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Bovistol B, bovistol D and strossmayerin: Sesquiterpene metabolites from the culture filtrate of the basidiomycete Coprinopsis strossmayeri

Basidiomycete fungi are a rich source of natural products with a diverse array of potentially exploitable bioactivities. Two dimeric sesquiterpenes, bovistol B (1) and D (2), and one monomeric sesquiterpene, strossmayerin (7), were isolated from the culture filtrate of the basidiomycete fungus Copri...

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Autores principales: Banks, Alice M., Song, Lijiang, Challis, Gregory L., Bailey, Andy M., Foster, Gary D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Public Library of Science 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7135263/
https://www.ncbi.nlm.nih.gov/pubmed/32251434
http://dx.doi.org/10.1371/journal.pone.0229925
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author Banks, Alice M.
Song, Lijiang
Challis, Gregory L.
Bailey, Andy M.
Foster, Gary D.
author_facet Banks, Alice M.
Song, Lijiang
Challis, Gregory L.
Bailey, Andy M.
Foster, Gary D.
author_sort Banks, Alice M.
collection PubMed
description Basidiomycete fungi are a rich source of natural products with a diverse array of potentially exploitable bioactivities. Two dimeric sesquiterpenes, bovistol B (1) and D (2), and one monomeric sesquiterpene, strossmayerin (7), were isolated from the culture filtrate of the basidiomycete fungus Coprinopsis strossmayeri. The structures were determined through a combination of MS and 1D/2D NMR spectroscopic techniques. Likely monomeric precursors, identified on the basis of HRMS analysis, allow a plausible biosynthetic pathway to be proposed for the biosynthesis of 1 and 2, involving the dimerisation of the monomer through a hetero-Diels-Alder mechanism. A gene cluster, including a putative sesquiterpene 1–11 cyclase, was identified through phylogenetic and RNA-seq analysis, and is proposed to be responsible for the biosynthesis of 1 and 2.
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spelling pubmed-71352632020-04-09 Bovistol B, bovistol D and strossmayerin: Sesquiterpene metabolites from the culture filtrate of the basidiomycete Coprinopsis strossmayeri Banks, Alice M. Song, Lijiang Challis, Gregory L. Bailey, Andy M. Foster, Gary D. PLoS One Research Article Basidiomycete fungi are a rich source of natural products with a diverse array of potentially exploitable bioactivities. Two dimeric sesquiterpenes, bovistol B (1) and D (2), and one monomeric sesquiterpene, strossmayerin (7), were isolated from the culture filtrate of the basidiomycete fungus Coprinopsis strossmayeri. The structures were determined through a combination of MS and 1D/2D NMR spectroscopic techniques. Likely monomeric precursors, identified on the basis of HRMS analysis, allow a plausible biosynthetic pathway to be proposed for the biosynthesis of 1 and 2, involving the dimerisation of the monomer through a hetero-Diels-Alder mechanism. A gene cluster, including a putative sesquiterpene 1–11 cyclase, was identified through phylogenetic and RNA-seq analysis, and is proposed to be responsible for the biosynthesis of 1 and 2. Public Library of Science 2020-04-06 /pmc/articles/PMC7135263/ /pubmed/32251434 http://dx.doi.org/10.1371/journal.pone.0229925 Text en © 2020 Banks et al http://creativecommons.org/licenses/by/4.0/ This is an open access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/) , which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.
spellingShingle Research Article
Banks, Alice M.
Song, Lijiang
Challis, Gregory L.
Bailey, Andy M.
Foster, Gary D.
Bovistol B, bovistol D and strossmayerin: Sesquiterpene metabolites from the culture filtrate of the basidiomycete Coprinopsis strossmayeri
title Bovistol B, bovistol D and strossmayerin: Sesquiterpene metabolites from the culture filtrate of the basidiomycete Coprinopsis strossmayeri
title_full Bovistol B, bovistol D and strossmayerin: Sesquiterpene metabolites from the culture filtrate of the basidiomycete Coprinopsis strossmayeri
title_fullStr Bovistol B, bovistol D and strossmayerin: Sesquiterpene metabolites from the culture filtrate of the basidiomycete Coprinopsis strossmayeri
title_full_unstemmed Bovistol B, bovistol D and strossmayerin: Sesquiterpene metabolites from the culture filtrate of the basidiomycete Coprinopsis strossmayeri
title_short Bovistol B, bovistol D and strossmayerin: Sesquiterpene metabolites from the culture filtrate of the basidiomycete Coprinopsis strossmayeri
title_sort bovistol b, bovistol d and strossmayerin: sesquiterpene metabolites from the culture filtrate of the basidiomycete coprinopsis strossmayeri
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7135263/
https://www.ncbi.nlm.nih.gov/pubmed/32251434
http://dx.doi.org/10.1371/journal.pone.0229925
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