JP2011051950A - 脂肪代謝改善剤、該脂肪代謝改善剤を含有する医薬及び食品、並びに新規フラボノイド化合物 - Google Patents
脂肪代謝改善剤、該脂肪代謝改善剤を含有する医薬及び食品、並びに新規フラボノイド化合物 Download PDFInfo
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Abstract
【解決手段】茶花、その抽出物又は茶花に含まれる化合物であって脂肪代謝改善作用を有する化合物を有効成分として含有する脂肪代謝改善剤、該脂肪代謝改善剤を含有するヒト又は動物用の医薬、及び茶花に含まれる新規フラボノイド化合物。
【選択図】 なし
Description
メタノール:ナカライテスク社製、一級
HPLC用メタノール:関東化学社製、特級
順相シリカゲルカラムクロマトグラフ用担体:富士シリシア社製、BW−200,150〜300メッシュ
逆相ODSカラムクロマトグラフ用担体:富士シリシア社製、Chromatorex ODS1020T,100〜200メッシュ
多孔質ポリマーカラムクロマトグラフ用担体:日本練水社製、ダイアイオンHP−20
福建省産茶花(Camellia sinensis)5.07kgを、50(10倍量)kgのメタノールで3時間還流下抽出し、その後抽出液を濾取し、メタノール抽出液を得た。濾過残渣にメタノールを加え、同様の抽出操作を計3回行い、それぞれメタノール抽出液を得た。得られたメタノール抽出液を合わせた後、減圧下溶媒留去しメタノール抽出エキス(1173.7g、植物からの収率23.1%。)を得た。
実施例1で得られたメタノール抽出エキス(1032.5g)を、酢酸エチル(AcOEt)と水で分配抽出した。得られたAcOEt移行部を減圧下溶媒留去し、AcOEt可溶部(149.7g、植物からの収率3.3%)を得た。さらに、水可溶部をDiaion HP−20カラムクロマトグラフィーに付し、水及びメタノールで順次、成分を溶出させて水溶出部(471.6g、植物からの収率10.5%)及びメタノール溶出部(373.4g、植物からの収率8.3%)を得た。
AcOEt可溶部(40g)を、順相シリカゲルカラムクロマトグラフィー[2.0kg、n−ヘキサン:酢酸エチル=(10:1→5:1→1:1→1:10)→クロロホルム→クロロホルム:メタノール=(5:1→1:1)→メタノール]で順次溶出し、溶出画分E1(7.6g)、E2(9.5g)、E3(1.8g)、E4(2.2g)、E5(3.9g)、E6(17.5g)、E7(2.9g)、E8(17.3g)、E9(2.5g)及びE10(2.1g)を得た。
溶出画分E5(3.9g)を、逆相ODSカラムクロマトグラフィー[120g、メタノール:水=(10:90→30:70→70:30→メタノール)にて画分し、溶出画分E5−1(332.0mg)、E5−2(46.0mg)、E5−3(234.4mg)、E5−4(143.0mg)、E5−5(352.5mg)、E5−6(457.7mg)、E5−7(40.4mg)、E5−8(146.2mg)、E5−9(149.2mg)、E5−10(101.1mg)、E5−11(82.1mg、0.0039%(茶花5.07kgからの化合物の単離収率。以下同様)、化合物(11)とする。)、E5−12(56.5mg)、E5−13(310mg)及びE5−14(1.7g)を得た。
溶出画分E6(17.5g)を、逆相ODSカラムクロマトグラフィー[600g、メタノール:水=(20:80→40:60→50:50→70:30→メタノール)にて画分し、溶出画分E6−1(804.2mg)、E6−2(245.3mg)、E6−3(241.5mg)、E6−4(2.6g)、E6−5(1.8g)、E6−6(2.2g)、E6−7(843.9mg)、E6−8(484.2mg)、E6−9(653.2mg)、E6−10(807.6mg)、E6−11(401.4mg)、E6−12(357.8mg)、E6−13(371.5mg)、E6−14(4.5g)を得た。画分E6−6(500mg)を逆相HPLC[移動相 MeOH:水=30:70、1%酢酸]を用いて分離精製し、化合物(15)(25.0mg、0.0053%)を単離した。
MeOH溶出部(160.2g)を、順相シリカゲルカラムクロマトグラフィー[3.0kg、クロロホルム:MeOH:水=10:3:1(下層)→6:4:1(下層)→MeOH]で順次溶出させて、溶出画分M1(18.7g)、M2(7.0g)、M3(22.7g)、M4(97.9g)、M5(7.5g)を得た。
溶出画分M3(22.7g)を、逆相ODSカラムクロマトグラフィー[700g、メタノール:水=(40:60→60:40→80:20→メタノール)にて画分し、溶出画分M3−1(3.68g)、M3−2(0.91g)、M3−3(5.10g)、M3−4(5.58g)、M3−5(2.78g)を得た。さらに得られた画分M3−3(500mg)を、逆相HPLC[移動相 MeOH:水=40:60、1%酢酸]を用いて分離精製し、化合物(2)(6.0mg、0.0032%)、化合物(3)(11.7mg、0.0062%)、化合物(4)(19.9mg、0.0106%)、化合物A(94.6mg、0.0504%)、化合物(5)(39.5mg、0.0211%)を得た。
