Antioxidant Features of Red Wine Pyranoanthocyanins: Experimental and Theoretical Approaches

This work is focused on the study of the antioxidant properties of red wine anthocyanin derivatives (carboxypyranoanthocyanins, methylpyranoanthocyanins, oxovitisins, and pyranoanthocyanin-phenolics) derived from malvidin-3-glucoside. Some antioxidant features were determined using the DPPH assay an...

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Veröffentlicht in:Journal of agricultural and food chemistry 2014-07, Vol.62 (29), p.7002-7009
Hauptverfasser: Azevedo, Joana, Oliveira, Joana, Cruz, Luis, Teixeira, Natércia, Brás, Natércia F, De Freitas, Victor, Mateus, Nuno
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container_end_page 7009
container_issue 29
container_start_page 7002
container_title Journal of agricultural and food chemistry
container_volume 62
creator Azevedo, Joana
Oliveira, Joana
Cruz, Luis
Teixeira, Natércia
Brás, Natércia F
De Freitas, Victor
Mateus, Nuno
description This work is focused on the study of the antioxidant properties of red wine anthocyanin derivatives (carboxypyranoanthocyanins, methylpyranoanthocyanins, oxovitisins, and pyranoanthocyanin-phenolics) derived from malvidin-3-glucoside. Some antioxidant features were determined using the DPPH assay and the ability to delay lipid peroxidation in a liposome membrane system by monitoring oxygen consumption. The pyranoanthocyanin-phenolics have higher antioxidant potential than that of malvidin-3-glucoside, suggesting that the addition of a catechol or flavanol moiety increases the antioxidant capacity. The only derivatives that showed lower antioxidant features than malvidin-3-glucoside were oxovitisins and methylpyranomalvidin-3-glucoside. Also, the radical scavenging capacity of these pyranoanthocyanins was computationally explored using DFT methods. All pyranoanthocyanins were suggested as good candidates as antioxidant compounds because they easily donate an H atom to the free radicals, originating stable species. Altogether, these results support the fact that the antioxidant potential arising from anthocyanins is not impaired by some of their transformations during red wine aging.
doi_str_mv 10.1021/jf404735j
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Agric. Food Chem</addtitle><description>This work is focused on the study of the antioxidant properties of red wine anthocyanin derivatives (carboxypyranoanthocyanins, methylpyranoanthocyanins, oxovitisins, and pyranoanthocyanin-phenolics) derived from malvidin-3-glucoside. Some antioxidant features were determined using the DPPH assay and the ability to delay lipid peroxidation in a liposome membrane system by monitoring oxygen consumption. The pyranoanthocyanin-phenolics have higher antioxidant potential than that of malvidin-3-glucoside, suggesting that the addition of a catechol or flavanol moiety increases the antioxidant capacity. The only derivatives that showed lower antioxidant features than malvidin-3-glucoside were oxovitisins and methylpyranomalvidin-3-glucoside. Also, the radical scavenging capacity of these pyranoanthocyanins was computationally explored using DFT methods. 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subjects anthocyanins
Anthocyanins - analysis
Anthocyanins - pharmacology
antioxidant activity
antioxidants
Antioxidants - analysis
Antioxidants - pharmacology
catechol
free radicals
lipid peroxidation
Lipid Peroxidation - drug effects
Liposomes
Models, Theoretical
monitoring
Oxygen - chemistry
oxygen consumption
red wines
Wine - analysis
wine aging
title Antioxidant Features of Red Wine Pyranoanthocyanins: Experimental and Theoretical Approaches
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