Fractionation and characterization of lignin-carbohydrate complexes (LCCs) of Eucalyptus globulus in residues left after MWL isolation. Part II: Analyses of xylan-lignin fraction (X-L)
Abstract
The residual wood meal left after milled wood lignin (MWL) isolation [milled wood residue (MWR)] of 5-year-old Eucalyptus globulus was fractionated to afford a xylan-lignin fraction (X-L) in 2.9% yield (based on MWR) by the method reported previously. X-L was further fractionated with the lignin solvent 1,4-dioxane/water (9:1, v/v) to give a soluble fraction (XL-F1; 24.0%) and an insoluble fraction (XL-F1-residue; 74.6%; both yields based on X-L). XL-F1-residue was further extracted with the good xylan solvent dimethyl sulfoxide and the soluble fraction was termed XL-F2 (43.0%; based on the XL-F1-residue). XL-F1 was mainly composed of lignin with a small amount of xylan and it is similar to purified MWL, whereas XL-F2 was mainly composed of xylan with some amount of lignin and it is similar to a fraction that was prepared by the extraction of crude MWL with acetic acid [lignin-carbohydrate complex (LCC)-AcOH]. The two-dimensional heteronuclear single quantum coherence nuclear magnetic resonance spectra of XL-F1 and XL-F2 were interpreted that the former has α-ether-type lignin-carbohydrate (LC) linkages and the latter might have LC linkages of the phenyl glycoside type, which are different from those in LCC-AcOH.
The authors gratefully acknowledge Oji Paper for the supply of xylanase.
References
Ando, D., Takano, T., Nakatsubo, F. (2012) Multi-steps degradation method for β-O-4 linkage in lignins: γ-TTSA method. Part 1: Reaction of non-phenolic dimeric β-O-4 model compounds. Holzforschung 66:331–339.10.1515/hf.2011.068Search in Google Scholar
Azuma, J., Takahashi, N., Koshijima, T. (1981) Isolation and characterization of lignin-carbohydrate complexes from the milled-wood lignin fraction of Pinus-densiflora Sieb. et Zucc. Carbohydr. Res. 93:91–104.Search in Google Scholar
Balakshin, M.Y., Capanema, E.A., Chang, H.M. (2007) MWL fraction with a high concentration of lignin-carbohydrate linkages: isolation and 2D NMR spectroscopic analysis. Holzforschung 61:1–7.10.1515/HF.2007.001Search in Google Scholar
Balakshin, M.Y., Capanema, E.A., Chang, H. (2008) Recent advances in the isolation and analysis of lignins and lignin-carbohydrate complexes. In: Characterization of Lignocellulosic Materials. Ed. Hu, T.Q. Blackwell Publishing Ltd., Oxford, UK. pp. 148–170.10.1002/9781444305425.ch9Search in Google Scholar
Balakshin, M., Capanema, E., Gracz, H., Chang, H., Jameel, H. (2011) Quantification of lignin – carbohydrate linkages with high-resolution NMR spectroscopy. Planta 233:1097–1110.10.1007/s00425-011-1359-2Search in Google Scholar PubMed
Barakat, A., Winter, H., Rondeau-Mouro, C., Saake, B., Chabbert, B., Cathala, B. (2007) Studies of xylan interactions and cross-linking to synthetic lignins formed by bulk and end-wise polymerization: a model study of lignin carbohydrate complex formation. Planta 226:267–281.10.1007/s00425-007-0479-1Search in Google Scholar PubMed
Björkman, A. (1956) Studies on finely divided wood. Part I. Extraction of lignin with neutral solvents. Svensk Papperstidn. 59:477–485.Search in Google Scholar
Borchardt, L.G., Piper, C.V. (1970) Gas-chromatographic method for carbohydrates as alditol-acetates. Tappi 53:257–260.Search in Google Scholar
Evtuguin, D.V., Tomas, J.L., Silva, A.M.S., Neto, C.P. (2003) Characterization of an acetylated heteroxylan from Eucalyptus globulus Labill. Carbohydr. Res. 338:597–604.Search in Google Scholar
Furuno, H., Takano, T., Hirosawa, S., Kamitakahara, H., Nakatsubo, F. (2006) Chemical structure elucidation of total lignins in woods. Part II: Analysis of a fraction of residual wood left after MWL isolation and solubilized in lithium chloride/N,N-dimethylacetamide. Holzforschung 60:653–658.10.1515/HF.2006.110Search in Google Scholar
