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Journal of Wood Science

Official Journal of the Japan Wood Research Society

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Characterization of lignin-carbohydrate linkages in the residual lignins isolated from chemical pulps of spruce (Picea abies) and beech wood (Fagus sylvatica)

Journal of Wood Science volume 53, pages 309–313 (2007)Cite this article

Abstract

To investigate the linkage types between carbohydrates and lignin, residual lignins were isolated from three different unbleached pulps [kraft, alkaline sulfite anthraquinone methanol (ASAM), and soda with anthraquinone (AQ) and methanol] of spruce and beech wood and then characterized by oxidation with 2,3-Dichloro-5,6-dicyanobenzoquinone and followed by Prehm’s methylation. In residual lignins, sugar moieties were bound to lignins via benzyl ether bonds. In particular, galactose and mannose are predominantly linked to lignin fragments in residual lignins of spruce wood, while xylose and galactose are favored in the formation of LC bonds in the residual lignins of beech wood. In the case of hexoses, primary hydroxyl groups (C6 position) preferentially take part in benzyl ether linkages. Hydroxyl groups in the C2 and C3 positions of xylose participate in LC bonds and a small portion of arabinose was notably connected to lignin via the C5 position. Approximately seven or eight sugars were connected in soda/AQ/methanol residual lignin per 100 C9 lignin units, while the frequencies of LC bonds in kraft and ASAM residual lignins were distinctively less at one to three sugars per 100 C9 lignin units.

References

  1. Björkman A (1957) Studies on finely divided wood. Part 3. Extraction of lignin-carbohydrate complexes with neutral solvents. Sven Papperstidn 60:243–251

    Google Scholar 

  2. Higuchi T (1985) Biosynthesis of lignin. In: Higuchi T (ed) Biosynthesis and biodegradation of wood components. Academic, Orlando, pp 141–160

    Chapter  Google Scholar 

  3. Watanabe T, Ohnishi J, Yamasaki Y, Kaizu S, Koshijima T (1989) Binding site analysis of the ether linkages between lignin and hemi-celluloses in lignin-carbohydrate complexes by DDQ-oxidation. Agric Biol Chem 53:2233–2252

    CAS  Google Scholar 

  4. Watanabe T (1989) Structural studies on the covalent bonds between lignin and carbohydrate in lignin-carbohydrate complexes by selective oxidation of the lignin with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. Wood Res 76:59–123

    CAS  Google Scholar 

  5. Joniak D, Kosikova B, Mlynar J (1987) Stability of p-hydroxy and p-methoxy benzyl ether lignin-saccharidic model compounds. Cell Chem Technol 21:121–127

    CAS  Google Scholar 

  6. Taneda H, Hosoya S, Nakano J, Chang HM (1987) Stability of ether type model compounds during chemical pulping processes. J Wood Chem Technol 7:117–118

    Google Scholar 

  7. Gierer J, Wännström S (1986) Formation of ether bonds between lignins and carbohydrates during alkaline pulping processes. Holzforschung 40:347–352

    Article  CAS  Google Scholar 

  8. Yamasaki T, Hosoya S, Chen CL, Gratzl JS, Chang HM (1981) Characterization of residual lignin in kraft pulp. Proceedings of 1st International Symposium on Wood Pulping Chemistry, June 9–12, Stockholm, Sweden, 2:34–42

  9. Minor JL (1986) Chemical linkage of polysaccharides to residual lignin in loblolly pine kraft pulps. J Wood Chem Technol 6:185–201

    Article  CAS  Google Scholar 

  10. Minor JL (1991) Location of lignin-bonded pectic polysaccharides. J Wood Chem Technol 11:159–169

    Article  CAS  Google Scholar 

  11. Hortling B, Turunen E, Sundquist J (1991) Isolation of residual lignin from enzymatically hydrolysed pulps by dissolution in aprotic (DMAC) and protic (alkali) solutions. Proceedings of 6th International Symposium on Wood Pulping Chemistry, April 30–May 4, Melbourne, Australia, 1:323–330

