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First published online November 24, 2004; 10.1104/pp.104.049312

Plant Physiology 136:4023-4036 (2004)
© 2004 American Society of Plant Biologists

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BIOCHEMICAL PROCESSES AND MACROMOLECULAR STRUCTURES

Phenolic Profiling of Caffeic Acid O-Methyltransferase-Deficient Poplar Reveals Novel Benzodioxane Oligolignols1

Kris Morreel2, John Ralph2, 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 (K.M., G.G., W.B., E.M.); 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., F.L.); Laboratorium Medicinale Scheikunde, Katholieke Universiteit Leuven, B–3000 Leuven, Belgium (R.B., P.H.); and Laboratory for Organic and Bioorganic Synthesis, Department of Organic Chemistry, Ghent University, B–9000 Ghent, Belgium (J.L.G., J.V.d.E.)

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.

1 This work was supported by the Fund for Scientific Research-Flanders (grant no. G0040.00N), the European Commission program (grant no. QLK5–CT–2000–01493 to E.M., P.H., and W.B.), in part by the Department of Energy Biosciences program (grant no. DE–AI02–00ER15067) and the U.S. Department of Agriculture-National Research Initiatives (grant no. 2001–02176 to J.R.), and the Instituut voor de aanmoediging van Innovatie door Wetenschap en Technologie in Vlaanderen (predoctoral fellowship to K.M.).

2 These authors contributed equally to the paper.

Article, publication date, and citation information can be found at www.plantphysiol.org/cgi/doi/10.1104/pp.104.049312.

* 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.




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