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Mar. Drugs, Volume 12, Issue 4 (April 2014), Pages 1699-2340

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Open AccessArticle A New Benzofuran Glycoside and Indole Alkaloids from a Sponge-Associated Rare Actinomycete, Amycolatopsis sp.
Mar. Drugs 2014, 12(4), 2326-2340; https://doi.org/10.3390/md12042326
Received: 30 January 2014 / Revised: 17 March 2014 / Accepted: 28 March 2014 / Published: 22 April 2014
Cited by 13 | PDF Full-text (1112 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Three new secondary metabolites, amycofuran (1), amycocyclopiazonic acid (2), and amycolactam (3), were isolated from the sponge-associated rare actinomycete Amycolatopsis sp. Based on combined spectroscopic analyses, the structures of 13 were determined to be a
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Three new secondary metabolites, amycofuran (1), amycocyclopiazonic acid (2), and amycolactam (3), were isolated from the sponge-associated rare actinomycete Amycolatopsis sp. Based on combined spectroscopic analyses, the structures of 13 were determined to be a new benzofuran glycoside and new indole alkaloids related to cyclopiazonic acids, a class that has previously only been reported in fungi. The absolute configurations of 1 and 3 were deduced by ECD calculations, whereas that of 2 was determined using the modified Mosher method. Amycolactam (3) displayed significant cytotoxicity against the gastric cancer cell line SNU638 and the colon cancer cell line HCT116. Full article
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Open AccessArticle Design, Synthesis and Biological Evaluation of Tasiamide Analogues as Tumor Inhibitors
Mar. Drugs 2014, 12(4), 2308-2325; https://doi.org/10.3390/md12042308
Received: 26 December 2013 / Revised: 5 March 2014 / Accepted: 18 March 2014 / Published: 22 April 2014
Cited by 5 | PDF Full-text (1041 KB) | HTML Full-text | XML Full-text
Abstract
Eighteen analogues of the marine cytotoxic linear peptide tasiamide were designed, synthesized and screened for their inhibitory activities against the growth of human nasopharyngeal carcinoma (KB) and human non-small cell lung tumor (A549) cell lines. The results indicated that minor modifications of the
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Eighteen analogues of the marine cytotoxic linear peptide tasiamide were designed, synthesized and screened for their inhibitory activities against the growth of human nasopharyngeal carcinoma (KB) and human non-small cell lung tumor (A549) cell lines. The results indicated that minor modifications of the C-terminuswith aromatic groups were tolerated, with the IC50 values between 1.29 and 12.88 μM against these two cancer cell lines. Truncation, minor modifications at the N-terminus or elimination of the N-methyl groups in N-Me-d-Gln and/or N-Me-d-Phe residues resulted in inactive analogues. Full article
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Open AccessCorrection Correction: Kallifatidis, G. et al. The Marine Natural Product Manzamine A Targets Vacuolar ATPases and Inhibits Autophagy in Pancreatic Cancer Cells. Mar. Drugs 2013, 11, 3500–3516
Mar. Drugs 2014, 12(4), 2305-2307; https://doi.org/10.3390/md12042305
Received: 12 March 2014 / Accepted: 27 March 2014 / Published: 21 April 2014
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Abstract
We found two errors in our previous published paper [1]. Figure 4A has a mistake in the units in the labels, where it shows mM instead of micromolar (µM). A correctly labeled Figure 4A ensues. In Figures 2 and 4, the size bar
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We found two errors in our previous published paper [1]. Figure 4A has a mistake in the units in the labels, where it shows mM instead of micromolar (µM). A correctly labeled Figure 4A ensues. In Figures 2 and 4, the size bar scale is micrometers (µm). We apologize for the inconvenience caused to our readers. [...] Full article
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Open AccessArticle The Marine-Derived Sipholenol A-4-O-3′,4′-Dichlorobenzoate Inhibits Breast Cancer Growth and Motility in Vitro and in Vivo through the Suppression of Brk and FAK Signaling
Mar. Drugs 2014, 12(4), 2282-2304; https://doi.org/10.3390/md12042282
Received: 11 February 2014 / Revised: 1 April 2014 / Accepted: 1 April 2014 / Published: 14 April 2014
Cited by 7 | PDF Full-text (1709 KB) | HTML Full-text | XML Full-text
Abstract
