Synthesis of beta-hederin and Hederacolchiside A1: triterpenoid saponins bearing a unique cytotoxicity-inducing disaccharide moiety.
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.
Cheng
Mao-Sheng
MS
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
Yan
Mao-Cai
MC
Liu
Yang
Y
Zheng
Li-Gang
LG
Liu
Jiao
J
D000970:Antineoplastic Agents / Q000737:chemistry*; D001089:Arabinose / Q000031:analogs & derivatives; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis*; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D012210:Rhamnose / Q000031:analogs & derivatives; D012503:Saponins / Q000138:chemical synthesis* / Q000737:chemistry
D000970:Antineoplastic Agents; D004187:Disaccharides; D012503:Saponins; C010177:beta-hederin; C412406:hederacolchiside A; D009828:Oleanolic Acid; D001089:Arabinose; D012210:Rhamnose