Trends in lignin modification: A comprehensive analysis of the effects of genetic manipulations/mutations on lignification and vascular integrity

Phytochemistry

Volumn 61, Issue 3, 2002, Pages 221-294

  Anterola, Aldwin M ^a   Lewis, Norman G ^a  

^a WASHINGTON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 COUMARATE 3 HYDROXYLASE; 4 COUMARATE:COENZYME A LIGASE; BIOPOLYMER; CAFFEATE O METHYLTRANSFERASE; CINNAMATE 4 MONOOXYGENASE; CINNAMIC ACID; CINNAMOYL COENZYME A O METHYLTRANSFERASE; CINNAMOYL COENZYME A REDUCTASE; CINNAMYL ALCOHOL; CINNAMYL ALCOHOL DEHYDROGENASE; FERULATE 5 HYDROXYLASE; HYDROXYL GROUP; LIGNIN; METHYLTRANSFERASE; OXIDOREDUCTASE; OXYGENASE; PARA COUMARIC ACID; PHENYLALANINE; PHENYLALANINE AMMONIA LYASE; UNCLASSIFIED DRUG;

ANGIOSPERM; BIOSYNTHESIS; CELL SPECIFICITY; CHEMICAL STRUCTURE; CHEMISTRY; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME REGULATION; ENZYMOLOGY; GENE EXPRESSION REGULATION; GENE MUTATION; GENETIC ENGINEERING; GENETIC MANIPULATION; GENETIC TRANSCRIPTION; GENETICS; GYMNOSPERM; LIGNIFICATION; METABOLIC REGULATION; METABOLISM; MUTATION; NONHUMAN; PHENOTYPE; PHYTOCHEMISTRY; PLANT DEVELOPMENT; PLANT GROWTH; REVIEW; TRANSGENIC PLANT; VASCULAR PLANT;

NASA DISCIPLINE PLANT BIOLOGY; NON-NASA CENTER;

GENE EXPRESSION REGULATION, PLANT; GENETIC ENGINEERING; LIGNIN; MOLECULAR STRUCTURE; MUTATION; PLANTS, GENETICALLY MODIFIED;

GYMNOSPERMAE; MAGNOLIOPHYTA;

EID: 0036798592     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0031-9422(02)00211-X     Document Type: Review

References (171)

1. Amrhein, N., Diederich, E., 1980. Turnover of isoflavones in Cicer arietinum L. Naturwissenschaften 67, 40-41.
2. Amrhein, N., Frank, G., Lemm, G., Luhmann, H.-B., 1983. Inhibition of lignin formation by L-α-aminooxy-β-phenylpropionic acid, an inhibitor of phenylalanine ammonia-lyase. European Journal of Cell Biology 29, 139-144.
3. Amrhein, N., Gerhardt, J., 1979. Superinduction of phenylalanine ammonia-lyase in gherkin hypocotyls caused by the inhibitor, L-α-aminooxy-β-phenylpropionic acid. Biochimica et Biophysica Acta 583, 434-442.
4. Amrhein, N., Gödeke, K.-H., 1977. α-Aminooxy-β-phenylpropionic acid-a potent inhibitor of L-phenylalanine ammonia-lyase in vitro and in vivo. Plant Science Letters 8, 313-317.
5. Amrhein, N., Holländer, H., 1979. Inhibition of anthocyanin formation in seedlings and flowers by the enantiomers of α-aminooxy-β-phenylpropionic acid and their N-benzyloxycarbonyl derivatives. Planta 144, 385-389.
6. Anterola, A.M., Jeon, J.-H., Davin, L.B., Lewis, N.G., 2002. Transcriptional control of monolignol biosynthesis in Pinus taeda: factors affecting monolignol ratios and carbon allocation in phenylpropanoid metabolism. The Journal of Biological Chemistry 277, 18272-18280.
7. Anterola, A.M., van Rensburg, H., van Heerden, P.S., Davin, L.B., Lewis, N.G., 1999. Multi-site modulation of flux during monolignol formation in loblolly pine (Pinus taeda). Biochemical and Biophysical Research Communications 261, 652-657.
8. Atanassova, R., Favet, N., Martz, F., Chabbert, B., Tollier, M.-T., Monties, B., Fritig, B., Legrand, M., 1995. Altered lignin composition in transgenic tobacco expressing O-methyltransferase sequences in sense and antisense orientation. The Plant Journal 8, 465-477.
9. Bak, S., Kahn, R.A., Nielsen, H.L., Møller, B.L., Halkier, B.A., 1998. Cloning of three A-type cytochromes P450, CYP71E1, CYP98, and CYP99 from Sorghum bicolor (L.) Moench by a PCR approach and identification by expression in Escherichia coli of CYP71E1 as a multifunctional cytochrome P450 in the biosynthesis of the cyanogenic glucoside dhurrin. Plant Molecular Biology 36, 393-405.
10. Barnes, R.F., Muller, L.D., Bauman, L.F., Colenbrander, V.F., 1971. In vitro dry matter disappearance of brown midrib mutants of maize (Zea mays L.). Journal of Animal Science 33, 881-884.
11. Bate, N.J., Orr, J., Ni, W., Meromi, A., Nadler-Hassar, T., Doerner, P.W., Dixon, R.A., Lamb, C.J., Elkind, Y., 1994. Quantitative relationship between phenylalanine ammonia-lyase levels and phenylpropanoid accumulation in transgenic tobacco identifies a rate-determining step in natural product synthesis. Proceedings of the National Academy of Sciences of the United States of America 91, 7608-7612.
12. Baucher, M., Bernard-Vailhé, M.A., Chabbert, B., Besle, J.-M., Opsomer, C., Van Montagu, M., Botterman, J., 1999. Down-regulation of cinnamyl alcohol dehydrogenase in transgenic alfalfa (Medicago sativa L.) and the effect on lignin composition and digestibility. Plant Molecular Biology 39, 437-447.
