Home Composition and antioxidant properties of extracts from Douglas fir bark
Article
Licensed
Unlicensed Requires Authentication

Composition and antioxidant properties of extracts from Douglas fir bark

  • Isabel Miranda , Joana Ferreira EMAIL logo , Sofia Cardoso and Helena Pereira
Published/Copyright: January 7, 2021
Become an author with De Gruyter Brill
Submit Manuscript Author Information
Holzforschung
From the journal Holzforschung Volume 75 Issue 7

Abstract

This study aimed to investigate the antioxidant ability and the chemical composition of apolar and polar extractives from Douglas-fir bark, cork and phloem, establishing a possible correlation with the structural variation along the tree stem and geographic location. Douglas-fir bark extractives’ composition were analyzed at three stem heights in trees from two locations. Cork and phloem extracts’ composition were analyzed in samples collected at stem base. Extractives content in Douglas-fir bark varied between 14 and 31% and polar extractives (11–29%) were dominant over non-polar. Lipophilic extracts were mainly composed of terpenoids, representing 27–77% of all compounds, highlighted by callitrisic acid (11–34%). Sterols were also abundant (6–45%), with β-sitosterol representing 7–33% of all compounds. Alkanoic acids were present in smaller amounts. Ethanol–water extracts showed high phenolic (562–762 mg GAE/g extract), flavonoid and condensed tannins contents (399–683 mg CE/g extract and 120–262 mg CE/g of extract), high scavenging (IC50 2.8 µg extract/mL) and reducing (12 mM Fe2+/g extract) abilities. Cork had high phenolic (819 mg GAE/g extract) and flavonoid contents (524 mg CE/g extract) and high antioxidant capacity (1080 mg TEAC/g extract). Detailed knowledge of Douglas-fir extracts demonstrates their potential as a source of fine chemicals towards different applications.

Keywords: antioxidant properties; bark; hydrophilic extracts; lipophilic extracts; Pseudotsuga menziesii
Corresponding author: Joana Ferreira, Centro de Estudos Florestais, Instituto Superior de Agronomia, Universidade de Lisboa, Tapada da Ajuda, 1349-017Lisboa, Portugal, E-mail:

Funding source: Fundação para a Ciência e a Tecnologia

Award Identifier / Grant number: AGR/UID00239/2013

Award Identifier / Grant number: PD/BD/52404/2013

Acknowledgements

We thank Instituto da Conservação da Natureza e das Florestas (ICNF) for helping with the tree selection, and the sawmills Albano Leite da Silva, LDA and VilaMadeiras – Comércio de Madeiras, LDA for allowing the sampling at the time of tree harvest. We thank Lídia Silva and Joaquina Martins for help with the chemical analysis.

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: Centro de Estudos Florestais (CEF) is a research unit funded by Fundação para a Ciência e a Tecnologia (FCT) (AGR/UID00239/2013). Sofia Cardoso acknowledges a FCT doctoral fellowship (PD/BD/52404/2013) under the Sustainable Forests and Products (SUSFOR) doctoral program.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

Abdalla, S., Pizzi, A., Ayed, N., Bouthoury, F.C., Charrier, B., Bahabri, F., and Ganash, A. (2014). MALDI-TOF analysis of Aleppo pine (Pinus halepensis) bark tannin. BioResource 9: 3396–3406, https://doi.org/10.15376/biores.9.2.3396-3406.Search in Google Scholar

Anttila, A.-K., Pirttilä, A.M., Häggman, H., Harju, A., Venäläinen, M., Haapala, A., Holmbom, B., and Julkunen-Tiitto, R. (2013). Condensed conifer tannins as antifungal agents in liquid culture. Holzforschung 67: 825–832, https://doi.org/10.1515/hf-2012-0154.Search in Google Scholar

