Massé R, Lalanne D, Messier F, Sylvestre M
Institut National de la Recherche Scientifique, Université du Québec Canada.
Biomed Environ Mass Spectrom. 1989 Sep;18(9):741-52. doi: 10.1002/bms.1200180917.
The microbial transformation of DDT, DDD and DDE was studied in Gram-negative strain B-206 and a number of phenolic metabolites were identified as the trimethylsilyl derivatives in the bacterial extracts by gas chromatography/mass spectrometry. The major metabolites of DDT were DDD, DDE, DDMU, 1,1,1-trichloro-2-(2-hydroxy-4-chlorophenyl)-2-(4'-chlorophenyl) ethane, 1,1,1-trichloro-2-(2-hydroxy-4-chlorophenyl)-2-(4'-hydroxyphenyl) ethane, and 1,1,1-trichloro-2,2-bis-(2-hydroxy-4-chlorophenyl) ethane. Conversely, DDD was mainly degraded into DDE, 1,1-dichloro-2-(2-hydroxy-4-chlorophenyl)-2-(4'-chlorophenyl) ethane and 1,1-dichloro-2-(2-hydroxy-4-chlorophenyl)-2-(4'-hydroxyphenyl) ethane. Finally, DDE was transformed into DDMU, 1,1-dichloro-2-(2-hydroxy-4-chlorophenyl)-2-(4'-chlorophenyl) ethylene, 1,1-dichloro-2-(2-hydroxy-4-chlorophenyl)-2-(4'hydroxyphenyl) ethylene and 1-chloro-2-(2-hydroxy-4-chlorophenyl)-2-(4'-chlorophenyl) ethylene. The phenolic metabolites exhibited [M - TMSCl]+., [M - HCl - TMSCl]+. and/or [M - HCl - TMSCl - Me]+ fragment ions which reflect the presence of an ortho hydroxyl group in these molecules. Other mass spectral features used to determine their structure are presented and a metabolic scheme accounting for their formation is proposed.
在革兰氏阴性菌株B - 206中研究了滴滴涕（DDT）、滴滴滴（DDD）和滴滴伊（DDE）的微生物转化过程，通过气相色谱/质谱法在细菌提取物中鉴定出多种酚类代谢产物为三甲基硅烷基衍生物。DDT的主要代谢产物为DDD、DDE、滴滴酮（DDMU）、1,1,1 - 三氯 - 2 -（2 - 羟基 - 4 - 氯苯基）- 2 -（4'-氯苯基）乙烷、1,1,1 - 三氯 - 2 -（2 - 羟基 - 4 - 氯苯基）- 2 -（4'-羟基苯基）乙烷以及1,1,1 - 三氯 - 2,2 - 双 -（2 - 羟基 - 4 - 氯苯基）乙烷。相反地，DDD主要降解为DDE、1,1 - 二氯 - 2 -（2 - 羟基 - 4 - 氯苯基）- 2 -（4'-氯苯基）乙烷和1,1 - 二氯 - 2 -（2 - 羟基 - 4 - 氯苯基）- 2 -（4'-羟基苯基）乙烷。最后，DDE转化为DDMU、1,1 - 二氯 - 2 -（2 - 羟基 - 4 - 氯苯基）- 2 -（4'-氯苯基）乙烯、1,1 - 二氯 - 2 -（2 - 羟基 - 4 - 氯苯基）- 2 -（4'-羟基苯基）乙烯以及1 - 氯 - 2 -（2 - 羟基 - 4 - 氯苯基）- 2 -（4'-氯苯基）乙烯。这些酚类代谢产物呈现出[M - TMSCl]+、[M - HCl - TMSCl]+和/或[M - HCl - TMSCl - Me]+碎片离子，这反映了这些分子中邻位羟基的存在。文中还展示了用于确定其结构的其他质谱特征，并提出了一个解释它们形成的代谢方案。
