The DFRC (Derivatization Followed by Reductive Cleavage) method and its applications for lignin characterization

Lignin: Structural Analysis, Applications in Biomaterials and Ecological Significance

Volumn , Issue , 2014, Pages 27-66

  Lu, Fachuang ^a   Ralph, John ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

Acetyl bromide; Biosynthesis; Lignin acylation; Lignocellulosics; Monolignol

Indexed keywords

ACYLATION; BIOCHEMISTRY; BIOSYNTHESIS; DIMERS;

ACETYL BROMIDE; DERIVATIZATION FOLLOWED BY REDUCTIVE CLEAVAGE; DETECTION AND IDENTIFICATIONS; LIGNIN CHARACTERIZATIONS; LIGNO-CELLULOSICS; MONOLIGNOL; STRUCTURAL IDENTIFICATION; TRANSGENIC PLANT LINES;

LIGNIN;

EID: 84940958293     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (115)

1. Ralph, J., Lundquist, K., Brunow, G. Lu, F., Kim, H., Schatz, P. F., Marita, J. M., Hatfield, R. D., Ralph, S. A. Christensen, J. H. & Boerjan, W. (2004). "Lignins: natural polymers from oxidative coupling of 4-hydroxyphenylpropanoids". Phytochemistry Reviews, 3 (1), 29-60.
2. Brunow, G., Lundquist, K. & Gellerstedt, G. (1999). "Lignin". in Analytical Methods in Wood Chemistry, Pulping, and Papermaking, eds. Sjöström, E. & Alén, R. (Springer-Verlag, Berlin, Germany), 77-124.
3. Sarkanen, K. V. (1971). "Dehydrogenative polymerization to lignin". in Lignins, Occurrence, Formation, Structure and Reactions, eds. Sarkanen, K. V. & Ludwig, C. H. (Wiley-Interscience, New York), 116-163.
4. Ralph, J., Brunow, G., Harris, P. J., Dixon, R. A., Schatz, P. F. & Boerjan, W. (2008). "Lignification: Are lignins biosynthesized via simple combinatorial chemistry or via proteinaceous control and template replication?". in Recent Advances in Polyphenol Research, Vol 1, eds. Daayf, F., El Hadrami, A., Adam, L., & Ballance, G. M. (Wiley-Blackwell Publishing, Oxford, UK), 36-66.
5. Harkin, J. M. (1967). "Lignin-a natural polymeric product of phenol oxidation". in Oxidative Coupling of Phenols, eds. Taylor, W. I. & Battersby, A. R. (Marcel Dekker, New York), 243-321.
6. Sarkanen, K. V. & Ludwig, C. H. (1971). Lignins, Occurrence, Formation, Structure and ReactionsWiley-Interscience, New York.
7. Gosselink, R. J. A., de Jong, E., Guran, B. & Abacherli, A. (2004). "Co-ordination network for lignin-standardisation, production and applications adapted to market requirements (EUROLIGNIN)". Industrial Crops and Products, 20 (2), 121-129.
8. Lapierre, C. (2010). "Determining lignin structure by chemical degradations". in Lignin and lignans: Advances in chemistry, eds. Heitner, C., Dimmel, D. R., & Schmidt, J. A. (CRC Press, Taylor & Francis Group, New York), 11-48.
9. Harkin, J. M. (1973). "Lignin". in Chemistry and Biochemistry of Herbage, ed. Butler, G. W. (Academic Press, London), 323-373.
10. Morohoshi, N. (1991). "Chemical characterization of wood and its components". in Wood and Cellulosic Chemistry, eds. David, N.-S. H. & Nobuo, S. (Marcel Dekker, New York), 331-392.
11. Sakakibara, A. (1991). "Chemistry of lignin". in Wood and Cellulosic Chemistry, eds. Hon, D. N.-S. & Shiraishi, N. (Marcel Dekker, New York), 113-175.
12. Lin, S. Y. & Dence, C. W. (1992). Methods in Lignin Chemistry Springer-Verlag, Heidelberg.
13. Heitner, C., Dimmel, D. R. & Schmidt, J. A. eds. (2010). Lignins and lignans: Advances in chemistry (CRC Press (Taylor & Francis Group), Boca Raton, FL).
