来自大头苋根部的齐墩果烷型和蒲公英赛烷型糖苷。

Oleanane and taraxerane glycosides from the roots of Gomphrena macrocephala.

作者信息

Kuroda Minpei, Aoshima Taku, Haraguchi Mitsue, Young Maria Claudia Marx, Sakagami Hiroshi, Mimaki Yoshihiro

机构信息

Laboratory of Medicinal Pharmacognosy, Tokyo University of Pharmacy and Life Sciences, School of Pharmacy, 1432-1, Horinouchi, Hachioji, Tokyo 192-0392, Japan.

出版信息

J Nat Prod. 2006 Nov;69(11):1606-10. doi: 10.1021/np068014r.

DOI:10.1021/np068014r

PMID:17125230

Abstract

Phytochemical screening of the roots of Gomphrena macrocephala, with particular attention to its triterpene glycoside constituents, has resulted in the isolation of two new oleanane glycosides (1 and 2) and a new taraxerane glycoside (3). The structures of 1-3 were determined as 11alpha,12alpha-epoxy-3beta-[(O-beta-D-glucuronopyranosyl)oxy]olean-28,13-olide (1), 11alpha,12alpha-epoxy-3beta-[(O-beta-D-galactopyranosyl-(1-->3)-O-[beta-D-glucopyranosyl-(1-->2)]-beta-D-glucuronopyranosyl)-oxy]olean-28,13-olide (2), and 11alpha,12alpha-epoxy-3beta-[(O-beta-D-glucuronopyranosyl)oxy]taraxer-14-en-28-oic acid beta-D-glucopyranosyl ester (3), respectively, on the basis of their spectroscopic data and the results of hydrolysis. The aglycones (1a and 3a) of 1-3 with an epoxy group showed cytotoxic activity against HSC-2 human oral squamous carcinoma cells.

摘要

对大头苋根进行植物化学筛选，尤其关注其三萜糖苷成分，结果分离出两种新的齐墩果烷糖苷（1和2）和一种新的蒲公英赛烷糖苷（3）。根据1 - 3的光谱数据和水解结果，其结构分别确定为11α,12α - 环氧 - 3β - [(O - β - D - 葡萄糖醛酸吡喃糖基)氧基]齐墩果 - 28,13 - 内酯（1）、11α,12α - 环氧 - 3β - [(O - β - D - 吡喃半乳糖基 - (1→3) - O - [β - D - 吡喃葡萄糖基 - (1→2)] - β - D - 葡萄糖醛酸吡喃糖基)氧基]齐墩果 - 28,13 - 内酯（2）以及11α,12α - 环氧 - 3β - [(O - β - D - 葡萄糖醛酸吡喃糖基)氧基]蒲公英赛 - 14 - 烯 - 28 - 酸β - D - 吡喃葡萄糖基酯（3）。1 - 3带有环氧基的苷元（1a和3a）对HSC - 2人口腔鳞状癌细胞显示出细胞毒性活性。