Mechanistic Insights into Myofibrillar Protein Oxidation by Fenton Chemistry Regulated by Gallic Acid

J Agric Food Chem. 2023 Aug 23;71(33):12587-12596. doi: 10.1021/acs.jafc.3c03284. Epub 2023 Aug 10.

Abstract

Gallic acid (GA, 3,4,5-trihydroxybenzoic acid) is a widely used natural food additive of interest to food chemistry researchers, especially regarding its effects on myofibrillar protein (MP) oxidation. However, existing studies regarding MP oxidation by GA-combined with Fenton reagents are inconsistent, and the detailed mechanisms have not been fully elucidated. This work validated hydroxyl radical (HO·) as the primary oxidant for MP carbonylation; in addition, it revealed three functions of GA in the Fenton oxidation of MP. By coordination with Fe(III), GA reduces Fe(III) to generate Fe(II), which is the critical reagent for HO· generation; meanwhile, the coordination improves the availability and reactivity of Fe(III) under weakly acidic and near-neutral pH, i.e., pH 4-6. Second, the intermediates formed during GA oxidation, including semiquinone and quinone, promoted Fenton reactivity by accelerating Fe catalytic cycling. Finally, GA can scavenge HO· radicals, thus exhibiting a certain degree of antioxidant property. All three functions contribute to MP oxidation as observed in GA-containing meat.

Keywords: Fenton reaction; antioxidant property; gallic acid; peroxidation; protein oxidation.

MeSH terms

  • Antioxidants / metabolism
  • Ferric Compounds* / chemistry
  • Gallic Acid* / chemistry
  • Hydrogen Peroxide / chemistry
  • Hydroxyl Radical
  • Oxidation-Reduction

Substances

  • Gallic Acid
  • Ferric Compounds
  • Antioxidants
  • Hydrogen Peroxide
  • Hydroxyl Radical