Synthesis and evaluation of acetylferulic paeonol ester and ferulic paeonol ester as potential antioxidants to inhibit fish oil oxidation

Food Chem. 2021 Dec 15:365:130384. doi: 10.1016/j.foodchem.2021.130384. Epub 2021 Jun 16.

Abstract

Acetylferulic paeonol ester (APE) and ferulic paeonol ester (FPE) were synthesized, and their structures were confirmed by NMR, mass spectra, IR and UV-vis data. The antioxidant properties of the synthesized compounds were evaluated using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and [(2-azino-bis (3-ethylbenzthiazoline)-6 -sulfonic acid] (ABTS) assay as well as the production of oxidation products (peroxides, conjugated dienes, thiobarbituric acid-reactive substances, free fatty acids and total aldehydes) in an elevated temperature (60 °C) storage trial of fish oil extracted from anchovy. Furthermore, the changes in fatty acid composition were monitored by gas chromatography-mass spectrometry. The results showed that APE was more effective in restraining fish oil oxidation compared to FPE, ferulic acid, paeonol and the commercial antioxidant-butylated hydroxytoluene (BHT). This study demonstrated molecular combinations obtained by covalent bonding two antioxidant active molecules can result in novel compounds with enhanced antioxidant activities.

Keywords: Antioxidant; Fatty acid; Ferulic acid; Fish oil; Paeonol; Radical scavenging.

MeSH terms

  • Acetophenones
  • Antioxidants*
  • Butylated Hydroxytoluene
  • Esters
  • Fish Oils*

Substances

  • Acetophenones
  • Antioxidants
  • Esters
  • Fish Oils
  • Butylated Hydroxytoluene
  • paeonol