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Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery
The heronapyrroles A–C have first been isolated from a marine-derived Streptomyces sp. (CMB-0423) in 2010. Structurally, these natural products feature an unusual nitropyrrole system to which a partially oxidized farnesyl chain is attached. The varying degree of oxidation of the sesquiterpenyl subun...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Beilstein-Institut
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077399/ https://www.ncbi.nlm.nih.gov/pubmed/24991272 http://dx.doi.org/10.3762/bjoc.10.121 |
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author | Schmidt, Jens Khalil, Zeinab Capon, Robert J Stark, Christian B W |
author_facet | Schmidt, Jens Khalil, Zeinab Capon, Robert J Stark, Christian B W |
author_sort | Schmidt, Jens |
collection | PubMed |
description | The heronapyrroles A–C have first been isolated from a marine-derived Streptomyces sp. (CMB-0423) in 2010. Structurally, these natural products feature an unusual nitropyrrole system to which a partially oxidized farnesyl chain is attached. The varying degree of oxidation of the sesquiterpenyl subunit in heronapyrroles A–C provoked the hypothesis that there might exist other hitherto unidentified metabolites. On biosynthetic grounds a mono-tetrahydrofuran-diol named heronapyrrole D appeared a possible candidate. We here describe a short asymmetric synthesis of heronapyrrole D, its detection in cultivations of CMB-0423 and finally the evaluation of its antibacterial activity. We thus demonstrate that biosynthetic considerations and the joint effort of synthetic and natural product chemists can result in the identification of new members of a rare class of natural products. |
format | Online Article Text |
id | pubmed-4077399 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-40773992014-07-02 Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery Schmidt, Jens Khalil, Zeinab Capon, Robert J Stark, Christian B W Beilstein J Org Chem Letter The heronapyrroles A–C have first been isolated from a marine-derived Streptomyces sp. (CMB-0423) in 2010. Structurally, these natural products feature an unusual nitropyrrole system to which a partially oxidized farnesyl chain is attached. The varying degree of oxidation of the sesquiterpenyl subunit in heronapyrroles A–C provoked the hypothesis that there might exist other hitherto unidentified metabolites. On biosynthetic grounds a mono-tetrahydrofuran-diol named heronapyrrole D appeared a possible candidate. We here describe a short asymmetric synthesis of heronapyrrole D, its detection in cultivations of CMB-0423 and finally the evaluation of its antibacterial activity. We thus demonstrate that biosynthetic considerations and the joint effort of synthetic and natural product chemists can result in the identification of new members of a rare class of natural products. Beilstein-Institut 2014-05-26 /pmc/articles/PMC4077399/ /pubmed/24991272 http://dx.doi.org/10.3762/bjoc.10.121 Text en Copyright © 2014, Schmidt et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
spellingShingle | Letter Schmidt, Jens Khalil, Zeinab Capon, Robert J Stark, Christian B W Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery |
title | Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery |
title_full | Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery |
title_fullStr | Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery |
title_full_unstemmed | Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery |
title_short | Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery |
title_sort | heronapyrrole d: a case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery |
topic | Letter |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077399/ https://www.ncbi.nlm.nih.gov/pubmed/24991272 http://dx.doi.org/10.3762/bjoc.10.121 |
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