Aroso, I.M., Araújo, A.R., Fernandes, J.S., Santos, T., Batista, M.T., Pires, R.A., Mano, J.F., and Reis, R.M. (2017). Hydroalcoholic extracts from the bark of Quercus suber L. (Cork): optimization of extraction conditions, chemical composition and antioxidant potential. Wood Sci. Technol. 51: 855–872, https://doi.org/10.1007/s00226-017-0904-y.Search in Google Scholar

Benzie, I.F. and Strain, J.J. (1996). The ferric reducing ability of plasma (FRAP) as a measure of “antioxidant power”: the FRAP assay. Anal. Biochem. 239: 70–76, https://doi.org/10.1006/abio.1996.0292.Search in Google Scholar PubMed

Bertaud, F., Tapin-Lingua, S., Pizzi, A., Navarrete, P., and Petit-Conil, M. (2012). Development of green adhesives for fiberboard manufacturing using tannins and lignin from pulp mill residues. Cell. Chem. Technol. 46: 449–455.Search in Google Scholar

Bianchi, S., Koch, G., Janzon, R., Ingo, I., Bodo, S., and Frédéric, P. (2015a). Hot water extraction of Norway spruce (Picea abies [Karst.]) bark: analyses of the influence of bark aging and process parameters on the extract composition. Holzforschung 70: 619–631, https://doi.org/10.1515/hf-2015-0160.Search in Google Scholar

Bianchi, S., Kroslakova, I., Janzon, R., Mayer, I., Saake, B., and Pichelin, F. (2015b). Characterization of condensed tannins and carbohydrates in hot water bark extracts of European softwood species. Phytochemistry 120: 53–61, https://doi.org/10.1016/j.phytochem.2015.10.006.Search in Google Scholar PubMed

Bonzanini, F., Bruni, R., Palla, G., Serlataite, N., and Caligiani, A. (2009). Identification and distribution of lignans in Punica granatum L. fruit endocarp, pulp, seeds, wood knots and commercial juices by GC–MS. Food Chem. 117: 745–749, https://doi.org/10.1016/j.foodchem.2009.04.057.Search in Google Scholar

Cai, Y., Sun, M., and Corke, H. (2003). Antioxidant activity of betalains from plants of the amaranthaceae. J. Agric. Food Chem. 51: 2288–2294, https://doi.org/10.1021/jf030045u.Search in Google Scholar PubMed

Cardoso, S. and Pereira, H. (2017). Characterization of Douglas-fir grown in Portugal: heartwood, sapwood, bark, ring width and taper. Eur. J. For. Res. 136: 597–607, https://doi.org/10.1007/s10342-017-1058-z.Search in Google Scholar

Cardoso, S., Ferreira, J., Quilhó, T., and Pereira, H. (2018). Cork of Douglas-fir bark: impact of structural and anatomical features on usage. Ind. Crops Prod. 99: 135–141, https://doi.org/10.1016/j.indcrop.2017.02.001.Search in Google Scholar

Conde, E., Cadahia, E., Garcia-Vallejo, M.C., and Simon, B.F. (1997). Low molecular weight polyphenols in cork of Quercus suber. J. Agric. Food Chem. 45: 2695–2700, https://doi.org/10.1021/jf960486w.Search in Google Scholar

Eglinton, G. and Hunneman, D.H. (1968). Gas chromatographic-mass spectrometric studies of long chain hydroxy acids—I: the constituent cutin acids of apple cuticle. Phytochemistry 7: 313–322, https://doi.org/10.1016/S0031-9422(00)86330-X.Search in Google Scholar

Ferreira, J.P.A., Miranda, I., Gominho, J., and Pereira, H. (2015). Selective fractioning of Pseudotsuga menziesii bark and chemical characterization in view of an integrated valorization. Ind. Crops Prod. 74: 998–1007, https://doi.org/10.1016/j.indcrop.2015.05.065.Search in Google Scholar

Ferreira, J., Miranda, I., Gominho, J., and Pereira, H. (2016). Chemical characterization of cork and phloem from Douglas-fir outer bark. Holzforschung 70: 475–483, https://doi.org/10.1515/hf-2015-0119.Search in Google Scholar

