A search for stress metabolites produced by the plant pathogenic fungus Leptosphaeria maculans (asexual stage Phoma lingam) cultured in high salt medium led to the isolation and structure elucidation of two metabolites associated with melanin biosynthesis and cell melanization, a self-protection mechanism against salt stress. The chemical structures of the metabolites were deduced by detailed analysis of 1D and 2D NMR spectroscopic data and chemical transformations.
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.
2.
HowlettBJ, IdnurmA, PedrasMSC. (2001) Leptosphaeria maculans, the causal agent of blackleg disease of Brassicas. Fungal Genetics and Biology, 33, 1-14.
3.
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.
4.
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.
5.
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, 1, 327–334.
6.
PedrasMSC, YuY. (2008) Stress-driven discovery of metabolites from the phytopathogenic fungus Leptosphaeria maculans: structure and activity of leptomaculins A-E. Bioorganic and Medicinal Chemistry, 16, 8063–8071.
7.
PedrasMSC, AbramsSR, Séguin-SwartzG. (1988) Isolation of the first naturally occurring epimonothiodioxopiperazine, a fungal toxin produced byPhoma lingam. Tetrahedron Letters, 29, 3471–3474.
8.
PedrasMSC, Séguin-SwartzG, AbramsSR. (1990) Minor phytotoxins from the blackleg fungusPhoma lingam. Phytochemistry, 29, 777–782.
9.
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.
10.
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.
11.
PedrasMSC, TaylorJL, NakashimaTT. (1993) A novel chemical signal from the “blackleg” fungus: beyond phytotoxins and phytoalexins. Journal of Organic Chemistry, 58, 4778–4780.
12.
EdwardsRL, LockettHJ. (1976) Constituents of the higher fungi. Part XVI. Bulgarhodin and bulgarein, novel benzofluoranthenequinones from the fungus Bulgaria inquinans (Fries). Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry, 20, 2149–2155.
13.
FujiiN, YamashitaY, SaitohY, NakanoH. (1993) Induction of mammalian DNA topoisomerase I-mediated DNA cleavage and DNA winding by bulgarein. Journal of Biological Chemistry, 268, 13160–13165.
14.
EistertB, WollheimR, FinkG, MinasH, KleinL. (1968) Reactions of β-dicarbonyl compounds and quinones with diazo alkanes. IX. Other reactions of phenanthrene quinone with aliphatic diazo compounds. Chemische Berichte, 101, 84–93.
15.
LangfelderK, StreibelM, JahnB, HaaseG, BrakhageAA. (2003) Biosynthesis of fungal melanins and their importance for human pathogenic fungi. Fungal Genetics and Biology, 38, 143–158.
16.
NosanchukJD, CasadevallA. (2003) The contribution of melanin to microbial pathogenesis. Cellular Microbiology, 5, 203–223.
17.
Gunde-CimermanN, PlemenitasA. (2006) Ecology and molecular adaptations of the halophilic black yeastHortaea werneckii. Reviews in Environmental Science and Biotechnology, 5, 323–331.
18.
DahiyaJS, RimmerSR. (1988) Accumulation of flaviolin, 4-hydroxyscytalone and 2-hydroxyjuglone in tricyclazole-treated cultures ofLeptosphaeria maculans. Phytochemistry, 27, 3481–3482.
19.
BellAA, WheelerMH. (1986) Biosynthesis and functions of fungal melanins. Annual Review of Phytopathology, 24, 411–451.
20.
PedrasMSC, KhanAQ. (1996) Biotransformation of the brassica phytoalexin brassicanal A by the blackleg fungus. Journal of Agricultural and Food Chemistry, 44, 3403–3407.
21.
RagotJP, SteeneckC, AlcarazML, TaylorRJK. (1999) The synthesis of 1,8-dihydroxynaphthalene-derived natural products: palmarumycin CP1, palmarumycin CP2, palmarumycin C11, CJ-12,371, deoxypreussomerin A and novel analogs. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry, 8, 1073–1082.