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Marine Drugs
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Synthesis of Marine Natural Products and Molecules Inspired by Marine...
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Synthesis of Marine Natural Products and Molecules Inspired by Marine Substances II

A special issue of Marine Drugs (ISSN 1660-3397). This special issue belongs to the section "Synthesis and Medicinal Chemistry of Marine Natural Products".

Deadline for manuscript submissions: closed (31 July 2021) | Viewed by 19350

Printed Edition Available!
A printed edition of this Special Issue is available here.

Special Issue Editor

Dr. Emiliano Manzo

E-Mail Website
Guest Editor
Institute of Biomolecular Chemistry (ICB), Consiglio Nazionale delle Ricerche (CNR), Via Campi Flegrei 34, 80078 Pozzuoli, Italy
Interests: marine natural products; chemical synthesis; immunomodulatory molecules; drug discovery
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,                

Marine natural products are characterized by high chemical diversity, biochemical specificity and other molecular properties that make them favorable as lead structures for drug discovery. In this field, one of the main problems is often the reduced natural availability of the isolated substances, which can complicate both the structural characterization and possible future developments. For these reasons, the study of bioactive marine metabolites should rely on the development of chemical synthesis and synthetic strategies aimed at preparation of pure compounds and analogs both for structural confirmation and/or for the large-scale preparation necessary for future applications.

Moreover, natural products can be a crucial starting point for the preparation of molecules structurally inspired by the latter, opening the way to new classes of biologically active compounds with pharmacological potential.

In consideration of the success of the Special Issue on "Synthesis of Marine Natural Products and Molecules Inspired by Marine Substances", and the relevant interest on the topic, we are pleased to announce the second version of this Special Issue.

This Special Issue aims to collect original research articles regarding synthetic strategies for secondary marine metabolites and/or analogs that can favor applications of these molecules and/or can solve structural challenges common in the field of natural substances.

Dr. Emiliano Manzo
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Marine Drugs is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2900 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Synthesis
  • Marine compounds
  • Immunomodulatory molecules
  • Metabolites

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Published Papers (6 papers)

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Editorial

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3 pages, 180 KiB  
Editorial
Synthesis of Marine Natural Products and Molecules Inspired by Marine Substances II
by Emiliano Manzo
Mar. Drugs 2021, 19(9), 518; https://doi.org/10.3390/md19090518 - 13 Sep 2021
Cited by 1 | Viewed by 1610
Abstract
The sea occupies more than 70% of the Earth’s surface and includes more than 300,000 organisms with huge biodiversity [...] Full article
(This article belongs to the Special Issue Synthesis of Marine Natural Products and Molecules Inspired by Marine Substances II)

