title: Amino acid decarboxylations produced by lipid-derived reactive carbonyls in amino acid mixtures.
abstract: The formation of 2-phenylethylamine and phenylacetaldehyde in mixtures of phenylalanine, a lipid oxidation product, and a second amino acid was studied to determine the role of the second amino acid in the degradation of phenylalanine produced by lipid-derived reactive carbonyls. The presence of the second amino acid usually increased the formation of the amine and reduced the formation of the Strecker aldehyde. The reasons for this behaviour seem to be related to the α-amino group and the other functional groups (mainly amino or similar groups) present in the side-chain of the amino acid. These groups are suggested to modify the lipid-derived reactive carbonyl but not the reaction mechanism because the Ea of formation of both 2-phenylethylamine and phenylacetaldehyde remained unchanged in all studied systems. All these results suggest that the amine/aldehyde ratio obtained by amino acid degradation can be modified by adding free amino acids during food formulation.
authors.affiliation: Instituto de la Grasa, Consejo Superior de Investigaciones Científicas, Carretera de Utrera km 1, Campus Universitario - Edificio 46, 41013 Seville, Spain.
authors.forename: Francisco J
authors.initials: FJ
authors.lastname: Hidalgo
authors.affiliation: Instituto de la Grasa, Consejo Superior de Investigaciones Científicas, Carretera de Utrera km 1, Campus Universitario - Edificio 46, 41013 Seville, Spain.
authors.forename: M Mercedes
authors.initials: MM
authors.lastname: León
authors.affiliation: Instituto de la Grasa, Consejo Superior de Investigaciones Científicas, Carretera de Utrera km 1, Campus Universitario - Edificio 46, 41013 Seville, Spain. Electronic address: rzamora@ig.csic.es.
authors.forename: Rosario
authors.initials: R
authors.lastname: Zamora
mesh_terms: D000079:Acetaldehyde / Q000031:analogs & derivatives* / Q000032:analysis / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D003653:Decarboxylation; D008055:Lipids / Q000737:chemistry*; D015416:Maillard Reaction; D010084:Oxidation-Reduction; D010627:Phenethylamines / Q000032:analysis* / Q000737:chemistry; D010649:Phenylalanine / Q000737:chemistry
chemical_list: D000596:Amino Acids; D008055:Lipids; D010627:Phenethylamines; C029261:phenethylamine; D010649:Phenylalanine; D000079:Acetaldehyde; C013192:phenylacetaldehyde
keywords: 2,4-Decadienal (PubChem ID: 5283349); 2,4-Heptadienal (PubChem ID: 5283321); 2-Octenal (PubChem ID: 5283324); 2-Phenylethylamine (PubChem ID: 1001); 4,5-Epoxy-2-decenal (PubChem ID: 15825667); 4,5-Epoxy-2-heptenal (PubChem ID: 6444055); 4-Hydroxy-2-nonenal (PubChem ID:5283344); 4-Oxo-2-nonenal (PubChem ID: 6445537); Amino acid degradation; Biogenic amines; Carbonyl-amine reactions; Lipid oxidation; Maillard reaction; Phenylacetaldehyde (PubChem ID: 998); Phenylalanine (PubChem ID: 6140); Strecker degradation