Sipholenol A is a natural sipholane triterpenoid isolated from the Red Sea sponge, Callyspongia siphonella. Previous studies showed the antimigratory and antiproliferative activities of the semisynthetic sipholenol A esters against breast cancer cell lines. This study investigated the effects of sipholenol A-4-
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Sipholenol A is a natural sipholane triterpenoid isolated from the Red Sea sponge, Callyspongia siphonella. Previous studies showed the antimigratory and antiproliferative activities of the semisynthetic sipholenol A esters against breast cancer cell lines. This study investigated the effects of sipholenol A-4-O-3′,4′-dichlorobenzoate (SPA) on the growth, migration and invasion of diverse human breast cancer cells. Results showed that SPA inhibited the growth of the human breast cancer cells, MDA-MB-231, MCF-7, BT-474 and T-47D, in a dose-dependent manner. Immunofluorescent analysis showed that SPA significantly reduced Ki-67-positive cells in MDA-MB-231 cells. Flow cytometry and Western blot analyses revealed that SPA treatment suppressed MDA-MB-231 cell growth by inducing cell cycle arrest at the G1 phase. In addition, SPA suppressed breast cancer cell migration, invasion and decreased Brk and FAK activation in a dose-dependent manner. Molecular docking study suggested a perfect fitting at the FAK’s FERM domain, inhibiting the main autophosphorylation site, Y397, which was further confirmed by Western blot analysis. Most known small molecule FAK inhibitors target the kinase domain, creating several off-target side effects. The in vivo studies showed that SPA treatment suppressed breast tumor growth and Ki-67, CD31, p-Brk and p-FAK expression in orthotopic breast cancer in nude mice. In conclusion, SPA inhibited the growth, invasion and migration of breast cancer cells possibly via deactivating Brk and FAK signaling, suggesting good potential for therapeutic use to control invasive breast cancer. Full article
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Open AccessArticle Effects of Chitin and Sepia Ink Hybrid Hemostatic Sponge on the Blood Parameters of Mice
Mar. Drugs 2014, 12(4), 2269-2281; https://doi.org/10.3390/md12042269
Received: 25 January 2014 / Revised: 18 March 2014 / Accepted: 25 March 2014 / Published: 10 April 2014
Cited by 9 | PDF Full-text (623 KB) | HTML Full-text | XML Full-text
Abstract
Chitin and sepia ink hybrid hemostatic sponge (CTSH sponge), a new biomedical material, was extensively studied for its beneficial biological properties of hemostasis and stimulation of healing. However, studies examining the safety of CTSH sponge in the blood system are lacking. This experiment
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Chitin and sepia ink hybrid hemostatic sponge (CTSH sponge), a new biomedical material, was extensively studied for its beneficial biological properties of hemostasis and stimulation of healing. However, studies examining the safety of CTSH sponge in the blood system are lacking. This experiment aimed to examine whether CTSH sponge has negative effect on blood systems of mice, which were treated with a dosage of CTSH sponge (135 mg/kg) through a laparotomy. CTSH sponge was implanted into the abdominal subcutaneous and a laparotomy was used for blood sampling from abdominal aortic. Several kinds of blood parameters were detected at different time points, which were reflected by coagulation parameters including thrombin time (TT), prothrombin time (PT), activated partial thromboplatin time (APTT), fibrinogen (FIB) and platelet factor 4 (PF4); anticoagulation parameter including antithrombin III (AT-III); fibrinolytic parameters including plasminogen (PLG), fibrin degradation product (FDP) and D-dimer; hemorheology parameters including blood viscosity (BV) and plasma viscosity (PV). Results showed that CTSH sponge has no significant effect on the blood parameters of mice. The data suggested that CTSH sponge can be applied in the field of biomedical materials and has potential possibility to be developed into clinical drugs of hemostatic agents. Full article
(This article belongs to the Special Issue Marine Biomaterials)
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Open AccessArticle Modification of Chitin with Kraft Lignin and Development of New Biosorbents for Removal of Cadmium(II) and Nickel(II) Ions
Mar. Drugs 2014, 12(4), 2245-2268; https://doi.org/10.3390/md12042245
Received: 4 February 2014 / Revised: 6 March 2014 / Accepted: 12 March 2014 / Published: 10 April 2014
Cited by 48 | PDF Full-text (1715 KB) | HTML Full-text | XML Full-text