13. Baucher, M., Chabbert, B., Pilate, G., Van Doorsselaere, J., Tollier, M.-T., Petit-Conil, M., Cornu, D., Monties, B., Van Montagu, M., Inzé, D., Jouanin, L., Boerjan, W., 1996. Red xylem and higher lignin extractability by down-regulating a cinnamyl alcohol dehydrogenase in poplar. Plant Physiology 112, 1479-1490.
14. Baucher, M., Monties, B., Van Montagu, M., Boerjan, W., 1998. Biosynthesis and genetic engineering of lignin. Critical Reviews in Plant Sciences 17, 125-197.
15. Bernard-Vailhé, M.-A., Cornu, A., Robert, D., Maillot, M.-P., Besle, J.-M., 1996. Cell wall degradability of transgenic tobacco stems in relation to their chemical extraction and lignin quality. Journal of Agricultural and Food Chemistry 44, 1164-1169.
16. Bialski, A.M., Luthe, C.E., Fong, J.L., Lewis, N.G., 1986. Sulphite-promoted delignification of wood: identification of paucidisperse lignosulphonates. Canadian Journal of Chemistry 64, 1336-1344.
17. Björkman, A., 1954. Isolation of lignin from finely divided wood with neutral solvents. Nature 174, 1057-1058.
18. Blee, K., Choi, J.W., O'Connell, A.P., Jupe, S.C., Schuch, W., Lewis, N.G., Bolwell, G.P., 2001. Antisense and sense expression of cDNA coding for CYP73A15, a class II cinnamate 4-hydroxylase, leads to a delayed and reduced production of lignin in tobacco. Phytochemistry 57, 1159-1166.
19. Blount, J.W., Korth, K.L., Masoud, S.A., Rasmussen, S., Lamb, C., Dixon, R.A., 2000. Altering expression of cinnamic acid 4-hydroxylase in transgenic plants provides evidence for a feedback loop at the entry point into the phenylpropanoid pathway. Plant Physiology 122, 107-116.
20. Boudet, A.-M., 1998. A new view of lignification. Trends in Plant Sciences 3, 67-71.
21. Brauns, F.E., 1939. Native lignin, I. Its isolation and methylation. Journal of the American Chemical Society 61, 2120-2127.
22. Brauns, F.E., 1952. The Chemistry of Lignin. Academic Press, New York.
23. Brill, E.M., Abrahams, S., Hayes, C.M., Jenkins, C.L., Watson, J.M., 1999. Molecular characterisation and expression of a wound-inducible cDNA encoding a novel cinnamyl-alcohol dehydrogenase enzyme in lucerne (Medicago sativa L.). Plant Molecular Biology 41, 279-291.
24. Busam, G., Junghanns, K.T., Kneusel, R.E., Kassemeyer, H.-H., Matern, U., 1997. Characterization and expression of caffeoylcoenzyme A 3-O-methyltransferase proposed for the induced resistance response of Vitis vinifera L., Plant Physiology 115, 1039-1048.
25. Camm, E.L., Towers, G.H.N., 1973. Phenylalanine ammonia lyase. Phytochemistry 12, 961-973.
26. Chabannes, M., Barakate, A., Lapierre, C., Marita, J.M., Ralph, J., Pean, M., Danoun, S., Halpin, C., Grima-Pettenati, J., Boudet, A.M., 2001. Strong decrease in lignin content without significant alteration of plant development is induced by simultaneous down- regulation of cinnamoyl CoA reductase (CCR) and cinnamyl alcohol dehydrogenase (CAD) in tobacco plants. The Plant Journal 28, 257-270.
27. Chapple, C.C.S., Vogt, T., Ellis, B.E., Somerville, C.R., 1992. An Arabidopsis mutant defective in the general phenylpropanoid pathway. The Plant Cell 4, 1413-1424.
28. Chattaway, M., 1952. The sapwood-heartwood transition. Australian Forestry 16, 25-34.
29. Chen, C., Meyermans, H., Van Doorsselaere, J., Van Montagu, M., Boerjan, W., 1998. A gene encoding caffeoyl coenzyme A 3-O- methyltransferase (CCoAOMT) from Populus trichocarpa (Accession No. AJ223621). Plant Physiology 117, 719.
30. 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 DC. Planta 207, 597-603.
31. Creighton, R.H.J., McCarthy, J.L., Hibbert, H., 1941. Studies on lignin and related compounds. LIX. Aromatic aldehydes from plant materials. Journal of the American Chemical Society 63, 3049-3052.
32. Croteau, R., Kutchan, T.M., Lewis, N.G., 2000. Natural products (secondary metabolites). In: Buchanan, B.B., Gruissem, W., Jones, R.L. (Eds.), Biochemistry and Molecular Biology of Plants. American Society of Plant Physiologist, Rockville, MD, pp. 1250-1318.
33. Davin, L.B., Lewis, N.G., 1992. Phenylpropanoid metabolism: biosynthesis of monolignols, lignans and neolignans, lignins and suberins. In: Stafford, H.A., Ibrahim, R.K. (Eds.), Phenolic Metabolism in Plants, Vol. 26. Plenum Press, New York and London, pp. 325-375.
34. Duke, S.O., Vaughn, K.C., 1982. Lack of involvement of polyphenol oxidase in ortho-hydroxylation of phenolic compounds in mung bean seedlings. Physiologia Plantarum 54, 381-385.
35. Dwivedi, U.N., Campbell, W.H., Yu, J., Datla, R.S.S., Bugos, R.C., Chiang, V.L., Podila, G.K., 1994. Modification of lignin biosynthesis in transgenic Nicotiana through expression of an antisense O-methyl-transferase gene from Populus. Plant Molecular Biology 26, 61-71.
