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Role of Vinylcatechin in the Formation of Pyranomalvidin-3-glucoside−(+)-Catechin

2008; American Chemical Society; Volume: 56; Issue: 22 Linguagem: Inglês

10.1021/jf8021496

1520-5118

Luís Cruz, Natércia Teixeira, Artur M. S. Silva, Nuno Mateus, José E. Rodríguez‐Borges, Víctor de Freitas,

Phytochemicals and Antioxidant Activities

Reactions between malvidin-3-glucoside (mv3glc) and 8-vinylcatechin were carried out to synthesize pyranomv3glc−(+)-catechin pigment and to study the formation of intermediates. A rapid decrease of mv3glc content concomitant with the formation of more complex structures such as mv3glc−vinylcatechin [precursor of pyranomv3glc−(+)-catechin pigment] and mv3glc−divinylcatechin was observed. On the other hand, 8-vinylcatechin undergoes acid-catalyzed dimerization in model wine solution, giving rise to 8-vinylcatechin dimers. These compounds were also found in the reaction between mv3glc and (+)-catechin mediated by acetaldehyde, which provides evidence for the formation of 8-vinylcatechin and its involvement in the formation of pyranoanthocyanins in aged red wines.