Why B-ring is the active center for genistein to scavenge peroxyl radical: a DFT study

Bioorg Med Chem Lett. 2003 Mar 10;13(5):909-11. doi: 10.1016/s0960-894x(03)00013-1.

Abstract

The structure-activity relationship for genistein to scavenge peroxyl radical was clarified by density functional theory (DFT) calculations using the B3LYP/6-31G(d,p) method. It was revealed that the conjugation of an electron-withdrawing 1,4-pyrone group with A-ring of genistein was not beneficial to enhance the radical-scavenging activities. Thus, hydroxyl in B-ring became the active center of genistein to scavenge peroxyl radical.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Free Radical Scavengers / chemistry
  • Free Radical Scavengers / pharmacology
  • Genistein / chemistry*
  • Genistein / pharmacology*
  • Hydroxides / chemistry
  • Models, Chemical
  • Peroxides / chemistry*
  • Pyrones / chemistry
  • Structure-Activity Relationship
  • Thermodynamics

Substances

  • Free Radical Scavengers
  • Hydroxides
  • Peroxides
  • Pyrones
  • perhydroxyl radical
  • Genistein