36. Eberhardt, T.L., Bernards, M.A., He, L., Davin, L.B., Wooten, J.B., Lewis, N.G., 1993. Lignification in cell suspension cultures of Pinus taeda. In situ characterization of a gymnosperm lignin. The Journal of Biological Chemistry 268, 21088-21096.
37. Ehlting, J., Büttner, D., Wang, Q., Douglas, C.J., Somssich, I.E., Kombrink, E., 1999. Three 4-coumarate:coenzyme A ligases in Arabidopsis thaliana represent two evolutionarily divergent classes in angiosperms. The Plant Journal 19, 9-20.
38. Elkind, Y., Edwards, R., Mavandad, M., Hedrick, S.A., Ribak, O., Dixon, R.A., Lamb, C.J., 1990. Abnormal plant development and down-regulation of phenylpropanoid biosynthesis in transgenic tobacco containing a heterologous phenylalanine ammonia-lyase gene. Proceedings of the National Academy of Sciences of the United States of America 87, 9057-9061.
39. Emerson, R. A., Beadle, G. W., Fraser, A. C., 1935. A Summary of Linkage Studies in Maize. Cornell University Agricultural Experimental Station Memoir 180.
40. Fahrendorf, T., Dixon, R.A., 1993. Stress responses in alfalfa (Medicago sativa L.) XVIII: molecular cloning and expression of the elicitor-inducible cinnamic acid 4-hydroxylase cytochrome P450. Archives of Biochemistry and Biophysics 305, 509-515.
41. Fell, D., 1997. Understanding the Control of Metabolism. Portland Press, Ltd, London.
42. Fergus, B.J., Goring, D.A.I., 1970a. The distribution of lignin in birch wood as determined by ultraviolet microscopy. Holzforschung 24, 118-124.
43. Fergus, B.J., Goring, D.A.I., 1970b. The location of guaiacyl and syringyl lignins in birch xylem tissue. Holzforschung 24, 113-117.
44. 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. The Plant Journal 30, 47-59.
45. 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. The Plant Journal 22, 223-234.
46. Freedman, D., Pisani, R., Purves, R., 1978. Statistics. Norton & Company, Inc, New York.
47. Fukasawa-Akada, T., Kung, S.-D., Watson, J.C., 1996. Phenylalanine ammonia-lyase gene structure, expression, and evolution in Nicotiana. Plant Molecular Biolgy 30, 711-722.
48. Fukushima, K., Matsui, N., Taguchi, S., Yasuda, S., 1997. On the roles of monolignol glucosides and monolignol pathway (coniferyl alcohol-5-hydroxyconiferyl alcohol-sinapyl alcohol) in lignin biosynthesis of Magnolia kobus. In: 9th International Symposium on Wood and Pulping Chemistry, 9-12 June 1997, Montreal, Quebec, Canada 28-(21-24).
49. Galliano, H., Heller, W., Sandermann, H.J., 1993. Ozone induction and purification of spruce cinnamyl alcohol dehydrogenase. Phytochemistry 32, 557-563.
50. Gang, D.R., Fujita, M., Davin, L.B., Lewis, N.G., 1998. The "abnormal lignins": mapping heartwood formation through the lignan biosynthetic pathway. In: Lewis, N.G., Sarkanen, S. (Eds.), Lignin and Lignan Biosynthesis, Vol. 697. ACS Symposium Series, Washington, DC, pp. 389-421.
51. Gentinetta, E., Bertolini, M., Rossi, I., Lorenzoni, C., Motto, M., 1990. Effect of brown midrib-3 mutant on forage quality and yield in maize. Journal of Genetics and Breeding 44, 21-26.
52. Goffner, D., Joffroy, I., Grima-Pettenati, J., Halpin, C., Knight, M.E., Schuch, W., Boudet, A.M., 1992. Purification and characterization of isoforms of cinnamyl alcohol dehydrogenase from eucalyptus xylem. Planta 188, 48-53.
53. Grand, C., 1984. Ferulic acid 5-hydroxylase: a new cytochrome P-450-dependent enzyme from higher plant microsomes involved in lignin synthesis. Federation of European Biochemical Societies Letters 169, 7-11.
54. 3) mutant corn seedlings. Physiologie Végétale 23, 905-911.
55. Grima-Pettenati, J., Feuillet, C., Goffner, D., Borderies, G., Boudet, A.M., 1993. Molecular cloning and expression of a Eucalyptus gunnii cDNA clone encoding cinnamyl alcohol dehydrogenase. Plant Molecular Biology 21, 1085-1095.
56. Guo, D., Chen, F., Inoue, K., Blount, J.W., Dixon, R.A., 2001. Downregulation of caffeic acid 3-O-methyltransferase and caffeoyl CoA 3-O-methyltransferase in transgenic alfalfa: impacts on lignin structure and implications for the biosynthesis of G and S lignin. The Plant Cell 13, 73-88.
57. Halpin, C., Holt, K., Chojecki, J., Oliver, D., Chabbert, B., Monties, B., Edwards, K., Barakate, A., Foxon, G.A., 1998. Brown-midrib maize (bm1)-a mutation affecting the cinnamyl alcohol dehydrogenase gene. The Plant Journal 14, 545-553.
58. Halpin, C., Knight, M.E., Foxon, G.A., Campbell, M.M., Boudet, A.M., Boon, J.J., Chabbert, B., Tollier, M.-T., Schuch, W., 1994. Manipulation of lignin quality by downregulation of cinnamyl alcohol dehydrogenase. The Plant Journal 6, 339-350.
59. He, L., Terashima, N., 1990. Formation and structure of lignin in monocotyledons. III. Heterogeneity of sugarcane (Saccharum officinarum L.) lignin with respect to the composition of structural units in different morphological regions. Journal of Wood Chemistry and Technology 10, 435-459.
60. Hepworth, D.G., Vincent, J.F.V., 1998. The mechanical properties of xylem tissue from tobacco plants (Nicotiana tabacum 'Samsun'). Annals of Botany 81, 751-759.
