Structural investigations on arabinogalactan-protein from wheat, isolated with yariv reagent

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 6, 2010, Pages 3621-3626

  Göllner, Esther M ^a   Wolfgang, Blaschek ^a   Birgit, Classen ^a  

^a UNIVERSITY OF KIEL   (Germany)

Author keywords

Arabinogalactan protein; Poaceae; Structural analysis; Triticum aestlvum; Wheat; Whole grain; Yariv

Indexed keywords

ARABINOGALACTAN PROTEINS; DRUG DERIVATIVE; GLUCOSIDE; MUCOPROTEIN; PHLOROGLUCINOL; PLANT EXTRACT; VEGETABLE PROTEIN; YARIV REAGENT;

ARTICLE; CHEMISTRY; ISOLATION AND PURIFICATION; MOLECULAR WEIGHT; PROTEIN CONFORMATION; WHEAT;

GLUCOSIDES; MOLECULAR WEIGHT; MUCOPROTEINS; PHLOROGLUCINOL; PLANT EXTRACTS; PLANT PROTEINS; PROTEIN CONFORMATION; TRITICUM;

POACEAE; TRITICUM; TRITICUM AESTIVUM;

EID: 77949863874     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf903843f     Document Type: Article

References (58)

1. Seifert, G. J.; Roberts, K. The biology of arabinogalactan proteins. Annu. Rev. Plant. Biol. 2007, 58, 137-161.
2. Showalter, A. M. Arabinogalactan-proteins: structure, expression and function. Cell. Mol. life Sci. 2001, 58 (10), 1399-1417.
3. Gaspar, Y.; Johnson, K. L.; McKenna, J. A.; Bacic, A.; Schultz, C. J. The complex structures of arabinogalactan-proteins and the journey towards understanding function. Plant MoI. Biol. 2001, 47, 161-176.
4. Bacic, A.; Currie, G.; Gilson, P.; Mau, S. L.; Oxley, D.; Schultz, C.; Sommer-Knudsen, J.; Clarke, A. E. Structural classes of arabinogalactan- proteins. In Cell and Developmental Biology of Arabinogalactan-Proteins; Nothnagel, E. A., Bacic, A., Clarke, A. E., Eds.; Kluwer Academic/Plenum Publishers: New York, 2000; pp 11-23.
5. Majewska-Sawka, A.; Nothnagel, E. A. The multiple roles of arabinogalactan proteins in plant development. Plant Phvsiol. 2000, 122, 3-9.
6. Gao, M.; Showalter, A. M. Yariv reagent treatment induces programmed cell death in Arabidopsis cell cultures and implicates arabinogalactan protein involvement. Plant J. 1999 , 19, 321-331.
7. Schultz, C.; Gilson, P.; Oxley, D.; Youl, J.; Bacic, A. GPI-anchors on arabinogalactan-proteins: implications for signalling in plants. Trends Plant Sci. 1998, 3 (11), 426-431.
8. Ding, L.; Zhu, J. K. A role for arabinogalactan-proteins in root epidermal cell expansion. Planta 1997, 203 (3), 289-294.
9. Letarte, J.; Simion, E.; Miner, M.; Kasha, K. J. Arabinogalactans and arabinogalactan-proteins induce embryogenesis in wheat (Triticum aestivum L.) microspore culture. Plant Cell Rev. 2006, 24 (12),691-698.
10. Alban, S.; Classen, B.; Brunner, G.; Blaschek, W. Differentiation between the complement modulating effects of an arabinogalactanprotein from Echinacea purpurea and heparin. Planta Med. 2002, 86, 1118-1124.
11. Thude, S.; Classen, B.; Blaschek, W.; Barz, D.; Thude, D. Binding studies of an arabinogalactan-protein from Echinacea purpurea to leucocytes. Phvtomedicine 2006, 13, 425-427.
12. Classen, B.; Thude, S.; Blaschek, W.; Wack, M.; Bodinet, C. Immunmodulatory effects of arabinogalactan-proteins from Baptisia and Echinacea. Phvtomedicine. 2006, 13, 688-694.
