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Marine Drugs
Volume 7
Issue 4
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Mar. Drugs, Volume 7, Issue 4 (December 2009) – 22 articles , Pages 483-849

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175 KiB  
Review
Terpenyl-Purines from the Sea
by Marina Gordaliza
Mar. Drugs 2009, 7(4), 833-849; https://doi.org/10.3390/md7040833 - 23 Dec 2009
Cited by 39 | Viewed by 15144
Abstract
Agelasines, asmarines and related compounds are natural products with a hybrid terpene-purine structure isolated from numerous genera of sponges (Agela sp., Raspailia sp.). Some agelasine analogs and related structures have displayed high general toxicity towards protozoa, and have exhibited broad-spectrum antimicrobial activity [...] Read more.
Agelasines, asmarines and related compounds are natural products with a hybrid terpene-purine structure isolated from numerous genera of sponges (Agela sp., Raspailia sp.). Some agelasine analogs and related structures have displayed high general toxicity towards protozoa, and have exhibited broad-spectrum antimicrobial activity against a variety of species, including Mycobacterium tuberculosis, and also an important cytotoxic activity against several cancer cell lines, including multidrug-resistant ones. Of particular interest in this context are the asmarines (tetrahydro[1,4]diazepino[1,2,3-g,h]purines), which have shown potent antiproliferative activity against several types of human cancer cell lines. This review summarizes the sources of isolation, chemistry and bioactivity of marine alkylpurines and their bioactive derivatives. Full article
(This article belongs to the Special Issue Alkaloid Analogs)
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311 KiB  
Article
Isolation of C11 Cyclopentenones from Two Didemnid Species, Lissoclinum sp. and Diplosoma sp.
by Takayuki Ogi, Palupi Margiastuti, Toshiaki Teruya, Junsei Taira, Kiyotake Suenaga and Katsuhiro Ueda
Mar. Drugs 2009, 7(4), 816-832; https://doi.org/10.3390/md7040816 - 17 Dec 2009
Cited by 22 | Viewed by 11910
Abstract
A series of new C11 cyclopentenones 1-7 was isolated, together with four known metabolites 9/10, 12 and 13, from the extract of the didemnid ascidian Lissoclinum sp. The other didemnid ascidian Diplosoma sp. [...] Read more.
A series of new C11 cyclopentenones 1-7 was isolated, together with four known metabolites 9/10, 12 and 13, from the extract of the didemnid ascidian Lissoclinum sp. The other didemnid ascidian Diplosoma sp. contained didemnenones 1, 2 and 5, and five known metabolites 8-12. The structures of 1-7 were elucidated by spectroscopic analyses. Cytotoxicity of the isolated compounds was evaluated against three human cancer cell lines (HCT116, A431 and A549). Full article
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281 KiB  
Article
Recovery of Proteolytic and Collagenolytic Activities from Viscera By-products of Rayfish (Raja clavata)
by Miguel Anxo Murado, María del Pilar González and José Antonio Vázquez
Mar. Drugs 2009, 7(4), 803-815; https://doi.org/10.3390/md7040803 - 15 Dec 2009
Cited by 28 | Viewed by 14197
Abstract
The aim of this work was to study the recovery of proteolytic and collagenolytic activities from rayfish (Raja clavata) viscera wastes. Initially, different parts of the gastrointestinal tract by-products (stomach, duodenum section including pancreas, final intestine) were evaluated. The extracts from [...] Read more.
The aim of this work was to study the recovery of proteolytic and collagenolytic activities from rayfish (Raja clavata) viscera wastes. Initially, different parts of the gastrointestinal tract by-products (stomach, duodenum section including pancreas, final intestine) were evaluated. The extracts from proximal intestine yielded the highest values of both enzymatic activities. Optimal conditions for protease activity quantification were established at pH = 6, T = 40 °C and incubation time ≤20 min. The mathematical equation used to model the joint effect of pH and temperature led to maximum activity at pH = 8.66 and 59.4 °C, respectively. Overcooled acetone was found to be best option for recovery of enzymatic activities in comparison with ethanol, PEG-4000, ammonium sulphate and ultrafiltration system. Finally, a simple and systematic protocol of partial purification and total recovery of proteases and collagenases was defined. Full article
(This article belongs to the Special Issue Enzymes from the Sea: Sources, Molecular Biology and Bioprocesses)
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Article
Towards Commercial Production of Sponge Medicines
by Marieke Koopmans, Dirk Martens and Rene H. Wijffels
Mar. Drugs 2009, 7(4), 787-802; https://doi.org/10.3390/md7040787 - 2 Dec 2009
Cited by 60 | Viewed by 16512
Abstract
Sponges can provide potential drugs against many major world-wide occurring diseases. Despite the high potential of sponge derived drugs no sustainable production method has been developed. Thus far it is not fully understood why, when, where and how these metabolites are produced in [...] Read more.
