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Research article - Peer-reviewed, 2020

Avenanthramides as lipoxygenase inhibitors

Landberg, Rikard; Sunnerheim, Kerstin; Dimberg, Lena H.

Abstract

Avenanthramides (AVAs) present in oats are amides of anthranilic and cinnamic acids. AVAs are potent antioxidants and have anti-inflammatory properties. There are various potential mechanisms for their anti-inflammatory effects, including inhibition of lipoxygenases (LOX), which catalyse oxygenation of polyunsaturated fatty acids into potent signal molecules involved in inflammatory processes. In this study, AVAs were screened for LOX inhibition in vitro and structure-activity relationships were examined. Twelve different AVAs at 0.6 mM were tested as LOX inhibitors. The corresponding free cinnamic acids, the AVA analogue Tranilast (R) and the known LOX inhibitor trans-resveratrol were included for comparison. It was found that AVAs comprising caffeic or sinapic acid exhibited significant lipoxygenase inhibition (60-90%) (P < 0.05), whereas low or no inhibition was observed with AVAs containing p-coumaric or ferulic acid. No difference in inhibition was seen on comparing AVAs with their free corresponding cinnamic acids, which implies that the anthranilic acid part of the avenanthramide molecule does not affect inhibition. Trans-resveratrol showed inhibition, whereas no inhibition was seen for Tranilast (R) at the concentrations used in this study. This study suggests that aventahtramides comprising caffeic acid or sinapic acid partly exert their antioxidant and anti-inflammatory effects via lipoxygenase inhibition.

Keywords

Food science; Food analysis; Pharmaceutical chemistry; Pharmaceutical science; Phenol; Oats; Cinnamic acid; Structure-activity relationship; Antioxidant; Anti-inflammatory; Anthranilic acid

Published in

Heliyon
2020, Volume: 6, number: 6, article number: e04304
Publisher: ELSEVIER SCI LTD

      SLU Authors

    • UKÄ Subject classification

      Food Science

      Publication identifier

      DOI: https://doi.org/10.1016/j.heliyon.2020.e04304

      Permanent link to this page (URI)

      https://res.slu.se/id/publ/117764