New metabolites in the degradation of fluorene by Arthrobacter sp. strain F101

Applied and Environmental Microbiology

Volumn 63, Issue 3, 1997, Pages 819-826

  Casellas, Merce ^a   Grifoll, Magdalena ^a   Bayona, Josep M ^b   Solanas, Anna Maria ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORENE DERIVATIVE; FLUORENONE DERIVATIVE;

ARTHROBACTER; ARTICLE; BIODEGRADATION; DRUG DEGRADATION; ENZYME ACTIVITY; HYDROLYSIS; METABOLITE;

ARTHROBACTER; ARTHROBACTER SP.;

EID: 0031025405     PISSN: 00992240     EISSN: None     Source Type: Journal    
DOI: 10.1128/aem.63.3.819-826.1997     Document Type: Article

References (41)

1. Baeyer, A., and V. Villiger. 1899. Einwerkung des Caro'schen Reagens auf Ketone. Ber. Dtsch. Chem. 32:3625-3633.
2. Bennett, A. P., E. J. Strang, P. W. Trudgill, and V. T. K. Wong. 1988. Purification and properties of ε-caprolactone hydrolases from Acinetobacter NCIB 9871 and Nocardia globerula CL1. J. Gen. Microbiol. 134:161-168.
3. Boldrin, B., A. Tiehm, and C. Fritzsche. 1993. Degradation of phenanthrene, fluorene, fluoranthene, and pyrene by a Mycobacterium sp. Appl. Environ. Microbiol. 59:1927-1930.
4. Burlingame, R., and P. J. Chapman. 1983. Catabolism of phenylpropionic acid and its 3-hydroxy derivative by Escherichia coli. J Bacteriol. 155:113-121.
5. Casellas, M., P. Fernandez, J. M. Bayona, and A. M. Solanas. 1995. Bioassay-directed chemical analysis of genotoxic components in urban airborne particulate matter from Barcelona (Spain). Chemosphere 30:725-740.
6. Chapman, P. J., G. Meerman, I. C. Gunsalus, R. Srinivasan, and K. L. Rinehart, Jr. 1966. A new acyclic metabolite in camphor oxidation. J. Am. Chem. Soc. 88:618-619.
7. Conrad, H. E., R. DuBus, and I. C. Gunsalus. 1961. An enzyme system for cyclic ketone lactonization. Biochem. Biophys. Res. Commun. 6:293-297.
8. Danz, M., D. Müller, and H. Räthe. 1992. Fluorenone and 2-benzoylfluorenone: different short-term effects on drug-metabolizing liver enzymes and on cell proliferation. Exp. Toxicol. Pathol. 44:259-261.
9. Davey, J. F., and P. W. Trudgill. 1977. The metabolism of trans-cyclohexan-1,2-diol by an Acinetobacter species. Eur. J. Biochem. 74:115-127.
10. Davies, J. L., and W. C. Evans. 1964. Oxidative metabolism of naphthalene by soil pseudomonads. The ring-fission mechanism. Biochem. J. 91:251-261.
11. Donoghue, N. A., D. B. Norris, and P. W. Trudgill. 1976. The purification and properties of cyclohexanone oxygenase from Nocardia globerula C.L. and Acinetobacter NCIB 9871. Eur. J. Biochem. 63:175-192.
12. Fernandez, P., M. Grifoll, A. M. Solanas, J. M. Bayona, and J. Albaigés. 1992. Bioassay-directed chemical analysis of genotoxic components in coastal marine sediments. Environ. Sci. Technol. 26:817-829.
13. Foght, J. M., and D. W. S. Westlake. 1988. Degradation of polycyclic aromatic hydrocarbons and aromatic heterocycles by a Pseudomonas species. Can. J. Microbiol. 34:1135-1141.
14. Foght, J. M., and D. W. S. Westlake. 1990. Expression of dibenzothiophene-degradative genes in two Pseudomonas species. Can. J. Microbiol. 36:718-724.
15. Gibson, D. T. 1971. Assay of enzymes of aromatic metabolism. Methods Microbiol. 6A:463-478.
16. Gibson, D. T., and V. Subramanian. 1984. Microbial degradation of aromatic hydrocarbons, p. 181-250. In D. T. Gibson (ed.), Microbial degradation of organic compounds. Marcel Dekker, Inc., New York, N.Y.
17. Grifoll, M., M. Casellas, J. M. Bayona, and A. M. Solanas. 1992. Isolation and characterization of a fluorene-degrading bacterium: identification of ring oxidation and ring-fission products. Appl. Environ. Microbiol. 58:2910-2917.
18. Grifoll, M., A. M. Solanas, and J. M. Bayona. 1992. Bioassay-directed chemical characterization of genotoxic agents in the dissolved and particulate water phases of Besos and Llobregat rivers (Barcelona, Spain). Arch. Environ. Contam. Toxicol. 23:19-25.
19. Grifoll, M., S. A. Selifonov, and P. J. Chapman. 1994. Evidence for a novel pathway in the degradation of fluorene by Pseudomonas sp. strain F274. Appl. Environ. Microbiol. 60:2438-2449.
