Skip to main content
Log in

Resveratrol, piceatannol, and isorhapontigenin from Norway spruce (Picea abies) debarking wastewater as inhibitors on the growth of nine species of wood-decaying fungi

  • Original
  • Published:
Wood Science and Technology Aims and scope Submit manuscript

Abstract

The diethyl ether extract obtained from solvent–solvent extraction of Norway spruce (Picea abies) debarking water, a byproduct from debarking of logs in the pulp and paper industry, was tested for inhibition of growth on agar plates of nine species of wood-decaying fungi: Antrodia sinuosa, Antrodia xantha, Coniophora puteana, Fomitopsis pinicola, Gloeophyllum sepiarium, Heterobasidion parviporum, Phlebiopsis gigantea, Serpula himantioides, and Serpula lacrymans. One fraction of the extract showed excellent antifungal activity for a majority of the species, with complete inhibition of growth for A. sinuosa, A. xantha, and G. sepiarium. The major constituents of the most active fraction were identified as the hydroxystilbenes resveratrol, isorhapontigenin (synonymous with methyl piceatannol), and piceatannol (synonymous with astringenin). The active compounds were isolated or synthesized and used individually for dose–response studies. It was found that isorhapontigenin and piceatannol inhibited all growth of A. sinuosa, A. xantha, and G. sepiarium in 0.35 % weight concentration. The hydroxystilbenes were the three most abundant substances in the debarking water and can be obtained as a mixture or in enriched forms. From some extraction steps of the raw debarking water, it would be possible to obtain the hydroxystilbenes in quantities that might be of commercial interest as efficient natural fungicides.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2

Similar content being viewed by others

References

  • Allen L, Back E (2000) Pitch control, wood resin and deresination. Tappi Press, Atlanta

    Google Scholar 

  • Andrus MB, Liu J, Meredith EL, Nartey E (2003) Synthesis of resveratrol using a direct decarbonylative Heck approach from resorcylic acid. Tetrahedron Lett 44:4819–4822

    Article  CAS  Google Scholar 

  • Asiegbu FO, Adomas A, Stenlid J (2005) Conifer root and butt rot caused by Heterobasidion annosum (Fr.) Bref. s.l. Mol Plant Pathol 6:395–409

    Article  PubMed  Google Scholar 

  • Bajpai M, Pande A, Tewari SK, Prakash D (2005) Phenolic contents and antioxidant activity of some food and medicinal plants. Int J Food Sci Nutr 56:287–291

    Article  CAS  PubMed  Google Scholar 

  • Bowyer JL, Shmulsky R, Haygreen JG (2003) Wood durability and protection. In: Bowyer JL, Shmulsky R, Haygreen JG (eds) Forest products and wood science, 4th edn. Iowa State Press, Iowa, pp 261–286

    Google Scholar 

  • Chang ST, Wu JH, Wang SY, Kang PL, Yang NS, Shyur LF (2001) Antioxidant activity of extracts from Acacia confuse bark and heartwood. J Agric Food Chem 49:3420–3424

    Article  CAS  PubMed  Google Scholar 

  • Chedgy RJ, Yuong WL, Breuil C (2009) Effects of leaching on fungal growth and decay of western redcedar. Can J Microbiol 55:578–586

    Article  CAS  PubMed  Google Scholar 

  • Co M, Fagerlund A, Engman L, Sunnerheim K, Sjöberg P, Turner C (2012) Extraction of antioxidants from spruce (Picea abies) bark using eco-friendly solvents. Phytochem Anal 32:1–11

    Article  Google Scholar 

  • Duke JA (1985) Handbook of medicinal herbs. CRSPress, Boca Raton

    Google Scholar 

  • Fagerlund Edfeldt A, Hedenström E, Edman M, Jonsson BG (2014) Effect of debarking waste water from Norway spruce (Picea abies) on the growth of five species of wood-decaying fungi. Z Naturforsch C 69:418–424

    Article  Google Scholar 

  • Fransesci VR, Krokene P, Christiansen E, Krekling T (2005) Anatomical and chemical defenses of conifer bark against bark beetles and other pests. New Phytol 167:353–375

    Article  Google Scholar 

  • Gao H, Shupe TF, Eberhardt TL, Hse CY (2007) Antioxidant activity of extracts from the wood and bark of Port Orford cedar. J Wood Sci 53:147–152

