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, and Yit-Heng Chooi

Org. Lett., 2018, 20, 6148–6152.

Publication Date: September 18, 2018


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 (26). 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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