纤毛醇 A-J，来源于中国传统植物纤毛弗氏耳蕨（B1.）的高度氧化的贝壳杉烷二萜

Fimbriatols A-J, Highly Oxidized ent-Kaurane Diterpenoids from Traditional Chinese Plant Flickingeria fimbriata (B1.) Hawkes.

机构信息

Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100193, P. R. China.

Beijing University of Chemical Technology, Beijing 100029, People's Republic of China.

出版信息

Sci Rep. 2016 Aug 3;6:30560. doi: 10.1038/srep30560.

DOI:10.1038/srep30560

PMID:27484744

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4971462/

Abstract

Fimbriatols A-J (1-10), ten new ent-kaurane diterpenoids possessing differently highly oxidized sites, were isolated from Flickingeria fimbriata (B1.) Hawkes. The structures of these new compounds were determined by HRESI-MS, NMR, CD spectra and X-ray diffraction analysis. Compound 1 displayed moderately inhibitory ratio (48.5%) compared with the positive compound NSC-87877 (81.6%) at the concentration of 0.022 μg/mL. Compounds 7-10 possess 3, 4-seco-ent-kaurane skeleton containing a disaccharide moiety with an unusual linkage at C-2' to C-1'' instead of the common linkage at C-6' to C-1'', and this is the first report in 600 more ent-kauranes found in nature, which might be originated from ent-kaurane diterpenoids through post-modified reactions of Baeyer-Villiger oxygenation and glycosylation.

摘要

纤毛醇 A-J（1-10），十种新的具有高度氧化位点的 ent-贝壳杉烷二萜，从 Flickingeria fimbriata（B1.）Hawkes 中分离得到。这些新化合物的结构通过 HRESI-MS、NMR、CD 光谱和 X 射线衍射分析确定。在浓度为 0.022μg/mL 时，化合物 1 与阳性化合物 NSC-87877（81.6%）相比，显示出中等抑制率（48.5%）。化合物 7-10 具有 3,4-seco-ent-贝壳杉烷骨架，含有一个二糖部分，在 C-2'到 C-1''处具有不常见的连接，而不是在 C-6'到 C-1''处的常见连接，这是在自然界中发现的 600 多种 ent-贝壳杉烷中首次报道，可能是通过 Baeyer-Villiger 氧化和糖基化的后修饰反应，从 ent-贝壳杉烷二萜衍生而来的。