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Marine Drugs
Volume 18
Issue 12
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Mar. Drugs, Volume 18, Issue 12 (December 2020) – 78 articles

Cover Story (view full-size image): The extract of a Pseudosuberites sp. sponge provided three new aryl alkaloids named suberitamides A–C. Assignment of the relative configuration of the four contiguous stereogenic centers in the conformationally flexible oxolane ring in suberitamide A was accomplished using a variety of contemporary NMR techniques. These included J-based methodologies that employed new NMR experiments for the accurate determination of heteronuclear coupling constants between protons and nonprotonated carbons. The ubiquitin ligase Cbl-b is an attractive potential target for immune system modulation, and suberitamides A and B inhibited autoubiquitination of Cbl-b at low micromolar concentrations. View this paper.
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21 pages, 3155 KiB  
Article
Targeted Isolation of Anti-Trypanosomal Naphthofuran-Quinone Compounds from the Mangrove Plant Avicennia lanata
by Noor Wini Mazlan, Carol Clements and RuAngelie Edrada-Ebel
Mar. Drugs 2020, 18(12), 661; https://doi.org/10.3390/md18120661 - 21 Dec 2020
Cited by 7 | Viewed by 3959
Abstract
The discovery of new secondary metabolites from natural origins has become more challenging in natural products research. Different approaches have been applied to target the isolation of new bioactive metabolites from plant extracts. In this study, bioactive natural products were isolated from the [...] Read more.
The discovery of new secondary metabolites from natural origins has become more challenging in natural products research. Different approaches have been applied to target the isolation of new bioactive metabolites from plant extracts. In this study, bioactive natural products were isolated from the crude organic extract of the mangrove plant Avicennia lanata collected from the east coast of Peninsular Malaysia in the Setiu Wetlands, Terengganu, using HRESI-LCMS-based metabolomics-guided isolation and fractionation. Isolation work on the crude extract A. lanata used high-throughput chromatographic techniques to give two new naphthofuranquinone derivatives, hydroxyavicenol C (1) and glycosemiquinone (2), along with the known compounds avicenol C (3), avicequinone C (4), glycoquinone (5), taraxerone (6), taraxerol (7), β-sitosterol (8) and stigmasterol (9). The elucidation and identification of the targeted bioactive compounds used 1D and 2D-NMR and mass spectrometry. Except for 6–9, all isolated naphthoquinone compounds (1–5) from the mangrove plant A. lanata showed significant anti-trypanosomal activity on Trypanosoma brucei brucei with MIC values of 3.12–12.5 μM. Preliminary cytotoxicity screening against normal prostate cells (PNT2A) was also performed. All compounds exhibited low cytotoxicity, with compounds 3 and 4 showing moderate cytotoxicity of 78.3% and 68.6% of the control values at 100 μg/mL, respectively. Full article
(This article belongs to the Special Issue Marine Antiparasitic Agent)
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22 pages, 10953 KiB  
Article
Physical Properties, Chemical Analysis, and Evaluation of Antimicrobial Response of New Polylactide/Alginate/Copper Composite Materials
by Marcin H. Kudzin, Maciej Boguń, Zdzisława Mrozińska and Anna Kaczmarek
Mar. Drugs 2020, 18(12), 660; https://doi.org/10.3390/md18120660 - 21 Dec 2020
Cited by 19 | Viewed by 3063
Abstract
In recent years, due to an expansion of antibiotic-resistant microorganisms, there has been growing interest in biodegradable and antibacterial polymers that can be used in selected biomedical applications. The present work describes the synthesis of antimicrobial polylactide-copper alginate (PLA–ALG–Cu2+) composite fibers [...] Read more.
In recent years, due to an expansion of antibiotic-resistant microorganisms, there has been growing interest in biodegradable and antibacterial polymers that can be used in selected biomedical applications. The present work describes the synthesis of antimicrobial polylactide-copper alginate (PLA–ALG–Cu2+) composite fibers and their characterization. The composites were prepared by immersing PLA fibers in aqueous solution of sodium alginate, followed by ionic cross-linking of alginate chains within the polylactide fibers with Cu(II) ions to yield PLA–ALG–Cu2+ composite fibers. The composites, so prepared, were characterized by scanning electron microscopy (SEM), UV/VIS transmittance and attenuated total reflection Fourier-transform infrared spectroscopy ATR-FTIR, and by determination of their specific surface area (SSA), total/average pore volumes (through application of the 5-point Brunauer–Emmett–Teller method (BET)), and ability to block UV radiation (determination of the ultraviolet protection factor (UPF) of samples). The composites were also subjected to in vitro antimicrobial activity evaluation tests against colonies of Gram-negative (E. coli) and Gram-positive (S. aureus) bacteria and antifungal susceptibility tests against Aspergillus niger and Chaetomium globosum fungal mold species. All the results obtained in this work showed that the obtained composites were promising materials to be used as an antimicrobial wound dressing. Full article
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26 pages, 2014 KiB  
Article
Cyanobacteria and Red Macroalgae as Potential Sources of Antioxidants and UV Radiation-Absorbing Compounds for Cosmeceutical Applications
by Julia Vega, José Bonomi-Barufi, Juan Luis Gómez-Pinchetti and Félix L. Figueroa
Mar. Drugs 2020, 18(12), 659; https://doi.org/10.3390/md18120659 - 21 Dec 2020
Cited by 60 | Viewed by 7849
Abstract
In recent years, research on natural products has gained considerable attention, particularly in the cosmetic industry, which is looking for new bio-active and biodegradable molecules. In this study, cosmetic properties of cyanobacteria and red macroalgae were analyzed. The extractions were conducted in different [...] Read more.
In recent years, research on natural products has gained considerable attention, particularly in the cosmetic industry, which is looking for new bio-active and biodegradable molecules. In this study, cosmetic properties of cyanobacteria and red macroalgae were analyzed. The extractions were conducted in different solvents (water, ethanol and two combinations of water:ethanol). The main molecules with antioxidant and photoprotective capacity were mycosporine-like amino acids (MAAs), scytonemin and phenolic compounds. The highest contents of scytonemin (only present in cyanobacteria) were observed in Scytonema sp. (BEA 1603B) and Lyngbya sp. (BEA 1328B). The highest concentrations of MAAs were found in the red macroalgae Porphyra umbilicalis, Gelidium corneum and Osmundea pinnatifida and in the cyanobacterium Lyngbya sp. Scytonema sp. was the unique species that presented an MAA with maximum absorption in the UV-B band, being identified as mycosporine-glutaminol for the first time in this species. The highest content of polyphenols was observed in Scytonema sp. and P. umbilicalis. Water was the best extraction solvent for MAAs and phenols, whereas scytonemin was better extracted in a less polar solvent such as ethanol:dH2O (4:1). Cyanobacterium extracts presented higher antioxidant activity than those of red macroalgae. Positive correlations of antioxidant activity with different molecules, especially polyphenols, biliproteins and MAAs, were observed. Hydroethanolic extracts of some species incorporated in creams showed an increase in the photoprotection capacity in comparison with the base cream. Extracts of these organisms could be used as natural photoprotectors improving the diversity of sunscreens. The combination of different extracts enriched in scytonemin and MAAs could be useful to design broad-band natural UV-screen cosmeceutical products. Full article
(This article belongs to the Special Issue Mycosporine-Like Amino Acids from Marine Resource)
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18 pages, 2558 KiB  
Review
The Structural Characteristics of Seaweed Polysaccharides and Their Application in Gel Drug Delivery Systems
by Haowei Zhong, Xiaoran Gao, Cui Cheng, Chun Liu, Qiaowen Wang and Xiao Han
Mar. Drugs 2020, 18(12), 658; https://doi.org/10.3390/md18120658 - 21 Dec 2020
Cited by 73 | Viewed by 8192
Abstract
In recent years, researchers across various fields have shown a keen interest in the exploitation of biocompatible natural polymer materials, especially the development and application of seaweed polysaccharides. Seaweed polysaccharides are a multi-component mixture composed of one or more monosaccharides, which have the [...] Read more.