Sponges can provide potential drugs against many major world-wide occurring diseases. Despite the high potential of sponge derived drugs no sustainable production method has been developed. Thus far it is not fully understood why, when, where and how these metabolites are produced in sponges. For the near future sea-based sponge culture seems to be the best production method. However, for controlled production in a defined system it is better to develop in vitro production methods, like in vitro sponge culture or even better sponge cell culture, culture methods for symbionts or the transfer of production routes into another host. We still have insufficient information about the background of metabolite production in sponges. Before production methods are developed we should first focus on factors that can induce metabolite production. This could be done in the natural habitat by studying the relation between stress factors (such as predation) and the production of bioactive metabolites. The location of production within the sponge should be identified in order to choose between sponge cell culture and symbiont culture. Alternatively the biosynthetic pathways could be introduced into hosts that can be cultured. For this the biosynthetic pathway of metabolite production should be unraveled, as well as the genes involved. This review discusses the current state of sponge metabolite production and the steps that need to be taken to develop commercial production techniques. The different possible production techniques are also discussed. Full article
(This article belongs to the Special Issue Bioactive Compound from Marine Sponges)
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Review
Marine Pyrrolocarbazoles and Analogues: Synthesis and Kinase Inhibition
by Sébastien Deslandes, Stefan Chassaing and Evelyne Delfourne
Mar. Drugs 2009, 7(4), 754-786; https://doi.org/10.3390/md7040754 - 1 Dec 2009
Cited by 43 | Viewed by 13987
Abstract
Granulatimide and isogranulatimide are alkaloids obtained from marine sources which have been shown to inhibit cell-cycle G2-checkpoint, targeting more particularly checkpoint 1 kinase (Chk1). At a structural level, they possess a characteristic pyrrolocarbazole framework also shared by the well-known rebeccamycin and staurosporine microbial [...] Read more.
Granulatimide and isogranulatimide are alkaloids obtained from marine sources which have been shown to inhibit cell-cycle G2-checkpoint, targeting more particularly checkpoint 1 kinase (Chk1). At a structural level, they possess a characteristic pyrrolocarbazole framework also shared by the well-known rebeccamycin and staurosporine microbial metabolites which have been described to inhibit topoisomerase I and diverse kinases, respectively. This review reports precisely on the synthesis and kinase inhibitory activities of pyrrolocarbazole-based analogues of granulatimide. Full article
(This article belongs to the Special Issue Alkaloid Analogs)
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Review
A Submarine Journey: The Pyrrole-Imidazole Alkaloids
by Barbara Forte, Beatrice Malgesini, Claudia Piutti, Francesca Quartieri, Alessandra Scolaro and Gianluca Papeo
Mar. Drugs 2009, 7(4), 705-753; https://doi.org/10.3390/md7040705 - 27 Nov 2009
Cited by 218 | Viewed by 21665
Abstract
In his most celebrated tale “The Picture of Dorian Gray”, Oscar Wilde stated that “those who go beneath the surface do so at their peril”. This sentence could be a prophetical warning for the practitioner who voluntarily challenges himself with trying to synthesize [...] Read more.
