JP5009619B2 - リパーゼ阻害剤 - Google Patents
リパーゼ阻害剤 Download PDFInfo
- Publication number
- JP5009619B2 JP5009619B2 JP2006528907A JP2006528907A JP5009619B2 JP 5009619 B2 JP5009619 B2 JP 5009619B2 JP 2006528907 A JP2006528907 A JP 2006528907A JP 2006528907 A JP2006528907 A JP 2006528907A JP 5009619 B2 JP5009619 B2 JP 5009619B2
- Authority
- JP
- Japan
- Prior art keywords
- gallate
- lipase
- epigallocatechin
- compound
- fat
- 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.)
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Images
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- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
- C07D311/62—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2 with oxygen atoms directly attached in position 3, e.g. anthocyanidins
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Description
で表される、フラバン-3-オール・モノマー類またはそのアシル化物の少なくとも一種を含むことを特徴とする。
リパーゼ阻害剤
本発明のフラバン-3-オール・モノマー類またはそのアシル化物は、他の成分を含まずに単独でリパーゼ阻害剤として使用することもでき、または溶媒や固体担体とともにリパーゼ阻害剤として使用することが可能である。溶媒または担体は、下記飲食料および/または医薬品としての使用を考えて、食品としてまたは医薬品として安全に使用できるものであることが好ましい。本発明のリパーゼ阻害剤は種々の用途を有し、例えば試験研究用、中性脂肪の蓄積を予防するための食品、医薬品の有効成分としての使用が例示される。
リパーゼ阻害活性測定方法
本発明のリパーゼ阻害剤は、リパーゼ、特に膵リパーゼに対する強い阻害作用を有する。その阻害活性は、実施例1に具体的に記載する方法で測定できる。
リパーゼ阻害剤含有飲食料
本発明のフラバン-3-オール・モノマー類またはそのアシル化物を含むリパーゼ活性阻害剤を、リパーゼ阻害活性成分として飲食料に添加して、食事からの脂肪分の摂取に伴う血中中性脂肪の望ましくない上昇を防止し、および/または上昇した血中中性脂肪を低減させることができる。飲食料の好ましい例は、日常的に摂取する飲食料、例えば、緑茶、麦茶、ウーロン茶、紅茶、コーヒー、スポーツドリンク、飲料水、調味料、ドレッシングである。しかし飲食料は、通常食するものであればよく、清涼飲料、カクテル、ビール、ウイスキー、焼酎、ワイン、清酒、調味料、ドレッシング、味付け米、加工食品、インスタント食品、レトルト食品、チョコレート、生クリーム、洋菓子、乳製品、健康食品、サプリメント等であってもよい。
リパーゼ活性阻害剤含有医薬品
本発明のフラバン-3-オール・モノマー類またはそのアシル化物を含むリパーゼ阻害剤は、食事由来の脂肪の吸収を抑制し、血中中性脂肪の望ましくない上昇を防止および/または低下させるための薬剤の有効成分としても使用できる。好ましい薬剤は、経口投与される薬剤であり、その例として、ドリンク剤、錠剤、カプセル剤、顆粒剤、散剤、キャンデー、ドロップ剤等があげられる。薬剤に含まれる本発明の化合物の量は、1回服用量当たり、0.1mg〜10gである。
リパーゼ活性の測定は、基質に蛍光性の4−メチルウンベリフェロンのオレイン酸エステル(4-UMO)を使用し、反応によって生成した4−メチルウンベリフェロンの蛍光を測定することにより実施した。
測定サンプル
(-)-epicatechin (化合物2)、(-)-epicatechin 3-O-gallate (化合物3)、(-)-epigallocatechin (化合物5)、(-)-epigallocatechin 3-O-gallate (化合物6)、(+)-catechin (化合物9)、 (-)-catechin 3-O-gallate (化合物10)、 (+)-gallocatechin (化合物11)、(-)-gallocatechin 3-O-gallate (化合物12)は和光純薬工業株式会社より購入した。
実施例2
可可茶(Camellia ptilophylla)の葉(乾燥物)100gを2000mlの熱水(90℃)で4分間抽出上記の凍結乾燥品を用いて以下のように精製を行った。凍結乾燥粉末の1%水溶液をSep-Pak C18 Cartridge (5 g, Waters製)に吸着させ、これを水洗浄した後、アセトニトリルにより溶出する画分を凍結乾燥した。この画分、250mgをDevelosil C30-UG-5 (20mm x 250mm、野村化学株式会社製)に負荷し、0.05% TFA存在下、5-30%アセトニトリルの直線勾配(5ml/min、180min)において溶出させ、A280nmの吸収をモニターしながら分画した。得られた画分を次いでYMC-Pak ODS (20 x 250mm、ワイエムシー株式会社製)に負荷し、0.1% TFA存在下、20-25%アセトニトリルの直線勾配(6ml/mim、60min)において溶出させ精製を行い、gallocatechin 3,5-di-O-gallate (13)を得た。
実施例3 カテキン類のリパーゼ阻害活性
カテキン類およびアシル化カテキン類のリパーゼ阻害活性を表1に示した。なお、図1には評価に供した化合物の化学構造式を記載した。
Claims (6)
- エピガロカテキン 3,5-ジ-O-ガレートを有効成分として含む、リパーゼ阻害剤。
- 食事由来の脂肪の吸収を抑制するための、請求項1記載のリパーゼ阻害剤。
