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Mar. Drugs, Volume 7, Issue 2 (June 2009), Pages 71-267

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Research

Jump to: Review, Other

Open AccessArticle Matrix Metalloproteinase Inhibitors (MMPIs) from Marine Natural Products: the Current Situation and Future Prospects
Mar. Drugs 2009, 7(2), 71-84; doi:10.3390/md7020071
Received: 22 December 2008 / Revised: 25 March 2009 / Accepted: 25 March 2009 / Published: 31 March 2009
Cited by 30 | PDF Full-text (141 KB) | HTML Full-text | XML Full-text
Abstract
Matrix metalloproteinases (MMPs) are a family of more than twenty five secreted and membrane-bound zinc-endopeptidases which can degrade extracellular matrix (ECM) components. They also play important roles in a variety of biological and pathological processes. Matrix metalloproteinase inhibitors (MMPIs) have been identified [...] Read more.
Matrix metalloproteinases (MMPs) are a family of more than twenty five secreted and membrane-bound zinc-endopeptidases which can degrade extracellular matrix (ECM) components. They also play important roles in a variety of biological and pathological processes. Matrix metalloproteinase inhibitors (MMPIs) have been identified as potential therapeutic candidates for metastasis, arthritis, chronic inflammation and wrinkle formation. Up to present, more than 20,000 new compounds have been isolated from marine organisms, where considerable numbers of these naturally occurring derivatives are developed as potential candidates for pharmaceutical application. Eventhough the quantity of marine derived MMPIs is less when compare with the MMPIs derived from terrestrial materials, huge potential for bioactivity of these marine derived MMPIs has lead to large number of researches. Saccharoids, flavonoids and polyphones, fatty acids are the most important groups of MMPIs derived from marine natural products. In this review we focus on the progress of MMPIs from marine natural products. Full article
Open AccessArticle Fibrinolytic Compounds Isolated from a Brown Alga, Sargassum fulvellum
Mar. Drugs 2009, 7(2), 85-94; doi:10.3390/md7020085
Received: 13 February 2009 / Accepted: 4 April 2009 / Published: 7 April 2009
Cited by 13 | PDF Full-text (296 KB) | HTML Full-text | XML Full-text
Abstract
Two of bioactive natural products were founded in a brown alga, Sargassum fulvellum. After isolation and purification, the molecular structures of these two products were investigated by NMR spectroscopy and GC-mass spectroscopy. The two compounds were identified to be 1- [...] Read more.
Two of bioactive natural products were founded in a brown alga, Sargassum fulvellum. After isolation and purification, the molecular structures of these two products were investigated by NMR spectroscopy and GC-mass spectroscopy. The two compounds were identified to be 1-O-palmitoyl-2-O-oleoyl-3-O-(α-D-glucopyranosyl) –glycerol (POGG) and 1-O-myristoyl-2-O-oleoyl-3-O-(α-D-glucopyranosyl) – glycerol (MOGG) which were obtained from Sargassum fulvellum for the first time. POGG and MOGG showed fibrinolytic activity in the reaction system of pro-u-PA and plasminogen. Full article
Open AccessArticle Broad-Spectrum Antimicrobial Epiphytic and Endophytic Fungi from Marine Organisms: Isolation, Bioassay and Taxonomy
Mar. Drugs 2009, 7(2), 97-112; doi:10.3390/md7020097
Received: 26 March 2009 / Revised: 12 April 2009 / Accepted: 16 April 2009 / Published: 17 April 2009
Cited by 34 | PDF Full-text (566 KB) | HTML Full-text | XML Full-text
Abstract
In the search for new marine derived antibiotics, 43 epi- and endophytic fungal strains were isolated from the surface or the inner tissue of different marine plants and invertebrates. Through preliminary and secondary screening, 10 of them were found to be able [...] Read more.
In the search for new marine derived antibiotics, 43 epi- and endophytic fungal strains were isolated from the surface or the inner tissue of different marine plants and invertebrates. Through preliminary and secondary screening, 10 of them were found to be able to produce broad-spectrum antimicrobial metabolites. By morphological and molecular biological methods, three active strains were characterized to be Penicillium glabrum, Fusarium oxysporum, and Alternaria alternata. Full article
