Signatures of cinnamyl alcohol dehydrogenase deficiency in poplar lignins

Phytochemistry

Volumn 65, Issue 3, 2004, Pages 313-321

  Lapierre, Catherine ^a   Pilate, Gilles ^b   Pollet, Brigitte ^a   Mila, Isabelle ^a   Leplé, Jean Charles ^b   Jouanin, Lise ^c   Kim, Hoon ^d,e   Ralph, John ^d,e  

^a AGROPARISTECH   (France)

^b National Institute for Agricultural Research   (France)

^c CEMAGREF   (France)

^d U S DAIRY FORAGE RESEARCH CENTER   (United States)

^e UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

Cinnamyl alcohol dehydrogenase; Coniferaldehyde; Lignin biosynthesis; Lignin structure; Poplar (Populus deltoides x Populus nigra; cv Ogy); Salicaceae; Sinapaldehyde; Thioacidolysis; Transgenic

Indexed keywords

ALCOHOL DEHYDROGENASE; ALDEHYDE DERIVATIVE; CINNAMYL ALCOHOL; LIGNIN;

ARTICLE; DOWN REGULATION; ENZYME ANALYSIS; ENZYME DEFICIENCY; LIGNIFICATION; PROTEIN DOMAIN; ROOM TEMPERATURE; SOLUBILITY;

POPULUS; POPULUS BEROLINENSIS; POPULUS DELTOIDES; POPULUS NIGRA; SALICACEAE;

EID: 0742272551     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2003.11.007     Document Type: Article

References (42)

