JPWO2007043302A1 - インスリン抵抗性改善剤 - Google Patents
インスリン抵抗性改善剤 Download PDFInfo
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- JPWO2007043302A1 JPWO2007043302A1 JP2007539847A JP2007539847A JPWO2007043302A1 JP WO2007043302 A1 JPWO2007043302 A1 JP WO2007043302A1 JP 2007539847 A JP2007539847 A JP 2007539847A JP 2007539847 A JP2007539847 A JP 2007539847A JP WO2007043302 A1 JPWO2007043302 A1 JP WO2007043302A1
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- insulin resistance
- compound
- insulin
- plant
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Abstract
Description
[製造例1]
以下、ユリ科に属する植物からの製造例として、アロエベラからの3−O−β−D−グルコピラノシル−4−メチルエルゴスト−7−エン−3−オールの製造例を示す。
アロエベラの葉肉(透明ゲル部分)100kgを、ホモジナイザーを用いて液状化し、ここに100リットルの酢酸エチル/ブタノール混合液(3:1)を添加して攪拌した。一晩放置した後、酢酸エチル/ブタノール混合液と水層を分液して、酢酸エチル/ブタノール混合液を回収した。この酢酸エチル/ブタノール混合液を減圧下濃縮して得られた酢酸エチル/ブタノール混合液抽出物の質量は、13.5gであった。上記水層および酢酸エチル/ブタノール混合液抽出物を用いて、後述の実施例3に示すインスリン負荷試験によるインスリン抵抗性改善作用に対する評価を行ったところ、酢酸エチル/ブタノール混合液抽出物に同作用が認められたので、この抽出物中の成分の分離、精製を試みた。
C-1:36.8, C-2:27.3, C-3:78.7, C-4:37.0, C-5:46.9, C-6:26.8, C-7:117.4, C-8:139.4, C-9:49.7, C-10:34.9, C-11:21.6, C-12:39.7, C-13:43.6, C-14:55.1, C-15:23.1, C-16:28.2, C-17:56.3, C-18:12.0, C-19:14.2, C-20:36.5, C-21:19.0, C-22:33.9, C-23:30.6, C-24:39.1, C-25:32.6, C-26:20.4, C-27:18.4, C-28:15.6, C-29:15.3
装置:GC-17A/GCMS5050A(SHIMADZU)
GCカラム:NEUTRA BOND-5(GL Scienses)
カラム温度:100℃(2分)→(10℃/分)→300℃(28分)
注入温度:250℃,
キャリアガス:He (1.3mL/分)
インターフェイス温度:300℃
MSモード:EI
イオン化エネルギー:70eV
標準物質:3−アセトキシ−4−メチルエルゴスト−7−エン:tR [min]=39.4; m/z 456[M]+, 441[M-CH3]+, 396[M-AcOH]+, 381[M-CH3-AcOH]+
(化合物1)
分子式:C35H60O6
分子量:576
化学式:下記化学式(1)
分子式:C29H50O
分子量:414
化学式:下記化学式(2)
分子式:C31H52O2
分子量:456
化学式:下記化学式(3)
アロエベラの葉肉(透明ゲル部分)を加熱乾燥し、粉砕した乾燥アロエベラ粉末0.3gに、60%、80%、又は100%エタノール60mlを加えた後、60℃で1時間加熱還流した。抽出液を1500rpmで20分間遠心分離し、上清を減圧下で濃縮して完全にエタノールを除去して、粗抽出物を得た。60%、80%、及び100%エタノールを用いた抽出により得られた粗抽出物の乾燥質量は、各々65mg、42mg、18mgであった。これらの粗抽出物が3−O−β−D−グルコピラノシル−4−メチルエルゴスト−7−エン−3−オールを含むことを、薄層クロマトグラフィーで確認した。
アロエベラの葉肉(透明ゲル部分)を加熱乾燥し、粉砕した乾燥アロエベラ粉末0.3gに、水60mlを加えた後、95℃で5時間加熱還流した。抽出液を1500rpmで20分間遠心分離し、上清を凍結乾燥して、75mgの粗抽出物を得た。この粗抽出物が3−O−β−D−グルコピラノシル−4−メチルエルゴスト−7−エン−3−オールを含むことを、薄層クロマトグラフィーで確認した。