    Article  CAS  Google Scholar 

  • Geissman TA (1963) Flavonoid compounds, tannins, lignins and related compounds. In: Florkin M, Stotz EM (eds) Comprehensive biochemistry, vol 9. Elsevier, Amsterdam, pp 213–250

  • Green F, Highley TL (1997) Mechanism of brown-rot decay: paradigm or paradox. Int Biodeterior Biodegrad 39:113–124

    Article  CAS  Google Scholar 

  • Hammerbacher A, Ralph SG, Bohlman J, Fenning TM, Gershenzon J, Schmidt A (2011) Biosynthesis of the major tetrahydroxystilbenes in spruce, astringin and isorhapontigenin, proceeds via resveratrol and is enhanced by fungal infection. Plant Physiol 157:876–890

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Harmon ME, Franklin JF, Swanson FJ, Sollins P, Gregory SV, Lattin JD, Anderson NH, Cline S, Aume N, Sedell J, Lienkaemper G, Cromack KJ, Cummins K (1986) Ecology of coarse woody debris in temperate ecosystems. Adv Ecol Res 15:133–302

    Article  Google Scholar 

  • Hart JH, Hillis WE (1974) Inhibition of wood-rotting fungi by stilbenes and other polyphenols in Eucalyptus sideroxylon. Phytopathology 64:939–948

    Article  CAS  Google Scholar 

  • Kleist G, Schmitt U (2001) Characterisation of a soft rot-like decay pattern caused by Coniophora puteana (Schum.) Karst. in sapelli wood (Entandrophragma cylindricum Sprague). Holzforschung 55:573–578

    CAS  Google Scholar 

  • Kylläinen O, Holmbom B (2004) Chemical composition of components in spruce bark waters. Pap Puu 86:289–292

    Google Scholar 

  • Ledakowicza S, Michniewicz M, Jagiella A, Stufka-Olczykb J, Martynelis M (2006) Elimination of resin acids by advanced oxidation processes and their impact on subsequent biodegradation. Water Res 40:3439–3446

    Article  Google Scholar 

  • Lee HS, Lee BW, Kim MR, Jun JG (2010) Syntheses of resveratrol and its hydroxylated derivatives as radical scavenger and tyrosinase inhibitor. Bull Korean Chem Soc 31:971–975

    Article  CAS  Google Scholar 

  • Leong YW, Harrison LJ, Powell AD (1999) Phenanthrene and other aromatic constituents of Bulbophyllum vaginatum. Phytochemistry 50:1237–1241

    Article  CAS  Google Scholar 

  • Leonowitz A, Matuszewska A, Luterek J, Ziegenhagen D, Wasilewska W, Cho NS, Hofrichter M, Rogalski J (1999) Biodegradation of lignin by white-rot fungi. Fungal Genet Biol 27:175–185

    Article  Google Scholar 

  • Mars CA, Cantrell DG, Hughes K, Hughes AS (2011) Composition de protection du bois utiles pour traiter des champignons tolerants au cuivre. (Composition for protection of wood against fungus resistant to copper), France Patent 2961426-A1 (in French)

  • Mason TL, Wasserman BP (1987) Inactivation of red beet beta-glucan synthase by native and oxidized phenolic compounds. Phytochemistry 26:2197–2202

    Article  CAS  Google Scholar 

  • Persson T, Jönsson AS (2010) Isolation of hemicelluloses by ultrafiltration of thermomechanical pulp mill process water: influence of operating conditions. Chem Eng Res Des 88:1548–1554

    Article  CAS  Google Scholar 

  • Pietarinen SP, Willför SM, Ahotupa MO, Hemming J, Holmbom BR (2006) Knotwood and bark extracts: strong antioxidants from waste materials. J Wood Sci 52:436–444

    Article  CAS  Google Scholar 

  • Rajala T, Peltoniemi M, Pennanen T, Mäkipää R (2010) Relationship between wood-inhabiting fungi determined by molecular analyses (denaturating gradient gel electrophoresis) and quality of decaying logs). Can J For Res 40:2384–2397

    Article  CAS  Google Scholar 

  • Schmidt O, Moreth U (1996) Biological characterization of poria indoor brown-rot fungi. Holzforschung 50:105–110

    Article  CAS  Google Scholar 

  • Schultz TP, Hubbard TF Jr, Jin LH, Fisher TH, Nicholas DD (1990) Role of stilbenes in the natural durability of wood: fungicidal structure-activity relationships. Phytochemistry 29:1501–1507

