Facile synthesis and cytotoxicity of triterpenoid saponins bearing a unique disaccharide moiety: hederacolchiside A1 and its analogues.
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.
Yan
Mao-Cai
MC
Key Lab of New Drugs Design and Discovery of Liaoning Province, School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, PR China.
Liu
Yang
Y
Lu
Wen-Xiang
WX
Wang
Hui
H
Sha
Yu
Y
Cheng
Mao-Sheng
MS
D002470:Cell Survival / Q000187:drug effects; D004187:Disaccharides / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012503:Saponins / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000737:chemistry*
D004187:Disaccharides; D012503:Saponins; D014315:Triterpenes; C412406:hederacolchiside A