Abstract
Novel, functional materials based on chitin of marine origin and lignin were prepared. The synthesized materials were subjected to physicochemical, dispersive-morphological and electrokinetic analysis. The results confirm the effectiveness of the proposed method of synthesis of functional chitin/lignin materials. Mechanism of chitin modification
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Novel, functional materials based on chitin of marine origin and lignin were prepared. The synthesized materials were subjected to physicochemical, dispersive-morphological and electrokinetic analysis. The results confirm the effectiveness of the proposed method of synthesis of functional chitin/lignin materials. Mechanism of chitin modification by lignin is based on formation of hydrogen bonds between chitin and lignin. Additionally, the chitin/lignin materials were studied from the perspective of waste water treatment. The synthetic method presented in this work shows an attractive and facile route for producing low-cost chitin/lignin biosorbents with high efficiency of nickel and cadmium adsorption (88.0% and 98.4%, respectively). The discovery of this facile method of synthesis of functional chitin/lignin materials will also have a significant impact on the problematic issue of the utilization of chitinous waste from the seafood industry, as well as lignin by-products from the pulp and paper industry. Full article
(This article belongs to the Special Issue Marine Biomaterials)
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Open AccessArticle Maritime Halophyte Species from Southern Portugal as Sources of Bioactive Molecules
Mar. Drugs 2014, 12(4), 2228-2244; https://doi.org/10.3390/md12042228
Received: 26 January 2014 / Revised: 28 February 2014 / Accepted: 28 March 2014 / Published: 10 April 2014
Cited by 19 | PDF Full-text (834 KB) | HTML Full-text | XML Full-text
Abstract
Extracts of five halophytes from southern Portugal (Arthrocnemum macrostachyum, Mesembryanthemum edule, Juncus acutus, Plantago coronopus and Halimione portulacoides), were studied for antioxidant, anti-inflammatory and in vitro antitumor properties. The most active extracts towards the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical were
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Extracts of five halophytes from southern Portugal (Arthrocnemum macrostachyum, Mesembryanthemum edule, Juncus acutus, Plantago coronopus and Halimione portulacoides), were studied for antioxidant, anti-inflammatory and in vitro antitumor properties. The most active extracts towards the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical were the methanol extracts of M. edule (IC50 = 0.1 mg/mL) and J. acutus (IC50 = 0.4 mg/mL), and the ether extracts of J. acutus (IC50 = 0.2 mg/mL) and A. macrostachyum (IC50 = 0.3 mg/mL). The highest radical scavenging activity (RSA) against the 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) radical was obtained in the ether extract of J. acutus (IC50 = 0.4 mg/mL) and H. portulacoides (IC50 = 0.9 mg/mL). The maximum total phenolic content (TPC) was found in the methanol extract of M. edule (147 mg gallic acid equivalents (GAE)/g) and in the ether extract of J. acutus (94 mg GAE/g). Significant decreases in nitric oxide (NO) production were observed after incubation of macrophages with lipopolysaccharide (LPS) and the chloroform extract of H. portulacoides (IC50 = 109 µg/mL) and the hexane extract of P. coronopus (IC50 = 98.0 µg/mL). High in vitro cytotoxic activity and selectivity was obtained with the ether extract of J. acutus. Juncunol was identified as the active compound and for the first time was shown to display selective in vitro cytotoxicity towards various human cancer cells. Full article
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Open AccessArticle Simple and Rapid Quality Control of Sulfated Glycans by a Fluorescence Sensor Assay—Exemplarily Developed for the Sulfated Polysaccharides from Red Algae Delesseria sanguinea
Mar. Drugs 2014, 12(4), 2205-2227; https://doi.org/10.3390/md12042205
Received: 26 January 2014 / Revised: 28 February 2014 / Accepted: 24 March 2014 / Published: 10 April 2014
Cited by 5 | PDF Full-text (851 KB) | HTML Full-text | XML Full-text
Abstract
Sulfated polysaccharides (SP) from algae are of great interest due to their manifold biological activities. Obstacles to commercial (especially medical) application include considerable variability and complex chemical composition making the analysis and the quality control challenging. The aim of this study was to
