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Synthesis 2006(5): 775-782  
DOI: 10.1055/s-2006-926316
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of the Cytotoxic Gitogenin 3β-O-[2-O-(α-l-Rhamnopyranosyl)-β-d-galactopyranoside] and its Congeners

Yingxia Li*a, Yichun Zhanga, Tiantian Guoa, Huashi Guana, Yan Haob, Biao Yu*b
a Key Laboratory of Marine Drugs, The Ministry of Education of China, Marine Drug and Food Institute, Ocean University of China, Qingdao 266003, P. R. of China
e-Mail: liyx417@ouc.edu.cn; e-Mail: byu@mail.sioc.ac.cn ;
b State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
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Publication History

Received 20 July 2005
Publication Date:
07 February 2006 (online)

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Abstract

(25R)-5a-Spirostan-2a,3b-diol (gitogenin) 3β-O-[2-O-(α-l-rhamnopyranosyl)-β-d-galactopyranoside] (1), a cytotoxic spirostan saponin isolated from the underground parts of Hosta longipes (Liliaceae), was concisely synthesized. In this context, its congeners 2-4 were also prepared. All four compounds showed comparable potency to dioscin in inhibition against the growth of tumor cells.

Key words

gitogenin 3β-O-[2-O-(α-l-rhamnopyranosyl)-β-d-galactopyranoside] - saponin - chacotrioside - synthesis - antitumor