Isorhamnetin and Hispidulin from Tamarix ramosissima Inhibit 2-Amino-1-Methyl-6-Phenylimidazo[4,5-b]Pyridine (PhIP) Formation by Trapping Phenylacetaldehyde as a Key Mechanism

Abstract

Tamarix has been widely used as barbecue skewers to obtain a good taste and a unique flavor of roast lamb in China. Many flavonoids have been identified from Tamarix, which is an important strategy employed to reduce the formation of heterocyclic amines (HAs) in roast meat. Isorhamnetin, hispidulin, and cirsimaritin from Tamarix ramosissima bark extract (TRE) effectively inhibit the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b] pyridine (PhIP), the most abundant HAs in foods, both in roast lamb patties and in chemical models. According to the results of the GC-MS analysis, TRE and the three flavonoids significantly reduced the contents of phenylacetaldehyde, an important intermediate involved in PhIP formation at three levels. A subsequent ultra performance liquid chromatography-mass spectrometry (UPLC-MS) analysis revealed that these flavonoids trapped phenylacetaldehyde by forming interaction adducts. The formation of three postulated adducts, 8-C-(E-phenylethenyl)isorhamnetin, 6-C-(E-phenylethenyl)isorhamnetin and 8-C-(E-phenylethenyl)hispidulin, in the chemical models and roast lamb patties was further confirmed by a TOF-MS/MS analysis. Our results demonstrate that TRE and the corresponding flavonoids trap phenylacetaldehyde to form adducts and thus inhibit PhIP formation, suggesting their great potential beneficial effects on human health.