Skip to main content
SpringerLink
Log in
Book cover

Phenolic Compound Biochemistry pp 63–149Cite as

Biosynthesis of Phenolic Compounds

  • Chapter

This is a preview of subscription content, log in via an institution.

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   109.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Akin, D. E., Hanna, W. W., Snook, M. E., Himmelsbach, D. S., Barton, F. E., and Windham, W. R., 1986, Normal-12 and brown midrib-12 sorghum. II. Chemical variation and digestibility, Agron. J. 78: 832-837.

    Article  CAS  Google Scholar 

  • Akin, D. E., and Rigsby, L. L. , 1991, Structure and digestibility of tissues in normal and brown midrib pearl millet (Pennisetum glaucum), J. Sci. Food Agric. 56: 523-538.

    Article  Google Scholar 

  • Akiyama, T., Magara, K., Matsumoto, Y., Meshitsuka, G., Ishizu, A., and Lundquist, K., 2000, Proof of the presence of racemic forms of arylglycerol-β-aryl ether structure in lignin: studies on the stereo structure of lignin by ozonation, J. Wood Sci. 46: 414–415.

    Article  CAS  Google Scholar 

  • Albert, S., Delseny, M., and Devic, M., 1997, BANYULS, a novel negative regulator of flavonoid biosynthesis in the Arabidopsis seed coat, Plant J. 11: 289-299.

    Article  PubMed  CAS  Google Scholar 

  • Anterola, A. M., and Lewis, N. G., 2002, Trends in lignin modification: a compehensive analysis of the effects of genetic manipulations/ mutations on lignification and vascular integrity, Phytochem. 61: 221-294.

    Article  CAS  Google Scholar 

  • Bao, W., O’Malley, D.M., Whetten, R. and Sederoff, R.R., 1993, A laccase associated with lignification in loblolly pine xylem, Science 260: 672-674.

    Article  PubMed  CAS  Google Scholar 

  • Barnes, R. F., Muller, L. D., Bauman, L. F., and Colenbrander, V. F. , 1971, In vitro dry matter disappearance of brown-midrib mutants of maize, J. Anim. Sci. 33: 881-884.

    Google Scholar 

  • Barrière, Y., Chabbert, B., Tollier, M. T., and Monties, B., 1994, Breeding silage maize with brown-midrib genes. Feeding value and biochemical characteristics, Agronomie 14: 15-25.

    Article  Google Scholar 

  • Barrière, Y., Ralph, J., Méchin, V., Guillaumie, S., Grabber, J. H., Argillier, O., Chabbert, B., and Lapierre, C., 2004, Genetic and molecular baisis of grass cell wall biosynthesis and degradability. II. Lessons from brown midrib mutants, C. R. Biologies 327: 847-860.

    Article  PubMed  CAS  Google Scholar 

  • Biermann, C.J., 1996, Handbook of Pulping and Papermaking, 2nd ed. Academic Press, San Diego, pp. 754.

    Google Scholar 

  • Behringer, F.J., and Medford, J. I., 1992, A plasmid rescue technique for the recovery of plant DNA disrupted by T-DNA insertion, Plant Mol. Biol. Rep 10: 190-198.

    Article  CAS  Google Scholar 

  • Belyaev, L., Marchenko, O. V., Filippov, S. P., Solomin, S. V., Stepanopa, T. B., and Kokorin, A. L., 2002, World Energy and Transition to Sustainable Development, Kluwer, Dordrecht, pp. 264.

    Google Scholar 

  • Bittinger, T. S., Cantrell, R. P., and Axtell, J. D., 1981, Allelism tests of the brown-midrib mutants of sorghum, J. Heredity 72: 147-148.

    Google Scholar 

  • Boerjan, W., Ralph, J., and Baucher, M., 2003, Lignin biosynthesis, Annu. Rev. Plant Biol. 54: 519-546.

    Article  PubMed  CAS  Google Scholar 

  • Bout, S., and Vermerris, W., 2003, A candidate gene-approach to clone the sorghum Brown midrib gene encoding caffeic acid O-methyltransferase, Mol. Genet. Genomics 269: 205-214.

    PubMed  CAS  Google Scholar 

  • Broomhead, A. J., Rahman, M. M. A., Dewick, P. M., Jackson, D. E., and Lucas, J.A., 1991, Matairesinol as precursor of Podophyllum lignans, Phytochem. 30: 1489–1492.

    Article  CAS  Google Scholar 

  • Brown, D. M., Zeef, L. A. H., Ellis, J., Goodacre, R., and Turnera, S. R., 2005, Identification of novel genes in Arabidopsis involved in secondary cell wall formation using expression profiling and reverse genetics, Plant Cell 17: 2281-2295.

    Article  PubMed  CAS  Google Scholar 

  • Canel, C., Moraes, R.M., Dayan, F.E., and Ferreira, D., 2000, Molecules of interest: podophyllotoxin, Phytochem. 54: 115-120.

    Article  CAS  Google Scholar 

  • Chabbert, B., Tollier, M. T., Monties, B., Barrière, Y., and Argillier, O., 1994, Biological variability in lignification of maize: expression of the brown midrib bm2 mutation, J. Sci. of Food Agric. 64: 455-460.

    Article  CAS  Google Scholar 

  • Chandler, V. L., Radicella, J. P., Robbins, T. P., Chen, J., and Turks, D., 1989, Two regulatory genes of the maize anthocyanin pathway are homologous: isolation of B utilizing R genomic sequences, Plant Cell 1: 1175-1183.

    Article  PubMed  CAS  Google Scholar 

  • Chang, C., Bowman, J. L., DeJohn, A. W., Lander, E. S., and Meyerowitz, E. M., 1988, Restriction fragment length polymorphism linkage map for Arabidopsis thaliana, Proc. Natl. Acad. Sci. USA 85: 6856-6860.

    Article  PubMed  CAS  Google Scholar 

  • Chang, V. S., and Holtzapple, M. T., 2000, Fundamental factors affecting biomass enzymatic reactivity, Appl. Biochem. Biotechnol. 84: 5-37.

    Article  PubMed  Google Scholar 

  • Chapple, C., 1998, Molecular-genetic analysis of plant cytochrome P450- dependent monooxygenases, Annu. Rev. Plant Physiol. Plant Mol. Biol. 49: 311-343.

    Article  PubMed  CAS  Google Scholar 

  • Chapple, C. C. S., Vogt, T., Ellis, B. E., and Sommerville, C. R., 1992, An Arabidopsis mutant defective in the general phenylpropanoid pathway, Plant Cell 4: 1413-1424.

    Article  PubMed  CAS  Google Scholar 

  • Charles, N., Mansfield, S. D., Mirochnik, O., and Duff, S. J.B., 2003, Effect of oxygen delignification operating parameters on downstream enzymatic hydrolysis of softwood substrates, Biotechnol. Progr. 19: 1606-1611.

    Article  CAS  Google Scholar 

  • Chen, C., Meyermans, H., Burggraeve, B., De Rycke, R. M., Inoue, K., De Vleesschauwer, V., Steenackers, M., Van Montagu, M. C., Engler, G. J., and Boerjan, W. A., 2000, Cell-specific and conditional expression of caffeoyl-coenzyme A-3-O-methyltransferase in poplar, Plant Physiol. 123: 853-867.