14. Lu, F. & Ralph, J. (1996). "Reactions of lignin model β-aryl ethers with acetyl bromide". Holzforschung, 50 (4), 360-364.
15. Rowlands, D. C., Greenless, K. W., Derfer, J. M. & Boord, C. E. (1952). "The use of alkyl ethers in olefin syntheses". Journal of Organic Chemistry, 17, 807-811.
16. Soday, F. J. & Boord, C. E. (1933). "Syntheses in the olefin series". Journal of the American Chemical Society, 55, 3293-3302.
17. Kochi, J. K., Singleton, D. M. & Andrews, L. J. (1968). "Alkenes from halides and epoxides by reductive eliminations with Cr(II) complexes". Tetrahedron, 24, 3503-3515.
18. Lu, F. & Ralph, J. (1997). "Derivatization followed by reductive cleavage (DFRC method), a new method for lignin analysis: protocol for analysis of DFRC monomers". Journal of Agricultural and Food Chemistry, 45 (7), 2590-2592.
19. Johnson, D. B., Moore, W. E. & Zank, L. C. (1961). "The spectrophotometric determination of lignin in small wood samples". Tappi, 44, 793-789.
20. Morrison, I. M. (1972). "Improvements in the acetyl bromide technique to determine lignin and digestibility and its application to legumes". Journal of the Science of Food and Agriculture, 23 (12), 1463-1469.
21. Iiyama, K. & Wallis, A. F. A. (1988). "An improved acetyl bromide procedure for determining lignin in woods and wood pulps". Wood Science and Technology, 22 (3), 271-280.
22. Lu, F. & Ralph, J. (1998). "The DFRC method for lignin analysis. Part 3. NMR studies". Journal of Wood Chemistry and Technology, 18 (2), 219-233.
23. Lu, F. & Ralph, J. (1997). "The DFRC method for lignin analysis. Part 1. A new method for β-aryl ether cleavage: lignin model studies". Journal of Agricultural and Food Chemistry, 45 (12), 4655-4660.
24. Lu, F. & Ralph, J. (1998). "The DFRC method for lignin analysis. Part 2. Monomers from isolated lignins". Journal of Agricultural and Food Chemistry, 46 (2), 547-552.
25. Peng, J., Lu, F. & Ralph, J. (1998). "The DFRC method for lignin analysis. Part 4. Lignin dimers isolated from DFRC-degraded loblolly pine wood". Journal of Agricultural and Food Chemistry, 46 (2), 553-560.
26. Jaramillo-Carmona, S., Fuentes-Alventosa, J. M., Rodriguez-Gutierrez, G., Waldron, K. W., Smith, A. C., Guillen-Bejarano, R., Fernandez-Bolanos, J., Jimenez-Araujo, A. & Rodriguez-Arcos, R. (2008). "Characterization of asparagus lignin by HPLC". Journal of Food Science, 73 (7), C526-C532.
27. Martone, P. T., Estevez, J. M., Lu, F., Ruel, K., Denny, M. W., Somerville, C. & Ralph, J. (2009). "Discovery of lignin in seaweed reveals convergent evolution of cell-wall architecture". Current Biology, 19 (2), 169-175.
28. Lu, F. & Ralph, J. (1999). "The DFRC method for lignin analysis. 7. The behavior of cinnamyl end-groups". Journal of Agricultural and Food Chemistry, 47 (5), 1981-1987.
29. Ralph, J., Lapierre, C., Lu, F., Marita, J. M., Pilate, G., Van Doorsselaere, J., Boerjan, W. & Jouanin, L. (2001). "NMR evidence for benzodioxane structures resulting from incorporation of 5-hydroxyconiferyl alcohol into lignins of O-methyl-transferasedeficient poplars". Journal of Agricultural and Food Chemistry, 49 (1), 86-91.
30. Peng, J., Lu, F. & Ralph, J. (1999). "The DFRC method for lignin analysis. Part 5. Isochroman lignin trimers from DFRC-degraded Pinus taeda". Phytochemistry, 50 (4), 659-666.
31. Ralph, J., Peng, J. & Lu, F. (1998). "Isochroman structures in lignin, a new β-1 pathway". Tetrahedron Letters, 39 (28), 4963-4964.
