Metabolism and detoxification of phytoalexins and analogs by phytopathogenic fungi

Phytochemistry

Volumn 66, Issue 4, 2005, Pages 391-411

  Pedras, M Soledade C ^a   Ahiahonu, Pearson W K ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

Brassicaceae; Cruciferae; Detoxification; Graminaceae; Leguminosae; Metabolism; Phytoalexins; Solanaceae

Indexed keywords

ACETONITRILE DERIVATIVE; BENZOIC ACID; CAMALEXIN; DAIDZEIN; EPOXIDE; FORMONONETIN; INDOLE DERIVATIVE; MEDICARPIN; PHYTOALEXIN; RESVERATROL;

ANGIOSPERM; BRASSICACEAE; CRUCIFERA; DETOXIFICATION; FUNGAL STRAIN; FUNGAL VIRULENCE; FUNGUS; LEGUME; METABOLISM; PATHOGENESIS; PATHOGENICITY; PLANT; PLANT FUNGUS INTERACTION; POACEAE; REVIEW; VIRULENCE;

BRASSICACEAE; FABACEAE; FUNGI; MAGNOLIOPHYTA; POACEAE; SOLANACEAE;

EID: 13444280375     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2004.12.032     Document Type: Review

References (106)

1. M. Adrian, H. Rajaei, P. Jeandet, J. Veneau, and R. Bessis Resveratrol oxidation in Botrytis cinerea conidia Phytopathology 88 1998 472 476
2. T. Akatsuka, O. Kodama, H. Sekido, Y. Kono, and S. Takeuchi Novel phytoalexins (oryzalexins A, B and C) isolated from rice blast leaves infected with Pyricularia oryzae. Part I: Isolation, characterization and biological activities of oryzalexins Agric. Biol. Chem. 49 1985 1689 1694
3. J.A. Bailey J.W. Mansfield Phytoalexins 1982 Blackie and Son Glasgow, UK 334
4. J.A. Bailey, R.S. Burden, A. Mynett, and C. Brown Metabolism of phaseollin by Septoria nodorum and other non-pathogens of Phaseolus vulgaris Phytochemistry 16 1977 1541 1544
5. J.N. Bilton, J.R. Dernam, and I.M. Smith 6a-Hydroxypterocarpans from red clover Phytochemistry 15 1976 1411 1412
6. O. Bratfaleanu, and B. Steinhauer Degradation of avenalumins by fungi in vitro and in vivo Mededelingen - Facultiet Landbouwkundige en Toegepaste Biologische Wetenschappen 59 1994 877 884
7. A. Breuil, M. Adrian, N. Pirio, P. Meunier, R. Bessis, and P. Jeandet Metabolism of stilbene phytoalexins by Botrytis cinerea Tetrahedron Lett. 39 1998 537 540
8. C.J.W. Brooks, and D.G. Watson Phytoalexins. Nat. Prod. Rep. 1985 427 459
9. T.D. Bykova, M.A. Davydova, O.L. Ozeretskovskaya, and N.A. Moiseeva Antifungal substances in apples Mikologiya i Fitopatologiya 11 1977 116 122
10. I.A.M. Cruickshank Studies on phytoalexins, IV. The antimicrobial spectrum of pisatin Aust. J. Biol. Sci. 15 1962 147 159
11. I.A.M. Cruickshank, and D.R. Perrin Isolation of a phytoalexin from Pisum sativum L Nature 187 1960 799 800
12. L.M. Delserone, K. McCluskey, D.E. Matthews, and H.D. VanEtten Pisatin demethylation by fungal pathogens and nonpathogens of pea: association with pisatin tolerance and virulence Physiol. Mol. Plant Pathol. 55 1999 317 326
13. T.P. Denny, and H.D. VanEtten Tolerance by Nectria haematococca MP VI of the chickpea (Cicer arietinum) phytoalexins medicarpin and maackiain Physiol. Plant. Pathol. 19 1981 419 437
14. T.P. Denny, and H.D. VanEtten Metabolism of the phytoalexins medicarpin and maackiain by Fusarium solani Phytochemistry 21 1982 1023 1028
15. T.P. Denny, P.S. Matthews, and H.D. VanEtten A possible mechanism of nondegradative tolerance of pisatin in Nectria haematococca MP VI Physiol. Molec. Plant Pathol. 30 1987 93 107
