Recent advances in understanding lignin biosynthesis

Annual Review of Plant Biology

Volumn 49, Issue , 1998, Pages 585-609

  Whetten, Ross W ^a,b   MacKay, John J ^b   Sederoff, Ronald R ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

^b GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Forage quality; Lignin composition; Metabolic plasticity; Monolignol biosynthesis; Pulp manufacturing

Indexed keywords

BIOSYNTHESIS; CELL WALL; GENETIC CHANGE; GENETIC MODIFICATION; LIGNIN; PLANT GENETICS;

EID: 0031734814     PISSN: 15435008     EISSN: None     Source Type: Book Series    
DOI: 10.1146/annurev.arplant.49.1.585     Document Type: Article

References (110)

1. Agarwal UP, Atalla RH. 1986. In-situ microprobe studies of plant cell walls: macromolecular organization and compositional variability in the secondary wall of Picea mariana (Mill.) B.S.P. Planta 169:325-32
2. Atalla RH, Agarwal UP. 1985. Raman microprobe evidence for lignin orientation in the cell walls of native woody tissue. Science 227:636-38
3. Atanassova R, Favet N, Martz F, Chabbert B, Tollier M-T, et al. 1995. Altered lignin composition in transgenic tobacco expressing O-methyltransferase sequences in sense and antisense orientation. Plant J. 8:465-77
4. Bao W, O'Malley DM, Whetten R, Sederoff RR. 1993. A laccase associated with lignification in loblolly pine xylem. Science 260:672-74
5. Bate N, Orr J, Ni W, Meromi A, Nadler-Hassar T, et al. 1994. Quantitative relationship between phenylalanine ammonia-lyase levels and phenylpropanoid accumulation in transgenic tobacco identifies a rate-determining step in natural product synthesis. Proc. Natl. Acad. Sci. USA 91:7608-12
6. Baucher M, Chabbert B, Pilate G, van Doorsselaere J, Tollier M-T, et al. 1996. Red xylem and higher lignin extractability by down-regulating cinnamyl alcohol dehydrogenase in poplar (Populus tremula and Populus alba). Plant Physiol. 112:1479-90
7. Besle JM, Cornu A, Jouany JP. 1994. Roles of structural phenylpropanoids in forage cell wall digestion. J. Sci. Food Agric. 64:171-90
8. Bligny R, Douce R. 1983. Excretion of laccase by sycamore (Acer pseudoplatanus L.) cells. Biochem. J. 209:489-96
9. Boerjan W, Meyermans H, Chen C, Leplé J-C, Christensen JH, et al. 1996. Genetic engineering of lignin biosynthesis in poplar. In Somatic Cell Genetics and Molecular Genetics of Trees, ed. MR Ahuja, W Boerjan, DB Neale, pp. 81-88. Dordrecht: Kluwer
10. Boudet AM, Grima-Pettenati J. 1996. Lignification genes: structure, function and regulation. Proc. Keystone Symp. Extracell. Matrix Plants: Mol. Cell. Dev. Biol., Tamarron, Colo., p. 7. New York: Wiley-Liss
11. Boudet AM, Lapierre C, Grima-Pettenati J. 1995. Biochemistry and molecular biology of lignification. New Phytol. 129:203-36
12. Browning BL. 1967. Methods of Wood Chemistry. Appleton, Wis: Inst. Pap. Chem. 384 pp.
13. Campbell MM, Sederoff RR. 1996. Variation in lignin content and composition. Plant Physiol. 110:3-13
14. Chabanet A, Goldberg R, Catesson AM, Quinet-Szely M, Delauney AM, Faye L. 1994. Plant Physiol. 106:1095
15. Chapple CC, Vogt T, Ellis BE, Somerville CR. 1992. An Arabidopsis mutant defective in the general phenylpropanoid pathway. Plant Cell 4:1413-24
16. Chen C-L. 1991. Lignin: occurrence in woody tissues, isolation, reactions, and structure. See Ref. 57a, pp. 183-261
17. Das NN, Das SC, Sarkar AK, Mukherjee AK. 1984. Lignin-xylan ester linkage in mesta fiber (Hibiscus cannabinus). Carbohydr. Res. 129:197-207
18. Davin LB, Bedgar DL, Katayama T, Lewis NG. 1992. On the stereoselective synthesis of (+)-pinoresinol in Forsythia suspensa from its achiral precursor, coniferyl alcohol. Phytochemistry 31:3869-74
