JP2005306795A - Skin care external preparation suitable as quasi-drug - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a means for suppressing sustained inflammation induced by high-dose ultraviolet irradiation. <P>SOLUTION: A skin care external preparation is obtained by including (1) 0.01-1 mass% of sophoraflavanone G of formula(a) and/or its salt and (2) 0.001-1 mass% of 6-acetyl-11,13-dihydrohelenalin of formula(b). In this preparation, it is preferable that the sophoraflavanone G is derived from a product that is obtained by liquid/liquid extraction with water and ethyl acetate of alcohol extract of Sophora flavescens, concentrating the resultant ethyl acetate phase followed by fractionation refining with column chromatography with silica gel as carrier and then removing the solvent, whereas, the 6-acetyl-11,13-dihydrohelenalin is derived from a product that is obtained by alcohol extraction of a plant body of Arnicae plant followed by solvent removal. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

  The present invention relates to an external preparation for skin, and more particularly to an external preparation for skin suitable for quasi-drugs that appealed for anti-inflammatory or melanin production suppression.

  With the progress of environmental pollution in recent years, the layer pressure of the atmospheric ozone layer has decreased and holes have been generated, and the amount of ultraviolet rays that penetrate the atmospheric layer and reach the ground has increased rapidly. It is well known. In other words, even if you live the same life as in the past, the exposure dose of ultraviolet rays is very large in modern times. In general, exposure to high doses of ultraviolet radiation is said to induce pigmentation that persists after the skin reaction has subsided, such as long-lasting inflammation and subsequent stains. It is said that this is because various inflammatory factors run away due to high-dose external irradiation and the homeostasis is greatly destroyed. There are many substances that have anti-inflammatory activity in the world, while there are few anti-inflammatory components effective for all or many inflammations. This is because there are many types of factors that are involved in inflammation and there are many points of action of anti-inflammatory components. It can be said that there are few or almost no sedation. Such long-lasting inflammation is not preferable for organisms because of the risk of inducing cancer. That is, development of means for suppressing persistent inflammation induced by high-dose ultraviolet irradiation is desired.

  It is already known that Sophoraflavanone G is contained in leguminous cucumbers (Sophora flavescens). It is also known to have a tyrosinase inhibitory action. (For example, refer nonpatent literature 1) About sophoraflavanone G, it is known that an antibacterial action, alpha-MSH inhibitory action, etc. exist. (For example, see Patent Document 1, Patent Document 2, Patent Document 3, and Patent Document 4)

  6-acetyl-11,13-dihydrohelenalin (6-Acetyl-11,13-dihydrohelenalin) is known to be contained in plants of the genus Arnicae, androgenic alopecia It is known that it is useful for the prevention or treatment of cancer. (For example, see Patent Document 5)

  Pigmented water extract of leguminous cucumber combined with aqueous ethanol extract of Arnica montana L., a plant belonging to the genus Rabbitaceae, and acylated ascorbic acid glucoside, a derivative of ascorbic acid, improves pigmentation The technology to do is already known. (See, for example, Patent Document 6) However, 1) 0.01 to 1% by mass of sophoraflavanone G and / or a salt thereof, and 2) 6-acetyl-11,13-dihydrohelenalin (6- Acetyl-11,13-dihydrohelenalin) 0.001-1% by mass is not known, and 1) Sophoraflavanone G and / or its salt 0.01-1% by mass 2) 6-Acetyl-11,13-dihydrohelenalin (6-Acetyl-11,13-dihydrohelenalin) 0.001 to 1% by mass, and 3) skin external preparation containing ascorbic acid or a derivative thereof is also completely known. It is not done. This is because the content of Sophoraflavanone G and / or a salt thereof can be blended only in an amount of less than 0.01% by simply extracting leguminous cucumbers with ethanol. This is because it is necessary to fractionate and purify the extract in order to contain Sophoraflavanone G at the above-mentioned quantitative ratio.

Japanese Patent Application Laid-Open No. 08-73364 JP 2000-44481 A JP 2001-220347 A JP 2003-95852 A Japanese translation of PCT publication No. 2003-522779 JP 2004-91436 A Soo J. Kim et.al., Biol., Pharm., Bull., 26 (9), 1348-1350, (2003)

  The present invention has been made under such circumstances, and an object of the present invention is to provide means for suppressing persistent inflammation induced by irradiation with a high dose of ultraviolet rays.