アロエベラの葉肉(透明ゲル部分)を加熱乾燥し、粉砕した乾燥アロエベラ粉末21kgに、クロロホルム/メタノール混合液(2:1)90リットルを加えた後、室温にて一晩浸漬したのちろ過し、濾過残渣に再びクロロホルム/メタノール混合液(2:1)90リットルを添加して同様な操作を計4回行った。得られた濾液(350リットル)を28℃で濃縮し、最終的に粗抽出物784gを得た。このうち780gの粗抽出物にクロロホルム/メタノール混合液(2:1)2リットルを添加し、1時間攪拌した後ろ過してクロロホルム/メタノール混合液層を回収した(A)。濾過残渣は、まず水2.5リットル及び酢酸エチル2リットルを順次添加して1時間攪拌後、酢酸エチル層(B)を回収し、残った水層にクロロホルム5リットルを再度添加し、1時間攪拌後、クロロホルム層(C)を回収した。
前記製造例1で製造した3−O−β−D−グルコピラノシル−4−メチルエルゴスト−7−エン−3−オールをDMSOに溶解した後、濃度が15μg/mlになるように蒸留水にて調製して試験試料とした。このときDMSOの最終濃度は0.2%になるように調整した。また、試験試料を含まない溶液を陰性試料とした。
6週齢、雄性ZDFラット(米国チャールスリバー社より購入)を高脂肪食(リサーチダイエット社製)を用いて1ヶ月間の予備飼育を行った後、1群6匹に群分けした。各群のラットに、1日1回ゾンデを用いて、試験試料又は陰性試料を体重400gにつき1mlずつ(37.5μg/kg体重)連日経口投与した。試料の投与開始から45日目に絶食下で採血し、血清中の遊離脂肪酸量を、NEFA C-テストワコー(和光純薬工業社製)にて測定した。
表1は、投与開始から45日目のラット血清中の遊離脂肪酸濃度を表している。陰性試料投与群に比して、試験試料投与群では血清中の遊離脂肪酸値が約53%と有意な低下が認められた。尚、投与期間中に病理的な所見からの副作用は全く見られなかった。なお、表中のp値はTukey-Kramer's testによる有意確率を示している。
本実施例2の試料には、前記実施例1で調製したものと同様の試験試料及び陰性試料を使用した。
6週齢、雄性ZDFラット(米国チャールスリバー社より購入)を高脂肪食(リサーチダイエット社製)を用いて1ヶ月間の予備飼育を行った後、1群6匹に群分けした。各群のラットに、1日1回ゾンデを用いて、試験試料又は陰性試料を体重400gにつき1mlずつ(37.5μg/kg体重)連日経口投与した。試料の投与開始から45日目に絶食下で採取した精巣周囲の脂肪1gに、0.5%ウシ血清アルブミンを含有するD−MEM/F12培地を1.5ml添加し、37℃で培養した。培養1時間後に回収した培養上清中のTNF−α及びMCP−1の濃度を、ELISA法(バイオソース社製)にて測定した。
表2は脂肪組織からのTNF−αの産生量を表している。また、表3は同様にMCP−1の産生量を表している。いずれの結果からも明らかなとおり、陰性試料投与群に比して試験試料を投与した群は、TNF−α、及びMCP−1ともに、有意な産生抑制効果が確認された。本実施例の結果から、本発明のインスリン抵抗性改善剤を投与することにより、インスリン抵抗性を増悪させる脂肪組織中でのインスリン抵抗性を惹起させるアディポサイトカインの産生が低減し、インスリン抵抗性の増悪予防効果を有することが明らかとなった。なお、表中のp値はTukey-Kramer's testによる有意確率を示している。
本実施例3の試料には、前記実施例1又は2で調製したものと同様の試験試料及び陰性試料を使用した。
6週齢、雄性ZDFラット(米国チャールスリバー社より購入)を高脂肪食(リサーチダイエット社製)を用いて1ヶ月間の予備飼育を行った後、1群6匹に群分けした。各群のラットに、1日1回ゾンデを用いて、試験試料又は陰性試料を体重400gにつき1mlずつ(37.5μg/kg体重)連日経口投与した。試料の投与開始から35日目にインスリン負荷試験を行った。本実施例におけるインスリン負荷試験は、ラットを4時間絶食させた後、ヒト・インスリン(イーライリリー社製)を10U/kg体重の用量で腹腔内投与し、インスリン投与開始から60分経過時まで経時的に血糖値の変化を測定することにより行った。
本実施例の結果は図1に示すとおりである。図1は、インスリン負荷試験の結果を表している。図1から明らかなとおり陰性試料を投与した群に比して、試験試料を投与した群の血糖値は、インスリン投与開始から15分〜60分のいずれの時点においても低値を示していることが明らかとなった。本実施例の結果から、本発明のインスリン抵抗性改善剤の投与により、インスリン感受性を亢進させることが判明した。
Claims (9)
- 前記植物がユリ科植物である請求項2に記載のインスリン抵抗性改善剤。
- 請求項1〜3のいずれか一項に記載のインスリン抵抗性改善剤を含有する飲食品。
- 前記化学式(1)で示される化合物を0.0001質量%以上含む請求項4に記載の飲食品。
- 前記植物がユリ科植物である請求項6に記載の使用。
- 前記植物がユリ科植物である請求項8に記載の方法。
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WO2007043302A1 (ja) | 2007-04-19 |
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