Dendrilla Membranosa Research Articles

On the identity of "Dendrilla membranosa" (Porifera, Dendroceratida) sensu Burton, and the specimens collected in Argentina, SW Atlantic Ocean

There has been confusion regarding the specimens identified as "Dendrilla membranosa (Pallas, 1766)" in Antarctic and subantarctic waters, considering that the original description corresponded to specimens from the Indian Ocean. In this study, we clarified the identification of the specimens collected in Argentinian waters, SW Atlantic Ocean, that should be identified as Dendrilla antarctica Topsent, 1905, updating its distributional range and considering the new records reported in the present study.

Amphipod diversity and metabolomics of the Antarctic spongeDendrilla antarctica

AbstractThe western Antarctic Peninsula harbours a diverse benthic marine community where dense canopies of macroalgae can dominate the shallow subtidal zone (0–40 m or greater). In the lower portion of this range (below 25–35 m depending on topography), invertebrates such as sponges and echinoderms can be found in greater abundance due to reduced competition for space from the algal species.Dendrilla antarctica(previouslyDendrilla membranosa) is a common demosponge that thrives in both communities and is known for producing diterpene secondary metabolites as a defence against sympatric sea star and amphipod predators. Omnivorous mesograzers such as amphipods inhabit both communities; however, they are in greatest abundance within the macroalgal canopy. Due to the differences between habitats, it was hypothesized that specific amphipod species not susceptible to the defensive metabolites ofD. antarcticawould take refuge from predators in the chemically defended sponge. Analysis of the metabolome and amphipod communities from sponges in both habitats found correlations of metabolic profile to both abundance and habitat. These studies serve to inform our understanding of the complex ecosystem of the Antarctic benthos that stands to be dramatically altered by the rapidly changing climate in the years to come.

Identification of Cytotoxicity of Marine Sponge Dendrilla Membranosa Against L929 Cell Line

Marine sponges are rich sources of pharmacological active compound. Marine sponge, Dendrilla membranosa was collected from the Vizhingam coast. The sponge extract was tested against eight human bacterial pathogens. The bioactive compounds present in marine sponge were determined by GC-MS analysis. The cytotoxic effect of the sponge was evaluated by using MTT assay. The extracts showed potent anti-bacterial activity against Staphylococcus aureus, Bacillus subtilis, Streptococcus pyogens. The bioactive compound present in marine sponge was identified by GC-MS analysis and the compounds are ethane, butane, formate pentane, Alpha d-galactopyranoside, 2-Ethylhexyl2-ethylhexanoate, Hexahydro hexitol, Styrene, Alpha-d glucopyranoside 1-pentyl-2-proppyl-1-octene, nonadecane, 1,2-benzenedicarboxylic acid, bis-2, Octanoic acid. The test material showed none cytotoxic response to fibroblasts cells. The results of present investigation revealed that, Dendrilla membranosa is a potential source of novel anticancer and antibacterial leads.

Synthesis of (+)-Darwinolide, a Biofilm-Penetrating Anti-MRSA Agent.

Darwinolide, a recently identified marine natural product from the Antarctic sponge Dendrilla membranosa, was previously shown to exhibit promising activity against the biofilm phase of methicillin-resistant Staphylococcus aureus. Its challenging tetracyclic rearranged spongian diterpenoid structure links a trimethylcyclohexyl subunit to a seven-membered core with two fused tetrahydrofuran units. Herein, we describe the first synthesis of (+)-darwinolide, which features a convergent aldol fragment coupling, an Ireland-Claisen rearrangement, and an organocatalytic desymmetrization as the key steps. Our results provide a foundation for the development of novel antibiofilm-specific antibiotics.

