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Mar. Drugs, Volume 8, Issue 2 (February 2010) – 10 articles , Pages 219-380

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183 KiB  
Communication
Anti-Parasitic Compounds from Streptomyces sp. Strains Isolated from Mediterranean Sponges
by Sheila Marie Pimentel-Elardo, Svitlana Kozytska, Tim S. Bugni, Chris M. Ireland, Heidrun Moll and Ute Hentschel
Mar. Drugs 2010, 8(2), 373-380; https://doi.org/10.3390/md8020373 - 23 Feb 2010
Cited by 164 | Viewed by 18477
Abstract
Actinomycetes are prolific producers of pharmacologically important compounds accounting for about 70% of the naturally derived antibiotics that are currently in clinical use. In this study, we report on the isolation of Streptomyces sp. strains from Mediterranean sponges, on their secondary metabolite production [...] Read more.
Actinomycetes are prolific producers of pharmacologically important compounds accounting for about 70% of the naturally derived antibiotics that are currently in clinical use. In this study, we report on the isolation of Streptomyces sp. strains from Mediterranean sponges, on their secondary metabolite production and on their screening for anti-infective activities. Bioassay-guided isolation and purification yielded three previously known compounds namely, cyclic depsipeptide valinomycin, indolocarbazole alkaloid staurosporine and butenolide. This is the first report of the isolation of valinomycin from a marine source. These compounds exhibited novel anti-parasitic activities specifically against Leishmania major (valinomycin IC50 < 0.11 µM; staurosporine IC50 5.30 µM) and Trypanosoma brucei brucei (valinomycin IC50 0.0032 µM; staurosporine IC50 0.022 µM; butenolide IC50 31.77 µM). These results underscore the potential of marine actinomycetes to produce bioactive compounds as well as the re-evaluation of previously known compounds for novel anti-infective activities. Full article
(This article belongs to the Special Issue Marine Anti-infective Agents)
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108 KiB  
Article
New Lobane and Cembrane Diterpenes from Two Comorian Soft Corals
by Isabelle Bonnard, Sabina B. Jhaumeer-Laulloo, Nataly Bontemps, Bernard Banaigs and Maurice Aknin
Mar. Drugs 2010, 8(2), 359-372; https://doi.org/10.3390/md8020359 - 23 Feb 2010
Cited by 34 | Viewed by 12673
Abstract
Preliminary biological investigation of a collection of Comorian soft corals resulted in the selection of two specimens, one of Sarcophyton and the other of Lobophytum, on the basis of their toxicity on larvae of the brine shrimp (Artemia salina) and inhibition of acetylcholinesterase, [...] Read more.
Preliminary biological investigation of a collection of Comorian soft corals resulted in the selection of two specimens, one of Sarcophyton and the other of Lobophytum, on the basis of their toxicity on larvae of the brine shrimp (Artemia salina) and inhibition of acetylcholinesterase, respectively. Bioassay-guided fractionations provided a known antitumor promoter cembrane diterpenoid, (+)-sarcophytol-A (1), along with a new lobane diterpenoid, carbomethoxyfuscol (2), from Sarcophyton sp., and a new cembranoid, crassumolide E (3), from Lobophytum sp. The structures of compounds 13 were determined by spectroscopic analysis and by comparison of the spectral data with previously reported values. The cembranoid 3 was found to exhibit a moderate inhibitory effect on acetylcholinesterase. Full article
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158 KiB  
Article
Marine Natural Meroterpenes: Synthesis and Antiproliferative Activity
by Annabel Simon-Levert, Christophe Menniti, Laurent Soulère, Anne-Marie Genevière, Chantal Barthomeuf, Bernard Banaigs and Anne Witczak
Mar. Drugs 2010, 8(2), 347-358; https://doi.org/10.3390/md8020347 - 23 Feb 2010
Cited by 27 | Viewed by 12845
Abstract
Meroterpenes are compounds of mixed biogenesis, isolated from plants, microorganisms and marine invertebrates. We have previously isolated and determined the structure for a series of meroterpenes extracted from the ascidian Aplidium aff. densum. Here, we demonstrate the chemical synthesis of three of [...] Read more.
Meroterpenes are compounds of mixed biogenesis, isolated from plants, microorganisms and marine invertebrates. We have previously isolated and determined the structure for a series of meroterpenes extracted from the ascidian Aplidium aff. densum. Here, we demonstrate the chemical synthesis of three of them and their derivatives, and evaluate their biological activity on two bacterial strains, on sea urchin eggs, and on cancerous and healthy human cells. Full article
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495 KiB  
Review
Bioactive Sesterterpenes and Triterpenes from Marine Sponges: Occurrence and Pharmacological Significance
by Sherif S. Ebada, WenHan Lin and Peter Proksch
Mar. Drugs 2010, 8(2), 313-346; https://doi.org/10.3390/md8020313 - 23 Feb 2010
Cited by 136 | Viewed by 17090
Abstract
Marine ecosystems (>70% of the planet's surface) comprise a continuous resource of immeasurable biological activities and immense chemical entities. This diversity has provided a unique source of chemical compounds with potential bioactivities that could lead to potential new drug candidates. Many marine-living organisms [...] Read more.