Ferreira, J., Miranda, I., and Pereira, H. (2018). Chemical composition of lipophilic extractives from six Eucalyptus barks. Wood Sci. Technol. 52: 1685–1699, https://doi.org/10.1007/s00226-018-1054-6.Search in Google Scholar

Foo, L.Y. and Karchesy, J.J. (1989). Polyphenolic glycoside from Douglas fir inner bark. Phytochemistry 28: 1237–1240, https://doi.org/10.1016/0031-9422(89)80217-1.Search in Google Scholar

Fradinho, D.M., Neto, C.P., Evtuguin, D., Jorge, F.C., Irle, M.A., Gil, M H., and Pedrosa de Jesus, J. (2002). Chemical characterisation of bark and of alkaline bark extracts from maritime pine grown in Portugal. Ind. Crops Prod. 16: 23–32, https://doi.org/10.1016/S0926-6690(02)00004-3.Search in Google Scholar

Garcia, D.E., Glasser, W.G., Pizzi, T.A., Osorio-Madrazo, A., and Laborie, M.-P. G. (2014). Synthesis and physicochemical properties of hydroxypropyl tannins from maritime pine bark (Pinus pinaster Ait). Holzforschung 68: 411–418, https://doi.org/10.1515/hf-2013-0145.Search in Google Scholar

Graça, J. and Pereira, H. (2000). Methanolysis of bark suberins: analysis of glycerol and acid monomers. Phytochem. Anal. 11: 45–51, https://doi.org/10.1002/(SICI)1099-1565(200001/02)11:1<45::AID-PCA481>3.0.CO;2-8.10.1002/(SICI)1099-1565(200001/02)11:1<45::AID-PCA481>3.0.CO;2-8Search in Google Scholar

Hergert, H.L. and Kurth, E.F. (1952). The chemical nature of the cork from Douglas-fir bark. TAPPI 35: 59–66.Search in Google Scholar

Holmes, G.W. (1961). The chemical composition of the extractives from the newly formed inner bark of Douglas-fir, Pseudotsuga menziesii (Mirn.) Franco. Corvallis: Oregon State College.Search in Google Scholar

Hubbard, J.K. and Kurth, E.F. (1949). Douglas-fir bark tannin. J. Am. Leather Chem. Assoc. XLIV: 8.Search in Google Scholar

Kähkönen, M.P., Hopia, A.I., Vuorela, H.J., Rauha, J.-P., Pihlaja, K., Kujala, T.S., and Heinonen, M. (1999). Antioxidant activity of plant extracts containing phenolic compounds. J. Agric. Food Chem. 47: 1954–1962, https://doi.org/10.1021/jf990146.Search in Google Scholar

Kolattukudy, P.E. and Agrawal, V.P. (1974). Structure and composition of aliphatic constituents of potato tuber skin (suberin). Lipids 9: 682–694, https://doi.org/10.1007/BF02532176.Search in Google Scholar

Kurth, E.F. (1950). The composition of the wax from Douglas-fir bark. J. Am. Chem. Soc. 72: 1685–1686, https://doi.org/10.1021/ja01160a072.Search in Google Scholar

Kurth, E.F. (1953). Chemicals from Douglas-fir bark (No. C-2). Oregon Forest Products Laboratory, Corvallis.Search in Google Scholar

Kurth, E.F. and Kiefer, H.J. (1950). Wax from Douglas-fir bark. TAPPI 33: 4.Search in Google Scholar

Lacoste, C., Čop, M., Kemppainen, K., Giovando, S., Pizzi, A., Laborie, M.-P., Sernek, M., and Celzard, A. (2015). Biobased foams from condensed tannin extracts from Norway spruce (Picea abies) bark. Ind. Crops Prod. 73: 144–153, https://doi.org/10.1016/j.indcrop.2015.03.089.Search in Google Scholar