61. Hepworth, D.G., Vincent, J.F.V., 1999. The growth response of the stems of genetically modified tobacco plants (Nicotiana tabacum 'Samsun') to flexural stimulation. Annals of Botany 83, 39-43.
62. Hepworth, D.G., Vincent, J.F.V., Schuch, W., 1998. Using viscoelastic properties of the woody tissue from tobacco plants (Nicotiana tabacum) to comment on the molecular structure of cell walls. Annals of Botany 81, 729-734.
63. Hibino, T., Takabe, K., Kawazu, T., Shibata, D., Higuchi, T., 1995. Increase of cinnamaldehyde groups in lignin of transgenic tobacco plants carrying an antisense gene for cinnamyl alcohol dehydrogenase. Bioscience, Biotechnology, and Biochemistry 59, 929-931.
64. Higuchi, T., Ito, T., Umezawa, T., Hibino, T., Shibata, D., 1994. Redbrown color of lignified tissues of transgenic plants with antisense CAD gene: wine-red lignin from coniferyl aldehyde. Journal of Biotechnology 37, 151-158.
65. Hu, W.-J., Harding, S.A., Lung, J., Popko, J.L., Ralph, J., Stokke, D.D., Tsai, C.-J., Chiang, V.L., 1999. Repression of lignin biosynthesis promotes cellulose accumulation and growth in transgenic trees. Nature Biotechnology 17, 808-812.
66. Hu, W.-J., Kawaoka, A., Tsai, C.-J., Lung, J., Osakabe, K., Ebinuma, H., Chiang, V.L., 1998. Compartmentalized expression of two structurally and functionally distinct 4-coumarate:CoA ligase genes in aspen (Populus tremuloides). Proceedings of the National Academy of Sciences of the United States of America 95, 5407- 5412.
67. Huang, X., Jeronimidis, G., Vincent, J.F.V., 1999. Mechanical properties of wood from transgenic poplar trees with modified lignification. The 2nd Symposium of Chinese Youth Scholars on Material Science and Technology 10, 1-9.
68. Humphreys, J.M., Hemm, M.R., Chapple, C., 1999. New routes for lignin biosynthesis defined by biochemical characterization of recombinant ferulate 5-hydroxylase, a multifunctional cytochrome P450-dependent monooxygenase. Proceedings of the National Academy of Sciences of the United States of America 96, 10045-10050.
69. Iiyama, K., Wallis, A.F.A., 1990. Determination of lignin in herbaceous plants by an improved acetyl bromide procedure. Journal of the Science of Food and Agriculture 51, 145-161.
70. Inoue, K., Sewalt, V.J.H., Ballance, G.M., Ni, W., Stürzer, C., Dixon, R.A., 1998. Developmental expression and substrate specificities of alfalfa caffeic acid 3-O-methyltransferase and caffeoyl coenzyme A 3-O-methyltransferase in relation to lignification. Plant Physiology 117, 761-770.
71. Jones, L., Ennos, A.R., Turner, S.R., 2001. Cloning and characterization of irregular xylem4 (irx4): a severely lignin-deficient mutant of Arabidopsis. The Plant Journal 26, 205-216.
72. Jorgenson, L.R., 1931. Brown midrib in maize and its linkage relations. Journal of the American Society of Agronomy 23, 549-557.
73. Jouanin, L., Goujon, T., de Nadaï, V., Martin, M.-T., Mila, I., Vallet, C., Pollet, B., Yoshinaga, A., Chabbert, B., Petit-Conil, M., Lapierre, C., 2000. Lignification in transgenic poplars with extremely reduced caffeic acid O-methyltransferase activity. Plant Physiology 123, 1363-1373.
74. Jung, H.-J.G., Ni, W., Chapple, C.C.S., Meyer, K., 1999. Impact of lignin composition on cell-wall degradability in an Arabidopsis mutant. Journal of the Science of Food and Agriculture 79, 922-928.
75. Kajita, S., Hishiyama, S., Tomimura, Y., Katayama, Y., Omori, S., 1997a. Structural characterization of modified lignin in transgenic tobacco plants in which the activity of 4-coumarate:coenzyme A ligase is depressed. Plant Physiology 114, 871-879.
76. Kajita, S., Katayama, Y., Omori, S., 1996. Alterations in the biosynthesis of lignin in transgenic plants with chimeric genes for 4-coumarate:coenzyme A ligase. Plant Cell Physiology 37, 957-965.
77. Kajita, S., Mashino, Y., Nishikubo, N., Katayama, Y., Omori, S., 1997b. Immunological characterization of transgenic tobacco plants with a chimeric gene for 4-coumarate:CoA ligase that have altered lignin in their xylem tissue. Plant Science 128, 109-118.
78. Kawaoka, A., Ebinuma, H., 2001. Transcriptional control of lignin biosynthesis by tobacco LIM protein. Phytochemistry 57, 1149- 1157.
79. Kawaoka, A., Kaothien, P., Yoshida, K., Endo, S., Yamada, K., Ebinuma, H., 2000. Functional analysis of tobacco LIM protein Ntliml involved in lignin biosynthesis. The Plant Journal 22, 289-301.
80. Klason, P., von Heidenstam, G., Norlin, E., 1908. Teoretiska undersökningar rörande kolning af ved. II. Torrdestillation af furu-, gran-, björk-och bokved. Arkiv för Kemi, Mineralogi och Geologi 3, 1-17.
81. 2+-dependent enzymes in cultured plant cells and its activation by an elicitor-induced pH shift. Archives of Biochemistry and Biophysics 269, 455-462.
82. Knight, M.E., Halpin, C., Schuch, W., 1992. Identification and characterisation of cDNA clones encoding cinnamyl alcohol dehydrogenase from tobacco. Plant Molecular Biology 19, 793-801.
83. Kojima, M., Takeuchi, W., 1989. Detection and characterization of p-coumaric acid hydroxylase in mung bean, Vigna mungo, seedlings. The Journal of Biochemistry 105, 265-270.
