Sulfur tuft and turkey tail: Biosynthesis and biodegradation of organohalogens by Basidiomycetes

Annual Review of Microbiology

Volumn 51, Issue , 1997, Pages 375-414

  De Jong, Ed ^a,b   Field, Jim A ^b  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^b WAGENINGEN UNIVERSITY   (Netherlands)

Author keywords

AOX; Basidiomycetes; Biodegradation; Biosynthesis; Chlorinated compounds; Organohalogens; Phanerochaete chrysosporium; Xenobiotics

Indexed keywords

ORGANOHALOGEN DERIVATIVE;

BASIDIOMYCETES; BIODEGRADATION; BIOSYNTHESIS; BIOTRANSFORMATION; BROMINATION; CHLORINATION; IODINATION; METABOLISM; NONHUMAN; PRIORITY JOURNAL; REVIEW;

ANTI-BACTERIAL AGENTS; BASIDIOMYCOTA; BIODEGRADATION, ENVIRONMENTAL; DIOXINS; ENVIRONMENTAL MICROBIOLOGY; ENVIRONMENTAL POLLUTANTS; HYDROCARBONS, AROMATIC; HYDROCARBONS, CHLORINATED; HYDROCARBONS, HALOGENATED; LIGNIN; OXIDATION-REDUCTION; PENTACHLOROPHENOL; POLYCHLORINATED BIPHENYLS;

BASIDIOMYCOTA; BJERKANDERA; CHRYSOSPORIUM; FUNGI; HERICIUM; PHANEROCHAETE CHRYSOSPORIUM; PHLEBIA; TRAMETES;

EID: 0030798602     PISSN: 00664227     EISSN: None     Source Type: Book Series    
DOI: 10.1146/annurev.micro.51.1.375     Document Type: Review

References (198)

1. Abernethy GA, Walker JRL. 1993. Degradation of the insecticide hydramethylnon by Phanerochaete chrysosporium. Biodegradation 4:131-39
2. Abraham BG, Berger RG. 1994. Higher fungi for generating aroma components through novel biotechnologies. J. Agric. Food Chem. 42:2344-48
3. Adeboya MO, Edwards RL, Lassoe T, Maitland DJ, Shields L, et al. 1996. Metabolites of the higher fungi. 29. Maldoxin, maldoxone, dihydromaldoxin, isodihydromaldoxin and dechlorodihydromaldoxin-a spirocyclohexadienone, a depsidone and three diphenyl ethers-keys in the depsidone biosynthetic pathway from a member of the fungus genus Xylaria. J. Chem. Soc. Perkin Trans. 1:1419-25
4. Alleman BC, Logan BE, Gilbertson RL. 1992. Toxicity of pentachlorophenol to 6 species of white rot fungi as a function of chemical dose. Appl. Environ. Microbiol. 58:4048-50
5. Alleman BC, Logan BE, Gilbertson RL. 1995. Degradation of pentachlorophenol by fixed films of white rot fungi in rotating tube bioreactors. Water Res. 29:61-67
6. Amato I. 1993. The crusade against chlorine. Science 261:152-54
7. Anchel M. 1952. Identification of drosophilin A as p-methoxytetrachlorophenol. J. Am. Chem. Soc. 74:2943
8. Anke T. 1995. The antifungal strobilurins and their possible ecological role. Can. J. Bot. 73(Suppl. 1 E-H):S940-45
9. Anke T, Besl H, Mocek U, Steglich W. 1983. Antibiotics from basidiomycetes. XVIII. Strobilurin C and oudemansin B, two new antifungal metabolites from Xerula species (Agaricales). J. Antibiot. 36:661-66
10. Anke T, Oberwinkler F, Steglich W, Schramm G. 1977. The strobilurins-new antibiotics from the basidiomycete Strobilurus tenacellus (Pers. ex Fr.) Sing. J. Antibiot. 30:806-10
11. Determination of volatile organic compounds in mushrooms. 1993. Short path thermal desorption application note No. 18. Ringoes, NJ: Sci. Instrum. Serv.
