JP5128826B2 - 新規なメチル化カテキン及びそれを含む組成 - Google Patents
新規なメチル化カテキン及びそれを含む組成 Download PDFInfo
- Publication number
- JP5128826B2 JP5128826B2 JP2007028419A JP2007028419A JP5128826B2 JP 5128826 B2 JP5128826 B2 JP 5128826B2 JP 2007028419 A JP2007028419 A JP 2007028419A JP 2007028419 A JP2007028419 A JP 2007028419A JP 5128826 B2 JP5128826 B2 JP 5128826B2
- Authority
- JP
- Japan
- Prior art keywords
- gallate
- methyl
- gallocatechin
- dimethyl
- epigallocatechin
- 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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Links
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- 235000005487 catechin Nutrition 0.000 title description 11
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- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims description 22
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- 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
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- 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
(1)化学式I
以下実施例により本発明を更に具体的に説明するが、本発明の範囲はこれらに限定されるものではない。
(酵素反応)
特開2006−141242号公報記載の方法で製造したメチル化カテキン生合成酵素の粗酵素液を用いて、酵素反応を行った。酵素反応液(100mM Tris-HCl(pH7.4)、0.2mM MgCl2、25μM EGCG、50μM SAM、粗酵素液の量は酵素反応液の1/5)を調製し、30℃にて16時間行った後、反応液中の濃度が0.04NになるようにHClを添加して反応を停止させた。反応液を55℃湯温中にて30分間保温し、遠心分離(7,000rpm×10min)後の上清をロータリーエバポレーターで濃縮した。濃縮液に等量の酢酸エチルを加えて振とうした後、遠心分離(7,000rpm×10min)により有機層を回収し、ロータリーエバポレーターを用いて濃縮乾固し、35(v/v)%メタノールに溶解した。得られた35(v/v)%メタノール溶解液を分取HPLCにて測定し、分取を行った。
分取HPLC条件
カラム:Inertsil ODS-3(20mm×250mm、ジーエルサイエンス社)
Inertsil ODS-3 ガードカラム(20mm×50mm、ジーエルサイエンス社)
移動相:35(v/v)%メタノール
流速:12mL/min、 検出器:UV280nm、
以上の条件で40min前後のピーク画分を回収し、ロータリーエバポレーターで濃縮した後、凍結乾燥して化合物粉末を得た。
TOF-MS測定
「UPLC/TOF-MS条件」
HPLC:ACQUITY UPLC(ウォーターズ社)
カラム:ACQUITY UPLC BEH C18(50 x 2.1 mm、1.7 mm:ウォーターズ社)
移動相:A液‐メタノール B 液‐0.1(v/v)%ギ酸水溶液
10(v/v)%A液(0 min)→ 50(v/v)%A液(5 min)
流速:0.6 mL/min、カラム温度:40℃、注入量:5 mL
検出器:LCT Premier(ウォーターズ社)
イオン源:ESI(ポジティブ、ネガティブ)、コーン電圧:30 V、キャピラリー電圧:2500 V
イオン源温度:120℃、デソルベーション温度:300℃、MSスキャン:m/z 100-1000
NMR測定
精製した化合物をCD3ODに溶解した。NMR測定にはXWIN-NMR AV 600(Bruker Biospin社)を用い、各種NMRスペクトル(1H、13C、HSQC、HMBC、COSY)を測定した。表1に測定結果を示した。その結果、化合物をエピ(3−O−メチル)ガロカテキン−3−O−(3、5−O−ジメチル)ガレートと決定した。
