Plant Physiol.
HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH TABLE OF CONTENTS
QUICK SEARCH:   [advanced]


     

First published online October 29, 2004; 10.1104/pp.104.049304

Plant Physiology 136:3537-3549 (2004)
© 2004 American Society of Plant Biologists

This Article
Right arrow Full Text
Right arrow Full Text (PDF)
Right arrow Supplemental Data
Right arrow All Versions of this Article:
136/3/3537    most recent
pp.104.049304v1
Right arrow Alert me when this article is cited
Right arrow Alert me if a correction is posted
Services
Right arrow Email this article to a friend
Right arrow Similar articles in this journal
Right arrow Similar articles in Web of Science
Right arrow Similar articles in PubMed
Right arrow Alert me to new issues of the journal
Right arrow Download to citation manager
Right arrow reprints & permissions
Citing Articles
Right arrow Citing Articles via HighWire
Right arrow Citing Articles via CrossRef
Right arrow Citing Articles via Web of Science (25)
Right arrow Citing Articles via Google Scholar
Google Scholar
Right arrow Articles by Morreel, K.
Right arrow Articles by Boerjan, W.
Right arrow Search for Related Content
PubMed
Right arrow PubMed Citation
Right arrow Articles by Morreel, K.
Right arrow Articles by Boerjan, W.
Agricola
Right arrow Articles by Morreel, K.
Right arrow Articles by Boerjan, W.
BIOCHEMICAL PROCESSES AND MACROMOLECULAR STRUCTURES

Profiling of Oligolignols Reveals Monolignol Coupling Conditions in Lignifying Poplar Xylem1,[w]

Kris Morreel, John Ralph, Hoon Kim, Fachuang Lu, Geert Goeminne, Sally Ralph, Eric Messens and Wout Boerjan*

Department of Plant Systems Biology, Flanders Interuniversity Institute for Biotechnology, Ghent University, B–9052 Ghent, Belgium (K.M., G.G., E.M., W.B.); United States Dairy Forage Research Center, Agricultural Research Service, United States Department of Agriculture, and Department of Forestry, University of Wisconsin, Madison, Wisconsin 53706 (J.R., H.K., F.L.); and United States Forest Products Laboratory, United States Department of Agriculture Forest Service, Madison, Wisconsin 53705 (S.R.)

Lignin is an aromatic heteropolymer, abundantly present in the walls of secondary thickened cells. Although much research has been devoted to the structure and composition of the polymer to obtain insight into lignin polymerization, the low-molecular weight oligolignol fraction has escaped a detailed characterization. This fraction, in contrast to the rather inaccessible polymer, is a simple and accessible model that reveals details about the coupling of monolignols, an issue that has raised considerable controversy over the past years. We have profiled the methanol-soluble oligolignol fraction of poplar (Populus spp.) xylem, a tissue with extensive lignification. Using liquid chromatography-mass spectrometry, chemical synthesis, and nuclear magnetic resonance, we have elucidated the structures of 38 compounds, most of which were dimers, trimers, and tetramers derived from coniferyl alcohol, sinapyl alcohol, their aldehyde analogs, or vanillin. All structures support the recently challenged random chemical coupling hypothesis for lignin polymerization. Importantly, the structures of two oligomers, each containing a {gamma}-p-hydroxybenzoylated syringyl unit, strongly suggest that sinapyl p-hydroxybenzoate is an authentic precursor for lignin polymerization in poplar.

1 This work was supported by the Fund for Scientific Research-Flanders (G.0040.00N) and by the European Commission program (QLK5–CT–2000–01493 to E.M. and W.B.), in part by the Department of Energy Biosciences program (DE–AI02–00ER15067) and by the U.S. Department of Agriculture-National Research Initiatives (2001–02176 to J.R.), and by the Instituut voor de aanmoediging van Innovatie door Wetenschap en Technologie in Vlaanderen (predoctoral fellowship to K.M.).

