Skip to main content

Detoxification of ferulic acid by ectomycorrhizal fungi

Mycorrhiza volume 13, pages 117–121 (2003)Cite this article

Abstract

The ectomycorrhizal fungi Laccaria amethystina and Lactarius deterrimus grown in liquid culture were used to study the fate of added ferulic acid. Laccaria amethystina degraded ferulic acid to the major metabolite vanillic acid. The intermediate vanillin was not detected. Lactarius deterrimus showed a completely different detoxification pattern. Two dimers and one trimer of ferulic acid could be identified as polymerization products of this fungus. A bioassay of the possible biological activities of ferulic acid and vanillic acid on these fungi revealed that vanillic acid was less toxic than ferulic acid for Laccaria amethystina but that both phenolic acids were toxic for Lactarius deterrimus. The results are discussed with respect to ectomycorrhizal fungal growth in the organic layer of forest soils and between living root cells of ectomycorrhizas.

This is a preview of subscription content, access via your institution.

Access options

Buy single article

Instant access to the full article PDF.

43,34 €

Price includes VAT (Finland)
Tax calculation will be finalised during checkout.

Fig. 1.
Fig. 2.

References

  • Bending GD, Read DJ (1997) Lignin and soluble phenolic degradation by ectomycorrhizal and ericoid mycorrhizal fungi. Mycol Res 101:1348--1354

    CAS  Google Scholar 

  • Christie T (1965) The effects of some phenolic compounds upon the growth of two species of Phytophthora. N Z J Agric Res 8:630--635

    CAS  Google Scholar 

  • De Boer TD, Backer HJ (1956) Diazomethane. In: Leonhard NJ (ed.) Organic synthesis. Wiley, New York

  • Faure D, Bouillant M, Jacoud C, Bally R (1996) Phenolic derivatives related to lignin metabolism as substrates for Azospirillum laccase activity. Phytochemistry 42:357--359

    Article  CAS  Google Scholar 

  • Feugey L, Strullu DG, Poupard P, Simoneau P (1999) Induced defence responses limit Hartig net formation in ectomycorrhizal birch roots. New Phytol 144:541--547

    Article  Google Scholar 

  • Fortin JA, Piché Y (1979) Cultivation of Pinus strobus root-hypocotyl explants for synthesis of ectomycorrhizae. New Phytol 83:109--119

    Google Scholar 

  • Friend J (1981) Plant phenolics, lignification and plant disease. In: Reinhold L, Harborne JB, Swain T (eds) Progress in phytochemistry, vol 7. Pergamon Press, Oxford, pp 197--261

  • Fry SC (1982) Phenolic components of the primary cell wall: feruloylated disaccharides of D-galactose and L-arabinose from spinach polysaccharide. Biochem J 203:493--504

    CAS  PubMed  Google Scholar 

  • Fry SC, Willis SC, Paterson AEJ (2000) Intraprotoplasmic and wall-localised formation of arabinoxylan-bound diferulates and larger ferulate coupling-products in maize cell-suspension cultures. Planta 211:679--692

    CAS  PubMed  Google Scholar 

  • Gallet C, Lebreton P (1995) Evolution of phenolic patterns in plants and associated litters and humus of a mountain forest ecosystem. Soil Biol Biochem 27:157--165

    CAS  Google Scholar 

  • Giltrap NJ (1982) Production of polyphenol oxidases by ectomycorrhizal fungi with special reference to Lactarius spp. Trans Br Mycol Soc 78:75—81

    CAS  Google Scholar 

  • Graf E (1992) Antioxidant potential of ferulic acid. Free Radical Biol Med 3:435--448

    Article  Google Scholar 

  • Gramss G, Günther T, Fritsche W (1998) Spot tests for oxidative enzymes in ectomycorrhizal, wood- and litter decaying fungi. Mycol Res 102:67--72

    Article  Google Scholar 

  • Günther T, Perner B, Gramss G (1998) Activities of phenol oxidizing enzymes of ectomycorrhizal fungi in axenic culture and in symbiosis with Scots pine (Pinus sylvestris L.). J Basic Microbiol 38:197--206

    Article  Google Scholar 

  • Haars A, Chet J, Hüttermann A (1981) Effect of phenolic compounds and tannin on growth and laccase activity of Fomes annosus. Eur J For Pathol 11:6--76

