1. School of Pharmaceutical Science and National Glycoengineering Research Center , Shandong University , Jinan , 250100 , PR China;2. The State Key Laboratory of Microbial Technology , Shandong University , Jinan , 250100 , PR China
Abstract:
An efficient synthesis of timosaponin AIII (TAIII) and five structurally modified analogs via a one-pot sequential glycosylation strategy is described. A partially protected D-galactopyranosyl thioglycoside was employed for regioselective glycosylation to facilitate the target synthesis. The antitumor activities of the synthetic saponins against human epithelial cervical cancer cell (HeLa) were preliminarily evaluated by means of CCK-8 assay. An L-rhamnosyl analog was discovered to display stronger inhibitory activity (IC50 3.3 μM) than TAIII (IC50 10.7 μM) to HeLa cell. Supplemental materials are available for this article. Go to the publisher's online edition of Journal of Carbohydrate Chemistry to view the free supplemental file.