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

Research output: Contribution to journalArticle

4 Citations (Scopus)

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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Pyrones
Polyketide Synthases
Polyketides
Oxygenases
wheat
pathogens
Aspergillus
Pathogens
Triticum
Seed
Genes
germination
Aspergillus nidulans
infectious diseases
Enzymes
Multigene Family
Germination
genes
enzymes
seeds

Cite this

Li, Hang ; Hu, Jinyu ; Wei, Haochen ; Solomon, Peter S. ; Vuong, Daniel ; Lacey, Ernest ; Stubbs, Keith A. ; Piggott, Andrew M. ; Chooi, Yit Heng. / Chemical Ecogenomics-Guided Discovery of Phytotoxic α-Pyrones from the Fungal Wheat Pathogen Parastagonospora nodorum. In: Organic Letters. 2018 ; Vol. 20, No. 19. pp. 6148-6152.
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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 journalArticle

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