  In view of such a situation, the present inventors have sought for means for suppressing persistent inflammation induced by irradiation with a high dose of ultraviolet rays, and as a result of intensive research efforts, 1) Sophoraflavanone G (Sophoraflavanone G) And / or its salt 0.01 to 1% by mass, and 2) 0.001 to 1% by mass of 6-acetyl-11,13-dihydrohelenalin (6-Acetyl-11,13-dihydrohelenalin). As a result, it was found that the external preparation for skin has such characteristics, and the present invention has been completed.

ソフォラフラバノンＧ

Sophora Flabanon G

６−アセチル−１１，１３−ジヒドロヘレナリン

6-acetyl-11,13-dihydrohelenaline

That is, the present invention is as follows.
(1) 1) Sophoraflavanone G (or Sophoraflavanone G) and / or its salt 0.01-1% by mass, and 2) 6-acetyl-11,13-dihydrohelenalin (6-Acetyl-11,13-dihydrohelenalin) The skin external preparation characterized by containing 0.001-1 mass%.
(2) The sophoraflavanone G is obtained by liquid-liquid extraction of an alcoholic extract of leguminous cucumbers (Sophora flavescens) with ethyl acetate and water, concentrating the ethyl acetate phase, and then separating by column chromatography using silica gel as a carrier. The external preparation for skin according to (1), wherein the preparation is derived from a product that has been refined and removed from the solvent.
(3) The 6-acetyl-11,13-dihydrohelenalin is derived from a plant body of Arnicae, which is extracted with alcohol and removed from a solvent. The skin external preparation as described in (1) or (2).
(4) The external preparation for skin according to (3), wherein the plant of the family Asteraceae is Arnica montana L.
(5) 1) Alcohol extract of leguminous cucumber (Sophora flavescens) is liquid-liquid extracted with ethyl acetate and water, and the ethyl acetate phase is concentrated, followed by fractional purification by column chromatography using silica gel as a carrier, It contains 0.02 to 2% by mass of the solvent removed and 2) 0.1 to 5% by mass of the plant of Arnicae plant extracted with alcohol after solvent removal. An external preparation for skin.
(6) The skin external preparation according to any one of (1) to (5), further comprising 0.1 to 10% by mass of ascorbic acid and / or a derivative thereof.
(7) The derivative of ascorbic acid is one or more selected from a salt of ascorbic acid, an ascorbic acid phosphate ester and a salt thereof, ascorbic acid-2-glucoside and a salt thereof, The external preparation for skin according to (6).
(8) Further, 0.05 to 0.5% by mass of one or more selected from glycyrrhizic acid, a salt thereof, an alkyl glycyrrhetinate and a salt thereof, is characterized in that (1) -(7) The external preparation for skin as described in any one of the above.
(9) The external preparation for skin according to (7) or (8), which is a quasi-drug that promotes melanin production inhibitory action or anti-inflammatory action.
(10) In the labeling, an indication that it is a quasi-drug that promotes the action of suppressing melanin production and / or the action of suppressing inflammation, and taking an appropriate amount in the usage method, stains and pigmentation Incorporate cut cotton into a part that is worrisome or lightly inflamed, and lightly scrape it and apply it by pressing, and the above application improves spots and pigmentation. (9), characterized in that it is configured to display or to suppress inflammation, and to indicate that the operation is immediately stopped when a feeling of tingling or burning is felt by the above operation. Topical skin preparation.

  ADVANTAGE OF THE INVENTION According to this invention, the means to suppress the persistent inflammation induced by high dose ultraviolet irradiation can be provided.

