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

Bioorg Med Chem Lett. 2008 Apr 15;18(8):2619-23. doi: 10.1016/j.bmcl.2008.03.028. Epub 2008 Mar 14.

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-kappaB inhibition, and O-methyl and O-ethylbakuchiols (6 and 7) inhibited HIF-1 and NF-kappaB activation without significantly decreasing the viability of the AGS and HeLa cells, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line, Tumor
  • Humans
  • Hypoxia-Inducible Factor 1 / antagonists & inhibitors*
  • Hypoxia-Inducible Factor 1 / metabolism
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • NF-kappa B / antagonists & inhibitors*
  • NF-kappa B / metabolism
  • Phenols / chemistry*
  • Phenols / pharmacology*
  • Psoralea / chemistry*
  • Seeds / chemistry
  • Structure-Activity Relationship
  • Terpenes / chemistry*

Substances

  • Hypoxia-Inducible Factor 1
  • NF-kappa B
  • Phenols
  • Terpenes
  • bakuchiol