Evidence from Serpula lacrymans that 2,5-dimethoxyhydroquinone is a lignocellulolytic agent of divergent brown rot basidiomycetes

Applied and Environmental Microbiology

Volumn 79, Issue 7, 2013, Pages 2377-2383

  Korripally, Premsagar ^a   Timokhin, Vitaliy I ^b   Houtman, Carl J ^c   Mozuch, Michael D ^c   Hammel, Kenneth E ^b,c  

^a MAHATMA GANDHI UNIVERSITY   (India)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

^c FOREST PRODUCTS LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROWN ROT BASIDIOMYCETES; CONIFEROUS FORESTS; CONVERGENT EVOLUTION; FENTON CHEMISTRY; LIGNOCELLULOLYTIC ENZYMES; PHYSIOLOGICAL CONDITION; SERPULA LACRYMANS; WHITE-ROT BASIDIOMYCETES;

BIOCHEMISTRY; DECAY (ORGANIC); FORESTRY; FUNGI; PHENOLS; PHYSIOLOGY; WOODEN BUILDINGS;

WOOD;

FERRIC ION; HYDROQUINONE DERIVATIVE; LIGNIN; LIGNOCELLULOSE;

ANCESTRY; BIOCHEMISTRY; BIODEGRADATION; CELLULOSE; CHELATE; CONIFEROUS FOREST; CONVERGENT EVOLUTION; DIVERGENCE; ENZYME ACTIVITY; FUNGAL DISEASE; FUNGUS; KETONE; LIGNIN; METABOLITE; PHYLOGENY; PHYSIOLOGY; POLYMER;

ARTICLE; BASIDIOMYCETES; METABOLISM; MICROBIOLOGY; OXIDATION REDUCTION REACTION; WOOD;

BASIDIOMYCOTA; FERRIC COMPOUNDS; HYDROQUINONES; LIGNIN; METABOLIC NETWORKS AND PATHWAYS; OXIDATION-REDUCTION; WOOD;

BIOCHEMISTRY; DECAY; FORESTRY; FUNGI; PHENOLS; PHYSIOLOGY; WOOD;

APHYLLOPHORALES; BASIDIOMYCOTA; BOLETALES; FUNGI; SERPULA LACRYMANS;

EID: 84875510259     PISSN: 00992240     EISSN: 10985336     Source Type: Journal    
DOI: 10.1128/AEM.03880-12     Document Type: Article

References (32)

