Studies on the Formation of 3-Deoxyglucosone- and Methylglyoxal-Derived Hydroimidazolones of Creatine during Heat Treatment of Meat.

Dicarbonyl compounds such as methylglyoxal (MGO) and 3-deoxyglucosone (3-DG) are formed via caramelization and the Maillard reaction in food during heating or in vivo as byproducts of glycolysis. Recently, it was shown that creatine, an amino compound linked to the energy metabolism in vertebrate muscle, reacts rapidly with methylglyoxal under physiological conditions to form N-(4-methyl-5-oxo-1-imidazolin-2-yl)sarcosine (MG-HCr), a methylglyoxal-derived hydroimidazolone of creatine. Based on the observation that heated meat contains only small amounts of MGO and 3-DG when compared to many other foodstuffs, the aim of this study was to investigate a possible reaction of creatine with 3-DG and MGO in meat. From incubation mixtures consisting of 3-DG and creatine, a new hydroimidazolone of creatine, namely N-(4-butyl-1,2,3-triol-5-oxo-1-imidazolin-2-yl)sarcosine (3-DG-HCr), was isolated and characterized via spectroscopic means. To quantitate 3-DG-HCr and MG-HCr, meat and fish products were analyzed via HPLC-MS/MS using isotopically labeled standard material. Whereas samples of raw fish and meat contained only trace amounts of the hydroimidazolones (below 5 μg/kg), up to 28.3 mg/kg MG-HCr and up to 15.3 mg/kg 3-DG-HCr were found in meat and fish products. The concentrations were dependent on the heat treatment and presumably on the smoking process. In comparison to the lysine and arginine derivatives CEL, pyrraline, and MG-H1, the derivatization rate of creatine as MG-HCr and 3-DG-HCr was higher than of lysine and arginine, which clearly demonstrates the 1,2-dicarbonyl scavenging properties of creatine in meat.