Arabidopsis peroxidase-catalyzed copolymerization of coniferyl and sinapyl alcohols: Kinetics of an endwise process

Phytochemistry

Volumn 71, Issue 14-15, 2010, Pages 1673-1683

  Demont Caulet, Nathalie ^a,b   Lapierre, Catherine ^a   Jouanin, Lise ^a   Baumberger, Stéphanie ^a   Méchin, Valérie ^a  

^a INSTITUT JEAN PIERRE BOURGIN   (France)

^b UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

Bulk; Coniferyl and sinapyl alcohols; Endwise; Lignin synthesis; Oligolignols structure; Plant peroxidase

Indexed keywords

CONIFERYL ALCOHOL; LIGNIN; PEROXIDASE; PHENOL DERIVATIVE; PHENYLPROPIONIC ACID DERIVATIVE; SINAPYL ALCOHOL;

ARABIDOPSIS; ARTICLE; CHEMISTRY; ENZYMOLOGY; METABOLISM; POLYACRYLAMIDE GEL ELECTROPHORESIS; POLYMERIZATION;

ARABIDOPSIS; ELECTROPHORESIS, POLYACRYLAMIDE GEL; LIGNIN; PEROXIDASES; PHENOLS; PHENYLPROPIONATES; POLYMERIZATION;

ARABIDOPSIS; ARABIDOPSIS THALIANA; ARMORACIA RUSTICANA;

EID: 77956340883     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2010.06.011     Document Type: Article

References (28)

