Quinones as Strecker degradation reagents in wine oxidation processes.
The Strecker aldehydes formed during the reaction between α-amino acids (phenylalanine or methionine) and either gallic acid, caffeic acid or (+)-catechin ortho-quinones were evaluated in wine-model systems. It was demonstrated that phenylacetaldehyde was formed by quinone intermediates at wine pH. The highest amounts of phenylacetaldehyde during the 10days of experiment (69±5µg/L/day; 7x>Control) were obtained from (+) catechin, followed by gallic acid (61±4µg/L/day; 6x>Control) and caffeic acid (41±4µg/L/day; 4x>Control). The intermediate structures delivered from the reaction of ortho-quinones with α-amino acids were demonstrated by MSn.
QOPNA/Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal; CBQF/Faculty of Biotechnology, Catholic University of Portugal, Rua Arquiteto Lobão Vital, Apartado 251, 4202-401 Porto, Portugal. Electronic address: cm.dias@ua.pt.
Carla Maria
CM
Oliveira
CICECO - Aveiro Institute of Materials/Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal.
Sónia A O
SA
Santos
CICECO - Aveiro Institute of Materials/Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal.
Armando J D
AJ
Silvestre
QOPNA/Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal.
António S
AS
Barros
CBQF/Faculty of Biotechnology, Catholic University of Portugal, Rua Arquiteto Lobão Vital, Apartado 251, 4202-401 Porto, Portugal; Stellenbosch University, Private Bag X1, Matieland, 7602 Stellenbosch, South Africa.
António César Silva
AC
Ferreira
QOPNA/Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal.
Artur M S
AM
Silva
D000596:Amino Acids / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry*; D010084:Oxidation-Reduction; D011809:Quinones / Q000737:chemistry*; D014920:Wine / Q000032:analysis*
D000596:Amino Acids; D007202:Indicators and Reagents; D011809:Quinones
(+)-Catechin (PubChem CID: 9064); Amino acids; Caffeic acid (PubChem CID: 689043); Gallic acid (PubChem CID: 370); Oxidation; Oxygen; Phenolics; Quinones; Strecker aldehydes; Wine