12. Archibald F, Paice MG, Jurasek L. 1990. Decolorization of kraft bleachery effluent chromophores by Coriolus (Trametes) versicolor. Enzyme Microb. Technol. 12:846-53
13. Arnone A, Cardillo R, Di Modugno V, Nasini G. 1988. Secondary mould metabolites. XXII. Isolation and structure elucidation of melledonals D and E and melleolides E-H, novel sesquiterpenoid aryl esters from Clitocybe elegans and Armillariamellea. Gaz. Chim. Ital. 118:517-21
14. Arnone A, Cardillo R, Nasini G. 1988. Secondary mould metabolites. XXIII. Isolation and structure elucidation of melleolides I and J and Armellides A and B, novel sesquiterpenoid aryl esters from Armillaria nova-zelandiae. Gaz. Chim. Ital. 118:523-27
15. Arnone A, Cardillo R, Nasini G. 1986. Structures of melleolides B-D, three antibacterial sesquiterpenoids from Armillariamellea. Phytochemistry 25:471-74
16. Arnone A, Cardillo R, Nasini G, Valdo Meille S. 1988. Secondary mould metabolites. Part 19. Structure elucidation and absolute configuration of melledonals B and C, novel antibacterial sesquiterpenoids from Armillariamellea. X-ray molecular structure of melledonal C. J. Chem. Soc. Perkin Trans. 1:503-10
17. Asplund G, Borén H, Carlsson U, Grimvall A. 1991. Soil peroxidase-mediated halogenation of fulvic acids. In Humic Substances in the Aquatic and Terrestrial Environment, ed. B Allard, H Borén, A Grimvall, pp. 475-84. Heidelberg: Springer-Verlag
18. Asplund G, Grimvall A. 1991. Organohalogens in nature-more widespread than previously assumed. Environ. Sci. Technol. 25:1346-50
19. Attieh JM, Hanson AD, Saini HS. 1995. Purification and characterization of a novel methyltransferase responsible for biosynthesis of halomethanes and methanethiol in Brassica oleracea. J. Biol. Chem. 270:9250-57
20. Barr DP, Aust SD. 1994. Mechanisms white rot fungi use to degrade pollutants. Environ. Sci. Technol. 28:A78-87
21. Bastian W. 1985. Vergleichende Untersuchungen zum Sekundärstoffwechsel an Coprophilen und Erd- oder Holzbewohnende Basidiomyceten. PhD thesis. Univ. Kaiserslautern, Germany (In German)
22. Beck HC, Lauritsen FR, Patrick JS, Cooks RG. 1996. Metabolism of halogenated compounds in the white rot fungus Bjerkandera adusta studied by membrane inlet mass spectrometry and tandem mass spectrometry. Biotechnol. Bioeng. 51:23-32
23. Becker U, Anke T, Sterner O. 1994. A novel halogenated compound possessing antibiotic and cytotoxic activities isolated from the fungus Resinicium pinicola (J. Erikss.). Z. Naturforsch. C 49:772-74
24. Bergbauer M, Eggert C, Kraepelin G. 1991. Degradation of chlorinated lignin compounds in a bleach plant effluent by the white-rot fungus Trametes versicolor. Appl. Microbiol. Biotechnol. 34:105-9
25. Bollag J-M, Dec J. 1995. Incorporation of halogenated substances into humic material. In Naturally-Produced Organohalogens, ed. A Grimvall, EWB de Leer, pp. 161-69. Dordrecht: Kluwer
26. Bollag J-M, Sjobald RD, Minard RD. 1977. Polymerization of phenolic intermediates of pesticides by a fungal enzyme. Experienta 33:1564-66
27. Brambilla U, Nasini G, Depava OV. 1995. Secondary mold metabolites. 49. Isolation, structural elucidation, and biomimetic synthesis of trametol, a new 1-arylpropane-1,2-diol produced by the fungus Trametes sp. J. Nat. Prod. 58: 1251-53
28. Bumpus JA, Powers RH, Sun T. 1993. Biodegradation of DDE (1,1-dichloro-2,2-bis(4-chlorophenyl)ethene) by Phanerochaete chrysosporium. Mycol. Res. 97:95-98
29. Bumpus JA, Tien M, Wright D, Aust SD. 1985. Oxidation of persistent environmental pollutants by a white-rot fungus. Science 228:1434-36
30. Buss H, Zimmer L. 1974. Natürliche polychlorierte Aromaten in Champignons. Chemosphere 3:123-26
31. Butruille D, Dominquez XA. 1972. Un nouveau produit naturel: 1,4-Dimethoxy-2-nitro-3,5,6-trichlorobenzene. Tetrahedron Lett. 3:211-12
32. Chang CW, Bumpus JA. 1993. Oligomers of 4-chloroaniline are intermediates formed during its biodegradation by Phanerochaete chrysosporium. FEMS Microbiol. Lett. 107:337-42
33. Cheng HH, Haider K, Harper SS. 1983. Catechol and chlorocatechols in soil: degradation and extractability. Soil Biol. Biochem. 15:311-17
34. Chilton WS, Tsou G. 1972. A chloro amino acid from Amanita solitaria. Phytochemistry 11:2853-57
35. Chilton WS, Tsou G, De Cato L Jr, Malone MH. 1973. The unsaturated norleucines from Amanita solitaria. Chemical and pharmacological studies. Lloydia 36:169-73
36. Chung NH, Aust SD. 1995. Veratryl alcohol-mediated indirect oxidation of pentachlorophenol by lignin peroxidase. Arch. Biochem. Biophys. 322:143-48
37. Chung NM, Aust SD. 1995. Degradation of pentachlorophenol in soil by Phanerochaete chrysosporium. J. Haz. Mat. 41:177-83
38. Claus H, Filip Z. 1990. Enzymatic oxidation of some substituted phenols and aromatic amines, and the behaviour of some phenoloxidases in the presence of soil related adsorbents. Water Sci. Technol. 22:69-77
39. Cowan MI, Glen AT, Hutchinson SA, Maccartney ME, Mackintosh JM, et al. 1973. Production of volatile metabolites by species of Fumes. Trans. Br. Mycol. Soc. 60:347-60
