Cross-linking of maize walls by ferulate dimerization and incorporation into lignin

Journal of Agricultural and Food Chemistry

Volumn 48, Issue 12, 2000, Pages 6106-6113

  Grabber, John H ^a   Ralph, John ^a   Hatfield, Ronald D ^a  

^a U S DAIRY FORAGE RESEARCH CENTER   (United States)

Author keywords

Cell wall; Cross linking; Dehydrogenation polymer; Diferulic acids; Ferulic acid; Gramineae; Lignin; Zea mays

Indexed keywords

FERULIC ACID; LIGNIN; PEROXIDASE; XYLAN;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS LINKING; DIMERIZATION; HYDROGENATION; MAIZE; NONHUMAN; POLYMERIZATION;

CELL WALL; COUMARIC ACIDS; DIMERIZATION; INDICATORS AND REAGENTS; LIGNIN; ZEA MAYS;

EID: 0034524722     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0006978     Document Type: Article

References (39)

1. Akin, D. E.; Hartley, R. D.; Rigsby, L. L.; Morrison III, W. H. Phenolic acids released from bermudagrass (Cynodon dactylon) by sequential sodium hydroxide treatment in relation to biodegradation of cell types. J. Sci. Food Agric. 1992, 58, 207-214.
2. Andreasen, M. F.; Christensen, L. P.; Meyer, A. S.; Hansen, A. Ferulic acid dehydrodimers in rye (Secale cereale L.). J. Cereal Sci. 2000, 31, 303-307.
3. Dimmel, D. R.; Schuller, L. F. Structural/reactivity studies. I. Soda reactions of lignin model compounds. J. Wood Chem. Technol. 1986a, 6, 535-564.
4. Dimmel, D. R.; Schuller, L. F. Structural/reactivity studies. II. Reactions of lignin model compounds with pulping additives. J. Wood Chem. Technol. 1986b, 6, 565-590.
5. Elder, T.; Ede, R. M. Coupling of coniferyl alcohol in the formation of dilignols: A molecular orbital study. Proceedings of the 8th International ' Symposium of Wood and Pulping Chemistry; Gummerus Kirjapaino Oy: Helsinki, Finland, 1995; Vol. 1, pp 115-122.
6. Gonzalez, L. F.; Rojas, M. G.; Perez, F. J. Diferulate and lignin formation is related to biochemical differences of wall-bound peroxidases. Phytochemistry 1999, 50, 711-717.
7. Grabber, J. H.; Hatfield, R. D.; Ralph, J.; Zon, J.; Amrhein, N. Ferulate cross-linking in cell walls isolated from maize cell suspensions. Phytochemistry 1995, 40, 1077-1082.
8. Grabber, J. H.; Ralph, J.; Hatfield, R. D.; Quideau, S.; Kuster, T.; Pell, A. N. Dehydrogenation Polymer-Cell Wall Complexes as a Model for Lignified Grass Walls. J. Agric. Food Chem. 1996, 44, 1453-1459.
9. Grabber, J. H.; Hatfield, R. D.; Ralph, J. Diferulate cross-links impede the enzymatic degradation of nonlignified maize walls. J. Sci. Food Agric. 1998a, 77, 193-200.
10. Grabber, J. H.; Ralph, J.; Hatfield, R. D. Ferulate cross-links limit the enzymatic degradation of synthetically lignified primary walls of maize. J. Agric. Food Chem. 1998b, 46, 2609-2614.
11. Hartley, R. D.; Jones, E. C. Diferulic acid as a component of cell walls of Lolium multiflorum. Phytochemistry 1976, 15, 1157-1160.
12. Hartley, R. D.; Morrison, W. H., III; Balza, F.; Towers, G. H. N. Substituted truxillic and truxinic acids in cell walls of Cynodon dactylon. Phytochemistry 1990, 29, 3699-3703.
13. Hatfield, R. D.; Ralph, J. Modeling the feasibility of intra-molecular dehydrodiferulate formation in grass walls. J. Sci. Food Agric. 1999, 79, 425-427.
14. Iiyama, K; Lam, T. B. T.; Stone, B. A. Phenolic acid bridges between polysaccharides and lignin in wheat internodes. Phytochemistry 1990, 29, 733-737.
15. Iiyama, K.; Lam, T. B. T.; Stone, B. Covalent cross-links in the cell wall. Plant Physiol. 1994, 104, 315-320.
16. Ishii, T. Isolation and characterization of a diferuloyl arabino-xylan hexasaccharide from bamboo shoot cell-walls. Carbohydr. Res. 1991, 219, 15-22.
17. Jacquet, G.; Pollet, B.; Lapierre, C.; Mhamdi, F.; Rolando, C. New ether-linked ferulic acid-coniferyl alcohol dimers identified in grass straws. J. Agric. Food Chem. 1995, 43, 2746-2751.
18. Karhunen, P.; Mikkola, J.; Parjunen, A.; Brunow, G. The behaviour of dibenzodioxocin structures in lignin during alkaline pulping processes. Nordic Pulp Paper Res. J. 1999, 24, 123-128.
