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Special Issue "Isolation and Structure Elucidation of Marine Secondary Metabolites"

A special issue of Marine Drugs (ISSN 1660-3397).

Deadline for manuscript submissions: 30 September 2018

Special Issue Editor

Guest Editor
Dr. Fernando Reyes

Area Head, Chemistry, Fundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía, Avda. del Conocimiento, 34. Edif. Centro de Desarrollo Farmacéutico y Alimentario, Parque Tecnológico de Ciencias de la Salud, 18016, Armilla, Granada, Spain
Website | E-Mail
Phone: +34 958993965
Interests: marine natural products; microbial natural products; bioassay-guided isolation and structure elucidation; antitumour compounds; antimicrobial compounds

Special Issue Information

Dear Colleagues,

Marine organisms have been a source for a vast number of secondary metabolites. These range from simple to highly-complex structures, some of which have found use in clinical practice due to their outstanding biological properties. Methods for the isolation and structural characterization of such molecules have experienced great advances over the last decade, allowing the elucidation of complex structures, even isolated at the nanomole scale. This Special Issue will cover aspects related to this field, highlighting papers on new isolation procedures or on the development of new methodology to tackle challenging structural elucidation problems. Articles covering the isolation and characterization of new marine metabolites, especially those with interesting biological properties, will also be considered.

Dr. Fernando Reyes
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 papers will be 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 1800 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.

Published Papers (4 papers)

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Research

Open AccessArticle Innovative Approach to Sustainable Marine Invertebrate Chemistry and a Scale-Up Technology for Open Marine Ecosystems
Mar. Drugs 2018, 16(5), 152; https://doi.org/10.3390/md16050152
Received: 3 April 2018 / Revised: 28 April 2018 / Accepted: 4 May 2018 / Published: 6 May 2018
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Abstract
Isolation of marine compounds from living invertebrates represents a major challenge for sustainable and environmentally friendly exploitation of marine bio-resources. To develop innovative technology to trap invertebrate compounds in the open sea, the proof of concept of a system combining external continuous circulation
[...] Read more.
Isolation of marine compounds from living invertebrates represents a major challenge for sustainable and environmentally friendly exploitation of marine bio-resources. To develop innovative technology to trap invertebrate compounds in the open sea, the proof of concept of a system combining external continuous circulation of water with XAD-amberlite solid-phase extraction was validated in an aquarium. In this work, we reported the elicitation of guanidine alkaloid production of Crambe crambe in the presence of Anemonia sulcata, both collected from the Mediterranean Sea. Besides the previously reported crambescidin 359 (1), and crambescidin acid (2), three new compounds were isolated; one carboxylated analog of 1 named crambescidin 401 (3), and two analogs of crambescin B, crambescin B 281 (4) and crambescin B 253 (5). Based on these results, a technology named Somartex® for “Self Operating MARine Trapping Extractor” was patented and built to transfer the concept from closed aquarium systems to open marine ecosystems. Full article
(This article belongs to the Special Issue Isolation and Structure Elucidation of Marine Secondary Metabolites)
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Graphical abstract

Open AccessFeature PaperArticle Phocoenamicins B and C, New Antibacterial Spirotetronates Isolated from a Marine Micromonospora sp.
Mar. Drugs 2018, 16(3), 95; https://doi.org/10.3390/md16030095
Received: 20 February 2018 / Revised: 13 March 2018 / Accepted: 14 March 2018 / Published: 16 March 2018
PDF Full-text (2540 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Phocoenamicins B and C (1 and 2), together with the known spirotetronate phocoenamicin (3), were isolated from cultures of Micromonospora sp. The acetone extract from a culture of this strain, isolated from marine sediments collected in the Canary Islands,
[...] Read more.
Phocoenamicins B and C (1 and 2), together with the known spirotetronate phocoenamicin (3), were isolated from cultures of Micromonospora sp. The acetone extract from a culture of this strain, isolated from marine sediments collected in the Canary Islands, displayed activity against methicillin-resistant Staphylococcus aureus (MRSA), Mycobacterium tuberculosis H37Ra and Mycobacterium bovis. Bioassay-guided fractionation of this extract using SP207ss column chromatography and preparative reversed-phased HPLC led to the isolation of the new compounds 1 and 2 belonging to the spirotetronate class of polyketides. Their structures were determined using a combination of HRMS, 1D and 2D NMR experiments and comparison with the spectra reported for phocoenamicin. Antibacterial activity tests of the pure compounds against these pathogens revealed minimal inhibitory concentration (MIC) values ranging from 4 to 64 µg/mL for MRSA, and 16 to 32 µg/mL for M. tuberculosis H37Ra, with no significant activity found against M. bovis and vancomycin-resistant Enterococcus faecium (VRE) at concentrations below 128 µg/mL, and weak activity detected against Bacillus subtilis grown on agar plates. Full article
(This article belongs to the Special Issue Isolation and Structure Elucidation of Marine Secondary Metabolites)
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Graphical abstract

