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Balibalosides, an Original Family of Glucosylated Sesterterpenes Produced by the Mediterranean Sponge Oscarella balibaloi

The chemical investigation of the recently described Mediterranean Homoscleromorpha sponge Oscarella balibaloi revealed an original family of five closely related glucosylated sesterterpenes 1–4, named balibalosides. Their structure elucidation was mainly inferred from NMR and HRMS data analyses. Ba...

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Autores principales: Audoin, Coralie, Bonhomme, Dominique, Ivanisevic, Julijana, de la Cruz, Mercedes, Cautain, Bastien, Monteiro, Maria Cândida, Reyes, Fernando, Rios, Laurent, Perez, Thierry, Thomas, Olivier P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3707155/
https://www.ncbi.nlm.nih.gov/pubmed/23648552
http://dx.doi.org/10.3390/md11051477
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author Audoin, Coralie
Bonhomme, Dominique
Ivanisevic, Julijana
de la Cruz, Mercedes
Cautain, Bastien
Monteiro, Maria Cândida
Reyes, Fernando
Rios, Laurent
Perez, Thierry
Thomas, Olivier P.
author_facet Audoin, Coralie
Bonhomme, Dominique
Ivanisevic, Julijana
de la Cruz, Mercedes
Cautain, Bastien
Monteiro, Maria Cândida
Reyes, Fernando
Rios, Laurent
Perez, Thierry
Thomas, Olivier P.
author_sort Audoin, Coralie
collection PubMed
description The chemical investigation of the recently described Mediterranean Homoscleromorpha sponge Oscarella balibaloi revealed an original family of five closely related glucosylated sesterterpenes 1–4, named balibalosides. Their structure elucidation was mainly inferred from NMR and HRMS data analyses. Balibalosides differ by the pattern of acetyl substitutions on the three sugar residues linked to the same aglycone sesterterpenoid core. From a biosynthetic perspective, these compounds may represent intermediates in the pathways leading to more complex sesterterpenes frequently found in Dictyoceratida, a sponge Order belonging to Demospongiae, a clade which is phylogenetically distinct from the Homoscleromorpha. While steroid and triterpenoid saponins were already well known from marine sponges, balibalosides are the first examples of glycosilated sesterterpenes.
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spelling pubmed-37071552013-07-10 Balibalosides, an Original Family of Glucosylated Sesterterpenes Produced by the Mediterranean Sponge Oscarella balibaloi Audoin, Coralie Bonhomme, Dominique Ivanisevic, Julijana de la Cruz, Mercedes Cautain, Bastien Monteiro, Maria Cândida Reyes, Fernando Rios, Laurent Perez, Thierry Thomas, Olivier P. Mar Drugs Article The chemical investigation of the recently described Mediterranean Homoscleromorpha sponge Oscarella balibaloi revealed an original family of five closely related glucosylated sesterterpenes 1–4, named balibalosides. Their structure elucidation was mainly inferred from NMR and HRMS data analyses. Balibalosides differ by the pattern of acetyl substitutions on the three sugar residues linked to the same aglycone sesterterpenoid core. From a biosynthetic perspective, these compounds may represent intermediates in the pathways leading to more complex sesterterpenes frequently found in Dictyoceratida, a sponge Order belonging to Demospongiae, a clade which is phylogenetically distinct from the Homoscleromorpha. While steroid and triterpenoid saponins were already well known from marine sponges, balibalosides are the first examples of glycosilated sesterterpenes. MDPI 2013-05-06 /pmc/articles/PMC3707155/ /pubmed/23648552 http://dx.doi.org/10.3390/md11051477 Text en © 2013 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Audoin, Coralie
Bonhomme, Dominique
Ivanisevic, Julijana
de la Cruz, Mercedes
Cautain, Bastien
Monteiro, Maria Cândida
Reyes, Fernando
Rios, Laurent
Perez, Thierry
Thomas, Olivier P.
Balibalosides, an Original Family of Glucosylated Sesterterpenes Produced by the Mediterranean Sponge Oscarella balibaloi
title Balibalosides, an Original Family of Glucosylated Sesterterpenes Produced by the Mediterranean Sponge Oscarella balibaloi
title_full Balibalosides, an Original Family of Glucosylated Sesterterpenes Produced by the Mediterranean Sponge Oscarella balibaloi
title_fullStr Balibalosides, an Original Family of Glucosylated Sesterterpenes Produced by the Mediterranean Sponge Oscarella balibaloi
title_full_unstemmed Balibalosides, an Original Family of Glucosylated Sesterterpenes Produced by the Mediterranean Sponge Oscarella balibaloi
title_short Balibalosides, an Original Family of Glucosylated Sesterterpenes Produced by the Mediterranean Sponge Oscarella balibaloi
title_sort balibalosides, an original family of glucosylated sesterterpenes produced by the mediterranean sponge oscarella balibaloi
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3707155/
https://www.ncbi.nlm.nih.gov/pubmed/23648552
http://dx.doi.org/10.3390/md11051477
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