In recent years, researchers across various fields have shown a keen interest in the exploitation of biocompatible natural polymer materials, especially the development and application of seaweed polysaccharides. Seaweed polysaccharides are a multi-component mixture composed of one or more monosaccharides, which have the functions of being anti-virus, anti-tumor, anti-mutation, anti-radiation and enhancing immunity. These biological activities allow them to be applied in various controllable and sustained anti-inflammatory and anticancer drug delivery systems, such as seaweed polysaccharide-based nanoparticles, microspheres and gels, etc. This review summarizes the advantages of alginic acid, carrageenan and other seaweed polysaccharides, and focuses on their application in gel drug delivery systems (such as nanogels, microgels and hydrogels). In addition, recent literature reports and applications of seaweed polysaccharides are also discussed. Full article
(This article belongs to the Special Issue Marine Polymers in Drug Release)
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123 pages, 12631 KiB  
Review
Bioactive Compounds from Marine Heterobranchs
by Conxita Avila and Carlos Angulo-Preckler
Mar. Drugs 2020, 18(12), 657; https://doi.org/10.3390/md18120657 - 21 Dec 2020
Cited by 26 | Viewed by 7514
Abstract
The natural products of heterobranch molluscs display a huge variability both in structure and in their bioactivity. Despite the considerable lack of information, it can be observed from the recent literature that this group of animals possesses an astonishing arsenal of molecules from [...] Read more.
The natural products of heterobranch molluscs display a huge variability both in structure and in their bioactivity. Despite the considerable lack of information, it can be observed from the recent literature that this group of animals possesses an astonishing arsenal of molecules from different origins that provide the molluscs with potent chemicals that are ecologically and pharmacologically relevant. In this review, we analyze the bioactivity of more than 450 compounds from ca. 400 species of heterobranch molluscs that are useful for the snails to protect themselves in different ways and/or that may be useful to us because of their pharmacological activities. Their ecological activities include predator avoidance, toxicity, antimicrobials, antifouling, trail-following and alarm pheromones, sunscreens and UV protection, tissue regeneration, and others. The most studied ecological activity is predation avoidance, followed by toxicity. Their pharmacological activities consist of cytotoxicity and antitumoral activity; antibiotic, antiparasitic, antiviral, and anti-inflammatory activity; and activity against neurodegenerative diseases and others. The most studied pharmacological activities are cytotoxicity and anticancer activities, followed by antibiotic activity. Overall, it can be observed that heterobranch molluscs are extremely interesting in regard to the study of marine natural products in terms of both chemical ecology and biotechnology studies, providing many leads for further detailed research in these fields in the near future. Full article
(This article belongs to the Special Issue Bioactive Molecules from Extreme Environments II)
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18 pages, 3011 KiB  
Article
Proteomic Analysis of the Venom of Jellyfishes Rhopilema esculentum and Sanderia malayensis
by Thomas C. N. Leung, Zhe Qu, Wenyan Nong, Jerome H. L. Hui and Sai Ming Ngai
Mar. Drugs 2020, 18(12), 655; https://doi.org/10.3390/md18120655 - 21 Dec 2020
Cited by 14 | Viewed by 4267
Abstract
Venomics, the study of biological venoms, could potentially provide a new source of therapeutic compounds, yet information on the venoms from marine organisms, including cnidarians (sea anemones, corals, and jellyfish), is limited. This study identified the putative toxins of two species of jellyfish—edible [...] Read more.
Venomics, the study of biological venoms, could potentially provide a new source of therapeutic compounds, yet information on the venoms from marine organisms, including cnidarians (sea anemones, corals, and jellyfish), is limited. This study identified the putative toxins of two species of jellyfish—edible jellyfish Rhopilema esculentum Kishinouye, 1891, also known as flame jellyfish, and Amuska jellyfish Sanderia malayensis Goette, 1886. Utilizing nano-flow liquid chromatography tandem mass spectrometry (nLC–MS/MS), 3000 proteins were identified from the nematocysts in each of the above two jellyfish species. Forty and fifty-one putative toxins were identified in R. esculentum and S. malayensis, respectively, which were further classified into eight toxin families according to their predicted functions. Amongst the identified putative toxins, hemostasis-impairing toxins and proteases were found to be the most dominant members (>60%). The present study demonstrates the first proteomes of nematocysts from two jellyfish species with economic and environmental importance, and expands the foundation and understanding of cnidarian toxins. Full article
(This article belongs to the Special Issue Marine Bioactive Peptides II: Structure, Function, and Therapeutic Potential)
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9 pages, 846 KiB  
Article
Inhibition of Biofilm Formation by Modified Oxylipins from the Shipworm Symbiont Teredinibacter turnerae
by Noel M. Lacerna II, Cydee Marie V. Ramones, Jose Miguel D. Robes, Myra Ruth D. Picart, Jortan O. Tun, Bailey W. Miller, Margo G. Haygood, Eric W. Schmidt, Lilibeth A. Salvador-Reyes and Gisela P. Concepcion
Mar. Drugs 2020, 18(12), 656; https://doi.org/10.3390/md18120656 - 20 Dec 2020
Cited by 7 | Viewed by 3792
Abstract
The bioactivity-guided purification of the culture broth of the shipworm endosymbiont Teredinibacter turnerae strain 991H.S.0a.06 yielded a new fatty acid, turneroic acid (1), and two previously described oxylipins (2–3). Turneroic acid (1) is an 18-carbon [...] Read more.
The bioactivity-guided purification of the culture broth of the shipworm endosymbiont Teredinibacter turnerae strain 991H.S.0a.06 yielded a new fatty acid, turneroic acid (1), and two previously described oxylipins (2–3). Turneroic acid (1) is an 18-carbon fatty acid decorated by a hydroxy group and an epoxide ring. Compounds 1–3 inhibited bacterial biofilm formation in Staphylococcus epidermidis, while only 3 showed antimicrobial activity against planktonic S. epidermidis. Comparison of the bioactivity of 1–3 with structurally related compounds indicated the importance of the epoxide moiety for selective and potent biofilm inhibition. Full article
(This article belongs to the Special Issue Marine Natural Products with Anti-biofilm and Anti-virulence Activity)
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20 pages, 1423 KiB  
Review
Polyphenols from Brown Seaweeds (Ochrophyta, Phaeophyceae): Phlorotannins in the Pursuit of Natural Alternatives to Tackle Neurodegeneration
by Mariana Barbosa, Patrícia Valentão and Paula B. Andrade
Mar. Drugs 2020, 18(12), 654; https://doi.org/10.3390/md18120654 - 18 Dec 2020
Cited by 21 | Viewed by 4511
Abstract
Globally, the burden of neurodegenerative disorders continues to rise, and their multifactorial etiology has been regarded as among the most challenging medical issues. Bioprospecting for seaweed-derived multimodal acting products has earned increasing attention in the fight against neurodegenerative conditions. Phlorotannins (phloroglucinol-based polyphenols exclusively [...] Read more.
