Carbonyl-trapping by phenolics and the inhibition of the formation of carcinogenic heterocyclic aromatic amines with the structure of aminoimidazoazaarene in beef patties

Abstract

Carcinogenic heterocyclic aromatic amines (HAAs) with the structure of aminoimidazoazaarene (PhIP, MeIQx, IQ, and MeIQ) are produced by reaction of creatin(in)e, ammonia, and reactive carbonyls (phenylacetaldehyde, acrolein, and crotonaldehyde). In an attempt to provide efficient methodologies for HAA reduction in beef patties, this study: identified phloroglucinol as the most efficient phenolic to reduce HAA formation (76-96% inhibition); isolated and characterized by NMR and MS phloroglucinol/phenylcetaldehyde and phloroglucinol/acrolein adducts; and determined by LC-MS/MS adduct formation in beef patties treated with phloroglucinol. Obtained results suggested that addition of trihydroxyphenols (including phloroglucinol) to beef patties should decrease HAA formation. This was confirmed by both immersing beef patties in apple (or pear) juice before cooking (>90% inhibition) and including wheat bran in patty recipe. All these results confirm the key role of reactive carbonyls in the formation of carcinogenic HAAs and propose carbonyl-trapping as a way for controlling HAA formation in food products.

Keywords: 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) (PubChem ID: 1530); 2-Amino-3,4-dimethyl-3H-imidazo[4,5-f]quinoline (MeIQ) (PubChem ID: 62274); 2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) (PubChem ID: 62275); 2-Amino-3-methyl-3H-imidazo[4,5-f]quinoline (IQ) (PubChem ID: 53462); Acrolein (2-propenal) (PubChem ID: 7847); Carbonyl-phenol reactions; Heterocyclic Aromatic Amines (HAAs); Lipid oxidation; Maillard reaction; Phenylacetaldehyde (PubChem ID: 998); Phloroglucinol; Reactive carbonyls.