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- Title
Poecillastrosides, Steroidal Saponins from the Mediterranean Deep-Sea Sponge Poecillastra compressa (Bowerbank, 1866).
- Authors
Calabro, Kevin; Kalahroodi, Elaheh Lotfi; Rodrigues, Daniel; Díaz, Caridad; de la Cruz, Mercedes; Cautain, Bastien; Laville, Rémi; Reyes, Fernando; Pérez, Thierry; Soussi, Bassam; Thomas, Olivier P.
- Abstract
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-20, poecillastrosides E-G (5-7) are characterized by a cyclopropane on the side-chain and a connection at O-30 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.
- Subjects
STEROIDAL alkaloids; SAPONINS; CYCLOPROPANE; MARINE biotechnology; MARICULTURE
- Publication
Marine Drugs, 2017, Vol 15, Issue 7, p199
- ISSN
1660-3397
- Publication type
Article
- DOI
10.3390/md15070199