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Marine Drugs
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Total Synthesis and Synthetic Approaches towards Marine Bioactive Natural Products...
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Total Synthesis and Synthetic Approaches towards Marine Bioactive Natural Products and Analogues

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 2024) | Viewed by 11790

Special Issue Editors

Prof. Dr. Francisco Sarabia

E-Mail Website
Guest Editor
Department of Organic Chemistry, Faculty of Science, University of Málaga, 29071 Málaga, Spain
Interests: natural products; bioactive compounds; total synthesis; antitumor; antibiotics; cyclodepsipeptides; cyclopeptides
Special Issues, Collections and Topics in MDPI journals
Dr. Ivan Cheng-Sanchez

E-Mail Website
Guest Editor
Department of Chemistry, University of Zurich, Zurich, Switzerland
Interests: total synthesis; natural products; medicinal chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Marine organisms have proven to be a rich and powerful source of bioactive natural products featuring diverse and complex molecular architectures and a broad array of biological activities. Since the importance and value of these natural products has become clear in biology and medicine, total synthesis is now essential for the development of such secondary metabolites, either as biological tools or as potential leads in medicine. The general problem that represents scarce and difficult-to-access marine natural products, as well as their structural determination, can be overcome via total synthesis. In addition, total synthesis and synthetic approaches, such as semisynthesis, allow access to analogues for structure–activity relationship (SAR) and drug discovery studies. Therefore, given the importance of this field, this Special Issue will cover total synthesis and the synthetic approaches to reflect the major role of this discipline and its implications in the development of bioactive compounds of marine origin.

Prof. Dr. Francisco Sarabia
Dr. Ivan Cheng-Sanchez
Guest Editors

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

  • total synthesis
  • marine natural products
  • biological activity
  • synthetic approaches
  • semisynthesis
  • analogues
  • structure–activity relationships
  • structural determination

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Published Papers (6 papers)

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Research

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13 pages, 1730 KiB  
Article
Total Synthesis and Biological Profiling of Putative (±)-Marinoaziridine B and (±)-N-Methyl Marinoaziridine A
by Anđela Buljan, Višnja Stepanić, Ana Čikoš, Sanja Babić Brčić, Krunoslav Bojanić and Marin Roje
Mar. Drugs 2024, 22(7), 310; https://doi.org/10.3390/md22070310 - 3 Jul 2024
Viewed by 1473
Abstract
The total synthesis of two new marine natural products, (±)-marinoaziridine B 7 and (±)-N-methyl marinoaziridine A 8, was accomplished. The (±)-marinoaziridine 7 was prepared in a six-step linear sequence with a 2% overall yield. The key steps in our strategy [...] Read more.
The total synthesis of two new marine natural products, (±)-marinoaziridine B 7 and (±)-N-methyl marinoaziridine A 8, was accomplished. The (±)-marinoaziridine 7 was prepared in a six-step linear sequence with a 2% overall yield. The key steps in our strategy were the preparation of the chiral epoxide (±)-5 using the Johnson Corey Chaykovsky reaction, followed by the ring-opening reaction and the Staudinger reaction. The N,N-dimethylation of compound (±)-7 gives (±)-N-methyl marinoaziridine A 8. The NMR spectra of synthetized (±)-marinoaziridine B 7 and isolated natural product did not match. The compounds are biologically characterized using relevant in silico, in vitro and in vivo methods. In silico ADMET and bioactivity profiling predicted toxic and neuromodulatory effects. In vitro screening by MTT assay on three cell lines (MCF-7, H-460, HEK293T) showed that both compounds exhibited moderate to strong antiproliferative and cytotoxic effects. Antimicrobial tests on bacterial cultures of Escherichia coli and Staphylococcus aureus demonstrated the dose-dependent inhibition of the growth of both bacteria. In vivo toxicological tests were performed on zebrafish Danio rerio and showed a significant reduction of zebrafish mortality due to N-methylation in (±)-8. Full article
(This article belongs to the Special Issue Total Synthesis and Synthetic Approaches towards Marine Bioactive Natural Products and Analogues)
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12 pages, 1352 KiB  
Article
Semisynthesis and Cytotoxic Evaluation of an Ether Analogue Library Based on a Polyhalogenated Diphenyl Ether Scaffold Isolated from a Lamellodysidea Sponge
by Kelsey S. Ramage, Aaron Lock, Jonathan M. White, Merrick G. Ekins, Milton J. Kiefel, Vicky M. Avery and Rohan A. Davis
Mar. Drugs 2024, 22(1), 33; https://doi.org/10.3390/md22010033 - 3 Jan 2024
Cited by 1 | Viewed by 2178
Abstract
The known oxygenated polyhalogenated diphenyl ether, 2-(2′,4′-dibromophenoxy)-3,5-dibromophenol (1), with previously reported activity in multiple cytotoxicity assays was isolated from the sponge Lamellodysidea sp. and proved to be an amenable scaffold for semisynthetic library generation. The phenol group of 1 was targeted [...] Read more.
The known oxygenated polyhalogenated diphenyl ether, 2-(2′,4′-dibromophenoxy)-3,5-dibromophenol (1), with previously reported activity in multiple cytotoxicity assays was isolated from the sponge Lamellodysidea sp. and proved to be an amenable scaffold for semisynthetic library generation. The phenol group of 1 was targeted to generate 12 ether analogues in low-to-excellent yields, and the new library was fully characterized by NMR, UV, and MS analyses. The chemical structures for 2, 8, and 9 were additionally determined via single-crystal X-ray diffraction analysis. All natural and semisynthetic compounds were evaluated for their ability to inhibit the growth of DU145, LNCaP, MCF-7, and MDA-MB-231 cancer cell lines. Compound 3 was shown to have near-equivalent activity compared to scaffold 1 in two in vitro assays, and the activity of the compounds with an additional benzyl ring appeared to be reliant on the presence and position of additional halogens. Full article
(This article belongs to the Special Issue Total Synthesis and Synthetic Approaches towards Marine Bioactive Natural Products and Analogues)
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11 pages, 1124 KiB  
Article
Oxidative Cyclization at ortho-Position of Phenol: Improved Total Synthesis of 3-(Phenethylamino)demethyl(oxy)aaptamine
by Yuki Nakatani, Risa Kimura, Tomoyo Kimata and Naoyuki Kotoku
Mar. Drugs 2023, 21(5), 311; https://doi.org/10.3390/md21050311 - 19 May 2023
Cited by 1 | Viewed by 1821
Abstract
A shorter synthesis of the demethyl(oxy)aaptamine skeleton was developed via oxidative intramolecular cyclization of 1-(2-azidoethyl)-6-methoxyisoquinolin-7-ol followed by dehydrogenation with a hypervalent iodine reagent. This is the first example of oxidative cyclization at the ortho-position of phenol that does not involve spiro-cyclization, resulting [...] Read more.
A shorter synthesis of the demethyl(oxy)aaptamine skeleton was developed via oxidative intramolecular cyclization of 1-(2-azidoethyl)-6-methoxyisoquinolin-7-ol followed by dehydrogenation with a hypervalent iodine reagent. This is the first example of oxidative cyclization at the ortho-position of phenol that does not involve spiro-cyclization, resulting in the improved total synthesis of 3-(phenethylamino)demethyl(oxy)aaptamine, a potent anti-dormant mycobacterial agent. Full article
(This article belongs to the Special Issue Total Synthesis and Synthetic Approaches towards Marine Bioactive Natural Products and Analogues)
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Review

