Constituents of the seeds of Cassia tora with inhibitory activity on soluble expoxide hydrolease

Bioorg Med Chem Lett. 2015 Nov 15;25(22):5097-101. doi: 10.1016/j.bmcl.2015.10.014. Epub 2015 Oct 8.

Abstract

Efforts to extract soluble epoxide hydrolase (sEH) inhibitors from food sources through bioactivity-guided fractionation of Cassia tora seed extracts led to the isolation of one new compound, 1, and 15 known compounds, 2-16. Structural elucidations were performed using 1D/2D NMR spectroscopy and mass spectrometry. Compounds 1, 3, 4, 6, 10, 11, and 13-16 exhibited inhibitory activities on sEH with IC50 values of 2.2±2.1-40.6±3.4 μM. Compound 13 was particularly active and exhibited a reversible-uncompetitive behavior in enzyme kinetic studies. A binding site on the enzyme for compound 13 was also predicted by Autodock 4.2 simulations.

Keywords: Cassia tora; Leguminosae; Molecular docking; Soluble epoxide hydrolase; Uncompetitive behavior.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anthraquinones / isolation & purification
  • Anthraquinones / pharmacology*
  • Cassia
  • Enzyme Inhibitors / isolation & purification
  • Enzyme Inhibitors / pharmacology*
  • Epoxide Hydrolases / antagonists & inhibitors*
  • Fluorometry
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Molecular Docking Simulation
  • Seeds

Substances

  • Anthraquinones
  • Enzyme Inhibitors
  • cassitoroside
  • Epoxide Hydrolases