84. Korth, K.L., Blount, J.W., Chen, F., Rasmussen, S., Lamb, C., Dixon, R.A., 2001. Changes in phenylpropanoid metabolites associated with homology-dependent silencing of phenylalanine ammonia-lyase and its somatic reversion in tobacco. Physiologia Plantarum 111, 137-143.
85. Kuc, J., Nelson, O.E., 1964. The abnormal lignins produced by the brown-midrib mutants of maize. I. The brown-midrib-I mutant. Archives of Biochemistry and Biophysics 105, 103-113.
86. Kuc, J., Nelson, O.E., Flanagan, P., 1968. Degradation of abnormal lignins in the brown-midrib mutants and double mutants of maize. Phytochemistry 7, 1435-1436.
87. Kühnl, T., Koch, U., Heller, W., Wellmann, E., 1987. Chlorogenic acid biosynthesis: characterization of a light-induced microsomal 5-O-(4-coumaroyl)-D-quinate/shikimate 3′-hydroxylase from carrot (Daucus carota L.) cell suspension cultures. Archives of Biochemistry and Biophysics 258, 226-232.
88. Lacombe, E., Hawkins, S., Van Doorsselaere, J., Piquemal, J., Goffner, D., Poeydomenge, O., Boudet, A.-M., Grima-Pettenati, J., 1997. Cinnamoyl CoA reductase, the first committed enzyme of the lignin branch biosynthetic pathway: cloning, expression and phylogenetic relationships. The Plant Journal 11, 429-441.
89. Lai, Y.Z., Sarkanen, K.V., 1971. Isolation and structural studies. In: Sarkanen, K.V., Ludwig, C.H. (Eds.), Lignins. Occurence, Formation, Structure and Reactions. Wiley Interscience, New York, pp. 165-240.
90. Lapierre, C., Monties, B., Rolando, C., 1986. Thioacidolysis of poplar lignins: identification of monomeric syringyl products and characterization of guaiacyl-syringyl lignin fractions. Holzforschung 40, 113-118.
91. Lapierre, C., Pollet, B., Petit-Conil, M., Toval, G., Romero, J., Pilate, G., Leplé, J.-C., Boerjan, W., Ferret, V., De Nadai, V., Jouanin, L., 1999. Structural alterations of lignins in transgenic poplars with depressed cinnamyl alcohol dehydrogenase or caffeic acid O-methyltransferase activity have an opposite impact on the efficiency of industrial kraft pulping. Plant Physiology 119, 153-163.
92. Lapierre, C., Tollier, M.-T., Monties, B., 1988. Mise en évidence d'un nouveau type d'unité constitutive dans les lignines d'un mutant de maïs bm3. Comptes Rendus de l'Académie des Sciences. Série III, Sciences de la Vie 307, 723-728.
93. Lauvergeat, V., Lacomme, C., Lacombe, E., Lasserre, E., Roby, D., Grima-Pettenati, J., 2001. Two cinnamoyl-CoA reductase (CCR) genes from Arabidopsis thaliana are differentially expressed during development and in response to infection with pathogenic bacteria. Phytochemistry 57, 1187-1195.
94. Lee, D., Meyer, K., Chapple, C., Douglas, C.J., 1997. Antisense suppression of 4-coumarate:coenzyme A ligase activity in Arabidopsis leads to altered lignin subunit composition. The Plant Cell 9, 1985-1998.
95. Lewis, N.G., 1999. A 20th century roller coaster ride: a short account of lignification. Current Opinion in Plant Biology 2, 153-162.
96. Lewis, N. G., Davin, L. B., 1994. Evolution of lignan and neolignan biochemical pathways. In: Nes, W. D., (Ed.), Isopentenoids and Other Natural Products: Evolution and Function. ACS Symposium Series No. 562, pp. 202-246.
97. Lewis, N.G., Davin, L.B., 1999. Lignans: biosynthesis and function. In: Barton, D.H.R., Sir, Nakanishi, K., Meth-Cohn, O. (Eds.), Comprehensive Natural Products Chemistry, Vol. 1. Elsevier, London, pp. 639-712.
98. Lewis, N.G., Davin, L.B., Sarkanen, S., 1998. Lignin and lignan biosynthesis: distinctions and reconciliations. In: Lewis, N.G., Sarkanen, S. (Eds.), Lignin and Lignan Biosynthesis, Vol. 697. ACS Symposium Series, Washington, DC, pp. 1-27.
99. Lewis, N. G., Davin, L. B., Sarkanen, S. 1999. The nature and function of lignins. In: Barton, D. H. R., Sir, Nakanishi, K., Meth-Cohn, O., (Eds.), Comprehensive Natural Products Chemistry, Vol. 3, pp. 617-745.
100. Lewis, N.G., Goring, D.A.I., Wong, A., 1983. Fractionation of lignosulphonates released during the early stages of delignification. Canadian Journal of Chemistry 61, 416-420.
101. Lewis, N.G., Yamamoto, E., 1990. Lignin: occurrence, biogenesis and biodegradation. Annual Review of Plant Physiology and Plant Molecular Biology 41, 455-497.
102. Lewis, N.G., Yean, W.Q., 1985. High performance size-exclusion chromatography of lignosulphonates. Journal of Chromatography 331, 419-424.
103. Li, L., Cheng, X.F., Leshkevich, J., Umezawa, T., Harding, S.A., Chiang, V.L., 2001. The last step in syringyl monolignol biosynthesis in angiosperms is regulated by a novel gene encoding sinapyl alcohol dehydrogenase. The Plant Cell 13, 1567-1585.
104. Li, L., Popko, J.L., Umezawa, T., Chiang, V.L., 2000. 5-Hydroxyconiferyl aldehyde modulates enzymatic methylation for syringyl monolignol formation, a new view of monolignol biosynthesis in angiosperms. The Journal of Biological Chemistry 275, 6537-6545.
