Abstract
The metabolism of fluorene, a tricyclic aromatic hydrocarbon, by Cunninghamella elegans ATCC 36112 was investigated. Approximately 69% of the [9-14C]fluorene added to cultures was metabolized within 120 h. The major ethyl acetate-soluble metabolites were 9-fluorenone (62%), 9-fluorenol, and 2-hydroxy-9-fluorenone (together, 7.0%). Similarly to bacteria, C. elegans oxidized fluorene at the C-9 position of the five-member ring to form an alcohol and the corresponding ketone. In addition, C. elegans produced the novel metabolite 2-hydroxy-9-fluorenone.
Full text
PDFSelected References
These references are in PubMed. This may not be the complete list of references from this article.
- Bjørseth A., Knutzen J., Skei J. Determination of polycyclic aromatic hydrocarbons in sediments and mussels from Saudafjord, W. Norway, by glass capillary gas chromatography. Sci Total Environ. 1979 Sep;13(1):71–86. doi: 10.1016/0048-9697(79)90018-4. [DOI] [PubMed] [Google Scholar]
- Bumpus J. A. Biodegradation of polycyclic hydrocarbons by Phanerochaete chrysosporium. Appl Environ Microbiol. 1989 Jan;55(1):154–158. doi: 10.1128/aem.55.1.154-158.1989. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Cerniglia C. E., Althaus J. R., Evans F. E., Freeman J. P., Mitchum R. K., Yang S. K. Stereochemistry and evidence for an arene oxide-NIH shift pathway in the fungal metabolism of naphthalene. Chem Biol Interact. 1983 Apr-May;44(1-2):119–132. doi: 10.1016/0009-2797(83)90134-5. [DOI] [PubMed] [Google Scholar]
- Grifoll M., Casellas M., Bayona J. M., Solanas A. M. Isolation and characterization of a fluorene-degrading bacterium: identification of ring oxidation and ring fission products. Appl Environ Microbiol. 1992 Sep;58(9):2910–2917. doi: 10.1128/aem.58.9.2910-2917.1992. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Grimmer G., Böhnke H. Profile analysis of polycyclic aromatic hydrocarbons and metal content in sediment layers of a lake. Cancer Lett. 1975 Nov;1(2):75–83. doi: 10.1016/s0304-3835(75)95429-4. [DOI] [PubMed] [Google Scholar]
- Hoffmann D., Rathkamp G. Quantitative determination of fluorenes in cigarette smoke and their formation by pyrosynthesis. Anal Chem. 1972 May;44(6):899–905. doi: 10.1021/ac60314a062. [DOI] [PubMed] [Google Scholar]
- Holland H. L., Khan S. H., Richards D., Riemland E. Biotransformation of polycyclic aromatic compounds by fungi. Xenobiotica. 1986 Aug;16(8):733–741. doi: 10.3109/00498258609043564. [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]
- 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]
- Monna L., Omori T., Kodama T. Microbial degradation of dibenzofuran, fluorene, and dibenzo-p-dioxin by Staphylococcus auriculans DBF63. Appl Environ Microbiol. 1993 Jan;59(1):285–289. doi: 10.1128/aem.59.1.285-289.1993. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Pothuluri J. V., Freeman J. P., Evans F. E., Cerniglia C. E. Fungal metabolism of acenaphthene by Cunninghamella elegans. Appl Environ Microbiol. 1992 Nov;58(11):3654–3659. doi: 10.1128/aem.58.11.3654-3659.1992. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Pothuluri J. V., Freeman J. P., Evans F. E., Cerniglia C. E. Fungal transformation of fluoranthene. Appl Environ Microbiol. 1990 Oct;56(10):2974–2983. doi: 10.1128/aem.56.10.2974-2983.1990. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Pothuluri J. V., Heflich R. H., Fu P. P., Cerniglia C. E. Fungal metabolism and detoxification of fluoranthene. Appl Environ Microbiol. 1992 Mar;58(3):937–941. doi: 10.1128/aem.58.3.937-941.1992. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Vassilaros D. L., Stoker P. W., Booth G. M., Lee M. L. Capillary gas chromatographic determination of polycyclic aromatic compounds in vertebrate fish tissue. Anal Chem. 1982 Jan;54(1):106–112. doi: 10.1021/ac00238a031. [DOI] [PubMed] [Google Scholar]
- 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]