathway shown in FIG. 1, and thereby suppresses the production of melanin which causes stains. In addition, it can be expected to fade and reduce the stains and freckles that have already formed along with the turnover of the skin, so it is effective as a skin-whitening essence to be used in cosmetics and bath salts. Further, since the external preparation for skin of the present invention has a bacterial activity, it is also effective in preventing sebaceous skin from dermatitis. Brief Description of Drawings

 FIG. 1 is a schematic diagram of a reaction path for explaining a mechanism of melanin production. FIG. 2 is a schematic diagram of a reaction path for explaining the principle of measuring the effect of removing active oxygen. FIG. 3 is a gas chromatography of a hexane extract of coconut leaves.

 FIG. 4 is a mass spectrum of peak component 2 in the gas chromatography shown in FIG.

 FIG. 5 is a mass spectrum of the peak component 6 in the gas chromatography shown in FIG.

 FIG. 6 is a mass spectrum of peak component 1 in the gas chromatography shown in FIG.

 FIG. 7 is a mass spectrum of peak component 3 in the gas chromatography of FIG.

 FIG. 8 is a dendrogram showing the tyrosinase activity inhibition rate and SOD activity in each fraction of the icon leaf extract. BEST MODE FOR CARRYING OUT THE INVENTION

 The external preparation for skin of the present invention contains, as an active ingredient, at least one selected from the group consisting of curdion, talcumol, neocurdione, and curcumenone. These compounds may be synthetic or may be extracts from natural products.

 Here, the cruzione means 1 (10) -germacrene-5,8-dione represented by the following chemical formula (1).

Clecmonore is a compound represented by the following chemical formula (2).

 Talcmenone is a compound represented by the following chemical formula (3)

ネオクルジオンは、 下記化学式 (4) で示される化合物である。

Neoculdione is a compound represented by the following chemical formula (4).

これらの化合物は、 いずれも経皮透過性に優れ、 皮膚内部に浸透して、 誇 1図 に示す反応経路において、 チロシナーゼ活性を阻害し、 これによりメラニンの生 成を抑制することができる。 また、 クルジオン及びクルクモール、 特にクノレジオ ンは、 大腸菌 （E s c h e r i c h i a c o l i) ， 枯草菌 （B a c i 1 1 u s s u b t i 1 i s ) 、 緑膽菌 (P s e u d omo n a s a e r u g i n o s a) 等の各種バクテリアゃカビ類に対して抗菌性を有している。

Each of these compounds has excellent transdermal permeability, penetrates into the skin, and inhibits tyrosinase activity in the reaction pathway shown in FIG. 1, thereby suppressing the production of melanin. In addition, curdion and curcumol, especially knollegion, are antibacterial against various bacteria such as Escherichiacoli, Bacillus subtilis (Baci 11 ussubti 1 is), and Bacillus subtilis (Pseudomo nasaeruginosa). have.

The external preparation for skin of the present invention may contain only one of the above active ingredients, but preferably contains all of them. In this regard, ゥ kon Leaf Extract contains cruzi ^ ", It contains talc mall, neocludion, and curcumenone, so it is easy and convenient to obtain.

 Here, “ゥ kon” refers to the scientific name rcurcumae R izomaJ, which is generally called autumn cum (Cucuma longa) and spring apple (curcuma aromatica).

 Conventionally, radish extract has been known to have a bile effect of its rhizome extract and its main component, curcumin (see Nanedo Co., Ltd., Revised 4th Edition of Pharmaceutical Sciences) and has been used as a crude drug. In recent years, curcumin has been used as an active ingredient such as an antioxidant in cosmetics, an anti-inflammatory agent, and a whitening ingredient, utilizing the antioxidant action of curcumin and the anti-inflammatory action of rhizome extract. Its efficacy is not known and it has been discarded.

成分 The components of the essential oil extracted from the leaves of the konkon are different from the rhizome extract composition. Gas chromatography Matogurafi first and mass spectral analysis of the results, the components of the content of 1 mass _^0/0 or more Ukon leaf extract component is 1, 8-Shineroru, Renaruru, a- Terubineoru, caryophyllene oxa Lee de, Kurujion, Gerumaku port down state, and are talc Mall, the content of Kurujion and talc mall is about 5 0 weight _^0/0. In addition to these, it contains neocurdione and curcumenone as trace components.

