ISSN:
1572-9729
Keywords:
biodegradation
;
quinoline
;
methylquinolines
;
anaerobic biotransformation
Source:
Springer Online Journal Archives 1860-2000
Topics:
Biology
,
Energy, Environment Protection, Nuclear Power Engineering
,
Agriculture, Forestry, Horticulture, Fishery, Domestic Science, Nutrition
Notes:
Abstract Quinoline (Q) and some isomers of methylquinoline (MQ) were transformed to hydroxylated products in freshwater sediment slurries incubated under methanogenic conditions at 25 °C. Methylquinoline transformation was not affected by a methyl group on the C-3 or C-4 carbon atom of the pyridine ring; 2-MQ, however, was not transformed. All isomers of dimethylquinoline (DMQ) tested (2,4-, 2,6-, 2,7-, and 2,8-DMQ) with a methyl group at the number 2 carbon also persisted in sediments after anaerobic incubation for one year at 25 °C. In most experiments, quinoline initially was transformed to 2-hydroxyquinoline (2-OH-Q), which was further metabolized to unidentified products. A second product, 4-CH3-2-OH-Q, was detected in some experiments. This product accumulated and was not further transformed. 6-, 7-, and 8-Methylquinoline (6-, 7-, 8-MQ) were hydroxylated to form the respective 2-OH-MQ products. These hydroxylated products accumulated and were not further transformed. Hydroxylation of Q and 6-, 7- and 8-MQ at the 2-carbon position was confirmed by GC/FTIR and GC/MS analyses. The transformations of Q and MQs were pH dependent with an optimal pH of 7–8. The results of this study suggest that two pathways may exist for the anaerobic transformation of quinoline; one pathway leads to the formation of a hydroxylated intermediate and the other to a methylated and hydroxylated intermediate. In addition, our results suggest that a methyl substituent on the number 2 carbon inhibits the anaerobic transformation of quinoline derivatives.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00700636
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