(1) Soforaflavanone G which is an essential component of the external preparation for skin of the present invention
The external preparation for skin of the present invention is characterized by containing Soforaflavanone G and / or a salt thereof in an amount of 0.01 to 1% by mass, more preferably 0.05 to 0.5% by mass. Soforaflavanone G contains 10-50 mg in 1 kg of dried cucumber plant, and when water or the like is used as an extraction solvent, this component is difficult to elute and is usually extracted with ethanol or the like. When removed, an amorphous material containing 0.01 to 0.05% by mass of sophoraflavanone G is obtained. By liquid-liquid extraction of this extract with ethyl acetate and water and concentrating the ethyl acetate phase, an amorphous containing 0.1 to 1% by mass of sophoraflavanone G can be obtained. Further, a fraction containing 30-50% by mass of sophoraflavanone G can be obtained by fractionating and purifying the product by silica gel column chromatography (elution solvent chloroform, chloroform / methanol mixed solution). When extracting with ethanol from kujin, a rhizome can be particularly preferably exemplified as a plant part to be used. Extraction is done by chopping up the plant body, etc., adding 1 to 10 times the solvent to this, adding it to room temperature for several days, and if it is near the boiling point for several hours, soaking with appropriate stirring do it. Thereafter, the mixture is cooled to room temperature, and then an insoluble matter is removed by filtration, if desired, followed by concentration under reduced pressure to obtain amorphous. The fraction purification of this product is preferably carried out while checking the situation by thin layer chromatography or the like, and when this is a mixed solvent of chloroform (95 parts by volume) and methanol (5 parts by volume), It appears as a spot at about Rf 0.1.

<Production Example 1>
1 kg of dried leguminous rhizomes was chopped, 10 l of ethanol was added thereto, heated under reflux for 3 hours with stirring, cooled to room temperature, and concentrated under reduced pressure. To this was added 2 l of water and 2 l of ethyl acetate, solubilized, and liquid-liquid extraction was performed. The ethyl acetate phase was taken and concentrated to give 105 g of amorphous. The amount of sophoraflavanone G contained in this product was determined to be 0.9% by mass. (ODS column 4.6 mm × 150 mm, column temperature 40 ° C., elution solvent 30% acetonitrile aqueous solution, flow rate 1 ml / min, detection ultraviolet part 220 nm, quantitative by absolute calibration curve using standard substance) silica gel column chromatography (chloroform, chloroform When the methanol mixture was purified with an elution solvent), 1.2 g of amorphous substance containing 38% by mass of sophoraflavanone G was obtained.

(2) 6-acetyl-11,13-dihydrohelenaline which is an essential component of the external preparation for skin of the present invention The external preparation for skin of the present invention contains 6-acetyl-11,13-dihydrohelenaline as an essential component. 001 to 1% by mass, more preferably 0.002 to 0.5% by mass. Such components are contained in a high concentration in plants of the genus Rabbitaceae, particularly flowers, flower spikes, buds and the like. As the plant, it is contained throughout the plant of the asteraceae Rabbitaceae, and there is no need to specifically limit the species thereof, for example, Arnica montana L., Arnica chamissonis ssp foliosa. Arnica fulgens, Arnica soraria Greene, Arnica cordifolia Hook, Arnica latifolia Bong, Arnica longifolia, Arnica sharininsis (Arnica chalinensis) ) Etc. can be used. Particularly preferred is Arnica montana L., which is the easiest to obtain. Usually, the dried products of flowers, spikes and buds of these plants contain 0.5 to 1.0% by mass of 6-acetyl-11,13-dihydrohelenalin. Most of these components can be extracted by immersing ethanol, hydrous ethanol containing 50% or more of ethanol, etc. in an amount of 1 to 10 times by mass with respect to the plant body. The immersion time is suitably several hours for temperatures near the boiling point and several days for temperatures near room temperature. After the immersion, if necessary, the insoluble matter is removed by filtration or the like, and then the solvent is removed by distillation under reduced pressure or the like, thereby obtaining an amorphous containing 20 to 60% by mass of the component. By containing 0.1 to 5% by mass of this substance, the above-mentioned quantitative ratio of 6-acetyl-11,13-dihydrohelenalin can be contained in the external preparation for skin. The content of 6-acetyl-11,13-dihydrohelenalin can be controlled by quantitative determination using high performance liquid chromatography. The conditions for high-speed liquid chromatography are, for example, ODS column 4.6 mm × 150 mm, column temperature 40 ° C., elution solvent 70% acetonitrile aqueous solution, flow rate 1 ml / min, detection ultraviolet region 220 nm, and absolute calibration curve using standard substance. Quantification etc. can be illustrated preferably.

