Color and Stability of Pigments Derived from the Acetaldehyde-Mediated Condensation between Malvidin 3-O-Glucoside and (+)-Catechin

[EN] A pigment derived from the acetaldehyde-mediated condensation between (+)-catechin and malvidin 3-O-glucoside has been prepared and isolated by semipreparative HPLC, and its characteristics of color and stability have been studied and compared with that of malvidin glucoside in aqueous solution...

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Authors: Escribano Bailón, María Teresa, Álvarez-García, Marta, Rivas Gonzalo, Julián C., Heredia, Francisco J., Santos Buelga, Celestino
Format: article
Status:Published version
Publication Date:2001
Country:España
Institution:Universidad de Salamanca (USAL)
Repository:GREDOS. Repositorio Institucional de la Universidad de Salamanca
OAI Identifier:oai:gredos.usal.es:10366/141044
Online Access:http://hdl.handle.net/10366/141044
Access Level:Open access
Keyword:Wine
Anthocyanins
Malvidin 3-O-glucoside
Flavanols
(+)-catechin
Pigments
Acetaldehyde
antocianinas
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repository_id_str
spelling Color and Stability of Pigments Derived from the Acetaldehyde-Mediated Condensation between Malvidin 3-O-Glucoside and (+)-CatechinEscribano Bailón, María TeresaÁlvarez-García, MartaRivas Gonzalo, Julián C.Heredia, Francisco J.Santos Buelga, CelestinoWineAnthocyaninsMalvidin 3-O-glucosideFlavanols(+)-catechinPigmentsAcetaldehydeAnthocyaninsantocianinas[EN] A pigment derived from the acetaldehyde-mediated condensation between (+)-catechin and malvidin 3-O-glucoside has been prepared and isolated by semipreparative HPLC, and its characteristics of color and stability have been studied and compared with that of malvidin glucoside in aqueous solutions. When the pH was increased from 2.2 to 5.5, the solution of the pigment became progressively more violet (ìmax ) 560 nm at pH 5.5), whereas similar solutions of the anthocyanin were almost colorless at pH 4.0. This behavior indicated that the anthocyanin moiety of the pigment was more protected against water attack, and thus the formation of its quinonoidal forms was favored. The color of the pigment also showed more stability with regard to bleaching by SO2 than that of malvidin glucoside. Nevertheless, the pigment was more sensitive to degradation in aqueous solution than the anthocyanin. The cleavage of the ethyl bridge that links the anthocyanin and the catechin constituted the first step in its degradation, as demonstrated by the formation of malvidin glucoside as a major product.202020202001info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10366/141044reponame:GREDOS. Repositorio Institucional de la Universidad de Salamancainstname:Universidad de Salamanca (USAL)InglésAttribution-NonCommercial-NoDerivatives 4.0 Internacionalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessoai:gredos.usal.es:10366/1410442026-06-07T06:28:51Z
dc.title.none.fl_str_mv Color and Stability of Pigments Derived from the Acetaldehyde-Mediated Condensation between Malvidin 3-O-Glucoside and (+)-Catechin
title Color and Stability of Pigments Derived from the Acetaldehyde-Mediated Condensation between Malvidin 3-O-Glucoside and (+)-Catechin
spellingShingle Color and Stability of Pigments Derived from the Acetaldehyde-Mediated Condensation between Malvidin 3-O-Glucoside and (+)-Catechin
Escribano Bailón, María Teresa
Wine
Anthocyanins
Malvidin 3-O-glucoside
Flavanols
(+)-catechin
Pigments
Acetaldehyde
Anthocyanins
antocianinas
title_short Color and Stability of Pigments Derived from the Acetaldehyde-Mediated Condensation between Malvidin 3-O-Glucoside and (+)-Catechin
title_full Color and Stability of Pigments Derived from the Acetaldehyde-Mediated Condensation between Malvidin 3-O-Glucoside and (+)-Catechin
title_fullStr Color and Stability of Pigments Derived from the Acetaldehyde-Mediated Condensation between Malvidin 3-O-Glucoside and (+)-Catechin
title_full_unstemmed Color and Stability of Pigments Derived from the Acetaldehyde-Mediated Condensation between Malvidin 3-O-Glucoside and (+)-Catechin
title_sort Color and Stability of Pigments Derived from the Acetaldehyde-Mediated Condensation between Malvidin 3-O-Glucoside and (+)-Catechin
dc.creator.none.fl_str_mv Escribano Bailón, María Teresa
Álvarez-García, Marta
Rivas Gonzalo, Julián C.
Heredia, Francisco J.
Santos Buelga, Celestino
author Escribano Bailón, María Teresa
author_facet Escribano Bailón, María Teresa
Álvarez-García, Marta
Rivas Gonzalo, Julián C.
Heredia, Francisco J.
Santos Buelga, Celestino
author_role author
author2 Álvarez-García, Marta
Rivas Gonzalo, Julián C.
Heredia, Francisco J.
Santos Buelga, Celestino
author2_role author
author
author
author
dc.subject.none.fl_str_mv Wine
Anthocyanins
Malvidin 3-O-glucoside
Flavanols
(+)-catechin
Pigments
Acetaldehyde
Anthocyanins
antocianinas
topic Wine
Anthocyanins
Malvidin 3-O-glucoside
Flavanols
(+)-catechin
Pigments
Acetaldehyde
Anthocyanins
antocianinas
description [EN] A pigment derived from the acetaldehyde-mediated condensation between (+)-catechin and malvidin 3-O-glucoside has been prepared and isolated by semipreparative HPLC, and its characteristics of color and stability have been studied and compared with that of malvidin glucoside in aqueous solutions. When the pH was increased from 2.2 to 5.5, the solution of the pigment became progressively more violet (ìmax ) 560 nm at pH 5.5), whereas similar solutions of the anthocyanin were almost colorless at pH 4.0. This behavior indicated that the anthocyanin moiety of the pigment was more protected against water attack, and thus the formation of its quinonoidal forms was favored. The color of the pigment also showed more stability with regard to bleaching by SO2 than that of malvidin glucoside. Nevertheless, the pigment was more sensitive to degradation in aqueous solution than the anthocyanin. The cleavage of the ethyl bridge that links the anthocyanin and the catechin constituted the first step in its degradation, as demonstrated by the formation of malvidin glucoside as a major product.
publishDate 2001
dc.date.none.fl_str_mv 2001
2020
2020
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10366/141044
url http://hdl.handle.net/10366/141044
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.rights.none.fl_str_mv Attribution-NonCommercial-NoDerivatives 4.0 Internacional
http://creativecommons.org/licenses/by-nc-nd/4.0/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Attribution-NonCommercial-NoDerivatives 4.0 Internacional
http://creativecommons.org/licenses/by-nc-nd/4.0/
eu_rights_str_mv openAccess
dc.source.none.fl_str_mv reponame:GREDOS. Repositorio Institucional de la Universidad de Salamanca
instname:Universidad de Salamanca (USAL)
instname_str Universidad de Salamanca (USAL)
reponame_str GREDOS. Repositorio Institucional de la Universidad de Salamanca
collection GREDOS. Repositorio Institucional de la Universidad de Salamanca
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.300724

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