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18 pages, 10784 KiB  
Review
Dimeric (Poly)Hydroxynaphthazarins, Metabolites of Echinoderms and Lichens: The History of the Synthesis and Structure Elucidation
by Dmitry N. Pelageev, Ksenia L. Borisova and Victor Ph. Anufriev
Mar. Drugs 2023, 21(7), 407; https://doi.org/10.3390/md21070407 - 19 Jul 2023
Viewed by 1194
Abstract
This review provides information on the synthesis and revision of the structures of natural dimeric (poly)hydroxynaphthazarins, metabolites of echinoderms and lichens, and on the refinement of the direction and mechanism of reactions in the synthesis of some of these compounds. Full article
(This article belongs to the Special Issue Total Synthesis and Synthetic Approaches towards Marine Bioactive Natural Products and Analogues)
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15 pages, 3683 KiB  
Review
An Overview of Aplysinopsins: Synthesis and Biological Activities
by Eslam R. El-Sawy and Gilbert Kirsch
Mar. Drugs 2023, 21(5), 268; https://doi.org/10.3390/md21050268 - 26 Apr 2023
Cited by 2 | Viewed by 1596
Abstract
Marine products are among the most promising sources of biologically active molecules. Aplysinopsins, tryptophan-derived marine natural products, were isolated from different natural marine sources including sponges, stony corals (hard corals) especially genus scleractinian, as well as sea anemone, in addition to one nudibranch. [...] Read more.
Marine products are among the most promising sources of biologically active molecules. Aplysinopsins, tryptophan-derived marine natural products, were isolated from different natural marine sources including sponges, stony corals (hard corals) especially genus scleractinian, as well as sea anemone, in addition to one nudibranch. Aplysinopsins were reported to be isolated from different marine organisms related to various geographic areas such as Pacific, Indonesia, Caribbean, and Mediterranean regions. This review gives an up-to-date overview of marine alkaloid aplysinopsins: their various sources, their synthesis, and the fact that many aplysinopsin derivatives are biologically active compounds. Full article
(This article belongs to the Special Issue Total Synthesis and Synthetic Approaches towards Marine Bioactive Natural Products and Analogues)
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Other

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17 pages, 2825 KiB  
Perspective
Marine Puupehenone and Puupehedione: Synthesis and Future Perspectives
by Antonio Rosales Martínez and Ignacio Rodríguez-García
Mar. Drugs 2023, 21(6), 322; https://doi.org/10.3390/md21060322 - 26 May 2023
Cited by 2 | Viewed by 1591
Abstract
Puupehenone and puupehedione are natural products isolated from marine organisms. These compounds display a broad spectrum of biological activities, the in vitro antitubercular activity of puupehenone being a stand out, and are equipped with an interesting structural complexity. These products have served to [...] Read more.
Puupehenone and puupehedione are natural products isolated from marine organisms. These compounds display a broad spectrum of biological activities, the in vitro antitubercular activity of puupehenone being a stand out, and are equipped with an interesting structural complexity. These products have served to stimulate the continual interest of the synthetic community. The first part of this article is a review of their total synthesis, using natural compounds which have the potential to be transformed into these marine compounds as starting materials; the synthetic routes employed to generate the basic skeleton; and the advances made to synthesize the pyran C ring with the required diastereoselectivity to obtain the natural products. Finally, this perspective shows a personal reflection of the authors on a possible unified and efficient retrosynthetic route that could allow easy access to these natural products, as well as their epimers at the C8 carbon and which could be used to address future biological issues in the production of pharmacologically active compounds. Full article
(This article belongs to the Special Issue Total Synthesis and Synthetic Approaches towards Marine Bioactive Natural Products and Analogues)
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