Genome Mining of Aspergillus hancockii Unearths Cryptic Polyketide Hancockinone A Featuring a Prenylated 6/6/6/5 Carbocyclic Skeleton

Hang Li, Si Shu, John A. Kalaitzis, Zhuo Shang, Daniel Vuong, Andrew Crombie, Ernest Lacey, Andrew M. Piggott, and Yit-Heng Chooi

Org. Lett. 2021, 23, 8789–8793

Publication Date: November 8, 2021


Activation of a cryptic polyketide synthase gene cluster hkn from Aspergillus hancockii via overexpression of the gene-cluster-specific transcription factor HknR led to the discovery of a novel polycyclic metabolite, which we named hancockinone A. The compound features an unprecedented prenylated 6/6/6/5 tetracarbocyclic skeleton and shows moderate antibacterial activity. Heterologous expression, substrate feeding, and in vitro assays confirmed the role of cytochrome P450 HknE in constructing the five-membered ring in hancockinone A from the precursor neosartoricin B.

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