<Production Example 2>
Add 2 liters of 90% ethanol to 1 kg of dried Arnica montana L. flowers and persimmons, heat to reflux for 3 hours, cool to room temperature, filter to remove insolubles, and remove under reduced pressure to remove solvent. Was removed to obtain 6.2 g of amorphous. As determined by high performance liquid chromatography, this product contained 42% by mass of 6-acetyl-11,13-dihydrohelenaline. In order to facilitate blending, 98 parts by mass of 1,3-butanediol was added to 2 parts by mass of this amorphous, solubilized to obtain Arnica liquid 1 (intermediate work product).

(3) External preparation for skin of the present invention The external preparation for skin of the present invention contains the above-mentioned essential components, suppresses persistent inflammation induced by high-dose ultraviolet irradiation, and duration of inflammation caused by high-dose ultraviolet irradiation Has the effect of shortening. By such an effect, a living body attack reaction caused by an inflammatory factor caused by prolonged inflammation can be suppressed mildly, and a living body damage can be reduced. In the external preparation for skin of the present invention, it is preferable to contain an active ingredient used for ultraviolet ray damage in addition to the essential ingredients. Examples of the active ingredient include ascorbic acid and derivatives of ascorbic acid. Preferred examples include melanin production inhibitors such as ellagic acid, tranexamic acid, and arbutin, and anti-inflammatory agents such as indomethacin, ketoprofen, glycyrrhizic acid and / or a salt thereof, and glycyrrhetinic acid and / or an ester thereof. As the melanin production inhibitor, ascorbic acid and / or a derivative thereof is more preferable, and as the anti-inflammatory agent, glycyrrhizic acid and / or a salt thereof, glycyrrhetinic acid and / or an alkyl ester thereof is more preferable. This is because high-dose ultraviolet irradiation is stable and safe.

  Ascorbic acid derivatives that can be used in the external preparation for skin of the present invention include ascorbic acid salts, ascorbic acid phosphates and salts thereof, ascorbic acid glycosides such as ascorbic acid-2-glucoside and salts thereof Etc. can be suitably exemplified. These salts can be used without particular limitation as long as they are usually used in quasi drugs, cosmetics, skin external medicines, etc., for example, alkali metal salts such as sodium salts and potassium salts Preferred examples include alkaline earth metal salts such as calcium and magnesium, organic amine salts such as ammonium salt, triethanolamine salt and triethylamine salt, and basic amino acid salts such as lysine salt and arginine salt. In the skin external preparation of the present invention, such a salt may contain only one species or may contain two or more species in combination. In the external preparation for skin of the present invention, ascorbic acid and a derivative thereof are preferably ascorbic acid-2-glucoside and / or a salt thereof. The preferable content of such ascorbic acid and / or a derivative thereof in the external preparation for skin of the present invention is 0.1 to 10% by mass, more preferably 1 to 10% by mass based on the total amount of external preparation for skin. 5% by mass. This is because if the amount is too small, the inhibitory action of ascorbic acid on melanin production may be impaired, and if it is too large, the effect may reach its peak.

  The topical skin preparation of the present invention contains one or more selected from glycyrrhizic acid, alkyl glycyrrhetinate, and salts thereof because the effects of the present invention can be made clearer. It is preferable. Such an ingredient is an ingredient known as an quasi-drug active ingredient, and glycyrrhizic acid and / or a salt thereof is preferably dipotassium glycyrrhetinate, and alkyl glycyrrhetinate and / or a salt thereof is stearyl glycyrrhetinate. Is preferred. The preferable content of such components is 0.05 to 0.5 mass% with respect to the total amount of the external preparation for skin. By containing this, when the topical skin preparation of the present invention is administered immediately after sunburn or the like, the inflammation is suppressed more quickly, the prognosis is improved, and the preventive effect of deterioration such as pigmentation is increased. .

