Quinones as Strecker degradation reagents in wine oxidation processes

Carla Maria Oliveira; Sónia A O Santos; Armando J D Silvestre; António S Barros; António César Silva Ferreira; Artur M S Silva

doi:10.1016/j.foodchem.2017.02.034

Quinones as Strecker degradation reagents in wine oxidation processes

Food Chem. 2017 Aug 1:228:618-624. doi: 10.1016/j.foodchem.2017.02.034. Epub 2017 Feb 10.

Authors

Carla Maria Oliveira¹, Sónia A O Santos², Armando J D Silvestre², António S Barros³, António César Silva Ferreira⁴, Artur M S Silva³

Affiliations

¹ 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.
² CICECO - Aveiro Institute of Materials/Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal.
³ QOPNA/Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal.
⁴ 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.

PMID: 28317771
DOI: 10.1016/j.foodchem.2017.02.034

Abstract

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.

Keywords: (+)-Catechin (PubChem CID: 9064); Amino acids; Caffeic acid (PubChem CID: 689043); Gallic acid (PubChem CID: 370); Oxidation; Oxygen; Phenolics; Quinones; Strecker aldehydes; Wine.

MeSH terms

Amino Acids / chemistry*
Indicators and Reagents / chemistry*
Oxidation-Reduction
Quinones / chemistry*
Wine / analysis*

Substances

Amino Acids
Indicators and Reagents
Quinones