New Cytotoxic Metabolites from the Sponge<i>Cacospongia scalaris</i>

Rueda, Ana Julia Velez; Zubı́a, Eva; Ortega, Marı́a J.; Carballo, José Luís; Salvá, Javier

doi:10.1021/jo961975y

Cited by 46 publications

(46 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Cacospongia spp. produce a wide variety of scalarane sesterterpenes, including scalaradial and desacetylscalaradial, with the concentrations of individual compounds ranging from 0.004% to 1% dry mass (Rueda et al 1997;Becerro et al 1998;Cambie et al 1998;Thacker et al 1998). Although we have no evidence to support variation in the number of secondary metabolites and the concentrations at which they occur in each counterpart species, we did find a higher percent yield of crude organic extract in tropical than in temperate sponges.…”

Section: Discussionmentioning

confidence: 99%

Biogeography of sponge chemical ecology: comparisons of tropical and temperate defenses

et al. 2003

View full text Add to dashboard Cite

Examples from both marine and terrestrial systems have supported the hypothesis that predation is higher in tropical than in temperate habitats and that, as a consequence, tropical species have evolved more effective defenses to deter predators. Although this hypothesis was first proposed for marine sponges over 25 years ago, our study provides the first experimental test of latitudinal differences in the effectiveness of sponge chemical defenses. We collected 20 common sponge species belonging to 14 genera from tropical Guam and temperate Northeast Spanish coasts (Indo-Pacific and Mediterranean biogeographic areas) and conducted field-based feeding experiments with large and small fish predators in both geographic areas. We use the term global deterrence to describe the deterrent activity of a sponge extract against all of the predators used in our experiments and to test the hypothesis that sponges from Guam are chemically better defended than their Mediterranean counterparts. Sympatric and allopatric deterrence refer to the average deterrent activity of a sponge against sympatric or allopatric predators. All of the sponges investigated in this study showed deterrent properties against some predators. However, 35% of the sponge species were deterrent in at least one but not in all the experiments, supporting the idea that predators can respond to chemical defenses in a species-specific manner. Tropical and temperate sponges have comparable global, sympatric, and allopatric deterrence, suggesting not only that chemical defenses from tropical and temperate sponges are equally strong but also that they are equally effective against sympatric and allopatric predators. Rather than supporting geographic trends in the production of chemical defenses, our data suggest a recurrent selection for chemical defenses in sponges as a general life-history strategy.

show abstract

Section: Discussionmentioning

confidence: 99%

Biogeography of sponge chemical ecology: comparisons of tropical and temperate defenses

et al. 2003

View full text Add to dashboard Cite

show abstract

“…Scalaradial (2) has also been found in other Cacospongia mollior specimens [12], as well as in other sponges and as chemical constituents of nudibranchs. For example, scalaradial (2) has been isolated from the sponge Cacospongia scalaris collected at Wakayama (Japan) [13], and collected at Tarifa Island (Spain) [14]. The sponges Spongia oceania collected at Pupukea (Hawai) [15], Cacospongia sp.…”

Section: Tetracyclic Scalaranesmentioning

confidence: 99%

Scalarane Sesterterpenoids

González

2010

CBC

View full text Add to dashboard Cite

show abstract

“…, 1998; Rueda et al. , 1997; Tsuchiya et al. , 1998), antifeedant (Terem and Scheuer, 1986), inhibition of platelet aggregation (Kazlauskas et al.…”

Section: Introductionmentioning

confidence: 99%

Analysis of sesterterpenoids from Aspergillus terreus using ESI‐QTOF and ESI‐IT

Fang

Han³

et al. 2010

Phytochemical Analysis

View full text Add to dashboard Cite

ABSTRACT:Introduction -Biosynthesis of terretonin was studied due to the interesting skeleton of this series of sesterterpenoids. Very recently, López-Gresa reported two new sesterterpenoids (terretonins E and F) which are inhibitors of the mammalian mitochondrial respiratory chain. Mass spectrometry (MS), especially tandem mass spectrometry, has been one of the most important physicochemical methods for the identification of trace natural products due to it rapidity, sensitivity and low levels of sample consumption. The potential application prospect and unique skeleton prompted us to study structural characterisation using MS. Objective -To obtain sufficient information for rapid structural elucidation of this class of compounds using MS. Methodology -The elemental composition of the product ions was confirmed by low-energy ESI-CID-QTOF-MS/MS analyses. The fragmentation pathways were postulated on the basis of ESI-QTOF-MS/MS/MS and ESI-IT-MSn spectra. Common features and major differences between ESI-QTOF-MS/MS and IT-MS n spectra were compared. For ESI-QTOF-MS/MS/MS experiments, capillary exit voltage was raised to induce in-source dissociation. Ammonium acetate or acetic acid were added into solutions to improve the intensity of [M + H]+ . The collision energy was optimised to achieve sufficient fragmentation. Some fragmentation pathways were unambiguously proposed by the variety of abundance of fragment ions at different collision energies even without MS n spectra. Results -Fragmentation pathways of five representative sesterterpenoids were elucidated using ESI-QTOF-MS/MS/MS and ESI-IT-MS

show abstract

New Cytotoxic Metabolites from the SpongeCacospongia scalaris

Cited by 46 publications

References 22 publications

Biogeography of sponge chemical ecology: comparisons of tropical and temperate defenses

Biogeography of sponge chemical ecology: comparisons of tropical and temperate defenses

Scalarane Sesterterpenoids

Analysis of sesterterpenoids from Aspergillus terreus using ESI‐QTOF and ESI‐IT

Contact Info

Product

Resources

About