Dehydrogenation polymer-cell wall complexes as a model for lignified grass walls

Journal of Agricultural and Food Chemistry

Volumn 44, Issue 6, 1996, Pages 1453-1459

  Grabber, John H ^a   Ralph, John ^a   Hatfield, Ronald D ^a   Quideau, Stéphane ^a,d   Kuster, Thomas ^b   Pell, Alice N ^c  

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

^b FOREST PRODUCTS LABORATORY   (United States)

^c Department of Population Medicine and Diagnostic Sciences   (United States)

^d PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

Cell wall; Dehydrogenation polymer; Fiber; Fiber degradability; Gramineae; Lignin; NMR; p hydroxycinnamyl alcohols; Peroxidase; Pyrolysis; Thioacidolysis; Transmission electron microscopy; Zea mays

Indexed keywords

POACEAE; ZEA MAYS;

EID: 0000677935     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf9502717     Document Type: Article

References (49)

1. Brown, A. Review of lignin in biomass. J. Appl. Biochem. 1985, 7, 371-387.
2. Brunow, G.; Sipila, J.; Makela, T. On the mechanism of formation of noncyclic benzyl ethers during lignin biosynthesis. Part 1. The reactivity of β-O-4 quinone methides with phenols and alcohols. Holzforschung 1989, 43, 55-59.
3. Chesson, A.; Stewart, C. S.; Dalgarno, K.; King, T. P. Degradation of isolated grass mesophyll, epidermis and fibre cell walls in the rumen and by celluloytic rumen bacteria in axenic culture. J. Appl. Bacteriol. 1986, 60, 327-336.
4. Erdtman, H. Outstanding problems in lignin chemistry. Ind. Eng. Chem. 1957, 49, 1385-1386.
5. Evans, J. J.; Himmelsbach, D. S. Incorporation of peroxidase into synthetic lignin. J. Agric. Food Chem. 1991, 39, 830-832.
6. Freudenberg, K. In Constitution and Biosynthesis of Lignin; Freudenberg, K., Neish, A. C., Eds.; Springer-Verlag: Berlin, 1968; pp 47-116.
7. Gagnaire, D.; Robert, D. A polymer model of lignin (D. H. P.) carbon-13 selectively labelled at the benzylic positions: synthesis and NMR study. Makromol. Chem. 1977, 178, 1477-1495.
8. 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.
9. Harlow, E.; Lane, D. Antibodies: A Laboratory Manual; Cold Spring Harbor Laboratory: Cold Spring Harbor, NY, 1988; p 508.
10. Hatfield, R. D. Cell wall polysacchride interactions and degradability. In Forage Cell Wall Structure and Digestibility; Jung, H. J., Buxton, D. R., Hatfield, R. D., Ralph, J., Eds.; ASA-CSSA-SSSA: Madison, WI, 1993; pp 285-313.
11. Hatfield, R. D.; Jung, H. G.; Ralph, J.; Buxton, D. R.; Weimer, P. J. A comparison of the insoluble residues produced by the Klason lignin and acid detergent lignin procedures. J. Sci. Food Agric. 1994, 65, 51-58.
12. Higuchi, T.; Ogino, K; Tanahashi, M. Effect of polysaccharides on dehydropolymerization of coniferyl alcohol. Wood Res. 1971, 51, 1-11.
13. Hosel, W.; Fiedler-Preiss, A.; Borgmann, E. Relationship of coniferin β-glucosidase to lignification in various plant cell suspension cultures. Plant Cell, Tissue Organ Cult. 1982, 1, 137-148.
14. Iiyama, K.; Lam, T. B. T.; Meikle, P. J.; Ng, K; Rhodes, D.; Stone, B. A. Cell wall biosynthesis and its regulation. In Forage Cell Wall Structure and Digestibility; Jung, H. G., Buxton, D. R., Hatfield, R. D., Ralph, J., Eds.; ASA-CSSA-SSSA: Madison, WI, 1993; pp 621-683.
