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Molecules 2018, 23(5), 1066; https://doi.org/10.3390/molecules23051066

Preparation and Antioxidant Activity of Ethyl-Linked Anthocyanin-Flavanol Pigments from Model Wine Solutions

1
School of Pharmacy, Shenyang Pharmaceutical University, Shenyang 110016, China
2
School of Functional Food and Wine, Shenyang Pharmaceutical University, Shenyang 110016, China
3
School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China
4
Pólo Dois Portos, Instituto National de Investigação Agrária e Veterinária, I.P., Quinta da Almoinha, Dois Portos 2565–191, Portugal
*
Author to whom correspondence should be addressed.
Received: 2 March 2018 / Revised: 18 April 2018 / Accepted: 24 April 2018 / Published: 3 May 2018
(This article belongs to the Collection Wine Chemistry)
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Abstract

Anthocyanin-flavanol pigments, formed during red wine fermentation and storage by condensation reactions between anthocyanins and flavanols (monomers, oligomers, and polymers), are one of the major groups of polyphenols in aged red wine. However, knowledge of their biological activities is lacking. This is probably due to the structural diversity and complexity of these molecules, which makes the large-scale separation and isolation of the individual compounds very difficult, thus restricting their further study. In this study, anthocyanins (i.e., malvidin-3-glucoside, cyanidin-3-glucoside, and peonidin-3-glucoside) and (–)-epicatechin were first isolated at a preparative scale by high-speed counter-current chromatography. The condensation reaction between each of the isolated anthocyanins and (–)-epicatechin, mediated by acetaldehyde, was conducted in model wine solutions to obtain ethyl-linked anthocyanin-flavanol pigments. The effects of pH, molar ratio, and temperature on the reaction rate were investigated, and the reaction conditions of pH 1.7, molar ratio 1:6:10 (anthocyanin/(–)-epicatechin/acetaldehyde), and reaction temperature of 35 °C were identified as optimal for conversion of anthocyanins to ethyl-linked anthocyanin-flavanol pigments. Six ethyl-linked anthocyanin-flavanol pigments were isolated in larger quantities and collected under optimal reaction conditions, and their chemical structures were identified by HPLC-QTOF-MS and ECD analyses. Furthermore, DPPH, ABTS, and FRAP assays indicate that ethyl-linked anthocyanin-flavanol pigments show stronger antioxidant activities than their precursor anthocyanins. View Full-Text
Keywords: anthocyanin; antioxidant activity; ethyl-linked anthocyanin-flavanol pigment anthocyanin; antioxidant activity; ethyl-linked anthocyanin-flavanol pigment
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).
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Li, L.; Zhang, M.; Zhang, S.; Cui, Y.; Sun, B. Preparation and Antioxidant Activity of Ethyl-Linked Anthocyanin-Flavanol Pigments from Model Wine Solutions. Molecules 2018, 23, 1066.

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