Skip to main content

Advertisement

Official Journal of the Japan Wood Research Society

Journal of Wood Science Cover Image

Screening for condensed tannin-degrading fungi with a synthetic 14C-labeled compound

Article metrics

  • 404 Accesses

Abstract

To find fungi that are potent for degradation of condensed tannin, a two-step screening was used. This involved measurement of fungal growth rate on Japanese cedar (Cryptomeria japonica) bark, followed by determination of [14C]-labeled CO2 generated from fungal degradation of synthetic [14C]-labeled condensed tannin model. In the first screening, 75 strains of wood rot fungi were tested, and 19 strains effectively decreased bark weight and/or the weight of the methanol-soluble fraction. For the second screening, [14C]-labeled condensed tannin model compound was synthesized in 11.8% yield based on radioactivity measurements. Over the incubation period, Coriolus hirsutus K-2671, Lentinus edodes Is, and Lampteromyces japonicus Nn showed higher cumulative [14C]-labeled CO2 emissions than the other strains and mineralized the [14C]-labeled condensed tannin model compound by 3.7%, 3.0%, and 3.0%, respectively. Fractionation of the methanol extracts from the medium by gel permeation chromatography after fungal treatment suggested that fungi that can induce the emission of significant levels of [14C]-labeled CO2 can extensively depolymerize condensed tannins.

References

  1. 1.

    Haslam E (1989) Plant polyphenols - vegetable tannins revisited. Cambridge University Press, Cambridge

  2. 2.

    Hillis WE (1985) In Higuchi T (ed) Biosynthesis and biodegradation of wood components. Academic, Orlando, p 209

  3. 3.

    Hillis WE (1987) Heartwood and tree exudates. Springer, Berlin Heidelberg New York, p 76

  4. 4.

    Navon A, Hare JD, Federici BA (1993) Interactions among Heliothis virescens larvae, cotton condensed tannin and the CryIA(c) δ-endotoxin of Bacillus thuringiensis. J Chem Ecol 19: 2485–2499

  5. 5.

    Ayres MP, Clausen TP, MacLean SF, Redman AM, Reichardt PB (1997) Diversity of structure and antiherbivore activity in condensed tannins. Ecology 78:1696–1712

  6. 6.

    Hammerschmidt R (1999) Induced disease resistance: how do induced plants stop pathogens? Physiol Mol Plant Pathol 55:77–84

  7. 7.

    Scalbert A (1991) Antimicrobial properties of tannins. Phytochemistry 30:3875–3883

  8. 8.

    Shirley BW (1996) Flavonoid biosynthesis: ‘new’ functions for an ‘old’ pathway. Trends Plant Sci 1:377–382

  9. 9.

    Bieza K, Lois R (2001) An Arabidopsis mutant tolerant to lethal ultraviolet-B levels shows constitutively elevated accumulation of flavonoids and other phenolics. Plant Physiol 126:1105–1115

  10. 10.

    Haslam E, Lilley TH (1988) Natural astringency in foodstuffs. A molecular interpretation. Crit Rev Food Sci Nutr 27:1–41

  11. 11.

    Hagerman AE, Butler LG (1981) The specificity of proanthocyanidin-protein interactions. J Biol Chem 256:4444–4497

  12. 12.

    Kashiwada Y, Nonaka G, Nishioka I, Chang JJ, Lee KH (1992) Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents. J Nat Prod 55:1033–1043

  13. 13.

    Tourino S, Selga A, Jimenez A, Julia L, Lozano C, Lizarraga DL, Cascante M, Torres JL (2005) Procyanidin fractions from pine (Pinus pinaster) bark: radical scavenging power in solution, antioxidant activity in emulsion, and antiproliferative effect in melanoma cells. J Agric Food Chem 53:4728–4735

  14. 14.

    Bourvellec CL, Guyot S, Renard CMGC (2004) Non-covalent interaction between procyanidins and apple cell wall material part I. Effect of some environmental parameters. Biochim Biophys Acta 1672:192–202

  15. 15.

    Chandra T, Krishnamurthy V, Madhavakrishna W, Nayyudamma Y (1973) Astringency in fruits: microbial degradation of wood apple tannin. Leather Sci 20:269–273

  16. 16.

    Grand WD (1976) Microbial degradation of condensed tannins. Science 193:1137–1139

  17. 17.

    Gamble GR, Akin DE, Makkar HPS, Becker K (1996) Biological degradation of tannins in sericea lespedeza (Lespedeza cuneta) by the white rot fungi Ceriporiopsis subvermispora and Cyathus stercoreus analyzed by solid-state 13C-nuclear magnetic resonance spectroscopy. Appl Environ Microbiol 62:3600–3604

  18. 18.

    Yoneda S, Kawamoto H, Nakatsubo J (1997) Synthesis of high molecular mass condensed tannin by cationic polymerization of flavan-3,4-carbonate. J Chem Soc Perkin Trans 1, pp 1025–1030

  19. 19.

    Coleman GH, Talbot WF (1933) sym-Tribromobenzene. Org Synth 13:96–98

  20. 20.

    McKillop A, Howarth BD, Kobylecki RJ, Ryszard J (1974) Simple and inexpensive procedure for the preparation of phloroglucinol and phloroglucinol trimethyl ether. Synth Commun 4:35–43

  21. 21.

    Kawamoto H, Nakatsubo F, Murakami K (1996) O-Benzylation of phloroglucinol via phloroglucinol triacetate. Synth Commun 26:531–534

  22. 22.

    Kirk TK, Connors WJ, Bleam RD, Hackett WF, Zeikus JG (1975) Preparation and microbial decomposition of synthetic [14C]lignins. Proc Nat Acad Sci USA 72:2515–2519

  23. 23.

    Coll PM, Fernández-Abalos JM, Villanueva JR, Santamaría R, Pérez P (1993) Purification and characterization of a phenoloxidase (laccase) from the lignin-degrading basidiomycete PM1 (CECT 2971). Appl Environ Microbiol 59:2607–2613

  24. 24.

    Kawai S, Umezawa T, Higuchi T (1988) Degradation mechanisms of phenolic beta-1 lignin substructure model compounds by laccase of Coriolus versicolor. Arch Biochem Biophys 262:99–110

  25. 25.

    Kofujita H, Nabeta K, Okuyama H, Miyake M (1989) Biodegradation of milled wood lignin on cellulose particle by Lentinus edodes. Mokuzai Gakkaishi 35:268–274

  26. 26.

    Osman AM, Wong KKY (2007) Laccase (EC 1.10.3.2) catalyses the conversion of procyanidin B-2 (epicatechin dimer) to type A-2. Tetrahedron Lett 48:1163–1167

  27. 27.

    Gnanamani A, Sekaran G, Babu M (2001) Removal of tannin from cross-linked and open chain polymeric tannin substrates using heme peroxidases of Phanerochaete chrysosporium. Bioprocess Biosyst Eng 24:211–217

  28. 28.

    Hosny M, Rosazza JPN (2002) Novel oxidations of (+)-catechin by horseradish peroxidase and laccase. J Agric Food Chem 50:5539–5545

Download references

Author information

Correspondence to Hisayoshi Kofujita.

Additional information

This article was presented at the 55th Annual Meeting of the Japan Wood Research Society, Kyoto, August 2005

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Kimura, F., Obara, N. & Kofujita, H. Screening for condensed tannin-degrading fungi with a synthetic 14C-labeled compound. J Wood Sci 55, 350–358 (2009) doi:10.1007/s10086-009-1035-3

Download citation

Key words

  • Condensed tannins
  • Biodegradation
  • Fungi