1. J.M. Alonso, A.N. Stepanova, T.J. Leisse, C.J. Kim, H. Chen, P. Shinn, D.K. Stevenson, J. Zimmerman, P. Barajas, R. Cheuk, C. Gadrinab, C. Heller, A. Jeske, E. Koesema, C.C. Meyers, H. Parker, L. Prednis, Y. Ansari, N. Choy, H. Deen, M. Geralt, N. Hazari, E. Hom, M. Karnes, C. Mulholland, R. Ndubaku, I. Schmidt, P. Guzman, L. Aguilar-Henonin, M. Schmid, D. Weigel, D.E. Carter, T. Marchand, E. Risseeuw, D. Brogden, A. Zeko, W.L. Crosby, C.C. Berry, and J.R. Ecker Genome-wide insertional mutagenesis of Arabidopsis thaliana Science 301 2003 653 657
2. W. Aoyama, S. Sasaki, S. Matsumura, T. Mitsunaga, H. Hirai, Y. Tsutsumi, and T. Nishida Sinapyl alcohol-specific peroxidase isoenzyme catalyzes the formation of the dehydrogenative polymer from sinapyl alcohol J. Wood Sci. 48 2002 497 504
3. A.R. Barcelo, L.V.G. Ros, and A.E. Carrasco Looking for syringyl peroxidases Trends Plant Sci. 12 2007 486 491
4. Baumberger, S., Fournand, D., Pollet, B., Lapierre, C., Ducrot, P.-H., 2003. Peroxidase-catalyzed polymerization of monolignols: HPSEC investigation of the oligomerization step. In: Proceedings of the 12th ISWPC, Madison, pp. 165-168.
5. N. Bouche, and D. Bouchez Arabidopsis gene knockout: phenotypes wanted Curr. Opin. Plant Biol. 4 2001 111 117
6. G. Brunow, I. Kilpelainen, J. Sipila, K. Syrjanen, P. Karhunen, H. Setala, and P. Rummakko Oxidative coupling of phenols and the biosynthesis of lignin N.G. Lewis, S. Sarkanen, Lignin and Lignan Biosynthesis 1998 American Chemical Society Washington, DC 131 147
7. D. Buffard, C. Breda, R.B. van Huystee, O. Asemota, M. Pierre, D.B. Ha, and R. Esnault Molecular cloning of complementary DNAs encoding two cationic peroxidases from cultivated peanut cells Proc. Natl. Acad. Sci. USA 87 1990 8874 8878
8. Evtuguin, D.V., Amado, F.M.L., 2003. Towards a better understanding of lignin assembly: the assessment of the sequential order of building blocks and inter-units linkages using electrospray ionisation mass spectrometry. In: Proceedings of the 12th ISWPC, Madison, pp. 277-280.
9. D. Fournand, and C. Lapierre Capillary zone electrophoresis of coniferyl alcohol oxidation products J. Agric. Food Chem. 49 2001 5727 5731
10. D. Fournand, B. Cathala, and C. Lapierre Initial steps of the peroxidase-catalyzed polymerization of coniferyl alcohol and/or sinapyl aldehyde: capillary zone electrophoresis study of pH effect Phytochemistry 62 2003 139 146
11. K. Freudenberg, and H.H. Hubner Hydroxycinnamyl alcohols and their dehydrogenation polymers Chem. Ber. 85 1952 1181 1191
12. C. Gabaldon, M. Lopez-Serrano, M.A. Pedreno, and A.R. Barcelo Cloning and molecular characterization of the basic peroxidase isoenzyme from Zinnia elegans, an enzyme involved in lignin biosynthesis Plant Physiol. 139 2005 1138 1154
13. T. Kishimoto, W. Chiba, K. Saito, K. Fukushima, Y. Uraki, and M. Ubukata Influence of syringyl to guaiacyl ratio on the structure of natural and synthetic lignins J. Agric. Food Chem. 58 2010 895 901
14. F.H. Ludley, and J. Ralph Improved preparation of coniferyl and sinapyl alcohols J. Agric. Food Chem. 44 1996 2942 2943
15. K. Marjamaa, E. Kukkola, T. Lundell, P. Karhunen, P. Saranpaa, and K.V. Fagerstedt Monolignol oxidation by xylem peroxidase isoforms of Norway spruce (Picea abies) and silver birch (Betula pendula) Tree Physiol. 26 2006 605 611
16. V. Méchin, S. Baumberger, B. Pollet, and C. Lapierre Peroxidase activity can dictate the in vitro lignin dehydrogenative polymer structure Phytochemistry 68 2007 571 579
17. Z. Minic, E. Jamet, L. Negroni, P.A. der Garabedian, M. Zivy, and L. Jouanin A sub-proteome of Arabidopsis thaliana mature stems trapped on Concanavalin A is enriched in cell wall glycoside hydrolases J. Exp. Bot. 58 2007 2503 2512
18. K. Morreel, J. Ralph, H. Kim, F.C. Lu, G. Goeminne, S. Ralph, E. Messens, and W. Boerjan Profiling of oligolignols reveals monolignol coupling conditions in lignifying poplar xylem Plant Physiol. 136 2004 3537 3549
19. K.L. Nielsen, C. Indiani, A. Henriksen, A. Feis, M. Becucci, M. Gajhede, G. Smulevich, and K.G. Welinder Differential activity and structure of highly similar peroxidases. Spectroscopic, crystallographic, and enzymatic analyses of lignifying Arabidopsis thaliana peroxidase A2 and horseradish peroxidase A2 Biochemistry 40 2001 11013 11021
20. M. Quiroga, C. Guerrero, M.A. Botella, A. Barcelo, I. Amaya, M.I. Medina, F.J. Alonso, S.M. de Forchetti, H. Tigier, and V. Valpuesta A tomato peroxidase involved in the synthesis of lignin and suberin Plant Physiol. 122 2000 1119 1127
21. S. Sasaki, T. Nishida, Y. Tsutsumi, and R. Kondo Lignin dehydrogenative polymerization mechanism: a poplar cell wall peroxidase directly oxidizes polymer lignin and produces in vitro dehydrogenative polymer rich in beta-O-4 linkage FEBS Lett. 562 2004 197 201
22. K. Syrjanen, and G. Brunow Regioselectivity in lignin biosynthesis. The influence of dimerization and cross-coupling J. Chem. Soc. Perkin Trans. 1 2000 183 187
23. U. Takahama, and T. Oniki Effects of ascorbate on the oxidation of derivatives of hydroxycinnamic acid and the mechanism of oxidation of sinapic acid by cell wall-bound peroxidases Plant Cell Physiol 35 1994 593 600
24. U. Takahama, T. Oniki, and H. Shimokawa A possible mechanism for the oxidation of sinapyl alcohol by peroxidase-dependent reactions in the apoplast: enhancement of the oxidation by hydroxycinnamic acids and components of the apoplast Plant Cell Physiol. 37 1996 499 504
25. Y. Tobimatsu, T. Takano, H. Kamitakahara, and F. Nakatsubo Studies on the dehydrogenative polymerizations (DHPs) of monolignol beta-glycosides: Part 4. Horseradish peroxidase-catalyzed copolymerization of isoconiferin and isosyringin Holzforschung 62 2008 495 500
26. Y. Tobimatsu, T. Takano, H. Kamitakahara, and F. Nakatsubo Studies on the dehydrogenative polymerization of monolignol beta-glycosides: Part 5. UV spectroscopic monitoring of horseradish peroxidase-catalyzed polymerization of monolignol glycosides Holzforschung 62 2008 501 507
27. Y. Tobimatsu, T. Takano, H. Kamitakahara, and F. Nakatsubo Studies on the dehydrogenative polymerizations of monolignol beta-glycosides. Part 3: Horseradish peroxidase-catalyzed polymerizations of triandrin and isosyringin J. Wood Chem. Technol. 28 2008 69 83
28. Y. Tobimatsu, T. Takano, H. Kamitakahara, and F. Nakatsubo Studies on the dehydrogenative polymerization of monolignol beta-glycosides. Part 6: Monitoring of horseradish peroxidase-catalyzed polymerization of monolignol glycosides by GPC-PDA Holzforschung 64 2010 173 181