title: Reactive carbonyl-scavenging ability of 2-aminoimidazoles: 2-amino-1-methylbenzimidazole and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP).
abstract: The carbonyl-scavenging ability of 2-amino-1-methylbenzimidazole (AMBI) and the heterocyclic aromatic amine 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) was investigated in an attempt to identify new routes that can modify the carbonyl content of foods. The reaction of both AMBI and PhIP with 2-alkenals, 2,4-alkadienals, 4-oxo-2-alkenals, 4,5-epoxy-2-alkenals, and 4-hydroxy-2-nonenal produced fluorescent adducts, whose structure was determined for the adduct produced between AMBI and 2-pentenal. This adduct was isolated and identified by one- and two-dimensional nuclear magnetic resonance and high-resolution mass spectrometry as 2,10-dihydro-2-ethyl-10-methylpyrimido[1,2-a]benzimidazole. The formation of these adducts was parallel to the elimination of AMBI and PhIP. The Ea of the reaction between PhIP and 4-oxo-2-nonenal was 27.4 kJ/mol. All these results suggest that 2-aminoimidazoles can be employed to modify the carbonyl content of foods. At the same time and because the reaction produces the disappearance of the amino compound, lipid-derived carbonyl compounds can be employed to eliminate 2-aminoimidazoles, which suggests a new strategy for the elimination of heterocyclic aromatic amines in foods.
authors.affiliation: Instituto de la Grasa, Consejo Superior de Investigaciones Científicas , Avenida Padre García Tejero 4, 41012 Seville, Spain.
authors.forename: Francisco J
authors.initials: FJ
authors.lastname: Hidalgo
authors.forename: Esmeralda
authors.initials: E
authors.lastname: Alcón
authors.forename: Rosario
authors.initials: R
authors.lastname: Zamora
mesh_terms: D016166:Free Radical Scavengers / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry*
chemical_list: D016166:Free Radical Scavengers; D005609:Free Radicals; D007093:Imidazoles; C014973:2-aminoimidazole; C049584:2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine
keywords: 2,4-alkadienals; 4,5-epoxy-2-alquenals; 4-hydroxy-2-nonenal; 4-oxo-2-alkenals; heterocyclic aromatic amines; reactive carbonyls