1. Adler E., Björkquist K.J., Häggroth S. Über die Ursache der Farbreaktionen des Holzes. Acta Chem. Scand. 2:1948;93-94.
2. Baucher M., Bernard-Vailhé M.-A., Chabbert B., Besle J.-M., Opsomer C., Van Montagu M., Botterman J. Down-regulation of cinnamyl alcohol dehydrogenase in transgenic alfalfa (Medicago sativa L.) and the effect on lignin composition and digestibility. Plant Mol. Biol. 39:1999;437-447.
3. Baucher M., Chabbert B., Pilate G., Van Doorsselaere J., Tollier M.-T., Petit-Conil M., Cornu M., Monties B., Van Montagu M., Inze D., Jouanin L., Boerjan W. Red xylem and higher lignin extractability by down-regulating a cinnamyl alcohol dehydrogenase. Plant Physiol. 112:1996;1479-1490.
4. Baumberger S., Dole P., Lapierre C. Using transgenic poplars to elucidate the relationship between the structure and the thermal properties of lignins. J. Agr. Food Chem. 50:2002;2450-2453.
5. Beckman E., Liesche O., Lehman F. Qualitative und Quantitative Unterschiede der Lignine einiger Holz- und Stroharten. Biochem. Z. 139:1923;491.
6. Brunow G., Kilpeläinen I., Sipilä J., Syrjänen K., Karhunen P., Setälä H., Rummakko P. Oxidative coupling of phenols and the biosynthesis of lignin. Lewis N.G., Sarkanen S. Lignin and Lignan Biosynthesis. 1998;131-147 American Chemical Society, New Orleans, LA.
7. Chen F., Duran A.L., Blount J.W., Summer L.W., Dixon R.A. Profiling phenolic metabolites in transgenic alfalfa modified in lignin biosynthesis. Phytochemistry. 64:2003;1013-1021.
8. Connors W.J., Chen C.-L., Pew J.C. Enzymic dehydrogenation of the lignin model coniferaldehyde. J. Org. Chem. 35:1970;1920-1924.
9. Deighton N., Richardson A., Stewart D., McDougall G.J. Cell-wall associated oxidases from the lignifying xylem of angiosperms and gymnosperms. monolignol oxidation Holzforschung. 53:1999;503-510.
10. Dence C. Lignin determination. Dence C., Lin S. Methods in Lignin Chemistry. 1992;29-34 Springer-Verlag, Berlin.
11. Dixon R.A., Chen F., Guo D., Parvathi K. The biosynthesis of monolignols. a "metabolic grid". or independent pathways to guaiacyl and syringyl units? Phytochemistry. 57:2001;1069-1084.
12. Grima-Pettenati J., Goffner D. Lignin genetic engineering revisited. Plant Sci. 145:1999;51-65.
13. Halpin C., Holt K., Chojecki J., Oliver D., Chabbert B., Monties B., Edwards K., Barakate A., Foxon G.A. Brown-midrib maize (bm1) - a mutation affecting the cinnamyl alcohol dehydrogenase gene. Plant J. 14:1998;545-553.
14. Halpin C., Knight M.E., Foxon G.A., Campbell M.M., Boudet A.-M., Boon J.J., Chabbert B., Tollier M.-T., Schuch W. Manipulation of lignin quality by downregulation of cinnamyl alcohol dehydrogenase. Plant J. 6:1994;339-350.
15. Higuchi T. Biochemistry and Molecular Biology of Wood. 1997;Springer-Verlag, New York.
16. Higuchi T., Ito T., Umezawa T., Hibino T., Shibata D. Red-brown color of lignified tissues of transgenic plants with antisense CAD gene. wine-red lignin from coniferyl aldehyde J. Biotechnol. 37:1994;151-158.
17. Humphrey J.M., Chapple C. Rewriting the lignin roadmap. Curr. Opin. Plant Biol. 5:2002;224-229.
18. Humphrey J.M., Hemm M.R., Chapple C. New routes for lignin biosynthesis defined by biochemical characterization of recombinant ferulate-5-hydroxylase, a multifunctional cytochrome P450-dependent monooxygenase. Proc. Natl. Acad. Sci. U.S.A. 96:1999;10045-10050.
19. Kim H., Ralph J., Yahiaoui N., Pean M., Boudet A.-M. Cross-coupling of hydroxycinnamyl aldehydes into lignins. Org. Lett. 2:2000;2197-2200.
20. Kim H., Ralph J., Lu F., Pilate G., Leplé J.-C., Pollet B., Lapierre C. Identification of the structure and origin of thioacidolysis marker compounds for cinnamyl alcohol dehydrogenase deficiency in angiosperms. J. Biol. Chem. 277:2002;47412-47419.
21. Kim H., Ralph J., Lu F., Ralph S.A., Boudet A.-M., MacKay J.J., Sederoff R.R., Ito T., Kawai S., Ohashi H., Higuchi T. NMR analysis of lignins in CAD-deficient plants. 1. Incorporation of hydroxycinnamaldehydes and hydroxybenzaldehydes into lignins. Org. Biomol. Chem. 1:2003;158-281.
22. Lapierre, C., Kim, H., Lu, F., Marita, J. M., Mila, I., Pollet, B., Ralph, J., 2001. Marker compounds for enzyme deficiencies in the lignin biosynthetic pathway. In: 11th International Symposium on Wood and Pulping Chemistry. Nice, France, Vol. II. Imprimerie des Deux-Ponts, Grenoble, pp. 23-26.
23. 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. 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. 119:1999;153-163.
