Marine Macrolides: Structure, Biosynthetic Aspects and Potential as a New Drugs

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

Deadline for manuscript submissions: closed (31 December 2020) | Viewed by 20439

Special Issue Editor

Centro de Investigacións Científicas Avanzadas (CICA) e Departamento de Química, Facultade de Ciencias, Universidade de A Coruña, 15071 A Coruña, Spain
Interests: organic structure elucidation; stereochemistry and configurational analysis by NMR and computational methods; organic synthesis of natural products; siderophores; pathogenic bacteria in aquaculture
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Special Issue Information

Dear Colleagues,

Macrolides are common structural scaffolds widespread in nature. The structures of these large-ring lactones usually are very difficult to elucidate, either for the minute amounts isolated or by their intricate flexible and highly substituted skeletons. Marine organism and their symbionts have produced a large number of structurally diverse macrolides with important biological activities. The sponges are the most important source of this type of secondary metabolites; however, dinoflagellate, algae, and tunicates have been also studied and, from a chemical structure point of view, very interesting polyene backbones have been discovered.

Good examples of known marine macrolides are the bryostatins, the spongistatins, or the halichondrins, the first marine macrolides established as powerful antimitotic agents. Since then there has been extensive attention in the halichondrin family. This interest is, without doubt, due to their outstanding potential as therapeutic agent demonstrated with the development of the already approved drug erybulin mesylate (Halaven™). This halichondrin B derivative is being used for metastatic breast cancer in patients who have received at least two prior chemotherapy regimens for late stage disease.

With these precedents, the goals of the proposed Special Issue will be to show marine macrolides from three different points of view: (a) Structural elucidation of their chemical structures, (b) description of their biological activities (c) the aspects related to the biosynthesis. Synthetic approaches to their skeletons will be also considered.

Prof. Jaime Rodríguez
Guest Editor

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Published Papers (3 papers)

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Research

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10 pages, 1648 KiB  
Article
Desertomycin G, a New Antibiotic with Activity against Mycobacterium tuberculosis and Human Breast Tumor Cell Lines Produced by Streptomyces althioticus MSM3, Isolated from the Cantabrian Sea Intertidal Macroalgae Ulva sp.
by Alfredo F. Braña, Aida Sarmiento-Vizcaíno, Ignacio Pérez-Victoria, Jesús Martín, Luis Otero, Juan José Palacios-Gutiérrez, Jonathan Fernández, Yamina Mohamedi, Tania Fontanil, Marina Salmón, Santiago Cal, Fernando Reyes, Luis A. García and Gloria Blanco
Mar. Drugs 2019, 17(2), 114; https://doi.org/10.3390/md17020114 - 12 Feb 2019
Cited by 32 | Viewed by 6959
Abstract
The isolation and structural elucidation of a structurally new desertomycin, designated as desertomycin G (1), with strong antibiotic activity against several clinically relevant antibiotic resistant pathogens are described herein. This new natural product was obtained from cultures of the marine actinomycete [...] Read more.
The isolation and structural elucidation of a structurally new desertomycin, designated as desertomycin G (1), with strong antibiotic activity against several clinically relevant antibiotic resistant pathogens are described herein. This new natural product was obtained from cultures of the marine actinomycete Streptomyces althioticus MSM3, isolated from samples of the intertidal seaweed Ulva sp. collected in the Cantabrian Sea (Northeast Atlantic Ocean). Particularly interesting is its strong antibiotic activity against Mycobacterium tuberculosis clinical isolates, resistant to antibiotics in clinical use. To the best of our knowledge, this is the first report on a member of the desertomycin family displaying such activity. Additionally, desertomycin G shows strong antibiotic activities against other relevant Gram-positive clinical pathogens such as Corynebacterium urealyticum, Staphylococcus aureus, Streptococcus pneumoniae, Streptococcus pyogenes, Enterococcus faecium, Enterococcus faecalis, and Clostridium perfringens. Desertomycin G also displays moderate antibiotic activity against relevant Gram-negative clinical pathogens such as Bacteroides fragilis, Haemophilus influenzae and Neisseria meningitidis. In addition, the compound affects viability of tumor cell lines, such as human breast adenocarcinoma (MCF-7) and colon carcinoma (DLD-1), but not normal mammary fibroblasts. Full article
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Review

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25 pages, 9923 KiB  
Review
Marine Macrolides with Antibacterial and/or Antifungal Activity
by Tomasz M. Karpiński
Mar. Drugs 2019, 17(4), 241; https://doi.org/10.3390/md17040241 - 23 Apr 2019
Cited by 57 | Viewed by 7703
Abstract
Currently, the increasing resistance of microorganisms to antibiotics is a serious problem. Marine organisms are the source of thousands of substances, which also have antibacterial and antifungal effects. Among them, marine macrolides are significant. In this review, the antibacterial and/or antifungal activities of [...] Read more.
Currently, the increasing resistance of microorganisms to antibiotics is a serious problem. Marine organisms are the source of thousands of substances, which also have antibacterial and antifungal effects. Among them, marine macrolides are significant. In this review, the antibacterial and/or antifungal activities of 34 groups of marine macrolides are presented. Exemplary groups are chalcomycins, curvulides, halichondramides, lobophorins, macrolactins, modiolides, scytophycins, spongistatins, or zearalanones. In the paper, 74 antibiotics or their analog sets, among which 29 with antifungal activity, 25 that are antibacterial, and 20 that are both antifungal and antibacterial are summarized. Also, 36 macrolides or their sets are produced by bacteria, 18 by fungi, ten by sponges, seven by algae, two by porifera, and one by nudibranch. Moreover, the chemical structures of representatives from each of the 34 groups of these antibiotics are presented. To summarize, marine organisms are rich in natural macrolides. Some of these may be used in the future in the treatment of bacterial and fungal infections. Marine macrolides can also be potential drugs applicable against pathogens resistant to currently known antibiotics. Full article
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15 pages, 3009 KiB  
Review
Marine Spirotetronates: Biosynthetic Edifices That Inspire Drug Discovery
by Alexander A. Braddock and Emmanuel A. Theodorakis
Mar. Drugs 2019, 17(4), 232; https://doi.org/10.3390/md17040232 - 19 Apr 2019
Cited by 17 | Viewed by 5302
Abstract
Spirotetronates are actinomyces-derived polyketides that possess complex structures and exhibit potent and unexplored bioactivities. Due to their anticancer and antimicrobial properties, they have potential as drug hits and deserve further study. In particular, abyssomicin C and tetrocarcin A have shown significant promise against [...] Read more.
Spirotetronates are actinomyces-derived polyketides that possess complex structures and exhibit potent and unexplored bioactivities. Due to their anticancer and antimicrobial properties, they have potential as drug hits and deserve further study. In particular, abyssomicin C and tetrocarcin A have shown significant promise against antibiotic-resistant S. aureus and tuberculosis, as well as for the treatment of various lymphomas and solid tumors. Improved synthetic routes to these compounds, particularly the class II spirotetronates, are needed to access sufficient quantities for structure optimization and clinical applications. Full article
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