Globally, the burden of neurodegenerative disorders continues to rise, and their multifactorial etiology has been regarded as among the most challenging medical issues. Bioprospecting for seaweed-derived multimodal acting products has earned increasing attention in the fight against neurodegenerative conditions. Phlorotannins (phloroglucinol-based polyphenols exclusively produced by brown seaweeds) are amongst the most promising nature-sourced compounds in terms of functionality, and though research on their neuroprotective properties is still in its infancy, phlorotannins have been found to modulate intricate events within the neuronal network. This review comprehensively covers the available literature on the neuroprotective potential of both isolated phlorotannins and phlorotannin-rich extracts/fractions, highlighting the main key findings and pointing to some potential directions for neuro research ramp-up processes on these marine-derived products. Full article
(This article belongs to the Special Issue Seaweeds Secondary Metabolites: Successes In and/or Probable Therapeutic Applications 2.0)
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23 pages, 752 KiB  
Article
Extraction Improvement of the Bioactive Blue-Green Pigment “Marennine” from Diatom Haslea ostrearia’s Blue Water: A Solid-Phase Method Based on Graphitic Matrices
by William Bélanger, Alexandre A. Arnold, François Turcotte, Richard Saint-Louis, Jean-Sébastien Deschênes, Bertrand Genard, Isabelle Marcotte and Réjean Tremblay
Mar. Drugs 2020, 18(12), 653; https://doi.org/10.3390/md18120653 - 18 Dec 2020
Cited by 6 | Viewed by 3014
Abstract
The compound “marennine” is a blue–green pigment produced by the benthic microalgae Haslea ostrearia, with pathogenicity reduction activities against some bacteria and promising potential as a natural pigment in seafood industries. After decades of research, the chemical family of this compound still [...] Read more.
The compound “marennine” is a blue–green pigment produced by the benthic microalgae Haslea ostrearia, with pathogenicity reduction activities against some bacteria and promising potential as a natural pigment in seafood industries. After decades of research, the chemical family of this compound still remains unclear, mainly because structural studies were impaired by the presence of co-extracted compounds in marennine isolates. To improve the purity of marennine extract, we developed a novel extraction method using a graphitic stationary phase, which provides various advantages over the previous procedure using tandem ultrafiltration. Our method is faster, more versatile, provides a better crude yield (66%, compared to 57% for ultrafiltration) and is amenable to upscaling with continuous photobioreactor cultivation. Our goal was to take advantage of the modulable surface properties of the graphitic matrix by optimizing its interactions with marennine. As such, the effects of organic modifiers, pH and reducing agents were studied. With this improvement on marennine purification, we achieved altogether the isolation of a fucoidan-related, sulfated polysaccharide from blue water. Characterization of the polysaccharides fraction suggests that roughly half of UV-absorbing compounds could be isolated from the marennine crude extracts. The identification of sulfated polysaccharides could be a major breakthrough for marennine purification, providing targeted isolation techniques. Likewise, the added value of Haslea ostrearia and the role of polysaccharides in previous marennine chemical characterization and bioactivity studies remain to be determined. Full article
(This article belongs to the Special Issue Bioactive Compounds from Marine Bivalves and Associated Micro-Organisms)
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18 pages, 3105 KiB  
Article
Heteroexpression of Aspergillus nidulans laeA in Marine-Derived Fungi Triggers Upregulation of Secondary Metabolite Biosynthetic Genes
by Ishrat Khan, Wan-Lin Xie, Yu-Chao Yu, Huan Sheng, Yan Xu, Jia-Qi Wang, Sanjit Chandra Debnath, Jin-Zhong Xu, Dao-Qiong Zheng, Wan-Jing Ding and Pin-Mei Wang
Mar. Drugs 2020, 18(12), 652; https://doi.org/10.3390/md18120652 - 18 Dec 2020
Cited by 10 | Viewed by 4189
Abstract
Fungi are a prospective resource of bioactive compounds, but conventional methods of drug discovery are not effective enough to fully explore their metabolic potential. This study aimed to develop an easily attainable method to elicit the metabolic potential of fungi using Aspergillus nidulans [...] Read more.
Fungi are a prospective resource of bioactive compounds, but conventional methods of drug discovery are not effective enough to fully explore their metabolic potential. This study aimed to develop an easily attainable method to elicit the metabolic potential of fungi using Aspergillus nidulans laeA as a transcription regulation tool. In this study, functional analysis of Aspergillus nidulans laeA (AnLaeA) and Aspergillus sp. Z5 laeA (Az5LaeA) was done in the fungus Aspergillus sp. Z5. Heterologous AnLaeA-and native Az5LaeA-overexpression exhibited similar phenotypic effects and caused an increase in production of a bioactive compound diorcinol in Aspergillus sp. Z5, which proved the conserved function of this global regulator. In particular, heteroexpression of AnLaeA showed a significant impact on the expression of velvet complex genes, diorcinol synthesis-related genes, and different transcription factors (TFs). Moreover, heteroexpression of AnLaeA influenced the whole genome gene expression of Aspergillus sp. Z5 and triggered the upregulation of many genes. Overall, these findings suggest that heteroexpression of AnLaeA in fungi serves as a simple and easy method to explore their metabolic potential. In relation to this, AnLaeA was overexpressed in the fungus Penicillium sp. LC1-4, which resulted in increased production of quinolactacin A. Full article
(This article belongs to the Special Issue Fungal Natural Products: An Ongoing Source for New Drug Leads)
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20 pages, 1369 KiB  
Review
Are There Any Beneficial Effects of Spirulina Supplementation for Metabolic Syndrome Components in Postmenopausal Women?
by Elena Bobescu, Andreea Bălan, Marius Alexandru Moga, Andreea Teodorescu, Maria Mitrică and Lorena Dima
Mar. Drugs 2020, 18(12), 651; https://doi.org/10.3390/md18120651 - 17 Dec 2020
Cited by 16 | Viewed by 6502
Abstract
Spirulina is a phytosynthetic filamentous cyanobacterium with microscopic dimensions, which naturally grows in the highly-salted alkaline lakes of Africa, Mexico, America, and Asia. Several bioactive peptides extracted from Spirulina were demonstrated to possess antimicrobial, antiviral, antitumor, immunomodulatory, antiallergic and antihypertensive properties. It has [...] Read more.
Spirulina is a phytosynthetic filamentous cyanobacterium with microscopic dimensions, which naturally grows in the highly-salted alkaline lakes of Africa, Mexico, America, and Asia. Several bioactive peptides extracted from Spirulina were demonstrated to possess antimicrobial, antiviral, antitumor, immunomodulatory, antiallergic and antihypertensive properties. It has been reported that the consumption of Spirulina could prevent or manage metabolic syndrome components. In women, metabolic disorders are more prevalent during menopause. Postmenopausal women present higher waist circumference, increased blood pressure, hypertriglyceridemia, hyperglycemia, and decreased HDL-cholesterol values, leading to an increased risk of cardiovascular events. Therefore, in order to prevent cardiovascular diseases, it is essential to manage the components of the metabolic syndrome during the postmenopausal period. As recent reports indicated the efficiency of Spirulina supplementation in the management of the metabolic syndrome components, our study aims to review all the clinical trials conducted on this topic. Our main objective is to have a better understanding of whether and how this cyanobacterium could manage the abnormalities included in the metabolic syndrome and if it could be used as a therapeutic approach in postmenopausal women with this condition. We selected relevant articles from PubMed, Google Scholar and CrossRef databases, and a total number of 20 studies met our criteria. All included clinical trials indicated that Spirulina has positive effects in managing metabolic syndrome components. Spirulina is a valuable cyanobacterium that can be used as a food supplement for the management of metabolic syndrome, and it is able to reduce the risk of cardiovascular events. The optimal dose and period of administration remain a debated subject, and future investigations are required. Considering the beneficial effects reported against each component of the metabolic syndrome, Spirulina could also be effective in the postmenopausal period, when this syndrome is the most prevalent, but there is a strong need for human clinical trials in order to sustain this observation. Full article
(This article belongs to the Special Issue Marine Natural Products That Target Metabolic Diseases)
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21 pages, 3670 KiB  
Article
Improved Stability and Activity of a Marine Peptide-N6NH2 against Edwardsiella tarda and Its Preliminary Application in Fish
by Huihui Han, Ting Li, Zhenlong Wang, Da Teng, Ruoyu Mao, Ya Hao, Na Yang, Xiumin Wang and Jianhua Wang
Mar. Drugs 2020, 18(12), 650; https://doi.org/10.3390/md18120650 - 17 Dec 2020
Cited by 25 | Viewed by 3099
Abstract
Edwardsiella tarda can cause fatal gastro-/extraintestinal diseases in fish and humans. Overuse of antibiotics has led to antibiotic resistance and contamination in the environment, which highlights the need to find new antimicrobial agents. In this study, the marine peptide-N6 was amidated at its [...] Read more.
