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

Deadline for manuscript submissions: closed (8 April 2022) | Viewed by 41217

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Prof. Dr. Jaime Rodríguez

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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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Dr. Fernando Reyes

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Fundación MEDINA, Avda del Conocimiento 34, Parque Tecnológico Ciencias Salud, E-18016 Granada, Spain
Interests: chromatography; mass spectrometry; liquid chromatography; natural product chemistry; nuclear magnetic resonance; bioactivity; medicinal chemistry; NMR structure elucidation; LC-MS/MS; MIC; compound isolation; structure elucidation; natural products; metabolite identification; alkaloids; pharmacognosy; bioassays; HPLC-UV; bioactive secondary metabolites; marine natural products
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Dr. Javier Fernández

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Instituto Universitario de Bio-Orgáncia Antonio González (IUBOAG), Universidad de la Laguna (ULL), 38206 San Cristobal de La Laguna, Spain
Interests: marine natural products; marine toxins; marine polyether; marine microalgae; biosynthesis; Laurencia; antiparasitic substances; phosphatase inhibitors
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Special Issue Information

Dear Colleagues,

Spain is surrounded for near 8000 km of coastline, which makes it one of the most important countries to study the chemistry and the biology of marine life. Compounds from classic marine natural product studies are dated from the beginning of the 1970s, with the first publications from marine organisms of the Canary Atlantic. These papers were published from one of the pioneers of marine natural products in Spain, late Prof. Antonio Gonzalez at the University of La Laguna in the Canary Islands, who set the precedent for some other research groups from the University of Cadiz, University of Salamanca, University of Santiago de Compostela, or CSIC.

In this Special Issue on “Marine Drugs Research in Spain”, we will pay tribute to these research schools, providing Spanish researchers and institutions with a platform for publishing biomedical and chemical studies of substances of marine origin. We welcome papers focused on structure elucidation and the synthesis of marine compounds, or any biological aspects about marine macro or microorganisms.

Prof. Dr. Jaime Rodríguez
Dr. Fernando Reyes
Dr. Javier Fernández
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

Structure elucidation
Synthesis
Bioactive compounds

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Published Papers (12 papers)

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Research

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23 pages, 4014 KiB

Open AccessArticle

Exploring Micromonospora as Phocoenamicins Producers

by Maria Kokkini, Cristina González Heredia, Daniel Oves-Costales, Mercedes de la Cruz, Pilar Sánchez, Jesús Martín, Francisca Vicente, Olga Genilloud and Fernando Reyes

Mar. Drugs 2022, 20(12), 769; https://doi.org/10.3390/md20120769 - 7 Dec 2022

Cited by 4 | Viewed by 2532

Abstract

Over the past few years, new technological and scientific advances have reinforced the field of natural product discovery. The spirotetronate class of natural products has recently grown with the discovery of phocoenamicins, natural actinomycete derived compounds that possess different antibiotic activities. Exploring the MEDINA’s strain collection, 27 actinomycete strains, including three marine-derived and 24 terrestrial strains, were identified as possible phocoenamicins producers and their taxonomic identification by 16S rDNA sequencing showed that they all belong to the Micromonospora genus. Using an OSMAC approach, all the strains were cultivated in 10 different media each, resulting in 270 fermentations, whose extracts were analyzed by LC-HRMS and subjected to High-throughput screening (HTS) against methicillin-resistant Staphylococcus aureus (MRSA), Mycobacterium tuberculosis H37Ra and Mycobacterium bovis. The combination of LC-UV-HRMS analyses, metabolomics analysis and molecular networking (GNPS) revealed that they produce several related spirotetronates not disclosed before. Variations in the culture media were identified as the most determining factor for phocoenamicin production and the best producer strains and media were established. Herein, we reported the chemically diverse production and metabolic profiling of Micromonospora sp. strains, including the known phocoenamicins and maklamicin, reported for the first time as being related to this family of compounds, as well as the bioactivity of their crude extracts. Although our findings do not confirm previous statements about phocoenamicins production only in unique marine environments, they have identified marine-derived Micromonospora species as the best producers of phocoenamicins in terms of both the abundance in their extracts of some major members of the structural class and the variety of molecular structures produced. Full article

(This article belongs to the Special Issue Marine Drugs Research in Spain)

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17 pages, 2085 KiB

Open AccessArticle

Carbon Source Influences Antioxidant, Antiglycemic, and Antilipidemic Activities of Haloferax mediterranei Carotenoid Extracts

by Micaela Giani, Luigia Gervasi, Monica Rosa Loizzo and Rosa María Martínez-Espinosa

