Demonstration of the occurrence of flavanol–anthocyanin adducts in wine and in model solutions
Section snippets
Materials
Organic solvents (methanol, acetonitrile and ethanol) and phenylmethanethiol were purchased form Merck (Darmstadt, Germany) and Fluka (Buchs, Switzerland), respectively. Taxifolin was purchased from Extrasynthèse (France).
Wine
Two flavanol–anthocyanin (F–A+) adducts (retention time 23.8 and 26.9 min), showing a mass signal at m/z=781, were detected in wine (Fig. 2). One of these adducts showed a UV-Vis spectrum similar to that of Mv3glc. Its concentration, expressed in Mv3glc equivalents, was estimated at 2 and 3 mg l−1, respectively, after 4 and 11 months of ageing. The other adduct (TR=26.9 min) was coeluted with Cy3glc; therefore it was not possible to obtain its UV-Vis spectrum.
Their MS/MS fragmentation (Fig. 3) gave
Conclusions
Hemisynthesis of F–A+ adducts was achieved by two different processes, yielding respectively cat–Mv3glc and Ec–Mv3glc. Their retention time in LC, their UV-Vis spectrum, and their mass fragmentation patterns are identical to those of pigments detected in wine, indicating that the latter are also F–A+ adducts. All of these products (in wine and those obtained by hemisynthesis) are resistant to thiolysis. Besides, we were able to confirm that the formation of these products in wine proceeds
Acknowledgements
The authors thank the Consejo Nacional de Ciencia y Tecnologia (CONACYT, Mexico) for providing a doctoral financement in a cooperation programme with the Société Française d’Exportation des Ressources Educatives (SFERE, France).
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