Edwardsiella tarda can cause fatal gastro-/extraintestinal diseases in fish and humans. Overuse of antibiotics has led to antibiotic resistance and contamination in the environment, which highlights the need to find new antimicrobial agents. In this study, the marine peptide-N6 was amidated at its C-terminus to generate N6NH2. The antibacterial activity of N6 and N6NH2 against E. tarda was evaluated in vitro and in vivo; their stability, toxicity and mode of action were also determined. Minimal inhibitory concentrations (MICs) of N6 and N6NH2 against E. tarda were 1.29–3.2 μM. Both N6 and N6NH2 killed bacteria by destroying the cell membrane of E. tarda and binding to lipopolysaccharide (LPS) and genomic DNA. In contrast with N6, N6NH2 improved the stability toward trypsin, reduced hemolysis (by 0.19% at a concentration of 256 μg/mL) and enhanced the ability to penetrate the bacterial outer and inner membrane. In the model of fish peritonitis caused by E. tarda, superior to norfloxacin, N6NH2 improved the survival rate of fish, reduced the bacterial load on the organs, alleviated the organ injury and regulated the immunity of the liver and kidney. These data suggest that the marine peptide N6NH2 may be a candidate for novel antimicrobial agents against E. tarda infections. Full article
(This article belongs to the Collection Bioactive Compounds from Marine Invertebrates)
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15 pages, 6191 KiB  
Article
Sustainable Low-Volume Analysis of Environmental Samples by Semi-Automated Prioritization of Extracts for Natural Product Research (SeaPEPR)
by Riyanti, Michael Marner, Christoph Hartwig, Maria A. Patras, Stevy I. M. Wodi, Frets J. Rieuwpassa, Frans G. Ijong, Walter Balansa and Till F. Schäberle
Mar. Drugs 2020, 18(12), 649; https://doi.org/10.3390/md18120649 - 17 Dec 2020
Cited by 8 | Viewed by 3604
Abstract
The discovery of novel natural products (NPs) that will serve as lead structures has to be an ongoing effort to fill the respective development pipelines. However, identification of NPs, which possess a potential for application in e.g., the pharma or agro sector, must [...] Read more.
The discovery of novel natural products (NPs) that will serve as lead structures has to be an ongoing effort to fill the respective development pipelines. However, identification of NPs, which possess a potential for application in e.g., the pharma or agro sector, must be as cost effective and fast as possible. Furthermore, the amount of sample available for initial testing is usually very limited, not least because of the fact that the impact on the environment, i.e., the sampled biosystem, should be kept minimal. Here, our pipeline SeaPEPR is described, in which a primary bioactivity screening of crude extracts is combined with the analysis of their metabolic fingerprint. This enabled prioritization of samples for subsequent microfractionation and dereplication of the active compounds early in the workflow. As a case study, 76 marine sponge-derived extracts were screened against a microbial screening panel. Thereunder, human pathogenic bacteria (Escherichia coli ATCC35218 and Staphylococcus aureus ATCC33592) and yeast (Candida albicans FH2173), as well as the phytopathogenic fungus Septoria tritici MUCL45407. Overall, nine extracts revealed activity against at least one test organism. Metabolic fingerprinting enabled assigning four active extracts into one metabolic group; therefore, one representative was selected for subsequent microfractionation. Dereplication of the active fractions showed a new dibrominated aplysinopsin and a hypothetical chromazonarol stereoisomer derivative. Furthermore, inhibitory activity against the common plant pest Septoria tritici was discovered for NPs of marine origin. Full article
(This article belongs to the Special Issue Natural Product Genomics and Metabolomics of Marine Bacteria)
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15 pages, 20413 KiB  
Article
The Reducing Effects of Pyrogallol-Phloroglucinol-6,6-Bieckol on High-Fat Diet-Induced Pyroptosis in Endothelial and Vascular Smooth Muscle Cells of Mice Aortas
by Seyeon Oh, Myeongjoo Son, Chul-Hyun Park, Ji Tae Jang, Kuk Hui Son and Kyunghee Byun
Mar. Drugs 2020, 18(12), 648; https://doi.org/10.3390/md18120648 - 16 Dec 2020
Cited by 21 | Viewed by 3369
Abstract
In hyperlipidemia, pyroptosis in endothelial cells (ECs) induces atherosclerosis via the toll-like receptor 4 (TLR4) pathway. We evaluated the effects of Ecklonia cava extract (ECE) and pyrogallol-phloroglucinol-6,6-bieckol (PPB) on pyroptosis of ECs and vascular smooth muscle cells (VSMCs), which leads to attenuation of [...] Read more.
In hyperlipidemia, pyroptosis in endothelial cells (ECs) induces atherosclerosis via the toll-like receptor 4 (TLR4) pathway. We evaluated the effects of Ecklonia cava extract (ECE) and pyrogallol-phloroglucinol-6,6-bieckol (PPB) on pyroptosis of ECs and vascular smooth muscle cells (VSMCs), which leads to attenuation of these cells and dysfunction of the aorta in high-fat-diet (HFD)-fed mice and in palmitate-treated ECs and VSMCs. The expression of TLR4 and nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB), which induce formation of NOD-LRR-and pyrin domain-containing protein 3 (NLRP3) inflammasomes, were increased by HFD and were decreased by ECE and PPB. The TLR4/NF-κB pathway was upregulated in palmitate-treated ECs and VSMCs and was decreased by ECE and PPB. The expressions of NLRP3/apoptosis-associated speck like protein containing a caspase recruitment domain, caspase-1, interleukin (IL)-1β, and IL-18 were increased by HFD and were decreased by ECE and PPB. Pyroptotic cells were increased by HFD and decreased by ECE and PPB. The expressions of the adhesion molecules, intercellular adhesion molecule and vascular cell adhesion molecule, and endothelin-1 were increased by HFD and were decreased by ECE and PPB. ECE and PPB decreased pyroptosis in the ECs and VSMCs, which was induced by HFD in the mouse aorta, and attenuated EC and VSMC dysfunction, an initiation factor of atherosclerosis. Full article
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14 pages, 1058 KiB  
Article
Improved Isolation Procedures for Okadaic Acid Group Toxins from Shellfish (Mytilus edulis) and Microalgae (Prorocentrum lima)
by Jane Kilcoyne, Stephen Burrell, Cíara Nulty, Rafael Salas, Elliott J. Wright, Isabelle Rajotte and Christopher O. Miles
Mar. Drugs 2020, 18(12), 647; https://doi.org/10.3390/md18120647 - 16 Dec 2020
Cited by 10 | Viewed by 2773
Abstract
Okadaic acid (OA) group toxins may accumulate in shellfish and can result in diarrhetic shellfish poisoning when consumed by humans, and are therefore regulated. Purified toxins are required for the production of certified reference materials used to accurately quantitate toxin levels in shellfish [...] Read more.
