A cytochrome P450 involved in the metabolism of abietane diterpenoids by Pseudomonas abietaniphila BKME-9

Journal of Bacteriology

Volumn 186, Issue 11, 2004, Pages 3631-3639

  Smith, Daryl J ^a   Martin, Vincent J J ^b   Mohn, William W ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^b LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABIETANE; CYTOCHROME P450; DEHYDROABIETIC ACID; DITERPENOID; DNA; OXYGENASE; PALUSTRIC ACID; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; BACTERIAL GENE; BACTERIUM CULTURE; BACTERIUM ISOLATION; BIODEGRADATION; DITQ GENE; ENZYME ACTIVITY; ESCHERICHIA COLI; GENE CLUSTER; GENE REARRANGEMENT; NONHUMAN; NUCLEOTIDE SEQUENCE; PLASMID; POLYMERASE CHAIN REACTION; PRIORITY JOURNAL; PSEUDOMONAS; PSEUDOMONAS ABIETANIPHILA BKME 9; SPECTROPHOTOMETRY; TDTD GENE;

CARBON MONOXIDE; CYTOCHROME P-450 ENZYME SYSTEM; DITERPENES, ABIETANE; MULTIGENE FAMILY; OPEN READING FRAMES; PSEUDOMONAS;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; NEGIBACTERIA; PAA; PSEUDOMONAS; PSEUDOMONAS ABIETANIPHILA; PSEUDOMONAS DITERPENIPHILA;

EID: 2442662867     PISSN: 00219193     EISSN: None     Source Type: Journal    
DOI: 10.1128/JB.186.11.3631-3639.2004     Document Type: Article

References (30)

