The Structure-Antioxidant Activity Relationship of Ferulates

Molecules. 2017 Mar 25;22(4):527. doi: 10.3390/molecules22040527.

Abstract

The antioxidant activity of ferulic acid (1), iso-ferulic acid (2), coniferyl aldehyde (3), methyl ferulate (4), and ethyl ferulate (5) were investigated using 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and ferric-reducing antioxidant power (FRAP) assays and autoxidation of triacylglycerols of commercially available sunflower oil (TGSO). The compounds tested for ability to scavenge ABTS radical cations was in the order of ferulic acid > coniferyl aldehyde ≈ iso-ferulic acid > ethyl ferulate ≈ methyl ferulate. The results of the FRAP assay for ferulic acid, iso-ferulic acid, and coniferyl aldehyde were similar to and higher than those of methyl ferulate and ethyl ferulate. In the lipid system, iso-ferulic acid showed weak antioxidant activity. The other ferulates exhibited much stronger, yet similar, activities.

Keywords: 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS); antioxidant activity; ferric-reducing antioxidant power (FRAP); ferulates; lipid oxidation; structure.

MeSH terms

  • Acrolein / analogs & derivatives*
  • Acrolein / chemistry
  • Acrolein / pharmacology
  • Antioxidants / chemistry*
  • Antioxidants / pharmacology
  • Caffeic Acids / chemistry*
  • Caffeic Acids / pharmacology
  • Coumaric Acids / chemistry*
  • Coumaric Acids / pharmacology
  • Molecular Structure
  • Oxidation-Reduction
  • Structure-Activity Relationship

Substances

  • Antioxidants
  • Caffeic Acids
  • Coumaric Acids
  • coniferaldehyde
  • ethyl ferulate
  • Acrolein
  • ferulic acid
  • methyl ferulate