Fujimoto, A., Matsumoto, Y., Meshitsuka, G., Chang, H-m. (2005) Quantitative evaluation of milling effects on lignin structure during the isolation process of milled wood lignin. J. Wood Sci. 51:89–91.10.1007/s10086-004-0682-7Search in Google Scholar
Galland, S., Mora, N., Abert-Vian, M., Rakotomanomana, N., Dangles, O. (2007) Chemical synthesis of hydroxycinnamic acid glucosides and evaluation of their ability to stabilize natural colors via anthocyanin copigmentation. J. Agric. Food Chem. 55:7573–7579.10.1021/jf071205vSearch in Google Scholar PubMed
Henriksson, G., Lawoko, M., Martin, M.E.E., Gellerstedt, G. (2007) Lignin-carbohydrate network in wood and pulps: a determinant for reactivity. Holzforschung 61:668–674.10.1515/HF.2007.097Search in Google Scholar
Hirosawa, S., Katahira, R., Nakatsubo, F. (2002) Chemical structural elucidation of total lignins in woods I: fractionation of the lignin in residual wood meal after extraction of milled wood lignin. J. Wood Sci. 48:46–50.10.1007/BF00766237Search in Google Scholar
Hu, Z., Yeh, T.F., Chang, H-M., Matsumoto, Y., Kadla, J.F. (2006) Elucidation of the structure of cellulolitic enzyme lignin. Holzforschung 60:389–397.10.1515/HF.2006.061Search in Google Scholar
Ibarra, D., Chavez, M.I., Rencoret, J., del Rio, J.C., Gutierrez, A., Romero, J., Camarero, S., Martinez, M.J., Jimenez-Barbero, J., Martinez, A.T. (2007) Structural modification of eucalypt pulp lignin in a totally chlorine-free bleaching sequence including a laccase-mediator stage. Holzforschung 61:634–646.10.1515/HF.2007.096Search in Google Scholar
Iiyama, K., Wallis, A.F.A. (1988) An improved acetyl bromide procedure for determining lignin in woods and wood pulps. Wood Sci. Technol. 22:271–280.Search in Google Scholar
Imamura, T., Watanabe, T., Kuwahara, M., Koshijima, T. (1994) Ester linkages between lignin and glucuronic acid in lignin-carbohydrate complexes from Fagus crenata. Phytochemistry 37:1165–1173.10.1016/S0031-9422(00)89551-5Search in Google Scholar
Karlsson, O., Pettersson, B., Westermark, U. (2001) The use of cellulase and hemicellulose to study lignin-cellulose as well as lignin-hemicellulose bonds in kraft pulps. J. Pulp Pap Sci. 27:196–201.Search in Google Scholar
Karlsson, O., Ikeda, T., Kishimoto, T., Magara, K., Matsumoto, Y., Hosoya, S. (2004) Isolation of lignin-carbohydrate bonds in wood. Model experiments and preliminary application to pine wood. J. Wood Sci. 50:142–150.10.1007/s10086-003-0542-xSearch in Google Scholar
Katahira, R., Nakatsubo, F. (2001) Determination of nitrobenzene oxidation products by GC and 1H-NMR spectroscopy using 5-iodovanillin as a new internal standard. J. Wood Sci. 47:378–382.10.1007/BF00766789Search in Google Scholar
Katahira, R., Ujihara, M., Nakatsubo, F. (2003) A novel selective cleavage method for β-O-4 substructures in lignins named TIZ method. I. Degradation of guaiacyl and syringyl models. J. Wood Chem. Technol. 23:71–87.Search in Google Scholar
Kim, H., Ralph, J. (2010) Solution-state 2D NMR of ball-milled plant cell wall gels in DMSO-d(6)/pyridine-d(5). Org. Biomol. Chem. 8:576–591.Search in Google Scholar
Kishimoto, T. (2009) Synthesis of lignin model compounds and their application to wood research. Mokuzai Gakkaishi 55:187–197.10.2488/jwrs.55.187Search in Google Scholar
Kishimoto, T., Ikeda, T., Karlsson, O., Magara, K., Hosoya, S. (2002) Reactivity of secondary hydroxyl groups in methyl beta-D-xylopyranoside toward a beta-O-4-type quinone methide. J Wood Sci. 48:32–37.10.1007/BF00766235Search in Google Scholar
Koshijima, T., Watanabe, T. (2003) Analysis of native bonds between lignin and carbohydrate by specific chemical reactions. In: Association between Lignin and Carbohydrate in Wood and Other Plant Tissues. Ed. Timell, T.E. Springer, Berlin. pp. 91–130.Search in Google Scholar
Lawoko, M., van Heiningen, A.R.P. (2011) Fractionation and characterization of completely dissolved ball milled hardwood. J. Wood Chem. Technol. 31:183–203.Search in Google Scholar
