METABOLISM OF 3-DEOXYGLUCOSONE, AN INTERMEDIATE COMPOUND IN THE MAILLARD REACTION, ADMINISTERED ORALLY OR INTRAVENOUSLY TO RATS

Tha Amadori rearrangement compound, the product in the early step of the Maillard reaction of proteins with glucose, is known to be degraded into 3-deoxyglucosone (3DG), a 2-oxoaldehyde. In order to elucidate the metabolic pathway of 3DG, [14C]3DG was synthesized from [14C]-glucose and administered to rats orally and intravenously. 2 h after oral administration of [14C]3DG, the percentages of radioactivity (RaI%) in stomach, small intestine and urine were 3.9, 60 and 6.4%, respectively, while RaI% in liver, kidney, spleen, blood and CO2 were less than 0.5%. The absorption rate of 3DG was obviously lower in comparison with that of glucose. 3 h after intravenous administration of [14C]3DG, the RaI% in urine was 72% and those in liver, kidney, spleen, blood and CO2 were less than 1%. It therefore appeared that the absorbed 3DG was not biologically utilized by the rats, but was rapidly excreted in the urine. Some metabolites of [14C]3DG were detected in urine by TLC-autoradiography. The main metabolite was purified and identified as 3-deoxyfructose by FD-MS and 13C-NMR spectroscopy, indicating that the aldehyde group of 3DG was reduced to an alcohol. © 1990.