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Structural Characterization of New Malvidin 3-Glucoside−Catechin Aryl/Alkyl-Linked Pigments

2004; American Chemical Society; Volume: 52; Issue: 17 Linguagem: Inglês

10.1021/jf0494433

1520-5118

João Pissarra, Sandra Lourenço, Ana M. Gonzaléz‐Paramás, Nuno Mateus, Celestino Santos‐Buelga, Artur M. S. Silva, Víctor de Freitas,

Fermentation and Sensory Analysis

The condensation reaction between malvidin 3-glucoside and catechin mediated by isobutyraldehyde, benzaldehyde, and isovaleraldehyde was conducted in model solutions at two pH values (1.5 and 3.2). The formation of new alkyl/aryl-linked adducts corresponding to the structures malvidin 3-glucoside-isobutylcatechin, malvidin 3-glucoside-benzylcatechin, and malvidin 3-glucoside-3-methylbutylcatechin was respectively observed from each aldehyde. The structural characterization of these new structures has been elucidated by 1D and 2D NMR, mass spectrometry, and UV-vis techniques. These new adducts showed the same lambda(max) in the visible region at 540 nm, which is bathochromically shifted 15 nm when compared with the original anthocyanin (lambda(max) = 525 nm).