Phenolic compounds have been traditionally employed for controlling heterocyclic aromatic amine formation, and diverse studies have shown that the use of phenolic compounds (and plant extracts rich in them) decreases the 2-amino-1-methyl-6-phenylimidazo[4,5-<i>b</i>]pyridine (PhIP) formed in foods. However, there is not a correlation between the antioxidant/free radical scavenging ability of phenolic compounds and the inhibition of PhIP formation. In fact, addition of some phenolic antioxidants are able to increase the PhIP produced. In an attempt to understand the commonly observed dual role of phenolics as promoters and inhibitors of processes involving both free radicals and carbonyl compounds, this study analyzes the effect of the 13-hydroperoxide of linoleic acid on the formation of PhIP in the presence of a wide array of phenolic compounds. As comparison, the same reactions were also studied by substituting the hydroperoxide with 4-oxo-2-nonenal, a carbonyl compound derived from it. The obtained results showed that some phenolics can act as promoters or inhibitors of PhIP depending on the presence or not of the lipid hydroperoxide. This behavior is explained by the production of lipid radicals that can oxidize phenolics and increase the concentration of the carbonyl compounds needed for the formation of PhIP. The structure-reactivity of phenolics in their promoting/inhibitory activity is discussed.

Lipid hydroperoxides and the either promoting or inhibitory role of phenolic compounds in 2-amino-1-methyl-6-phenylimidazo[4,5-<i>b</i>]pyridine (PhIP) formation

254th National Meeting (2017)

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Lipid hydroperoxides and the either promoting or inhibitory role of phenolic compounds in 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) formation