32. Karhunen, P., Rummakko, P., Sipilä, J., Brunow, G. & Kilpeläinen, I. (1995). "Dibenzodioxocins; a novel type of linkage in softwood lignins". Tetrahedron Letters, 36 (1), 169-170.
33. Brunow, G. (1998). "Oxidative coupling of phenols and the biosynthesis of lignin". in Lignin and Lignan Biosynthesis, eds. Lewis, N. G. & Sarkanen, S. (American Chemical Society, Washington, DC), 131-147.
34. Lu, F. & Ralph, J. (1999). "Detection and determination of p-coumaroylated units in lignins". Journal of Agricultural and Food Chemistry, 47 (5), 1988-1992.
35. Ralph, J. & Lu, F. (1998). "The DFRC method for lignin analysis. Part 6. A modified method to determine acetate regiochemistry on native and isolated lignins". Journal of Agricultural and Food Chemistry, 46 (11), 4616-4619.
36. Lu, F. & Ralph, J. (2002). "Preliminary evidence for sinapyl acetate as a lignin monomer in kenaf". Journal of the Chemical Society, Chemical Communications, (1), 90-91.
37. Lu, F. & Ralph, J. (2008). "Novel tetrahydrofuran structures derived from β-β-coupling reactions involving sinapyl acetate in Kenaf lignins". Organic & Biomolecular Chemistry, 6 (20), 3681-3694.
38. Holtman, K. M., Chang, H. M., Jameel, H. & Kadla, J. F. (2003). "Elucidation of lignin structure through degradative methods: Comparison of modified DFRC and thioacidolysis". Journal of Agricultural and Food Chemistry, 51 (12), 3535-3540.
39. 31P NMR". Journal of Agricultural and Food Chemistry, 49 (2), 536-542.
40. Ralph, J., Peng, J., Lu, F., Hatfield, R. D. & Helm, R. F. (1999). "Are lignins optically active?". Journal of Agricultural and Food Chemistry, 47 (8), 2991-2996.
41. Grabber, J. H. (2005). "How do lignin composition, structure, and cross-linking affect degradability? A review of cell wall model studies". Crop Science, 45 (3), 820-831.
42. Moore, K. J. & Jung, H. J. G. (2001). "Lignin and fiber digestion". Journal of Range Management, 54 (4), 420-430.
43. Robinson, A. R. & Mansfield, S. D. (2009). "Rapid analysis of poplar lignin monomer composition by a streamlined thioacidolysis procedure and near-infrared reflectancebased prediction modeling". Plant Journal, 58 (4), 706-714.
44. Santoro, N., Cantu, S. L., Tornqvist, C. E., Falbel, T. G., Bolivar, J. L., Patterson, S. E., Pauly, M. & Walton, J. D. (2010). "A high-throughput platform for screening milligram quantities of plant biomass for lignocellulose digestibility". BioEnergy Research, 3 (1), 93-102.
45. Ralph, J. (1996). "An unusual lignin from Kenaf". Journal of Natural Products, 59 (4), 341-342.
46. Ralph, J. & Grabber, J. H. (1996). "Dimeric β-ether thioacidolysis products resulting from incomplete ether cleavage". Holzforschung, 50 (5), 425-428.
47. Yue, F., Lu, F., Sun, R.-C. & Ralph, J. (2012). "Syntheses of lignin-derived thioacidolysis monomers and their uses as quantitation standards". Journal of Agricultural and Food Chemistry, 60 (4), 922-928.
48. Guerra, A., Filpponen, I., Lucia, L. A. & Argyropoulos, D. S. (2006). "Comparative evaluation of three lignin isolation protocols for various wood species". Journal of Agricultural and Food Chemistry, 54 (26), 9696-9705.
49. Jaaskelainen, A. S., Sun, Y., Argyropoulos, D. S., Tamminen, T. & Hortling, B. (2003). "The effect of isolation method on the chemical structure of residual lignin". Wood Science and Technology, 37 (2), 91-102.
50. Guerra, A., Filpponen, I., Lucia, L. A., Saquing, C., Baumberger, S. & Argyropoulos, D. S. (2006). "Toward a better understanding of the lignin isolation process from wood". Journal of Agricultural and Food Chemistry, 54 (16), 5939-5947.
