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Biotransformation of biphenyl by the filamentous fungus Talaromyces helicus

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Abstract

The filamentous fungusTalaromyces helicus , isolated from oil-contaminated sludge, oxidizes biphenyl via 4-hydroxybiphenyl to the dihydroxylated derivatives 4,4′-dihydroxybiphenyl and 3,4-dihydroxybiphenyl, which, to a certain extent, are converted to glycosyl conjugates. The sugar moiety of the conjugate formed from 4,4′-dihydroxybiphenyl was identified as glucose. Further metabolites: 2-hydroxybiphenyl, 2,5-dihydroxylated biphenyl, and the ring cleavage product 4-phenyl-2-pyrone-6-carboxylic acid accumulated only in traces. From these results the main pathway for biotransformation of biphenyl in T. helicus could be proposed to be the excretion of dihydroxylated derivatives (>75%) and their glucosyl conjugates (<25%).

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References

  • Bergmeyer, H.U., Bernt, E., Schmidt, F. & Stork, H. 1974 In Bergmeyer, H.U. Methoden der enzymatischen Analyse, vol. 2, 3rd edn. pp. 1241–1246. Weinheim: Verlag Chemie. ISBN 3-527-25530-3.

  • C.E. Cerniglia (1997) ArticleTitleFungal metabolism of polycyclic aromatic hydrocarbons: past, present and future applications in bioremediation Journal of Industrial Microbiology and Biotechnology 19 324–333

    Google Scholar 

  • C.E. Cerniglia J.P. Freeman R.K. Mitchum (1982) ArticleTitleGlucuronide and sulfate conjugation in the fungal metabolism of aromatic hydrocarbons Applied and Environmental Microbiology 43 1070–1075

    Google Scholar 

  • J.C. Cox J.H. Golbeck (1985) ArticleTitleHydroxylation of biphenyl by Aspergillus parasiticus: approaches to yield improvement in fermentor cultures Biotechnology and Bioengineering 27 1395–1402

    Google Scholar 

  • T.D. De Boer H.J. Backer (1956) ArticleTitleDiazomethane Organic Synthesis 36 14–16

    Google Scholar 

  • R.H. Dodge C. Cerniglia D.T. Gibson (1979) ArticleTitleFungal metabolism of biphenyl Biochemical Journal 178 223–230

    Google Scholar 

  • M. Gesell E. Hammer M. Specht W. Francke F. Schauer (2001) ArticleTitleBiotransformation of biphenyl by Paecilomyces lilacinus and characterization of ring cleavage products Applied and Environmental Microbiology 67 1551–1557

    Google Scholar 

  • J.H. Golbeck S.A. Albaugh R. Radmer (1983) ArticleTitleMetabolism of biphenyl by Aspergillus toxicaricus: induction of hydroxylating activity and accumulation of water-soluble conjugates Journal of Bacteriology 156 49–57

    Google Scholar 

  • E. Hammer F. Schauer (1997) ArticleTitleFungal hydroxylation dibenzofuran Mycological Research 101 433–436

    Google Scholar 

  • E. Hammer L. Schoefer A. Schaefer K. Hundt F. Schauer (2001) ArticleTitleFormation of glucoside conjugates during biotransformation of dibenzofuran by Penicillium canescens Applied Microbiology and Biotechnology 57 390–394

    Google Scholar 

  • I. Hakkinen S. Hernberg P. Karli E. Vikkula (1973) ArticleTitleDiphenyl poisening in fruit paper production Archives of Environmental Health 26 70–74

    Google Scholar 

  • R. Hanschke F. Schauer (1996) ArticleTitleImproved ultrastructural preservation of yeast cells for scanning electron microscopy Journal of Microscopy 184 81–87

    Google Scholar 

  • D.D. Kaufman J. Blake (1973) ArticleTitleMicrobial degradation of several acetamide, acylanilide, carbamate, toluidine, and urea pesticides Soil Biology and Biochemistry 5 297–308

    Google Scholar 

  • J. Lange E. Hammer M. Specht W. Francke F. Schauer (1998) ArticleTitleBiodegradation of biphenyl by the ascomycetous yeast Debaryomyces vanrijiae Applied Microbiology and Biotechnology 50 364–368

    Google Scholar 

  • T. Meyer R.R. Scheline (1976) ArticleTitleThe metabolism of biphenyl. II. Phenolic metabolites in the rat Acta Pharmacologica and Toxicologica 39 419–432

    Google Scholar 

  • D.P. Mobley H.L. Finkbeiner S.H. Lockwood J. Spivack (1993) ArticleTitleSynthesis of 3-arylmuconolactones using biphenyl metabolism in Aspergillus Tetrahedron 49 3273–3780

    Google Scholar 

  • T.W. Schultz D.H. Kraut G.S. Sayler A.C. Layton (1998) ArticleTitleEstrogenicity of selected biphenyls evaluated using a recombinant yeast assay Environmental Toxicology and Chemistry 17 1727–1729

    Google Scholar 

  • F.M. Seigle-Murandi S.M.A. Krivobok R.L. Steinman J.L. Benoit-Guyod G. Thiault (1991) ArticleTitleBiphenyl oxide hydroxylation by Cunninghamella echinulata Journal of Agricultural and Food Chemistry 39 428–430

    Google Scholar 

  • R. Sietmann E. Hammer J. Moody C.E. Cerniglia F. Schauer (2000) ArticleTitleHydroxylation of biphenyl by the yeast Trichosporon mucoides Archives of Microbiology 174 353–361

    Google Scholar 

  • R. Sietmann E. Hammer F. Schauer (2002) ArticleTitleBiotransformation of biarylic compounds by yeasts of the genus Trichosporon Systematic and Applied Microbiology 25 332–339

    Google Scholar 

  • R. Sietmann E. Hammer M. Specht C.E. Cerniglia F. Schauer (2001) ArticleTitleNovel ring cleavage products in the biotransformation of biphenyl by the yeast Trichosporon mucoides Applied and Environmental Microbiology 67 4158–4165

    Google Scholar 

  • R.V. Smith J.P. Rosazza (1974) ArticleTitleMicrobial models of mammalian metabolism. Aromatic hydroxylation Archives of Biochemistry and Biophysics 161 551–558

    Google Scholar 

  • R.V. Smith P.J. Davis A.M. Clark S. Glover-Milton (1980) ArticleTitleHydroxylations of biphenyl in fungi Journal of Applied Bacteriology 49 65–73

    Google Scholar 

  • J.B. Sutherland A.L. Selby J.P. Freeman P.P. Fu D.W. Miller C.E. Cerniglia (1992) ArticleTitleIdentification of xyloside conjugates formed from anthracene by Rhizoctonia solani Mycological Research 96 506–517

    Google Scholar 

  • D. Zhang Y Yang J.E. Leakey C.E. Cerniglia (1996) ArticleTitlePhase I and phase II enzymes produced by Cunninghamella elegans for the metabolism of xenobiotics FEMS Microbiology Letters 138 221–226

    Google Scholar 

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Correspondence to Elke Hammer.

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Romero, M.C., Hammer, E., Hanschke, R. et al. Biotransformation of biphenyl by the filamentous fungus Talaromyces helicus. World J Microbiol Biotechnol 21, 101–106 (2005). https://doi.org/10.1007/s11274-004-2779-y

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  • DOI: https://doi.org/10.1007/s11274-004-2779-y

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