A New Chemical Pathway Yielding A-Type Vitisins in Red Wines

A new chemical pathway yielding A-type vitisins in red wines is proposed herein from the reaction between anthocyanins and oxaloacetic acid (OAA). This new chemical path is thought to occur in the first stages of the wine production even during the fermentation process. This is due to the revealed h...

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Main Authors: Paula Araújo, Ana Fernandes, Victor de Freitas, Joana Oliveira
Format: Article
Language:English
Published: MDPI AG 2017-04-01
Series:International Journal of Molecular Sciences
Subjects:
Online Access:http://www.mdpi.com/1422-0067/18/4/762
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spelling doaj-856bc9b7a8bc44c3883e4036486b17812020-11-24T22:23:08ZengMDPI AGInternational Journal of Molecular Sciences1422-00672017-04-0118476210.3390/ijms18040762ijms18040762A New Chemical Pathway Yielding A-Type Vitisins in Red WinesPaula Araújo0Ana Fernandes1Victor de Freitas2Joana Oliveira3Laboratório Associado para a Química Verde, Departamento de Química e Bioquímica, Faculdade de Ciências da Universidade do Porto, Rua do Campo Alegre, 687, 4169-007 Porto, PortugalLaboratório Associado para a Química Verde, Departamento de Química e Bioquímica, Faculdade de Ciências da Universidade do Porto, Rua do Campo Alegre, 687, 4169-007 Porto, PortugalLaboratório Associado para a Química Verde, Departamento de Química e Bioquímica, Faculdade de Ciências da Universidade do Porto, Rua do Campo Alegre, 687, 4169-007 Porto, PortugalLaboratório Associado para a Química Verde, Departamento de Química e Bioquímica, Faculdade de Ciências da Universidade do Porto, Rua do Campo Alegre, 687, 4169-007 Porto, PortugalA new chemical pathway yielding A-type vitisins in red wines is proposed herein from the reaction between anthocyanins and oxaloacetic acid (OAA). This new chemical path is thought to occur in the first stages of the wine production even during the fermentation process. This is due to the revealed high reactivity of OAA with anthocyanins compared with the already known precursor (pyruvic acid, PA). In model solutions at wine pH (3.5), when malvidin-3-O-glucoside (mv-3-glc) is in contact with OAA and PA a decrease in the OAA concentration is observed along with the formation of A-type vitisin. Moreover, part of the OAA is also chemically converted into PA in model solutions. The reaction yields were also determined for OAA and PA using different mv-3-glc:organic acid molar ratios (1:0.5, 1:1, 1:5, 1:10; 1:50, and 1:100) and these values were always higher for OAA when compared to PA, even at the lowest molar ratio (1:0.5). The reaction yields were higher at pH 2.6 in comparison to pH 1.5 and 3.5, being less affected at pH 3.5 for OAA. These results support the idea that OAA can be at the origin of A-type vitisins in the first stages of wine production and PA in the subsequent ageing process.http://www.mdpi.com/1422-0067/18/4/762malvidin-3-O-glucosidepyruvic acidoxaloacetic acidcarboxypyranomalvidin-3-O-glucoside vitisinanthocyaninsred wines
collection DOAJ
language English
format Article
sources DOAJ
author Paula Araújo
Ana Fernandes
Victor de Freitas
Joana Oliveira
spellingShingle Paula Araújo
Ana Fernandes
Victor de Freitas
Joana Oliveira
A New Chemical Pathway Yielding A-Type Vitisins in Red Wines
International Journal of Molecular Sciences
malvidin-3-O-glucoside
pyruvic acid
oxaloacetic acid
carboxypyranomalvidin-3-O-glucoside vitisin
anthocyanins
red wines
author_facet Paula Araújo
Ana Fernandes
Victor de Freitas
Joana Oliveira
author_sort Paula Araújo
title A New Chemical Pathway Yielding A-Type Vitisins in Red Wines
title_short A New Chemical Pathway Yielding A-Type Vitisins in Red Wines
title_full A New Chemical Pathway Yielding A-Type Vitisins in Red Wines
title_fullStr A New Chemical Pathway Yielding A-Type Vitisins in Red Wines
title_full_unstemmed A New Chemical Pathway Yielding A-Type Vitisins in Red Wines
title_sort new chemical pathway yielding a-type vitisins in red wines
publisher MDPI AG
series International Journal of Molecular Sciences
issn 1422-0067
publishDate 2017-04-01
description A new chemical pathway yielding A-type vitisins in red wines is proposed herein from the reaction between anthocyanins and oxaloacetic acid (OAA). This new chemical path is thought to occur in the first stages of the wine production even during the fermentation process. This is due to the revealed high reactivity of OAA with anthocyanins compared with the already known precursor (pyruvic acid, PA). In model solutions at wine pH (3.5), when malvidin-3-O-glucoside (mv-3-glc) is in contact with OAA and PA a decrease in the OAA concentration is observed along with the formation of A-type vitisin. Moreover, part of the OAA is also chemically converted into PA in model solutions. The reaction yields were also determined for OAA and PA using different mv-3-glc:organic acid molar ratios (1:0.5, 1:1, 1:5, 1:10; 1:50, and 1:100) and these values were always higher for OAA when compared to PA, even at the lowest molar ratio (1:0.5). The reaction yields were higher at pH 2.6 in comparison to pH 1.5 and 3.5, being less affected at pH 3.5 for OAA. These results support the idea that OAA can be at the origin of A-type vitisins in the first stages of wine production and PA in the subsequent ageing process.
topic malvidin-3-O-glucoside
pyruvic acid
oxaloacetic acid
carboxypyranomalvidin-3-O-glucoside vitisin
anthocyanins
red wines
url http://www.mdpi.com/1422-0067/18/4/762
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