Phytotoxins, elicitors and other secondary metabolites from phytopathogenic "blackleg" fungi: Structure, phytotoxicity and biosynthesis

Natural Product Communications

Volumn 4, Issue 9, 2009, Pages 1291-1304

  Pedras, M Soledade C ^a   Yu, Yang ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

Cerebroside; Depsilairdin; Dioxopiperazine; Elicitor; ETP; Fungal metabolite; L. maculans; Leptosphaeria biglobosa; Phoma lingam; Phomalide; Phytotoxin; Polyketide; Sesquiterpene; Sirodesmin

Indexed keywords

CEREBROSIDE; DEPSIPEPTIDE; ETHIONAMIDE; FUNGAL METABOLITE; PIPERAZINEDIONE; PLANT TOXIN; POLYKETIDE; SESQUITERPENE; STEROL; UNCLASSIFIED DRUG; MACROLIDE; PHYTOHORMONE; PIPERAZINE DERIVATIVE;

BIOSYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; FUNGUS; FUNGUS CULTURE; FUNGUS ISOLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LEPTOSPHAERIA BIGLOBOSA; LEPTOSPHAERIA MACULANS; METABOLITE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PHYTOTOXICITY; PLANT DISEASE; REVIEW; SALT STRESS; CHEMISTRY; METABOLISM; MICROBIOLOGY;

LEPTOSPHAERIA BICOLOR; LEPTOSPHAERIA BIGLOBOSA; LEPTOSPHAERIA MACULANS;

DEPSIPEPTIDES; FUNGI; MACROLIDES; PIPERAZINES; PLANT DISEASES; PLANT GROWTH REGULATORS; SESQUITERPENES; STEROLS;

EID: 73349140856     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x0900400927     Document Type: Review

References (72)

