De Novo synthesis of 4,5-dimethoxycatechol and 2,5- dimethoxyhydroquinone by the brown rot fungus Gloeophyllum trabeum

Applied and Environmental Microbiology

Volumn 65, Issue 2, 1999, Pages 674-679

  Paszczynski, Andrzej ^a   Crawford, Ronald ^a   Funk, David ^a   Goodell, Barry ^b  

^a UNIVERSITY OF IDAHO   (United States)

^b UNIVERSITY OF MAINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,5 DIMETHOXYHYDROQUINONE; 4,5 DIMETHOXYCATECHOL; CATECHOL DERIVATIVE; GLUCOSE; HYDROQUINONE DERIVATIVE; IRON CHELATING AGENT; UNCLASSIFIED DRUG;

ARTICLE; BROWN ROT FUNGUS; ELECTRON TRANSPORT; FUNGUS CULTURE; FUNGUS GROWTH; GLOEOPHYLLUM TRABEUM; NONHUMAN; OXIDATION REDUCTION REACTION; SYNTHESIS;

FUNGI; GLOEOPHYLLUM TRABEUM;

EID: 0033013291     PISSN: 00992240     EISSN: None     Source Type: Journal    
DOI: 10.1128/aem.65.2.674-679.1999     Document Type: Article

References (32)

