Skip to main content
NCBI home page
Applied and Environmental Microbiology logoLink to Applied and Environmental Microbiology
. 1992 Sep;58(9):2910–2917. doi: 10.1128/aem.58.9.2910-2917.1992

Isolation and characterization of a fluorene-degrading bacterium: identification of ring oxidation and ring fission products.

M Grifoll 1, M Casellas 1, J M Bayona 1, A M Solanas 1
PMCID: PMC183026  PMID: 1444405

Abstract

An Arthrobacter sp. strain, F101, able to use fluorene as the sole source of carbon and energy, was isolated from sludge from an oil refinery wastewater treatment plant. During growth in the presence of fluorene, four major metabolites were detected and isolated by thin-layer chromatography and high-performance liquid chromatography. 9-Fluorenol, 9H-fluoren-9-one, and 3,4-dihydrocoumarin were identified by UV spectra, mass spectrometry, and 300-MHz proton nuclear magnetic resonance. The fourth metabolite has been characterized, but precise identification was not possible. Since strain F101 is not able to grow with fluorenone, two different pathways of fluorene biodegradation are suggested: one supports cell growth and produces 3,4-dihydrocoumarin as an intermediate and probably the unidentified metabolite, and the other produces 9-fluorenol and 9H-fluoren-9-one and appears to be a dead-end route.

Full text

PDF
2910

Images in this article

2912Image
on p.2912

Selected References

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

  1. CONRAD H. E., DUBUS R., GUNSALUS I. C. An enzyme system for cyclic ketone lactonization. Biochem Biophys Res Commun. 1961 Nov 29;6:293–297. doi: 10.1016/0006-291x(61)90382-5. [DOI] [PubMed] [Google Scholar]
  2. Cerniglia C. E. Microbial metabolism of polycyclic aromatic hydrocarbons. Adv Appl Microbiol. 1984;30:31–71. doi: 10.1016/s0065-2164(08)70052-2. [DOI] [PubMed] [Google Scholar]
  3. Davies J. I., Evans W. C. Oxidative metabolism of naphthalene by soil pseudomonads. The ring-fission mechanism. Biochem J. 1964 May;91(2):251–261. doi: 10.1042/bj0910251. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Donoghue N. A., Norris D. B., Trudgill P. W. The purification and properties of cyclohexanone oxygenase from Nocardia globerula CL1 and Acinetobacter NCIB 9871. Eur J Biochem. 1976 Mar 16;63(1):175–192. doi: 10.1111/j.1432-1033.1976.tb10220.x. [DOI] [PubMed] [Google Scholar]
  5. EVANS W. C., FERNLEY H. N., GRIFFITHS E. OXIDATIVE METABOLISM OF PHENANTHRENE AND ANTHRACENE BY SOIL PSEUDOMONADS. THE RING-FISSION MECHANISM. Biochem J. 1965 Jun;95:819–831. doi: 10.1042/bj0950819. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Engesser K. H., Strubel V., Christoglou K., Fischer P., Rast H. G. Dioxygenolytic cleavage of aryl ether bonds: 1,10-dihydro-1,10-dihydroxyfluoren-9-one, a novel arene dihydrodiol as evidence for angular dioxygenation of dibenzofuran. FEMS Microbiol Lett. 1989 Nov;53(1-2):205–209. doi: 10.1016/0378-1097(89)90392-3. [DOI] [PubMed] [Google Scholar]
  7. Grifoll M., Solanas A. M., Bayona J. M. Characterization of genotoxic components in sediments by mass spectrometric techniques combined with Salmonella/microsome test. Arch Environ Contam Toxicol. 1990 Mar-Apr;19(2):175–184. doi: 10.1007/BF01056084. [DOI] [PubMed] [Google Scholar]
  8. Guerin W. F., Jones G. E. Mineralization of phenanthrene by a Mycobacterium sp. Appl Environ Microbiol. 1988 Apr;54(4):937–944. doi: 10.1128/aem.54.4.937-944.1988. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Heitkamp M. A., Franklin W., Cerniglia C. E. Microbial metabolism of polycyclic aromatic hydrocarbons: isolation and characterization of a pyrene-degrading bacterium. Appl Environ Microbiol. 1988 Oct;54(10):2549–2555. doi: 10.1128/aem.54.10.2549-2555.1988. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Kelley I., Freeman J. P., Evans F. E., Cerniglia C. E. Identification of a Carboxylic Acid Metabolite from the Catabolism of Fluoranthene by a Mycobacterium sp. Appl Environ Microbiol. 1991 Mar;57(3):636–641. doi: 10.1128/aem.57.3.636-641.1991. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. LOWRY O. H., ROSEBROUGH N. J., FARR A. L., RANDALL R. J. Protein measurement with the Folin phenol reagent. J Biol Chem. 1951 Nov;193(1):265–275. [PubMed] [Google Scholar]
  12. Lu P. Y., Metcalf R. L., Carlson E. M. Environmental fate of five radio-labeled coal conversion by-products evaluated in a laboratory model ecosystem. Environ Health Perspect. 1978 Jun;24:201–208. doi: 10.1289/ehp.7824201. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Mormile M. R., Atlas R. M. Mineralization of the dibenzothiophene biodegradation products 3-hydroxy-2-formyl benzothiophene and dibenzothiophene sulfone. Appl Environ Microbiol. 1988 Dec;54(12):3183–3184. doi: 10.1128/aem.54.12.3183-3184.1988. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. Mortelmans K., Haworth S., Lawlor T., Speck W., Tainer B., Zeiger E. Salmonella mutagenicity tests: II. Results from the testing of 270 chemicals. Environ Mutagen. 1986;8 (Suppl 7):1–119. [PubMed] [Google Scholar]
  15. Mueller J. G., Chapman P. J., Blattmann B. O., Pritchard P. H. Isolation and characterization of a fluoranthene-utilizing strain of Pseudomonas paucimobilis. Appl Environ Microbiol. 1990 Apr;56(4):1079–1086. doi: 10.1128/aem.56.4.1079-1086.1990. [DOI] [PMC free article] [PubMed] [Google Scholar]
  16. Møller M., Hagen I., Ramdahl T. Mutagenicity of polycyclic aromatic compounds (PAC) identified in source emissions and ambient air. Mutat Res. 1985 Aug-Sep;157(2-3):149–156. doi: 10.1016/0165-1218(85)90110-7. [DOI] [PubMed] [Google Scholar]
  17. Schocken M. J., Gibson D. T. Bacterial oxidation of the polycyclic aromatic hydrocarbons acenaphthene and acenaphthylene. Appl Environ Microbiol. 1984 Jul;48(1):10–16. doi: 10.1128/aem.48.1.10-16.1984. [DOI] [PMC free article] [PubMed] [Google Scholar]
  18. Smith M. R. The biodegradation of aromatic hydrocarbons by bacteria. Biodegradation. 1990;1(2-3):191–206. doi: 10.1007/BF00058836. [DOI] [PubMed] [Google Scholar]
  19. Stanier R. Y., Palleroni N. J., Doudoroff M. The aerobic pseudomonads: a taxonomic study. J Gen Microbiol. 1966 May;43(2):159–271. doi: 10.1099/00221287-43-2-159. [DOI] [PubMed] [Google Scholar]
  20. Weissenfels W. D., Beyer M., Klein J. Degradation of phenanthrene, fluorene and fluoranthene by pure bacterial cultures. Appl Microbiol Biotechnol. 1990 Jan;32(4):479–484. doi: 10.1007/BF00903787. [DOI] [PubMed] [Google Scholar]

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

RESOURCES