Skip to main content

Chemical composition and cellular structure of corks from Quercus suber trees planted in Bulgaria and Turkey

Abstract

The chemical composition and cellular structure of corks from cork oak (Quercus suber) trees grown in Bulgaria and Turkey were studied for the first time to gain insight into the quality of cork from areas external to the species natural distribution. The cellular structural arrangement of Bulgarian and Turkish corks was similar to Portuguese cork, but chemical composition differed significantly. In general, Bulgarian and Turkish corks contained higher amount of ash and lignin and lower amount of extractives than Portuguese cork. Bulgarian cork contained less suberin and more polysaccharides than Turkish and Portuguese corks. The differences in the suberin/lignin ratio (1.4, 1.1 and 2.0 in corks from Bulgaria, Turkey and Portugal, respectively) suggest differences in mechanical behavior, namely in compression. Suberin composition was similar in all corks, but differences in relative proportion of families and compounds were present, indicating natural variation related to cork origin. Lipophilic extractives differed between corks: Betulinic acid was the main triterpene in Bulgarian cork, while friedelin dominated the lipophilic extractives in Portuguese and Turkish corks. A new lupane-type pentacyclic triterpene was found in Bulgarian and Turkish corks.

This is a preview of subscription content, access via your institution.

Fig. 1

References

  1. Blanch GP, Villen J, Herraiz M (1998) Rapid analysis of free erythrodiol and uvaol in olive oils by coupled reverse-phase liquid chromatography-Gas chromatography. J Agric Food Chem 46:1027–1030

    CAS  Article  Google Scholar 

  2. Castola V, Marongiu B, Bighelli A, Floris C, Laï A, Casanova J (2005) Extractives of cork (Quercus suber L.): chemical composition of dichloromethane and supercritical CO2 extracts. Ind Crop Prod 21:65–69

    CAS  Article  Google Scholar 

  3. De la Puerta R, Martinez-Dominguez E, Ruiz-Gutierrez V (2000) Effect of minor components of virgin olive oil on topical antiinflammatory assays. Z Naturforsch C 55:814–819

    Article  PubMed  Google Scholar 

  4. Domingues RMA, Sousa GDA, Silva CM, Freire CSR, Silvestre AJD, Neto CP (2011) High value triterpenic compounds from the outer barks of several Eucalyptus species cultivated in Brazil and in Portugal. Ind Crop Prod 33:158–164

    CAS  Article  Google Scholar 

  5. Eglinton G, Hunneman DH (1968) Gas chromatographic-mass spectrometric studies of long chain hydroxy acids-I: the constituent cutin acids of apple cuticle. Phytochemistry 7:313–322

    CAS  Article  Google Scholar 

  6. Ekman R (1983) The Suberin Monomers and Triterpenoids from the Outer Bark of Betula verrucosa Ehrh. Holzforschung 37:205–211

    CAS  Article  Google Scholar 

  7. Ferreira JPA, Miranda I, Gominho J, Pereira H (2015a) Selective fractioning of Pseudotsuga menziesii bark and chemical characterization in view of an integrated valorization. Ind Crop Prod 74:998–1007

    CAS  Article  Google Scholar 

  8. Ferreira JPA, Miranda I, Gominho J, Pereira H (2015b) Chemical characterization of cork and phloem from Douglas fir outer bark. Holzforschung 70:475–483

    Google Scholar 

  9. Graça J, Pereira H (1997) Cork suberin: a glyceryl-based polyester. Holzforschung 51:225–234

    Article  Google Scholar 

  10. Graça J, Pereira H (2000) Methanolysis of bark suberins: analysis of glycerol and acid monomers. Phytochem Anal 11:45–51

    Article  Google Scholar 

  11. Jäger S, Laszczyk MN, Scheffler A (2008) A preliminary pharmacokinetic study of betulin, the main pentacyclic triterpene from extract of outer bark of birch (Betulae alba cortex). Molecules 13:3224–3235

    Article  PubMed  Google Scholar 

  12. Juan ME, Wenzel U, Daniel H, Planas JM (2008) Resveratrol induces apoptosis through ROS-dependent mitochondria pathway in HT-29 human colorectal carcinoma cells. J Agric Food Chem 56:4813–4818

