Lignin-ferulate cross-links in grasses. Part 4. Incorporation of 5-5-coupled dehydrodiferulate into synthetic lignin

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 16, 1997, Pages 2351-2358

  Quideau, Stéphane ^a   Ralph, John ^b  

^a TEXAS TECH UNIVERSITY   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000870167     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a701808h     Document Type: Article

References (61)

1. J. Ralph, J. H. Grabber and R. D. Hatfield, Carbohydr. Res., 1995, 275, 167.
2. J. Ralph, R. F. Helm and S. Quideau, J. Chem. Soc., Perkin Trans. 1, 1992, 2971.
3. J. Ralph, R. F. Helm, S. Quideau and R. D. Hatfield, J. Chem. Soc., Perkin Trans. 1, 1992, 2961.
4. H. G. Jung and D. A. Deetz, in Forage Cell Wall Structure and Digestibility, ed. H. G. Jung, D. R. Buxton and R. D. Hatfield, J. Ralph, ASA-CSSA-SSSA, Madison, 1993, pp. 315-346.
5. S. C. Fry and J. C. Miller, in Plant Cell Wall Polymers, Biogenesis and Biodegradation, ed. N. G. Lewis and M. G. Paice, Amer. Chem. Soc., Washington DC, 1989, pp. 33-46.
6. E. Yamamoto, G. H. Bokelman and N. G. Lewis, in Plant Cell Wall Polymers, Biogenesis and Biodegradation, ed. N. G. Lewis and M. G. Paice, Amer. Chem. Soc., Washington, DC, 1989, pp. 68-88.
7. R. D. Hartley and C. W. Ford, in Plant Cell Wall Polymers, Biogenesis and Biodegradation, ed. N. G. Lewis and M. G. Paice, Amer. Chem. Soc., Washington, 1989, pp. 137-145.
8. H. G. Jung and J. Ralph, in Microbial and Plant Opportunities to Improve Lignocellulose Utilization by Ruminants, ed. D. E. Akin, L. G. Ljungdahl, J. R. Wilson and P. J. Harris, Elsevier, New York, 1990, pp. 173-182.
9. J. Ralph and R. F. Helm, in Forage Cell Wall Structure and Digestibility, ed. H. G. Jung, D. R. Buxton and R. D. Hatfield, J. Ralph, ASA-CSSA-SSSA, Madison, 1993, pp. 201-246.
10. G. P. Bolwell, Phytochemistry, 1988, 27, 1235
11. (Chem. Abstr., 120, 27426).
12. G. P. Bolwell, Int. Rev. Cytol., 1993, 146, 261.
13. J. Ralph, R. D. Hatfield, J. H. Grabber, H. G. Jung, S. Quideau and R. F. Helm, in Lignin and Lignan Biosynthesis, ed. N. G. Lewis and S. Sarkanen, Amer. Chem. Soc., 1997, in press.
14. J. Ralph, S. Quideau, J. H. Grabber and R. D. Hatfield, J. Chem. Soc., Perkin Trans. 1, 1994, 3485.
15. T. Geissmann and H. Neukom, Helv. Chim. Acta, 1971, 54, 1108.
16. S. C. Fry, Planta, 1979, 146, 343.
17. H. U. Markwalder and H. Neukom, Phytochemistry, 1976, 15, 836.
18. R. D. Hartley and E. C. Jones, Phytochemistry, 1976, 15, 1157.
19. V. Micard, J. H. Grabber, J. Ralph, C. M. G. C. Renard and J.-F. Thibault, Phytochemistry, 1997, 44, 1365.
20. A. Oosterveld, J. H. Grabber, G. Beldman, J. Ralph and A. G. J. Voragen, Carbohydr. Research, 1997, 300, 179.
21. M. Sánchez, M. J. Peña, G. Revilla and I. Zarra, Plant Physiol., 1996, 111, 941.
22. J. H. Grabber, R. D. Hatfield, J. Ralph, J. Zon and N. Armhein, Phytochemistry, 1995, 40, 1077.
23. K. W. Waldron, A. J. Parr, A. Ng and J. Ralph, Phytochem. Anal., 1996, 7, 305
24. (Chem. Abstr., 126, 72156).
25. J. H. Grabber, J. Ralph, R. D. Hatfield, S. Quideau, T. Kuster and A. N. Pell, J. Agric. Food Chem., 1996, 44, 1453.
26. A. J. Parr, K. W. Waldron, A. Ng and M. L. Parker, J. Sci. Food Agric., 1996, 71, 501.
27. G. Jacquet, B. Pollet, C. Lapierre, F. Mhamdi and C. Rolando, J. Agric. Food Chem., 1995, 43, 2746.
