海绵糖苷，来自海洋海绵Amphimedon sp.的3-烷基吡啶糖苷

Amphimedosides, 3-alkylpyridine glycosides from a marine sponge Amphimedon sp.

作者信息

Takekawa Yoshihiko, Matsunaga Shigeki, van Soest Rob W M, Fusetani Nobuhiro

机构信息

Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-8657, Japan.

出版信息

J Nat Prod. 2006 Oct;69(10):1503-5. doi: 10.1021/np060122q.

DOI:10.1021/np060122q

PMID:17067172

Abstract

Five 3-alkylpyridine alkaloids, amphimedosides A-E (1-5), have been isolated from a marine sponge Amphimedon sp. The structures of 1-5 have been determined by analysis of NMR and FABMS data and chiral GC analyses of the acid hyrolyzates. In particular, the site of glycosylation in 1 was confirmed by the 1H-15N HMBC experiment, and the location of the double bond in 5 was assigned on the basis of tandem FABMS data. Amphimedosides are the first examples of beta-D-glucosylated 3-alkylpyridine alkaloids and exhibited cytotoxic activities comparable with those of the nonglycosylated congeners.

摘要

从海洋海绵Amphimedon sp.中分离出了5种3-烷基吡啶生物碱，即两性霉素A-E（1-5）。通过对核磁共振（NMR）和快原子轰击质谱（FABMS）数据的分析以及对酸水解产物的手性气相色谱分析，确定了1-5的结构。特别是，通过1H-15N HMBC实验确定了1中糖基化的位点，并根据串联FABMS数据确定了5中双键的位置。两性霉素是β-D-葡萄糖基化3-烷基吡啶生物碱的首个实例，其细胞毒性活性与非糖基化同系物相当。