Synthesis of (+)‐Darwinolide, a Biofilm‐Penetrating Anti‐MRSA Agent

AbstractDarwinolide, a recently identified marine natural product from the Antarctic sponge Dendrilla membranosa, was previously shown to exhibit promising activity against the biofilm phase of methicillin‐resistant Staphylococcus aureus. Its challenging tetracyclic rearranged spongian diterpenoid structure links a trimethylcyclohexyl subunit to a seven‐membered core with two fused tetrahydrofuran units. Herein, we describe the first synthesis of (+)‐darwinolide, which features a convergent aldol fragment coupling, an Ireland–Claisen rearrangement, and an organocatalytic desymmetrization as the key steps. Our results provide a foundation for the development of novel antibiofilm‐specific antibiotics.

Immuno-Modulatory and Anti-Inflammatory Effects of Dihydrogracilin A, a Terpene Derived from the Marine Sponge Dendrilla membranosa.

We assessed the immunomodulatory and anti-inflammatory effects of 9,11-dihydrogracilin A (DHG), a molecule derived from the Antarctic marine sponge Dendrilla membranosa. We used in vitro and in vivo approaches to establish DHG properties. Human peripheral blood mononuclear cells (PBMC) and human keratinocytes cell line (HaCaT cells) were used as in vitro system, whereas a model of murine cutaneous irritation was adopted for in vivo studies. We observed that DHG reduces dose dependently the proliferative response and viability of mitogen stimulated PBMC. In addition, DHG induces apoptosis as revealed by AnnexinV staining and downregulates the phosphorylation of nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB), signal transducer and activator of transcription (STAT) and extracellular signal–regulated kinase (ERK) at late time points. These effects were accompanied by down-regulation of interleukin 6 (IL-6) production, slight decrease of IL-10 and no inhibition of tumor necrosis factor-alpha (TNF-α) secretion. To assess potential properties of DHG in epidermal inflammation we used HaCaT cells; this compound reduces cell growth, viability and migration. Finally, we adopted for the in vivo study the croton oil-induced ear dermatitis murine model of inflammation. Of note, topical use of DHG significantly decreased mouse ear edema. These results suggest that DHG exerts anti-inflammatory effects and its anti-edema activity in vivo strongly supports its potential therapeutic application in inflammatory cutaneous diseases.

Darwinolide, a New Diterpene Scaffold That Inhibits Methicillin-Resistant Staphylococcus aureus Biofilm from the Antarctic Sponge Dendrilla membranosa.

A new rearranged spongian diterpene, darwinolide, has been isolated from the Antarctic Dendroceratid sponge Dendrilla membranosa. Characterized on the basis of spectroscopic and crystallographic analysis, the central seven-membered ring is hypothesized to originate from a ring-expansion of a spongian precursor. Darwinolide displays 4-fold selectivity against the biofilm phase of methicillin-resistant Staphylococcus aureus compared to the planktonic phase and may provide a scaffold for the development of therapeutics for this difficult to treat infection.

Development and Application of a Novel SPE-Method for Bioassay-Guided Fractionation of Marine Extracts.

The biological diversity of marine habitats is a unique source of chemical compounds with potential use as pharmaceuticals, cosmetics and dietary supplements. However, biological screening and chemical analysis of marine extracts pose specific technical constraints and require adequate sample preparation. Here we report an improved method on Solid Phase Extraction (SPE) to fractionate organic extracts containing high concentration of salt that hampers the recovery of secondary metabolites. The procedure uses a water suspension to load the extracts on a poly(styrene-divynylbenzene)-based support and a stepwise organic solvent elution to effectively desalt and fractionate the organic components. The novel protocol has been tested on MeOH-soluble material from three model organisms (Reniera sarai, Dendrilla membranosa and Amphidinium carterae) and was validated on a small panel of 47 marine samples, including sponges and protists, within discovery programs for identification of immuno-stimulatory and anti-infective natural products.

Ecological and antileishmanial activity of diterpenes derived from the Antarctic sponge Dendrilla membranosa

The cold waters of Antarctica harbor bountiful marine life and biodiversity that promotes competition and the biosynthesis of defensive secondary metabolites. One inhabitant, the vibrant yellow sponge Dendrilla membranosa, is known to inhibit feeding of Antarctic predators such as sea stars and amphipods. A metabolomics approach was undertaken to identify whether sponges within the amphipod-rich algal canopy adopt different chemical profiles to account for the increased predation pressure. In addition, our group has identified the membranolides from D. membranosa. This suite of methoxylated compounds possess potent and selective activity against the leishmaniasis-causing parasite Leishmania donovani. The origin of these compounds will be investigated as artifacts from methanolic degradation of aplysulphurin.