溶出画分M4(97.9g)を、逆相ODSカラムクロマトグラフィー[3.0kg、メタノール:水=(50:50→70:30→メタノール)にて画分し、溶出画分M4−1(26.2g)、M4−2(4.60g)、M4−3(22.5g)、M4−4(39.7g)、M4−5(8.60g)を得た。さらに得られた画分M4−1(500mg)を、逆相HPLC[移動相 MeOH:水=40:60、1%酢酸]を用いて分離精製し、化合物(6)(7.6mg、0.021%)、化合物(7)(8.3mg、0.023%)、化合物B(15.3mg、0.042%)、化合物(8)(17.3mg、0.047%)、化合物(9)(139.1mg、0.381%)、化合物(10)(10.2mg、0.0028%)及び化合物(1)(9.8mg、0.027%)を得た。
実施例4、5で得られた化合物(11)〜(15)、並びに、実施例7、8で得られた化合物(1)〜(10)及び化合物A、Bについて、1H−NMR及び13C−NMR等の測定を行った。それらの測定値と、公知文献記載の物理化学的データの数値との比較から、化合物(2)〜(15)及び化合物A、Bは、それぞれ、以下に示す公知化合物であることが確認された。それぞれの構造及び[]内に化合物名を示す。
・化合物(3):前記の構造式(3)で表される化合物[ケルセチン3−O−β−D−グルコピラノシド]
・化合物(4):前記の構造式(4)で表される化合物[ケンフェロール3−O−β−D−ガラクトピラノシド]
・化合物(5):前記の構造式(5)で表される化合物[ケンフェロール3−O−β−D−グルコピラノシド]
・化合物(6):前記の構造式(6)で表される化合物[ルチン]
・化合物(7):前記の構造式(7)で表される化合物[アピゲニン6C−β−D−グルコピラノシル8C−α−L−アラビノシド]
・化合物(9):前記の構造式(9)で表される化合物[ケンフェロール3−O−β−D−グルコピラノシル−(1→3)−α−L−ラムノピラノシル−(1→6)−β−D−ガラクトピラノシド]
・化合物(10):前記の構造式(10)で表される化合物[ミリセチン3−O−β−D−ガラクトピラノシド]
・化合物(11):前記の構造式(11)で表される化合物[ケンフェロール]
・化合物(12):前記の構造式(12)で表される化合物[ケルセチン]
・化合物(13):前記の構造式(13)で表される化合物[(−)−エピカテキン]
・化合物(14):前記の構造式(14)で表される化合物[(−)−エピカテキン3−O−ガレート]
・化合物(15):前記の構造式(15)で表される化合物[(−)−エピガロカテキン3−O−ガレート]
・化合物(B):[ケルセチン3−O−ネオヘスペリドシド]
・旋光度:[α]D 26: −38.9°(c=1.35,MeOH)
・紫外吸収スペクトル[MeOH,nm,(log ε)]:272.5(4.12)
・高分解能質量分析(High−resolution FAB−MS):
理論値 C34H50O21Na [M+Na]+: 809.2116
実測値 : 809.2112
・赤外吸収スペクトル(KBr,cm−1): 3469、1686、1541、1076
・Pos.FAB−MS:m/z 809[M+Na]+
・Neg.FAB−MS:m/z 785[M−H]−、623[M−C6H12O5]−、315[M−C18H31O14]−
実施例1、2で得られたメタノール抽出エキス、AcOEt可溶部、メタノール溶出部及び水溶出部、実施例4、5で得られた化合物(11)〜(15)、並びに、実施例7、8で得られた化合物(1)〜(10)及び化合物A、Bについて、脂肪代謝改善作用の指標として、HepG2細胞を用いた細胞内脂肪代謝促進作用試験を実施した。試験方法を以下に示す。
大日本住友製薬より購入したヒト肝がん由来HepG2細胞を用いた。培地はminimum essential medium Eagle(MEM,シグマ−アルドリッチ社)に、10%(v/v)fatal calf serum(FCS)及び100units/mLペニシリンG、100μg/mLストレプトマイシン及び0.1mM非必須アミノ酸(インビトロジェン社)を添加して使用した。細胞の培養は、75cm2培養フラスコ(ファルコン社)中で行い、5%CO2雰囲気下37℃にて行った。継代操作は,培養した細胞をダルベッコPBS(−)(日水製薬社)で洗浄した後、0.02%(w/v)トリプシン(ディフコ社)及び0.05%(w/v)EDTA・2Na(同人化学社)を含むPBS(−)により剥離して、定法に従い行った。
Claims (5)
- チャの花もしくは花蕾、水、低級脂肪族アルコールもしくは低級脂肪族アルコールの含水物によりチャの花もしくは花蕾を抽出して得られる抽出液、又は前記抽出液を濃縮して得られる抽出エキス、を有効成分として含むことを特徴とする脂肪代謝改善剤。
