Hypoxia-inducible factor-1 and nuclear factor-kappa B inhibitory meroterpene analogues of bakuchiol, a constituent of the seeds of Psoralea corylifolia

Abstract

Two new meroterpenoids, 12,13-dihydro-12,13-dihydroxybakuchiol (2) and (12'S)-bisbakuchiol C (3), were isolated from the seeds of Psoralea corylifolia L. (Fabaceae). The structures of 2 and 3 were elucidated by spectroscopic and chemical methods. Six meroterpenoids isolated from P. corylifolia and three semi-synthetic analogues were evaluated for HIF-1 and NF-kappa B inhibition, and O-methyl and O-ethylbakuchiols (6 and 7) inhibited HIF-1 and NF-kappa B activation without significantly decreasing the viability of the AGS and HeLa cells, respectively. (c) 2008 Elsevier Ltd. All rights reserved.