Skip to main content
PMC home page
Applied and Environmental Microbiology logoLink to Applied and Environmental Microbiology
. 1997 Dec;63(12):4759–4764. doi: 10.1128/aem.63.12.4759-4764.1997

Carboxylation as an initial reaction in the anaerobic metabolism of naphthalene and phenanthrene by sulfidogenic consortia.

X Zhang 1, L Y Young 1
PMCID: PMC168798  PMID: 9471963

Abstract

The anaerobic biodegradation of naphthalene (NAP) and phenanthrene (PHE) was investigated by using sediment collected from the Arthur Kill in New York/New Jersey harbor. The initial cultures were composed of 10% sediment and 90% mineral medium containing 20 mM sulfate. Complete loss of NAP and PHE (150 to 200 muM) was observed after 150 days of incubation. Upon refeeding, NAP and PHE were utilized within 14 days. The utilization of both compounds was inhibited in the presence of 20 mM molybdate. [14C]NAP and [14C]PHE were mineralized to 14CO2. The activities could be maintained and propagated by subculturing in mineral medium. In the presence of halogenated analogs, 2-naphthoate was detected in NAP-utilizing enrichments. The mass spectrum of the derivatized 2-napththoate from the enrichment supplemented with both [13C]bicarbonate and NAP indicates the incorporation of 13CO2 into NAP. In the PHE-utilizing enrichment, a metabolite was detected by both high-pressure liquid chromatography and gas chromatography-mass spectrometry analyses. The molecular ion and fragmentation pattern of its mass spectrum indicate that it was phenanthrenecarboxylic acid. The results obtained with [13C] bicarbonate indicate that 13CO2 was incorporated into PHE. It appears, therefore, that carboxylation is an initial key reaction for the anaerobic metabolism and NAP and PHE. To our knowledge, this is the first report providing evidence for intermediates of PAH degradation under anaerobic conditions.

Full Text

The Full Text of this article is available as a PDF (188.3 KB).

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Coates J. D., Anderson R. T., Lovley D. R. Oxidation of Polycyclic Aromatic Hydrocarbons under Sulfate-Reducing Conditions. Appl Environ Microbiol. 1996 Mar;62(3):1099–1101. doi: 10.1128/aem.62.3.1099-1101.1996. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Coates J. D., Woodward J., Allen J., Philp P., Lovley D. R. Anaerobic degradation of polycyclic aromatic hydrocarbons and alkanes in petroleum-contaminated marine harbor sediments. Appl Environ Microbiol. 1997 Sep;63(9):3589–3593. doi: 10.1128/aem.63.9.3589-3593.1997. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Gorny N., Schink B. Anaerobic degradation of catechol by Desulfobacterium sp. strain Cat2 proceeds via carboxylation to protocatechuate. Appl Environ Microbiol. 1994 Sep;60(9):3396–3400. doi: 10.1128/aem.60.9.3396-3400.1994. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Goyal A. K., Zylstra G. J. Molecular cloning of novel genes for polycyclic aromatic hydrocarbon degradation from Comamonas testosteroni GZ39. Appl Environ Microbiol. 1996 Jan;62(1):230–236. doi: 10.1128/aem.62.1.230-236.1996. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Gunster D. G., Bonnevie N. L., Gillis C. A., Wenning R. J. Assessment of chemical loadings to Newark Bay, New Jersey from petroleum and hazardous chemical accidents occurring from 1986 to 1991. Ecotoxicol Environ Saf. 1993 Apr;25(2):202–213. doi: 10.1006/eesa.1993.1019. [DOI] [PubMed] [Google Scholar]
  6. Harwood C. S., Gibson J. Shedding light on anaerobic benzene ring degradation: a process unique to prokaryotes? J Bacteriol. 1997 Jan;179(2):301–309. doi: 10.1128/jb.179.2.301-309.1997. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. He Z., Wiegel J. Purification and characterization of an oxygen-sensitive reversible 4-hydroxybenzoate decarboxylase from Clostridium hydroxybenzoicum. Eur J Biochem. 1995 Apr 1;229(1):77–82. doi: 10.1111/j.1432-1033.1995.tb20440.x. [DOI] [PubMed] [Google Scholar]
  8. He Z., Wiegel J. Purification and characterization of an oxygen-sensitive, reversible 3,4-dihydroxybenzoate decarboxylase from Clostridium hydroxybenzoicum. J Bacteriol. 1996 Jun;178(12):3539–3543. doi: 10.1128/jb.178.12.3539-3543.1996. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Heider J., Fuchs G. Anaerobic metabolism of aromatic compounds. Eur J Biochem. 1997 Feb 1;243(3):577–596. doi: 10.1111/j.1432-1033.1997.00577.x. [DOI] [PubMed] [Google Scholar]
  10. Kim E., Aversano P. J., Romine M. F., Schneider R. P., Zylstra G. J. Homology between genes for aromatic hydrocarbon degradation in surface and deep-subsurface Sphingomonas strains. Appl Environ Microbiol. 1996 Apr;62(4):1467–1470. doi: 10.1128/aem.62.4.1467-1470.1996. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Lack A., Fuchs G. Evidence that phenol phosphorylation to phenylphosphate is the first step in anaerobic phenol metabolism in a denitrifying Pseudomonas sp. Arch Microbiol. 1994;161(2):132–139. doi: 10.1007/BF00276473. [DOI] [PubMed] [Google Scholar]
  12. Marinucci A. C., Bartha R. Apparatus for monitoring the mineralization of volatile C-labeled compounds. Appl Environ Microbiol. 1979 Nov;38(5):1020–1022. doi: 10.1128/aem.38.5.1020-1022.1979. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Mihelcic J. R., Luthy R. G. Degradation of polycyclic aromatic hydrocarbon compounds under various redox conditions in soil-water systems. Appl Environ Microbiol. 1988 May;54(5):1182–1187. doi: 10.1128/aem.54.5.1182-1187.1988. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. Phelps C. D., Kazumi J., Young L. Y. Anaerobic degradation of benzene in BTX mixtures dependent on sulfate reduction. FEMS Microbiol Lett. 1996 Dec 15;145(3):433–437. doi: 10.1111/j.1574-6968.1996.tb08612.x. [DOI] [PubMed] [Google Scholar]
  15. Sharak Genthner B. R., Townsend G. T., Lantz S. E., Mueller J. G. Persistence of polycyclic aromatic hydrocarbon components of creosote under anaerobic enrichment conditions. Arch Environ Contam Toxicol. 1997 Jan;32(1):99–105. doi: 10.1007/s002449900160. [DOI] [PubMed] [Google Scholar]
  16. Zhang X., Wiegel J. Reversible Conversion of 4-Hydroxybenzoate and Phenol by Clostridium hydroxybenzoicum. Appl Environ Microbiol. 1994 Nov;60(11):4182–4185. doi: 10.1128/aem.60.11.4182-4185.1994. [DOI] [PMC free article] [PubMed] [Google Scholar]
  17. al-Bashir B., Cseh T., Leduc R., Samson R. Effect of soil/contaminant interactions on the biodegradation of naphthalene in flooded soil under denitrifying conditions. Appl Microbiol Biotechnol. 1990 Dec;34(3):414–419. doi: 10.1007/BF00170071. [DOI] [PubMed] [Google Scholar]

Articles from Applied and Environmental Microbiology are provided here courtesy of American Society for Microbiology (ASM)

RESOURCES