In his most celebrated tale “The Picture of Dorian Gray”, Oscar Wilde stated that “those who go beneath the surface do so at their peril”. This sentence could be a prophetical warning for the practitioner who voluntarily challenges himself with trying to synthesize marine sponge-deriving pyrrole-imidazole alkaloids. This now nearly triple-digit membered community has been growing exponentially in the last 20 years, both in terms of new representatives and topological complexity − from simple, achiral oroidin to the breathtaking 12-ring stylissadines A and B, each possessing 16 stereocenters. While the biosynthesis and the role in the sponge economy of most of these alkaloids still lies in the realm of speculations, significant biological activities for some of them have clearly emerged. This review will account for the progress in achieving the total synthesis of the more biologically enticing members of this class of natural products. Full article
(This article belongs to the Special Issue Synthesis around Marine Natural Products)
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Article
The Antinociceptive and Anti-Inflammatory Activities of Caulerpin, a Bisindole Alkaloid Isolated from Seaweeds of the Genus Caulerpa
by Éverton Tenório De Souza, Daysianne Pereira de Lira, Aline Cavalcanti de Queiroz, Diogo José Costa da Silva, Anansa Bezerra de Aquino, Eliane A. Campessato Mella, Vitor Prates Lorenzo, George Emmanuel C. De Miranda, João Xavier De Araújo-Júnior, Maria Célia De Oliveira Chaves, José Maria Barbosa-Filho, Petrônio Filgueiras de Athayde-Filho, Bárbara Viviana De Oliveira Santos and Magna Suzana Alexandre-Moreira
Mar. Drugs 2009, 7(4), 689-704; https://doi.org/10.3390/md7040689 - 26 Nov 2009
Cited by 137 | Viewed by 20126
Abstract
The antinociceptive and anti-inflammatory activity of caulerpin was investigated. This bisindole alkaloid was isolated from the lipoid extract of Caulerpa racemosa and its structure was identified by spectroscopic methods, including IR and NMR techniques. The pharmacological assays used were the writhing and the [...] Read more.
The antinociceptive and anti-inflammatory activity of caulerpin was investigated. This bisindole alkaloid was isolated from the lipoid extract of Caulerpa racemosa and its structure was identified by spectroscopic methods, including IR and NMR techniques. The pharmacological assays used were the writhing and the hot plate tests, the formalin-induced pain, the capsaicin-induced ear edema and the carrageenaninduced peritonitis. Caulerpin was given orally at a concentration of 100 μmol/kg. In the abdominal constriction test caulerpin showed reduction in the acetic acid-induced nociception at 0.0945 μmol (0.0103–1.0984) and for dypirone it was 0.0426 μmol (0.0092–0.1972). In the hot plate test in vivo the inhibition of nociception by caulerpin (100 μmol/kg, p.o.) was also favorable. This result suggests that this compound exhibits a central activity, without changing the motor activity (seen in the rotarod test). Caulerpin (100 μmol/kg, p.o.) reduced the formalin effects in both phases by 35.4% and 45.6%, respectively. The possible anti-inflammatory activity observed in the second phase in the formalin test of caulerpin (100 μmol/kg, p.o.) was confirmed on the capsaicin-induced ear edema model, where an inhibition of 55.8% was presented. Indeed, it was also observed in the carrageenan-induced peritonitis that caulerpin (100 μmol/kg, p.o.) exhibited anti-inflammatory activity, reducing significantly the number of recruit cells by 48.3%. Pharmacological studies are continuing in order to characterize the mechanism(s) responsible for the antinociceptive and anti-inflammatory actions and also to identify other active principles present in Caulerpa racemosa. Full article
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Article
Effects and Interactions of Medium Components on Laccase from a Marine-Derived Fungus Using Response Surface Methodology
by Donna D’Souza-Ticlo, Sandeep Garg and Chandralata Raghukumar
Mar. Drugs 2009, 7(4), 672-688; https://doi.org/10.3390/md7040672 - 25 Nov 2009
Cited by 22 | Viewed by 12081
Abstract
The effects of various synthetic medium components and their interactions with each other ultimately impact laccase production in fungi. This was studied using a laccasehyper-producing marine-derived basidiomycete, Cerrena unicolor MTCC 5159. Inducible laccases were produced in the idiophase only after addition of an [...] Read more.
The effects of various synthetic medium components and their interactions with each other ultimately impact laccase production in fungi. This was studied using a laccasehyper-producing marine-derived basidiomycete, Cerrena unicolor MTCC 5159. Inducible laccases were produced in the idiophase only after addition of an inducer such as CuSO4. Concentration of carbon and nitrogen acted antagonistically with respect to laccase production. A combination of low nitrogen and high carbon concentration favored both biomass and laccase production. The most favorable combination resulted in 917 U L-1 of laccase. After sufficient growth had occurred, addition of a surfactant such as Tween 80 positively impacted biomass and increased the laccase activity to around 1,300 U L-1. Increasing the surface to volume ratio of the culture vessel further increased its activity to almost 2,000 U L-1. Full article
(This article belongs to the Special Issue Enzymes from the Sea: Sources, Molecular Biology and Bioprocesses)
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333 KiB  
Article
Total Synthesis and Absolute Configuration of the Marine Norditerpenoid Xestenone
by Koichiro Ota, Takao Kurokawa, Etsuko Kawashima and Hiroaki Miyaoka
Mar. Drugs 2009, 7(4), 654-671; https://doi.org/10.3390/md7040654 - 24 Nov 2009
Cited by 9 | Viewed by 11309
Abstract
Xestenone is a marine norditerpenoid found in the northeastern Pacific sponge Xestospongia vanilla. The relative configuration of C-3 and C-7 in xestenone was determined by NOESY spectral analysis. However the relative configuration of C-12 and the absolute configuration of this compound were [...] Read more.