Research

Jump to: Editorial, Review

13 pages, 7613 KiB  
Article
Total Synthesis and Anti-Inflammatory Bioactivity of (−)-Majusculoic Acid and Its Derivatives
by Hong-Xiu Xiao, Qing-Xiang Yan, Zhi-Hui He, Zheng-Biao Zou, Qing-Qing Le, Ting-Ting Chen, Bing Cai, Xian-Wen Yang and Su-Lan Luo
Mar. Drugs 2021, 19(6), 288; https://doi.org/10.3390/md19060288 - 21 May 2021
Cited by 10 | Viewed by 2302
Abstract
The first total synthesis of marine natural product, (−)-majusculoic acid (1) and its seven analogs (9–15), was accomplished in three to ten steps with a yield of 3% to 28%. The strategy featured the application of the [...] Read more.
The first total synthesis of marine natural product, (−)-majusculoic acid (1) and its seven analogs (9–15), was accomplished in three to ten steps with a yield of 3% to 28%. The strategy featured the application of the conformational controlled establishment of the trans-cyclopropane and stereochemical controlled bromo-olefination or olefination by Horner–Wadsworth–Emmons (HWE) reaction. The potential anti-inflammatory activity of the eight compounds (1 and 9–15) was evaluated by determining the nitric oxide (NO) production in the lipopolysaccharide (LPS)-induced mouse macrophages RAW264.7. (−)-Majusculoic acid (1), methyl majusculoate (9), and (1R,2R)-2-((3E,5Z)-6-bromonona-3,5-dien-1-yl)cyclopropane-1-carboxylic acid (12) showed significant effect with inhibition rates of 33.68%, 35.75%, and 43.01%, respectively. Moreover, they did not show cytotoxicity against RAW264.7 cells, indicating that they might be potential anti-inflammatory agents. Full article
(This article belongs to the Special Issue Synthesis of Marine Natural Products and Molecules Inspired by Marine Substances II)
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15 pages, 4966 KiB  
Article
Compounds Identified from Marine Mangrove Plant (Avicennia alba) as Potential Antiviral Drug Candidates against WDSV, an In-Silico Approach
by Mohammed Othman Aljahdali, Mohammad Habibur Rahman Molla and Foysal Ahammad
Mar. Drugs 2021, 19(5), 253; https://doi.org/10.3390/md19050253 - 28 Apr 2021
Cited by 39 | Viewed by 4718
Abstract
Walleye dermal sarcoma virus (WDSV) is a type of retrovirus, which affects most of the adult walleye fishes during the spawning time. The virus causes multiple epithelial tumors on the fish’s skin and fins that are liable for more than 50% of the [...] Read more.
Walleye dermal sarcoma virus (WDSV) is a type of retrovirus, which affects most of the adult walleye fishes during the spawning time. The virus causes multiple epithelial tumors on the fish’s skin and fins that are liable for more than 50% of the mortality rate of fish around the world. Till now, no effective antiviral drug or vaccine candidates have been developed that can block the progression of the disease caused by the pathogen. It was found that the 582-amino-acid (aa) residues long internal structural gag polyprotein of the virus plays an important role in virus budding and virion maturation outside of the cell. Inhibition of the protein can block the budding and virion maturation process and can be developed as an antiviral drug candidate against the virus. Therefore, the study aimed to identify potential natural antiviral drug candidates from the tropical mangrove marine plant Avicennia alba, which will be able to block the budding and virion maturation process by inhibiting the activity of the gag protein of the virus. Initially, a homology modeling approach was applied to identify the 3D structure, followed by refinement and validation of the protein. The refined protein structures were then utilized for molecular docking simulation. Eleven phytochemical compounds have been isolated from the marine plant and docked against the virus gag polyprotein. Three compounds, namely Friedlein (CID244297), Phytosterols (CID12303662), and 1-Triacontanol (CID68972) have been selected based on their docking score −8.5 kcal/mol, −8.0 kcal/mol and −7.9 kcal/mol, respectively, and were evaluated through ADME (Absorption, Distribution, Metabolism and Excretion), and toxicity properties. Finally, molecular dynamics (MD) simulation was applied to confirm the binding stability of the protein-ligands complex structure. The ADME and toxicity analysis reveal the efficacy and non-toxic properties of the compounds, where MD simulation confirmed the binding stability of the selected three compounds with the targeted protein. This computational study revealed the virtuous value of the selected three compounds against the targeted gag polyprotein and will be effective and promising antiviral candidates against the pathogen in a significant and worthwhile manner. Although in vitro and in vivo study is required for further evaluation of the compounds against the targeted protein. Full article
(This article belongs to the Special Issue Synthesis of Marine Natural Products and Molecules Inspired by Marine Substances II)
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Review