    Article  CAS  Google Scholar 

  • Shen J, Kaur I, Baktash MM, He Z, Ni Y (2013) A combined process of activated carbon adsorption, ion exchange resin treatment and membrane concentration for recovery of dissolved organics in pre-hydrolysis liquor of the Kraft-based dissolving pulp production process. Bioresour Technol 127:59–65

    Article  CAS  PubMed  Google Scholar 

  • Silayo A, Ngadjui BT, Abegaz BM (1999) Homoisoflavonoids and stilbenes from the bulbs of Scilla nervosa subsp. Rigidifolia. Phytochemistry 52:947–955

    Article  CAS  Google Scholar 

  • Singh T, Singh AP (2012) A review on natural products as wood protectant. Wood Sci Technol 46:851–870

    Article  CAS  Google Scholar 

  • Solhaug KA (1990) Stilbene glucosides in bark and needles from picea species. Scand J For Res 5:1–4

    Article  Google Scholar 

  • Sumthong P, Romero-Gonzales R, Verpoorte R (2008) Identification of anti-wood rot compounds in teak (Tectona grandis L.f.) sawdust extract. J Wood Chem Technol 28:247–260

    Article  CAS  Google Scholar 

  • Sun H, Korhonen K, Hantula J, Asiegbu FO, Kasanen R (2009) Use of a breeding approach for improving biocontrol efficacy of Phlebiopsis gigantean strains against Heterobasidion infection of Norway spruce stumps. FEMS Microbiol Ecol 69:266–273

    Article  CAS  PubMed  Google Scholar 

  • Suzuki MR, Hunt CG, Houtman CJ, Dalebroux ZD, Hammel KE (2006) Fungal hydroquinones contribute to brown rot of wood. Environ Microbiol 8:2214–2223

    Article  CAS  PubMed  Google Scholar 

  • Thakkar K, Geahlen RL, Cushman M (1993) Synthesis and protein-tyrosine kinase inhibitory activity of polyhydroxylated stilbene analogues of piceatannol. J Med Chem 36:2950–2955

    Article  CAS  PubMed  Google Scholar 

  • Wang SY, Chen RF, Chan ST (2005) Antifungal activities of essential oils and their constituents from indigenous cinnamon (Cinnamomum osmophloeum) leaves against wood decay fungi. Bioresour Technol 96:813–818

    Article  CAS  PubMed  Google Scholar 

  • Willför SM, Ahotupa MO, Hemming JE, Reunanen MHT, Eklund PC, Sjöholm RE, Eckerman CSE, Pohjamo SP, Holmbom BR (2003) Antioxidant activity of knotwood extractives and phenolic compounds of selected tree species. J Agric Food Chem 51:7600–7606

    Article  PubMed  Google Scholar 

  • Willför S, Nisula L, Hemming J, Reunanen M, Holmbom B (2004) Bioactive phenolic substances in industrially important tree species: part 1: knots and stemwood of different spruce species. Holzforschung 58:335–344

    Google Scholar 

  • Wu JH, Tung YT, Wang SY, Shyur LF, Kuo YH, Chang ST (2005) Phenolic antioxidants from the heartwood of Acacia confusa. J Agric Food Chem 53:5917–5921

    Article  CAS  PubMed  Google Scholar 

  • Yang DQ (2009) Potential utilization of plant and fungal extracts for wood protection. For Prod J 59:97–103

    Google Scholar 

  • Yang DQ, Wang XM, Shen J, Wan H (2004) Antifungal properties of barks of various wood species. For Prod J 54:37–39

    Google Scholar 

  • Yelle DJ, Ralph J, Lu F, Hammel KE (2008) Evidence for cleavage of lignin by a brown rot basidiomycete. Environ Microbiol 10:1844–1849

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgments

We are grateful for the financial support from the EU (Objective 2, South Forest Counties region) and the County Administrative Board of Västernorrland. We also thank Oddmund Björkås for supplying us with debarking water from the Ortviken paper mill in Sundsvall, Sweden, and Saba Hagos for assisting with some experiments with the fungi.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Erik Hedenström.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hedenström, E., Fagerlund Edfeldt, A., Edman, M. et al. Resveratrol, piceatannol, and isorhapontigenin from Norway spruce (Picea abies) debarking wastewater as inhibitors on the growth of nine species of wood-decaying fungi. Wood Sci Technol 50, 617–629 (2016). https://doi.org/10.1007/s00226-016-0814-4

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00226-016-0814-4

Keywords

Navigation