Dysideanones F-G and dysiherbols D-E, unusual sesquiterpene quinones with rearranged skeletons from the marine sponge Dysidea avara / 中国天然药物

Four new sesquiterpene quinone meroterpenoids, dysideanones F-G (1-2) and dysiherbols D-E (3-4), were isolated from the marine sponge Dysidea avara collected from the South China Sea. The new structures were elucidated by extensive analysis of spectroscopic data including HR-MS and 1D and 2D NMR spectra, and their absolute configurations were assigned by single-crystal X-ray diffraction and ECD calculations. Anti-inflammatory evaluation showed that dysiherbols D-E (3-4) exhibited moderate inhibitory activity on TNF-α-induced NF-κB activation in human HEK-293T cells with IC50 values of 10.2 and 8.6 μmol·L-1, respectively.

In vitro and in vivo genotoxicity and cytotoxicity analysis of protein extract from Aplysina fulva sponges

This study evaluated the physicochemical and morphological properties of a marine sponge protein extract (PE) using scanning electron microscopy (SEM), Energy dispersive X-ray spectroscopy (EDS), analysis of mass loss and pH and in vitro and in vivo. Scanning electron microscopy showed that PE fibers present a granular aspect and irregular structure and the element carbon followed by oxygen was detected in the EDS analysis. Moreover, a 29% of mass loss was observed after 14 days and the pH slightly modified after 14 days. Cell viability of fibroblast cells (L929) of control and PE at a concentration of 25% demonstrated higher values compared to the groups. Osteoblast cell viability of PE at 25 and 50% was significantly higher. Comet assay on day 1 showed higher values for PE at 25%. In addition, in vivo experiments demonstrated that in the treated animals, the bone defects were filled with biomaterial particles, granulation tissue and some areas of newly formed bone. Furthermore, similar immunoexpression of Runx-2 and Cox-2 was observed. Taken together, all results suggest that PE is biocompatible, present non-citotoxicity in the in vitro studies (at the lower concentration) and in the in vivo studies and it can be considered as an alternative source of collagen for tissue engineering proposals.

New bisabolane-type phenolic sesquiterpenoids from the marine sponge Plakortis simplex / 中国天然药物

Six new bisabolane-type phenolic sesquiterpenoids, including plakordiols A-D (1-4), (7R, 10R)-hydroxycurcudiol (5) and (7R, 10S)-hydroxycurcudiol (6) were isolated from the marine sponge Plakortis simplex collected from the South China Sea. Their structures were determined based on extensive analysis of spectroscopic data. Their configurations were assigned by coupling constant analysis, NOESY correlations, and the modified Mosher's method. Furthermore, their cytotoxic and antibacterial activities were evaluated.

Antimicrobial and cytotoxic activities of marine sponge-derived fungal extracts isolated from Dactylospongia sp.

This study is the first report on the antimicrobial and cytotoxic activities of fungal extracts isolated from marinesponge Dactylospongia sp., which is collected from Mandeh Island, West Sumatra, Indonesia. The isolation of fungalwas conducted using dilution method with Sabouraud Dextrose Agar + chloramphenicol (0.05%) as a medium. Thepure isolated fungal was cultivated on rice medium at temperature 25°C–27°C and then extracted using ethyl acetatesolvent. The ethyl acetate extract of each isolated fungal was tested for antimicrobial and cytotoxic activities. Ninefungal strains have been isolated from this sponge. Two ethyl acetate extracts of fungal strains (Dc03 and Dc04) werecategorized as having strong inhibition against the growth of Staphylococcus aureus, Escherichia coli, methicillinresistant S. aureus, and multidrug-resistant Pseudomonas aeruginosa in a concentration of 5% with zone inhibitionin range of 12.31 ± 0.54–16.14 ± 0.75 mm. The cytotoxic activity screening of the ethyl acetate extracts of fungalstrains was done by using the brine shrimp lethality test. Four fungal strains had LC50 below 80 µg/ml (Dc03, Dc04,Dc05, and Dc08) and were further tested with MTT (3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide)assay on T47D cell line. These selected fungi were identified molecularly as Cladosporium halotolerans MN859971,Penicillium citrinum MN859968, Aspergillus versicolor MN859970, and Aspergillus sydowii MN859969, respectively.The results suggest that these fungal strains are quite rich in the production of bioactive compounds that are veryeffective as antibacterial and cytotoxic agents

