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The effect of pH on the transformation of syringic and vanillic acids by the laccases of Rhizoctonia praticola and Trametes versicolor

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Abstract

Laccases (benzenediol: oxygen oxidoreductases, EC 1.10.3.2) from Rhizoctonia praticola and Trametes versicolor formed different products from syringic and vanillic acids at different pH values, but both enzymes generated the same chemicals at a particular pH. The products were separated by thin-layer and high-performance liquid chromatography. Four compounds were determined from syringic acid (m/z 168, 334, 350 and 486) at pH 6.9, but only two of these (m/z 168 and 334) were found at pH 3.5. In the case of vanillic acid two isomeric dimers (m/z 304) and 2-methoxy-1,4-benzoquinone (m/z 138) were identified. The dimers were formed at both pH values (pH 3.5 and 6.9), but 2-methoxy-1,4-benzoquinone appeared only at pH 3.5.

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References

  • Ander P, Eriksson KE (1978) Lignin degradation and utilization by microorganisms. Prog Ind Microbiol 14:1–58

    Google Scholar 

  • Ander P, Hatakka A, Erksson KE (1980) Vanillic acid metabolism by the white-rot fungus Sporotrichum pulverulentum. Arch Microbiol 125:189–202

    Google Scholar 

  • Bollag J-M, Liu S-Y, Minard RD (1982) Enzymatic oligomerization of vanillic acid. Soil Biol Biochem 14:157–163

    Google Scholar 

  • Bollag J-M, Sjoblad RD, Liu S-Y (1979) Characterization of an enzyme from Rhizoctonia praticola which polymerizes phenolic compounds. Can J Microbiol 25:229–233

    Google Scholar 

  • Fahraeus G, Reinhammar B (1967) Large scale production and purification of laccase from cultures of the fungus Polyporus versicolor and some properties of laccase A. Acta Chem Scand 21:2367–2378

    Google Scholar 

  • Flaig W, Beutelspacher H, Rietz E (1975) Chemical composition and physical properties of humic substances. In: Gieseking JE (ed) Soil components, vol 1. Springer, Berlin Heidelberg New York, pp 1–211

    Google Scholar 

  • Flaig W, Haider K (1961) Reaktionen mit oxydierenden Enzymen aus Mikroorganismen. Planta Med 9:123–139

    Google Scholar 

  • Fukuzumi T, Uraushihara S, Oohashi T, Shibamoto T (1964) 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

    Google Scholar 

  • Ishihara T, Ishihara M (1976) Oxidation of syringic acid by fungal laccase. J Jap Wood Res Soc 22:371–375

    Google Scholar 

  • Ishihara T, Miyazaki M (1972) Oxidation of milled wood lignin by fungal laccase. J Jap Wood Res Soc 18:415–419

    Google Scholar 

  • Katase T (1981) The different forms of which p-hydroxybenzoic, vanillic, and ferulic acids exist in a peat soil. Soil Sci 132:436–443

    Google Scholar 

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

    Google Scholar 

  • Leonowicz A, Grzywnowicz K (1981) Quantitative estimation of laccase forms in some white-rot fungi using syringaldazine as a substrate. Enzyme Microbiol Technol 3:55–58

    Google Scholar 

  • Liu S-Y, Minard RD, Bollag J-M (1981) Oligomerization of syringic acid, a lignin derivative, by a phenoloxidase. Soil Sci Soc Am J 45:1100–1105

    Google Scholar 

  • Lowry ON, Rosenbough NJ, Farr AL, Randall RJ (1951) Protein measurement with the Folin-phenol reagent. J Biol Chem 1973:265–275

    Google Scholar 

  • Mayaudon J, Sakar JM (1975) Laccases de Polyporus versicolor dans le sol et la litière. Soil Biol Biochem 7:31–34

    Google Scholar 

  • McIlvaine TC (1921) A buffer solution for colorimetric comparison. J Biol Chem 49:183–186

    Google Scholar 

  • Sundman V, Haro K (1966) Or the mechanism by which cyclolignanolytic Agrobacteria might cause humification. Finska Kemists Medd 75:111–118

    Google Scholar 

  • Whitehead DC, Dibb H, Hartley RD (1982) Phenolic compounds in soil as influenced by the growth of different plant species. J Appl Ecol 19:579–588

    Google Scholar 

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Leonowicz, A., Edgehill, R.U. & Bollag, JM. The effect of pH on the transformation of syringic and vanillic acids by the laccases of Rhizoctonia praticola and Trametes versicolor . Arch Microbiol 137, 89–96 (1984). https://doi.org/10.1007/BF00414446

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  • DOI: https://doi.org/10.1007/BF00414446

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