Marine Drugs

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Open AccessReview

Recent Advances in the Synthesis of 2-Pyrones

by Jong Seok Lee

Mar. Drugs 2015, 13(3), 1581-1620; https://doi.org/10.3390/md13031581 - 23 Mar 2015

Cited by 100 | Viewed by 10642

The present review summarizes the recent progresses in the synthesis of 2-pyrones and the application to the synthesis of marine natural products. Especially, much attention was placed on the transition metal catalyzed synthetic methodologies in this review. Full article

(This article belongs to the Special Issue Synthesis around Marine Natural Products)

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Open AccessArticle

The Marine Metabolite SZ-685C Induces Apoptosis in Primary Human Nonfunctioning Pituitary Adenoma Cells by Inhibition of the Akt Pathway in Vitro

by Xin Wang, Ting Tan, Zhi-Gang Mao, Ni Lei, Zong-Ming Wang, Bin Hu, Zhi-Yong Chen, Zhi-Gang She, Yong-Hong Zhu and Hai-Jun Wang

Mar. Drugs 2015, 13(3), 1569-1580; https://doi.org/10.3390/md13031569 - 23 Mar 2015

Cited by 23 | Viewed by 6473

Abstract

Nonfunctioning pituitary adenoma (NFPA) is one of the most common types of pituitary adenoma. The marine anthraquinone derivative SZ-685C has been isolated from the secondary metabolites of the mangrove endophytic fungus Halorosellinia sp. (No. 1403) which is found in the South China Sea. [...] Read more.

Nonfunctioning pituitary adenoma (NFPA) is one of the most common types of pituitary adenoma. The marine anthraquinone derivative SZ-685C has been isolated from the secondary metabolites of the mangrove endophytic fungus Halorosellinia sp. (No. 1403) which is found in the South China Sea. Recent research has shown that SZ-685C possesses anticancer and tumor suppressive effects. The tetrazolium-based colorimetric assay (MTT assay) to investigate the different effect of the marine compound SZ-685C on the proliferation of primary human NFPA cells, rat normal pituitary cells (RPCs) and rat prolactinoma MMQ cell lines. Hoechst 33342 dye/propidium iodide (PI) double staining and fluorescein isothiocyanate-conjugated Annexin V/PI (Annexin V-FITC/PI) apoptosis assays detected an enhanced rate of apoptosis in cells treated with SZ-685C. Enhanced expression levels of caspase 3 and phosphate and tensin homolog (PTEN) were determined by Western blotting. Notably, the protein expression levels of Akt were decreased when the primary human NFPA cells were treated with SZ-685C. Here, we show that SZ-685C induces apoptosis of human NFPA cells through inhibition of the Akt pathway in vitro. The understanding of apoptosis has provided the basis for novel targeted therapies that can induce death in cancer cells or sensitize them to established cytotoxic agents and radiation therapy. Full article

(This article belongs to the Collection Marine Compounds and Cancer)

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Open AccessArticle

Kalkitoxin Inhibits Angiogenesis, Disrupts Cellular Hypoxic Signaling, and Blocks Mitochondrial Electron Transport in Tumor Cells

by J. Brian Morgan, Yang Liu, Veena Coothankandaswamy, Fakhri Mahdi, Mika B. Jekabsons, William H. Gerwick, Frederick A. Valeriote, Yu-Dong Zhou and Dale G. Nagle

Mar. Drugs 2015, 13(3), 1552-1568; https://doi.org/10.3390/md13031552 - 20 Mar 2015

Cited by 36 | Viewed by 7561

Abstract

The biologically active lipopeptide kalkitoxin was previously isolated from the marine cyanobacterium Moorea producens (Lyngbya majuscula). Kalkitoxin exhibited N-methyl-d-aspartate (NMDA)-mediated neurotoxicity and acted as an inhibitory ligand for voltage-sensitive sodium channels in cultured rat cerebellar granule neurons. Subsequent studies revealed [...] Read more.

The biologically active lipopeptide kalkitoxin was previously isolated from the marine cyanobacterium Moorea producens (Lyngbya majuscula). Kalkitoxin exhibited N-methyl-d-aspartate (NMDA)-mediated neurotoxicity and acted as an inhibitory ligand for voltage-sensitive sodium channels in cultured rat cerebellar granule neurons. Subsequent studies revealed that kalkitoxin generated a delayed form of colon tumor cell cytotoxicity in 7-day clonogenic cell survival assays. Cell line- and exposure time-dependent cytostatic/cytotoxic effects were previously observed with mitochondria-targeted inhibitors of hypoxia-inducible factor-1 (HIF-1). The transcription factor HIF-1 functions as a key regulator of oxygen homeostasis. Therefore, we investigated the ability of kalkitoxin to inhibit hypoxic signaling in human tumor cell lines. Kalkitoxin potently and selectively inhibited hypoxia-induced activation of HIF-1 in T47D breast tumor cells (IC₅₀ 5.6 nM). Mechanistic studies revealed that kalkitoxin inhibits HIF-1 activation by suppressing mitochondrial oxygen consumption at electron transport chain (ETC) complex I (NADH-ubiquinone oxidoreductase). Further studies indicate that kalkitoxin targets tumor angiogenesis by blocking the induction of angiogenic factors (i.e., VEGF) in tumor cells. Full article

(This article belongs to the Collection Marine Compounds and Cancer)

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Graphical abstract

353 KiB

Open AccessCorrection

Correction: Rasmussen, B.B., et al. Global and Phylogenetic Distribution of Quorum Sensing Signals, Acyl Homoserine Lactones, in the Family of Vibrionaceae. Mar. Drugs 2014, 12, 5527–5546

by Bastian Barker Rasmussen, Kristian Fog Nielsen, Henrique Machado, Jette Melchiorsen, Lone Gram and Eva C. Sonnenschein

Mar. Drugs 2015, 13(3), 1548-1551; https://doi.org/10.3390/md13031548 - 20 Mar 2015

Viewed by 4457

Abstract

The authors wish to make the following corrections to this paper [1]: Due to duplicated and missing data in Table 3, Page 5533, replace: [...] Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes)

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Open AccessReview

Chitin and Chitosan as Direct Compression Excipients in Pharmaceutical Applications

by Adnan A. Badwan, Iyad Rashid, Mahmoud M.H. Al Omari and Fouad H. Darras

Mar. Drugs 2015, 13(3), 1519-1547; https://doi.org/10.3390/md13031519 - 19 Mar 2015

Cited by 78 | Viewed by 12275

Abstract

Despite the numerous uses of chitin and chitosan as new functional materials of high potential in various fields, they are still behind several directly compressible excipients already dominating pharmaceutical applications. There are, however, new attempts to exploit chitin and chitosan in co-processing techniques [...] Read more.