    Article  PubMed  CAS  Google Scholar 

  • Chen, W., Chao, G., and Singh, K. B., 1996, The promoter of a H2O2- inducible, Arabidopsis glutathione S-transferase gene contains closely linked OBF- and OBP1- binding sites, Plant J. 10: 955-966.

    Article  PubMed  CAS  Google Scholar 

  • Cheng, W.-H., Taliercio, E. W., and Chourey, P. S., 1996, The Miniature1 seed locus of maize encodes a cell wall invertase required for normal development of endosperm and maternal cells in the pedicel, Plant Cell 8: 971-983.

    Article  PubMed  CAS  Google Scholar 

  • Cherney, J. H., Axtell, J. D., Hassen, M. M., and Anliker, K. S., 1988, Forage quality characterization of a chemically induced brown-midrib mutant in pearl millet, Crop Sci. 28: 783-787.

    Article  Google Scholar 

  • Cherney, D. J. R., Patterson, J. A., and Johnson, K. D., 1990, Digestibility and feeding value of pearl millet as influenced by the brown-midrib, lowlignin trait, J. Anim. Sci. 68: 4345-4351.

    PubMed  CAS  Google Scholar 

  • Cherney, J. H., Cherney, D. J. R., Akin, D. E., and Axtell, J. D., 1991, Potential of brown-midrib, low-lignin mutants for improving forage quality, Adv. Agron. 46: 157-198.

    Article  CAS  Google Scholar 

  • Cone, K. C., Burr, F. A., and Burr, B., 1986, Molecular analysis of the maize anthocyanin regulatory locus C1, Proc. Natl. Acad. Sci. USA 83: 9631-9635.

    Article  PubMed  CAS  Google Scholar 

  • Cone, K. C., Cocciolone, S. M., Burr, F. A., and Burr, B., 1993a, Maize anthocyanin regulatory gene pl is a duplicate of c1 that functions in the plant, Plant Cell 5: 1795-1805.

    Article  CAS  Google Scholar 

  • Cone, K. C, Cocciolone, S. M., Moehlenkamp, C. A., Weber, T., Drummond, B. J., Tagliani, L. A., Bowen, B. A., Perrot, G. H., 1993b, Role of the regulatory gene pl in the photocontrol of maize anthocyanin pigmentation, Plant Cell 5: 1807-1816.

    Article  CAS  Google Scholar 

  • Davin, B. L., and Lewis, N. G., 2005, Lignin primary structures and dirigent sites, Curr. Opin. Biotechnol. 16: 1-9.

    Article  CAS  Google Scholar 

  • Davin, L. B., and Lewis, N. G., 2000, Dirigent proteins and dirigent sites explain the mystery of specificity of radical precursor coupling in lignan and lignin biosynthesis, Plant Physiol. 123: 453-461.

    Article  PubMed  CAS  Google Scholar 

  • Davin, L. B., Wang, H.-B., Crowell, A. L., Bedgar, D. L., Martin, D. M., Sarkanen, S., and Lewis, N. G., 1997, Stereoselective bimolecular phenoxy radical coupling by auxilary (dirigent) protein without an active center, Science 275: 362-366.

    Article  PubMed  CAS  Google Scholar 

  • Debeaujon, I., Peeters, A. J. M., Léon-Kloosterziel, K. M., and Koornneef, M., 2001, The TRANSPARENT TESTA12 gene of Arabidopsis encodes a multidrug secondary transporter-like protein required for flavonoid sequestration in vacuoles of the seed coat endothelium, Plant Cell 13: 853-872.

    Article  PubMed  CAS  Google Scholar 

  • Degenhart, N.R., B.K. Werner, and G.W. Burton, 1995, Forage yield and quality of a brown midrib mutant in pearl millet, Crop Sci. 35: 986–988.

    Article  Google Scholar 

  • Dellaporta, S. L., Greenblatt, I., Kermicle, J. L., Hicks, J. B., and Wessler, S. R., 1988, Molecular cloning of the maize R-nj allele by transpson tagging with Ac, Stadler Genet. Symp. 18: 263-282.

    Google Scholar 

  • Dennis, D. T., and Blakeley, S. D., 2000, Carbohydrate metabolism, in: Biochemistry and Molecular Biology of Plants, Buchanan, B. B., Gruissem, W., Jones, R. J., eds., John Wiley & Sons, Somerset, NJ, pp. 630-675.

    Google Scholar 

  • Denton, F. R., 1998, Beetle juice, Science 281: 1285.

    Article  PubMed  CAS  Google Scholar 

  • Devic, M., Guilleminot, J., Debeaujon, I., Bechtold, N., Bensaude, E., Koornneef, M., Pelletier, G., Delseny, M., 1999, The BANYULS gene encodes a DFR-like protein and is a marker of early seed coat development, Plant J. 19: 387-398.

    Article  PubMed  CAS  Google Scholar 

  • Dias, A. P., and Grotewold, E., 2003, Manipulating the accumulation of phenolics in maize cultured cells using transcription factors, Biochem. Eng. J. 14: 207-216.

    Article  CAS  Google Scholar 

  • Doerge, R. W., 2002, Mapping and analysis of quantitative trait loci in experimental populations, Nature Rev. Gen. 3: 43-53.

    Article  CAS  Google Scholar 

  • Dooner, H., and Nelson, O. E., 1977, Controlling element-induced alterations in UDPglucose: flavonoid glucosyltransferase, the enzyme specified by the bronze locus in maize, Proc. Natl. Acad. Sci. USA 74: 5623-5627.

    Article  PubMed  CAS  Google Scholar 

  • Draude, K. M., Kurniawan, C. B., and Duff, S. J. B., 2001, Effect of oxygen delignification on the rate and extend of enzymatic hydrolysis of lignocellulosic material, Biores. Technol. 79: 113-120.

    Article  CAS  Google Scholar 

  • Evtuguin, D. V., and Amada, F. M. L., 2003, Application of electrospray ionization mass spectrometry to the elucidation of the primary structure of lignin, Macromol. Biosci. 3: 339-343.

    Article  CAS  Google Scholar 

  • Federoff, N. V., Furtek, D., and Nelson, O. E., 1984, Cloning of the bronze locus in maize by a simple and generalizable procedure using the transposable controlling element Activator (Ac), Proc. Natl. Acad. Sci. USA 81: 3825-3829.

    Article  Google Scholar 

  • Feinbaum, R. L., and Ausubel, F. M., 1988, Transcriptional regulation of the Arabidopsis thaliana chalcone synthase gene, Mol. Cell. Biol. 8: 1985- 1992.

    PubMed  CAS  Google Scholar 

  • Fieldes, M. A., and Dixon, B., 1988, Malate dehydrogenase isozymes in flax genotroph leaves: differences in apparent molecular weight and charge between and within L and S, Biochem. Genet. 26: 249-260.

    Article  PubMed  CAS  Google Scholar 

  • Fontaine, A. S., Bout, S., Barrière, Y., and Vermerris, W., 2003, Variation in cell wall composition among forage maize (Zea mays L.) inbred lines and its impact in digestibility analysis of neutral detergent fiber composition by pyrolysis-gas chromatography-mass spectrometry, J. Agric. Food Chem. 51: 8080-8087.