  12. Choi JW, Faix O, Meier D (2001) Characterization of residual lignins from chemical pulps of spruce (Picea abies L.) and beech (Fagus sylvatica L.) by analytical pyrolysis-gas chromatography/mass spectrometry. Holzforschung 55:185–192

    Article  CAS  Google Scholar 

  13. Prehm P (1980) Methylation of carbohydrates by methyl trifluoromethanesulfonate in tri-methyl phosphate. Carbohydr Res 78: 372–374

    Article  CAS  Google Scholar 

  14. Carpita NC, Shea EM (1990) Linkage structure of carbohydrates by gas chromatography-mass spectrometry (GC-MS) of partially methylated alditol acetates. In: Biermann CJ, McGinnis GD (eds) Analysis of carbohydrate by GLC and MS. CRC, Boca Raton, pp 157–216

  15. Schwager C (1996) Isolierung von Lignn-Kohlenhydrat-Komplexen und ihre charakterisierung durch enzymatischen und chemischen Abbau sowie Matrixunterschüzte Laserdesorptios-Massenspektrometrie. Dissertation, University of Oldenburg, Oldenburg, Germany

    Google Scholar 

  16. Iversen T, Westermark U (1986) Lignin-carbohydrate bonds in residual lignin isolated from pine kraft pulp. Holzforschung 40:19–22

    Article  CAS  Google Scholar 

  17. Tamminen T, Vuorinen T, Tenkanen M, Hausalo T, Hortling B (1995) Analysis of lignin and lignin-carbohydrate complexes isolated from black liquor. Proceedings of 8th International Symposium on Wood Pulping Chemistry, June 6–9, Helsinki, Finland, 2:297–302

  18. Timell TE (1967) Recent progress in the chemistry of wood hemicellulose. Wood Sci Technol 1:45–70

    Article  CAS  Google Scholar 

  19. Isogai A, Ishizu A, Nakano J (1987) Residual lignin in unbleached kraft pulp. Part 2. Analysis of unbleached kraft pulp by new permethylation method. J Wood Chem Technol 7:463–484

    Article  CAS  Google Scholar 

  20. Kosikova B, Ebringerova A (1994) Lignin-carbohydrate bonds in a residual soda spruce pulp. Wood Sci Technol 28:291–296

    Article  CAS  Google Scholar 

  21. Karlsson O, Westermark U (1996) Evidence for chemical bonds between lignin and cellulose in kraft pulps. J Pulp Pap Sci 22:397–401

    Google Scholar 

  22. Obst JR (1982) Frequency and alkali resistance of lignin-carbohydrate bonds in wood. TAPPI 65:109–112

    CAS  Google Scholar 

  23. Takahashi N, Koshijima T (1988) Ester linkages between lignin and glucuronoxylan in a lignin-carbohydrate complex from beech (Fagus crenata) wood. Wood Sci Technol 22:231–241

    Article  CAS  Google Scholar 

  24. Hosoya S, Taneda H, Chang HM (1989) Formation and reactions of ether-type lignin carbohydrate complex. Proceedings of 5th International Symposium on Wood Pulping Chemistry, May 22–25, Raleigh, NC, USA, 1:69–73

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Authors and Affiliations

  1. Division of Wood Chemistry and Microbiology, Korea Forest Research Institute, Seoul, 130-712, Republic of Korea

    Joon Weon Choi & Don-Ha Choi

  2. Institute of Wood Chemistry and Chemical Technology of Wood, Federal Research Center for Forestry and Forest Products (BFH), Hamburg, 21031, Germany

    Oskar Faix

Authors
  1. Joon Weon Choi
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  2. Don-Ha Choi
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  3. Oskar Faix
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Correspondence to Joon Weon Choi.

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The publication of this article was made possible by an Emachu Research Fund. The authors are grateful for the fund.

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Choi, J.W., Choi, DH. & Faix, O. Characterization of lignin-carbohydrate linkages in the residual lignins isolated from chemical pulps of spruce (Picea abies) and beech wood (Fagus sylvatica). J Wood Sci 53, 309–313 (2007). https://doi.org/10.1007/s10086-006-0860-x

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  • DOI: https://doi.org/10.1007/s10086-006-0860-x

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