40. Cremin P, Donnelly DMX, Weifender JL, Hostettmann K. 1995. Liquid chromatographic-thermospray mass spectrometric analysis of sesquiterpenes of Armillaria (Eumycota, Basidiomycotina) species. J. Chrom. 710:273-85
41. Dahlman O, Morck R, Ljungquist P, Reimann A, Johansson C, et al. 1993. Chlorinated structural elements in high molecular weight organic matter from unpolluted waters and bleached-kraft mill effluents. Environ. Sci. Technol. 27:1616-20
42. Dahlman O, Reimann A, Ljungquist P, Mörck R, Johansson C, et al. 1994. Characterization of chlorinated aromatic structures in high molecular weight BKME-materials and in fulvic acids from industrially unpolluted waters. Water Sci. Technol. 29:81-91
43. Dec J, Bollag J-M. 1988. Microbial release and degradation of catechol and chlorophenols bound to synthetic humic acid. Soil Sci. Soc. Am. J. 52:1366-71
44. Dec J, Bollag J-M. 1994. Dehalogenation of chlorinated phenols during oxidative coupling. Environ. Sci. Technol. 28:484-90
45. Dec J, Bollag J-M. 1995. Effect of various factors on dehalogenation of chlorinated phenols and anilines during oxidative coupling. Environ. Sci. Technol. 29:657-63
46. De Jong E, Cazemier AE, Field JA, de Bont JAM. 1994. Physiological role of chlorinated aryl alcohols biosynthesized de novo by the white rot fungus Bjerkandera sp. strain BOS55. Appl. Environ. Microbiol. 60:271-77
47. De Jong E, Field JA, De Bont JAM. 1994. Aryl alcohols in the physiology of ligninolytic fungi. FEMS Microbiol. Rev. 13:153-88
48. De Jong E, Field JA, Dings JAFM, Wijnberg JBPA, de Bont JAM. 1992. De novo biosynthesis of chlorinated aromatics by the white-rot fungus Bjerkandera sp. BOS55. Formation of 3-chloroanisaldehyde from glucose. FEBS Lett. 305:220-24
49. De Jong E, Field JA, Spinnler HE, Wijnberg JBPA, de Bont JAM. 1994. Significant biogenesis of chlorinated aromatics by fungi in natural environments. Appl. Environ. Microbiol. 60:264-70
50. Dietrich D, Hickey WJ, Lamar R. 1995. Degradation of 4,4′-dichlorobiphenyl, 3, 3′,4,4′-tetrachlorobiphenyl, and 2,2′,4,4′, 5,5′-hexachlorobiphenyl by the white rot fungus Phanerochaete chrysosporium. Appl. Environ. Microbiol. 61:3904-9
51. Donnelly DMX, Coveney DJ, Fukuda N, Polonsky J. 1986. New sesquiterpene arylesters from Armillaria mellea. J. Nat. Prod. 49:111-18
52. Donnelly PK, Entry JA, Crawford DL. 1993. Degradation of atrazine and 2,4-dichlorophenoxyacetic acid by mycorrhizal fungi at 3 nitrogen concentrations in vitro. Appl. Environ. Microbiol. 59:2642-47
53. Ellis MB, Ellis JP. 1990. Fungi without Gills (Hymenomycetes and Gasteromycetes). London: Chapman & Hall. 329 pp.
54. Entry JA, Donnelly PK, Emmingham WH. 1996. Mineralization of atrazine and 2,4-d in soils inoculated with Phanerochaete chrysosporium and Trappea darken. Appl. Soil Ecol. 3:85-90
55. Esaki N, Takada H, Moriguchi M, Hatanaka SI, Tanaka H, et al. 1989. Mechanism-based inactivation of L-methionine gamma-lyase by L-2-amino-4-chloro-4-pentenoate. Biochemistry 28:2111-16
56. Farhangrazi ZS, Sinclair R, Yamazaki I, Powers LS. 1992. Haloperoxidase activity of Phanerochaete chrysosporium lignin peroxidases H2 and H8. Biochemistry 31:10763-68
57. Ferrey ML, Koskinen WC, Blanchette RA, Burnes TA. 1994. Mineralization of alachlor by lignin-degrading fungi. Can. J. Microbiol. 40:795-98
58. Field JA, de Jong E, Feijoo Costa G, de Bont JAM. 1993. Screening for ligninolytic fungi applicable to the biodegradation of xenobiotics. Trends Biotechnol. 11:44-49
59. Field JA, Stams AJM, Kato M, Schraa G. 1995. Enhanced biodegradation of aromatic pollutants in cocultures of anaerobic and aerobic bacterial consortia. Antonie van Leeuwenhoek 67:47-77
60. Field JA, Verhagen FJM, de Jong E. 1995. Natural organohalogen production by basidiomycetes. Trends Biotechnol. 13:451-56
61. Frankland JC. 1982. Biomass and nutrient cycling by decomposer basidiomycetes. In Decomposer Basidiomycetes: Their Biology and Ecology, ed. JC Frankland, JN Hedger, MJ Swift, pp. 241-61. Cambridge: Cambridge Univ. Press
62. Fukui H, Presnell TL, Joyce TW, Chang HM. 1992. Dechlorination and detoxification of bleach plant effluent by Phanerochaete chrysosporium. J. Biotechnol. 24:267-75
63. Fulthorpe RR, Rhodes AN, Tiedje JM. 1996. Pristine soils mineralize 3-chlorobenzoate and 2,4-dichlorophenoxyacetate via different microbial populations. Appl. Environ. Microbiol. 62:1159-66
64. Gill M, Giménez A. 1990. Pigments of fungi. Part 17. (S)-(+)-Dermochrysone, (+)-dermolactone, dermoquinone, and related pigments; new nonoketides from the fungus Dermocybe sanguinea (sensu Cleland). J. Chem. Soc. Perkin Trans. 1:2585-91
65. Graedel TE, Keene WC. 1996. The budget and cycle of earth's natural chlorine. Pure Appl. Chem. 68:1689-97
66. Gribble GW. 1996. The diversity of natural organohalogens in living organisms. Pure Appl. Chem. 68:1699-712
67. Gribble GW. 1996. Naturally Occurring Organohalogen Compounds-A Comprehensive Survey. New York: Springer Verlag. 498 pp.
