Sponge Compounds Research Articles

Dragon exploration system on marine sponge compounds interactions

BackgroundNatural products are considered a rich source of new chemical structures that may lead to the therapeutic agents in all major disease areas. About 50% of the drugs introduced in the market in the last 20 years were natural products/derivatives or natural products mimics, which clearly shows the influence of natural products in drug discovery.ResultsIn an effort to further support the research in this field, we have developed an integrative knowledge base on Marine Sponge Compounds Interactions (Dragon Exploration System on Marine Sponge Compounds Interactions - DESMSCI) as a web resource. This knowledge base provides information about the associations of the sponge compounds with different biological concepts such as human genes or proteins, diseases, as well as pathways, based on the literature information available in PubMed and information deposited in several other databases. As such, DESMSCI is aimed as a research support resource for problems on the utilization of marine sponge compounds. DESMSCI allows visualization of relationships between different chemical compounds and biological concepts through textual and tabular views, graphs and relational networks. In addition, DESMSCI has built in hypotheses discovery module that generates potentially new/interesting associations among different biomedical concepts. We also present a case study derived from the hypotheses generated by DESMSCI which provides a possible novel mode of action for variolins in Alzheimer’s disease.ConclusionDESMSCI is the first publicly available (http://www.cbrc.kaust.edu.sa/desmsci) comprehensive resource where users can explore information, compiled by text- and data-mining approaches, on biological and chemical data related to sponge compounds.

Salty sea regulators of cystic fibrosis

New, bioactive marine sponge compounds that function as inhibitors of the poly (ADP-ribose) polymerase family of proteins have now been identified to promote the correction of cystic fibrosis. Poly (ADP-ribose) polymerase inhibitors may be managers of proteostasis biology, consistent with their role (or roles) in remediation of inflammatory states.

Marine Sponge: A Potential Source for Methoxylated Polybrominated Diphenyl Ethers in the Asia-Pacific Food Web

Marine sponges collected in Palau, Micronesia, were investigated for hydroxylated or methoxylated analogues of brominated diphenyl ethers (BDEs), brominated dibenzo-p-dioxin (BDD), and brominated biphenyls. The neutral fractions of Haliclona sp. and Callyspongia sp. contained 2'-methoxy-2,3',4,5'-tetraBDE, 6-methoxy-2,2',4,4'-tetraBDE, 2',6-dimethoxy-2,3',4,5-tetraBDE 2,2'-dimethoxy-3,3',5,5'-tetrabromobiphenyl, several methoxy-triBDEs, and dimethoxy-penta-/hexaBDEs. The methoxylated BDEs in sponges were strikingly similar to those of local fish living in the western Pacific Ocean. The total concentrations of these compounds (ΣMeO-PBDE) in both sponges were 63.5 μg/g extractable organic matter (EOM) for Haliclona sp. and 36.5 μg/g EOM for Callyspongia sp., which were about 2 orders of magnitude higher than the levels seen in tropical coral reef fish (unicornfish or surgeonfish) (280-290 ng/g lipid) and groupers (550 ng/g lipid) from Okinawan coastal waters. The phenolic fractions of both sponges contained hydroxy-methoxy tetra-/pentaBDEs as well as hydroxy-tetraBDD, in addition to the corresponding phenolic tetraBDE analogues. Although the total concentrations of phenolic products (27-80 μg/g EOM) in both sponges fell within a range comparable to the methoxylated products, ΣOH-PBDE in local fish were trace level (less than 10 ng/g lipid of) or undetectable. This survey indicates that marine sponges are a possible source of the MeO-PBDE analogues that biomagnify via the food chain to the higher trophic organisms in the western Pacific, whereas the distribution of the corresponding hydroxylated analogues is limited.

Induction of apoptosis in endometrial cancer cells by psammaplysene A involves FOXO1