Lima, L., Miranda, I., Knapic, S., Quilhó, T., and Pereira, H. (2018). Chemical and anatomical characterization, and antioxidant properties of barks from 11 Eucalyptus species. Eur. J. Wood Wood Prod. 76: 783–792, https://doi.org/10.1007/s00107-017-1247-y.Search in Google Scholar

Makino, R., Ohara, S., and Hashida, K. (2011). Radical scavenging characteristics of condensed tannins from barks of various tree species compared with quebracho wood tannin. Holzforschung 65: 651–657, https://doi.org/10.1515/hf.2011.086.Search in Google Scholar

Martin-Dupont, F., Gloagluen, V., Guilloton, M., Granet, R., and Kraucsz, P. (2007). Study of the chemical interaction between barks and heavy metal cations in the sorption process. J. Environ. Sci. Health Part A 41: 149–160, https://doi.org/10.1080/10934520500349250.Search in Google Scholar PubMed

Mazzoleni, V., Caldentey, P., and Silva, A. (1998). Phenolic compounds in cork used for production of wine stoppers as affected by storage and boiling of cork slabs. Am. J. Enol. Vitic. 49: 6–10.Search in Google Scholar

Meagher, L.P., Beecher, G.R., Flanagan, V.P., and Li, B.W. (1999). Isolation and characterization of the lignans, isolariciresinol and pinoresinol, in flax seed meal. J. Agric. Food Chem. 47: 3173–3180, https://doi.org/10.1021/jf981359y.Search in Google Scholar PubMed

Miranda, I., Gominho, J., Mirra, I., and Pereira, H. (2013). Fractioning and chemical characterization of barks of Betula pendula and Eucalyptus globulus. Ind. Crop. Prod. 41: 299–305, https://doi.org/10.1016/j.indcrop.2012.04.024.Search in Google Scholar

Neiva, D.M., Araújo, S., Gominho, J., Carneiro, A.C., and Pereira, H. (2018). An integrated characterization of Picea abies industrial bark regarding chemical composition, thermal properties and polar extracts activity. PLoS ONE 13: e0208270, https://doi.org/10.1371/journal.pone.0208270.Search in Google Scholar PubMed PubMed Central

Nunes, E., Quilhó, T., and Pereira, H. (1999). Anatomy and chemical composition of Pinus pinea L. bark. Ann. For. Sci. 56: 479–484, https://doi.org/10.1051/forest:19990604.10.1051/forest:19990604Search in Google Scholar

Nunes, E., Quilhó, T., and Pereira, H. (1996). Anatomy and chemical composition of Pinus pinaster bark. IAWA J. 17: 141–150, https://doi.org/10.1163/22941932-90001444.Search in Google Scholar

Pan, S., Pu, Y., Foston, M., and Ragauskas, A.J. (2013). Compositional characterization and pyrolysis of loblolly pine and Douglas-fir bark. BioEnergy Res. 6: 24–34, https://doi.org/10.1007/s12155-012-9223-1.Search in Google Scholar

Penalvo, J.L., Haajanen, K.M., Botting, N., and Adlercreutz, H. (2005). Quantification of lignans in food using isotope dilution gas chromatography/mass spectrometry. J. Agric. Food Chem. 53: 9342–9347, https://doi.org/10.1021/jf051488w.Search in Google Scholar PubMed

Percival, G.R. (1948). Utilization of Douglas fir bark. Faculty of the School of Forestry Oregon State College, Oregon.Search in Google Scholar

Pinto, P.C.R.O., Sousa, A.F., Silvestre, A.J.D., Neto, C.P., Gandini, A., Eckerman, C., and Holmbom, B. (2009). Quercus suber and Betula pendula outerbarks as renewable sources of oleochemicals: a comparative study. Ind. Crop. Prod. 29: 126–132, https://doi.org/10.1016/j.indcrop.2008.04.015.Search in Google Scholar