エピガロカテキン−3−O−ガレートからエピ(3−O−メチル)ガロカテキン−3−O−(3、5−O−ジメチル)ガレートへの変換効率の確認を行った。酵素反応液(100mM Tris-HCl(pH7.4)、0.2mM MgCl2、粗酵素液の量は酵素反応液の1/5)を調製し、エピガロカテキン−3−O−ガレート 10mgに対してSAMを10mg,20mg又は50mg添加した後、30℃にて反応させた。反応開始0.25,0.5,1,2,3,4,8時間後に経時的に反応液5mLを回収し、反応液中の濃度が0.04NになるようにHClを添加して反応を停止させた。酢酸エチルを8mL加えた後攪拌し、遠心分離(3000rpm×5min)により有機層を回収し200μlの1%アスコルビン酸を添加、吸引濃縮を行った上でHPLCにてエピ(3−O−メチル)ガロカテキン−3−O−(3、5−O−ジメチル)ガレートの生成量を測定した。その結果、反応時間の経過とともにエピ(3−O−メチル)ガロカテキン−3−O−(3、5−O−ジメチル)ガレートの生成量は増加し、さらにSAMの添加量が多いほど、変換効率は増す傾向であった。変換効率の推移を図1に示す。
マウスマスト細胞からのヒスタミン遊離抑制作用を指標にエピ(3−O−メチル)ガロカテキン−3−O−(3、5−O−ジメチル)ガレートの効果を確認した。比較対象としてエピガロカテキン−3−O−ガレートとそれと比較して高い抗アレルギー作用を有することが知られているエピガロカテキン−3−O−(3−O−メチル)ガレートを用いた。マウスマスト細胞はBMMC(マウス骨髄誘導マスト細胞)を用い、10%非動化FBS(牛胎児血清)、10%D11培養上清(IL-3の給源として)、5mMグルタミン酸Na、50μM 2-メルカプトエタノール添加RPMI1640培地で培養した。細胞(1×107cells/mL)は、抗DNP−マウスIgE抗体で一晩感作した後、翌日Tyrode液に遊離させて披験試料とともに10分インキュベート後、DNP−HAS(抗原)を添加して脱顆粒を誘発し(20分)、上清中のヒスタミン量を液体クロマトグラフ法で測定した。抗アレルギー性はコントロールである蒸留水との相対値の低いものほど高いと判断した。その結果、図2に示されるようにエピ(3−O−メチル)ガロカテキン−3−O−(3、5−O−ジメチル)ガレートは比較対象のエピガロカテキン−3−O−ガレート及びエピガロカテキン−3−O−(3−O−メチル)ガレートと比較して、さらに高いヒスタミン遊離抑制効果を示した。
Claims (7)
- エピ(3−O−メチル)ガロカテキン−3−O−(3,5−O−ジメチル)ガレート。
- 請求項1に記載のエピ(3−O−メチル)ガロカテキン−3−O−(3,5−O−ジメチル)ガレートを含むことを特徴とする組成物。
- 請求項1に記載のエピ(3−O−メチル)ガロカテキン−3−O−(3,5−O−ジメチル)ガレートを含むことを特徴とする抗アレルギー剤。
- 請求項1に記載のエピ(3−O−メチル)ガロカテキン−3−O−(3,5−O−ジメチル)ガレートを含むことを特徴とする飲食品。
- 請求項1に記載のエピ(3−O−メチル)ガロカテキン−3−O−(3,5−O−ジメチル)ガレートを含むことを特徴とする医薬品又は医薬部外品。
- 請求項1に記載のエピ(3−O−メチル)ガロカテキン−3−O−(3,5−O−ジメチル)ガレートを含むことを特徴とする化粧品。
- エピガロカテキン−3−O−ガレートを基質として、メチル化カテキン生合成酵素を反応させることを特徴とする請求項1に記載のエピ(3−O−メチル)ガロカテキン−3−O−(3,5−O−ジメチル)ガレートの製造方法。
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JP2007028419A JP5128826B2 (ja) | 2007-02-07 | 2007-02-07 | 新規なメチル化カテキン及びそれを含む組成 |
CNA2008800043673A CN101605772A (zh) | 2007-02-07 | 2008-01-21 | 新型甲基化儿茶素和包含该甲基化儿茶素的组合物 |
US12/449,345 US20100324312A1 (en) | 2007-02-07 | 2008-01-21 | Novel methylated catechin and composition containing the same |
PCT/JP2008/050685 WO2008096586A1 (ja) | 2007-02-07 | 2008-01-21 | 新規なメチル化カテキン及びそれを含む組成 |
EP08703535A EP2119712A4 (en) | 2007-02-07 | 2008-01-21 | NEW METHYLATED CATECHIN AND COMPOSITION CONTAINING THIS |
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KR101722427B1 (ko) * | 2015-04-27 | 2017-04-04 | 강원대학교산학협력단 | 메틸화카테킨을 유효성분으로 함유하는 암세포의 성장억제용 조성물 |
