Synthesis of Lignin in Transgenic and Mutant Plants
Part 1. Lignin, Humic Substances and Coal
Dr. Jeffrey F. D. Dean,
Dr. Jeffrey F. D. Dean
- [email protected]
- +01-7065421710 | Fax: +01-7065428356
University of Georgia, Daniel B. Warnell School of Forest Resources, Athens, USA, GA 30602-2152
Search for more papers by this authorDr. Jeffrey F. D. Dean,
Dr. Jeffrey F. D. Dean
- [email protected]
- +01-7065421710 | Fax: +01-7065428356
University of Georgia, Daniel B. Warnell School of Forest Resources, Athens, USA, GA 30602-2152
Search for more papers by this authorAbstract
- Introduction
- Potential Applications
- Pulp and Paper
- Solid Wood Products
- Textile Fibers
- Biomass Conversion
- Novel Products
- Challenges
- Potential Applications
- Historical Outline
- Chemistry
- Biology
- Lignin Mutants
- Brown Midrib Monocots
- Loblolly Pine
- Arabidopsis
- Lignin Transgenics
- The Shikimate Pathway and Phenylalanine Ammonia Lyase
- Cinnamate 4-Hydroxylase and 4-Coumarate-3-Hydroxylase
- 4-Coumarate:CoA Ligase
- O-Methyltransferases
- Cinnamoyl-CoA Reductase
- Ferulate 5-Hydroxylase
- Cinnamyl Alcohol Dehydrogenase
- Coniferin β-Glucosidase
- Peroxidases and Other Oxidases
- Transcription Factors and Other Targets
- Outlook and Perspectives
- Patents
References
- Amin, M. N., Begum, M., Shahjahan, M., Rahman, M. S., Baksh, T. (1998) Bleaching process for increasing whiteness and lightfastness of kenaf and kenaf-jute blended fabrics, Cell. Chem. Technol. 32, 497–504.
- Andersen, S. O., Peter, M. G., Roepstorff, P. (1996) Cuticular sclerotization in insects, Comp. Biochem. Physiol. B 113, 689–705.
- Anderson, M., Roberts, J. (1998) Arabidopsis, Boca Raton, FL: CRC Press.
- Angelini, L. G., Lazzeri, A., Levita, G., Fontanelli, D., Bozzi, C. (2000) Ramie (Boehmeria nivea (L.) Gaud.) and Spanish Broom (Spartium junceum L.) fibres for composite materials: agronomical aspects, morphology and mechanical properties, Ind. Crop. Prod. 11, 145–161.
- Argyropoulos, D. S. (1999) Advances in Lignocellulosics Characterization, Atlanta: Tappi Press.
- 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, Plant J. 8, 465–477.
- Barriere, Y., Argillier, O. (1993) Brown-midrib genes of maize – A review, Agronomie 13, 865–876.
- Bate, N. J., Orr, J., Ni, W. T., Meromi, A., Nadlerhassar, 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, Proc. Natl. Acad. Sci. USA 91, 7608–7612.
- Baucher, M., Chabbert, B., Pilate, G., Van Doorsselaere, J., Tollier, M. T., Petit-Conil, M., Cornu, D., Monties, B., Van Montagu, M., Inze, D., Jouanin, L., Boerjan, W. (1996) Red xylem and higher lignin extractability by down-regulating a cinnamyl alcohol dehydrogenase in poplar, Plant Physiol. 112, 1479–1490.
- Baucher, M., Monties, B., Van Montagu, M., Boerjan, W. (1998a) Biosynthesis and genetic engineering of lignin, Crit. Rev. Plant Sci. 17, 125–197.
- Baucher, M., Christensen, J. H., Meyermans, H., Chen, C. Y., Van Doorsselaere, J., Leple, J. C., Pilate, G., Petit-Conil, M., Jouanin, L., Chabbert, B., Monties, B., Van Montagu, M., Boerjan, W. (1998b) Applications of molecular genetics for biosynthesis of novel lignins, Polym. Degrad. Stabil. 59, 47–52.