16. A.E. Desjardins, and H.D. VanEtten Partial purification of pisatin demethylase, a cytochrome P-450 from the pathogenic fungus Nectria haematococca Arch. Microbiol. 144 1986 84 90
17. A.E. Desjardins, H.W. Gardner, and R.D. Plattner Detoxification of the potato phytoalexin lubimin by Gibberella pulicaris Phytochemistry 28 1989 431 437
18. D. Durango, W. Quinones, F. Torres, Y. Rosero, J. Gil, and F. Echeverri Phytoalexin accumulation in Colombian bean varieties and aminosugars as elicitors Molecules 7 2002 817 832
19. J. Enkerli, G. Bhatt, and S.F. Covert Maackiain detoxification contributes to the virulence of Nectria haematococca MP VI on chickpea Mol. Plant-Microbe Interact. 11 1998 317 326
20. H. Esaki, H. Onozaki, Y. Morimitsu, S. Kawakishi, and T. Osawa Potent antioxidative isoflavones isolated from soybeans fermented with Aspergillus saitoi Biosci. Biotechnol. Biochem. 62 1998 740 746
21. M. Essenberg Prospects for strengthening plant defenses through phytoalexin engineering Physiol. Mol. Plant Pathol. 59 2001 71 81
22. A. Farooq, and S. Tahara Fungal metabolism of flavonoids and related phytoalexins Curr. Top. Phytochem. 2 1999 1 33
23. D.L. Funnell, P.S. Matthews, and H.D. VanEtten Identification of new pisatin demethylase genes (PDA5 and PDA7) in Nectria haematococca and non-Mendelian segregation of pisatin demethylating ability and virulence on pea due to loss of chromosomal elements Fungal Gen. Biol. 37 2002 121 133
24. H.W. Gardner, A.E. Desjardins, D. Weisleder, and R.D. Plattner Biotransformation of the potato phytoalexin, lubimin, by Gibberella pulicaris. Identification of major products Biochim. Biophys. Acta. 966 1988 347 356
25. H.W. Gardner, A.E. Desjardins, S.P. McCormick, and D. Weisleder Detoxification of the potato phytoalexin rishitin by Gibberella pulicaris Phytochemistry 37 1994 1001 1005
26. E. Glawischnig, B.G. Hansen, C.E. Olsen, and B.A. Halkier Camalexin is synthesized from indole-3-acetaldoxime, a key branching point between primary and secondary metabolism in Arabidopsis Proc. Nat. Acad. Sci. USA 101 2004 8245 8250
27. D. Gross Antimicrobial defense compounds in Gramineae Zeitsch. Pflanzen. Pflanzen. 96 1989 535 553
28. R. Hain, H.J. Reif, E. Krause, R. Langebartels, H. Kindl, B. Vornam, W. Wiese, E. Schmelzer, P.H. Schreier, R.H. Stocker, and K. Strenzel Disease resistance results from foreign phytoalexin expression in a novel plant Nature 361 1993 153 156
29. R. Hammerschmidt, and E.K. Dann The role of phytoalexins in plant protection Novartis Foundat. Symp. 223 1999 175 190
30. J.B. Harborne The comparative biochemistry of phytoalexin induction in plants Biochem. System. Ecol. 27 1999 335 367
31. J.A. Hargreaves, J.W. Mansfield, D.T. Coxon, and K.R. Price Wyerone epoxide as a phytoalexin in Vicia faba and its metabolism by Botrytis cinerea and B. fabae in vitro Phytochemistry 15 1976 1119 1121
32. V.J. Higgins Induced conversion of the phytoalexin maackiain by the alfalfa pathogen Stemphylium botryosum Physiol. Plant Pathol. 6 1975 5 18
33. V.J. Higgins, A. Stoessl, and M.C. Heath Conversion of phaseollin to phaseollinisoflavan by Stemphylium botryosum Phytopathology 64 1974 105 107
34. J.D. Hipskind, and N.L. Paiva Constitutive accumulation of a resveratrol-glucoside in transgenic alfalfa increases resistance to Phoma medicaginis Mol. Plant-Microbe Interact. 13 2000 551 562
