The phenolic profile of maize primary cell wall changes in cellulose-deficient cell cultures

Phytochemistry

Volumn 71, Issue 14-15, 2010, Pages 1684-1689

  Mélida, Hugo ^a   García Angulo, Penélope ^a   Alonso Simón, Ana ^a   Álvarez, Jesús M ^a   Acebes, José Luis ^a   Encina, Antonio ^a  

^a UNIVERSITY OF LEÓN   (Spain)

Author keywords

Cell wall; DCB; Dichlobenil; Ferulic acid; HPLC; Hydroxycinnamate; Maize; p Coumaric acid; Zea mays

Indexed keywords

CELLULOSE; DICHLOBANIL; NITRILE; PHENOL DERIVATIVE;

ARTICLE; CELL WALL; CHEMICAL STRUCTURE; CHEMISTRY; CULTURE TECHNIQUE; DRUG EFFECT; MAIZE; METABOLISM;

CELL CULTURE TECHNIQUES; CELL WALL; CELLULOSE; MOLECULAR STRUCTURE; NITRILES; PHENOLS; ZEA MAYS;

ZEA MAYS;

EID: 77956340809     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2010.06.013     Document Type: Article

References (40)

1. A. Alonso-Simón, A.E. Encina, P. García-Angulo, J.M. Álvarez, and J.L. Acebes FTIR spectroscopy monitoring of cell wall modifications during the habituation of bean (Phaseolus vulgaris L.) callus cultures to dichlobenil Plant Sci. 167 2004 1273 1281
2. T. Azuma, N. Okita, T. Nanmori, and T. Yasuda Relationship between the deposition of phenolic acids in the cell walls and the cessation of rapid growth in internodes of floating rice Plant Prod. Sci. 8 2005 447 453
3. M.M.D.O. Buanafina Feruloylation in grasses: current and future perspectives Mol. Plant 2 2009 861 872
4. M. Bunzel, J. Ralph, J. Marita, and H. Steinhart Identification of 4-O-5'-coupled diferulic acid from insoluble cereal fiber J. Agric. Food Chem. 48 2000 3166 3169
5. M. Bunzel, J. Ralph, C. Funk, and H. Steinhart Isolation and identification of a ferulic acid dehydrotrimer from saponified maize bran insoluble fiber Eur. Food Res. Technol. 217 2003 128 133
6. M. Bunzel, J. Ralph, C. Funk, and H. Steinhart Structural elucidation of new ferulic acid-containing phenolic dimers and trimers isolated from maize bran Tetrahedron Lett. 46 2005 5845 5850
7. M. Bunzel, J. Ralph, P. Bruening, and H. Steinhart Structural identification of dehydrotriferulic and dehydrotetraferulic acids isolated from insoluble maize bran fiber J. Agric. Food Chem. 54 2006 6409 6418
8. S.J. Burr, and S.C. Fry Extracellular cross-linking of maize arabinoxylans by oxidation of feruloyl esters to form oligoferuloyl esters and ether-like bonds Plant J. 58 2009 554 567
9. N.C. Carpita Cell wall development in maize coleoptiles Plant Physiol. 76 1984 205 212
10. D.P. Delmer Cellulose biosynthesis Annu. Rev. Plant Physiol. Plant Mol. Biol. 38 1987 259 290
11. S.C. Fry Feruloylated pectins from the primary-cell wall - their structure and possible functions Planta 157 1983 111 123
12. S.C. Fry Primary cell wall metabolism: tracking the careers of wall polymers in living plant cells New Phytol. 161 2004 641 675
13. S.C. Fry, S.C. Willis, and A.E.J. Paterson Intraprotoplasmic and wall-localised formation of arabinoxylan-bound diferulates and larger ferulate coupling-products in maize cell-suspension cultures Planta 211 2000 679 692
14. C. Funk, J. Ralph, H. Steinhart, and M. Bunzel Isolation and structural characterisation of 8-O-4/8-O-4- and 8-8/8-O-4-coupled dehydrotriferulic acids from maize bran Phytochemistry 66 2005 363 371
15. T. Geissman, and H. Neukom Cross-linking of phenolcarboxylates of polysaccharides by oxidative phenolic coupling Helv. Chim. Acta 54 1971 1108 1112
16. J.H. Grabber, R.D. Hatfield, J. Ralph, J. Zon, and N. Amrhein Ferulate cross-linking in cell-walls isolated from maize cell-suspensions Phytochemistry 40 1995 1077 1082
17. J.H. Grabber, R.D. Hatfield, and J. Ralph Diferulate cross-links impede the enzymatic degradation of non-lignified maize walls J. Sci. Food Agric. 77 1998 193 200
18. T. Higuchi, Y. Ito, M. Shimada, and I. Kawamura Chemical properties of milled wood lignin of grasses Phytochemistry 6 1967 1551 1556
19. T. Ishii Structure and functions of feruloylated polysaccharides Plant Sci. 127 1997 111 127