19. Lam, T. B. T.; Iiyama, K; Stone, B. A. Changes in phenolic acids from internode walls of wheat and Phalaris during maturation. Phytochemistry 1992, 31, 2655-2658.
20. Markwalder, H. U.; Neukom, H. Diferulic acid as a possible cross-link in hemicelluloses from wheat germ. Phytochemistry 1976, 15, 836-837.
21. Musel, G.; Schindler, T.; Bergfeld, R.; Ruel, K.; Jacquet, G.; Lapierre, C.; Speth, V.; Schopfer, P. Structure and distribution of lignin in primary and secondary cell walls of maize coleoptiles analyzed by chemical and immunological probes. Planta 1997, 201, 146-159.
22. Myton, K. E.; Fry, S. C. Dithiothreitol and cobalt effects on membrane-associated peroxidases oxidizing feruloyl-CoA. Phytochemistry 1995, 38, 573-577.
23. Oosterveld, A.; Grabber, J. H.; Beldman, G.; Ralph, J.; Voragen, A. G. J. Formation of ferulic acid dehydrodimers through oxidative cross-linking of sugar beet pectin. Carbohydr. Res. 1997, 300, 179-181.
24. Quideau, S.; Ralph, J. Lignin-ferulate cross-links in grasses. Part 4. Incorporation of 5-5-coupled diferulate into lignin. J. Chem. Soc., Perkin Trans, 1 1997, 2351-2358.
25. Ralph, J.; Zhang, Y. A new synthesis of (Z)-cohiferyl alcohol, and characterization of its derived synthetic lignin. Tetrahedron 1998, 54, 1349-1354.
26. Ralph, J.; Helm, R. F.; Quideau, S. Lignin-feruloyl ester cross-links in grasses. Part 2. Model compound syntheses. J. Chem. Soc., Perkin Trans. 1 1992a, 2971-2980.
27. Ralph, J.; Helm, R. F.; Quideau, S.; Hatfield, R. D. Lignin-feruloyl ester cross-links in'grasses. Part 1. Incorporation of feruloyl esters into coniferyl alcohol dehydrogfenation polymers. J. Chem. Soc., Perkin Trans. 1 1992b, 2961-2969.
28. Ralph, J.; Quideau, S.; Grabber, J. H.; Hatfield, R. D. Identification and synthesis of new ferulic acid dehydrodimers present in grass cell walls. J. Chem. Soc., Perkin Trans. 1 1994, 3485-3498.
29. Ralph, J.; Grabber, J. H.; Hatfield, R. D. Lignin-ferulate cross-links in grasses: active incorporation of ferulate polysaccharide esters into ryegrass lignins. Carbohydr. Res. 1995, 275, 167-178.
30. Ralph, J.; Garcia-Conesa, M. T.; Williamson, G. Simple preparation of 8-5-coupled diferulate. J. Agric. Food Chem. 1998, 46, 2531-2532.
31. Russell, W. R.; Forrester, A. R.; Chesson, A.; Burkitt, M. J. Oxidative coupling during lignin polymerization is determined by unpaired electron delocalization within parent phenylpropanoid radicals. Arch. Biochem. Biophys. 1996, 332, 357-366.
32. Sarkanen, K. V.; Ludwig, C. H. Lignins, Occurrence, Formation, Structure and Reactions; Wiley-Interscience: New York, 1971.
33. Schooneveld-Bergmans, M. E. F.; Dignum, M. J. W.; Grabber, J. H.; Beldman, G.; Voragen, A. G. J. Studies on the oxidative cross-linking of feruloylated arabinoxylans from wheat flour and wheat bran. Carbohydr. Polym. 1999, 38, 309-317.
34. Schopfer, P. Hydrogen peroxide-mediated cell-wall stiffening in vitro in maize coleoptiles. Planta 1996, 199, 43-49.
35. Syrjanen, K.; Brunow, G. Oxidative cross coupling of p-hydroxycinnamic alcohols with dimeric arylglycerol β-aryl ether lignin model compounds. The effect of oxidation potentials. J. Chem. Soc., Perkin Trans. 11998, 3425-3429.
36. Syrjanen, K; Brunow, G. Regioselectivity in lignin biosynthesis. The influence of dimerization and cross-coupling. J. Chem. Soc., Perkin Trans. 1 2000, 183-187.
37. Tan, K.-S.; Hoson, T.; Masuda, Y.; Kamisaka, S. Involvement of cell wall-bound diferulic acid in light-induced decrease in growth rate and cell wall extensibility of Oryza coleoptiles. Plant Cell Physiol. 1992, 33, 103-108.
38. Turner, L. B.; Mueller-Harvey, I.; McAllan, A. B. Light-induced isomerization and dimerization of cinnamic acid derivatives in cell walls. Phytochemistry 1993, 33, 791-796.
39. Wallace, G.; Fry, S. C. In vitro peroxidase-catalyzed oxidation of ferulic acid esters. Phytochemistry 1995, 39, 1293-1299.