Effects of Indonesian marine sponges ethanol extracts on the lipid profile of hyperlipidemic rats

This study was aimed to investigate the effects of ethanol extracts of Indonesian marine sponges (Callyspongia sp.,Melophlus sarasinorum, and Xestospongia sp.) on the lipid profile of hyperlipidemic rats. The antihyperlipidemicstudy of these sponges is firstly reported in this study. Experimental hyperlipidemic rats were induced by daily intakeof propylthiouracil (1.8 mg/200 g b.wt and quail yolk (10 ml/kg) for the duration of 3 weeks. Hyperlipidemic ratgroups were administered orally with three doses (30, 60, and 120 mg/kg) of the ethanol extracts for 1-week onward.Blood sample was then collected via intracardiac puncture and serum was biochemically analyzed. Ethanol extractsof Callyspongia sp., M. sarasinorum, and Xestospongia sp. at doses of 60 and 120 mg/kg exhibited a significantreduction of cholesterols, triglycerides, and low-density lipoprotein. These doses also significantly increased the highdensity lipoprotein level. Levels of atherogenic indices (Atherogenic Index, Atherogenic Index Plasma, Castelli’s RiskIndex-I, and Castelli’s Risk Index-II) were also decreased by both doses with percentages protection ranging from70.6% to 81.6%. These results showed that ethanol extracts of Callyspongia sp., M. sarasinorum, and Xestospongiasp. exhibited a lipid-lowering activity in hyperlipidemic rats. Hence, these extracts could be used as sources of leadmolecules in the development of natural lipid-lowering agents from marine species

In vitro cytotoxic activity assay of bacteria extract derived marine sponge Haliclona fascigera toward Hela, WiDr, T47D, and Vero cell line

Symbiotic association between marine sponge and microorganism was a promising chance in the discovery of leadcompound of anticancer. This association was probably concluded that symbiotic microorganism would contain thesame secondary metabolites with the host. In this continuation research, we had isolated symbiotic bacteria from amarine sponge and tested for cytotoxic activity. Twenty-six isolates of bacteria derived from marine sponge Haliclonafascigera were isolated from Setan Island, West Sumatra, Indonesia. Screening of cytotoxic activity by BSLT methodand MTT assay was conducted toward 21 ethyl acetate extracts of symbiotic bacteria with weight >50 mg. Onebacterial extract with code H2N was very toxic according to BSLT test, while 18 isolates were toxic with LC50 rangingfrom 31.17 to 283.38 ppm. All of the bacterial extracts did not show a good percentage of viability (>50%) againstHela, WiDr, T47D, dan Vero cell line in MTT assay. However, bacterial extract with code H2N have shown potentialcytotoxic compared to other extracts. As per the phytochemical study, this extract probably contained terpenoid group.Based on biochemical examination this bacterium, H2N, was identified as Bacillus sp.3.

Anti-Tumour Activity Of Bromopyrrole Alkaloids Against Human Breast Tumour (MCF-7) Through Apoptosis Induction

Objective: The present study was conducted to screen the cytotoxicity and initiation of apoptosis in MCF-7 human breast tumour cells using the Indian sponge Acanthostylotela cornuta of the Gulf of Mannar. Methods: The crude methanol extract of A. cornuta was fractionated using a reversed phase silica gel column chromatography. The purity of the active fraction of bromopyrrole alkaloids was confirmed with Gas Chromatography-Mass Spectrometry (GCMS). The bromopyrrole alkaloids induce apoptotic changes in MCF-7 cells were studied with electrophoresis, caspase assay, and different staining analysis. The MCF-7 cells were analyzed by Flow cytometry to determine their DNA content. Results: Bromopyrrole alkaloids of A. cornuta showed cytotoxicity against MCF-7 human breast tumour cells with the IC50 value of 8.0μg/ml. The bromopyrrole compounds induced cells exhibited scatted red fluorescence, showing the presence of several residual bodies and condensation of chromatin. Caspase-3, pro-caspase-9, caspase-9 and Poly-ADP-Ribose-Polymerase (PARP) activity were occurred in bromopyrrole alkaloids treated tumour cell. The cell cycle arrest is conceivable that the compound prevented the progression of cell cycle through the G phase resulting from inhibition of survival, leading them to undergo apoptosis. Conclusion: Bromopyrrole alkaloids of A. cornuta possess antitumor activity which was arrested the G phase in cell cycle that clearly indicated its nature as that of antitumour drugs.

