Caribbean Sponge Research Articles

Glycolipids from Sponges. Part 8: Plakopolyprenoside from the Marine Sponge Plakortis simplex. An Improved Procedure for Isolation of Glycolipids as Peracetyl Derivatives

Plakopolyprenoside, a unique cytotoxic glycolipid composed of a C 35 linear polyisoprenoid alcohol and a dixylosyl carbohydrate chain was isolated from the Caribbean sponge Plakortis simplex as its pentaacetate. Because the isolation of native plakopolyprenoside was unfeasible, acetylation with trideuteroacetic anhydride was used to ensure that no acetyl group was already present in the natural compound. The structure of plakopolyprenoside was established from spectral data. Plakopolyprenoside is cytotoxic against the J774 cell line.

Synthesis of marine sesterterpenoid dysidiolide

Dysidiolide, a novel sesterterpenoid isolated from the Caribbean sponge Dysidia etheria de Laubenfels, has been shown an inhibitor of protein phosphatase cdc25A. The authors established a stereocontrolled total synthesis of (±)-dysidiolide using an intramolecular Diels–Alder reaction as the key step.

Chemistry of verongida sponges. 10. Secondary metabolite composition of the caribbean sponge Verongula gigantea.

A detailed analysis of the secondary metabolites of the Caribbean sponge Verongula gigantea has been performed. A number of bromotyrosine derivatives, 1, 2, and 6-17, were identified, one of which (17) is a novel compound. Its structure was determined on the basis of spectroscopic evidence. Additionally, aureol (18) and 5, 6-dibromo-N,N-dimethyltryptamine (19) were isolated from one of the five analyzed specimens.

Defenses of Caribbean sponges against invertebrate predators. I. Assays with hermit crabs

MEPS Marine Ecology Progress Series Contact the journal Facebook Twitter RSS Mailing List Subscribe to our mailing list via Mailchimp HomeLatest VolumeAbout the JournalEditorsTheme Sections MEPS 195:125-132 (2000) - doi:10.3354/meps195125 Defenses of Caribbean sponges against invertebrate predators. I. Assays with hermit crabs Brett Waddell, Joseph R. Pawlik* Biological Sciences and Center for Marine Science Research, University of North Carolina at Wilmington, Wilmington, North Carolina 28403-3297, USA *Corresponding author. E-mail: pawlikj@uncwil.edu ABSTRACT: Hermit crabs (Decapoda: Anomura) are typically omnivorous and are common on Caribbean coral reefs. Sponges are sessile, fleshy, and high in protein and energy content, yet hermit crabs do not appear to prey on them. Assays were performed with the Caribbean reef hermit crab Paguristes punticeps to determine whether secondary metabolites or skeletal elements of Caribbean sponges that were incorporated into artificial foods affected feeding. Of 30 sponge species assayed, 26 (87%) yielded organic extracts that deterred feeding by P. punticeps. There was substantial interspecific and intraspecific variability in patterns of chemical deterrence. Sponges of the families Axinellidae, Agelasidae, Aplysinidae, Aplysinellidae, and Thorectidae typically yielded deterrent extracts. Three common sponge species, Mycale laevis, Callyspongia vaginalis, and Niphates erecta, were consistently non-deterrent, while other species, including Spheciospongia othella, Chondrilla nucula, Callyspongia plicifera, Niphates digitalis, and Xestospongia muta, were variably deterrent. These results are in general agreement with those of a previous survey of Caribbean sponge chemical defenses using the common reef fish Thalassoma bifasciatum. However, some results differed: Geodia neptuni and Iotrochota birotulata were consistently palatable to T. bifasciatum, but were deterrent to P. punticeps. Several species that were consistently deterrent to T. bifasciatum were variably deterrent to P. punticeps, including Aplysina cauliformis, Aplysina fulva, Ircinia strobilina, Amphimedon compressa, and Mycale laxissima. Neither spicules (from Agelas clathrodes, Ectyoplasia ferox, and Xestospongia muta) nor spiculated spongin skeleton (from A. clathrodes and X. muta) deterred feeding by P. punticeps. Spicules and spiculated spongin were similarly non-deterrent to the fish T. bifasciatum in a previous survey. The results of this study further suggest that chemical defenses are important in the ecology of Caribbean sponges, while skeletal components do not serve an antipredatory function. KEY WORDS: Sponge · Predation · Crab · Chemical defense · Caribbean · Chemical ecology Full text in pdf format PreviousNextExport citation RSS - Facebook - Tweet - linkedIn Cited by Published in MEPS Vol. 195. Publication date: March 31, 2000 Print ISSN:0171-8630; Online ISSN:1616-1599 Copyright © 2000 Inter-Research.

