Solanopubamine, a rare steroidal alkaloid from Solanum schimperianum: Synthesis of some new alkyl and acyl derivatives, their anticancer and antimicrobial evaluation

Solanopubamine (3β-amino-5α, 22αh, 25βh-solanidan-23β-ol), a steroidal alkaloid was isolated from the alkaloidal fraction of solanum schimperianum in significant yield. its structure was established by ir, positive esi-ms, 1d and 2d nmr. the presence of -3β-nh2 and -23β-oh groups was achieved through methylation, acetylation or coupling with octadecanoic and undec-11-enoic acids to produce six derivatives (2–7). their structures were confirmed by spectroscopic analyses. solanopubamine and semi-synthetic analogs are investigated for their in vitro cytotoxicity against a panel of human cancer cell lines and anti-microbial activity. solanopubamine showed good antifungal activity only against candida albicans and c. tenuis with mic of 12.5 μg/ml. semi-synthesized compounds (2–7) have failed to show anti-tumor and anti-microbial activities.