19. Davin LB, Wang H-B, Crowell AL, Bedgar DL, Martin DM, et al. 1997. Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center. Science 275:362-66
20. Dean JFD, Eriksson KEL. 1994. Laccase and the deposition of lignin in vascular plants. Holzforschung 48:21-33
21. Dean JFD, LaFayette PR, Rugh CL, Merkle SA, Eriksson KEL. 1996. The role of laccase in lignin biosynthesis. In Proc. Keystone Symp. Extracell. Matrix Plants: Mol. Cell. Dev. Biol., Tamarron, Colo., p. 6. New York: Wiley-Liss
22. Dharmawardhana DP, Ellis BE, Carlson JE. 1995. A β-glucosidase from lodgepole pine xylem specific for the lignin precursor coniferin. Plant Physiol. 107:331-39
23. Douglas CJ. 1996. Phenylpropanoid metabolism and lignin biosynthesis: from weeds to trees. Trends Plant Sci. 1:171-78
24. Driouch A, Lainé AC, Vian B, Faye L. 1992. Characterization and localization of laccase forms in stem and cell cultures of sycamore. Plant J. 2:13-24
25. Elkind Y, Edwards R, Mavandad M, Hedrick SA, Ribak O. et al. 1990. Abnormal plant development and down-regulation of phenylpropanoid biosynthesis in transgenic tobacco containing a heterologous phenylalanine ammonialyase gene. Proc. Natl. Acad. Sci. USA 87:9057-61
26. Erdtman H. 1933. Dehydrierungen in der Coniferylreihe. (1) Dehydrodieugenol und dehydrodiisoeugenol. Z. Biochem. 258:172-80
27. Freudenberg K. 1959. Biosynthesis and constitution of lignin. Nature 183:1152-55
28. Freudenberg K. 1965. Lignin: its constitution and formation from p-hydroxycinnamyl alcohols. Science 148:595-600
29. Freudenberg K. 1968. The constitution and biosynthesis of lignin. In Constitution and Biosynthesis of Lignin, ed. K Freudenberg, AC Neish, pp. 47-116. New York: Springer-Verlag
30. Freudenberg K, Harkin JM. 1963. The glucosides of cambial sap of spruce. Phytochemistry 2:189-93
31. Freudenberg K, Harkin JM, Reichert M, Fukuzumi T. 1958. Die an der Verholzung beteiligten Enzyme. Die Dehydrierung des Sinapinalkohols. Chem. Ber. 91:581-90
32. Freudenberg K, Neish AC. 1968. Constitution and Biosynthesis of Lignin. In Molecular Biology, Biochemistry and Biophysics, Vol. 2, ed. A Kleinzeller, GF Springer, HG Wittman. New York: Springer-Verlag. 129 pp.
33. Freudenberg K, Richtzenhain H. 1943. Enzymatische Versuche zur Entstehung des Lignins. Ber. Dtsch. Chem. Ges. (Chem. Ber.) 76:997-1006
34. Fry SC. 1987. Intracellular feruloylation of pectic polysaccharides. Planta 171:205-11
35. Grabber JH, Quideau S, Ralph J. 1996. p-coumaroylated syringyl units in maize lignin: implications for β-ether cleavage by thioacidolysis. Phytochemistry 43:1189-94
36. Grabber JH, Ralph J, Hatfield RD. 1998. Severe inhibition of cell-wall degradation by lignins formed with coniferaldehyde. J. Sci. Food Agric. In press
37. Gross GG, Mansell RL, Zenk MH. 1975. Hydroxycinnamate:Coenzyme A ligase from lignifying tissue of higher plants. Biochem. Physiol. Pflanz. 168:S41-S51
38. Halpin C, Knight ME, Foxon GA, Campbell MM, Boudet AM, et al. 1994. Manipulation of lignin quality by downregulation of cinnamyl alcohol dehydrogenase. Plant J. 6:339-50
39. Harkin JM, Obst TR. 1973. Lignification in trees: indication of exclusive peroxidase participation. Science 180:296-97
40. 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. Biosci. Biotechnol. Biochem. 59:929-31
41. Higuchi T. 1959. Studies on the biosynthesis of lignin. In Biochemistry of Wood, ed. K Kratzl, G Billek, pp. 161-88. New York: Pergamon
42. Higuchi T. 1985. Biosynthesis of lignin. In Biosynthesis and Biodegradation of Wood Components, ed. T Higuchi, pp. 141-60. New York: Academic
43. Ibrahim R, Grisebach H. 1976. Purification and properties of UDP-glucose: coniferyl alcohol glucosyltransferase from suspension cultures of Paul's Scarlet rose. Arch. Biochem. Biophys. 176:700-8