68. Griffith GS, Rayner ADM, Wildman HG. 1994. Extracellular metabolites and mycelial morphogenesis of Hypholoma fasciculare and Phlebia radiata (Hymenomycetes). Nova Hedwigia 59:311-29
69. Grimvall A. 1995. Evidence of naturally produced and man-made organohalogens in water and sediments. See Ref. 69a, pp. 3-20
70. Grimvall A, de Leer EWB, eds. 1995. Naturally-Produced Organohalogens. Dordrecht: Kluwer
71. Grove JF. 1981. Volatile compounds from the mycelium of the mushroom Agaricus bisporus. Phytochemistry 20:2021-22
72. Gutierrez A, Caramelo L, Prieto A, Martinez MJ, Martinez AT. 1994. Anisaldehyde production and aryl-alcohol oxidase and dehydrogenase activities in ligninolytic fungi of the genus Pleurotus. Appl. Environ. Microbiol. 60:1783-88
73. Häggblom MM. 1992. Microbial breakdown of halogenated aromatic pesticides and related compounds. FEMS Microbiol. Rev. 103:29-72
74. Haggblom MM, Apajalahti JHA, Salkinoja-Salonen MS. 1988. O-Methylation of chlorinated para-hydroquinones by Rhodococcus chlorophenolicus. Appl. Environ. Microbiol. 54:1818-24
75. Hammel KE, Tardone PJ. 1988. The oxidative 4-dechlorination of polychlorinated phenols is catalyzed by extracellular fungal lignin peroxidases. Biochemistry 27:6563-68
76. Harper DB. 1994. Biosynthesis of halogenated methanes. Biochem. Soc. Trans. 22:1007-11
77. Harper DB, Buswell JA, Kennedy JT, Hamilton JTG. 1990. Chloromethane, methyl donor in veratryl alcohol biosynthesis in Phanerochaete chrysosporium and other lignin-degrading fungi. Appl. Environ. Microbiol. 56:3450-57
78. Harper DB, Hamilton JTG, Kennedy JT, McNally KJ. 1989. Chloromethane, a novel methyl donor for biosynthesis of esters and anisoles in Phellinus pomaceus. Appl. Environ. Microbiol. 55:1981-89
79. Harper DB, Kennedy JT. 1986. Effect of growth conditions on halomethane production by Phellinus species: biological and environmental implications. J. Gen. Microbiol. 132:1231-46
80. Harper DB, Kennedy JT, Hamilton JTG. 1988. Chloromethane biosynthesis in poroid fungi. Phytochemistry 27:3147-53
81. Harper DB, McRoberts WC, Kennedy JT. 1996. Comparison of the efficacies of Chloromethane, methionine, and s-adenosylmethionine as methyl precursors in the biosynthesis of veratryl alcohol and related compounds in Phanemchaete chrysosporium. Appl. Environ. Microbiol. 62:3366-70
82. Hatanaka SI, Furukawa J, Aoki T, Akatsuka H, Nagasawa E. 1994. (2S)-2-Amino-5-chloro-4-hydroxy-5-hexenoic acid, a new chloroamino acid, and related compounds from Amanita gymnopus. Mycoscience 35:391-94
83. Hatanaka SI, Kaneko S, Niimura Y, Kinoshita F, Soma GI. 1974. L-2-Amino-4-chloro-4-pentenoic acid, a new natural ammo acid from Amanita pseudoporphyria Hongo. Tetrahedron Lett. 45:3931-32
84. Hatanaka SI, Niimura Y, Takishima K. 1985. Non-protein amino acids of unsaturated norleucine-type in Amanita pseudoporphyria. Trans. Mycol. Soc. Jpn. 26:61-68
85. Hatanaka SI, Okada K, Nagasawa E. 1995. Isolation and identification of (2S)-2-Amino-5-chloro-4-hydroxy-5-hexenoic acid from an Amanita of the section Roanokenses (Amanitaceae). Mycoscience 36:395-97
86. Hautzel R, Anke H. 1990. Screening of Basidiomycetes and Ascomycetes for plant growth regulating substances. Introduction of the gibberellic acid induced de novo synthesis of hydrolytic enzymes in embryoless seeds of Triticum aestivum as test system. Z. Naturforsch. C 45:1093-98
87. Hautzel R, Anke H, Sheldrik WS. 1990. Mycenon, a new metabolite from a Mycena species TA 87202 (Basidiomycetes) as an inhibitor of isocitrate lyase. J. Antibiot. 18:1240-44
88. Hibbett DS, Donoghue MJ. 1995. Progress toward a phylogenetic classification of the polyporaceae through parsimony analysis of mitochondrial ribosomal DNA sequences. Can. J. Bot. 73(Suppl. 1 E-H):S853-61
89. Hickey WJ, Fuster DJ, Lamar RT. 1994. Transformation of atrazine in soil by Phanerochaete chrysosporiurn. Soil Biol. Biochem. 26:1665-71
90. Hjelm O. 1996. Organohalogens in coniferous forest soil. PhD thesis. Linköping Stud. Arts Sci. 139, Linköping, Sweden
91. Hjelm O, Asplund G. 1995. Chemical characterization of organohalogens in a coniferous forest soil. See Ref. 69a, pp. 105-11
92. Hjelm O, Boren H, Öberg G. 1996. Analysis of halogenated organic compounds in coniferous forest soil from a Lepista nuda (wood blewitt) fairy ring. Chemosphere 32:1719-28
93. Hjelm O, Johansson MB, Oberg-Asplund G. 1995. Organically bound halogens in coniferous forest soil - distribution pattern and evidence of in situ production. Chemosphere 30:2353-64
94. Hoekstra EJ, Lassen P, van Leeuwen JGE, de Leer EWB, Carlsen L. 1995. Formation of organic chlorine compounds of low molecular weight in the chloroperoxidase-mediated reaction between chloride and humic material. See Ref. 69a, pp. 149-58
