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Appl Environ Microbiol. 1994 January; 60(1): 271–277.
PMCID: PMC201299
Physiological Role of Chlorinated Aryl Alcohols Biosynthesized De Novo by the White Rot Fungus Bjerkandera sp. Strain BOS55
Ed de Jong,* Anne E. Cazemier, Jim A. Field, and Jan A. M. de Bont
Division of Industrial Microbiology, Department of Food Science, Agricultural University, 6700 EV Wageningen, The Netherlands
* Corresponding author. Mailing address: Department of Food Science, Division of Industrial Microbiology, Agricultural University, P.O. Box 8129, 6700 EV Wageningen, The Netherlands. Phone: 31 8370 84976. Fax: 31 8370 84978. Electronic mail address: JandeBont@Algemeen.IM.WAU.NL.
Abstract
The white rot fungus Bjerkandera sp. strain BOS55 produces veratryl, anisyl, 3-chloroanisyl, and 3,5-dichloroanisyl alcohol and the corresponding aldehydes de novo from glucose. All metabolites are produced simultaneously with the extracellular ligninolytic enzymes and have an important physiological function in the fungal ligninolytic system. Both mono- and dichlorinated anisyl alcohols are distinctly better substrates for the extracellular aryl alcohol oxidases than veratryl alcohol. The aldehydes formed are readily recycled by reduction by washed fungal mycelium, thus creating an extracellular H2O2 production system regulated by intracellular enzymes. Lignin peroxidase does not oxidize the chlorinated anisyl alcohols either in the absence or in the presence of veratryl alcohol. It was therefore concluded that the chlorinated anisyl alcohols are well protected against the fungus's own aggressive ligninolytic enzymes. The relative amounts of veratryl alcohol and the chlorinated anisyl alcohols differ significantly according to the growth conditions, indicating that production of veratryl alcohol and the production of the (chlorinated) anisyl metabolites are independently regulated. We conclude that the chlorinated anisyl metabolites biosynthesized by the white rot fungus Bjerkandera sp. strain BOS55 can be purposefully produced for ecologically significant processes such as lignin degradation.
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  • Akamatsu, Y; Ma, DB; Higuchi, T; Shimada, M. A novel enzymatic decarboxylation of oxalic acid by the lignin peroxidase system of white-rot fungus Phanerochaete chrysosporium. FEBS Lett. 1990 Aug 20;269(1):261–263. [PubMed]
  • Bourbonnais, R; Paice, MG. Veratryl alcohol oxidases from the lignin-degrading basidiomycete Pleurotus sajor-caju. Biochem J. 1988 Oct 15;255(2):445–450. [PubMed]
  • Bradford, MM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem. 1976 May 7;72:248–254. [PubMed]
  • Cai, D; Tien, M. Kinetic studies on the formation and decomposition of compounds II and III. Reactions of lignin peroxidase with H2O2. J Biol Chem. 1992 Jun 5;267(16):11149–11155. [PubMed]
  • Cancel, AM; Orth, AB; Tien, M. Lignin and veratryl alcohol are not inducers of the ligninolytic system of Phanerochaete chrysosporium. Appl Environ Microbiol. 1993 Sep;59(9):2909–2913. [PubMed]
  • Daniel, Geoffrey; Volc, Jindrich; Kubatova, Elena; Nilsson, Thomas. Ultrastructural and Immunocytochemical Studies on the H(2)O(2)-Producing Enzyme Pyranose Oxidase in Phanerochaete chrysosporium Grown under Liquid Culture Conditions. Appl Environ Microbiol. 1992 Nov;58(11):3667–3676. [PubMed]
  • de Jong, E; Field, JA; de Bont, JA. Evidence for a new extracellular peroxidase. Manganese-inhibited peroxidase from the white-rot fungus Bjerkandera sp. BOS 55. FEBS Lett. 1992 Mar 24;299(1):107–110. [PubMed]
  • de Jong, E; Field, JA; Dings, JA; Wijnberg, JB; de Bont, JA. De-novo biosynthesis of chlorinated aromatics by the white-rot fungus Bjerkandera sp. BOS55. Formation of 3-chloro-anisaldehyde from glucose. FEBS Lett. 1992 Jul 6;305(3):220–224. [PubMed]
  • de Jong, Ed; Field, Jim A; Spinnler, Henri-Eric; Wijnberg, Joannes B P A; de Bont, Jan A M. Significant Biogenesis of Chlorinated Aromatics by Fungi in Natural Environments. Appl Environ Microbiol. 1994 Jan;60(1):264–270. [PubMed]
  • Dosoretz, Carlos G; Chen, Hsin-Chih; Grethlein, Hans E. Effect of Environmental Conditions on Extracellular Protease Activity in Lignolytic Cultures of Phanerochaete chrysosporium. Appl Environ Microbiol. 1990 Feb;56(2):395–400. [PubMed]
  • Dosoretz, CG; Dass, SB; Reddy, CA; Grethlein, HE. Protease-mediated degradation of lignin peroxidase in liquid cultures of Phanerochaete chrysosporium. Appl Environ Microbiol. 1990 Nov;56(11):3429–3434. [PubMed]