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27 pages, 12822 KiB  
Review
Recent Developments on the Synthesis and Bioactivity of Ilamycins/Rufomycins and Cyclomarins, Marine Cyclopeptides That Demonstrate Anti-Malaria and Anti-Tuberculosis Activity
by Uli Kazmaier and Lukas Junk
Mar. Drugs 2021, 19(8), 446; https://doi.org/10.3390/md19080446 - 03 Aug 2021
Cited by 14 | Viewed by 3829
Abstract
Ilamycins/rufomycins and cyclomarins are marine cycloheptapeptides containing unusual amino acids. Produced by Streptomyces sp., these compounds show potent activity against a range of mycobacteria, including multidrug-resistant strains of Mycobacterium tuberculosis. The cyclomarins are also very potent inhibitors of Plasmodium falciparum. Biosynthetically [...] Read more.
Ilamycins/rufomycins and cyclomarins are marine cycloheptapeptides containing unusual amino acids. Produced by Streptomyces sp., these compounds show potent activity against a range of mycobacteria, including multidrug-resistant strains of Mycobacterium tuberculosis. The cyclomarins are also very potent inhibitors of Plasmodium falciparum. Biosynthetically the cyclopeptides are obtained via a heptamodular nonribosomal peptide synthetase (NRPS) that directly incorporates some of the nonproteinogenic amino acids. A wide range of derivatives can be obtained by fermentation, while bioengineering also allows the mutasynthesis of derivatives, especially cyclomarins. Other derivatives are accessible by semisynthesis or total syntheses, reported for both natural product classes. The anti-tuberculosis (anti-TB) activity results from the binding of the peptides to the N-terminal domain (NTD) of the bacterial protease-associated unfoldase ClpC1, causing cell death by the uncontrolled proteolytic activity of this enzyme. Diadenosine triphosphate hydrolase (PfAp3Aase) was found to be the active target of the cyclomarins in Plasmodia. SAR studies with natural and synthetic derivatives on ilamycins/rufomycins and cyclomarins indicate which parts of the molecules can be simplified or otherwise modified without losing activity for either target. This review examines all aspects of the research conducted in the syntheses of these interesting cyclopeptides. Full article
(This article belongs to the Special Issue Synthesis of Marine Natural Products and Molecules Inspired by Marine Substances II)
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24 pages, 6954 KiB  
Review
Marine Alkaloids: Compounds with In Vivo Activity and Chemical Synthesis
by Paulo E. S. Munekata, Mirian Pateiro, Carlos A. Conte-Junior, Rubén Domínguez, Asad Nawaz, Noman Walayat, Elena Movilla Fierro and José M. Lorenzo
Mar. Drugs 2021, 19(7), 374; https://doi.org/10.3390/md19070374 - 28 Jun 2021
Cited by 14 | Viewed by 3693
Abstract
Marine alkaloids comprise a class of compounds with several nitrogenated structures that can be explored as potential natural bioactive compounds. The scientific interest in these compounds has been increasing in the last decades, and many studies have been published elucidating their chemical structure [...] Read more.
Marine alkaloids comprise a class of compounds with several nitrogenated structures that can be explored as potential natural bioactive compounds. The scientific interest in these compounds has been increasing in the last decades, and many studies have been published elucidating their chemical structure and biological effects in vitro. Following this trend, the number of in vivo studies reporting the health-related properties of marine alkaloids has been increasing and providing more information about the effects in complex organisms. Experiments with animals, especially mice and zebrafish, are revealing the potential health benefits against cancer development, cardiovascular diseases, seizures, Alzheimer’s disease, mental health disorders, inflammatory diseases, osteoporosis, cystic fibrosis, oxidative stress, human parasites, and microbial infections in vivo. Although major efforts are still necessary to increase the knowledge, especially about the translation value of the information obtained from in vivo experiments to clinical trials, marine alkaloids are promising candidates for further experiments in drug development. Full article
(This article belongs to the Special Issue Synthesis of Marine Natural Products and Molecules Inspired by Marine Substances II)
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15 pages, 2481 KiB  
Review
Divergent Strategy in Marine Tetracyclic Meroterpenoids Synthesis
by Antonio Rosales Martínez, Ignacio Rodríguez-García and Josefa L. López-Martínez
Mar. Drugs 2021, 19(5), 273; https://doi.org/10.3390/md19050273 - 13 May 2021
Cited by 4 | Viewed by 2389
Abstract
The divergent total synthesis strategy can be successfully applied to the preparation of families of natural products using a common late-stage pluripotent intermediate. This approach is a powerful tool in organic synthesis as it offers opportunities for the efficient preparation of structurally related [...] Read more.
The divergent total synthesis strategy can be successfully applied to the preparation of families of natural products using a common late-stage pluripotent intermediate. This approach is a powerful tool in organic synthesis as it offers opportunities for the efficient preparation of structurally related compounds. This article reviews the synthesis of the marine natural product aureol, as well as its use as a common intermediate in the divergent synthesis of other marine natural and non-natural tetracyclic meroterpenoids. Full article
(This article belongs to the Special Issue Synthesis of Marine Natural Products and Molecules Inspired by Marine Substances II)
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