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Structure revision of cryptosporioptides and determination of the genetic basis for dimeric xanthone biosynthesis in fungi

Claudio Greco Orcid Logo, Kate de Mattos-Shipley, Andrew M. Bailey Orcid Logo, Nicholas P. Mulholland, Jason L. Vincent, Christine L. Willis Orcid Logo, Russell J. Cox Orcid Logo, Thomas J. Simpson Orcid Logo

Chemical Science, Volume: 10, Issue: 10, Pages: 2930 - 2939

Swansea University Author: Claudio Greco Orcid Logo

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DOI (Published version): 10.1039/c8sc05126g

Abstract

Three novel dimeric xanthones, cryptosporioptides A–C were isolated from Cryptosporiopsis sp. 8999 and their structures elucidated. Methylation of cryptosporioptide A gave a methyl ester with identical NMR data to cryptosporioptide, a compound previously reported to have been isolated from the same...

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Published in: Chemical Science
ISSN: 2041-6520 2041-6539
Published: Royal Society of Chemistry (RSC) 2019
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URI: https://cronfa.swan.ac.uk/Record/cronfa61524
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last_indexed 2023-01-13T19:22:19Z
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spelling 2022-10-20T12:31:36.6751338 v2 61524 2022-10-10 Structure revision of cryptosporioptides and determination of the genetic basis for dimeric xanthone biosynthesis in fungi cacac6459bd7cf4a241f63661006036f 0000-0003-3067-0999 Claudio Greco Claudio Greco true false 2022-10-10 BGPS Three novel dimeric xanthones, cryptosporioptides A–C were isolated from Cryptosporiopsis sp. 8999 and their structures elucidated. Methylation of cryptosporioptide A gave a methyl ester with identical NMR data to cryptosporioptide, a compound previously reported to have been isolated from the same fungus. However, HRMS analysis revealed that cryptosporioptide is a symmetrical dimer, not a monomer as previously proposed, and the revised structure was elucidated by extensive NMR analysis. The genome of Cryptosporiopsis sp. 8999 was sequenced and the dimeric xanthone (dmx) biosynthetic gene cluster responsible for the production of the cryptosporioptides was identified. Gene disruption experiments identified a gene (dmxR5) encoding a cytochrome P450 oxygenase as being responsible for the dimerisation step late in the biosynthetic pathway. Disruption of dmxR5 led to the isolation of novel monomeric xanthones. Cryptosporioptide B and C feature an unusual ethylmalonate subunit: a hrPKS and acyl CoA carboxylase are responsible for its formation. Bioinformatic analysis of the genomes of several fungi producing related xanthones, e.g. the widely occurring ergochromes, and related metabolites allows detailed annotation of the biosynthetic genes, and a rational overall biosynthetic scheme for the production of fungal dimeric xanthones to be proposed. Journal Article Chemical Science 10 10 2930 2939 Royal Society of Chemistry (RSC) 2041-6520 2041-6539 21 1 2019 2019-01-21 10.1039/c8sc05126g COLLEGE NANME Biosciences Geography and Physics School COLLEGE CODE BGPS Swansea University We thank BBSRC (BB/J006289/1, BB/L01386X/1) and Syngenta for funding. LCMS instruments were provided by EPSRC (EP/F066104/1) and DFG (INST 187/621). 500 MHz NMR (EP/L011999/1) was provided by EPSRC. 2022-10-20T12:31:36.6751338 2022-10-10T17:25:36.8478898 Faculty of Science and Engineering School of Biosciences, Geography and Physics - Biosciences Claudio Greco 0000-0003-3067-0999 1 Kate de Mattos-Shipley 2 Andrew M. Bailey 0000-0002-7594-3703 3 Nicholas P. Mulholland 4 Jason L. Vincent 5 Christine L. Willis 0000-0002-3919-3642 6 Russell J. Cox 0000-0002-1844-0157 7 Thomas J. Simpson 0000-0003-0777-1935 8 61524__25517__253e946d66ec4bb5b300084ef4030323.pdf 61524_VoR.pdf 2022-10-20T12:30:32.9594790 Output 1859478 application/pdf Version of Record true This article is licensed under a Creative Commons Attribution 3.0 Unported Licence true eng http://creativecommons.org/licenses/by/3.0/
title Structure revision of cryptosporioptides and determination of the genetic basis for dimeric xanthone biosynthesis in fungi
spellingShingle Structure revision of cryptosporioptides and determination of the genetic basis for dimeric xanthone biosynthesis in fungi
Claudio Greco
title_short Structure revision of cryptosporioptides and determination of the genetic basis for dimeric xanthone biosynthesis in fungi
title_full Structure revision of cryptosporioptides and determination of the genetic basis for dimeric xanthone biosynthesis in fungi
title_fullStr Structure revision of cryptosporioptides and determination of the genetic basis for dimeric xanthone biosynthesis in fungi
title_full_unstemmed Structure revision of cryptosporioptides and determination of the genetic basis for dimeric xanthone biosynthesis in fungi
title_sort Structure revision of cryptosporioptides and determination of the genetic basis for dimeric xanthone biosynthesis in fungi
author_id_str_mv cacac6459bd7cf4a241f63661006036f
author_id_fullname_str_mv cacac6459bd7cf4a241f63661006036f_***_Claudio Greco
author Claudio Greco
author2 Claudio Greco
Kate de Mattos-Shipley
Andrew M. Bailey
Nicholas P. Mulholland
Jason L. Vincent
Christine L. Willis
Russell J. Cox
Thomas J. Simpson
format Journal article
container_title Chemical Science
container_volume 10
container_issue 10
container_start_page 2930
publishDate 2019
institution Swansea University
issn 2041-6520
2041-6539
doi_str_mv 10.1039/c8sc05126g
publisher Royal Society of Chemistry (RSC)
college_str Faculty of Science and Engineering
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hierarchy_top_id facultyofscienceandengineering
hierarchy_top_title Faculty of Science and Engineering
hierarchy_parent_id facultyofscienceandengineering
hierarchy_parent_title Faculty of Science and Engineering
department_str School of Biosciences, Geography and Physics - Biosciences{{{_:::_}}}Faculty of Science and Engineering{{{_:::_}}}School of Biosciences, Geography and Physics - Biosciences
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description Three novel dimeric xanthones, cryptosporioptides A–C were isolated from Cryptosporiopsis sp. 8999 and their structures elucidated. Methylation of cryptosporioptide A gave a methyl ester with identical NMR data to cryptosporioptide, a compound previously reported to have been isolated from the same fungus. However, HRMS analysis revealed that cryptosporioptide is a symmetrical dimer, not a monomer as previously proposed, and the revised structure was elucidated by extensive NMR analysis. The genome of Cryptosporiopsis sp. 8999 was sequenced and the dimeric xanthone (dmx) biosynthetic gene cluster responsible for the production of the cryptosporioptides was identified. Gene disruption experiments identified a gene (dmxR5) encoding a cytochrome P450 oxygenase as being responsible for the dimerisation step late in the biosynthetic pathway. Disruption of dmxR5 led to the isolation of novel monomeric xanthones. Cryptosporioptide B and C feature an unusual ethylmalonate subunit: a hrPKS and acyl CoA carboxylase are responsible for its formation. Bioinformatic analysis of the genomes of several fungi producing related xanthones, e.g. the widely occurring ergochromes, and related metabolites allows detailed annotation of the biosynthetic genes, and a rational overall biosynthetic scheme for the production of fungal dimeric xanthones to be proposed.
published_date 2019-01-21T05:39:36Z
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