JP2019530710A - 新規なクエルセチン系化合物 - Google Patents
新規なクエルセチン系化合物 Download PDFInfo
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- JP2019530710A JP2019530710A JP2019519405A JP2019519405A JP2019530710A JP 2019530710 A JP2019530710 A JP 2019530710A JP 2019519405 A JP2019519405 A JP 2019519405A JP 2019519405 A JP2019519405 A JP 2019519405A JP 2019530710 A JP2019530710 A JP 2019530710A
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- Japan
- Prior art keywords
- mass
- glucopyranoside
- rhamnopyranosyl
- compound
- quercetin
- Prior art date
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/60—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Microbiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- General Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Alternative & Traditional Medicine (AREA)
- Botany (AREA)
- Medical Informatics (AREA)
- Mycology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
Description
一具現例によると、前記R1は、下記の化学式2で表される化合物であってよい。
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質量%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。
前記クエルセチン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]のベータ−アミロイド凝集阻害効果を蛍光分析法(Thioflavin T assay)で確認した。
前記クエルセチン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。
Claims (9)
- 下記の化学式1で表される化合物、その異性体、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。
- 前記R1は下記の化学式2で表される化合物である、請求項1に記載の化合物、その異性体、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。
- 前記R2は下記の化学式3で表される化合物である、請求項1に記載の化合物、その異性体、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。
- 前記R3は下記の化学式4で表される化合物である、請求項1に記載の化合物、その異性体、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。
- 前記化合物は、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])である、請求項1に記載の化合物、その異性体、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。
- 前記化合物は、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、請求項1に記載の化合物、その異性体、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。
- 請求項1〜6のいずれか一項に記載の化合物、その異性体、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製造方法。
- 当該製造方法は緑茶を醗酵させた後に分離することである、請求項7に記載の製造方法。
- 前記醗酵は後発酵方式によるものである、請求項8に記載の製造方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2016-0135299 | 2016-10-18 | ||
KR1020160135299A KR102635192B1 (ko) | 2016-10-18 | 2016-10-18 | 신규한 퀘르세틴계 화합물 |
PCT/KR2017/011404 WO2018074794A1 (ko) | 2016-10-18 | 2017-10-16 | 신규한 퀘르세틴계 화합물 |
Publications (2)
Publication Number | Publication Date |
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JP2019530710A true JP2019530710A (ja) | 2019-10-24 |
JP7004706B2 JP7004706B2 (ja) | 2022-02-04 |
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JP2019519405A Active JP7004706B2 (ja) | 2016-10-18 | 2017-10-16 | 新規なクエルセチン系化合物 |
Country Status (5)
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US (1) | US10550142B2 (ja) |
JP (1) | JP7004706B2 (ja) |
KR (1) | KR102635192B1 (ja) |
CN (1) | CN110088117B (ja) |
WO (1) | WO2018074794A1 (ja) |
Families Citing this family (1)
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CN113812625A (zh) * | 2021-06-03 | 2021-12-21 | 湖南农业大学 | 六堡茶在制备防治淀粉样蛋白疾病的功能性产品中的应用 |
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KR100975199B1 (ko) | 2007-11-30 | 2010-08-10 | (주)아모레퍼시픽 | 발효녹차의 제조방법 및 제조된 발효녹차 |
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2016
- 2016-10-18 KR KR1020160135299A patent/KR102635192B1/ko active IP Right Grant
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2017
- 2017-10-16 CN CN201780078476.9A patent/CN110088117B/zh active Active
- 2017-10-16 US US16/343,307 patent/US10550142B2/en active Active
- 2017-10-16 JP JP2019519405A patent/JP7004706B2/ja active Active
- 2017-10-16 WO PCT/KR2017/011404 patent/WO2018074794A1/ko active Application Filing
Non-Patent Citations (1)
Title |
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MANIR,M.M. ET AL: "Tea catechins and flavonoids from the leaves of Camellia sinensis inhibityeast alcohol dehydrogenase", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 20, no. 7, JPN6021031338, 2012, pages 2376 - 2381, XP055477192, ISSN: 0004572425, DOI: 10.1016/j.bmc.2012.02.002 * |
Also Published As
Publication number | Publication date |
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CN110088117A (zh) | 2019-08-02 |
US10550142B2 (en) | 2020-02-04 |
KR102635192B1 (ko) | 2024-02-13 |
US20190241601A1 (en) | 2019-08-08 |
WO2018074794A1 (ko) | 2018-04-26 |
CN110088117B (zh) | 2022-12-06 |
JP7004706B2 (ja) | 2022-02-04 |
KR20180042751A (ko) | 2018-04-26 |
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