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WO2010030000A1 - Agent de blanchiment de la peau et préparation cutanée externe pour le blanchiment de la peau - Google Patents

Agent de blanchiment de la peau et préparation cutanée externe pour le blanchiment de la peau Download PDF

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Publication number
WO2010030000A1
WO2010030000A1 PCT/JP2009/065936 JP2009065936W WO2010030000A1 WO 2010030000 A1 WO2010030000 A1 WO 2010030000A1 JP 2009065936 W JP2009065936 W JP 2009065936W WO 2010030000 A1 WO2010030000 A1 WO 2010030000A1
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WO
WIPO (PCT)
Prior art keywords
whitening
glycoside
glucopyranosyl
skin
iridoid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2009/065936
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English (en)
Japanese (ja)
Inventor
俊博 秋久
悦代 金子
健一 清野
瞬 栃澤
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Nihon University
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Nihon University
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Filing date
Publication date
Application filed by Nihon University filed Critical Nihon University
Priority to JP2010528764A priority Critical patent/JPWO2010030000A1/ja
Publication of WO2010030000A1 publication Critical patent/WO2010030000A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/602—Glycosides, e.g. rutin

Definitions

  • the present invention relates to a whitening agent and a whitening skin external preparation for acting on tyrosinase that produces melanin that causes spots, freckles, and sunburn to suppress the production of melanin.
  • whitening agents conventionally used as whitening cosmetics, ⁇ -arbutin, kojic acid, vitamin C derivatives, lucinol, tranexamic acid and the like are frequently used as whitening active ingredients. These whitening active ingredients are known to exert a whitening effect by acting directly or indirectly on an enzyme called tyrosinase, which is important for the production of melanin, and suppressing the production of melanin in the skin.
  • Patent Documents 1 and 2 describe that ⁇ -arbutin composed of hydroquinone- ⁇ -D-glucopyranoside has an excellent skin beautifying effect.
  • Patent Document 3 describes the separation / separation from leaves and fruits, rhizomes, bark, etc. of Gentianaceae plants, Vibrioaceae plants, Rubiaceae plants, Euphorbiaceae plants, Ominaeaceae plants, Honeysuckle family plants, Oleaceae plants Extracted cornuside, loganin, sweroside and moloniside pentaacetate are described as having excellent whitening effects.
  • the present invention has been made to eliminate such inconveniences, and its object is to provide a novel whitening agent and a skin whitening external preparation for whitening that have both excellent whitening effect and high safety. Objective.
  • the first invention A whitening agent comprising one or more of terpene glycosides, sugar fatty acid esters and iridoid glycosides as a whitening active ingredient for inhibiting melanin production.
  • the second invention, 1st invention WHEREIN The said terpene glycoside, sugar fatty-acid ester, and iridoid glycoside are whitening agents characterized by being an extract of noni fruit.
  • the terpene glycoside is (1) a 3-methyl-3-butenyl primeveroside of (1) a hemiterpene glycoside, or (2) A whitening agent characterized by being one or more compounds of 3-methyl-3-butenyl geniobioside of hemiterpene glycoside.
  • the fourth invention is in the first or second invention, the sugar fatty acid ester is (3) 2-O- ( ⁇ -D glucopyranosyl) -1-O-hexanoyl- ⁇ -D-glucopyranose (2-O- ( ⁇ -D -Glucopyranosyl) -1-O-hexanoyl- ⁇ -D-glucopyranose) or (4) 6-O- ( ⁇ -D-glucopyranosyl) -1-O-hexanoyl- ⁇ -D-glucopyranose (6-O -( ⁇ -D-glucopyranosyl) -1-O-hexanoyl- ⁇ -D-glucopyrose) or (5) 2,6-di-O- ( ⁇ -D-glucopyranosyl) -1-O-hexanoyl ⁇ - D-glucopyranose (2,6-di-O- ( ⁇ -D-glucopyranosyl) -1-O-hexanoyl
