Poecillastrosides, Steroidal Saponins from the Mediterranean Deep-Sea Sponge Poecillastra compressa (Bowerbank, 1866)
The first chemical investigation of the Mediterranean deep-sea sponge Poecillastra compressa (Bowerbank, 1866) led to the identification of seven new steroidal saponins named poecillastrosides A–G (1–7). All saponins feature an oxidized methyl at C-18 into a primary alcohol or a carboxylic acid. Whi...
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| Format: | Article |
| Language: | English |
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MDPI AG
2017-06-01
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| Series: | Marine Drugs |
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| Online Access: | http://www.mdpi.com/1660-3397/15/7/199 |
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| author | Kevin Calabro Elaheh Lotfi Kalahroodi Daniel Rodrigues Caridad Díaz Mercedes de la Cruz Bastien Cautain Rémi Laville Fernando Reyes Thierry Pérez Bassam Soussi Olivier P. Thomas |
| author_facet | Kevin Calabro Elaheh Lotfi Kalahroodi Daniel Rodrigues Caridad Díaz Mercedes de la Cruz Bastien Cautain Rémi Laville Fernando Reyes Thierry Pérez Bassam Soussi Olivier P. Thomas |
| author_sort | Kevin Calabro |
| collection | DOAJ |
| description | The first chemical investigation of the Mediterranean deep-sea sponge Poecillastra compressa (Bowerbank, 1866) led to the identification of seven new steroidal saponins named poecillastrosides A–G (1–7). All saponins feature an oxidized methyl at C-18 into a primary alcohol or a carboxylic acid. While poecillastrosides A–D (1–4) all contain an exo double bond at C-24 of the side-chain and two osidic residues connected at O-2′, poecillastrosides E–G (5–7) are characterized by a cyclopropane on the side-chain and a connection at O-3′ between both sugar units. The chemical structures were elucidated through extensive spectroscopic analysis (High-Resolution Mass Spectrometry (HRESIMS), 1D and 2D NMR) and the absolute configurations of the sugar residues were assigned after acidic hydrolysis and cysteine derivatization followed by LC-HRMS analyses. Poecillastrosides D and E, bearing a carboxylic acid at C-18, were shown to exhibit antifungal activity against Aspergillus fumigatus. |
| first_indexed | 2024-04-11T22:45:59Z |
| format | Article |
| id | doaj.art-2864e11f8b4c4525bccc7fdd5f2a582e |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-11T22:45:59Z |
| publishDate | 2017-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-2864e11f8b4c4525bccc7fdd5f2a582e2022-12-22T03:58:46ZengMDPI AGMarine Drugs1660-33972017-06-0115719910.3390/md15070199md15070199Poecillastrosides, Steroidal Saponins from the Mediterranean Deep-Sea Sponge Poecillastra compressa (Bowerbank, 1866)Kevin Calabro0Elaheh Lotfi Kalahroodi1Daniel Rodrigues2Caridad Díaz3Mercedes de la Cruz4Bastien Cautain5Rémi Laville6Fernando Reyes7Thierry Pérez8Bassam Soussi9Olivier P. Thomas10School of Chemistry, National University of Ireland Galway, University Road, H91 TK33 Galway, IrelandGéoazur, Université Côte d’Azur, CNRS, OCA, IRD, 250 rue Albert Einstein, 06560 Valbonne, FranceGéoazur, Université Côte d’Azur, CNRS, OCA, IRD, 250 rue Albert Einstein, 06560 Valbonne, FranceFundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía, Avda. del Conocimiento 34, Parque Tecnológico de Ciencias de la Salud, E-18016 Armilla, Granada, SpainFundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía, Avda. del Conocimiento 34, Parque Tecnológico de Ciencias de la Salud, E-18016 Armilla, Granada, SpainFundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía, Avda. del Conocimiento 34, Parque Tecnológico de Ciencias de la Salud, E-18016 Armilla, Granada, SpainCosmo International Ingredients, 855 avenue du Docteur Maurice Donat, 06250 Mougins, FranceFundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía, Avda. del Conocimiento 34, Parque Tecnológico de Ciencias de la Salud, E-18016 Armilla, Granada, SpainInstitut Méditerranéen de Biodiversité et d’Ecologie marine et continentale, CNRS—Aix-Marseille University, IRD—University Avignon, Station Marine d’Endoume, rue de la batterie des lions, 13007 Marseille, FranceGéoazur, Université Côte d’Azur, CNRS, OCA, IRD, 250 rue Albert Einstein, 06560 Valbonne, FranceSchool of Chemistry, National University of Ireland Galway, University Road, H91 TK33 Galway, IrelandThe first chemical investigation of the Mediterranean deep-sea sponge Poecillastra compressa (Bowerbank, 1866) led to the identification of seven new steroidal saponins named poecillastrosides A–G (1–7). All saponins feature an oxidized methyl at C-18 into a primary alcohol or a carboxylic acid. While poecillastrosides A–D (1–4) all contain an exo double bond at C-24 of the side-chain and two osidic residues connected at O-2′, poecillastrosides E–G (5–7) are characterized by a cyclopropane on the side-chain and a connection at O-3′ between both sugar units. The chemical structures were elucidated through extensive spectroscopic analysis (High-Resolution Mass Spectrometry (HRESIMS), 1D and 2D NMR) and the absolute configurations of the sugar residues were assigned after acidic hydrolysis and cysteine derivatization followed by LC-HRMS analyses. Poecillastrosides D and E, bearing a carboxylic acid at C-18, were shown to exhibit antifungal activity against Aspergillus fumigatus.http://www.mdpi.com/1660-3397/15/7/199spongesaponinsdeep-seaPoecillastra compressa |
| spellingShingle | Kevin Calabro Elaheh Lotfi Kalahroodi Daniel Rodrigues Caridad Díaz Mercedes de la Cruz Bastien Cautain Rémi Laville Fernando Reyes Thierry Pérez Bassam Soussi Olivier P. Thomas Poecillastrosides, Steroidal Saponins from the Mediterranean Deep-Sea Sponge Poecillastra compressa (Bowerbank, 1866) Marine Drugs sponge saponins deep-sea Poecillastra compressa |
| title | Poecillastrosides, Steroidal Saponins from the Mediterranean Deep-Sea Sponge Poecillastra compressa (Bowerbank, 1866) |
| title_full | Poecillastrosides, Steroidal Saponins from the Mediterranean Deep-Sea Sponge Poecillastra compressa (Bowerbank, 1866) |
| title_fullStr | Poecillastrosides, Steroidal Saponins from the Mediterranean Deep-Sea Sponge Poecillastra compressa (Bowerbank, 1866) |
| title_full_unstemmed | Poecillastrosides, Steroidal Saponins from the Mediterranean Deep-Sea Sponge Poecillastra compressa (Bowerbank, 1866) |
| title_short | Poecillastrosides, Steroidal Saponins from the Mediterranean Deep-Sea Sponge Poecillastra compressa (Bowerbank, 1866) |
| title_sort | poecillastrosides steroidal saponins from the mediterranean deep sea sponge poecillastra compressa bowerbank 1866 |
| topic | sponge saponins deep-sea Poecillastra compressa |
| url | http://www.mdpi.com/1660-3397/15/7/199 |
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