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J Agric Food Chem. 2003 Mar 26;51(7):1919-23.

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

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  • 1Centro de Investigação em Química, Departamento de Química, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre 687, 4169-007 Porto, Portugal.


Two newly formed anthocyanin-derived pigments that revealed unique spectroscopic features, showing maximum absorption in their UV-vis spectra at 575 nm, were isolated by TSK Toyopearl HW-40 (S) gel column chromatography and semipreparative HPLC from an aged Port red wine. Further characterization by ESI/MS and NMR ((1)H, gCOSY) showed them to belong to a new class of pigments described here for the first time, the structure of which consisted of a pyranoanthocyanin moiety linked to a flavanol by a vinyl bridge. The extended conjugation of the pi electrons throughout all the pigment molecule is likely to confer a higher stability on it and is probably the origin of the intense blue color. The formation of these pigments was found to arise from the reaction between anthocyanin-pyruvic acid adducts and vinyl-flavanol adducts.

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