Xestenone is a marine norditerpenoid found in the northeastern Pacific sponge Xestospongia vanilla. The relative configuration of C-3 and C-7 in xestenone was determined by NOESY spectral analysis. However the relative configuration of C-12 and the absolute configuration of this compound were not determined. The authors have now achieved the total synthesis of xestenone using their developed one-pot synthesis of cyclopentane derivatives employing allyl phenyl sulfone and an epoxy iodide as a key step. The relative and absolute configurations of xestenone were thus successfully determined by this synthesis. Full article
(This article belongs to the Special Issue Synthesis around Marine Natural Products)
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196 KiB  
Article
Antiplasmodial Activities of Homogentisic Acid Derivative Protein Kinase Inhibitors Isolated from a Vanuatu Marine Sponge Pseudoceratina sp.
by Nicolas Lebouvier, Valérie Jullian, Isabelle Desvignes, Séverine Maurel, Arnaud Parenty, Dominique Dorin-Semblat, Christian Doerig, Michel Sauvain and Dominique Laurent
Mar. Drugs 2009, 7(4), 640-653; https://doi.org/10.3390/md7040640 - 23 Nov 2009
Cited by 37 | Viewed by 13622
Abstract
As part of our search for new antimalarial drugs in South Pacific marine sponges, we have looked for inhibitors of Pfnek-1, a specific protein kinase of Plasmodium falciparum. On the basis of promising activity in a preliminary screening, the ethanolic crude extract [...] Read more.
As part of our search for new antimalarial drugs in South Pacific marine sponges, we have looked for inhibitors of Pfnek-1, a specific protein kinase of Plasmodium falciparum. On the basis of promising activity in a preliminary screening, the ethanolic crude extract of a new species of Pseudoceratina collected in Vanuatu was selected for further investigation. A bioassay-guided fractionation led to the isolation of a derivative of homogentisic acid [methyl (2,4-dibromo-3,6-dihydroxyphenyl)acetate, 4a] which inhibited Pfnek-1 with an IC50 around 1.8 μM. This product was moderately active in vitro against a FcB1 P. falciparum strain (IC50 = 12 μM). From the same sponge, we isolated three known compounds [11,19-dideoxyfistularin-3 (1), 11-deoxyfistularin-3 (2) and dibromo-verongiaquinol (3)] which were inactive against Pfnek-1. Synthesis and biological evaluation of some derivatives of 4a are reported. Full article
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279 KiB  
Article
3-O-Methylfunicone, a Selective Inhibitor of Mammalian Y-Family DNA Polymerases from an Australian Sea Salt Fungal Strain
by Yoshiyuki Mizushina, Hirohisa Motoshima, Yasuhiro Yamaguchi, Toshifumi Takeuchi, Ken Hirano, Fumio Sugawara and Hiromi Yoshida
Mar. Drugs 2009, 7(4), 624-639; https://doi.org/10.3390/md7040624 - 23 Nov 2009
Cited by 41 | Viewed by 13953
Abstract
We isolated a pol inhibitor from the cultured mycelia extract of a fungal strain isolated from natural salt from a sea salt pan in Australia, which was identified as 3-O-methylfunicone by spectroscopic analyses. This compound selectively inhibited the activities of mammalian Y-family DNA [...] Read more.
