Enzymatic mechanisms involved in phenanthrene degradation by the white rot fungus Pleurotus ostreatus

Applied and Environmental Microbiology

Volumn 63, Issue 7, 1997, Pages 2495-2501

  Bezalel, Lea ^a   Hadar, Yitzhak ^a   Cerniglia, Carl E ^b  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b NATIONAL CENTER FOR TOXICOLOGICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHENANTHRENE; POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; BIOTRANSFORMATION; ENZYME ACTIVITY; HYDROXYLATION; NONHUMAN; PHANEROCHAETE; XENOBIOTIC METABOLISM;

FUNGI; PHANEROCHAETE; PLEUROTUS OSTREATUS;

EID: 0030861449     PISSN: 00992240     EISSN: None     Source Type: Journal    
DOI: 10.1128/aem.63.7.2495-2501.1997     Document Type: Article

References (49)

1. Barclay, C. D., G. F. Farquhar, and R. L. Legge. 1495. Biodegradation and sorption of polyaromatic hydrocarbons by Phanerochaete chrysosporium, Appl. Microbiol. Biotechnol. 42:958-963.
2. Bezalel, L., Y. Hadar, and C. E. Cerniglia. 1996. Mineralization of polycyclic aromatic hydrocarbons by the white rot fungus Pleurotus ostreatus. Appl. Environ. Microbiol. 62:292-295.
3. Bezalel, L., Y. Hadar, P. P. Fu, J. P. Freeman, and C. E. Cerniglia. 1996. Metabolism of phenanthrene by the white rot fungus Pleurotus ostreatus. Appl. Environ. Microbiol. 62:2547-2553.
4. Bezalel, L., Y. Hadar, P. P. Fu, J. P. Freeman, and C. E. Cerniglia. 1996. Initial oxidation products in the metabolism of pyrene, anthracene, fluorene, and dibenzothiophene by the white rot fungus Pleurotus ostreatus. Appl. Environ. Microbiol. 62:2554-2559.
5. Bourbonnais, R., M. G. Paice, I. D. Reid, P. Lanthier, and M. Yaguchi. 1995. Lignin oxidation by laccase isozymes from Trametes versicolor and role of the mediator 2,2′-azinobis(3-ethylbenzthiazoline-6-sulfonate) in kraft lignin depolymerization. Appl. Environ. Microbiol. 61:1876-1880.
6. Bumpus, J. A. 1989. Biodegradation of polycyclic aromatic hydrocarbons by Phanerochaete chrysosporium. Appl. Environ. Microbiol. 55:154-158.
7. Bumpus, J. A., M. Tien, D. Wright, and S. D. Aust. 1985. Oxidation of persistent environmental pollutants by a white-rot fungus. Science 228:1434-1436.
8. Casillas, R. P., S. A. Crow, T. M. Heinze, J. Deck, and C. E. Cerniglia. 1996. Initial oxidative and subsequent conjugative metabolites produced during the metabolism of phenanthrene by fungi. J. Ind. Microbiol. 16:205-215.
9. Cerniglia, C. E. 1993. Biodegradation of polycyclic aromatic hydrocarbons. Curr. Opin. Biotechnol. 4:331-338.
10. Cerniglia, C. E., and D. T. Gibson. 1979. Oxidation of benzo[a]pyrene by the filamentous fungus Cunninghamella elegans. J. Biol. Chem. 254:12174-12180.
11. Cerniglia, C. E., J. B. Sutherland, and S. A. Crow. 1992. Fungal metabolism of aromatic hydrocarbons, p. 193-217. In G. Winkelmann (ed.), Microbial degradation of natural products. VCH Press, Weinheim, Germany.
12. Daly, A. K. 1995. Molecular basis of polymorphic drug metabolism. J. Mol. Med. 73:539-553.
13. Dhawale, S. W., S. S. Dhawale, and D. Dean-Ross. 1992. Degradation of phenanthrene by Phanerochaete chrysosporium occurs under ligninolytic as well as nonligninolytic conditions. Appl. Environ. Microbiol. 58:3000-3006.
