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Four new suomilides isolated from the cyanobacterium Nostoc sp. KVJ20 and proposal of their biosynthetic origin

The suomilide and the banyasides are highly modified and functionalized non-ribosomal peptides produced by cyanobacteria of the order Nostocales. These compound classes share several substructures, including a complex azabicyclononane core, which was previously assumed to be derived from the amino a...

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Autores principales: Schneider, Yannik K.-H., Liaimer, Anton, Isaksson, Johan, Wilhelmsen, Oda S. B., Andersen, Jeanette H., Hansen, Kine Ø., Hansen, Espen H.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10157211/
https://www.ncbi.nlm.nih.gov/pubmed/37152725
http://dx.doi.org/10.3389/fmicb.2023.1130018
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author Schneider, Yannik K.-H.
Liaimer, Anton
Isaksson, Johan
Wilhelmsen, Oda S. B.
Andersen, Jeanette H.
Hansen, Kine Ø.
Hansen, Espen H.
author_facet Schneider, Yannik K.-H.
Liaimer, Anton
Isaksson, Johan
Wilhelmsen, Oda S. B.
Andersen, Jeanette H.
Hansen, Kine Ø.
Hansen, Espen H.
author_sort Schneider, Yannik K.-H.
collection PubMed
description The suomilide and the banyasides are highly modified and functionalized non-ribosomal peptides produced by cyanobacteria of the order Nostocales. These compound classes share several substructures, including a complex azabicyclononane core, which was previously assumed to be derived from the amino acid tyrosine. In our study we were able to isolate and determine the structures of four suomilides, named suomilide B – E (1–4). The compounds differ from the previously isolated suomilide A by the functionalization of the glycosyl group. Compounds 1–4 were assayed for anti-proliferative, anti-biofilm and anti-bacterial activities, but no significant activity was detected. The sequenced genome of the producer organism Nostoc sp. KVJ20 enabled us to propose a biosynthetic gene cluster for suomilides. Our findings indicated that the azabicyclononane core of the suomilides is derived from prephenate and is most likely incorporated by a proline specific non-ribosomal peptide synthetase-unit.
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spelling pubmed-101572112023-05-05 Four new suomilides isolated from the cyanobacterium Nostoc sp. KVJ20 and proposal of their biosynthetic origin Schneider, Yannik K.-H. Liaimer, Anton Isaksson, Johan Wilhelmsen, Oda S. B. Andersen, Jeanette H. Hansen, Kine Ø. Hansen, Espen H. Front Microbiol Microbiology The suomilide and the banyasides are highly modified and functionalized non-ribosomal peptides produced by cyanobacteria of the order Nostocales. These compound classes share several substructures, including a complex azabicyclononane core, which was previously assumed to be derived from the amino acid tyrosine. In our study we were able to isolate and determine the structures of four suomilides, named suomilide B – E (1–4). The compounds differ from the previously isolated suomilide A by the functionalization of the glycosyl group. Compounds 1–4 were assayed for anti-proliferative, anti-biofilm and anti-bacterial activities, but no significant activity was detected. The sequenced genome of the producer organism Nostoc sp. KVJ20 enabled us to propose a biosynthetic gene cluster for suomilides. Our findings indicated that the azabicyclononane core of the suomilides is derived from prephenate and is most likely incorporated by a proline specific non-ribosomal peptide synthetase-unit. Frontiers Media S.A. 2023-04-20 /pmc/articles/PMC10157211/ /pubmed/37152725 http://dx.doi.org/10.3389/fmicb.2023.1130018 Text en Copyright © 2023 Schneider, Liaimer, Isaksson, Wilhelmsen, Andersen, Hansen and Hansen. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Microbiology
Schneider, Yannik K.-H.
Liaimer, Anton
Isaksson, Johan
Wilhelmsen, Oda S. B.
Andersen, Jeanette H.
Hansen, Kine Ø.
Hansen, Espen H.
Four new suomilides isolated from the cyanobacterium Nostoc sp. KVJ20 and proposal of their biosynthetic origin
title Four new suomilides isolated from the cyanobacterium Nostoc sp. KVJ20 and proposal of their biosynthetic origin
title_full Four new suomilides isolated from the cyanobacterium Nostoc sp. KVJ20 and proposal of their biosynthetic origin
title_fullStr Four new suomilides isolated from the cyanobacterium Nostoc sp. KVJ20 and proposal of their biosynthetic origin
title_full_unstemmed Four new suomilides isolated from the cyanobacterium Nostoc sp. KVJ20 and proposal of their biosynthetic origin
title_short Four new suomilides isolated from the cyanobacterium Nostoc sp. KVJ20 and proposal of their biosynthetic origin
title_sort four new suomilides isolated from the cyanobacterium nostoc sp. kvj20 and proposal of their biosynthetic origin
topic Microbiology
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10157211/
https://www.ncbi.nlm.nih.gov/pubmed/37152725
http://dx.doi.org/10.3389/fmicb.2023.1130018
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