Skip to main content
Log in

Structural Differences Between Lignin Model Polymers Synthesized from Various Monomers

  • Original Paper
  • Published:
Journal of Polymers and the Environment Aims and scope Submit manuscript

Abstract

In a plant cell wall, lignin is synthesized from several monomeric precursors, combined in various ratios. The variation in monomer type and quantity enables multifunctional role of lignin in plants. Thus, it is important to know how different combinations of lignin monomers impact variability of bond types and local structural changes in the polymer. Lignin model polymers are a good model system for studies of relation between variations of the starting monomers and structural variations within the polymer. We synthesized lignin model polymers from three monomers, CF—based on coniferyl alcohol and ferulic acid in monomer proportions 5:1 and 10:1 (w/w), CP—based on coniferyl alcohol and p-coumaric acid in proportion 10:1 (w/w) and CA—based on pure coniferyl alcohol. We studied structural modifications in the obtained polymers, by combining fluorescence microscopy and spectroscopy, FT-IR and Raman spectroscopy, in parallel with determination of polymers’ molecular mass distribution. The differences in the low M w region of the distribution curves of the 10:1 polymers in comparison with the CA polymer may be connected with the increased content of C=C bonds and decreased content of condensed structures, as observed in FT-IR spectra and indicated by the analysis of fluorescence spectra. The 5:1 CF polymer contains a different type of structure in comparison with the 10:1 CF polymers, reflected in its simpler M w distribution, higher homogeneity of the fluorescence emitting structures and in the appearance of a new high-wavelength emission component. We propose that this component may originate from π-conjugated chains, which are longer in this polymer. The results are a contribution to the understanding of the involvement of structural variations of lignin polymers in the cell wall structural plasticity.

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
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Lewis NG, Yamamoto E (1990) Annu. Rev Plant Physiol Plant Mol Biol 41:455

    Article  CAS  Google Scholar 

  2. Whetten R, Sederoff R (1995) Plant Cell 7:1001

    Article  CAS  Google Scholar 

  3. Boerjan W, Ralph J, Baucher M (2003) Annu Rev Plant Biol 54:519

    Article  CAS  Google Scholar 

  4. Anterola AM, Lewis NG (2002) Phytochemistry 61:221

    Article  CAS  Google Scholar 

  5. Humphreys JM, Chapple C (2002) Curr Opin Plant Biol 5:224

    Article  CAS  Google Scholar 

  6. Can˜o-Delgado A, Penfield S, Smith C, Catley M, Bevan M (2003) Plant J 34:351

    Article  Google Scholar 

  7. Tronchet M, Balague C, Kroj T, Jouanin L, Roby D (2010) Mol Plant Pathol 11:83

    Article  CAS  Google Scholar 

  8. Magalh˜aes Silva Moural JC, Bonine CAV, de Oliveira Fernandes Viana J, Carnier Dornelas M, Mazzafera P (2010) J Integr Plant Biol 52:360

    Article  Google Scholar 

  9. Lewis NG, Newman J, Just G, Ripmeister J (1987) Macromolecules 20:1752

    Article  CAS  Google Scholar 

  10. Konschin H, Sundholm F, Sundholm G (1976) Fluorescence characteristics of lignin model compounds. Acta Chem Scand B 30:262

    Article  Google Scholar 

  11. Lang M, Stober F, Lichtenthaler HK (1991) Radiat Environ Biophys 30:333

    Article  CAS  Google Scholar 

  12. Lundquist K, Josefsson B, Nyquist G (1978) Holzforschung 32:27

    Article  CAS  Google Scholar 

  13. Tylli H, Forsskåhl I, Olkkonen C (1995) J Photochem Photobiol A Chem 87:181

    Article  CAS  Google Scholar 

  14. Radotić K, Kalauzi A, Djikanović D, Jeremić M, Leblanc RM, Cerović ZG (2006) J Photochem Photobiol B Biol 83:1

    Article  Google Scholar 

  15. Kalauzi A, Mutavdžić D, Đjikanović D, Radotić K, Jeremić M (2007) J Fluoresc 17:319

    Article  CAS  Google Scholar 

  16. Freudenberg K (1956) Angew Chem 68:84

    Article  CAS  Google Scholar 

  17. Wayman M, Obiaga TI (1974) Can J Chem 52:2102

    Article  CAS  Google Scholar 

  18. Siano DB, Metzler DE (1969) J Chem Phys 51:1856

    Article  CAS  Google Scholar 

  19. Djikanović D, Kalauzi A, Jeremić M, Mićić M, Radotić K (2007) Coll Surf B Biointerfaces 5(4):188

    Article  Google Scholar 

  20. Donaldson L, Radotić K, Kalauzi A, Djikanović D, Jeremić M (2010) J Struct Biol 169:106

    Article  Google Scholar 

  21. Levine I (1988) Physical chemistry. McGraw Hill Book Company, New York

    Google Scholar 

  22. Ralph J, Hatfield RD, Quideau S, Helm RF, Grabber JH, Jung HJ (1994) J Am Chem Soc 116:9448

    Article  CAS  Google Scholar 

  23. Menden B, Kohlhoff M, Moersch BM (2007) Phytochemistry 68:513–520

    Article  CAS  Google Scholar 

  24. Sun R, Sun XF, Wang SQ, Zhu W, Wang XY (2002) Ind Crop Prod 15:179

    Article  CAS  Google Scholar 

  25. Lam TB, Iliyama K, Stone BA (1992) Phytochemistry 31:2655

    Article  CAS  Google Scholar 

  26. Iiyama K, Lam TB, Stone BA (1994) Plant Physiol 104:315

    CAS  Google Scholar 

  27. Djikanović D, Kalauzi A, Jeremić M, Xu J, Mićić M, Whyte JD, Leblanc RM, Radotić K (2011) Coll Surf B Biointerface 91:41

    Article  Google Scholar 

  28. Weng J, Chapple C (2010) New Phytol 187:273

    Article  CAS  Google Scholar 

  29. Vanholme R, Demedts B, Morreel K, Ralph J, Boerjan W (2010) Plant Physiol 153:895

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the grants 173017 and 45022 from the Ministry of Education and Science of the Republic of Serbia.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ksenija Radotić.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Djikanović, D., Simonović, J., Savić, A. et al. Structural Differences Between Lignin Model Polymers Synthesized from Various Monomers. J Polym Environ 20, 607–617 (2012). https://doi.org/10.1007/s10924-012-0422-9

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10924-012-0422-9

Keywords

Navigation