Interaction of Flavanols with Amino Acids: Postoxidative Reactivity of the B-Ring of Catechin with Glycine

Flavanol-related structures such as epicatechin and catechins have been associated with potential antioxidant activity in food and are known to interfere with the Mail lard reaction through scavenging of reactive dicarbonyl compounds. High-resolution ESI-TOF mass spectrometry and an isotope labeling technique were used to assess the reactivity of glycine with (+)-catechin heated under oxidative conditions at 120 degrees C for 70 min. Evidence based on accurate mass analysis of the products obtained and the isotope incorporation pattern of [C-13- 1]glycine, [C-13-2]glycine, and [N-15]glycine experiments indicated that (+)-catechin formed various adducts with glycine; two of them incorporated a single amino acid, and three adducts incorporated two amino acid moieties. Some of these adducts underwent dehydration reaction at ring C, and in some the C-ring remained intact. Detailed MS/MS analyses of the fragmentation patterns of these adducts have confirmed the addition of amino acid moieties to the oxidized B-ring of (+)-catechin through the formation of Schiff bases. Formation of such nonvolatile (+)-catechin/amino acid adducts provides insight into how amino acid can have the potential of modifying the antioxidant properties of (+)-catechin and how catechin in turn has the potential of modifying the profile of the Mail lard reaction.