Role of dehydrodiferulates in maize resistance to pests and diseases

International Journal of Molecular Sciences

Volumn 11, Issue 2, 2010, Pages 691-703

  Santiago, Rogelio ^a   Malvar, Rosa A ^a  

^a MISIÓN BIOLÓGICA DE GALICIA CSIC   (Spain)

Author keywords

Corn borer; Dehydrodimers; Ferulic acid; Gibberella ear; Maize resistance mechanism; Maize weevil; Plant cell walls; Stalk rot

Indexed keywords

BENZOFURAN DERIVATIVE; COUMARIC ACID; DEHYDRODIFERULATE DERIVATIVE; FERULIC ACID; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

CHEMICAL STRUCTURE; CROSS LINKING; DISEASE RESISTANCE; EAR ROT; EUROPEAN CORN BORER; FUSARIUM GRAMINEARUM; GENE MAPPING; GENETIC RESISTANCE; GIBBERELLA; HOST RESISTANCE; INSECT; MAIZE; NONHUMAN; PLANT BREEDING; PLANT CELL; PLANT DISEASE; PLANT GENE; PLANT LEAF; PLANT PEST; QUANTITATIVE TRAIT LOCUS; REVIEW; STEM ROT; WEEVIL;

CORN BORER; DEHYDRODIMERS; FERULIC ACID; GIBBERELLA EAR; MAIZE RESISTANCE-MECHANISM; MAIZE WEEVIL; PLANT CELL WALLS; STALK ROT;

ANIMALS; CELL WALL; COUMARIC ACIDS; DISEASE RESISTANCE; GIBBERELLA; INSECTS; PLANT DISEASES; POLYSACCHARIDES; ZEA MAYS;

FUNGI; GIBBERELLA; HEXAPODA; SITOPHILUS ZEAMAIS; ZEA MAYS;

EID: 77649195305     PISSN: None     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms11020691     Document Type: Review

References (93)