Lawoko, M., Henriksson, G., Gellerstedt, G. (2005) Structural differences between the lignin-carbohydrate complexes present in wood and in chemical pulps. Biomacromolecules 6:3467–3473.10.1021/bm058014qSearch in Google Scholar PubMed
Lawoko, M., Henriksson, G., Gellerstedt, G. (2006) Characterization of lignin-carbohydrate complexes (LCCs) of spruce wood (Picea abies L.) isolated with two methods. Holzforschung 60:156–161.10.1515/HF.2006.025Search in Google Scholar
Li, K., Helm, R.F. (1995) Synthesis and rearrangement reactions of ester-linked lignin-carbohydrate model compounds. J. Agric. Food Chem. 43:2098–2103.10.1021/jf00056a026Search in Google Scholar
Li, J., Martin-Sampedro, R., Pedrazzi, C., Gellerstedt, G. (2011) Fractionation and characterization of lignin-carbohydrate complexes (LCCs) from Eucalyptus fibers. Holzforschung 65:43–50.10.1515/hf.2011.013Search in Google Scholar
Lu, F.C., Ralph, J. (2003) Non-degradative dissolution and acetylation of ball-milled plant cell walls: high-resolution solution-state NMR. Plant J. 35:535–544.10.1046/j.1365-313X.2003.01817.xSearch in Google Scholar
Mazur, M., Hope-Ross, K., Kadla, J.F., Sederoff, R., Chang, H.M. (2007) Synthesis of hydroxyphenylpropanoid beta-D-glucosides. J Wood Chem. Technol. 27:1–8.Search in Google Scholar
Miyagawa, Y., Kamitakahara, H., Takano, T., Nakatsubo, F. (2012) Fractionation and characterization of lignin carbohydrate complexes (LCCs) of Eucalyptus globulus in residues left after MWL isolation. Part I: Analysis of hemicellulose-lignin fraction (HC-L). Holzforschung 66:459–465.10.1515/hf.2011.177Search in Google Scholar
Rencoret, J., Marques, G., Gutierrez, A., Ibarra, D., Li, J., Gellerstedt, G., Santos, J.I., Jimenez-Barbero, J., Martinez, A.T., del Rio, J.C. (2008) Structural characterization of milled wood lignins from different eucalypt species. Holzforschung 62:514–526.10.1515/HF.2008.096Search in Google Scholar
Rencoret, J., Gutierrez, A., Nieto, L., Jimenez-Barbero, J., Faulds, C.B., Kim, H., Ralph, J., Martinez, A.T., del Rio, J.C. (2011) Lignin composition and structure in young versus adult Eucalyptus globulus plants. Plant Physiol. 155: 667–682.10.1104/pp.110.167254Search in Google Scholar
Teleman, A., Lundqvist, J., Tjerneld, F., Stalbrand, H., Dahlman, O. (2000) Characterization of acetylated 4-O-methylglucuronoxylan isolated from aspen employing 1H and 13C NMR spectroscopy. Carbohydr. Res. 329:807–815.Search in Google Scholar
Teleman, A., Tenkanen, M., Jacobs, A., Dahlman, O. (2002) Characterization of O-acetyl-(4-O-methylglucurono)xylan isolated from birch and beech. Carbohydr Res. 337:373–377.10.1016/S0008-6215(01)00327-5Search in Google Scholar
Terashima, N., Ralph, S.A., Landucci, L.L. (1996) New facile syntheses of monolignol glucosides; p-glucocoumaryl alcohol, coniferin, and syringin. Holzforschung 50:151–155.Search in Google Scholar
Tokimatsu, T., Umezawa, T., Shimada, M. (1996) Synthesis of four diastereomeric lignin carbohydrate complexes (LCC) model compounds composed of a β-O-4 lignin model linked to methyl β-D-glucoside. Holzforschung 50:156–160.10.1515/hfsg.1996.50.2.156Search in Google Scholar
Toikka, M., Brunow, G. (1999) Lignin-carbohydrate model compounds. Reactivity of methyl 3-O-(alpha-L-arabinofuranosyl)-beta-D-xylopyranoside and methyl beta-D-xylopyranoside towards a beta-O-4-quinone methide. J. Chem. Soc. Perkin Trans. 1:1877–1883.10.1039/a900434cSearch in Google Scholar
Toikka, M., Sipila, J., Teleman, A., Brunow, G. (1998) Lignin-carbohydrate model compounds. Formation of lignin-methyl arabinoside and lignin-methyl galactoside benzyl ethers via quinone methide intermediates. J. Chem Soc. Perkin Trans. 1:3813–3818.10.1039/a805627gSearch in Google Scholar
Villaverde, J.J., Li, J.B., Ek, M., Ligero, P., de Vega, A. (2009) Native lignin structure of Miscanthus x giganteus and its changes during acetic and formic acid fractionation. J. Agric. Food. Chem. 57:6262–6270.Search in Google Scholar
