Control of diferulate formation in dicotyledonous and gramineous cell-suspension cultures

Planta

Volumn 227, Issue 2, 2008, Pages 439-452

  Lindsay, Shona E ^a,b   Fry, Stephen C ^a  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

^b UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

Cell wall; Cross links; Dehydrodiferulate; Ferulate; Spinacia; Zea

Indexed keywords

CARBON; CINNAMIC ACID; CINNAMIC ACID DERIVATIVE; COUMARIC ACID; DIFERULIC ACID; PHENOL DERIVATIVE; POLYSACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; CULTURE MEDIUM; CULTURE TECHNIQUE; CYTOLOGY; METABOLISM; METHODOLOGY; PLANT; TIME;

CARBON RADIOISOTOPES; CELL CULTURE TECHNIQUES; CINNAMATES; COUMARIC ACIDS; CULTURE MEDIA; PHENOLS; PLANTS; POLYSACCHARIDES; TIME FACTORS;

ACER; ARABIDOPSIS; HORDEUM; LYCOPERSICON ESCULENTUM; SPINACIA; SPINACIA OLERACEA; ZEA; ZEA MAYS;

EID: 40949119425     PISSN: 00320935     EISSN: 14322048     Source Type: Journal    
DOI: 10.1007/s00425-007-0630-z     Document Type: Article

References (46)

