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Issue 4, 2018, Issue in Progress
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Atypical antioxidant activity of non-phenolic amino-coumarins

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Abstract

Coumarin compounds have been described as anti-inflammatories, and chemotherapeutic agents as well as antioxidants. However, the origin of the antioxidant activity of non phenolic coumarins remains obscure. In the present report, we demonstrate that non-phenolic 7-dialkyl-aminocoumarins may also have significant antioxidant properties against free radicals derived from 2,2′-azobis(2-amidinopropane) dihydrochloride under aerobic conditions. This atypical behaviour is due to the presence of traces of very reactive hydroxycinnamic acid-type compounds. Changing functional groups at the C-3 and C-4 positions shifts the reactivity of the compounds from peroxyl to alkoxyl free radicals. Kinetic and theoretical studies based on Density Functional Theory support the formation of reactive hydroxycinnamic acid and directly link the antioxidant behaviour of the compounds to hydrogen atom transfer.

Graphical abstract: Atypical antioxidant activity of non-phenolic amino-coumarins

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Publication details

The article was received on 31 Oct 2017, accepted on 27 Dec 2017 and first published on 09 Jan 2018


Article type: Paper
DOI: 10.1039/C7RA12000A
RSC Adv., 2018,8, 1927-1933
  • Open access: Creative Commons BY license
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    Atypical antioxidant activity of non-phenolic amino-coumarins

    D. Zúñiga-Núñez, P. Barrias, G. Cárdenas-Jirón, M. S. Ureta-Zañartu, C. Lopez-Alarcón, F. E. Morán Vieyra, C. D. Borsarelli, E. I. Alarcon and A. Aspée, RSC Adv., 2018, 8, 1927
    DOI: 10.1039/C7RA12000A

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