15. Iiyama, K.; Lam, T. B. T.; Stone, B. Covalent cross-links in the cell wall. Plant Physiol. 1994, 104, 315-320.
16. Imamura, T.; Watanabe, T.; Kuwahara, M.; Koshijima, T. Ester linkages between lignin and glucuronic acid in lignincarbohydrate complexes from Fagus crenata. Phytochemistry 1994, 37, 1165-1173.
17. Ingold, E.; Sugiyama, M.; Komamine, A. Secondary cell wall formation: changes in cell wall constituents during the differentiation of isolated mesophyll cells of Zinnia elegans tracheary elements. Plant Cell Physiol. 1988,29, 295-303.
18. Jung, H. J. G.; Buxton, D. R. Forage quality variation among maize inbreds: relationships of cell-wall composition and in-vitro degradability for stem internodes. J. Sci. Food Agric. 1994, 66, 313-322.
19. Jung, H. G.; Deetz, D. A. Cell wall lignification and degradability. In Forage Cell Wall Structure and Digestibility; Jung, H. G., Buxton, D. R., Hatfield, R. D., Ralph, J., Eds.; ASA-CSSA-SSSA: Madison, WI, 1993; pp 315-346.
20. Kieliszewski, M.; Lamport, D. T. A. Purification and partial characterization of a hydroxyproline-rich glycoprotein in a graminaceous monocot, Zea mays. Plant Physiol. 1987, 85, 823-827.
21. Kieliszewski, M.; Lamport, D. T. A. Tying the knots in the extensin network. In Self-Assembling Architecture, Proceedings of the 46th Symposium of the Society for Developmental Biology; Varner, J. E., Ed.; St. Paul, MN, 1988; pp 61-77.
22. Kirk, T. K.; Connors, W. J.; Bleam, W. D.; Hackett, W. F., Zeikus, J. G. Preparation and microbial decomposition of synthetic (14C) lignins. Proc. Natl. Acad. Sci U.S.A. 1975, 72, 2513-2519.
23. Kritchevsky, D. Evaluation of Publicly Available Scientific Evidence Regarding Certain Nutrient-Disease Relationships: Dietary Fiber and Cancer No. 5; Center for Food Safety and Applied Nutrition, Food and Drug Administration. Department of Health and Human Services: Washington, DC, 1991.
24. Lapierre, C.; Monties, B.; Rolando, C. Thioacidolysis of lignin: comparison with acidolysis. J. Wood Chem. Technol. 1985, 5, 277-292.
25. Lapierre, C.; Pollet, B.; Monties, B.; Rolando, C. Thioacidolysis of spruce lignin: GC-MS analysis of the main dimers recovered after Raney nickel desulphuration. Holzforschung 1991, 45, 61-68.
26. Lewis, N. G.; Newman, J.; Just, G.; Ripmeister, J. Determination of bonding patterns of carbon-13 specifically enriched dehydrogenatively polymerized lignin in solution and solid state. Macromolecules 1987a, 20, 1752-1756.
27. Lewis, N. G.; Yamamoto, E.; Wooten, J. B.; Just, G.; Ohashi, H.; Towers, G. H. N. Monitoring biosynthesis of wheat cellwall phenylpropanoids in situ. Science 1987b, 237, 1344-1346.
28. McDougall, G. J. Changes in cell wall-associated peroxidases during the lignification of flax fibres. Phytochemistry 1992, 31, 3385-3389.
29. Mueller-Harvey, I.; Hartley, R. D.; Harris, P. J.; Curzon, E. H. Linkage of p-coumaryl and feruloyl groups to cell wall polysaceharides of barley straw. Carbohydr. Res. 1986,148, 71-85.
30. Nakashima, J.; Takabe, K.; Saiki, H. Artificial lignification within unlignified cell walls of Populus koreana. Mokuzai Gakkaishi 1992, 38, 1136-1142.
31. Nilsson, T.; Daniel, G.; Kirk, T. K; Obst, J. R. Chemistry and microscopy of wood decay by some higher ascomyeetes. Holzforschung 1989, 43, 11-17.