  In the external preparation for skin of the present invention, in addition to the above-mentioned components, optional components that are usually used in cosmetics and external preparations for skin can be contained. Such optional ingredients include, for example, macadamia nut oil, avocado oil, corn oil, olive oil, rapeseed oil, sesame oil, castor oil, safflower oil, cottonseed oil, jojoba oil, coconut oil, palm oil, liquid lanolin, hydrogenated coconut oil Oils such as hardened oil, mole, castor oil, beeswax, candelilla wax, carnauba wax, ibotarou, lanolin, reduced lanolin, hard lanolin, jojoba wax, waxes, liquid paraffin, squalane, pristane, ozokerite, paraffin, ceresin, petrolatum , Hydrocarbons such as microcrystalline wax, higher fatty acids such as oleic acid, isostearic acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, undecylenic acid, cetyl alcohol, stearyl alcohol, isostearyl Alcohol, behenyl alcohol, octyldodecanol, higher alcohol such as myristyl alcohol, cetostearyl alcohol, cetyl isooctanoate, isopropyl myristate, hexyldecyl isostearate, diisopropyl adipate, di-2-ethylhexyl sebacate, cetyl lactate, malic acid Diisostearyl, di-2-ethylhexanoic acid ethylene glycol, dicaprate neopentyl glycol, di-2-heptylundecanoic acid glycerin, tri-2-ethylhexanoic acid glycerin, tri-2-ethylhexanoic acid trimethylolpropane, tri Synthetic ester oils such as trimethylolpropane isostearate and pentane erythritol tetra-2-ethylhexanoate, dimethylpolysiloxane, methylphenylpoly Loxane, linear polysiloxane such as diphenylpolysiloxane, cyclic polysiloxane such as octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexanesiloxane, amino-modified polysiloxane, polyether-modified polysiloxane, alkyl-modified polysiloxane, Oil agents such as silicone oil such as modified polysiloxane such as fluorine-modified polysiloxane, anionic surfactants such as fatty acid soap (sodium laurate, sodium palmitate, etc.), potassium lauryl sulfate, triethanolamine ether of alkyl sulfate, chloride Cationic surfactants such as stearyltrimethylammonium, benzalkonium chloride, laurylamine oxide, imidazoline-based amphoteric surfactants (2-cocoyl-2-imida Zolinium hydroxide-1-carboxyethyloxy disodium salt, etc.), betaine surfactants (alkyl betaine, amide betaine, sulfobetaine, etc.), amphoteric surfactants such as acylmethyltaurine, sorbitan fatty acid esters (sorbitan) Monostearate, sorbitan sesquioleate, etc.), glycerin fatty acids (glyceryl monostearate, etc.), propylene glycol fatty acid esters (propylene glycol monostearate, etc.), hardened castor oil derivatives, glycerin alkyl ethers, POE sorbitan fatty acid esters (POE sorbitan monooleate, polyoxyethylene sorbitan monostearate, etc.), POE sorbite fatty acid esters (POE-sorbitol monolaurate, etc.), POE glycerin fatty acid ester Tells (POE-glycerol monoisostearate, etc.), POE fatty acid esters (polyethylene glycol monooleate, POE distearate, etc.), POE alkyl ethers (POE2-octyldodecyl ether, etc.), POE alkyl phenyl ethers (POE nonylphenyl) Ethers, etc.), Pluronic types, POE / POP alkyl ethers (POE / POP2-decyltetradecyl ether, etc.), Tetronics, POE castor oil / hardened castor oil derivatives (POE castor oil, POE hardened castor oil, etc.), Nonionic surfactants such as sucrose fatty acid ester and alkyl glucoside, polyethylene glycol, glycerin, 1,3-butylene glycol, erythritol, sorbitol, xylitol, maltitol, propylene Polyols such as recall, dipropylene glycol, diglycerin, isoprene glycol, 1,2-pentanediol, 2,4-hexylene glycol, 1,2-hexanediol, 1,2-octanediol, pyrrolidone carboxylic acid Moisturizing ingredients such as sodium, lactic acid, sodium lactate, guar gum, quince seed, carrageenan, galactan, gum arabic, pectin, mannan, starch, xanthan gum, curdlan, methylcellulose, hydroxyethylcellulose, carboxymethylcellulose, methylhydroxypropylcellulose, chondroitin sulfate , Dermatan sulfate, glycogen, heparan sulfate, hyaluronic acid, sodium hyaluronate, tragacanth gum, keratan sulfate, chondroitin, mucoitin sulfate, hyaluronan Droxyethyl guar gum, carboxymethyl guar gum, dextran, keratosulfuric acid, locust bean gum, succinoglucan, caronic acid, chitin, chitosan, carboxymethylchitin, agar, polyvinyl alcohol, polyvinylpyrrolidone, carboxyvinyl polymer, sodium polyacrylate, Thickeners such as polyethylene glycol and bentonite, surface may be treated, powder such as mica, talc, kaolin, synthetic mica, calcium carbonate, magnesium carbonate, silicic anhydride (silica), aluminum oxide, barium sulfate The surface may be treated, bengara, yellow iron oxide, black iron oxide, cobalt oxide, ultramarine, bitumen, titanium oxide, zinc oxide inorganic pigments, the surface may be treated, mica titanium, Fish phosphorus foil, bismuth oxychloride Pearl agents, which may be raked Red 202, Red 228, Red 226, Yellow 4, Blue 404, Yellow 5, Red 505, Red 230, Red 223, Orange 201 No., Red No. 213, Yellow No. 204, Yellow No. 203, Blue No. 1, Green No. 201, Purple No. 201, Red No. 204, and the like, polyethylene powder, polymethyl methacrylate, nylon powder, organopolysiloxane elastomer Organic powders such as paraaminobenzoic acid UV absorbers, anthranilic acid UV absorbers, salicylic acid UV absorbers, cinnamic acid UV absorbers, benzophenone UV absorbers, sugar UV absorbers, 2- ( 2′-hydroxy-5′-t-octylphenyl) benzotriazole, 4-methoxy-4′-t-butyldibenzoylmethane, etc. External line absorbers, lower alcohols such as ethanol and isopropanol, vitamin A or derivatives thereof, vitamin B6 hydrochloride, vitamin B6 tripalmitate, vitamin B6 dioctanoate, vitamin B2 or derivatives thereof, vitamin B12, vitamin B15 or derivatives thereof, etc. Vitamin E such as vitamin B, α-tocopherol, β-tocopherol, γ-tocopherol, vitamin E acetate, vitamin D, vitamin H, pantothenic acid, panthetin, pyrroloquinoline quinone, and the like can be preferably exemplified . The skin external preparation of this invention can be manufactured by processing these according to a conventional method.