  • the iridoid glycoside is (8) 9-epi-6-methoxygeniposidic acid of an iridoid type monoterpene glycoside, or (9) Asperuloside acid (Asperulosic acid) or (10) Deacetylyl asperulosic acid of iridoid type monoterpene glycoside (Deacetyl asperulosic acid) or (11) Scand of iridoid type monoterpene glycoside It is a whitening agent characterized by being one or more compounds of sidomethyl ester (Scandoside methyl ester).
  • the sixth invention is a skin whitening external preparation characterized by containing any one or more of terpene glycosides, sugar fatty acid esters and iridoid glycosides as a whitening active ingredient for suppressing melanin production in the skin.
  • the seventh invention In a sixth aspect of the invention, the terpene glycoside, sugar fatty acid ester and iridoid glycoside are a noni fruit extract, which is a skin whitening external preparation.
  • the whitening agent of the present invention contains any one or more of terpene glycoside, sugar fatty acid ester and iridoid glycoside as a whitening active ingredient, as demonstrated in the examples below, Excellent whitening effect compared to whitening agents that use whitening active ingredients such as ⁇ -arbutin that has been approved. In addition, as for safety, it can exhibit excellent safety equivalent to or better than that of active whitening ingredients such as ⁇ -arbutin currently approved as a whitening agent.
  • the skin external preparation for whitening of this invention contains any one or more among terpene glycoside, sugar fatty acid ester, and iridoid glycoside as a whitening active ingredient for skin melanin production suppression. If this skin whitening preparation for skin whitening is applied to the skin, it can act on tyrosinase that produces melanin that causes spots, freckles, and sunburn, thereby effectively suppressing the production of melanin in the skin.
  • FIG. 2 is a process diagram (first stage) showing the fractionation of noni fruit extract and the isolation process of each compound (1) to (11) according to the present invention.
  • FIG. 2 is a process chart (second stage) showing the fractionation of noni fruit extract and the isolation process of each compound (1) to (11) according to the present invention.
  • FIG. 6 is a graph showing measurement results of melanin production inhibition rates of each compound (1) to (11) and a reference compound (arbutin).
  • FIG. 6 is a graph showing the measurement results of cell viability of each compound (1) to (11) and a reference compound (arbutin).
  • the whitening agent and the whitening skin external preparation according to the present invention contain any one or more of terpene glycosides, sugar fatty acid esters and iridoid glycosides as whitening active ingredients for inhibiting melanin production. That is, these terpene glycosides, sugar fatty acid esters, and iridoid glycosides may be contained singly or in full, or in appropriate combinations.
  • a 3-methyl-3-butenylprimeveroside (3-Methyl-3) of a hemiterpene glycoside having a chemical structure represented by the following chemical formula 1 in particular is used.
  • -Butenyl primeveroside) (1) hereinafter, this compound is referred to as compound (1) as appropriate
  • hemiterpene glycoside 3-methyl-3-butenyl gentithiobioside 3- Any one or more of the two types of compounds (1) and (2) such as methyl-3-butenediol (2) (hereinafter, this compound is referred to as compound (2) as appropriate) is suitable.
  • the compound (1) is a novel compound discovered from the noni fruit extract by the present inventor as shown in the following examples.
  • the two types of compounds (1) and (2) can be used alone or in combination.
  • 9-epi-6-methoxygeniposidic acid (8-epi-6-methoxygeniposidic acid) (8) is an iridoid monoterpene glycoside having a chemical structure represented by the following chemical formula 8.
