New cytotoxic withanolides from Physalis peruviana

Abstract

Investigation of the extracts of Physalis peruviana L. has led to the isolation of seven new withanolides, phyperunolide A (1), phyperunolide B (2), phyperunolide C (3), phyperunolide D (4), peruvianoxide (5), phyperunolide E (16), and phyperunolide F (17) together with ten known withanolides. The structure and absolute stereochemistry of all compounds were elucidated on the basis of CD and NMR spectral analysis, respectively. Compounds 1, 6, 7, and 9 showed cytotoxicity against lung cancer (A549), breast cancer (MDA-MB-231 and MCF7), and liver cancer (Hep G2 and Hep 3B) cancer cell lines. The presence of 5β,6β-epoxy-2-en-1-ones in withanolides is greatly helpful in cytotoxicity, it is a key known important factor to cytotoxicity; however, interestingly, the unusual 5-chloride withanolide, 9, displayed significant activity. © 2009 Elsevier Ltd. All rights reserved.