 ク ル Culdion, the main component of konkon leaf extract, is hardly contained in konkon rhizome extract, and conversely, curcumin, which is known as an active ingredient of rhizome extract, is hardly contained in konkon leaf extract. .

 As described above, the konkon leaf extract contains a high proportion of the effective ingredients for the skin, such as curdion and curcumol, and also contains the effective ingredients such as neocurdione and talcumnone. It is more convenient to include konkon leaf extract than to include it. In addition to the effective use of konkon leaf that had been discarded in the past, ゥ the effect of plus alfa based on minerals (such as terpenes) and minerals other than the above-mentioned active ingredients contained in konkon leaf extract. Can be expected.

The extraction solvent used for obtaining the konkon leaf extract containing the active ingredient as described above may be selected in consideration of the purpose of use, the type of the product to be provided, the processing to be performed later, and the like. Water; methanol, ethanol, propyl Alcohols, lower alcohols such as isopropyl alcohol and butanol-polyhydric alcohols such as propylene glycol, 1,3-butylene glycol and glycerin; ketones such as acetone and methylethyl ketone; ethyl acetate and butyl acetate; Esters; hydrocarbons such as hexane and heptane; and ethers such as ethyl ether and tetrahydrofuran. However, knollezion, talcumol, neoculdione, and talcumenone, which are active ingredients for whitening, all have high solubility in hydrophobic organic solvents such as hexane, so that an extract with a high content of these whitening components is necessary to obtain an extract with a high content of these whitening components. Extraction is preferably performed using a hydrophobic organic solvent, preferably one selected from the group consisting of hexane, getyl ether and ethyl acetate, or a mixture thereof, and more preferably hexane.

 The extraction may be performed in multiple stages, for example, extraction of coconut leaf powder with methanol followed by extraction with hexane.However, in order to increase the content of whitening components, hydrophobic organic It is preferable to include an extraction step with a solvent. The extract-containing solution extracted with these solvents may be used as it is as an external preparation for the skin, or may be used after being subjected to treatments such as concentration, dilution, filtration, and drying as needed. After the extraction, the beaded aqueous organic solvent may be volatilized by drying or the like to obtain a powder having a high whitening component content.

 On the other hand, when the extract is contained in an external preparation for skin together with an extraction solvent, it is preferable to use low-grade alcohol, water or a mixture thereof, particularly a mixture of water and ethanol as the extraction solvent.

The external preparation for skin of the present invention uses curdion, curcumol, neocurdione, a synthetic product of talc-menone, an isolated product from natural products, or konjac leaf extract, which may be contained in an appropriate solvent or base. As an additive, it may be added to cosmetics or quasi-drugs. The content is appropriately selected according to the final product. Final products include skin cleansing creams, cleansing lotions, facial cleansers, soaps, and other skin cleansing agents in addition to skin agents, lotions, and cosmetic creams; skin conditioners such as moisturizing lotions, soft lotions, and astringent lotions. Protective agents such as milky lotions, emollient milks, and vanishing creams; activators such as massage creams, massage lotions, foam packs, and peel-off packs; bath salts; and poultices. In each case, the active ingredient is transdermally incorporated into the skin, It can work for fading, reducing and disappearing.

 Depending on the final product, the skin external preparation of the present invention is a solid that does not impair the effect of the extract. It can contain humectants, UV absorbers, thickeners, dyes, antioxidants, and chelating components. Oil bases include beeswax and cocoa oil; carnapa wax, higher fatty acids, solid paraffin, solid oily raw materials such as cetyl alcohol, stearyl alcohol; semi-solid oily raw materials such as serine and lanolin; squalane, olive oil; Castor oil, palm oil, peanut oil, liquid paraffin, oleic acid, linoleic acid, octyldodecyl myristate, silicone oil and the like can be used.

 Examples of the aqueous base include humectants such as glycerin, sorbitol, polyethylene glycol, pyrrolidone carboxylic acid and its salts, collagen, hyaluronic acid and its salts, chondroitin sulfate and its salts; carboxymethyl cellulose sodium, polyvinyl alcohol Thickeners such as Ni / Rare Coal ', xanthan gum, canoleboxybininole polymer, hydroxypropyl cellulose, and gum arabic are used.

 Examples of the surfactant include nonionic surfactants such as polyethylene glycol isostearate, sorbitan stearate, glycerin fatty acid ester, polyoxyethylene hexylde, and silyl ether; vanionics such as sodium lauryl sulfate and sodium lauryl phosphate; Cationic surfactants such as stearyldimethylbenzylammonium chloride; natural surfactants such as sucrose fatty acid ester, casein sodium, lecithin, and collagen are used.