51. Guerra, A., Régis, M., Ferraz, A., Lu, F. & Ralph, J. (2004). "Structural characterization of lignin during Pinus taeda wood treatment with Ceripotiopsis subvermispora". Applied and Environmental Microbiology, 70 (7), 4073-4078.
52. Yelle, D. J., Ralph, J., Lu, F. & Hammel, K. E. (2008). "Evidence for cleavage of lignin by a brown rot basidomycete". Environmental Microbiology, 10 (7), 1844-1849.
53. Jin, Z. F., Akiyama, T., Chung, B. Y., Matsumoto, Y., Iiyama, K. & Watanabe, S. (2003). "Changes in lignin content of leaf litters during mulching". Phytochemistry, 64 (5), 1023-1031.
54. Bunzel, M., Ralph, J., Lu, F., Hatfield, R. D. & Steinhart, H. (2004). "Lignins and ferulate-coniferyl alcohol cross-coupling products in cereal grains". Journal of Agricultural and Food Chemistry, 52 (21), 6496-6502.
55. Bunzel, M. & Ralph, J. (2008). "Are cereal grains lignified?". American Association of Cereal Chemists International (AACCI).
56. Guerra, A., Norambuena, M., Freer, J. & Argyropoulos, D. S. (2008). "Determination of arylglycerol-beta-aryl ether linkages in enzymatic mild acidolysis lignins (EMAL), Comparison of DFRC/P-31 NMR with thioacidolysis". Journal of Natural Products, 71 (5), 836-841.
57. Crestini, C., Melone, F., Sette, M. & Saladino, R. (2011). "Milled Wood Lignin, A Linear Oligomer". Biomacromolecules, 12 (11), 3928-3935.
58. Weng, J. K., Li, X., Bonawitz, N. D. & Chapple, C. (2008). "Emerging strategies of lignin engineering and degradation for cellulosic biofuel production". Current Opinion in Biotechnology, 19 (2), 166-172.
59. Baucher, M., Halpin, C., Petit-Conil, M. & Boerjan, W. (2003). "Lignin, Genetic engineering and impact on pulping". Crit. Rev. Biochem. Mol. Biol., 38 (4), 305-350.
60. Vanholme, R., Morreel, K., Darrah, C., Oyarce, P., Grabber, J. H., Ralph, J. & Boerjan, W. (2012). "Metabolic engineering of novel lignin in biomass crops". New Phytologist, 196 (4), 978-1000.
61. Bonawitz, N. D. & Chapple, C. (2013). "Can genetic engineering of lignin deposition be accomplished without an unacceptable yield penalty?". Current Opinion in Biotechnology, 24 (2), 336-343.
62. Baucher, M., Monties, B., Van Montagu, M. & Boerjan, W. (1998). "Biosynthesis and genetic engineering of lignin". Crit. Rev. in Plant Sci., 17 (2), 125-197.
63. Vanholme, R., Morreel, K., Ralph, J. & Boerjan, W. (2008). "Lignin engineering". Current Opinion in Plant Biology, 11 (3), 278-285.
64. Vanholme, R., Cesarino, I., Rataj, K., Xiao, Y., Sundin, L., Goeminne, G., Kim, H., Cross, J., Morreel, K., Araujo, P. et al. (2013). "Caffeoyl shikimate esterase (CSE), a newly discovered gene in the lignin biosynthetic pathway". Science, 341 (6150), 1103-1106.
65. Withers, S., Lu, F., Kim, H., Zhu, Y., Ralph, J. & Wilkerson, C. G. (2012). "Identification of a grass-specific enzyme that acylates monolignols with p-coumarate". Journal of Biological Chemistry, 287 (11), 8347-8355.
66. Higuchi, T. (1990). "Lignin biochemistry: biosynthesis and biodegradation". Wood Science and Technology, 24 (1), 23-63.
67. Fukushima, K. (2001). "Regulation of syringyl to guaiacyl ratio in lignin biosynthesis". Journal of Plant Research, 114 (1116), 499-508.
68. Chen, F., Yasuda, S. & Fukushima, K. (1999). "Evidence for a novel biosynthetic pathway that regulates the ratio of syringyl to guaiacyl residues in lignin in the differentiating xylem of Magnolia kobus". Planta, 207 (4), 597-603.
