Plant Physiol. Illumina
HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH
QUICK SEARCH:   [advanced]


     

Plant Physiology Preview
Published on November 24, 2004; 10.1104/pp.104.049312

This Article
Right arrow Full Text (Plant Physiology Preview (PDF))
Right arrow All Versions of this Article:
136/4/4023    most recent
pp.104.049312v1
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 (20)
Right arrow Citing Articles via Google Scholar
Google Scholar
Right arrow Articles by Morreel, K.
Right arrow Articles by Messens, E.
Right arrow Search for Related Content
PubMed
Right arrow PubMed Citation
Right arrow Articles by Morreel, K.
Right arrow Articles by Messens, E.
Agricola
Right arrow Articles by Morreel, K.
Right arrow Articles by Messens, E.

Received July 7, 2004
Returned for revision September 28, 2004
Accepted September 28, 2004

Phenolic Profiling of Caffeic Acid O-Methyltransferase-Deficient Poplar Reveals Novel Benzodioxane Oligolignols

Kris Morreel , John Ralph , Fachuang Lu , Geert Goeminne , Roger Busson , Piet Herdewijn , Jan L. Goeman , Johan Van der Eycken , Wout Boerjan *, and Eric Messens

Department of Plant Systems Biology, Flanders Interuniversity Institute for Biotechnology, Ghent University, B-9052 Ghent, Belgium
United States Dairy Forage Research Center, Agricultural Research Service, United States Department of Agriculture, and Department of Forestry, University of Wisconsin, Madison, Wisconsin 53706
Laboratorium Medicinale Scheikunde, Katholieke Universiteit Leuven, B-3000 Leuven, Belgium
Laboratory for Organic and Bioorganic Synthesis, Department of Organic Chemistry, Ghent University, B-9000 Ghent, Belgium

* Corresponding author; email: wout.boerjan{at}psb.ugent.be.

Caffeic acid O-methyltransferase (COMT) catalyzes preferentially the methylation of 5-hydroxyconiferaldehyde to sinapaldehyde in monolignol biosynthesis. Here, we have compared HPLC profiles of the methanol-soluble phenolics fraction of xylem tissue from COMT-deficient and control poplars (Populus spp.), using statistical analysis of the peak heights. COMT down-regulation results in significant concentration differences for 25 of the 91 analyzed peaks. Eight peaks were exclusively detected in COMT-deficient poplar, of which four could be purified for further identification using mass spectrometry/mass spectrometry, nuclear magnetic resonance, and spiking of synthesized reference compounds. These new compounds were derived from 5-hydroxyconiferyl alcohol or 5-hydroxyconiferaldehyde and were characterized by benzodioxane moieties, a structural type that is also increased in the lignins of COMT-deficient plants. One of these four benzodioxanes amounted to the most abundant oligolignol in the HPLC profile. Furthermore, all of the differentially accumulating oligolignols involving sinapyl units were either reduced in abundance or undetectable. The concentration levels of all identified oligolignols were in agreement with the relative supply of monolignols and with their chemical coupling propensities, which supports the random coupling hypothesis. Chiral HPLC analysis of the most abundant benzodioxane dimer revealed the presence of both enantiomers in equal amounts, indicating that they were formed by radical coupling reactions under simple chemical control rather than guided by dirigent proteins.




This article has been cited by other articles:


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