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Official Journal of the Japan Wood Research Society

Extractives of Quercus crispula sapwood infected by the pathogenic fungi Raffaelea quercivora I: comparison of sapwood extractives from noninfected and infected samples

A Correction to this article was published on 27 April 2018


The extracts of Quercus crispula infected by the ambrosia fungus, Raffaelea quercivora, were investigated. Phenol and tannin analyses indicated that normal sapwood (NS) contained a considerable amount of hydrolysable tannins, while infected colored sapwood (IS) contained less hydrolysable tannins and more phenols than NS. In treating pentagalloyl glucose (PGG), which is a model compound of hydrolysable tannins, with a culture medium of R. quercivora, PGG was rapidly hydrolyzed to produce gallic acid. The resulting gallic acid decreased in concentration over the subsequent cultivation period eventually disappeared. Measuring tannase and laccase activities of the culture medium of R. quercivora, tannase activity increased gradually from the beginning, while laccase activity increased rapidly at 5 days of incubation and disappeared at 8 days. An oxidative product from gallic acid treated with laccase was isolated by preparative high performance liquid chromatography, and was identified as purprogallincarboxylic acid (PGCA) by nuclear magnetic resonance spectroscopy and electron-impact mass spectrometry. PGCA was present in a 70% aqueous acetone extract of IS, and showed slight growth inhibition against R. quercivora.


  1. Ito S, Kubono T, Sahashi N, Yamada T (1998) Associated fungi with the mass mortality of oak trees (in Japanese). J Jpn For Soc 80:170–175

    Google Scholar 

  2. Kubono T, Ito S (2002) Raffaelea quercivora sp. nov. associated with mortality of Japanese oak and the ambrosia beetle (Platypus quercivorus). Mycoscience 43:255–260

    Article  Google Scholar 

  3. Bauch J (1986) Verfärbungen von Rund- und Schnittholz und Möglichkeiten für vorbeugende Schutzmaßnahmen. Holz-Zentralbl 112:2217–2218

    Google Scholar 

  4. Armondo GM, Marc F, Bernhard K (1997) Chemical and UV-VIS spectroscopic study on kiln brown stain formation in radiata pine. In: Proceedings of the 9th International Symposium of Wood and Pulping Chemistry. Montreal, Canada, June 9–-12, pp 70.1–70.5

  5. Lidija M (1975) Formation of tyloses in felled Quercus rubra L. Wood Sci Technol 9:3–14

    Article  Google Scholar 

  6. Armondo GM, Marc F, Bernhard K, Frank L (2000) The chemical nature of kiln brown stain in radiata pine. Holzforschung 54: 12–22

    Google Scholar 

  7. Rizzi GP (1994) The Maillard reactions in food. In: Labuza TP, Reineccius GA, Morrier VM, O’Brien J, Baynes JW (eds) Maillard reactions in chemistry, food and health. Royal Society of Chemistry, Cambridge, UK, pp 11–19

    Google Scholar 

  8. Threander O, Nelson DA (1988) Aqueous high temperature transformation of carbohydrates relative to utilisation of biomass. Adv Carbohydr Chem Biochem 46:273–326

    Article  Google Scholar 

  9. Murray LL, Durria AAM (1996) An enzyme extract from Douglasfir sapwood and its relationship to brown staining. Wood Fiber Sci 28:2–6

    Google Scholar 

  10. Laver ML, Durria AAM (1997) Chemical brown staining of Douglas-fir wood: characterization of a wood enzyme extract. Forest Prod J 47:93–97

    CAS  Google Scholar 

  11. Bauch J, Hundt H, Weissmann G, Lange W, Kubel H (1991) On the causes of yellow discolourations of oak heartwood (Quercus sect. robur) during drying. Holzforschung 45:79–85

    Article  Google Scholar 

  12. Battestin V, Macedo GA (2006) Tannase production by Paecilomyces variotii. Bioresource Technol 98:1832–1837

    Article  Google Scholar 

  13. Takagi K, Shimomura K, Koizumi Y, Mitsunaga T, Abe I (1999) Tyrosinase inhibitors from the pericarp of jatoba (Hymenaea courbaril L.) (in Japanese with English summary). Nat Med 53:15–21

    CAS  Google Scholar 

  14. Takagi K, Mitsunaga T (2002) A tyrosinase inhibitor from the asam (Mangifera quadrifida). Nat Med 56:97–103

    CAS  Google Scholar 

  15. Richard T, Vitrac X, Merillon JM, Monti JP (2005) Role of peptide primary sequence in polyphenol-protein recognition: an example with neurotensin. Biochim Biophys Acta 1726:238–243

    Article  CAS  PubMed  Google Scholar 

  16. Yoshihara I, Akamatsu I, Ueshima H, Fujii T (1985) Screening of white rot fungi which has strong resolution activity against lignin (in Japanese). Jpn TAPPI J 39:65–74

    Article  Google Scholar 

  17. Karl H (1954) Über die Bildung der Purpurogallincarbonsäure durch fermentative Oxydation der Gallussäure. (zugleich II Mitteilung über gerbstoffartige Substanzen). Archiv der Pharmazie 287:497–503

    Article  Google Scholar 

  18. Panizzi L, Caponi C, Catalano S, Cioni PL, Morelli I (2002) In vitro antimicrobial activity of extracts and isolation constituents of Rubus ulmifolius. J Ethnopharmacol 79:165–168

    Article  CAS  PubMed  Google Scholar 

  19. Shukla YN, Anil S, Sunil K, Susil K (1999) Phytotoxic and antimicrobial constituents of Argyreia speciosa and Oenothera biennis. J Ethnopharmacol 67:241–245

    Article  CAS  PubMed  Google Scholar 

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Correspondence to Tohru Mitsunaga.

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Part of this study was presented at the 57th Annual Meeting of the Japan Wood Research Society, Hiroshima, Japan, 2007

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Imai, K., Mitsunaga, T., Takemoto, H. et al. Extractives of Quercus crispula sapwood infected by the pathogenic fungi Raffaelea quercivora I: comparison of sapwood extractives from noninfected and infected samples. J Wood Sci 55, 126–132 (2009).

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Key words

  • Raffaelea quercivora
  • Quercus crispula
  • Gallotannins
  • Ellagitannins
  • Tannase