Marine ecosystems (>70% of the planet's surface) comprise a continuous resource of immeasurable biological activities and immense chemical entities. This diversity has provided a unique source of chemical compounds with potential bioactivities that could lead to potential new drug candidates. Many marine-living organisms are soft bodied and/or sessile. Consequently, they have developed toxic secondary metabolites or obtained them from microorganisms to defend themselves against predators [1]. For the last 30–40 years, marine invertebrates have been an attractive research topic for scientists all over the world. A relatively small number of marine plants, animals and microbes have yielded more than 15,000 natural products including numerous compounds with potential pharmaceutical potential. Some of these have already been launched on the pharmaceutical market such as Prialt® (ziconotide; potent analgesic) and Yondelis® (trabectedin or ET-743; antitumor) while others have entered clinical trials, e.g., alpidin and kahalalide F. Amongst the vast array of marine natural products, the terpenoids are one of the more commonly reported and discovered to date. Sesterterpenoids (C25) and triterpenoids (C30) are of frequent occurrence, particularly in marine sponges, and they show prominent bioactivities. In this review, we survey sesterterpenoids and triterpenoids obtained from marine sponges and highlight their bioactivities. Full article
(This article belongs to the Special Issue Terpenoids of Marine Origin)
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161 KiB  
Review
Chitins and Chitosans as Immunoadjuvants and Non-Allergenic Drug Carriers
by Riccardo A. A. Muzzarelli
Mar. Drugs 2010, 8(2), 292-312; https://doi.org/10.3390/md8020292 - 21 Feb 2010
Cited by 360 | Viewed by 22678
Abstract
Due to the fact that some individuals are allergic to crustaceans, the presumed relationship between allergy and the presence of chitin in crustaceans has been investigated. In vivo, chitin is part of complex structures with other organic and inorganic compounds: in arthropods [...] Read more.
Due to the fact that some individuals are allergic to crustaceans, the presumed relationship between allergy and the presence of chitin in crustaceans has been investigated. In vivo, chitin is part of complex structures with other organic and inorganic compounds: in arthropods chitin is covalently linked to proteins and tanned by quinones, in fungi it is covalently linked to glucans, while in bacteria chitin is diversely combined according to Gram(+/-) classification. On the other hand, isolated, purified chitin is a plain polysaccharide that, at the nano level, presents itself as a highly associated structure, recently refined in terms of regularity, nature of bonds, crystallinity degree and unusual colloidal behavior. Chitins and modified chitins exert a number of beneficial actions, i.e., (i) they stimulate macrophages by interacting with receptors on the macrophage surface that mediate the internalization of chitin particles to be degraded by lysozyme and N-acetyl-β-glucosaminidase (such as Nod-like, Toll-like, lectin, Dectin-1, leukotriene 134 and mannose receptors); (ii) the macrophages produce cytokines and other compounds that confer non-specific host resistance against bacterial and viral infections, and anti-tumor activity; (iii) chitin is a strong Th1 adjuvant that up-regulates Th1 immunity induced by heat-killed Mycobacterium bovis, while down- regulating Th2 immunity induced by mycobacterial protein; (iv) direct intranasal application of chitin microparticles into the lung was also able to significantly down-regulate allergic response to Dermatophagoids pteronyssinus and Aspergillus fumigatus in a murine model of allergy; (v) chitin microparticles had a beneficial effect in preventing and treating histopathologic changes in the airways of asthmatic mice; (vi) authors support the fact that chitin depresses the development of adaptive type 2 allergic responses. Since the expression of chitinases, chitrotriosidase and chitinase-like proteins is greatly amplified during many infections and diseases, the common feature of chitinase-like proteins and chitinase activity in all organisms appears to be the biochemical defense of the host. Unfortunately, conceptual and methodological errors are present in certain recent articles dealing with chitin and allergy, i.e., (1) omitted consideration of mammalian chitinase and/or chitotriosidase secretion, accompanied by inactive chitinase-like proteins, as an ancestral defensive means against invasion, capable to prevent the insurgence of allergy; (2) omitted consideration of the fact that the mammalian organism recognizes more promptly the secreted water soluble chitinase produced by a pathogen, rather than