Inhibition of the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b] pyridine (PhIP) and 2-amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline (MeIQx) by phenolics in model systems and beef patties

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dc.contributor.authorCaro-Cabarcas, Angye D.
dc.contributor.authorAlcon, Esmeralda
dc.contributor.authorMariotti-Celis, María Salomé
dc.contributor.authorPedreschi, Franco
dc.contributor.authorHidalgo, Francisco J.
dc.contributor.authorZamora, Rosario
dc.date.accessioned2025-06-18T21:18:26Z
dc.date.available2025-06-18T21:18:26Z
dc.date.issued2025-03-28
dc.description.abstractThe comparative inhibition of the formation of 2-amino-1-methyl-6- phenylimidazo[4,5-b]pyridine (PhIP) and 2-amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline (MeIQx) by phenolics in both model systems and beef patties was studied to better understand the protective role of these compounds. Model systems were selected to produce PhIP and MeIQx by carbonyl-amine reactions. Obtained results showed that their formation was inhibited up to 100 % by assayed phenolics. Among simple phenolics, m-diphenols were usually more effective than o-diphenols, and MeIQx was better inhibited than PhIP because m-diphenols both produce the Strecker degradation of amino acids to a lower extent than o-diphenols, and trap acrolein (responsible for MeIQx formation) better than phenylacetaldehyde (responsible for PhIP formation). When complex phenolics were assayed, other groups also contributed to the observed protective function. However, relative inhibitions of both compounds in model systems and beef patties were correlated, therefore suggesting that the formation of PhIP and MeIQx also occurs in beef patties by carbonyl-amine reactions.
dc.identifier.citationFood Chemistry, Vol. 481, N°144091 (2025) p. 1-11.
dc.identifier.doihttps://doi.org/10.1016/j.foodchem.2025.144091
dc.identifier.issn0308-8146
dc.identifier.issne1873-7072
dc.identifier.orcidhttps://orcid.org/0000-0003-1357-812X
dc.identifier.urihttps://hdl.handle.net/20.500.12254/4163
dc.language.isoen
dc.publisherElsevier
dc.rightsAtribución-NoComercial-CompartirIgual 3.0 Chile (CC BY-NC-SA 3.0 CL)
dc.rights.urihttp://creativecommons.org/licenses/by-nc-sa/3.0/cl/
dc.subjectCarbonyl-amine reactions
dc.subjectCarbonyl-phenol reactions
dc.subjectReactions food carbonylome
dc.subjectHeterocyclic aromatic amines
dc.subjectMaillard reaction
dc.titleInhibition of the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b] pyridine (PhIP) and 2-amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline (MeIQx) by phenolics in model systems and beef patties
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