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Synthesis of beta-hederin and Hederacolchiside A1: triterpenoid saponins bearing a unique cytotoxicity-inducing disaccharide moiety |
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| Authors: | Cheng Mao-Sheng Yan Mao-Cai Liu Yang Zheng Li-Gang Liu Jiao |
| Institution: | Key Lab of New Drugs Design and Discovery of Liaoning Province, School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, PR China. mscheng@syphu.edu.cn |
| Abstract: | A facile synthetic approach toward oleanolic acid glycoside bearing alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl moiety, a unique oligosaccharide that strongly induces antitumor activity of oleanane-type triterpenoid saponins, was developed. Based on this approach beta-hederin (oleanolic acid 3-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside) was efficiently prepared from oleanolic acid through stepwise glycosylation in linear eight steps with 52% overall yield, while Hederacolchiside A1 (oleanolic acid 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->4)]-alpha-L-arabinopyranoside) in linear 13 steps with 20% overall yield. |
| Keywords: | β-Hederin Hederacolchiside A1 l-Rhamnopyranosyl-(1→2)-α-l-arabinopyranoside" target="_blank">α-l-Rhamnopyranosyl-(1→2)-α-l-arabinopyranoside Cytotoxicity-inducing oligosaccharide Triterpenoid saponin Stepwise glycosylation |
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