Roffael, E., Dix, B., and Okum, J. (2000). Use of spruce tannin as binder in particleboards and medium density fiberboards (MDF). Holz Roh. Werkst. 58: 301–305, https://doi.org/10.1007/s001070050432.Search in Google Scholar

Santos, S.A.O, Pinto, P.C.R.O., Silvestre, A.J.D., and Neto, C.P. (2010). Chemical composition and antioxidant activity of phenolic extracts of cork from Quercus suber L. Ind. Crops Prod. 31: 521–526, https://doi.org/10.1016/j.indcrop.2010.02.001.Search in Google Scholar

Santos, S.A.O, Villaverde, J.J., Sousa, A.F., Coelho, J., Neto, C.P., and Silvestre, A.J.D. (2013). Phenolic composition and antioxidant activity of industrial cork by-products. Ind. Crops Prod. 47: 262–269, https://doi.org/10.1016/j.indcrop.2013.03.015.Search in Google Scholar

Seki, K., Saito, N., and Aoyama, M. (1997). Removal of heavy metal ions from solutions by coniferous barks. Wood Sci. Technol. 31: 441–447, https://doi.org/10.1007/BF00702566.Search in Google Scholar

Sen, A., Miranda, I., Santos, S., Graça, J., and Pereira, H. (2010). The chemical composition of cork and phloem in the rhytidome of Quercus cerris bark. Ind. Crop. Prod. 31: 417–422, https://doi.org/10.1016/j.indcrop.2010.01.002.Search in Google Scholar

Sen, A., Miranda, I., Ferreira, J., Lourenço, A., and Pereira, H. (2018). Chemical composition and cellular structure of ponytail palm (Beaucarnea recurvata) cork. Ind. Crop. Prod. 124: 845–855, https://doi.org/10.1016/j.indcrop.2018.08.057.Search in Google Scholar

Sharma, O. and Bhat, T.N. (2009). DPPH antioxidant assay revisited. Food Chem. 113: 1202–1205, https://doi.org/10.1016/j.foodchem.2008.08.008.Search in Google Scholar

Sicilia, T., Niemeyer, H.B., Honig, D.M., and Metzler, M. (2003). Identification and stereochemical characterization of lignans in flaxseed and pumpkin seeds. J. Agric. Food Chem. 51: 1181–1188, https://doi.org/10.1021/jf0207979.Search in Google Scholar

Singleton, V.L. and Rossi, J.A. (1965). Colorimetry of total phenolics with phosphomolybdic-phosphotungstic acid reagents. Am. J. Enol. Vitic. 16: 144–158.Search in Google Scholar

Smeds, A.I., Eklund, P.C., Sjöholm, R.E., Willfor, S.M., Nishibe, S., and Deyama, T. (2007). Quantification of a broad spectrum of lignans in cereals, oilseeds, and nuts. J. Agric. Food Chem. 55: 1337–1346, https://doi.org/10.1021/jf0629134.Search in Google Scholar

Telysheva, G., Dizhbite, T., Bikovens, O., Ponomarenko, J., Janceva, S., and Krasilnikova, J. (2011). Structure and antioxidant activity of diarylheptanoids extracted from bark of grey alder (Alnus incana) and potential of biorefinery-based bark processing of European trees. Holzforschung 65: 623–629, https://doi.org/10.1515/hf.2011.096.Search in Google Scholar

Touati, R., Santos, S.A.O., Rocha, S.M., Belhhamek, K., and Silvestre, A.J.D. (2015). The potential of cork from Quercus suber L. grown in Algeria as a source of bioactive lipophilic and phenolic compounds. Ind. Crops Prod. 76: 936–945, https://doi.org/10.1016/j.indcrop.2015.07.074.Search in Google Scholar

Trivelato, P., Mayer, C., Barakat, A., Fulcrand, H., and Aouf, C. (2016). Douglas bark dry fractionation for polyphenols isolation: from forestry waste to added value products. Ind. Crops Prod. 86: 12–15, https://doi.org/10.1016/j.indcrop.2016.03.014.Search in Google Scholar