1. Ander, P., and L. Marzullo. 1997. Sugar oxidoreductases and veratryl alcohol oxidase as related to lignin degradation. J. Biotechnol. 53:115-131.
2. Barr, D. P., and S. D. Aust. 1994. Effect of superoxide and superoxide dismutase on lignin peroxidase-catalyzed veratryl alcohol oxidation. Arch. Biochem. Biophys. 311:378-382.
3. Black, T. H. 1983. The preparation and reactions of diazomethane. Aldrichimica Acta 16:3-10.
4. Bonnarme, P., J. Perez, and T. M. Jefferies. 1991. Regulation of ligninase production in white-rot fungi, p. 200-206. In G. Leatham and M. Himmel (ed.), Enzymes in biomass conversion. American Chemical Society, Washington, D.C.
5. Bonthrone, W., and J. W. Cornforth. 1969. The methylation of catechol. J. Chem. Soc. (C) 1969:1202-1204.
6. Brock, B. J., and M. H. Gold. 1996. 1,4-Benzoquinone reductase from the basidiomycete Phanerochaete chrysosporium: spectral and kinetic analysis. Arch. Biochem. Biophys. 331:31-40.
7. Brock, B. J., S. Rieble, and M. H. Gold. 1995. Purification and characterization of a 1,4-benzoquinone reductase from the basidiomycete Phanerochaete chrysosporium. Appl. Eniron. Microbiol. 61:3076-3081.
8. Bumpus, J. A. 1998. Perspectives on the use of white rot fungi in bioremediation technologies, p. 67-109. In S. K. Sikdar and R. L. Irvine (ed.). Biodegradation technology developments. Bioremediation, principles and practice, vol. 2. Technomic Publishing Co., Lancaster, Pa.
9. de Boer, T. J., and H. J. Backer. 1963. Diazomethane, p. 250-253. In N. Rabjohn (ed.), Organic synthesis, vol. 4. John Wiley & Sons, New York, N. Y.
10. Enoki, A., T. Hirano, and H. Tanaka. 1992. Extracellular substance from brown-rot basidiomycete C. trabeum that produces and reduces hydrogen peroxide. Mater. Org. 27:247-261.
11. Enoki, A., S. Itakura, and H. Tanaka. 1997. The involvement of extracellular substances for reducing molecular oxygen to hydroxyl radical and ferric iron to ferrous iron in wood degradation by wood decay fungi. J. Biotechnol. 53:265-272.
12. Eriksson, K.-E. L., R. A. Blanchette, and P. Ander. 1990. Microbial and enzymatic degradation of wood and wood components. Springer-Verlag, New York, N.Y.
13. Furniss, B. S., A. J. Hannaford, P. W. Smith, and A. R. Tatchell. 1989. Quinones, p. 1261. In A. I. Vogel (ed.), Vogel's textbook of practical organic chemistry, 5th ed. Longman, London, England.
14. Goodell, B., J. Jellison, J. Liu, G. Daniel, A. Paszczynski, F. Fekete, S. Krishnamurthy, L. Jun, and G. Xu. 1997. Low molecular weight chelators and phenolic compounds isolated from wood decay fungi and their role in the fungal biodegradation of wood. J. Biotechnol. 53:133-162.
15. Guillen, F., M. J. Martinez, C. Munoz, and A. T. Martinez. 1997. Quinone redox cycling in the ligninolytic fungus Pleurotus eryngii leading to extracellular production of superoxide anion radical. Arch. Biochem. Biophys. 339: 190-199.
16. Hammel, K. E., K. A. Jensen, M. D. Mozuch, L. L. Landucci, M. Tien, and E. A. Pease. 1993. Ligninolysis by a purified lignin peroxidase. J. Biol. Chem. 268:12274-12281.
17. Higuchi, T. 1985. Biosynthesis and biodegradation of wood components. Academic Press, Inc., London, England.
18. Holdom, M. D., R. J. Hay, and A. J. Hamilton. 1996. The Cu,Zn superoxide dismutases of Aspergillus flavus, Aspergillus niger, Aspergillus terreus: purification and biochemical comparison with the Aspergillus fumigatus Cu,Zn superoxide dismutase. Infect. Immun. 64:3326-3332.
19. Hyde, S. M., and P. M. Wood. 1997. A mechanism for production of hydroxyl radicals by the brown-rot fungus Coniophora puteana: Fe(III) reduction by cellobiose dehydrogenase and Fe(II) oxidation al a distance from the hyphae. Microbiology 143:259-266.
20. Kawai, S., K. A. Jensen, W. Bao, and K. E. Hammel. 1995. New polymeric model substrates for the study of microbial ligninolysis. Appl. Environ. Microbiol. 61:3407-3414.
21. Kersten, P., M. Tien, B. Kalyanaraman, and K. Kirk. 1985. The ligninase of Phanerochaete chrysosporium generates cation radicals from methoxybenzenes. Biol. Chem. 260:2609-2612.
22. Kuwahara, M., T. Ishida, Y. Mijagawa, and C. Kawakami. 1984. Production of extracellular NAD and NADP by a lignin degrading fungus Phanerochaete chrysosporium. J. Ferment. Technol. 62:237-242.
23. Neilands, J., and K. Nakamura. 1991. Detection, determination, isolation, characterisation and regulation of microbial iron chelates, p. 1-14. In G. Winkelmann (ed.). Handbook of microbial iron chelators, CRC Press, Inc., Boca Raton, Fla.
24. Paszczynski, A., and R. L. Crawford. 1995. Potential for bioremediation of xenobiotic compounds by the white-rot fungus Phanerochaete chrysosporium. Biotechnol. Prog. 11:368-379.
25. Poulos, T. L. 1993. Peroxidases. Curr. Biol. 4:484-489.
26. Prati, L., and M. A. Rossi. 1995. A simple route to 4,5-dialkoxy-o-quinones by catalytic oxidation of phenol. Gaz. Chim. Ital. 125:83-86.
27. Schmidthalter, D. R., and G. Canevascini. 1993. Isolation and characterization of cellobiose dehydrogenase from the brown-rot fungus Coniophora puteana (Schum ex Fr) Karst. Arch. Biochem. Biophys. 300:559-563.
28. Shimada, M., Y. Akamtsu, T. Tokimatsu, K. Mii, and T. Hattori. 1997. Possible biochemical roles of oxalic acid as a low molecular weight compound involved in brown-rot and white-rot wood decays. J. Biotechnol. 53:103-113.
29. Varagant, J. 1981. Hydroquinone, resorcinol, and catechol, p. 39-69. In Kirk-Othmer encyclopedia of chemical technology, 3rd ed., vol. 13. John Wiley & Sons, New York, N.Y.
30. Wanzlick, H.-W., and U. Jahnke. 1968. Basenkatalysierte Alkoholaddition an in situ erzeugte o-Chinone. Chem. Ber. 101:3744-3752.
31. Winkelmann, G. 1991. CRC handbook of microbial iron chelators. CRC Press, Inc., Boca Raton, Fla.
32. Zapanta, L. S., and M. Tien. 1997. The roles of veratryl alcohol and oxalate in fungal lignin degradation. J. Biotechnol. 53:93-102.