JP7121757B2 - 新規なクエルセチン系化合物を含む美白用組成物 - Google Patents
新規なクエルセチン系化合物を含む美白用組成物 Download PDFInfo
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- JP7121757B2 JP7121757B2 JP2019564863A JP2019564863A JP7121757B2 JP 7121757 B2 JP7121757 B2 JP 7121757B2 JP 2019564863 A JP2019564863 A JP 2019564863A JP 2019564863 A JP2019564863 A JP 2019564863A JP 7121757 B2 JP7121757 B2 JP 7121757B2
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- 239000008101 lactose Substances 0.000 description 1
- 208000012929 large congenital melanocytic nevus Diseases 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 206010024217 lentigo Diseases 0.000 description 1
- 208000011080 lentigo maligna melanoma Diseases 0.000 description 1
- 229940010454 licorice Drugs 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000000684 melanotic effect Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- JPTOCTSNXXKSSN-UHFFFAOYSA-N methylheptenone Chemical compound CCCC=CC(=O)CC JPTOCTSNXXKSSN-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
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- 208000004649 neutrophil actin dysfunction Diseases 0.000 description 1
- 208000024645 nevus of Ito Diseases 0.000 description 1
- 201000000032 nodular malignant melanoma Diseases 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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- 235000020333 oolong tea Nutrition 0.000 description 1
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- JXJIQCXXJGRKRJ-KOOBJXAQSA-N pseudoionone Chemical compound CC(C)=CCC\C(C)=C\C=C\C(C)=O JXJIQCXXJGRKRJ-KOOBJXAQSA-N 0.000 description 1
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
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- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
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- 208000030457 superficial spreading melanoma Diseases 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000015961 tonic Nutrition 0.000 description 1
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- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 1
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- OKKJLVBELUTLKV-FIBGUPNXSA-N trideuteriomethanol Chemical compound [2H]C([2H])([2H])O OKKJLVBELUTLKV-FIBGUPNXSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- DCSCXTJOXBUFGB-UHFFFAOYSA-N verbenone Natural products CC1=CC(=O)C2C(C)(C)C1C2 DCSCXTJOXBUFGB-UHFFFAOYSA-N 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Images
Classifications
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- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
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- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/82—Theaceae (Tea family), e.g. camellia
