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  • 1.
    Fagerlund, Amelie
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Sunnerheim, Kerstin
    Dimberg, Lena H.
    Radical-scavenging and antioxidant activity of avenanthramides2009In: Food Chemistry, ISSN 0308-8146, E-ISSN 1873-7072, Vol. 113, no 2, p. 550-556Article in journal (Refereed)
    Abstract [en]

    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.

  • 2. Lee-Manion, M.
    et al.
    Price, K.
    Strain, J.
    Dimberg, H.
    Sunnerheim, Kerstin
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Welch, W.
    In Vitro Antioxidant Activity and Antigenotoxic Effects of Avenanthramides and Related Compounds2009In: Journal of Agricultural and Food Chemistry, ISSN 0021-8561, E-ISSN 1520-5118, Vol. 57, no 22, p. 10619-10624Article in journal (Refereed)
    Abstract [en]

    Avenanthramides are substituted N-cinnamoylanthranilic acids, with hydroxycinnamic acid and anthranilic acid moieties. These alkaloid phenols, which are unique to oats, may confer health benefits via antioxidant or other mechanisms. Synthetic avenanthramides, hydroxycinnamic acids, Tranilast, and ascorbic acid were evaluated for antioxidant activity using two assays, DPPH (2,2-diphenyl-1-picrylhydrazyl) and FRAP (ferric reducing antioxidant potential), and for antigenotoxicity using the Comet assay with stressed human adenocarcinoma colon cells. Of all the compounds tested, N-(3',4'-dihydroxy-(E)-cinnamoyl)-5-hydroxyanthranilic acid (2c), an abundant oat avenanthramide, generally had the highest activity in all three assays. The drug Tranilast showed antigenotoxic effects, but not antioxidant activity, suggesting that antigenotoxicity is not dependent on antioxidant effects. Overall, results show that avenanthramides exert antioxidant and antigenotoxic activities that are comparable to those of ascorbic acid and which have the potential to exert beneficial physiological effects.

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