Eryloside E from an atlantic sponge Erylus goffrilleri

Gulavita, Nanda K.; Wright, Amy E.; Kelly‐Borges, Michelle; Longley, Ross E.; Yarwood, Donna R.; Sills, Matthew A.

doi:10.1016/s0040-4039(00)73338-7

Cited by 46 publications

(52 citation statements)

References 6 publications

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“…Erylosides A to F (excluding B) were isolated from E. lendenfeldi (Carmely et al 1989), Erylus sp. (D'Auria et al 1992), E. goffrilleri (Gulavita et al 1994), and E. formosus (Stead et al 2000). Despite the consistent naming of these compounds, the erylosides represent 3 different aglycone carbon skeletons and are quite distinct in their patterns of glycosylation.…”

Section: Discussionmentioning

confidence: 99%

“…These compounds have been reported to possess interesting pharmacological activities, such as cytotoxicity (Cafieri et al 1999), immunosuppressive activity (Gulavita et al 1994), and thrombin receptor antagonist activity (Stead et al 2000). However, until now there have been no published reports of the ecological roles of these compounds, and no discussion in the literature of the chemical defenses of these sponges except in the survey of crude extracts by Pawlik et al (1995).…”

Section: Discussionmentioning

confidence: 99%

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Triterpene glycosides defend the Caribbean reef sponge Erylus formosus from predatory fishes

Kubanek¹,

Pawlik²,

Eve³

et al. 2000

Mar. Ecol. Prog. Ser.

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The reef sponge Erylus formosus (Demospongiae: Geodiidae) from the Bahamas and southern Florida contains a suite of triterpene glycosides that, at a natural volumetric concentration, deters predation by the fish Thalassoma bifasciatum in laboratory assays, and a natural assemblage of reef fishes in field assays. Antifeedant metabolites were isolated by bioassay-guided fractionation of extracts of E. formosus using standard chromatographic methods and identified by nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry. Included in the deterrent mixture from E. formosus collected in the Bahamas and Florida were at least 6 related triterpene glycosides possessing identical aglycones but with different sugar residues. Two additional compounds with a penasterol triterpene core (formoside, and an N-acetyl galactosamine derivative, formoside B) were found in specimens from the Bahamas but not Florida. Formoside, while being the major deterrent metabolite of E. formosus from the Bahamas, is less potent than the other triterpene glycosides on a weight per volume basis. As a mixture, the triterpene glycosides protect E. formosus from predatory reef fishes, but when these compounds were separated into fractions some failed to deter feeding at natural concentrations. As compounds of this type are beginning to be recognized as prevalent sponge metabolites, we suggest that terpene glycosides may have important ecological functions, just as a defensive role has been ascribed to similar compounds in sea stars, sea cucumbers, and terrestrial plants.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Triterpene glycosides defend the Caribbean reef sponge Erylus formosus from predatory fishes

Kubanek¹,

Pawlik²,

Eve³

et al. 2000

Mar. Ecol. Prog. Ser.

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“…For other members of the eryloside family, interesting pharmacological properties have also been reported. While eryloside F shows a potent and relatively selective thrombin receptor antagonist activity and inhibits human platelet aggregation in vitro, 9 eryloside E displays immunosuppressive activity, 8 and nobiloside is a neuraminidase inhibitor. 13 From an ecological point of view, the mixtures of eryloside-type triterpenes from Carribean collections have been shown to contribute to the chemical defense of the sponge Erylus formosus.…”

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confidence: 99%

New steroidal saponins from the sponge Erylus lendenfeldi

Fouad¹,

Al-Trabeen²,

Badran³

et al. 2004

Arkivoc

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Our search for biologically active marine natural products has led to the isolation of two new steroidal saponins, eryloside K (2) and eryloside L (3) together with the known antitumor and antifungal glycoside eryloside A (1) from the organic extract of the sponge Erylus lendenfeldi (Geodiidae) collected in the Red Sea. The structures of the new compounds were elucidated on the basis of comprehensive spectral analyses ( 1 H, 13 C, COSY, HMQC, HMBC and TOCSY NMR) as well as GC/MS analysis to infer the absolute stereochemistry of the sugar moieties. Eryloside K (2) is the 24,25-didehydro congener of 1, while eryloside L (3) features an unusual 8α,9α-epoxy-4α-methyl-8,9-secocholesta-7,9(11),14-triene skeleton which appears to be unprecedented in nature. Eryloside A (1) displayed antibacterial activity against Bacillus subtilis and Escherichia coli together with antifungal activity against Candida albicans.

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“…The first eryloside congener isolated from the Red Sea sponge Erylus lendenfeldi was Eryloside A, which has demonstrated significant antitumor activity against murine leukemia P388 cells, as well as antifungal activity against Candida albicans. Erylosides E and F, isolated from, respectively, the Atlantic sponge E. goffrilleri [47] and E. formosus, revealed immunosuppressive and potent thrombin receptor antagonistic activities [48] .…”

Section: Steroidal Saponinsmentioning

confidence: 99%

Novel natural product discovery from obligate symbiotic organisms of marine sponges

Monaco

Quinlan

2018

J Nat Agents Mol Ther

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A rich source for the discovery of novel, pharmacologically active natural products have been the terrestrial plants and microbes, accounting for about 85% of the approved natural products in pharmaceutical use, and about 60% of approved pharmaceuticals and new drug applications submission annually. Discovery in the marine environment has lagged due to the difficulty of exploration in this ecological niche. Such exploration began in the 1950's, after technological advances such as scuba diving which allowed collection of marine organisms, primarily to a depth of about 15 m, which was the limit of that technology. Natural products from filter feeding marine invertebrates and in particular, sponges, have proven to be a rich source of structurally unique pharmacologically active compounds, with over 16,000 molecules isolated thus far and a continuing pace of discovery at hundreds of novel bioactive molecules per year. All classes of pharmaceuticals have been represented in this discovery process, including antiprotozoals, pesticides, TGF-beta inhibitors, cationic channel blockers, anticancer, cytotoxic, antiviral, anti-inflammatory and antibacterial compounds. Important biosynthetic pathways found in sponges which give rise to these compounds include the terpenoid, fatty acid, polyketoid, quinone reductase, alkaloid, isoprenoid, and non-ribosomal protein synthase pathways as summarized in this article.

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Eryloside E from an atlantic sponge Erylus goffrilleri

Cited by 46 publications

References 6 publications

Triterpene glycosides defend the Caribbean reef sponge Erylus formosus from predatory fishes

Triterpene glycosides defend the Caribbean reef sponge Erylus formosus from predatory fishes

New steroidal saponins from the sponge Erylus lendenfeldi

Novel natural product discovery from obligate symbiotic organisms of marine sponges

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