Watanabe, T., Ohnishi, J., Yamasaki, Y., Kaizu, S., Koshijima, T. (1989) Binding-site analysis of the ether linkages between lignin and hemicelluloses in lignin-carbohydrate complexes by DDQ-oxidation. Agric. Biol. Chem. 53:2233–2252.Search in Google Scholar
Westbye, P., Köhnke, T., Gatenholm, P. (2008) Fractionation and characterization of xylan rich extracts from birch. Holzforschung 62:31–37.10.1515/HF.2008.005Search in Google Scholar
Yelle, D.J., Ralph, J., Frihart, C.R. (2008) Characterization of nonderivatized plant cell walls using high-resolution solution-state NMR spectroscopy. Magn. Reson. Chem. 46:508–517.Search in Google Scholar
Yuan, T.-Q., Sun, S.-N., Xu, F., Sun, R.-C. (2011a) Characterization of lignin structures and lignin-carbohydrate complex (LCC) linkages by quantitative 13C and 2D HSQC NMR spectroscopy. J. Agric. Food. Chem. 59:10604–10614.10.1021/jf2031549Search in Google Scholar PubMed
Yuan, T.Q., Sun, S.N., Xu, F., Sun, R.C. (2011b) Structural characterization of lignin from triploid of Populus tomentosa Carr. J. Agric. Food. Chem. 59:6605–6615.10.1021/jf2003865Search in Google Scholar PubMed
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Articles in the same Issue
- Masthead
- Masthead
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- Novel cellulose-based composites based on nanofibrillated plant and bacterial cellulose: recent advances at the University of Aveiro – a review
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- Alkali consumption of aliphatic carboxylic acids during alkaline pulping of wood and nonwood feedstocks
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- Development and evaluation of new curing agents derived from glycerol for formaldehyde-free soy-based adhesives in wood composites
- Formation of highly hydrophobic wood surfaces using silica nanoparticles modified with long-chain alkylsilane
- The fracture behavior of birch and spruce in the radial-tangential crack propagation direction at the scale of the growth ring
- Flatwise Young’s modulus and flatwise shear modulus of plywood measured by flexural vibration test
- A numerical and experimental study regarding the influence of some process parameters on the damage state in wood chips
- Treatment of wood with silica sols against attack by wood-decaying fungi and blue stain
- Mimicking of the strength loss in the Vasa: model experiments with iron-impregnated recent oak
- Improved heat insulation system (Mirrorpanel) for construction of wood buildings
- Meetings
- Meetings
Articles in the same Issue
- Masthead
- Masthead
- Review
- Novel cellulose-based composites based on nanofibrillated plant and bacterial cellulose: recent advances at the University of Aveiro – a review
- Original Articles
- Quantitative structural characterization of the lignins from the stem and pith of bamboo (Phyllostachys pubescens)
- Fractionation and characterization of lignin-carbohydrate complexes (LCCs) of Eucalyptus globulus in residues left after MWL isolation. Part II: Analyses of xylan-lignin fraction (X-L)
- Alkali consumption of aliphatic carboxylic acids during alkaline pulping of wood and nonwood feedstocks
- Improvement of kraft pulp bleaching by treatments with laccase, urea, and refining
- Development and evaluation of new curing agents derived from glycerol for formaldehyde-free soy-based adhesives in wood composites
- Formation of highly hydrophobic wood surfaces using silica nanoparticles modified with long-chain alkylsilane
- The fracture behavior of birch and spruce in the radial-tangential crack propagation direction at the scale of the growth ring
- Flatwise Young’s modulus and flatwise shear modulus of plywood measured by flexural vibration test
- A numerical and experimental study regarding the influence of some process parameters on the damage state in wood chips
- Treatment of wood with silica sols against attack by wood-decaying fungi and blue stain
- Mimicking of the strength loss in the Vasa: model experiments with iron-impregnated recent oak
- Improved heat insulation system (Mirrorpanel) for construction of wood buildings
- Meetings
- Meetings