  The skin external preparation of the present invention thus obtained has an action of suppressing persistent inflammation induced by high-dose ultraviolet irradiation and shortening the duration of inflammation caused by high-dose ultraviolet irradiation. By such an effect, the biological attack reaction caused by the inflammatory factor caused by prolonged inflammation can be moderately suppressed, and the biological damage can be reduced. The external preparation for skin of the present invention can be applied to both cosmetics including quasi-drugs and external preparations for skin. However, in the case of containing ascorbic acids, this is the melanin production of quasi-drugs. Since it is classified as an active ingredient as a component that exhibits an inhibitory action, it is preferably applied to quasi drugs. This is because a form in which a use form in a quasi-drug is clearly displayed and used in a situation in which the user is clearly aware of the use form is particularly preferable for the expression of the effect. In addition, when it contains one or more selected from glycyrrhizic acid, alkyl glycyrrhetinate and salts thereof, it has the characteristics as an active ingredient of quasi drugs resulting from these anti-inflammatory effects. It is possible and preferable to use it as a quasi-drug with anti-inflammatory action. That is, the external preparation for skin of the present invention has an indication that it is a quasi-drug that has an action of suppressing melanin production and / or an action of suppressing inflammation, and an appropriate amount in the method of use. Incorporate it into a cut cotton etc. in a site that is worried about spots or pigmentation, or a site that is slightly inflamed, lightly rub it, apply it by pressing, A quasi-drug with indications to improve stains and pigmentation, or to reduce inflammation, and to stop use immediately if you feel irritation or burning due to the above operations It is preferable to apply to.

  Hereinafter, the present invention will be described in more detail with reference to examples, but it is needless to say that the present invention is not limited to such examples.