We isolated a pol inhibitor from the cultured mycelia extract of a fungal strain isolated from natural salt from a sea salt pan in Australia, which was identified as 3-O-methylfunicone by spectroscopic analyses. This compound selectively inhibited the activities of mammalian Y-family DNA polymerases (pols) (i.e., pols η, ι and κ). Among these pols, human pol κ activity was most strongly inhibited, with an IC50 value of 12.5 μM. On the other hand, the compound barely influenced the activities of the other families of mammalian pols, such as A-family (i.e., pol γ), B-family (i.e., pols α, δ and ε) or X-family (i.e., pols β, λ and terminal deoxynucleotidyl transferase), and showed no effect on the activities of fish pol δ, plant pols, prokaryotic pols and other DNA metabolic enzymes, such as calf primase of pol α, human immunodeficiency virus type-1 (HIV-1) reverse transcriptase, human telomerase, T7 RNA polymerase, mouse IMP dehydrogenase (type II), human topoisomerases I and II, T4 polynucleotide kinase or bovine deoxyribonuclease I. This compound also suppressed the growth of two cultured human cancer cell lines, HCT116 (colon carcinoma cells) and HeLa (cervix carcinoma cells), and UV-treated HeLa cells exhibited lower clonogenic survival in the presence of inhibitor. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes)
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783 KiB  
Article
Marine Benthic Diatoms Contain Compounds Able to Induce Leukemia Cell Death and Modulate Blood Platelet Activity
by Siv Kristin Prestegard, Linn Oftedal, Rosie Theresa Coyne, Gyrid Nygaard, Kaja Helvik Skjærven, Gjert Knutsen, Stein Ove Døskeland and Lars Herfindal
Mar. Drugs 2009, 7(4), 605-623; https://doi.org/10.3390/md7040605 - 18 Nov 2009
Cited by 47 | Viewed by 13555
Abstract
In spite of the high abundance and species diversity of diatoms, only a few bioactive compounds from them have been described. The present study reveals a high number of mammalian cell death inducing substances in biofilm-associated diatoms sampled from the intertidal zone. Extracts [...] Read more.
In spite of the high abundance and species diversity of diatoms, only a few bioactive compounds from them have been described. The present study reveals a high number of mammalian cell death inducing substances in biofilm-associated diatoms sampled from the intertidal zone. Extracts from the genera Melosira, Amphora, Phaeodactylum and Nitzschia were all found to induce leukemia cell death, with either classical apoptotic or autophagic features. Several extracts also contained inhibitors of thrombin-induced blood platelet activation. Some of this activity was caused by a high content of adenosine in the diatoms, ranging from 0.07 to 0.31 μg/mg dry weight. However, most of the bioactivity was adenosine deaminase-resistant. An adenosine deaminase-resistant active fraction from one of the extracts was partially purified and shown to induce apoptosis with a distinct phenotype. The results show that benthic diatoms typically found in the intertidal zone may represent a richer source of interesting bioactive compounds than hitherto recognized. Full article
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Article
A New Epoxy-cadinane Sesquiterpene from the Marine Brown Alga Dictyopteris divaricata
by Yuan-Yuan Qiao, Nai-Yun Ji, Wei Wen, Xiu-Li Yin and Qin-Zhao Xue
Mar. Drugs 2009, 7(4), 600-604; https://doi.org/10.3390/md7040600 - 17 Nov 2009
Cited by 20 | Viewed by 11386
Abstract
A new epoxy-cadinane sesquiterpene, 4β,5β-epoxycadinan-1β-ol (1), and six known cadinane sesquiterpenes: cadinan-1,4,5-triol (2), 4α,5β-dihydroxycubenol (3), cubenol (4), cadinan-3-ene-1,5-diol (5), cubenol-3-one (6), and torreyol (7), were isolated from a sample of marine brown alga [...] Read more.
A new epoxy-cadinane sesquiterpene, 4β,5β-epoxycadinan-1β-ol (1), and six known cadinane sesquiterpenes: cadinan-1,4,5-triol (2), 4α,5β-dihydroxycubenol (3), cubenol (4), cadinan-3-ene-1,5-diol (5), cubenol-3-one (6), and torreyol (7), were isolated from a sample of marine brown alga Dictyopteris divaricata collected off the coast of Yantai (China). Their structures were established by detailed MS and NMR spectroscopic analysis, as well as comparison with literature data. Full article
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Article
Inhibitory Effect of N,N-Didesmethylgrossularine-1 on Inflammatory Cytokine Production in Lipopolysaccharide-Stimulated RAW 264.7 Cells
by Taiko Oda, Jong-Soo Lee, Yuta Sato, Yasuaki Kabe, Satoshi Sakamoto, Hiroshi Handa, Remy E. P. Mangindaan and Michio Namikoshi
Mar. Drugs 2009, 7(4), 589-599; https://doi.org/10.3390/md7040589 - 17 Nov 2009
Cited by 21 | Viewed by 11911
Abstract
N,N-Didesmethylgrossularine-1 (DDMG-1), a compound with a rare α-carboline structure, was isolated from an Indonesian ascidian Polycarpa aurata as responsible for the observed inhibitory activity against TNF-α production in lipopolysaccharide-stimulated murine macrophage-like RAW264.7 cells. DDMG-1 inhibited the mRNA level of mTNF-α, [...] Read more.
