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

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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.

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

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Publication details

The article was received on 23 Aug 2018, accepted on 23 Nov 2018 and first published on 26 Nov 2018


Article type: Edge Article
DOI: 10.1039/C8SC03778G
Citation: Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY license
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    Characterisation of the biosynthetic pathway to agnestins A and B reveals the reductive route to chrysophanol in fungi

    A. J. Szwalbe, K. Williams, Z. Song, K. de Mattos-Shipley, Jason L. Vincent, A. M. Bailey, C. L. Willis, R. J. Cox and T. J. Simpson, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C8SC03778G

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