The identification of a new heterocyclic amine mutagen from a heated mixture of creatine, glutamic acid and glucose.
A new heterocyclic amine mutagen was isolated from a dry-heated reaction of the natural meat components creatine, glutamic acid and glucose. Heating creatine and glutamic acid alone had only one seventh of the Ames/Salmonella mutagenic activity of the glucose, creatine and glutamic acid mixture. The major mutagenic compound was purified by HPLC using the Ames/Salmonella test to guide the purification. The mutagen has a molecular weight of 244 and a composition of C12H12N4O2 as determined by high-resolution mass spectrometry. NMR and IR spectral data suggest the structure is a 2,6-diamino-3,4-dimethyl-7-oxo-pyrano[4,3-g]benzimidazole. Mutagenic activity in strains TA1538, TA98 and TA100, was approximately 7000, 5200, and 550 revertants per microgram, respectively. The formation of this mutagen from natural meat components suggests that it may be present in cooked food. The preferential formation of this mutagen with glucose shows that glucose can be important in dry-heated mutagen-forming reactions.
Biomedical Sciences Division, University of California, Lawrence Livermore National Laboratory 94550.
M G
MG
Knize
E
E
Hopmans
J A
JA
Happe
D002851:Chromatography, High Pressure Liquid; D003401:Creatine / Q000737:chemistry*; D005947:Glucose / Q000737:chemistry*; D005971:Glutamates / Q000737:chemistry*; D018698:Glutamic Acid; D006358:Hot Temperature; D007093:Imidazoles / Q000737:chemistry / Q000302:isolation & purification / Q000633:toxicity*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009153:Mutagens; D012486:Salmonella typhimurium / Q000235:genetics; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
D005971:Glutamates; D007093:Imidazoles; D009153:Mutagens; C070381:2,6-diamino-3,4-dimethyl-7-oxopyrano(4,3-g)benzimidazole; D018698:Glutamic Acid; D005947:Glucose; D003401:Creatine