Despite the numerous uses of chitin and chitosan as new functional materials of high potential in various fields, they are still behind several directly compressible excipients already dominating pharmaceutical applications. There are, however, new attempts to exploit chitin and chitosan in co-processing techniques that provide a product with potential to act as a direct compression (DC) excipient. This review outlines the compression properties of chitin and chitosan in the context of DC pharmaceutical applications. Full article

(This article belongs to the Special Issue Advances in Marine Chitin and Chitosan)

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Open AccessReview

Toxic Picoplanktonic Cyanobacteria—Review

by Natalia Jakubowska and Elżbieta Szeląg-Wasielewska

Mar. Drugs 2015, 13(3), 1497-1518; https://doi.org/10.3390/md13031497 - 18 Mar 2015

Cited by 78 | Viewed by 9515

Abstract

Cyanobacteria of a picoplanktonic cell size (0.2 to 2.0 µm) are common organisms of both freshwater and marine ecosystems. However, due to their small size and relatively short study history, picoplanktonic cyanobacteria, in contrast to the microplanktonic cyanobacteria, still remains a poorly studied [...] Read more.

Cyanobacteria of a picoplanktonic cell size (0.2 to 2.0 µm) are common organisms of both freshwater and marine ecosystems. However, due to their small size and relatively short study history, picoplanktonic cyanobacteria, in contrast to the microplanktonic cyanobacteria, still remains a poorly studied fraction of plankton. So far, only little information on picocyanobacteria toxicity has been reported, while the number of reports concerning their presence in ecosystems is increasing. Thus, the issue of picocyanobacteria toxicity needs more researchers’ attention and interest. In this report, we present information on the current knowledge concerning the picocyanobacteria toxicity, as well as their harmfulness and problems they can cause. Full article

(This article belongs to the Special Issue Emerging Marine Toxins)

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Open AccessArticle

Mechanistic Insight into the Elastin Degradation Process by the Metalloprotease Myroilysin from the Deep-Sea Bacterium Myroides profundi D25

by Jie Yang, Hui-Lin Zhao, Bai-Lu Tang, Xiu-Lan Chen, Hai-Nan Su, Xi-Ying Zhang, Xiao-Yan Song, Bai-Cheng Zhou, Bin-Bin Xie, Anthony S. Weiss and Yu-Zhong Zhang

Mar. Drugs 2015, 13(3), 1481-1496; https://doi.org/10.3390/md13031481 - 18 Mar 2015

Cited by 6 | Viewed by 6433

Abstract

Elastases have been widely studied because of their important uses as medicine and meat tenderizers. However, there are relatively few studies on marine elastases. Myroilysin, secreted by Myroides profundi D25 from deep-sea sediment, is a novel elastase. In this study, we examined the [...] Read more.

Elastases have been widely studied because of their important uses as medicine and meat tenderizers. However, there are relatively few studies on marine elastases. Myroilysin, secreted by Myroides profundi D25 from deep-sea sediment, is a novel elastase. In this study, we examined the elastin degradation mechanism of myroilysin. When mixed with insoluble bovine elastin, myroilysin bound hydrophobically, suggesting that this elastase may interact with the hydrophobic domains of elastin. Consistent with this, analysis of the cleavage pattern of myroilysin on bovine elastin and recombinant tropoelastin revealed that myroilysin preferentially cleaves peptide bonds with hydrophobic residues at the P1 and/or P1′ positions. Scanning electron microscopy (SEM) of cross-linked recombinant tropoelastin degraded by myroilysin showed preferential damages of spherules over cross-links, as expected for a hydrophobic preference. The degradation process of myroilysin on bovine elastin fibres was followed by light microscopy and SEM, revealing that degradation begins with the formation of crevices and cavities at the fibre surface, with these openings increasing in number and size until the fibre breaks into small pieces, which are subsequently fragmented. Our results are helpful for developing biotechnological applications for myroilysin. Full article

(This article belongs to the Special Issue Green Chemistry Approach to Marine Products)

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Open AccessArticle

Purification and Partial Characterization of a New Antitumor Protein from Tegillarca granosa

by Shuangshuang Lv, Jingjing Gao, Ting Liu, Jianhua Zhu, Jian Xu, Liyan Song, Jincai Liang and Rongmin Yu

Mar. Drugs 2015, 13(3), 1466-1480; https://doi.org/10.3390/md13031466 - 17 Mar 2015

Cited by 13 | Viewed by 6096

Abstract

A new protein, coded as D2-3, was obtained from the marine organism Tegillarca granosa L. by anion exchange and hydrophobic chromatography. The purity of D2-3 was over 99.0% as measured by RP-HPLC. Its molecular weight was shown to be 20.320 kDa by ESI-MS/MS, [...] Read more.

A new protein, coded as D2-3, was obtained from the marine organism Tegillarca granosa L. by anion exchange and hydrophobic chromatography. The purity of D2-3 was over 99.0% as measured by RP-HPLC. Its molecular weight was shown to be 20.320 kDa by ESI-MS/MS, and the isoelectric point of D2-3 was 4.70. The antitumor activity of D2-3 against four human tumor cell lines was measured by MTT assay. The conformational structure of D2-3 was further characterized by UV-vis, FT-IR and CD spectroscopy. Partial amino acid sequences of D2-3 were determined to be LMMTDVEESR, SSHMLSECRRK, KNGRNVDISHKDKG, SSDPTLMDPDDTNKDR, SSDKNTCSKTEYYTR and SSETMPYDVLDTNEMR via MALDI-TOF-MS and de novo sequencing. Full article

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Open AccessArticle

Ciona intestinalis as a Marine Model System to Study Some Key Developmental Genes Targeted by the Diatom-Derived Aldehyde Decadienal

by Anna Lettieri, Rosaria Esposito, Adrianna Ianora and Antonietta Spagnuolo

Mar. Drugs 2015, 13(3), 1451-1465; https://doi.org/10.3390/md13031451 - 17 Mar 2015

Cited by 9 | Viewed by 5648

Abstract

The anti-proliferative effects of diatoms, described for the first time in copepods, have also been demonstrated in benthic invertebrates such as polychaetes, sea urchins and tunicates. In these organisms PUAs (polyunsaturated aldehydes) induce the disruption of gametogenesis, gamete functionality, fertilization, embryonic mitosis, and [...] Read more.

