质谱和核磁共振在天然产物复杂糖基结构解析中的应用：以丝兰甾体皂苷为例

Application of MS and NMR to the structure elucidation of complex sugar moieties of natural products: exemplified by the steroidal saponin from Yucca filamentosa L.

作者信息

Plock A, Beyer G, Hiller K, Gründemann E, Krause E, Nimtz M, Wray V

机构信息

Institut für Pharmazie, Humboldt-Universität zu Berlin, Germany.

出版信息

Phytochemistry. 2001 Jun;57(3):489-96. doi: 10.1016/s0031-9422(01)00035-8.

DOI:10.1016/s0031-9422(01)00035-8

PMID:11393530

Abstract

An approach, using well characterized procedures, is presented that should be of general applicability for the structural elucidation of complex sugar moieties of natural products. The methods used are exemplified by the structure elucidation of a new gitogenin-based steroidal saponin that has a strong leishmanicidal activity similar to preparations used in clinical practice and has been isolated by bioactivity-guided fractionation of the ethanolic extract of Yucca filamentosa L. leaves. The saponin has been characterized as 3-O-((beta-D-glucopyranosyl-(1-->3)- beta-D-glucopyranosy-(1-->2))(alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->3))-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranosyl)-25R,5alpha-spirostan-2alpha,3beta-diol.

摘要

本文介绍了一种方法，该方法采用了特征明确的程序，应普遍适用于天然产物复杂糖部分的结构解析。所使用的方法以一种新的基于吉托皂苷元的甾体皂苷的结构解析为例，该皂苷具有与临床实践中使用的制剂相似的强大杀利什曼原虫活性，并且是通过对丝兰属植物叶乙醇提取物进行生物活性导向分级分离而分离得到的。该皂苷已被鉴定为3-O-((β-D-吡喃葡萄糖基-(1→3)-β-D-吡喃葡萄糖基-(1→2))(α-L-吡喃鼠李糖基-(1→4)-β-D-吡喃葡萄糖基-(1→3))-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃半乳糖基)-25R,5α-螺甾烷-2α,3β-二醇。