1. Fitt BDL, Brun H, Barbetti MJ, Rimmer SR. (2006) World-wide importance of phoma stem canker (Leptosphaeria maculans and L. biglobosa) on oilseed rape (Brassica napus). European Journal of Plant Pathology, 114, 3-15.
2. Howlett BJ, Idnurm A, Pedras MSC. (2001) Leptosphaeria maculans, the causal agent of blackleg disease of Brassicas. Fungal Genetics and Biology, 33, 1-14.
3. Chen Y, Fernando WGD. (2006) Prevalence of pathogenicity groups of Leptosphaeria maculans in western Canada and North Dakota, USA. Canadian Journal of Plant Pathology, 28, 533-539. (Pubitemid 46841837)
4. Kutcher HR, Keri M, McLaren DL, Rimmer, SR. (2007) Pathogenic variability of Leptosphaeria maculans in western Canada. Canadian Journal of Plant Pathology, 29, 388-393. (Pubitemid 351548130)
5. Wolpert TJ, Dunkle LD, Ciuffetti LM. (2002) Host-selective toxins and avirulence determinants: what's in a name? Annual Review of Phytopathology, 40, 251-285.
6. Strange RN. (2007) Phytotoxins produced by microbial plant pathogens. Natural Product Reports, 24, 127-144.
7. Tharayil N, Bhowmik P, Alpert P, Walker E, Amarasiriwardena D, Xing, B. (2009) Dual purpose secondary compounds: phytotoxin of Centaurea diffusa also facilitates nutrient uptake. New Phytologist, 181, 424-434. (Pubitemid 352840352)
8. Montesano M, Brader G, Palva ET. (2003) Pathogen derived elicitors: searching for receptors in plants. Molecular Plant Pathology, 4, 73-79. (Pubitemid 36093361)
9. Jones DA, Takemoto D. (2004) Plant innate immunity: direct and indirect recognition of general and specific pathogen-associated molecules. Current Opinion in Immunology, 16, 48-62.
10. Nurnberger T, Brunner F, Kemmerling B, Piater L. (2004) Inate immunity in plants and animals: striking similarities and obvious differences. Immunological Reviews, 198, 249-266.
11. Jones, JDG, Dangl JL. (2006) The plant immune system. Nature, 444, 323-329.
12. Walters D, Walsh D, Newton A, Lyon G. (2005) Induced resistance for plant disease control: maximizing the efficacy of resistance elicitors. Phytopathology, 95, 1368-1373.
13. Boller T. (1995) Chemoperception of microbial signals in plant-cells. Annual Review of Plant Physiology and Plant Molecular Biology, 46, 189-214.
14. Kloek AP, Verbsky ML, Sharma SB, Schoelz JE, Vogel J, Klessig DF, Kunkel BN. (2001) Resistance to Pseudomonas syringae conferred by an Arabidopsis thaliana coronatine-insensitive (coi1) mutation occurs through two distinct mechanisms. Plant Journal, 26, 509-522. (Pubitemid 32667714)
15. Allwood JW, Ellis DI, Goodacre R. (2008) Biomarker metabolites capturing the metabolite variance present in a rice plant developmental period. Physiologia Plantarum, 132, 117-135.
16. Elyashberg ME, Williams A, Martin GE. (2008) Computer-assisted structure verification and elucidation tools in NMR-based structure elucidation. Progress in Nuclear Magnetic Resonance Spectroscopy, 53, 1-104.
17. Nuzillard JM, Emerenciano VDP. (2006) Automatic structure elucidation through data base search and 2D NMR spectral analysis. Natural Product Communications, 1, 57-64.
18. Kuhn S, Egert B, Neumann S, Steinbeck C. (2008) Building blocks for automated elucidation of metabolites: Machine learning methods for NMR prediction. BMC Bioinformatics, 9, 400.
19. Steinbeck C. (2004) Recent developments in automated structure elucidation of natural products. Natural Product Reports, 21, 512-518.
20. Pedras MSC. (2001) Phytotoxins from fungi causing blackleg disease on crucifers: isolation, structure determination, detection, and phytotoxic activity. Recent Research Developments in Phytochemistry, 5, 109-117.
21. McGee DC, Petrie GA. (1978) variability of Leptosphaeria maculans in relation to blackleg of oilseed rape. Phytopathology, 68, 625-630.
22. Williams RH, Fitt BDL. (1999) Differentiating A and B groups of Leptosphaeria maculans, causal agent of stem canker (blackleg) of oilseed rape. Plant Pathology, 48, 161-175.
23. Shoemaker RA, Brun H. (2001) The teleomorph of the weakly aggressive segregate of Leptosphaeria maculans. Canadian Journal of Botany, 79, 412-419.
24. Taylor JL, Pedras MSC, Morales VM. (1995) Horizontal transfer in the phytopathogenic fungal genus Leptosphaeria and hostrange expansion. Trends in Microbiology, 3, 202-206.
25. Pedras MSC, Taylor JL, Morales VM. (1995) Phomaligin A and other yellow pigments in Phoma lingam and P. wasabiae. Phytochemistry, 38, 1215-1222.