The anti-proliferative effects of diatoms, described for the first time in copepods, have also been demonstrated in benthic invertebrates such as polychaetes, sea urchins and tunicates. In these organisms PUAs (polyunsaturated aldehydes) induce the disruption of gametogenesis, gamete functionality, fertilization, embryonic mitosis, and larval fitness and competence. These inhibitory effects are due to the PUAs, produced by diatoms in response to physical damage as occurs during copepod grazing. The cell targets of these compounds remain largely unknown. Here we identify some of the genes targeted by the diatom PUA 2-trans-4-trans-decadienal (DD) using the tunicate Ciona intestinalis. The tools, techniques and genomic resources available for Ciona, as well as the suitability of Ciona embryos for medium-to high-throughput strategies, are key to their employment as model organisms in different fields, including the investigation of toxic agents that could interfere with developmental processes. We demonstrate that DD can induce developmental aberrations in Ciona larvae in a dose-dependent manner. Moreover, through a preliminary analysis, DD is shown to affect the expression level of genes involved in stress response and developmental processes. Full article

(This article belongs to the Special Issue Metabolites in Diatoms)

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Open AccessArticle

A New Cyclic Hexapeptide and a New Isocoumarin Derivative from the Marine Sponge-Associated Fungus Aspergillus similanensis KUFA 0013

by Chadaporn Prompanya, Carla Fernandes, Sara Cravo, Madalena M. M. Pinto, Tida Dethoup, Artur M. S. Silva and Anake Kijjoa

Mar. Drugs 2015, 13(3), 1432-1450; https://doi.org/10.3390/md13031432 - 17 Mar 2015

Cited by 68 | Viewed by 7503

Abstract

A new isocoumarin derivative, similanpyrone C (1), a new cyclohexapeptide, similanamide (2), and a new pyripyropene derivative, named pyripyropene T (3) were isolated from the ethyl acetate extract of the culture of the marine sponge-associated fungus Aspergillus [...] Read more.

A new isocoumarin derivative, similanpyrone C (1), a new cyclohexapeptide, similanamide (2), and a new pyripyropene derivative, named pyripyropene T (3) were isolated from the ethyl acetate extract of the culture of the marine sponge-associated fungus Aspergillus similanensis KUFA 0013. The structures of the compounds were established based on 1D and 2D NMR spectral analysis, and in the case of compound 2 the stereochemistry of its amino acid constituents was determined by chiral HPLC analysis of the hydrolysate by co-injection with the d and l amino acids standards. Compounds 2 and 3 were evaluated for their in vitro growth inhibitory activity against MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer) and A373 (melanoma) cell lines, as well as antibacterial activity against reference strains and the environmental multidrug-resistant isolates (MRS and VRE). Only compound 2 exhibited weak activity against the three cancer cell lines, and neither of them showed antibacterial activity. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)

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Open AccessCommunication

Solvent Separating Secondary Metabolites Directly from Biosynthetic Tissue for Surface-Assisted Laser Desorption Ionisation Mass Spectrometry

by David Rudd, Kirsten Benkendorff and Nicolas H. Voelcker

Mar. Drugs 2015, 13(3), 1410-1431; https://doi.org/10.3390/md13031410 - 16 Mar 2015

Cited by 10 | Viewed by 6159

Abstract

Marine bioactive metabolites are often heterogeneously expressed in tissues both spatially and over time. Therefore, traditional solvent extraction methods benefit from an understanding of the in situ sites of biosynthesis and storage to deal with heterogeneity and maximize yield. Recently, surface-assisted mass spectrometry [...] Read more.

Marine bioactive metabolites are often heterogeneously expressed in tissues both spatially and over time. Therefore, traditional solvent extraction methods benefit from an understanding of the in situ sites of biosynthesis and storage to deal with heterogeneity and maximize yield. Recently, surface-assisted mass spectrometry (MS) methods namely nanostructure-assisted laser desorption ionisation (NALDI) and desorption ionisation on porous silicon (DIOS) surfaces have been developed to enable the direct detection of low molecular weight metabolites. Since direct tissue NALDI-MS or DIOS-MS produce complex spectra due to the wide variety of other metabolites and fragments present in the low mass range, we report here the use of “on surface” solvent separation directly from mollusc tissue onto nanostructured surfaces for MS analysis, as a mechanism for simplifying data annotation and detecting possible artefacts from compound delocalization during the preparative steps. Water, ethanol, chloroform and hexane selectively extracted a range of choline esters, brominated indoles and lipids from Dicathais orbita hypobranchial tissue imprints. These compounds could be quantified on the nanostructured surfaces by comparison to standard curves generated from the pure compounds. Surface-assisted MS could have broad utility for detecting a broad range of secondary metabolites in complex marine tissue samples. Full article

(This article belongs to the Special Issue Marine Natural Products - Advances in Separation, Characterisation and Chemical Profiling Methodologies)

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Open AccessArticle

New Antimicrobial Bromotyrosine Analogues from the Sponge Pseudoceratina purpurea and Its Predator Tylodina corticalis

by Michael P. Gotsbacher and Peter Karuso

Mar. Drugs 2015, 13(3), 1389-1409; https://doi.org/10.3390/md13031389 - 16 Mar 2015

Cited by 28 | Viewed by 5979

Abstract

Bioassay-guided fractionation of extracts from temperate Australian collections of the marine sponge Pseudoceratina purpurea resulted in the isolation and characterisation of two new and six known bromotyrosine-derived alkaloids with antibiotic activity. Surprisingly, a single specimen of the mollusc Tylodina corticalis, which was [...] Read more.