105. Li, L., Popko, J.L., Zhang, X.-H., Osakabe, K., Tsai, C.-J., Joshi, C.P., Chiang, V.L., 1997. A novel multifunctional O-methyl- transferase implicated in a dual methylation pathway associated with lignin biosynthesis in loblolly pine. Proceedings of the National Academy of Sciences of the United States of America 94, 5461-5466.
106. Liang, X., Dron, M., Cramer, C.L., Dixon, R.A., Lamb, C.J., 1989. Differential regulation of phenylalanine ammonia-lyase genes during plant development and by environmental cues. The Journal of Biological Chemistry 264, 14486-14492.
107. Lindermayr, C., Möllers, B., Fliegmann, J., Uhlmann, A., Lottspeich, F., Meimberg, H., Ebel, J., 2002. Divergent members of a soybean (Glycine max L.) 4-coumarate:coenzyme A ligase gene family: primary structure, catalytic properties and differential expression. European Journal of Biochemistry 296, 1304-1315.
108. Lorenz, D., Morris, D., 1995. How much energy does it take to make a gallon of ethanol? http://www.carbohydrateeconomy.org.
109. + dehydrogenase from spruce (Picea abies L.) and soybean (Glycine max L.). European Journal of Biochemistry 119, 115-124.
110. Luthe, C.E., Lewis, N.G., 1986. Identification and characterization of paucidisperse lignosulphonates. Holzforschung 40 (Suppl.), 153-157.
111. Mansell, R.L., Babbel, G.R., Zenk, M.H., 1976. Multiple forms and specificity of coniferyl alcohol dehydrogenase from cambial regions of higher plants. Phytochemistry 15, 1849-4853.
112. Marita, J.M., Ralph, J., Hatfield, R.D., Chapple, C., 1999. NMR characterization of lignins in Arabidopsis altered in the activity of ferulate 5-hydroxylase. Proceedings of the National Academy of Sciences of the United States of America 96, 12328-12332.
113. Martz, F., Maury, S., Pinçon, G., Legrand, M., 1998. cDNA cloning, substrate specificity and expression study of tobacco caffeoyl-CoA 3-O-methyltransferase, a lignin biosynthetic enzyme. Plant Molecular Biology 36, 427-437.
114. Matsui, N., Chen, F., Yasuda, S., Fukushima, K., 2000. Conversion of guaiacyl to syringyl moieties on the cinnamyl alcohol pathway during the biosynthesis of lignin in angiosperms. Planta 210, 831-835.
115. Maury, S., Geoffroy, P., Legrand, M., 1999. Tobacco O-methyl-transferases involved in phenylpropanoid metabolism. The different caffeoyl-coenzyme A/5-hydroxyferuloyl-coenzyme A 3/5-O-methyl-transferase and caffeic acid/5-hydroxyferulic acid 3/5-O-methyl-transferase classes have distinct substrate specificities and expression patterns. Plant Physiology 121, 215-223.
116. Meng, H., Campbell, W.H., 1998. Substrate profiles and expression of caffeoyl coenzyme A and caffeic acid O-methyltransferases in secondary xylem of aspen during seasonal development. Plant Molecular Biology 38, 513-520.
117. 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 of the United States of America 95, 6619-6623.
118. Meyermans, H., Morreel, K., Lapierre, C., Pollet, B., De Bruyn, A., Busson, R., Herdewijn, P., Devreese, B., Van Beeumen, J., Marita, J.M., Ralph, J., Chen, C., Burggraeve, B., Van Montagu, M., Messens, E., Boerjan, W., 2000. Modifications in lignin and accumulation of phenolic glucosides in poplar xylem upon down-regulation of caffeoyl-coenzyme A O-methyltransferase, an enzyme involved in lignin biosynthesis. The Journal of Biological Chemistry 275, 36899-36909.
119. Muller, L.D., Barnes, R.F., Bauman, L.F., Colenbrander, V.F., 1971. Variations in lignin and other structural components of brown midrib mutants of maize. Crop Science 11, 413-415.
120. Nedelkina, S., Jupe, S.C., Blee, K.A., Schalk, M., Werck-Reichhart, D., Bolwell, G.P., 1999. Novel characteristics and regulation of a divergent cinnamate 4-hydroxylase (CYP73A15) from French bean: engineering expression in yeast. Plant Molecular Biology 39, 1079-1090.
121. Ni, W., Paiva, N.L., Dixon, R.A., 1994. Reduced lignin in transgenic plants containing a caffeic acid O-methyltransferase antisense gene. Transgenic Research 3, 120-126.
122. Nose, M., Bernards, M.A., Furlan, M., Zajicek, J., Eberhardt, T.L., Lewis, N.G., 1995. Towards the specification of consecutive steps in macromolecular lignin assembly. Phytochemistry 39, 71-79.
123. Ohashi, H., Yamamoto, E., Lewis, N.G., Towers, G.H.N., 1987. 5-Hydroxyferulic acid in Zea mays and Hordeum vulgare cell walls. Phytochemistry 26, 1915-1916.
124. O'Malley, D., Porter, S., Sederoff, R., 1992. Purification, characterization, and cloning of cinnamyl alcohol dehydrogenase in loblolly pine (Pinus taeda L.). Plant Physiology 98, 1364-1371.
125. Osakabe, K., Tsao, C.C., Li, L., Popko, J.L., Umezawa, T., Carraway, D.T., Smeltzer, R.H., Joshi, C.P., Chiang, V.L., 1999. Coniferyl aldehyde 5-hydroxylation and methylation direct syringyl lignin biosynthesis in angiosperms. Proceedings of the National Academy of Sciences of the United States of America 96, 8955-8960.
126. Padmapriya, A.A., Just, G., Lewis, N.G., 1985. A new method for the esterification of sulphonic acids. Synthetic Communications 15, 1057-1062.