Screening of cytotoxic activities toward WiDr and Vero cell lines of ethyl acetate extracts of fungi-derived from the marine sponge Acanthostrongylophora ingens

Ethyl acetate extracts of fungi-derived from the marine sponge Acanthostrongylophora ingens were tested forcytotoxic activity against WiDr and Vero cell lines. Three of fungi extracts exhibited strong cytotoxicity with percentageof viability (≤50%) occurring at concentrations of 100 µg/ml. One isolate (IB141) showed specific cytotoxicityagainst WiDr cells whreas not against Vero cells. This isolate was identified based on molecular characterizationusing sequence analysis of the partial 18S rRNA gene. The result indicated that IB141 was identical to Aspergillusochraceus. A comparatively high part of positive bio-activity screening results were acquired in this study, displayingthat the fungi-derived from the marine sponge A. ingens have potential as a source of new anti-cancer agents.

Primmorph extracts and mesohyls of marine sponges inhibitproliferation and migration of hepatocellular carcinoma cells in vitro / 药物分析学报

Cancer recurrence and severe side effects of currently being used chemotherapeutic agents reduce their clinical efficacy. Thus, there is a constant need to develop alternative anticancer drugs. Sustainable supply is an important challenge facing marine-based drug discovery. Primmorph, a 3D cell culture system, could provide a sustainable source to produce metabolites for anticancer drugs from marine sponges. In the present work, the anticancer activity of primmorph extracts and mesohyls of Negombata magnifica, Hemimycle arabica, Crella spinulata, and Stylissa carteri sponges was evaluated. Anti-proliferative activity was studied in terms of cytotoxicity, colony formation, cell cycle, and apoptosis. Migration was assessed by migration assay and matrix metalloproteinase activity. The expression of proliferation and migration-related genes was analyzed using real time PCR. Migration and proliferation activities of HepG2 cells were inhibited by treatment with primmorph extracts and mesohyls of N. magnifica, H. arabica, and C. spinulata. The mesohyl of S. carteri did not show any anticancer activity although the primmorph extract led to cell cycle arrest. Among the selected sponge species, the prim-morph extract of C. spinulata was the most promising anticancer agent regarding antiproliferative and antimigratory activities. In addition, primmorph extracts have the advantage of working under well-defined and controlled conditions, which allows the easy application as a bioreactor.

Chemical constituents from the marine sponge Theonella swinhoei / 药学实践杂志

Objective To investigate the chemical constituents of the marine sponge Theonella swinhoei collected from the Xisha Islands in the South China Sea .Methods The petroleum ether and dichloromethane extract of the marine sponge T . swinhoei were purified by solvent extraction and chromatographic methods including vacuum liquid chromatography (VLC) , medium pressureliquidchromatography(MPLC),thinlayerchromatography(TLC)onsilicagel,highperformanceliquidchro-matography(HPLC) ,and Sephadex LH-20 .The chemical structures were determined by spectroscopic analysis and comparison with the reported data .Results Eight compounds were isolated and their structures were determined as cholest-7-ene-3β,5α, 6β-triol (1) ,ergosta-7 ,22-diene-3β,5α,6β-triol (2) ,25-norcycloartane-3β,6α,16β,24-tetraol (3) ,sinuflexibilin D (4) ,14-de-oxycrassin (5) ,N-(2-phenylethyl)-(9Z)-tetradecanamide(6) ,N-(2-phenylethyl)-tetradecanamide (7) ,7 ,8-dimethyl-isoallox-azine (8) .Conclusion Compounds 1～ 7 were isolated from the sponge of genus Theonella for the first time .

Antimicrobial activity of endophytic fungi from marine Sponge Haliclona fascigera.

