Antioxidant properties of (-)-epicatechin-3-gallate and its inhibition of Cr(VI)-induced DNA damage and Cr(IV)- or TPA-stimulated NF-kappaB activation

Mol Cell Biochem. 2000 Mar;206(1-2):125-32. doi: 10.1023/a:1007012403691.

Abstract

Electron spin resonance (ESR) spin trapping was utilized to investigate the scavenging effects on hydroxyl radicals (*OH) and superoxide radicals (O2*-) by (-)-epigallocatechin-3-gallate (EGCG), one of the major anticancer compounds in tea. The spin trap used was 5,5-dimethyl-pyrroline N-oxide (DMPO). The Fenton reaction (Fe2+ + H2O2-->Fe3+ + *OH + OH-) was used as a source of *OH radicals. EGCG efficiently scavenges *OH radicals with reaction rate of 4.62 x 10(11) M(-1)sec(-1), which is an order of magnitude higher than several well recognized antioxidants, such as ascorbate, glutathione and cysteine. It also scavenges O2*- radicals as demonstrated by using xanthine and xanthine oxidase system as a source of O2*- radicals. Through its antioxidant properties, EGCG exhibited a protective effect against DNA damage induced by Cr(VI). EGCG also inhibited activation of nuclear transcription factor NF-kappaB induced by Cr(IV) and 12-o-tetradecanoylphorbol-13-acetate (TPA). The present studies provide a mechanistic basis for the reported anticarcinogenic properties of EGCG and related tea products.

MeSH terms

  • Antioxidants / pharmacology*
  • Catechin / analogs & derivatives*
  • Catechin / pharmacology*
  • Cells, Cultured
  • Chromates / antagonists & inhibitors*
  • Chromates / pharmacology
  • Chromium / antagonists & inhibitors*
  • Chromium / pharmacology
  • DNA Damage / drug effects*
  • Electron Spin Resonance Spectroscopy
  • Electrophoresis, Polyacrylamide Gel
  • Free Radical Scavengers
  • Humans
  • Hydroxyl Radical / metabolism
  • Jurkat Cells / metabolism
  • NF-kappa B / metabolism*
  • Superoxides / metabolism
  • Tetradecanoylphorbol Acetate / antagonists & inhibitors*
  • Tetradecanoylphorbol Acetate / pharmacology

Substances

  • Antioxidants
  • Chromates
  • Free Radical Scavengers
  • NF-kappa B
  • Chromium
  • Superoxides
  • chromium hexavalent ion
  • Hydroxyl Radical
  • Catechin
  • epicatechin gallate
  • Tetradecanoylphorbol Acetate