  According to the formulation shown below, a quasi-drug (emulsion: appealing for anti-inflammatory action and melanin production inhibitory action) which is an external preparation for skin of the present invention was prepared. That is, weigh each component of A, B and C, heat to 80 ° C., gradually add B to the emulsified with stirring, emulsify, then add C to neutralize, cool with stirring, and cool emulsion 1 Obtained.

B)
Behenyl alcohol 0.5% by mass
Cetyl isooctanoate 2% by mass
Squalane 8% by mass
Dimethicone 2% by mass
Sorbitan sesquistearate 1.5% by mass
POE (45) stearic acid 1% by mass
Cetyl stearate 0.5% by mass
Behenic acid 0.5% by mass
Stearyl glycyrrhetinate 0.1% by mass
B)
1,3-butanediol 5% by mass
Glycerin 5% by mass
1,2-pentanediol 5% by mass
50% by weight of water
Ascorbic acid-2-glucoside 2% by mass
Carboxyvinyl polymer 0.3% by mass
Amorphous of Production Example 1 0.5% by mass
(Soforaflavanone G0.19% by mass)
Arnica liquid 1 of Production Example 2 0.5% by mass
(0.0042% by mass of 6-acetyl-11,13-dihydrohelenaline)
Achillea millefolium extract 0.5% by mass
C)
16.5% by mass of water
Potassium hydroxide 0.6% by mass

<Test Example 1>
About emulsion 1, the effect was investigated using five panelists. That is, six 2 cm × 3 cm size sites were created on the back of the panel, one of which was an untreated control and one was an irradiation control. The remaining four locations were used as sample administration sites. As samples, emulsion 1 and the emulsion 1 of Example 1 were replaced with water (Comparative Example 1), and the Arnica solution 1 of Example 1 of emulsion 1 was replaced with water. The comparative example 2 and the amorphous of the production example 1 of the emulsion 1 and the one obtained by replacing the arnica liquid 1 of the production example 2 with water (comparative example 3) were used after adjustment. Five sites except the untreated control were irradiated with ultraviolet rays (light source: SE lamp) 4 times the minimum erythema volume (MED) measured in advance, and 0.05 ml of sample was administered 30 minutes after irradiation. No sample was administered to the irradiated control site. Thereafter, the sample was administered once a day for 14 days, and the colors were measured 24 hours, 72 hours, 7 days, and 15 days after irradiation, and the color difference (ΔE) relative to the untreated site was determined. These average values are shown in Table 1.

  In the same manner as in Example 1, according to the formulation shown below, emulsion 2 (a quasi-drug: an anti-inflammatory action and an inhibitory action on melanin production) was prepared as an external preparation for skin of the present invention. When evaluated in the same manner as in Test Example 1, the results shown in Table 2 were obtained. Thus, in the external preparation for skin of the present invention, the preferred content of sophoraflavanone G and / or a salt thereof is 0.01 to 1% by mass, more preferably 0.05 to 0.5% by mass. I understand.

B)
Behenyl alcohol 0.5% by mass
Cetyl isooctanoate 2% by mass
Squalane 8% by mass
Dimethicone 2% by mass
Sorbitan sesquistearate 1.5% by mass
POE (45) stearic acid 1% by mass
Cetyl stearate 0.5% by mass
Behenic acid 0.5% by mass
Stearyl glycyrrhetinate 0.1% by mass
B)
1,3-butanediol 5% by mass
Glycerin 5% by mass
1,2-pentanediol 5% by mass
50% by weight of water
Ascorbic acid-2-glucoside 2% by mass
Carboxyvinyl polymer 0.3% by mass
Amorphous 0.1% by mass of Production Example 1
(Soforaflavanone G0.04% by mass)
Arnica liquid 1 of Production Example 2 0.5% by mass
(0.0042% by mass of 6-acetyl-11,13-dihydrohelenaline)
Achillea millefolium extract 0.5% by mass
C)
16.9% by weight of water
Potassium hydroxide 0.6% by mass

  In the same manner as in Example 1, the emulsion 3 (quasi-drug: anti-inflammatory action and melanin production inhibitory action) was prepared according to the formulation shown below. When evaluated in the same manner as in Test Example 1, the results shown in Table 3 were obtained. Thus, in the skin external preparation of the present invention, the preferable content of 6-acetyl-11,13-dihydrohelenalin is 0.001 to 1% by mass, more preferably 0.002 to 0.5% by mass. %.