26. Elliott CE, Gardiner DM, Thomas G, Cozijnsen A, De Wouw AV, Howlett BJ. (2007) Production of the toxin sirodesmin PL by Leptosphaeria maculans during infection of Brassica napus. Molecular Plant Pathology, 8, 791-802. (Pubitemid 47568900)
27. Férézou JP, Riche C, Quesneau-Thierry A, Pascard-Billy C, Barbier M, Bousquet JF, Boudart G. (1977) Structures of two toxins isolated from cultures of the fungus Phoma lingam Tode: sirodesmin PL and deacetylsirodesmin PL. Nouveau Journal de Chimie, I, 327-333.
28. Pedras MSC, Abrams SR, Séguin-Swartz G. (1988) Isolation of the first naturally occurring epimonothiodioxopiperazine, a fungal toxin produced by Phoma lingam. Tetrahedron Letters, 29, 3471-3474.
29. Pedras MSC, Séguin-Swartz G, Abrams SR. (1990) Minor phytotoxins from the blackleg fungus Phoma lingam. Phytochemistry, 29, 777-782.
30. Hurne AM, Chai CLL, Moerman K, Waring P. (2002) Influx of calcium through a redox-sensitive plasma membrane channel in thymocytes causes early necrotic cell death induced by the epipolythiodioxopiperazine toxins. Journal of Biological Chemistry, 277, 31631-31638. (Pubitemid 34968966)
31. Hurne AM, Chai CLL, Waring P. (2000) Inactivation of rabbit muscle creatine kinase by reversible formation of an internal disulfide bond induced by the fungal toxin gliotoxin. Journal of Biological Chemistry, 275, 25202-25206.
32. Pedras MSC, Abrams SR, Séguin-Swartz G, Quail JW, Jia ZC. (1989) Phomalirazine, a novel toxin from the phytopathogenic fungus Phoma lingam. Journal of the American Chemical Society, 111, 1904-1905. (Pubitemid 19074314)
33. Pedras MSC, Yu Y. (2008) Stress-driven discovery of metabolites from the phytopathogenic fungus Leptosphaeria maculans: Structure and activity of leptomaculins A-E. Bioorganic & Medicinal Chemistry, 16, 8063-8071.
34. Pedras MSC, Smith KC, Taylor, JL. (1998) Production of 2,5-dioxopiperazine by a new isolate type of the blackleg fungus Phoma lingam. Phytochemistry, 49, 1575-1577.
35. Pedras MSC, Biesenthal CJ. (2001) Isolation, structure determination, and phytotoxicity of unusual dioxopiperazines from the phytopathogenic fungus Phoma lingam. Phytochemistry, 58, 905-909.
36. Pedras MSC, Chumala PB. (2005) Phomapyrones from blackleg causing phytopathogenic fungi: isolation, structure determination, biosyntheses and biological activity. Phytochemistry, 66, 81-87.
37. Pedras MSC, Taylor JL, Nakashima TT. (1993) A novel chemical signal from the "blackleg" fungus: beyond phytotoxins and phytoalexins. Journal of Organic Chemistry, 58, 4778-4780.
38. Pedras MSC, Biesenthal CJ. (1998) Production of the host-selective phytotoxin phomalide by isolates of Leptosphaeria maculans and its correlation with sirodesmin PL production. Canadian Journal of Microbiology, 44, 547-553.
39. Ward DE, Vazquez A, Pedras MSC. (1999) Probing host-selective phytotoxicity: Synthesis and biological activity of phomalide, isophomalide, and dihydrophomalide. Journal of Organic Chemistry, 64, 1657-1666.
40. Pedras MSC, Chumala PB, Quail JW, (2004) Chemical mediators: The remarkable structure and host-selectivity of depsilairdin, a sesquiterpenic depsipeptide containing a new amino acid. Organic Letters, 6, 4615-4617.
41. Pardeshi SG, Ward DE. (2008) Enantiospecific total synthesis of lairdinol A. Journal of Organic Chemistry, 73, 1071-1076.
42. Pedras MSC, Erosa-Lopez CC, Quail JW, Taylor JL. (1999) Phomalairdenone: A new host-selective phytotoxin from a virulent type of the blackleg fungus Phoma lingam. Bioorganic & Medicinal Chemistry Letters, 9, 3291-3294.
43. Pedras MSC, Chumala PB, Venkatesham U. (2005) New sesquiterpenic phytotoxins establish unprecedented relationship between different groups of blackleg fungal isolates. Bioorganic & Medicinal Chemistry, 13, 2469-2475.
44. Corbett RE., Smith RAJ. (1967) Selin-11-en-4alpha-ol from essential oil of Podocarpus dacrydioides. Tetrahedron Letters, 1009-1012.
45. Bohlmann F, Misra LN, Jakupovic J, Robinson H, King RM. (1984) New sesquiterpene lactone type from Dugaldia hoopesii. Journal of Natural Products, 47, 658-662. (Pubitemid 14038900)
46. Griffiths KM, Bacic A, Howlett BJ. (2003) Sterol composition of mycelia of the plant pathogenic ascomycete Leptosphaeria maculans. Phytochemistry, 62, 147-153. (Pubitemid 36857581)
47. Pedras MSC, Morales VM, Taylor JL. (1994) Phomapyrones: three metabolites from the blackleg fungus. Phytochemistry, 36, 1315-1318.
48. Larsen TO, Perry NB., Andersen B. (2003) Infectopyrone, a potential mycotoxin from Alternaria infectoria. Tetrahedron Letters, 44, 4511-4513.