Objective Endometrial cancer is the most common type of gynecologic cancer in the United States. In this study, we propose that a marine sponge compound, psammaplysene A (PsA) induces apoptosis in endometrial cancer cells through forced nuclear expression of FOXO1. Methods Ishikawa and ECC1 cells were treated with varying doses of PsA. FOXO1 protein localization was observed using immunofluorescent staining of cells. The effects of PsA on cell viability and proliferation were assessed using a cell viability assay and a BrdU incorporation assay respectively. Cell cycle analysis was performed using flow cytometry. To assess the role of FOXO1 in PsA-induced apoptosis, FOXO1 was silenced in ECC1 cells using siRNA technique, and overexpressed in Ishikawa cells using an adenovirus containing FOXO1 cDNAs. Western blots were used to measure levels of FOXO1 and cleaved PARP proteins. Results Treatment of both ECC1 and Ishikawa cells with PsA caused an increase in nuclear FOXO1 protein, a dramatic decrease in cell viability of approximately 5-fold ( p < 0.05) and minimal effect on proliferation. Furthermore, treatment of cells with PsA doubled the percentage of cells in the G2/M phase ( p < 0.05). PsA induced apoptosis in endometrial cancer cells. When FOXO1 was silenced in ECC1 cells and treated with PsA, the incidence of apoptosis decreased. In addition, overexpression of FOXO1 with PsA treatment increased apoptosis. Conclusions Increasing nuclear FOXO1 function is important for the induction of apoptosis of endometrial cancer cells by PsA.

The sponge genetree server—providing a phylogenetic backbone for poriferan evolutionary studies

Unravelling the phylogenetic relationships of sponges (Phylum Porifera) is an important as well as challenging task. It helps the understanding of character evolution among early branching metazoans but also aids in bioprospecting for valuable bioactive sponge compounds. However, the phylogenetic relationships among Porifera are largely unsolved, because the simple poriferan bauplan frequently prevents unambiguous taxonomic species assignment and a clear definition of morphological synapomorphies is difficult (see e.g. Boury-Esnault 2006). DNA sequence markers are frequently employed to overcome morphological shortcomings in phylogeny (e.g. Kelly Borges et al. 1991) and taxonomy (e.g. DNA barcoding, see Wörheide &amp; Erpenbeck 2007). However, some DNA markers suffer from insufficient phylogenetic signal (see e.g. Duran et al. 2004 and Wörheide 2006 on CO1 in population studies) and unequal evolutionary rates among taxa (see e.g. Erpenbeck et al. 2004 on 28S in Haplosclerida). Therefore, a careful evaluation and selection of molecular markers for each individual project is required.

Sipholenol A, a marine‐derived sipholane triterpene, potently reverses P‐glycoprotein (ABCB1)‐mediated multidrug resistance in cancer cells

Through extensive screening of marine sponge compounds, the authors have found that sipholenol A, a sipholane triterpene isolated from the Red Sea sponge, Callyspongia siphonella, potently reversed multidrug resistance (MDR) in cancer cells that overexpressed P-glycoprotein (P-gp). In experiments, sipholenol A potentiated the cytotoxicity of several P-gp substrate anticancer drugs, including colchicine, vinblastine, and paclitaxel, but not the non-P-gp substrate cisplatin, and significantly reversed the MDR of cancer cells KB-C2 and KB-V1 in a concentration-dependent manner. Furthermore, sipholenol A had no effect on the response to cytotoxic agents in cells lacking P-gp expression or expressing MDR protein 1 or breast cancer resistance protein. Sipholenol A (IC(50) > 50 microM) is not toxic to all the cell lines that were used, regardless of their membrane transporter status. Accumulation and efflux studies with the P-gp substrate [(3)H]-paclitaxel demonstrated that sipholenol A time-dependently increased the intracellular accumulation of [(3)H]-paclitaxel by directly inhibiting P-gp-mediated drug efflux. In addition, sipholenol A did not alter the expression of P-gp after treating KB-C2 and KB-V1 cells for 36 h and 72 h. However, it efficaciously stimulated the activity of ATPase of P-gp and inhibited the photolabeling of this transporter with its transport substrate [(125)I]-iodoarylazidoprazosin. Overall, the present results indicate that sipholenol A efficiently inhibits the function of P-gp through direct interactions, and sipholane triterpenes are a new class of potential reversing agents for treatment of MDR in P-gp-overexpressing tumors.

