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

SummaryA 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.

[1]  G. N. Richards,et al.  Chemical structures in a lignin-carbohydrate complex isolated from the bovine rumen , 1982 .

[2]  D. Goring,et al.  Structural studies on the chemical bonds between lignins and carbohydrates in spruce wood , 1980, Wood Science and Technology.

[3]  J. Joseleau,et al.  Characterization of structurally similar neutral and acidic tetrasaccharides obtained from the enzymic hydrolyzate of a 4-O-methyl-D-glucurono-D-xylan. , 1974, Carbohydrate research.

[4]  J. Azuma,et al.  Isolation and characterisation of lignin-carbohydrate complexes from the milled-wood lignin fraction of Pinus densiflora sieb. et zucc. , 1981 .

[5]  H. Mikawa,et al.  Studies on the Cooking Mechanism of Wood. XII. On the Nature of the weakly Acidic Group of Lignosulphonic Acid , 1955 .

[6]  J. Obst.  Frequency and alkali resistance of lignin-carbohydrate bonds in wood , 1982 .

[7]  J. Azuma,et al.  A NEW FERULOYLATED TRISACCHARIDE FROM BAGASSE , 1983 .

[8]  J. Merewether,et al.  Studies of a Lignin-Carbohydrate Complex. Pt. I. The Isolation of a Water Soluble Lignin-Carbohydrate Complex from Alkali Extraction of Eucalyptus obliqua , 2009 .

[9]  K. Tanaka,et al.  Reactions of guaiacylglycerol beta guaiacyl ether with several sugars. i. reaction of quinonemethide with D glucuronic acid , 1976 .

[10]  E. Fry.  Tri-O-acetyl-β-D-glucopyranurono-6,1-lactone , 1955 .

[11]  J. Galambos,et al.  The reaction of carbazole with carbohydrates. II. Effect of borate and sulfamate on the ultraviolet absorption of sugars. , 1967, Analytical biochemistry.

[12]  D. Fengel,et al.  Studies on the lignin of the bamboo species Phyllostachys makinoi Hay. , 1985, Wood Science and Technology.

[13]  R. Taylor,et al.  Stoichiometric depolymerization of polyuronides and glycosaminoglycuronans to monosaccharides following reduction of their carbodiimide-activated carboxyl groups. , 1972, Biochemistry.

[14]  J. Mccarthy,et al.  Lignin. XII.1The High Resolution Nuclear Magnetic Resonance Spectroscopy of Protons in Compounds Related to Lignin , 1964 .

[15]  R. Varma,et al.  A simple method for the detection and quantitative determination of hexuronic acids and pentoses. , 1974, Analytical biochemistry.

[16]  T. Koshijima,et al.  Molecular properties of lignin-carbohydrate complexes from beech (Fagus crenata) and pine (Pinus densiflora) woods , 1988, Wood Science and Technology.

[17]  G. N. Richards,et al.  Problems of Lactonisation in the analysis of uronic acids , 1968 .

[18]  I. Morrison,et al.  The degradation of isolated hemicelluloses and lignin-hemicellulose complexes by cell-free, rumen hemicellulases , 1982 .

[19]  J. Galambos,et al.  The reaction of carbazole with carbohydrates. I. Effect of borate and sulfamate on the carbazole color of sugars. , 1967, Analytical biochemistry.

[20]  R. Hartley.  Carbohydrate esters of ferulic acid as components of cell-walls of Lolium multiflorum☆ , 1973 .

[21]  T. E. Timell.  Isolation and Properties of an O-Acetyl-4-O-methylglucurono-xyloglycan from the Wood of White Birch (Betula papyrifera)1 , 1960 .

[22]  J. Mccarthy,et al.  Lignin. XIII.1 The High Resolution Nuclear Magnetic Resonance Spectroscopy of Protons in Acetylated Lignins , 1964 .

[23]  T. Iversen.  Lignin-carbohydrate bonds in a lignin-carbohydrate complex isolated from spruce , 1985, Wood Science and Technology.

[24]  S. Das,et al.  Lignin-xylan ester linkage in mesta fiber (Hibiscus cannabinus) , 1984 .

[25]  J. Joseleau,et al.  Glycosidic Bonds between Lignin and Carbohydrates , 1986 .

[26]  B. Kos̆iková,et al.  On the Properties of Benzyl Ether Bonds in the Lignin-Saccharidic Complex Isolated from Spruce , 1979 .