the insoluble and well protected chitin within the pathogen itself; (3) superficial and incomplete reports and investigations on chitin as an allergen, without mentioning the potent allergen from crustacean flesh, tropomyosine; (4) limited perception of the importance of the chemical/biochemical characteristics of the isolated chitin or chitosan for the replication of experiments and optimization of results; and (5) lack of interdisciplinarity. There is quite a large body of knowledge today on the use of chitosans as biomaterials, and more specifically as drug carriers for a variety of applications: the delivery routes being the same as those adopted for the immunological studies. Said articles, that devote attention to the safety and biocompatibility aspects, never reported intolerance or allergy in individuals and animals, even when the quantities of chitosan used in single experiments were quite large. Therefore, it is concluded that crab, shrimp, prawn and lobster chitins, as well as chitosans of all grades, once purified, should not be considered as "crustacean derivatives", because the isolation procedures have removed proteins, fats and other contaminants to such an extent as to allow them to be classified as chemicals regardless of their origin. Full article
(This article belongs to the Special Issue Marine Chitin and Chitosan)
203 KiB  
Article
Iodocionin, a Cytotoxic Iodinated Metabolite from the Mediterranean Ascidian Ciona edwardsii
by Anna Aiello, Ernesto Fattorusso, Concetta Imperatore, Marialuisa Menna and Werner E.G. Müller
Mar. Drugs 2010, 8(2), 285-291; https://doi.org/10.3390/md8020285 - 21 Feb 2010
Cited by 26 | Viewed by 10451
Abstract
Chemical investigation of the Mediterranean ascidian Ciona edwardsii has been performed, leading to the isolation of two halogenated compounds: a new tyrosine-iodinated derivative iodocionin (1) and the relevant brominated analogue (2), previously isolated from a Caribbean sponge. The structure [...] Read more.
Chemical investigation of the Mediterranean ascidian Ciona edwardsii has been performed, leading to the isolation of two halogenated compounds: a new tyrosine-iodinated derivative iodocionin (1) and the relevant brominated analogue (2), previously isolated from a Caribbean sponge. The structure of the new compound 1 has been assigned on the basis of spectroscopic analysis.Both compounds were tested for cytotoxicity in vitro against two different cancer cell lines, L5178Y (mouse lymphoma) and PC-12 (rat pheochromocytoma). Iodocionin was shown to possess significant and selective activity against lymphoma cells with an IC50 of 7.75 μg/mL. Full article
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349 KiB  
Review
Alkaloids in Marine Algae
by Kasım Cemal Güven, Aline Percot and Ekrem Sezik
Mar. Drugs 2010, 8(2), 269-284; https://doi.org/10.3390/md8020269 - 04 Feb 2010
Cited by 167 | Viewed by 21424
Abstract
This paper presents the alkaloids found in green, brown and red marine algae. Algal chemistry has interested many researchers in order to develop new drugs, as algae include compounds with functional groups which are characteristic from this particular source. Among these compounds, alkaloids [...] Read more.
This paper presents the alkaloids found in green, brown and red marine algae. Algal chemistry has interested many researchers in order to develop new drugs, as algae include compounds with functional groups which are characteristic from this particular source. Among these compounds, alkaloids present special interest because of their pharmacological activities. Alkaloid chemistry has been widely studied in terrestrial plants, but the number of studies in algae is insignificant. In this review, a detailed account of macro algae alkaloids with their structure and pharmacological activities is presented. The alkaloids found in marine algae may be divided into three groups: 1. Phenylethylamine alkaloids, 2. Indole and halogenated indole alkaloids, 3. Other alkaloids. Full article
(This article belongs to the Special Issue Alkaloid Analogs)
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460 KiB  
Article
Oyster (Crassostrea gigas) Hydrolysates Produced on a Plant Scale Have Antitumor Activity and Immunostimulating Effects in BALB/c Mice
by Yu-Kai Wang, Hai-Lun He, Guo-Fan Wang, Hao Wu, Bai-Cheng Zhou, Xiu-Lan Chen and Yu-Zhong Zhang
Mar. Drugs 2010, 8(2), 255-268; https://doi.org/10.3390/md8020255 - 02 Feb 2010
Cited by 135 | Viewed by 16118
Abstract
Oyster extracts have been reported to have many bioactive peptides. But the function of oyster peptides produced by proteolysis is still unknown. In this study, the oligopeptide-enriched hydrolysates from oyster (Crassostrea gigas) were produced using the protease from Bacillus sp. SM98011 [...] Read more.