  • this compound is appropriately referred to as compound (8)), or asperuloside acid (9) (hereinafter, this compound is appropriately referred to as compound (9)) having the chemical structure represented by chemical formula 9 below
  • Four types of compounds (8) to (11) such as scandoside methyl ester (11) (hereinafter, this compound is referred to as compound (11) as appropriate) of iridoid-type monoterpene glycoside having Any one or more compounds are suitable.
  • These four types of compounds (8) to (11) may be contained alone or in whole, or may be contained in appropriate combination.
  • the whitening agent and the whitening skin external preparation of the present invention contain any one or more of these terpene glycosides, sugar fatty acid esters and iridoid glycosides as whitening active ingredients.
  • the whitening effect superior to the whitening agent using the whitening active ingredient such as ⁇ -arbutin currently approved can be exhibited.
  • it can exhibit excellent safety equivalent to or better than that of active whitening ingredients such as ⁇ -arbutin currently approved as a whitening agent.
  • the skin external preparation for whitening of this invention contains any one or more among terpene glycoside, sugar fatty acid ester, and iridoid glycoside as a whitening active ingredient for skin melanin production suppression. If this skin whitening preparation for skin whitening is applied to the skin, it can act on tyrosinase that produces melanin that causes spots, freckles, and sunburn, thereby effectively suppressing the production of melanin in the skin.
  • the terpene glycoside, sugar fatty acid ester and iridoid glycoside compounds (1) to (11) according to the present invention can also be produced by a known chemical synthesis method. Extraction and separation and purification from natural products containing (1) to (11), particularly noni (Morinda citrifolia) fruit, can be efficiently obtained.
  • the extraction / separation / purification method of the compounds (1) to (11) from the noni fruit is not particularly limited, and the compounds obtained by known natural product component extraction / separation / purification methods and various chromatographies are used.
  • the extraction / separation / purification method can be used.
  • noni fruits are heated and refluxed with an organic solvent such as methanol to obtain an extract.
  • the extract is distributed with chloroform water or the like, and the water-soluble fraction is extracted with ethyl acetate or the like.
  • the ethyl acetate fraction is fractionated and isolated into each compound by known chromatography and the like.
  • the water fraction after extraction with ethyl acetate is further extracted with butanol to obtain a butanol fraction and a water fraction, and the butanol fraction is further fractionated by various known chromatographic methods, etc. Can be done.
  • the powdery or fine crystalline In addition to being able to use the compound as a whitening agent as it is, it can also be dissolved or dispersed in water, an organic solvent or a mixture thereof and adjusted to a liquid or pellet form and used as an antioxidant. Furthermore, it can be mixed with an excipient, a thickener, a gelling agent, etc., and adjusted to a granular, gel, or viscous liquid and used as a whitening agent.
  • the dosage form of the whitening agent of the present invention is arbitrary, ampoules, capsules, powders, granules, pills, tablets, solids, liquids, gels, bubbles, emulsions, creams, ointments , Sheet-like, mousse-like, powder-dispersed, multilayer, aerosol-like pharmaceuticals, quasi-drugs, and cosmetics.
  • a skin whitening external preparation using any one or more of terpene glycosides, sugar fatty acid esters and iridoid glycosides which are whitening active ingredients of the present invention
