Abstract
The degradation of three polycyclic aromatic hydrocarbons (PAH), pyrene (PYR), benz[a]anthracene (BAA), and benzo[a]pyrene (BaP), by Mycobacterium sp. strain RJGII-135 was studied. The bacterium was isolated from an abandoned coal gasification site soil by analog enrichment techniques and found to mineralize [14C]PYR. Further degradation studies with PYR showed three metabolites formed by Mycobacterium sp. strain RJGII-135, including 4,5-phenanthrene-dicarboxylic acid not previously isolated, 4-phenanthrene-carboxylic acid, and 4,5-pyrene-dihydrodiol. At least two dihydrodiols, 5,6-BAA-dihydrodiol and 10,11-BAA-dihydrodiol, were confirmed by high-resolution mass spectral and fluorescence analyses as products of the biodegradation of BAA by Mycobacterium sp. strain RJGII-135. Additionally, a cleavage product of BAA was also isolated. Mass spectra and fluorescence data support two different routes for the degradation of BaP by Mycobacterium sp. strain RJGII-135. The 7,8-BaP-dihydrodiol and three cleavage products of BaP, including 4,5-chrysene-dicarboxylic acid and a dihydro-pyrene-carboxylic acid metabolite, have been isolated and identified as degradation products formed by Mycobacterium sp. strain RJGII-135. These latter results represent the first example of the isolation of BaP ring fission products formed by a bacterial isolate. We propose that while this bacterium appears to attack only one site of the PYR molecule, it is capable of degrading different sites of the BAA and BaP molecules, and although the sites of attack may be different, the ability of this bacterium to degrade these PAH is well supported. The proposed pathways for biodegradation of these compounds by this Mycobacterium sp. strain RJGII-135 support the dioxygenase enzymatic processes reported previously for other bacteria. Microorganisms like Mycobacterium sp. strain RJGII-135 will be invaluable in attaining the goal of remediation of sites containing mixtures of these PAH.
Full Text
The Full Text of this article is available as a PDF (232.6 KB).
Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- Baker T. S., Harry J. V., Russell J. W., Myers R. L. Rapid method for the GC/MS confirmation of 11-nor-9-carboxy-delta 9-tetrahydrocannabinol in urine. J Anal Toxicol. 1984 Nov-Dec;8(6):255–259. doi: 10.1093/jat/8.6.255. [DOI] [PubMed] [Google Scholar]
- Boldrin B., Tiehm A., Fritzsche C. Degradation of phenanthrene, fluorene, fluoranthene, and pyrene by a Mycobacterium sp. Appl Environ Microbiol. 1993 Jun;59(6):1927–1930. doi: 10.1128/aem.59.6.1927-1930.1993. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Gibson D. T., Mahadevan V., Jerina D. M., Yogi H., Yeh H. J. Oxidation of the carcinogens benzo [a] pyrene and benzo [a] anthracene to dihydrodiols by a bacterium. Science. 1975 Jul 25;189(4199):295–297. doi: 10.1126/science.1145203. [DOI] [PubMed] [Google Scholar]
- Grosser R. J., Warshawsky D., Vestal J. R. Indigenous and enhanced mineralization of pyrene, benzo[a]pyrene, and carbazole in soils. Appl Environ Microbiol. 1991 Dec;57(12):3462–3469. doi: 10.1128/aem.57.12.3462-3469.1991. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Heitkamp M. A., Freeman J. P., Miller D. W., Cerniglia C. E. Pyrene degradation by a Mycobacterium sp.: identification of ring oxidation and ring fission products. Appl Environ Microbiol. 1988 Oct;54(10):2556–2565. doi: 10.1128/aem.54.10.2556-2565.1988. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Holder C. L., Korfmacher W. A., Slikker W., Jr, Thompson H. C., Jr, Gosnell A. B. Mass spectral characterization of doxylamine and its rhesus monkey urinary metabolites. Biomed Mass Spectrom. 1985 Apr;12(4):151–158. doi: 10.1002/bms.1200120403. [DOI] [PubMed] [Google Scholar]
- Kelley I., Freeman J. P., Evans F. E., Cerniglia C. E. Identification of metabolites from the degradation of fluoranthene by Mycobacterium sp. strain PYR-1. Appl Environ Microbiol. 1993 Mar;59(3):800–806. doi: 10.1128/aem.59.3.800-806.1993. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Mahaffey W. R., Gibson D. T., Cerniglia C. E. Bacterial oxidation of chemical carcinogens: formation of polycyclic aromatic acids from benz[a]anthracene. Appl Environ Microbiol. 1988 Oct;54(10):2415–2423. doi: 10.1128/aem.54.10.2415-2423.1988. [DOI] [PMC free article] [PubMed] [Google Scholar]