Interaction of cruciferous phytoanticipins with plant fungal pathogens: Indole glucosinolates are not metabolized but the corresponding desulfo-derivatives and nitriles are

Phytochemistry

Volumn 72, Issue 18, 2011, Pages 2308-2316

  Pedras, M Soledade C ^a   Hossain, Sajjad ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

Alternaria brassicicola; Brassicaceae; Crucifer; Indole glucosinolate; Myrosinase activity; Rhizoctonia solani; Sclerotinia sclerotiorum; Secondary metabolism

Indexed keywords

GLUCOSINOLATE; INDOLE DERIVATIVE; NITRILE;

ALTERNARIA; ARTICLE; ASCOMYCETES; BRASSICACEAE; CHEMISTRY; DISEASE RESISTANCE; HYPHOMYCETES; METABOLISM; MICROBIOLOGY; PHYSIOLOGY;

ALTERNARIA; ASCOMYCOTA; BRASSICACEAE; DISEASE RESISTANCE; GLUCOSINOLATES; INDOLES; NITRILES; RHIZOCTONIA;

ALTERNARIA; ALTERNARIA BRASSICICOLA; BRASSICACEAE; FUNGI; HYPHOMYCETES; SCLEROTINIA SCLEROTIORUM; THANATEPHORUS CUCUMERIS;

EID: 80054957478     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2011.08.018     Document Type: Article

References (43)