44. Kajita S, Hishiyama S, Tomimura Y, Katayama Y, Omori S. 1997. Structural characterization of modified lignin in transgenic tobacco plants in which the activity of 4-coumarate: Coenzyme A ligase is depressed. Plant Physiol. 114:871-79
45. Kajita S, Katayama Y, Omoi S. 1996. Alterations in the biosynthesis of lignin in transgenic plants with chimeric genes for 4-coumarate:CoA ligase. Plant Cell Physiol. 37:957-65
46. Kauffman SA. 1993. The Origins of Order: Self Organization and Selection in Evolution. New York: Oxford Univ. Press. 709 pp.
47. Keller B, Sauer N, Lamb CJ. 1988. Glycine-rich proteins in bean: gene structure and assocation of the protein with the vascular system. EMBO J. 7:3625-34
48. Kutsuki H, Higuchi T. 1978. The formation of lignin in Erythrina cristagalli. Mokuzai Gakkaishi 24:625-31
49. Kutsuki H, Shimada M, Higuchi T. 1982. Distribution and roles of p-hydroxycinnamate:CoA ligase in lignin biosynthesis. Photochemistry 21:267-71
50. Lagrimini LM. 1991. Wound-induced deposition of polyphenols in transgenic plants overexpressing peroxidase. Plant Physiol. 96:577-83
51. Lagrimini LM, Gingas V, Finger F, Rothstein S, Liu TTY. 1997. Characterization of antisense transformed plants deficient in the tobacco anionic peroxidase. Plant Physiol. 114:1187-96
52. Lam TBT, Iiyama K, Stone BA. 1992. Cinnamic acid bridges between cell wall polymers in wheat and phalaris internodes. Phytochemistry 31:1179-83
53. Lam TBT, Iiyama K, Stone BA. 1994. An approach to the estimation of ferulic acid bridges in unfractioned cell walls of wheat internodes. Phytochemistry 37:327-33
54. Lapierre C. 1993. Application of new methods for the investigation of lignin structure. In Forage Cell Wall Structure and Digestibility, ed. HG Jung, DR Buxton, RD Hatfield, J Ralph, pp. 133-66. Madison, Wis: ASA-CSSA-SSSA
55. 13C Bidimensionelle des lignines du peuplier: étude des corrélations entre atomes de carbone et réexamen par la methode INADEQUATE des attributions des signaux du spectre. Holzforschung 41:51-58
56. Lee D, Meyer K, Chappie C, Douglas CJ. 1997. Down-regulation of 4-coumarate:CoA ligase (4CL) in Arabidopsis: effect on lignin composition and implications for the control of monolignol biosynthesis. Plant Cell. 9:1985-98
57. Leinhos V, Udagama-Randeniya PV, Savidge RA. 1994. Purification of an acidic coniferin-hydrolysing β-glucosidase from developing xylem of Pinus banksiana. Phytochemistry 37:311-15
58. 57a. Lewin M, Goldstein IS, eds. 1991. Wood Structure and Composition. New York: Dekker
59. Lewis NG, Yamamoto E. 1990. Lignin: occurrence, biogenesis and biodegradation. Annu. Rev. Plant Physiol. Plant Mol. Biol. 41:455-96
60. Lewis NG, Yamamoto E, Wooten JB, Just G, Ohoshi H, Towers GHN. 1987. Monitoring biosynthesis of wheat cellwall phenylpropanoids in situ. Science 237:1344-46
61. Li LG, Popko JL, Zhang XH, Osakabe K, Tsai C-J, et al. 1997. A novel multifunctional O-methyltransferase implicated in a dual methylation pathway associated with lignin biosynthesis in loblolly pine. Proc. Natl. Acad. Sci. USA 94:5461-66
62. Lin SY, Dence CW. 1992. Methods in Lignin Chemistry. Berlin: Springer-Verlag. 578 pp.
63. Liu L, Dean JFD, Friedman WE, Eriksson KE. 1994. A laccase-like phenoloxidase is correlated with lignin biosynthesis in Zinnia elegans stem tissue. Plant J. 6:213-24
64. Lu F, Ralph J. 1997. Derivatization followed by reductive cleavage (DFRC method), a new method for lignin analysis: protocol for analysis of DFRC monomers J. Agric. Food Chem. 45:2590-92
65. Lüderitz T, Schatz G, Grisebach H. 1982. Enzymic synthesis of lignin precursors-purification and properties of 4-coumarate:CoA ligase from cambial sap of spruce (Picea abies L). Eur. J. Biochem. 123:583-86