127. Parvathi, K., Chen, F., Guo, D., Blount, J.W., Dixon, R.A., 2001. Substrate preferences of O-methyltransferases in alfalfa suggest new pathways for 3-O-methylation of monolignols. The Plant Journal 25, 193-202.
128. Pearce, G., Marchand, P.A., Griswold, J., Lewis, N.G., Ryan, C.A., 1998. Accumulation of feruloyltyramine and p-coumaroyltyramine in tomato leaves in response to wounding. Phytochemistry 47, 659-664.
129. Pichon, M., Courbou, I., Beckert, M., Boudet, A.-M., Grima-Pettenati, J., 1998. Cloning and characterization of two maize cDNAs encoding cinnamoyl-CoA reductase (CCR) and differential expression of the corresponding genes. Plant Molecular Biology 38, 671-676.
130. Pinçon, G., Maury, S., Hoffmann, L., Geoffroy, P., Lapierre, C., Pollet, B., Legrand, M., 2001. Repression of O-methyltransferase genes in transgenic tobacco affects lignin synthesis and plant growth. Phytochemistry 57, 1167-1176.
131. Piquemal, J., Lapierre, C., Myton, K., O'Connell, A., Schuch, W., Grima-Pettenati, J., Boudet, A.-M., 1998. Down-regulation of cinnamoyl-CoA reductase induces significant changes of lignin profiles in transgenic tobacco plants. The Plant Journal 13, 71-83.
132. Provan, G.J., Scobbie, L., Chesson, A., 1997. Characterisation of lignin from CAD and OMT deficient Bm mutants of maize. Journal of the Science of Food and Agriculture 73, 133-142.
133. Ralph, J., 1997. Recent advances in characterizing 'non-traditional' lignins. 9th International symposium on wood and pulping chemistry 1, PL2/1-PL2/7.
134. Ralph, J., Hatfield, R.D., 1991. Pyrolysis-GC-MS characterization of forage materials. Journal of Agricultural and Food Chemistry 39, 1426-1437.
135. Ralph, J., Hatfield, R.D., Piquemal, J., Yahiaoui, N., Pean, M., Lapierre, C., Boudet, A.M., 1998. NMR characterization of altered lignins extracted from tobacco plants down-regulated for lignification enzymes cinnamyl-alcohol dehydrogenase and cinnamoyl-CoA reductase. Proceedings of the National Academy of Sciences of the United States of America 95, 12803-12808.
136. Ralph, J., Lapierre, C., Lu, F., Marita, J.M., Pilate, G., Doorsselaere, J.V., Boerjan, W., Jouanin, L., 2001. NMR evidence for benzodioxane structures resulting from incorporation of 5-hydroxy-coniferyl alcohol into lignins of O-methyltransferase-deficient poplars. Journal of Agricultural and Food Chemistry 49, 86-91.
137. Ralph, J., MacKay, J.J., Hatfield, R.D., O'Malley, D.M., Whetten, R.W., Sederoff, R.R., 1997. Abnormal lignin in a loblolly pine mutant. Science 277, 235-239.
138. Rubery, P.H., Fosket, D.E., 1969. Changes in phenylalanine ammonia lyase activity during xylem differentiation in Coleus and soybean. Planta 87, 54-62.
139. Sakakibara, A., Sasaya, T., Miki, K., Takahashi, H., 1987. Lignans and Brauns' lignins from softwoods. Holzforschung 41, 1-11.
140. Sarkanen, K.V., Ludwig, C.H., 1971. Definition and nomenclature. In: Sarkanen, K.V., Ludwig, C.H. (Eds.), Lignins. Occurrence, Formation, Structure and Reactions. Wiley Interscience, New York, pp. 1-41.
141. Sarkanen, S., 1998. Template polymerization in lignin biosynthesis. In: Lewis, N.G., Sarkanen, S. (Eds.), Lignin and Lignan Biosynthesis, Vol. 697. ACS Symposium Series, Washington, DC, pp. 194-208.
142. Schmitt, D., Pakusch, A.-E., Matern, U., 1991. Molecular cloning, induction, and taxonomic distribution of caffeoyl-CoA 3-O-methyl-transferase, an enzyme involved in disease resistance. The Journal of Biological Chemistry 266, 17416-17423.
143. Schoch, G., Goepfert, S., Morant, M., Hehn, A., Meyer, D., Ullmann, P., Werck-Reichhart, D., 2001. CYP98A3 from Arabidopsis thaliana is a 3′-hydroxylase of phenolic esters, a missing link in the phenyl-propanoid pathway. The Journal of Biological Chemistry 276, 36566-36574.
144. Sewalt, V.J.H., Ni, W., Blount, J.W., Jung, H.G., Masoud, S.A., Howles, P.A., Lamb, C., Dixon, R.A., 1997a. Reduced lignin content and altered lignin composition in transgenic tobacco downregulated in expression of L-phenylalanine ammonia-lyase or cinnamate 4-hydroxylase. Plant Physiology 115, 41-50.
145. Sewalt, V.J.H., Ni, W., Jung, H.G., Dixon, R.A., 1997b. Lignin impact on fiber degradation: increased enzymatic digestibility of genetically engineered tobacco (Nicotiana tabacum) stems reduced in lignin content. Journal of Agricultural and Food Chemistry 45, 1977-1983.
146. Smart, C.C., Amrhein, N., 1985. The influence of lignification on the development of vascular tissue in Vigna radiata L.. Protoplasma 124, 87-95.
147. Smith, D.C.C., 1955. p-Hydroxybenzoate groups in the lignin of aspen (Populus tremula). Journal of the Chemical Society 2347-2351.
148. Tamagnone, L., Merida, A., Parr, A., MacKay, S., Culianez-Macia, F.A., Roberts, K., Martin, C., 1998. The AmMYB308 and AmMYB330 transcription factors from antirrhinum regulate phenylpropanoid and lignin biosynthesis in transgenic tobacco. The Plant Cell 10, 135-154.