35. B. Höhl, M. Arnemann, L. Schwenen, D. Stöckl, G. Bringmann, J. Jansen, and W. Barz Degradation of the pterocarpan phytoalexin (-)-maackiain by Ascochyta rabiei Z. Naturforsch. 44c 1989 771 776
36. B.J. Howlett, A. Idnurm, and M.S.C. Pedras Leptosphaeria maculans the causal agent of blackleg disease of brassicas Fungal Gen. Biol. 33 2001 1 14
37. J.L. Ingham Induced and constitutive isoflavonoids from stems of chickpeas (Cicer arietinum L.) inoculated with spores of Helminthosporium carbonum Ullstrup Phytopatholog. Zeitschrift 87 1976 353 367
38. J.L. Ingham Fungal modification of pterocarpan phytoalexins from Melilotus alba and Trifolium pratense Phytochemistry 15 1976 1489 1495
39. P. Jeandet, A.C. Douillet-Breuil, R. Bessis, S. Debord, M. Sbaghi, and M. Adrian Phytoalexins from the Vitaceae: biosynthesis, phytoalexin gene expression in transgenic plants, antifungal activity, and metabolism J. Agric. Food Chem. 50 2002 2731 2741
40. P.J. Kuhn, and D.A. Smith Isolation from Fusarium solani f. sp. phaseoli of an enzymic system responsible for kievitone and phaseollidin detoxification Physiol. Plant Pathol. 14 1979 179 190
41. D. Li, K.R. Chung, D.A. Smith, and C.L. Schardl The Fusarium solani gene encoding kievitone hydratase, a secreted enzyme that catalyzes detoxification of a bean phytoalexin Mol. Plant-Microbe Interact. 8 1995 388 397
42. M.C. Lucy, H.D. Matthews, and H.D. VanEtten Metabolic detoxification of the phytoalexins maackiain and medicarpin by Nectria haematococca field isolates: relationship to virulence on chickpea Physiol. Mol. Plant. Pathol. 33 1988 187 199
43. S.F. Mackintosh, D.E. Matthews, and H.D. VanEtten Two additional genes for pisatin demethylation and their relationship to the pathogenicity of Nectria haematococca on pea Mol. Plant-Microbe Interact. 2 1989 354 362
44. A.P. Maloney, and H.D. VanEtten A gene from the fungal plant pathogen Nectria haematococca that encodes the phytoalexin-detoxifying enzyme pisatin demethylase defines a new cytochrome P450 family Mol. General Genetics 243 1994 506 514
45. D.E. Matthews, and H.D. VanEtten Detoxification of the phytoalexin pisatin by a fungal cytochrome P-450 Arch. Biochem. Biophys. 224 1983 494 505
46. S. Mayama The role of avenalumin in the resistance of oats to crown rust Kagawa Daigaku Nogakubu Kiyo 42 1983 1 64
47. V.P.W. Miao, and H.D. VanEtten Genetic analysis of the role of phytoalexin detoxification in virulence of the fungus Nectria haematococca on chickpea (Cicer arietinum) Appl. Environ. Microbiol. 58 1992 809 814
48. V.P.W. Miao, and H.D. VanEtten Three genes for metabolism of the phytoalexin maackiain in the plant pathogen Nectria haematococca: meiotic instability and relationship to a new gene for pisatin demethylase Appl. Environ. Microbiol. 58 1992 801 808
49. K. Monde, A. Tanaka, and M. Takasugi Trapping experiment with aniline for a biosynthetic intermediate of sulfur containing cruciferous phytoalexins J. Org. Chem. 61 1996 9053 9054
50. J.P. Morrissey, and A.E. Osbourn Fungal resistance to plant antibiotics as a mechanism of pathogenesis Microbiol. Mol. Biol. Rev. 63 1999 708 724
51. K.O. Müller, and H. Börger Experimentelle Untersuchungen uber die Phytophthora: Resistenz der Kartoffel Arb. Biol. Anst. Reichsanst. 23 1940 189 231
