Acylated anthocyanin inhibited the formation of heterocyclic amines in hybrid chemical model system and its underlying mechanism

Abstract

Enzymatic acylation was employed to synthesize acylated anthocyanin, and a hybrid chemical model system was used for the formation of heterocyclic amines. And the inhibition effect and underline mechanism were investigated by analyzing the variations in important precursors and intermediates. Results confirmed that cyanidin-3-(6-cinnamoyl) -glycosidase (C3(6C)G) with a purity of 98.9% was obtained. HPLC identified seven types of heterocyclic amines (IQ, MeIQx, 4, 8-DimeiqX, Norharman, Harman, PhIP, and AαC) generated in the chemical model. (C3(6C)G) showed a good concentration-dependent manner for the inhibition effect on most HCAs except for MeIQx and PhIP. It also suppressed the glucose content, showed a dose-dependent manner in creatine/creatinine inhibition, and could scavenge formaldehyde, acetaldehyde, and phenylacetaldehyde. Two potential pathways might be involved: 1. by inhibiting the content of precursors (glucose and creatinine), competing with the formation of amino acids, to suppress HCAs generation; 2 through the removal of reactive carbonyl, reducing its reaction with creatinine.

Keywords

• Acylated anthocyanin
• Chemical models heterocyclic amine
• Inhibition
• Enzymatic acylation