Chemical Structures of Novel Maillard Reaction Products under Hyperglycemic Conditions

Two novel and two known compounds, 4-quinolylaldoxime and indole-3-aldehyde, were isolated from a reaction mixture consisting of D-glucose and L-tryptophan at physiological temperature and pH. The chemical structures of the two novel compounds were elucidated by spectroscopic analysis such as X-ray crystallography. One of the novel compound and the indole-3-aldehyde showed mutagenicity toward Salmonella typhimurium YG1024 with S9 mix. Furthermore, 4-quinolylaldoxime was detected from streptozotocin-induced diabetic rat plasma by LC-MS/MS analysis; however, the isolated compounds were not detected in rat diet extracts. To our knowledge, this is the first report in which 4-quinolylaldoxime was detected in rat plasma. These results suggest that amino-carbonyl reaction products may be formed in diabetic condition and induce genetic damage.