95. Hsu C-S, Suzuji M, Yamada Y. 1971. Chemical constituents of fungi 1 1,4-dimethoxy-2,3,5,6-tetrachlorobenzene (O-Drosophilin A) from Phellinus yucatensis. Chem. Abstr. 115864a, Vol. 75
96. Huff T, Kuball HG, Anke T. 1994. 7-Chloro-4,6-dimethoxy-1 (3H)-isobenzofurane and basidalin: Antibiotic secondary metabolites from Leucoagaricus carneifolia Gillet (Basidiomycetes). Z. Naturforsch. C 49:407-10
97. Hutchinson SA. 1971. Biological activity of volatile fungal metabolites. Trans. Br. Mycol. Soc. 57:185-200
98. Iimura Y, Hartikainen P, Tatsumi K. 1996. Dechlorination of tetrachloroguaiacol by laccase of white-rot basidiomycete Coriolus versicolor. Appl. Microbiol. Biotechnol. 45:434-39
99. Jain SC, Kumar R, Bharadvaja A, Parmar VS, Errington W, et al. 1996. Novel products of some wood rotting fungi, Abstr. IUPAC Symp. Chem. Nat. Prod, 20th. Chicago, Sept. 15-20, p. SE-35
100. Jensen KA, Evans KMC, Kirk TK, Hammel KE. 1994. Biosynthetic pathway for veratryl alcohol in the ligninolytic fungus Phanerochaete chrysosporium. Appl. Environ. Microbiol. 60:709-14
101. Johansson C, Borén H, Grimvall A, Dahlman O, Mörck R, et al. 1995. Halogenated structural elements in naturally occurring organic matter. See Ref. 69a, pp. 95-103
102. Joshi DK, Gold MH. 1993. Degradation of 2,4,5-trichlorophenol by the lignin-degrading basidiomycete Phanerochaete chrysosporium. Appl. Environ. Microbiol. 59:1779-85
103. JunShan Y, Yuwu C, Xiaozhang F, Dequan Y, Xiaotian L. 1984. Chemical constituents of Armillariamellea mycelium I. Isolation and characterization of armillarin and armillaridin. Planta Med. 50:288-90
104. Kalyanaraman B. 1995. Radical intermediates during degradation of lignin-model compounds and environmental pollutants-an electron spin resonance study. Xenobiotica 25:667-75
105. Kavanagh F, Hervey A, Robbins WJ. 1952. Antibiotic substances from basidiomycetes. IX. Drosophila subarata (Batsch:Fr) Quel. Proc. Natl. Acad. Sci. USA 38:555-60
106. Keller G. 1982. Pigmentations Untersuchungen bei europäischen Arten aus der Gattung Dermocybe (Fr.) Wünsche. Sydowia 35:110-26
107. Keller G, Ammirati JF. 1983. Chemotaxonomic significance of anthraquinone derivatives in North America species of Dermocybe section sanguineae. Mycotaxon 18:357-77
108. Kennedy DW, Aust SD, Bumpus JA. 1990. Comparative biodegradation of alkyl halide insecticides by the whiterot fungus, Phanerochaete chrysosporium (BKM-F-1767). Appl. Environ. Microbiol. 56:2347-53
109. Khindaria A, Grover TA, Aust SD. 1995. Reductive dehalogenation of aliphatic halocarbons by lignin peroxidase of Phanerochaete chrysosporium. Environ. Sci. Technol. 29:719-25
110. Kirk TK, Farrell RL. 1987. Enzymatic 'combustion': the microbial degradation of lignin. Annu. Rev. Microbiol. 41:465-505
111. Köhler A, Jäger A, Willershausen H, Graf H. 1988. Extracellular ligninase of Phanerochaete chrysosporium Burdsall has no role in the degradation of DDT. Appl. Microbiol. Biotechnol. 29:618-20
112. Kremer S, Anke H, Sterner O. 1992. Metabolism of chlorinated phenols by members of the genus Mycena. Preprints: Soil Decontam. Using Biol. Process., Karlsruhe, FRG, pp. 298-304. 6-9 Dec.
113. Kremer S, Sterner O. 1996. Metabolism of 3,4-dichloroaniline by the basidiomycete Filoboletus species TA9054. J. Agric. Food Chem. 44:1155-59
114. Kremer S, Sterner O, Anke H. 1992. Degradation of pentachlorophenol by Mycena avenacea TA-8480-identification of initial dechlorinated metabolites. Z. Naturforsch. C 47:561-66
115. Lamar RT, Davis MW, Dietrich DM, Glaser JA. 1994. Treatment of a pentachlorophenol- and creosote-contaminated soil using the lignin-degrading fungus Phanerochaete sordida: a field demonstration. Soil Biol. Biochem. 26:1603-11
116. Lamar RT, Dietrich DM. 1990. In situ depletion of pentachlorophenol from contaminated soil by Phanerochaete spp. Appl. Environ. Microbiol. 56:3093-100
117. Lamar RT, Dietrich DM. 1992. Use of lignin-degrading fungi in the disposal of pentachlorophenol-treated wood. J. Ind. Microbiol. 9:181-91
118. Lamar RT, Glaser JA, Kirk TK. 1990. Fate of pentachlorophenol (PCP) in sterile soils inoculated with the white-rot basidiomycete Phanerochaete chrysosporium: mineralization, volatilization and depletion of PCP. Soil Biol. Biochem. 22:433-40
119. Lauritsen FR, Kotiaho T, Lloyd D. 1993. Rapid and direct monitoring of volatile fermentation products in the fungus Bjerkandera adusta by membrane inlet tandem mass spectrometry. Biol. Mass Spectrom. 22:585-89
