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

Abstract EN

Solanopubamine (3b-amino-5a, 22aH, 25bH-solanidan-23b-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 -3b-NH2 and -23b-OH groups was achieved through methylation, acetylation or coupling with octadecanoic and undec 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 lg / mL.

Semi-synthesized compounds (2–7) have failed to show anti-tumor and anti-microbial activities.