Abstract
The white rot basidiomycete Phanerochaete chrysosporium metabolized guaiacylglycol-β-guaiacyl ether (I) in high nitrogen, shaking and stationary cultures. 2-(o-Methoxyphenoxy) ethanol (X), 2-(o-methoxyphenoxy) acetic acid (IX) and methoxy-phydroquinone (MHQ) were identified as products of the metabolism of (I). P. chrysosporium also metabolized guaiacylglycerol-β-guaiacyl ether (IV) in high nitrogen stationary cultures. 2-(o-Methoxyphenoxy)-1,3 propanediol (XII) and 3-hydroxy, 2-(o-methoxy-phenyxy) propionic acid (XIV) were identified as products of the metabolism of (IV). Finally, P. chrysosporium metabolized α-deoxyguaiacylglycol-β-guaiacyl ether (VI) and α-deoxyguaiacylglycerol-β-guaiacyl ether (VII) in limiting nitrogen cultures. 2-(o-Methoxyphenoxy) ethanol (X) and 2-(o-methoxyphenoxy)-1,3 propanediol (XII) were identified as products of the metabolism of VI and VII respectively indicating α hydroxylation of those substrates with subsequent alkyl-phenyl bond cleavage. Metabolites were identified after comparison with chemically synthesized standards by GLC-mass spectrometry.
Similar content being viewed by others
Abbreviations
- GLC :
-
Gas liquid chromatography
- TMSi :
-
trimethylsilyl
- TLC :
-
thin layer chromatography
- MHQ :
-
methoxyhydroquinone
References
Adler, E., Lindgren, B. O., Saeden, U.: The beta-guaiacyl ether of alpha-veratryl-glycerol as a lignin model. Svensk Papperstidning. 55, 245–253 (1952)
Buswell, J. A., Ander, P., Pettersson, B., Eriksson, K. E.: Oxidative decarboxylation of vanillic acid by Sporotrichum pulverulentum. FEBS Lett. 103, 98–101 (1979)
Crawford, R. L., Kirk, T. K., Harkin, J. M., McCoy, E.: Bacterial cleavage of an arylglycerol-β-aryl ether bond. Appl. Microbiol. 25, 322–324 (1973)
Enoki, A., Goddsby, G. P., Gold, M. H.: Metabolism of the lignin dimers veratrylglycerol-β-guaiacyl ether and 4-ethoxy-3-methoxyphenylglycerol-β-guaiacyl ether by Phanerochaete chrysosporium. Arch. Microbiol. 125, 227–232 (1980)
Feiser, L. F., Feiser, M.: Reagents for organic synthesis. Vol. I. New York: John Wiley and Sons 1967
Fukuzumi, T., Katayama, Y.: Bacterial degradation of dimer relating to structure of lignin I. Mokuzai Gakkaishi. 27, 214–215 (1977)
Gold, M. H., Cheng, T. M.: Induction of colonial growth and replica plating of the white rot basidiomycete Phanerochaete chrysosporium. Appl. Env. Microbiol. 35, 1223–1225 (1978)
Kirk, T. K.: Effects of microorganisms on lignin. Ann. Rev. Phytopathol. 9, 185–210 (1971)
Kirk, T. K., Harkin, J. M., Cowling, E. B.: Oxidation of guaiacyl and veratrylglycerol-β-guaiacyl ether by Polyporous versicolor and Stereum frustulatum. Biochim. Biophys. Acta 165, 134–144 (1968a)
Kirk, T. K., Harkin, J. M., Cowling, E. B.: Degradation of the lignin model compound syringlyglycol-β-guaiacyl ether by Polyporous versicolor and Stereum frustulatum. Biochim. Biophys. Acta 165, 145–163 (1968b)
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, 227–285 (1978)
Krisnangkura, K., Gold, M. H.: Peroxidase catalyzed oxidative decarboxylation of vanillic acid to methoxy-p-hydroquinone. Phytochem. 18, 2019–2021 (1979)
Lai, Y. Z., Sarkanen, K. V.: Isolation and structural studies In: Lignins: occurrence, formation, structure and reactions (K. V. Sarkanen, C. H. Ludwig, eds.), pp. 165–230. New York: Wiley-Interscience 1971
Leopold, B.: Aromatic keto and hydroxyl-polyethers as lignin models III. Acta Chem Scand. 4, 1523–1537 (1950)
Lundquist, K., Kirk, T. K.: De novo synthesis and decomposition of veratryl alcohol by a lignin-degrading basidiomycete. Phytochem. 17, 1676 (1978)
Palmer, C. S., McWherter, P. W.: Ethyl bromomalonate. Org. Syn., Coll. 1, 245–246 (1944)
Pew, J. C., Connors, W. J.: New structures from the enzymic dehydrogenation of lignin model p-hydroxy-α-carbinols. J. Org. Chem. 34, 580–584 (1969)
Sarkanen, K. V.: Precursors and their polymerization. In: Lignins: occurrence, formation, structure and reactions (K. V. Sarkanen, Ch. Ludwig, eds.), pp. 95–155 New York: Wiley-Interscience 1971
Weinstein, D. A., Gold, M. H.: Synthesis of guaiacyglycol and glycerol-β-o-(β-methylumbelliferyl) Ethers: lignin model substrates for the possible fluorometic assay of β-etherases. Holzforschung 33, 134–135 (1979)
Weinstein, D. A., Krisnangkura, K., Mayfield, M. B., Gold, M. H.: Metabolism of radiolabeled β-guaiacyl ether linked lignin dimeric compounds by Phanerochaete chrysosporium. Appl. Env. Microbiol. 39, 535–540 (1980)
Yajima, Y., Enoki, A., Mayfield, M. B., Gold, M. H.: Vanillate hydroxylase from the white rot basidiomycete Phanerochaete chrysosporium. Arch. Microbiol. 123, 319–321 (1979)
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Goldsby, G.P., Enoki, A. & Gold, M.H. Alkyl-phenyl cleavage of the lignin model compounds guaiacylglycol and glycerol-β-guaiacyl ether by Phanerochaete chrysosporium . Arch. Microbiol. 128, 190–195 (1980). https://doi.org/10.1007/BF00406157
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00406157