  • Faison, BD; Kirk, TK. Factors Involved in the Regulation of a Ligninase Activity in Phanerochaete chrysosporium. Appl Environ Microbiol. 1985 Feb;49(2):299–304. [PubMed]
  • FARMER, VC; HENDERSON, ME; RUSSELL, JD. Reduction of certain aromatic acids to aldehydes and alcohols by Polystictus versicolor. Biochim Biophys Acta. 1959 Sep;35:202–211. [PubMed]
  • FARMER, VC; HENDERSON, ME; RUSSELL, JD. Aromatic-alcohol-oxidase activity in the growth medium of Polystictus versicolor. Biochem J. 1960 Feb;74:257–262. [PubMed]
  • Fawer, MS; Stierli, J; Cliffe, S; Fiechter, A. The characterisation of immobilised lignin peroxidase by flow injection analysis. Biochim Biophys Acta. 1991 Jan 8;1076(1):15–22. [PubMed]
  • Field, JA; de Jong, E; Feijoo Costa, G; de Bont, JA. Biodegradation of polycyclic aromatic hydrocarbons by new isolates of white rot fungi. Appl Environ Microbiol. 1992 Jul;58(7):2219–2226. [PubMed]
  • Guillén, F; Martínez, AT; Martínez, MJ. Substrate specificity and properties of the aryl-alcohol oxidase from the ligninolytic fungus Pleurotus eryngii. Eur J Biochem. 1992 Oct 15;209(2):603–611. [PubMed]
  • Haemmerli, SD; Leisola, MS; Sanglard, D; Fiechter, A. Oxidation of benzo(a)pyrene by extracellular ligninases of Phanerochaete chrysosporium. Veratryl alcohol and stability of ligninase. J Biol Chem. 1986 May 25;261(15):6900–6903. [PubMed]
  • Harvey, PJ; Floris, R; Lundell, T; Palmer, JM; Schoemaker, HE; Wever, R. Catalytic mechanisms and regulation of lignin peroxidase. Biochem Soc Trans. 1992 May;20(2):345–349. [PubMed]
  • Kelley, RL; Reddy, CA. Purification and characterization of glucose oxidase from ligninolytic cultures of Phanerochaete chrysosporium. J Bacteriol. 1986 Apr;166(1):269–274. [PubMed]
  • Kersten, PJ. Glyoxal oxidase of Phanerochaete chrysosporium: its characterization and activation by lignin peroxidase. Proc Natl Acad Sci U S A. 1990 Apr;87(8):2936–2940. [PubMed]
  • Kersten, PJ; Kalyanaraman, B; Hammel, KE; Reinhammar, B; Kirk, TK. Comparison of lignin peroxidase, horseradish peroxidase and laccase in the oxidation of methoxybenzenes. Biochem J. 1990 Jun 1;268(2):475–480. [PubMed]
  • Kersten, PJ; Kirk, TK. Involvement of a new enzyme, glyoxal oxidase, in extracellular H2O2 production by Phanerochaete chrysosporium. J Bacteriol. 1987 May;169(5):2195–2201. [PubMed]
  • Kimura, Y; Asada, Y; Kuwahara, M. Screening of basidiomycetes for lignin peroxidase genes using a DNA probe. Appl Microbiol Biotechnol. 1990 Jan;32(4):436–442. [PubMed]
  • Kirk, TK; Farrell, RL. Enzymatic "combustion": the microbial degradation of lignin. Annu Rev Microbiol. 1987;41:465–505. [PubMed]
  • Lundell, Taina; Leonowicz, Andrzej; Rogalski, Jerzy; Hatakka, Annele. Formation and Action of Lignin-Modifying Enzymes in Cultures of Phlebia radiata Supplemented with Veratric Acid. Appl Environ Microbiol. 1990 Sep;56(9):2623–2629. [PubMed]
  • Muheim, A; Waldner, R; Sanglard, D; Reiser, J; Schoemaker, HE; Leisola, MS. Purification and properties of an aryl-alcohol dehydrogenase from the white-rot fungus Phanerochaete chrysosporium. Eur J Biochem. 1991 Jan 30;195(2):369–375. [PubMed]
  • Paszczynski, A; Crawford, RL. Degradation of azo compounds by ligninase from Phanerochaete chrysosporium: involvement of veratryl alcohol. Biochem Biophys Res Commun. 1991 Aug 15;178(3):1056–1063. [PubMed]
  • Popp, JL; Kalyanaraman, B; Kirk, TK. Lignin peroxidase oxidation of Mn2+ in the presence of veratryl alcohol, malonic or oxalic acid, and oxygen. Biochemistry. 1990 Nov 20;29(46):10475–10480. [PubMed]
  • Popp, JL; Kirk, TK. Oxidation of methoxybenzenes by manganese peroxidase and by Mn3+. Arch Biochem Biophys. 1991 Jul;288(1):145–148. [PubMed]
  • Sannia, G; Limongi, P; Cocca, E; Buonocore, F; Nitti, G; Giardina, P. Purification and characterization of a veratryl alcohol oxidase enzyme from the lignin degrading basidiomycete Pleurotus ostreatus. Biochim Biophys Acta. 1991 Jan 23;1073(1):114–119. [PubMed]
  • Shah, MM; Grover, TA; Barr, DP; Aust, SD. On the mechanism of inhibition of the veratryl alcohol oxidase activity of lignin peroxidase H2 by EDTA. J Biol Chem. 1992 Oct 25;267(30):21564–21569. [PubMed]
  • Valli, K; Wariishi, H; Gold, MH. Oxidation of monomethoxylated aromatic compounds by lignin peroxidase: role of veratryl alcohol in lignin biodegradation. Biochemistry. 1990 Sep 18;29(37):8535–8539. [PubMed]
  • Wariishi, H; Valli, K; Gold, MH. Manganese(II) oxidation by manganese peroxidase from the basidiomycete Phanerochaete chrysosporium. Kinetic mechanism and role of chelators. J Biol Chem. 1992 Nov 25;267(33):23688–23695. [PubMed]