    Article  PubMed  CAS  Google Scholar 

  • Franke, R., Hemm, M. R., Denault, J. W., Ruegger, M. O., Humphreys, J. M., and Chapple, C., 2002a, Changes in the secondary metabolism and deposition of an unusual lignin in the ref8 mutant of Arabidopsis, Plant J. 30: 33-45.

    Article  CAS  Google Scholar 

  • Franke, R., Humphreys, J. M., Hemm, M. R., Denault, J. W., Ruegger, M. O., Cusumano, J. C., and Chapple, C., 2002b, The Arabidopsis REF8 gene encodes the 3-hydroxylase of phenylpropanoid metabolism, Plant J. 30: 33-45.

    Article  CAS  Google Scholar 

  • Freudenberg, K., 1965, Lignin: Its constitution and formation from phydroxycinnamyl alcohols, Science 148: 595-600.

    Article  PubMed  CAS  Google Scholar 

  • Frey, M., Chomet, P., Glawischnig, E., Stettner, C., Grün, S., Winklmair, A., Eisenreich, W., Bacher, A., Meeley, R. B., Briggs, S. P., Simcox, K., and Gierl, A., 1997, Analysis of a chemical plant defense mechanism in grasses, Science 277 : 696-699.

    Article  PubMed  CAS  Google Scholar 

  • Gang, D. R., Costa, M. A., Fujita, M., Dinkova-Kostova, A. T., Wang, H.- B., Burlat, V., Martin, W., Sarkanen, S., Davin, L. B., and Lewis, N. G., 1999, Regiochemical control of monolignol radical coupling: a new paradigm for lignin and lignan biosynthesis, Chem. & Biol. 6: 143-151.

    Article  CAS  Google Scholar 

  • Gelvin, S. B., 2000, Agrobacterium and plant genes involved in T-DNA transfer and integration, Annu. Rev. Plant Physiol. Plant Mol. Biol. 51: 223-256.

    Article  PubMed  CAS  Google Scholar 

  • Gelvin, S. B., 2003, Agrobacterium-mediated plant transformation: the biology behind the "gene-jockeying" tool, Microbiol. Mol. Biol. Rev. 67: 16-37.

    Article  PubMed  CAS  Google Scholar 

  • Goicoechea, M., Lacombe, E., Legay, S., Mihaljevic, S., Rech, P., Jauneau, A., Lapierre, C., Pollet, B., Verhaegen, D., Chaubet-Gigot, N., and Grima-Pettenati, J., 2005, EgMYB2, a new transcriptional activator from Eucalyptus xylem, regulates secondary cell wall formation and lignin biosynthesis, Plant J. 43: 553-567.

    Google Scholar 

  • Goffner, D., Campbell, M.M., Campargue, C., Clastre, M., Borderies, G., Boudet, A. and Boudet, A.M., 1994, Purification and characterization of cinnamoyI-CoA: NADP oxidoreductase in Eucalyptus gunnii, Plant Physiol. 106: 625-632.

    PubMed  CAS  Google Scholar 

  • Goujon, T., Sibout, R., Eudes, A., MacKay, J., and Jouanin, L., 2003, Genes involved in the biosynthesis of lignin precursors in Arabidopsis thaliana, Plant Physiol. Biochem. 41: 677-687.

    Article  CAS  Google Scholar 

  • Grabber, J. H., Ralph, J., Hatfield, R. D., Quideau, S., Kuster T., Pell, A. N., 1996, Dehydrogenation polymer-cell wall complexes as a model for lignified grass walls, J. Agric. Food Chem. 44: 1453–1459.

    Article  CAS  Google Scholar 

  • Gracey, A. Y., and Cossins, A. R., 2003, Application of microarray technology in environmental and comparative physiology, Annu. Rev. Physiol. 65: 231-259.

    Article  PubMed  CAS  Google Scholar 

  • Gross, G.G., 1983, Synthesis of mono-, di- and trigalloyl-β-D-glucose by β - glucogallin-dependent galloyltransferases from oak leaves, Z. Naturforsch. 38c: 519-523.

    CAS  Google Scholar 

  • Grotewold, E., Athma, P, and Peterson, T., 1991, Alternatively spliced products of the maize P gene encode proteins with homology to the DNA-Binding domain of myb-like transcription factors, Proc. Natl. Acad. Sci. USA 88: 4587-4591.

    Article  PubMed  CAS  Google Scholar 

  • Grotewold, E., Drummond, B. J., Boen, B., and Peterson, T., 1994, The myb-homologous P gene controls phlobaphene pigmentation in maize floral organs by directly activating a flavonoid biosynthetic gene subset, Cell 76: 543-553.

    Article  PubMed  CAS  Google Scholar 

  • Guan, S. Y., Mylnar, J., and Sarkanen, S., 1997, Dehydrogenative polymerization of coniferyl alcohol on macromolecular lignin templates, Phytochem. 45: 911–918.

    Article  CAS  Google Scholar 

  • Halpin, C., Holt, K., Chojecki, J., Oliver, D., Chabbert, B., Monties, B., Edwards, K., Barakate, A., and Foxon, G. A., 1998, Brown-midrib maize (bm1) - a mutation affecting the cinnamyl alcohol dehydrogenase gene, Plant J. 14: 545-553.

    Article  PubMed  CAS  Google Scholar 

  • Hartley, R. D., Morrison, W. H., Borneman, W. S., Rigsby, L. L., O’Neill, M., Hanna, W. W., and Akin, D. E., 1992, Phenolic constituents of cell wall types of normal and brown midrib mutants of pearl millet (Pennisetum glaucum (L.) R. Br.) in relation to wall biodegradability, J. Sci. Food Agric. 59: 211-216.

    Article  CAS  Google Scholar 

  • Harkin, J. M., and Obst, J. R., 1973, Lignification in trees: indication of exclusive peroxidase participation, Science 180:296-298.

    Article  PubMed  CAS  Google Scholar 

  • Hatfield, R., and Vermerris, W., 2001, Lignin formation in plants: the dilemma of linkage specificity, Plant Physiol. 126: 1351-1357.

    Article  PubMed  CAS  Google Scholar 

  • Higuchi, T., 1985, Biosynthesis of lignin, in: Biosynthesis and Biodegradation of Wood Components, T. Higuchi, ed., Academic Press, Orlando, pp. 141-160.

    Google Scholar 

  • Heller, W., and Kühnl, T., 1985, Elicitor induction of a microsomal 5-O-(4- coumaroyl) shikimate 3’-hydroxylase in parsley cell suspension cultures, Arch. Biochem. Biophys. 241: 453-460.

    Google Scholar 

  • Herrmann, K., and Weaver, L. M., 1999, The shikimate pathway, Annu. Rev. Plant Physiol. Plant Mol. Biol. 50: 473-503.

    Article  PubMed  CAS  Google Scholar 

  • Hoffmann, L., Besseau, S., Geoffroy, P., Ritzenthaler, Ch., Meyer, D., Lapierre, C., Pollet, B., and Legrand, M., 2004, Silencing of hydroxycinnamoyl-coenzyme A shikimate/quinate hydroxyltransferase affects phenylpropanoid biosynthesis, Plant Cell 16: 1446-1465.