52. M.S.C. Pedras Metabolism of cruciferous phytoalexins by phytopathogenic fungi: mimicking or overcoming plant defenses? Recent Res. Dev. Phytochem. 2 1998 259 267
53. M.S.C. Pedras Prospects for controlling plant fungal diseases: alternatives based on chemical ecology and biotechnology Can. J. Chem. 82 2004 1329 1335
54. M.S.C. Pedras, and P.W.K. Ahiahonu Probing the phytopathogenic stem rot fungus with phytoalexin analogs: unprecedented glucosylation of camalexin and 6-methoxycamalexin Bioorg. Med. Chem. 10 2002 3307 3312
55. M.S.C. Pedras, and P.W.K. Ahiahonu Phytotoxin production and phytoalexin elicitation by the phytopathogenic fungus Sclerotinia sclerotiorum J. Chem. Ecol. 30 2004 2163 2179
56. M.S.C. Pedras, and A.Q. Khan Biotransformation of the brassica phytoalexin brassicanal A by the blackleg fungus J. Agric. Food Chem. 44 1996 3403
57. M.S.C. Pedras, and A.Q. Khan Unprecedented detoxification of the cruciferous phytoalexin camalexin by a root phytopathogen Bioorg. Med. Chem. Lett. 7 1997 2255 2260
58. M.S.C. Pedras, and A.Q. Khan Biotransformation of the phytoalexin camalexin by the phytopathogen Rhizoctonia solani Phytochemistry 53 2000 59 69
59. M.S.C. Pedras, and J. Liu Designer phytoalexins: probing camalexin detoxification pathways in the phytopathogen Rhizoctonia solani Org. Biomol. Chem. 2 2004 1070 1076
60. M.S.C. Pedras, and S. Montaut Probing metabolic pathways in fungal pathogens of crucifers: biotransformation of 4-hydroxyphenylacetaldoxime, and their metabolites Bioorg. Med. Chem. 11 2003 3115 3120
61. M.S.C. Pedras, and F.I. Okanga Probing the phytopathogenic blackleg fungus with a phytoalexin homolog J. Org. Chem. 63 1998 416 417
62. M.S.C. Pedras, and F.I. Okanga Strategies of cruciferous pathogenic fungi: detoxification of the phytoalexin cyclobrassinin by mimicry J. Agric. Food Chem. 47 1999 1196 1202
63. M.S.C. Pedras, and F.I. Okanga Metabolism of analogs of the phytoalexin brassinin by plant pathogenic fungi Can. J. Chem. 78 2000 338 346
64. M.S.C. Pedras, and J.L. Taylor Metabolic transformation of the phytoalexin brassinin by the blackleg fungus J. Org. Chem. 56 1991 2619 2621
65. M.S.C. Pedras, and J.L. Taylor Metabolism of the phytoalexin brassinin by the blackleg fungus J. Nat. Prod. 56 1993 731 738
66. M.S.C. Pedras, I. Borgmann, and J.L. Taylor Biotransformation of brassinin is a detoxification mechanism in the "blackleg" fungus Phytochemistry 11 1992 1 7
67. M.S.C. Pedras, A.Q. Khan, K.C. Smith, and S.L. Stettner Preparation, biotransformation, and antifungal activity of methyl benzyldithiocarbamates Can. J. Chem. 75 1997 825 828
68. M.S.C. Pedras, A.Q. Khan, and J.L. Taylor The phytoalexin camalexin is not metabolized by Phoma lingam, Alternaria brassicae, or phytopathogenic bacteria Plant Sci. 139 1998 1 8
69. M.S.C. Pedras, F.I. Okanga, A.Q. Khan, and I.L. Zaharia Phytoalexins from crucifers: synthesis, biosynthesis, and biotransformation Phytochemistry 53 2000 161 176
70. M.S.C. Pedras, C. Nycholat, S. Montaut, Y. Xu, and A.Q. Khan Chemical defenses of crucifers: elicitation and metabolism of phytoalexins and indole-3-acetonitrile in brown mustard and turnip Phytochemistry 59 2002 611 625
