Synthesis of gypsogenin and gypsogenic acid derivatives with antitumor activity by damaging cell membranes†
Forty-five gypsogenin and gypsogenic acid derivatives were synthesized and screened for their cytotoxic activities. Their structures were established using IR, 1H NMR, 13C NMR, and LC-MS spectroscopic data, and they were subjected to extensive biological testing. In the MTT assays, nearly all the compounds displayed good cytotoxicity in the low μM range for several human tumor cell lines (A549, MC3-8, TE-1, HepG-2 and MCF-7). The preliminary bioassay test suggested that most of these gypsogenin and gypsogenic acid derivatives showed different degrees of antitumor activities. In particular, some compounds displayed moderate antitumor activity. They were shown to destroy cell membranes and increase their permeability, which led to the outflow of intracellular nucleic acid.