Fungi associated with marine sponge Haliclona fascigera has shown a promising source in the search for new antimicrobial compounds. We have isolated 25 endophytic fungi from the sponge, which were cultured in Sabouraud Dextrose Broth (SDB) for 4 weeks at 25-27ºC. The ethyl acetate extracts of the isolates-broth were then tested for its antimicrobial activity against Staphylococcus aureus, Escherichia coli, and Candida albicans by using agar diffusion method. The zone of inhibition was measured and expressed in millimeters. There were 8 isolates of the fungi that considered active to Staphylococcus aureus, i.e. HF2 isolate (14,5 mm), HF8 isolate (12,5 mm), HF9 isolate (14 mm), HF13 isolate (16,5 mm), HF14 isolate (11 mm), HF19 isolate (14,5 mm), HF21 isolate (14,5 mm), HF22 isolate (13 mm), and 1 isolate active to C. albicans, i.e. HF16 isolate (12,5 mm). The identification of the bioactive fungi isolates was done by comparing its macroscopic and microscopic characteristic based on literature. From the study, it can be concluded that fungi associated with marine sponge Haliclona fascigera possesses potentially antimicrobial activity which might be due to the presence of bioactive metabolite compounds.

Screening of Endophytic Bacteria Isolated from Marine Sponge Haliclona fascigera for Inhibition against Clinical Isolates of Methicillin Resistant Staphylococcus aureus (MRSA).

Marine endophytic bacteria are a valuable source of novel antibacterial in combating pathogenic isolates of methicillin-resistant Staphylococcus aureus (MRSA), a global nosocomial problem today. The aim of this study was to assess in vitro anti-MRSA activity of extracts from bacteria endophyte of marine sponge Haliclona fascigera collected from Setan Island, South Coast of West Sumatra, Indonesia. Anti-MRSA activity test carried out by the agar diffusion method using paper disk. The endophytic bacteria from sponge were isolated using dilution method and pour plate method on NA media. From the sponge were obtained 26 isolates of bacterial endophytic then propagated in NB media. The liquid media was then extracted using ethyl acetate solvent. Antimicrobial activity test carried out by the agar diffusion method using paper disk. The antibacterial activity assay was conducted with the extract concentrations of 5 %. Chloramphenicol was used as a positive control agent. The zone of inhibition was measured and expressed in millimeters. There were 12 isolates of the bacteria that considered active to MRSA. Mean of inhibition zones ranged from 11.1±0.17 to 15.17±0.76. Characterization and identification of endophytic bacteria were conducted to several bioactive bacteria. The identification method was performed using Gram staining and biochemical test.

Antimicrobial potential of the marine intertidal sponge, Ircinia fusca from west coast of India .

In vitro antimicrobial screening of marine sponge (Porifera) Ircinia fusca collected from west coast of India, against selected bacteria and fungi was conducted in this study. Crude sponge extracts of the marine organism Ircinia fusca demonstrated activity against eight microbes tested. The extracts showing good antimicrobial activity are undergoing further analysis to identify the active constituents.

Bromotyrosine derivatives from marine sponges inhibit the HIV-1 replication in vitro / Replication in vitro bromotirosinas derivadas de esponjas marinas inhiben la replicación in vitro del VIH-1

