F 420H 2-dependent degradation of aflatoxin and other furanocoumarins is widespread throughout the Actinomycetales

PLoS ONE

Volumn 7, Issue 2, 2012, Pages

  Lapalikar, Gauri V ^a   Taylor, Matthew C ^a   Warden, Andrew C ^a   Scott, Colin ^a   Russell, Robyn J ^a   Oakeshott, John G ^a  

^a CSIRO   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

AFLATOXIN; ANGELICIN; F420 DEPENDENT REDUCTASE A; F420 DEPENDENT REDUCTASE B; FUROCOUMARIN DERIVATIVE; METHOXSALEN; OXIDOREDUCTASE; PENTOSALEN; UNCLASSIFIED DRUG; ANTIINFECTIVE AGENT; BACTERIAL PROTEIN; COUMARIN; COUMARIN DERIVATIVE; F420H2 DEHYDROGENASE; KHELLIN; PSORALEN DERIVATIVE; RIBOFLAVIN DERIVATIVE; XENOBIOTIC AGENT;

ACTINOMYCETALES; ARTICLE; CATALYSIS; CLADISTICS; DEGRADATION; ENZYME ACTIVITY; HETEROLOGOUS EXPRESSION; HYDROLYSIS; MASS SPECTROMETRY; MYCOBACTERIUM SMEGMATIS; NONHUMAN; CHEMISTRY; GENE EXPRESSION REGULATION; METABOLISM; METHODOLOGY; PHYLOGENY; SPECIES DIFFERENCE;

ACTINOMYCETALES; HARNESS; MYCOBACTERIUM SMEGMATIS; PROTEOBACTERIA;

AFLATOXINS; ANTI-BACTERIAL AGENTS; BACTERIAL PROTEINS; COUMARINS; FLAVINS; GENE EXPRESSION REGULATION; HYDROLYSIS; KHELLIN; MASS SPECTROMETRY; METHOXSALEN; MYCOBACTERIUM SMEGMATIS; OXIDOREDUCTASES; PHYLOGENY; PSORALENS; SPECIES SPECIFICITY; XENOBIOTICS;

EID: 84857540921     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0030114     Document Type: Article

References (44)