 Examples of the pH adjuster include potassium carbonate, sodium hydrogen carbonate, and ammonium hydrogen carbonate.

In addition, those which can be added as required, such as para-dimethylaminobenzoic acid, ethyl ethyl perocyanate, ethyl ethyl diisopropylcinnamate, 2-hydroxy-4-methoxybenzophenone, triethanolamine salicylate, etc. UV absorbers; preservatives such as ethyl paraben and butyl paraben; anti-inflammatory agents such as glycyrrhizic acid derivatives, glycinoleretinic acid derivatives, salicylic acid derivatives, hinokitiol, zinc oxide, allantoin; vitamins such as retinol noremitinate Antioxidants such as vitamin Bs such as riboflavin and nicotinic acid amide, vitamin Ds such as cholecalciferol, d1—vitamin E such as 1-tocopherol; sodium erythorbic acid. Antioxidants such as sage extract and parahydroxydisole; activators such as royal jelly and cholesterol derivatives; various amino acids; blood circulation promoters such as _γ- oryzanol, dextran sodium sulfate; coloring agents such as titanium yellow, carsamin and safflower; Other plant extracts are included.

 The skin whitening agent of the present invention is a cosmetic or quasi-drug mainly for skin whitening, among skin external preparations, and contains 0.5 to 5% by mass of curdion and 0.5 to 5% by mass of curcumol. . Alternatively, konkon leaf extract is contained in an amount of 1 to 20% by mass, depending on the extraction method.ゥ When konkon leaf extract is contained together with an extraction solvent, it is preferable to use an extract extracted with a water-ethanol mixture because of its relationship with skin irritation. As other ingredients, if the skin lightening agent is a lotion, it is diluted with purified water, and if necessary, the above-mentioned humectant, thickener, pH regulator, preservative, fragrance, oxidation What is necessary is just to contain an inhibitor, a surfactant, an ultraviolet absorber, etc. In the case of a semi-solid or gel-like cosmetic cream / cleansing cream, an oily base and an aqueous base may be used as appropriate instead of purified water. Example

 [Preparation of konkon extract]

 ゥ Container leaf extract No. 1:

 The leaf powder of spring corn, produced by Oki Silk, was immersed in 30% ethanol for 2 days and then filtered. The residue was immersed again in 30% ethanol for 2 days and filtered. The obtained filtrate (ethanol extract) was concentrated under reduced pressure, sterilized by heating at 80 ° C, cooled, and filtered to obtain a corn leaf extract. 200 g of this konkon leaf extract was dissolved in 30% ethanol water to make a 1 liter solution (containment of konkon leaf extract: 20%).

 ゥ Contain leaf extract No 2:

 700 g of leaf powder of Shunkon, Yamakawa-cho, was immersed in 4 liters of hexane for 2 days, and then filtered. The residue was immersed again in 4 liters of hexane for 2 days and filtered. The obtained filtrate (hexane extract) was concentrated under reduced pressure to obtain a corn leaf extract.ゥ Conn root extract:

The root powder of spring corn produced in Oki was immersed in 30% ethanol for 2 days and then filtered. The residue was immersed again in 30% ethanol for 2 days and filtered. The resulting filtrate (e) The ethanol extract was concentrated under reduced pressure, sterilized by heating at 80 ° C, cooled, and filtered to obtain a root extract. 200 g of the konkon root extract was dissolved in 30% ethanol water to make a 1 liter solution (20% konkon root extract content).

 (Active oxygen removal effect)

 The active oxygen remover was measured for N. leaf extract No. 1 and N. root extract by NBT test.

 The NBT test consists of a coloring reagent (phosphate buffer of pH 8.0 containing 0.24 mM of nitro blue tetrazolium (NBT) and 0.4 mM of xanthine) and an enzyme solution (0.049 U / ml of xanthinoxidase). Is added to the sample solution, and the amount of diformazan generated by the reaction shown in Fig. 2 is measured to determine the amount of xanthine (the active oxygen radicals generated by O-oxidation). The more hydrogen ions (active oxygen radical scavenging function), the smaller the amount of NBT converted to diformazan.