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- 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
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9783—Angiosperms [Magnoliophyta]
- A61K8/9789—Magnoliopsida [dicotyledons]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
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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
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/331—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using water, e.g. cold water, infusion, tea, steam distillation, decoction
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/333—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using mixed solvents, e.g. 70% EtOH
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Mycology (AREA)
- Botany (AREA)
- Biotechnology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Microbiology (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Nutrition Science (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Alternative & Traditional Medicine (AREA)
- Medical Informatics (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines Containing Plant Substances (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Non-Alcoholic Beverages (AREA)
- Cosmetics (AREA)
Description
緑茶(Camellia sinensis var. Yabukita)葉で作った緑茶に水を添加して水分含量を40重量%に調整した。これにバチルス・サブチリス(Bacillus subtillis)5×106cfu/gを接種し、50℃で3日間醗酵させた後に80℃で4日間醗酵させた。
前記後発酵茶試料150gをアセトンで分画してカテキン誘導体及びカフェインを除去し、他の化合物が濃縮された可溶物を収得した。前記アセトン可溶物40gに対し一次的にシリカゲルコラムクロマトグラフィーを利用して、クロロホルム:メタノールの5:1(v/v)混合物を溶媒として分画物を得た。
新規物質31及び32のチロシナーゼ(tyrosinase)活性抑制効果を評価した。
新規物質31及び32のメラニン生成抑制効果を、優れた皮膚美白効果を有すると知られているコウジ酸と比べて測定した。
クエルセチン3-O-[3-O”-(E)-p-クマロイル][β-D-グルコピラノシル-(1→3)-O-α-L-ラムノピラノシル-(1→6)-O-β-D-グルコピラノシド]と、クエルセチン3-O-[3-O”-(E)-p-クマロイル][α-L-ラムノピラノシル-(1→6)-O-β-D-グルコピラノシド]の皮膚累積刺激性の有無を確認し、皮膚に使用できる濃度範囲を算出するために、HRIPT(Human repeated insult patch tests)を実施した。
クエルセチン3-O-[3-O”-(E)-p-クマロイル][β-D-グルコピラノシル-(1→3)-O-α-L-ラムノピラノシル-(1→6)-O-β-D-グルコピラノシド]又はクエルセチン3-O-[3-O”-(E)-p-クマロイル][α-L-ラムノピラノシル-(1→6)-O-β-D-グルコピラノシド]10mg、L-カルニチン80~140mg、大豆油180mg、パーム油2mg、植物性硬化油8mg、黄蝋4mg及びレシチン6mgを混合し、通常の方法に従い1カプセルに充填して軟質カプセル剤を製造した。
クエルセチン3-O-[3-O”-(E)-p-クマロイル][β-D-グルコピラノシル-(1→3)-O-α-L-ラムノピラノシル-(1→6)-O-β-D-グルコピラノシド]又はクエルセチン3-O-[3-O”-(E)-p-クマロイル][α-L-ラムノピラノシル-(1→6)-O-β-D-グルコピラノシド]10mg、ガラクトオリゴ糖200mg、乳糖60mg及び麦芽糖140mgを混合し、流動層乾燥機を用いて顆粒化した後、糖エステル(sugar ester)6mgを添加して、打錠機で打錠して錠剤を製造した。
クエルセチン3-O-[3-O”-(E)-p-クマロイル][β-D-グルコピラノシル-(1→3)-O-α-L-ラムノピラノシル-(1→6)-O-β-D-グルコピラノシド]又はクエルセチン3-O-[3-O”-(E)-p-クマロイル][α-L-ラムノピラノシル-(1→6)-O-β-D-グルコピラノシド]5mg、無水結晶ブドウ糖250mg及び澱粉550mgを混合し、流動層造粒機を用いて顆粒に成形した後、包に充填して顆粒剤を製造した。