69. Yamauchi, K., Yasuda, S. & Fukushima, K. (2002). "Evidence for the biosynthetic pathway from sinapic acid to syringyl lignin using labeled sinapic acid with stable isotope at both methoxy groups in Robinia pseudoacacia and Nerium indicum". Journal of Agricultural and Food Chemistry, 50 (11), 3222-3227.
70. Yamauchi, K., Yasuda, S., Hamada, K., Tsutsumi, Y. & Fukushima, K. (2003). "Multiform biosynthetic pathway of syringyl lignin in angiosperms". Planta, 216 (3), 496-501.
71. Whetten, R. & Sederoff, R. (1995). "Lignin Biosynthesis". Plant Cell, 7, 1001-1013.
72. Tsuji, Y., Chen, F., Yasuda, S. & Fukushima, K. (2004). "The behavior of deuteriumlabeled monolignol and monolignol glucosides in lignin blosynthesis in angiosperms". Journal of Agricultural and Food Chemistry, 52 (1), 131-134.
73. Tsuji, Y., Chen, F., Yasuda, S. & Fukushima, K. (2005). "Unexpected behavior of coniferin in lignin biosynthesis of Ginkgo biloba L". Planta, 222 (1), 58-69.
74. Smith, D. C. C. (1955). "Ester groups in lignin". Nature, 176, 267-268.
75. Ralph, J. & Helm, R. F. (1993). "Lignin/hydroxycinnamic acid/polysaccharide complexes: Synthetic models for regiochemical characterization". in Forage Cell Wall Structure and Digestibility, eds. Jung, H. G., Buxton, D. R., Hatfield, R. D., & Ralph, J. (American Society of Agronomy, Crop Science Society of America, Soil Science Society of America, Madison, WI), 201-246.
76. Nakano, J., Ishizu, A. & Migita, N. (1961). "Studies on lignin. XXXII. Ester groups of lignin". Tappi, 44 (1), 30-32.
77. 13C NMR study of milled wood lignins from hybrid Salix Clones". Holzforschung, 46 (6), 505-511.
78. Sarkanen, K. V., Chang, H.-M. & Allan, G. G. (1967). "Species variation in lignins. III. Hardwood lignins". Tappi, 50 (12), 587-590.
79. Shimada, M., Fukuzuka, T. & Higuchi, T. (1971). "Ester linkages of p-coumaric acid in bamboo and grass lignins". Tappi, 54 (1), 72-78.
80. Nakamura, Y. & Higuchi, T. (1976). "Ester linkage of p-coumaric acid in bamboo lignin". Holzforschung, 30 (6), 187-191.
81. Nakamura, Y. & Higuchi, T. (1978). "Ester linkage of p-coumaric acid in bamboo lignin. II. Syntheses of coniferyl p-hydroxybenzoate and coniferyl p-coumarate as possible precursors of aromatic acid esters in lignin". Cellul. Chem. Technol., 12 (2), 199-208.
82. Nakamura, Y. & Higuchi, T. (1978). "Ester linkage of p-coumaric acid in bamboo lignin. III. Dehydrogenative polymerization of coniferyl p-hydroxybenzoate and coniferyl p-coumarate". Cellul. Chem. Technol., 12 (2), 209-221.
83. Ralph, J., Hatfield, R. D., Quideau, S., Helm, R. F., Grabber, J. H. & Jung, H.-J. G. (1994). "Pathway of p-coumaric acid incorporation into maize lignin as revealed by NMR". Journal of the American Chemical Society, 116 (21), 9448-9456.
84. Helm, R. F. & Ralph, J. (1993). "Stereospecificity for zinc borohydride reduction of a-aryloxy-β-hydroxy ketones". Journal of Wood Chemistry and Technology, 13 (4), 593-601.
85. Li, K. & Helm, R. F. (1995). "Synthesis and rearrangement reactions of ester-linked lignin-carbohydrate model compounds". Journal of Agricultural and Food Chemistry, 43, 2098-2103.
86. 31P and 2D NMR spectroscopy. The occurrence of ester bonds and a-O-4 substructures". Journal of Agricultural and Food Chemistry, 45 (4), 1212-1219.
