Skip to main content
SpringerLink
Log in

Antioxidant flavonoids from knotwood of Jack pine and European aspen

Antioxidative Flavonoide aus dem Astholz von Jack Pine und Aspe

  • ORIGINALARBEITEN ORIGINALS
  • Published:
Holz als Roh- und Werkstoff Aims and scope Submit manuscript

Abstract

Flavonoids have recently been found in large amounts in knotwood and stemwood of several tree species. Six flavonoids, two flavonoid glucosides, and one cinnamic acid derivative were isolated from Jack pine and European aspen knotwood and structurally characterised using GC-MS, HR-MS, and NMR spectroscopic analyses. Isolated compounds were further assessed on basis of their potency to inhibit lipid peroxidation and scavenge peroxyl radicals. All tested compounds possessed antioxidant properties close to that of the reference compound Trolox.

Zusammenfassung

Im Ast- und Stammholz verschiedener Baumarten hat man in jüngerer Zeit größere Mengen von Flavonoiden gefunden. Sechs Flavonoide, zwei Flavonoidglykoside und ein Zimtsäurederivat wurden aus dem Astholz von Jack Pine und Aspe isoliert und mittels GC-MS, HR-MS und NMR Spektralanalysen strukturell bestimmt. Ausgehend von deren Potential, eine Lipidperoxidation zu hemmen und Peroxylradikale abzufangen, wurden die isolierten Verbindungen weiter untersucht. Alle untersuchten Verbindungen verfügten über antioxidative Eigenschaften, die denjenigen der Referenzverbindung Trolox weitgehend entsprachen.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Ahotupa M, Mäntylä E, Kangas L (1997) Antioxidant properties of the triphenylethylene antiestrogen drug toremifene. Naunyn-Schmiedeberg’s Arch Pharmacol 356(3):297--302

    Article  CAS  Google Scholar 

  2. Arjun Banskota H, Nagaoka T, Sumioka L-Y, Tezuka Y, Awale S, Midorikawa K, Matsushige K, Kadota S (2002) Antiproliferative activity of the Netherlands propolis and its active principles in cancer cell lines. J Ethnopharmacol 80(1):67--73

    Article  Google Scholar 

  3. Bankova V, Popova M, Bogdanov S, Sabatini A-M (2002) Chemical composition of European propolis: expected and unexpected results. J Biosci 57(5/6):530--533

    CAS  Google Scholar 

  4. Holmbom B, Eckerman C, Eklund P, Hemming J, Nisula L, Reunanen M, Sjöholm R, Sundberg A, Sundberg K, Willför S (2004) Knots in trees -- a new rich source of lignans. Phytochem Rev 2(3):331--340

    Article  Google Scholar 

  5. Hopia AI, Heinonen M (1999) Antioxidant activity of flavonol aglycones and their glycosides in methyl linoleate. J Am Oil Chem Soc 76(1):139--144

    CAS  Google Scholar 

  6. Jung HA, Jung ME, Kim JY, Chung HY, Choi JS (2003) Inhibitory activity of flavonoids from Prunus davidiana and other flavonoids on total ROS and hydroxyl radical generation. Arch Pharm Res 26(10):809--815

    Article  PubMed  CAS  Google Scholar 

  7. Jung JH, McLaughlin JL (1990) 13C-1H NMR long-range coupling and deuterium isotope effects of flavanones. Phytochemistry 29(4):1271--1275

    Article  CAS  Google Scholar 

  8. Kumazawa S, Hamasaka T, Nakayama T (2003) Antioxidant activity of propolis of various geographic origins. Food Chem 84(3):329--339

    Article  CAS  Google Scholar 

  9. Kuroyanagi M, Yamamoto Y, Fukushima S, Ueno A, Noro T, Miyase T (1982) Chemical studies on the constituents of Polygonum nodosum. Chem Pharm Bull 30(5):1602--1608

    CAS  Google Scholar 

  10. Kuroyanagi M, Noro T, Fukushima S, Aiyama R, Ikuta A, Itokawa I, Morita M (1983) Studies of constituents of seeds of Alpinia katsumadai Hayata. Chem Pharm Bull 31(5):1544--1550

    CAS  Google Scholar 

  11. Lindberg LE, Willför SM, Holmbom BR (2004) Antibacterial effects of knotwood extractives on paper mill bacteria. J Ind Microbiol Biotechnol 31(3):137--147

    Article  PubMed  CAS  Google Scholar 

  12. Obst JR (1998) Special (secondary) metabolites from wood. In: Bruce A, Palfreyman JW (eds) Forest Products Biotechnology. Taylor & Francis, London, pp 151--165

    Google Scholar 

  13. Ondrias K, Stasko A, Hromadova M, Suchy V, Nagy M (1997) Pinobanksin inhibits peroxidation of low density lipoprotein and it has electron donor properties reducing α-tocopherol radicals. Die Pharmazie 52(7):566--567

