Selective inhibition of monoamine oxidase A by hispidol

Bioorg Med Chem Lett. 2018 Feb 15;28(4):584-588. doi: 10.1016/j.bmcl.2018.01.049. Epub 2018 Jan 31.

Abstract

Hispidol, an aurone, isolated from Glycine max Merrill, was found to potently and selectively inhibit an isoform of recombinant human monoamine oxidase-A (MAO-A), with an IC50 value of 0.26 µM, and to inhibit MAO-B, but with lower potency (IC50 = 2.45 µM). Hispidol reversibly and competitively inhibited MAO-A with a Ki value of 0.10 µM with a potency much greater than toloxatone (IC50 = 1.10 µM), a marketed drug. It also reversibly and competitively inhibited MAO-B (Ki = 0.51 µM). Sulfuretin, an analog of hispidol, effectively inhibited MAO-A (IC50 = 4.16 µM) but not MAO-B (IC50 > 80 µM). A comparison of their chemical structures showed that the 3'-hydroxyl group of sulfuretin might reduce its inhibitory activities against MAO-A and MAO-B. Flexible docking simulation revealed that the binding affinity of hispidol for MAO-A (-9.1 kcal/mol) was greater than its affinity for MAO-B (-8.7 kcal/mol). The docking simulation showed hispidol binds to the major pocket of MAO-A or MAO-B. The findings suggest hispidol is a potent, selective, reversible inhibitor of MAO-A, and that it be considered a novel lead compound for development of novel reversible inhibitors of MAO-A.

Keywords: Hispidol; Molecular docking; Monoamine oxidase A; Selective competitive inhibitor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzofurans / chemistry*
  • Binding Sites
  • Clorgyline / chemistry
  • Flavonoids / chemistry
  • Humans
  • Inhibitory Concentration 50
  • Kinetics
  • Molecular Docking Simulation
  • Monoamine Oxidase / chemistry
  • Monoamine Oxidase Inhibitors / chemistry*
  • Oxazolidinones / chemistry
  • Picolinic Acids / chemistry

Substances

  • Benzofurans
  • Flavonoids
  • Monoamine Oxidase Inhibitors
  • Oxazolidinones
  • Picolinic Acids
  • lazabemide
  • toloxatone
  • Monoamine Oxidase
  • monoamine oxidase A, human
  • Clorgyline
  • sulfuretin