Oyster extracts have been reported to have many bioactive peptides. But the function of oyster peptides produced by proteolysis is still unknown. In this study, the oligopeptide-enriched hydrolysates from oyster (Crassostrea gigas) were produced using the protease from Bacillus sp. SM98011 at laboratory level, and scaled up to pilot (100 L) and plant (1,000 L) levels with the same conditions. And the antitumor activity and immunostimulating effects of the oyster hydrolysates in BALB/c mice were investigated. The growth of transplantable sarcoma-S180 was obviously inhibited in a dose-dependent manner in BALB/c mice given the oyster hydrolysates. Mice receiving 0.25, 0.5 and 1 mg/g of body weight by oral gavage had 6.8%, 30.6% and 48% less tumor growth, respectively. Concurrently, the weight coefficients of the thymus and the spleen, the activity of natural killer (NK) cells, the spleen proliferation of lymphocytes and the phagocytic rate of macrophages in S180-bearing mice significantly increased after administration of the oyster hydrolysates. These results demonstrated that oyster hydrolysates produced strong immunostimulating effects in mice, which might result in its antitumor activity. The antitumor and immunostimulating effects of oyster hydrolysates prepared in this study reveal its potential for tumor therapy and as a dietary supplement with immunostimulatory activity. Full article
(This article belongs to the Special Issue Enzymes from the Sea: Sources, Molecular Biology and Bioprocesses)
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428 KiB  
Article
Natural Occurrence of 2′,5′-Linked Heteronucleotides in Marine Sponges
by Annika Lopp, Tönu Reintamm, Anne Kuusksalu, Indrek Tammiste, Arno Pihlak and Merike Kelve
Mar. Drugs 2010, 8(2), 235-254; https://doi.org/10.3390/md8020235 - 02 Feb 2010
Cited by 9 | Viewed by 12395
Abstract
2′,5′-oligoadenylate synthetases (OAS) as a component of mammalian interferon-induced antiviral enzymatic system catalyze the oligomerization of cellular ATP into 2′,5′-linked oligoadenylates (2-5A). Though vertebrate OASs have been characterized as 2′-nucleotidyl transferases under in vitro conditions, the natural occurrence of 2′,5′-oligonucleotides other than 2-5A [...] Read more.
2′,5′-oligoadenylate synthetases (OAS) as a component of mammalian interferon-induced antiviral enzymatic system catalyze the oligomerization of cellular ATP into 2′,5′-linked oligoadenylates (2-5A). Though vertebrate OASs have been characterized as 2′-nucleotidyl transferases under in vitro conditions, the natural occurrence of 2′,5′-oligonucleotides other than 2-5A has never been demonstrated. Here we have demonstrated that OASs from the marine sponges Thenea muricata and Chondrilla nucula are able to catalyze in vivo synthesis of 2-5A as well as the synthesis of a series 2′,5′-linked heteronucleotides which accompanied high levels of 2′,5′-diadenylates. In dephosphorylated perchloric acid extracts of the sponges, these heteronucleotides were identified as A2′p5′G, A2′p5′U, A2′p5′C, G2′p5′A and G2′p5′U. The natural occurrence of 2′-adenylated NAD+ was also detected. In vitro assays demonstrated that besides ATP, GTP was a good substrate for the sponge OAS, especially for OAS from C. nucula. Pyrimidine nucleotides UTP and CTP were also used as substrates for oligomerization, giving 2′,5′-linked homo-oligomers. These data refer to the substrate specificity of sponge OASs that is remarkably different from that of vertebrate OASs. Further studies of OASs from sponges may help to elucidate evolutionary and functional aspects of OASs as proteins of the nucleotidyltransferase family. Full article
(This article belongs to the Special Issue Enzymes from the Sea: Sources, Molecular Biology and Bioprocesses)
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426 KiB  
Review
The Tetrodotoxin Binding Site Is within the Outer Vestibule of the Sodium Channel
by Harry A. Fozzard and Gregory M. Lipkind
Mar. Drugs 2010, 8(2), 219-234; https://doi.org/10.3390/md8020219 - 01 Feb 2010
Cited by 108 | Viewed by 15262
Abstract
Tetrodotoxin and saxitoxin are small, compact asymmetrical marine toxins that block voltage-gated Na channels with high affinity and specificity. They enter the channel pore’s outer vestibule and bind to multiple residues that control permeation. Radiolabeled toxins were key contributors to channel protein purification [...] Read more.
Tetrodotoxin and saxitoxin are small, compact asymmetrical marine toxins that block voltage-gated Na channels with high affinity and specificity. They enter the channel pore’s outer vestibule and bind to multiple residues that control permeation. Radiolabeled toxins were key contributors to channel protein purification and subsequent cloning. They also helped identify critical structural elements called P loops. Spacial organization of their mutation-identified interaction sites in molecular models has generated a molecular image of the TTX binding site in the outer vestibule and the critical permeation and selectivity features of this region. One site in the channel’s domain I P loop determines affinity differences in mammalian isoforms. Full article
(This article belongs to the Special Issue Tetrodotoxin 2011)
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