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^*

^*Corresponding author for this work

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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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Copyright the Publisher 2018. Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher.

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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.",

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doi = "10.1021/acs.orglett.8b02617",

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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

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AB - 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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