- 血中中性脂肪の上昇を抑制するための、請求項1記載のリパーゼ阻害剤。
- 中性脂肪の蓄積を予防するための、請求項1記載のリパーゼ阻害剤。
- エピガロカテキン 3,5-ジ-O-ガレートを一回服用量当り0.1mg〜10g含む、請求項1〜4のいずれか1項記載のリパーゼ阻害剤。
- エピガロカテキン 3,5-ジ-O-ガレートを用いる、食事由来の脂肪の吸収を抑制する方法、又は血中中性脂肪の上昇を抑制する方法(ヒトに対する医療行為を除く。)。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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JP2006528907A JP5009619B2 (ja) | 2004-07-05 | 2005-07-05 | リパーゼ阻害剤 |
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Application Number | Priority Date | Filing Date | Title |
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JP2004198285 | 2004-07-05 | ||
JP2004198285 | 2004-07-05 | ||
JP2006528907A JP5009619B2 (ja) | 2004-07-05 | 2005-07-05 | リパーゼ阻害剤 |
PCT/JP2005/012394 WO2006004110A1 (ja) | 2004-07-05 | 2005-07-05 | リパーゼ阻害剤 |
Publications (2)
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JPWO2006004110A1 JPWO2006004110A1 (ja) | 2008-04-24 |
JP5009619B2 true JP5009619B2 (ja) | 2012-08-22 |
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US (1) | US7939559B2 (ja) |
EP (1) | EP1772148B1 (ja) |
JP (1) | JP5009619B2 (ja) |
KR (1) | KR20070045221A (ja) |
CN (1) | CN1980655B (ja) |
ES (1) | ES2641759T3 (ja) |
HK (1) | HK1103643A1 (ja) |
TW (1) | TW200604190A (ja) |
WO (1) | WO2006004110A1 (ja) |
Families Citing this family (13)
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JP5261808B2 (ja) * | 2005-04-18 | 2013-08-14 | アサヒグループホールディングス株式会社 | 脂肪蓄積抑制剤、医薬品及び脂肪蓄積抑制作用を新たに付与する方法 |
JP2008094797A (ja) * | 2006-10-16 | 2008-04-24 | Morinaga & Co Ltd | 肥満抑制剤及び該肥満抑制剤を含む高脂肪含有飲食品 |
JP2010143832A (ja) * | 2008-12-16 | 2010-07-01 | Suntory Holdings Ltd | リパーゼ阻害剤 |
JP2010184909A (ja) * | 2009-02-13 | 2010-08-26 | Rheology Kino Shokuhin Kenkyusho:Kk | 機能性組成物およびこの組成物を含有する医薬又は健康食品 |
JP5694149B2 (ja) | 2009-05-21 | 2015-04-01 | サントリーホールディングス株式会社 | ベンゾトロポロン環含有化合物を含む抗肥満剤 |
CN102578094B (zh) * | 2011-01-13 | 2013-06-12 | 中国中化股份有限公司 | (+)-表枇杷素的农药用途 |
EP2557079A1 (en) * | 2011-08-09 | 2013-02-13 | Nestec S.A. | Synthesis of catechin and epicatechin conjugates |
JP2014064505A (ja) * | 2012-09-25 | 2014-04-17 | Fujifilm Corp | 食品用組成物および脂質吸収抑制剤 |
CN105949162B (zh) * | 2016-05-09 | 2018-02-09 | 许爱娥 | 咖啡酸衍生物在治疗白癜风中的应用 |
CN108542903B (zh) * | 2018-04-11 | 2019-02-26 | 中山万汉制药有限公司 | 一种含有奥利司他与植物来源脂肪酶抑制剂的药物组合物 |
JP7377220B2 (ja) | 2018-06-05 | 2023-11-09 | フラッグシップ パイオニアリング イノベーションズ ブイ, インコーポレイテッド | 代謝障害および非アルコール性脂肪肝疾患の治療のための活性薬剤およびその使用方法 |
CN111410643B (zh) * | 2020-02-12 | 2023-05-12 | 安徽农业大学 | 一种新的肉桂酰酯儿茶素及四种新的苯丙素黄烷生物碱制备和应用 |
CN115073432B (zh) * | 2022-07-06 | 2024-02-27 | 安徽农业大学 | 甲基化黄烷醇生物碱及其提取、合成、检测和应用 |
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JPH0761927A (ja) * | 1993-08-25 | 1995-03-07 | Lotte Co Ltd | リパーゼ阻害剤およびこれを添加した飲食品 |
JP2000226329A (ja) * | 1998-12-04 | 2000-08-15 | Meiji Milk Prod Co Ltd | Mmp阻害剤 |