    Article  PubMed  CAS  Google Scholar 

  • Hoffmann, L., Maury, S., Martz, F., Geoffroy, P., and Legrand, M., 2003, Purification, cloning, and properties of an acyltransferase controlling shikimate and quinate ester intermediates in phenylpropanoid metabolism, J. Biol. Chem 278: 95-103.

    Article  PubMed  CAS  Google Scholar 

  • Hofmann, A. S., and Gross, G. G., 1990, Biosynthesis of gallotannins: formation of polygalloylglucoses by enzymatic acylation of 1,2,3,4,6- penta-O-galloylglucose, Arch. Biochem. Biophys. 283:530-532.

    Article  PubMed  CAS  Google Scholar 

  • Humphreys, J. M., and Chapple, C., 2002, Rewriting the lignin road map, Curr. Opin. Plant Biol. 5: 224-229.

    Article  PubMed  CAS  Google Scholar 

  • Humphreys, J. M., Hemm, M. R., and Chapple, C., 1999, New routes for lignin biosythesis defined by biochemical characterization of recombinant ferulate 5-hydroxylase, a multifunctional cytochrome P450- dependent monooxygenase, Proc. Natl. Acad. Sci. USA 96: 10045- 10050.

    Article  PubMed  CAS  Google Scholar 

  • Huntley, S. K., Ellis, D., Gilbert, M., Chapple, C., and Mansfield, S. D., 2003, Significant increases in pulping efficiency in C4H-F5Htransformed poplars: improved chemical savings and reduced environmental toxins, J. Agric. Food Chem. 51: 6178-6183.

    Article  PubMed  CAS  Google Scholar 

  • Innes, M. A., Gelfand, D. H., Sinsky, J. J., 1999, PCR Applications. Protocols for Functional Genomics, Academic Press, San Diego, pp. 566.

    Google Scholar 

  • International Rice Genome Sequencing Project, 2005, The map-based sequence of the rice genome, Nature 436: 793-800.

    Google Scholar 

  • Johnson, C. S., Kolevski, B., and Smyth, D. R., 2002, TRANSPARENT TESTA GLABRA2, a trichome and seed coat development gene of Arabidopsis, encodes a WRKY transcription factor, Plant Cell 14: 1359- 1375.

    Article  PubMed  CAS  Google Scholar 

  • Joseleau, J.-P., and Ruel, K., 1997, Study of lignification by noninvasive techniques in growing maize internodes, Plant Physiol. 114: 1123-1133.

    Article  PubMed  CAS  Google Scholar 

  • Kawaoka, A., Kaothien, P., Yoshida, K., Endo, S., Yamda, K., and Ebinuma, H., 2000, Functional analysis of tobacco LIM protein, Ntlim1, involved in lignin biosynthesis, Plant J. 22: 289-301.

    Article  PubMed  CAS  Google Scholar 

  • Kruger, N.J., and Von Schaewen, A., 2003, The oxidative pentose phosphate pathway: structure and organization, Curr. Opin. Plant Biol. 6: 236-246.

    Google Scholar 

  • Kühnl, T., Koch, U., Heller, W., and 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, Arch. Biochem. Biophys. 258: 226- 232.

    Article  PubMed  Google Scholar 

  • Kühnl, T., Koch, U., Heller, W., and Wellmann, E., 1989, Elicitor induced S-adenosyl-L-methionine: caffeoyl-CoA 3-O-methyltransferase from carrot cell suspension, Plant Sci. 60: 21-25.

    Article  Google Scholar 

  • Ladisch, M. R., Ladisch, C. M., and Tsao, G. T, 1978, Cellulose to sugars: New path gives quantitative yield, Science 201: 743-745.

    Article  PubMed  CAS  Google Scholar 

  • Lacombe, E., Hawkins, S., Van Doorsselaere, J., Piquemal, J., Goffner, D., Poeydomenge, O., Boudet, A.-M., and Grima-Pettenati, J., 1997, Cinnamoyl CoA reductase, the first committed enzyme of the lignin branch biosynthetic pathway: cloning, expression and phylogenetic relationships, Plant J. 11: 429-441.

    Google Scholar 

  • Lam, T. B. T., Iayama, K., and Stone, B. A., 1996, Lignin and hydroxycinnamic acids in walls of brown midrib mutants of sorghum, pearl millet and maize stems, J. Sci. Food Agric. 71: 174-178.

    Article  CAS  Google Scholar 

  • Larson, R., and Coe, E. H., 1977, Gene-dependent flavonoid glucosyltransferase in maize, Biochem. Genet. 15: 153-156.

    Article  PubMed  CAS  Google Scholar 

  • Lechelt, C., Peterson, T., Laird, A., Chen, J., Dellaporta, S., Dennis, E., Starlinger, P., and Peacock, W. J., 1989, Isolation and molecular analysis of the maize P locus, Mol. Gen. Genet. 219: 225-234.

    Article  PubMed  CAS  Google Scholar 

  • Lehfeldt, C., Shirley, A. M., Meyer, K., Ruegger, M. O., Cusumano, J. C., Viitanen, P. V., Strack, D., and Chapple, C., 2000 , Cloning of the SNG1 gene of Arabidopsis reveals a role for a serine carboxypeptidase-like protein as an acyltransferase in secondary metabolism, Plant Cell 12: 1295-1306.

    Article  PubMed  CAS  Google Scholar 

  • Leon, J., Shulaev, V., Yalpani, N., Lawton, M. A. and Raskin, I., 1995, Benzoic acid 2-hydroxylase, a soluble oxygenase from tobacco, catalyzes salicylic acid biosynthesis, Proc. Natl. Acad. Sci. USA 92: 10413-10417.

    Article  PubMed  CAS  Google Scholar 

  • Lewis, N. G., and Davin, L. B., 1998, The biochemical control of monolignol coupling and structure during lignan and lignin biosynthesis. In: Lignin and Lignan Biosynthesis, Vol. 697, N. G. Lewis, and S. Sarkanen, eds., ACS Symposium Series, Washington, DC, pp. 334-361.

    Google Scholar 

  • Lewis, N. G., 1999, A 20th century roller coaster ride: a short account of lignification, Curr. Opin. Plant Biol. 2: 153-162.

    Article  PubMed  CAS  Google Scholar 

  • Li, L., Cheng, X. F., Leshkevich, J., Umezawa, T., Harding, S. A., and Chiang, V. L., 2001, The last step of syringyl monolignol biosynthesis in angiosperms is regulated by a novel gene encoding sinapyl alcohol dehydrogenase, Plant Cell 13: 1567-1585.

    Article  PubMed  CAS  Google Scholar 

  • Li, Y. H., Kajita, S., Kawai, S., Katayama, Y., and Morohoshi, N., 2003, Down-regulation of an anionic peroxidase in transgenic aspen and its effect on lignin characteristics, J. Plant Res. 116: 175–182.

    Article  PubMed  CAS  Google Scholar 

  • Lim, E.-.K, Li, Y., Parr, A., Jackson, R., Ashford, D. A., and Bowles, D. J., 2001, Identification of glucosyltransferase genes involved in sinapate metabolism and lignin synthesis in Arabidopsis, J. Biol. Chem. 276: 4344-4349.

