Characterisation of the biosynthetic pathway to agnestins A and B reveals the reductive route to chrysophanol in fungi

Szwalbe, Agnieszka J; Williams, Katherine; Song, Zhongshu; De Mattos-Shipley, Kate; Vincent, Jason L; Bailey, Andrew M; Willis, Christine L; Cox, Russell J; Simpson, Thomas J

Abstract

Two new dihydroxy-xanthone metabolites, agnestins A and B, were isolated from Paecilomyces variotii along with a number of related benzophenones and xanthones including monodictyphenone. The structures were elucidated by NMR analyses and X-ray crystallography. The agnestin (agn) biosynthetic gene cluster was identified and targeted gene disruptions of the PKS, Baeyer-Villiger monooxygenase, and other oxido-reductase genes revealed new details of fungal xanthone biosynthesis. In particular, identification of a reductase responsible for in vivo anthraquinone to anthrol conversion confirms a previously postulated essential step in aromatic deoxygenation of anthraquinones, e.g. emodin to chrysophanol.

• Journal Article Type: Article
• Acceptance Date: Nov 23, 2018
• Online Publication Date: Nov 26, 2018
• Publication Date: Nov 26, 2018
• Deposit Date: Apr 10, 2024
• Publicly Available Date: Apr 10, 2024
• Journal: Chemical Science
• Print ISSN: 2041-6520
• Electronic ISSN: 2041-6539
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 10
• Issue: 1
• Pages: 233-238
• DOI: https://doi.org/10.1039/C8SC03778G
• Keywords: Synthetic Biology
• Public URL: https://uwe-repository.worktribe.com/output/11881298
• Publisher URL: http://dx.doi.org/10.1039/C8SC03778G