Effect of interaction between phenolic compounds and copper ion on antioxidant and pro-oxidant activities

Toxicol In Vitro. 2011 Oct;25(7):1320-7. doi: 10.1016/j.tiv.2011.04.024. Epub 2011 May 10.

Abstract

Phenolic compounds are widely used in food and cosmetics to prevent undesirable oxidation. On the other hand, phenolic compounds are also strong reducing agents and under in vitro conditions and in the presence of copper ion, they can act as pro-oxidants. In this study, we conducted electron spin resonance (ESR) measurements for the increase in reactive oxygen species (ROS) in relation to their structure and interaction with transition metals. Moreover, the antioxidant activity was assessed with the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay, and the pro-oxidant effect of phenolic compounds on DNA damage was assessed by measuring 8-hydroxy-2'-deoxyguanosine (8-OHdG), which is effectively formed during oxidative damage. In conclusion, ortho-dihydroxyl groups that can chelate with Cu(2+) induce the greatest pro-oxidant activity. Moreover, the interaction between phenolic compounds and copper induced to H(2)O(2). The obtained results indicated that ROS participated in oxidative DNA damage induced by phenolic compounds in the presence of Cu(2+).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 8-Hydroxy-2'-Deoxyguanosine
  • Biphenyl Compounds
  • Copper / toxicity*
  • DNA / drug effects
  • DNA Damage
  • Deoxyguanosine / analogs & derivatives
  • Deoxyguanosine / analysis
  • Electron Spin Resonance Spectroscopy
  • Free Radical Scavengers / pharmacology*
  • Hydroxyl Radical / metabolism
  • Phenols / pharmacology*
  • Picrates

Substances

  • Biphenyl Compounds
  • Free Radical Scavengers
  • Phenols
  • Picrates
  • Hydroxyl Radical
  • Copper
  • 8-Hydroxy-2'-Deoxyguanosine
  • DNA
  • calf thymus DNA
  • 1,1-diphenyl-2-picrylhydrazyl
  • Deoxyguanosine