    Article  PubMed  CAS  Google Scholar 

  • Liu, Y.-G., Mitsukawa, N., Oosumi, T., and Whittier, R. F., 1995, Efficient isolation and mapping of Arabidopsis thaliana T-DNA insert junctions by thermal assymetric interlaced PCR, Plant J. 8: 457-463.

    Article  PubMed  CAS  Google Scholar 

  • Lorenzen, M., Racicot, V., Strack, D., Chapple, C., 1996, Sinapic acid ester metabolism in wild type and a sinapoylglucose-accumulating mutant of Arabidopsis, Plant Physiol. 112: 1625-1630.

    Article  PubMed  CAS  Google Scholar 

  • Lourith, N., Katayama, T., and Suzuki, T., 2005, Stereochemistry and biosynthesis of 8-O-4’ neolignans in Eucommia ulmoides: diastereoselective formation of guaiacylglycerol 8-O-4’-(sinapyl alcohol) ether, J. Wood Sci. 51: 370-378.

    Article  CAS  Google Scholar 

  • Marita, J., Vermerris, W., Ralph, J., and Hatfield, R. D., 2003, Variations in the cell wall composition of maize brown midrib mutants, J. Agric. Food Chem. 51: 1313-1321.

    Article  PubMed  CAS  Google Scholar 

  • McClintock, B., 1947, Cytogenetic studies of maize and Neurospora, Carnegie Inst. Wash. Year Book 46: 146-152.

    Google Scholar 

  • McDougall, G. J., Stewart, D., and Morrison, I. M., 1996, Tyrosine residues enhance cross-linking of synthetic proteins into lignin dehydrogenation products, Phytochem. 41: 43-47.

    Article  CAS  Google Scholar 

  • McLaughlin, M., and Walbot, V., 1987, Cloning of a mutable bz2 allele of maize by transposon tagging and differential hybridization, Genetics 117: 771-776.

    PubMed  CAS  Google Scholar 

  • Messen, A., Höhmann, S., Martin, W., Schnable, P.S., Peterson, P.A., Saedler, H., and Gierl, A., 1990, The En/Spm transposable element of Zea mays contains splice sites at the termini generating a novel intron from a dSpm element in the A2 gene. EMBO J. 9: 3051 3057.

    Google Scholar 

  • Meyer, K., Cusumano, J. C., Sommerville, C., and Chapple, C. C. S., 1996, Ferulate-5-hydroxylase from Arabidopsis thaliana defines a new family of cytochrome P-450 dependent monooxygenases, Proc. Natl. Acad. Sci. USA 93: 6869-6874.

    Article  PubMed  CAS  Google Scholar 

  • 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., and 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. 275: 36899–36909.

    Article  PubMed  CAS  Google Scholar 

  • Mosier, N., Wyman, C., Dale, B., Elander, R., Lee, Y. Y., Holtzapple, M., and Ladisch, M., 2005, Features of promising technologies for pretreatment of lignocellulosic biomass, Biores. Technol. 96: 673-686.

    Article  CAS  Google Scholar 

  • Nair, R. B., Bastress, K. L., Ruegger, M. O., Denault, J. W., and Chapple, C., 2004, The Arabidopsis thaliana REDUCED EPIDERMAL FLUORESCENCE1 gene encodes an aldehyde dehydrogenase involved in ferulic acid and sinapic acid biosynthesis, Plant Cell 16: 544-554.

    Article  PubMed  CAS  Google Scholar 

  • Nakayama, T., Sato, T., Fukui, Y., Yonekura-Sakakibara, K., Hayashi, H., Tanaka, Y., Kusumi, T., and Nishino, T., 2001, Specifcity analysis and mechanism of aurone synthesis catalyzed by aureusidin synthase, a polyphenol oxidase homolog responsible for flower coloration, FEBS Lett. 499: 107-111.

    Article  PubMed  CAS  Google Scholar 

  • Nakayama, T., Yonekura-Sakakibara, K., Sato, T., Kikuchi, S., Fukui, Y., Fukuchi-Mizutani, M., Ueda, T., Nakao, M., Tanaka, Y., Kusumi, T., and Nishino, T., 2000, Aureusidin synthase: A polyphenol oxidase homolog responsible for flower coloration, Science 290: 1163-1167.

    Article  PubMed  CAS  Google Scholar 

  • Nesi, N., Jond, C., Debeaujon, I., Caboche, M., and Lepiniec, L., 2001, The Arabidopsis TT2 gene encodes an R2R3 MYB domain protein that acts as a key determinant for proanthocyanidin accumulation in developing seed, Plant Cell 13: 2099-2114.

    Google Scholar 

  • Newman L. J., Perazza, D. E., Juda, L., Campbell, M. M., 2004, Involvement of the R2R3-MYB, AtMYB61, in the ectopic lignification and dark-photomorphogenic components of the det3 mutant phenotype. Plant J. 37: 239–250.

    CAS  Google Scholar 

  • Niemetz, R., and Gross, G. G., 2003, Oxidation of pentagalloylglucose to the ellagitannin, tellimagrandin II, by a phenol oxidase from Tellima grandiflora leaves, Phytochem. 62: 301-306.

    Article  CAS  Google Scholar 

  • Niemetz, R., and Gross, G. G., 2005, Enzymology of gallotannin and ellagitannin biosynthesis, Phytochem. 66: 2001-2011.

    Article  CAS  Google Scholar 

  • Niesbach-Klösgen, U., Barzen, E., Bernhardt, J., Rohde, W., Schwarz- Sommer, Z., Reif, H. J., Wienand U., and Saedler, H., 1987, Chalcone synthase genes in plants: A tool to study evolutional relationships, J. Mol. Evol. 26: 213-225.

    Article  Google Scholar 

  • Nimz, H. H., and Ludemann, H. D., 1976, Carbon 13 nuclear magnetic resonance spectra of lignins: 6. Lignin and DHP acetates. Holzforsch. 30: 33–40.

    Article  CAS  Google Scholar 

  • O’Malley, D. M., Whetten, R., Bao, W., Chen, C.-L., and Sederoff, R. R., 1993, The role of laccases in lignification, Plant J. 4: 751-757.

    Article  CAS  Google Scholar 

  • O’Reilly, C., Shepherd, N. S., Pereira, A., Schwarz-Sommer, Z., Betram, I., Robertson, D. S., Peterson, P. A., and Saedler, H., 1985, Molecular cloning of the a1 locus of Zea mays using the transposable elements En and Mu1, EMBO J. 4: 877-882.

    PubMed  CAS  Google Scholar 

  • Osakabe, K., Tsao, C. C., Li, L., Popko, J. L., Umezawa, T., Carraway, D. T., Smeltzer, R. H., Joshi, C. P., and Chiang, V. L., 1999, Coniferyl aldehyde 5-hydroxylation and methylation direct syringyl lignin biosynthesis in angiosperms, Proc. Natl. Acad. Sci. USA 96: 8955-8960.

    Article  PubMed  CAS  Google Scholar 

  • Ossipov, V., Salminen, J., Ossipova, S., Haukioja, E., and Pihlaja, K., 2003, Gallic acid and hydrolyzable tannins are formed in birch leaves from an intermediate compound of the shikimate pathway, Biochem. Syst. Ecol. 31: 3–16.