N,N-Didesmethylgrossularine-1 (DDMG-1), a compound with a rare α-carboline structure, was isolated from an Indonesian ascidian Polycarpa aurata as responsible for the observed inhibitory activity against TNF-α production in lipopolysaccharide-stimulated murine macrophage-like RAW264.7 cells. DDMG-1 inhibited the mRNA level of mTNF-α, IκB-α degradation, and binding of NF-κB to the target DNA site in LPS-stimulated RAW 264.7 cells. Moreover, DDMG-1 had an inhibitory effect on the production of IL-8, which is produced in CD14+-THP-1 cells stimulated by LPS. DDMG-1 is thus a promising drug candidate lead compound for the treatment of chronic inflammatory diseases, such as rheumatoid arthritis. Full article
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Article
Violacein-Producing Collimonas sp. from the Sea Surface Microlayer of Costal Waters in Trøndelag, Norway
by Sigrid Hakvåg, Espen Fjærvik, Geir Klinkenberg, Sven Even F. Borgos, Kjell D. Josefsen, Trond E. Ellingsen and Sergey B. Zotchev
Mar. Drugs 2009, 7(4), 576-588; https://doi.org/10.3390/md7040576 - 12 Nov 2009
Cited by 73 | Viewed by 15786
Abstract
A new strain belonging to the genus Collimonas was isolated from the sea surface microlayer off the coast of Trøndelag, Norway. The bacterium, designated Collimonas CT, produced an antibacterial compound active against Micrococcus luteus. Subsequent studies using LC-MS identified this antibacterial compound [...] Read more.
A new strain belonging to the genus Collimonas was isolated from the sea surface microlayer off the coast of Trøndelag, Norway. The bacterium, designated Collimonas CT, produced an antibacterial compound active against Micrococcus luteus. Subsequent studies using LC-MS identified this antibacterial compound as violacein, known to be produced by several marine-derived bacteria. Fragments of the violacein biosynthesis genes vioA and vioB were amplified by PCR from the Collimonas CT genome and sequenced. Phylogenetic analysis of these sequences demonstrated close relatedness of the Collimonas CT violacein biosynthetic gene cluster to those in Janthinobacterium lividum and Duganella sp., suggesting relatively recent horizontal gene transfer. Considering diverse biological activities of violacein, Collimonas CT shall be further studied as a potential producer of this compound. Full article
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Article
Detailed NMR, Including 1,1-ADEQUATE, and Anticancer Studies of Compounds from the Echinoderm Colobometra perspinosa
by Anthony D. Wright, Jonathan L. Nielson, Dianne M. Tapiolas, Cherie A. Motti, Simon P. B. Ovenden, Philip S. Kearns and Catherine H. Liptrot
Mar. Drugs 2009, 7(4), 565-575; https://doi.org/10.3390/md7040565 - 12 Nov 2009
Cited by 34 | Viewed by 12212
Abstract
From the dichloromethane/methanol extract of the crinoid Colobometra perspinosa, collected south east of Richards Island (Bedara), Family Islands, Central Great Barrier Reef, Australia, 3-(1'-hydroxypropyl)-1,6,8-trihydroxy-9,10-anthraquinone [one of the two stereoisomers of rhodoptilometrin, (1)], 3-propyl-1,6,8-trihydroxy-9,10-anthraquinone (3), 2-[(phenylacetyl)amino]ethanesulfonic acid (4), and 4-hydroxybutanoic acid (5) were [...] Read more.
