半日花烷型、三环和四环降二萜类化合物的转化及其对恶性疟原虫的体外活性

Transformations of manool. tri- and tetracyclic norditerpenoids with in vitro activity against Plasmodium falciparum.

作者信息

van Wyk Albert W W, Lobb Kevin A, Caira Mino R, Hoppe Heinrich C, Davies-Coleman Michael T

机构信息

Department of Chemistry, Rhodes University, Grahamstown, South Africa.

出版信息

J Nat Prod. 2007 Aug;70(8):1253-8. doi: 10.1021/np0701071. Epub 2007 Jul 11.

DOI:10.1021/np0701071

PMID:17625894

Abstract

The known 17-norisopimar-15-ene-8beta,13beta-diol (5) and five new semisynthetic norditerpenoids, ethyl 17-norabiet-13(15)-E-en-8beta-ol-16-oate (6), ethyl 17-norabiet-13(15)-Z-en-8beta-ol-16-oate (7), 17-norpimaran-13alpha-ethoxy-8,16-olactone (8), 17-norisopimarane-8beta,15-diol (9), and 17-norarabiet-13(15)-ene-8beta,16-diol (10), were prepared from manool (11). Standard spectroscopic data including X-ray crystal analysis were used to determine the structures of 5-10. All five compounds exhibited in vitro antiplasmodial activity against the malarial parasite Plasmodium falciparum at varying microg mL(-1) concentrations.

摘要

已知的17-降异海松-15-烯-8β,13β-二醇（5）以及五个新的半合成去甲二萜类化合物，即17-去甲枞酸-13(15)-E-烯-8β-醇-16-乙酯（6）、17-去甲枞酸-13(15)-Z-烯-8β-醇-16-乙酯（7）、17-降海松烷-13α-乙氧基-8,16-内酯（8）、17-降异海松烷-8β,15-二醇（9）和17-去甲枞酸-13(15)-烯-8β,16-二醇（10），是从马尼醇（11）制备得到的。利用包括X射线晶体分析在内的标准光谱数据来确定5-10的结构。所有这五个化合物在不同的微克/毫升浓度下均表现出对疟原虫恶性疟原虫的体外抗疟活性。