66. MacKay JJ, O'Malley DM, Presnell T, Fitzgerald LB, Campbell MM, et al. 1997. Inheritance, gene expression, and lignin characterization in a mutant pine deficient in cinnamyl alcohol dehydrogenase. Proc. Natl. Acad. Sci. USA 94:8255-60
67. McDougall GJ, Stewart D, Morrison IM. 1996. Tyrosine residues enhance crosslinking of synthetic proteins into ligninlike dehydrogenation products. Phytochemistry 41:43-47
68. Meyer K, Cusumano JC, Ruegger M, Bell-Lelong DA, Chapple CCS. 1997. Regulation and manipulation of lignin monomer composition by expression and overexpression of ferulate 5-hydroxylase, a cytochrome P450-dependent monooxygenase required for syringyl lignin biosynthesis. Presented at Int. Wood Biotechnol. Symp., 2nd, Canberra, Pap. 9
69. Meyer K, Kohler A, Kauss H. 1991. Biosynthesis of ferulic acid esters of plant cell wall polysaccharides in endomembranes from parsley cells. FEBS Lett. 290:209-12
70. Monties B. 1989. Lignins. In Plant Phenolics, ed. JB Harbourne, 1:113-57, Methods in Plant Biochemistry, ed. PM Dey, JB Harbourne. New York: Academic
71. Monties B. 1989. Lignins. In Plant Phenolics, ed. JB Harbourne, 1:113-57, Methods in Plant Biochemistry, ed. PM Dey, JB Harbourne. New York: Academic
72. Musha Y, Goring DAI. 1975. Distribution of syringyl and guaiacyl moieties in hardwoods as indicated by ultraviolet microscopy. Wood Sci. Technol. 9:45-58
73. Myton KE, Fry SC. 1994. Intraprotoplasmic feruloylation of arabinoxylans in Festuca arundinacea cell cultures. Planta 193:326-30
74. Nakamura W. 1967. Studies on the biosynthesis of lignin. 1. Disproof against the catalytic activity of laccase in the oxidation of coniferyl alcohol. J. Biochem. Jpn. 62:54-60
75. Nose M, Bernards MA, Furlan M, Zajicek J, Eberhardt TL, Lewis NG. 1995. Towards the specification of consecutive steps in macromolecular lignin assembly. Phytochemistry 39:71-79
76. O'Connell AP, Holt K, Halpin C, Schuch W. 1996. Manipulation of lignin biosynthesis in transgenic plants. Proc. Keystone Symp. Extracell. Matrix Plants: Mol. Cell. Dev. Biol., Tamarron, Colo., p. 19. New York: Wiley-Liss
77. O'Malley DM, Whetten R, Bao W, Chen C-L, Sederoff RR. 1993. The role of laccase in lignification. Plant J. 4:751-57
78. Pillonel C, Mulder MM, Boon JJ, Forster B, Binder A. 1991. Involvement of cinnamyl-alcohol dehydrogenase in the control of lignin formation in Sorghum bicolor L. Moench. Planta 185:538-44
79. Radotic K, Simic-Krstic J, Jeremic M, Trifunovic M. 1994. A study of lignin formation at the molecular level by scanning tunneling microscopy. Biophys. J. 66:1763-67
80. Ralph J. 1996. An unusual lignin from kenaf. J. Nat. Prod. 59:341-42
81. Ralph J. 1997. Recent advances in characterizing "nontraditional" lignins. Presented at Int. Symp. Wood Pap. Chem., PL2-1-PL2-7, Montreal
82. Ralph J, Grabber JH, Hatfield RD. 1995. Lignin-ferulate crosslinks in grasses: active incorporation of ferulate polysaccha- ride esters into ryegrass lignins. Carbohydr. Res. 275:167-78
83. Ralph J, Hatfield RD, Quideau S, Helm RF, Grabber JH, Jung H-JG. 1994. Pathway of p-coumaric acid incorporation into maize lignin as revealed by NMR. J. Am. Chem. Soc. 116:9448-56
84. Ralph J, MacKay JJ, Hatfield RD, O'Malley DM, Whetten RW, Sederoff RR. 1997. Abnormal lignin in a loblolly pine mutant. Science 277:235-39
85. Richardson A, McDougall GJ. 1997. A laccase-type polyphenol oxidase from lignifying xylem of tobacco. Phytochemistry 44:229-35
86. Robinson DG. 1985. Synthesis and Secretion of Extracellular Macromolecules in Plant Membranes. New York: Wiley
87. Ros Barcelo A. 1995. Peroxidase and not laccase is the enzyme responsible for cell wall lignification in the secondary thickening of xylem vessels in Lupinus. Protoplasma 186:41-44
