Structural identification of dehydrotriferulic and dehydrotetraferulic acids isolated from insoluble maize bran fiber

Journal of Agricultural and Food Chemistry

Volumn 54, Issue 17, 2006, Pages 6409-6418

  Bunzel, Mirko ^a   Ralph, John ^b,c   Brüning, Philipp ^a   Steinhart, Hans ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

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

^c UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

Arabinoxylans; Cell wall cross linking; Dehydrotetramer; Dehydrotrimer; Dietary fiber; Ferulate; Ferulic acid; NMR; Radical coupling; Tetraferulate; Tetraferulic acid; Triferulate; Triferulic acid; Zea mays L.

Indexed keywords

COUMARIC ACID; FERULIC ACID;

ARTICLE; CELL WALL; CHEMICAL STRUCTURE; CHEMISTRY; DIETARY FIBER; GEL CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MAIZE; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLUBILITY;

CELL WALL; CHROMATOGRAPHY, GEL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COUMARIC ACIDS; DIETARY FIBER; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR STRUCTURE; SOLUBILITY; ZEA MAYS;

ZEA MAYS;

EID: 33748560454     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf061196a     Document Type: Article

References (30)

1. 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.
2. Piber, M.; Koehler, P. Identification of dehydroferulic acid-tyrosine in rye and wheat: Evidence for a covalent cross-link between arabinoxylans and proteins. J. Agric. Food Chem. 2005, 53, 5276-5284.
3. Ishii, T. Structure and functions of feruloylated polysaccharides. Plant Sci. 1997, 127, 111-127.
4. Saulnier, L.; Crepeau, M. J.; Lahaye, M.; Thibault, J. F.; Garcia-Conesa, M. T.; Kroon, P. A.; Williamson, G. Isolation and structural determination of two 5,5′-diferuloyl oligosaccharides indicate that maize heteroxylans are covalently cross-linked by oxidatively coupled ferulates. Carbohydr. Res. 1999, 320, 82-92.
5. 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.
6. Levigne, S.; Ralet, M.-C.; Quemener, B.; Thibault, J. F. Isolation of diferulic bridges ester-linked to arabinan in sugar beet cell walls. Carbohydr. Res. 2004, 539, 2315-2319.
7. Bunzel, M.; Ralph, J.; Steinhart, H. Association of non-starch polysaccharides and ferulic acid in grain amaranth (Amaranthus caudatus L.) dietary fiber. Mol. Nutr. Food Res. 2005, 49, 551-559.
8. Hartley, R. D.; Morrison, W. H.; Himmelsbach, D. S.; Borneman, W. S. Cross-linking of cell-wall phenolic arabinoxylans in gramineous plants. Phytochemistry 1990, 29, 3705-3709.
9. Geissmann, T.; Neukom, H. Vernetzung von Phenolcarbonsäureestern von Polysacchariden durch oxidative phenolische Kupplung. Helv. Chim. Acta 1971, 54, 1108-1112.
10. 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.
11. Kamisaka, S.; Takeda, S.; Takahashi, K.; Shibata, K. Diferulic and ferulic acid in the cell-wall of Avena coleoptiles-Their relationships to mechanical properties of the cell-wall. Physiol. Plant. 1990, 78, 1-7.
12. 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.
13. 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.
14. Ng, A.; Greenshields, R. N.; Waldron, K. W. Oxidative cross-linking of corn bran hemicellulose: Formation of ferulic acid dehydrodimers. Carbohydr. Res. 1997, 303, 459-462.
15. Oosterveld, A.; Beldman, G.; Voragen, A. G. J. Oxidative cross-linking of pectic polysaccharides from sugar beet pulp. Carbohydr. Res. 2000, 328, 199-207.
16. 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.
17. Hatfield, R. D.; Ralph, J.; Grabber, J. H. Cell wall structural foundations: Molecular basis for improving forage digestibilities. Crop Sci. 1999, 39, 27-37.
18. Fry, S. C.; Willis, S. C.; Paterson, A. E. J. Intraprotoplasmic and wall-localised formation of arabinoxylan-bound diferulates and larger ferulate coupling-products in maize cell-suspension cultures. Planta 2000, 211, 679-692.
19. 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.
20. 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.
21. Bunzel, M.; Ralph, J.; Funk, C.; Steinhart, H. Isolation and identification of a ferulic acid dehydrotrimer from saponified maize bran insoluble fiber. Eur. Food Res. Technol. 2003, 217, 128-133.
22. 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.
23. 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.
24. Schatz, P. F.; Ralph, J.; Lu, F.; Guzei, I. A.; Bunzel, M. Synthesis and identification of 2,5-bis(4-hydroxy-3-methoxyphenyl)-tetrahydrofuran-3,4- dicarboxylic acid, an unanticipated ferulate 8-8-coupling product acylating cereal plant cell walls. Org. Biomol. Chem. 2006, 4, 2801-2806.
25. Waldron, K. W.; Parr, A. J.; Ng, A.; Ralph, J. Cell wall esterified phenolic dimers: Identification and quantification by reverse phase high performance liquid chromatography and diode array detection. Phytochem. Anal. 1996, 7, 305-312.
26. Hatfield, R. D.; Ralph, J. Modelling the feasibilty of intramolecular dehydrodiferulate formation in grass walls. J. Sci. Food Agric. 1999, 79, 425-427.
27. Dervilly-Pinel, G.; Thibault, J. F.; Saulnier, L. Experimental evidence for a semi-flexible conformation for arabinoxylans. Carbohydr. Res. 2001, 330, 365-372.
28. Kerr, E. M.; Fry, S. C. Pre-formed xyloglucans and xylans increase in molecular weight in three distinct compartments of a maize cell-suspension culture. Planta 2003, 217, 327-339.
29. Obel, N.; Porchia, A. C.; Scheller, H. V. Intracellular feruloylation of arabinoxylan in wheat: Evidence for feruloyl-glucose as precursor. Planta 2003, 216, 620-629.
30. Ralph, J.; Lundquist, K.; Brunow, G.; Lu, F.; Kim, H.; Schatz, P. F.; Marita, J. M.; Hatfield, R. D.; Ralph, S. A.; Christensen, J. H.; Boerjan, W. Lignins: Natural polymers from oxidative coupling of 4-hydroxyphenylpropanoids. Phytochem. Rev. 2004, 3, 29-60.