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Sulfated polysaccharides (SP) from algae are of great interest due to their manifold biological activities. Obstacles to commercial (especially medical) application include considerable variability and complex chemical composition making the analysis and the quality control challenging. The aim of this study was to evaluate a simple microplate assay for screening the quality of SP. It is based on the fluorescence intensity (FI) increase of the sensor molecule Polymer-H by SP and was originally developed for direct quantification of SP. Exemplarily, 65 SP batches isolated from the red alga Delesseria sanguinea (D.s.-SP) and several other algae polysaccharides were investigated. Their FI increase in the Polymer-H assay was compared with other analytical parameters. By testing just one concentration of a D.s.-SP sample, quality deviations from the reference D.s.-SP and thus both batch-to-batch variability and stability can be detected. Further, structurally distinct SP showed to differ in their concentration-dependent FI profiles. By using corresponding reference compounds, the Polymer-H assay is therefore applicable as identification assay with high negative predictability. In conclusion, the Polymer-H assay showed to represent not only a simple method for quantification, but also for characterization identification and differentiation of SP of marine origin. Full article
(This article belongs to the Special Issue Marine Glycoconjugates)
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Open AccessArticle Pelagia noctiluca (Scyphozoa) Crude Venom Injection Elicits Oxidative Stress and Inflammatory Response in Rats
Mar. Drugs 2014, 12(4), 2182-2204; https://doi.org/10.3390/md12042182
Received: 23 January 2014 / Revised: 20 March 2014 / Accepted: 21 March 2014 / Published: 10 April 2014
Cited by 13 | PDF Full-text (1301 KB) | HTML Full-text | XML Full-text
Abstract
Cnidarian toxins represent a rich source of biologically active compounds. Since they may act via oxidative stress events, the aim of the present study was to verify whether crude venom, extracted from the jellyfish Pelagia noctiluca, elicits inflammation and oxidative stress processes,
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Cnidarian toxins represent a rich source of biologically active compounds. Since they may act via oxidative stress events, the aim of the present study was to verify whether crude venom, extracted from the jellyfish Pelagia noctiluca, elicits inflammation and oxidative stress processes, known to be mediated by Reactive Oxygen Species (ROS) production, in rats. In a first set of experiments, the animals were injected with crude venom (at three different doses 6, 30 and 60 µg/kg, suspended in saline solution, i.v.) to test the mortality and possible blood pressure changes. In a second set of experiments, to confirm that Pelagia noctiluca crude venom enhances ROS formation and may contribute to the pathophysiology of inflammation, crude venom-injected animals (30 µg/kg) were also treated with tempol, a powerful antioxidant (100 mg/kg i.p., 30 and 60 min after crude venom). Administration of tempol after crude venom challenge, caused a significant reduction of each parameter related to inflammation. The potential effect of Pelagia noctiluca crude venom in the systemic inflammation process has been here demonstrated, adding novel information about its biological activity. Full article
(This article belongs to the collection Bioactive Compounds from Marine Invertebrates)
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Open AccessReview Briarane Diterpenoids Isolated from Gorgonian Corals between 2011 and 2013
Mar. Drugs 2014, 12(4), 2164-2181; https://doi.org/10.3390/md12042164
Received: 22 January 2014 / Revised: 20 March 2014 / Accepted: 21 March 2014 / Published: 10 April 2014
Cited by 18 | PDF Full-text (697 KB) | HTML Full-text | XML Full-text
Abstract
The structures, names, bioactivities and references of 138 briarane-type diterpenoids, including 87 new compounds, are summarized in this review. All the briarane-type compounds mentioned in this review article were obtained from gorgonian corals including the genus Briareum, Dichotella, Junceella and Verrucella
