Abstract
The white rot fungus Phanerochaete chrysosporium metabolized the lignin model compounds veratylglycerol-β-guaiacyl ether I and 4-ethoxy-3-methoxy-phenylglycerol-β-guaiacyl ether V in stationary culture under an atmosphere of 100% oxygen and under nitrogen limiting conditions. 2-(o-methoxyphenoxy)-ethanol VII was identified as a product of the metabolism of both substrates. Veratryl alcohol and 4-ethoxy-3-methoxybenzyl alcohol IV were identified as metabolites of I and V respectively. Metabolites were identified after comparison with chemically synthesized standards by mass spectrometry. These results indicate the existence of an enzyme system capable of directly cleaving the etherated dimers I and V at the α, β bond. The additional identification of 2-(o-methoxyphenoxy)-1,3 propanediol IX as a metabolic product indicates that cleavage of the alkyl-phenyl bond of these dimers or their metabolites also occurs.
Similar content being viewed by others
Abbreviations
- GLC:
-
Gas liquid chromatography
- TMSi:
-
trimethylsilyl
- TLC:
-
Thin layer chromatography
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)
Axelrod, J.: The enzymatic cleavage of aromatic ethers. Biochem. J. 63, 634–639 (1956)
Berlin, J., Barz, W.: Oxidative decarboxylation of para-hydroxybenzoic acids by peroxidases under in vivo and in vitro conditions. Z. Naturforsch. 30c, 650–658 (1975)
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)
Farmer, V. C., Henderson, M. E. K., Russel, J. D.: Reduction of certain aromatic acids to aldehydes and alcohols by Polystictus versicolor. Biochim. Biophys. Acta 35, 202–211 (1959)
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)
Fukuzumi, T., Takatuka, H., Minami, K.: Enzymic degradation of lignin V. The effects of NADH on the enzymic cleavage of the arylakyl ether bond in veratrylglycerol-β-guaiacyl ether as lignin model compound. Arch. Biochem. Biophys. 129, 396–403 (1969)
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.: Degradation of the lignin model compound syringylglycol-β-guaiacyl ether by Polyporous versicolor and Stereum frustulatum. Biochim. Biophys. Acta 165, 145–163 (1968)
Kirk, T. K., Lorenz, L. F.: Oxygenation of 4-alkoxyl groups in alkoxybenzoic acids by Polyporous dichrous. Appl. Microbiol. 27, 360–367 (1974)
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)
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
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)
Sarkanen, K. V.: Precursors and their polymerization. In: Lignins: occurrence, formation, structure and reactions (K. V. Sarkanen, C. H. Ludwig, eds.), pp. 95–155. New York: Wiley-Interscience 1971
Weinstein, D. A., Gold, M. H.: Synthesis of guaiacylglycol and glycerol-β-0-(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. App. Env. Microbiol. (1980, in press)
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
Enoki, A., Goldsby, G.P. & Gold, M.H. Metabolism of the lignin model compounds veratrylglycerol-β-guaiacyl ether and 4-ethoxy-3-methoxyphenylglycerol-β-guaiacyl ether by Phanerochaete chrysosporium . Arch. Microbiol. 125, 227–231 (1980). https://doi.org/10.1007/BF00446881
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00446881