- Baucher, M., Bernard-Vailhe, 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 Mol. Biol. 39, 437–447.
- 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 Physiol. 122, 107–116.
- Boerjan, W., Baucher, M., Chabbert, B., Petit-Conil, M., Leple, J. C., Pilate, G., Cornu, D., Monties, B., Van Montagu, M., Van Doorsselaere, J., Tsai, C.-J., Podila, G. K., Joshi, C. P., Chiang, V. L. (1997) Genetic modification of lignin biosynthesis in quaking aspen and poplar, in: Micropropagation, Genetic Engineering, and Molecular Biology of Populus ( N. B. Klopfenstein, Y. W. Chun, M. S. Kim, M. R. Ahuja, Eds.), pp. 193–205. Fort Collins, CO: U.S. Department of Agriculture, Forest Service, Rocky Mountain Forest and Range Experiment Station.
- Boudet, A. M. (2000) Lignins and lignification: Selected issues, Plant Physiol. Biochem. 38, 81–96.
- Butler, M. J., Day, A. W. (1998) Fungal melanins: a review, Can. J. Microbiol. 44, 1115–1136.
- Buxton, D. R., Redfearn, D. D. (1997) Plant limitations to fiber digestion and utilization, J. Nutr. 127, S814–S818.
- Campbell, M. M., Sederoff, R. R. (1996) Variation in lignin content and composition – Mechanism of control and implications for the genetic improvement of plants, Plant Physiol. 110, 3–13.
- Chabbert, B., Tollier, M. T., Monties, B., Barriere, Y., Argillier, O. (1994) Biological variability in lignification of maize – expression of the brown midrib bm3 mutation in three maize cultivars, J. Sci. Food Agric. 64, 349–355.
- Chapple, C. C. S., Vogt, T., Ellis, B. E., Somerville, C. R. (1992) An Arabidopsis mutant defective in the general phenylpropanoid pathway, Plant Cell 4, 1413–1424.
- Cherney, J. H., Cherney, D. J. R., Akin, D. E., Axtell, J. D. (1991) Potential of brown-midrib, low-lignin mutants for improving forage quality, Adv. Agron. 46, 157–198.
- Dawson, J., Sozen, E., Vizir, I., Van Waeyenberge, S., Wilson, Z. A., Mulligan, B. J. (1999) Characterization and genetic mapping of a mutation (ms35) which prevents anther dehiscence in Arabidopsis thaliana by affecting secondary wall thickening in the endothecium, New Phytol. 144, 213–222.
- Dean, J. F. D. (1997) Lignin analysis, in: Plant Biochemistry/Molecular Biology Laboratory Manual ( W. V. Dashek, Ed.), pp. 199–215. Boca Raton, FL: CRC Press, Inc.
- Dean, J. F. D., LaFayette, P. R., Rugh, C., Tristram, A. H., Hoopes, J. T., Merkle, S. A., Eriksson, K-E. L. (1998) Laccases associated with lignifying tissues, ACS Symp. Ser. 697, 96–108.
- De Candolle, A.-P. (1832) Physiologie Végétale, Pt. II, p. 165. Paris, Béchet Jeune.
- Delwiche, C. F., Graham, L. E., Thompson, N. (1989) Lignin-like compounds and sporopollenin in Coleochaete, an algal model for land plant ancestry, Science 245, 399–401.
- Dharmawardhana, D. P., Ellis, B. E., Carlson, J. E. (1999) cDNA cloning and heterologous expression of coniferin beta-glucosidase, Plant Mol. Biol. 40, 365–372.
- Dixon, R. A., Lamb, C. J., Masoud, S., Sewalt, V. J. H., Paiva, N. L. (1996) Metabolic engineering: prospects for crop improvement through the genetic manipulation of phenylpropanoid biosynthesis and defense responses – A review, Gene 179, 61–71.