120. Lee D, Takahashi M, Tsunoda K. 1992. Fungal detoxification of organoiodine wood perservatives. Holzforschung 46:81-86
121. Lestan D, Lamar RT. 1996. Development of fungal inocula for bioaugmentation of contaminated soils. Appl. Environ. Microbiol. 62:2045-52
122. Lyr H. 1962. Detoxification of heartwood toxins and chlorophenols by higher fungi. Nature 195:289-90
123. Maloney SW, Manem J, Mallevialle J, Flessinger F. 1986. Transformation of trace organic compounds in drinking water by enzymatic oxidative coupling. Environ. Sci. Technol. 20:249-53
124. Martens R, Wetzstein H-G, Zadrazil F, Capelari M, Hoffmann P, et al. 1996. Degradation of the fluoroquinolone Enrofloxacin by wood-rotting fungi. Appl. Environ. Microbiol. 62:4206-9
125. Marzullo L, Cannio R, Giardina P, Santini MT, Sannia G. 1995. Veratryl alcohol oxidase from Pleurotus ostreatus participates in lignin biodegradation and prevents polymerization of laccase-oxidized substrates. J. Biol. Chem. 270:3823-27
126. Masaphy S, Levanon D, Henis Y. 1996. Degradation of atrazine by the lignocellulolytic fungus Pleurotus pulmonarius during solid-state fermentation. Biores. Technol. 56:207-14
127. McInnes AG, Walter JA, Wright JLC, Vining LC, Ranade N, et al. 1990. Biosynthesis of mollisin by Mollisia caesia. Can. J. Chem. 68:1-4
128. McNally KJ, Harper DB. 1991. Methylation of phenol by chloromethane in the fungus Phellinus pomaceus. J. Gen. Microbiol. 137:1029-32
129. Mester T, Swarts HJ, Romero i Sole S, de Bont JAM, Field JA. 1997. Stimulation of aryl metabolite production in the basidiomycete Bjerkandera sp. strain BOS55 with biosynthetic precursors and lignin degradation products. Appl. Environ. Microbiol. 63:1987-94
130. Michel FC Jr, Reddy CA, Forney LJ. 1995. Microbial degradation and humification of the lawn care pesticide 2,4-dichlorophenoxyacetic acid during the composting of yard trimmings. Appl. Environ. Microbiol. 61:2566-71
131. Mileski GJ, Bumpus JA, Jurek MA, Aust SD. 1988. Biodegradation of pentachlorophenol by the white-rot fungus Phanerochaete chrysosporium. Appl. Environ. Microbiol. 54:2885-89
132. Morgan P, Lee SA, Lewis ST, Sheppard AN, Watkinson RJ. 1993. Growth and biodegradation by white-rot fungi inoculated into soil. Soil Biol. Biochem. 25:279-87
133. Moriguchi M, Hara Y, Hatanaka S-I. 1987. Antibacterial activity of L-2-amino-4-chloro-4-pentenoic acid isolated from Amanita pseudoporphyria Hongo. J. Antibiot. 15:904-6
134. Mougin C, Pericaud C, Malosse C, Laugero C, Asther M. 1996. Biotransformation of the insecticide lindane by the white rot basidiomycete Phanerochaete chrysosporium. Pestic. Sci. 47:51-59
135. Muller G, Nkusi G, Scholer HF. 1996. Natural organohalogens in sediments. J. Prak. Chem. 338:23-29
136. Nair MSR, Hervey A. 1979. Structure of lepiochlorin, an antibiotic metabolite of a fungus cultivated by ants. Phytochemistry 18:326-27
137. Nauta MM, Vellinga EC. 1995. Atlas van Nederlandse paddestoelen. Rotterdam: Balkema Uitgevers (In Dutch)
138. Neidleman SL, Geigert J. 1986. Biohalogenation: Principles, Basic Roles and Applications. Chichester, UK: Wiley. 203 pp.
139. Neilson AH. 1996. An environmental perspective on the biodegradation of organochlorine xenobiotics. Int. Biodet. Biodegr. 37:3-21
140. Öberg G, Brunberg H, Hjelm O. 1996. Production of organically bound chlorine during degradation of Birch wood by common white-rot fungi. Soil Biol. Biochem. In press
141. Ohta T, Matsuda M, Takahashi T, Nakajima S, Nozoe S. 1995. (S)-cis-2-amino-5-chloro-4-pentenoic acid from the fungus Amanita vergineoides. Chem. Pharm. Bull. 43:899-900
142. Ohta T, Nakajima S, Hatanaka SI, Yamamoto M, Shimmen Y, et al. 1987. A chlorohydrin amino acid from Amanita abrupta. Phytochemistry 26:565-66
143. Ohta T, Takahashi A, Matsuda M, Kamo S, Agatsuma T, et al. 1995. Russuphelol, a novel optically active chlorohydroquinone tetramer from the mushroom Russula subnigricans. Tetrahedron Lett. 36:5223-26
144. Okamoto K, Shimada A, Shirai R, Sakamoto H, Yoshida S, et al. 1993. Antimicrobial chlorinated orcinol derivatives from mycelia of Hericium erinaceum. Phytochemistry 34:1445-46
145. Okeke BC, Smith JE, Paterson A, Watsoncraik IA. 1996. Influence of environmental parameters on pentachlorophenol biotransformation in soil by Lentinula edodes and Phanerochaete chrysosporium. Appl. Microbiol. Biotechnol. 45:263-66
146. Pallerla S, Chambers RP. 1996. New urethane prepolymer immobilized fungal bioreactor for decolorization and dechlorination of kraft bleach effluents. TAPPI J. 79(5):155-61
147. Paszczynski A, Crawford RL. 1995. Potential for bioremediation of xenobiotic compounds by the white-rot fungus Phanerochaete chrysosporium. Biotechnol. Progr. 11:368-79