B)
Behenyl alcohol 0.5% by mass
Cetyl isooctanoate 2% by mass
Squalane 8% by mass
Dimethicone 2% by mass
Sorbitan sesquistearate 1.5% by mass
POE (45) stearic acid 1% by mass
Cetyl stearate 0.5% by mass
Behenic acid 0.5% by mass
Stearyl glycyrrhetinate 0.1% by mass
B)
1,3-butanediol 5% by mass
Glycerin 5% by mass
1,2-pentanediol 5% by mass
50% by weight of water
Ascorbic acid-2-glucoside 2% by mass
Carboxyvinyl polymer 0.3% by mass
Amorphous of Production Example 1 0.5% by mass
(Soforaflavanone G0.19% by mass)
Arnica liquid 1 of Production Example 2 0.1% by mass
(0.001% by mass of 6-acetyl-11,13-dihydrohelenaline)
Achillea millefolium extract 0.5% by mass
C)
16.9% by weight of water
Potassium hydroxide 0.6% by mass

  The present invention can be applied to an external preparation for skin useful for ultraviolet radiation care.

Claims (10)

1) Sophoraflavanone G and / or its salt 0.01-1% by mass, and 2) 6-acetyl-11,13-dihydrohelenalin 0.001 Skin external preparation characterized by containing -1 mass%.

Sophora Flabanon G

6-acetyl-11,13-dihydrohelenaline The sophoraflavanone G is liquid-liquid extracted with ethyl acetate and water from an alcohol extract of leguminous cucumber (Sophora flavescens). After concentrating the ethyl acetate phase, it is fractionated and purified by column chromatography using silica gel as a carrier. The external preparation for skin according to claim 1, wherein the external preparation is derived from a solvent-removed product. The 6-acetyl-11,13-dihydrohelenaline is derived from a plant body of the plant Arnicae belonging to the genus Arnicae, which has been extracted with alcohol and solvent-free. The external preparation for skin according to 1 or 2. The external preparation for skin according to claim 3, wherein the plant of the Asteraceae Rabbitaceae is Arnica montana L .. 1) Alcohol extract of leguminous cucumber (Sophora flavescens) was liquid-liquid extracted with ethyl acetate and water, the ethyl acetate phase was concentrated, fractionated and purified by column chromatography using silica gel as a carrier, and the solvent was removed. Characterized in that it contains 0.02 to 2% by mass of the product and 0.1 to 5% by mass of the plant body of Arnicae plant extracted with alcohol and solvent-free. Topical agent. Furthermore, 0.1-10 mass% of ascorbic acid and / or its derivative is contained, The skin external preparation in any one of Claims 1-5 characterized by the above-mentioned. The derivative of ascorbic acid is one or more selected from a salt of ascorbic acid, an ascorbic acid phosphate ester and a salt thereof, ascorbic acid-2-glucoside and a salt thereof, Item 6. A topical skin preparation according to Item 6. Furthermore, 0.05-0.5 mass% of 1 type or 2 types or more selected from glycyrrhizic acid, its salt, alkyl glycyrrhetinic acid, and its salt are contained, The any one of Claims 1-7 characterized by the above-mentioned. The skin external preparation of Claim 1. The external preparation for skin according to claim 7 or 8, which is a quasi-drug that promotes melanin production inhibitory action or anti-inflammatory action. In the labeling, the indication that it is a quasi-drug that promotes the action of suppressing melanin production and / or the action of suppressing inflammation, and in its usage, take an appropriate amount, and worry about spots and pigmentation. It is included in cut cotton or the like in a part that is or slightly inflamed, and it is used by applying it by lightly rubbing and pressing, and the effect of improving spots and pigmentation by the application, Alternatively, the skin external application according to claim 9, wherein a display indicating that the inflammation is suppressed and a display indicating that the use is immediately stopped when a feeling of irritation or burning is felt by the operation are configured. Agent.