- Dong, J. Z., McHughen, A. (1993) Transgenic flax plants from Agrobacterium-mediated transformation – incidence of chimeric regenerants and inheritance of transgenic plants, Plant Sci. 91, 139–148.
- Dusi, D. M. A., Dubald, M., Dealmeida, E. R. P., Caldas, L. S., Gander, E. S. (1993) Transgenic plants of ramie (Boehmeria nivea Gaud) obtained by Agrobacterium-mediated transformation., Plant Cell Rep. 12, 625–628.
- 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-methyltransferase gene from Populus, Plant Mol. Biol. 26, 61–71.
- El Mansouri, I., Mercado, J. A., Santiago-Domenech, N., Pliego-Alfaro, F., Valpuesta, V., Quesada, M. A. (1999) Biochemical and phenotypical characterization of transgenic tomato plants overexpressing a basic peroxidase, Physiol. Plant. 106, 355–362.
- Faix, O. (1992) New aspects of lignin utilization in large amounts, Papier 46, 733–740.
- Freudenberg, K. (1968) Constitution and Biosynthesis of Lignin ( K. Freudenberg, A. C. Neish, Eds.), pp. 114–115. New York: Springer-Verlag.
- Grima-Pettenati, J., Goffner, D. (1999) Lignin genetic engineering revisited, Plant Sci. 145, 51–65.
- Grunwald, C., Deutsch, F., Eckstein, D., Fladung, M. (2000) Wood formation in rolC transgenic aspen trees, Trees-Struct. Funct. 14, 297–304.
- 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 down-regulation of cinnamyl alcohol-dehydrogenase, Plant J. 6, 339–350.
- 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, Plant J. 14, 545–553.
- Halpin, C., Barakate, A., Abbott, J., El Amrani, A. (1999) Arabidopsis laccases, Forest Biotechnology 99, July 11–16, 1999, University of Oxford, England (poster 29).
- Hatfield, R. D., Ralph, J., Grabber, J. H. (1999) Cell wall structural foundations: molecular basis for improving forage digestibilities, Crop Sci. 39, 27–37.
- Helm, R. F. (2000) Lignin-polysaccharide interactions in woody plants, ACS Symp. Ser. 742, 161–171.
- Hepworth, D. G., Vincent, J. F. V. (1998) The mechanical properties of xylem tissue from tobacco plants (Nicotiana tabacum ‘Samsun’), Ann. Bot. 81,751–759.
- 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, 929–931.
- Higuchi, T., Ito, T., Umezawa, T., Hibino, T., Shibata, D. (1994) Red-brown color of lignified tissues of transgenic plants with antisense CAD gene – wine-red lignin from coniferyl aldehyde, J. Biotechnol. 37, 151–158.
- Htun, M., Salmen, L. (1996) The importance of understanding the physical and chemical properties of wood to achieve energy efficiency in mechanical pulping, Woch. Papierfabrik. 124, 232–235.
- 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 Biotechnol. 17, 808–812.
- 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, Proc. Natl. Acad. Sci. USA 96, 10045–10050.
- Imison, J. (1822) Elements of Science and Art, Vol. II., p. 131. London: A. & R. Spottiswoode.
- Jones, J. D., Henstrand, J. M., Handa, A. K., Herrmann, K. M., Weller, S. C. (1995) Impaired wound induction of 3-deoxy-D-arabino-heptulosonate-7-phosphate (DAHP) synthase and altered stem development in transgenic potato plants expressing a DAHP synthase antisense construct, Plant Physiol. 108, 1413–1421.
- 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 Physiol. 37, 957–965.
- 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 Physiol. 114, 871–879.
- 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 Sci. 128, 109–118.
- Kennedy, R. W. (1995) Coniferous wood quality in the future – concerns and strategies, Wood Sci. Technol. 29, 321–338.
- Kim, H., Ralph, J., Yahiaoui, N., Pean, M., Boudet, A.-M. (2000) Cross-coupling of hydroxycinnamyl aldehydes into lignins, Org. Lett. 2, 2197–2200.