- 下記の構造式(1)で表されるフラボノイド化合物
下記の構造式(2)で表されるフラボノイド化合物
下記の構造式(3)で表されるフラボノイド化合物
下記の構造式(4)で表されるフラボノイド化合物
下記の構造式(5)で表されるフラボノイド化合物
下記の構造式(6)で表されるフラボノイド化合物
下記の構造式(7)で表されるフラボノイド化合物
下記の構造式(8)で表されるフラボノイド化合物
下記の構造式(9)で表されるフラボノイド化合物
下記の構造式(10)で表されるフラボノイド化合物
下記の構造式(11)で表されるフラボノイド化合物
下記の構造式(12)で表されるフラボノイド化合物
下記の構造式(13)で表されるカテキン化合物
下記の構造式(14)で表されるカテキン化合物、及び
下記の構造式(15)で表されるカテキン化合物
からなる群の中から選ばれる化合物を有効成分として含むことを特徴とする脂肪代謝改善剤。 - 請求項1又は請求項2に記載の脂肪代謝改善剤を含有することを特徴とするヒト又は動物用の医薬。
- 請求項1又は請求項2記載の脂肪代謝改善剤を含有することを特徴とする食品。
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US20130171277A1 (en) * | 2011-12-30 | 2013-07-04 | Amorepacific Corporation | Composition for preventing or improving metabolic syndrome comprising tea plant leaf, flower and seed extract |
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0917610A (ja) * | 1995-06-26 | 1997-01-17 | Mitsui High Tec Inc | センサ−リ−ドの製造方法 |
JPH11107A (ja) * | 1997-06-12 | 1999-01-06 | Res Inst For Prod Dev | 高カテキン類含有チャ葉 |
JP2002080362A (ja) * | 2000-06-21 | 2002-03-19 | Kao Corp | Ppar依存的遺伝子転写活性化剤 |
US20080286254A1 (en) * | 2007-05-17 | 2008-11-20 | Kaneka Corporation | Composition comprising licorice polyphenol |
-
2009
- 2009-09-03 JP JP2009204012A patent/JP5620660B2/ja active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0917610A (ja) * | 1995-06-26 | 1997-01-17 | Mitsui High Tec Inc | センサ−リ−ドの製造方法 |
JPH11107A (ja) * | 1997-06-12 | 1999-01-06 | Res Inst For Prod Dev | 高カテキン類含有チャ葉 |
JP2002080362A (ja) * | 2000-06-21 | 2002-03-19 | Kao Corp | Ppar依存的遺伝子転写活性化剤 |
US20080286254A1 (en) * | 2007-05-17 | 2008-11-20 | Kaneka Corporation | Composition comprising licorice polyphenol |
Non-Patent Citations (4)
Title |
---|
JPN6013046503; J Natural Products, Vol.68 No.9 (2005) p.1360-1365 * |
JPN6013046504; 日本農芸化学会2008年度大会講演要旨集, (2008) p.45(2A12a05) * |
JPN6013046505; 日本農芸化学会2009年度大会講演要旨集, (2009.03.05) p.134(2P1075A) * |
JPN6013046508; Nutrition & Metabolism, Vol.6 (2009.05.01) * |
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US9452192B2 (en) * | 2011-12-30 | 2016-09-27 | Amorepacific Corporation | Composition for preventing or improving metabolic syndrome comprising tea plant leaf, flower and seed extract |
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