    Article  CAS  Google Scholar 

  • Palonen, H., Tjerneld, F., Zacchi, G., and Tenkanen, M., 2004, Adsorption of Trichoderma reesei CBH I and EG II and their catalytic domains on steam pretreated softwood and isolated lignin, J. Biotechnol. 107: 65-72.

    Article  PubMed  CAS  Google Scholar 

  • Patten, A. M., Cardenas, C. L., Cochrane, F. C., Laskar, D. D., Bedgar, D. L., Davin, L. B., and Lewis, N. G., 2005, Reassessment of effects on lignification and vascular development in the irx4 Arabidopsis mutant, Phytochem. 17 :2092-2107.

    Article  CAS  Google Scholar 

  • Patzlaff, A., Newman, L. J., Dubos, C., Whetten, R. W., Smith, C., McInnis, S., Bevan, M. W., Sederoff, R. R., and Campbell, M. M., 2003, Characterisation of a pine MYB that regulates lignification, Plant J. 36: 743-754.

    Article  PubMed  CAS  Google Scholar 

  • Paz-Ares, J., Goshal, D., and Saedler, H., 1990, Molecular analysis of the C1-I allele from Zea mays : A dominant mutant of the regulatory C1 locus, EMBO J. 9: 315-321.

    PubMed  CAS  Google Scholar 

  • Paz-Ares, J., Goshal, D., Wienand, U., Peterson, P. A., and Saedler, H., 1987, The regulatory c1 locus of Zea mays encodes a protein with homology to myb proto-oncogene products and with structural similarities to transcriptional activators, EMBO J. 6: 3553-3558.

    PubMed  CAS  Google Scholar 

  • Paz-Ares, J., Wienand, U., Peterson, P. A., and Saedler, H., 1986, Molecular cloning of the c locus of Zea mays: A locus regulating the anthocyanin pathway, EMBO J. 5: 829-833.

    PubMed  CAS  Google Scholar 

  • Pelletier, M.K., and Shirley, B.W., 1996, Analysis of flavanone 3- hydroxylase in Arabidopsis seedlings: Coordinate regulation with chalcone synthase and chalcone isomerase, Plant Physiol. 111: 339–345.

    Google Scholar 

  • Pflieger, S., Lefebvre, V., and Causse, M. 2001, The candidate gene approach in plant genetics: a review, Mol. Breeding 7: 275-291.

    Article  CAS  Google Scholar 

  • Pilate, G., Guiney, E., Holt, K., Petit-Conil, M., Lapierre, C., Leplé, J. C., Pollet, B., Mila, I., Webster, E. A., Marstorp, H. G., Hopkins, D. W., Jouanin, L., Boerjan, W., Schuch, W., Cornu, D., and Halpin, C., 2002, Field and pulping performances of transgenic trees with altered lignification, Nature Biotechnol. 20: 607-612.

    Article  CAS  Google Scholar 

  • Pillonel, C., Mulder, M. M., Boon, J. J., Forster, B., and Binder, A., 1991, Involvement of cinnamyl-alcohol dehydrogenase in the control of lignin formation in Sorghum bicolor L. Moench, Planta 185: 538-544.

    Article  CAS  Google Scholar 

  • Plaxton, W. C., 1996, The organization and regulation of plant glycolysis, Annu. Rev. Plant Physiol. Plant Mol. Biol. 47: 185-214.

    Article  PubMed  CAS  Google Scholar 

  • Plaxton, W., and McManus, M, 2006, Control of primary metabolism in plants, Blackwell Publishing, Oxford, pp. 400.

    Google Scholar 

  • Porter, K. S., Axtell, J. D., Lechtenberg, V. L., and Colenbrander, V. F., 1978, Phenotype, fiber composition, and in vitro dry matter disappearance of chemically induced brown midrib (bmr) mutants of sorghum, Crop Sci. 18: 205-209.

    Article  CAS  Google Scholar 

  • Radicella, J. P., Turks, D., and Chandler, V. L., 1991, Cloning and nucleotide sequence of a cDNA encoding B-Peru, a regulatory protein of the anthocyanin pathway in maize, Plant Mol. Biol. 17: 127-130.

    Article  PubMed  CAS  Google Scholar 

  • Radicella, J. P., Brown, D., Tolar, L. A., and Chandler, V. L., 1992, Allelic diversity of the maize B regulatory gene: Different leader and promoter sequences of two B alleles determine distinct tissue specificities of anthocyanin production, Genes Dev. 6: 2152-2164.

    Article  PubMed  CAS  Google Scholar 

  • Raes, J., Rohde, A., Christensen, J. H., Van de Peer, Y., and Boerjan, W., 2003, Genome-wide characterization of the lignification toolbox in Arabidopsis, Plant Physiol. 133: 1051-1071.

    Article  PubMed  CAS  Google Scholar 

  • Ralph, J., and Helm, R.F., 1993, Lignin/ hydroxycinnamic acid/ polysaccharide complexes: synthetic models for regiochemical characterization, in: Jung, H. G., Buxton, D. R., Hatfield, R. D., and Ralph J., eds., Forage Cell Wall Structure and Digestibility, ASACSSA- SSSA, Madison, WI., pp. 201-246.

    Google Scholar 

  • 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., and Boerjan, W., 2004, Lignins: natural polymers from oxidative coupling of 4- hydroxyphenylpropanoids, Phytochem. 3: 29-60.

    Article  CAS  Google Scholar 

  • Ralph, J., Peng, J., Lu, F., Hatfield, R. D., and Helm, R. F., 1999, Are lignins optically active?, J. Agric. Food Chem. 47: 2991-2996.

    Article  PubMed  CAS  Google Scholar 

  • Ranocha P., Chabannes, M., Chamayou, S., Danoun, S., Jauneau, A., Boudet, A.-M., and Goffner, D., 2002, Laccase down-regulation causes alterations in phenolic metabolism and cell wall structure in poplar, Plant Physiol. 129: 145-155.

    Article  PubMed  CAS  Google Scholar 

  • Reddy, G. M., and Coe, E. H., jr., 1962, Intertissue specific complementation: A simple technique for direct analysis of gene sequence, Science 138: 149-150.

    Article  PubMed  CAS  Google Scholar 

  • Ribnicky, D. M., Shulaev, V., and Raskin, I., 1998, Intermediates of salicylic acid biosynthesis in tobacco, Plant Physiol. 118, 565-572.

    Article  PubMed  CAS  Google Scholar 

  • Ribot, E. M., 1998, Rapid amplification of transposon ends for the isolation, cloning and sequencing of transposon-disrupted chromosomal genes, BioTechniques 24: 16-20.

    PubMed  CAS  Google Scholar 

  • Robbins, T. P., Walker, E. L., Kermicle, J. L., Alleman, M., and Dellaporta, S. L., 1991, Meiotic instability of the R-r complex arising from displaced intragenic exchange and intrachromosomal rearrangement, Genetics, 129: 271-283.

    PubMed  CAS  Google Scholar 

  • Roesler, J., Krekel, F., Amrhein, N., and Schmid, J., 1997, Maize phenylalanine ammonia-lyase has tyrosine ammonia-lyase activity, Plant Physiol. 113: 175-179.

    Article  CAS  Google Scholar 

  • Rogers, L. A., and Campbell, M. M., 2004, The genetic control of lignin deposition during plant growth and development, New Phytol. 164: 17- 30.