1. Floudas D, Binder M, Riley R, Barry K, Blanchette RA, Henrissat B, Martínez AT, Otillar R, Spatafora JW, Yadav JS, Aerts A, Benoit I, Boyd A, Carlson A, Copeland A, Coutinho PM, de Vries RP, Ferreira P, Findley K, Foster B, Gaskell J, Glotzer D, Gorecki P, Heitman J, Hesse C, Hori C, Igarashi K, Jurgens JA, Kallen N, Kersten P, Kohler A, Kües U, Kumar TKA, Kuo A, LaButti K, Larrondo LF, Lindquist E, Ling A, Lombard V, Lucas S, Lundell T, Martin R, McLaughlin DJ, Morgenstern I, Morin E, Murat C, Nagy LG, Nolan M, Ohm RA, Patyshakuliyeva A, Rokas A, Ruiz-Duenas FJ, Sabat G, Salamov A, Samejima M, Schmutz J, Slot JC, St John F, Stenlid J, Sun H, Sun S, Syed K, Tsang A, Wiebenga A, Young D, Pisabarro A, Eastwood DC, Martin F, Cullen D, Grigoriev IV, Hibbett DS. 2012. The Paleozoic origin of enzymatic lignin decomposition reconstructed from 31 fungal genomes. Science. 336:1715-1719.
2. Boerjan W, Ralph J, Baucher M. 2003. Lignin biosynthesis. Annu. Rev. Plant Biol. 54:519-546.
3. Eastwood DC, Floudas D, Binder M, Majcherczyk A, Schneider P, Aerts A, Asiegbu FO, Baker SE, Barry K, Bendiksby M, Blumentritt M, Coutinho PM, Cullen D, de Vries RP, Gathman A, Goodell B, Henrissat B, Ihrmark K, Kauserud H, Kohler A, LaButti K, Lapidus A, Lavin JL, Lee YH, Lindquist E, Lilly W, Lucas S, Morin E, Murat C, Oguiza JA, Park J, Pisabarro AG, Riley R, Rosling A, Salamov A, Schmidt O, Schmutz J, Skrede I, Stenlid J, Wiebenga A, Xie XF, Kües U, Hibbett DS, Hoffmeister D, Hogberg N, Martin F, Grigoriev IV, Watkinson SC. 2011. The plant cell wall-decomposing machinery underlies the functional diversity of forest fungi. Science 333:762-765.
4. Cowling EB. 1961. Comparative biochemistry of the decay of sweetgum sapwood by white-rot and brown-rot fungi. USDA Tech. Bull. 1258. US Government Printing Office, Washington, DC.
5. Eriksson KE, Blanchette RA, Ander P. 1990. Microbial and enzymatic degradation of wood and wood components. Springer, Berlin, Germany.
6. Hatakka A, Hammel KE. 2010. Fungal biodegradation of lignocelluloses, p 319-340. In HofrichterM(ed), Mycota, 2nd ed, vol 10. Springer, Berlin, Germany.
7. Arantes V, Jellison J, Goodell B. 2012. Peculiarities of brown-rot fungi and biochemical Fenton reaction with regard to their potential as a model for bioprocessing biomass. Appl. Microbiol. Biotechnol. 94:323-338
8. Goodell B, Jellison J, Liu J, Daniel G, Paszczynski A, Fekete F, Krishnamurthy S, Jun L, Xu G. 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
9. Jensen KA, Houtman CJ, Ryan ZC, Hammel KE. 2001. Pathways for extracellular Fenton chemistry in the brown rot basidiomycete Gloeophyllum trabeum. Appl. Environ. Microbiol. 67:2705-2711.
10. Kerem Z, Jensen KA, Hammel KE. 1999. Biodegradative mechanism of the brown rot basidiomycete Gloeophyllum trabeum: evidence for an extracellular hydroquinone-driven Fenton reaction. FEBS Lett. 446:49-54.
11. Newcombe D, Paszczynski A, Gajewska W, Kroger M, Feis G, Crawford R. 2002. Production of small molecular weight catalysts and the mechanism of trinitrotoluene degradation by several Gloeophyllum species. Enzyme Microb. Technol. 30:506-517.
12. Paszczynski A, Crawford R, Funk D, Goodell B. 1999. De novo synthesis of 4,5-dimethoxycatechol and 2,5-dimethoxyhydroquinone by the brown rot fungus Gloeophyllum trabeum. Appl. Environ. Microbiol. 65:674-679.
13. Wei DS, Houtman CJ, Kapich AN, Hunt CG, Cullen D, Hammel KE. 2010. Laccase and its role in production of extracellular reactive oxygen species during wood decay by the brown rot basidiomycete Postia placenta. Appl. Environ. Microbiol. 76:2091-2097.
14. Besl H, Bresinsky A, Kopanski L, Steglich W. 1978. Pilzpigmente. XXXV. 3-O-Methylvariegatsäure und verwandte Pulvinsäurederivate aus Kulturen von Hygrophoropsis aurantiaca (Boletales). Z. Naturforsch. C 33:820-825.
15. Gill M, Steglich W. 1987. Pigments of fungi (macromycetes). Prog. Chem. Org. Nat. Prod. 51:1-317.
16. Steglich W, Furtner W, Prox A. 1968. Neue Pulvinsäure-Derivate aus Xerocomus chrysenteron (Bull. ex St. Amans) Quél. und Untersuchungen zur Frage des Vorkommens von Anthrachinonpigmenten bei Boletaceen. Z. Naturforsch. B 23:1044-1050.
17. Shimokawa T, Nakamura M, Hayashi N, Ishihara M. 2004. Production of 2,5-dimethoxyhydroquinone by the brown-rot fungus Serpula lacrymans to drive extracellular Fenton reaction. Holzforschung 58:305-310.
18. Suzuki MR, Hunt CG, Houtman CJ, Dalebroux ZD, Hammel KE. 2006. Fungal hydroquinones contribute to brown rot of wood. Environ. Microbiol. 8:2214-2223.
19. 3+2] cyclization-Suzuki cross-coupling' strategy. Tetrahedron 61: 2055-2063.
20. Hunt C, Kenealy W, Horn E, Houtman C. 2004. A biopulping mechanism: creation of acid groups on fiber. Holzforschung 58:434-439.
21. Dominik P, Kaupenjohann M. 2000. Simple spectrophotometric determination of Fe in oxalate and HCl soil extracts. Talanta 51:701-707.
22. Tien M, Kirk TK. 1988. Lignin peroxidase of Phanerochaete chrysosporium. Methods Enzymol. 161:238-249.
23. Kirk TK, Connors WJ, Bleam RD, Hackett WF, Zeikus JG. 1975. Preparation and microbial decomposition of 14C-lignins. Proc. Natl. Acad. Sci. U. S. A. 72:2515-2519.
24. Curling SF, Clausen CA, Winandy JE. 2002. Relationships between mechanical properties, weight loss, and chemical composition of wood during incipient brown-rot decay. Forest Prod. J. 52:34-39.
25. Ortiz R, Jamet A, Herrera P, Vindigni G, Pereira A. 2011. Influencia del deterioro incipiente producido por el hongo de pudrición parda Serpula lacrymans, sobre las propiedades mecánicas de compresión normal y paralela a la fibra en madera de Pinus radiata D. Don. Inf. Constr. 63:69-74.
26. Guillén F, Muñoz C, Gómez-Toribio V, Martínez AT, Martínez MJ. 2000.Oxygen activation during oxidation of methoxyhydroquinones by laccase from Pleurotus eryngii. Appl. Environ. Microbiol. 66:170-175.
27. O'Brien PJ. 1991. Molecular mechanisms of quinone cytotoxicity. Chem.-Biol. Interact. 80:1-41.
28. Hyde SM, Wood PM. 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 at a distance from the hyphae. Microbiology 143:259-266.
29. Varela E, Tien M. 2003. Effect of pH and oxalate on hydroquinonederived hydroxyl radical formation during brown rot wood degradation. Appl. Environ. Microbiol. 69:6025-6031.
30. Michaelis L, Friedheim E. 1931. Potentiometric studies on complex iron systems. J. Biol. Chem. 91:343-353.
31. Sagone AL, Decker MA, Wells RM, Democko C. 1980. A new method for the detection of hydroxyl radical production by phagocytic cells. Biochim. Biophys. Acta 628:90-97.
32. Bu'Lock JD. 1955. Constituents of the higher fungi. Part IV. A quinone from Polyporus fumosus. J. Chem. Soc. 1955:575-576.