Iron chelation by the powerful antioxidant flavonoid quercetin

J Agric Food Chem. 2006 Aug 23;54(17):6343-51. doi: 10.1021/jf060986h.

Abstract

Chelation of the bare and hydrated iron(II) cation by quercetin has been investigated at the DF/B3LYP level in the gas phase. Several complexed species arising from neutral and anionic forms of the ligand have been taken into account. Both 1:1 and 1:2 metal/flavonoid stoichiometries have been considered. Results indicate that among the potential sites of chelation present on quercetin, the oxygen atoms belonging to the 3-hydroxy and 4-oxo, and to the 5-hydroxy and 4-oxo groups, are the preferred ones. Time-dependent density functional theory (TDDFT) calculations, used to reproduce the electronic UV-vis spectra of isolated quercetin and its complexes with Fe2+, were also performed in methanol and dimethylsulfoxide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / chemistry*
  • Cations
  • Dimethyl Sulfoxide
  • Ferrous Compounds / chemistry*
  • Iron Chelating Agents / chemistry*
  • Methanol
  • Models, Molecular
  • Quercetin / chemistry*
  • Spectrophotometry

Substances

  • Antioxidants
  • Cations
  • Ferrous Compounds
  • Iron Chelating Agents
  • Quercetin
  • Methanol
  • Dimethyl Sulfoxide