Title of article :
Solanopubamine, a rare steroidal alkaloid from Solanum schimperianum: Synthesis of some new alkyl and acyl derivatives, their anticancer and antimicrobial evaluation
Author/Authors :
Al-Rehaily, Adnan J. King Saud University - College of Pharmacy - Department of Pharmacognosy, Saudi Arabia , Ahmad, Mohammad S. King Saud University - College of Pharmacy - Department of Pharmacognosy,, Saudi Arabia , Mustafa, Jamal King Saud University - College of Pharmacy - Department of Pharmacognosy, Saudi Arabia , Al-Oqail, Mai M. King Saud University - College of Pharmacy - Department of Pharmacognosy,, Saudi Arabia , Hassan, Wafaa H. King Saud University - College of Pharmacy - Department of Pharmacognosy, Saudi Arabia , Khan, Shabana I. University of Mississippi - National Center for Natural Product Research, School of Pharmacy, USA , Khan, Ikhlas A. King Saud University - College of Pharmacy - Department of Pharmacognosy, Saudi Arabia , Khan, Ikhlas A. University of Mississippi - School of Pharmacy, National Center for Natural Product Research, USA
Abstract :
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.
Keywords :
Solanum schimperianum , Solanaceae , Solanopubamine , Anticancer and antimicrobial activities
