Wood Science and Technology

, Volume 22, Issue 3, pp 231–241 | Cite as

Ester linkages between lignin and glucuronoxylan in a lignin-carbohydrate complex from beech (Fagus crenata) wood

  • N. Takahashi
  • T. Koshijima


A water-soluble lignin-carbohydrate complex (LCC) isolated from beech (Fagus crenata) MWL was investigated. Results from gelfiltration chromatography and the infrared spectrum of the LCC treated with alkali under mild conditions indicated that the LCC contained alkali-labile bonds. Decrease of uronic acid content and the detection of 4-O-methylglucose in the sodium borohydride-reduced LCC suggested the presence of an ester linkage between lignin and glucuronic acid in the glucuronoxylan. Conductometric titration also indicated the existence of glucuronic acid ester linked to lignin. From these results, it is concluded that the LCC contained an ester linkage between lignin and glucuronoxylan and that about one-third of the glucuronic acid present in the LCC was involved in this ester linkage.


Sodium Ester Chromatography Lignin Titration 
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  1. Azuma, J.; Takahashi, N.; Koshijima, T. 1981: Isolation and characterization of lignincarbohydrate complexes from the milled wood lignin fraction of Pinus densiflora. Sieb. et Zucc. Carbohyd. Res. 93: 91–104Google Scholar
  2. Azuma, J.; Takahashi, N.; Isaka, M.; Koshijima, T. 1985: Lignin-carbohydrate complexes extracted with aqueous dioxane from beech wood. Mokuzai Gakkaishi 31: 587–594Google Scholar
  3. Blake, J. D.; Richards, G. N. 1968: Problems of lactonisation in the analysis of uronic acids. Carbohyd. Res. 8: 275–281Google Scholar
  4. Brice, R. E.; Morrison, I. M. 1982: The degradation of isolated hemicelluloses and ligninhemicellulose complexes by cell-free, rumen hemicellulases. Carbohyd. Res. 101: 93–100Google Scholar
  5. Comtat, J.; Joseleau, J.-P.; Bosso, C.; Barnoud, F. 1974: Characterisation of structurally similar neutral and acidic tetrasaccharides obtained from the enzymic hydrolyzate of a 4-O-methyl-d-glucurono-d-xylan. Carbohyd. Res. 38: 217–224Google Scholar
  6. Das, N. N.; Das, S. C.; Sarkar, A. K.; Mukherjee, A. K. 1984: Lignin-xylan ester linkage in mesta fiber. Carbohyd. Res. 129: 197–207Google Scholar
  7. Eriksson, Ö.; Goring, D. A. I. 1980: Structural studies on the chemical bonds between lignins and carbohydrates in spruce wood. Wood Sci. Technol. 14: 267–279Google Scholar
  8. Fengel, D.; Shao, X. 1985: Studies on the lignin of the bamboo species Phyllostachys makinoi Hay. Wood Sci. Technol. 19: 131–137Google Scholar
  9. Fry, E. M. 1955: Tri-O-acetyl-β-d-glucopyranurono-6,1-lactone. J. Am. Chem. Soc. 77: 3915–3916Google Scholar
  10. Galambos, J. T. 1967: The reaction of carbazole with carbohydrates. Anal. Biochem. 19: 119–132Google Scholar
  11. Hartley, R. D. 1973: Carbohydrate esters of ferulic acid as components of cell-walls of Lolium multiflorum. Phytochemistry 12: 661–665Google Scholar
  12. Iversen, T. 1985: Lignin-carbohydrate bonds in a lignin-carbohydrate complex isolated from spruce. Wood Sci. Technol. 19: 243–251Google Scholar
  13. Joseleau, J.-P.; Gancet, C. 1981: Selective degradations of the lignin-carbohydrate complex from aspen wood. Svensk Papperstidn. 84: 123–127Google Scholar
  14. Joseleau, J.-P.; Kesraoui, R. 1986: Glycosidic bonds between lignin and carbohydrates. Holzforschung 40: 163–168Google Scholar
  15. Kato, A.; Azuma, J.; Koshijima, T. 1983: A new feruloylated trisaccharide from bagasse. Chem. Lett. 137–140Google Scholar
  16. Koshijima, T. 1979: In: Nakano J. (Ed): Chemistry of lignin. pp. 42. Uni-koho pressGoogle Scholar
  17. Košiková, B.; Joniak, D.; Kosáková, L. 1979: On the properties of benzylether bonds in the lignin-saccharidic complex isolated from spruce. Holzforschung 33: 11–14Google Scholar
  18. Lindberg, B.; Lönngren, J. 1978: Specific degradation of polysaccharides containing uronic acid residues. Methods in carbohyd. chem. 7: 142–148Google Scholar
  19. Ludwig, C. H.; Nist, B. J.; McCarthy, J. L. 1964: Magnetic resonance of protons in lignin-related compounds and acetylated lignins. J. Am. Chem. Soc. 86: 1186–1202Google Scholar
  20. Merewether, J. W. T.; Samsuzzaman, L. A. M. 1972: Studies of a lignin-carbohydrate complex. Holzforschung 26: 11–18Google Scholar
  21. Mikawa, H.; Sato, K.; Takasaki, C.; Ebisawa, K. 1955: Studies on the cooking mechanism of wood. XII. On the nature of the weakly acidic group of lignosulphonic acid. Bull. Chem. Soc. Japan 28: 653–660Google Scholar
  22. Neilson, M. J.; Richards, G. N. 1982: Chemical structures in a lignin-carbohydrate complex isolated from the bovine rumen. Carbohyd. Res. 104: 121–138Google Scholar
  23. Obst, J. R. 1982: Frequency and alkali resistance of lignin-carbohydrate bonds in wood. Tappi 65: 109–112Google Scholar
  24. Overberger, C. G.; Anselne, J.-P. 1963: A convenient synthesis of phenyldiazomethane. J. Org. Chem. 28: 592–593Google Scholar
  25. Takahashi, N.; Koshijima, T. 1988: Molecular properties of lignin-carbohydrate complexes from beech (Fagus crenata) and pine (Pinus densiflora) woods. Wood Sci. Technol. 22: 177–189Google Scholar
  26. Tanaka, K.; Nakatsubo, F.; Higuchi, T. 1976: Reactions of guaiacylglycerol-β-guaiacyl ether with several sugars. I. Reaction of quinonemethide with d-glucuronic acid. 22: 589–590Google Scholar
  27. Taylor, R. L.; Conrad, M. E. 1972: Stoichiometric depolymerization of polyuronides and glycosaminoglycuronans to monosaccharides following reduction of their carbodiimideactivated carboxyl groups 11: 1383–1388Google Scholar
  28. Timell, T. E. 1960: Isolation and properties of an O-acetyl-4-O-methylglucurono-xyloglycan from the wood of white birch. J. Am. Chem. Soc. 82: 5211–5215Google Scholar
  29. Toda, H. 1960: Microanalysis of glucuronic acid and glacturonic acid. Sen-i Gakkaishi 16: 719–729Google Scholar
  30. Wardi, A. H.; Allen, W. S.; Varma, R. 1974: A simple method for the detection and quantitative determination of hexuronic acids and pentoses. Anal. Biochem. 57: 268–273Google Scholar

Copyright information

© Springer-Verlag 1988

Authors and Affiliations

  • N. Takahashi
    • 1
  • T. Koshijima
    • 1
  1. 1.Research Section of Wood Chemistry Wood research InstituteKyoto UniversityKyotoJapan

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