The metabolites produced by the fungal species Leptosphaeria maculans and L. biglobosa under different culture conditions, together with their phytotoxic activities are reviewed. In addition, the biosynthetic studies of blackleg metabolites carried out to date are described and suggestions for species reclassification are provided.
FittBDL, BrunH, BarbettiMJ, RimmerSR. (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.
HowlettBJ, IdnurmA, PedrasMSC. (2001) Leptosphaeria maculans, the causal agent of blackleg disease of Brassicas. Fungal Genetics and Biology, 33, 1–14.
3.
ChenY, FernandoWGD. (2006) Prevalence of pathogenicity groups of Leptosphaeria maculans in western Canada and North Dakota, USA. Canadian Journal of Plant Pathology, 28, 533–539.
4.
KutcherHR, KeriM, McLarenDL, RimmerSR. (2007) Pathogenic variability of Leptosphaeria maculans in western Canada. Canadian Journal of Plant Pathology, 29, 388–393.
5.
WolpertTJ, DunkleLD, CiuffettiLM. (2002) Host-selective toxins and avirulence determinants: what's in a name?Annual Review of Phytopathology, 40, 251–285.
6.
StrangeRN. (2007) Phytotoxins produced by microbial plant pathogens. Natural Product Reports, 24, 127–144.
7.
TharayilN, BhowmikP, AlpertP, WalkerE, AmarasiriwardenaD, XingB. (2009) Dual purpose secondary compounds: phytotoxin of Centaurea diffusa also facilitates nutrient uptake. New Phytologist, 181, 424–434.
8.
MontesanoM, BraderG, PalvaET. (2003) Pathogen derived elicitors: searching for receptors in plants. Molecular Plant Pathology, 4, 73–79.
9.
JonesDA, TakemotoD. (2004) Plant innate immunity: direct and indirect recognition of general and specific pathogen-associated molecules. Current Opinion in Immunology, 16, 48–62.
10.
NurnbergerT, BrunnerF, KemmerlingB, PiaterL. (2004) Inate immunity in plants and animals: striking similarities and obvious differences. Immunological Reviews, 198, 249–266.
11.
JonesJDG, DanglJL. (2006) The plant immune system. Nature, 444, 323–329.
12.
WaltersD, WalshD, NewtonA, LyonG. (2005) Induced resistance for plant disease control: maximizing the efficacy of resistance elicitors. Phytopathology, 95, 1368–1373.
13.
BollerT. (1995) Chemoperception of microbial signals in plant-cells. Annual Review of Plant Physiology and Plant Molecular Biology, 46, 189–214.
14.
KloekAP, VerbskyML, SharmaSB, SchoelzJE, VogelJ, KlessigDF, KunkelBN. (2001) Resistance to Pseudomonas syringae conferred by an Arabidopsis thaliana coronatine-insensitive (coi1) mutation occurs through two distinct mechanisms. Plant Journal, 26, 509–522.
15.
AllwoodJW, EllisDI, GoodacreR. (2008) Biomarker metabolites capturing the metabolite variance present in a rice plant developmental period. Physiologia Plantarum, 132, 117–135.
16.
ElyashbergME, WilliamsA, MartinGE. (2008) Computer-assisted structure verification and elucidation tools in NMR-based structure elucidation. Progress in Nuclear Magnetic Resonance spectroscopy, 53, 1–104.
17.
NuzillardJM, EmerencianoVDP. (2006) Automatic structure elucidation through data base search and 2D NMR spectral analysis. Natural Product Communications, 1, 57–64.
18.
KuhnS, EgertB, NeumannS, SteinbeckC. (2008) Building blocks for automated elucidation of metabolites: Machine learning methods for NMR prediction. BMC Bioinformatics, 9, 400.
19.
SteinbeckC. (2004) Recent developments in automated structure elucidation of natural products. Natural Product Reports, 21, 512–518.
20.
PedrasMSC. (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.
McGeeDC, PetrieGA. (1978) variability of Leptosphaeria maculans in relation to blackleg of oilseed rape. Phytopathology, 68, 625–630.
22.
WilliamsRH, FittBDL. (1999) Differentiating A and B groups of Leptosphaeria maculans, causal agent of stem canker (blackleg) of oilseed rape. Plant Pathology, 48, 161–175.
23.