13. Robinson, R. R; Swennen, K.; Feirtag, J.; Slavin, J. L. Effects of dietry arabinogalactan on gastrointestinal and blood parameters in healthy human subjects. J. Am. Coll. Nutr. 2001, 20 (4), 279-285.
14. Yariv, J.; Lis, H.; Katchalski, E. Precipitation of arabic acid and some seed polysaccharides by glycosylphenylazo dyes. Biochem. J. 1967, 105, 1C-2C.
15. Yariv, J.; Rapport, M. M.; Graf, L. The interaction of glycosides and saccharides with, antibody to the corresponding phenylazo glycosides. Biochem. ,J 1962, 85, 383-388.
16. Jermyn, M. A.; Yeow, Y. M.; Woods, E. F. Class of lectins present in the tissues of seed Plants. Aust. J. Plant Phvsiol. 1975, 2(4), 501-531.
17. Fincher, G. B.; Stone, B. A. A water-soluble arabinogalactanpeptide from wheat endosperm. Aust. J, Biol. Sci. 1974, 27 (2), 117-132.
18. Ingelbrecht, J. A.; Loosveld, A. M. A.; Grobet, P. J.; Schols, H.; Bakx, E.; Delcour, J. A. Characterization of the carbohydrate part of arabinogalactan peptides in Triticum durum Desf. semolina. Cereal Chem. 2002, 79 (2), 322-325.
19. Loosveld, A. M. A.; Delcour, J. A. The significance of arabinogalactan-peptide for wheat flour bread-making. J. Cereal Sci. 2000, 32 (2), 147-157.
20. Loosveld, A. M. A.; Maes, C.; Van Casteren, W. H. M.; Schols, H. A.; Grobet, P. J.; Delcour, J. A. Structural variation and levels of water-extractable arabinogalactan-peptide in European wheat flours. Cereal Chem. 1998, 75 (6), 815-819.
21. McNamara, M. K.; Stone, B. A. Isolation, characterization and chemical synthesis of a galactosyl-hydroxyproline linkage compound from wheat endosperm arabinogalactan-peptide. Lehensm. Wiss..Technol. 1981. 14 (4). 182-187.
22. Schroder, M.; Soe, J. B.; Zargahi, M. R.; Rouau, X. Production of substrate for galactose oxidase by depolymerisation of an arabinogalactan- peptide from wheat flour. J., Agric, Food Chem 1999, 47, 1483-1488.
23. Guttieri, M. J.; Souza, E. J.; Sneller, C. Nonstarch polysaccharides in wheat flour wire-cut cookie making. J. Agric. Food Chem 2008, 56, 10927-10932.
24. Kreuger, M.; van Hoist, G. J. Arabinogalactan-protein epitopes in somatic embryogenesis oi'Daucus carota L. Planta 1995, 197, 135141.
25. Gleeson, P. A.; Clarke, A. E. Structural studies on the major component of Gladiolus style mucilage, an arabinogalactan-protein. Biochem. J. 1979, 181, 607-621.
26. Tan, L.; Qiu, F.; Lamport, D. T. A.; Kieliszewski, M. J. Structure of a hydroxyproline (Hyp)-arabinogalactan polysaccharide from repetitive Ala-Hyp expressed in transgenic Nicotiana tabacum. J. Biol. Chem. 2004, 279 (13), 13156-13165.
27. Blakeney, A.B.; Harris, P. J.; Henry, R. J.; Stone, B. A. A simple and rapid preparation of alditol acetates for monosaccharide analysis. Carbohvdr. Res. 1983. 113. 291-299.
28. Inngjerdingen, K. T.; Debes, S. C.; Inngjerdingen, M.; Hokputsa, S.; Harding, S. E.; Rolstad, B.; Michaelsen, T. E.; Diallo, D.; Paulsen, B. S. Bioactive pectic polysaccharides from Glinus oppositifolius (L.) Aug. DC., a Malian medicinal plant, isolation and partial characterization. J. Ethnopharmaeol. 2005, 101, 204-214.