Open AccessArticle Ecdysonelactones, Ecdysteroids from the Tropical Eastern Pacific Zoantharian Antipathozoanthus hickmani
Mar. Drugs 2018, 16(2), 58; https://doi.org/10.3390/md16020058
Received: 3 January 2018 / Revised: 1 February 2018 / Accepted: 8 February 2018 / Published: 11 February 2018
Cited by 1 | PDF Full-text (763 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Despite a large occurrence, especially over the Pacific Ocean, the chemical diversity of marine invertebrates belonging to the order Zoantharia is largely underexplored. For the two species of the genus Antipathozoanthus no chemical study has been reported so far. The first chemical investigation
[...] Read more.
Despite a large occurrence, especially over the Pacific Ocean, the chemical diversity of marine invertebrates belonging to the order Zoantharia is largely underexplored. For the two species of the genus Antipathozoanthus no chemical study has been reported so far. The first chemical investigation of Antipathozoanthus hickmani collected at the Marine Protected Area “El Pelado”, Santa Elena, Ecuador, led to the isolation of four new ecdysteroid derivatives named ecdysonelactones. The structures of ecdysonelactones A–D (14) were determined based on their spectroscopy data, including 1D and 2D NMR and HRMS. The four compounds of this family of ecdysteroids feature an unprecedented γ-lactone fused at the C-2/C-3 position of ring A. These derivatives exhibited neither antimicrobial nor cytotoxic activities. Full article
(This article belongs to the Special Issue Isolation and Structure Elucidation of Marine Secondary Metabolites)
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Graphical abstract

Open AccessArticle Identification, Characteristics and Mechanism of 1-Deoxy-N-acetylglucosamine from Deep-Sea Virgibacillus dokdonensis MCCC 1A00493
Mar. Drugs 2018, 16(2), 52; https://doi.org/10.3390/md16020052
Received: 2 December 2017 / Revised: 1 February 2018 / Accepted: 2 February 2018 / Published: 7 February 2018
PDF Full-text (2377 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Xanthomonas oryzae pv. oryzae, which causes rice bacterial blight, is one of the most destructive pathogenic bacteria. Biological control against plant pathogens has recently received increasing interest. 1-Deoxy-N-acetylglucosamine (1-DGlcNAc) was extracted from the supernatant of Virgibacillus dokdonensis MCCC 1A00493 fermentation
[...] Read more.
Xanthomonas oryzae pv. oryzae, which causes rice bacterial blight, is one of the most destructive pathogenic bacteria. Biological control against plant pathogens has recently received increasing interest. 1-Deoxy-N-acetylglucosamine (1-DGlcNAc) was extracted from the supernatant of Virgibacillus dokdonensis MCCC 1A00493 fermentation through antibacterial bioassay-guided isolation. Its structure was elucidated by LC/MS, NMR, chemical synthesis and time-dependent density functional theory (TD-DFT) calculations. 1-DGlcNAc specifically suppressed X. oryzae pv. oryzae PXO99A (MIC was 23.90 μg/mL), but not other common pathogens including Xanthomonas campestris pv. campestris str.8004 and Xanthomonas oryzae pv. oryzicola RS105. However, its diastereomer (2-acetamido-1,5-anhydro-2-deoxy-d-mannitol) also has no activity to X. oryzae pv. oryzae. This result suggested that activity of 1-DGlcNAc was related to the difference in the spatial conformation of the 2-acetamido moiety, which might be attributed to their different interactions with a receptor. Eighty-four unique proteins were found in X. oryzae pv. oryzae PXO99A compared with the genome of strains8004 and RS105 by blastp. There may be unique interactions between 1-DGlcNAc and one or more of these unique proteins in X. oryzae pv. oryzae. Quantitative real-time PCR and the pharmMapper server indicated that proteins involved in cell division could be the targets in PXO99A. This research suggested that specificity of active substance was based on the active group and spatial conformation selection, and these unique proteins could help to reveal the specific mechanism of action of 1-DGlcNAc against PXO99A. Full article
(This article belongs to the Special Issue Isolation and Structure Elucidation of Marine Secondary Metabolites)
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