クエルセチン3-O-[3-O”-(E)-p-クマロイル][β-D-グルコピラノシル-(1→3)-O-α-L-ラムノピラノシル-(1→6)-O-β-D-グルコピラノシド]又はクエルセチン3-O-[3-O”-(E)-p-クマロイル][α-L-ラムノピラノシル-(1→6)-O-β-D-グルコピラノシド]2mg、ブドウ糖10g、クエン酸0.6g、及び液状オリゴ糖25gを混合した後、精製水300mlを加えて各瓶に200mlずつ充填する。瓶に充填した後、130℃で4~5秒間殺菌してドリンク剤を製造した。
クエルセチン3-O-[3-O”-(E)-p-クマロイル][β-D-グルコピラノシル-(1→3)-O-α-L-ラムノピラノシル-(1→6)-O-β-D-グルコピラノシド]又はクエルセチン3-O-[3-O”-(E)-p-クマロイル][α-L-ラムノピラノシル-(1→6)-O-β-D-グルコピラノシド]20mg、適量の注射用滅菌蒸留水、適量のpH調節剤を用いて通常の方法に従い注射剤を製造した。
下記の表6に記載された組成にて通常の方法に従い健康食品を製造した。
クエルセチン3-O-[3-O”-(E)-p-クマロイル][β-D-グルコピラノシル-(1→3)-O-α-L-ラムノピラノシル-(1→6)-O-β-D-グルコピラノシド]又はクエルセチン3-O-[3-O”-(E)-p-クマロイル][α-L-ラムノピラノシル-(1→6)-O-β-D-グルコピラノシド]0.2重量%、L-アスコルビン酸-2-リン酸マグネシウム塩1.00重量%、水溶性コラーゲン(1%水溶液)5.00重量%、クエン酸ナトリウム0.10重量%、クエン酸0.05重量%、甘草エキス0.20重量%、1,3-ブチレングリコール3.00重量%、残量として精製水を用いて柔軟化粧水(スキンローション)を製造した。
クエルセチン3-O-[3-O”-(E)-p-クマロイル][β-D-グルコピラノシル-(1→3)-O-α-L-ラムノピラノシル-(1→6)-O-β-D-グルコピラノシド]又はクエルセチン3-O-[3-O”-(E)-p-クマロイル][α-L-ラムノピラノシル-(1→6)-O-β-D-グルコピラノシド]0.2重量%、ポリエチレングリコールモノステアレート2.00重量%、自己乳化型モノステアリン酸グリセリン5.00重量%、プロピレングリコール4.00重量%、スクアレン6.00重量%、トリ2-エチルヘキサングリセリル6.00重量%、スフィンゴ糖脂質1.00重量%、1,3-ブチレングリコール7.00重量%、蜜蝋5.00重量%、残量として精製水を用いてクリーム状製剤を製造した。
クエルセチン3-O-[3-O”-(E)-p-クマロイル][β-D-グルコピラノシル-(1→3)-O-α-L-ラムノピラノシル-(1→6)-O-β-D-グルコピラノシド]又はクエルセチン3-O-[3-O”-(E)-p-クマロイル][α-L-ラムノピラノシル-(1→6)-O-β-D-グルコピラノシド]0.2重量%、ポリビニルアルコール21.00重量%、L-アスコルビン酸-2-リン酸マグネシウム塩3.00重量%、ラウロイルヒドロキシプロリン5.00重量%、水溶性コラーゲン(1%水溶液)8.00重量%、1,3-ブチレングリコール7.00重量%、エタノール7.00重量%、残量として精製水を用いて組成物を製造し、これを用いてパックを製造した。
Claims (12)
- クエルセチン3-O-[3-O”-(E)-p-クマロイル][β-D-グルコピラノシル-(1→3)-O-α-L-ラムノピラノシル-(1→6)-O-β-D-グルコピラノシド](Quercetin3-O-[3-O”-(E)-p-coumaroyl][β-D-glucopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→6)-O-β-D-glucopyranoside])又はクエルセチン3-O-[3-O”-(E)-p-クマロイル][α-L-ラムノピラノシル-(1→6)-O-β-D-グルコピラノシド](Quercetin3-O-[3-O”-(E)-p-coumaroyl][α-L-rhamnopyranosyl-(1→6)-O-β-D-glucopyranoside])である化合物、その薬学的に許容可能な塩、その水和物、その溶媒和物、又はこれを含む後発酵茶抽出物を有効成分として含む皮膚美白用組成物。
- 当該組成物は、チロシナーゼ活性及びメラニン生成の一つ以上を抑制するものである、請求項1に記載の皮膚美白用組成物。
- 当該組成物は、しみ、そばかす、黒色点、母斑、黒色腫、紫外線による色素沈着、薬物による色素沈着、炎症後色素沈着、及び皮膚炎から発生する色素沈着からなる群より選ばれる一つ以上を予防、改善又は治療するものである、請求項1又は2に記載の皮膚美白用組成物。
- 前記抽出物は、熱水、C1~C6の低級アルコール、及びこれらの混合溶媒から選ばれた一種以上の溶媒による抽出物である、請求項1~3のいずれか一項に記載の皮膚美白用組成物。
- 前記低級アルコールはエタノールである、請求項4に記載の皮膚美白用組成物。
- 前記抽出物は、抽出後にケトンで分画した分画物である、請求項1~5のいずれか一項に記載の皮膚美白用組成物。
- 前記ケトンはアセトンである、請求項6に記載の皮膚美白用組成物。
- 前記化合物、その薬学的に許容可能な塩、その水和物、又はその溶媒和物の含量は、前記組成物の総重量に対し、0.00001重量%~10重量%の範囲である、請求項1~7のいずれか一項に記載の皮膚美白用組成物。
- 前記組成物中の後発酵茶抽出物の含量は、前記組成物の総重量に対し、0.1重量%~90重量%の範囲である、請求項1~8のいずれか一項に記載の皮膚美白用組成物。
- 前記抽出物は、前記化学式1で表される化合物、その光学異性体、その薬学的に許容可能な塩、その水和物、又はその溶媒和物が、抽出物の総重量を基準に、0.00001重量%~20重量%の範囲で含まれたものである、請求項1~9のいずれか一項に記載の皮膚美白用組成物。
- 前記組成物の投与による前記化学式1で表される化合物、その光学異性体、その薬学的に許容可能な塩、その水和物、又はその溶媒和物の投与量は、0.00001mg/kg/日~100mg/kg/日の範囲である、請求項1~10のいずれか一項に記載の皮膚美白用組成物。
- 前記組成物は、食品組成物、化粧料組成物、又は薬学組成物である、請求項1~11のいずれか一項に記載の皮膚美白用組成物。
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