Structural transformation of miscanthus ×giganteus lignin fractionated under mild formosolv, basic organosolv, and cellulolytic enzyme conditions

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 1, 2012, Pages 144-152

  Wang, Kun ^a,b   Bauer, Stefan ^b   Sun, Run Cang ^a,c  

^a BEIJING FORESTRY UNIVERSITY   (China)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

cellulolytic enzyme; fractionation; Lignin; Miscanthus giganteus; organosolv; structural characteristic

Indexed keywords

ACIDIC CONDITIONS; ACIDIC HYDROLYSIS; ALKYL ETHERS; ANALYTICAL TECHNIQUES; CARBOHYDRATE CONTENT; CARBON-CARBON BOND; CELLULOLYTIC ENZYME; DERIVATIZATION FOLLOWED BY REDUCTIVE CLEAVAGE; FOURIER TRANSFORM INFRARED; GUAIACYL; LIGNIN FRACTION; MISCANTHUS; NON-DESTRUCTIVE TECHNIQUE; ORGANOSOLV; ORIGINAL STRUCTURES; S/G RATIO; STRUCTURAL CHARACTERISTICS; STRUCTURAL CHARACTERIZATION; STRUCTURAL ELUCIDATION; STRUCTURAL TRANSFORMATION; THIOACIDOLYSIS;

ACETYLATION; ALKALINITY; BAST FIBERS; CARBOHYDRATES; CONDENSATION; CONDENSATION REACTIONS; ENZYMES; ETHERS; FRACTIONATION; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SIZE EXCLUSION CHROMATOGRAPHY;

LIGNIN;

CELLULASE; LIGNIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; INFRARED SPECTROSCOPY; ISOLATION AND PURIFICATION; MOLECULAR WEIGHT; POACEAE;

CELLULASE; LIGNIN; MOLECULAR STRUCTURE; MOLECULAR WEIGHT; POACEAE; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

ACETYLATION; ALKALINITY; CARBOHYDRATES; CONDENSATION; ENZYMES; FIBERS; FRACTIONATION; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RELAXATION; ORGANOSOLV LIGNINS; PHLOEM;

MISCANTHUS;

EID: 84862965682     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf2037399     Document Type: Article

References (48)