    Google Scholar 

  • Hutchison LJ (1990) Studies on the systematics of ectomycorrhizal fungi in axenic culture. III. Patterns of polyphenol oxidase activity. Mycologia 82:424--435

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  • Lagrange H, Jay-Allgmand C, Lapeyrie F (2001) Rutin, the phenolglycoside from eucalyptus root exudates, stimulates Pisolithus hyphal growth at picomolar concentrations. New Phytol 149:349--355

    Google Scholar 

  • Mason PA (1980) Aseptic synthesis of sheathing (ecto-) mycorrhizas. In: Ingram DS, Helgeson JP (eds) Tissue culture methods for plant pathologists. Blackwell, Oxford, pp 173--178

  • Micard V, Grabber H, RalpH J, Renard CMGC, Thibault J-F (1997) Dehydroferulic acids from sugar-beet pulp. Phytochemistry 44:1365--1368

    Article  CAS  Google Scholar 

  • Münzenberger B (1991) Lösliche und zellwandgebundene Phenole in Mykorrhizen und nicht mykorrhizierten Wurzeln der Fichte [Picea abies (L.) Karst.] und des Erdbeerbaumes (Arbutus unedo L.) und ihre Bedeutung in der Pilz-Wurzel-Interaktion. PhD thesis. University of Tübingen, Tübingen

  • Münzenberger B, Heilemann J, Strack D, Kottke, I. Oberwinkler F (1990) Phenolics of mycorrhizas and non-mycorrhizal roots of Norway spruce. Planta 182:142--148

    Google Scholar 

  • Münzenberger B, Kottke I, Oberwinkler F (1995) Reduction of phenolics in mycorrhizas of Larix decidua Mill. Tree Physiol 15:191--196

    Google Scholar 

  • Rahouti M, Seigle-Murandi F, Steiman, R, Eriksson K-E (1989) Metabolism of ferulic acid by Paecilomyces variotii and Pestalotia palmarum. Appl Environ Microbiol 55:2391--2398

    CAS  Google Scholar 

  • Rosazza JPN, Huang Z, Dostal L, Volm T, Rousseau B (1995) Review: biocatalytic transformations of ferulic acid: an abundant aromatic natural product. J Ind Microbiol 15:457--471

    CAS  PubMed  Google Scholar 

  • Wacker TL, Safir GR, Stephens CT (1990) Effects of ferulic acid on Glomus fasciculatum and associated effects on phosphorus uptake and growth of asparagus (Asparagus officinalis L.). J Chem Ecol 16:901--909

    CAS  Google Scholar 

  • Ward G, Hadar Y, Bilkis I, Konstantinovsky L, Dosoretz CG (2001) Initial steps of ferulic acid polymerization by lignin peroxidase. J Biol Chem 276:1873--1874

    Article  PubMed  Google Scholar 

Download references

Acknowledgements

We are indebted to R. Wehrens (ZALF), J. Busse (ZALF) and U. Hintsche (IPB) for technical assistance and B. Jaschok-Kentner and C. Kakoschke for recording NMR data.

Author information

Affiliations

  1. Institute of Primary Production and Microbial Ecology, Centre of Agricultural Landscape and Land Use Research (ZALF), Eberswalder Strasse 84, 15374, Müncheberg, Germany

    B. Münzenberger

  2. Institute of Microbiology and Molecular Biology, University of Greifswald, Friedrich-Ludwig-Jahnstrasse 15, 17489, Greifswald, Germany

    E. Hammer & F. Schauer

  3. Department Structural Biology, German Research Centre for Biotechnology (GBF), Mascheroder Weg 1, 38124, Braunschweig, Germany

    V. Wray

  4. Institute of Plant Biochemistry (IPB), Weinberg 3, 06120, Halle, Germany

    J Schmidt & D. Strack

Authors
  1. B. Münzenberger
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. Hammer
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. Wray
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. F. Schauer
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. J Schmidt
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. D. Strack
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to B. Münzenberger.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Münzenberger, B., Hammer, E., Wray, V. et al. Detoxification of ferulic acid by ectomycorrhizal fungi. Mycorrhiza 13, 117–121 (2003). https://doi.org/10.1007/s00572-003-0226-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00572-003-0226-9

Keywords

  • Ectomycorrhizal fungi
  • Ferulic acid
  • Laccaria amethystina
  • Lactarius deterrimus
  • Phenolics