87. del Rio, J. C., Rencoret, J., Prinsen, P., Martínez, Á. T., Ralph, J. & Gutiérrez, A. (2012). "Structural characterization of wheat straw lignin as revealed by analytical pyrolysis, 2D-NMR, and reductive cleavage methods". Journal of Agricultural and Food Chemistry, 60 (23), 5922-5935.
88. Das, N. N., Das, S. C., Sarkar, A. K. & Mukherjee, A. K. (1984). "Lignin-xylan ester linkage in mesta fiber (Hibiscus cannabinus)". Carbohydr. Res, 129, 197-207.
89. Björkman, A. (1956). "Studies on finely divided wood. Part I. Extraction of lignin with neutral solvents". Sven. Papperstidn., 59 (13), 477-485.
90. Lundquist, K. (1992). "Characterization in Solution, Spectroscopic Methods. 5.3. Proton (1H) NMR Spectroscopy". in Methods in Lignin Chemistry, eds. Lin, S. Y. & Dence, C. W. (Springer-Verlag, Berlin), 242-249.
91. del Rio, J. C., Marques, G., Rencoret, J., Martinez, A. T. & Gutierrez, A. (2007). "Occurrence of naturally acetylated lignin units". Journal of Agricultural and Food Chemistry, 55 (14), 5461-5468.
92. del Rio, J. C., Rencoret, J., Marques, G., Gutierrez, A., Ibarra, D., Santos, J. I., Jimenez-Barbero, J., Zhang, L. M. & Martinez, A. T. (2008). "Highly Acylated (acetylated and/or p-coumaroylated) native lignins from diverse herbaceous plants". Journal of Agricultural and Food Chemistry, 56 (20), 9525-9534.
93. Rencoret, J., Ralph, J., Marques, G., Gutiérrez, A., Martínez, á. T. & del Rio, J. C. (2013). "Structural characterization of the lignin from coconut (Cocos nucifera) coir fibers". Journal of Agricultural and Food Chemistry, 61 (10), 2434-2445.
94. del Río, J. C., Prinsen, P., Rencoret, J., Nieto, L., Jiménez-Barbero, J., Ralph, J., Martínez, á. T. & Gutiérrez, A. (2012). "Structural characterization of the lignin in the cortex and pith of elephant grass (Pennisetum purpureum) stems". Journal of Agricultural and Food Chemistry, 60 (14), 3619-3634.
95. Lu, F. & Ralph, J. (2005). in Thirteenth International Symposium on Wood, Fiber, and Pulping Chemistry (APPITA, Australia, Auckland, New Zealand), 233-237.
96. Petrik, D., Karlen, S. D., Cass, C., Padmakshan, D., Lu, F., Liu, S., Le Bris, P., Antelme, S., Santoro, N., Wilkerson, C. G. et al. (2014). "p-Coumaroyl-CoA Monolignol Transferase (PMT) acts specifically in the lignin biosynthetic pathway in Brachypodium distachyon". The Plant Journal, in press (accepted 12/17/2013).
97. Rook, J. A., Muller, L. D. & Shank, D. B. (1977). "Intake and digestibility of brown-midrib silage by lactating dairy cows". J. Dairy Sci., 60 (12), 1894-1904.
98. Barriere, Y., Charcosset, A., Denoue, D., Madur, D., Bauland, C. & Laborde, J. (2010). "Genetic Variation for Lignin Content and Cell Wall Digestibility in Early Maize Lines Derived from Ancient Landraces". Maydica, 55 (1), 65-74.
99. Boudet, A. M., Kajita, S., Grima-Pettenati, J. & Goffner, D. (2003). "Lignins and lignocellulosics, a better control of synthesis for new and improved uses". Trends in Plant Science, 8 (12), 576-581.
100. Chen, F. & Dixon, R. A. (2007). "Lignin modification improves fermentable sugar yields for biofuel production". Nature Biotechnology, 25 (7), 759-761.
101. Humphreys, J. M. & Chapple, C. (2002). "Rewriting the lignin roadmap". Current Opinion in Plant Biology, 5 (3), 224-229.
102. Marita, J. M., Vermerris, W., Ralph, J. & Hatfield, R. D. (2003). "Variations in the cell wall composition of maize brown midrib mutants". Journal of Agricultural and Food Chemistry, 51 (5), 1313-1321.
