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

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

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

13 Citations (Scopus)
187 Downloads (Pure)

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.

Original languageEnglish
Pages (from-to)233-238
Number of pages6
JournalChemical Science
Volume10
Issue number1
DOIs
Publication statusPublished - 7 Jan 2019

Structured keywords

  • BrisSynBio
  • Bristol BioDesign Institute

Keywords

  • Synthetic Biology

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