- Kosikova, B., Duris, M., Demianova, V. (2000) Conversion of lignin biopolymer into surface-active derivatives, Eur. Polym. J. 36, 1209–1212.
- Kuc, J., Nelson, O. (1964) The abnormal lignins produced by the brown-midrib mutants of maize. I. The brown-midrib-1 mutant, Arch. Biochem. Biophys. 105, 103–113.
- LaFayette, P. R., Eriksson, K-E. L., Dean, J. F. D. (1999) Characterization and heterologous expression of laccase cDNAs from xylem tissues of yellow-poplar (Liriodendron tulipifera), Plant Mol. Biol. 40, 23–35.
- Lagrimini, L. M. (1991) Wound-induced deposition of polyphenols in transgenic plants overexpressing peroxidase, Plant Physiol. 96, 577–583.
- Lagrimini, L. M., Gingas, V., Finger, F., Rothstein, S., Liu, T. T. Y. (1997) Characterization of antisense transformed plants deficient in the tobacco anionic peroxidase, Plant Physiol. 114, 1187–1196.
- Lapierre, C., Pollet, B., Petit-Conil, M., Toval, G., Romero, J., Pilate, G., Leple, 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 Physiol. 119, 153–163.
- Lapierre, C., Pollet, B., Petit-Conil, M., Pilate, G., Leple, C., Boerjan, W., Jouanin, L. (2000) Genetic engineering of poplar lignins: Impact of lignin alteration on kraft pulping performances, ACS Symp. Ser. 742, 145–160.
- Lechtenberg, V. L., Muller, L. D., Bauman, L. F., Rhykerd, C. L., Barnes, R. F. (1972) Laboratory and in vitro evaluation of inbred and F2 populations of brown midrib mutants of Zea mays L, Agron. J. 64, 657–660.
- 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, Plant Cell 9, 1985–1998.
- Lewis, N. G. (1999) A 20th century roller coaster ride: a short account of lignification, Curr. Opin. Plant Biol. 2, 153–162.
- Li, Y., Sarkanen, S. (2000) Thermoplastics with very high lignin contents, ACS Symp. Ser. 742, 351–366.
- Li, L. G., 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, J. Biol. Chem. 275, 6537–6545.
- Liljegren, S. J., Ditta, G. S., Eshed, H. Y., Savidge, B., Bowman, J. L., Yanofsky, M. F. (2000) SHATTERPROOF MADS-box genes control seed dispersal in Arabidopsis, Nature 404, 766–770.
- MacKay, J. J., O'Malley, D. M., Presnell, T., Booker, F. L., Campbell, M. M., Whetten, R. W., Sederoff, R. R. (1997) Inheritance, gene expression, and lignin characterization in a mutant pine deficient in cinnamyl alcohol dehydrogenase, Proc. Natl. Acad. Sci. USA 94, 8255–8260.
- MacKay, J., Presnell, T., Jameel, H., Taneda, H., O'Malley, D., Sederoff, R. (1999) Modified lignin and delignification with a CAD-deficient loblolly pine, Holzforschung 53, 403–410.
- Maher, E. A., Bate, N. J., Ni, W. T., Elkind, Y., Dixon, R. A., Lamb, C. J. (1994) Increased disease susceptibility of transgenic tobacco plants with suppressed levels of preformed phenylpropanoid products, Proc. Natl. Acad. Sci. USA 91, 7802–7806.
- 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, Proc. Natl. Acad. Sci. USA 96, 12328–12332.
- Maury, S., Geoffroy, P., Legrand, M. (1999) Tobacco O-methyltransferases involved in phenylpropanoid metabolism. The different caffeoyl-coenzyme A/5-hydroxyferuloyl-coenzyme A 3/5-O-methyltransferase and caffeic acid/5-hydroxyferulic acid 3/5-O-methyltransferase classes have distinct substrate specificities and expression patterns, Plant Physiol. 121, 215–223.