148. Peipp H, Sonnenbichler J. 1992. Secondary fungal metabolites and their biological activities. II. Occurrence of antibiotic compounds in cultures of Armillaria ostoye growing in the presence of an antagonistic fungus or host plant cells. Biol. Chem. Hoppe Seyler 373:675-83
149. Pelaez F, Martinez MJ, Martinez AT. 1995. Screening of 68 species of Basidiomycetes for enzymes involved in lignin degradation. Mycol. Res. 99:37-42
150. Pfefferle W, Anke H, Bross M, Steglich W. 1990. Inhibition of solubilized chitin synthase by chlorinated aromatic compounds isolated from mushroom cultures. Agric. Biol. Chem. 54:1381-84
151. Pieper DH, Timmis KN, Ramos JL. 1996. Designing bacteria for the degradation of nitro- and chloroaromatic pollutants [Review]. Naturwissenschaften 83:201-13
152. Pieper DH, Winkler R, Sandermann H. 1992. Formation of a toxic dimerization product of 3,4-dichloroaniline by lignin peroxidase from Phanerochaete chrysosporium. Angew. Chem. 31:68-70
153. Pryke DC, McKenzie DJ. 1996. Substitution of chlorine dioxide for chlorine in Canadian bleached chemical pulp mills. Pulp Pap. Can. 97(1):27-29
154. Pyysalo H. 1976. Identification of volatile compounds in seven edible fresh mushrooms. Acta Chem. Scand. B 30:235-44
155. Qian FG, Xu GY, Du SJ, Li MH. 1990. Isolation and identification of two new pyrone compounds from the culture of Hericium erinaceus. Acta Pharm. Sin. 25:522-25
156. Rappe C. 1996. Sources and environmental concentrations of dioxins and related compounds. Pure Appl. Chem. 68:1781-89
157. Renganathan V, Miki K, Gold MH. 1987. Haloperoxidase reactions catalyzed by lignin peroxidase, an extracellular enzyme from the basidiomycete Phanerochaete chrysosporium. Biochemistry 26:5127-32
158. Ricotta A, Unz RF, Bollag JM. 1996. Role of a laccase in the degradation of pentachlorophenol. Bull. Environ. Contam. Toxicol. 57:560-67
159. Roper JC, Sarkar JM, Dec J, Bollag JM. 1995. Enhanced enzymatic removal of chlorophenols in the presence of cosubstrates. Water Res. 29:2720-24
160. Rotard W, Christmann W, Knoth W. 1994. Background levels of PCDD/F in soils of Germany. Chemosphere 29:2193-200
161. Roy-Arcand L, Archibald FS. 1991. Direct dechlorination of chlorophenolic compounds by laccases from Trametes (Coriolus) versicolor. Enzyme Microb. Technol. 13:194-203
162. Schwarz M, Marr J, Kremer S, Sterner O, Anke H. 1992. Biodegradation of xenobiotic compounds by fungi: metabolism of 3,4-dichloroaniline by Schizophyllum species and Auriculariopsis ampla and induction of indigo production. Preprints: Soil Decontam. Using Biol. Proc., 6-9 Dec. Karlsruhe, FRG, pp. 459-64
163. Shah MM, Grover TA, Aust SD. 1993. Reduction of CCI4 to the trichloromethyl radical by lignin peroxidase H2 from Phanerochaete chrysosporium. Biochem. Biophys. Res. Commun. 191:887-92
164. Singh P, Rangaswami S. 1966. Occurrence of O-methyl-drosophilin A in Fumes fastuosus Lev. Tetrahedron Lett. 11:1229-31
165. Smith ML, Bruhn JN, Anderson JB. 1992. The fungus Armillaria bulbosa is among the largest and oldest living organisms. Nature 356:428-31
166. Solomon KR. 1996. Chlorine in the bleaching of pulp and paper. Pure Appl. Chem. 68:1721-30
167. Sonnenbichler J, Bliestle IM, Peipp H, Holdenrieder O. 1989. Secondary fungal metabolites and their biological activities, I. Isolation of antibiotic compounds from cultures of Heterobasidion annosum synthesized in the presence of antagonistic fungi or host plant cells. Biol. Chem. Hoppe Seyler 370:1295-303
168. Sonnenbichler J, Dietrich J, Peipp H. 1994. Secondary fungal metabolites and their biological activities. 5. Investigations concerning the induction of the biosynthesis of toxic secondary metabolites in Basidiomycetes. Biol. Chem. Hoppe Seyler 375:71-79
169. Spinnler HE, de Jong E, Mauvais G, Semon E, Lequere JL. 1994. Production of halogenated compounds by Bjerkandera adusta. Appl. Microbiol. Biotechnol. 42:212-21
170. Steglich W, Lösel W, Austel V. 1969. Anthrachinon-pigmente aus Dermocybe sanguinea (Wulf. ex Fr.) Wünsche and D. semisanguinea (Fr.). Chem. Ber. 102:4104-18
171. Steiman R, Benoit-Guyod JL, Seigle-Murandi F, Sage L, Toe A. 1994. Biodegradation of pentachlorophenol by micromycetes. 2. Ascomycetes, basidiomycetes, and yeasts. Environ. Toxicol. Water Qual. 9:1-6
172. Suzuki T. 1983. Methylation and hydroxylation of pentachlorophenol by Mycobacterium sp. isolated from soil. Pestic. Sci. 8:419-28
173. Swarts HJ, Teunissen PJM, Verhagen FJM, Field JA, Wijnberg JBPA. 1997. Chlorinated anisyl metabolites produced by basidiomycetes. Mycol. Res. 101:372-74
