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Facile synthesis of saponins containing 2,3-branched oligosaccharides by using partially protected glycosyl donors.

ABSTRACT: 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.

SUBMITTER: Gu G

PROVIDER: S-EPMC4140558 | biostudies-literature | 2004 Aug

REPOSITORIES: biostudies-literature

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Facile synthesis of saponins containing 2,3-branched oligosaccharides by using partially protected glycosyl donors.

Gu Guofeng G Du Yuguo Y Linhardt Robert J RJ

The Journal of organic chemistry 20040801 16

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 ...[more]

PMID: 15287807

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