Ulososide B, a new unusual norlanostane-triterpene glycoside and its genuine aglycone from the Madagascar sponge Ulosa sp.

Antonov, Alexander S.; Kalinovsky, Anatoly I.; Stonik, V. A.

doi:10.1016/s0040-4039(98)00589-9

Cited by 33 publications

(35 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The few sponges that are known to contain triterpene or steroidal glycosides have come from the demosponge orders Astrophorida/Choristida (Asteropus sarasinosum, Kitagawa et al 1987, Kobayashi et al 1991; Erylus spp., see below), Halichondrida (Ulosa sp., Antonov et al 1994Antonov et al , 1998, and Axinellida (Ectyoplasia ferox, Cafieri et al 1999). Of these, sponges of the genus Erylus have yielded a large number (approx.…”

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.

View full text Add to dashboard Cite

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.

show abstract

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.

View full text Add to dashboard Cite

show abstract

“…Antonov et al . have isolated five glycosides with oxidized 14-nor-methyl-lanostane type aglycones, namely ulososides A–E ( 65 – 69 ) from the sponge collected off the waters of the North-Western Madagascar [37,38,39]. Ulososides A ( 65 ) [37], C ( 67 ), D ( 68 ) and E ( 69 ) [39] possess 22 S ,23 R -diol fragment and 24 S -methyl in side chains of their aglycones, like brassinolides.…”

Section: Tetracyclic Triterpene Glycosidesmentioning

confidence: 99%

“…Ulososides A ( 65 ) [37], C ( 67 ), D ( 68 ) and E ( 69 ) [39] possess 22 S ,23 R -diol fragment and 24 S -methyl in side chains of their aglycones, like brassinolides. Ulososide B ( 66 ) contains a 23ξ-hydroxy group in its aglycone side chain, but has no 24-methyl group [38]. Compounds 65 is a bioside with a rare 1,6-bond between D-glucose and terminal D-glucuronic acid, while 66 – 68 are monosides, containing 2-( N -acetylamino)-2-deoxy-β-D-glucose or D-glucose as carbohydrate moieties.…”

Section: Tetracyclic Triterpene Glycosidesmentioning

confidence: 99%

Glycosides from Marine Sponges (Porifera, Demospongiae): Structures, Taxonomical Distribution, Biological Activities and Biological Roles

et al. 2012

View full text Add to dashboard Cite

show abstract

“…1). Although triterpene glycosides and steroidal glycosides are common in echinoderms (Burnell and ApSimon 1983;Stonik and Elyakov 1988), and have long been ascribed defensive roles in terrestrial plants (Applebaum and Birk 1979), their presence in sponges is a relatively recent discovery (Kitagawa et al 1987;Carmely et al 1989;Kobayashi et al 1991;D'Auria et al 1992;Antonov et al 1994Antonov et al , 1998Gulavita et al 1994;Jaspars and Crews 1994;Cafieri et al 1999;Stead et al 2000;Kubanek et al 2001;Campagnuolo et al 2001) and their natural functions are largely unknown (except Kubanek et al 2000).…”

Section: Introductionmentioning

confidence: 99%

Multiple defensive roles for triterpene glycosides from two Caribbean sponges

et al. 2002

View full text Add to dashboard Cite

Despite their high nutritional value and a lack of physical defenses, most marine sponges appear to be minimally affected by predators, competitors, and fouling organisms, possibly due to sponge chemical defenses. In the last 15 years, several triterpene glycosides have been isolated from sponges, but their ecological or physiological roles are largely unknown. We tested triterpene glycosides from Erylus formosus and Ectyoplasia ferox, Caribbean sponges belonging to two different orders, in field and laboratory assays for effects on fish feeding, attachment by potential biofilm-forming bacteria, fouling by invertebrates and algae, and overgrowth by neighboring sponges. Formoside and other triterpene glycosides from Erylus formosus deterred predation, microbial attachment, and fouling by invertebrates and algae. Triterpene glycosides from Ectyoplasia ferox were found to be antipredatory and allelopathic. Thus, triterpene glycosides in these sponges appear to have multiple ecological functions. Tests with different triterpene glycosides at several concentrations indicated that small differences in molecular structure affect ecological activity. In order to establish whether triterpene glycosides could be involved in water-borne versus surface-mediated interactions, the presence of triterpene glycosides in the seawater surrounding live sponges was measured using two in situ sampling methods followed by HPLC and NMR spectral analysis. Water-borne triterpene glycosides were below detection limits for both species. However, top sponge layers and swabs of the surfaces of both sponges contained sufficiently high concentrations of triterpene glycosides to deter bacterial settlement and fouling of Erylus formosus surfaces and overgrowth of Ectyoplasia ferox by neighboring sponges. Enemies of these sponges appear to be deterred by surface contact of triterpene glycosides rather than by water-borne interactions. The dual strategy of employing one group of compounds for multiple purposes and minimizing the loss of compounds into seawater suggests that these organisms utilize chemical defenses with efficiency.

show abstract

Ulososide B, a new unusual norlanostane-triterpene glycoside and its genuine aglycone from the Madagascar sponge Ulosa sp.

Cited by 33 publications

References 9 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

Glycosides from Marine Sponges (Porifera, Demospongiae): Structures, Taxonomical Distribution, Biological Activities and Biological Roles

Multiple defensive roles for triterpene glycosides from two Caribbean sponges

Contact Info

Product

Resources

About