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

    Research output: Contribution to journalArticlepeer-review

    23 Citations (Scopus)
    23 Downloads (Pure)

    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 languageEnglish
    Pages (from-to)6148–6152
    Number of pages5
    JournalOrganic Letters
    Volume20
    Issue number19
    DOIs
    Publication statusPublished - 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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