Characterization of recombinant nitrile-specifier proteins (NSPs) of Arabidopsis thaliana: Dependency on Fe(II) ions and the effect of glucosinolate substrate and reaction conditions

Phytochemistry

Volumn 84, Issue , 2012, Pages 7-17

  Kong, Xiang Yi ^a,b   Kissen, Ralph ^a   Bones, Atle M ^a  

^a NORWEGIAN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Norway)

^b UNIVERSITY OF OSLO   (Norway)

Author keywords

Arabidopsis thaliana; Epithiospecifier protein; Fe(II) ion; Glucosinolates; Isothiocyanates; Myrosinase; Nitrile specifier proteins; Nitriles

Indexed keywords

ARABIDOPSIS PROTEIN; FERROUS ION; GLUCOSINOLATE; GLYCOSIDASE; ION; NITRILE; RECOMBINANT PROTEIN; THIOGLUCOSIDASE;

ARABIDOPSIS; ARTICLE; BIOCATALYSIS; CHEMISTRY; CONFORMATION; GENETICS; HYDROLYSIS; METABOLISM; PH;

ARABIDOPSIS; ARABIDOPSIS PROTEINS; BIOCATALYSIS; FERROUS COMPOUNDS; GLUCOSINOLATES; GLYCOSIDE HYDROLASES; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; IONS; MOLECULAR CONFORMATION; NITRILES; RECOMBINANT PROTEINS;

ARABIDOPSIS; ARABIDOPSIS THALIANA; ESCHERICHIA COLI;

EID: 84868095082     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2012.08.004     Document Type: Article

References (39)