1. Wagacha JM, Muthomi JW, (2008) Mycotoxin problem in Africa: Current status, implications to food safety and health and possible management strategies. International Journal of Food Microbiology 124: 1-12.
2. Ciegler A, Lillehoj EB, Peterson RE, Hall HH, (1966) Microbial Detoxification of Aflatoxin. Applied Microbiology 14: 934-&.
3. Teniola OD, Addo PA, Brost IM, Farber P, Jany KD, et al. (2005) Degradation of aflatoxin B-1 by cell-free extracts of Rhodococcus erythropolis and Mycobacterium fluoranthenivorans sp nov DSM44556(T). International Journal of Food Microbiology 105: 111-117.
4. Hormisch D, Brost I, Kohring GW, Giffhorn E, Kroppenstedt RM, et al. (2004) Mycobacterium fluoranthenivorans sp nov., a fluoranthene and aflatoxin B-1 degrading bacterium from contaminated soil of a former coal gas plant. Systematic and Applied Microbiology 27: 653-660.
5. Alberts JF, Engelbrecht Y, Steyn PS, Holzapfel W, van Zyl W, (2006) Biological degradation of aflatoxin B-1 by Rhodococcus erythropolis cultures. International Journal of Food Microbiology 109: 121-126.
6. Taylor MC, Jackson CJ, Tattersall DB, French N, Peat TS, et al. (2010) Identification and characterization of two families of F420 H2-dependent reductases from Mycobacteria that catalyse aflatoxin degradation. Mol Microbiol 78: 561-575.
7. Purwantini E, Gillis TP, Daniels L, (1997) Presence of F420-dependent glucose-6-phosphate dehydrogenase in Mycobacterium and Nocardia species, but absence from Streptomyces and Corynebacterium species and methanogenic Archaea. FEMS Microbiology Letters 146: 129-134.
8. Isabelle D, Simpson DR, Daniels L, (2002) Large-scale production of coenzyme F420-5,6 by using Mycobacterium smegmatis. Applied and Environmental Microbiology 68: 5750-5755.
9. Bashiri G, Rehan AM, Greenwood DR, Dickson JMJ, Baker EN, (2010) Metabolic Engineering of Cofactor F420 Production in Mycobacterium smegmatis. Plos One 5: e15803.
10. de Poorter LMI, Geerts WJ, Keltjens JT, (2005) Hydrogen concentrations in methane-forming cells probed by the ratios of reduced and oxidized coenzyme F-420. Microbiology-Sgm 151: 1697-1705.
11. Jacobson F, Walsh C, (1984) Properties of 7,8-Didemethyl-8-Hydroxy-5-Deazaflavins Relevant to Redox Coenzyme Function in Methanogen Metabolism. Biochemistry 23: 979-988.
12. Kakinuma K, Kaneda M, Chiba T, Ohnishi T, (1986) Electron-Spin-Resonance Studies on a Flavoprotein in Neutrophil Plasma-Membranes- Redox Potentials of the Flavin and Its Participation in Nadph Oxidase. Journal of Biological Chemistry 261: 9426-9432.
13. Draper RD, Ingraham LL, (1968) A Potentiometric Study of Flavin Semiquinone Equilibrium. Archives of Biochemistry and Biophysics 125: 802-&.
14. Ebert S, Rieger PG, Knackmuss HJ, (1999) Function of coenzyme F420 in aerobic catabolism of 2,4,6-trinitrophenol and 2,4-dinitrophenol by Nocardioides simplex FJ2-1A. Journal of Bacteriology 181: 2669-2674.
15. Heiss G, Hofmann KW, Trachtmann N, Walters DM, Rouviere P, et al. (2002) npd gene functions of Rhodococcus (opacus) erythropolis HL PM-1 in the initial steps of 2,4,6-trinitrophenol degradation. Microbiology-Sgm 148: 799-806.
16. Purwantini E, Mukhopadhyay B, (2009) Conversion of NO2 to NO by reduced coenzyme F420 protects mycobacteria from nitrosative damage. Proceedings of the National Academy of Sciences of the United States of America 106: 6333-6338.
17. Ebert S, Fischer P, Knackmuss HJ, (2001) Converging catabolism of 2,4,6-trinitrophenol (picric acid) and 2,4-dinitrophenol by Nocardioides simplex FJ2-1A. Biodegradation 12: 367-376.
18. Guerra-Lopez D, Daniels L, Rawat M, (2007) Mycobacterium smegmatis mc(2) 155 fbiC and MSMEG_2392 are involved in triphenylmethane dye decolorization and coenzyme F420 biosynthesis. Microbiology-Sgm 153: 2724-2732.
19. Li W, Khullar A, Chou S, Sacramo A, Gerratana B, (2009) Biosynthesis of Sibiromycin, a Potent Antitumor Antibiotic. Applied and Environmental Microbiology 75: 2869-2878.
20. Gerratana B, (2010) Biosynthesis, synthesis, and biological activities of pyrrolobenzodiazepines. Med Res Rev.
21. Singh R, Manjunatha U, Boshoff HIM, Ha YH, Niyomrattanakit P, et al. (2008) PA-824 Kills Nonreplicating Mycobacterium tuberculosis by Intracellular NO Release. Science 322: 1392-1395.
22. Choi KP, Bair TB, Bae YM, Daniels L, (2001) Use of transposon Tn5367 mutagenesis and a nitroimidazopyran-based selection system to demonstrate a requirement for fbiA and fbiB in coenzyme F420 biosynthesis by Mycobacterium bovis BCG. Journal of Bacteriology 183: 7058-7066.
