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

doi:10.1039/C8SC03778G

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 journal › Article (Academic Journal) › peer-review

50 Citations (Scopus)

304 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 language	English
Pages (from-to)	233-238
Number of pages	6
Journal	Chemical Science
Volume	10
Issue number	1
DOIs	https://doi.org/10.1039/C8SC03778G
Publication status	Published - 7 Jan 2019

Research Groups and Themes

BrisSynBio
Bristol BioDesign Institute
Organic & Biological

Keywords

synthetic biology
Synthetic Biology

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

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.",

keywords = "synthetic biology, Synthetic Biology",

author = "Szwalbe, \{Agnieszka J.\} and Katherine Williams and Zhongshu Song and \{De Mattos-Shipley\}, Kate and Vincent, \{Jason L.\} and Bailey, \{Andrew M.\} and Willis, \{Christine L.\} and Cox, \{Russell J.\} and Simpson, \{Thomas J.\}",

year = "2019",

month = jan,

day = "7",

doi = "10.1039/C8SC03778G",

language = "English",

volume = "10",

pages = "233--238",

journal = "Chemical Science",

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T1 - Characterisation of the biosynthetic pathway to agnestins A and B reveals the reductive route to chrysophanol in fungi

AU - Szwalbe, Agnieszka J.

AU - Williams, Katherine

AU - Song, Zhongshu

AU - De Mattos-Shipley, Kate

AU - Vincent, Jason L.

AU - Bailey, Andrew M.

AU - Willis, Christine L.

AU - Cox, Russell J.

AU - Simpson, Thomas J.

PY - 2019/1/7

Y1 - 2019/1/7

N2 - 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.

AB - 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.

KW - synthetic biology

KW - Synthetic Biology

UR - https://www.scopus.com/pages/publications/85059139651

U2 - 10.1039/C8SC03778G

DO - 10.1039/C8SC03778G

M3 - Article (Academic Journal)

C2 - 30746079

AN - SCOPUS:85059139651

SN - 2041-6520

VL - 10

SP - 233

EP - 238

JO - Chemical Science

JF - Chemical Science

IS - 1

ER -

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

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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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Research Groups and Themes

Keywords

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BrisSynBio: Bristol Centre for Synthetic Biology

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