    Article  CAS  Google Scholar 

  • Rogers, L. A., Dubos, C., Surman, C., Willment, J., Cullis, I. F., Mansfield, S. D., and Campbell, M. M., 2005, Comparison of lignin deposition in three ectopic lignification mutants, New Phytol. 168: 123.

    Article  PubMed  CAS  Google Scholar 

  • Saballos, A., Vermerris, W, and Ejeta, G., 2005, Allelic variation among brown midrib mutants of sorghum, 50th CSSA Annual Meeting, Salt Lake City, UT.

    Google Scholar 

  • Sablowski, R. W., Moyano, E., Culianez-Macia, F. A., Schuch, W., Martin, C., and Bevan, M., 1994. A flower-specific Myb protein activates transcription of phenylpropanoid biosynthetic genes, EMBO J. 13: 128– 137.

    Google Scholar 

  • Sagasser, M., Lu, G.-H., Hahlbrock, K., and Weisshaar, B., 2002, A. thaliana TRANSPARENT TESTA1 is involved in seed coat development and defines the WIP subfamily of plant zinc finger proteins, Genes Dev. 16: 138-149.

    Article  CAS  Google Scholar 

  • Saiki, R. K., Scharf, S., Faloona, F., Mullis, K. B., Horn, G. T., Erlich, H. A., Arnheim, N., 1985, Enzymatic amplification of β-globin genomic sequences and restriction site analysis for diagnosis of sickle cell anemia, Science 230: 1350-1354.

    Article  PubMed  CAS  Google Scholar 

  • Saito, K., Kobayashi, M., Gong, Z. Z., Tanaka, Y., and Yamazaki, M., 1999. Direct evidence for anthocyanidin synthase as a 2-oxoglutaratedependent oxygenase: molecular cloning and functional expression of cDNA from a red forma of Perilla frutescens, Plant J. 17: 181-190.

    Article  PubMed  Google Scholar 

  • Schoenbohm, C., Martens, S., Eder, C., Forkmann, G., and Weisshaar, B., 2000, Identification of the Arabidopsis thaliana flavonoid 3’-hydroxylase gene and functional expression of the encoded P450 enzyme, Biol. Chem. 381: 749–753.

    Google Scholar 

  • Schoch, G., Goepfert, S., Morant, M., Hehn, A., Meyer, D., Ullmann, P., and Werck-Reichhart, D., 2001, CYP98A3 from Arabidopsis thaliana is a 3’-hydroxylase of phenolic esters, a missing link in the phenylpropanoid pathway, J. Biol. Chem. 276: 36566-36574.

    Article  PubMed  CAS  Google Scholar 

  • Schröder, J., and Schröder, G., 1990, Stilbene and chalcone synthases: related enzymes with key functions in plant-specific pathways, Z. Naturforsch. 45: 1-8.

    Google Scholar 

  • Schulze, A., and Downward, J., 2001, Navigating gene expression using microarrays — a technology review, Nature Cell Biol. 3: E190 - E195

    Article  PubMed  CAS  Google Scholar 

  • Schwarz-Sommer, Z., Shepherd, N., Tacke, E., Gierl, A., Rohde, W., Le Clerq, L., Mattes, M., Berndtgen, R., Peterson, P. A., and Saedler, H., 1987, Influence of transposable elements on the structure and function of the A1 gene of Zea mays, EMBO J. 6: 287-294.

    PubMed  CAS  Google Scholar 

  • Schwarz-Sommer, Z., Davies, B., and Hudson, A., 2003, An everlasting pioneer: the story of Antirrhinum research, Nature Rev. Genetics 4: 656- 664.

    Google Scholar 

  • Sederoff, R. R., Mackay, J. J., Ralph, J., and Hatfield, R. D., 1999, Unexpected variation in lignin, Curr. Opin. Plant Biol. 2: 145-152.

    Article  PubMed  CAS  Google Scholar 

  • Seidel, V., Windhövel, J., Eaton, G., Alfermann, W. A., Arroo, R. R., Medarde, M., Petersen, M., Woolley, J. G., 2002, Biosynthesis of podophyllotoxin in Linum album cell cultures, Planta 215: 1031-1039.

    Article  PubMed  CAS  Google Scholar 

  • Shirley, A. M., and Chapple, C., 2003, Biochemical characterization of sinapoylglucose:choline sinapoyltransferase, a serine carboxypeptidaselike protein that functions as an acyltransferase in plant secondary metabolism, J. Biol. Chem. 278: 19870-19877.

    Article  PubMed  CAS  Google Scholar 

  • Shirley, B. W., Hanley, S, and Goodman, H, M., 1992, Effects of ionizing radiation on a plant genome: analysis of two Arabidopsis transparent testa mutations, Plant Cell 4: 333-347.

    Article  PubMed  CAS  Google Scholar 

  • Sibout, R., Eudes, A., Pollet, B., Goujon, T., Mila, I., Granier, F., Seguin, A., Lapierre, C., and Jouanin, L., 2003, Expression pattern of two paralogs encoding cinnamyl alcohol dehydrogenases in Arabidopsis. Isolation and characterization of the corresponding mutants, Plant Physiol. 132: 848-860.

    Article  PubMed  CAS  Google Scholar 

  • Sterijades, R., Dean, J. F. D., Gamble, G., Himmelsbach, D. S., and Eriksson, K.-E. L., 1993, Extracellular laccase and peroxidases from sycamore maple (Acer pseudoplatanus) cell suspension cultures. Reactions with monolignols and lignin model compounds, Planta 190: 75-87.

    Google Scholar 

  • Suzuki, S., Lam, T. B. T., and Iiyama, K. 1997, 5-Hydroxyguaiacyl nuclei as aromatic constituents of native lignin, Phytochem. 46: 695-700.

    Article  CAS  Google Scholar 

  • Syrjanen., K, and Brunow, G., 2000, Regioselectivity in lignin biosynthesis: the influence of dimerization and crosscoupling, J. Chem. Soc. Perkin. Trans. I 1: 183–187.

    Article  Google Scholar 

  • Tamagnone, L., Merida, A., Parr, A., MAckay, S., Culianez-Macia, F. A., Roberts, K., and Martin, C., 1998, The AmMYB308 and AmMYB330 transcription factors from Antirrhinum regulate phenylpropanoid and lignin biosynthesis in transgenic tobacco, Plant Cell 10: 135-154.

    Article  PubMed  CAS  Google Scholar 

  • Tan, B. C., Schwartz, S. H., Zeevaart, J. A. D., and McCarthy, D. R., 1997, Genetic control of abscisic acid biosynthesis in maize, Proc. Natl. Acad. Sci. USA 94: 12235-12240.

    Google Scholar 

  • Terashima, N., Atalla, R. H., Ralph, S. A., Landucci, L. L., Lapierre, C., and Monties, B., 1996, New preparations of lignin polymer models under conditions that approximate cell well lignification: I. Synthesis of novel lignin polymer models and their structural characterization by 13C NMR., Holzforsch. 49: 521–527.

    Article  Google Scholar 

  • Terashima, N., Fukushima, K., He, L.-F., and Takabe, K., 1993, Comprehensive model of the lignified plant cell wall, in: Forage Cell Wall Structure and Digestibility, Jung, H. G., Buxton, D. R., Hatfield, R. D., and Ralph J., eds., ASA- CSSA-SSSA, Madison, WI., pp. 247-270.

