Cargando…
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...
Autores principales: | , , , , , , , , , |
---|---|
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 |
_version_ | 1782276475543617536 |
---|---|
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. |
format | Online Article Text |
id | pubmed-3707155 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT audoincoralie balibalosidesanoriginalfamilyofglucosylatedsesterterpenesproducedbythemediterraneanspongeoscarellabalibaloi AT bonhommedominique balibalosidesanoriginalfamilyofglucosylatedsesterterpenesproducedbythemediterraneanspongeoscarellabalibaloi AT ivanisevicjulijana balibalosidesanoriginalfamilyofglucosylatedsesterterpenesproducedbythemediterraneanspongeoscarellabalibaloi AT delacruzmercedes balibalosidesanoriginalfamilyofglucosylatedsesterterpenesproducedbythemediterraneanspongeoscarellabalibaloi AT cautainbastien balibalosidesanoriginalfamilyofglucosylatedsesterterpenesproducedbythemediterraneanspongeoscarellabalibaloi AT monteiromariacandida balibalosidesanoriginalfamilyofglucosylatedsesterterpenesproducedbythemediterraneanspongeoscarellabalibaloi AT reyesfernando balibalosidesanoriginalfamilyofglucosylatedsesterterpenesproducedbythemediterraneanspongeoscarellabalibaloi AT rioslaurent balibalosidesanoriginalfamilyofglucosylatedsesterterpenesproducedbythemediterraneanspongeoscarellabalibaloi AT perezthierry balibalosidesanoriginalfamilyofglucosylatedsesterterpenesproducedbythemediterraneanspongeoscarellabalibaloi AT thomasolivierp balibalosidesanoriginalfamilyofglucosylatedsesterterpenesproducedbythemediterraneanspongeoscarellabalibaloi |