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Avenanthramides in Oats (Avena sativa L.) and Structure−Antioxidant Activity Relationships
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 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.
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Cited by
Chemistry and biochemistry of dietary polyphenols
Tsao, R. (2010) · Nutrients · doi:10.3390/nu2121231 · Cited by 2,415
Foti, M. C., Daquino, C., & Geraci, C. (2004) · The Journal of Organic Chemistry · doi:10.1021/jo035758q · Cited by 599
Mattila, P., Pihlava, J.-M., & Hellström, J. (2005) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf051437z · Cited by 567
Ayaz, A., Zaman, W., Radák, Z., & Gu, Y. (2024) · Antioxidants · doi:10.3390/antiox13040437 · Cited by 26
Metadata
- Authors
- Bratt, K., Sunnerheim, K., Bryngelsson, S., Fagerlund, A., Engman, L., Andersson, R. E., & Dimberg, L. H.
- Venue
- Journal of Agricultural and Food Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-01-01
- Volume
- 51
- Issue
- 3
- Pages
- 594-600
- ISSN
- 0021-8561 (ISSN-L)
- 1520-5118
- OpenAlex
- W2121415256
- Cited by
- 195
- References
- 0
- FWCI
- 2.58
- Type
- journal article
- Language
- en
- Open access
- closed
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- Bratt, K., Sunnerheim, K., Bryngelsson, S., Fagerlund, A., Engman, L., Andersson, R. E., & Dimberg, L. H. (2003). Avenanthramides in Oats (Avena sativa L.) and Structure−Antioxidant Activity Relationships. Journal of Agricultural and Food Chemistry. https://doi.org/10.1021/jf020544f
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