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Avenanthramides in Oats (Avena Sativa L.) and Structure-Activity Relationships
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
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2003 (English)In: Journal of Agricultural and Food Chemistry, ISSN 0021-8561, E-ISSN 1520-5118, Vol. 51, no 3, p. 594-600Article in journal (Refereed) Published
Abstract [en]

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 1p 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.

Place, publisher, year, edition, pages
2003. Vol. 51, no 3, p. 594-600
Keywords [en]
Avena sativa; avenanthramide; caffeic acid; cinnamic acid; p-coumaric acid; dehydrodicinnamic acid dilactone; DPPH; ferulic acid; radical scavengers; sinapic acid
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:miun:diva-12812DOI: 10.1021/jf020544fOAI: oai:DiVA.org:miun-12812DiVA, id: diva2:378272
Available from: 2010-12-15 Created: 2010-12-15 Last updated: 2017-12-11Bibliographically approved
In thesis
1. Naturally occurring phenols with antioxidant, antifungal and anti-browsing activity
Open this publication in new window or tab >>Naturally occurring phenols with antioxidant, antifungal and anti-browsing activity
2014 (English)Doctoral thesis, comprehensive summary (Other academic)
Place, publisher, year, edition, pages
Sundsvall: Mid Sweden University, 2014. p. 68
Series
Mid Sweden University doctoral thesis, ISSN 1652-893X ; 198
National Category
Chemical Sciences
Identifiers
urn:nbn:se:miun:diva-24028 (URN)978-91-87557-77-4 (ISBN)
Public defence
2014-09-26, 11:00
Supervisors
Available from: 2015-01-02 Created: 2015-01-02 Last updated: 2015-03-13Bibliographically approved

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Sunnerheim, KerstinFagerlund, Amelie

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