title: Antagonism between lipid-derived reactive carbonyls and phenolic compounds in the Strecker degradation of amino acids.
abstract: The Strecker-type degradation of phenylalanine in the presence of 2-pentanal and phenolic compounds was studied to investigate possible interactions that either promote or inhibit the formation of Strecker aldehydes in food products. Phenylacetaldehyde formation was promoted by 2-pentenal and also by o- and p-diphenols, but not by m-diphenols. This is consequence of the ability of phenolic compounds to be converted into reactive carbonyls and produce the Strecker degradation of the amino acid. When 2-pentenal and phenolic compounds were simultaneously present, an antagonism among them was observed. This antagonism is suggested to be a consequence of the ability of phenolic compounds to either react with both 2-pentenal and phenylacetaldehyde, or compete with other carbonyl compounds for the amino acids, a function that is determined by their structure. All these results suggest that carbonyl-phenol reactions may be used to modulate flavor formation produced in food products by lipid-derived reactive carbonyls.
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: Rosa M
authors.initials: RM
authors.lastname: Delgado
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. Electronic address: rzamora@ig.csic.es.
authors.forename: Rosario
authors.initials: R
authors.lastname: Zamora
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D008055:Lipids / Q000737:chemistry*; D015416:Maillard Reaction; D010636:Phenols / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D008055:Lipids; D010636:Phenols
keywords: 1,2,4-Trihydroxybenzene (PubChem ID: 10787); 2-Pentenal (PubChem ID: 5364752); Benzoquinone (PubChem ID: 4650); Carbonyl–amine reactions; Carbonyl–phenol reactions; Catechol (PubChem ID: 289); Hydroquinone (PubChem ID: 785); Lipid oxidation; Maillard reaction; Phenolic compounds; Phenylacetaldehyde (PubChem ID: 998); Phenylalanine (PubChem ID: 994); Phloroglucinol (PubChem ID: 359); Pyrogallol (PubChem ID: 1057); Resorcinol (PubChem ID: 5054); Strecker degradation