A comparative study of the actions of alkylpyridinium salts from a marine sponge and related synthetic compounds in rat cultured hippocampal neurones

BackgroundPolymeric alkylpyridinium salts (poly-APS), are chemical defences produced by marine sponges including Reniera sarai. Poly-APS have previously been shown to effectively deliver macromolecules into cells. The efficiency of this closely follows the ability of poly-APS to form transient pores in membranes, providing strong support for a pore-based delivery mechanism. Recently, water soluble compounds have been synthesised that are structurally related to the natural polymers but bear a different number of pyridinium units. These compounds may share a number of bio-activities with poly-APS. Using electrophysiology, calcium imaging and 1,6-diphenyl-1,3,5-hexatriene imaging, the pore forming properties of poly-APS and four related synthetic oligomers have been tested on primary cultured rat hippocampal neurones.ResultsAcute application of poly-APS (0.5 μg/ml), reduced membrane potential, input resistance and suppressed action potential firing. Poly-APS evoked inward cation currents with linear current-voltage relationships similar to actions of pore formers on other cell types. Poly-APS (0.005–5 μg/ml) also produced Ca2+ transients in ~41% of neurones. The dose-dependence of poly-APS actions were complex, such that at 0.05 μg/ml and 5 μg/ml poly-APS produced varying magnitudes of membrane permeability depending on the order of application. Data from surface plasmon resonance analysis suggested accumulation of poly-APS in membranes and subsequent enhanced poly-APS binding. Even at 10–100 fold higher concentrations, none of the synthetic compounds produced changes in electrophysiological characteristics of the same magnitude as poly-APS. Of the synthetic oligomers tested compounds 1 (monomeric) and tetrameric 4 (5–50 μg/ml) induced small transient currents and 3 (trimeric) and 4 (tetrameric) produced significant Ca2+ transients in hippocampal neurones.ConclusionPoly-APS induced pore formation in hippocampal neurones and such pores were transient, with neurones recovering from exposure to these polymers. Synthetic structurally related oligomers were not potent pore formers when compared to poly-APS and affected a smaller percentage of the hippocampal neurone population. Poly-APS may have potential as agents for macromolecular delivery into CNS neurones however; the smaller synthetic oligomers tested in this study show little potential for such use. This comparative analysis indicated that the level of polymerisation giving rise to the supermolecular structure in the natural compounds, is likely to be responsible for the activity here reported.

Status and Perspective of Sponge Chemosystematics

In addition to their pharmaceutical applications, sponges are an important source of compounds that are used to elucidate classification patterns and phylogenetic relationships. Here we present a review and outlook on chemosystematics in sponges in seven sections: Secondary metabolites in sponges; Further applications of bioactive compound research in sponges; Sponge chemotaxonomy; Pitfalls of sponge chemotaxonomy; The chemotaxonomic suitability of sponge compounds; Potential synapomorphic markers in sponges; and The future of sponge chemotaxonomy.

Characterization of water‐soluble organoarsenic compounds in marine sponges

AbstractTo provide a better understanding of the arsenic cycle in the marine ecosystem and marine biotechnological viewpoints, the present study is intended to identify arsenic compounds contained in marine sponges. Marine sponges were collected off the coastal waters of Magsaysay Islet within Bohol Sea near Mindanao (Philippines) and in the Seto Inland Sea (Japan) by skin‐diving. Water‐soluble arsenic compounds were extracted with methanol–water (1: 1, v/v) from freeze‐dried samples of 13 marine sponges. The extracts were analyzed using high‐performance liquid chromatography (HPLC) with an inductively coupled plasma mass spectrometer (ICP/MS) serving as an arsenic‐specific detector. All marine sponges contained arsenobetaine [(CH3)3As+ CH2COO−], 2,3‐dihydroxypropyl 5‐deoxy‐5‐(dimethylarsinoyl)‐β‐ribofuranoside (arseno‐sugar X), and 3‐glycerophosphoryl‐2‐hydroxy‐1‐[5‐deoxy‐5‐(dimethylarsinoyl)‐β‐ribofuranosyloxy]propane (arseno‐sugar X1), among which arseno‐sugarX1 was most abundant in the Jaspis spp., Suberites spp. and four Japanese sponges. Also, a linear relationship existed between total water‐soluble arsenic and arsenobetaine Copyright © 2006 John Wiley &amp; Sons, Ltd.

Biology of the Porifera: cell culture

The discovery that dissociated sponge cells will reaggregate to form a functional organism was the basis for the establishment of sponge cell cultures that have been used as a model for the study of fundamental processes in developmental biology and immunology. More recent is the discovery of unique bioactive compounds in marine sponges, and the feasibility of in vitro production of these chemicals is being evaluated. Techniques are well established for cell dissociation; development of several nutrient media formulations has resulted in improvements in viability and cell division; and molecular approaches to identification of genes responsible for regulation of cell cycling may provide unique perspectives in culture optimization. The use of novel substrates for immobilization of cells offers alternatives for proliferation and scale-up. All of these results support the potential for development of a model system for the study of basic metabolic processes involved in cell differentiation, as well as an in vitro production system for sponge-derived bioactive compounds. Perhaps more important, however, is the development of cell lines of these "simple" metazoans to facilitate basic cell physiology and molecular biology research that may be applied to understanding more complex metazoan systems, including humans.