32. Ohnishi, J.; Watanabe, T.; Koshijima, T. Synthesis of dehydrogenation polymer-polyose complexes by peroxidase. Phytochemistry 1992, 31, 1185-1190.
33. Pell, A. N.; Schofield, P. Computerized monitoring of gas production to measure forage digestion in vitro. J. Dairy Sci. 1993, 76, 1063-1073.
34. Quideau, S.; Ralph, J. Facile large-scale synthesis of coniferyl, sinapyl, and p-coumaryl alcohol. J. Agric. Food Chem. 1992, 40, 1108-1110.
35. Quideau, S.; Ralph, J. A biomimetic route to lignin model compounds via silver (I) oxide oxidation 1. Synthesis of dilignols and non-cyclic benzyl aryl ethers. Holzforschung 1994, 48, 12-22.
36. Ralph, J.; Hatfield, R. D. Pyrolysis-GC-MS characterization of forage materials. J. Agric. Food Chem. 1991, 39, 1426-1437.
37. Ralph, J.; Helm, R. F.; Quideau, S,; Hatfield, R. D. Ligninferuloyl ester cross-links in grasses. Part 1. Incorporation of feruloyl esters into coniferyl alcohol dehydrogenation polymers. J. Chem. Soc., Perkin Trans, 1 1992, 2961-2969.
38. Ralph, J.; Hatfield, R. D.; Quideau, S.; Helm, R. F.; Grabber, J.; Jung, H. G. Pathway of p-coumaric acid incorporation into maize lignin as revealed by NMR. J. Am. Chem. Soc. 1994a, 116, 9448-9456.
39. 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 1994b, 3485-3498.
40. Sipila, J.; Brunow, G. On the mechanism of formation of noncyclic benzyl ethers during lignin biosynthesis. Part 2. The effect of pH on the reaction between a β-O-4 type quinone methide and vanillyl alcohol in water-dioxane solutions. The stability of non-cyclic benzyl aryl ethers during lignin biosynthesis. Holzforschung 1991, 45, 275-278.
41. Terashima, N.; Seguchi, Y. Heterogeneity in formation of lignin, IX. Factors influencing the formation of condensed structures in lignins. Cellulose Chem. Technol. 1988, 22, 147-154.
42. Terashima, N.; Fukushima, K.; He, L.-F.; Takabe, K. Comprehensive model of the lignified plant cell wall. In Forage Cell Wall Structure and Digestibility; Jung, H. G., Buxton, D. R., Hatfield, R. D., Ralph, J., Eds.; ASA-CSSA-SSSA: Madison, WI, 1993; pp 247-270.
43. Theander, O.; Westerlund, E. A. Studies on dietary fiber. 3. Improved procedures for analysis of dietary fiber. J. Agric. Food Chem. 1986, 34, 330-336.
44. Tollier, M.-T.; Lapierre, C.; Monties, B.; Francesch, C.; Rolando, C. Structural variations in synthetic lignins (DHPs) according to the conditions of their preparation. Proceedings of the Sixth International Symposium, of Wood and Pulping Chemistry; Australian Pulp and Paper Industries Technical Association: Melbourne, Australia, 1991; Vol. 2, pp 35-41.
45. Whitmore, F. W. Lignin-carbohydrate complex formed in isolated cell walls of callus. Phytochemistry 1978,17, 421-425.
46. Whitmore, F. W. Lignin-protein complex in cell walls of Pinus ellliottii: amino acid constituents. Phytochemistry 1982,21, 315-318.
47. Wilson, J. R. Organization of forage plant tissues. In Forage Cell Wall Structure and Digestibility; Jung, H. G., Buxton, D. R., Hatfield, R. D., Ralph, J., Eds.; ASA-CSSA-SSSA: Madison, WI, 1993; pp 1-27.
48. Ye, Z.-H.; Varner, J. E. Tissue-specific expression of cell wall proteins in developing soybean tissues. Plant Cell 1991, 3, 23-37.
49. Zon, J.; Amrhein, N. Inhibitors of phenylalanine ammonia lyase: 2-aminoindan-2-phosphonic acid and related compounds. Justus Liebigs Ann. Chem. 1992, 625-628.