Mar. Drugs 2022, 20(11), 659; https://doi.org/10.3390/md20110659 - 24 Oct 2022

Cited by 25 | Viewed by 2881

Abstract

Haloarchaeal carotenoids have attracted attention lately due to their potential antioxidant activity. This work studies the effect of different concentrations of carbon sources on cell growth and carotenoid production. Carotenoid extract composition was characterized by HPLC-MS. Antioxidant activity of carotenoid extracts obtained from cell cultures grown under different nutritional conditions was determined by 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and 1,1-diphenyl-2-picrylhydrazyl (DPPH), Ferric Reducing Ability Power (FRAP) and β-carotene bleaching assays. The ability of these carotenoid extracts to inhibit α-glucosidase, α-amylase, and lipase enzymes was also assessed to determine if they could be used to reduce blood glucose and lipid absorption. The maximum production of carotenoids (92.2 µg/mL) was observed combining 12.5% inorganic salts and 2.5% of glucose/starch. Antioxidant, hypoglycemic, and antilipidemic studies showed that higher carbon availability in the culture media leads to changes in the extract composition, resulting in more active haloarchaeal carotenoid extracts. Carotenoid extracts obtained from high-carbon-availability cell cultures presented higher proportions of all-trans-bacterioruberin, 5-cis-bacterioruberin, and a double isomeric bacterioruberin, whereas the presence 9-cis-bacterioruberin and 13-cis-bacterioruberin decreased. The production of haloarchaeal carotenoids can be successfully optimized by changing nutritional conditions. Furthermore, carotenoid composition can be altered by modifying carbon source concentration. These natural compounds are very promising in food and nutraceutical industries. Full article

(This article belongs to the Special Issue Marine Drugs Research in Spain)

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17 pages, 4036 KiB

Open AccessArticle

Connection of Isolated Stereoclusters by Combining ¹³C-RCSA, RDC, and J-Based Configurational Analyses and Structural Revision of a Tetraprenyltoluquinol Chromane Meroterpenoid from Sargassum muticum

by Juan Carlos C. Fuentes-Monteverde, Nilamoni Nath, Abel M. Forero, Elena M. Balboa, Armando Navarro-Vázquez, Christian Griesinger, Carlos Jiménez and Jaime Rodríguez

Mar. Drugs 2022, 20(7), 462; https://doi.org/10.3390/md20070462 - 18 Jul 2022

Cited by 3 | Viewed by 3011

Abstract

The seaweed Sargassum muticum, collected on the southern coast of Galicia, yielded a tetraprenyltoluquinol chromane meroditerpene compound known as 1b, whose structure is revised. The relative configuration of 1b was determined by J-based configurational methodology combined with an iJ/DP4 statistical analysis and further confirmed by measuring two anisotropic properties: carbon residual chemical shift anisotropies (¹³C-RCSAs) and one-bond ¹H-¹³C residual dipolar couplings (¹D_CH-RDCs). The absolute configuration of 1b was deduced by ECD/OR/TD-DFT methods and established as 3R,7S,11R. Full article

(This article belongs to the Special Issue Marine Drugs Research in Spain)

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16 pages, 1964 KiB

Open AccessArticle

S-Assimilation Influences in Carrageenan Biosynthesis Genes during Ethylene-Induced Carposporogenesis in Red Seaweed Grateloupia imbricata

by Diana del Rosario-Santana, Rafael R. Robaina and Pilar Garcia-Jimenez

Mar. Drugs 2022, 20(7), 436; https://doi.org/10.3390/md20070436 - 29 Jun 2022

Cited by 3 | Viewed by 2386

Abstract

The synthesis of cell-wall sulfated galactans proceeds through UDP galactose, a major nucleotide sugar in red seaweed, whilst sulfate is transported through S-transporters into algae. Moreover, synthesis of ethylene, a volatile plant growth regulator that plays an important role in red seaweed reproduction, occurs through S-adenosyl methionine. This means that sulfur metabolism is involved in reproduction events as well as sulfated galactan synthesis of red seaweed. In this work we study the effects of methionine and MgSO₄ on gene expression of polygalactan synthesis through phosphoglucomutase (PGM) and galactose 1 phosphate uridyltransferase (GALT) and of sulfate assimilation (S-transporter and sulfate adenylyltransferase, SAT) using treatment of ethylene for 15 min, which elicited cystocarp development in Grateloupia imbricata. Also, expressions of carbohydrate sulfotransferase and galactose-6-sulfurylase in charge of the addition and removal of sulfate groups to galactans backbone were examined. Outstanding results occurred in the presence of methionine, which provoked an increment in transcript number of genes encoding S-transporter and assimilation compared to controls regardless of the development stage of thalli. Otherwise, methionine diminished the transcript levels of PGM and GALT and expressions are associated with the fertilization stage of thalli of G. imbricata. As opposite, methionine and MgSO₄ did not affect the transcript number of carbohydrate sulfotransferase and galactose-6-sulfurylase. Nonetheless, differential expression was obtained for sulfurylases according to the development stages of thalli of G. imbricata. Full article

(This article belongs to the Special Issue Marine Drugs Research in Spain)

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12 pages, 1338 KiB

Open AccessArticle

Antimicrobial Diterpene Alkaloids from an Agelas citrina Sponge Collected in the Yucatán Peninsula

by Dawrin Pech-Puch, Abel M. Forero, Juan Carlos Fuentes-Monteverde, Cristina Lasarte-Monterrubio, Marta Martinez-Guitian, Carlos González-Salas, Sergio Guillén-Hernández, Harold Villegas-Hernández, Alejandro Beceiro, Christian Griesinger, Jaime Rodríguez and Carlos Jiménez