Halogenated Natural Products in Five Species of Antarctic Sponges: Compounds with POP-like Properties?

Purified extracts of five species of Antarctic sponges (Demospongiae: Kirkpatrickia variolosa, Artemisina apollinis, Phorbas glaberrima, and Halichondria sp. and Calcarea: Leucetta antarctica) from King George Island were analyzed by GC/MS for the presence of persistent and lipophilic halogenated compounds to identify bioaccumulative halogenated natural products. Sample extracts were prepared using methods identical for the determination of POPs, namely, microwave-assisted extraction with organic solvents, gel permeation chromatography, and column chromatography on deactivated silica. In addition, samples were treated with sulfuric acid to remove acid-destructible compounds. PCBs were not detectable and only traces of lindane, p,p'-DDE, and alpha-HCH were detected in these samples in decreasing order of abundance, underscoring their uncontaminated state. In contrast, 146 brominated compounds were identified by correct isotopic ratios m/z 79 and 81, 50% of which eluted prior to lindane including the most abundant peaks. Each sponge sample contained > or = 35 brominated compounds of natural origin, 14 of which were detected in all species. Estimated concentrations ranged from the high ng/kg to mg/kg (air-dried weights) and relative distributions of the same compounds in different sponges were highly variable. The high abundance of these compounds relative to known anthropogenic pollutants strongly suggests a natural origin. Multiple mode (EI-, ECNI-, and PCI-) GC/MS enabled identification of an aliphatic ketone tentatively identified as 1,1,2-tribromo-oct-1-en-3-one, present in all species but highest in Phorbas glaberrima. Several halogenated phenols including 2,4,6-tribromophenol were also abundant in Phorbas glaberrima as were halogenated anisoles in lower relative abundances. The halogenated phenols were analyzed without derivatization. The sample of Halichondria sp. contained the dibromotrichloro monoterpene MHC-1, a recently described environmental contaminant in fish and seals. Retrospective analysis of other marine samples confirmed that 2,4,6-tribromophenol was present in seal blubber from both the Arctic and the Antarctic. The presence of naturally occurring organohalogens such as 2,4,6-tribromophenol and MHC-1 in Antarctic marine invertebrates thus provides a link to their occurrence in marine mammals.

A New Class of Ethylene—Propylene—Diene Terpolymers Produced from Constrained Geometry Metallocene Catalysts

Abstract Until recently, ethylene/propylene/diene (EPDM) terpolymers have been manufactured exclusively using vanadium based Ziegler—Natta catalyst systems. The vanadium based catalysts are known to have both product and process limitations. These limitations are due to a complex combination of factors including monomer reactivity, catalyst activity, reactor temperatures and pressures. Single-site metallocene constrained geometry catalyst (CGC) technology enables the manufacture of EPDM terpolymers at higher reactor temperature and catalyst efficiency than standard Ziegler—Natta catalyst systems. The unique combination of monomer, catalyst and process technology enables the manufacture of highly crystalline EPDMs having ethylene contents over 90 wt %. This study investigated these new highly crystalline EPDM terpolymers and their differentiation from commercially available EPDMs. The results indicated that these new EPDMs had very high green strength and barrier properties, yet could be cured by conventional vulcanization techniques. The cure response of these EPDMs to either peroxide or sulfur increased with increasing ethylene content. Sulfur cured vulcanizates had much higher tensile strength than peroxide cured vulcanizates. These new EPDMs demonstrated utility as additives to enhance the abrasion, hot tear, and tensile properties of natural rubber compounds. Sponge compounds, having the unique combination of polyethylene physical properties and the utility of sulfur vulcanization were developed from these new polymers.