1. N. Agerbirk, and C.E. Olsen Glucosinolate structures in evolution Phytochemistry 77 2012 16 45
2. N. Agerbirk, C.E. Olsen, and H. Sorensen Initial and final products, nitriles, and ascorbigens produced in myrosinase-catalyzed hydrolysis of indole glucosinolates J. Agric. Food Chem. 46 1998 1563 1571
3. I. Ahuja, J. Rohloff, and A.M. Bones Defence mechanisms of Brassicaceae: Implications for plant-insect interactions and potential for integrated pest management A Rev. Agron. Sustainable Dev. 30 2010 311 348
4. R. Bernardi, A. Negri, S. Ronchi, and S. Palmieri Isolation of the epithiospecifier protein from oil-rape (Brassica napus ssp oleifera) seed and its characterization FEBS Lett. 467 2000 296 298
5. M. Björkman, I. Klingen, A.N. Birch, A.M. Bones, T.J. Bruce, T.J. Johansen, R. Meadow, J. Molmann, R. Seljasen, L.E. Smart, and D. Stewart Phytochemicals of Brassicaceae in plant protection and human health-influences of climate, environment and agronomic practice Phytochemistry 72 2011 538 556
6. R. Björkman, and B. Lönnerdal Studies on myrosinases III. Enzymatic properties of myrosinases from Sinapis alba and Brassica napus seeds Biochim. Biophys. Acta 327 1973 121 131
7. A.M. Bones, and J.T. Rossiter The myrosinase-glucosinolate system, its organisation and biochemistry Physiol. Plant. 97 1996 194 208
8. A.M. Bones, and J.T. Rossiter The enzymic and chemically induced decomposition of glucosinolates Phytochemistry 67 2006 1053 1067
9. B.H. Borgen, O.P. Thangstad, I. Ahuja, J.T. Rossiter, and A.M. Bones Removing the mustard oil bomb from seeds: Transgenic ablation of myrosin cells in oilseed rape (Brassica napus) produces MINELESS seeds J. Exp. Bot. 61 2010 1683 1697
10. P.D. Brown, J.G. Tokuhisa, M. Reichelt, and J. Gershenzon Variation of glucosinolate accumulation among different organs and developmental stages of Arabidopsis thaliana Phytochemistry 62 2003 471 481
11. L. Buchwaldt, L.M. Larsen, A. Plöger, and H. Sorensen Fast polymer liquid chromatography isolation and characterization of plant myrosinase, beta-thioglucoside glucohydrolase, isoenzymes J. Chromatogr. 363 1986 57 69
12. M. Burow, A. Bergner, J. Gershenzon, and U. Wittstock Glucosinolate hydrolysis in Lepidium sativum- identification of the thiocyanate-forming protein Plant Mol. Biol. 63 2007 49 61
13. M. Burow, A. Losansky, R. Muller, A. Plock, D.J. Kliebenstein, and U. Wittstock The genetic basis of constitutive and herbivore-induced ESP-independent nitrile formation in Arabidopsis Plant Physiol. 149 2009 561 574
14. M. Burow, J. Markert, J. Gershenzon, and U. Wittstock Comparative biochemical characterization of nitrile-forming proteins from plants and insects that alter myrosinase-catalysed hydrolysis of glucosinolates FEBS J. 273 2006 2432 2446
15. M. Burow, Z.Y. Zhang, J.A. Ober, V.M. Lambrix, U. Wittstock, J. Gershenzon, and D.J. Kliebenstein ESP and ESM1 mediate indol-3-acetonitrile production from indol-3-ylmethyl glucosinolate in Arabidopsis Phytochemistry 69 2008 663 671
16. J.W. Fahey, A.T. Zalcmann, and P. Talalay The chemical diversity and distribution of glucosinolates and isothiocyanates among plants Phytochemistry 56 2001 5 51
17. H.L. Foo, L.M. Gronning, L. Goodenough, A.M. Bones, B.E. Danielsen, D.A. Whiting, and J.T. Rossiter Purification and characterisation of epithiospecifier protein from Brassica napus: Enzymic intramolecular sulphur addition within alkenyl thiohydroximates derived from alkenyl glucosinolate hydrolysis FEBS Lett. 468 2000 243 246
18. R. Gmelin, and A.I. Virtanen A new type of enzymatic cleavage of mustard oil glucosides. Formation of allylthiocyanate in Thlaspi arvense L. and benzylthiocyanate in Lepidium rurale L. and Lepidium sativum L Acta Chem. Scand. 13 1959 1474 1475
19. R.J. Hopkins, N.M. van Dam, and J.J.A. van Loon Role of glucosinolates in insect-plant relationships and multitrophic interactions Annu. Rev. Entomol. 54 2009 57 83
20. R.B. Kapust, J. Tozser, J.D. Fox, D.E. Anderson, S. Cherry, T.D. Copeland, and D.S. Waugh Tobacco etch virus protease: Mechanism of autolysis and rational design of stable mutants with wild-type catalytic proficiency Protein Eng. 14 2001 993 1000
21. M.O. Kelleher, M. McMahon, I.M. Eggleston, M.J. Dixon, K. Taguchi, M. Yamamoto, and J.D. Hayes 1-Cyano-2,3-epithiopropane is a novel plant-derived chemopreventive agent which induces cytoprotective genes that afford resistance against the genotoxic alpha, beta-unsaturated aldehyde acrolein Carcinogenesis 30 2009 1754 1762
22. R. Kissen, and A.M. Bones Nitrile-specifier proteins involved in glucosinolate hydrolysis in Arabidopsis thaliana J. Biol. Chem. 284 2009 12057 12070
23. R. Kissen, E. Hyldbakk, C.-W.V. Wang, C.G. Sormo, J.T. Rossiter, and A.M. Bones Ecotype dependent expression and alternative splicing of epithiospecifier protein (ESP) in Arabidopsis thaliana Plant Mol. Biol. 78 2012 361 375
24. R. Kissen, J.T. Rossiter, and A.M. Bones The 'mustard oil bomb': Not so easy to assemble?! Localization, expression and distribution of the components of the myrosinase enzyme system Phytochem. Rev. 8 2009 69 86
25. D.J. Kliebenstein, J. Kroymann, P. Brown, A. Figuth, D. Pedersen, J. Gershenzon, and T. Mitchell-Olds Genetic control of natural variation in Arabidopsis glucosinolate accumulation Plant Physiol. 126 2001 811 825
26. J.C. Kuchernig, A. Backenkohler, M. Lubbecke, M. Burow, and U. Wittstock A thiocyanate-forming protein generates multiple products upon allylglucosinolate breakdown in Thlaspi arvense Phytochemistry 72 2011 1699 1709
27. D.O. Lambeth, G.R. Ericson, M.A. Yorek, and P.D. Ray Implications for in vitro studies of the autoxidation of ferrous ion and the iron-catalyzed autoxidation of dithiothreitol Biochim. Biophys. Acta 719 1982 501 508
28. V. Lambrix, M. Reichelt, T. Mitchell-Olds, D.J. Kliebenstein, and J. Gershenzon The Arabidopsis epithiospecifier protein promotes the hydrolysis of glucosinolates to nitriles and influences Trichoplusia ni herbivory Plant Cell 13 2001 2793 2807
29. B. Matthäus, and H.J. Fiebig Simultaneous determination of isothiocyanates, indoles, and oxazolidinethiones in myrosinase digests of rapeseeds and rapeseed meal by HPLC J. Agric. Food Chem. 44 1996 3894 3899
30. N.V. Matusheski, R. Swarup, J.A. Juvik, R. Mithen, M. Bennett, and E.H. Jeffery Epithiospecifier protein from broccoli (Brassica oleracea L. ssp italica) inhibits formation of the anticancer agent sulforaphane J. Agric. Food Chem. 54 2006 2069 2076
31. R. Mithen, R. Bennett, and J. Marquez Glucosinolate biochemical diversity and innovation in the Brassicales Phytochemistry 71 2010 2074 2086
32. S. Palmieri, R. Iori, and O. Leoni Myrosinase from Sinapis alba L. - A new method of purification for glucosinolate analyses J. Agric. Food Chem. 34 1986 138 140
33. B.L. Petersen, S.X. Chen, C.H. Hansen, C.E. Olsen, and B.A. Halkier Composition and content of glucosinolates in developing Arabidopsis thaliana Planta 214 2002 562 571
34. M. Schlüter, and R. Gmelin Abnormale enzymatische Spaltung von 4-Methylthiobutylglucosinolat in Frischpflanzen von Eruca sativa Phytochemistry 11 1972 3427 3431
35. H.L. Tookey Crambe thioglucosidase - separation of a protein required for epithiobutane formation Abstracts of Papers of the Am. Chem. Soc. 1973 231
36. M. Traka, and R. Mithen Glucosinolates, isothiocyanates and human health Phytochem. Rev. 8 2009 269 282
37. C.W. Wheat, H. Vogel, U. Wittstock, M.F. Braby, D. Underwood, and T. Mitchell-Olds The genetic basis of a plant-insect coevolutionary key innovation Proc. Natl. Acad. Sci. USA 104 2007 20427 20431
38. X.F. Yan, and S.X. Chen Regulation of plant glucosinolate metabolism Planta 226 2007 1343 1352
39. M.D. Zabala, M. Grant, A.M. Bones, R. Bennett, Y.S. Lim, R. Kissen, and J.T. Rossiter Characterisation of recombinant epithiospecifier protein and its over-expression in Arabidopsis thaliana Phytochemistry 66 2005 859 867