Structural characteristics that determine the inhibitory role of phenolic compounds on 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) formation.

Abstract:

:In an attempt to understand the structural characteristics of phenolic compounds that favour the inhibition of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) formation, this study analyzes the role of twenty-five phenolic compounds on the PhIP produced in phenylalanine/creatinine/oxidised lipid reaction mixtures. The results showed that phenols having two hydroxy groups at meta positions of the aromatic ring were the most efficient inhibitors. The presence of alkyl or carboxylic groups as additional substituents in the aromatic ring slightly reduced the inhibitory effect. On the other hand, the introduction of additional hydroxy and amino groups mostly cancelled the inhibitory effect, which was also mostly absent in ortho and para dihydroxy derivatives. In complex phenols, the presence of several rings with opposite effects produced a reduced inhibitory effect. All these results suggest that it is possible to predict if a phenolic derivative will inhibit the formation of PhIP, or not, based on its structure.

journal_name

Food Chem

journal_title

Food chemistry

authors

Salazar R,Arámbula-Villa G,Hidalgo FJ,Zamora R

doi

10.1016/j.foodchem.2013.11.105

subject

Has Abstract

pub_date

2014-05-15 00:00:00

pages

480-6

eissn

0308-8146

issn

1873-7072

pii

S0308-8146(13)01793-7

journal_volume

151

pub_type

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