UV-visible spectroscopic investigation of the 8,8-methylmethine catechin-malvidin 3-glucoside pigments in aqueous solution: structural transformations and molecular complexation with chlorogenic acid - INRAE - Institut national de recherche pour l’agriculture, l’alimentation et l’environnement Access content directly
Journal Articles Journal of Agricultural and Food Chemistry Year : 2006

UV-visible spectroscopic investigation of the 8,8-methylmethine catechin-malvidin 3-glucoside pigments in aqueous solution: structural transformations and molecular complexation with chlorogenic acid

Erika Salas
  • Function : Author
  • PersonId : 976329
Veronique V. Cheynier
Hélène Fulcrand

Abstract

The physicochemical properties of 8,8-methylmethine catechin-malvidin 3-O-glucoside isomers, commonly referred to as catechin-ethyl-malvidin 3-O-glucoside, have been studied in aqueous solutions and compared with those of the parent anthocyanin (malvidin 3-O-glucoside). The hydration and acidity constants (pKh and pKa) of the catechin-ethyl-malvidin 3-O-glucoside pigments and malvidin 3-O-glucoside were determined by UV-visible spectroscopic measurements. The ethyl-linked catechin-malvidin 3-O-glucoside pigments present higher stability toward hydration than the parent anthocyanin. The high resistance of these ethyl-linked pigments toward the hydration is related to the self-association that offers optimal protection from the nucleophilic attack of water. Moreover, the ethyl link may confer to the molecule enough flexibility to undergo intramolecular interaction, further protecting it from hydration and bisulfite discoloration. In the wine pH range (3.2-4.0), due to the low pKa and high pKh values, the ethyl-linked pigments are present as colored forms (flavylium cation and quinonoid bases).

Dates and versions

hal-02663990 , version 1 (31-05-2020)

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Montserrat Dueñas, Erika Salas, Veronique V. Cheynier, Olivier O. Dangles, Hélène Fulcrand. UV-visible spectroscopic investigation of the 8,8-methylmethine catechin-malvidin 3-glucoside pigments in aqueous solution: structural transformations and molecular complexation with chlorogenic acid. Journal of Agricultural and Food Chemistry, 2006, 54 (1), pp.189-196. ⟨10.1021/jf0516989⟩. ⟨hal-02663990⟩
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