1. Carpita, N.C.; Defernez, M.; Findlay, K.; Wells, B.; Shoue, D.A.; Catchpole, G.; Wilson, R.H.; McCann, M.C. Cell wall architecture of the elongating maize coleoptile. Plant Physiol. 2001, 127, 551-565.
2. Ishii, T. Structure and functions of feruloylated polysaccharides. Plant Sci. 1997, 127, 111-127.
3. Hatfield, R.D.; Wilson, J.R.; Mertens, D.R. Composition of cell walls isolated from cell types of grain sorghum stems. J. Sci. Food Agric. 1999, 79, 891-899.
4. Saulnier, L.; Thibault, J.F. Ferulic acid and diferulic acids as components of sugar-beet pectins and maize bran heteroxylans. J. Sci. Food Agric. 1999, 79, 396-402.
5. Ralph, J.; Hatfield, R.D.; Quideau, S.; Helm, R.F.; Grabber, J.H.; Jung, H.J.G. Pathway of p-coumaric acid incorporation into maize lignin as revealed by NMR. J. Am. Chem. Soc. 1994, 116, 9448-9456.
6. Grabber, J.H.; Quideau, S.; Ralph, J. p-Coumaroylated syringyl units in maize lignin; implications for β-ether cleavage by thioacidolysis. Phytochemistry 1996, 43, 1189-1194.
7. Lu, F.; Ralph, J. Detection and determination of p-coumaroylated units in lignins. J. Agric. Food Chem. 1999, 47, 1988-1992.
8. Morrison, T.A.; Jung, H.J.G.; Buxton, D.R.; Hatfield, R.D. Cell-wall composition of maize internodes of varying maturity. Crop Sci. 1998, 38, 455-460.
9. Vailhe, M.A.B.; Provan, G.J.; Scobbie, L.; Chesson, A.; Maillot, M.P.; Cornu, A.; Besle, J.M. Effect of phenolic structures on the degradability of cell walls isolated from newly extended apical internode of tall fescue (Festuca arundinacea Schreb.). J. Agric. Food Chem. 2000, 48, 618-623.
10. Migne, C.; Prensier, G.; Utille, J.P.; Angibeaud, P.; Cornu, A.; Grenet, E. Immunocytochemical localisation of p-coumaric acid and feruloyl-arabinose in the cell walls of maize stem. J. Sci. Food Agric. 1998, 78, 373-381.
11. MacAdam, J.W.; Grabber, J.H. Relationship of growth cessation with the formation of diferulate cross-links and p-coumaroylated lignins in tall fescue. Planta 2002, 215, 785-793.
12. Jung, H.J.G. Maize stem tissues: Ferulate deposition in developing internode cell walls. Phytochemistry 2003, 63, 543-549.
13. Grabber, J.H.; Ralph, J.; Lapierre, C.; Barrière, Y. Genetic and molecular basis of grass cell wall degradability. I. Lignin-cell wall matrix interactions. Comptes Rendus Biol. 2004, 327, 455-465.
14. Biggs, K.J.; Fry, S.C. Phenolic cross-linking in the plant cell wall. In Physiology of Expansion During Plant Growth: Proceedings of the Second Annual Pennsylvania State Symposium in Plant Physiology; Cosgrove, D.J., Knieval, D.P., Eds.; American Society of Plant Physiologists: Rockville, PA, USA, 1987; pp. 46-57.
15. Brett, C.T.; Waldron, K.W. Cell walls in diet and health. In Physiology and Biochemistry of Plant Cell Walls; Black, M., Charlwood, B.V., Eds.; Chapman and Hall: London, UK, 1996; pp. 222-238.
16. Bunzel, M. Chemistry and occurrence of hydroxycinnamate oligomers. Phytochem. Rev. 2009, doi 10.1007/s11101-009-9139-3.
17. Allerdings, E.; Ralph, J.; Schatz, P.F.; Gniechwitz, D.; Steinhart, H.; Bunzel, M. Isolation and structural identification of diarabinosyl 8-O-4-dehydrodiferulate from maize bran insoluble fibre. Phytochemistry 2005, 66, 113-124.
18. Ralph, J.; Grabber, J.H.; Hatfield, R.D. Lignin-ferulate crosslinks in grasses: Active incorporation of ferulate polysaccharide esters into ryegrass lignins. Carbohydr. Res. 1995, 275, 167-178.
19. Grabber, J.H.; Ralph, J.; Hatfield, R.D. Cross-linking of maize walls by ferulate dimerization and incorporation into lignin. J. Agric. Food Chem. 2000, 48, 6106-6113.
