Mechanism of eugenol from bay leaf in inhibiting heterocyclic aromatic amines in grilled beef: Insights from experimental models and computational chemistry.

This study investigated inhibitory mechanisms of eugenol, the primary bioactive compound in bay leaf, against formation of free and protein-bound heterocyclic aromatic amines (HAAs) in grilled beef. Bay leaf exhibited the strongest inhibitory efficacy among the tested spices, reducing total free (43.10%) and protein-bound (68.88%) HAAs in grilled beef. In chemical models, eugenol mitigated free and bound HAA formation by up to 71.88% and 91.89%, respectively. Density functional theory calculations suggested that eugenol potentially interacted with creatine, phenylacetaldehyde, and 2,5-dimethylpyrazine via hydrogen bonding and van der Waals interactions, which may contribute to the inhibition of free HAA formation. Spectroscopic analyses and molecular dynamics simulations demonstrated that eugenol stably bound to myosin residues, inducing a more compact structure that sterically shielded reactive amino acid sites and inhibited bound HAA formation. These findings offer molecular insights into using natural phenolic compounds for mitigating heat-induced chemical hazards in protein-rich foods.