Breast implant classification with MR imaging correlation: (CME available on RSNA link)

Rupture is now recognized as an important and common complication of breast implants. Magnetic resonance (MR) imaging is the most accurate method for evaluating implant integrity but requires an understanding of the numerous variations in implant construction that are encountered clinically. To assist in diagnosis, the authors provide an MR-oriented breast implant classification scheme based on data from 4,014 patients (>9,966 current or previous implants), the literature, and other primary documentation. This scheme consists of 14 implant types: 1) single-lumen silicone gel-filled, 2) single-lumen gel-saline adjustable, 3) single-lumen saline-, dextran-, or polyvinyl pyrrolodone-filled, 4) standard double-lumen, 5) reverse double-lumen, 6) reverse-adjustable double-lumen, 7) gel-gel double-lumen, 8) triple-lumen, 9) Cavon "cast gel", 10) custom, 11) solid pectus, 12) sponge (simple or compound), 13) sponge (adjustable), and 14) other. The MR imaging and mammographic appearance of many implant types is correlated with their actual appearance after explantation. A brief history of prosthetic breast augmentation and reconstruction is also provided to allow this classification method to be placed in historical perspective. Knowledge of the variety of breast implant types will help reduce misdiagnoses by providing imagers with better understanding of the expected appearances of breast implants. This classification scheme will allow stratification of data for studying incidence, prevalence, and risk factors for and causes of implant failure, as well as permitting better correlation with patient symptoms and surgical outcome.

Charge Density Distribution in the “Proton Sponge” Compound 1,8-Bis(dimethylamino)naphthalene

This is the first low-temperature, high-resolution X-ray and neutron diffraction study of charge distribution in an uncomplexed proton sponge compound. In the parent compound of this class, 1,8-bis(dimethylamino)naphthalene (DMAN), a small degree of asymmetry of the naphthalene moiety is induced by weak, asymmetric intermolecular interactions. The only manifestation of this asymmetry is at the level of the Laplacian of the charge distribution. Comparing the DMAN molecule with its cation shows the consequences of protonation, such as shortening of the C−C, and lengthening of the C(ar)−H and C−N bond lengths. These changes are even more apparent in CP properties, with ρb on average smaller in the cation than in the neutral molecule. Relationships between CP and structural parameters viz. ρb vs Laplacian, Laplacian vs bond length, and ρb vs bond length depend on bond type, and are different for DMAN and its cation. Comparison with ab initio calculated values reveals some systematic discrepancies. Only two cr...

The SRPT—An automatic parallel plate plastimeter for controlling compound processibility

The SRPT—the stress relaxation processibility tester—may be applied for the same purposes as any parallel plate plastimeter, such as the Williams, Defo and Wallace plastimeters, but has advantages over each of these. Testing with the SRPT is fast, simple and automatic. The SRPT also measures stress relaxation, which is not possible with the other parallel plate plastimeters. This facility allows SRPT data to be interpreted in terms not only of plasticity but also of nerve. Applications for the SRPT include raw material control, mixing control, scorch protection and the control of compounds for moulding, calendering and extrusion. Potential applications include measurement of green strength, the control of sponge compounds, and the prediction of die swell behaviour. Processibility can be assessed by using a simple ‘processibility plot’, but certain rules must be observed when evaluating the SRPT for this purpose.

FEEDING AND PHARMACOLOGICAL PROPERTIES OFANISODORIS NOBILISINDIVIDUALS (MOLLUSCA; NUDIBRANCHIA) SELECTING DIFFERENT NOXIOUS SPONGES PLUS DETRITUS

Individual differences in Anisodoris nobilis food selection were sought in the natural environment, to determine why their digestive glands differed pharmacologically. Of 73 stationary A. nobilis specimens turned over in the initial survey, 84% of those on sponges and 65% of those on detritus had their mouths everted; no others were feeding. Microacoustic observations showed that an individual stops on a sponge, everts its proboscis for a long period, then rasps the sponge. Field studies of individual diets were made without disturbing the animals, by tabulating the foods on which each nudibranch was found to be stationary.Twelve individual nudibranchs observed subtidally about three times daily for 8 days differed significantly in the sponge species they selected. Each individual was found stopped on detritus during roughly 50% of the observations, remaining there for 1 day at a time. Each nudibranch stopped for <2 days on a sponge, sometimes returning to that spot during subsequent days. Among individuals transplanted to different feeding sites, each everted its mouth only when on the sponge species it had been eating at the previous site. Two months of subsequent, scattered observations showed occasional longer-term feeding differences.Noxious histamine (present in each sponge) and doridosine (found only in the nudibranch) accounted for different pharmacological properties in bioassays of Anisodoris digestive gland extracts. Histamine disappeared when the nudibranchs ate detritus, which suggests that this mixed diet purges sponge compounds from the nudibranch. Extracts from edible sponges administered to nudibranchs caused fleeing, while extracts of avoided sponges caused violent contractions, increased mucus production, and even death.