Bioassay-guided fractionation of extracts from temperate Australian collections of the marine sponge Pseudoceratina purpurea resulted in the isolation and characterisation of two new and six known bromotyrosine-derived alkaloids with antibiotic activity. Surprisingly, a single specimen of the mollusc Tylodina corticalis, which was collected while feeding on P. purpurea, contained only a few of the compounds found in the sponge suggesting selective accumulation and chemical modification of sponge metabolites. Full article

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Open AccessArticle

Astaxanthin Protects Steroidogenesis from Hydrogen Peroxide-Induced Oxidative Stress in Mouse Leydig Cells

by Jyun-Yuan Wang, Yue-Jia Lee, Mei-Chia Chou, Renin Chang, Chih-Hsien Chiu, Yao-Jen Liang and Leang-Shin Wu

Mar. Drugs 2015, 13(3), 1375-1388; https://doi.org/10.3390/md13031375 - 16 Mar 2015

Cited by 43 | Viewed by 7814

Abstract

Androgens, especially testosterone produced in Leydig cells, play an essential role in development of the male reproductive phenotype and fertility. However, testicular oxidative stress may cause a decline in testosterone production. Many antioxidants have been used as reactive oxygen species (ROS) scavengers to [...] Read more.

Androgens, especially testosterone produced in Leydig cells, play an essential role in development of the male reproductive phenotype and fertility. However, testicular oxidative stress may cause a decline in testosterone production. Many antioxidants have been used as reactive oxygen species (ROS) scavengers to eliminate oxidative stress to protect steroidogenesis. Astaxanthin (AST), a natural extract from algae and plants ubiquitous in the marine environment, has been shown to have antioxidant activity in many previous studies. In this study, we treated primary mouse Leydig cells or MA-10 cells with hydrogen peroxide (H₂O₂) to cause oxidative stress. Testosterone and progesterone production was suppressed and the expression of the mature (30 kDa) form of StAR protein was down-regulated in MA-10 cells by H₂O₂ and cAMP co-treatment. However, progesterone production and expression of mature StAR protein were restored in MA-10 cells by a one-hour pretreatment with AST. AST also reduced ROS levels in cells so that they were lower than the levels in untreated controls. These results provide additional evidence of the potential health benefits of AST as a potential food additive to ease oxidative stress. Full article

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Open AccessArticle

Structural Analysis and Anti-Complement Activity of Polysaccharides from Kjellmaniella crsaaifolia

by Wenjing Zhang, Weihua Jin, Delin Sun, Luyu Zhao, Jing Wang, Delin Duan and Quanbin Zhang

Mar. Drugs 2015, 13(3), 1360-1374; https://doi.org/10.3390/md13031360 - 16 Mar 2015

Cited by 16 | Viewed by 6233

Abstract

Two polysaccharides, named KCA and KCW, were extracted from Kjellmaniella crassifolia using dilute hydrochloric acid and water, respectively. Composition analysis showed that these polysaccharides predominantly consisted of fucose, with galactose, mannose and glucuronic acid as minor components. After degradation and partial desulfation, electrospray [...] Read more.

Two polysaccharides, named KCA and KCW, were extracted from Kjellmaniella crassifolia using dilute hydrochloric acid and water, respectively. Composition analysis showed that these polysaccharides predominantly consisted of fucose, with galactose, mannose and glucuronic acid as minor components. After degradation and partial desulfation, electrospray ionization mass spectrometry (ESI-MS) was performed, which showed that the polysaccharides consisted of sulfated fucooligosaccharides, sulfated galactofucooligosaccharides and methyl glycosides of mono-sulfated/multi-sulfated fucooligosaccharides. The structures of the oligomeric fragments were further characterized by electrospray ionization collision-induced dissociation tandem mass spectrometry (ESI-CID-MS² and ESI-CID-MS³). Moreover, the activity of KCA and KCW against the hemolytic activity of both the classical and alternative complement pathways was determined. The activity of KCA was found to be similar to KCW, suggesting that the method of extraction did not influence the activity. In addition, the degraded polysaccharides (DKCA and DKCW) displayed lower activity levels than the crude polysaccharides (KCA and KCW), indicating that molecular weight had an effect on activity. Moreover, the desulfated fractions (ds-DKCA and ds-DKCW) showed less or no activity, which confirmed that sulfate was important for activity. In conclusion, polysaccharides from K. crassifolia may be good candidates for the treatment of diseases involving the complement pathway. Full article

(This article belongs to the Collection Marine Polysaccharides)

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Open AccessArticle

The Anticancer Effect of (1S,2S,3E,7E,11E)-3,7,11, 15-Cembratetraen-17,2-olide(LS-1) through the Activation of TGF-β Signaling in SNU-C5/5-FU, Fluorouracil-Resistant Human Colon Cancer Cells

by Eun-Ji Kim, Jung-Il Kang, Jeon-Won Kwak, Chan-Hee Jeon, Nguyen-Huu Tung, Young-Ho Kim, Cheol-Hee Choi, Jin-Won Hyun, Young-Sang Koh, Eun-Sook Yoo and Hee-Kyoung Kang

Mar. Drugs 2015, 13(3), 1340-1359; https://doi.org/10.3390/md13031340 - 16 Mar 2015

Cited by 10 | Viewed by 7557

Abstract

The anticancer effect of (1S,2S,3E,7E,11E)-3,7,11,15-cembratetraen-17,2-olide (LS-1) from Lobophytum sp. has been already reported in HT-29 human colorectal cancer cells. In this study, we examined the effect of LS-1 on the apoptosis induction of [...] Read more.