    CAS  Article  PubMed  Google Scholar 

  13. Kayacık H, ve Eliçin G (1965) Bahçeköy’de Orman Fakültesi Tatbikat Sahasında Mantar Meşesi (Quercus suber L.) Denemesinden Bugüne Kadar Elde Edilen Sonuçlar. İ.Ü. Orman Fakültesi Dergisi, Seri A, 15:23–31 English edition: Results of the establishment of cork oak (Q. suber L.) plantations in the experimental field of Faculty of Forestry, Bahcekoy, Istanbul. J Fac For Istanbul Univ A, 15:23–31

  14. Knapp DR (1979) Handbook of Analytical Derivatization Reactions. John Wiley & Sons, New York

    Google Scholar 

  15. Kolattukudy P, Agrawal V (1974) Structure and composition of aliphatic constituents of potato tuber skin (suberin). Lipids 9:682–691

    CAS  Article  Google Scholar 

  16. Kozlowski TT, Pallardy SG (1997) Growth control in woody plants. Academic Press, San Diego

    Google Scholar 

  17. Marques AV, Rencoret J, Gutiérrez A, del Rio JC, Pereira H (2015) Ferulates and lignin structural composition in cork. Holzforschung. doi:10.1515/hf-2015-0014

    Google Scholar 

  18. Marquez-Martin A, De la Puerta R, Frenandez-Arche A, Ruiz-Gutierrez V (2006) Supressive effect of maslinic acid from pomace olive oil on oxidative stress and cytokine production in stimulated murine macrophages. Free Radic Res 40:295–302

    CAS  Article  PubMed  Google Scholar 

  19. Martín R, Ibeas E, Carvalho-Tavares J, Hernández M, Ruiz-Gutierrez V, Nieto ML (2009) Natural triterpenic diols promote apoptosis in astrocytoma cells through ROS-mediated mitochondrial depolarization and JNK activation. PLoS One 4:e5975

    Article  PubMed  PubMed Central  Google Scholar 

  20. Miranda I, Gominho J, Pereira H (2013) Cellular structure and chemical composition of cork from the Chinese cork oak (Quercus variabilis). J Wood Sci 59:1–9

    CAS  Article  Google Scholar 

  21. Moure A, Cruz JM, Franco D, Domínguez JM, Sineiro F, Domínguez H, Núñez MJ, Parajó JC (2001) Natural antioxidants from residual sources. Food Chem 72:145–171

    CAS  Article  Google Scholar 

  22. Neyisçi T, Yesilkaya Y, Usta Z (1987) Akdeniz bolgesinde Mantar Mesesi (Quercus suber L.) yetistirilmesi olaklarinin arastirilmasi (Studies on the introduction of cork oak (Quercus suber L.) to the Mediterranean region of Turkey). Ormancilik Arastirma Enstitusu Yayinlari, Teknik bulten serisi no 193 (in Turkish) English edition: Cork oak in the Mediterranean region (Quercus suber L.) cultivated the Investigation of Colak (Studies on the introduction of cork oak (Quercus suber L.) to the Mediterranean region of Turkey) Forest Research Institute Publications, Technical bulten Series No 193

  23. Oliveira V, Rosa ME, Pereira H (2014) Variability of the compression properties of cork. Wood Sci Technol 48:937–948

    CAS  Article  Google Scholar 

  24. Olivella MA, del Rio JC (2011) Suberin composition from different bark layers of Quercus suber L. by Py-GC/MS in the presence of tetramethylammoniumhydroxide (TMAH). Bioresources 6:4936–4941

    Google Scholar 

  25. Pereira H (1988a) Structure and chemical composition of cork from Calotropis procera (AIT.) R. BR. IAWA J 9:53–58

    Article  Google Scholar 

  26. Pereira H (1988b) Chemical composition and variability of cork from Quercus suber L. Wood Sci Technol 22:211–218

    CAS  Article  Google Scholar 

  27. Pereira H (1992) The thermochemical degradation of cork. Wood Sci Technol 26:259–269

    CAS  Article  Google Scholar 

  28. Pereira H (2007) Cork: biology, production and uses. Elsevier Press, London

    Google Scholar 

  29. Pereira H (2013) Variability of the chemical composition of cork. BioResources 8:2246–2256

    CAS  Google Scholar 

  30. Pereira H (2015) The rationale behind cork properties: a review of structure and chemistry. BioResources 10:6207–6229