1. Sakakibara, A.; Sano, Y. Chemistry of lignin. In Wood and Cellulosic Chemistry; Hon, D. N.-S., Shiraish, N., Eds.; Marcel Dekker, Inc.: New York, 2001; pp 109-111.
2. Ralph, J.; Brunow, G.; Boerjan, W. Lignins. In Encyclopedia of Life Sciences; Rose, F., Osborne, K., Eds.; John Wiley and Sons, Ltd.: Chichester, U.K., 2003; pp 1-10.
3. Boerjian, W.; Ralph, J.; Baucher, M. Lignin biosynthesis Annu. Rev. Plant Biol. 2003, 54, 519-549
4. Ralph, J.; Bunzel, M.; Marita, J. M.; Hatfield, R. D.; Lu, F.; Kim, H.; Schatz, P. F.; Grabber, J. H.; Steinhart, H. Peroxidase-dependent cross-linking reactions of p -hydroxycinnamates in plant cell walls Phytochem. Rev. 2004, 3, 79-96 (Pubitemid 41184542)
5. Stewart, D. Lignin as a base material for materials applications: Chemistry, application and economics Ind. Crops Prod. 2008, 27, 202-207 (Pubitemid 350297865)
6. Vazques, G.; Rodriguez-Bona, C.; Freire, S.; Gonzalez-Alvarez, J.; Antorrena, G. Acetosolv pine lignin as copolymer in resins for manufacture of exterior grade plywoods Bioresour. Technol. 1999, 70, 209-214 (Pubitemid 29253534)
7. Simionescu, C. I.; Rusan, V.; Macoveanu, M. M.; Cazacu, G.; Lipsa, R.; Vasile, C.; Stoleriu, A.; Ioanid, A. Lignin/epoxy composites Compos. Sci. Technol. 1993, 48, 317-323 (Pubitemid 23690135)
8. Bjorkman, A. Studies on finely divided wood. Part I. Extraction of lignin with neutral solvents Sven. Papperstidn. Nordisk Cellulosa 1956, 59, 477-485
9. Whiting, P.; Goring, D. A. I. The morphological origin of milled wood lignin Sven. Papperstidn. Nordisk Cellulosa 1981, 84, R120-R122
10. Chang, H. M.; Cowling, E. B.; Brown, W.; Adler, E.; Miksche, G. Comparative studies on cellulolytic enzyme lignin and milled wood lignin of sweetgum and spruce Holzforschung 1975, 29 (5) 153-159
11. Holtman, K. M.; Kadla, J. F. Solution-state nuclear magnetic resonance study of the similarities between milled wood lignin and cellulolytic enzyme lignin J. Agric. Food Chem. 2004, 52, 720-726
12. Zhang, A. P.; Lu, F. C.; Sun, R. C.; Ralph, J. Isolation of cellulolytic enzyme lignin from wood preswollen/dissolved in dimethyl sulfoxide/ N -methylimidazole J. Agric. Food Chem. 2010, 58, 3446-3450
13. Pan, X. J.; Xie, D.; Yu, R. W.; Lam, D.; Saddler, J. N. Pretreatment of lodgepole pine killed by mountain pine beetle using the ethanol organosolv process: Fractionation and process optimization Ind. Eng. Chem. Res. 2007, 46, 2609-2617 (Pubitemid 46652798)
14. Pan, X. J.; Xie, D.; Yu, R. W.; Lam, D.; Saddler, J. N. The bioconversion of mountain pine beetle-killed lodgepole pine to fuel ethanol using the organosolv process Biotechnol. Bioeng. 2008, 101, 39-48
15. Hallac, B. B.; Sannigrahi, P.; Pu, Y. Q.; Ray, M.; Murphy, R. J.; Ragauskas, A. J. Effect of ethanol organosolv pretreatment on enzymatic hydrolysis of Buddleja davidii stem biomass Ind. Eng. Chem. Res. 2010, 49, 1467-1472
16. Park, N.; Kim, H. Y.; Koo, B. W.; Yeo, H.; Choi, I. G. Oraganosolv pretreatment with various catalysts for enhancing enzymatic hydrolysis of pitch pine (Pinus rigida) Bioresour. Technol. 2010, 101, 7046-7053
17. Xu, F.; Sun, J. X.; Sun, R. C.; Fowler, P.; Baird, M. S. Comparative study of organosolv lignins from wheat straw Ind. Crops Prod. 2006, 23, 180-193 (Pubitemid 43276249)
18. Ligero, P.; Villaverde, J. J.; Vega, A.; Baob, M. Acetosolv delignification of depithed cardoon (Cynara cardunculus) stalks Ind. Crops Prod. 2007, 25, 294-300
19. Wang, K.; Jiang, J. X.; Xu, F.; Sun, R. C. Influence of steaming pressure on steam explosion pretreatment of Lespedeza stalks (Lespedeza cyrtobotrya). II. Characteristics of degraded lignin J. Appl. Polym. Sci. 2010, 116, 1617-1625
20. Xu, F.; Jiang, J. X.; Sun, R. C.; Tang, J. N.; Sun, J. X.; Su, Y. Q. Fractional isolation and structural characterization of mile ball-milled lignin in high yield and purity from Eucommia ulmoides Oliv Wood Sci. Technol. 2008, 42, 211-226 (Pubitemid 351438167)
21. Wang, K.; Jiang, J. X.; Xu, F.; Sun, R. C.; Baird, M. S. Influence of steam pressure on the physicochemical properties of degraded hemicelluloses obtained from steam-exploded Lespedeza stalks Bioresources 2010, 5, 1717-1732
22. Somerville, C.; Youngs, H.; Taylor, C.; Davis, S. C.; Long, S. P. Feedstocks for lignocellulosic biofuels Science 2010, 329, 790-792
23. Long, S. P.; Beale, C. V. Resource capture by Miscanthus. In Miscanthus for Energy and Fibre; Jones, M. B.; Walsh, M., Eds.; James and James: London, U.K., 2001; pp 10-20.
24. Beale, C. V.; Long, S. P. Can perennial C4 grasses attain high efficiencies of radiant energy conversion in cool climates? Plant, Cell Environ. 1995, 18, 641-650
