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Vanillic acid metabolism by the white-rot fungus Sporotrichum pulverulentum

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Abstract

Vanillic acid metabolism was studied in wild-type Sporotrichum pulverulentum and three different mutants. Vanillic acid was found to be oxidatively decarboxylated to methoxyhydroquinone (MHQ) and simultaneously reduced to vanillin and vanillyl alcohol to different degrees depending upon the cultivation conditions. The reducing pathway cannot be utilized unless the fungus has access to an easily metabolized carbon source such as glucose or cellobiose, while decarboxylation takes place in cultures with only vanillic acid present. Polymerization reactions also occurred in the culture solutions. Some evidence for reoxidation of vanillin and vanillyl alcohol was obtained in vivo, and in vitro experiments using horseradish peroxidase.

Using vanillic acids labelled in the carboxyl, methoxyl and the aromatic ring it was shown that decarboxylation occures before ring-cleavage, which in turn takes place earlier than the release of 14CO2 from O14CH3-vanillate. The 14CO2 evolution from the methoxyl group is repressed by 1% cellobiose as compared to 0.25% cellobiose, but is stimulated by 26 mM nitrogen (as asparagine plus NH4NO3) compared to 2.6 mM nitrogen. Since S. pulverulentum appears to require three hydroxyl groups attached to the benzene ring before ring-cleavage can occur, preparation for ring-cleavage is apparently achieved by hydroxylation rather than by demethylation.

A scheme for metabolism of vanillic acid by S. pulverulentum based upon these results is proposed.

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Abbreviations

WT:

wild type Sporotrichum pulverulentum

MHQ:

methoxyhydroquinone

MQ:

methoxyquinone

NKM:

Norkrans medium

DMS:

dimethylsuccinate

DHP:

dehydropolymer of coniferyl alcohol

References

  • Adler, E.: Lignin chemistry — past, present and future. Wood Sci. Technol. 11, 169–218 (1977)

    Google Scholar 

  • Ander, P., Eriksson, K.-E.: Influence of carbohydrates on lignin degradation by the white-rot fungus Sporotrichum pulverulentum. Svensk Papperstidn. 18, 643–652 (1975)

    Google Scholar 

  • Ander, P., Eriksson, K.-E.: The improtance of phenol oxidase activity in lignin degradation by the white-rot fungus Sporotrichum pulverulentum. Arch. Microbiol. 109, 1–8 (1976)

    Google Scholar 

  • Ander, P., Eriksson, K.-E.: Selective degradation of wood components by white-rot fungi. Physiol. Plant. 41, 239–248 (1977)

    Google Scholar 

  • Ander, P., Eriksson, K.-E.: Lignin degradation and utilization by micro-organisms. In: Progress in industrial microbiology, Vol. 14, M. J. Bull, ed., pp. 1–58. Amsterdam: Elsevier 1978

    Google Scholar 

  • Ander, P., Hatakka, A., Eriksson, K.-E.: Degradation of lignin and lignin-related substances by Sporotrichum pulverulentum (Phanerochaete chrososporium). In: Lignin biodegradation: Microbiology, chemistry and applications (T. K. Kirk, T., Higuchi, H.-m. Chang, eds.). Boca Raton: CRC Press Inc. 1980 (in press)

    Google Scholar 

  • Berlin, J., Barz, W.: Oxidative decarboxylation of parahydroxybensoic acids by peroxidases under in vivo and in vitro conditions. Z. Naturforsch. 30c, 650–658 (1975)

    Google Scholar 

  • Buswell, J. A., Ander, P., Pettersson, B., Eriksson, K.-E.: Oxidative decarboxylation of vanillic acid by Sporotrichum pulverulentum. FEBS Letters 103, 98–101 (1979a)

    Google Scholar 

  • Buswell, J. A., Hamp, S., Eriksson, K.-E.: Intracellular quinone reduction in Sporotrichum pulverulentum by a NAD(P)H: quinone oxidoreducase. Possible role in vanillic acid catabolism. FEBS Letters 108, 229–232 (1979)

    Google Scholar 

  • Buswell, J. A., Eriksson, K.-E.: Aromatic ring cleavage by the white-rot fungus Sporotrichum pulverulentum. FEBS Letters 104, 258–261 (1979)

    Google Scholar 

  • Cain, R. B., Bilton, R. F., Darrah, J. A.: The metabolism of aromatic acids by micro-organisms. Metabolic pathways in the fungi. Biochem. J. 108, 797–832 (1968)

    Google Scholar 

  • Farmer, V. C., Henderson, M. E. K., Russell, J. D.: Aromatic-alcohol-oxidase activity in the growth medium of Polystictus versicolor. Biochem. J. 74, 257–262 (1960)

    Google Scholar 

  • Fenn, P., Kirk, T. K.: Ligninolytic system of Phanerochaete chrysosporium: Inhibition by o-phthalate. Arch. Microbiol. 123, 307–309 (1979)

    Google Scholar 

  • Flaig, W., Haider, K.: Die Verwertung phenolischer Verbindungen durch Weißfäulepilze. Arch. Mikrobiol. 40, 212–223 (1961)

    Google Scholar 

  • Fukuzumi, T., Uraushihara, S., Oohashi, T., Shibamoto, T.: Enzymatic degradation of lignin. III. Oxidation accompanying carbon dioxide liberation of vanillic acid, vanilloylformic acid and guaiacylpyruvic acid by enzyme of Polystictus sanguineus and Poria subacida. J. Jap. Wood Res. Soc. 10, 242–250 (1964)