20. Piber, M.; Koehler, P. Identification of dehydro-ferulic acidtyrosine in rye and wheat: Evidence for a covalent cross-link between arabinoxylans and proteins. J. Agric. Food Chem. 2005, 53, 5276-5284.
21. Geissmann, T.; Neukom, H. Vernetzung von Phenolcarbonsäureestern von Polysacchariden durch oxydative phenolische Kupplung. Helv. Chim. Acta 1971, 54, 1108-1112.
22. Markwalder, H.U.; Neukom, H. Diferulic acid as a possible cross-link in hemicelluloses from wheat germ. Phytochemistry 1976, 15, 836-837.
23. Nordkvist, E.; Salomonsson, A.C.; Aman, P. Distribution of insoluble bound phenolic acids in barley grain. J. Sci. Food Agric. 1984, 35, 657-661.
24. Kamisaka, S.; Takeda, S.; Takahashi, K.; Shibata, K. Diferulic and ferulic acids in the cell wall of oat coleoptiles-their relationships to mechanical properties of the cell wall. Physiol. Plant 1990, 78, 1-7.
25. 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. 1994, 1, 3485-3498.
26. Parr, A.J.; Waldron, K.W.; Ng, A.; Parker, M.L. The wall-bound phenolics of Chinese water chestnut (Eleocharis dulcis). J. Sci. Food Agric. 1996, 71, 501-507.
27. Parr, A.J.; Ng, A.; Waldron, K.W. Ester-linked phenolic components of carrot cell walls. J. Agric. Food Chem. 1997, 45, 2468-2471.
28. Saulnier, L.; Thibault, J.F. Ferulic acid and diferulic acids as components of sugar-beet pectins and maize bran heteroxylans. J. Sci. Food Agric. 1999, 79, 396-402.
29. Bunzel, M.; Ralph, J.; Marita, J.; Steinhart, H. Identification of 4-O-5-coupled diferulic acid from insoluble cereal fiber. J. Agric. Food Chem. 2000, 48, 3166-3169.
30. Bunzel, M.; Ralph, J.; Marita, J.M.; Hatfield, R.D.; Steinhart, H. Diferulates as structural components in soluble and insoluble cereal dietary fibre. J. Sci. Food Agric. 2001, 81, 653-660.
31. Bunzel, M.; Funk, C; Steinhart, H. Semipreparative isolation of dehydrodiferulic and dehydrotriferulic acids as standard substances from maize bran. J. Sep. Sci. 2004, 27, 1080-1086.
32. Bunzel, M.; Ralph, J.; Funk, C.; Steinhart, H. Structural elucidation of new ferulic acid-containing phenolic dimers and trimers isolated from maize bran. Tetrahedron Lett. 2005, 46, 5845-5850.
33. Bunzel, M.; Ralph, J.; Brüning, P.; Steinhart, H. Structural identification of dehydrotriferulic and dehydrotetraferulic acids from insoluble maize bran fiber. J. Agric. Food Chem. 2006, 54, 6409-6418.
34. Rouau, X.; Cheynier, V.; Surget, A.; Gloux, D.; Barron, C.; Meudec, E.; Louis-Montero, J.; Criton, M. A dehydrotrimer of ferulic acid from maize bran. Phytochemistry 2003, 63, 899-903.
35. Funk, C.; Ralph, J.; Steinhart, H.; Bunzel, M. Isolation and structural characterisation of 8-O-4/8-O-4- and 8-8/8-O-4-coupled dehydrotriferulic acids from maize bran. Phytochemistry 2005, 66, 363-371.
36. Ralph, J.; Bunzel, M.; Marita, J.M.; Hatfield, R.D.; Lu, F.; Kim, H.; Schatz, P.F.; Grabber, J.H.; Steinhart, H. Peroxidase-dependent cross-linking reactions of p-hydroxycinnamates in plant cell walls. Phytochem. Rev. 2004, 3, 79-96.
37. Zarra, I.; Sanchez, M.; Queijeiro, E.; Pena, M.J.; Revilla, G. The cell wall stiffening mechanism in Pinus pinaster Aiton: Regulation by apoplastic levels of ascorbate and hydrogen peroxide. J. Sci. Food Agric. 1999, 79, 416-420.
38. Waldron, K.W.; Smith, A.C.; Parr, A.J.; Ng, A.; Parker, M.L. New approaches to understanding and controlling cell separation in relation to fruit and vegetable texture. Trends Food Sci. Technol. 1997, 8, 213-221.
39. Ng, A.; Harvey, A.J.; Parker, M.L.; Smith, A.C.; Waldron, K.W. Effect of oxidative coupling on the thermal stability of texture and cell wall chemistry of beet boot (Beta vulgaris). J. Agric. Food Chem. 1998, 46, 3365-3370.