71. M.S.C. Pedras, P.B. Chumala, and M. Suchy Phytoalexins from Thlaspi arvense, a wild crucifer resistant to virulent Leptosphaeria maculans: structures, syntheses and antifungal activity Phytochemistry 64 2003 949 956
72. M.S.C. Pedras, M. Jha, and P.W.K. Ahiahonu The synthesis and biosynthesis of phytoalexins produced by cruciferous plants Curr. Org. Chem. 7 2003 1635 1647
73. M.S.C. Pedras, P.W.K. Ahiahonu, and M. Hossain Brassinin detoxification by Sclerotinia sclerotiorum requires an inducible glucosyl transferase Phytochemistry 65 2004 2685 2694
74. M.S.C. Pedras, S. Montaut, and M. Suchy New phytoalexins from rutabaga: structures, syntheses, biosyntheses, and biological activity J. Org. Chem. 69 2004 4471 4476
75. R. Pezet, V. Pont, and K. Hoang-Van Evidence for oxidative detoxification of pterostilbene and resveratrol by a laccase-like stilbene oxidase produced by Botrytis cinerea Physiol. Mol. Plant. Pathol. 39 1991 441 450
76. L.S. Puckhaber, R.D. Stipanovic, and A.A. Bell Kenaf Phytoalexin: toxicity of o-hibiscanone and its hydroquinone to the plant pathogens Verticillium dahliae and Fusarium oxysporum f. sp. vasinfectum J. Agric. Food Chem. 46 1998 4744 4747
77. T. Rouxel, A. Kollman, and M.H. Ballesdent Phytoalexins from the crucifers M. Daniel R.P. Purkayastha Handbook of Phytoalexin Metabolism and Action 1995 Marcel Dekker, Inc. New York 229 261
78. W. Schäfer, D. Straney, L. Ciuffetti, and H.D. VanEtten One enzyme makes a fungal pathogen, but not a saprophyte, virulent on a new host plant Science 246 1989 247 249
79. D.A. Smith Toxicity of phytoalexins J.A. Bailey J.W. Mansfield Phytoalexins 1982 Blackie & Son Glasgow, UK 218 252
80. C.J. Smith Accumulation of phytoalexins: defense mechanism and stimulus response system New Phytol. 132 1996 1 45
81. D.A. Smith, J.M. Harrer, and T.E. Cleveland Simultaneous detoxification of phytoalexins by Fusarium solani f. sp. phaseoli Phytopathology 71 1981 1212 1215
82. S. Soby, S. Caldera, R. Bates, and H.D. VanEtten Detoxification of the phytoalexins maackiain and medicarpin by fungal pathogens of alfalfa Phytochemistry 41 1996 759 765
83. P.W. Steiner Alfalfa phytoalexin degradation by Stemphylium botryosum in relation to pathogenicity and virulence Diss. Abstr. Int. B 38 1977 5467 5468
84. S. Tahara, E. Misumi, J. Mizutani, and J.L. Ingham Fungal metabolism of the prenylated isoflavone 2,3-dehydrokievitone Z. Naturforsch. 42c 1987 1055 1062
85. M. Takasugi, N. Katsui, and A. Shirata Isolation of three novel sulfur-containing phytoalexins from the Chinese cabbage Brassica campestris L. ssp. pekinensis (Cruciferae) J. Chem. Soc., Chem. Commun. 1986 1077 1078
86. J.E. Thomzik, K. Stenzel, R. Stocker, P.H. Schreier, R. Hain, and D.J. Stahl Synthesis of a grapevine phytoalexin in transgenic tomatoes (Lycopersicon esculentum Mill.) conditions resistance against Phytophthora infestans Physiol. Molec. Plant Pathol. 51 1997 265 278
87. C.S. Turbek, D. Li, G.H. Choi, C.L. Schardl, and D.A. Smith Induction and purification of kievitone hydratase from Fusarium solani f. sp. phaseoli Phytochemistry 29 1990 2841 2846
88. C.S. Turbek, D.A. Smith, and C.L. Schardl An extracellular enzyme from Fusarium solani f. sp. phaseoli, which catalyzes hydration of the isoflavonoid phytoalexin phaseollidin FEMS Microbiol. Lett. 94 1992 187 190
