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Characterisation of the biosynthetic pathway to agnestins A and B reveals the reductive route to chrysophanol in fungi
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 cl...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Royal Society of Chemistry
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6335632/ https://www.ncbi.nlm.nih.gov/pubmed/30746079 http://dx.doi.org/10.1039/c8sc03778g |
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author | 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. |
author_facet | 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. |
author_sort | Szwalbe, Agnieszka J. |
collection | PubMed |
description | 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. |
format | Online Article Text |
id | pubmed-6335632 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-63356322019-02-11 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. Chem Sci Chemistry 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. Royal Society of Chemistry 2018-11-26 /pmc/articles/PMC6335632/ /pubmed/30746079 http://dx.doi.org/10.1039/c8sc03778g Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0) |
spellingShingle | Chemistry 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. Characterisation of the biosynthetic pathway to agnestins A and B reveals the reductive route to chrysophanol in fungi |
title | Characterisation of the biosynthetic pathway to agnestins A and B reveals the reductive route to chrysophanol in fungi
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title_full | Characterisation of the biosynthetic pathway to agnestins A and B reveals the reductive route to chrysophanol in fungi
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title_fullStr | Characterisation of the biosynthetic pathway to agnestins A and B reveals the reductive route to chrysophanol in fungi
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title_full_unstemmed | Characterisation of the biosynthetic pathway to agnestins A and B reveals the reductive route to chrysophanol in fungi
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title_short | Characterisation of the biosynthetic pathway to agnestins A and B reveals the reductive route to chrysophanol in fungi
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title_sort | characterisation of the biosynthetic pathway to agnestins a and b reveals the reductive route to chrysophanol in fungi |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6335632/ https://www.ncbi.nlm.nih.gov/pubmed/30746079 http://dx.doi.org/10.1039/c8sc03778g |
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