23. Manjunatha UH, Boshoff H, Dowd CS, Zhang L, Albert TJ, et al. (2006) Identification of a nitroimidazo-oxazine-specific protein involved in PA-824 resistance in Mycobacterium tuberculosis. Proceedings of the National Academy of Sciences of the United States of America 103: 431-436.
24. Selengut JD, Haft DH, (2010) Unexpected Abundance of Coenzyme F420-Dependent Enzymes in Mycobacterium tuberculosis and Other Actinobacteria. Journal of Bacteriology 192: 5788-5798.
25. Bashiri G, Squire CJ, Moreland NJ, Baker EN, (2008) Crystal structures of F420-dependent glucose-6-phosphate dehydrogenase FGD1 involved in the activation of the anti-tuberculosis drug candidate PA-824 reveal the basis of coenzyme and substrate binding. Journal of Biological Chemistry 283: 17531-17541.
26. Tamura K, Dudley J, Nei M, Kumar S, (2007) MEGA4: Molecular evolutionary genetics analysis (MEGA) software version 4.0. Molecular Biology and Evolution 24: 1596-1599.
27. Griese JJ, R PJ, Schwarzinger S, Dobbek H, (2006) Xenobiotic reductase A in the degradation of quinoline by Pseudomonas putida 86: physiological function, structure and mechanism of 8-hydroxycoumarin reduction. J Mol Biol 361: 140-152.
28. Berkessel A, Cleemann F, Mukherjee S, Muller TN, Lex J, (2005) Highly efficient dynamic kinetic resolution of azlactones by urea-based bifunctional organocatalysts. Angewandte Chemie-International Edition 44: 807-811.
29. Otani S, Takatsu M, Nakano M, Kasai S, Miura R, et al. (1974) Roseoflavin, a New Antimicrobial Pigment from Streptomyces. Journal of Antibiotics 27: 88-89.
30. Mack M, Grill S, (2006) Riboflavin analogs and inhibitors of riboflavin biosynthesis. Applied Microbiology and Biotechnology 71: 265-275.
31. Grill S, Busenbender S, Pfeiffer M, Kohler U, Mack M, (2008) The bifunctional flavokinase/flavin adenine dinucleotide synthetase from Streptomyces davawensis produces inactive flavin cofactors and is not involved in resistance to the antibiotic roseoflavin. Journal of Bacteriology 190: 1546-1553.
32. Pitts JN, (1983) Formation and Fate of Gaseous and Particulate Mutagens and Carcinogens in Real and Simulated Atmospheres. Environmental Health Perspectives 47: 115-140.
33. Brodersen R, Kjaer A, (1946) The Antibacterial Action and Toxicity of Some Unsaturated Lactones. Acta Pharmacologica et Toxicologica 2: 109-120.
34. Hamamoto T, Uozumi T, Beppu T, (1985) Biosynthetic-Studies of Leptomycins. Journal of Antibiotics 38: 533-535.
35. Barnes MR, Duetz WA, Williams PA, (1997) A 3-(3-hydroxyphenyl)propionic acid catabolic pathway in Rhodococcus globerulus PWD1: cloning and characterization of the hpp operon. J Bacteriol 179: 6145-6153.
36. Strickland S, Massey V, (1973) The purification and properties of the flavoprotein melilotate hydroxylase. J Biol Chem 248: 2944-2952.
37. Bugg TD, Sanvoisin J, Spence EL, (1997) Exploring the catalytic mechanism of the extradiol catechol dioxygenases. Biochem Soc Trans 25: 81-85.
38. Spence EL, Kawamukai M, Sanvoisin J, Braven H, Bugg TD, (1996) Catechol dioxygenases from Escherichia coli (MhpB) and Alcaligenes eutrophus (MpcI): sequence analysis and biochemical properties of a third family of extradiol dioxygenases. Journal of Bacteriology 178: 5249-5256.
39. Kaneko M, Ohnishi Y, Horinouchi S, (2003) Cinnamate:coenzyme A ligase from the filamentous bacterium Streptomyces coelicolor A3(2). J Bacteriol 185: 20-27.
40. Lynen F, Ochoa S, (1953) Enzymes of Fatty Acid Metabolism. Biochimica et Biophysica Acta 12: 299-314.
41. Bornemann C, Jardine MA, Spies HSC, Steenkamp DJ, (1997) Biosynthesis of mycothiol: elucidation of the sequence of steps in Mycobacterium smegmatis. Biochemical Journal 325: 623-629.
42. Alexeev I, Sultana A, Mantsala P, Niemi J, Schneider G, (2007) Aclacinomycin oxidoreductase (AknOx) from the biosynthetic pathway of the antibiotic aclacinomycin is an unusual flavoenzyme with a dual active site. Proc Natl Acad Sci U S A 104: 6170-6175.
43. Chung JY, Fujii I, Harada S, Sankawa U, Ebizuka Y, (2002) Expression, purification, and characterization of AknX anthrone oxygenase, which is involved in aklavinone biosynthesis in Streptomyces galilaeus. J Bacteriol 184: 6115-6122.
44. Oja T, Palmu K, Lehmussola H, Lepparanta O, Hannikainen K, et al. (2008) Characterization of the alnumycin gene cluster reveals unusual gene products for pyran ring formation and dioxan biosynthesis. Chem Biol 15: 1046-1057.