The anticancer effect of (1S,2S,3E,7E,11E)-3,7,11,15-cembratetraen-17,2-olide (LS-1) from Lobophytum sp. has been already reported in HT-29 human colorectal cancer cells. In this study, we examined the effect of LS-1 on the apoptosis induction of SNU-C5/5-FU, fluorouracil-resistant human colon cancer cells. Furthermore, we investigated whether the apoptosis-induction effect of LS-1 could arise from the activation of the TGF-β pathway. In SNU-C5/5-FU treated with LS-1 of 7.1 μM (IC₅₀), we could observe the various apoptotic characteristics, such as the increase of apoptotic bodies, the increase of the sub-G1 hypodiploid cell population, the decrease of the Bcl-2 level, the increase of procaspase-9 cleavage, the increase of procaspase-3 cleavage and the increase of poly(ADP-ribose) polymerase cleavage. Interestingly, the apoptosis-induction effect of LS-1 was also accompanied by the increase of Smad-3 phosphorylation and the downregulation of c-Myc in SNU-C5/5-FU. LS-1 also increased the nuclear localization of phospho-Smad-3 and Smad-4. We examined whether LS-1 could downregulate the expression of carcinoembryonic antigen (CEA), a direct inhibitor of TGF-β signaling. LS-1 decreased the CEA level, as well as the direct interaction between CEA and TGF-βR1 in the apoptosis-induction condition of SNU-C5/5-FU. To examine whether LS-1 can induce apoptosis via the activation of TGF-β signaling, the SNU-C5/5-FU cells were treated with LS-1 in the presence or absence of SB525334, a TGF-βRI kinase inhibitor. SB525334 inhibited the effect of LS-1 on the apoptosis induction. These findings provide evidence demonstrating that the apoptosis-induction effect of LS-1 results from the activation of the TGF-β pathway via the downregulation of CEA in SNU-C5/5-FU. Full article

(This article belongs to the Collection Marine Compounds and Cancer)

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Open AccessArticle

Inventory of Fatty Acid Desaturases in the Pennate Diatom Phaeodactylum tricornutum

by Lina-Juana Dolch and Eric Maréchal

Mar. Drugs 2015, 13(3), 1317-1339; https://doi.org/10.3390/md13031317 - 16 Mar 2015

Cited by 57 | Viewed by 7874 | Correction

Abstract

The diatom Phaeodactylum is rich in very long chain polyunsaturated fatty acids (PUFAs). Fatty acid (FA) synthesis, elongation, and desaturation have been studied in depth in plants including Arabidopsis, but for secondary endosymbionts the full picture remains unclear. FAs are synthesized up [...] Read more.

The diatom Phaeodactylum is rich in very long chain polyunsaturated fatty acids (PUFAs). Fatty acid (FA) synthesis, elongation, and desaturation have been studied in depth in plants including Arabidopsis, but for secondary endosymbionts the full picture remains unclear. FAs are synthesized up to a chain length of 18 carbons inside chloroplasts, where they can be incorporated into glycerolipids. They are also exported to the ER for phospho- and betaine lipid syntheses. Elongation of FAs up to 22 carbons occurs in the ER. PUFAs can be reimported into plastids to serve as precursors for glycerolipids. In both organelles, FA desaturases are present, introducing double bonds between carbon atoms and giving rise to a variety of molecular species. In addition to the four desaturases characterized in Phaeodactylum (FAD2, FAD6, PtD5, PtD6), we identified eight putative desaturase genes. Combining subcellular localization predictions and comparisons with desaturases from other organisms like Arabidopsis, we propose a scheme at the whole cell level, including features that are likely specific to secondary endosymbionts. Full article

(This article belongs to the Special Issue Metabolites in Diatoms)

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Open AccessArticle

Cytotoxic and Antibacterial Angucycline- and Prodigiosin- Analogues from the Deep-Sea Derived Streptomyces sp. SCSIO 11594

by Yongxiang Song, Guangfu Liu, Jie Li, Hongbo Huang, Xing Zhang, Hua Zhang and Jianhua Ju

Mar. Drugs 2015, 13(3), 1304-1316; https://doi.org/10.3390/md13031304 - 16 Mar 2015

Cited by 66 | Viewed by 8273

Abstract

Two new C-glycoside angucyclines, marangucycline A (1) and marangucycline B (2), along with three known compounds, dehydroxyaquayamycin (3), undecylprodigiosin (4) and metacycloprodigiosin (5), have been identified as products of the deep-sea sediment strain [...] Read more.

Two new C-glycoside angucyclines, marangucycline A (1) and marangucycline B (2), along with three known compounds, dehydroxyaquayamycin (3), undecylprodigiosin (4) and metacycloprodigiosin (5), have been identified as products of the deep-sea sediment strain Streptomyces sp. SCSIO 11594. New structures were elucidated on the basis of HRESIMS, 1D and 2D NMR analyses and comparisons to previously reported datasets. Compounds 2 and 4 displayed in vitro cytotoxicity against four cancer cell lines A594, CNE2, HepG2, MCF-7 superior to those obtained with cisplatin, the positive control. Notably, compound 2 bearing a keto-sugar displayed significant cytotoxicity against cancer cell lines with IC₅₀ values ranging from 0.24 to 0.56 μM; An IC₅₀ value of 3.67 μM was found when using non-cancerous hepatic cell line HL7702, demonstrating the cancer cell selectivity of 2. Compounds 1–3 were proved to have weak antibacterial activities against Enterococcus faecalis ATCC29212 with an MIC value of 64.0 μg/mL. Moreover, 3 displayed selective antibacterial activity against methicillin-resistant Staphylococcus epidermidis shhs-E1 with an MIC value of 16.0 μg/mL. Full article

(This article belongs to the Collection Marine Compounds and Cancer)

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Open AccessArticle

Lumazine Peptides from the Marine-Derived Fungus Aspergillus terreus

by Minjung You, Lijuan Liao, Soo Hyun Hong, Wanki Park, Dah In Kwon, Jeeyeon Lee, Minsoo Noh, Dong-Chan Oh, Ki-Bong Oh and Jongheon Shin

Mar. Drugs 2015, 13(3), 1290-1303; https://doi.org/10.3390/md13031290 - 12 Mar 2015

Cited by 36 | Viewed by 7241

Abstract

Terrelumamides A (1) and B (2), two new lumazine-containing peptides, were isolated from the culture broth of the marine-derived fungus Aspergillus terreus. From the results of combined spectroscopic and chemical analyses, the structures of these compounds were determined [...] Read more.