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JPS6011912B2 (ja) | 1981-07-30 | 1985-03-28 | 日本新薬株式会社 | タンニン |
JPH01102022A (ja) | 1987-10-14 | 1989-04-19 | Advance Co Ltd | 肥満予防剤 |
JPH0223929A (ja) * | 1988-07-13 | 1990-01-26 | Toshiba Corp | 内視鏡 |
JPH03219872A (ja) | 1990-01-25 | 1991-09-27 | Meiji Seika Kaisha Ltd | リパーゼ阻害剤 |
JP3088787B2 (ja) | 1991-07-08 | 2000-09-18 | 三井農林株式会社 | シュクラーゼ活性阻害剤 |
JP3532999B2 (ja) | 1995-03-24 | 2004-05-31 | 株式会社ロッテ | 新規なタンニン類およびこれを有効成分とするリパーゼ阻害剤 |
JP3828953B2 (ja) | 1995-05-24 | 2006-10-04 | 日本製粉株式会社 | リパーゼ阻害剤 |
JPH09291039A (ja) | 1995-12-26 | 1997-11-11 | Suntory Ltd | プロシアニジンを有効成分とする抗肥満剤 |
CA2405348A1 (en) * | 2000-04-13 | 2001-11-01 | Ocean Spray Cranberries, Inc. | Novel compositions derived from cranberry and grapefruit and therapeutic uses therefor |
JP4719372B2 (ja) | 2000-06-21 | 2011-07-06 | 花王株式会社 | Ppar依存的遺伝子転写活性化剤 |
JP2002104982A (ja) | 2000-09-27 | 2002-04-10 | Erubu:Kk | 茶葉からのカテキン類の抽出方法 |
JP2003095942A (ja) | 2001-09-21 | 2003-04-03 | Ito En Ltd | 脂肪細胞におけるグルコース取込阻害剤及びglut4トランスロケーション抑制剤、筋肉細胞におけるグルコース取込活性化剤並びに脂肪軽減飲食物 |
CN1297301C (zh) * | 2004-04-01 | 2007-01-31 | 暨南大学 | 可可茶提取物用于制备预防及改善肥胖及其临床症状的药物及食品的应用 |
-
2005
- 2005-07-05 TW TW094122730A patent/TW200604190A/zh unknown
- 2005-07-05 JP JP2006528907A patent/JP5009619B2/ja active Active
- 2005-07-05 US US11/631,506 patent/US7939559B2/en active Active
- 2005-07-05 WO PCT/JP2005/012394 patent/WO2006004110A1/ja active Application Filing
- 2005-07-05 KR KR1020077002624A patent/KR20070045221A/ko not_active Application Discontinuation
- 2005-07-05 EP EP05758209.0A patent/EP1772148B1/en active Active
- 2005-07-05 CN CN2005800222720A patent/CN1980655B/zh active Active
- 2005-07-05 ES ES05758209.0T patent/ES2641759T3/es active Active
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2007
- 2007-10-31 HK HK07111743.0A patent/HK1103643A1/xx not_active IP Right Cessation
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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JPH03228664A (ja) * | 1990-02-02 | 1991-10-09 | Meiji Seika Kaisha Ltd | 脂質の消化吸収抑制機能を有する食品 |
JPH0761927A (ja) * | 1993-08-25 | 1995-03-07 | Lotte Co Ltd | リパーゼ阻害剤およびこれを添加した飲食品 |
JP2000226329A (ja) * | 1998-12-04 | 2000-08-15 | Meiji Milk Prod Co Ltd | Mmp阻害剤 |
Also Published As
Publication number | Publication date |
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EP1772148A4 (en) | 2010-02-24 |
ES2641759T3 (es) | 2017-11-13 |
CN1980655B (zh) | 2011-02-02 |
KR20070045221A (ko) | 2007-05-02 |
EP1772148B1 (en) | 2017-09-13 |
CN1980655A (zh) | 2007-06-13 |
HK1103643A1 (en) | 2007-12-28 |
US7939559B2 (en) | 2011-05-10 |
EP1772148A1 (en) | 2007-04-11 |
TW200604190A (en) | 2006-02-01 |
US20080207747A1 (en) | 2008-08-28 |
WO2006004110A1 (ja) | 2006-01-12 |
JPWO2006004110A1 (ja) | 2008-04-24 |
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