In vitro metabolism of obovatol and its effect on cytochrome P450 enzyme activities in human liver microsomes

Biopharm Drug Dispos. 2013 May;34(4):195-202. doi: 10.1002/bdd.1837. Epub 2013 Mar 26.

Abstract

Obovatol, a major constituent of the leaves of Magnolia obovata Thunb, is known to inhibit nuclear factor-κB activity and arachidonic acid-induced platelet aggregation. This study was performed to identify the metabolites of obovatol in human liver microsomes. Human liver microsomes incubated with obovatol in the presence of NADPH and/or UDPGA resulted in the formation of six metabolites, M1-M6. M1 and M2 were identified as hydroxyobovatol, on the basis of liquid chromatography/tandem mass spectrometric (LC-MS/MS) analysis. M1, M2 and obovatol were further metabolized to their glucuronide conjugates, obovatol-glucuronide (M3), obovatol-diglucuronide (M4) and hydroxyobovatol-glucuronide (M5 and M6). The inhibitory potency of obovatol on eight major human P450s was also investigated in human liver microsomes. In these experiments, obovatol strongly inhibited CYP2C19-mediated S-mephenytoin hydroxylase activity with an IC(50) value of 0.8 µM, which could have implications for drug-drug interactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aryl Hydrocarbon Hydroxylases / metabolism
  • Chromatography, Liquid
  • Cytochrome P-450 CYP2C19
  • Cytochrome P-450 Enzyme System / drug effects*
  • Cytochrome P-450 Enzyme System / metabolism
  • Humans
  • Inhibitory Concentration 50
  • Magnolia / chemistry
  • Microsomes, Liver / enzymology*
  • NADP / metabolism
  • Phenyl Ethers / administration & dosage
  • Phenyl Ethers / metabolism
  • Phenyl Ethers / pharmacology*
  • Tandem Mass Spectrometry
  • Uridine Diphosphate Glucuronic Acid / metabolism

Substances

  • Phenyl Ethers
  • Uridine Diphosphate Glucuronic Acid
  • NADP
  • obovatal
  • Cytochrome P-450 Enzyme System
  • Aryl Hydrocarbon Hydroxylases
  • CYP2C19 protein, human
  • Cytochrome P-450 CYP2C19