Okadaic acid (OA) group toxins may accumulate in shellfish and can result in diarrhetic shellfish poisoning when consumed by humans, and are therefore regulated. Purified toxins are required for the production of certified reference materials used to accurately quantitate toxin levels in shellfish and water samples, and for other research purposes. An improved procedure was developed for the isolation of dinophysistoxin 2 (DTX2) from shellfish (M. edulis), reducing the number of purification steps from eight to five, thereby increasing recoveries to ~68%, compared to ~40% in a previously reported method, and a purity of >95%. Cell densities and toxin production were monitored in cultures of Prorocentrum lima, that produced OA, DTX1, and their esters, over ~1.5 years with maximum cell densities of ~70,000 cells mL−1 observed. Toxin accumulation progressively increased over the study period, to ~0.7 and 2.1 mg L−1 of OA and DTX1 (including their esters), respectively, providing information on appropriate harvesting times. A procedure for the purification of OA and DTX1 from the harvested biomass was developed employing four purification steps, with recoveries of ~76% and purities of >95% being achieved. Purities were confirmed by LC-HRMS, LC-UV, and NMR spectroscopy. Additional stability observations led to a better understanding of the chemistry of these toxins. Full article
(This article belongs to the Special Issue Novel Methods for Marine Toxins Detection and Quantification)
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13 pages, 3949 KiB  
Article
α-Conotoxin TxID and [S9K]TxID, α3β4 nAChR Antagonists, Attenuate Expression and Reinstatement of Nicotine-Induced Conditioned Place Preference in Mice
by Xiaodan Li, Shen You, Jian Xiong, Yamin Qiao, Jinpeng Yu, Dongting Zhangsun and Sulan Luo
Mar. Drugs 2020, 18(12), 646; https://doi.org/10.3390/md18120646 - 16 Dec 2020
Cited by 7 | Viewed by 2699
Abstract
Tobacco smoking has become a prominent health problem faced around the world. The α3β4 nicotinic acetylcholine receptor (nAChR) is strongly associated with nicotine reward and withdrawal symptom. α-Conotoxin TxID, cloned from Conus textile, is a strong α3β4 nAChR antagonist, which has weak inhibition [...] Read more.
Tobacco smoking has become a prominent health problem faced around the world. The α3β4 nicotinic acetylcholine receptor (nAChR) is strongly associated with nicotine reward and withdrawal symptom. α-Conotoxin TxID, cloned from Conus textile, is a strong α3β4 nAChR antagonist, which has weak inhibition activity of α6/α3β4 nAChR. Meanwhile, its analogue [S9K]TxID only inhibits α3β4 nAChR (IC50 = 6.9 nM), and has no inhibitory activity to other nAChRs. The present experiment investigates the effect of α3β4 nAChR antagonists (TxID and [S9K]TxID) on the expression and reinstatement of nicotine-induced conditioned place preference (CPP) and explores the behaviors of acute nicotine in mice. The animal experimental results showed that TxID and [S9K] TxID could inhibit the expression and reinstatement of CPP, respectively. Moreover, both had no effect in acute nicotine experiment and the locomotor activity in mice. Therefore, these findings reveal that the α3β4 nAChR may be a potential target for anti-nicotine addiction treatment. [S9K]TxID, α3β4 nAChR antagonist, exhibit a superior effect for anti-nicotine addiction, which is promising to develop a novel smoking cessation drug. Full article
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27 pages, 12995 KiB  
Review
Bioactivity Potential of Marine Natural Products from Scleractinia-Associated Microbes and In Silico Anti-SARS-COV-2 Evaluation
by Eman Maher Zahran, Amgad Albohy, Amira Khalil, Alyaa Hatem Ibrahim, Heba Ali Ahmed, Ebaa M. El-Hossary, Gerhard Bringmann and Usama Ramadan Abdelmohsen
Mar. Drugs 2020, 18(12), 645; https://doi.org/10.3390/md18120645 - 16 Dec 2020
Cited by 33 | Viewed by 5874
Abstract
Marine organisms and their associated microbes are rich in diverse chemical leads. With the development of marine biotechnology, a considerable number of research activities are focused on marine bacteria and fungi-derived bioactive compounds. Marine bacteria and fungi are ranked on the top of [...] Read more.
Marine organisms and their associated microbes are rich in diverse chemical leads. With the development of marine biotechnology, a considerable number of research activities are focused on marine bacteria and fungi-derived bioactive compounds. Marine bacteria and fungi are ranked on the top of the hierarchy of all organisms, as they are responsible for producing a wide range of bioactive secondary metabolites with possible pharmaceutical applications. Thus, they have the potential to provide future drugs against challenging diseases, such as cancer, a range of viral diseases, malaria, and inflammation. This review aims at describing the literature on secondary metabolites that have been obtained from Scleractinian-associated organisms including bacteria, fungi, and zooxanthellae, with full coverage of the period from 1982 to 2020, as well as illustrating their biological activities and structure activity relationship (SAR). Moreover, all these compounds were filtered based on ADME analysis to determine their physicochemical properties, and 15 compounds were selected. The selected compounds were virtually investigated for potential inhibition for SARS-CoV-2 targets using molecular docking studies. Promising potential results against SARS-CoV-2 RNA dependent RNA polymerase (RdRp) and methyltransferase (nsp16) are presented. Full article
(This article belongs to the Special Issue Marine Natural Products against Coronaviruses)
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44 pages, 1402 KiB  
Review
Microalgae Encapsulation Systems for Food, Pharmaceutical and Cosmetics Applications
by Marta V. Vieira, Lorenzo M. Pastrana and Pablo Fuciños
Mar. Drugs 2020, 18(12), 644; https://doi.org/10.3390/md18120644 - 15 Dec 2020
Cited by 91 | Viewed by 12233
Abstract
Microalgae are microorganisms with a singular biochemical composition, including several biologically active compounds with proven pharmacological activities, such as anticancer, antioxidant and anti-inflammatory activities, among others. These properties make microalgae an interesting natural resource to be used as a functional ingredient, as well [...] Read more.
Microalgae are microorganisms with a singular biochemical composition, including several biologically active compounds with proven pharmacological activities, such as anticancer, antioxidant and anti-inflammatory activities, among others. These properties make microalgae an interesting natural resource to be used as a functional ingredient, as well as in the prevention and treatment of diseases, or cosmetic formulations. Nevertheless, natural bioactives often possess inherent chemical instability and/or poor solubility, which are usually associated with low bioavailability. As such, their industrial potential as a health-promoting substance might be severely compromised. In this context, encapsulation systems are considered as a promising and emerging strategy to overcome these shortcomings due to the presence of a surrounding protective layer. Diverse systems have already been reported in the literature for natural bioactives, where some of them have been successfully applied to microalgae compounds. Therefore, this review focuses on exploring encapsulation systems for microalgae biomass, their extracts, or purified bioactives for food, pharmaceutical, and cosmetic purposes. Moreover, this work also covers the most common encapsulation techniques and types of coating materials used, along with the main findings regarding the beneficial effects of these systems. Full article
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6 pages, 206 KiB  
Editorial
Marine Compounds and Cancer: Updates 2020
by Sergey A. Dyshlovoy and Friedemann Honecker
Mar. Drugs 2020, 18(12), 643; https://doi.org/10.3390/md18120643 - 15 Dec 2020
Cited by 30 | Viewed by 4034
Abstract
By the end of the year 2020, there are nine marine-derived anticancer drugs available on the market, and the field is currently growing exponentially [...] Full article
(This article belongs to the Collection Marine Compounds and Cancer)
16 pages, 2081 KiB  
Article
Dietary Supplementation of Astaxanthin Improved the Growth Performance, Antioxidant Ability and Immune Response of Juvenile Largemouth Bass (Micropterus salmoides) Fed High-Fat Diet
by Shiwei Xie, Peng Yin, Lixia Tian, Yingying Yu, Yongjian Liu and Jin Niu
Mar. Drugs 2020, 18(12), 642; https://doi.org/10.3390/md18120642 - 15 Dec 2020
Cited by 59 | Viewed by 4631
Abstract
High-fat diet (HFD) usually induces oxidative stress and astaxanthin is regarded as an excellent anti-oxidant. An 8-week feeding trial was conducted to investigate the effects of dietary astaxanthin supplementation on growth performance, lipid metabolism, antioxidant ability, and immune response of juvenile largemouth bass [...] Read more.