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Open AccessArticle Chemopreventive Effects of Sarcophine-diol on Ultraviolet B-induced Skin Tumor Development in SKH-1 Hairless Mice
Mar. Drugs 2009, 7(2), 153-165; doi:10.3390/md7020153
Received: 27 March 2009 / Revised: 16 April 2009 / Accepted: 28 April 2009 / Published: 30 April 2009
Cited by 13 | PDF Full-text (318 KB) | HTML Full-text | XML Full-text
Abstract
Sarcophine-diol (SD), one of the structural modifications of sarcophine, has shown chemopreventive effects on 12-dimethylbenz(a)anthracene-initiated and 12-O- tetradecanoylphorbol-13-acetate-promoted skin tumor development in female CD-1 mice. The objective of this study was to determine the chemopreventive effects of SD on UVB-induced [...] Read more.
Sarcophine-diol (SD), one of the structural modifications of sarcophine, has shown chemopreventive effects on 12-dimethylbenz(a)anthracene-initiated and 12-O- tetradecanoylphorbol-13-acetate-promoted skin tumor development in female CD-1 mice. The objective of this study was to determine the chemopreventive effects of SD on UVB-induced skin tumor development in hairless SKH-1 mice, a model more relevant to human skin cancer, and to determine the possible mechanisms of action. Carcinogenesis was initiated and promoted by UVB radiation. Female hairless SKH-1 mice were divided into two groups having 27 mice in each group: control and SD treatment. The control group was topically treated with 100 μL acetone and SD treatment group was topically treated with SD (30 μg/100 μL in acetone) 1 hour before each UVB radiation for 32 weeks. Tumor counts were recorded on a weekly basis for 30 weeks. Effects of SD on the expression of caspases were investigated to elucidate the possible mechanism of action. The proteins from epidermal homogenates of experimental mice were used for SDS-PAGE and Western blotting using specific antibodies against caspase-3, caspase-8 and caspase-9 respectively. TUNEL assay was used for determining DNA fragmented apoptotic cells in situ. Results showed that at the end of experiment, tumor multiplicity in control and SD treatment groups was 25.8 and 16.5 tumors per mouse respectively. Furthermore, Topical treatment of SD induced DNA fragmented apoptotic cells by upgrading the expressions of cleaved caspase-3 and caspase-8. This study clearly suggested that SD could be an effective chemopreventive agent for UVB-induced skin cancer by inducing caspase dependent apoptosis. Full article
Open AccessArticle Sphaeroane and Neodolabellane Diterpenes from the Red Alga Sphaerococcus coronopifolius
Mar. Drugs 2009, 7(2), 184-195; doi:10.3390/md7020184
Received: 17 April 2009 / Revised: 4 May 2009 / Accepted: 18 May 2009 / Published: 19 May 2009
Cited by 8 | PDF Full-text (318 KB) | HTML Full-text | XML Full-text
Abstract
Investigation of minor metabolites in the extracts of the red alga Sphaerococcus coronopifolius collected from the rocky coasts of Corfu Island in the Ionian Sea yielded two new diterpene alcohols, sphaerollanes I,and II (1, 2) featuring neodolabellane skeletons, and the new sphaeroane [...] Read more.
Investigation of minor metabolites in the extracts of the red alga Sphaerococcus coronopifolius collected from the rocky coasts of Corfu Island in the Ionian Sea yielded two new diterpene alcohols, sphaerollanes I,and II (1, 2) featuring neodolabellane skeletons, and the new sphaeroane diterpene alcohol 16-hydroxy-9S*-acetoxy-8-epi-isosphaerodiene-2 (3), along with two previously reported metabolites 4, 5. The structures of the new natural products, as well as their relative stereochemistry, were elucidated on the basis of extensive spectral analysis, including 2D-NMR experiments. Full article
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Open AccessArticle Deoxyamphimedine, a Pyridoacridine Alkaloid, Damages DNA via the Production of Reactive Oxygen Species
Mar. Drugs 2009, 7(2), 196-209; doi:10.3390/md7020196
Received: 5 February 2009 / Revised: 12 May 2009 / Accepted: 16 May 2009 / Published: 25 May 2009
Cited by 15 | PDF Full-text (515 KB) | HTML Full-text | XML Full-text
