Induced biosyntheses of a novel butyrophenone and two aromatic polyketides in the plant pathogen Stagonospora nodorum

Yang, Xiao‐Long; Awakawa, Takayoshi; Wakimoto, Toshiyuki; Abe, Ikuro

doi:10.1007/s13659-013-0055-2

Cited by 25 publications

(17 citation statements)

References 19 publications

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“…Given that secondary metabolites have been shown to be involved in fungal pathogenesis (Mobius and Hertweck, ; Collemare and Lebrun, ), it is reasonable to postulate that some of the secondary metabolites encoded by the 38 biosynthetic gene clusters in P. nodorum could play important roles in its interactions with the host. Despite previous efforts to uncover the phytotoxins and other secondary metabolites from P. nodorum (Devys et al ., 1978; 1980; 1982, 1992; Tan et al ., ; Yang et al ., ), this is the first report of a perylenequinone isolated from this important wheat pathogen. Nevertheless, elsinochromes have been isolated from related Stagonospora and Phaeosphaeria fungi (Nicolet and Tabacchi, ; Li et al ., ).…”

Section: Discussionmentioning

confidence: 99%

Functional genomics‐guided discovery of a light‐activated phytotoxin in the wheat pathogen Parastagonospora nodorum via pathway activation

Chooi

Zhang

et al. 2017

Environmental Microbiology

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Parastagonospora nodorum is an important pathogen of wheat. The contribution of secondary metabolites to this pathosystem is poorly understood. A biosynthetic gene cluster (SNOG_08608-08616) has been shown to be upregulated during the late stage of P. nodorum wheat leaf infection. The gene cluster shares several homologues with the Cercospora nicotianae CTB gene cluster encoding the biosynthesis of cercosporin. Activation of the gene cluster by overexpression (OE) of the transcription factor gene (SNOG_08609) in P. nodorum resulted in the production of elsinochrome C, a perelyenequinone phytotoxin structurally similar to cercosporin. Heterologous expression of the polyketide synthase gene elcA from the gene cluster in Aspergillus nidulans resulted in the production of the polyketide precursor nortoralactone common to the cercosporin pathway. Elsinochrome C could be detected on wheat leaves infected with P. nodorum, but not in the elcA disruption mutant. The compound was shown to exhibit necrotic activity on wheat leaves in a light-dependent manner. Wheat seedling infection assays showed that ΔelcA exhibited reduced virulence compared with wild type, while infection by an OE strain overproducing elsinochrome C resulted in larger lesions on leaves. These data provided evidence that elsinochrome C contributes to the virulence of P. nodorum against wheat.

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Section: Discussionmentioning

confidence: 99%

Functional genomics‐guided discovery of a light‐activated phytotoxin in the wheat pathogen Parastagonospora nodorum via pathway activation

Chooi

Zhang

et al. 2017

Environmental Microbiology

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“…The study found that the concentration of alternariol in the culture of an sch1 mutant strain is 200-fold greater than the wild-type P. nodorum , although the relationship between sch1 and alternariol biosynthesis is still unknown. Another new compound, (+)-4ʹ-methoxy-(2S)-methylbutyrophenone ( Figure 2 ), was isolated from P. nodorum recently by supplementing epigenetic modifiers to the culture medium (Yang et al 2013 ). These two most recent P. nodorum SM studies have highlighted that both genetic and epigenetic approaches can be used to induce the expression of otherwise silent SM pathways in laboratory culture conditions (Brakhage & Schroeckh 2011 ).…”

Section: Parastagonospora Nodorum Pathobiology and Secondarymentioning

confidence: 99%

“…So far, all characterized fungal PR-PKSs were shown to produce 6-methylsalicylic acid ( Figure 3 ). Since no 6-methylsalicylic acid has been isolated from P. nodorum and SNOG_00477 is the only PR-PKS in P. nodorum , this makes SNOG_00477 a promising candidate PKS gene for mellein production (Yang et al 2013 ). SNOG_14927 is another possible candidate PKS suggested by Yang et al ( 2013 ); it has the identical domain architecture as SNOG_00477 and 6-methylsalicylic acid PR-PKSs.…”

Section: Genomic Outlook For the Sm Biosynthetic Potential Of mentioning

confidence: 99%

A genome-wide survey of the secondary metabolite biosynthesis genes in the wheat pathogenParastagonospora nodorum

2014

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The model pathogen Parastagonospora nodorum is a necrotroph and the causal agent of the wheat disease Septoria nodorum blotch (SNB). The sequenced P. nodorum genome has revealed that the fungus harbours a large number of secondary metabolite genes. Secondary metabolites are known to play important roles in the virulence of plant pathogens, but limited knowledge is available about the SM repertoire of this wheat pathogen. Here, we review the secondary metabolites that have been isolated from P. nodorum and related species of the same genus and provide an in-depth genome-wide overview of the secondary metabolite gene clusters encoded in the P. nodorum genome. The secondary metabolite gene survey reveals that P. nodorum is capable of producing a diverse range of small molecules and exciting prospects exist for discovery of novel virulence factors and bioactive molecules.

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“…So far, none of the products of these secondary metabolite gene clusters have been identified, and only a few secondary metabolites have been identified in this species (7). These metabolites include (R)-mellein and derivatives (8,9), septorines (10,11), mycophenolic acid (8), alternariol (12), and (ϩ)-4=-methoxy-(2S)-methylbutyrophenone (13).…”

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confidence: 99%

An In Planta -Expressed Polyketide Synthase Produces ( R )-Mellein in the Wheat Pathogen Parastagonospora nodorum

Chooi

Krill

Barrow

et al. 2015

Appl Environ Microbiol

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dParastagonospora nodorum is a pathogen of wheat that affects yields globally. Previous transcriptional analysis identified a partially reducing polyketide synthase (PR-PKS) gene, SNOG_00477 (SN477), in P. nodorum that is highly upregulated during infection of wheat leaves. Disruption of the corresponding SN477 gene resulted in the loss of production of two compounds, which we identified as (R)-mellein and (R)-O-methylmellein. Using a Saccharomyces cerevisiae yeast heterologous expression system, we successfully demonstrated that SN477 is the only enzyme required for the production of (R)-mellein. This is the first identification of a fungal PKS that is responsible for the synthesis of (R)-mellein. The P. nodorum ⌬SN477 mutant did not show any significant difference from the wild-type strain in its virulence against wheat. However, (R)-mellein at 200 g/ml inhibited the germination of wheat (Triticum aestivum) and barrel medic (Medicago truncatula) seeds. Comparative sequence analysis identified the presence of mellein synthase (MLNS) homologues in several Dothideomycetes and two sodariomycete genera. Phylogenetic analysis suggests that the MLNSs in fungi and bacteria evolved convergently from fungal and bacterial 6-methylsalicylic acid synthases.

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Induced biosyntheses of a novel butyrophenone and two aromatic polyketides in the plant pathogen Stagonospora nodorum

Cited by 25 publications

References 19 publications

Functional genomics‐guided discovery of a light‐activated phytotoxin in the wheat pathogen Parastagonospora nodorum via pathway activation

Functional genomics‐guided discovery of a light‐activated phytotoxin in the wheat pathogen Parastagonospora nodorum via pathway activation

A genome-wide survey of the secondary metabolite biosynthesis genes in the wheat pathogenParastagonospora nodorum

An In Planta -Expressed Polyketide Synthase Produces ( R )-Mellein in the Wheat Pathogen Parastagonospora nodorum

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