Terrelumamides A (1) and B (2), two new lumazine-containing peptides, were isolated from the culture broth of the marine-derived fungus Aspergillus terreus. From the results of combined spectroscopic and chemical analyses, the structures of these compounds were determined to be linear assemblies of 1-methyllumazine-6-carboxylic acid, an amino acid residue and anthranilic acid methyl ester connected by peptide bonds. These new compounds exhibited pharmacological activity by improving insulin sensitivity, which was evaluated in an adipogenesis model using human bone marrow mesenchymal stem cells. In addition, the compounds exhibited fluorescence changes upon binding to DNA, demonstrating their potential applications to DNA sequence recognition. Full article

(This article belongs to the Special Issue Marine Peptides and Their Mimetics)

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Open AccessArticle

Acetylated Chitosan Oligosaccharides Act as Antagonists against Glutamate-Induced PC12 Cell Death via Bcl-2/Bax Signal Pathway

by Cui Hao, Lixia Gao, Yiran Zhang, Wei Wang, Guangli Yu, Huashi Guan, Lijuan Zhang and Chunxia Li

Mar. Drugs 2015, 13(3), 1267-1289; https://doi.org/10.3390/md13031267 - 12 Mar 2015

Cited by 39 | Viewed by 8699

Abstract

Chitosan oligosaccharides (COSs), depolymerized products of chitosan composed of β-(1→4) d-glucosamine units, have broad range of biological activities such as antitumour, antifungal, and antioxidant activities. In this study, peracetylated chitosan oligosaccharides (PACOs) and N-acetylated chitosan oligosaccharides (NACOs) were prepared from the COSs [...] Read more.

Chitosan oligosaccharides (COSs), depolymerized products of chitosan composed of β-(1→4) d-glucosamine units, have broad range of biological activities such as antitumour, antifungal, and antioxidant activities. In this study, peracetylated chitosan oligosaccharides (PACOs) and N-acetylated chitosan oligosaccharides (NACOs) were prepared from the COSs by chemcal modification. The structures of these monomers were identified using NMR and ESI-MS spectra. Their antagonist effects against glutamate-induced PC12 cell death were investigated. The results showed that pretreatment of PC12 cells with the PACOs markedly inhibited glutamate-induced cell death in a concentration-dependent manner. The PACOs were better glutamate antagonists compared to the COSs and the NACOs, suggesting the peracetylation is essential for the neuroprotective effects of chitosan oligosaccharides. In addition, the PACOs pretreatment significantly reduced lactate dehydrogenase release and reactive oxygen species production. It also attenuated the loss of mitochondrial membrane potential. Further studies indicated that the PACOs inhibited glutamate-induced cell death by preventing apoptosis through depressing the elevation of Bax/Bcl-2 ratio and caspase-3 activation. These results suggest that PACOs might be promising antagonists against glutamate-induced neural cell death. Full article

(This article belongs to the Collection Marine Polysaccharides)

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Open AccessArticle

6-Bromohypaphorine from Marine Nudibranch Mollusk Hermissenda crassicornis is an Agonist of Human α7 Nicotinic Acetylcholine Receptor

by Igor E. Kasheverov, Irina V. Shelukhina, Denis S. Kudryavtsev, Tatyana N. Makarieva, Ekaterina N. Spirova, Alla G. Guzii, Valentin A. Stonik and Victor I. Tsetlin

Mar. Drugs 2015, 13(3), 1255-1266; https://doi.org/10.3390/md13031255 - 12 Mar 2015

Cited by 24 | Viewed by 7609

Abstract

6-Bromohypaphorine (6-BHP) has been isolated from the marine sponges Pachymatisma johnstoni, Aplysina sp., and the tunicate Aplidium conicum, but data on its biological activity were not available. For the nudibranch mollusk Hermissenda crassicornis no endogenous compounds were known, and [...] Read more.

6-Bromohypaphorine (6-BHP) has been isolated from the marine sponges Pachymatisma johnstoni, Aplysina sp., and the tunicate Aplidium conicum, but data on its biological activity were not available. For the nudibranch mollusk Hermissenda crassicornis no endogenous compounds were known, and here we describe the isolation of 6-BHP from this mollusk and its effects on different nicotinic acetylcholine receptors (nAChR). Two-electrode voltage-clamp experiments on the chimeric α7 nAChR (built of chicken α7 ligand-binding and glycine receptor transmembrane domains) or on rat α4β2 nAChR expressed in Xenopus oocytes revealed no action of 6-BHP. However, in radioligand analysis, 6-BHP competed with radioiodinated α-bungarotoxin for binding to human α7 nAChR expressed in GH₄C₁ cells (IC₅₀ 23 ± 1 μM), but showed no competition on muscle-type nAChR from Torpedo californica. In Ca²⁺-imaging experiments on the human α7 nAChR expressed in the Neuro2a cells, 6-BHP in the presence of PNU120596 behaved as an agonist (EC₅₀ ~80 μM). To the best of our knowledge, 6-BHP is the first low-molecular weight compound from marine source which is an agonist of the nAChR subtype. This may have physiological importance because H. crassicornis, with its simple and tractable nervous system, is a convenient model system for studying the learning and memory processes. Full article

(This article belongs to the Special Issue Emerging Marine Toxins)

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Open AccessReview

Potential Threats Posed by New or Emerging Marine Biotoxins in UK Waters and Examination of Detection Methodology Used in Their Control: Brevetoxins

by Andrew D. Turner, Cowan Higgins, Keith Davidson, Andrea Veszelovszki, Daniel Payne, James Hungerford and Wendy Higman

Mar. Drugs 2015, 13(3), 1224-1254; https://doi.org/10.3390/md13031224 - 12 Mar 2015

Cited by 37 | Viewed by 8206

Abstract

Regular occurrence of brevetoxin-producing toxic phytoplankton in commercial shellfishery areas poses a significant risk to shellfish consumer health. Brevetoxins and their causative toxic phytoplankton are more limited in their global distribution than most marine toxins impacting commercial shellfisheries. On the other hand, trends [...] Read more.