High-fat diet (HFD) usually induces oxidative stress and astaxanthin is regarded as an excellent anti-oxidant. An 8-week feeding trial was conducted to investigate the effects of dietary astaxanthin supplementation on growth performance, lipid metabolism, antioxidant ability, and immune response of juvenile largemouth bass (Micropterus salmoides) fed HFD. Four diets were formulated: the control diet (10.87% lipid, C), high-fat diet (18.08% lipid, HF), and HF diet supplemented with 75 and 150 mg kg−1 astaxanthin (HFA1 and HFA2, respectively). Dietary supplementation of astaxanthin improved the growth of fish fed HFD, also decreased hepatosomatic index and intraperitoneal fat ratio of fish fed HFD, while having no effect on body fat. Malondialdehyde content and superoxide dismutase activity were increased in fish fed HFD, astaxanthin supplementation in HFD decreased the oxidative stress of fish. The supplementation of astaxanthin in HFD also reduced the mRNA levels of Caspase 3, Caspase 9, BAD, and IL15. These results suggested that dietary astaxanthin supplementation in HFD improved the growth performance, antioxidant ability and immune response of largemouth bass. Full article
(This article belongs to the Special Issue Marine Carotenoids)
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25 pages, 2111 KiB  
Review
Ecological and Industrial Implications of Dynamic Seaweed-Associated Microbiota Interactions
by Farid Menaa, P. A. U. I. Wijesinghe, Gobika Thiripuranathar, Bushra Uzair, Haroon Iqbal, Barkat Ali Khan and Bouzid Menaa
Mar. Drugs 2020, 18(12), 641; https://doi.org/10.3390/md18120641 - 14 Dec 2020
Cited by 50 | Viewed by 9182
Abstract
Seaweeds are broadly distributed and represent an important source of secondary metabolites (e.g., halogenated compounds, polyphenols) eliciting various pharmacological activities and playing a relevant ecological role in the anti-epibiosis. Importantly, host (as known as basibiont such as algae)–microbe (as known as epibiont such [...] Read more.
Seaweeds are broadly distributed and represent an important source of secondary metabolites (e.g., halogenated compounds, polyphenols) eliciting various pharmacological activities and playing a relevant ecological role in the anti-epibiosis. Importantly, host (as known as basibiont such as algae)–microbe (as known as epibiont such as bacteria) interaction (as known as halobiont) is a driving force for coevolution in the marine environment. Nevertheless, halobionts may be fundamental (harmless) or detrimental (harmful) to the functioning of the host. In addition to biotic factors, abiotic factors (e.g., pH, salinity, temperature, nutrients) regulate halobionts. Spatiotemporal and functional exploration of such dynamic interactions appear crucial. Indeed, environmental stress in a constantly changing ocean may disturb complex mutualistic relations, through mechanisms involving host chemical defense strategies (e.g., secretion of secondary metabolites and antifouling chemicals by quorum sensing). It is worth mentioning that many of bioactive compounds, such as terpenoids, previously attributed to macroalgae are in fact produced or metabolized by their associated microorganisms (e.g., bacteria, fungi, viruses, parasites). Eventually, recent metagenomics analyses suggest that microbes may have acquired seaweed associated genes because of increased seaweed in diets. This article retrospectively reviews pertinent studies on the spatiotemporal and functional seaweed-associated microbiota interactions which can lead to the production of bioactive compounds with high antifouling, theranostic, and biotechnological potential. Full article
(This article belongs to the Special Issue Invertebrate or Macroalgae-Associated Microbiome: A New Source of Bioactive Compounds with Therapeutical, Biotechnological Applications)
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7 pages, 213 KiB  
Commentary
Bioactive Molecules from Extreme Environments
by Daniela Giordano
Mar. Drugs 2020, 18(12), 640; https://doi.org/10.3390/md18120640 - 14 Dec 2020
Cited by 36 | Viewed by 4366
Abstract
Marine organisms inhabiting extreme habitats are a promising reservoir of bioactive compounds for drug discovery. Extreme environments, i.e., polar and hot regions, deep sea, hydrothermal vents, marine areas of high pressure or high salinity, experience conditions close to the limit of life. In [...] Read more.
Marine organisms inhabiting extreme habitats are a promising reservoir of bioactive compounds for drug discovery. Extreme environments, i.e., polar and hot regions, deep sea, hydrothermal vents, marine areas of high pressure or high salinity, experience conditions close to the limit of life. In these marine ecosystems, “hot spots” of biodiversity, organisms have adopted a huge variety of strategies to cope with such harsh conditions, such as the production of bioactive molecules potentially valuable for biotechnological applications and for pharmaceutical, nutraceutical and cosmeceutical sectors. Many enzymes isolated from extreme environments may be of great interest in the detergent, textile, paper and food industries. Marine natural products produced by organisms evolved under hostile conditions exhibit a wide structural diversity and biological activities. In fact, they exert antimicrobial, anticancer, antioxidant and anti-inflammatory activities. The aim of this Special Issue “Bioactive Molecules from Extreme Environments” was to provide the most recent findings on bioactive molecules as well as enzymes isolated from extreme environments, to be used in biotechnological discovery pipelines and pharmaceutical applications, in an effort to encourage further research in these extreme habitats. Full article
(This article belongs to the Special Issue Bioactive Molecules from Extreme Environments)
21 pages, 3314 KiB  
Article
Morphogenetic (Mucin Expression) as Well as Potential Anti-Corona Viral Activity of the Marine Secondary Metabolite Polyphosphate on A549 Cells
by Werner E. G. Müller, Meik Neufurth, Shunfeng Wang, Rongwei Tan, Heinz C. Schröder and Xiaohong Wang
Mar. Drugs 2020, 18(12), 639; https://doi.org/10.3390/md18120639 - 14 Dec 2020
Cited by 25 | Viewed by 4052
Abstract
The mucus layer of the nasopharynx and bronchial epithelium has a barrier function against inhaled pathogens such as the coronavirus SARS-CoV-2. We recently found that inorganic polyphosphate (polyP), a physiological, metabolic energy (ATP)-providing polymer released from blood platelets, blocks the binding of the [...] Read more.
