Extent of incorporation of hydroxycinnamaldehydes into lignin in cinnamyl alcohol dehydrogenase-downregulated plants

Wendy Roslyn Russell, G J Provan, M J Burkitt, Andrew Chesson

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Down-regulation of cinnamyl alcohol dehydrogenase leads to an accumulation of cinnamaldehydes available for incorporation into the developing lignin polymer. Using electron spin resonance spectroscopy we have demonstrated that the parent radical of 4-hydroxy-3-methoxycinnamaldehyde is generated by peroxidase catalysed oxidation. The extent of radical generation is similar to that of 4-hydroxy-3-methoxycinnamyl alcohol and is increased by further aromatic methoxylation. From the distribution of the electron-spin density, it was predicted that the regiochemistry of 4-hydroxy-3-methoxycinnamaldehyde coupling would be similar to that of the corresponding alcohol, with the possibility of a higher degree of 8-O-4 linkages occurring. These predictions were confirmed by polymerisation studies, which also showed that after radical coupling the a,ß-enone structure was regenerated. This suggests that, although the cross-linking and physical properties of cinnamaldeyde rich lignins differ from that of normal lignins, cinnamaldehydes are incorporated into the lignin polymer under the same controlling factors as the cinnamyl alcohols.

Original languageEnglish
Pages (from-to)73-85
Number of pages13
JournalJournal of Biotechnology
Volume79
Issue number1
Early online date27 Mar 2000
DOIs
Publication statusPublished - 14 Apr 2000

Keywords

  • Cinnamyl alcohol dehydrogenase
  • Lignin biosynthesis
  • Phenylpropanoid
  • ESR
  • NMR
  • Downregulation

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