Defenses of Caribbean sponges against invertebrate predators. II. Assays with sea stars

Defenses of Caribbean sponges against invertebrate predators. II. Assays with sea stars

Allelopathic activities of sponge extracts

Although there is anecdotal evidence for allelopathic interactions between benthic invertebrates engaged in spatial competition, only a few studies have established the involvement of chemical agents in field experiments. We have developed a technique in which crude organic extracts of marine sponges were incorporated into hard, stable gels that serve as a substratum for overgrowth by invertebrates in the field. Overgrowth organisms were secured to the center of assay plates and allowed to grow laterally over control gels and gels containing a crude organic sponge extract that was volumetrically equivalent to the concentration found in sponge tissues. Extracts of 20 species of Caribbean sponges were assayed in Florida using 3 overgrowth sponges: Tedania ignis, Lissodendoryx isodictialis, and Haliclona hogarthi. In addition, extracts of the sponge Aplysilla longispina were assayed in North Carolina using the tunicate Diplosoma listerianum as the over- growth organism. The allelopathic effects varied between extracts of different sponge species, but were consistent across overgrowth organisms. Of the sponge extracts tested, 30% inhibited sponge growth (Amphimedon compressa, Aplysilla longispina, Aplysina cauliformis, Dysidea etheria, Ectyo- plasia ferox, and Phorbas amaranthus), while 15% promoted overgrowth (Agelas wiedenmeyeri, Geodia gibberosa, and Halichondria sp.). The remaining 55% of sponge extracts had no effect on sponge growth. The technique described herein represents a more ecologically relevant method than past techniques for assaying the allelopathic properties of extracts of marine organisms. Moreover, this study provides evidence that sponge metabolites may act as allomones by preventing overgrowth of some sponge species, and as both allomones and kairomones by enhancing overgrowth of others.

Biosynthetically diverse compounds from a saltwater culture of sponge-derived Aspergillus niger.

The new compound, asperic acid (1), and the known compounds hexylitaconic acid (2), malformin C (3), pyrophen (4), and asperazine (5) were isolated from the saltwater culture of Aspergillus niger derived from a Caribbean sponge, Hyrtios proteus. The structure elucidation of asperic acid is presented.

Metabolites from the sponge plakortis simplex. II. : Isolation of four bioactive lactone compounds and of a novel related amino acid

Seven lactone metabolites namely the known plakortones B-D ( 1-3) the novel plakortones E ( 4) and F ( 5) and two novel δ-lactones, named simplactones A ( 6) and B ( 7) have been isolated from the Caribbean sponge Plakortis simplex, and their structures characterized by spectroscopic and chemical means. In addition the unprecedented amino acid 8 has been isolated from the same source, and a hypothesis of its biogenetic relationship with simplactones is herein reported. Plakortones B-F and compound 8 exhibited in vitro cytotoxic activity on WEHI 164, murine fibrosarcoma cell line.

Structures and absolute stereochemistry of isocyanide and isothiocyanate amphilectenes from the Caribbean sponge Cribochalina sp.

Three new diterpenes ( 5–7), based on amphilectene skeleton, were isolated from the Caribbean sponge Cribochalina sp.. All contain isocyanide and isothiocyanate functions and are epimers at C-7 of previously characterized diterpenoids. The structures of 5–7 were established by spectroscopic techniques. The sponge extract also showed the presence of the known metabolite 4, together with the new bicyclic diterpene 8, potential precursor of the co-occurring amphilectenes. For the first time, the absolute configuration of the amphilectene skeleton has been assigned by applying the modified Mosher's method on a derivative of the main compound 4. The isocyanide 4 reduced the proliferation of lymphocytes T and B under various stimuli.

11-Deoxyfistularin-3, a new cytotoxic metabolite from the caribbean sponge Aplysina fistularis insularis.

11-Deoxyfistularin-3 (1), a new bromotyrosine derivative, was isolated among other known compounds such as fistularin-3 (2), aerothionin (3), and 11-oxoaerothionin (4) from the Caribbean sponge Aplysinafistularis (Aplysinellidae). The structure of 1 was determined by spectroscopic analysis and showed in vitro activity against the human breast carcinoma cell line MCF-7.