[w] The online version of this article contains Web-only data.

Article, publication date, and citation information can be found at www.plantphysiol.org/cgi/doi/10.1104/pp.104.049304.

* Corresponding author; e-mail wout.boerjan{at}psb.ugent.be; fax 32–9–331–3809.

Received July 7, 2004; returned for revision September 28, 2004; accepted September 28, 2004.




This article has been cited by other articles:


Home page
 Plant Physiol.Home page
J. J. Stewart, T. Akiyama, C. Chapple, J. Ralph, and S. D. Mansfield
The Effects on Lignin Structure of Overexpression of Ferulate 5-Hydroxylase in Hybrid Poplar1
Plant Physiology, June 1, 2009; 150(2): 621 - 635.
[Abstract] [Full Text] [PDF]

Home page
 J. Biol. Chem.Home page
J. G. Kopycki, M. T. Stubbs, W. Brandt, M. Hagemann, A. Porzel, J. Schmidt, W. Schliemann, M. H. Zenk, and T. Vogt
Functional and Structural Characterization of a Cation-dependent O-Methyltransferase from the Cyanobacterium Synechocystis sp. Strain PCC 6803
J. Biol. Chem., July 25, 2008; 283(30): 20888 - 20896.
[Abstract] [Full Text] [PDF]

Home page
 Proc. Natl. Acad. Sci. USAHome page
L. Pauwels, K. Morreel, E. De Witte, F. Lammertyn, M. Van Montagu, W. Boerjan, D. Inze, and A. Goossens
Mapping methyl jasmonate-mediated transcriptional reprogramming of metabolism and cell cycle progression in cultured Arabidopsis cells
PNAS, January 29, 2008; 105(4): 1380 - 1385.
[Abstract] [Full Text] [PDF]

Home page
 Plant CellHome page
J.-C. Leple, R. Dauwe, K. Morreel, V. Storme, C. Lapierre, B. Pollet, A. Naumann, K.-Y. Kang, H. Kim, K. Ruel, et al.
Downregulation of Cinnamoyl-Coenzyme A Reductase in Poplar: Multiple-Level Phenotyping Reveals Effects on Cell Wall Polymer Metabolism and Structure
PLANT CELL, November 1, 2007; 19(11): 3669 - 3691.
[Abstract] [Full Text] [PDF]

Home page
 J. Biol. Chem.Home page
J. Ralph, T. Akiyama, H. Kim, F. Lu, P. F. Schatz, J. M. Marita, S. A. Ralph, M. S. S. Reddy, F. Chen, and R. A. Dixon
Effects of Coumarate 3-Hydroxylase Down-regulation on Lignin Structure
J. Biol. Chem., March 31, 2006; 281(13): 8843 - 8853.
[Abstract] [Full Text] [PDF]

Home page
 J. Biol. Chem.Home page
B. Youn, S. G. A. Moinuddin, L. B. Davin, N. G. Lewis, and C. Kang
Crystal Structures of Apo-form and Binary/Ternary Complexes of Podophyllum Secoisolariciresinol Dehydrogenase, an Enzyme Involved in Formation of Health-protecting and Plant Defense Lignans
J. Biol. Chem., April 1, 2005; 280(13): 12917 - 12926.
[Abstract] [Full Text] [PDF]

Home page
 Plant Physiol.Home page
K. Morreel, J. Ralph, F. Lu, G. Goeminne, R. Busson, P. Herdewijn, J. L. Goeman, J. Van der Eycken, W. Boerjan, and E. Messens
Phenolic Profiling of Caffeic Acid O-Methyltransferase-Deficient Poplar Reveals Novel Benzodioxane Oligolignols
Plant Physiology, December 1, 2004; 136(4): 4023 - 4036.
[Abstract] [Full Text] [PDF]


HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH TABLE OF CONTENTS
ASPB Publications PLANT PHYSIOLOGY® THE PLANT CELL
Copyright © 2004 by the American Society of Plant Biologists