149. Tanaka, M., Kojima, M., 1991. Purification and characterization of p-coumaroyl-D-glucose hydroxylase of sweet potato (lpomoea batatas) roots. Archives of Biochemistry and Biophysics 284, 151-157.
150. The Arabidopsis Genome Initiative, 2000. Analysis of the genome sequence of the flowering plant Arabidopsis thaliana. Nature 408, 796-815.
151. Timell, T.E., 1986. Compression Wood in Gymnosperms. Springer- Verlag, Berlin.
152. Tsai, C.-J., Popko, J.L., Mielke, M.R., Hu, W.-J., Podila, G.K., Chiang, V.L., 1998. Suppression of O-methyltransferase gene by homologous sense transgene in quaking aspen causes red-brown wood phenotypes. Plant Physiology 117, 101-112.
153. Van Doorsselaere, J., Baucher, M., Chognot, E., Chabbert, B., Tollier, M.-T., Petit-Conil, M., Leplé, J.-C., Pilate, G., Cornu, D., Monties, B., Van Montagu, M., Inzé, D., Boerjan, W., Jouanin, L., 1995a. A novel lignin in poplar trees with a reduced caffeic acid/5-hydroxyferulic acid O-methyltransferase activity. The Plant Journal 8, 855-864.
154. Van Doorsselaere, J., Baucher, M., Feuillet, C., Boudet, A.M., Van Montagu, M., Inze, D., 1995b. Isolation of cinnamyl alcohol dehydrogenase cDNAs from two important economic species: alfalfa and poplar. Demonstration of a high homology of the gene within angiosperms. Plant Physiology and Biochemistry 33, 105-109.
155. van Heerden, P.S., Towers, G.H.N., Lewis, N.G., 1996. Nitrogen metabolism in lignifying Pinus taeda cell cultures. The Journal of Biological Chemistry 271, 12350-12355.
156. van Rensburg, H., Anterola, A.M., Levine, L.H., Davin, L.B., Lewis, N.G., 2000. Monolignol compositional determinants in loblolly pine: aromatic amino acid metabolism and associated rate-limiting steps. In: Glasser, W.G., Northey, R.A., Schultz, T.P. (Eds.), Lignin: Historical, Biological, and Materials Perspectives, Vol. 742. ACS Symposium Series, Washington, DC, pp. 118-144.
157. Van Soest, P.J., Robertson, J.B., Lewis, B.A., 1991. Methods for dietary fiber, neutral detergent fiber, and nonstarch polysaccharides in relation to animal nutrition. Journal of Dairy Science 74, 3583-3597.
158. Vignols, F., Rigau, J., Torres, M.A., Capellades, M., Puigdomènech, P., 1995. The brown midrib3 (bm3) mutation in maize occurs in the gene encoding caffeic acid O-methyltransferase. The Plant Cell 7, 407-416.
159. Wang, Z.-X., Li, S.-M., Löscher, R., Heide, L., 1997. 4-Coumaroyl coenzyme A 3-hydroxylase activity from cell cultures of Lithospermum erythrorhizon and its relationship to polyphenol oxidase. Archives of Biochemistry and Biophysics 347, 249-255.
160. Weller, R.F., Phipps, R.H., Cooper, A., 1985. The effect of the brown midrib-3 gene on the maturity and yield of forage maize. Grass and Forage Science 40, 335-339.
161. Westing, A.H., 1965. Formation and function of compression wood in gymnosperms. Botanical Reviews 31, 381-480.
162. Whiting, P., Goring, D.A.I., 1982. Chemical characterization of tissue fractions from the middle lamella and secondary wall of black spruce tracheids. Wood Science and Technology 16, 261-267.
163. Wyrambik, D., Grisebach, H., 1975. Purification and properties of isoenzymes of cinnamyl-alcohol dehydrogenase from soybean-cellsuspension cultures. European Journal of Biochemistry 59, 9-15.
164. Yahiaoui, N., Marque, C., Myton, K.E., Negrel, J., Boudet, A.M., 1998. Impact of different levels of cinnamyl alcohol dehydrogenase down-regulation on lignins of transgenic tobacco plants. Planta 204, 8-15.
165. Ye, Z.-H., 1997. Association of caffeoyl coenzyme A 3-O-methyl-transferase expression with lignifying tissues in several dicot plants. Plant Physiology 115, 1341-1350.
166. Ye, Z.-H., Varner, J.E., 1995. Differential expression of two O-methyltransferases in lignin biosynthesis in Zinnia elegans. Plant Physiology 108, 459-467.
167. Zhang, X.H., Dickson, E.E., Chinnappa, C.C., 1995. Nucleotide sequence of a cDNA clone encoding caffeoyl-coenzyme A 3-O-methyltransferase of Stellaria longipes (Caryophyllaceae). Plant Physiology 108, 429-430.
168. Zhong, R., Morrison III, W.H., Himmelsbach, D.S., Poole II, F.L., Ye, Z.-H., 2000. Essential role of caffeoyl coenzyme A O-methyl-transferase in lignin biosynthesis in woody poplar plants. Plant Physiology 124, 563-577.
169. Zhong, R., Morrison III, W.H., Negrel, J., Ye, Z.-H., 1998. Dual methylation pathways in lignin biosynthesis. The Plant Cell 10, 2033-2045.
170. Zou, J., Taylor, D.C., 1994. Isolation of an Arabidopsis thaliana cDNA homologous to parsley (Petroselinum crispum) S-adenosyl-L-methionine: trans-caffeoyl-coenzyme A 3-O-methyltransferase, an enzyme involved in disease resistance. Plant Physiology and Biochemistry 32, 423-427.
171. Zuber, M.S., Colbert, T.R., Bauman, L.F., 1977. Effect of brownmidrib-3 mutant in maize (Zea mays L.) on stalk strength. Zeitschrift für Pflanzenzüchtung 79, 310-314.