Isolation and identification of a new mutagen, 2-amino-4-hydroxy-methyl-3, 8-dimethylimidazo[4,5-f] quinoxaline (4-CH2OH-8-MeIQx), from beef extract

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Abstract
By monitoring the mutagenicity to a new Salmonella tester strain, YG1024, which has a much higher level of 0- acetyltransferase activity than S.typhimurium TA98, we found two new mutagenic compounds in bacteriological-grade beef extract. One of them (compound I), which had a similar UV spectrum to that of 2-amlno-3,4,8-trimethylimidazo [4,5-f]quinoxaline (4,8-DiMeIQx), was isolated and shown to account for ˜2% of the total mutagenicity of the materials adsorbed to blue cotton, and its concentration was estimated to be 6.0 ng/g beef extract. This amount of compound in beef extract was insufficient to allow measurements of various spectra, but its level was increased ˜9-fold by heating beef extract with creatine and threonine at 200°C for 5 h. From UV and mass spectra of the compound obtained from beef extract heated with creatine plus threonine, it was deduced to be a hydroxymethyl derivative of anminodimethylimidazoquinoxaline. Compound I was isolated from the urine of rats given 4,8-DiMeIQx and identified as 2-amino-4-hydroxymethyl-3,8-dimethylimidazo [4,5-f]quinoxaline (4-CH2OH-8-MeIQx) by 1H-NMR analysis. 4-CH2OH-8-MeIQx induced 326 000 revertants of YG1024 and 99 000 revertants of TA98 per μg in the presence of S9 mix.

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