Background: Human immunodeficiency virus type 1 (HIV-1) infection and Acquired immunodeficiency syndrome are mayor global public health issues. HIV-1 infection is now manageable as a chronic disease thanks to the development of antiretroviral therapy; however, the existence of HIV drug resistance and collateral effects have increased the search for therapeutic alternatives. Compounds of marine resources have been studied for their antiviral potential. Objectives: To evaluate the antiviral activity of isolated bromotyrosine-derivative compounds from the Colombian marine sponges, Verongula rigida and Aiolochoria crassa against HIV-1 infection in vitro. Methods: Cytotoxicity of 11 bromotyrosine-derivative compounds was determined by the MTT assay. Inhibition of HIV-1 replication was performed using the U373-MAGI cell line, which was infected with recombinant green fluorescent protein (GFP)-expressing viruses pseudotyped, in the presence or absence of the compounds. The percentage of infected cells was evaluated by flow cytometry. In addition, the inhibition of reverse transcription and nuclear import was determined by quantification of early and late reverse transcription products and 2-LTR circles, respectively, using quantitative PCR. Results: Aeroplysinin-1, purealidin B and 3-bromo-5-hydroxy-Omethyltyrosine inhibited the HIV-1 replication in a dose-dependent manner, with a median maximum percentage of inhibition of 74% (20 µM), 57% (80 µM) and 47% (80 µM), respectively. Importantly, none of these concentrations were cytotoxic. Aeroplysinin-1, 19-deoxyfistularin 3, purealidin B, fistularin 3 and 3-bromo-5-hydroxy-O-methyltyrosine inhibited the nuclear import efficiently; while 3,5-dibromoN,N,N,O-tetramethyltyraminium, aeroplysinin-1, purealidin B, fistularin 3 and 3-bromo-5-hydroxy-Omethyltyrosine inhibited X4 HIV-1 cell entry with a median maximum percentage of inhibition ranging between 2 to 30%. Conclusions: Aeroplysinin-1, 19-deoxyfistularin 3, purealidin B, fistularin 3 and 3-bromo-5-hydroxy-O-methyltyrosine inhibited HIV replication at different steps. This study opens the possibility of chemically synthesizing these compounds and evaluating them as alternative therapies against HIV-1.

Purification and characterization of structural and functional properties of two lectins from a marine sponge Spheciospongia vesparia.

The purification, structural and functional characterization of two different lectins (named Svl-1 and Svl-2) has been reported from the marine sponge Spheciospongia vesparia. Purification procedure includes ammonium sulfate precipitation, combined with chromatography including Octyl-Sepharose-(NH4)SO4 hydrophobic column and DEAE-Toyopearl anion-exchange column using a high performance liquid chromatography. The similarities in function, specificity for saccharides, molecular weight, amino acid content and the N-terminal sequence of two lectins suggest that these proteins are isolectins. Amino acid composition and fluorescence analyses reveal that they contain an intrachain disulfide bridge, which might contribute to their high thermal stability. Furthermore, the purified lectins exhibit antibacterial activity against the gram-negative bacteria Pseudomonas aeruginosa and E. coli, indicating that they may be involved in a recognition strategy and may play a role in the defense response function of the sponge. This is the first report on the isolation of lectins from the S. vesparia. The purified lectins represent a potential possible candidate for future application in the recognition or treatment of cancer cells.

Chemical constituents of Axinella sp. from the South China Sea / 中国药学杂志

OBJECTIVE: To study the chemical constituents of Axinella sp. from the South China Sea. METHODS: The compounds were isolated and purified by silica gel, Sephadex LH-20, and semi-preparative reverse-phase HPLC(C18). Their structures were identified by their spectral data. RESULTS: Ten compounds were isolated from Axinella sp. and their structures were identified as cyclo-(Val-Pro) (1), cyclo-(Tyr-Pro) (2), cyclo-(Phe-Pro) (3), cyclo-(Leu-Pro) (4), cyclo-(Ile-Pro) (5), 2'-deoxyinosine (6), 2'-deoxyadenosine(7), spongothymidine (8), spongouridine (9) and 2'-deoxyuridine (10). CONCLUSION: All the compounds were isolated from Callyspongia sp. for the first time.

Actividades biológicas del extracto acuoso de la esponja Aplysina lacunosa (Porifera: Aplysinidae) / Biological activities of the aqueous extract of the sponge Aplysina lacunosa (Porifera: Aplysinidae)