Characterization of membranolides B-H from Dendrilla membranosa and their activity against leishmaniasis

Leishmaniasis is a neglected tropical disease that affects nearly one million people per year and can be fatal if left untreated. In a screening program, the Antarctic sponge Dendrilla membranosa was found to produce diterpenoid secondary metabolites with activity against the leishmaniasis-causing parasite Leishmania donovani. Dichloromethane/methanol (1:1) extracts of the sponge yielded aplysulphurin, its tetrahydro- derivative, and a suite of membranolides, some of which displayed potent bioactivity. In an investigation of membranolides B-H, aplysulphurin was subjected to methanolic treatments and the newly formed compounds were isolated. Upon characterization, these compounds showed identical spectral characteristics to the methoxy-bearing membranolides. The IC50 values of these compounds were assessed in a structure activity relationship (SAR) study targeting anti-leishmanial efficacy.

Further membranolide diterpenes from the antarctic sponge dendrilla membranosa.

Chemical investigation of the Antarctic sponge Dendrilla membranosa collected from the vicinity of Palmer Station on Anvers Island, Antarctica, yielded three new diterpenes, membranolides B-D (2-4), as well as three previously reported sponge metabolites. Membranolides C and D (3, 4), bearing carboxylic acid functional groups, display Gram-negative antibiotic and antifungal activities.

Conformational analysis and absolute stereochemistry of ‘spongian’-related metabolites

New degraded and rearranged diterpenoids, 5– 8 , have been isolated from the Antarctic sponge Dendrilla membranosa. The structure and relative stereochemistry of these compounds were determined by spectroscopic data. The absolute stereochemistry of 5 was determined by spectroscopic data using a chiral reagent. Conformational studies allowed us to assign also the absolute stereochemistry of 6– 8 , as well as those previously isolated spongian-derived metabolites with known relative stereochemistries.

Dendrinolide, a New Degraded Diterpenoid from the Antarctic Sponge Dendrilla membranosa

A new glacian diterpenoid, named dendrinolide (5), was isolated, together with the 9,11-dihydrogracilin A (1), from the Me2CO extract of the Antarctic sponge Dendrilla membranosa. Its structure has been elucidated by interpretation of spectral data and comparison with the similar product 6, previously found in the Mediterranean sponge Spongionella gracilis.

Structure of a keto derivative of 9,11-dihydrogracilin A

The X-ray analysis was carried out on the 8-keto derivative of 9,11-dihydrogracilin A, 1,3,3a,4,5,6,7,7a-octahydro-4-oxo-5-(1,3,3-trimethylcyclohexyl)1,3-isobenzofurandiol diacetate, the major metabolite from the Antarctic sponge Dendrilla membranosa. The present study confirms the norditerpenoid skeleton of the spongian type proposed for the natural product by Molinski & Faulkner [J. Org. Chem. (1987), 52, 296-298] on the basis of spectral data and chemical correlations, and also fixes the unknown relative stereochemistry at C10. This result gives further support to the hypothesis regarding the biogenetic origin of the gracilins. The six-membered rings are both in chair conformations and the furan ring is in an envelope form

