Phytochemistry Reviews

, Volume 3, Issue 1–2, pp 79–96

Peroxidase-dependent cross-linking reactions of p-hydroxycinnamates in plant cell walls

  • John Ralph
  • Mirko Bunzel
  • Jane M. Marita
  • Ronald D. Hatfield
  • Fachuang Lu
  • Hoon Kim
  • Paul F. Schatz
  • John H. Grabber
  • Hans Steinhart
Article

DOI: 10.1023/B:PHYT.0000047811.13837.fb

Cite this article as:
Ralph, J., Bunzel, M., Marita, J.M. et al. Phytochemistry Reviews (2004) 3: 79. doi:10.1023/B:PHYT.0000047811.13837.fb

Abstract

Peroxidases are heavily implicated in plant cell wall cross-linking reactions, altering the properties of the wall and impacting its utilization. Polysaccharide-polysaccharide cross-linking in grasses is achieved by dehydrodimerization of hydroxycinnamate-polysaccharide esters; a complex array of hydroxycinnamic acid dehydrodimers are released by saponification. Ferulates are the major cross-linking agents, but sinapate-ferulate cross-products have been discovered implicating sinapates in a similar role. New dehydrodimers have been authenticated, expanding our knowledge of the chemistry, role, and extent of cross-linking reactions. Ferulate dehydrotrimers have been discovered; whether these trimers truly cross-link three independent polysaccharide chains or only two remains to be determined. Hydroxycinnamates and their dehydrodimers also undergo radical coupling reactions with lignin monomers and possibly oligomers, resulting in lignin-polysaccharide cross-linking in the wall. Both polysaccharide-polysaccharide and lignin-polysaccharide cross-links inhibit the enzymatic hydrolysis of cell walls. The cross-linking process has particular relevance to plant physiology, human and animal nutrition and health, and food technology.

Abbreviations: CW – cell wall; DFA – dehydrodiferulic acid (or dehydrodiferulate in context); DSA – dehydrodisinapic acid; TFA – dehydrotriferulic acid; SA – sinapic acid (1S); TA – thomasidioic acid (5C3SS); IDF – insoluble dietary fiber; SDF – soluble dietary fiber; GC-MS – gas chromatography-mass spectrometry; NMR – nuclear magnetic resonance (spectroscopy).

sinapate sinapic acid ferulate ferulic acid hydroxycinnamic acid radical coupling cell wall cross-linking lignin dehydrogenation oxidative coupling dehydrodimer dehydrotrimer radical 

Copyright information

© Kluwer Academic Publishers 2004

Authors and Affiliations

  • John Ralph
    • 1
    • 2
  • Mirko Bunzel
    • 3
  • Jane M. Marita
    • 1
    • 2
  • Ronald D. Hatfield
    • 1
  • Fachuang Lu
    • 1
    • 2
  • Hoon Kim
    • 1
    • 2
  • Paul F. Schatz
    • 1
  • John H. Grabber
    • 1
  • Hans Steinhart
    • 3
  1. 1.U.S. Dairy Forage Research CenterUSDA-Agricultural Research ServiceMadisonU.S.A
  2. 2.Department of ForestryUniversity of Wisconsin-MadisonMadisonU.S.A
  3. 3.Institute of Biochemistry and Food ChemistryUniversity of HamburgHamburgGermany

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