14. Dlugonski, J., K. Bartnicka, I. Zemelko, V. Chojecka, and L. Sedlaczek. 1991. Determination of cytochrome P450 in Cunninghamella elegans intact protoplasts and cell-free preparations capable of steroid hydroxylation. J. Basic Microbiol. 31:347-356.
15. Gierow, P., and B. Jergil. 1982. Spectrophotometric method for glucose-6-phosphate phosphatase. Methods Enzymol. 89:44-47.
16. Guan, J., H. M. J. Braks, A. Kerkennar, and M. A. deWaard. 1992. Interaction of microsomal cytochrome P450 isozymes isolated from Penicillium italicum with DMI fungicides. Pestic. Biochem. Physiol. 42:24-34.
17. Habig, W. H., M. J. Pabst, and W. B. Jakoby. 1974. Glutathione S-transferases. J. Biol. Chem. 249:7130-7139.
18. Hadar, Y., Z. Kerem, and B. Gorodecki. 1993. Biodegradation of lignocellulosic agricultural wastes by Pleurotus ostreatus. J. Biotechnol. 30:133-139.
19. Hammel, K. E. 1995. Organopollutant degradation by ligninolytic fungi, p. 331-346. In L. Y. Young and C. E. Cerniglia (ed.), Microbial transformation and degradation of toxic organic chemicals. Wiley-Liss, Inc., New York, N.Y.
20. Hammel, K. E., W. Z. Gai, B. Green, and M. A. Moen. 1992. Oxidative degradation of phenanthrene by the ligninolytic fungus Phanerochaete chrysosporium. Appl. Environ. Microbiol. 58:1832-1838.
21. Hammel, K. E., B. Green, and W. Z. Gai. 1991. Ring fission of anthracene by a eukaryote. Proc. Natl. Acad. Sci. USA 88:10605-10608.
22. Hartmans, S., M. J. Van der Werf, and J. A. M. De Bont. 1990. Bacterial degradation of styrene involving a novel flavin adenine dinucleotide-dependent styrene monooxygenase. Appl. Environ. Microbiol. 56:1347-1351.
23. Hildebrandt, A. G., I. Roots, M. Tjoe, and G. Heinemeyer, 1978. Hydrogen peroxide in hepatic microsomes. Methods Enzymol. 52:342-350.
24. Holland, H. L. 1994. Models for the regiochemistry and stereochemistry of microbial hydroxylation and sulfoxidation. Catalysis Today 22:427-440.
25. Jacobs, M. H. J., A. J. Van Den Wijngaard, M. Pentenga, and D. B. Janssen. 1991. Characterization of the epoxide hydrolase from an epichlorohydrin-degrading Pseudomonas sp. Eur. J. Biochem. 202:1217-1222.
26. Jerina, D. M. 1983. Metabolism of aromatic hydrocarbons by the cytochrome P450 system and epoxide hydrolase. Drug Metab. Dispos. 11:1-4.
27. Kalb, V. F., J. C. L. C. R. Dey, C. W. Woods, and T. R. Sutter. 1986. Isolation of a cytochrome P450 structural gene from Saccharomyces cerevisiae. Gene 45:237-245.
28. Lange, B., S. Kremer, O. Sterner, and H. Anke, 1994. Pyrene metabolism in Crinipellis stipitaria: identification of trans-4,5-dihydro-4,5-dihydroxypyrene and 1-pyrenylsulfate in strain JK364. Appl. Environ. Microbiol. 60:3602-3607.
29. Leakey, J. E. A., H. D. Cunny, J. Bazare, Jr., P. J. Webb, J. C. Lipscomb, W. Slikker, Jr., R. J. Feuers, P. H. Duffy, and R. W. Hart. 1989. Effects of aging and caloric restriction on hepatic drug metabolizing enzymes in the Fischer 344 rat. II. Effects on conjugating enzymes. Mech. Ageing Dev. 48:157-166.
30. Masaphy, S., D. Levanon, Y. Henis, K. Venkateswarlu, and S. L. Kelley. 1995. Microsomal and cytosolic cytochrome P450 mediated benzo[a]pyrene hydroxylation in Pleurotus pulmonarius. Biotechnol. Lett 17:969-974.
