来自南非软珊瑚克氏克劳德珊瑚的西松烷二萜类化合物。

Cembrane diterpenes from the southern African soft coral Cladiella kashmani.

作者信息

Gray C A, Davies-Coleman M T, Schleyer M H

机构信息

Department of Chemistry, Rhodes University, Grahamstown, 6140, South Africa.

出版信息

J Nat Prod. 2000 Nov;63(11):1551-3. doi: 10.1021/np000179r.

DOI:10.1021/np000179r

PMID:11087607

Abstract

Two known cembrane diterpenes, flaccidoxide (1) and (1Z,3E,7E,11S, 12S,14S)-11,12-epoxy cembra-1,3,7-trien-14-ol (2), and the new cembrane diterpene flaccidoxide-13-acetate (3) were isolated from specimens of Cladiella kashmani collected off Ponto do Oura, Mozambique. The modified Mosher's method established the previously unassigned absolute configuration of 1 as (1Z,3E,7E,11S,12S,13S, 14R)-14-acetoxy-11,12-epoxy cembra-1,3,7-trien-13-ol. Acetylation of 1 yielded 3 and thus confirmed the structure of 3 as (1Z,3E,7E,11S, 12R,13S,14R)-13,14-diacetoxy-11,12-epoxy cembra-1,3,7-triene. All three diterpenes were toxic to the brine shrimp Artemia salina.

摘要

从莫桑比克蓬托杜奥拉采集的卡什曼软珊瑚（Cladiella kashmani）标本中分离出两种已知的西松烷二萜类化合物，软珊瑚醇（1）和（1Z,3E,7E,11S,12S,14S）-11,12-环氧西松-1,3,7-三烯-14-醇（2），以及新的西松烷二萜类化合物软珊瑚醇-13-乙酸酯（3）。改良的莫舍尔方法确定了1之前未确定的绝对构型为（1Z,3E,7E,11S,12S,13S,14R）-14-乙酰氧基-11,12-环氧西松-1,3,7-三烯-13-醇。1的乙酰化反应生成了3，从而证实了3的结构为（1Z,3E,7E,11S,12R,13S,14R）-13,14-二乙酰氧基-11,12-环氧西松-1,3,7-三烯。所有这三种二萜类化合物对卤虫（Artemia salina）均有毒性。