Evaluation of the redox properties and anti/pro-oxidant effects of selected flavonoids by means of a DNA-based electrochemical biosensor

Anal Bioanal Chem. 2003 May;376(2):168-73. doi: 10.1007/s00216-003-1884-3. Epub 2003 Apr 24.

Abstract

Quercetin and rutin as well as catechin and epigallocatechin gallate were investigated, as widely distributed representatives of flavonols and flavanols, respectively, regarding their anti/pro-oxidant properties. The flavonoids are irreversibly oxidized at a dsDNA-modified screen-printed electrode within 0.368 to 0.449 V vs. SHE without binding to DNA. Using the DNA biosensor the detection scheme of a DNA prevention/degradation exploits the [Co(phen)(3)](3+) complex as an electrochemical DNA marker. Antioxidant activity of flavonoids was tested in a model cleavage mixture composed of 5 x 10(-7) mol L(-1) [Cu(phen)(2)](2+) as the catalyst, 1 x 10(-3) mol L(-1) ascorbic acid as the chemical reductant and atmospheric oxygen as the natural oxidant where reactive oxygen radicals are generated. The antioxidant activity increases with the concentration of flavonoids reaching a maximum where pro-oxidative behaviour becomes of importance. The pro-oxidant potency of flavonoids depends on the presence of atmospheric oxygen and follows the order quercetin>rutin>epigallocatechin gallate>catechin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / analysis
  • Antioxidants / chemistry*
  • Biosensing Techniques / methods*
  • Catechin / analogs & derivatives*
  • Catechin / analysis
  • Catechin / chemistry
  • DNA / chemistry*
  • Electrochemistry / methods*
  • Flavonoids / analysis
  • Flavonoids / chemistry*
  • Molecular Structure
  • Oxidants / analysis
  • Oxidants / chemistry*
  • Oxidation-Reduction
  • Quercetin / analysis
  • Quercetin / chemistry
  • Rutin / analysis
  • Rutin / chemistry

Substances

  • Antioxidants
  • Flavonoids
  • Oxidants
  • Rutin
  • Catechin
  • DNA
  • Quercetin
  • epigallocatechin gallate