  • lotion, emulsion, cream Basic cosmetics such as ointments, lotions, oils and packs, soaps, cleansing creams, cleansing lotions, skin cleansers such as face wash, shampoos, rinses, treatments, etc., hair creams, hair sprays, hair tonics , Hair gel, hair lotion, hair oil, hair essence, hair water, hair wax, hair foam and other hair styling, hair growth, hair nourishing, 1 part hair dye, 2 part hair dye, hair color etc.
  • Permanent preparations such as permanent wave agents and hair straighteners, hair cosmetics such as wave retention agents, foundations, white powder Makeup cosmetics such as funny, lipstick, blusher, eye shadow, eyeliner, mascara, eyebrows, eyelashes, etc., cosmetics for finishing such as beauty nails, oral compositions such as perfumes, toothpastes, gargles, etc.
  • Cosmetic compositions topical pharmaceutical preparations, ointments, haptics, bath preparations, medicated toothpastes, medicinal oral compositions such as mouth fresheners, medicinal cosmetics, permanent wave solvents, hair dyes, hair restorers, hair removal inhibitors, removal It can be used in the form of a hair solvent liquid odor / deodorant such as hair agent, quasi-drugs such as sanitary goods, sanitary cotton, wet tissue, and external medicines.
  • a hair solvent liquid odor / deodorant such as hair agent
  • quasi-drugs such as sanitary goods, sanitary cotton, wet tissue, and external medicines.
  • the blending amount of the terpene glycoside, sugar fatty acid ester and iridoid glycoside, which are the whitening active ingredients of the present invention, is slightly different depending on the type and quality of the whitening agent and the skin external preparation for whitening, and the expected degree of action. Therefore, although it is not particularly limited, it is generally used in a concentration range of 0.0001% by mass or more in the total amount of the preparation, preferably 0.01 to 20.0% by mass is effective.
  • the whitening agent and the skin external preparation for whitening of the present invention further suppress pigmentation exemplified below.
  • tyrosinase activity inhibitor melanocyte melanin production inhibitor, melanin production promoter, moisturizer, cell activator / metabolic activator, antioxidant, active oxygen scavenger / radical production inhibitor, fat metabolism promoter, ultraviolet light Protective agent / UV absorption enhancer, astringent, anti-inflammatory agent / interleukin production inhibitor / anti-inflammatory agent, antiseborrheic agent, antibacterial agent / antiviral agent, blood flow promoter / vascular stimulator, antiandrogen agent, structure Proteolytic enzymes (elastase, collagenase, keratin protease, serine protease, integrin degrading enzyme, involucrin degrading enzyme, filaggrin content Enzyme, laminin degrading enzyme, fibronectin degrading enzyme, proteoglycan degrading enzyme, etc.) activity inhibitor, structural protein synthesis promoter, mucopolysaccharide (hyaluronic acid, chondroitin
  • hormones, sequestering agents, pH adjusters, chelating agents, antiseptic / antibacterial agents, refreshing agents, stabilizers, emulsifiers, animal / plant proteins and their degradation products, animal / plant polysaccharides and their Degradation products, animal / plant glycoproteins and their degradation products, anti-inflammatory agents, antiallergic agents, wound treatment agents, foaming agents, thickeners, enzymes, purified water (electronic water, small clusters, etc.), deodorant / A deodorant etc. can be used in combination.
  • ⁇ -arbutin which is a known whitening active ingredient having a chemical structure represented by the following chemical formula 12, was similarly evaluated for melanin production inhibitory effect and cytotoxicity under the same conditions.
  • the EtOAc fraction was subjected to silica gel column chromatography (SiO 2 CC) and octadecyl silica column chromatography (ODS CC), and then again silica gel column chromatography (SiO 2 CC). ) And reversed-phase high performance liquid chromatography (RP-HPLC) to obtain three types of compounds (9), (10) and (11) and two types of compounds (6) and (7), respectively.