Secobatzellines A and B, Two New Enzyme Inhibitors from a Deep-Water Caribbean Sponge of the Genus Batzella

Secobatzelline A (1), a new batzelline natural analogue, and secobatzelline B (2), a likely artifact formed during the isolation procedure, have been isolated from a deep-water marine sponge of the genus Batzella. Secobatzellines A and B inhibited the phosphatase activity of calcineurin, and secobatzelline A inhibited the peptidase activity of CPP32. Both compounds showed in vitro cytotoxicity against P-388 and A-549 cell lines. The isolation and structure elucidation of secobatzellines A (1) and B (2) are described.

Enantioselective synthesis of (3 R,4 E)-19-methylicos-4-en-1-yn-3-ol, a bioactive metabolite of the marine sponge Cribrochalina vasculum

The first stereoselective synthesis of (3 R,4 E)-19-methylicos-4-en-1-yn-3-ol, an immunosuppressive and antitumoral metabolite isolated from the Caribbean sponge Cribrochalina vasculum, has been achieved and its stereostructure has been confirmed. The key step of the synthesis involves a borane-mediated reduction of the parent ( E)-19-methyl-1-trimethylsilylicos-4-en-1-yn-3-one in the presence of a chiral oxazaborolidine.

ChemInform Abstract: Ectyoplasides A—B — Unique Triterpene Oligoglycosides from the Caribbean Sponge Ectyoplasia ferox.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Bromoisoxazoline Alkaloids from the Caribbean Sponge Aplysina insularis

Abstract An investigation of a specimen of the Caribbean sponge Aplysina insularis resulted in the isolation of fourteen bromoisoxazoline alkaloids (1 - 14), of which 14-oxo-aerophobin-2 (1)* is a novel derivative. Structure elucidation of the compounds have been established from spectral studies and data for 1 are reported. Constituents 2 to 6 and 11 to 14 have not been identified sofar in Aplysina insularis species. The presence of the known compounds 7 to 9 in Aplysina insularis indicates that their use for chemotaxonomical purposes is questionable.

Antimicrobial activity of Caribbean sponge extracts

AME Aquatic Microbial Ecology Contact the journal Facebook Twitter RSS Mailing List Subscribe to our mailing list via Mailchimp HomeLatest VolumeAbout the JournalEditorsSpecials AME 19:279-284 (1999) - doi:10.3354/ame019279 Antimicrobial activity of Caribbean sponge extracts Rochelle W. Newbold1, Paul R. Jensen2, William Fenical2, Joseph R. Pawlik1,* 1Biological Sciences and Center for Marine Science Research, University of North Carolina at Wilmington, Wilmington, North Carolina 28403-3297, USA 2Scripps Institution of Oceanography, Center for Marine Biotechnology and Biomedicine, University of California, San Diego, La Jolla, California 92093-0236, USA *Addressee for correspondence. E-mail: pawlikj@uncwil.edu ABSTRACT: Marine sponges produce a diversity of unusual chemical compounds, but the ecological functions of these metabolites remain largely unknown. To determine if sponge secondary metabolites have ecologically significant antimicrobial effects, organic extracts from 33 species of Caribbean sponges were assayed for antibiotic activity against a test panel of marine bacteria. The test panel consisted of 8 strains representing 6 genera of marine bacteria and included an opportunistic pathogen (Vibrio parahaemolyticus), a common fouling bacterium (Deleya marina), and strains isolated from seawater and healthy and necrotic Caribbean sponges. Extracts were tested for antibiotic activity at concentrations that were volumetrically equivalent to those found in sponge tissues (whole-tissue concentrations). Bioassay results revealed that 16 species (48%) exhibited antibiotic activity against at least 1 bacterial isolate and that the 2 bacteria isolated from necrotic sponge tissues were the most sensitive test strains (inhibited by 40% of the extracts). Extracts from Amphimedon compressa, Amphimedon erina, Aplysina lacunosa, and Ptilocaulis spiculifera inhibited the largest numbers of test strains and exhibited the most potent antibiotic activities with values frequently exceeding those of a control antibiotic (gentamicin). The pattern of antimicrobial activity was different for 15 of 16 active sponge species, suggesting that diverse taxa do not produce similar antibacterial metabolites. Overall, only 23% of the extract/bacterial interactions exhibited antibacterial activity, indicating that, in general, conspicuous members of the Caribbean sponge community do not produce broad-spectrum antibacterial metabolites. All of the species yielding antibacterial extracts also deterred feeding by reef fishes in a previous study, suggesting that some secondary metabolites may have evolved multiple defensive functions. Stevensine, a compound from Axinella corrugata (= Teichaxinella morchella) known to deter feeding by predatory reef fishes, exhibited weak antimicrobial activity, suggesting that this potent feeding deterrent is not solely responsible for the antimicrobial activity detected in the crude sponge extract. KEY WORDS: Chemical defense · Antimicrobial · Sponges · Secondary metabolites Full text in pdf format PreviousNextExport citation RSS - Facebook - Tweet - linkedIn Cited by Published in AME Vol. 19, No. 3. Publication date: October 27, 1999 Print ISSN: 0948-3055; Online ISSN: 1616-1564 Copyright © 1999 Inter-Research.

