Facile synthesis of saponins containing 2,3-branched oligosaccharides by using partially protected glycosyl donors.
Two natural saponins 1 and 2, isolated from Solanum indicum L., and containing 2,3-branched sugar moieties, have been efficiently synthesized. Partially protected monosaccharide and disaccharide donors were used to facilitate target synthesis. Stereo factors were critical in incorporating 2,3-branched sugars on steroid aglycones. Saponin 1 was synthesized in five steps and 30% overall yield, while saponin 2 was obtained using six straightforward sequential reactions in 31% overall yield. Saponin 2 shows promising cytotoxic activity toward human hepatocellular carcinoma BEL-7402 with an IC50 of <6 microg/mL.
Gu
Guofeng
G
Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China.
Du
Yuguo
Y
Linhardt
Robert J
RJ
D000972:Antineoplastic Agents, Phytogenic / Q000032:analysis / Q000138:chemical synthesis* / Q000494:pharmacology; D004144:Diosgenin / Q000031:analogs & derivatives / Q000032:analysis / Q000138:chemical synthesis* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006031:Glycosylation; D006801:Humans; D020128:Inhibitory Concentration 50; D008516:Medicine, Chinese Traditional; D015394:Molecular Structure; D009844:Oligosaccharides / Q000737:chemistry*; D012503:Saponins / Q000032:analysis / Q000138:chemical synthesis* / Q000494:pharmacology; D032322:Solanum / Q000737:chemistry*; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured
D000972:Antineoplastic Agents, Phytogenic; D009844:Oligosaccharides; D012503:Saponins; C489113:diosgenyl 3-O-(alpha-L-rhamnopyranosyl-(1-2)-(beta-D-xylopyranosyl-(1-3))-beta-D-galactopyranoside); D004144:Diosgenin