Willför, S.M., Hemming, J., Reunanen, M., and Holmbom, B.R. (2003a). Phenolic and lipophilic extractives in Scots pine knots and stemwood. Holzforschung 57: 359–372, https://doi.org/10.1515/HF.2003.054.Search in Google Scholar

Willför, S.M., Hemming, J., Reunanen, M., Eckerman, C., and Holmbom, B.R. (2003b). Lignans and lipophilic extractives in Norway spruce knots and stemwood. Holzforschung 57: 27–36, https://doi.org/10.1515/HF.2003.005.Search in Google Scholar

Yazaki, Y. and Collins, P.J. (1994). Wood adhesives from Pinus radiata bark. Holz als Roh Werkst. 52: 185–190, https://doi.org/10.1007/BF02615220.Search in Google Scholar

Zhishen, J., Mengcheng, T., and Jianming, W. (1999). The determination of flavonoid contents in mulberry and their scavenging effects on superoxide radicals. Food Chem. 64: 555–559, https://doi.org/10.1016/S0308-8146(98)00102-2.Search in Google Scholar

Received: 2020-04-13
Accepted: 2020-11-27
Published Online: 2021-01-07
Published in Print: 2021-07-27

© 2020 Walter de Gruyter GmbH, Berlin/Boston

Articles in the same Issue

  1. Frontmatter
  2. Original articles
  3. Wood identification of two anatomically similar Cupressaceae species based on two-dimensional microfibril angle mapping
  4. Treatment of wood with atmospheric plasma discharge: study of the treatment process, dynamic wettability and interactions with a waterborne coating
  5. Impact of hygrothermal treatment on the physical properties and chemical composition of Moso bamboo (Phyllostachys edulis)
  6. Inverse characterisation of gradient distribution of the modulus of bamboo using a four-point bending test
  7. Correlation between bacterial decay and chemical changes in waterlogged archaeological wood analysed by light microscopy and Py-GC/MS
  8. Artificial neural networks modelling based on visual analysis of coated cross laminated timber (CLT) to predict color change during outdoor exposure
  9. Wood-adhesive bond loaded in mode II: experimental and numerical analysis using elasto-plastic and fracture mechanics models
  10. Influences of liquefied lignin content on the properties of waterborne polyurethane prepared with different chain extenders
  11. Composition and antioxidant properties of extracts from Douglas fir bark
https://doi.org/10.1515/hf-2020-0097
Keywords for this article
antioxidant properties; bark; hydrophilic extracts; lipophilic extracts; Pseudotsuga menziesii

Articles in the same Issue

  1. Frontmatter
  2. Original articles
  3. Wood identification of two anatomically similar Cupressaceae species based on two-dimensional microfibril angle mapping
  4. Treatment of wood with atmospheric plasma discharge: study of the treatment process, dynamic wettability and interactions with a waterborne coating
  5. Impact of hygrothermal treatment on the physical properties and chemical composition of Moso bamboo (Phyllostachys edulis)
  6. Inverse characterisation of gradient distribution of the modulus of bamboo using a four-point bending test
  7. Correlation between bacterial decay and chemical changes in waterlogged archaeological wood analysed by light microscopy and Py-GC/MS
  8. Artificial neural networks modelling based on visual analysis of coated cross laminated timber (CLT) to predict color change during outdoor exposure
  9. Wood-adhesive bond loaded in mode II: experimental and numerical analysis using elasto-plastic and fracture mechanics models
  10. Influences of liquefied lignin content on the properties of waterborne polyurethane prepared with different chain extenders
  11. Composition and antioxidant properties of extracts from Douglas fir bark
Sign up now to receive a 20% welcome discount
Institutional Access
How does access work?
Have an idea on how to improve our website?
Please write us.
© 2025 De Gruyter Brill
Downloaded on 12.9.2025 from https://www.degruyterbrill.com/document/doi/10.1515/hf-2020-0097/html
Scroll to top button