    Google Scholar 

  • The Arabidopsis Genome Initiative, 2000, Analysis of the genome sequence of the flowering plant Arabidopsis thaliana, Nature 408: 796-815.

    Google Scholar 

  • Theres, N., Scheele, T., and Starlinger, P., 1987, Cloning of the Bz2 locus of Zea mays using the transposable element Ds as a gene tag, Mol. Gen. Genet. 209: 193-197.

    Article  PubMed  CAS  Google Scholar 

  • Tobias, C. M, and Chow, E. K., 2005, Structure of the cinnamyl-alcohol dehydrogenase gene family in rice and promoter activity of a member associated with lignification, Planta 220: 678-688.

    Article  PubMed  CAS  Google Scholar 

  • Tropf, S., Lanz, T., Rensing, S. A., Schröder, J., and Schröder, G., 1994, Evidence that stilbene synthases have developed from chalcone synthases several times in the course of evolution, J. Mol. Evol. 38: 610-618.

    Google Scholar 

  • Vermerris, W., and Boon, J. J., 2001, Tissue-specific patterns of lignification are disturbed in the brown midrib2 mutant of maize (Zea mays L.), J. Agric. Food Chem. 49: 721-728.

    Article  PubMed  CAS  Google Scholar 

  • Vignols, F., Rigau, J., Torres, M. A., Capellades, M., and Puigdomènech, P., 1995, The brown-midrib3 (bm3) mutation in maize occurs in the gene encoding caffeic acid O-methyl transferase, Plant Cell 7: 407-416.

    Google Scholar 

  • Weaver, L. M., and Herrmann, K., 1997, Dynamics of the shikimate pathway in plants, Trends Plant Sci. 2: 346-351.

    Article  Google Scholar 

  • Walbot, V., 1992, Strategies for mutagenesis and gene cloning using transposon tagging and T-DNA insertional mutagenesis, Annu. Rev. Plant Physiol. Plant Mol. Biol. 43: 49-82.

    Article  CAS  Google Scholar 

  • Walker, A. R., Davison, P. A., Bolognesi-Winfield, A. C., James, C. M., Srinivasan, N., Blundell, T. L., Esch, J. J., Marks, M. D., and Gray, J. C., 1999, The TRANSPARENT TESTA GLABRA1 locus, which regulates trichome differentiation and anthocyanin biosynthesis in Arabidopsis, encodes a WD40 repeat protein, Plant Cell 11: 1337-1350.

    Article  PubMed  CAS  Google Scholar 

  • Wayne, M. L., and McIntyre, L. M., 2002, Combining mapping and arraying: an approach to candidate gene identification, Proc. Natl. Acad. Sci. USA 99: 14903-14906.

    Google Scholar 

  • Wegenmayer, H., Ebel, J. and Grisebach, H., 1976, Enzymic synthesis of lignin precursors: Purification and properties of a cinnamoyl-CoA: NADPH reductase from cell suspension cultures of soybean (Glycine max L.), Eur. J. Biochem. 65: 529-536.

    Article  Google Scholar 

  • Werner, I., Bacher, A., and Eisenreich, W., 1997, Retrobiosynthetic NMR studies with 13C-labeled glucose. Formation of gallic acid in plants and fungi, J. Biol. Chem. 272: 25474-25482.

    Article  PubMed  CAS  Google Scholar 

  • Werner, R. A., Rossmann, A., Schwarz, C., Bacher, A., Schmidt, H.-L., and Eisenreich, W., 2004, Biosynthesis of gallic acid in Rhus typhina: discrimination between alternative pathways from natural oxygen isotope abundance, Phytochem. 65: 2809-2813.

    Article  CAS  Google Scholar 

  • Wienand U., Weydeman, U., Niesbach-Klösgen, U., Peterson, P. A., and Saedler, H., 1986, Molecular cloning of the c2 locus of Zea mays, the gene coding for chalcone synthase, Mol. Gen. Genet. 203: 202-207.

    Article  CAS  Google Scholar 

  • Wildermuth M. C., Dewdney, J., Wu, G., and Ausubel, F. M., 2001, Isochorismate synthase is required to synthesize salicylic acid for plant defence, Nature 414: 562-565.

    Article  PubMed  CAS  Google Scholar 

  • Winkel-Shirley, B., 2001, Flavonoid biosynthesis. A colorful model for genetics, biochemistry, cell biology, and biotechnology, Plant Physiol. 126: 485-493.

    Article  PubMed  CAS  Google Scholar 

  • Xia, Z.-Q., Costa, M. A., Proctor, J., Davin, L. B., and Lewis, N. G., 2000, Dirigent-mediated podophyllotoxin biosynthesis in Linum flavum and Podophyllum peltatum, Phytochem. 55: 537-549.

    Article  CAS  Google Scholar 

  • Xie, D.-Y., Sharma, S. B., Paiva, N. L., Ferreira, D., and Dixon, R. A., 2003, Role of anthocyanidin reductase, encoded by BANYULS in plant flavonoid biosynthesis, Science 299: 396-399.

    Article  PubMed  CAS  Google Scholar 

  • Yang, B., and Wyman, C. E., 2000, Effect of xylan and lignin removal by batch and flowthrough pretreatment on the enzymatic digestibility of corn stover cellulose, Biotechnol. Bioeng. 86: 88-95.

    Article  CAS  Google Scholar 

  • Ye, Z.-H., Kneusel, R. E., Matern, U., and Varner, J. E., 1994, An alternative methylation pathway in lignin biosynthesis in Zinnia, Plant Cell 6: 1427-1439.

    Article  PubMed  CAS  Google Scholar 

For further reading

  • Davies, K., 2005, Plant Pigments and Their Manipulation, Blackwell Publishing, Oxford, 352 pp.

    Google Scholar 

  • Dennis, D. T., and Blakeley, S. D., 2000, Carbohydrate metabolism, in: Biochemistry and Molecular Biology of Plants, Buchanan, B. B., Gruissem, W., Jones, R. J., eds., John Wiley & Sons, Somerset, NJ, pp. 630-675.

    Google Scholar 

  • Plaxton, W., and McManus, M, 2006, Control of Primary Metabolism in Plants, Blackwell Publishing, Oxford, 400 pp..

    Google Scholar 

  • Verpoort, R., and Alfermann, A.W., 2000, Metabolic Engineering of Plant Secondary Metabolism, Kluwer, Dordrecht, 286 pp.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Genetics Institute Cancer & Genetics Research Complex, University of Florida, 1376 Mowry Road, Gainesville, FL 32610-3610, USA

    Wilfred Vermerris

  2. Purdue University, West Lafayette, IN, USA

    Ralph Nicholson

Authors
  1. Wilfred Vermerris
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ralph Nicholson
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

Copyright information

© 2008 Springer Science+Business Media B.V.

About this chapter

Cite this chapter

Vermerris, W., Nicholson, R. (2008). Biosynthesis of Phenolic Compounds. In: Phenolic Compound Biochemistry. Springer, Dordrecht. https://doi.org/10.1007/978-1-4020-5164-7_3

Download citation

Publish with us

Policies and ethics

Search

Navigation