Abstract
Marine pyridoacridines are a class of aromatic chemicals that share an 11H-pyrido[4,3,2-mn]acridine skeleton. Pyridoacridine alkaloids display diverse biological activities including cytotoxicity, fungicidal and bactericidal properties, production of reactive oxygen species (ROS) and topoisomerase inhibition. These activities are often [...] Read more.
Marine pyridoacridines are a class of aromatic chemicals that share an 11H-pyrido[4,3,2-mn]acridine skeleton. Pyridoacridine alkaloids display diverse biological activities including cytotoxicity, fungicidal and bactericidal properties, production of reactive oxygen species (ROS) and topoisomerase inhibition. These activities are often dependent on slight modifications to the pyridoacridine skeleton. Here we demonstrate that while structurally similar to neoamphimedine and amphimedine, the biological activity of deoxyamphimedine differs greatly. Deoxyamphimedine damages DNA in vitro independent of topoisomerase enzymes through the generation of reactive oxygen species. Its activity was decreased in low oxygen, with the removal of a reducing agent and in the presence of anti-oxidants. Deoxyamphimedine also showed enhanced toxicity in cells sensitive to single or double strand DNA breaks, consistent with the in vitro activity. Full article
Open AccessArticle New Azaphilones, Seco-Chaetomugilins A and D, Produced by a Marine-Fish-Derived Chaetomium globosum
Mar. Drugs 2009, 7(2), 249-257; doi:10.3390/md7020249
Received: 18 May 2009 / Revised: 11 June 2009 / Accepted: 15 June 2009 / Published: 16 June 2009
Cited by 14 | PDF Full-text (380 KB) | HTML Full-text | XML Full-text
Abstract
Seco-chaetomugilins A and D were isolated from a strain of Chaetomium globosum that was originally isolated from the marine fish Mugil cephalus, and their absolute stereostructures were elucidated on the basis of spectroscopic analyses, including 1D and 2D NMR techniques, [...] Read more.
Seco-chaetomugilins A and D were isolated from a strain of Chaetomium globosum that was originally isolated from the marine fish Mugil cephalus, and their absolute stereostructures were elucidated on the basis of spectroscopic analyses, including 1D and 2D NMR techniques, along with the chemical transformation from known chaetomugilins A and D. Seco-chaetomugilin D exhibited growth inhibitory activity against cultured P388, HL-60, L1210, and KB cells. Full article
(This article belongs to the Special Issue Synthesis around Marine Natural Products)
Open AccessArticle Expression, Purification and Bioactivities Analysis of Recombinant Active Peptide from Shark Liver
Mar. Drugs 2009, 7(2), 258-267; doi:10.3390/md7020258
Received: 20 April 2009 / Revised: 13 June 2009 / Accepted: 13 June 2009 / Published: 22 June 2009
Cited by 5 | PDF Full-text (1277 KB) | HTML Full-text | XML Full-text
Abstract
The Active Peptide from Shark Liver (APSL) was expressed in E. coli BL21 cells. The cDNA encoding APSL protein was obtained from shark regenerated hepatic tissue by RT-PCR, then it was cloned in the pET-28a expression vector. The expressed fusion protein was [...] Read more.
The Active Peptide from Shark Liver (APSL) was expressed in E. coli BL21 cells. The cDNA encoding APSL protein was obtained from shark regenerated hepatic tissue by RT-PCR, then it was cloned in the pET-28a expression vector. The expressed fusion protein was purified by Ni-IDA affinity chromatography. SDS-PAGE and HPLC analysis showed the purity of the purified fusion protein was more than 98%. The recombinant APSL (rAPSL) was tested for its biological activity both in vitro, by its ability to improve the proliferation of SMMC7721 cells, and in vivo, by its significant protective effects against acute hepatic injury induced by CCl4 and AAP (acetaminophen) in mice. In addition, the rAPSL could decrease the blood glucose concentration of mice with diabetes mellitus induced by alloxan. Paraffin sections of mouse pancreas tissues showed that rAPSL (3 mg/kg) could effectively protect mouse islets from lesions induced by alloxan, which indicated its potential application in theoretical research and industry. Full article
(This article belongs to the Special Issue Alkaloid Analogs)

