来自溪边睫毛苔的生物活性及其他倍半萜类化合物。

Bioactive and other sesquiterpenes from Chiloscyphus rivularis.

作者信息

Wu C, Gunatilaka A A, McCabe F L, Johnson R K, Spjut R W, Kingston D G

机构信息

Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg 24061, USA.

出版信息

J Nat Prod. 1997 Dec;60(12):1281-6. doi: 10.1021/np970251u.

DOI:10.1021/np970251u

PMID:9463110

Abstract

Bioassay-directed fractionation of the methyl ethyl ketone extract of Chiloscyphus rivularis yielded five new sesquiterpenes, 12-hydroxychiloscyphone (2), chiloscypha-2,7-dione (3), 12-hydroxychiloscypha-2,7-dione (4), chiloscypha-2,7,9-trione (5), and rivulalactone (6) in addition to the known sesquiterpenes, 4-hydroxyoppositan-7-one (7), chiloscyphone (1), and isointermedeol (8). The structure and stereochemistry of rivulalactone, a novel trinorsesquiterpene, was confirmed by its synthesis starting from 1. Compound 2 showed selective bioactivity in our yeast-based DNA-damaging assay and cytotoxicity to human lung carcinoma cells.

摘要

对溪边唇鳞苔的甲乙酮提取物进行生物活性导向分离，除了已知的倍半萜4-羟基奥波西坦-7-酮（7）、唇鳞苔酮（1）和异间苯二酚（8）外，还得到了5个新的倍半萜，12-羟基唇鳞苔酮（2）、唇鳞苔-2,7-二酮（3）、12-羟基唇鳞苔-2,7-二酮（4）、唇鳞苔-2,7,9-三酮（5）和溪苔内酯（6）。通过以化合物1为起始原料合成，确定了新型三降倍半萜溪苔内酯的结构和立体化学。化合物2在我们基于酵母的DNA损伤试验中显示出选择性生物活性，对人肺癌细胞具有细胞毒性。