Facile synthesis and cytotoxicity of triterpenoid saponins bearing a unique disaccharide moiety: hederacolchiside A1 and its analogues |
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Authors: | Yan Mao-Cai Liu Yang Lu Wen-Xiang Wang Hui Sha Yu Cheng Mao-Sheng |
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Affiliation: | Key Lab of New Drugs Design and Discovery of Liaoning Province, School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, PR China. |
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Abstract: | An improved synthetic approach toward hederacolchiside A1, an antitumor triterpenoid saponin bearing a unique disaccharide moiety, was established. This approach began from a partially protected intermediate and avoided tedious protection-deprotection manipulation. An abnormal ring conformation (1C4) of the center arabinose residue was found in the intermediate, which may account for the unusual regioselectivity between 3-OH and 4-OH of arabinose. Two analogues of hederacolchiside A1 were then facilely prepared by this approach and exhibited significant cytotoxicity in preliminary in vitro assay. |
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Keywords: | Hederacolchiside A1 Triterpenoid saponin Cytotoxicity Regioselective glycosylation 1C4 conformation Arabinose |
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