Glycolipids from sponges. VII. 1 simplexides, novel immunosuppressive glycolipids from the caribbean sponge Plakortis simplex

The new glycolipids simplexides ( 1) have been isolated from the marine sponge Plakortis simplex, and their structure determined by spectroscopic data and microgram-scale chemical degradation. Simplexides are composed of long-chain secondary alcohols glycosylated by a disaccharide chain, and represent a new structural kind of glycolipids. Simplexides strongly inhibit proliferation of activated T-cells by a non-cytotoxic mechanism and can be regarded as simple model molecules for designing immunosuppressive drugs.

Ectyoplasides A–B – Unique Triterpene Oligoglycosides from the Caribbean SpongeEctyoplasia ferox

Two novel norlanostane triglycosides, ectyoplasides A (1) and B (2), have been isolated from the methanolic extracts of the Caribbean sponge Ectyoplasiaferox (Raspaliidae, Axinellida). Their structures have been established by extensive application of high-resolution FABMS and two-dimensional NMR techniques, supported by chemical and enzymatic degradation methods. Ectyoplasides A and B have been shown to possess identical sugar chains (composed of two β-galactose units and one α-arabinose unit), but to differ in their aglycone moieties, which possess nortriterpene skeletons with an unprecedented substitution pattern on ring A. Ectyoplasides A and B show moderate cytotoxic activity when tested in vitro towards various cell lines

Spongivory by Parrotfish in Florida Mangrove and Reef Habitats

Abstract. Although parrotfish are generally reported to be herbivorous, increasing evidence suggests that some Caribbean species feed on sponges. After observing grazing scars on the barrel sponge, Xestospongia muta, 40 sponges were videotaped on three reefs for >0.5 h to determine the frequency of parrotfish bites on this species. A total of 10 h of video recording captured 45 bites on normally coloured X. muta and 527 bites on four bleached X. muta by the parrotfish Sparisoma aurofrenarum, Scarus croicensis and Scarus taeniopterus. The viscera gut and liver of 55 parrotfish collected from mangrove and reef habitats were digested in nitric acid and analysed for spicule content. The parrotfish collected in the mangroves mostly Scarus guacamaia and Sparisoma chrysopterum had significantly higher masses of spicules in their viscera than did parrotfish collected on the reef Sparisoma aurofrenatum, Sparisoma viride, Sparisoma chrysopterum, Scarus vetula, Scarus coelestinus and Scarus taeniopterus. The spicules of Geodia gibhrrosa, a chemically undefended sponge that is common in the mangroves but rare in exposed locations on the reef, were abundant in the viscera of parrotfish collected in the mangroves. These results provide further evidence that fish predation has an important effect on the distribution and abundance of Caribbean sponges.

Discorhabdin P, a new enzyme inhibitor from a deep-water Caribbean sponge of the genus Batzella.

Discorhabdin P (1), a new discorhabdin analogue, has been isolated from a deep-water marine sponge of the genus Batzella. Discorhabdin P (1) inhibited the phosphatase activity of calcineurin and the peptidase activity of CPP32. It also showed in vitro cytotoxicity against P-388 and A-549 cell lines. The isolation and structure elucidation of discorhabdin P (1) are described.

Coral reef sponges: Do predatory fishes affect their distribution?

The predatory activities of fishes are thought to have little impact on the distribution and abundance of sponges on Caribbean coral reefs. To test this premise, 15 species of sponges were transplanted from mangrove and grassbed habitats, where spongivorous fishes are rare, to shallow patch reefs, where spongivorous fishes are common. Twelve of these 15 sponge species could also be found in cryptic locations, but not in conspicuous locations, on nearby reefs. After 3 d, there was significant loss of wet mass of uncaged sponges versus caged sponges for nine sponge species because of consumption by spongivores, primarily angelfishes. A mean of >50% of the sponge tissue was consumed for seven species: Chondrilla nucula, Chondrosia collectrix, Geodia gibberosa, Halichondria sp., Halichondria melanodocia, Myriastra kalitetilla, and Tedania ignis. These results, in addition to other recent data on the chemical defenses of Caribbean reef sponges against generalist predatory fishes, suggest that predation plays an important role in structuring the reef sponge community and that predation limits the distribution of some Caribbean sponges.