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Identification of the structure and origin of a thioacidolysis marker compound for ferulic acid incorporation into angiosperm lignins (and an indicator for cinnamoyl CoA reductase deficiency)

(2008) PLANT JOURNAL. 53(2). p.368-379
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Abstract
A molecular marker compound, derived from lignin by the thioacidolysis degradative method, for structures produced when ferulic acid is incorporated into lignin in angiosperms (poplar, Arabidopsis, tobacco), has been structurally identified as 1,2,2-trithioethyl ethylguaiacol [1-(4-hydroxy-3-methoxyphenyl)-1,2,2-tris(ethylthio)ethane]. Its truncated side chain and distinctive oxidation state suggest that it derives from ferulic acid that has undergone bis-8-O-4 (cross) coupling during lignification, as validated by model studies. A diagnostic contour for such structures is found in two-dimensional C-13-H-1 correlated (HSQC) NMR spectra of lignins isolated from cinnamoyl CoA reductase (CCR)-deficient poplar. As low levels of the marker are also released from normal (i.e. non-transgenic) plants in which ferulic acid may be present during lignification, notably in grasses, the marker is only an indicator for CCR deficiency in general, but is a reliable marker in woody angiosperms such as poplar. Its derivation, together with evidence for 4-O-etherified ferulic acid, strongly implies that ferulic acid is incorporated into angiosperm lignins. Its endwise radical coupling reactions suggest that ferulic acid should be considered an authentic lignin precursor. Moreover, ferulic acid incorporation provides a new mechanism for producing branch points in the polymer. The findings sharply contradict those reported in a recent study on CCR-deficient Arabidopsis.
Keywords
downregulation, lignin monomer, transgenic, mutant, radical coupling, NMR, ALCOHOL-DEHYDROGENASE DEFICIENCY, O-METHYLTRANSFERASE ACTIVITY, DOWN-REGULATION, TOBACCO PLANTS, CELL-WALLS, ARABIDOPSIS-THALIANA, TRANSGENIC POPLARS, CAD-DEFICIENT, LIGNIFICATION

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Citation

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MLA
Ralph, John, Hoon Kim, Fachuang Lu, et al. “Identification of the Structure and Origin of a Thioacidolysis Marker Compound for Ferulic Acid Incorporation into Angiosperm Lignins (and an Indicator for Cinnamoyl CoA Reductase Deficiency).” PLANT JOURNAL 53.2 (2008): 368–379. Print.
APA
Ralph, J., Kim, H., Lu, F., Grabber, J. H., Leplé, J.-C., Berrio-Sierra, J., Derikvand, M. M., et al. (2008). Identification of the structure and origin of a thioacidolysis marker compound for ferulic acid incorporation into angiosperm lignins (and an indicator for cinnamoyl CoA reductase deficiency). PLANT JOURNAL, 53(2), 368–379.
Chicago author-date
Ralph, John, Hoon Kim, Fachuang Lu, John H Grabber, Jean-Charles Leplé, Jimmy Berrio-Sierra, Mohammad Mir Derikvand, Lise Jouanin, Wout Boerjan, and Catherine Lapierre. 2008. “Identification of the Structure and Origin of a Thioacidolysis Marker Compound for Ferulic Acid Incorporation into Angiosperm Lignins (and an Indicator for Cinnamoyl CoA Reductase Deficiency).” Plant Journal 53 (2): 368–379.
Chicago author-date (all authors)
Ralph, John, Hoon Kim, Fachuang Lu, John H Grabber, Jean-Charles Leplé, Jimmy Berrio-Sierra, Mohammad Mir Derikvand, Lise Jouanin, Wout Boerjan, and Catherine Lapierre. 2008. “Identification of the Structure and Origin of a Thioacidolysis Marker Compound for Ferulic Acid Incorporation into Angiosperm Lignins (and an Indicator for Cinnamoyl CoA Reductase Deficiency).” Plant Journal 53 (2): 368–379.
Vancouver
1.
Ralph J, Kim H, Lu F, Grabber JH, Leplé J-C, Berrio-Sierra J, et al. Identification of the structure and origin of a thioacidolysis marker compound for ferulic acid incorporation into angiosperm lignins (and an indicator for cinnamoyl CoA reductase deficiency). PLANT JOURNAL. 2008;53(2):368–79.
IEEE
[1]
J. Ralph et al., “Identification of the structure and origin of a thioacidolysis marker compound for ferulic acid incorporation into angiosperm lignins (and an indicator for cinnamoyl CoA reductase deficiency),” PLANT JOURNAL, vol. 53, no. 2, pp. 368–379, 2008.
@article{409988,
  abstract     = {A molecular marker compound, derived from lignin by the thioacidolysis degradative method, for structures produced when ferulic acid is incorporated into lignin in angiosperms (poplar, Arabidopsis, tobacco), has been structurally identified as 1,2,2-trithioethyl ethylguaiacol [1-(4-hydroxy-3-methoxyphenyl)-1,2,2-tris(ethylthio)ethane]. Its truncated side chain and distinctive oxidation state suggest that it derives from ferulic acid that has undergone bis-8-O-4 (cross) coupling during lignification, as validated by model studies. A diagnostic contour for such structures is found in two-dimensional C-13-H-1 correlated (HSQC) NMR spectra of lignins isolated from cinnamoyl CoA reductase (CCR)-deficient poplar. As low levels of the marker are also released from normal (i.e. non-transgenic) plants in which ferulic acid may be present during lignification, notably in grasses, the marker is only an indicator for CCR deficiency in general, but is a reliable marker in woody angiosperms such as poplar. Its derivation, together with evidence for 4-O-etherified ferulic acid, strongly implies that ferulic acid is incorporated into angiosperm lignins. Its endwise radical coupling reactions suggest that ferulic acid should be considered an authentic lignin precursor. Moreover, ferulic acid incorporation provides a new mechanism for producing branch points in the polymer. The findings sharply contradict those reported in a recent study on CCR-deficient Arabidopsis.},
  author       = {Ralph, John and Kim, Hoon and Lu, Fachuang and Grabber, John H and Leplé, Jean-Charles and Berrio-Sierra, Jimmy and Derikvand, Mohammad Mir and Jouanin, Lise and Boerjan, Wout and Lapierre, Catherine},
  issn         = {0960-7412},
  journal      = {PLANT JOURNAL},
  keywords     = {downregulation,lignin monomer,transgenic,mutant,radical coupling,NMR,ALCOHOL-DEHYDROGENASE DEFICIENCY,O-METHYLTRANSFERASE ACTIVITY,DOWN-REGULATION,TOBACCO PLANTS,CELL-WALLS,ARABIDOPSIS-THALIANA,TRANSGENIC POPLARS,CAD-DEFICIENT,LIGNIFICATION},
  language     = {eng},
  number       = {2},
  pages        = {368--379},
  title        = {Identification of the structure and origin of a thioacidolysis marker compound for ferulic acid incorporation into angiosperm lignins (and an indicator for cinnamoyl CoA reductase deficiency)},
  url          = {http://dx.doi.org/10.1111/j.1365-313X.2007.03345.x},
  volume       = {53},
  year         = {2008},
}

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