Absolute stereostructure of carabrane-type sesquiterpene and vasorelaxant-active sesquiterpenes from Zedoariae Rhizoma

被引：56

作者：

Matsuda, H ^{[1
]}

Morikawa, T ^{[1
]}

Ninomiya, K ^{[1
]}

Yoshikawa, M ^{[1
]}

机构：

[1] Kyoto Pharmaceut Univ, Yamashina Ku, Kyoto 6078412, Japan

来源：

TETRAHEDRON | 2001年 / 57卷 / 40期

关键词：

pharmacologically active compounds; terpenes and terpenoids; cyclopropanes; stereochemistry;

D O I：

10.1016/S0040-4020(01)00828-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The aqueous acetone extract of Zedoariae Rhizoma was found to show inhibitory effects on contractions induced by high concentrations of potassium cation (K+) in isolated rat aortic strips. From the extract, two new carabrane-type sesquiterpenes, curcarabranols A and B, were isolated together with a few carabrane-type sesquiterpenes, such as curcumenone and 4S-dihydrocurcumenone. Their absolute stereostructures were determined on the basis of chemical and physicochemical evidence, which included the application of the modified Mosher's method and chemical conversion from curcumenone to curcarabranols A and B. In addition, several sesquiterpenes and diaryl-heptanoids (e.g. germacrone, glechomanolide, isocurucmenol, beta -eudesmol, and beta -dictyopterol) showed potent inhibitory effects on contractions induced by high concentrations of K+ in isolated rat aortic strips (inhibition > 80% at 100 muM), while they did not inhibit norepinephrine-induced contractions, so that the vasorelaxant activities of these sesquiterpenes were presumed to be dependent on their calcium channel-blocking activity. (C) 2001 Elsevier Science Ltd. AE rights reserved.

引用

页码：8443 / 8453

页数：11

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