Knize M G, Roper M, Shen N H, Felton J S
Biomedical Sciences Division, University of California, Lawrence Livermore National Laboratory, Livermore 94550.
Carcinogenesis. 1990 Dec;11(12):2259-62. doi: 10.1093/carcin/11.12.2259.
New analytical data allow the structure of a potent mutagen previously reported present in cooked meats to be proposed. The mutagen was isolated from a fried mixture of beef, creatine and milk, simulating a meat recipe previously shown to produce this compound. High-resolution mass spectra indicate a mol. wt of 202 and the formula C10H10N4O. Mutagenic activity was 10,000 TA1538 revertants per microgram in the Ames Salmonella test. From the NMR data, peaks showing an amino group at 6.812 p.p.m. and an N-methyl group at 3.520 p.p.m. were found, typical for the amino-imidazo structure commonly found in cooked meats. Additional signals at 2.440 p.p.m. (three protons), 7.653 (one proton) and 6.531 (one proton) were observed. A structure of 2-amino-(1 or 3),6-dimethylfuro[2,3(or 3,2)-e]imidazo- [4,5-b]pyridine was proposed based on the mass and NMR spectral data and comparison to literature compounds. The methylimidazofuropyridine reported here is probably related to another mutagen in cooked meats with a mol. wt of 216 with an additional methyl group on either the furan or pyridine rings.
新的分析数据使得此前报道的存在于熟肉中的一种强效诱变剂的结构得以提出。该诱变剂是从牛肉、肌酸和牛奶的油炸混合物中分离出来的，模拟了之前显示会产生这种化合物的一种肉类食谱。高分辨率质谱表明其分子量为202，分子式为C₁₀H₁₀N₄O。在艾姆斯沙门氏菌试验中，诱变活性为每微克10000个TA1538回复突变体。根据核磁共振数据，发现了在6.812 ppm处显示氨基以及在3.520 ppm处显示N - 甲基的峰，这是熟肉中常见的氨基咪唑结构的典型特征。还观察到在2.440 ppm（三个质子）、7.653（一个质子）和6.531（一个质子）处的其他信号。基于质谱和核磁共振光谱数据以及与文献化合物的比较，提出了2 - 氨基 - (1或3),6 - 二甲基呋喃并[2,3(或3,2)-e]咪唑并[4,5 - b]吡啶的结构。此处报道的甲基咪唑并呋喃并吡啶可能与熟肉中的另一种诱变剂有关，后者分子量为216，在呋喃环或吡啶环上带有一个额外的甲基。