    PubMed  CAS  Google Scholar 

  14. Pietarinen S (2005) Extractives in Stemwood and Knots of Acacia and Aspen Trees. Doctoral Thesis, Faculty of Chemical Engineering, Åbo Akademi University, Åbo, Finland

  15. Pietarinen S, Willför S, Sjöholm R, Holmbom B (2005a) Bioactive phenolic substances in important tree species. Part 3. Knots and stemwood of Acacia crassicarpa and A. mangium. Holzforschung 59(1):94--101

    Article  CAS  Google Scholar 

  16. Pietarinen SP, Willför SM, Vikström FA, Holmbom BR (2005b) Aspen knots, a rich source of flavonoids. J Wood Chem Technol, in press

  17. Pietarinen S, Willför S, Ahotupa M, Hemming J, Holmbom B (2005c) Knotwood and bark extracts -- Strong antioxidants from waste materials. J Wood Sci, in press

  18. Prescott AG, Stamford PJN, Wheeler G, Firmin JL (2002) In vitro properties of a recombinant flavonol synthase from Arabidopsis thaliana. Phytochemistry 60(6):589--593

    Article  PubMed  CAS  Google Scholar 

  19. Rice-Evans CA, Miller NJ, Paganga G (1996) Structure-antioxidant activity relationship of flavonoids and phenolic acids. Free Radical Biol Med 20(7):933--956

    Article  CAS  Google Scholar 

  20. Rudloff E, Sato A (1965) Chemical composition of the heartwood extractive of Pinus banksiana and Pinus resinosa. In: Proc 1st Can Wood Chem Symp, Toronto (1963), pp 69--73

  21. Sala A, Recio MC, Schinella GR, Mànez S, Giner RM, Cerdà-Nicolàs M, Rìos J-L (2003) Assessment of the anti-inflammatory activity and free radical scavenger activity of tiliroside. Eur J Pharmacol 461(1):53--61

    Article  PubMed  CAS  Google Scholar 

  22. Santos AC, Uyemura SA, Lopes JC, Bazon JN, Mingatto FE, Curti C (1998) Effect of naturally occurring flavonoids on lipid peroxidation and membrane permeability transition in mitochondria. Free Radical Biol Med 24(9):1455--1461

    Article  CAS  Google Scholar 

  23. Silva AMS, Alkorta I, Elguero J, Silva VLM (2001) A 13C NMR study of the structure of four cinnamic acids and their methyl esters. J Mol Struct 595(1-3):1--6

    Article  CAS  Google Scholar 

  24. Velikova M, Bankova V, Sorkun K, Houcine S, Tsvetkova I, Kujumgiev A (2000) Propolis from the Mediterranean region: chemical composition and antimicrobial activity. J Biosci 55(9/10):790--193

    CAS  Google Scholar 

  25. Willför SM, Ahotupa MO, Hemming JE, Reunanen MHT, Eklund PC, Sjöholm RE, Eckerman CSE, Pohjamo SP, Holmbom BR (2003) Antioxidative activity of knotwood extractives and phenolic compounds of selected tree species. J Agric Food Chem 51(26):7600--7606

    Article  PubMed  CAS  Google Scholar 

  26. Willför SM, Nisula L, Hemming JE, Reunanen MHT, Holmbom BR (2004) Bioactive phenolic substances in industrially important tree species. Part 1: Knots and stemwood of different spruce species. Holzforschung 58(4):335--344

    Article  CAS  Google Scholar 

  27. Zheng W, Wang SY (2001) Antioxidative capacity and phenolic compounds in selected herbs. J Agric Food Chem 49(11):5165--5170

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry and Biochemistry, University of Agricultural Sciences and Veterinary Medicine Cluj-Napoca, Str. Manastur 3–5, 3400, Cluj-Napoca, Romania

    M. Neacsu

  2. Laboratory of Organic Chemistry, Process Chemistry Centre, Åbo Akademi University, Biskopsgatan 8, 20500, Turku/Åbo, Finland

    P. C. Eklund & R. E. Sjöholm

  3. Laboratory of Wood and Paper Chemistry, Process Chemistry Centre, Åbo Akademi University, Porthansgatan 3, 20500, Turku/Åbo, Finland

    S. P. Pietarinen, B. R. Holmbom & S. M. Willför

  4. BioCity B 4, MCA Research Laboratory, Tykistökatu 6B, 20520, Turku/Åbo, Finland

    M. O. Ahotupa

Authors
  1. M. Neacsu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. P. C. Eklund
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. R. E. Sjöholm
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. P. Pietarinen
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. M. O. Ahotupa
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. B. R. Holmbom
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. S. M. Willför
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. M. Willför.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Neacsu, M., Eklund, P.C., Sjöholm, R.E. et al. Antioxidant flavonoids from knotwood of Jack pine and European aspen . Holz Roh Werkst 65, 1–6 (2007). https://doi.org/10.1007/s00107-006-0121-0

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00107-006-0121-0

Keywords

Search

Navigation