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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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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cited_by cdi_FETCH-LOGICAL-c610t-578e5b3c9b5b72ea0818726140521692b4d7ff501a6a4662db069417f18c14913
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container_end_page 12/199
container_issue 7
container_start_page 199
container_title Marine drugs
container_volume 15
creator 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
description 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 .
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ispartof Marine drugs, 2017-06, Vol.15 (7), p.199-12/199
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1660-3397
language eng
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source Publicly Available Content Database; PubMed Central
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
title Poecillastrosides, Steroidal Saponins from the Mediterranean Deep-Sea Sponge Poecillastra compressa (Bowerbank, 1866)
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-14T12%3A39%3A22IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_doaj_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Poecillastrosides,%20Steroidal%20Saponins%20from%20the%20Mediterranean%20Deep-Sea%20Sponge%20Poecillastra%20compressa%20(Bowerbank,%201866)&rft.jtitle=Marine%20drugs&rft.au=Calabro,%20Kevin&rft.date=2017-06-26&rft.volume=15&rft.issue=7&rft.spage=199&rft.epage=12/199&rft.pages=199-12/199&rft.issn=1660-3397&rft.eissn=1660-3397&rft_id=info:doi/10.3390/md15070199&rft_dat=%3Cproquest_doaj_%3E2108427827%3C/proquest_doaj_%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c610t-578e5b3c9b5b72ea0818726140521692b4d7ff501a6a4662db069417f18c14913%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2108427827&rft_id=info:pmid/28672858&rfr_iscdi=true