40. Parker, C.C.; Parker, M.L.; Smith, A.C.; Waldron, K.W. Thermal stability of texture in Chinese water chestnut may be dependent on 8, 80-diferulic acid (aryltetralyn form). J. Agric. Food Chem. 2003, 51, 2034-2039.
41. Waldron, K.W.; Parker, M.L.; Smith, A.C. Plant cell walls and food quality. Comp. Rev. Food Sci. Food Safety 2003, 2, 128-146.
42. Robertson, J.A.; Faulds, C.B.; Smith, A.C.; Waldron, K.W. Peroxidase-mediated oxidative crosslinking and its potential to modify mechanical properties in water-soluble polysaccharide extracts and cereal grain residues. J. Agric. Food Chem. 2008, 56, 1720-1726.
43. Oosterveld, A.; Beldman, G.; Voragen, A.G.J. Oxidative cross-linking of pectic polysaccharides from sugar beet pulp. Carbohydr. Res. 2000, 328, 199-207.
44. Grabber, J.H. How do lignin composition, structure, and cross-linking affect degradability? A review of cell wall model studies. Crop Sci. 2005, 45, 820-831.
45. Jung, H.J.G.; Casler, M.D. Maize stem tissues: Impact of development on cell wall degradability. Crop Sci. 2006, 46, 1801-1809.
46. Gianessi, L.; Sankula, S.; Reigner, N. Plant Biotechnology: Potential impact for improving pest management in european agriculture, maize case study. The National Center for Food and Agricultural Policy; 2003. Full report available: http://www.ncfap.org/documents/ExecutiveSummaryJune.pdf (accessed November 12, 2009).
47. Bergvinson, D.J.; Arnason, J.T.; Hamilton, R.I.; Mihm J.A.; Jewell, D.C. Determining leaf toughness and its role in maize resistance to the European corn borer (Lepidoptera: Pyralidae). J. Econ. Entomol. 1994, 87, 1743-1748.
48. Bergvinson, D.J.; Hamilton, R.I.; Arnason, J.T. Leaf profile of maize resistance factors to European corn borer, Ostrinia nubilalis. J. Chem. Ecol. 1995, 21, 343-354.
49. Bergvinson, D.J.; Arnason, J.T.; Hamilton, R.I. Phytochemical changes during recurrent selection for resistance to the European corn borer. Crop Sci. 1997, 37, 1567-1572.
50. Ramputh, A.I. Soluble and cell wall Bound phenolic-mediated insect resistance in corn and sorghum. Ph.D. Dissertation, Ottawa-Carleton Institute of Biology: Ottawa, ON, Canada, 2002.
51. Brisson, L.F.; Tenhaken, R.; Lamb, C. Function of oxidative cross-linking of cell wall structural proteins in plant disease resistance. Plant Cell 1994, 6, 1703-1712.
52. Richardson, A.; Stewart, D.; McDougall, G.J. Identification and partial characterization of a coniferyl alcohol oxidase from lignifying xylem of Sitka spruce (Picea sitchensis). Planta 1997, 203, 35-43.
53. Fry, S.C. Cross-linking of matrix polymers in the growing cell walls of angiosperms. Ann. Rev. Plant Physiol. 1986, 37, 165-186.
54. Ramputh, A.I.; Arnason, J.T.; Cass, L.; Simmonds, J.A. Reduced herbivory of the European corn borer (Ostrinia nubilalis) on corn transformed with germin, a wheat oxalate oxidase gene. Plant Sci. 2002, 162, 431-440.
55. Mao, J.; Burt, A.J.; Ramputh, A-I.; Simmonds , J.; Cass, L.; Hubbard, K.; Miller, S.; Altosaar, I.; Arnason, J.T. Diverted secondary metabolism and improved resistance to European corn borer (Ostrinia nubilalis) in maize (Zea mays L.) transformed with wheat oxalate oxidase. J. Agric. Food Chem. 2007, 55, 2582-2589.
56. Santiago, R.; Butrón, A.; Arnason, J.T.; Reid, L.M.; Souto, X.C.; Malvar, R.A. Putative role of pith cell wall phenylpropanoids in Sesamia nonagrioides (Lepidoptera: Noctuidae) resistance. J. Agric. Food Chem. 2006, 54, 2274-2279.
57. Santiago, R.; Butrón, A.; Reid, L.M.; Arnason, J.T.; Sandoya, G.; Souto, X.C.; Malvar, R.A. Diferulate content of maize sheaths is associated with resistance to the Mediterranean corn borer Sesamia nonagrioides (Lepidoptera: Noctuidae). J. Agric. Food Chem. 2006, 54, 9140-9144.
