Antioxidant activity and mechanism of action of some synthesised phenolic acid amides of aromatic amines

Emma Marinova, Lubomir Georgiev, Iskra Totseva, Katya Seizova and Tsenka Milkova
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Emma Marinova: Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria
Lubomir Georgiev: South-West University "Neofit Rilski", Blagoevgrad, Bulgaria
Iskra Totseva: Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria
Katya Seizova: Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria
Tsenka Milkova: South-West University "Neofit Rilski", Blagoevgrad, Bulgaria

Czech Journal of Food Sciences, 2013, vol. 31, issue 1, 5-13

Abstract: The antioxidative activities and mechanism of action were studied of eight synthesised cinnamoyl- and hydroxycinnamoyl amides of biogenic amines (caffeoyldopamine, cinnamoyldopamine, p-coumaroyldopamine, feruloyldopamine, sinapoyldopamine, caffeoylphenylethylamine, caffeoyltyramine, and caffeoyltryptamine) in a wide concentration range (2.5-20 × 10-4M) during autoxidation of triacylglycerols of sunflower oil. It was established that all amides exhibited excellent antioxidant activity, higher than or comparable with that of caffeic acid. The best activity was shown by caffeoyldopamine followed by cinnamoyldopamine and caffeoyltyramine. The analysis of the kinetic data obtained showed that the presence of hydroxyl groups in the amino part (derivatives of dopamine and tyramine) led to direct oxidation of the molecules during the process and stabilisation of the resulting radicals. In contrast, the amides without hydroxyl groups in the amino part participated in the side reaction with peroxides and the resulting radicals took part in one side reaction of the chain propagation as did caffeic acid.

Keywords: cinnamic acid derivatives; phenylpropenoyl amides of aromatic amines; triacylglycerols of sunflower oil (search for similar items in EconPapers)
Date: 2013
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Persistent link: https://EconPapers.repec.org/RePEc:caa:jnlcjf:v:31:y:2013:i:1:id:280-2011-cjfs

DOI: 10.17221/280/2011-CJFS

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