Glycosidal Structure Modification And Evaluation In Vitro Cytotoxicity Of The Glycoside Of Solamargine

Solasodine—the glycoside of solamargine shows various biological activities. Therefor, the structure of solasodine was modified with a series of monosaccharides, and the in vitro cytotoxicity of monosaccharidal derivatives of solasodine was also evaluated.Herein,5a,5b,5c,5d,5e and 5f were synthesized respectively starting from monosaccharides D-(+)-Glucose (la), D-Galactose (lb), L-(+)-Rhamnose (1c), D-(+)-Glucosamine hydrochloride (1d), L (+)-Arabinose (le) and D-(+)-Xylose (1f) by four steps including benzoylation of monosaccharides, bromination of fully benzoylated monosaccharide 2a,2b,2c,2d,2e and 2f, glycosidation of partly benzoylated monosaccharide bromides 3a,3b,3c,3d,3e and 3f with solasodine and hydrolysis of partly benzoylated monosaccharide glycosides of solasodine 4a,4b,4c,4d,4e and 4f.The in vitro cytotoxicity of 5a,5b,5c,5d,5e and 5f against five tumor cell lines, A549, QGY7703, HL60, Colon205, MDA-MD-435 (231) was evaluated. The result showed that 5d was more potent than 5a,5b,5c,5e and 5f against the tested five tumor cell lines. The IC50 (μg/ml) values of 5d against the tested five tumor cell lines were 9.94,13.35,11.55,5.03 and 5.60 (231) respectively. The synthesis of 5d,5e and their cytotoxicity against the tested five tumor cell lines was firstly reported.