Metabolic pathways of quinoline, indole and their methylated analogs by Desulfobacterium indolicum (DSM 3383)
Metabolic pathways of quinoline, indole and their methylated analogs by Desulfobacterium indolicum (DSM 3383)
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DOI：
10.1007/s002530050929
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发表时间：
1997-03-01
影响因子：
5
通讯作者：
Hansen, AB
中科院分区：
文献类型：
--
作者：
Johansen, SS;Licht, D;Hansen, AB
比较了吲哚脱硫杆菌对喹啉、异喹啉和3-、4-、6-和8-甲基喹啉的转化与含氮类似物吲哚和1-、2-、3-和7-甲基吲哚的转化。采用高效液相色谱-紫外检测、薄层色谱、气相色谱/质谱联用和质子核磁共振波谱法鉴定代谢产物。所有降解的化合物最初在2位被D羟基化。吲哚在第二个转化步骤中观察到喹啉的新降解产物，其中3，4-二氢-2-喹啉酮积累。该环还原的化合物进一步转化为未鉴定的产物。吲哚的转化途径的特点是众所周知的步骤，通过羟吲哚，靛红，邻氨基苯甲酸。在孵育162天内，未观察到羟基化甲基类似物：3-和7-甲基羟吲哚以及3-和4-甲基-2-喹啉酮的进一步转化。这些降解产物以化学计量的量积累，而6-和8-甲基-2-喹啉酮进一步降解为化学计量的6-和8-甲基-3，4-二氢-2-喹啉酮。异喹啉、2-甲基喹啉、1-和2-甲基吲哚不被D.吲哚这些观察结果表明，在位置2处或接近位置2的甲基导致微生物攻击的阻断，并且在杂环处甲基化的羟基喹啉的转化也被阻断或空间抑制。观察到一些甲基化化合物的不完全转化，例如3-和6-甲基喹啉以及3-和7-甲基吲哚，相对于10-15 mg/l的初始浓度，残留浓度为0.5-4 mg/l。
The transformation of quinoline, isoquinoline and 3-, 4-, 6- and 8-methylquinoline by Desulfobacterium indolicum was compared with that of the N-containing analogues indole and 1-, 2-, 3- and 7-methylindole. The metabolites were identified using high-performance liquid chromatography with UV detection, thin-layer chromatography, combined gas chromatography/mass spectrometry and proton NMR spectroscopy. All degraded compounds were initially hydroxylated at position 2 by D. indolicum. A new degradation product of quinoline was observed in the second transformation step, where 3,4-dihydro-2-quinolinone accumulated. This ring-reduced compound was further transformed into unidentified products. The transformation pathway of indole was characterized by well-known steps through oxindole, isatin, and anthranilic acid. No further transformation of the hydroxylated methyl analogues: 3- and 7-methyloxindole and 3- and 4-methyl-2-quinolinone, was observed within 162 days of incubation. These degradation products accumulated in stoichiometric amounts, while 6- and 8-methyl-2-quinolinone were further degraded to 6- and 8-methyl-3,4-dihydro-2-quinolinone in stoichiometric amounts. Isoquinoline, 2-methylquinoline and 1- and 2-methylindole were not degraded by D. indolicum. These observations indicate that a methyl group at or close to position 2 results in blockage of the microbial attack, and that transformation of hydroxyquinolines methylated at the heterocyclic ring also was blocked or sterically inhibited. An incomplete transformation of some methylated compounds was observed, e.g. for 3- and 6-methylquinoline and 3- and 7-methylindole, with residual concentrations of 0.5-4 mg/l in relation to initial concentrations of 10-15 mg/l.