  • silica gel column chromatography SiO 2 CC
  • ODS CC octadecyl silica column chromatography
  • RP-HPLC reversed-phase high performance liquid chromatography
  • the water fraction (H 2 O fraction) after extraction with EtOAc was then extracted with butanol (n-BuOH) to obtain 61.0 g of n-BuOH fraction and 120.8 g of water fraction. (H 2 O fraction) was obtained.
  • the n-BuOH fraction was further fractionated by Diaion HP-20 column chromatography (CC), of which 30% MeOH (8.7 g) and 50% MeOH elution fraction ( As shown in FIG. 2, 6.8 g) was further fractionated by various chromatographies as described above, and 11 kinds of compounds (1) to (11) were isolated from the noni fruit MeOH extract.
  • the compound (8) is a novel compound having a structure of 9-epi-6-methoxygeniposidic acid (9-epi-6-methoxygeniposidic acid), an iridoid monoterpene glycoside.
  • Compound (1) which is a novel compound, is 3-methyl-3-butenyl primebioside, which is a hemiterpene glycoside having a chemical structure represented by Chemical Formula 1.
  • the spectrum data of this compound (1) is shown below.
  • the compound (2) is a hemiterpene glycoside 3-methyl-3-butenyl gentiobioside having a chemical structure represented by the chemical formula 2 (3-Methyl-3-butenyl geniobioside).
  • the spectral data of this compound (2) is shown below.
  • Compound (3) is a sugar fatty acid ester 2-O- ( ⁇ -D-glucopyranosyl) -1-O-hexanoyl- ⁇ -D-glucopyranose (2-O- ( ⁇ -D-glucopyranyl) -1-O-hexanoyl- ⁇ -D-glucopyranose).
  • the spectral data of this compound (3) is shown below.
  • Compound (4) is a sugar fatty acid ester 6-O- ( ⁇ -D-glucopyranosyl) -1-O-hexanoyl- ⁇ -D-glucopyranose (6-O- ( ⁇ -D-glucopyranyl) -1-O-hexanoyl- ⁇ -D-glucopyranose).
  • the spectral data of this compound (4) is shown below.
  • the compound (5) is a sugar fatty acid ester 2,6-di-O- ( ⁇ -D-glucopyranosyl) -1-O-hexanoyl- ⁇ -D-glucopyranose (2, 6-di-O- ( ⁇ -D-glucopyranosyl) -1-O-hexanoyl- ⁇ -D-glucopyranose).
  • the spectral data of this compound (5) is shown below.
  • the compound (6) is a sugar fatty acid ester 6-O- ( ⁇ -D-glucopyranosyl) -1-O-octanoyl- ⁇ -D-glucopyranose (6-O- ( ⁇ -D-glucopyranosyl) -1-O-octanoyl- ⁇ -D-glucopyranose).
  • the spectral data of this compound (6) is shown below.
  • Compound (7) is a sugar fatty acid ester of 2,6-di-O- ( ⁇ -D-glucopyranosyl) -1-O-octanoyl- ⁇ -D-glucopyranose (2, 6-di-O- ( ⁇ -D-glucopyranosyl) -1-O-octanoyl- ⁇ -D-glucopyranose).
  • the spectral data of this compound (7) is shown below.
  • Compound (8) which is a novel compound, is 9-epi-6-methoxygeniposidic acid, an iridoid-type monoterpene glycoside having the chemical structure represented by Chemical Formula 8.
  • the spectral data of this compound (8) is shown below.
  • 1 H-NMR (600 MHz, CD 3 OD): ⁇ 7.38 (1H, s, H-3), 5.84 (1H, brs, H-7), 5.61 (1H, d, J 3.
  • Compound (9) is an iridoid-type monoterpene glycoside having a chemical structure represented by the chemical formula 9 (Asperulosic acid). The spectral data of this compound (9) is shown below.
  • Compound (10) is an iridoid-type monoterpene glycoside having a chemical structure represented by Chemical Formula 10 (deacetylasperulosic acid).
  • the spectral data of this compound (10) is shown below.
  • Compound (11) is a scandoside methyl ester of an iridoid-type monoterpene glycoside having the chemical structure represented by Chemical Formula 11.
  • the spectral data of this compound (11) is shown below.
  • B16 melanoma 4A5 cells were used, seeded with 500 ⁇ l of 1 ⁇ 10 4 cells / ml on a 24 well plate, and cultured for 24 hours. After culturing, the B16 melanoma 4A5 cells are treated with ⁇ -MSH (Melanocyte-Stimulating-Hormone), 11 kinds of noni fruit-derived compounds (1) to (11) and ⁇ -arbutin (Arbutin) according to the present invention described above. Added as a sample.
  • ⁇ -MSH Melocyte-Stimulating-Hormone