Regular occurrence of brevetoxin-producing toxic phytoplankton in commercial shellfishery areas poses a significant risk to shellfish consumer health. Brevetoxins and their causative toxic phytoplankton are more limited in their global distribution than most marine toxins impacting commercial shellfisheries. On the other hand, trends in climate change could conceivably lead to increased risk posed by these toxins in UK waters. A request was made by UK food safety authorities to examine these toxins more closely to aid possible management strategies, should they pose a threat in the future. At the time of writing, brevetoxins have been detected in the Gulf of Mexico, the Southeast US coast and in New Zealand waters, where regulatory levels for brevetoxins in shellfish have existed for some time. This paper reviews evidence concerning the prevalence of brevetoxins and brevetoxin-producing phytoplankton in the UK, together with testing methodologies. Chemical, biological and biomolecular methods are reviewed, including recommendations for further work to enable effective testing. Although the focus here is on the UK, from a strategic standpoint many of the topics discussed will also be of interest in other parts of the world since new and emerging marine biotoxins are of global concern. Full article

(This article belongs to the Special Issue Emerging Marine Toxins)

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Open AccessReview

Anticancer Activity of Sea Cucumber Triterpene Glycosides

by Dmitry L. Aminin, Ekaterina S. Menchinskaya, Evgeny A. Pisliagin, Alexandra S. Silchenko, Sergey A. Avilov and Vladimir I. Kalinin

Mar. Drugs 2015, 13(3), 1202-1223; https://doi.org/10.3390/md13031202 - 06 Mar 2015

Cited by 119 | Viewed by 13007

Abstract

Triterpene glycosides are characteristic secondary metabolites of sea cucumbers (Holothurioidea, Echinodermata). They have hemolytic, cytotoxic, antifungal, and other biological activities caused by membranotropic action. These natural products suppress the proliferation of various human tumor cell lines in vitro and, more [...] Read more.

Triterpene glycosides are characteristic secondary metabolites of sea cucumbers (Holothurioidea, Echinodermata). They have hemolytic, cytotoxic, antifungal, and other biological activities caused by membranotropic action. These natural products suppress the proliferation of various human tumor cell lines in vitro and, more importantly, intraperitoneal administration in rodents of solutions of some sea cucumber triterpene glycosides significantly reduces both tumor burden and metastasis. The anticancer molecular mechanisms include the induction of tumor cell apoptosis through the activation of intracellular caspase cell death pathways, arrest of the cell cycle at S or G2/M phases, influence on nuclear factors, NF-κB, and up-down regulation of certain cellular receptors and enzymes participating in cancerogenesis, such as EGFR (epidermal growth factor receptor), Akt (protein kinase B), ERK (extracellular signal-regulated kinases), FAK (focal adhesion kinase), MMP-9 (matrix metalloproteinase-9) and others. Administration of some glycosides leads to a reduction of cancer cell adhesion, suppression of cell migration and tube formation in those cells, suppression of angiogenesis, inhibition of cell proliferation, colony formation and tumor invasion. As a result, marked growth inhibition of tumors occurs in vitro and in vivo. Some holothurian triterpene glycosides have the potential to be used as P-gp mediated MDR reversal agents in combined therapy with standard cytostatics. Full article

(This article belongs to the Collection Marine Compounds and Cancer)

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Open AccessArticle

Biotransfer of β-N-Methylamino-l-alanine (BMAA) in a Eutrophicated Freshwater Lake

by Sandra Lage, Heléne Annadotter, Ulla Rasmussen and Sara Rydberg

Mar. Drugs 2015, 13(3), 1185-1201; https://doi.org/10.3390/md13031185 - 02 Mar 2015

Cited by 46 | Viewed by 7480

Abstract

β-N-Methylamino-l-alanine (BMAA), a neurotoxic non-protein amino acid, plays a significant role as an environmental risk factor in neurodegenerative diseases, such as amyotrophic lateral sclerosis. BMAA producers occur globally, colonizing almost all habitats and represent species from distinct phytoplanktonic groups, i.e., [...] Read more.

β-N-Methylamino-l-alanine (BMAA), a neurotoxic non-protein amino acid, plays a significant role as an environmental risk factor in neurodegenerative diseases, such as amyotrophic lateral sclerosis. BMAA producers occur globally, colonizing almost all habitats and represent species from distinct phytoplanktonic groups, i.e., cyanobacteria, diatoms, and dinoflagellates. Bioaccumulation of BMAA in invertebrate and vertebrate organisms has also been registered around the globe. In the Baltic Sea, BMAA has been detected in several commercial fish species, raising the question of the bioaccumulation of BMAA in Swedish limnic systems. Here we find the presence of BMAA in water samples from Lake Finjasjön and identify its bioaccumulation patterns in both plankti-benthivorous and piscivorous fish, according to fish species, total weight, gender, and season of collection. For the first time, a large number of fish individuals were used in order to draw conclusions on BMAA bioaccumulation in a closed ecological community based on a statistical approach. We may, therefore, conclude that feeding patterns (plankti-benthivorous) and increased age of fish may lead to a higher tissue concentration of BMAA. Full article

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Open AccessReview

Emergence and Epidemiology of Ciguatera in the Coastal Cities of Southern China

by Thomas Y. K. Chan

Mar. Drugs 2015, 13(3), 1175-1184; https://doi.org/10.3390/md13031175 - 02 Mar 2015

Cited by 14 | Viewed by 7203

Abstract

In the present review of 23 published case studies, the main objective is to report the emergence and epidemiology of ciguatera in the coastal cities of southern China. There was a sudden surge in ciguatera outbreaks in 2004. Ciguatera mostly occurred in the [...] Read more.

In the present review of 23 published case studies, the main objective is to report the emergence and epidemiology of ciguatera in the coastal cities of southern China. There was a sudden surge in ciguatera outbreaks in 2004. Ciguatera mostly occurred in the Guangdong Province. In Shenzhen, the incidence of ciguatera in 2004 was estimated to be over 7.5 per million people. In Foshan and Zhongshan, three large outbreaks each affecting over 100–200 subjects (caused by tiger grouper served at banquets) accounted for the much higher incidence of ciguatera in 2004 (>48.7 and >129.9 per million people). Humphead wrasse and areolated coral grouper were the other important ciguatoxic fish. In some subjects, risk factors for increased likelihood of (severe) ciguatera were present, namely concomitant alcohol consumption and ingestion of large reef fishes and CTX-rich fish parts. To prevent large outbreaks and severe illness, large apex predators from coral reefs should never be served at banquets and the public should realize the increased risk of severe symptoms due to ingestion of CTX-rich fish parts with alcohol. The systematic collection of accurate details, implementation of risk assessment process and continuing education for the public on prevention are of obvious importance. Full article

(This article belongs to the Special Issue Emerging Marine Toxins)

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Chitin and Chitosan Preparation from Marine Sources. Structure, Properties and Applications

by Islem Younes and Marguerite Rinaudo

Mar. Drugs 2015, 13(3), 1133-1174; https://doi.org/10.3390/md13031133 - 02 Mar 2015

Cited by 1673 | Viewed by 56083

Abstract

This review describes the most common methods for recovery of chitin from marine organisms. In depth, both enzymatic and chemical treatments for the step of deproteinization are compared, as well as different conditions for demineralization. The conditions of chitosan preparation are also discussed, [...] Read more.