1 ゥ konkon leaf extract No. 1 or 10 μl of konkon root extract, add 10 Ομ1 of the coloring reagent, stir with a mixer for 1 minute, add 100 l of enzyme solution, add stirring, and stir for L minutes Then, the mixture was heated at 37 ° C. for 28 minutes. Then, add 20 μl of a reaction stop solution (sodium dodecyl sulfate 69 OmM), and stir for 5 minutes to stop the reaction. The absorbance E _s at 5 60 nm was measured.

Instead of the enzyme solution, using distilled water 100 1 as Planck liquid, similarly performed on the absorbance was measured E _{SB 1} in 560 nm.

As a control, the absorbance at 560 nin (EB ₁ ) when the enzyme solution was added using 10 μl of distilled water instead of the sample aqueous solution and the black solution was used instead of the enzyme solution absorbance at 56011111 _£] ^ ₁ was measured.

 From the measured absorbance, the active oxygen removal rate was determined based on the following equation.

Active oxygen removal rate = U— (E _S -E _SB1 ) ÷ (E _B1 — E _BB1 )} xl 00 ゥ Container leaf extract No. 1 has an active oxygen removal rate of 34.4%, indicating that the activity of ゥThe oxygen removal rate was 63%.ゥ It can be said that the active oxygen removal function of konkon leaf extract is lower than that of konkon root extract.ゥ Concrete root extract contains curcumin, which generates hydrogen ions. ク ル It is probable that cruzione and knorecmol, which are the main components of konkon leaf extract, are not expected to generate any x-radicals. (Tyrosinase activity inhibitory action)

 The konkon leaf extract No. 1 and the konkon root extract were examined for their inhibitory effect on the activity of tyroxynase, an enzyme involved in melanin production.

The measurement was carried out using an enzyme solution (0.1 unit Zmg, 10%) and a phosphate buffer solution (L-DOPA (L-dihydroxyphenylalanine)) maintained at pH 6-6.2 as a substrate. using the Z 1 5 M of N a ₂ HP O ₄ solution 200 meters l and lZl 5 M of KH ₂ P0 ₄ solution 800m solution was dissolved in a mixture) of l, the sample solution was添Ka卩, the dopaquinone This was performed by measuring the amount of production. L-DOPA reacts as shown in Fig. 1 to produce dopaquinone, a source of melanin production, and tyrosinase enzymes are involved in this reaction. Therefore, the sample inhibits the tyrosinase enzyme reaction, thereby reducing the amount of dopaquinone produced and consequently the melanin production can be suppressed.

Specifically, as the tyrosinase enzyme solution, a filtrate obtained by subjecting a suspension obtained by calorizing a phosphate buffer solution to 10 _g of phosphate buffer to 1 _g of acetone powder prepared from potato tubers to obtain a suction solution was used.

 Add 1 μl of substrate solution and 20 μl of enzyme solution to 20 μl of konkon leaf extract No. 1 or 20 μl of konkon root extract, which are sample liquids, mix and react at 30 ° C for 15 minutes After that, 20 μl of 0.1 N hydrochloric acid was added as an anti-stop solution.

 After the reaction, the absorbance (S) was measured at 400 nm.

 The absorbance (B) was measured at 40 nm using a phosphate buffer instead of the sample solution and the substrate as a blank. The tyrosinase inhibition rate was calculated by the following equation.

 Tyrosinase inhibition rate = (B-S) / Β100

 The tyrosinase activity inhibition rate of ゥ kon leaf extract 液 ο.1 was 14.9% and the tyrosinase activity inhibition rate of ゥ konkon root extract was 7.7%. It can be seen that the ゥ kon leaf extract has about twice the tyrosinase activity inhibitory effect of the ゥ kon root extract.

[Relationship between konkon leaf extract and tyrosinase activity inhibitory effect due to differences in extraction methods] ゥ Separate konkon leaf extract No. 1 with hexane and water, and inhibit tyrosinase activity for both hexane and water fractions. The ratio was measured in the same manner as described above. The tyrosinase activity inhibition rate of the hexane fraction was 46.9%, whereas the water fraction The minute was 38%. In the hexane fraction, the inhibition of larosinase activity was increased as compared with the radish leaf extract No. 1, whereas in the water fraction, the reversal phenomenon of promoting tyrosinase activity was observed.