58. Santiago, R.; Sandoya, G.; Butrón, A.; Barros, J.; Malvar, R.A. Changes in phenolic concentrations during recurrent selection for resistance to the Mediterranean corn borer (Sesamia nonagrioides Lef.). J. Agric. Food Chem. 2008, 56, 8017-8022.
59. Markham, R.H.; Bosque-Pérez, N.A.; Borgemeister, C.; Meikle, W.G. Developing pest management strategies for the maize weevil, Sitophilus zeamais, and the large grain borer, Prostephanus truncatus, in the humid and sub-humid tropics. FAO Plant Prot. Bull. 1994, 42, 125-136.
60. Tigar, B.J.; Osborne, P.E.; Key, G.E.; Flores-S, M.E.; Vazquez-A.M. Insect pest associated with rural maize stores in Mexico with particular reference to Prostephanus truncatus (Coleoptera: Bostrichidae). J. Stored Prod. Res. 1994, 30, 267-281.
61. Dobie, P. The contribution of the Tropical Stored Products Centre to the study of insect resistance in stored maize. Trop. Stored Prod. Inf. 1977, 34, 7-22.
62. Serratos, A.; Arnason, J.T.; Nozzolillo, C.; Lambert, J.D.H.; Philogène, B.J.R; Fulcher, G.; Davidson, K.; Peacock, L.; Atkinson, J.; Morand, P. Factors contributing to resistance of exotic maize populations to maize weevil, Sitophilus zeamais. J. Chem. Ecol. 1987, 13, 751-762.
63. Tipping, P.W.; Legg, D.E.; Rodriguez, J.G.; Poneleit, C.G. Influence of maize pericarp surface relief on the resistance to the maize weevil. J. Kans. Entomol. Soc. 1988, 61, 237-241.
64. Arnason, J.T.; Baum, B.; Gale, J.; Lambert, J.D.H.; Bergvinson, D.; Philogène, B.J.R.; Serratos, J.A.; Mihm, J.A.; Jewell, D.C. Variation in resistance of Mexican landraces of maize to maize weevil Sitophilus zeamais, in relation to taxonomic and biochemical parameters. Euphytica 1994, 74, 227-236.
65. Arnason, J.T.; Conilh de Beyssac, B.; Philogène, B.J.R.; Bergvinson, D.; Serratos, J.A.; Mihm, J.A. Mechanism of resistance in maize grain to the maize weevil and the larger grain borer. In Insect Resistance Maize: Recent Advances and Utilization; Proceedings of an International Symposium; Mexico, D.F., Ed.; Mexico, 23 November-3 December, 1997; pp. 91-95.
66. Classen, D.; Arnason, J.T.; Serratos, J.A.; Lambert, J.D.H.; Nozzolillo, C.; Philogène, B.J.R. Correlation of phenolic acid content of maize to resistance to Sitophilus zeamais, the maize weevil, in CIMMYT's collections. J. Chem. Ecol. 1990, 16, 301-315.
67. García-Lara, S.; Bergvinson, D.; Burt, A.J.; Ramputh, A-I.; Díaz-Pontones, D.M.; Arnason, J.T. The role of pericarp cell wall components in maize weevil resistance. Crop Sci. 2004, 44, 1546-1552.
68. Sutton, J.C. Epidemiology of wheat head blight and maize ear rot caused by Fusarium graminearum. Can. J. Plant Pathol. 1982, 4, 195-209.
69. Mirocha, C.J.; Pathre, S.Y.; Schauerhamer, B.; Christensen, C.M. Natural occurrence of Fusarium toxins in feedstuff. Appl. Environ. Microbiol. 1976, 32, 553-556.
70. Pitt, J.I. Toxigenic fungi and mycotoxins. Br. Med. Bull. 2000, 56, 184-192.
71. Steyn, P.S.; Stander, M.A. Mycotoxins as causal factors of diseases in humans. J. Toxicol. Toxin Rev. 1999, 18, 229-243.
72. Reid, L.M.; Mather, D.E.; Arnason, J.T.; Hamilton, R.I.; Bolton, A.T. Changes in phenolic constituents of maize silk infected with Fusarium graminearum. Can. J. Bot. 1992, 70, 1697-1702.
73. Assabgui, R.A.; Reid, L.M.; Hamilton, R.I., Arnason, J.T. Correlation of kernel (E)-ferulic acid content of maize with resistance to Fusarium graminearum. Phytopathology 1993, 83, 949-953.
74. Miller, J.D.; Miles, M.; Davis, A.F. Kernel concentrations of 4-acetylbenzoxazolin-2-one and diferuloylputrescine in maize genotypes and Gibberella ear rot. J. Agric. Food Chem. 1997, 45, 4456-4459.