20. T. Ishii, and T. Hiroi Linkage of phenolic-acids to cell-wall polysaccharides of bamboo shoot Carbohydr. Res. 206 1990 297 310
21. S. Kamisaka, S. Takeda, K. Takahashi, and K. Shibata Diferulic and ferulic acid in the cell-wall of Avena coleoptiles - their relationships to mechanical-properties of the cell-wall Physiol. Plant. 78 1990 1 7
22. Y. Kato, and D.J. Nevins Isolation and identification of O-(5-O-feruloyl-alpha-l-arabinofuranosyl)-(1-3)-O-beta-d-xylopyranosyl-(1-4) -d-xylopyranose as a component of Zea shoot cell-walls Carbohydr. Res. 137 1985 139 150
23. E.M. Kerr, and S.C. Fry Extracellular cross-linking of xylan and xyloglucan in maize cell-suspension cultures: the role of oxidative phenolic coupling Planta 219 2004 73 83
24. S.E. Lindsay, and S.C. Fry Control of diferulate formation in dicotyledonous and gramineous cell-suspension cultures Planta 227 2008 439 452
25. E.P. Lorences, and S.C. Fry Absolute measurement of cell expansion in plant cell suspension cultures Plant Cell Tiss. Organ Cult. 24 1991 211 215
26. V.V. Lozovaya, T.A. Gorshkova, N.I. Rumyantseva, A.V. Ulanov, A.I. Valieva, E.V. Yablokova, C.S. Mei, and J.M. Widholm Cell wall-bound phenolics in cells of maize (Zea mays, Gramineae) and buckwheat (Fagopyrum tataricum, Polygonaceae) with different plant regeneration abilities Plant Sci. 152 2000 79 85
27. J.W. MacAdam, and J.H. Grabber Relationship of growth cessation with the formation of diferulate cross-links and p-coumaroylated lignins in tall fescue leaf blades Planta 215 2002 785 793
28. L.I. Mastrangelo, M.S. Lenucci, G. Piro, and G. Dalessandro Evidence for intra- and extra-protoplasmic feruloylation and cross-linking in wheat seedling roots Planta 229 2009 343 355
29. H. Mélida, P. García-Angulo, A. Alonso-Simón, A. Encina, J. Álvarez, and J.L. Acebes Novel type II cell wall architecture in dichlobenil-habituated maize calluses Planta 229 2009 617 631
30. T. Murashige, and F. Skoog A revised medium for rapid growth and bio assays with tobacco tissue cultures Physiol. Plant. 15 1962 473 497
31. N. Obel, A.C. Porchia, and H.V. Scheller Intracellular feruloylation of arabinoxylan in wheat: evidence for feruloyl-glucose as precursor Planta 216 2003 620 629
32. M.L. Parker, A. Ng, and K.W. Waldron The phenolic acid and polysaccharide composition of cell walls of bran layers of mature wheat (Triticum aestivum L. cv. Avalon) grains J. Sci. Food Agric. 85 2005 2539 2547
33. J. Ralph, S. Quideau, J.H. Grabber, and R.D. Hatfield Identification and synthesis of new ferulic acid dehydrodimers present in grass cell-walls J. Chem. Soc. - Perkin Trans. 1 1994 3485 3498
34. X. Rouau, V. Cheynier, A. Surget, D. Gloux, C. Barron, E. Meudec, J. Louis-Montero, and M. Criton A dehydrotrimer of ferulic acid from maize bran Phytochemistry 63 2003 899 903
35. L. Saulnier, M.J. Crepeau, M. Lahaye, J.F. Thibault, M.T. Garcia-Conesa, P.A. Kroon, and G. Williamson Isolation and structural determination of two 5,5′-diferuloyl oligosaccharides indicate that maize heteroxylans are covalently cross-linked by oxidatively coupled ferulates Carbohydr. Res. 320 1999 82 92
36. E. Shedletzky, M. Shmuel, T. Trainin, S. Kalman, and D. Delmer Cell wall structure in cells adapted to growth on the cellulose synthesis inhibitor 2,6-dichlorobenzonitrile. A comparison between 2 dicotyledonous plants and a gramineous monocot Plant Physiol. 100 1992 120 130
37. M.M. Smith, and R.D. Hartley Occurrence and nature of ferulic acid substitution of cell-wall polysaccharides in graminaceous plants Carbohydr. Res. 118 1983 65 80
38. K.C. Vaughn Cellulose biosynthesis inhibitor herbicides P. Böger, K. Wakabayashi, K. Hirai, Herbicide Classes in Development 2002 Springer-Verlag Berlin 139 150
39. K.W. Waldron, A.J. Parr, A. Ng, and J. Ralph Cell wall esterified phenolic dimers: identification and quantification by reverse phase high performance liquid chromatography and diode array detection Phytochem. Anal. 7 1996 305 312
40. G. Wende, and S.C. Fry O-feruloylated, O-acetylated oligosaccharides as side-chains of grass xylans Phytochemistry 44 1997 1011 1018