    CAS  Article  Google Scholar 

  31. Pereira H, Rosa ME, Fortes MA (1987) The cellular structure of cork from Quercus suber L. IAWA Bull 8:213–218

    Article  Google Scholar 

  32. Petrov M (1994) The cork oak and its propagation in Bulgaria. BAS Publisher Marin Drinov, Sofia, pp 1–210 (in Bulgarian, English summary)

    Google Scholar 

  33. Petrov M, Genov K (2004) 50 Years of cork oak (Quercus suber L.) in Bulgaria. Nauka za Gorata (For Sci) 3:93–101

    Google Scholar 

  34. Rios P, Cabral V, Santos S, Mori F, Graça J (2014) The chemistry of Kielmeyera coriacea outer bark: a potential source for cork. Eur J Wood Prod 72:509–519

    CAS  Article  Google Scholar 

  35. Rodriguez-Rodriguez R, Simonsen U (2012) Natural triterpenoids from olive oil: potential activities against cancer. In: Diederich M, Noworyta K (eds) Natural compounds as inducers of cell death. Springer, New York, pp 447–461

    Chapter  Google Scholar 

  36. Sen A, Miranda I, Santos S, Graça J, Pereira H (2010) The chemical composition of cork and phloem in the rhytidome of Quercus cerris bark. Ind Crop Prod 31:417–422

    CAS  Article  Google Scholar 

  37. Sen A, van den Bulcke J, Defoirdt N, van Acker JV, Pereira H (2014) Thermal behavior of cork and cork components. Thermochim Acta 582:94–100

    CAS  Article  Google Scholar 

  38. Sen A, Melo MMR, Silvestre AJD, Pereira H, Silva CM (2015) Prospective pathway for a green and enhanced friedelin production through supercritical fluid extraction of Quercus cerris cork. J Supercrit Fluids 97:247–255

    CAS  Article  Google Scholar 

  39. Sousa AF, Pinto PCRO, Silvestre AJD, Neto CP (2006) Triterpenic and other lipophilic compounds from industrial cork byproducts. J Agric Food Chem 54:6888–6893

    CAS  Article  PubMed  Google Scholar 

  40. TAPPI 13 wd-74 (TAPPI 13 os-54 combined with TAPPI 222 om-11). Lignin in wood. http://www.tappi.org/content/pdf/standards/numeric_index_tms.pdf. Accessed 21 Apr 2016

  41. TAPPI 249 cm-09. Carbohydrate composition of extractive-free wood and wood pulp by gas-liquid chromatography. http://www.tappi.org/content/pdf/standards/numeric_index_tms.pdf. Accessed 22 Mar 2016

  42. TAPPI T 15 os-58. Ash in wood. http://www.tappi.org/content/pdf/standards/numeric_index_tms.pdf. Accessed 4 Apr 2016

  43. Wandji J, Tillequin F, Mulholland DA, Wansi JD, Fomum TZ, Fuendjiep V, Libot F, Tsabang N (2002) Fatty acid esters of triterpenoids and steroid glycosides from Gambeya Africana. Planta Med 68:822–826

    CAS  Article  PubMed  Google Scholar 

Download references

Acknowledgments

The first author acknowledges a postdoctoral fellowship from the FCT (Fundação para a Ciência e a Tecnologia) Portugal. Centro de Estudos Florestais (CEF) is a research unit supported by the national funding of FCT (PEst-OE/AGR/UI0239/2014). Thanks are due to Dens and Pavlo for their help in the samplings in Bulgaria.

Author information

Affiliations

Authors

Corresponding author

Correspondence to Joana Ferreira.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Sen, A., Zhianski, M., Glushkova, M. et al. Chemical composition and cellular structure of corks from Quercus suber trees planted in Bulgaria and Turkey. Wood Sci Technol 50, 1261–1276 (2016). https://doi.org/10.1007/s00226-016-0836-y

Download citation

Keywords

  • Betulinic Acid
  • Suberin
  • Electron Impact Mass Spectrum
  • Lipophilic Extractive
  • Maslinic Acid