29. Harris, P. J.; Henry, R. J.; Blakeney, A. B.; Stone, B. A. An improved procedure for the methylation analysis of oligosaccharides and polysaccharides. Carbohvdr. Res. 1984, 127, 59-73.
30. Stegemann, H.; Stalder, K. H. Determination of hydroxyproline. Clin., Chim, Acta 1967 ,18, 267-273.
31. Ordaz-Ortiz, J. J.; Saulnier, L. Structural variability of arabinoxylans from wheat flour. Comparison of water-extractable and xylanase-extractable arabinoxylans. J. Cereal Sci. 2005, 42, 119125.
32. Wood, P. J.; Beer, M. U. Functional oat products. In Functional Food: Biochemical and Processing Aspects 1; Mazza, G., Ed.; Techonomic Puplishing: Lancaster, PA, 1998; pp 1-37.
33. Nothnagel, E. A. Proteoglycans and related components in plant cells. Int. Rev. Cvtl. 1997, 174, 195-291.
34. Nunes, F. M.; Reis, A.; Silva, A. M. S.; Domingues, M. R. M.; Coimbra, A. M. Rhamnoarabinosyl and rhamnoarabinoarabinosyl side chains as structural features of coffee arabinogalactans. Phv- tochemistry 2008, 69, 1573-1585.
35. Putoczki, T. L.; Pettolino, F.; Griffin, M. D. W.; Moeller, R.; Gerrard, J. A.; Bacic, A.; Jackson, S. L. Characterization of the structure, expression and function of Pinus radiata D. Don arabinogalactan-proteins. Planta 2007, 226, 1131-1142.
36. Neukom, H.; Markwalder, H. Isolation and characterization of an arabinogalactan from wheat flour. Carbohvdr. Res. n 1975, 39, 387389.
37. Herbst, B.; Classen, B.; Blaschek, W. Characterisation of arabinogalactan-proteins from Viscum album L. berries and herb. In Misteltoe in Therapy of Tumor 2; Scheer, R., Aiban, S., Becker, H., Holzgrabe, U., Kemper, F. H., Kreis, W., Matthes, H., Schilcher, H., Eds.; KVC Publisher: Essen, Germany, 2009; pp 121-132.
38. Van den Bulck, K.; Swennen, K.; Loosveld, A. M. A.; Courtin, C. M.; Brijs, K.; Proost, P.; Van Damme, J.; Van Campenhout, S.; Mort, A.; Delcour, J. A. Isolation of cereal arabinogalactan-peptides and structural comparison of their carbohydrate and peptide moieties J. Cereal Sci. 2005, 41, 59-67.
39. Izydorczyk, M.; Biliaderis, G G.; Bushuk, W. Comparison of the structure and composition of water-soluble pentosans from different wheat varieties. Cereal Chem. 1991, 68 (2), 139-144.
40. Aspinall, G. O. Chemical characterization and structure determination of polysaccharides. In The Polysaccharides 1; Aspinall, G. 0., Ed.; Academic Press: NewYork, 1982; pp 35-131.
41. Willats, W.; McCartney, L.; Mackie, W.; Knox, J. P. Pectin: cell biology and prospects for functional analysis. Plant. Mol. Biol. 2001, 47, 9-27.
42. Thude, S.; Classen, B. High molecular weight constituents from, roots of Echinacea pallida: an arabinogalactan-protein and an arabinan. Phvtochemistrv 2005, 66 (9), 1026-1032.
43. Classen, B.; Witthohn, K.; Blaschek, W. Characterization of an arabinogalactan-protein isolated from pressed juice of Echinacea purpurea by precipitation with the Β-glucosyl Yariv reagent. Carbohvdr. Res. 2000, 327, 497-504.