31. Matthew, D. E., and H. D. VanEtten. 1983. Detoxification of the phytoalexin pisatin by a fungal cytochrome P450. Arch. Biochem. Biophys. 224:494-505.
32. Mischitz, M., K. Faber, and A. Willetts. 1995. Isolation of a highly enantioselective epoxide hydrolase from Rhodococcus sp. NCIMB 11216. Biotechnol. Lett. 17:893-898.
33. Morgan, P., S. T. Lewis, and R. J. Watkinson. 1991. Comparison of abilities of white rot fungi to mineralize selected xenobiotic compounds. Appl. Microbiol. Biotechnol. 34:693-696.
34. Nellaiah, H., C. Morisseau, A. Archelas, R. Furstoss, and J. C. Baratti. 1996. Enantioselective hydrolysis of p-nitrostyrene by an epoxide hydrolase preparation from Aspergillus niger. Biotechnol. Bioeng. 49:70-77.
35. Oesch, F. 1974. Purification and specificity of a human microsomal epoxide hydratase. Biochem. J. 139:77-88.
36. Oesch, F., and M. Golan. 1980. Specificity of mouse liver cytosolic epoxide hydrolase for K-region epoxides derived from polycyclic aromatic hydrocarbons. Cancer Lett. 9:169-175.
37. Omura, T., and R. Sato. 1964. The carbon monooxide-binding pigment of liver microsomes. II. Solubilization, purification and properties. J. Biol. Chem. 239:2379-2385.
38. Ortiz De Montellano, P. R. 1995. Structure mechanism and inhibition of cytochrome P450. Drug Metab. Dispos. 23:1181-1187.
39. Papadopoulos, D., H. Jornvall, J. Rydstrom, and J. W. DePierre. 1994. Purification and initial characterization of microsomal epoxide hydrolase from human adrenal gland. Biochem. Biophys. Acta 1206:253-262.
40. Sariaslani, F. S. 1991. Microbial cytochrome P450 and xenobiotic metabolism. Adv. Appl. Microbiol. 36:133-178.
41. Seidegard, J., and J. W. DePierre. 1983. Microsomal epoxide hydrolase: properties, regulation and function. Biochim. Biophys. Acta 695:251-270.
42. Shoun, H., Y. Sudo, and T. Beppu. 1985. Subterminal hydroxylation of fatty acids by a cytochrome P450-dependent enzyme system from a fungus. Fusarium oxysporum. J. Biochem. 97:755-763.
43. Sutherland, J. B. 1992. Detoxification of polycyclic aromatic hydrocarbons by fungi. J. Ind. Microbiol. 9:53-61.
44. Sutherland, J. B., A. L. Selby, J. P. Freeman, F. E. Evans, and C. E. Cerniglia. 1991. Metabolism of phenanthrene by Phanerochaete chrysosporium. Appl. Environ. Microbiol. 57:3310-3316.
45. Van Den Brink, H. J. M., C. M. J. Van Zeijl, J. F. Brons, C. A. M. J. J. Van Den Hondel, and R. F. M. Van Gorcom. 1995. Cloning and characterization of the NADPH cytochrome P450 oxidoreductase gene from the filamentous fungus Aspergillus niger. DNA Cell Biol. 14:719-729.
46. Whittaker, J. W., A. M. Orville, and J. D. Lipscomb. 1990. Protocatechuate 3,4-dioxygenase from Brevibacterium fuscum. Methods Enzymol. 188:82-88.
47. Wojtas-Wasilewska, M., and J. Trojanowski. 1980. Purification and properties of protocatechuate 3,4-dioxygenase from Chaetomium piluliferum induced with phenylhydroxybenzoic acid. Acta Biochem. Pol. 27:21-34.
48. Wojtas-Wasilewska, M., J. Trojanowski, and J. Luterek. 1983. Aromatic ring cleavage of protocatechuic acid by the white rot fungus Pleurotus ostreatus. Acta Biochem. Pol. 30:291-302.
49. Zhang, D., Y. Yang, J. E. A. Leakey, and C. E. Cerniglia. 1996. Phase I and phase II enzymes produced by Cunninghamella elegans for the metabolism of xenobiotics. FEMS Microbiol. Lett. 138:221-226.