New Sesquiterpene and Brominated Metabolites from the Tropical Marine Sponge Dysidea sp.

Cameron, George M.; Stapleton, Bronwin; Simonsen, Shane M.; Brecknell, Douglas J.; Garson, Mary J.

doi:10.1016/s0040-4020(00)00434-8

Cited by 66 publications

(61 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…3) previously reported from sponges belonging to Dysidea genus. These molecules have been isolated by Si-gel chromatography and identified as: pallescensin-B (1) ), (−)-furodysinin (2) (Guella et al 1985), which was also found in some Hypselodoris species 1994), (−)-dehydroherbadysidolide (3) (Cameron et al 2000) and (−)-herbadysidolide (4) (Charles et al 1978). Compounds 1-4 have been identified by comparison of 1 H-NMR, mass spectra and [α] D value with literature data.…”

Section: Resultsmentioning

confidence: 99%

Chemical studies on Indopacific Ceratosoma nudibranchs illuminate the protective role of their dorsal horn

et al. 2005

View full text Add to dashboard Cite

Section: Resultsmentioning

confidence: 99%

Chemical studies on Indopacific Ceratosoma nudibranchs illuminate the protective role of their dorsal horn

et al. 2005

View full text Add to dashboard Cite

“…These characteristics make sponges excellent organisms in which to study variation in the production of secondary metabolites and the relationship between environmental factors and symbionts. Sponges of the genus Dysidea produce a high diversity of secondary metabolites including terpenes, sterols, chlorinated amino acids, alkaloids and polybrominated diphenyl ethers (Dunlop et al 1982, Carmeli et al 1988, Fu & Schmitz 1996, Bandaranayake et al 1997, Cameron et al 2000, Stapleton et al 2001see Venkateswarlu et al 1998 for a review of the extensive literature on secondary metabolites isolated from Dysidea spp.). The secondary chemistry of the tropical species D. herbacea has been extensively investigated.…”

Section: Introductionmentioning

confidence: 99%

Effects of depth and light on secondary metabolites and cyanobacterial symbionts of the sponge Dysidea granulosa

Becerro¹,

Paul²

2004

Mar. Ecol. Prog. Ser.

View full text Add to dashboard Cite

The tropical sponge Dysidea granulosa contains a number of symbiotic heterotrophic bacteria and large quantities of the photosynthetic cyanobacterium Oscillatoria spongeliae, which are reported to be responsible for the production of ecologically active polybrominated diphenyl ethers (BDEs) in Dysidea spp. In order to better understand the relationship between these symbionts and the production of BDEs, we looked at the variation in secondary chemistry in 3 populations of D. granulosa and the relationship between cyanobacteria and secondary chemistry in the sponge, and experimentally assessed the role that depth and light play in this relationship by transplanting sponges in the field. At a population scale, the concentration of BDEs is positively correlated with the concentration of chlorophyll a (chl a), both varying significantly between populations. Yet, in sponges experimentally transplanted to a deeper site, the concentration of chl a decreased significantly while BDE concentration remained stable. We specifically tested the importance of light in determining levels of symbionts and BDEs by placing sponges under transparent, UV-opaque, and black Plexiglas plates. After 5 wk, levels of BDEs and chl a had decreased significantly, although these trends differed between light treatment, suggesting a lack of direct correlation between BDEs and cyanobacterial populations. This was also supported by a within-sponge analysis of chl a and BDEs, since high levels of compounds were found in the choanosome of the sponge, whereas chl a and cyanobacterial contents were minimal. Our data suggest that the relationship between the levels of BDEs in D. granulosa and its photosynthetic symbionts is more complex than expected. Variation in the levels of secondary metabolites and symbionts seems to be related at a population scale, but unrelated at an individual scale.

show abstract

“…(-)-Euryfuran (22) and (+)-pallescensin A (23) have also been reported from both nudibranchs and sponges [20,22,23]. For H. jacksoni, eight animals collected from two separate locations (Mudjimba Island, Mooloolaba; Shag Rock, Moreton Bay) were combined prior to extraction owing to their small size, yielding the new metabolite (-)-(5R,6Z)-dendrolasin-5-acetate (24) along with the known sesquiterpenes (+)-agassizin (25) [20], (-)-furodysin (26), (-)-furodysinin (27) [24], (-)-euryfuran, (-)-dehydroherbadysidolide (28) [25], and (+)-pallescensone (29) [26]. Finally eight specimens of H. whitei (collection site Shag Rock) provided (-)-euryfuran, (-)-furodysin, (-)-furosydinin, and dendrolasin.…”

Section: The Chemistry Of Hypselodoris Sppmentioning

confidence: 99%

Chemoecological studies on marine natural products: terpene chemistry from marine mollusks

Mudianta

White²,

Suciati

et al. 2014

Pure and Applied Chemistry

Self Cite

View full text Add to dashboard Cite

Some species of nudibranchs (Mollusca) protect themselves from predatory attacks by storing defensive terpene chemicals acquired from dietary sponges (Porifera) in specialized body parts called MDFs (mantle dermal formations), often advertising their unpalatability to potential predators by means of bright coloration patterns. Consequently, the survival of these trophic specialist species is closely related to the possibility of obtaining the defensive tools from sponges that live in their immediate vicinity; therefore, it is important to determine as precisely as possible the chemical composition of nudibranch extracts prior to any ecological studies addressing issues that involve their alimentary behavior and their defensive strategies, including the significance of their color patterns. Some of our recent studies on the chemical composition of terpene extracts from nudibranchs belonging to the genera Chromodoris and Hypselodoris are summarized. We also report the development of a method to assay extracts and purified metabolites for their feeding deterrent activity against co-occurring generalist predators. In a recent chemoecological study, showing that repugnant terpene chemicals are accumulated at extremely high concentrations in exposed parts of the nudibranchs' bodies, the feeding deterrence assays were carried out on the generalist marine shrimp Palaemon elegans, very common in the Mediterranean. We have modified this assay for use with the Australian shrimp species P. serenus, and confirmed the ecological validity of the assay by analysis of extracts from species of sponges and mollusks that live in the same habitat as P. serenus. The deterrent properties of haliclonacyclamine alkaloids isolated from the sponge Haliclona sp. were demonstrated, with the alkaloid mixture demonstrating palatability deterrence at concentrations as low as 0.05 mg/mL, and complete deterrence at 0.75 mg/mL. In contrast, the diterpene thuridillin metabolites from the sacoglossan mollusk Thuridilla splendens did not deter feeding by P. serenus.

show abstract

New Sesquiterpene and Brominated Metabolites from the Tropical Marine Sponge Dysidea sp.

Cited by 66 publications

References 20 publications

Chemical studies on Indopacific Ceratosoma nudibranchs illuminate the protective role of their dorsal horn

Chemical studies on Indopacific Ceratosoma nudibranchs illuminate the protective role of their dorsal horn

Effects of depth and light on secondary metabolites and cyanobacterial symbionts of the sponge Dysidea granulosa

Chemoecological studies on marine natural products: terpene chemistry from marine mollusks

Contact Info

Product

Resources

About