Soluble Epoxide Hydrolase Inhibitory Activity of Components Isolated from Apios americana Medik

Molecules. 2017 Aug 30;22(9):1432. doi: 10.3390/molecules22091432.

Abstract

A new compound 1, 5-methoxy-2,5,7,4'-tetrahydroxy-coumaronochromone, along with seven known compounds (2-8), were isolated from Apios americana using open column chromatography. Their structures were established based on an analysis of 1D and 2D NMR, and MS spectra. Among these, two compounds 1 and 2 showed inhibitory activity on soluble epoxide hydrolase (sEH) at a concentration below 50 μM. The respective competitive (1) and mixed (2) inhibitors were revealed to have Ki values of 21.0 ± 0.8 and 14.5 ± 1.5 μM, based on the Dixon plot. The potential inhibitor (2) was visually presented in a predicted binding pose in the receptor by molecular docking. Additionally, molecular dynamics were performed for a detailed understanding of their complex by Gromacs 4.6.5 package.

Keywords: Apios americana; leguminosae; molecular simulation; sEH inhibitor.

MeSH terms

  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Epoxide Hydrolases / antagonists & inhibitors*
  • Fabaceae / chemistry*
  • Kinetics
  • Ligands
  • Magnetic Resonance Spectroscopy
  • Molecular Docking Simulation
  • Molecular Dynamics Simulation
  • Phytochemicals / chemistry
  • Phytochemicals / isolation & purification*
  • Phytochemicals / pharmacology*
  • Solubility

Substances

  • Enzyme Inhibitors
  • Ligands
  • Phytochemicals
  • Epoxide Hydrolases