Antimicrobial activities of Antarctic sponges

Methanol-toluene extracts of 17 common Antarctic marine sponges collected from shallow waters in McMurdo Sound in October–December 1989 were tested for suppression of growth of bacteria (gram-positive and negative), yeasts and fungi. Weak to moderate levels of antimicrobial activity occurred in all sponges. Antimicrobial activity was more common when gram-negative bacteria were exposed to sponge extracts; 47% of the sponge extracts caused growth inhibition in one or more gram-positive bacteria, while 100% of the extracts caused growth inhibition in gram-negative bacteria. Particularly strong activity was observed against two species of gram-positive bacteria exposed to extracts of the sponge Latrunculia apicalis and against one strain of gram-negative bacterium exposed to extracts of the sponge Haliclona sp. Antimicrobial responses against yeasts and fungi were generally non-existent or weak, with the exception of the yeast Candida tropicalis, which was strongly inhibited by extracts of the sponges Homaxonella balfourensis, Dendrilla membranosa, Kirkpatrickia variolosa, Gellius benedeni, Cinachyra antarctica and Scolymastia joubinia. Antimicrobial activity in these polar sponges is widespread but generally weaker than that found in temperate and tropical sponges.

An antibacterial pigment from the sponge dendrilla membranosa.

Abstract The antimicrobial component of the Antarctic sponge, Dendrilla membranosa, was identified as 4,5,8-trihydroxyquinoline-2-car☐ylic acid ( 3) by interpretation of spectral data and confirmed by synthesis.

ChemInform Abstract: Metabolites of the Antarctic Sponge Dendrilla membranosa.

ChemInformVolume 18, Issue 32 Natural Products ChemInform Abstract: Metabolites of the Antarctic Sponge Dendrilla membranosa. T. F. MOLINSKI, T. F. MOLINSKI CNRS, Lab. Synth. Org. Fac. Sci., 72017 Le Mans, FranceSearch for more papers by this authorD. J. FAULKNER, D. J. FAULKNER CNRS, Lab. Synth. Org. Fac. Sci., 72017 Le Mans, FranceSearch for more papers by this author T. F. MOLINSKI, T. F. MOLINSKI CNRS, Lab. Synth. Org. Fac. Sci., 72017 Le Mans, FranceSearch for more papers by this authorD. J. FAULKNER, D. J. FAULKNER CNRS, Lab. Synth. Org. Fac. Sci., 72017 Le Mans, FranceSearch for more papers by this author First published: August 11, 1987 https://doi.org/10.1002/chin.198732301AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume18, Issue32August 11, 1987 RelatedInformation

Investigation of the relationship between invertebrate predation and biochemical composition, energy content, spicule armament and toxicity of benthic sponges at McMurdo Sound, Antarctica

The biochemical and energetic composition, spicule content, and toxicity of benthic sponges was investigated in McMurdo Sound, Antarctica from October through December 1984. The predominant organic constituent of sponges was soluble and insoluble protein. Levels of total protein ranged from 17.0 to 55.9% dr. wt. Levels of lipid and carbohydrate were low, ranging from 2.1 to 9.6 and 0.6 to 3.5% dr. wt, respectively. Levels of ash were high and variable (32 t0 79% dr. wt), reflecting species-specific differences in spicule contents. Calculated energy contents of sponges were low, with a mean of 9.8±3.5 kJ g-1 dr. wt; ranging from 5.1 kJ g-1 dr. wt in Sphaerotylus antarcticus to 17.4 kJ g-1 dr. wt in Dendrilla membranosa. Insoluble protein accounted for the greatest contribution to the energetic composition of the sponges, while lipid and carbohydrate combined contributed to less than 25% of the overall energy. Normalized spicule volumes of sponges ranged from 0.15 to 0.38 cm3 g-1 dr. wt. Ichthyotoxicity assays indicated that 9 (56%) of 16 antarctic sponge species were toxic. The most highly toxic species were Mycale acerata and Leucetta leptorhapsis. The high incidence of toxicity in antarctic sponges indicates that the current hypothesis suggesting a simple inverse relationship between toxicity and latitude in marine sponges is invalid. There was little correspondence between the energetic composition or spicule contents of the sponges and feeding patterns (electivity indices) of sponge-eating predators. Although the asteroid Perknaster fuscus antarcticus specializes on the highly toxic, fast-growing M. acerata, most antarctic sponge-eating predators appear to be generalists which feed on the more abundant, non- to mildly-toxic, sponge species. This feeding strategy is based on exploitation of low energy, sedentary prey, which require a minimal energy output to harvest.