Poecillastrosides, Steroidal Saponins from the Mediterranean Deep-Sea Sponge Poecillastra compressa (Bowerbank, 1866)

The first chemical investigation of the Mediterranean deep-sea sponge (Bowerbank, 1866) led to the identification of seven new steroidal saponins named poecillastrosides A-G ( - ). All saponins feature an oxidized methyl at C-18 into a primary alcohol or a carboxylic acid. While poecillastrosides A-...

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Bibliographic Details
Published in:Marine drugs 2017-06, Vol.15 (7), p.199-12/199
Main Authors: Calabro, Kevin, Kalahroodi, Elaheh Lotfi, Rodrigues, Daniel, Díaz, Caridad, Cruz, Mercedes de la, Cautain, Bastien, Laville, Rémi, Reyes, Fernando, Pérez, Thierry, Soussi, Bassam, Thomas, Olivier P
Format: Article
Language:English
Subjects:
a-c
Alcohols
Animals
Antifungal activity
asteropus-sarasinosum
Bioactive compounds
Biological Sciences
Biologiska vetenskaper
Carboxylic acids
Chains
Continental interfaces, environment
Cyclopropane
Deep sea
Deep sea environments
Deep water
Earth Sciences
ectyoplasia-ferox
Environmental Sciences
erylus-lendenfeldi
Fungicides
Mass spectrometry
Mass spectroscopy
Molecular Structure
mycale-laxissima
NMR
Nuclear magnetic resonance
Organic chemistry
pandaros-acanthifolium
Pharmacology & Pharmacy
Poecillastra compressa
Porifera - chemistry
Porifera - metabolism
Residues
Saccharides
Saponins
Saponins - chemistry
Saponins - metabolism
Sciences of the Universe
side-chain
sponge
starfish certonardoa-semiregularis
Sugar
triterpenoid
water marine sponge
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Summary:The first chemical investigation of the Mediterranean deep-sea sponge (Bowerbank, 1866) led to the identification of seven new steroidal saponins named poecillastrosides A-G ( - ). All saponins feature an oxidized methyl at C-18 into a primary alcohol or a carboxylic acid. While poecillastrosides A-D ( - ) all contain an double bond at C-24 of the side-chain and two osidic residues connected at O-2', poecillastrosides E-G ( - ) 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 .
ISSN:1660-3397
1660-3397
DOI:10.3390/md15070199