- Merkle, S. A., Dean, J. F. D. (2000) Forest tree biotechnology, Curr. Opin. Biotechnol. 11, 298–302.
- Meyer, K., Cusumano, J. C., Somerville, C., Chapple, C. C. S. (1996) Ferulate-5-hydroxylase from Arabidopsis thaliana defines a new family of cytochrome P450-dependent monooxygenases, Proc. Natl. Acad. Sci. USA 93, 6869–6874.
- 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, Proc. Natl. Acad. Sci. USA 95, 6619–6623.
- 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 Montague, 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, J. Biol. Chem. (in press).
- Miksche, G. E., Yasuda, S. (1978) Lignin of ‘giant’ mosses and some related species, Phytochemistry 17, 503–504.
- Monties, B. (1998) Novel structures and properties of lignins in relation to their natural and induced variability in ecotypes, mutants and transgenic plants, Polym. Degrad. Stabil. 59, 53–64.
- Mullin, T. J., Bertrand, S. (1998) Environmental release of transgenic trees in Canada – potential benefits and assessment of biosafety, Forest. Chron. 74, 203–219.
- Ni, W. T., Paiva, N. L., Dixon, R. A. (1994) Reduced lignin in transgenic plants containing a caffeic acid O-methyltransferase antisense gene, Trans. Res. 3, 120–126.
- Nilsson, L. J., Larson, E. D., Gilbreath, K., Gupta, A. (1995) Energy Efficiency and the Pulp and Paper Industry, ACEEE Summer Study on Energy Efficiency in Industry: ‘Partnership, Productivity, and Environment’, August 1–4, Grand Island, NY (http://www.aceee.org/pubs/ie962.htm)
- Osakabe, K., Tsao, C. C., Li, L. G., 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, Proc. Natl. Acad. Sci. USA 96, 8955–8960.
- Payen, A. (1838) Study of the composition of the natural tissue of plants and of lignin, Comptes Rendues 7, 1052.
- 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, Plant J. 13, 71–83.
- Provan, G. J., Scobbie, L., Chesson, A. (1997) Characterisation of lignin from CAD and OMT deficient Bm mutants of maize, J. Sci. Food Agric. 73, 133–142.
- Ralph, J., Lu, F. C. (1998) The DFRC method for lignin analysis. 6. A simple modification for identifying natural acetates on lignins, J. Agric. Food Chem. 46, 4616–4619.
- 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.
- 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, Proc. Natl. Acad. Sci. USA 95, 12803–12808.
- Ralph, J., Hatfield, R. D., Marita, J. M., Lu, F., Peng, J., Kim, H., Grabber, J. H., MacKay, J. J, O'Malley, D. M., Sederoff, R. R., Chapple, C., Chiang, V., Boudet, A. M. (1999a) Lignin structure in lignin-biosynthetic-pathway mutants and transgenics; new opportunities for engineering lignin?, 10th International Symposium on Wood and Pulping Chemistry, June 7–10, Yokohama, Japan (http://www.dfrc.ars.usda.gov/ FullTextPDFs/ISWPC99-Mutants.pdf)
- Ralph, J., Kim, H., Peng, J., Lu, F. (1999b) Arylpropane-1,3-diols in lignins from normal and CAD-deficient pines, Org. Lett. 1, 323–326
- Ralph, J., Lapierre, C., Lu, F., Marita, J. M., Pilate, G., Van Doorsselaere, J., Boerjan, W., Jouanin, L. (2000) NMR evidence for benzodioxane structures resulting from incorporation of 5-hydroxyconiferyl alcohol into lignins of O-methyl-transferase-deficient poplars, J. Agric. Food Chem. (in press).
- Rasmussen, S., Dixon, R. A. (1999) Transgene-mediated and elicitor-induced perturbation of metabolic channeling at the entry point into the phenylpropanoid pathway, Plant Cell 11, 1537–1551.
- Ray, H., Douches, D. S., Hammerschmidt, R. (1998) Transformation of potato with cucumber peroxidase: expression and disease response, Physiol. Mol. Plant Pathol. 53, 93–103.