88. Rösier J, Krekel F, Amrhein N, Schmid J. 1997. Maize phenylalanine ammonialyase has tyrosine ammonia-lyase activity. Plant Physiol. 113:175-79
89. Sarkanen KV, Chang H-M, Allan GG. 1967. Species variation in lignins. III. Hardwood lignins. Tappi J. 50:587-90
90. Sarkanen KV, Hergert HL. 1971. Classification and distribution. In Lignins, Occurrence, Formation, Structure and Reactions, ed. KV Sarkanen, CH Ludwig, pp. 43-94. New York: Wiley
91. Savidge RA. 1989. Coniferin, a biochemical indicator of commitment to tracheid differentiation in conifers. Can. J. Bot. 67:2663-68
92. Savidge RA, Udagama-Randeniya P. 1992. Cell wall-bound coniferyl alcohol oxidase associated with lignification in conifers. Phytochemistry 31:2959-66
93. Sederoff R, Chang HM. 1991. Lignin biosynthesis. See Ref. 57a, pp. 263-85
94. Sewalt VJH, Ni W, Blount JW, Jung HG, Masoud SA, et al. 1997. Reduced lignin content and altered lignin composition in transgenic tobacco down-regulated in expression of L-phenylalanine ammonialyase or cinnamate 4-hydroxylase. Plant Physiol. 115:41-50
95. Somssich IE, Bollmann J, Hahlbrock K, Kombrink E, Schulz W. 1989. Differential early activation of defense-related genes in elicitor-treated parsley cells. Plant Mol. Biol. 12:227-34
96. Somssich IE, Wernert P, Kiedrowski S, Hahlbrock K. 1996. Arabidopsis thaliana defense-related protein ELI3 is an aromatic alcohol:NADP+ oxidoreductase. Proc. Natl. Acad. Sci. USA 93:14199-203
97. Sterjiades R, Dean JFD, Eriksson KEL. 1992. Laccase from sycamore maple (Acer pseudoplatanus) polymerizes monolignols. Plant Physiol. 99:1162-68
98. Sterjiades R, Dean JFD, Gamble G, Himmelsbach DS, Eriksson K-EL. 1993. Extracellular laccases and peroxidases from sycamore maple (Acer pseudoplatanus) cell-suspension cultures - reactions with monolignols and lignin model compounds. Planta 190:75-87
99. Terazawa M, Okuyama H, Miyake M. 1984. Seasonal variations of phenolic glycosides in the cambial sap of wood. Mokuzai Gakkaishi 30:329-34
100. Trezzini GF, Horrichs A, Somssich IE. 1993. Isolation of putative defense-related genes from Arabidopsis thaliana and expression in fungal elicitor-treated cells. Plant Mol. Biol. 21:385-89
101. Tsai C-J, Mielke M, Popko J, Monossol J, Hu W, et al. 1997. Altered lignin composition in quaking aspen through manipulation of caffeic acid/5-hydroxy ferulic acid O-methyltransferase gene expression. Presented at Int. Wood Biotechnol. Symp., 2nd, Canberra, Pap. 12
102. Udagama-Randeniya P, Savidge R. 1995. Coniferyl alcohol oxidase - a catechol oxidase? Trees 10:102-7
103. Van Doorsselaere J, Baucher M, Chognot E, Chabbert B, Tollier M-T, et al. 1995. A novel lignin in poplar trees with reduced caffeic acid/5-hydroxyferulic acid O-methyltransferase activity. Plant J. 8:855-64
104. Voo KS, Whetten RW, O'Malley DM, Sederoff RR. 1995. 4-coumarate:CoA ligase in xylem of loblolly pine. Plant Physiol. 108:85-97
105. Whetten R, Sederoff R. 1995. Lignin biosynthesis. Plant Cell 7:1001-13
106. Whitmore FW. 1978. Lignin-carbohydrate complex formed in isolated cell walls of callus. Phytochemistry 17:421-25
107. Yao K, De Luca V, Brisson N. 1995. Creation of a metabolic sink for tryptophan alters the phenylpropanoid pathway and the susceptibility of potato to Phytophthora infestans. Plant Cell 7:1787-99
108. Ye Z-H, Kneusel RE, Matern U, Varner JE. 1994. An alternative methylation pathway in lignin biosynthesis in Zinnia. Plant Cell 6:1427-39
109. Ye Z-H, Varner JE. 1995. Differential expression of two O-methyltransferases in lignin biosynthesis in Zinnia elegans. Plant Physiol. 108:459-67
110. Zakis GF. 1994. Functional Analysis of Lignins and Their Derivatives. Atlanta: TAPPI. 94 pp.