Avenanthramides in Oats (Avena sativa L.) and structure-antioxidant activity relationsships

Abstract

Eight avenanthramides, amides of anthranilic acid (1) and 5-hydroxyanthranilic acid (2), respectively, and the four cinnamic acids p-coumaric (p), caffeic (c), ferulic (f), and sinapic (s) acid, were synthesized for identification in oat extracts and for structure-antioxidant activity studies. Three compounds (2p, 2c, and 2f) were found in oat extracts. As assessed by the reactivity toward 1,1-diphenyl-2-picrylhydrazyl (DPPH), all avenanthramides except 1 p showed activity. Initially, the antioxidant activity of the avenanthramides decreased in a similar order as for the corresponding cinnamic acids, that is: sinapic > caffeic > ferulic > p-coumaric acid. The avenanthramides derived from 2 were usually slightly more active than those derived from 1. All avenanthramides inhibited azo-initiated peroxidation of linoleic acid. 1c and 1s were initially the most effective compounds. The relative order of antioxidant activities was slightly different for the DPPH and the linoleic acid assays run in methanol and chlorobenzene, respectively

Keywords

Avena sativa; avenanthramide; caffeic acid; cinnamic acid; p-coumaric acid; dehydrodicinnamic acid dilactone; DPPH; ferulic acid; radical scavengers; sinapic acid

Published in

Journal of Agricultural and Food Chemistry
2003, Volume: 51, number: 3, pages: 594-600 Publisher: American Chemical Society

SLU Authors

• Andersson, Rolf

  • Department of Molecular Sciences, Swedish University of Agricultural Sciences
    

• Dimberg, Lena

  • Department of Molecular Sciences, Swedish University of Agricultural Sciences
    

UKÄ Subject classification

Food Science
Agricultural Science


Publication identifier

DOI: https://doi.org/10.1021/jf020544f

Permanent link to this page (URI)

https://res.slu.se/id/publ/520