- Savidge, R. A., Forster, H. (1998) Seasonal activity of uridine 5′-diphosphoglucose: coniferyl alcohol glucosyltransferase in relation to cambial growth and dormancy in conifers, Can. J. Bot. 76, 486–493.
- Schulze, F. (1856) Zur kenntnis des lignins und seines vorkommens im planzenkörper. Festschrift zur 400sten jubelfeier der Universität Greifswald.
- Sederoff, R. R., MacKay, J. J., Ralph, J., Hatfield, R. D. (1999) Unexpected variation in lignin, Curr. Opin. Plant Biol. 2, 145–152.
- Sewalt, V. J. H., Ni, W. T., Jung, H. G., Dixon, R. A. (1997a) Lignin impact on fiber degradation: Increased enzymatic digestibility of genetically engineered tobacco (Nicotiana tabacum) stems reduced in lignin content, J. Agric. Food Chem. 45, 1977–1983.
- Sewalt, V. J. H., Ni, W. T., Blount, J. W., Jung, H. G., Masoud, S. A., Howles, P. A., Lamb, C., Dixon, R. A. (1997b) Reduced lignin content and altered lignin composition in transgenic tobacco down-regulated in expression of L-phenylalanine ammonia-lyase or cinnamate 4-hydroxylase, Plant Physiol. 115, 41–50.
- Siegel, S. M. (1969) Evidence for the presence of lignin in moss gametophytes, Am. J. Bot. 56, 175–179.
- Sitbon, F., Hennion, S., Sundberg, B., Little, C. H. A., Olsson, O., Sandberg, G. (1992) Transgenic tobacco plants coexpressing the Agrobacterium tumefaciens iaaM and iaaH genes display altered growth and indole acetic acid metabolism, Plant Physiol. 99, 1062–1069.
- Sitbon, F., Hennion, S., Little, C. H. A., Sundberg, B. (1999) Enhanced ethylene production and peroxidase activity in IAA-overproducing transgenic tobacco plants is associated with increased lignin content and altered lignin composition, Plant Sci. 141, 165–173.
- Smeder, B., Liljedahl, S. (1996) Market oriented identification of important properties in developing flax fibres for technical uses, Ind. Crop Prod. 5, 149–162.
- Stafford, H. A. (1981) Compartmentation in natural product biosynthesis by multienzyme complexes, in: The Biochemistry of Plants, Vol. 7 ( E. E. Conn, Ed.), pp. 117–137. New York: Academic Press.
- Stewart, D., Yahiaoui, N., McDougall, G. J., Myton, K., Marque, C., Boudet, A. M., Haigh, J. (1997) Fourier-transform infrared and Raman spectroscopic evidence for the incorporation of cinnamaldehydes into the lignin of transgenic tobacco (Nicotiana tabacum L) plants with reduced expression of cinnamyl alcohol dehydrogenase, Planta 201, 311–318.
- Suzuki, S., Lam, T. B. T., Iiyama, K. (1997) 5-Hydroxyguaiacyl nuclei as aromatic constituents of native lignin, Phytochemistry 46, 695–700.
- 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, Plant Cell 10, 135–154.
- Thring, R. W., Katikaneni, S. P. R., Bakhshi, N. N. (2000) The production of gasoline range hydrocarbons from Alcell (R) lignin using HZSM-5 catalyst, Fuel Proc. Technol. 62, 17–30.
- Tjeerdsma, B. F., Boonstra, M., Pizzi, A., Tekely, P., Militz, H. (1998) Characterisation of thermally modified wood: molecular reasons for wood performance improvement, Holz Als Roh-Und Werkstoff 56, 149–153.
- 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 Physiol. 117, 101–112.
- Udagamarandeniya, P. V., Savidge, R. A. (1995) Coniferyl alcohol oxidase – a catechol oxidase, Trees-Struct. Funct. 10, 102–107.