ShoemakerRA, BrunH. (2001) The teleomorph of the weakly aggressive segregate of Leptosphaeria maculans. Canadian Journal of Botany, 79, 412–419.
24.
TaylorJL, PedrasMSC, MoralesVM. (1995) Horizontal transfer in the phytopathogenic fungal genus Leptosphaeria and hostrange expansion. Trends in Microbiology, 3, 202–206.
25.
PedrasMSC, TaylorJL, MoralesVM. (1995) Phomaligin A and other yellow pigments in Phoma lingam and P. wasabiae. Phytochemistry, 38, 1215–1222.
26.
ElliottCE, GardinerDM, ThomasG, CozijnsenA, De WouwAV, HowlettBJ. (2007) Production of the toxin sirodesmin PL by Leptosphaeria maculans during infection of Brassica napus. Molecular Plant Pathology, 8, 791–802.
27.
FérézouJP, RicheC, Quesneau-ThierryA, Pascard-BillyC, BarbierM, BousquetJF, BoudartG. (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.
PedrasMSC, AbramsSR, Séguin-SwartzG. (1988) Isolation of the first naturally occurring epimonothiodioxopiperazine, a fungal toxin produced by Phoma lingam. Tetrahedron Letters, 29, 3471–3474.
29.
PedrasMSC, Séguin-SwartzG, AbramsSR. (1990) Minor phytotoxins from the blackleg fungus Phoma lingam. Phytochemistry, 29, 777–782.
30.
HurneAM, ChaiCLL, MoermanK, WaringP. (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.
31.
HurneAM, ChaiCLL, WaringP. (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.
PedrasMSC, AbramsSR, Séguin-SwartzG, QuailJW, JiaZC. (1989) Phomalirazine, a novel toxin from the phytopathogenic fungus Phoma lingam. Journal of the American Chemical Society, 111, 1904–1905.
33.
PedrasMSC, YuY. (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.
PedrasMSC, SmithKC, TaylorJL. (1998) Production of 2,5-dioxopiperazine by a new isolate type of the blackleg fungus Phoma lingam. Phytochemistry, 49, 1575–1577.
35.
PedrasMSC, BiesenthalCJ. (2001) Isolation, structure determination, and phytotoxicity of unusual dioxopiperazines from the phytopathogenic fungus Phoma lingam. Phytochemistry, 58, 905–909.
36.
PedrasMSC, ChumalaPB. (2005) Phomapyrones from blackleg causing phytopathogenic fungi: isolation, structure determination, biosyntheses and biological activity. Phytochemistry, 66, 81–87.
37.
PedrasMSC, TaylorJL, NakashimaTT. (1993) A novel chemical signal from the “blackleg” fungus: beyond phytotoxins and phytoalexins. Journal of Organic Chemistry, 58, 4778–4780.
38.
PedrasMSC, BiesenthalCJ. (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.
WardDE, VazquezA, PedrasMSC. (1999) Probing host-selective phytotoxicity: Synthesis and biological activity of phomalide, isophomalide, and dihydrophomalide. Journal of Organic Chemistry, 64, 1657–1666.
40.
PedrasMSC, ChumalaPB, QuailJW, (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.
PardeshiSG, WardDE. (2008) Enantiospecific total synthesis of lairdinol A. Journal of Organic Chemistry, 73, 1071–1076.
42.
PedrasMSC, Erosa-LopezCC, QuailJW, TaylorJL. (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.
PedrasMSC, ChumalaPB, VenkateshamU. (2005) New sesquiterpenic phytotoxins establish unprecedented relationship between different groups of blackleg fungal isolates. Bioorganic & Medicinal Chemistry, 13, 2469–2475.
44.
CorbettRE., SmithRAJ. (1967) Selin-11-en-4alpha-ol from essential oil of Podocarpus dacrydioides. Tetrahedron Letters, 1009–1012.
45.
BohlmannF, MisraLN, JakupovicJ, RobinsonH, KingRM. (1984) New sesquiterpene lactone type from Dugaldia hoopesii. Journal of Natural Products, 47, 658–662.
46.
GriffithsKM, BacicA, HowlettBJ. (2003) Sterol composition of mycelia of the plant pathogenic ascomycete Leptosphaeria maculans. Phytochemistry, 62, 147–153.
47.