1. Altschul, S. F., T. L. Madden, A. A. Schaffer, J. Zhang, Z. Zhang, W. Miller, and D. J. Lipman. 1997. Gapped BLAST and PSI-BLAST: a new generation of protein database search programs. Nucleic Acids Res. 25:3389-3402.
2. Ausubel, F. M., R. Brent, R. E. Kingston, D. D. Moore, J. G. Seidman, J. A. Smith, and K. Struhl (ed.). 1992. Short protocols in molecular biology, 2nd ed. John Wiley & Sons, New York, N.Y.
3. Bicho, P. A., V. Martin, and J. N. Saddler. 1995. Growth, induction, and substrate specificity of dehydroabietic acid-degrading bacteria isolated from a kraft mill effluent enrichment. Appl. Environ. Microbiol. 61:3245-3250.
4. Clarke, A. R. 1996. Analysis of ligand binding by enzymes, p. 199-221. In B. D. Hames, D. Rickwood, and P. Engel (ed.), Enzymology labfax. Academic Press, San Diego, Calif.
5. Feio, S. S., S. Franca, A. M. Silva, B. Gigante, J. C. Roseiro, and M. J. Marcelo Curto. 2002. Antimicrobial activity of methyl cis-7-oxo deisopropyldehydroabietate on Botrytis cinerea and Lophodermium seditiosum: ultrastructural observations by transmission electron microscopy. J. Appl. Microbiol. 93:765-771.
6. Fernandez, M. A., M. P. Tornos, M. D. Garcia, B. de las Heras, A. M. Villar, and M. T. Saenz. 2001. Anti-inflammatory activity of abietic acid, a diterpene isolated from Pimenta racemosa var. grissea. J. Pharm. Pharmacol. 53:867-872.
7. Funk, C., and R. Croteau. 1994. Diterpenoid resin acid biosynthesis in conifers: characterization of two cytochrome P450-dependent monooxygenases and an aldehyde dehydrogenase involved in abietic acid biosynthesis. Arch. Biochem. Biophys. 308:258-266.
8. Gerhardt, P., R. G. E. Murray, W. A. Wood, and N. R. Krieg. 1994. Methods for general and molecular bacteriology. American Society for Microbiology, Washington, D.C.
9. Gigante, B., C. Santos, A. M. Silva, M. J. Curto, M. S. Nascimento, E. Pinto, M. Pedro, F. Cerqueira, M. M. Pinto, M. P. Duarte, A. Laires, J. Rueff, J. Goncalves, M. I. Pegado, and M. L. Valdeira. 2003. Catechols from abietic acid synthesis and evaluation as bioactive compounds. Bioorg. Med. Chem. 11:1631-1638.
10. Hawkes, D. B., G. W. Adams, A. L. Burlingame, P. R. Ortiz de Montellano, and J. J. De Voss. 2002. Cytochrome P450(cin) (CYP176A), isolation, expression, and characterization. J. Biol. Chem. 277:27725-27732.
11. Jefcoate, C. R. 1978. Measurement of substrate and inhibitor binding to microsomal cytochrome P-450 by optical-difference spectroscopy. Methods Enzymol. 52:258-279.
12. Kinouchi, Y., H. Ohtsu, H. Tokuda, H. Nishino, S. Matsunaga, and R. Tanaka. 2000. Potential antitumor-promoting diterpenoids from the stem bark of Picea glehni. J. Nat. Prod. 63:817-820.
13. LaFever, R. E., B. S. Vogel, and R. Croteau. 1994. Diterpenoid resin acid biosynthesis in conifers: enzymatic cyclization of geranylgeranyl pyrophosphate to abietadiene, the precursor of abietic acid. Arch. Biochem. Biophys. 313:139-149.
14. Martin, V. J., and W. W. Mohn. 2000. Genetic investigation of the catabolic pathway for degradation of abietane diterpenoids by Pseudomonas abietaniphila BKME-9. J. Bacteriol. 182:3784-3793.
15. Martin, V. J., and W. W. Mohn. 1999. A novel aromatic-ring-hydroxylating dioxygenase from the diterpenoid-degrading bacterium Pseudomonas abietaniphila BKME-9. J. Bacteriol. 181:2675-2682.
16. Mohn, W. W. 1995. Bacteria obtained from a sequencing batch reactor that are capable of growth on dehydroabietic acid. Appl. Environ. Microbiol. 61:2145-2150.
17. Morgan, C. A., and R. C. Wyndham. 2002. Characterization of tdt genes for the degradation of tricyclic diterpenes by Pseudomonas diterpeniphila A19-6a. Can. J. Microbiol. 48:49-59.
18. Morgan, C. A., and R. C. Wyndham. 1996. Isolation and characterization of resin acid degrading bacteria found in effluent from a bleached kraft pulp mill. Can. J. Microbiol. 42:423-430.
19. Ortiz de Montellano, P. R. 1995. Cytochrome P450: structure, mechanism, and biochemistry, 2nd ed. Plenum Press, New York, N.Y.
20. Peterson, J. A., and Y. Ishimura. 1971. Reaction mechanism of bacterial cytochrome P-450-catalyzed camphor methylene hydroxylation. Chem.-Biol. Interact. 3:300-302.
21. Peterson, J. A., J. Y. Lu, J. Geisselsoder, S. Graham-Lorence, C. Carmona, F. Witney, and M. C. Lorence. 1992. Cytochrome P-450terp. Isolation and purification of the protein and cloning and sequencing of its operon. J. Biol. Chem. 267:14193-14203.
22. Schweizer, H. P., and T. T. Hoang. 1995. An improved system for gene replacement and xylE fusion analysis in Pseudomonas aeruginosa. Gene 158:15-22.
23. Simons, R., U. Priefer, and A. Puhler. 1983. A broad host range mobilization system for in vivo genetic engineering: transposon mutagenesis in gram negative bacteria. Bio/Technology 1:784-790.
24. Smith, P. K., R. I. Krohn, G. T. Hermanson, A. K. Mallia, F. H. Gartner, M. D. Provenzano, E. K. Fujimoto, N. M. Goeke, B. J. Olson, and D. C. Klenk. 1985. Measurement of protein using bicinchoninic acid. Anal. Biochem. 150:76-85.
25. Stassi, D., S. Donadio, M. J. Staver, and L. Katz. 1993. Identification of a Saccharopolyspora erythraea gene required for the final hydroxylation step in erythromycin biosynthesis. J. Bacteriol. 175:182-189.
26. Ulusu, N. N., D. Ercil, M. K. Sakar, and E. F. Tezcan. 2002. Abietic acid inhibits lipoxygenase activity. Phytother. Res. 16:88-90.
27. Unger, B., I. Gunsalus, and S. Sligar. 1986. Nucleotide sequence of the Pseudomonas putida cytochrome P-450cam gene and its expression in Escherichia coli. J. Biol. Chem. 261:1158-1163.
28. Wust, M., and R. B. Croteau. 2002. Hydroxylation of specifically deuterated limonene enantiomers by cytochrome p450 limonene-6-hydroxylase reveals the mechanism of multiple product formation. Biochemistry 41:1820-1827.
29. Yanisch-Perron, C., J. Vieira, and J. Messing. 1985. Improved M13 phage cloning vectors and host strains: nucleotide sequences of the M13mp18 and pUC19 vectors. Gene 33:103-119.
30. Zon, L. I., D. M. Dorfman, and S. H. Orkin. 1989. The polymerase chain reaction colony miniprep. BioTechniques 7:696-698.