14 イオン輸送に関与する複合脂質の合成研究(口頭発表の部)
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概要
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I. Glycosphingolipid: Soya-cerebrosides I and II Soya-cerebrosides I and II, two new glycosphingolipids, were isolated from the seeds of Glycine max and their chemical structures including the fatty acid compositions (major: 2R-hydroxypalmitoyl-type) were elucidated on the basis of their physical data and chemical derivatizations. By using the apparatus W-08, it has been found that soya-cerebrosides I and II exhibit ion-binding activity for Ca^<++> ions. Further, by the method for measuring ion-permeability, it has been revealed that soya-cerebroside II exhibits activity to increase internal Ca^<++> ions of human erythrocytes. So that, we have synthesized 2R-hydroxypalmitoyl and palmitoyl analogs of soya-cerebroside II from a chiral C4-epoxide, the synthon of our synthetic study of complex lipids. The 2R-hydroxypalmitoyl analog has been shown to exhibit ion-binding and membrane-permeable activities for Ca^<++> ions, while the palmitoyl analog to show very little activities. II. Coronand Epoxides derived from Geraniol and E, E-Farnesol Each two coronand-type epoxides (GL_2E_2, GL_2E_4 and FL_1E_2, FL_2E_4) were synthesized respectively from geraniol and E,E-farnesol. GL_2E_4 exhibited ion-transport activity for Ca^<++> ion and ion-permeability for K^+ and Ca^<++> ions while FL_2E_4 exhibited ion-transport activity and permeability for K^+ ions. Each six diastereomers of GL_2E_4 and FL_2E_4 were separated by HPLC and their activities were shown as affected by the epoxide configurations. III. Podand Epoxides derived from Geraniol and E,E-Farnesol Totally 16 podand-type epoxides (GE-1〜GE-8 and FE-1-FE-8) were synthesized from geraniol and E,E-farnesol. GE-8, ω-hydroxy methyl ester diepoxide, exhibited ion-binding, ion-transport and ion permeable activities for Ca^<++> ions. Four optically active GE-8 (13,14,15,16) were then synthesized by employing Sharpless asymmetric epoxidation. As for ion-binding activity for Ca^<++> ions, syn-type GE-8 (13,15) exhibited more higher activity than anti-type GE-8 (14,16), and further one of syn-type GE-8 (15) showed quite stronger ion-permeability than another syn-type GE-8 (13). These findings indicate that human erythrocyte membranes clearly distinguish between two enantiomers, 13 and 15.
- 天然有機化合物討論会の論文
- 1991-09-07
著者
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成田 憲彦
大阪大学薬学部
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北川 勲
阪大・薬
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渋谷 博孝
阪大・薬
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黒須 三千夫
阪大・薬
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成田 憲彦
阪大・薬
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片山 精司
阪大・薬
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皆川 和之
阪大・薬
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黒須 三千夫
Faculty of Pharmaceutical Sciences, Osaka University
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黒須 三千夫
阪大薬
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皆川 和之
大阪大学薬学部
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片山 精司
大阪大学薬学部
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