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The structures, names, bioactivities and references of 138 briarane-type diterpenoids, including 87 new compounds, are summarized in this review. All the briarane-type compounds mentioned in this review article were obtained from gorgonian corals including the genus Briareum, Dichotella, Junceella and Verrucella. Some of these compounds showed potential bioactivities. Full article
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Open AccessArticle Two New Cytotoxic Indole Alkaloids from a Deep-Sea Sediment Derived Metagenomic Clone
Mar. Drugs 2014, 12(4), 2156-2163; https://doi.org/10.3390/md12042156
Received: 7 February 2014 / Revised: 7 March 2014 / Accepted: 10 March 2014 / Published: 8 April 2014
Cited by 7 | PDF Full-text (555 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Two new indole alkaloids, metagenetriindole A (1) and metagenebiindole A (2), were identified from deep-sea sediment metagenomic clone derived Escherichia coli fermentation broth. The structures of new compounds were elucidated by spectroscopic methods. The two new indole alkaloids demonstrated moderately cytotoxic activity against
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Two new indole alkaloids, metagenetriindole A (1) and metagenebiindole A (2), were identified from deep-sea sediment metagenomic clone derived Escherichia coli fermentation broth. The structures of new compounds were elucidated by spectroscopic methods. The two new indole alkaloids demonstrated moderately cytotoxic activity against CNE2, Bel7402 and HT1080 cancer cell lines in vitro. Full article
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Open AccessCommunication Cladieunicellins M–Q, New Eunicellins from Cladiella sp.
Mar. Drugs 2014, 12(4), 2144-2155; https://doi.org/10.3390/md12042144
Received: 3 March 2014 / Revised: 20 March 2014 / Accepted: 27 March 2014 / Published: 8 April 2014
Cited by 5 | PDF Full-text (690 KB) | HTML Full-text | XML Full-text
Abstract
Five new 7α-hydroxyeunicellin-based diterpenoids, designated as cladieunicellins M–Q (15), were isolated from a Formosan octocoral Cladiella sp. The structures of 15 were elucidated on the basis of spectroscopic methods and by comparison of the data with those
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Five new 7α-hydroxyeunicellin-based diterpenoids, designated as cladieunicellins M–Q (15), were isolated from a Formosan octocoral Cladiella sp. The structures of 15 were elucidated on the basis of spectroscopic methods and by comparison of the data with those of the related metabolites. Cytotoxicity of metabolites 15 against the human leukemia Molt 4 and HL 60 is also described. Among them, compounds 1, 3 and 5 exhibited moderate cytotoxicity toward Molt 4 cells with IC50 values 16.43, 14.17 and 15.55 μM, respectively. Preliminary SAR (structure activity relationship) information was obtained from these compounds and their analogues. Full article
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Open AccessArticle Action of Clathrodin and Analogues on Voltage-Gated Sodium Channels
Mar. Drugs 2014, 12(4), 2132-2143; https://doi.org/10.3390/md12042132
Received: 3 January 2014 / Revised: 21 February 2014 / Accepted: 25 March 2014 / Published: 4 April 2014
Cited by 7 | PDF Full-text (744 KB) | HTML Full-text | XML Full-text
Abstract
Clathrodin is a marine alkaloid and believed to be a modulator of voltage-gated sodium (NaV) channels. Since there is an urgent need for small molecule NaV channel ligands as novel therapeutics, clathrodin could represent an interesting lead compound. Therefore, clathrodin
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Clathrodin is a marine alkaloid and believed to be a modulator of voltage-gated sodium (NaV) channels. Since there is an urgent need for small molecule NaV channel ligands as novel therapeutics, clathrodin could represent an interesting lead compound. Therefore, clathrodin was reinvestigated for its potency and NaV channel subtype selectivity. Clathrodin and its synthetic analogues were subjected to screening on a broad range of NaV channel isoforms, both in voltage clamp and patch clamp conditions. Even though clathrodin was not found to exert any activity, some analogues were capable of modulating the NaV channels, hereby validating the pyrrole-2-aminoimidazole alkaloid structure as a core structure for future small molecule-based NaV channel modulators. Full article
(This article belongs to the Special Issue Alkaloid Analogs)
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Open AccessArticle Insights and Ideas Garnered from Marine Metabolites for Development of Dual-Function Acetylcholinesterase and Amyloid-β Aggregation Inhibitors
