Literature DB >> 35438989

Role of Oak Ellagitannins in the Synthesis of Vitisin A and in the Degradation of Malvidin 3-O-Glucoside: An Approach in Wine-Like Model Systems.

Cristina Alcalde-Eon1, María-Teresa Escribano-Bailón1, Ignacio García-Estévez1.   

Abstract

Recent studies highlight the influence that oak ellagitannins can have on wine astringency and color. Direct reactions between flavanols or anthocyanins with vescalagin have been reported to occur, but participation of these compounds in the formation of other types of derivatives has only been suggested but not demonstrated. This study aims at evaluating, in wine-like model systems, the possible different roles of the main oak ellagitannins, castalagin and vescalagin, alone or combined, in the synthesis of vitisin A and in the degradation of malvidin 3-O-glucoside. In the presence of pyruvic acid, the anthocyanin disappeared mainly as a result of the synthesis of vitisin A, whereas in its absence, degradation reactions prevailed. In general, ellagitannins increased the synthesis of vitisin A, decreased the total content of degradation products, and changed the degradation profile, with differences observed between castalagin and vescalagin. The results of the study revealed that the fate of malvidin 3-O-glucoside is conditioned by the presence of ellagitannins.

Entities:  

Keywords:  2,4,6-trihydroxybenzaldehyde; castalagin; degradation products; malvidin 3-O-glucoside; oak ellagitannins; syringic acid; vescalagin; vitisin A

Mesh:

Substances:

Year:  2022        PMID: 35438989      PMCID: PMC9585584          DOI: 10.1021/acs.jafc.2c00615

Source DB:  PubMed          Journal:  J Agric Food Chem        ISSN: 0021-8561            Impact factor:   5.895


  26 in total

1.  Vitisin A content in Chilean wines from Vitis vinifera Cv. Cabernet Sauvignon and contribution to the color of aged red wines.

Authors:  Michael Schwarz; Peter Quast; Dietrich von Baer; Peter Winterhalter
Journal:  J Agric Food Chem       Date:  2003-10-08       Impact factor: 5.279

2.  Evolution of castalagin and vescalagin in ethanol solutions. Identification of new derivatives.

Authors:  J L Puech; C Mertz; V Michon; C Le Guernevé; T Doco; C Hervé Du Penhoat
Journal:  J Agric Food Chem       Date:  1999-05       Impact factor: 5.279

3.  Isolation and structural characterization of new anthocyanin-derived yellow pigments in aged red wines.

Authors:  Jingren He; Celestino Santos-Buelga; Artur M S Silva; Nuno Mateus; Victor de Freitas
Journal:  J Agric Food Chem       Date:  2006-12-13       Impact factor: 5.279

4.  HPLC-DAD-ESI-MS/MS characterization of pyranoanthocyanins pigments formed in model wine.

Authors:  Dora Blanco-Vega; Francisco Javier López-Bellido; José María Alía-Robledo; Isidro Hermosín-Gutiérrez
Journal:  J Agric Food Chem       Date:  2011-08-17       Impact factor: 5.279

5.  Interactions between grape anthocyanins and pyruvic acid, with effect of pH and acid concentration on anthocyanin composition and color in model solutions.

Authors:  C Romero; J Bakker
Journal:  J Agric Food Chem       Date:  1999-08       Impact factor: 5.279

6.  A new class of blue anthocyanin-derived pigments isolated from red wines.

Authors:  Nuno Mateus; Artur M S Silva; Julian C Rivas-Gonzalo; Celestino Santos-Buelga; Victor de Freitas
Journal:  J Agric Food Chem       Date:  2003-03-26       Impact factor: 5.279

7.  Hemisynthesis and structural and chromatic characterization of delphinidin 3-O-glucoside-vescalagin hybrid pigments.

Authors:  Ignacio García-Estévez; Rémi Jacquet; Cristina Alcalde-Eon; Julián C Rivas-Gonzalo; M Teresa Escribano-Bailón; Stéphane Quideau
Journal:  J Agric Food Chem       Date:  2013-11-15       Impact factor: 5.279

8.  Conformational interpretation of vescalagin and castalagin physicochemical properties.

Authors:  Nicolas Vivas; Michel Laguerre; Isabelle Pianet de Boissel; Nathalie Vivas de Gaulejac; Marie-Françoise Nonier
Journal:  J Agric Food Chem       Date:  2004-04-07       Impact factor: 5.279

9.  The identification of degradation products and degradation pathway of malvidin-3-glucoside and malvidin-3,5-diglucoside under microwave treatment.

Authors:  Mengyao Zhao; Yinghua Luo; Yuan Li; Xin Liu; Jihong Wu; Xiaojun Liao; Fang Chen
Journal:  Food Chem       Date:  2013-06-11       Impact factor: 7.514

10.  A comprehensive investigation of guaiacyl-pyranoanthocyanin synthesis by one-/two-dimensional NMR and UPLC-DAD-ESI-MS(n).

Authors:  Anna Vallverdú-Queralt; Emmanuelle Meudec; Nayla Ferreira-Lima; Nicolas Sommerer; Olivier Dangles; Véronique Cheynier; Christine Le Guernevé
Journal:  Food Chem       Date:  2015-12-24       Impact factor: 7.514

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