Summary
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.
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References
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: 91–104
Azuma, J.; Takahashi, N.; Isaka, M.; Koshijima, T. 1985: Lignin-carbohydrate complexes extracted with aqueous dioxane from beech wood. Mokuzai Gakkaishi 31: 587–594
Blake, J. D.; Richards, G. N. 1968: Problems of lactonisation in the analysis of uronic acids. Carbohyd. Res. 8: 275–281
Brice, R. E.; Morrison, I. M. 1982: The degradation of isolated hemicelluloses and ligninhemicellulose complexes by cell-free, rumen hemicellulases. Carbohyd. Res. 101: 93–100
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: 217–224
Das, N. N.; Das, S. C.; Sarkar, A. K.; Mukherjee, A. K. 1984: Lignin-xylan ester linkage in mesta fiber. Carbohyd. Res. 129: 197–207
Eriksson, Ö.; Goring, D. A. I. 1980: Structural studies on the chemical bonds between lignins and carbohydrates in spruce wood. Wood Sci. Technol. 14: 267–279
Fengel, D.; Shao, X. 1985: Studies on the lignin of the bamboo species Phyllostachys makinoi Hay. Wood Sci. Technol. 19: 131–137
Fry, E. M. 1955: Tri-O-acetyl-β-d-glucopyranurono-6,1-lactone. J. Am. Chem. Soc. 77: 3915–3916
Galambos, J. T. 1967: The reaction of carbazole with carbohydrates. Anal. Biochem. 19: 119–132
Hartley, R. D. 1973: Carbohydrate esters of ferulic acid as components of cell-walls of Lolium multiflorum. Phytochemistry 12: 661–665
Iversen, T. 1985: Lignin-carbohydrate bonds in a lignin-carbohydrate complex isolated from spruce. Wood Sci. Technol. 19: 243–251
Joseleau, J.-P.; Gancet, C. 1981: Selective degradations of the lignin-carbohydrate complex from aspen wood. Svensk Papperstidn. 84: 123–127
Joseleau, J.-P.; Kesraoui, R. 1986: Glycosidic bonds between lignin and carbohydrates. Holzforschung 40: 163–168
Kato, A.; Azuma, J.; Koshijima, T. 1983: A new feruloylated trisaccharide from bagasse. Chem. Lett. 137–140
Koshijima, T. 1979: In: Nakano J. (Ed): Chemistry of lignin. pp. 42. Uni-koho press
Košiková, B.; Joniak, D.; Kosáková, L. 1979: On the properties of benzylether bonds in the lignin-saccharidic complex isolated from spruce. Holzforschung 33: 11–14
Lindberg, B.; Lönngren, J. 1978: Specific degradation of polysaccharides containing uronic acid residues. Methods in carbohyd. chem. 7: 142–148
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: 1186–1202
Merewether, J. W. T.; Samsuzzaman, L. A. M. 1972: Studies of a lignin-carbohydrate complex. Holzforschung 26: 11–18
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: 653–660
Neilson, M. J.; Richards, G. N. 1982: Chemical structures in a lignin-carbohydrate complex isolated from the bovine rumen. Carbohyd. Res. 104: 121–138
Obst, J. R. 1982: Frequency and alkali resistance of lignin-carbohydrate bonds in wood. Tappi 65: 109–112
Overberger, C. G.; Anselne, J.-P. 1963: A convenient synthesis of phenyldiazomethane. J. Org. Chem. 28: 592–593
Takahashi, N.; Koshijima, T. 1988: Molecular properties of lignin-carbohydrate complexes from beech (Fagus crenata) and pine (Pinus densiflora) woods. Wood Sci. Technol. 22: 177–189
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: 589–590
Taylor, R. L.; Conrad, M. E. 1972: Stoichiometric depolymerization of polyuronides and glycosaminoglycuronans to monosaccharides following reduction of their carbodiimideactivated carboxyl groups 11: 1383–1388
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: 5211–5215
Toda, H. 1960: Microanalysis of glucuronic acid and glacturonic acid. Sen-i Gakkaishi 16: 719–729
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: 268–273
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Takahashi, N., Koshijima, T. Ester linkages between lignin and glucuronoxylan in a lignin-carbohydrate complex from beech (Fagus crenata) wood. Wood Sci.Technol. 22, 231–241 (1988). https://doi.org/10.1007/BF00386018
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DOI: https://doi.org/10.1007/BF00386018