Skip to main content

Degradation and oligomerization of syringic acid by distinctive ecological groups of fungi

Microbial Ecology volume 21, pages 73–84 (1991)Cite this article

Abstract

Forty-four terrestrial and aeroaquatic and aquatic fungi, including fifteen species causing white-rot, four species causing brown-rot, and some species causing soft-rot of wood, were tested for their ability to degrade the monomer syringic acid, which is released during decay of angiosperm lignin. None of the white- or brown-rot species caused any detectable degradation of syringic acid under the test conditions; however, six typical white-rot fungi strongly oligomerized syringic acid, both with and without cosubstrate. The main polymerization product was identified as a 1,3-dimethylpyrogallol oligomer by13C-NMR. Other minor metabolic products were methylated and hydroxylated derivatives. Oligomerization depended on the presence of 1 or 2 methoxy groups in ortho position to the hydroxy group of the substrate.

Among the remaining fungi,Exophiala jeanselmei, Fusarium eumartii, andPaecilomyces variotii completely and rapidly degraded syringic acid (5 g/liter) within 48 to 100 hours. A further seven species were able to degrade syringic acid to some extent when glucose was added. Methylated and demethylated metabolic intermediates were identified by GC/MS.

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.

References

  1. Adler E (1977) Lignin chemistry-Past, present and future. Wood Science and Technology 11:169–218.

    Article  CAS  Google Scholar 

  2. Bergbauer M, Eggert C, Kraepelin G (1989) Polymerization and depolymerization of waste water lignins by white-rot fungi. In: Kirk TK, Chang HM (eds) Biotechnology in pulp and paper manufacture. Applications and fundamental investigations Butterworth-Heinemann, Boston, pp 263–269

    Google Scholar 

  3. Bergbauer M, Kraepelin G (1987) Degradation of lignin model compounds under waste water conditions. In: Odier E (ed) Lignin enzymic and microbial degradation. Paris, pp 283–290

  4. Blaich R, Esser K (1975) Function of enzymes in wood destroying fungi. II. Multiple forms of laccase in white rot fungi Arch Microbiol, 103:271–277

    Article  CAS  Google Scholar 

  5. Bollag J-M, Leonowicz A (1984) Comparative studies of extracellular fungal laccases. Appl Environ Microbiol 48:849–854

    CAS  PubMed  Google Scholar 

  6. Bourbonnais R, Paice MG (1987) Oxidation and reduction of lignin-related aromatic compounds byAureobasidium pullulans. Appl Microbiol. Biotechnol 26:164–169.

    Article  CAS  Google Scholar 

  7. Dill I, Kraepelin G (1988) Der Abbau von Lignin/Cellulose durch Weißfäule-Pilze: Einfluß spezifischer ökologischer Faktoren. Forum Mikrobiologie 11:484–489

    CAS  Google Scholar 

  8. Eriksson K-E, Gupta JK, Nishida A, Rao M (1984) Syringic acid metabolism by some whiterot, soft-rot and brown-rot fungi. J Gen Microbiol 130:2457–2464

    CAS  Google Scholar 

  9. Evans CT, Hanna K, Payne C, Conrad D, Misawa M (1987) Biotransformation oftrans-cinnamic acid to L-phenylalanine: Optimization of reaction conditions using whole yeast cells. Enzyme Microb Technol 9:417–421

    Article  CAS  Google Scholar 

  10. Fisher PJ (1977) New methods of detecting and studying saprophytic behaviour of aero-aquatic hyphomycetes from stagnant water. Trans Br Mycol Soc 68:407–411

    Google Scholar 

  11. 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 

  12. Gonzalez B, Merino A, Almeida M, Vicuna R (1986) Comparative growth of natural bacterial isolates on various lignin-related compounds. Appl Environ Microbiol 52:1438–1432

    Google Scholar 

  13. Gunasekara SA, Webster J, Legg CJ (1983) Effect of nitrate and phosphate on weight of pine and oak wood caused by aquatic and aeroaquatic hyphomycetes. Trans Br Mycol Soc 80:507–514

    Article  Google Scholar 

  14. Gupta JK, Jebsen C, Kneifel H (1986) Sinapic acid degradation by the yeastRhodotorula glutinis. J Gen Microbiol 132:2793–2799

    CAS  Google Scholar 

  15. Haider K, Trojanowski J (1975) Decomposition of specifically14C-labelled phenols and dehydropolymers of coniferyl alcohol as models for lignin degradation by soft and white rot fungi. Arch Microbiol 105:33–41.