28. J. H. Grabber and J. Ralph, Phytochemistry, 1997, submitted.
29. R. A. Teutonico, M. W. Dudley, J. D. Orr, D. G. Lynn and A. N. Binns, Plant Physiol., 1991, 97, 288.
30. F. Chioccara, S. Poli, B. Rindone, T. Pilati, G. Brunow, P. Pietikäinen and H. Setälä, Acta Chem. Scand., 1993, 47, 610.
31. S. Quideau and J. Ralph, Holzforschung, 1994, 48, 12
32. (Chem. Abstr., 120, 273338j) .
33. J. Baumgartner and H. Neukom, Chimia, 1972, 26, 366.
34. J. Newman, R. N. Rej, G. Just and N. G. Lewis, Holzforschung, 1986, 40, 369
35. (Chem. Abstr., 106, 34887s).
36. R. F. Helm, J. Ralph and R. D. Hatfield, Carbohydr. Res., 1992, 229, 183-194.
37. S. Quideau and J. Ralph, J. Agric. Food Chem., 1992, 40, 1108.
38. P. Karhunen, P. Rummakko, J. Sipila, G. Brunow and I. Kilpeläinen, Tetrahedron Lett., 1995, 36, 4501.
39. P. Karhunen, P. Rummakko, J. Sipilä, G. Brunow and I. Kilpeläinen, Tetrahedron Lett., 1995, 36, 169.
40. P. Karhunen, P. Rummakko, A. Pajunen and G. Brunow, J. Chem. Soc., Perkin Trans. 1, 1996, 2303.
41. A. Bax and S. Subramanian, J. Magn. Reson., 1986, 67, 565.
42. A. Bax and M. F. Summers, J. Am. Chem. Soc., 1986, 108, 2093.
43. L. Lerner and A. Bax, J. Magn. Reson., 1986, 69, 375.
44. G. W. Vuister, R. Boelens, R. Kaptein, R. E. Hurd, B. John and P. C. M. Van Zijl, J. Am. Chem. Soc., 1991, 113, 9688.
45. J. A. Gavin, J. L. Pons and M. A. Delsuc, J. Magn. Reson., Ser. A, 1996, 122, 64
46. (Chem. Abstr., 125, 242124).
47. K. Iiyama, T. B. T. Lam and B. Stone, Plant Physiol., 1994, 104, 315.
48. T. B. T. Lam, K. Iiyama and B. A. Stone, Phytochemistry, 1992, 31, 2655.
49. J. H. Grabber, R. D. Hatfield and J. Ralph, J. Sci. Food Agric., 1997, submitted.
50. R. D. Hatfield, J. H. Grabber and J. Ralph, Modeling cross-links within wall matrices: impact upon polysaccharide degradation, Keystone Symposium on the Extracellular Matrix of Plants Tamarron, CO, 1996, poster 110.
51. J. Ralph, R. D. Hatfield, S. Quideau, R. F. Helm and J. H. Grabber, Cell wall cross-linking in grasses by ferulates and dehydrodiferulates, Keystone Symposium on the Extracellular Matrix of Plants Tamarron, CO, 1996, paper 012.
52. J. H. Grabber, R. D. Hatfield and J. Ralph, Altering lignin composition, structure, and cross-linking: potential impact on cell wall degradation, 1996 National Amer. Chem. Soc. New Orleans, LA, 1996, paper Cell-54.
53. R. D. Hatfield and J. Ralph, Molecular modeling of dehydrodiferulates: Are intramolecular dimers feasible within grass walls?, 1996 National Amer. Chem. Soc. New Orleans, LA, 1996, paper Cell-55.
54. S. A. Ralph, J. Ralph, W. L. Landucci and L. L. Landucci, Available over Internet at http://www.dfrc.wisc.edulsoftware.html, or send E-mail to jralph@facstaff.wisc.edu, 1996.
55. K. Elbs and H. Lerch, J. Prakt. Chem., 1916, 93, 4.
56. Y. Omote, Y. Fujinuma and N. Sugiyama, Nippon Kagaku Zasshi, 1968, 89, 94
57. (Chem. Abstr., 69, 51787).
58. K. Freudenberg, V. Jovanovic and F. Topfmeier, Chem. Ber., 1961, 94, 3227.
59. H. Richtzenhain, Chem. Ber., 1949, 82, 447.
60. S. Quideau and J. Ralph, J. Chem. Soc., Perkin Trans. 1, 1993, 653.
61. K. Weinges, F. Nader and K. Künster, in Chemistry of Lignans, ed. C. B. S. Rao, Andhra University Press, Visakhapatnam, 1978, pp. 1-37.