75. Bily, A.C.; Reid, L.M.; Taylor, J.H.; Johnston, D.; Malouin, C.; Buró, A.J.; Bakan, B.; Regnault-Roger, C.; Pauls, K.P.; Arnason, J.T.; Philogène B.J.R. Dehydrodimers of ferulic acid in maize grain pericarp and aleurone: Resistance factors to Fusarium graminearum. Phytopathology 2003, 93, 712-719.
76. Grabber, J.H.; Hatfield, R.H., Ralph, J. Diferulate cross-links impede the enzymatic degradation of non-lignified maize walls. J. Sci. Food Agric. 1998, 77, 193-200.
77. Obel, N.; Porchia, A.C.; Scheller, H.V. Dynamic changes in cell wall polysaccharides during wheat seedling development. Phytochemistry 2002, 60, 603-610.
78. Manka, M. Cellulolytic and pectolytic activity of Fusarium isolates pathogenic to corn seedlings. Acta Microbiol. Pol. 1980, 30, 25-32.
79. Huang, Z.; White, D.G.; Payne, G.A. Corn seed proteins inhibitory to Aspergillus flavus and aflatoxin biosynthesis. Phytopathology 1997, 87, 622-627.
80. Bakan, B.; Bily, A.C.; Melcion, D.; Cahagnier, B.; Regnault-Roger, C.; Philogène, B.J.R.; Richard-Molard D. Possible role of plant phenolics in the production of trichothecenes by Fusarium graminearum strains on different fractions of maize kernels. J. Agric. Food Chem. 2003, 51, 2826-2831.
81. Snijders, C.H. A breeding for resistance to Fusarium in wheat and maize. In Mycotoxins in Grain: Compounds Other than Aflatoxin; Miller, J.D., Trenholm, H.L., Eds.; Eagan Press: St. Paul, MN, USA, 1994.
82. Gilberton, R.L.; Brown, W.M.; Ruppel, E.G. Prevalence and virulence of Fusarium spp. associated with stalk rot of corn in Colorado. Plant Dis. 1985, 69, 1065-1068.
83. Marasas, W.F.O.; Nelson, P.E.; Tousson, T.A. Toxigenic Fusarium Species: Identity and Mycotoxicology; The Pennsylvania State University Press: Pennsylvania, USA, 1984.
84. Miller, J.D.; Young, J.C.; Trenholm, H.L. Fusarium toxins in field corn. I. Time course of fungal growth and production of deoxynivalenol and other mycotoxins. Can. J. Bot. 1983, 61, 3080-3087.
85. Young, J.C.; Miller, J.D. Appearance of fungus, ergosterol and Fusarium mycotoxins in the husk, axial stem and stalk after ear inoculation of field corn. Can. J. Plant Sci. 1985, 65, 47-53.
86. Purushothaman, D. Changes in phenolic compounds in rice cultivars as influenced by Xanthomonas oryzae. Il Riso 1976, 25, 88-91.
87. Baranowski, J.D.; Davidson, P.M.; Nagel, C.W.; Branen, A.L. Inhibition of Saccharomyces cerevisiae by naturally occurring hydroxycinnamates. J. Food Sci. 1980, 45, 592-594.
88. Kasenberg, T.R.; Traquair, J.A. Effects of phenolics on growth of Fusarium oxysporum f. sp. radicis-lycopersici in vitro. Can. J. Bot. 1988, 66, 1174-1177.
89. McKeehen, J.D.; Busch, R.H.; Fulcher, R.G. Evaluation of wheat (Triticum aestivum L.) phenolic acids during grain development and their contribution to Fusarium resistance. J. Agric. Food Chem. 1999, 47, 1476-1482.
90. Fry, S.C. Intracellular feruloylation of pectic polysaccharides. Planta 1987, 171, 205-211.
91. Santiago, R.; Reid, L.M.; Arnason, J.T.; Zhu, X.Y.; Martinez, N.; Malvar, R.A. Phenolics in maize genotypes differing in susceptibility to Gibberella stalk rot (Fusarium graminearum Schwabe). J. Agric. Food Chem. 2007, 55, 5186-5193.
92. Ikegawa, T.; Mayama, S.; Nakayashiki, H.; Kato, H. Accumulation of diferulic acid during the hypersensitive response of oat leaves to Puccinia coronata f. sp. avena and its role in the resistance of oat tissues to cell wall degrading enzymes. Physiol. Mol. Plant Pathol. 1996, 48, 245-256.
93. Matern, U.; Grimmig, B. Polyphenols in plant pathology. In Polyphenolic Phenomena; Scalbert, A., Ed.; INRA Editions: Paris, France, 1993.