Isolation of soluble epoxide hydrolase inhibitor of capsaicin analogs from Capsicum chinense Jacq. cv. Habanero

Int J Biol Macromol. 2019 Aug 15:135:1202-1207. doi: 10.1016/j.ijbiomac.2019.06.028. Epub 2019 Jun 6.

Abstract

Capsaicin (1) and dihydrocapsaicin (2) were isolated from the aerial parts of Capsicum chinense Jacq. cv. Habanero. In in vitro studies, the exhibited potent inhibitory activity against soluble epoxide hydrolase (sEH), with IC50 values of 5.6 ± 1.2 and 7.3 ± 0.7 μM. Enzyme kinetics suggested that the two compounds (1 and 2) were competitive inhibitors with Ki values of 2.5 ± 1.0 and 4.7 ± 2.3 μM, respectively. Molecular docking and molecular dynamic studies showed that capsaicin analogs (1 and 2) bound strongly with Asp335, Tyr383, and Tyr466 residues in the active site. These results suggest that the two inhibitors (1 and 2) represent potentially therapeutic inhibitors of sEH.

Keywords: Capsaicin analogs; Capsicum chinense; Molecular simulation; sEH inhibitor.

MeSH terms

  • Capsaicin / chemistry
  • Capsaicin / isolation & purification
  • Capsaicin / pharmacology*
  • Capsicum / chemistry*
  • Catalytic Domain
  • Enzyme Activation
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification
  • Enzyme Inhibitors / pharmacology*
  • Epoxide Hydrolases / antagonists & inhibitors
  • Epoxide Hydrolases / chemistry*
  • Hydrogen Bonding
  • Kinetics
  • Molecular Conformation
  • Molecular Docking Simulation
  • Molecular Dynamics Simulation
  • Molecular Structure
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology*
  • Solubility
  • Spectrum Analysis
  • Structure-Activity Relationship

Substances

  • Enzyme Inhibitors
  • Plant Extracts
  • Epoxide Hydrolases
  • Capsaicin