174. Swarts HJ, Verhagen FJM, Field JA, Wijnberg JBPA. 1996. Novel chlorometabolites produced by Bjerkandera species. Phytochemistry 42:1699-701
175. Swift MJ. 1982. Basidiomycetes as components of forest ecosystems. In Decomposer Bosidiomycetes: Their Biology and Ecology, ed. JC Frankland, JN Hedger, MJ Swift, pp. 307-37. Cambridge: Cambridge Univ. Press
176. Takahashi A, Agatsuma T, Matsuda M, Ohta T, Nunozawa T, et al. 1992. Russuphelin A, a new cytotoxic substance from the mushroom Russala subnigricans Hongo. Chem. Pharm. Bull. 40:3185-88
177. Takahashi A, Agatsuma T, Ohta T, Nunozawa T, Endo T, et al. 1993. Russuphelin-B, Russuphelin-C, Russuphelin-D, Russuphelin-E and Russuphelin-F, new cytotoxic substances from the mushroom Russula subnigricans Hongo. Chem. Pharm. Bull. 41:1726-29
178. Tatsumi K, Freyer A, Minard RD, Bollag J-M. 1994. Enzyme-mediated coupling of 3,4-dichloroaniline and ferulic acid: a model for pollutant binding to humic materials. Environ. Sci. Technol. 28:210-15
179. Teunissen PJM, Swarts HJ, Field JA. 1997. Screening of ligninolytic basidiomycetes for the production of Drosophilin A (tetrachloro-4-methoxyphenol) and Drosophilin A methyl ether (tetrachloro-1,4-dimethoxybenzene). Appl. Microbiol. Biotechnol. In press
180. Thaller V, Turner JL. 1972. Natural acetylenes Part XXXV. Polyacetylenic acid and benzenoid metabolites from cultures of the fungus Lepista diemii Singer. J. Chem. Soc. Perkin Trans. 1:2032-34
181. Thomas AF. 1973. An analysis of the flavor of the dried mushroom, Boletus edulis. J. Agric. Food Chem. 21:955-58
182. Thomas DR, Carswell KS, Georgiou G. 1992. Mineralization of biphenyl and PCBs by the white rot fungus Phanerochaete chrysosporium. Biotechnol. Bioeng. 40:1395-1402
183. Turner EM, Wright M, Ward T, Osborne DJ, Self RJ. 1975. Production of ethylene and other volatiles and changes in cellulase and laccase activities during the life cycle of the cultivated mushroom Agaricus bisporus. J. Gen. Microbiol. 91:167-76
184. Turner WB, Aldridge DC. 1983. Fungal Metabolites II. London: Academic. 631 pp.
185. Valli K, Gold MH. 1991. Degradation of 2,4-dichlorophenol by the lignin- degrading fungus Phanerochaete chrysosporium. J. Bacteriol. 173:345-52
186. Valli K, Wariishi H, Gold MH. 1992. Degradation of 2,7-dichlorodibenzo-p-dioxin by the lignin-degrading basidiomycete Phanerochaete chrysosporium. J. Bacteriol. 174:2131-37
187. van Eijk GW. 1975. Drosophilin A methyl ether from Mycena megaspora.
188. Verhagen FJM, Swarts HJ, Kuyper TW, Wijnberg JBPA, Field JA. 1996. The ubiquity of natural adsorbable organic halogen production among basidiomycetes. Appl. Microbiol. Biotechnol. 45:710-18
189. Vyas BRM, Sasek V, Matucha M, Bubner M. 1994. Degradation of 3,3′,4,4′-tetrachlorobiphenyl by selected white rot fungi. Chemosphere 28:1127-34
190. Wang SH, Ferguson JF, McCarthy JL. 1992. The decolorization and dechlorination of Kraft bleach plant effluent solutes by use of 3 fungi-Ganaderma lucidum, Coriolus versicolor and Hericium erinaceus. Holzforschung 46:219-23
191. Whitney RD. 1995. Root-rotting fungi in white spruce, black spruce, and balsam fir in Northern Ontario. Can. J. For. Res. 25:1209-30
192. Wunder A, Anke T, Klostermeyer D, Steglich W. 1996. Lactarane type sesquiterpenoids as inhibitors of leukotriene biosynthesis and other, new metabolites from submerged cultures of Lentinellus cochleatus (Pers. ex Fr.) Karst. Z. Naturforsch. C 51:493-99
193. Wuosmaa AM, Hager LP. 1990. Methyl chloride transferase: a carbocation route for biosynthesis of halometabolites. Science 249:160-62
194. Yadav JS, Quensen JF, Tiedje JM, Reddy CA. 1995. Degradation of polychlorinated biphenyl mixtures (Aroclors 1242, 1254, and 1260) by the white rot fungus Phanerochaete chrysosporium as evidenced by congener-specific analysis. Appl. Environ. Microbiol. 61:2560-65
195. Yadav JS, Reddy CA. 1993. Mineralization of 2,4-dichlorophenoxyacetic acid (2,4-D) and mixtures of 2,4-D and 2,4,5-trichlorophenoxyacetic acid by Phanerochaete chrysosporium. Appl. Environ. Microbiol. 59:2904-8
196. Yadav JS, Wallace RE, Reddy CA. 1995. Mineralization of mono- and dichlorobenzenes and simultaneous degradation of chloro- and methyl-substituted benzenes by the white rot fungus Phanerochaete chrysosporium. Appl. Environ. Microbiol. 61:677-80
197. Yamamura Y, Fukuhara M, Takabatake E, Ho N, Hashimoto T. 1986. Hepatoxic action of a poisonous mushroom, Amanita abrupta, in mice and its toxic component. Toxicology 38:161-73
198. Zeddel A, Majcherczyk A, Hüttermann A. 1993. Degradation of polychlorinated biphenyls by white-rot fungi Pleurotus ostreatus and Trametes versicolor in a solid state system. Toxicol. Environ. Chem. 40:255-66