    Article  CAS  Google Scholar 

  16. Henderson, MEK (1963) Fungal metabolism of certain aromatic compounds related to lignin. Pure and Appl Chem F7:589–602

    Article  Google Scholar 

  17. Heresztyn, T. (1986) Metabolism of volatile phenolic compounds from hydroxycinnamic acids byBrettanomyces yeast. Arch Microbiol 146:96–98

    Article  CAS  Google Scholar 

  18. Higuchi, T. (1981) Biodegradation of lignin. Wood Research 67:47–58.

    CAS  Google Scholar 

  19. Ishihara, T., Ishihara, M. (1976) Oxidation of syringic acid by fungal laccase. Mokuzai Gakkashi 22:371–375

    CAS  Google Scholar 

  20. Ishihara T (1983) Effect of pH in the oxidation of syringic acid by fungal laccase. Mokuzai Gakkaishi 29:801–805

    CAS  Google Scholar 

  21. Jokela J, Pellinen J, Salkinoja-Salonen M (1987) Initial steps in the pathway for bacterial degradation of two tetrameric lignin model compounds. Appl Environ Microbiol 53:2642–2649

    CAS  PubMed  Google Scholar 

  22. Katayama, T, Nakatsubo, F, Higuchi T (1980) Initial reactions in the fungal degradation of guaiacyl-β-coniferyl ether, a lignin substructure model. Arch Microbiol 126:127–132

    Article  CAS  Google Scholar 

  23. Katayama T, Nakatsubo F, Higuchi, T (1981) Degradation of aryl-glycerol-β-aryl ethers, lignin substructure models, byFusarium solani. Arch Microbiol 130:198–203

    Article  CAS  Google Scholar 

  24. Kern, HW, Kirk TK (1987) Influence of molecular size and ligninase pretreatment on degradation of lignins byXanthomonas sp. strain 99. Appl Environ Microbiol 53:2242–2246

    CAS  PubMed  Google Scholar 

  25. Kern HW, Webb LE, Eggeling L (1984) Characterization of a ligninolytic bacterial isolate: Taxonomic relatedness and oxidation of some lignin related compounds. System Appl Microbiol 5:433–447

    CAS  Google Scholar 

  26. Kirk TK, Schultz E, Connors WJ, Lorenz LF, Zeikus JG (1978) Influence of culture parameters on lignin metabolism byPharnerochaete chrysosporium. Arch Microbiol 117:277–285

    Article  CAS  Google Scholar 

  27. Kirk TK (1987) Enzymatic combustion: The degradation of lignin by white-rot fungi. In: Odier (ed) Lignin enzymic and microbial degradation. Paris, pp 51–56

  28. Leonowicz A, Edgehill RU, Bollag J-M (1984) The effect of pH on the transformation of syringic and vanillic acid by the laccases ofRhizoctonia praticola andTrametes versicolor. Arch Microbiol 137:89–96

    Article  CAS  Google Scholar 

  29. 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

    CAS  Article  Google Scholar 

  30. Lundquist K, Kristersson P (1985) Exhaustive laccase-catalysed oxidation of a lignin model compound (vanillyl glycol) produces methanol and polymeric quinoid products. Biochem. J 229:277–279

    CAS  PubMed  Google Scholar 

  31. Milstein O, Vered Y, Shragina L, Gressel J, Flowers HM, Hüttermann A (1983) Metabolism of lignin related aromatic compounds byAspergillus japonicus Arch Microbiol 135:147–154.

    Article  CAS  Google Scholar 

  32. Namba H, Nakatsubo F, Higuchi T (1983) Degradation of β-1 linked dilignols byFusarium solani M-13-1. Wood Research 69:52–60.

    CAS  Google Scholar 

  33. Norris DM (1980) Degradation of14C-labelled lignins and14C-labelled aromatic acids byFusarium solani. Appl Environ Microbiol 40:376–380

    CAS  PubMed  Google Scholar 

  34. Sparnins VL, Dagley S (1975) Alternative routes of aromatic catabolism inPseudomonas acidovorans andPseudomonas putida: Gallic acid as a substrate and inhibitor of dioxygenases. J Bacteriol 124:1374–1381.

    CAS  PubMed  Google Scholar 

  35. Stalpers JA (1978) Identification of wood-inhabiting Aphyllophorales in pure culture (Studies in Mycology 16) Centraalbureau voor Schimmelcultures, Baarn, p 248

    Google Scholar 

  36. Vicuna R, Gonzalez B, Mozuch MD, Kirk TK (1987) Metabolism of lignin model compounds of the arylglycerol-β-aryl ether type byPseudomonas acidovorans D3. Appl Environ Microbiol 53:2605–2609

    CAS  PubMed  Google Scholar 

  37. Wariishi, H, Morohoshi N, Haraguchi T (1987) Degradation of lignin by the extracellular enzymes ofCoriolus versicolor VIIIEffective degradation of syringyl type β-aryl ether lignin model compound by laccase III. Mokuzai Gakkaishi 33:892–898.

    CAS  Google Scholar 

  38. Weissenböck G (1976) Ligninbiosynthese und Lignifizierung pflanzlicher Zellwände. Biologie in Unserer Zeit 6:140–147.

    Article  Google Scholar 

Download references

Author information

Affiliations

  1. Institut für Biochemie und Molekulare Biologie, Abteilung Botanik und Mikrobiologische Chemie, Technische Universität Berlin, Franklinstrasse 29 OE 5/1, 1000, Berlin 10, Federal Republic of Germany

    Matthias Bergbauer

Authors
  1. Matthias Bergbauer
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Bergbauer, M. Degradation and oligomerization of syringic acid by distinctive ecological groups of fungi. Microb Ecol 21, 73–84 (1991). https://doi.org/10.1007/BF02539145

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02539145

Keywords

  • Lignin
  • Vanillic Acid
  • Syringic Acid
  • Lignin Model Compound
  • Exophiala