 [Identification of active ingredients contained in ゥ cone leaf hexane extraction ^]

 (4) Gas chromatographic analysis of corn leaf extract No. 2 gave the results shown in Fig. 3. Components corresponding to peaks 1, 2, 3, and 6 shown in FIG. 3 were separated, and mass spectrum analysis and NMR analysis and melting point were measured. The mass spectrum of peak component 2 (conditions: GCEI) was as shown in Fig. 4, and it was identified that it was a cruzion. The mass spectrum of peak component 6 (condition: GCE I) was as shown in FIG. 5, and it was identified as talcumol. The mass spectrum (condition: GCCI) of peak component 1 was as shown in FIG. 6, and it was identified as talcummenone. The mass spectrum of the peak component 3 (condition: GCCI) is as shown in Fig. 1, and it was identified as neocludione.

 [ゥ Tyrosinase inhibitory activity and SOD activity of active ingredients contained in corn leaf extract]

 In the same manner as in the coconut leaf extract No. 1, 179 g of an ethanol-derived product was obtained from the spring corn leaf in Yamakawa Town, and this extract was further separated with hexane and water to obtain a hexane fraction (O 64 g) and a water fraction (1500.6 g). The hexane fraction was chromatographed using a column packed with silica gel (BW-127ZH from Fuji Shirijia Chemical). First, a mixture of hexane and ethyl acetate in a ratio of 3: 1 was used to separate the fractions into three fractions (fraction 1: 0.2 g, fraction 2: O. 04 g, fraction 3: 0.12) g), 0.2 g of curcumeno Z from fraction 1 and 0.03 g of curdione from fraction 2.

 Next, fraction 3 was subjected to silica gel chromatography and fractionated into three fractions using a solvent in which hexane and ethyl acetate were mixed at a ratio of 10: 1 (fraction 4:24 mg, fraction 5:15 mg, fraction 5:15 mg, 6:29 mg], 1.2 mg of neocurdione from fraction 4, and 12 mg of curcumonele from fraction 5.

The tyrosinase inhibitory activity and the SOD activity of each fraction fractionated above were measured according to the above-mentioned methods. The results are shown in FIG. In addition, the relationship between concentration and tyrosinase activity was investigated for culdione, talcumol, kunocumenone, and neoculdione isolated from each fraction. The results are shown in Table 1.

 table 1

表 1から、 いずれの成分も高いチロシナーゼ阻害活性を示し、 美白成分として 有用であることが確認できた。 従って、 クルジオン及びクルクモーノレを主成分と し、 さらにネオクルジオン、 タルクメノンを含有するゥコン葉エキスは、 高い美 白効果を期待できる。

From Table 1, it was confirmed that each of the components exhibited high tyrosinase inhibitory activity and was useful as a whitening component. Accordingly, a konkon leaf extract containing curdione and curcumonele as main components and further containing neocurdione and talcumnone can be expected to have a high whitening effect.

 [ゥ Isolation of konkon leaf main component and tyrosinase inhibitory activity]

 After putting 1 g of coconut leaf extract No. 2 into a column packed with silica gel: a, a mixture of hexane and ethyl acetate (hexane: ethyl acetate 3: 1), ethyl acetate, chloroform, methanol In this order, it evolved and eluted. The eluate obtained was analyzed for its components, and it was found that crudion was contained in the mixed liquid fraction of hexane and ethyl acetate, and talcumol was contained in the ethyl acetate fraction (purity 90% or less_ ^ ).

When the solvent of the above-mentioned mixed solution fraction of hexane and ethyl acetate and the solvent of the ethyl acetate fraction were distilled off, white crystals were obtained. The yield of crudion was 0.37 _§ and the yield of talcumol was 0.23 g.

 The tyrosinase activity of each of the white crystals of Culdione and Talcmol was measured according to the method described above. Note that none of these crystals was soluble in water; they were dissolved in a small amount of dimethyl sulfoxide (DIMSO) and then dispersed in water to form a sample solution.

The tyrosinase inhibitory activity of the Culdione solution was 62.1%, and the tyrosinase inhibitory activity of the talcumone solution was 55.4%. [Effect as lotion]

 The corn extract No. 1 was diluted with purified water to prepare a 2% lotion of konkon leaf extract.

 Six panelists used this lotion for two months instead of applying it after washing in the morning, before makeup, and after washing in the evening.The following results were obtained. Was.

 None 1 (24-year-old woman) Stain became thin and skin became white

 Paneler 2 (60-year-old woman)

 Paneler 3 (five-year-old woman) Spots decreased to less than half in about two months.