From the dichloromethane/methanol extract of the crinoid Colobometra perspinosa, collected south east of Richards Island (Bedara), Family Islands, Central Great Barrier Reef, Australia, 3-(1'-hydroxypropyl)-1,6,8-trihydroxy-9,10-anthraquinone [one of the two stereoisomers of rhodoptilometrin, (1)], 3-propyl-1,6,8-trihydroxy-9,10-anthraquinone (3), 2-[(phenylacetyl)amino]ethanesulfonic acid (4), and 4-hydroxybutanoic acid (5) were isolated. Comparison of 1H- and 13C-NMR data for rhodoptilometrin (1) with those reported in the literature showed significant differences for some resonances associated with rings A and C. In an attempt to provide accurately assigned 1H- and 13C-NMR data, as well as to confirm the structure of 1, a thorough NMR investigation of this compound was undertaken. Measurements included: concentration dependent 13C, 1D selective NOE, HSQC, HMBC and 1,1-ADEQUATE. The NMR data for 4 and 5 are reported here for the first time, as is their occurrence from the marine environment. The in vitro anticancer activity of the original extract was found to be associated with 1, 3 and 5. Full article
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Review
Impact of Marine Drugs on Animal Reproductive Processes
by Francesco Silvestre and Elisabetta Tosti
Mar. Drugs 2009, 7(4), 539-564; https://doi.org/10.3390/md7040539 - 6 Nov 2009
Cited by 7 | Viewed by 11324
Abstract
The discovery and description of bioactive substances from natural sources has been a research topic for the last 50 years. In this respect, marine animals have been used to extract many new compounds exerting different actions. Reproduction is a complex process whose main [...] Read more.
The discovery and description of bioactive substances from natural sources has been a research topic for the last 50 years. In this respect, marine animals have been used to extract many new compounds exerting different actions. Reproduction is a complex process whose main steps are the production and maturation of gametes, their activation, the fertilisation and the beginning of development. In the literature it has been shown that many substances extracted from marine organisms may have profound influence on the reproductive behaviour, function and reproductive strategies and survival of species. However, despite the central importance of reproduction and thus the maintenance of species, there are still few studies on how reproductive mechanisms are impacted by marine bioactive drugs. At present, studies in either marine and terrestrial animals have been particularly important in identifying what specific fine reproductive mechanisms are affected by marine-derived substances. In this review we describe the main steps of the biology of reproduction and the impact of substances from marine environment and organisms on the reproductive processes. Full article
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Article
Lyngbyastatins 8–10, Elastase Inhibitors with Cyclic Depsipeptide Scaffolds Isolated from the Marine Cyanobacterium Lyngbya semiplena
by Jason C. Kwan, Kanchan Taori, Valerie J. Paul and Hendrik Luesch
Mar. Drugs 2009, 7(4), 528-538; https://doi.org/10.3390/md7040528 - 3 Nov 2009
Cited by 74 | Viewed by 12972
Abstract
Investigation of an extract from the marine cyanobacterium Lyngbya semiplena, collected in Tumon Bay, Guam, led to the identification of three new cyclodepsipeptides, lyngbyastatins 8–10 (1–3). The structures of 1–3 were determined by NMR, MS, ESIMS fragmentation and chemical degradation. Compounds 1–3 [...] Read more.
Investigation of an extract from the marine cyanobacterium Lyngbya semiplena, collected in Tumon Bay, Guam, led to the identification of three new cyclodepsipeptides, lyngbyastatins 8–10 (1–3). The structures of 1–3 were determined by NMR, MS, ESIMS fragmentation and chemical degradation. Compounds 1–3 are closely related to lyngbyastatins 4–7. Like the latter compounds, we found 1–3 to inhibit porcine pancreatic elastase, with IC50 values of 123 nM, 210 nM and 120 nM, respectively. Full article
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Article
A New Polyunsaturated Brominated Fatty Acid from a Haliclona Sponge
by Satoe Aratake, Agus Trianto, Novriyandi Hanif, Nicole J. De Voogd and Junichi Tanaka
Mar. Drugs 2009, 7(4), 523-527; https://doi.org/10.3390/md7040523 - 2 Nov 2009
Cited by 20 | Viewed by 12629
Abstract
A new polyunsaturated brominated fatty acid possessing acetylenic bonds 1 was isolated from the Indonesian sponge Haliclona sp. The structure of compound 1 was elucidated by analyzing its spectral data. It showed moderate cytotoxicity against cultured cells. Full article
(This article belongs to the Special Issue Bioactive Compound from Marine Sponges)
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Article
Preliminary Characterization of Extracellular Allelochemicals of the Toxic Marine Dinoflagellate Alexandrium tamarense Using a Rhodomonas salina Bioassay
by Haiyan Ma, Bernd Krock, Urban Tillmann and Allan Cembella
Mar. Drugs 2009, 7(4), 497-522; https://doi.org/10.3390/md7040497 - 2 Nov 2009
Cited by 77 | Viewed by 13961
Abstract
Members of the marine dinoflagellate genus Alexandrium are known to exude allelochemicals, unrelated to well-known neurotoxins (PSP-toxins, spirolides), with negative effects on other phytoplankton and marine grazers. Physico/chemical characterization of extracellular lytic compounds of A. tamarense, quantified by Rhodomonas salina bioassay, showed [...] Read more.