PedrasMSC, MoralesVM, TaylorJL. (1994) Phomapyrones: three metabolites from the blackleg fungus. Phytochemistry, 36, 1315–1318.
48.
LarsenTO, PerryNB., AndersenB. (2003) Infectopyrone, a potential mycotoxin from Alternaria infectoria. Tetrahedron Letters, 44, 4511–4513.
49.
ParisiA, PiattelliM, TringaliC, LioGMD. (1993) Identification of the phytotoxin mellein in culture fluids of Phoma tracheiphila. Phytochemistry, 32, 865–867.
PedrasMSC, MoralesVM, TaylorJL, (1993) Phomaligols and phomaligadiones: new metabolites from the blackleg fungus. Tetrahedron, 49, 8317–8322.
52.
PedrasMSC. (1996) The chemistry of cyclohexenediones produced by the blackleg fungus. Canadian Journal of Chemistry, 74, 1597–1601.
53.
PedrasMSC, YuY. (2009) Salt stress induces production of melanin related metabolites in the phytopathogenic fungus Leptosphaeria maculans. Natural Product Communications, 4, 53–58.
54.
DahiyaJS, RimmerSR, (1988) Accumulation of flaviolin, 4-hydroxyscytalone and 2-hydroxyjuglone in tricyclazole-treated cultures of Leptosphaeria maculans. Phytochemistry, 27, 3481–3482.
55.
PedrasMSC, YuY. (2008) Structure and biological activity of maculansin A, a phytotoxin from the phytopathogenic fungus Leptosphaeria maculans. Phytochemistry, 69, 2966–2971.
56.
PedrasMSC, ChumalaPB, JinW, IslamMS, HauckDW. (2009) The phytopathogenic fungus Alternaria brassicicola: phytotoxin production and phytoalexin elicitation. Phytochemistry, 70, 394–402.
57.
PedrasMSC, ChumalaPB, YuY. (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.
JiaoY, YoshiharaT, AkimotoM, IchiharaA. (1994) Two phenolic compounds from Valsa ambiens. Bioscience Biotechnology and Biochemistry, 58, 784–785.
59.
KeenNT. (1975) specific elicitors of plant phytoalexin production - determinants of race specificity in pathogens. Science, 187, 74–75.
60.
HahnMG. (1996) Microbial elicitors and their receptors in plants. Annual Review of Phytopathology, 34, 387–412.
61.
YuY. (2008) Elicitors and phytotoxins from the blackleg fungus: structure, bioactivity and biosynthesis. University of Saskatchewan, 198 pp.
62.
UmemuraK, TaninoS, NagatsukaT, KogaJ, IwataM, NagashimaK, AmemiyaY. (2004) Cerebroside elicitor confers resistance to Fusarium disease in various plant species. Phytopathology, 94, 813–818.
63.
FérézouJP, Quesneau-ThierryA, BarbierM, KollmannA, BousquetJF. (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 TransactionsI, 113–115.
64.
Bu'LockJD, CloughLE, (1992) Sirodesmin biosynthesis. Australian Journal of Chemistry, 45, 39–45.
65.
FérézouJP, Quesneau-ThierryA, ServyC, ZissmannE, BarbierM. (1980) Sirodesmin PL biosynthesis in Phoma lingam tode. Journal of the Chemical Society, Perkin TransactionsI, 1739–1746.
66.
GardinerDM, CozijnsenAJ, WilsonLM, PedrasMSC, HowlettBJ. (2004) The sirodesmin biosynthetic gene cluster of the plant pathogenic fungus Leptosphaeria maculans. Molecular Microbiology, 53, 1307–1318.
67.
PedrasMSC, YuY. (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.
PedrasMSC, GadagiRS, JhaM, Sarma-MamillapalleVK. (2007) Detoxification of the phytoalexin brassinin by isolates of Leptosphaeria maculans pathogenic on brown mustard involves an inducible hydrolase. Phytochemistry, 68, 1572–1578
69.
PedrasMSC, JhaM, MinicZ, OkeolaOG. (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.
PedrasMSC, ZhengQA, Sarma-MamillapalleVK. (2007) The phytoalexins from Brassicaceae: Structure, biological activity, synthesis and biosynthesis. Natural Product Communications, 2, 319–330.
71.
PedrasMSC, BiesenthalCJ. (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.
PedrasMSC, ChumalaPB, YuY. (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.