Structural determination of a new mutagenic heterocydic amine, 2-amino-1,7,9-trimethylimidazo[4,5-g]quinoxaline (7,9-DiMeIgQx), present in beef extract |
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Authors: | Nukaya Haruo; Koyota Souichi; Jinno Fumihiro; Ishida Histoshi; Wakabayashi Keiji; Kurosaka Reiko; Kim In-Soo; Yamaizumi Ziro; Ushiyama Hirofumi; Sugimura Takashi; Nagao Minako; Tsuji Kuniro |
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Institution: | School of Pharmaceutical Science, University of Shizuoka 521 Yada, Shizuoka 422
1Carcinogenesis National Cancer Center Research Institute 1-1 Tsukiji 5-chome, Chuo-ku, Tokyo 104
2Biology Divisions, National Cancer Center Research Institute 1-1 Tsukiji 5-chome, Chuo-Ku, Tokyo 104
3Division of Food Hygiene, The Tokyo Metropolitan Research Laboratory of Public Health 241 Hyakunincho 3-chome, Shiriju-ku, Tokyo 169, Japan |
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Abstract: | We previously found two new mutagens, compounds I and II, inbacteriological-grade beef extract by monitoring the mutagenicityto a new Salmonella strain, YG1024; compound I was identifiedas 2-amino-4-hydroxymethyl-3,8-dimethyli-midazo4,5-f]quinoxaline(4-CH2OH-8-MeIQX) In the present study, we isolated compoundII from the beef extract, which accounted for 2% of the totalmutagenicity of materials adsorbed on blue cotton. Further,we found that a large quantity of compound II was produced byheating a mixture of creatine, threonine and glucose (1:1:0.5)at 200°C for 5 h, the level being 860-fold of that in thebeef extract. The structure of this compound was determinedto be 2-amino-1,7,9-trimethylimidazo4,5-g]quinoxaline (7,9-DiMeIgQx)by X-ray crystallography. The amount of 7,9-DiMeIgQx in bacteriological-gradebeef extract was estimated to be 53 ng/g. This compound induced13 800 and 670 revertants of S.typhimurium YG1024 and TA98 respectively,per µg in the presence of S9 mix. |
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