103. Lu, F., Marita, J. M., Lapierre, C., Jouanin, L., Morreel, K., Boerjan, W. & Ralph, J. (2010). "Sequencing around 5-hydroxyconiferyl alcohol-derived units in caffeic acid Omethyltransferase-deficient poplar lignins". Plant Physiology, 153 (2), 569-579.
104. Hwang, B. H. & Sakakibara, A. (1981). "Hydrogenolysis of protolignin. XVIII. Isolation of a new dimeric compound with a heterocycle involving α,β-diether". Holzforschung, 35 (6), 297-300.
105. Jouanin, L., Goujon, T., de Nadaï, V., Martin, M.-T., Mila, I., Vallet, C., Pollet, B., Yoshinaga, A., Chabbert, B., Petit-Conil, M. et al. (2000). "Lignification in transgenic poplars with extremely reduced caffeic acid O-methyltransferase activity". Plant Physiology, 123 (4), 1363-1373.
106. Ralph, J., Lapierre, C., Marita, J., Kim, H., Lu, F., Hatfield, R. D., Ralph, S. A., Chapple, C., Franke, R., Hemm, M. R. et al. (2001). "Elucidation of new structures in lignins of CAD-and COMT-deficient plants by NMR". Phytochemistry, 57 (6), 993-1003.
107. Weng, J.-K., Mo, H. & Chapple, C. (2010). "Over-expression of F5H in COMTdeficient Arabidopsis leads to enrichment of an unusual lignin and disruption of pollen wall formation". The Plant Journal, 64 (6), 898-911.
108. Meyer, K., Shirley, A. M., Cusumano, J. C., Bell-Lelong, D. A. & Chapple, C. (1998). "Lignin monomer composition is determined by the expression of a cytochrome P450-dependent monooxygenase in Arabidopsis". Proceedings of the National Academy of Sciences, USA, 95 (12), 6619-6623.
109. Franke, R., McMichael, C. M., Meyer, K., Shirley, A. M., Cusumano, J. C. & Chapple, C. (2000). "Modified lignin in tobacco and poplar plants over-expressing the Arabidopsis gene encoding ferulate 5-hydroxylase". Plant Journal, 22 (3), 223-234.
110. Huntley, S. K., Ellis, D., Gilbert, M., Chapple, C. & Mansfield, S. D. (2003). "Significant increases in pulping efficiency in C4H-F5H-transformed poplars, Improved chemical savings and reduced environmental toxins". Journal of Agricultural and Food Chemistry, 51 (21), 6178-6183.
111. Vanholme, R., Ralph, J., Akiyama, T., Lu, F., Rencoret Pazo, J., Christensen, J., Rohde, A., Morreel, K., DeRycke, R., Kim, H. et al. (2010). "Engineering traditional monolignols out of lignins by concomitant up-regulation F5H1 and down-regulation of COMT in Arabidopsis ". The Plant Journal, 64 (6), 885-897.
112. Franke, R., Hemm, M. R., Denault, J. W., Ruegger, M. O., Humphreys, J. M. & Chapple, C. (2002). "Changes in secondary metabolism and deposition of an unusual lignin in the ref8 mutant of Arabidopsis". Plant Journal, 30 (1), 47-59.
113. Zhang, K. W., Qian, Q., Huang, Z. J., Wang, Y. Q., Li, M., Hong, L. L., Zeng, D. L., Gu, M. H., Chu, C. C. & Cheng, Z. K. (2006). "Gold Hull and Internode2 encodes a primarily multifunctional cinnamyl-alcohol dehydrogenase in Rice". Plant Physiology, 140 (3), 972-983.
114. Schilmiller, A. L., Stout, J., Weng, J. K., Humphreys, J., Ruegger, M. O. & Chapple, C. (2009). "Mutations in the cinnamate 4-hydroxylase gene impact metabolism, growth and development in Arabidopsis". Plant Journal, 60 (5), 771-782.
115. Li, X. J., Yang, Y., Yao, J. L., Chen, G. X., Li, X. H., Zhang, Q. F. & Wu, C. Y. (2009). "FLEXIBLE CULM 1 encoding a cinnamyl-alcohol dehydrogenase controls culm mechanical strength in rice". Plant Molecular Biology, 69 (6), 685-697.