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JP5714809B2 (ja) * | 2009-06-24 | 2015-05-07 | アサヒ飲料株式会社 | 茶エキスの製造方法、茶粉末の製造方法及び茶エキス又は茶粉末に含まれるカテキン中のメチル化カテキンの濃度を高める方法。 |
WO2011000593A1 (en) * | 2009-06-30 | 2011-01-06 | Unilever Plc | Method for determining susceptibility of individuals to polyphenols |
JP5936841B2 (ja) * | 2011-10-05 | 2016-06-22 | 森永製菓株式会社 | 8−ジメチルアリル−(−)−エピガロカテキン−3−o−ガレート |
JP6062666B2 (ja) * | 2012-06-14 | 2017-01-18 | 森永製菓株式会社 | 水溶性向上剤、水溶性向上方法、及び、水溶液調製方法 |
CN103113384B (zh) * | 2013-02-27 | 2015-05-20 | 安徽农业大学 | 一种名为茯砖素b的儿茶素类衍生物及其制备方法和应用 |
WO2016013654A1 (ja) * | 2014-07-24 | 2016-01-28 | 株式会社プロテクティア | アレルゲン活性の抑制剤およびその用途 |
US20170326100A1 (en) * | 2014-12-09 | 2017-11-16 | Amorepacific Corporation | Composition for activating longevity gene |
KR102681552B1 (ko) * | 2016-09-27 | 2024-07-04 | (주)아모레퍼시픽 | 소장 상피세포에서의 카테킨 흡수 증진제 |
CN115252519A (zh) * | 2022-08-03 | 2022-11-01 | 浙江熙正霖生物科技有限公司 | 一种具有生物活性成分的护发精华液及其制备方法 |
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JPS61145177A (ja) | 1984-12-18 | 1986-07-02 | Mitsubishi Chem Ind Ltd | カテキン誘導体 |
JP3637355B2 (ja) | 1998-11-20 | 2005-04-13 | 独立行政法人農業・生物系特定産業技術研究機構 | 抗アレルギー剤 |
JP2002255810A (ja) | 2001-02-27 | 2002-09-11 | Tokyo Food Techno Kk | 新規抗菌剤、新規カテキン誘導体およびその製造方法 |
US7122573B2 (en) * | 2002-12-06 | 2006-10-17 | Sri International | Analogs of green tea polyphenols as chemotherapeutic and chemopreventive agents |
WO2005074960A1 (ja) * | 2004-02-06 | 2005-08-18 | Asahi Soft Drinks Co., Ltd. | 機能性飲料及び組成物 |
JP2006141242A (ja) * | 2004-11-17 | 2006-06-08 | National Agriculture & Bio-Oriented Research Organization | メチル化カテキン生合成酵素をコードする遺伝子 |
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 |
JP4997523B2 (ja) * | 2006-01-13 | 2012-08-08 | 独立行政法人農業・食品産業技術総合研究機構 | 抗アレルギー剤及びこれを含有する飲食品、外用剤、化粧料 |
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KR101722427B1 (ko) * | 2015-04-27 | 2017-04-04 | 강원대학교산학협력단 | 메틸화카테킨을 유효성분으로 함유하는 암세포의 성장억제용 조성물 |
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US20100324312A1 (en) | 2010-12-23 |
EP2119712A4 (en) | 2011-05-11 |
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EP2119712A1 (en) | 2009-11-18 |
CN101605772A (zh) | 2009-12-16 |
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