44. Mollard, M.; Basile, D. Acacia Senegal cells cultured in suspension secrete a hydroxyproline-deficient arabinogalactan protein. Plant Physiol. Biochem. 2000, 32, 703-709.
45. Wack, M.; Classen, B.; Blaschek, W. An acidic arabinogalactanprotein from the roots of Baptisia tinctoria. Planta Med- 2005, 71, 814-818.
46. Kieliszewski, M. J.; Kamyab, A.; Leykam, J. F.; Lamport, D. T. A. A histidine-rich extensin from Zea mays is an arabinogalactan protein. Plant Phvsiol 1992, 99 (2), 538-547.
47. Wack, M. Isolation and characterization of arabinogalactan-proteins from Baptisia tinctoria and Baptisia australis. Dissertation, Christian-Albrechts- University of Kiel, Germany, 2004.
48. 13C-NMR spectroscopy to identify complex polysaccharide fractions from the plant cell wall. Phvsiol. Veg. 1984, 22 (4), 461-470.
49. Samuelsen, A.; Paulsen, B. S.; Wold, J. K.; Knutsen, S. H.; Yamada, H. Characteruzation of a biologically active arabinogalactan from the leaves of Plantago major L. Carbohvdr. Polvm. 1998, 35, 145-153.
50. Gane, A. M.; Craik, D.; Munro, S. L. A.; Howlett, G. J.; Clarke, A. E.; Bacic, A. Structural analysis of the carbohydrate moiety of arabinogalactan- proteins from stigmas and styles of Nicotiana alata. Carbohvdr. Res. 1995, 277, 67-85.
51. Strahm, A.; Amado, R.; Neukom, H. Hydroxyproline-galactoside as a protein-polysaccharide linkage in a water soluble arabinogalactan-peptide from wheat endosperm. Phvtochemistry 1981, 20 (5), 1061-1063.
52. Loosveld, A. M. A.; Grobet, P. J.; Delcour, J. A. Contents and structural features of water-extractable arabinogalactan in wheat flour fractions. J. Agric. Food. Chem. 1997, 45, 1998-2002.
53. Van den Bulck, K.; Loosveld, A. M. A.; Courtin, G M.; Proost, P.; Van Damme, J.; Robben, J.; Mort, A.; Delcour, J. A. Amino acid sequence of wheat flour arabinogalactan-peptide, identical to part of grain softness protein GSP-I, leads to improved structural model. Cereal Chem. 2002, 79 (3), 329-331.
54. Anderson, R. L.; Clarke, A. E.; Jermyn, M. A.; Knox, R. B.; Stone, B. A. A carbohydrate-binding arabinogalactan-protein from, liquid cultures of endosperm from Lolium multiflorum. Aust. J. Plant Phvsiol. 1977, 4, 143-158.
55. Bacic, A.; Currie, G.; Gilson, P.; Mau, S. L.; Oxley, D.; Schultz, C.; Sommer-Knudsen, J.; Clarke, A. E. Structural classes of arabinogalactan- proteins. In Cell and Developmental Biology of Arabinogalactan-Proteins; Nothnagel, E. A., Bacic, A, Clarke, A. E., Eds.; Kluwer Academic/Plenum Publishers: New York, 2000; pp 11-23.
56. Fincher, G. B.; Stone, B. A.; Clarke, A. E. Arabinogalactanproteins: structure, biosynthesis, and function, Poaceae. Annu. Rev, Plant Phvsiol. 1983, 34, 47-70.
57. Qi, W.; Fong, C.; Lamport, D. T. A. Gum arabic glycoprotein is a twisted hairy rope: a new model based on O-galactosylhydroxyproline as the polysaccharide attachment site. Plant Phvsiol. 1991, 96 (3), 848-855.
58. Tsumuraya, Y.; Hasimoto, Y.; Yamamoto, S.; Shibuya, N. Structure of L-arabino-D-galactan-containing glycoproteins from, radish leaves. Carbohydr. Res. 1984, 134 (2), 215-228.