Substituent inductive effects on the electrochemical oxidation of flavonoids studied by squarewave voltammetry and ab initio calculations

Netzahualcoyotl Arroyo-Curras, Víctor M. Rosas-García, Marcelo Videa

Research output: Contribution to journalArticle

Abstract

Flavonoids are natural products commonly found in the human diet that show antioxidant, anti-inflammatory and anti-hepatotoxic activities. These nutraceutical properties may relate to the electrochemical activity of flavonoids. To increase the understanding of structure-electrochemical activity relations and the inductive effects that OH substituents have on the redox potential of flavonoids, we carried out square-wave voltammetry experiments and ab initio calculations of eight flavonoids selected following a systematic variation in the number of hydroxyl substituents and their location on the flavan backbone: three flavonols, three anthocyanidins, one anthocyanin and the flavonoid backbone flavone. We compared the effect that the number of -OH groups in the ring B of flavan has on the oxidation potential of the flavonoids considered, finding linear correlations for both flavonols and anthocyanidins (R2 = 0.98). We analyzed the effects that position and number of -OH substituents have on electron density distributions via ab initio quantum chemical calculations. We present direct correlations between structural features and oxidation potentials that provide a deeper insight into the redox chemistry of these molecules.

Original languageEnglish (US)
Article number1422
JournalMolecules
Volume21
Issue number11
DOIs
Publication statusPublished - Nov 1 2016

    Fingerprint

Keywords

  • Ab initio
  • Antioxidants
  • Electron density distribution
  • Flavonoids
  • Voltammetry

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this