89. Van den Heuvel, H.D. VanEtten, J.W. Serum, D.L. Coffen, and T.H. Williams Identification of 1a-hydroxyphaseollone, a phaseollin metabolite produced by Fusarium solani Phytochemistry 13 1974 1129 1131
90. H.D. VanEtten, S.K. Pueppke, and T.C. Kelsey 3,6a-Dihydroxy-8,9- methylenedioxy pterocarpan as a metabolite of pisatin produced by Fusarium solani f. sp. pisi Phytochemistry 14 1975 1103 1105
91. H.D. VanEtten, P.S. Matthews, K.J. Tegtmeier, M.F. Dietert, and J.I. Stein The association of pisatin tolerance and demethylation with virulence on pea in Nectria haematococca Physiol. Plant Pathol. 16 1980 257 268
92. H.D. VanEtten, D.E. Matthews, and D.A. Smith Metabolism of phytoalexins J.A. Bailey J.W. Mansfield Phytoalexins 1982 Blackie and Son Glasgow, UK 181 217
93. H.D. VanEtten, D.E. Matthews, and P.S. Matthews Phytoalexin detoxification: Importance for pathogenicity and practical implications Ann. Rev. Phytopathol. 27 1989 143 164
94. H.D. VanEtten, D. Funnell-Baerg, C. Wasmann, and K. McCluskey Location of pathogenicity genes on dispensable chromosomes in Nectria haematococca MP VI Antonie van Leeuwenhoek 65 1994 263 267
95. H.D. VanEtten, J.W. Mansfield, J.A. Bailey, and E.E. Farmer Two classes of plant antibiotics: phytoalexins versus "phytoanticipins" The Plant Cell 6 1994 1191 1192
96. H.D. VanEtten, R.W. Sandrock, C.C. Wasmann, S.D. Soby, K. McCluskey, and P. Wang Detoxification of phytoanticipins and phytoalexins by phytopathogenic fungi Can. J. Bot. 73 1 1995 S518 S525
97. H.D. VanEtten, E. Temporini, and C. Wasmann Phytoalexin (and phytoanticipin) tolerance as a virulence trait: why is it not required by all pathogens? Physiol. Mol. Plant Pathol. 59 2001 83 93
98. E.W.B. Ward, and A. Stoessl Postinfectional inhibitors from plants. III. Detoxification of capsidiol, an antifungal compound from peppers Phytopathology 62 1972 1186 1187
99. K.M. Weltring Phytoalexins in the relation between plants and their fungal pathogens U. Stahl P. Tudzynski Molecular Biology of Filamentous Fungi 1991 VCH 111 124
100. K.M. Weltring, and M. Altenburger Metabolism of the phytoalexin rishitin by Gibberella pulicaris is highly reduced in liquid culture Z. Naturforsch. 53c 1998 806 810
101. K.M. Weltring, and W. Barz Degradation of 3,9-dimethoxypterocarpan and medicarpin by Fusarium proliferatum Z. Naturforsch. C 35C 1980 399 405
102. K.M. Weltring, K. Mackenbrock, and W. Barz Demethylation, methylation and 3′-hydroxylation of isoflavones by Fusarium fungi Z. Naturforsch. 37c 1982 570 574
103. K.M. Weltring, W. Barz, and P.M. Dewick Degradation of the phytoalexin medicarpin by Fusarium oxysporum Phytochemistry 22 1983 2883 2884
104. I.M. Whitehead, A.L. Atkinson, D.R. Threlfall, and R. David Studies on the biosynthesis and metabolism of the phytoalexin lubimin and related compounds in Datura stramonium L Planta 182 1990 81 88
105. Q. Wu, and H.D. VanEtten Introduction of plant and fungal genes into pea (Pisum sativum L.) hairy roots reduces their ability to produce pisatin and affects their response to a fungal pathogen Mol. Plant-Microbe Interact. 17 2004 798 804
106. Q. Yue, C.W. Bacon, and M.D. Richardson Biotransformation of 2-benzoxazolinone and 6-methoxybenzoxazolinone by Fusarium moniliforme Phytochemistry 48 1998 451 454