The mucus layer of the nasopharynx and bronchial epithelium has a barrier function against inhaled pathogens such as the coronavirus SARS-CoV-2. We recently found that inorganic polyphosphate (polyP), a physiological, metabolic energy (ATP)-providing polymer released from blood platelets, blocks the binding of the receptor binding domain (RBD) to the cellular ACE2 receptor in vitro. PolyP is a marine natural product and is abundantly present in marine bacteria. Now, we have approached the in vivo situation by studying the effect of polyP on the human alveolar basal epithelial A549 cells in a mucus-like mucin environment. These cells express mucins as well as the ectoenzymes alkaline phosphatase (ALP) and adenylate kinase (ADK), which are involved in the extracellular production of ATP from polyP. Mucin, integrated into a collagen-based hydrogel, stimulated cell growth and attachment. The addition of polyP to the hydrogel significantly increased cell attachment and also the expression of the membrane-tethered mucin MUC1 and the secreted mucin MUC5AC. The increased synthesis of MUC1 was also confirmed by immunostaining. This morphogenetic effect of polyP was associated with a rise in extracellular ATP level. We conclude that the nontoxic and non-immunogenic polymer polyP could possibly also exert a protective effect against SARS-CoV-2-cell attachment; first, by stimulating the innate antiviral response by strengthening the mucin barrier with its antimicrobial proteins, and second, by inhibiting virus attachment to the cells, as deduced from the reduction in the strength of binding between the viral RBD and the cellular ACE2 receptor. Full article
(This article belongs to the Special Issue Marine Natural Products against Coronaviruses)
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11 pages, 1532 KiB  
Communication
Protection of Alcohol Dehydrogenase against Freeze–Thaw Stress by Ice-Binding Proteins Is Proportional to Their Ice Recrystallization Inhibition Property
by Young Hoon Lee, Kitae Kim, Jun Hyuck Lee and Hak Jun Kim
Mar. Drugs 2020, 18(12), 638; https://doi.org/10.3390/md18120638 - 13 Dec 2020
Cited by 3 | Viewed by 2787
Abstract
Ice-binding proteins (IBPs) have ice recrystallization inhibition (IRI) activity. IRI property has been extensively utilized for the cryopreservation of different types of cells and tissues. Recent reports demonstrated that IRI can also play a significant role in protecting proteins from freezing damage during [...] Read more.
Ice-binding proteins (IBPs) have ice recrystallization inhibition (IRI) activity. IRI property has been extensively utilized for the cryopreservation of different types of cells and tissues. Recent reports demonstrated that IRI can also play a significant role in protecting proteins from freezing damage during freeze–thaw cycles. In this study, we hypothesized that the protective capability of IBPs on proteins against freeze–thaw damage is proportional to their IRI activity. Hence we used two IBPs: one with higher IRI activity (LeIBP) and the other with lower activity (FfIBP). Yeast alcohol dehydrogenase (ADH) was used as a freeze-labile model protein. IBPs and ADH were mixed, frozen at −20 °C, and thawed repeatedly. The structure of ADH was assessed using fluorescence emission spectra probed by 1-anilinonaphthalene-8-sulfonate over the repeated freeze–thaw cycles. The activity was monitored at 340 nm spectrophotometrically. Fluorescence data and activity clearly indicated that ADH without IBP was freeze-labile. However, ADH maintained about 70% residual activity after five repeated cycles at a minimal concentration of 0.1 mg mL-1 of high IRI-active LeIBP, but only 50% activity at 4 mg mL−1 of low active FfIBP. These results showed that the protection of proteins from freeze–thaw stress by IBPs is proportional to their IRI activity. Full article
(This article belongs to the Special Issue Enzymes and Ice Binding Proteins from Marine Cold-Adapted Organisms)
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21 pages, 2240 KiB  
Article
Identification and Characterization of a New Type III Polyketide Synthase from a Marine Yeast, Naganishia uzbekistanensis
by Laure Martinelli, Vanessa Redou, Bastien Cochereau, Ludovic Delage, Nolwenn Hymery, Elisabeth Poirier, Christophe Le Meur, Gaetan Le Foch, Lionel Cladiere, Mohamed Mehiri, Nathalie Demont-Caulet and Laurence Meslet-Cladiere
Mar. Drugs 2020, 18(12), 637; https://doi.org/10.3390/md18120637 - 11 Dec 2020
Cited by 4 | Viewed by 3518
Abstract
A putative Type III Polyketide synthase (PKSIII) encoding gene was identified from a marine yeast, Naganishia uzbekistanensis strain Mo29 (UBOCC-A-208024) (formerly named as Cryptococcus sp.) isolated from deep-sea hydrothermal vents. This gene is part of a distinct phylogenetic branch compared to all known [...] Read more.
A putative Type III Polyketide synthase (PKSIII) encoding gene was identified from a marine yeast, Naganishia uzbekistanensis strain Mo29 (UBOCC-A-208024) (formerly named as Cryptococcus sp.) isolated from deep-sea hydrothermal vents. This gene is part of a distinct phylogenetic branch compared to all known terrestrial fungal sequences. This new gene encodes a C-terminus extension of 74 amino acids compared to other known PKSIII proteins like Neurospora crassa. Full-length and reduced versions of this PKSIII were successfully cloned and overexpressed in a bacterial host, Escherichia coli BL21 (DE3). Both proteins showed the same activity, suggesting that additional amino acid residues at the C-terminus are probably not required for biochemical functions. We demonstrated by LC-ESI-MS/MS that these two recombinant PKSIII proteins could only produce tri- and tetraketide pyrones and alkylresorcinols using only long fatty acid chain from C8 to C16 acyl-CoAs as starter units, in presence of malonyl-CoA. In addition, we showed that some of these molecules exhibit cytotoxic activities against several cancer cell lines. Full article
(This article belongs to the Special Issue 3rd International Conference of the Marine Fungal Natural Products (MaFNaP))
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11 pages, 1722 KiB  
Article
Antimicrobial and Antioxidant Polyketides from a Deep-Sea-Derived Fungus Aspergillus versicolor SH0105
by Lu-Jia Yang, Xiao-Yue Peng, Ya-Hui Zhang, Zhi-Qing Liu, Xin Li, Yu-Cheng Gu, Chang-Lun Shao, Zhuang Han and Chang-Yun Wang
Mar. Drugs 2020, 18(12), 636; https://doi.org/10.3390/md18120636 - 11 Dec 2020
Cited by 23 | Viewed by 3303
Abstract
Fifteen polyketides, including four new compounds, isoversiol F (1), decumbenone D (2), palitantin B (7), and 1,3-di-O-methyl-norsolorinic acid (8), along with 11 known compounds (3–6 and 9–15), [...] Read more.
Fifteen polyketides, including four new compounds, isoversiol F (1), decumbenone D (2), palitantin B (7), and 1,3-di-O-methyl-norsolorinic acid (8), along with 11 known compounds (3–6 and 9–15), were isolated from the deep-sea-derived fungus Aspergillus versicolor SH0105. Their structures and absolute configurations were determined by comprehensive spectroscopic data, including 1D and 2D NMR, HRESIMS, and ECD calculations, and it is the first time to determine the absolute configuration of known decumbenone A (6). All of these compounds were evaluated for their antimicrobial activities against four human pathogenic microbes and five fouling bacterial strains. The results indicated that 3,7-dihydroxy-1,9-dimethyldibenzofuran (14) displayed obvious inhibitory activity against Staphylococcus aureus (ATCC 27154) with the MIC value of 13.7 μM. In addition, the antioxidant assays of the isolated compounds revealed that aspermutarubrol/violaceol-I (15) exhibited significant 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity with the IC50 value of 34.1 μM, and displayed strong reduction of Fe3+ with the ferric reducing antioxidant power (FRAP) value of 9.0 mM under the concentration of 3.1 μg/mL, which were more potent than ascorbic acid. Full article
(This article belongs to the Special Issue Marine Natural Product Chemistry: A Themed Issue Dedicated to Prof. Dr. Peter Proksch on His Research Career)
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21 pages, 1906 KiB  
Article
Herring Milt and Herring Milt Protein Hydrolysate Are Equally Effective in Improving Insulin Sensitivity and Pancreatic Beta-Cell Function in Diet-Induced Obese- and Insulin-Resistant Mice
by Yanwen Wang, Sandhya Nair and Jacques Gagnon
Mar. Drugs 2020, 18(12), 635; https://doi.org/10.3390/md18120635 - 11 Dec 2020
Cited by 13 | Viewed by 2994
Abstract
Although genetic predisposition influences the onset and progression of insulin resistance and diabetes, dietary nutrients are critical. In general, protein is beneficial relative to carbohydrate and fat but dependent on protein source. Our recent study demonstrated that 70% replacement of dietary casein protein [...] Read more.
