Chemical Transformation of Terpenoids. X. Ionophoretic Activities of Macrocyclic Lactone Epoxides Synthesized from Geraniol

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• Two coronand-type 18-membered lactone epoxides, i.e., geranyl dimeric lactone diepoxide (GL_2E_2,10) and tetraepoxide (GL_2E_4,11), were synthesized from geraniol as diastereomeric mixtures. Among them, GL_2E_4 (11) was shown to exhibit ion-transport activity for Ca^<2+> ion in the test using a W-07 (liquid-membrane type) apparatus and ion-permeation activities for Ca^<2+> and K^+ ions across the human erythrocyte membrane. Isolation of six component diastereomers of GL_2E_4 (11) [GL_2E_4-1 (11c), -2 (11d), -3 (11e), -4 (11f), -5 (11g), -6 (11h)], was effected by HPLC separation of two diastereomeric tetraepoxides (11a, 11b) which were prepared from two diepoxides (GL_2E_2-1,10a and GL_2E_2-2,10b). The relative stereostructures of these diastereomers were determined by a combination of X-ray diffraction and ^1H-NMR analyses. Among the six diastereomers, S_2-symmetrical GL_2E_4-4 (11f) exhibited the strongest ion-transport activity for Ca^<2+> ion while C_2-symmetrical GL_2E_4-6 (11h) exhibited the strongest ion-permeation activity for Ca^<2+> ion across the human erythrocyte membrane.

• 社団法人日本薬学会の論文
• 1994-02-15

著者

• 北川 勲

  Faculty of Pharmaceutical Sciences, Osaka University

• 成田 憲彦

  大阪大学薬学部

• 石田 寿昌

  大阪薬大

• 渋谷 博孝

  福山大学

• 渋谷 博孝

  Faculty of Pharmaceutical Sciences, Osaka University

• 石田 寿昌

  大阪薬科大学

• 大橋 一慶

  福山大学

• 大橋 一慶

  Faculty of Science, Shizuoka University

• 成田 憲彦

  Faculty of Pharmaceutical Sciences, Osaka University

• 石田 寿昌

  Osaka University of Pharmaceutical Sciences

• 北川 勲

  大阪大学

• 北川 勲

  Faculty Of Pharmaceutical Sciences Osaka University

• 石田 寿晶

  大阪薬科大学

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