Review

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Open AccessReview Advances in Marine Microbial Symbionts in the China Sea and Related Pharmaceutical Metabolites
Mar. Drugs 2009, 7(2), 113-129; doi:10.3390/md7020113
Received: 1 March 2009 / Accepted: 14 April 2009 / Published: 20 April 2009
Cited by 26 | PDF Full-text (317 KB) | HTML Full-text | XML Full-text
Abstract
Marine animals and plants such as sponges, sea squirts, corals, worms and algae host diverse and abundant symbiotic microorganisms. Marine microbial symbionts are possible the true producers or take part in the biosynthesis of some bioactive marine natural products isolated from the [...] Read more.
Marine animals and plants such as sponges, sea squirts, corals, worms and algae host diverse and abundant symbiotic microorganisms. Marine microbial symbionts are possible the true producers or take part in the biosynthesis of some bioactive marine natural products isolated from the marine organism hosts. Investigation of the pharmaceutical metabolites may reveal the biosynthesis mechanisms of related natural products and solve the current problem of supply limitation in marine drug development. This paper reviews the advances in diversity revelation, biological activity and related pharmaceutical metabolites, and functional genes of marine microbial symbionts from the China Sea. Full article
(This article belongs to the Special Issue Marine Drugs Studies in China)
Open AccessReview Marine Antimalarials
Mar. Drugs 2009, 7(2), 130-152; doi:10.3390/md7020130
Received: 7 April 2009 / Revised: 20 April 2009 / Accepted: 22 April 2009 / Published: 23 April 2009
Cited by 53 | PDF Full-text (328 KB) | HTML Full-text | XML Full-text
Abstract
Malaria is an infectious disease causing at least 1 million deaths per year, and, unfortunately, the chemical entities available to treat malaria are still too limited. In this review we highlight the contribution of marine chemistry in the field of antimalarial research [...] Read more.
Malaria is an infectious disease causing at least 1 million deaths per year, and, unfortunately, the chemical entities available to treat malaria are still too limited. In this review we highlight the contribution of marine chemistry in the field of antimalarial research by reporting the most important results obtained until the beginning of 2009, with particular emphasis on recent discoveries. About 60 secondary metabolites produced by marine organisms have been grouped into three structural types and discussed in terms of their reported antimalarial activities. The major groups of metabolites include isonitrile derivatives, alkaloids and endoperoxide derivatives. The following discussion evidences that antimalarial marine molecules can efficiently integrate the panel of lead compounds isolated from terrestrial sources with new chemical backbones and, sometimes, with unique functional groups. Full article
(This article belongs to the Special Issue Marine Anti-infective Agents)
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Open AccessReview Aplysinopsins - Marine Indole Alkaloids: Chemistry, Bioactivity and Ecological Significance
Mar. Drugs 2009, 7(2), 166-183; doi:10.3390/md7020166
Received: 6 May 2009 / Revised: 15 May 2009 / Accepted: 18 May 2009 / Published: 19 May 2009
Cited by 30 | PDF Full-text (202 KB) | HTML Full-text | XML Full-text
Abstract
Aplysinopsins are tryptophan-derived marine natural products isolated from numerous genera of sponges and scleractinian corals, as well as from one sea anemone and one nudibranch. Aplysinopsins are widely distributed in the Pacific, Indonesia, Caribbean, and Mediterranean regions. Up to date, around 30 [...] Read more.
Aplysinopsins are tryptophan-derived marine natural products isolated from numerous genera of sponges and scleractinian corals, as well as from one sea anemone and one nudibranch. Aplysinopsins are widely distributed in the Pacific, Indonesia, Caribbean, and Mediterranean regions. Up to date, around 30 analogues occurring in Nature have been reported. Natural aplysinopsins differ in the bromination pattern of the indole ring, variation in the structure of the C ring, including the number and position of N-methylation, the presence and configuration of the C-8-C-1’ double bond, and the oxidation state of the 2-aminoimidazoline fragment. Aplysinopsins can also occur in the form of dimers. This review summarizes 30 years’ research on aplysinopsins. The origin, isolation sources, chemistry, bioactivity, and ecological functions of aplysinopsins are comprehensively reviewed. Full article
Open AccessReview Antitumor Compounds from Marine Actinomycetes
Mar. Drugs 2009, 7(2), 210-248; doi:10.3390/md7020210
Received: 25 May 2009 / Revised: 8 June 2009 / Accepted: 11 June 2009 / Published: 11 June 2009
Cited by 105 | PDF Full-text (346 KB) | HTML Full-text | XML Full-text
Abstract
Chemotherapy is one of the main treatments used to combat cancer. A great number of antitumor compounds are natural products or their derivatives, mainly produced by microorganisms. In particular, actinomycetes are the producers of a large number of natural products with different [...] Read more.
Chemotherapy is one of the main treatments used to combat cancer. A great number of antitumor compounds are natural products or their derivatives, mainly produced by microorganisms. In particular, actinomycetes are the producers of a large number of natural products with different biological activities, including antitumor properties. These antitumor compounds belong to several structural classes such as anthracyclines, enediynes, indolocarbazoles, isoprenoides, macrolides, non-ribosomal peptides and others, and they exert antitumor activity by inducing apoptosis through DNA cleavage mediated by topoisomerase I or II inhibition, mitochondria permeabilization, inhibition of key enzymes involved in signal transduction like proteases, or cellular metabolism and in some cases by inhibiting tumor-induced angiogenesis. Marine organisms have attracted special attention in the last years for their ability to produce interesting pharmacological lead compounds. Full article
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Other

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Open AccessCorrection Correction: Singh, M.P., et al. Cytoskyrins and Cytosporones Produced by Cytospora sp. CR200: Taxonomy, Fermentation and Biological Activities. Mar. Drugs 2007, 5, 71-84.
Mar. Drugs 2009, 7(2), 95-96; doi:10.3390/md70200095
Received: 1 April 2009 / Published: 14 April 2009
PDF Full-text (73 KB) | HTML Full-text | XML Full-text
Abstract We found an error in Figure 1 in our paper published in the Marine Drugs [1]. The structure of Cytosporones A and B are corrected as follows: [..] Full article

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