Efficient one-pot synthesis of tigogenin saponins and their antitumor activities.
An efficient synthesis of naturally occurring tigogenin triglycoside 1a and its three derivatives 1b-d bearing different carbohydrate moieties, as well as their antitumor activities, is described. Partially protected thiogalactosides bearing unprotected 2,4-OH or 4-OH groups were used to facilitate regioselective reactions for one-pot sequential multi-step glycosylation, which has significantly simplified the target molecule synthesis. The synthetic saponins 1a-d exhibited much higher anti-tumor activities than the positive control cisplatin against the human epithelial cervical cancer cell (HeLa) as evaluated by CCK-8 assay.
National Glycoengineering Research Center, Shandong University, Jinan 250010, PR China. Electronic address: guofenggu@sdu.edu.cn.
Guofeng
G
Gu
National Glycoengineering Research Center, Shandong University, Jinan 250010, PR China.
Lian
L
An
National Glycoengineering Research Center, Shandong University, Jinan 250010, PR China.
Min
M
Fang
National Glycoengineering Research Center, Shandong University, Jinan 250010, PR China. Electronic address: zwguo@sdu.edu.cn.
Zhongwu
Z
Guo
D049109:Cell Proliferation / Q000187:drug effects*; D002945:Cisplatin / Q000494:pharmacology; D005260:Female; D006031:Glycosylation / Q000187:drug effects; D006367:HeLa Cells; D006801:Humans; D012503:Saponins / Q000138:chemical synthesis* / Q000494:pharmacology; D013150:Spirostans / Q000138:chemical synthesis* / Q000494:pharmacology; D013862:Thiogalactosides / Q000138:chemical synthesis / Q000494:pharmacology; D014280:Triglycerides / Q000138:chemical synthesis* / Q000494:pharmacology; D002583:Uterine Cervical Neoplasms / Q000188:drug therapy / Q000473:pathology
D012503:Saponins; D013150:Spirostans; D013862:Thiogalactosides; D014280:Triglycerides; C046297:sarsasapogenin; D002945:Cisplatin
Antitumor activity; One-pot sequential glycosylation; Saponin; Thioglycoside