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  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
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  • Epidemiology (AREA)
  • Dermatology (AREA)
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  • Cosmetics (AREA)
  • Saccharide Compounds (AREA)

Abstract

La présente invention concerne un agent de blanchiment de la peau et une préparation cutanée externe destinée à blanchir la peau. Ledit agent et ladite préparation comprennent au moins un élément sélectionné parmi un glycoside terpène, un ester d'acide gras de sucrose et un glycoside iridoïde en tant que principe actif de blanchiment de la peau permettant d'inhiber la production de mélanine. L'agent de blanchiment de la peau et la préparation cutanée externe peuvent présenter un excellent effet blanchisseur pour la peau, et se révèlent extrêmement sûrs.
PCT/JP2009/065936 2008-09-12 2009-09-11 Agent de blanchiment de la peau et préparation cutanée externe pour le blanchiment de la peau Ceased WO2010030000A1 (fr)

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JP2010528764A JPWO2010030000A1 (ja) 2008-09-12 2009-09-11 美白剤および美白用皮膚外用剤

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JP2008234913 2008-09-12
JP2008-234913 2008-09-12

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011195519A (ja) * 2010-03-19 2011-10-06 Maruzen Pharmaceut Co Ltd メラニン産生抑制剤、グルタチオン産生促進剤、ヒアルロン酸産生促進剤、及びインボルクリン産生促進剤、並びに皮膚化粧料
WO2012147861A1 (fr) * 2011-04-27 2012-11-01 ロート製薬株式会社 Composition pour inhibition de la production d'endosérine-1 et composition pour promotion de la prolifération cellulaire
CN103242390A (zh) * 2012-02-08 2013-08-14 鲁南制药集团股份有限公司 一种提取去乙酰车叶草苷酸甲酯和鸡矢藤次苷甲酯的方法
JP2019038754A (ja) * 2017-08-23 2019-03-14 一丸ファルコス株式会社 皮膚外用剤

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JP2001213752A (ja) * 2000-01-28 2001-08-07 Kanebo Ltd 化粧料
JP2005145945A (ja) * 2003-11-14 2005-06-09 Tahiti Ambition:Kk 皮膚機能賦活化粧料組成物

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JP2001213752A (ja) * 2000-01-28 2001-08-07 Kanebo Ltd 化粧料
JP2005145945A (ja) * 2003-11-14 2005-06-09 Tahiti Ambition:Kk 皮膚機能賦活化粧料組成物

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Title
"Abstracts of Annual Meeting of Pharmaceutical Society of Japan, 05 March 2008 (05.03.2008)", vol. 128, article SHUN TOCHIZAWA ET AL.: "Noni Kajitsu no To Shibosan Ester, Hemiterpene Haitotai Oyobi Iridoid Seibun", pages: 99 *
"Abstracts of Annual Meeting of Pharmaceutical Society of Japan, 05 March 2008 (05.03.2008)", vol. 128, TAHITIAN NONI INC., article MEGUMI MASUDA ET AL.: "Tahiti-san Noni (Morinda citrifolia) no Bihaku - Bihada Sayo ni Tsuite", pages: 72 *
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011195519A (ja) * 2010-03-19 2011-10-06 Maruzen Pharmaceut Co Ltd メラニン産生抑制剤、グルタチオン産生促進剤、ヒアルロン酸産生促進剤、及びインボルクリン産生促進剤、並びに皮膚化粧料
WO2012147861A1 (fr) * 2011-04-27 2012-11-01 ロート製薬株式会社 Composition pour inhibition de la production d'endosérine-1 et composition pour promotion de la prolifération cellulaire
JPWO2012147861A1 (ja) * 2011-04-27 2014-07-28 ロート製薬株式会社 エンドセリン−１産生抑制用組成物、及び細胞増殖促進用組成物
CN103242390A (zh) * 2012-02-08 2013-08-14 鲁南制药集团股份有限公司 一种提取去乙酰车叶草苷酸甲酯和鸡矢藤次苷甲酯的方法
CN103242390B (zh) * 2012-02-08 2017-02-15 鲁南制药集团股份有限公司 一种提取去乙酰车叶草苷酸甲酯和鸡矢藤次苷甲酯的方法
JP2019038754A (ja) * 2017-08-23 2019-03-14 一丸ファルコス株式会社 皮膚外用剤

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