49. Parisi A, Piattelli M, Tringali C, Lio GMD. (1993) Identification of the phytotoxin mellein in culture fluids of Phoma tracheiphila. Phytochemistry, 32, 865-867.
50. Dickinson JM. (1993) Microbial pyran-2-ones and dihydropyran-2-ones. Natural Product Reports, 10, 71-98.
51. Pedras MSC, Morales VM, Taylor JL, (1993) Phomaligols and phomaligadiones: new metabolites from the blackleg fungus. Tetrahedron, 49, 8317-8322. (Pubitemid 23281037)
52. Pedras MSC. (1996) The chemistry of cyclohexenediones produced by the blackleg fungus. Canadian Journal of Chemistry, 74, 1597-1601.
53. Pedras MSC, Yu Y. (2009) Salt stress induces production of melanin related metabolites in the phytopathogenic fungus Leptosphaeria maculans. Natural Product Communications, 4, 53-58.
54. Dahiya JS, Rimmer SR, (1988) Accumulation of flaviolin, 4-hydroxyscytalone and 2-hydroxyjuglone in tricyclazole-treated cultures of Leptosphaeria maculans. Phytochemistry, 27, 3481-3482.
55. Pedras MSC, Yu Y. (2008) Structure and biological activity of maculansin A, a phytotoxin from the phytopathogenic fungus Leptosphaeria maculans. Phytochemistry, 69, 2966-2971.
56. Pedras MSC, Chumala PB, Jin W, Islam MS, Hauck DW. (2009) The phytopathogenic fungus Alternaria brassicicola: phytotoxin production and phytoalexin elicitation. Phytochemistry, 70, 394-402.
57. Pedras MSC, Chumala PB, Yu Y. (2007) The phytopathogenic fungi Leptosphaeria maculans and Leptosphaeria biglobosa: chemotaxonomical characterization of isolates and metabolite production in different culture media. Canadian Journal of Microbiology, 53, 364-371.
58. Jiao Y, Yoshihara T, Akimoto M, Ichihara A. (1994) Two phenolic compounds from Valsa ambiens. Bioscience Biotechnology and Biochemistry, 58, 784-785.
59. Keen NT. (1975) Specific elicitors of plant phytoalexin production - determinants of race specificity in pathogens. Science, 187, 74-75.
60. Hahn MG. (1996) Microbial elicitors and their receptors in plants. Annual Review of Phytopathology, 34, 387-412.
61. Yu, Y. (2008) Elicitors and phytotoxins from the blackleg fungus: structure, bioactivity and biosynthesis. University of Saskatchewan, 198 pp.
62. Umemura K, Tanino S, Nagatsuka T, Koga J, Iwata M, Nagashima K, Amemiya Y. (2004) Cerebroside elicitor confers resistance to Fusarium disease in various plant species. Phytopathology, 94, 813-818. (Pubitemid 38965259)
63. Férézou JP, Quesneau-Thierry A, Barbier M, Kollmann A, Bousquet JF. (1980) Structure and synthesis of phomamide a new piperazine-2,5-dione related to the sirodesmins isolated from the culture medium of Phoma lingam. Journal of the Chemical Society, Perkin Transactions I, 113-115.
64. Bu'Lock JD, Clough LE, (1992) Sirodesmin biosynthesis. Australian Journal of Chemistry, 45, 39-45.
65. Férézou JP, Quesneau-Thierry A, Servy C, Zissmann E, Barbier M. (1980) Sirodesmin PL biosynthesis in Phoma lingam tode. Journal of the Chemical Society, Perkin Transactions I, 1739-1746.
66. Gardiner DM, Cozijnsen AJ, Wilson LM, Pedras MSC, Howlett BJ. (2004) The sirodesmin biosynthetic gene cluster of the plant pathogenic fungus Leptosphaeria maculans. Molecular Microbiology, 53, 1307-1318.
67. Pedras MSC, Yu Y. (2009) Mapping the sirodesmin PL biosynthetic pathway - A remarkable intrinsic steric deuterium isotope effect on a 1H NMR chemical shift determines beta-proton exchange in tyrosine. Canadian Journal of Chemistry, 87, 564-570.
68. Pedras MSC, Gadagi RS, Jha, M, Sarma-Mamillapalle, VK. (2007) Detoxification of the phytoalexin brassinin by isolates of Leptosphaeria maculans pathogenic on brown mustard involves an inducible hydrolase. Phytochemistry, 68, 1572-1578 (Pubitemid 46764778)
69. Pedras MSC, Jha M, Minic Z, Okeola OG. (2007) Isosteric probes provide structural requirements essential for detoxification of the phytoalexin brassinin by the fungal pathogen Leptosphaeria maculans. Bioorganic & Medicinal Chemistry, 15, 6054-6061.
70. Pedras MSC, Zheng QA, Sarma-Mamillapalle VK. (2007) The phytoalexins from Brassicaceae: Structure, biological activity, synthesis and biosynthesis. Natural Product Communications, 2, 319-330.
71. Pedras MSC, Biesenthal CJ. (2000) HPLC analyses of cultures of Phoma spp.: differentiation among groups and species through secondary metabolite profiles. Canadian Journal of Microbiology, 46, 685-691.
72. Pedras MSC, Chumala PB, Yu Y. (2007) The phytopathogenic fungi Leptosphaeria maculans and Leptosphaeria biglobosa: Chemotaxonomical characterization of isolates and metabolite production in different culture media. Canadian Journal of Microbiology, 53, 364-371.