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

• Published in: Journal of agricultural and food chemistry Vol. 49; no. 3; pp. 1213 - 1217
• Main Authors: Escribano-Bailón, Teresa, Álvarez-García, Marta, Rivas-Gonzalo, Julian C, Heredia, Francisco J, Santos-Buelga, Celestino
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01-03-2001
• Subjects: Acetaldehyde; Anthocyanins - chemistry; Anthocyanins - isolation & purification; Biological and medical sciences; Catechin - chemistry; Fermented food industries; Food industries; Fruit - chemistry; Fundamental and applied biological sciences. Psychology; Hydrogen-Ion Concentration; Pigments, Biological - chemical synthesis; Pigments, Biological - chemistry; Seeds - chemistry; Solutions; Water; Wines and vinegars; Anthocyanin; Flavanol; Catechin; Condensation reaction; Stability; Bleaching; Color; Pigments; pH; Red wine; Acetaldehyde; Coloration
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf001081l

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 (λmax = 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. Keywords: Wine; anthocyanins; malvidin 3-O-glucoside; flavanols; (+)-catechin; pigments; acetaldehyde