1. Assabgui RA, Reid LM, Hamilton RI, Arnason JT (1993) Correlation of kernel (E)-ferulic acid content of maize with resistance to Fusarium graminearium. Phytopathology 83:949-952
2. Baydoun EA-H, Pavlencheva N, Cummings CM, Waldron KW, Brett CT (2004) Control of dehydrodiferulate cross-linking in pectins from sugar-beet tissues. Phytochemistry 65:1107-1115
3. Bunzel M, Ralph J, Brüning P, Steinhart H (2006) Structural identification of dehydrotriferulic and dehydrotetraferulic acids isolated from insoluble maize bran fibre. J Agric Food Chem 54:6409-6418
4. Bunzel M, Ralph J, Funk C, Steinhart H (2003) Isolation and identification of a ferulic acid dehydrotrimer from saponified maize bran insoluble fibre. Eur Food Res Technol 217:128-133
5. Dawson RMC, Elliott DC, Elliott WH, Jones KM (1986) Data for biochemical research, 3rd edn. Clarendon, Oxford
6. r apoplastic inhibitor. Planta 223:77-89
7. Fry SC (1979) Phenolic components of the primary cell wall and their possible rôle in the hormonal regulation of growth. Planta 146:343-351
8. Fry SC (1982) Phenolic components of the primary cell wall: feruloylated disaccharides of d-galactose and l-arabinose from spinach polysaccharide. Biochem J 203:493-504
9. Fry SC (1983) Feruloylated pectins from the primary cell wall: their structure and possible functions. Planta 157:111-123
10. 14C-labelled cinnamate into hydrolase-resistant components of the primary cell wall of spinach. Phytochemistry 23:59-64
11. Fry SC (1987) Intracellular feruloylation of pectic polysaccharides. Planta 171:205-211
12. Fry SC (2000) The growing plant cell wall: chemical and metabolic analysis. Reprint edn. Blackburn Press, Caldwell, NJ
13. Fry SC (2004) Oxidative coupling of tyrosine and ferulic acid residues: intra- and extra-protoplasmic occurrence, predominance of trimers and larger products, and possible role in inter-polymeric cross-linking. Phytochem Rev 3:97-111
14. Fry SC, Willis SC, Paterson EJ (2000) Intraprotoplasmic and wall-localised formation of arabinoxylan-bound diferulates and larger ferulate coupling-products and maize cell-suspension cultures. Planta 211:679-692
15. Funk C, Ralph J, Steinhart H, Bunzel M (2005) Isolation and structural characterisation of 8-O-4/8-O-4-and 8-8/8-O-4-coupled dehydrotriferulic acids from maize bran. Phytochemistry 66:363-371
16. Geissmann T, Neukom H (1971) Vernetzung von Phenolcarbonsäureestern von Polysacchariden durch oxydative phenolische Kupplung. Helv Chim Acta 54:1108-1112
17. Harborne JB, Corner JJ (1961) Plant polyphenols. 4. Hydroxycinnamic acid-sugar derivatives. Biochem J 81:242-250
18. Harris PJ, Hartley RD (1976) Detection of bound ferulic acid in cell-walls of Gramineae by ultraviolet fluorescence microscopy. Nature 259:508-510
19. Harris PJ, Hartley RD (1980) Phenolic constituents of the cell-walls of monocotyledons. Biochem Syst Ecol 8:153-160
20. Hartley RD (1973) Carbohydrate esters of ferulic acid as components of cell-walls of Lolium multiflorum. Phytochemistry 12:661-665
21. Hartley RD, Harris PJ (1981) Phenolic constituents of the cell-walls of dicotyledons. Biochem Syst Ecol 9:189-203
22. Hartley RD, Jones EC (1976) Diferulic acid as a component of cell walls of Lolium multiflorum. Phytochemistry 15:1157-1160
23. Higuchi T, Ito Y, Kawamura I (1967) p-Hydroxyphenylpropane component of grass lignin and role of tyrosine-ammonia lyase in its formation. Phytochemistry 6:875-881
24. Hu W-J, Harding SA, Lung J, Popko JL, Ralph J, Stokke DD, Tsai C-J, Chiang VL (1999) Repression of lignin biosynthesis promotes cellulose accumulation and growth in transgenic trees. Nat Biotechnol 17:808-812
25. Ishii T (1991) Isolation and characterisation of diferuloyl arabinoxylan hexasaccharide from bamboo shoot cell-walls. Carbohydr Res 219:15-22
26. Ishii T (1997) Structure and function of feruloylated polysaccharides. Plant Sci 127:111-127
27. Kato Y, Nevins DJ (1985) Isolation and identification of O-(5-O-feruloyl-α-L-arabinofuranosyl)-(1→3)-O-β-D-xylopyranosyl- (1→4)-D-xylopyranose as a component of Zea shoot cell-walls. Carbohydr Res 137:139-150
28. Kohler A, Kauss H (1997) Transfer of hydroxycinnamoyl residues to microsomal protein from parsley. Phytochemistry 44:225-228
29. Kolattukudy PE (1981) Structure, biosynthesis, and biodegradation of cutin and suberin. Annu Rev Plant Physiol Plant Mol Biol 32:539-567
30. Koukol J, Conn EE (1961) Metabolism of aromatic compounds in higher plants. 4. Purification and properties of phenylalanine deaminase of Hordeum vulgare. J Biol Chem 236:2692-2698
31. Levigne SV, Ralet MCJ, Quéméner BC, Pollet BNL, Lapierre C, Thibault JFJ (2004) Isolation from sugar beet cell walls of Arabinan oligosaccharides esterified by two ferulic acid monomers. Plant Physiol 134:1173-1180
32. Markwalder HU, Neukom H (1976) Diferulic acid as a possible crosslink in hemicelluloses from wheat germ. Phytochemistry 15:836-37
33. Myton KE, Fry SC (1994) Intraprotoplasmic feruloylation of arabinoxylans in Festuca arundinacea cell cultures. Planta 193:326-330
34. Neish AC (1961) Formation of meta-coumaric and para-coumaric acids by enzymatic deamination of the corresponding isomers of tyrosine. Phytochemistry 1:1-24
35. Obel N, Porchia AC, Scheller HV (2003) Intracellular feruloylation of arabinoxylan in wheat: evidence for feruloyl-glucose as precursor. Planta 216:620-629
36. Popper ZA, Fry SC (2005) Widespread occurrence of a covalent linkage between xyloglucan and acidic polysaccharides in suspension-cultures angiosperm cells. Ann Bot 96:91-99
37. Ralet MC, André-Leroux G, Quéméner B, Thibault JF (2005) Sugar beet (Beta vulgaris) pectins are covalently cross-linked through diferulic bridges in the cell wall. Phytochemistry 66:2800-2814
38. Ralph J, Quideau S, Grabber JH, Hatfield RD (1994) Identification and synthesis of new ferulic acid dehydrodimers present in grass cell walls. J Chem Soc Perkin Trans 1:3485-3498
39. Rouau X, Cheynier V, Surget A, Gloux D, Barron C, Meudec E, Louis-Montero J, Criton M (2003) A dehydrotetrimer of ferulic acid from maize bran. Phytochemistry 63:899-903
40. Saulnier L, Vigouroux J, Thibault J-F (1995) Isolation and partial characterisation of feruloylated oligosaccharides from maize bran. Carbohydr Res 272:241-253
41. Smith MM, Hartley RD (1983) Occurrence and nature of ferulic acid substitution of cell-wall polysaccharides in graminaceous plants. Carbohydr Res 118:65-80
42. Waldron KW, Parr AJ, Ng A, Ralph J (1996) Cell wall esterified phenolic dimers: Identification and quantification by reverse phase high performance liquid chromatography and diode array detection. Phytochem Anal 7:305-312
43. Wende G, Fry SC (1997) 2-O-β-D-Xylanopyranosyl-(5-O-feruloyl)-L- arabinose, a widespread component of grass cell walls. Phytochemistry 44:1019-1030
44. Wende G, Waldron KW, Smith AC, Brett CT (2000) Tissue-specific developmental changes in cell-wall ferulate and dehydrodiferulates in sugar beet. Phytochemistry 55:103-110
45. Whitmore FW (1974) Phenolic acids in wheat coleoptile cell walls. Plant Physiol 53:728-731
46. Yoshida-Shimokawa T, Yoshida S, Kakegawa K, Ishii T (2001) Enzymic feruloylation of arabinoxylan-trisaccharide by feruloyl-CoA : arabinoxylan-trisaccharide O-hydroxycinnamoyl transferase from Oryza sativa. Planta 212:470-474