Members of the marine dinoflagellate genus Alexandrium are known to exude allelochemicals, unrelated to well-known neurotoxins (PSP-toxins, spirolides), with negative effects on other phytoplankton and marine grazers. Physico/chemical characterization of extracellular lytic compounds of A. tamarense, quantified by Rhodomonas salina bioassay, showed that the lytic activity, and hence presumably the compounds were stable over wide ranges of temperatures and pH and were refractory to bacterial degradation. Two distinct lytic fractions were collected by reversed-phase solid-phase extraction. The more hydrophilic fraction accounted for about 2% of the whole lytic activity of the A. tamarense culture supernatant, while the less hydrophilic one accounted for about 98% of activity. Although temporal stability of the compounds is high, substantial losses were evident during purification. Lytic activity was best removed from aqueous phase with chloroform-methanol (3:1). A “pseudo-loss” of lytic activity in undisturbed and low-concentrated samples and high activity of an emulsion between aqueous and n-hexane phase after liquid-liquid partition are strong evidence for the presence of amphipathic compounds. Lytic activity in the early fraction of gel permeation chromatography and lack of activity after 5 kD ultrafiltration indicate that the lytic agents form large aggregates or macromolecular complexes. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes)
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159 KiB  
Correction
Correction: Hong, K. et al. Actinomycetes for Marine Drug Discovery Isolated from Mangrove Soils and Plants in China. Mar. Drugs 2009, 7, 24–44
by Kui Hong, An-Hui Gao, Qing-Yi Xie, Hao Gao, Ling Zhuang, Hai-Peng Lin, Hai-Ping Yu, Jia Li, Xin-Sheng Yao, Michael Goodfellow and Ji-Sheng Ruan
Mar. Drugs 2009, 7(4), 495-496; https://doi.org/10.3390/md7040495 - 21 Oct 2009
Cited by 7 | Viewed by 12883
Abstract
We found an error in our paper published in Marine Drugs [1]. [...] Full article
289 KiB  
Communication
Microarray-Based Transcriptional Profiling of Renieramycin M and Jorunnamycin C, Isolated from Thai Marine Organisms
by Kornvika Charupant, Khanit Suwanborirux, Naomi Daikuhara, Masashi Yokoya, Rie Ushijima-Sugano, Takatoshi Kawai, Takashi Owa and Naoki Saito
Mar. Drugs 2009, 7(4), 483-494; https://doi.org/10.3390/md7040483 - 19 Oct 2009
Cited by 13 | Viewed by 12065
Abstract
Renieramycin M and jorunnamycin C, two isoquinolinequinone compounds differing only at the C-22 ester side chain, were evaluated for their cytotoxic effects on human colon (HCT116) and breast (MDA-MB-435) cancer cell lines. These two compounds displayed potent cancer cell growth inhibition, their IC [...] Read more.
Renieramycin M and jorunnamycin C, two isoquinolinequinone compounds differing only at the C-22 ester side chain, were evaluated for their cytotoxic effects on human colon (HCT116) and breast (MDA-MB-435) cancer cell lines. These two compounds displayed potent cancer cell growth inhibition, their IC50 values reaching nanomolar order. To examine their effects on transcription, we carried out oligonucleotide microarray analysis with focus on the similarities and differences between the two compounds in terms of transcriptional profiles. We found that the down-regulation of PTPRK (protein tyrosine phosphatase receptor type K) can be considered as a biomarker responsive to the cytotoxic effects of this class of antitumor marine natural products. Full article
(This article belongs to the Special Issue Marine Actinomycetes: A New Source of Natural Products)
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