24. Lapierre C., Pollet B., Rolando C. New insights into the molecular architecture of hardwood lignins by chemical degradation methods. Res. Chem. Intermed. 21:1995;397-412.
25. Lapierre C., Tollier M.T., Monties B. Mise en évidence d'un nouveau type d'unité constitutive dans les lignines d'un mutant de Maïs bm3. C. R. Acad. Sci. Série III, Sciences de la Vie. 307:1988;723-728.
26. Li L., Popko J.L., Umezawa T., Chiang V.L. 5-Hydroxyconiferyl aldehyde modulates enzymatic methylation for syringyl monolignol formation. a new view of monolignol synthesis in angiosperms J. Biol. Chem. 275:2000;6537-6545.
27. Li L., Cheng X.F., Leshkevich J., Umezawa T., Harding S.A., Chiang V.L. The last step of syringyl monolignol biosynthesis in angiosperms is regulated by a novel gene encoding sinapyl alcohol dehydrogenase. Plant Cell. 13:2001;1567-1585.
28. Marita J.M., Vermerris W., Ralph J., Hatfield R.D. Variations in the cell wall composition of maize brown midrib mutants. J. Agr. Food Chem. 51:2003;1313-1321.
29. Noël N., Leplé J.-C., Pilate G. Optimization of in vitro propagation and regeneration for Populus×interamericana and Populus×euramericana hybrids (P. deltoides, P. trichocarpa, and P. nigra). Plant Cell Rep. 20:2002;1150-1155.
30. Osakabe K., Tsao C.C., Li L., Popko J.L., Umezawa T., Carraway D.T., Smeltzer R.H., Joshi C.P., Chiang V.L. Coniferyl aldehyde 5-hydroxylation and methylation direct syringyl lignin biosynthesis in angiosperms. Proc. Natl. Acad. Sci. U.S.A. 96:1999;8955-8960.
31. Parvathi K., Chen F., Guo D., Blount J.W., Dixon R.A. Substrate preferences of O-methyltransferases in alfalfa suggest new pathways for 3-O-methylation of monolignols. Plant J. 25:2001;193-202.
32. Pillonel C., Mulder M.M., Boon J.J., Forster B., Binder A. Involvement of cinnamyl alcohol dehydrogenase in the control of lignin formation in Sorghum bicolor L. Moench. Planta. 185:1991;538-544.
33. Ralph J., Hatfield R.D., Piquemal J., Yahiaoui N., Pean M., Lapierre C., Boudet A.-M. 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. U.S.A. 95:1998;12803-12808.
34. Ralph J., Lapierre C., Marita J., Kim H., Lu F., Hatfield R.D., Ralph S.A., Chapple C., Franke R., Hemm M.R., Van Doorsselaere J., Sederoff R.R., O'Malley D.M., Scott J.T., MacKay J.J., Yahiaoui N., Boudet A.-M., Pean M., Pilate G., Jouanin L., Boerjan W. Elucidation of new structures in lignins of CAD- and COMT-deficient plants by NMR. Phytochemistry. 57:2001;993-1003.
35. Ros Barcelo A., Pomar F. Oxidation of cinnamyl alcohols and aldehydes by a basic peroxidase from lignifying Zinnia elegans hypocotyls. Phytochemistry. 57:2001;1105-1113.
36. Russell W.R., Provan G.J., Burkitt M.J., Chesson A. Extent of incorporation of hydroxycinnamaldehydes into lignin in cinnamyl alcohol dehydrogenase-downregulated plants. J. Biotechnol. 79:2000;73-85.
37. Sibout R., Eudes A., Pollet B., Goujon T., Mila I., Granier F., Séguin A., Lapierre C., Jouanin L. Expression pattern of two paralogs encoding cinnamyl alcohol dehydrogenases in Arabidopsis. Isolation and characterization of the corresponding mutants. Plant Physiol. 132:2003;848-860.
38. Steeves V., Förster H., Pommer U., Savidge R. Coniferyl alcohol metabolism in conifers- I Glucosidic turnover of cinnamyl aldehydes by UDPG:coniferyl alcohol glucosyltransferase from pine cambium. Phytochemistry. 57:2001;1085-1093.
39. Stewart D., Yahiaoui N., McDougall G.J., Myton K., Marque C., Boudet A.-M., Haigh J. 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. 201:1997;311-318.
40. Van Doorsselaere J., Baucher M., Feuillet C., Boudet A.-M., Van Montagu M., Inzé D. Isolation of cinnamyl alcohol dehydrogenase cDNAs from two important economic species: alfalfa and poplar. Demonstration of a high homology of the gene within angiosperms. Plant Physiol. Biochem. 33:1995;105-109.
41. Van Doorsselaere J., Baucher M., Chognot E., Chabbert B., Tollier M.-T., Petit-Conil M., Leplé J.-C., Pilate G., Cornu D., Monties B., Van Montagu M., Inzé D., Boerjan W., Jouanin L. A novel lignin in poplar trees with a reduced caffeic acid/5-hydroxyferulic acid O-methyltransferase activity. Plant J. 8:1995;855-864.
42. Yahiaoui N., Marque C., Myton K.E., Negrel J., Boudet A.-M. Impact of different levels of cinnamyl alcohol dehydrogenase down-regulation on lignins of transgenic tobacco plants. Planta. 204:1998;8-15.