This review describes the most common methods for recovery of chitin from marine organisms. In depth, both enzymatic and chemical treatments for the step of deproteinization are compared, as well as different conditions for demineralization. The conditions of chitosan preparation are also discussed, since they significantly impact the synthesis of chitosan with varying degree of acetylation (DA) and molecular weight (MW). In addition, the main characterization techniques applied for chitin and chitosan are recalled, pointing out the role of their solubility in relation with the chemical structure (mainly the acetyl group distribution along the backbone). Biological activities are also presented, such as: antibacterial, antifungal, antitumor and antioxidant. Interestingly, the relationship between chemical structure and biological activity is demonstrated for chitosan molecules with different DA and MW and homogeneous distribution of acetyl groups for the first time. In the end, several selected pharmaceutical and biomedical applications are presented, in which chitin and chitosan are recognized as new biomaterials taking advantage of their biocompatibility and biodegradability. Full article

(This article belongs to the Special Issue Advances in Marine Chitin and Chitosan)

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Open AccessArticle

Bioactive Isopimarane Diterpenes from the Fungus, Epicoccum sp. HS-1, Associated with Apostichopus japonicus

by Xuekui Xia, Jun Qi, Yayue Liu, Airong Jia, Yonggang Zhang, Changheng Liu, Cuiling Gao and Zhigang She

Mar. Drugs 2015, 13(3), 1124-1132; https://doi.org/10.3390/md13031124 - 02 Mar 2015

Cited by 23 | Viewed by 6387

Abstract

One new isopimarane diterpene (1), together with two known compounds, 11-deoxydiaporthein A (2) and iso-pimara-8(14),15-diene (3) were isolated from the culture of Epicoccum sp., which was associated with Apostichopus japonicus. Their structures were determined by the analysis [...] Read more.

One new isopimarane diterpene (1), together with two known compounds, 11-deoxydiaporthein A (2) and iso-pimara-8(14),15-diene (3) were isolated from the culture of Epicoccum sp., which was associated with Apostichopus japonicus. Their structures were determined by the analysis of 1D and 2D NMR, as well as mass spectroscopic data. The absolute configuration of Compound 1 was deduced by a single-crystal X-ray diffraction experiment using CuKα radiation. In the bioactivity assay, both Compounds 1 and 2 exhibited α-glucosidase inhibitory activity with IC₅₀ values of 4.6 ± 0.1 and 11.9 ± 0.4 μM, respectively. This was the first report on isopimarane diterpenes with α-glucosidase inhibitory activity. Full article

(This article belongs to the Special Issue Bioactive Compounds from Marine Microbes)

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Anticancer Properties of Lamellarins

by Christian Bailly

Mar. Drugs 2015, 13(3), 1105-1123; https://doi.org/10.3390/md13031105 - 19 Feb 2015

Cited by 141 | Viewed by 8750

Abstract

In 1985 the first lamellarins were isolated from a small oceanic sea snail. Today, more than 50 lamellarins have been inventoried and numerous derivatives synthesized and tested as antiviral or anticancer agents. The lead compound in the family is lamellarin D, characterized as [...] Read more.

In 1985 the first lamellarins were isolated from a small oceanic sea snail. Today, more than 50 lamellarins have been inventoried and numerous derivatives synthesized and tested as antiviral or anticancer agents. The lead compound in the family is lamellarin D, characterized as a potent inhibitor of both nuclear and mitochondrial topoisomerase I but also capable of directly interfering with mitochondria to trigger cancer cell death. The pharmacology and chemistry of lamellarins are discussed here and the mechanistic portrait of lamellarin D is detailed. Lamellarins frequently serve as a starting point in the design of anticancer compounds. Extensive efforts have been devoted to create novel structures as well as to improve synthetic methods, leading to lamellarins and related pyrrole-derived marine alkaloids. Full article

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Open AccessArticle

Fucoidan from Macrocystis pyrifera Has Powerful Immune-Modulatory Effects Compared to Three Other Fucoidans

by Wei Zhang, Tatsuya Oda, Qing Yu and Jun-O Jin

Mar. Drugs 2015, 13(3), 1084-1104; https://doi.org/10.3390/md13031084 - 19 Feb 2015

Cited by 143 | Viewed by 11079

Abstract

Fucoidan, a sulfated polysaccharide purified from brown algae, has a variety of immune-modulation effects, such as promoting activation of dendritic cells (DCs), natural killer (NK) cells and T cells, and enhancing anti-viral and anti-tumor responses. However, the immune-modulatory effect of fucoidan from different [...] Read more.

Fucoidan, a sulfated polysaccharide purified from brown algae, has a variety of immune-modulation effects, such as promoting activation of dendritic cells (DCs), natural killer (NK) cells and T cells, and enhancing anti-viral and anti-tumor responses. However, the immune-modulatory effect of fucoidan from different seaweed extracts has not been thoroughly analyzed and compared. We analyzed fucoidans obtained from Ascophyllum nodosum (A. nodosum), Macrocystis pyrifera (M. pyrifera), Undaria pinnatifida (U. pinnatifida) and Fucus vesiculosus (F. vesiculosus) for their effect on the apoptosis of human neutrophils, activation of mouse NK cells, maturation of spleen DCs, proliferation and activation of T cells, and the adjuvant effect in vivo. Fucoidans from M. pyrifera and U. pinnatifida strongly delayed human neutrophil apoptosis at low concentration, whereas fucoidans from A. nodosum and F. vesiculosus delayed human neutrophil apoptosis at higher concentration. Moreover, fucoidan from M. pyrifera promoted NK cell activation and cytotoxic activity against YAC-1 cells. In addition, M. pyrifera fucoidan induced the strongest activation of spleen DCs and T cells and ovalbumin (OVA) specific immune responses compared to other fucoidans. These data suggest that fucoidan from M. pyrifera can be potentially useful as a therapeutic agent for infectious diseases, cancer and an effective adjuvant for vaccine. Full article

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Mar. Drugs, Volume 13, Issue 3 (March 2015) – 28 articles , Pages 1084-1620

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