Although genetic predisposition influences the onset and progression of insulin resistance and diabetes, dietary nutrients are critical. In general, protein is beneficial relative to carbohydrate and fat but dependent on protein source. Our recent study demonstrated that 70% replacement of dietary casein protein with the equivalent quantity of protein derived from herring milt protein hydrolysate (HMPH; herring milt with proteins being enzymatically hydrolyzed) significantly improved insulin resistance and glucose homeostasis in high-fat diet-induced obese mice. As production of protein hydrolysate increases the cost of the product, it is important to determine whether a simply dried and ground herring milt product possesses similar benefits. Therefore, the current study was conducted to investigate the effect of herring milt dry powder (HMDP) on glucose control and the associated metabolic phenotypes and further to compare its efficacy with HMPH. Male C57BL/6J mice on a high-fat diet for 7 weeks were randomized based on body weight and blood glucose into three groups. One group continued on the high-fat diet and was used as the insulin-resistant/diabetic control and the other two groups were given the high-fat diet modified to have 70% of casein protein being replaced with the same amount of protein from HMDP or HMPH. A group of mice on a low-fat diet all the time was used as the normal control. The results demonstrated that mice on the high-fat diet increased weight gain and showed higher blood concentrations of glucose, insulin, and leptin, as well as impaired glucose tolerance and pancreatic β-cell function relative to those on the normal control diet. In comparison with the high-fat diet, the replacement of 70% dietary casein protein with the same amount of HMDP or HMPH protein decreased weight gain and significantly improved the aforementioned biomarkers, insulin sensitivity or resistance, and β-cell function. The HMDP and HMPH showed similar effects on every parameter except blood lipids where HMDP decreased total cholesterol and non-HDL-cholesterol levels while the effect of HMPH was not significant. The results demonstrate that substituting 70% of dietary casein protein with the equivalent amount of HMDP or HMPH protein protects against obesity and diabetes, and HMDP is also beneficial to cholesterol homeostasis. Full article
(This article belongs to the Special Issue Marine Natural Products That Target Metabolic Diseases)
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20 pages, 804 KiB  
Review
Advances in Studies on the Pharmacological Activities of Fucoxanthin
by Han Xiao, Jiarui Zhao, Chang Fang, Qi Cao, Maochen Xing, Xia Li, Junfeng Hou, Aiguo Ji and Shuliang Song
Mar. Drugs 2020, 18(12), 634; https://doi.org/10.3390/md18120634 - 11 Dec 2020
Cited by 43 | Viewed by 5398
Abstract
Fucoxanthin is a natural carotenoid derived mostly from many species of marine brown algae. It is characterized by small molecular weight, is chemically active, can be easily oxidized, and has diverse biological activities, thus protecting cell components from ROS. Fucoxanthin inhibits the proliferation [...] Read more.
Fucoxanthin is a natural carotenoid derived mostly from many species of marine brown algae. It is characterized by small molecular weight, is chemically active, can be easily oxidized, and has diverse biological activities, thus protecting cell components from ROS. Fucoxanthin inhibits the proliferation of a variety of cancer cells, promotes weight loss, acts as an antioxidant and anti-inflammatory agent, interacts with the intestinal flora to protect intestinal health, prevents organ fibrosis, and exerts a multitude of other beneficial effects. Thus, fucoxanthin has a wide range of applications and broad prospects. This review focuses primarily on the latest progress in research on its pharmacological activity and underlying mechanisms. Full article
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17 pages, 6832 KiB  
Article
A Computer-Aided Drug Design Approach to Predict Marine Drug-Like Leads for SARS-CoV-2 Main Protease Inhibition
by Susana P. Gaudêncio and Florbela Pereira
Mar. Drugs 2020, 18(12), 633; https://doi.org/10.3390/md18120633 - 10 Dec 2020
Cited by 25 | Viewed by 4357
Abstract
The investigation of marine natural products (MNPs) as key resources for the discovery of drugs to mitigate the COVID-19 pandemic is a developing field. In this work, computer-aided drug design (CADD) approaches comprising ligand- and structure-based methods were explored for predicting SARS-CoV-2 main [...] Read more.
The investigation of marine natural products (MNPs) as key resources for the discovery of drugs to mitigate the COVID-19 pandemic is a developing field. In this work, computer-aided drug design (CADD) approaches comprising ligand- and structure-based methods were explored for predicting SARS-CoV-2 main protease (Mpro) inhibitors. The CADD ligand-based method used a quantitative structure–activity relationship (QSAR) classification model that was built using 5276 organic molecules extracted from the ChEMBL database with SARS-CoV-2 screening data. The best model achieved an overall predictive accuracy of up to 67% for an external and internal validation using test and training sets. Moreover, based on the best QSAR model, a virtual screening campaign was carried out using 11,162 MNPs retrieved from the Reaxys® database, 7 in-house MNPs obtained from marine-derived actinomycetes by the team, and 14 MNPs that are currently in the clinical pipeline. All the MNPs from the virtual screening libraries that were predicted as belonging to class A were selected for the CADD structure-based method. In the CADD structure-based approach, the 494 MNPs selected by the QSAR approach were screened by molecular docking against Mpro enzyme. A list of virtual screening hits comprising fifteen MNPs was assented by establishing several limits in this CADD approach, and five MNPs were proposed as the most promising marine drug-like leads as SARS-CoV-2 Mpro inhibitors, a benzo[f]pyrano[4,3-b]chromene, notoamide I, emindole SB beta-mannoside, and two bromoindole derivatives. Full article
(This article belongs to the Special Issue Virtual Screening of Marine Natural Products)
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16 pages, 8950 KiB  
Article
Bioactive Steroids from the Red Sea Soft Coral Sinularia polydactyla
by Mohamed A. Tammam, Lucie Rárová, Marie Kvasnicová, Gabriel Gonzalez, Ahmed M. Emam, Aldoushy Mahdy, Miroslav Strnad, Efstathia Ioannou and Vassilios Roussis
Mar. Drugs 2020, 18(12), 632; https://doi.org/10.3390/md18120632 - 10 Dec 2020
Cited by 23 | Viewed by 4038
Abstract
Six new (1, 2, 6, 8, 13, and 20) and twenty previously isolated (3–5, 7, 9–12, 14–19, and 21–26) steroids featuring thirteen different [...] Read more.
Six new (1, 2, 6, 8, 13, and 20) and twenty previously isolated (3–5, 7, 9–12, 14–19, and 21–26) steroids featuring thirteen different carbocycle motifs were isolated from the organic extract of the soft coral Sinularia polydactyla collected from the Hurghada reef in the Red Sea. The structures and the relative configurations of the isolated natural products have been determined based on extensive analysis of their NMR and MS data. The cytotoxic, anti-inflammatory, anti-angiogenic, and neuroprotective activity of compounds 3–7, 9–12, 14–20, and 22–26, as well as their effect on androgen receptor-regulated transcription was evaluated in vitro in human tumor and non-cancerous cells. Steroids 22 and 23 showed significant cytotoxicity in the low micromolar range against the HeLa and MCF7 cancer cell lines, while migration of endothelial cells was inhibited by compounds 11, 12, 22, and 23 at 20 µM. The results of the androgen receptor (AR) reporter assay showed that compound 11 exhibited the strongest inhibition of AR at 10 µM, while it is noteworthy that steroids 10, 16, and 20 displayed increased inhibition of AR with decreasing concentrations. Additionally, compounds 11 and 23 showed neuroprotective activity on neuron-like SH-SY5Y cells. Full article
(This article belongs to the Special Issue Bioactive Natural Products from the Red Sea)
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