 Paneler 4 (male aged 46) Sobacas decreased to around 1Z4 in about one month.

 Paneler 5 (37-year-old woman) The pores are no longer darkened.

 Paneler 6 (31-year-old woman) Eczema and acne core came off without pus.

 As can be seen from the results of panelists 1-4, the lotion of the present invention is effective in fading, reducing and eliminating stains and freckles. Paneler 5 is not a stain or buckwheat, but it can be seen that the skin lotion of the present invention has a whitening effect such as reduced blackening and pigment fading.

 Paneler 6 does not have a whitening effect such as pigment fading, but it is thought to be due to the antibacterial effect of the extract of konkon leaf.

 (Antibacterial effect)

 700 g of konkon leaf powder from Kumamoto was extracted with 4 liters of methanol at room temperature for 24 hours, filtered, and separated into a methanol extract and a residue. The residue was immersed again in 4 liters of methanol, filtered in the same manner, and then subjected to methanol extraction again. The obtained methanol extracts were combined and concentrated under reduced pressure to obtain 122. 1 g of a methanol extract.

The obtained methanol extract was separated into a hexane layer and a methanol layer using 1 liter of hexane, and each layer was concentrated under reduced pressure to obtain 38.7971 g of the hexane extract. And 49.938 g of methanol extract. Antibacterial activity of both hexane and methanol extracts by paper disk method using E. coli as an indicator When the activity was examined, no antibacterial activity was observed in the methanol extract, and antibacterial activity was observed in the hexane extract.

 Then, the hexane extract was subjected to steam distillation to obtain 0.323 g of an essential oil component. Using this essential oil component, an antibacterial test was performed using Escherichia coli as an indicator, DMS〇 as a negative control using a microplate method, and benzoic acid as a positive control. Indicated.

 The hexane extract was subjected to silica gel chromatography to obtain a curdion-containing fraction and a curcumol-containing fraction. For each fraction, antibacterial activity against various bacteria was examined by the paper disk method and the microplate method. The results are shown in Table 2 (paper disc method) and Table 3 (microplate method).

 In the table, “ten” indicates that the substance has antibacterial activity, and the number is large, indicating that the activity is strong. "One" indicates no antimicrobial activity.

Table 2

Test strain Crudion Knorecmol

 Bacillis subtilis + + + + + +

 Flavobactirium lutescens + + + +

 Escherichia coli + + + + +

 Micrococcus luteus + +

 Pseudomonas aeruginosa + +

 Aspergillus flavus ― ―

 Aspergillus niger + +

 Aspergillus japonicus ― ―

 Aspergillus oryzae +++

 Aspergillus sojae ― Ichi

 Fusarium solani + + +

 F sarium oxysporum + + +

Saccharomyces cerevisiae ++ Table 3

表 2及び表 3の結果から、 クルジオン及びタルクモールの含有率は、 種々のバ クテリァ及び一部の力ビについて、 抗菌活性を有することが確認できた。 産業上の利用可能性

From the results shown in Tables 2 and 3, it was confirmed that the content of cruzione and talcumol had antibacterial activity for various bacterium and some power plants. Industrial applicability

 Since the skin external preparation of the present invention has a high tyrosinase activity inhibitory activity and also has an antibacterial activity, it is used as a skin external preparation for the purpose of whitening cosmetics, prevention of acne and spots and treatment. be able to.

Claims

The scope of the claims 1. An external preparation for skin containing, as an active ingredient, at least one selected from the group consisting of curdione, talcmol, neocurdione, and talcmenone. 2. ゥ kon (Curcuma e Rhizoma) An external preparation for skin containing leaf extract.  3. The external preparation for skin according to claim 2, wherein the extract of cocoon leaves is an extract extracted with a hydrophobic organic solvent.  4. The external preparation for skin according to claim 4, wherein the hydrophobic organic solvent is at least one selected from the group consisting of hexane, getyl ether and ethyl acetate. 5. Kurujion a 0.5 to 5 mass _^0/0 and Kurukumoru a 0.5 to 5 wt% you containing skin lightening agent.  6. A skin whitening agent containing 1 to 20% by mass of konkon leaf extract extracted with water and ethanol.  7. A cosmetic containing any one of claims 1 to 6.  8. A method of extracting whitening ingredients from konkon leaf powder,  An extraction method comprising a step of extracting with a hydrophobic organic solvent.