Mar. Drugs 2014, 12(4), 2114-2131; https://doi.org/10.3390/md12042114
Received: 10 December 2013 / Revised: 27 February 2014 / Accepted: 12 March 2014 / Published: 4 April 2014
Cited by 5 | PDF Full-text (2061 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Due to the diversity of biological activities that can be found in aquatic ecosystems, marine metabolites have been an active area of drug discovery for the last 30 years. Marine metabolites have been found to inhibit a number of enzymes important in the
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Due to the diversity of biological activities that can be found in aquatic ecosystems, marine metabolites have been an active area of drug discovery for the last 30 years. Marine metabolites have been found to inhibit a number of enzymes important in the treatment of human disease. Here, we focus on marine metabolites that inhibit the enzyme acetylcholinesterase, which is the cellular target for treatment of early-stage Alzheimer’s disease. Currently, development of anticholinesterase drugs with improved potency, and drugs that act as dual acetylcholinesterase and amyloid-β aggregation inhibitors, are being sought to treat Alzheimer’s disease. Seven classes of marine metabolites are reported to possess anti-cholinesterase activity. We compared these metabolites to clinically-used acetylcholinesterase inhibitors having known mechanisms of inhibition. We performed a docking simulation and compared them to published experimental data for each metabolite to determine the most likely mechanism of inhibition for each class of marine inhibitor. Our results indicate that several marine metabolites bind to regions of the acetylcholinesterase active site that are not bound by the clinically-used drugs rivastigmine, galanthamine, donepezil, or tacrine. We use the novel poses adopted for computational drug design of tighter binding anticholinesterase drugs likely to act as inhibitors of both acetylcholinesterase activity and amyloid-β aggregation inhibition. Full article
(This article belongs to the collection Bioactive Compounds from Marine Invertebrates)
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Open AccessArticle Molecular Response to Toxic Diatom-Derived Aldehydes in the Sea Urchin Paracentrotus lividus
Mar. Drugs 2014, 12(4), 2089-2113; https://doi.org/10.3390/md12042089
Received: 7 February 2014 / Revised: 21 March 2014 / Accepted: 25 March 2014 / Published: 4 April 2014
Cited by 14 | PDF Full-text (698 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Diatoms are dominant photosynthetic organisms in the world’s oceans and represent a major food source for zooplankton and benthic filter-feeders. However, their beneficial role in sustaining marine food webs has been challenged after the discovery that they produce secondary metabolites, such as polyunsaturated
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Diatoms are dominant photosynthetic organisms in the world’s oceans and represent a major food source for zooplankton and benthic filter-feeders. However, their beneficial role in sustaining marine food webs has been challenged after the discovery that they produce secondary metabolites, such as polyunsaturated aldehydes (PUAs), which negatively affect the reproductive success of many invertebrates. Here, we report the effects of two common diatom PUAs, heptadienal and octadienal, which have never been tested before at the molecular level, using the sea urchin, Paracentrotus lividus, as a model organism. We show that both PUAs are able to induce teratogenesis (i.e., malformations), as already reported for decadienal, the better-studied PUA of this group. Moreover, post-recovery experiments show that embryos can recover after treatment with all three PUAs, indicating that negative effects depend both on PUA concentrations and the exposure time of the embryos to these metabolites. We also identify the time range during which PUAs exert the greatest effect on sea urchin embryogenesis. Finally, we report the expression levels of thirty one genes (having a key role in a broad range of functional responses, such as stress, development, differentiation, skeletogenesis and detoxification processes) in order to identify the common targets affected by PUAs and their correlation with morphological abnormalities. This study opens new perspectives for understanding how marine organisms afford protection from environmental toxicants through an integrated network of genes. Full article
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