Influence of hydroxyl substitution on flavanone antioxidants properties

Food Chem. 2017 Jan 15:215:501-7. doi: 10.1016/j.foodchem.2016.07.183. Epub 2016 Aug 3.

Abstract

The aim of our study was to determine the effect of the position of the hydroxyl group on the antioxidant properties of flavonoid derivatives. For this purpose, we performed electrochemical analysis and quantum-mechanical calculations to describe the mechanisms of electrochemical oxidation, and we selected the two methods of ABTS (2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) and DPPH (2,2-diphenyl-1-picryl-hydrazyl-hydrate), which allowed us to determine the ability to scavenge free radicals. On the basis of the research, we found that the derivatives of flavonoids, which have a hydroxyl group substituted at the R-3 position on the C ring, have outstanding antioxidant activity. Flavone, which had an OH group substituted at the R-6 and R-7 position on the ring A, showed similar antioxidant activity to flavone without -OH groups in the structure and slightly higher activity than the di-substituted flavone on the ring A.

Keywords: ABTS; Antioxidant; DPPH; Electrochemical oxidation; Flavones; UV–VIS.

MeSH terms

  • Antioxidants / chemistry*
  • Electrochemical Techniques / methods*
  • Flavanones / chemistry*
  • Hydroxyl Radical / chemistry*
  • Oxidation-Reduction

Substances

  • Antioxidants
  • Flavanones
  • Hydroxyl Radical
  • flavanone