- Vailhe, M. A. B., Cornu, A., Robert, D., Maillot, M. P., Besle, J. M. (1996a) Cell wall degradability of transgenic tobacco stems in relation to their chemical extraction and lignin quality, J. Agric. Food Chem. 44, 1164–1169.
- Vailhe, M. A. B., Migne, C., Cornu, A., Maillot, M. P., Grenet, E., Besle, J. M., Atanassova, R., Martz, F., Legrand, M. (1996b) Effect of modification of the O-methyltransferase activity on cell wall composition, ultrastructure and degradability of transgenic tobacco, J. Sci. Food Agric. 72, 385–391.
- Vailhe, M. A. B., Besle, J. M., Maillot, M. P., Cornu, A., Halpin, C., Knight, M. (1998) Effect of down-regulation of cinnamyl alcohol dehydrogenase on cell wall composition and on degradability of tobacco stems, J. Sci. Food Agric. 76, 505–514.
- Van Doorsselaere, J., Baucher, M., Chognot, E., Chabbert, B., Tollier, M. T., Petit-Conil, M., Leple, J. C., Pilate, G., Cornu, D., Monties, B., VanMontagu, M., Inze, D., Boerjan, W., Jouanin, L. (1995) A novel lignin in poplar trees with a reduced caffeic acid 5-hydroxyferulic acid O-methyltransferase activity, Plant J. 8, 855–864.
- Vignols, F., Rigau, J., Torres, M. A., Capellades, M., Puigdomenech, P. (1995) The brown midrib3 (bm3) mutation in maize occurs in the gene encoding caffeic acid O-methyltransferase, Plant Cell 7, 407–416.
- Vinzant, T. B., Ehrman, C. I., Adney, W. S., Thomas, S. R., Himmel, M. E. (1997) Simultaneous saccharification and fermentation of pretreated hardwoods – Effect of native lignin content, Appl. Biochem. Biotechnol. 62, 99–104.
- Wang, Z. X., Li, S. M., Loscher, R., Heide, L. (1997) 4-Coumaroyl coenzyme A 3-hydroxylase activity from cell cultures of Lithospermum erythrorhizon and its relationship to polyphenol oxidase, Arch. Biochem. Biophys. 347, 249–255.
- Weaver, L. M., Herrmann, K. M. (1997) Dynamics of the shikimate pathway in plants, Trends Plant Sci. 2, 346–351.
- Whetten, R., Sederoff, R. (1991) Genetic engineering of wood, Forest Ecol. Manag. 43, 301–316.
- Winkel-Shirley, B. (1999) Evidence for enzyme complexes in the phenylpropanoid and flavonoid pathways, Physiol. Plant. 107, 142–149.
- Wu, G. S., Shortt, B. J., Lawrence, E. B., Leon, J., Fitzsimmons, K. C., Levine, E. B., Raskin, I., Shah, D. M. (1997) Activation of host defense mechanisms by elevated production of H2O2 in transgenic plants, Plant Physiol. 115, 427–435.
- 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.
- Yao, K. N., Deluca, 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, 1787–1799.
- Ye, Z. H. (1997) Association of caffeoyl coenzyme A 3-O-methyltransferase expression with lignifying tissues in several dicot plants, Plant Physiol. 115, 1341–1350.
- Ye, Z. H., Varner, J. E. (1995) Differential expression of 2-O-methyltransferases in lignin biosynthesis in Zinnia elegans, Plant Physiol. 108, 459–467.
- Zhong, R. Q., Morrison, W. H., Negrel, J., Ye, Z. H. (1998) Dual methylation pathways in lignin biosynthesis, Plant Cell, 10, 2033–2045.
- Zhong, R. Q., Ripperger, A., Ye, Z. H. (2000) Ectopic deposition of lignin in the pith of stems of two Arabidopsis mutants, Plant Physiol. 123, 59–69.
Citing Literature
Biopolymers Online: Biology • Chemistry • Biotechnology • Applications
Browse other articles of this reference work: