Lin J K, Wu S S, Chen J T
Proc Natl Sci Counc Repub China B. 1986 Oct;10(4):280-6.
Food-borne amines have been considered as the potential precursors of endogenous carcinogenic N-nitroso compounds in humans. A compound which yields a direct mutagen after nitrite treatment was isolated from soy sauce and was identified as 1-methyl-1,2,3,4-tetrahydro-2-carboline-3-carboxylic acid (MTCA) (Wakabayashi, et al., 1983). The mutagenicities of other carboline derivatives such as harman, norharman, harmaline, harmalol, harmine, and harmol were studied. Like MTCA, the nitrosated carboline derivatives showed higher mutagenic activity as compared to their corresponding parent compounds. The demethylated analogue of MTCA, 1,2,3,4-tetrahydro-2-carboline-3-carboxylic acid was synthesized and its nitrosated products were shown to be mutagenic to Salmonella typhimurium TA 100 and TA 98. The potent mutagen Trp-P-2 is a typical 3-carboline derivative. The mutagenicity of Trp-P-2 was suppressed remarkably after nitrosation. Several 3-carboline derivatives also showed the similar property. Nitrosation of MTCA gave several derivatives which were isolated and showed direct mutagenicity to Salmonella typhimurium TA 98. Further characterization of these new carboline derivatives is in progress.
食源性胺类被认为是人体内内源性致癌N-亚硝基化合物的潜在前体。从酱油中分离出一种经亚硝酸盐处理后产生直接诱变剂的化合物，并鉴定为1-甲基-1,2,3,4-四氢-2-咔啉-3-羧酸（MTCA）（若林等人，1983年）。对其他咔啉衍生物如哈尔满、去甲哈尔满、骆驼蓬碱、去氢骆驼蓬碱、骆驼蓬胺和去氢骆驼蓬胺的诱变性进行了研究。与MTCA一样，亚硝化咔啉衍生物与其相应的母体化合物相比，表现出更高的诱变活性。合成了MTCA的去甲基类似物1,2,3,4-四氢-2-咔啉-3-羧酸，并证明其亚硝化产物对鼠伤寒沙门氏菌TA 100和TA 98具有诱变性。强效诱变剂Trp-P-2是一种典型的3-咔啉衍生物。亚硝化后，Trp-P-2的诱变性显著降低。几种3-咔啉衍生物也表现出类似的性质。MTCA的亚硝化产生了几种衍生物，这些衍生物被分离出来，并对鼠伤寒沙门氏菌TA 98表现出直接诱变性。这些新的咔啉衍生物的进一步表征正在进行中。
