New phospholipid fatty acids from the Caribbean sponge<i>Ectyoplasia ferox</i>

Carbelleira, Néstor M.; Maldonado, Marie E.

doi:10.1007/bf02535143

Cited by 24 publications

(18 citation statements)

References 11 publications

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“…The rare 19 : 1∆4 acid was found in the sponge Amphimedon viridis [45]. N 20 and N 22 monoenic FAs with a double bond at the 5th, 7th, 9th, 11th, 13th, and 15th carbon atom were found in many marine sponges [31,32]. Their content was usually lower than that of N 16 and N 18 monoenic FAs but higher than that of other short-chain monoenes.…”

Section: Monoenic Fasmentioning

confidence: 99%

Fatty Acids and Other Lipids of Marine Sponges

Rodkina

2005

Russ J Mar Biol

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At the present, the structure of lipids and fatty acids (FA) of almost 250 species of marine sponges has been studied. It was shown that sponges are leaders in FA diversity among aquatic animals. The great majority of the works on research of FA structure in sponges was focused on representatives of the class Demospongiae and was carried out on organisms from tropical and subtropical areas, whereas sponges from the boreal region remain poorly studied.

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Section: Monoenic Fasmentioning

confidence: 99%

Fatty Acids and Other Lipids of Marine Sponges

Rodkina

2005

Russ J Mar Biol

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“…From the four species described so far within this genus, chemical studies have only been undertaken on E. ferox and this point also raised our interest. Triterpenoid saponins, named ectyoplasides and feroxosides, were identified as major chemical components of this species [9,10], but polar lipids were also reported [11,12,13]. These compounds were suggested to possess ecological roles, but also to have pharmaceutical potential.…”

Section: Introductionmentioning

confidence: 99%

Ulososides and Urabosides — Triterpenoid Saponins from the Caribbean Marine Sponge Ectyoplasia ferox

et al. 2013

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Three new triterpene glycosides, named ulososide F (1), urabosides A (2) and B (3), together with the previously reported ulososide A (4), were isolated from the Caribbean marine sponge Ectyoplasia ferox. Their structures were elucidated using extensive interpretation of 1D and 2D-NMR data, as well as HRESIMS. The aglycon of all compounds is a rare 30-norlonastane and the sugar residues were identified after acid hydrolysis and GC analyses. Cytotoxicities of the isolated compounds were evaluated against Jurkat and CHO cell lines by a MTT in vitro assay as well as a hemolysis assay. Unexpectedly, all these saponin derivatives showed very low activity in our bioassays.

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“…For example, the 22-Me-5,9–24:2 and the unusual 23-Me-5,9–24:2 were identified in the lipid extract of the sponge Geodinella robusta [4], the 23-Me-5,9–25:2 was initially identified in the sponge Cribrochalina vasculum [5], while the 25-Me-5,9–26:2 and the 24-Me-5,9–26:2 were first identified in the sponge Petrosia ficiformis [6] and most recently in the Caribbean sponge Pseudospongosorites suberitoides [7]. All of these iso / anteiso Δ5,9 FA have, as a common biosynthetic precursor, either iso -15:0 and/or anteiso -15:0 that are also typically found in sponges but that definitively originate from bacterial symbionts within the sponge [8].…”

Section: Introductionmentioning

confidence: 99%

Novel Very Long‐Chain α‐Methoxylated Δ5,9 Fatty Acids from the Sponge Asteropus niger Are Effective Inhibitors of Topoisomerases IB

Carballeira

Montano

Amador

et al. 2015

Lipids

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The novel fatty acids (2R,5Z,9Z)-2-methoxy-25-methyl-5,9-hexacosadienoic acid (1a) and (2R,5Z,9Z)-2-methoxy-24-methyl-5,9-hexacosadienoic acid (1b) were isolated in 80% purity from the Caribbean sponge Asteropus niger by chloroform/methanol extraction followed by solvent partitioning and silica gel column chromatography. The compounds were characterized by utilizing a combination of gas chromatography-mass spectrometry, nuclear magnetic resonance, and circular dichroism. Acids 1a and 1b were not detected in the phospholipids (PtdCho and PtdIns) of the sponge, but rather as free FA and possibly in glycosylceramides. The mixtures of 1a and 1b displayed cytotoxicity towards THP-1 and HepG2 cells with EC50’s between 41 and 35 μg/mL. Apoptosis was not the preferred mode of cell death induced by 1a–1b in the THP-1 cells. This implies other types of cytotoxicity mechanisms, such as membrane disruption and/or the inhibition (EC50 = 1.8 μg/mL) of the human topoisomerase IB enzyme (hTopIB), with a mechanism of inhibition different from the one displayed by camptothecin (CPT). In a separate experiment, the mixture of 1a and 1b also displayed cytotoxicity towards ex vivo mouse splenocytes infected with Leishmania infantum amastigotes (IC50 = 0.17 mg/mL) and free living promastigotes (IC50 = 0.34 mg/mL). It was also found that the FA were inhibitory of the Leishmania topoisomerase IB (LTopIB) with an EC50 = 5.1 μg/mL. Taken together, 1a and 1b represent a new class of FA with potential as TopIB inhibitors that preferentially inhibit hTopIB over LTopIB.

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New phospholipid fatty acids from the Caribbean spongeEctyoplasia ferox

Cited by 24 publications

References 11 publications

Fatty Acids and Other Lipids of Marine Sponges

Fatty Acids and Other Lipids of Marine Sponges

Ulososides and Urabosides — Triterpenoid Saponins from the Caribbean Marine Sponge Ectyoplasia ferox

Novel Very Long‐Chain α‐Methoxylated Δ5,9 Fatty Acids from the Sponge Asteropus niger Are Effective Inhibitors of Topoisomerases IB

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