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Mar. Drugs 2013, 11(5), 1477-1489; doi:10.3390/md11051477
Article

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

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Received: 25 March 2013; in revised form: 9 April 2013 / Accepted: 22 April 2013 / Published: 6 May 2013
(This article belongs to the Special Issue Marine Secondary Metabolites)
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Abstract: The chemical investigation of the recently described Mediterranean Homoscleromorpha sponge Oscarella balibaloi revealed an original family of five closely related glucosylated sesterterpenes 14, 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.
Keywords: sponge; Oscarella; Homoscleromorpha; sesterterpenes; saponins sponge; Oscarella; Homoscleromorpha; sesterterpenes; saponins
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Audoin, C.; Bonhomme, D.; Ivanisevic, J.; Cruz, M.; Cautain, B.; Monteiro, M.C.; Reyes, F.; Rios, L.; Perez, T.; Thomas, O.P. Balibalosides, an Original Family of Glucosylated Sesterterpenes Produced by the Mediterranean Sponge Oscarella balibaloi. Mar. Drugs 2013, 11, 1477-1489.

AMA Style

Audoin C, Bonhomme D, Ivanisevic J, Cruz M, Cautain B, Monteiro MC, Reyes F, Rios L, Perez T, Thomas OP. Balibalosides, an Original Family of Glucosylated Sesterterpenes Produced by the Mediterranean Sponge Oscarella balibaloi. Marine Drugs. 2013; 11(5):1477-1489.

Chicago/Turabian Style

Audoin, Coralie; Bonhomme, Dominique; Ivanisevic, Julijana; Cruz, Mercedes ; Cautain, Bastien; Monteiro, Maria C.; Reyes, Fernando; Rios, Laurent; Perez, Thierry; Thomas, Olivier P. 2013. "Balibalosides, an Original Family of Glucosylated Sesterterpenes Produced by the Mediterranean Sponge Oscarella balibaloi." Mar. Drugs 11, no. 5: 1477-1489.


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