Biological activity of an aqueons extract of the sponge Aplysina lacunosa (Porifera: Aplysinidae). The aqueous extract and protein precipitate of Aplysina lacunosa (Pallas, 1776) were studied to assess their hemagglutinating, hemolysing, antibacterial, and antifungal activities. Specimens of the marine sponge were collected in El Morro de Tigüitigüe, Santa Fe, Sucre state, Venezuela. The active protein was separated by molecular exclusion chromatography and its molar mass estimated by SDS-PAGE electrophoresis. The sponge A. lacunosa has a protein with a molar mass of about 43 000 Daltons which is capable of agglutinating human erythrocytes of the blood groups A, B, and O in a strong and unspecific mode. The assayed samples did not evidence any hemolysing activity. As for the antibacterial assay, only the aqueous extract was able to inhibit the growth of Enterococcus faecalis, Bacillus cereus, Escherichia coli, and Salmonella enteritidis, with inhibition halos of 24, 20, 24, and 22 mm, respectively. None of the samples exhibited antifungal activity. The chemical analysis of the aqueous extract revealed the presence of several secondary metabolites. It is presumed that its hemagglutinating activity is mediated by agglutinative proteins. The antibacterial activity could be attributed to the presence of saponins, alkaloids, tannins, and polyphenols, which are highly antimicrobial compounds. Poriferans are a rich source of bioactive compounds that can be used in the development of new drugs potentially useful in medicine. Rev. Biol. Trop. 54 (Suppl. 3): 189-200. Epub 2007 Jan. 15.

Evaluamos el extracto acuoso y precipitado de proteínas de Aplysina lacunosa, en relación con su actividad hemaglutinante, hemolizante, antibacteriana y antimicótica. Los ejemplares de la esponja marina fueron recolectados en el Morro de Tigüitigüe, Santa Fe, Estado Sucre, Venezuela. La proteína activa fue separada por cromatografía de exclusión molecular; y su masa molar fue estimada por electroforesis SDS-PAGE. La esponja A. lacunosa posee una proteína con masa molar aproximada de 4.000 Daltons capaz de aglutinar fuertemente y de manera inespecífica los eritrocitos humanos de los grupos sanguíneos A, B y O. No se observó actividad hemolizante por parte de las muestras ensayadas. Únicamente el extracto acuoso fue capaz de inhibir el crecimiento de Enterococcus faecalis, Bacillus cereus, Escherichia coli y Salmonella enteritidis con halos de inhibición de 24, 20, 24, 22 mm, respectivamente; ninguna de las muestras exhibió actividad antifúngica. El análisis químico del extracto acuoso reveló la presencia de diversos metabolitos secundarios. Se presume que la actividad hemaglutinante se deba a la presencia de proteínas aglutinantes. La actividad antibacteriana podría atribuirse a la presencia de saponinas, alcaloides, taninos y polifenoles, compuestos altamente antimicrobianos. Los poríferos constituyen una fuente rica de compuestos bioactivos que pueden ser utilizados para el desarrollo de nuevos fármacos.

Studies on the tumor cytotoxic constituents from the marine sponge Hyrtios erectus / 中国海洋药物

Objective To investigate the cytotoxic constituents from the sponge Hyrtios erectus.Methods The constituents were isolated and purified by column chromatography,and their structures were identified by physicochemical data,spectral data,and comparison with data of references.The cytotoxic activity of all the compounds was determined by MTT mothod.Results Five compounds were isolated from the lipid extract of Hyrtios erectus,and their structures were elucidated as Hyrtiosal(Ⅰ),12?-Hydroxy-16-scalaren-24,25-olide(Ⅱ),5-Hydroxy-1H-indole-3-ethanol(Ⅲ),cholesterol(Ⅳ),and dibutylphthalate(Ⅴ) respectively.Conclusion Compound were isolated from Hyrtios erectus for the first time, and compound Ⅰand Ⅱ showed strong cytotoxic activity.

Research advances of Glycosphingolipids / 中国海洋药物

Marine Glycosphingolipids(GSLs) compounds mainly come from marine ogranisms of marine sponge and starfish. The advances of study on GSLs compounds in recent two decades were reviewed. The relationship between chemical structure and biological functions of GSLs compounds was also described.

Studies on chemical constituents of the marine sponge Clathria fasciculate from the South China Sea(Ⅱ) / 中国海洋药物

Four organic compounds were isolated from the ethyl acetate soluble fraction of the marine sponge Clathria fasciculate which collected from the South China Sea. Their structures were determined by GC-MS, FAB, IR, 1HNMR, 13CNMR and COSY spectra as: clolest-4-en-3-one(Ⅰ). stigmast-4-en-3-one(Ⅱ). (Z)-17-tetracosene-l-ol(Ⅲ) and3-(17Z-tetracosenyloxy)-1 , 2-propanediol(Ⅳ). It's the second report of the first serial studies of the chemical constituents of the marine sponge Clathria fasciculate.