1. N. Agerbirk, M. De Vos, J.H. Kim, and G. Jander Indole glucosinolate breakdown and its biological effects Phytochem. Rev. 8 2009 101 120
2. I. Ahuja, J. Rohloff, and A.M. Bones Defence mechanisms of Brassicaceae: implications for plant-insect interactions and potential for integrated pest management Agron. Sustain. Dev. 30 2010 311 348
3. A. Aires, V.R. Mota, M.J. Saavedra, A.A. Monteiro, M. Simoes, E.A.S. Rosa, and R.N. Bennett Initial in vitro evaluations of the antibacterial activities of glucosinolate enzymatic hydrolysis products against plant pathogenic bacteria J. Appl. Microb. 106 2009 2096 2105
4. M.D. Bolton, B.P.H.J. Thomma, and B.D. Nelson Sclerotinia sclerotiorum (lib.) de Bary: biology and molecular traits of a cosmopolitan pathogen Mol. Plant Pathol. 7 2006 1 16
5. A.M. Bones, and J.T. Rossiter The enzymic and chemically induced decomposition of glucosinolates Phytochemistry 67 2006 1053 1067 (Pubitemid 43833458)
6. G. Brader, M.D. Mikkelsen, and B.A. Halkier Altering glucosinolate profiles modulates disease resistance in plants Plant J. 46 2006 758 767 (Pubitemid 43780623)
7. S. Chevolleau, N. Gasc, P. Rollin, and J. Tulliez Enzymatic, chemical, and thermal breakdown of 3H-labeled glucobrassicin, the parent indole glucosinolate J. Agric. Food Chem. 1997 45 1997 4290 4296 (Pubitemid 127491622)
8. D.L. Cooke, P.D. Jenkins, and D.M. Lewis Production of phytotoxic spore germination liquids by Alternaria brassicae and A. brassicicola and their effect on species of the family Brassicaceae Ann. Appl. Biol. 131 1997 413 426 (Pubitemid 28111341)
9. 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 (Pubitemid 32063165)
10. G.R. Fenwick, and R.K. Heaney Glucosinolates and their breakdown products in cruciferous crops, foods and feeding stuffs Food Chem. 11 1983 249 271
11. S.S. Galletti, E.O. Leoni, S. Cinti, and C. Cerato Aspergillus flavus transformation of glucosinolates to nitriles by an arylsulfatase and a β-thio-glucosidase Soil Biol. Biochem. 40 2008 2170 2173
12. K. Góralska, M. Dynowska, and E. Ciska Fungistatic properties of glucosinolates - a reconnaissance study Polish J. Environ. Stud. 18 2009 377 382
13. K.R. Grose, and L.F. Bjeldanes Oligomerization of indole-3-carbinol in aqueous acid Chem. Res. Toxicol. 5 1993 188 193
14. B.A. Halkier, and J. Gershenzon Biology and biochemistry of glucosinolates Annu. Rev. Plant Biol. 57 2006 303 333 (Pubitemid 44061027)
15. 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
16. M. Luebeck Molecular characterization of Rhizoctonia solani Appl. Mycol. Biotechnol. 4 2004 205 224
17. L.M. Manici, L. Lazzeri, and S. Palmieri In vitro fungitoxic activity of some glucosinolates and their enzyme derived products toward plant pathogenic fungi J. Agric. Food Chem. 45 1997 2768 2773 (Pubitemid 127477018)
18. M.D. Mikkelsen, B.L. Petersen, E. Glawischnig, A.B. Jensen, E. Andreasson, and B.A. Halkier Modulation of CYP79 genes and glucosinolate profiles in Arabidopsis by defense signaling pathways Plant Physiol. 131 2003 298 308 (Pubitemid 36141226)
19. R. Nagarajan, and P.T. Perumal Potassium hydrogen sulfate-catalyzed reactions of indoles: a mild, expedient synthesis of bis-indolylmethanes Chem. Lett. 33 2004 288 289 (Pubitemid 38661965)
20. M. Ohtsuru, I. Tsuruo, and T. Hata The production and stability of intracellular myrosinase from Aspergillus niger Agric. Biol. Chem. 37 1973 967 971
21. M.S.C. Pedras The chemical ecology of crucifers and their fungal pathogens: boosting plant defenses and inhibiting pathogen invasion Chem. Rec. 8 2008 109 115
22. M.S.C. Pedras, and P.W.K. Ahiahonu Metabolism and detoxification of phytoalexins and analogs by phytopathogenic fungi Phytochemistry 66 2005 391 411 (Pubitemid 40215069)
23. M.S.C. Pedras, and S. Montaut Probing metabolic pathways in fungal pathogens of crucifers: biotransformation of indole-3-acetaldoxime, 4-hydroxyphenylacetaldoxime, and their metabolites Bioorg. Med. Chem. 11 2003 3115 3120 (Pubitemid 36773571)
24. M.S.C. Pedras, and D.P.O. Okinyo Remarkable incorporation of the first sulfur containing indole derivative: another piece in the biosynthetic puzzle of crucifer phytoalexins Org. Biomol. Chem. 6 2008 51 54 (Pubitemid 350255958)
25. M.S.C. Pedras, and M. Suchy Detoxification pathways of the phytoalexins brassilexin and sinalexin in Leptosphaeria maculans: isolation and synthesis of the elusive intermediate 3-formylindolyl-2-sulfonic acid Org. Biomol. Chem. 3 2005 2002 2007 (Pubitemid 40751373)
26. M.S.C. Pedras, and E.E. Yaya Phytoalexins from Brassicaceae: news from the front Phytochemistry 71 2010 1191 1197
27. Pedras, M.S.C.; Yaya, E.; Glawischnig, E.; 2011. The phytoalexins from cultivated and wild crucifers: Chemistry and biology. Nat. Prod. Rep.; 28, 1381-1405.
28. M.S.C. Pedras, E. Yaya, and S. Hossain Unveiling the phytoalexin biosynthetic puzzle in salt cress: unprecedented incorporation of glucobrassicin into wasalexins A and B Org. Biomol. Chem. 8 2010 5150 5158
29. M.S.C. Pedras, Q.A. Zheng, R.S. Gadagi, and S.R. Rimmer Phytoalexins and polar metabolites from the oilseeds canola and rapeseed: differential metabolic responses to the biotroph Albugo candida and to abiotic stress Phytochemistry 69 2008 894 910 (Pubitemid 351222604)
30. M.S.C. Pedras, Q.A. Zheng, and V.K. Sarma-Mamillapalle The phytoalexins from Brassicaceae: structure, biological activity, synthesis and biosynthesis Nat. Prod. Commun. 2 2007 319 330
31. E. Piironen, and A.I. Virtanen The synthesis of ascorbigen from ascorbic acid and 3-hydroxymethylindole Acta Chem. Scand. 16 1962 1286 1287
32. N. Rakariyatham, B. Butr-Indr, H. Niamsup, and L. Shank Improvement of myrosinase activity of Aspergillus sp. NR4617 by chemical mutagenesis Electron. J. Biotechnol. 9 2006 379 385
33. S.R. Rimmer, and L. Buchwaldt Diseases D.S. Kimber, D.I. McGregor, Brassica Oilseeds: Production and Utilization 1995 CAB International Wallingford, Oxon, UK 111 140
34. A.A.B. Robertson, and N.P. Botting Synthesis of deuterium labeled desulfoglucosinolates as internal standards of LC-MS analysis Tetrahedron 55 1999 13269 13284 (Pubitemid 29502276)
35. P. Rollin, and A. Tatibouet Glucosinolates: the synthetic approach C. R. Chim. 14 2011 194 210
36. M. Shikita, J.W. Fahey, T.R. Golden, W.D. Holtzclaw, and P. Talalay An unusual case of 'uncompetitive activation ' by ascorbic acid: purification and kinetic properties of a myrosinase from Raphanus sativus seedlings Biochem. J. 341 1999 725 732 (Pubitemid 29389204)
37. C.J. Smith Accumulation of phytoalexins: defence mechanism and stimulus response system New Phytol. 132 1996 1 45
38. J.P. Smits, and W.B.J. Knol Glucosinolate degradation by Aspergillus clavatus and Fusarium oxysporum in liquid and solid-state fermentation Appl. Microbiol. Biotechnol. 38 1993 696 701 (Pubitemid 23054283)
39. M. Somei, A. Tanimoto, H. Orita, F. Yamada, and O. Toshiharu Synthesis of wasabi phytoalexin (methyl-1-methoxyindole-3-carboxylate) and its 5-iodo derivative, and their nucleophilic substitution reactions Heterocycles 54 2001 425 432 (Pubitemid 32162754)
40. I.E. Sønderby, F. Geu-Flores, and B.A. Halkier Biosynthesis of glucosinolates - gene discovery and beyond Trends Plant Sci. 15 2010 283 290
41. M. Traka, and R. Mithen Glucosinolates, isothiocyanates and human health Phytochem. Rev. 8 2009 269 282
42. A.P. Vig, G. Rampal, T.S. Thind, and S. Arora Bio-protective effects of glucosinolates - a review LWT - Food Sci. Technol. 42 2009 1561 1572
43. S.J.K. Vishwanath, M.P. Singh, and R.P. Awasthi Induction of resistance in mustard (Brassica juncea) against Alternaria black spot with an avirulent Alternaria brassicae isolate-D Eur. J. Plant Pathol. 105 1999 217 220 (Pubitemid 29212134)