25. Brosse, N.; Sannigrahi, P.; Ragauskas, A. Pretreatment of Miscanthus ×giganteus using the ethanol organosolv process for ethanol production Ind. Eng. Chem. Res. 2009, 48, 8328-8334
26. Villaverde, J. J.; Li, J.; Ek, M.; Ligero, P.; Vega, A. Native lignin structure of Miscanthus ×giganteus and its changes during acetic and formic acid fractionation J. Agric. Food Chem. 2009, 57, 6262-6270
27. Sluiter, A.; Hames, B.; Ruiz, R.; Scarlata, C.; Sluiter, J. Determination of Structural Carbohydrates and Lignin in Biomass; Laboratory Analytical Procedures (LAP) for Standard Biomass Analysis; National Renewable Energy Laboratory (NREL): Golden, CO, 2007; http://www.nrel.gov/biomass/analytical- procedures.html.
28. Guerra, A.; Filpponen, I.; Lucia, L. A.; Saquing, C.; Baumberger, S.; Argyropoulos, D. S. Toward a better understanding of the lignin isolation process from wood J. Agric. Food Chem. 2006, 54, 5939-5947 (Pubitemid 44342225)
29. Lu, F.; Ralph, J. DFRC method for lignin analysis. 1. New method for β-aryl ether cleavage: lignin model studies J. Agric. Food Chem. 1997, 45, 4655-4660 (Pubitemid 127485821)
30. Ikeda, T.; Holtman, K.; Kadla, J. F.; Chang, H. M.; Jameel, H. Studies on the effect of ball milling on lignin structure using a modified DFRC method J. Agric. Food Chem. 2002, 50, 129-135 (Pubitemid 34038520)
31. Rolando, C.; Monties, B.; Lapierre, C. Thioacidolysis. In Methods in Lignin Chemistry; Lin, S. Y.; Dence, C. W., Eds.; Springer-Verlag: Berlin, Germany, 1992; pp 487-497.
32. Capanema, E. A.; Balakshin, M. Y.; Kadla, J. F. A comprehensive approach for quantitative lignin characterization by NMR spectroscopy J. Agric. Food Chem. 2004, 52, 1850-1860
33. Capanema, E. A.; Balakshin, M. Y.; Kadla, J. F. Quantitative characterization of a hardwood milled wood lignin by nuclear magnetic resonance spectroscopy J. Agric. Food Chem. 2005, 53, 9639-9649 (Pubitemid 43027165)
34. Liitia, T. M.; Maunu, S. L.; Hortling, B.; Toikka, M.; Kilpelainen, I. Analysis of technical lignins by two- and three-dimensional NMR spectroscopy J. Agric. Food Chem. 2003, 51, 2136-2143
35. Ralph, S. A.; Ralph, J.; Landucci, L. NMR Database of Lignin and Cell Wall Model Compounds; United States Forest Products Laboratory: Madison, WI, 2004; http://ars.usda.gov/Services/docs.htm?docid=10491 (accessed Jan 2009).
36. Martinez, A. T.; Rencoret, J.; Marques, G.; Gutierrez, A.; Ibarra, D.; Jimenez-Barbero, J.; del Rio, J. C. Monolignol acylation and lignin structure in some nonwoody plants: A 2D-NMR study Phytochemistry 2008, 69, 2831-2843
37. Lu, F. C.; Ralph, J. Non-degradative dissolution and acetylation of ball-milled plant cell walls: High-resolution solution-state NMR Plant J. 2003, 35, 535-544 (Pubitemid 37056834)
38. Takahashi, N.; Koshijima, T. Ester linkages between lignin and glucuronoxylan in a lignin-carbohydrate complex from beech (Fagus crenata) wood Wood Sci. Technol. 1988, 22, 231-241
39. Sun, J. X.; Xu, F.; Sun, X. F.; Xiao, B.; Sun, R. C. Physico-chemical and thermal characterization of cellulose from barley straw Polym. Degrad. Stab. 2005, 88, 521-531 (Pubitemid 40338138)
40. Pellinen, J.; Salkinoja-Salonen, M. High-performance size exclusion chromatography of lignin and its derivatives J. Chromatogr. 1985, 328, 299-308
41. Connors, W. J.; Sarlcanen, S.; McCarthy, J. L. Gel chromatography and association complexes of lignin Holzforschung 1980, 34, 80-85
42. Lawoko, M.; Henriksson, G.; Gellerstedt, G. Characterisation of lignin-carbohydrate complexes (LCCs) of spruce wood (Picea abies L.) isolated with two methods Holzforschung 2006, 60, 156-161 (Pubitemid 43383305)
43. Li, J.; Henriksson, G.; Gellerstedt, G. Lignin depolymerization/ repolymerization and its critical role for delignification of aspen wood by steam explosion Bioresour. Technol. 2007, 98, 3061-3068 (Pubitemid 46603259)
44. del Rio, J. C; Rencoret, J.; Marques, G.; Gutierrez, A.; Ibarra, D.; Santos, J. I.; Jimenez-Barbero, J.; Zhang, L.; Martinez, A. T. Highly acylated (acetylated and/or p -coumaroylated) native lignins from diverse herbaceous plants J. Agric. Food Chem. 2008, 56, 9525-9534
45. Lu, F.; Ralph, J. Derivatization followed by reductive cleavage (DFRC method): A new method for lignin analysis: Protocol for analysis of DFRC monomers J. Agric. Food Chem. 1997, 45, 2590-2592 (Pubitemid 127476987)
46. 31P NMR J. Agric. Food Chem. 2001, 49, 536-542 (Pubitemid 32172588)
47. Faix, O. Fourier transform infrared spectroscopy. In Methods in Lignin Chemistry; Lin, S. Y.; Dence, C. W., Eds.; Springer-Verlag: Berlin, Germany, 1992; pp 83-109.
48. Sannigrahi, P.; Ragauskas, A. J.; Miller, S. J. Lignin structural modifications resulting from ethanol organosolv treatment of loblolly pine Energy Fuels 2010, 24, 683-689