Advanced search
1 file | 293.28 KB Add to list

Phenolic profiling of caffeic acid O-methyltransferase-deficient poplar reveals novel benzodioxane oligolignols

(2004) PLANT PHYSIOLOGY. 136(4). p.4023-4036
Author
Organization
Abstract
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.
Keywords
CINNAMYL ALCOHOL-DEHYDROGENASE, LIGNIN BIOSYNTHESIS, DOWN-REGULATION, COENZYME-A, TRANSGENIC ALFALFA, MONOLIGNOL BIOSYNTHESIS, SUBSTRATE PREFERENCES, SINAPYL ALCOHOL, CAD-DEFICIENT, PLANTS

Downloads

  • phenolic profiling.pdf
    • full text (Published version)
    • |
    • open access
    • |
    • PDF
    • |
    • 293.28 KB

Citation

Please use this url to cite or link to this publication:

MLA
Morreel, Kris, et al. “Phenolic Profiling of Caffeic Acid O-Methyltransferase-Deficient Poplar Reveals Novel Benzodioxane Oligolignols.” PLANT PHYSIOLOGY, vol. 136, no. 4, 2004, pp. 4023–36, doi:10.1104/pp.104.049312.
APA
Morreel, K., Ralph, J., Lu, F. L., Goeminne, G., Busson, R., Herdewijn, P., … Messens, E. (2004). Phenolic profiling of caffeic acid O-methyltransferase-deficient poplar reveals novel benzodioxane oligolignols. PLANT PHYSIOLOGY, 136(4), 4023–4036. https://doi.org/10.1104/pp.104.049312
Chicago author-date
Morreel, Kris, John Ralph, Fachuang Lu Lu, Geert Goeminne, Roger Busson, Piet Herdewijn, Jan Goeman, Johan Van der Eycken, Wout Boerjan, and Eric Messens. 2004. “Phenolic Profiling of Caffeic Acid O-Methyltransferase-Deficient Poplar Reveals Novel Benzodioxane Oligolignols.” PLANT PHYSIOLOGY 136 (4): 4023–36. https://doi.org/10.1104/pp.104.049312.
Chicago author-date (all authors)
Morreel, Kris, John Ralph, Fachuang Lu Lu, Geert Goeminne, Roger Busson, Piet Herdewijn, Jan Goeman, Johan Van der Eycken, Wout Boerjan, and Eric Messens. 2004. “Phenolic Profiling of Caffeic Acid O-Methyltransferase-Deficient Poplar Reveals Novel Benzodioxane Oligolignols.” PLANT PHYSIOLOGY 136 (4): 4023–4036. doi:10.1104/pp.104.049312.
Vancouver
1.
Morreel K, Ralph J, Lu FL, Goeminne G, Busson R, Herdewijn P, et al. Phenolic profiling of caffeic acid O-methyltransferase-deficient poplar reveals novel benzodioxane oligolignols. PLANT PHYSIOLOGY. 2004;136(4):4023–36.
IEEE
[1]
K. Morreel et al., “Phenolic profiling of caffeic acid O-methyltransferase-deficient poplar reveals novel benzodioxane oligolignols,” PLANT PHYSIOLOGY, vol. 136, no. 4, pp. 4023–4036, 2004.
@article{349210,
  abstract     = {{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.}},
  author       = {{Morreel, Kris and Ralph, John and Lu, Fachuang Lu and Goeminne, Geert and Busson, Roger and Herdewijn, Piet and Goeman, Jan and Van der Eycken, Johan and Boerjan, Wout and Messens, Eric}},
  issn         = {{0032-0889}},
  journal      = {{PLANT PHYSIOLOGY}},
  keywords     = {{CINNAMYL ALCOHOL-DEHYDROGENASE,LIGNIN BIOSYNTHESIS,DOWN-REGULATION,COENZYME-A,TRANSGENIC ALFALFA,MONOLIGNOL BIOSYNTHESIS,SUBSTRATE PREFERENCES,SINAPYL ALCOHOL,CAD-DEFICIENT,PLANTS}},
  language     = {{eng}},
  number       = {{4}},
  pages        = {{4023--4036}},
  title        = {{Phenolic profiling of caffeic acid O-methyltransferase-deficient poplar reveals novel benzodioxane oligolignols}},
  url          = {{http://doi.org/10.1104/pp.104.049312}},
  volume       = {{136}},
  year         = {{2004}},
}

Altmetric
View in Altmetric
Web of Science
Times cited: