Abstract

Avenanthramides are amides of cinnamoyl-anthranilic acids and, among cereals, are exclusively found in oats. This study investigated the structure-antioxidant activities of 15 avenanthramides with different substitution patterns in the two aromatic rings, seven of which were new avenanthramides synthesised and characterised in this study. Radical-scavenging activity was tested as reactivity towards 1,1-diphenyl-2-picrylhydrazyl (DPPH(-)). The activity increased with the number of radical-stabilising groups ortho to the phenolic hydroxy group. Both aromatic rings were independently important for activity, while conjugation across the amide bond was of minor importance. Antioxidant activity was determined as inhibition of linoleic acid oxidation. In contrast to the radical-scavenging activity, antioxidant activity was observed for most avenanthramides, and also for compounds with only one hydroxy group in either of the aromatic rings. Compared with alpha-tocopherol, the avenanthramides protected linoleic acid from oxidation to a smaller extent initially, but the effect lasted for a longer time. (C) 2008 Elsevier Ltd. All rights reserved.

Keywords

Antioxidants; Avenanthramides; 1,1-Diphenyl-2-picrylhydrazyl; DPPH; Linoleic acid; Oats

Published in

Food Chemistry
2009, Volume: 113, number: 2, pages: 550-556
Publisher: ELSEVIER SCI LTD

SLU Authors

• Dimberg, Lena

  • Department of Molecular Sciences, Swedish University of Agricultural Sciences
    

UKÄ Subject classification

Food Science


Publication identifier

DOI: https://doi.org/10.1016/j.foodchem.2008.07.101

Permanent link to this page (URI)

https://res.slu.se/id/publ/44526