Chemical Ecogenomics-Guided Discovery of Phytotoxic α-Pyrones from the Fungal Wheat Pathogen Parastagonospora nodorum

Hang Li; Jinyu Hu; Haochen Wei; Peter S. Solomon; Daniel Vuong; Ernest Lacey; Keith A. Stubbs; Andrew M. Piggott; Yit Heng Chooi

doi:10.1021/acs.orglett.8b02617

Chemical Ecogenomics-Guided Discovery of Phytotoxic α-Pyrones from the Fungal Wheat Pathogen Parastagonospora nodorum

Hang Li, Jinyu Hu, Haochen Wei, Peter S. Solomon, Daniel Vuong, Ernest Lacey, Keith A. Stubbs, Andrew M. Piggott, Yit Heng Chooi

School of Molecular Sciences

Research output: Contribution to journal › Article › peer-review

25 Citations (Web of Science)

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Abstract

A biosynthetic gene cluster that is significantly upregulated in the fungal wheat pathogen Parastagonospora nodorum during plant infection was reconstructed heterologously in Aspergillus nidulans. This led to the discovery of five new α-pyrone polyketides, alternapyrones B-F (2-6). Compounds 5 and 6, which contain a highly substituted dihydrofuran, exhibited phytotoxicity on wheat seed germination. It is demonstrated that only three enzymes, one highly reducing polyketide synthase and two multifunctional P450 oxygenases, are needed to synthesize the structurally complex products.

Original language	English
Pages (from-to)	6148-6152
Number of pages	5
Journal	Organic Letters
Volume	20
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.8b02617
Publication status	Published - 5 Oct 2018

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10.1021/acs.orglett.8b02617

Li et al., 2018Chemical Ecogenomics-Guided Discovery of Phytotoxic α-Pyrones from the Fungal Wheat Pathogen Parastagonospora nodorumAccepted author manuscript, 1.86 MB

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title = "Chemical Ecogenomics-Guided Discovery of Phytotoxic α-Pyrones from the Fungal Wheat Pathogen Parastagonospora nodorum",

abstract = "A biosynthetic gene cluster that is significantly upregulated in the fungal wheat pathogen Parastagonospora nodorum during plant infection was reconstructed heterologously in Aspergillus nidulans. This led to the discovery of five new α-pyrone polyketides, alternapyrones B-F (2-6). Compounds 5 and 6, which contain a highly substituted dihydrofuran, exhibited phytotoxicity on wheat seed germination. It is demonstrated that only three enzymes, one highly reducing polyketide synthase and two multifunctional P450 oxygenases, are needed to synthesize the structurally complex products.",

author = "Hang Li and Jinyu Hu and Haochen Wei and Solomon, {Peter S.} and Daniel Vuong and Ernest Lacey and Stubbs, {Keith A.} and Piggott, {Andrew M.} and Chooi, {Yit Heng}",

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Chemical Ecogenomics-Guided Discovery of Phytotoxic α-Pyrones from the Fungal Wheat Pathogen Parastagonospora nodorum. / Li, Hang; Hu, Jinyu; Wei, Haochen; Solomon, Peter S.; Vuong, Daniel; Lacey, Ernest; Stubbs, Keith A.; Piggott, Andrew M.; Chooi, Yit Heng.

In: Organic Letters, Vol. 20, No. 19, 05.10.2018, p. 6148-6152.

Research output: Contribution to journal › Article › peer-review

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T1 - Chemical Ecogenomics-Guided Discovery of Phytotoxic α-Pyrones from the Fungal Wheat Pathogen Parastagonospora nodorum

AU - Li, Hang

AU - Hu, Jinyu

AU - Wei, Haochen

AU - Solomon, Peter S.

AU - Vuong, Daniel

AU - Lacey, Ernest

AU - Stubbs, Keith A.

AU - Piggott, Andrew M.

AU - Chooi, Yit Heng

PY - 2018/10/5

Y1 - 2018/10/5

N2 - A biosynthetic gene cluster that is significantly upregulated in the fungal wheat pathogen Parastagonospora nodorum during plant infection was reconstructed heterologously in Aspergillus nidulans. This led to the discovery of five new α-pyrone polyketides, alternapyrones B-F (2-6). Compounds 5 and 6, which contain a highly substituted dihydrofuran, exhibited phytotoxicity on wheat seed germination. It is demonstrated that only three enzymes, one highly reducing polyketide synthase and two multifunctional P450 oxygenases, are needed to synthesize the structurally complex products.

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JO - Organic Letters

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Chemical Ecogenomics-Guided Discovery of Phytotoxic α-Pyrones from the Fungal Wheat Pathogen Parastagonospora nodorum

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Two new phytotoxins in Septoria nodorum blotch: Biosynthesis and functions

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Chemical Ecogenomics-Guided Discovery of Phytotoxic α-Pyrones from the Fungal Wheat Pathogen Parastagonospora nodorum

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Two new phytotoxins in Septoria nodorum blotch: Biosynthesis and functions

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