    Google Scholar 

  • Haider, K., Lim, S.-U., Flaig, W.: Untersuchungenüber die Einwirkung von Mikroorganismen auf 14C-markierte phenolische Verbindungen. Landwirtsch. Forschung 15, 196–204 (1962)

    Google Scholar 

  • Haider, K., Martin, J. P., Reitz, E.: Decomposition in soil of 14C-labelled coumaryl alcohols; Free and linked into dehydropolymer and plant lignins and model humic acids. Soil Sci. Soc. Am. J. 41, 556–562 (1977)

    Google Scholar 

  • Haider, K., Trojanowski, J.: Decomposition of specifically 14C-labelled phenols and dehydropolymers of coniferyl alcohol as models for lignin degradation by soft and white-rot fungi. Arch. Microbiol. 105, 33–41 (1975)

    Google Scholar 

  • Harkin, J. M., Larsen, M. J., Obst, J. R.: Use of syringaldazine for detection of laccase in sporophores of wood rotting fungi. Mycologia (N.Y.) LXVI, 469–476 (1974)

    Google Scholar 

  • Higuchi, T.: Formation and biological degradation of lignins. In: Advances in enzymology, Vol. 34 (F. F. Nord, ed.), pp. 207–283. New York: Intersc. Publ. 1971

    Google Scholar 

  • Ishihara, T., Miyazaki, M.: Formation of a new crystalline compound from vanillic acid by the action of crude of Polyporus versicolor. J. Jap. Wood Res. Soc. 16, 181–184 (1970)

    Google Scholar 

  • Ishikawa, H., Schubert, W. J., Nord, F. F.: Investigations on lignin and lignification. The degradation by Polyporus versicolor and Fomes fomentarius of aromatic compounds structurally related to softwood lignin. Arch. Biochem. Biophys. 100, 140–149 (1963)

    Google Scholar 

  • Keyser, P., Kirk, T. K., Zeikus, J. G.: Ligninolytic enzyme system of Phanerochaete chrysosporium: Synthetized in the absence of lignin in response to nitrogen starvation. J. Bacteriol. 135, 790–797 (1978)

    Google Scholar 

  • Kirk, T. K., Chang, H.-m.: Decomposition of lignin by white-rot fungi. II. Characterization of heavily degraded lignins from decayed spruce. Holzforschung 29, 56–64 (1975)

    Google Scholar 

  • Kirk, T. K., Lorenz, L. F.: Methoxyhydroquinone, an intermediate of vanillate catabolism by Polyporus dichrous. Appl. Microbiol. 26, 173–175 (1973)

    Google Scholar 

  • Kirk, T. K., Schultz, E., Connors, W. J., Lorenz, L. F., Zeikus, J. G.: Influence of culture parameters on lignin metabolism by Phanerochaete chrysosporium. Arch. Microbiol. 117, 277–285 (1978)

    Google Scholar 

  • Krisnangkura, K., Mayfield, M. B., Gold, M. H., Moore, K., Kirk, T. K.: Regulation of lignin model compound metabolism by Phanerochaete chrysosporium. Abstract from ACS/CSJ Chemical Congress, Honolulu, Hawaii (1979)

  • Lundquist, K., Kirk, T. K.: De novo synthesis and decomposition of veratryl alcohol by a lignin-degrading basidiomycete. Phytochemistry 17, 1676 (1978)

    Google Scholar 

  • Nishida, A., Fukuzumi, T.: Formation of coniferyl alcohol from ferulic acid by the white-rot fungus Trametes. Phytochemistry 17, 417–419 (1978)

    Google Scholar 

  • Ohta, M., Higuchi, T., Iwahara, S.: Microbial degradation of dehydrodiconiferylacohol, a lignin substructure model. Arch. Microbiol. 121, 23–28 (1979)

    Google Scholar 

  • Sparnins, V., Anderson, J. J., Omans, J., Dagley, S.: Degradation of 4-hydroxyphenylacetic acid by Trichosporon cutaneum. J. Bacteriol. 136, 449–451 (1978)

    Google Scholar 

  • Sundman, V.: A study of lignanolytic soil bacteria with special reference to α-conidendrin decomposition. Acta Polyt. Scand., Chemistry including Metallurgy Series No. 40, Helsinki 1965, pp. 116 (1965)

  • Westermark, U., Eriksson, K.-E.: Carbohydrate-dependent enzymic quinone reduction during lignin degradation. Acta Chem. Scand. B28, 204–208 (1974a)

    Google Scholar 

  • Westermark, U., Eriksson, K.-E.: Cellobiose: quinone oxidoreductase, a new wood-degrading enzyme from white-rot fungi. Acta Chem. Scand. B28, 209–214 (1974b)

    Google Scholar 

  • Zenk, M. H., Gross, G. G.: Reduction von Veratrumsäure zu Veratrylaldehyd und Veratrylalkohol durch zellfreie Extrakte von Polystictus versicolor L. Z. Pflanzenphysiol. 53, 356–362 (1965)

    Google Scholar 

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Author notes

  1. Annele Hatakka

    Present address: Department of Microbiology, University of Helsinki, SF-00710, Helsinki 71, Finland

Authors and Affiliations

  1. Chemistry Department, Swedish Forest Products Research Laboratory, Box 5604, S-114 86, Stockholm, Sweden

    Paul Ander, Annele Hatakka & Karl-Erik Eriksson

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Ander, P., Hatakka, A. & Eriksson, KE. Vanillic acid metabolism by the white-rot fungus Sporotrichum pulverulentum . Arch. Microbiol. 125, 189–202 (1980). https://doi.org/10.1007/BF00446876

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  • DOI: https://doi.org/10.1007/BF00446876

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