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

Research output: Contribution to journalArticleResearchpeer review

Authors

  • 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

External Research Organisations

  • University of Bristol
  • Syngenta
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Details

Original languageEnglish
Pages (from-to)233-238
Number of pages6
JournalChemical science
Volume10
Issue number1
Publication statusPublished - 1 Jan 2019
Externally publishedYes

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.

ASJC Scopus subject areas

Cite this

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 et al.
In: Chemical science, Vol. 10, No. 1, 01.01.2019, p. 233-238.

Research output: Contribution to journalArticleResearchpeer review

Szwalbe, AJ, Williams, K, Song, Z, De Mattos-Shipley, K, Vincent, JL, Bailey, AM, Willis, CL, Cox, RJ & Simpson, TJ 2019, 'Characterisation of the biosynthetic pathway to agnestins A and B reveals the reductive route to chrysophanol in fungi', Chemical science, vol. 10, no. 1, pp. 233-238. https://doi.org/10.1039/C8SC03778G
Szwalbe, A. J., Williams, K., Song, Z., De Mattos-Shipley, K., Vincent, J. L., Bailey, A. M., Willis, C. L., Cox, R. J., & Simpson, T. J. (2019). Characterisation of the biosynthetic pathway to agnestins A and B reveals the reductive route to chrysophanol in fungi. Chemical science, 10(1), 233-238. https://doi.org/10.1039/C8SC03778G
Szwalbe AJ, Williams K, Song Z, De Mattos-Shipley K, Vincent JL, Bailey AM et al. Characterisation of the biosynthetic pathway to agnestins A and B reveals the reductive route to chrysophanol in fungi. Chemical science. 2019 Jan 1;10(1):233-238. doi: 10.1039/C8SC03778G
Szwalbe, Agnieszka J. ; Williams, Katherine ; Song, Zhongshu et al. / Characterisation of the biosynthetic pathway to agnestins A and B reveals the reductive route to chrysophanol in fungi. In: Chemical science. 2019 ; Vol. 10, No. 1. pp. 233-238.
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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.",
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AU - Williams, Katherine

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AU - De Mattos-Shipley, Kate

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