20. Grifoll, M., S. A. Selifonov, C. V. Gatlin, and P. J. Chapman. 1995. Actions of a versatile fluorene-degrading bacterial isolate on polycylic aromatic hydrocarbons. Appl. Environ. Microbiol. 61:3711-3723.
21. Gunsalus, I. C., and V. P. Marshall. 1971. Monoterpene dissimilation: chemical and genetic models. Crit. Rev. Microbiol. 1:291-310.
22. Heitkamp, M. A., J. P. Freeman, D. W. Miller, and C. E. Cerniglia. 1988. Pyrene degradation by a Mycobacterium sp.: identification of ring oxidation and ring fission products. Appl. Environ. Microbiol. 54:2556-2565.
23. Hsieh, Y., M. B. Thompson, and C. H. Ward. 1980. Toxicity of water soluble extracts of No. 2 fuel oil to the freshwater alga Selenastrum capricornutum. Dev. Ind. Microbiol. 21:401-109.
24. Kosuge, T., and E. E. Conn. 1962. The metabolism of aromatic compounds in higher plants. J. Biol. Chem. 237:1653-1656.
25. Lowry, O. H., N. J. Rosebrough, A. L. Farr, and R. J. Randall. 1951. Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193:265-275.
26. Neidhardt, F. C., J. L. Ingraham, and M. Schaechter. 1990. Physiology of the bacterial cell. Sinauer Associates, Inc., Sunderland, Miss.
27. Resnick, S. M., D. S. Torok, K. Lee, J. M. Brand, and D. T. Gibson. 1994. Regiospecific and stereoselective hydroxylation of 1-indanone and 2-indanone by naphthalene dioxygenase and toluene dioxygenase. Appl. Environ. Microbiol. 60:3323-3328.
28. Rontani, J. F., E. Rambeloarisoa, J. C. Bertrand, and G. Giusti. 1985. Degradation of alkyl-substituted benzenes and their photo-oxidation products by a marine mixed bacterial population. Mar. Environ. Res. 16:301-314.
29. Selifonov, S. A., M. Grifoll, J. E. Gurst, and P. J. Chapman. 1993. Isolation and characterization of (+)-1,1α-dihydroxy-1-hydrofluoren-9-one formed by angular dioxygenation in the bacterial catabolism of fluorene. Biochem. Biophys. Res. Commun. 193:67-76.
30. Selifonov, S. A., M. Grifoll, R. W. Eaton, and P. J. Chapman. 1996. Oxidation of naphthenoaromatic and methyl-substituted aromatic compounds by naphthalene 1,2-dioxygenase. Appl. Environ. Microhiol. 62:507-514.
31. Shimizu, S., M. Kataoka, K. Shimizu, M. Hirakata, K. Sakamoto, and H. Yamada. 1992. Purification and characterization of a novel lactonohydrolase, catalyzing the hydrolysis of aldonate lactones and aromatic lactones, from Fusarium oxysporum. Eur. J. Biochem. 209:383-390.
32. Silverstein, R. M., G. Clayton Barsler, and J. C. Morrill. 1981. Spectrometric identification of organic compounds. John Wiley and Sons, New York, N.Y.
33. Smith, M. R. 1990. The biodegradation of aromatic hydrocarbons by bacteria. Biodegradation 1:191-206.
34. Socrates, G. 1980. Infrared characteristic group frequencies. John Wiley and Sons, New York, N.Y.
35. Stirling, L. A., and R. J. Watkinson. 1977. Microbial metabolism of alicyclic hydrocarbons: isolation and properties of a cyclohexane-degrading bacterium. J. Gen. Microbiol. 99:119-125.
36. Thomas, P., H. W. Wofford, and J. M. Neff. 1981. Biochemical stress responses of striped mullet (Mugil cephalus) to fluorene analogs. Aquat. Toxicol. 1:329-342.
37. Trenz, S. P., K. H. Engesser, P. Fischer, and H.-J. Knackmuss. 1994. Degradation of fluorene by Brevibacterium sp. strain DPO 1361: a novel C-C bond cleavage mechanism via 1,10-dihydro-1,10-dihydroxyfluoren-9-one. J. Bacteriol. 176:789-795.
38. Wackett, L. P., L. D. Kwart, and D. T. Gibson. 1988. Benzylic monoxygenation catalyzed by toluene dioxygenase from Pseudomonas putida. Biochemistry 27:1360-1367.
39. Weissenfels, W. D., M. Beyer, J. Klein, and H. J. Rehm. 1991. Microbial metabolism of fluoranthene: isolation and identification of ring fission products. Appl. Microbiol. Biotechnol. 34:528-535.
40. Williams, D. R., P. W. Trudgill, and D. G. Taylor. 1989. Metabolism of 1,8-cineole by a Rhodococcus species: ring cleavage reactions. J. Gen. Microbiol. 135:1957-1967.
41. Wise, S. A., B. A. Benner, G. D. Burd, S. N. Chester, R. E. Rebbert, and M. M. Schantz. 1988. Determination of polycyclic aromatic hydrocarbons in a coal standard reference material. Anal. Chem. 60:887-894.