Mar. Drugs 2022, 20(5), 298; https://doi.org/10.3390/md20050298 - 28 Apr 2022

Cited by 10 | Viewed by 3106

Abstract

Three new diterpene alkaloids, (+)-8-epiagelasine T (1), (+)-10-epiagelasine B (2), and (+)-12-hydroxyagelasidine C (3), along with three known compounds, (+)-ent-agelasine F (4), (+)-agelasine B (5), and (+)-agelasidine C (6), were isolated from the sponge Agelas citrina, collected on the coasts of the Yucatán Peninsula (Mexico). Their chemical structures were elucidated by 1D and 2D NMR spectroscopy, HRESIMS techniques, and a comparison with literature data. Although the synthesis of (+)-ent-agelasine F (4) has been previously reported, this is the first time that it was isolated as a natural product. The evaluation of the antimicrobial activity against the Gram-positive pathogens Staphylococcus aureus, Streptococcus pneumoniae, Enterococcus faecalis showed that all of them were active, with (+)-10-epiagelasine B (2) being the most active compound with an MIC in the range of 1–8 µg/mL. On the other hand, the Gram-negative pathogenes Acinetobacter baumannii, Pseudomonas aeruginosa, and Klebsiella pneumoniae were also evaluated, and only (+)-agelasine B (5) showed a moderate antibacterial activity with a MIC value of 16 μg/mL. Full article

(This article belongs to the Special Issue Marine Drugs Research in Spain)

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14 pages, 2775 KiB

Open AccessArticle

Conceptual DFT-Based Computational Peptidology, Pharmacokinetics Study and ADMET Report of the Veraguamides A–G Family of Marine Natural Drugs

by Norma Flores-Holguín, Joaquín Ortega-Castro, Juan Frau and Daniel Glossman-Mitnik

Mar. Drugs 2022, 20(2), 97; https://doi.org/10.3390/md20020097 - 24 Jan 2022

Cited by 10 | Viewed by 3019

Abstract

As a continuation of our research on the chemical reactivity, pharmacokinetics and ADMET properties of cyclopeptides of marine origin with potential therapeutic abilities, in this work our already presented integrated molecular modeling protocol has been used for the study of the chemical reactivity and bioactivity properties of the Veraguamides A–G family of marine natural drugs. This protocol results from the estimation of the conceptual density functional theory (CDFT) chemical reactivity descriptors together with several chemoinformatics tools commonly considered within the process of development of new therapeutic drugs. CP-CDFT is a branch of computational chemistry and molecular modeling dedicated to the study of peptides, and it is a protocol that allows the estimation with great accuracy of the CDFT-based reactivity descriptors and the associated physical and chemical properties, which can aid in determining the ability of the studied peptides to behave as potential useful drugs. Moreover, the superiority of the MN12SX density functional over other long-range corrected density functionals for the prediction of chemical and physical properties in the presence of water as the solvent is clearly demonstrated. The research was supplemented with an investigation of the bioactivity of the molecular systems and their ADMET (absorption, distribution, metabolism, excretion, and toxicity) parameters, as is customary in medicinal chemistry. Some instances of the CDFT-based chemical reactivity descriptors’ capacity to predict the pKas of peptides as well as their potential as AGE inhibitors are also shown. Full article

(This article belongs to the Special Issue Marine Drugs Research in Spain)

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26 pages, 2521 KiB

Open AccessEditor’s ChoiceArticle

Computer-Aided Drug Design (CADD) to De-Orphanize Marine Molecules: Finding Potential Therapeutic Agents for Neurodegenerative and Cardiovascular Diseases

by Laura Llorach-Pares, Alfons Nonell-Canals, Conxita Avila and Melchor Sanchez-Martinez

Mar. Drugs 2022, 20(1), 53; https://doi.org/10.3390/md20010053 - 5 Jan 2022

Cited by 7 | Viewed by 4838

Abstract

Computer-aided drug design (CADD) techniques allow the identification of compounds capable of modulating protein functions in pathogenesis-related pathways, which is a promising line on drug discovery. Marine natural products (MNPs) are considered a rich source of bioactive compounds, as the oceans are home to much of the planet’s biodiversity. Biodiversity is directly related to chemodiversity, which can inspire new drug discoveries. Therefore, natural products (NPs) in general, and MNPs in particular, have been used for decades as a source of inspiration for the design of new drugs. However, NPs present both opportunities and challenges. These difficulties can be technical, such as the need to dive or trawl to collect the organisms possessing the compounds, or biological, due to their particular marine habitats and the fact that they can be uncultivable in the laboratory. For all these difficulties, the contributions of CADD can play a very relevant role in simplifying their study, since, for example, no biological sample is needed to carry out an in-silico analysis. Therefore, the amount of natural product that needs to be used in the entire preclinical and clinical study is significantly reduced. Here, we exemplify how this combination between CADD and MNPs can help unlock their therapeutic potential. In this study, using a set of marine invertebrate molecules, we elucidate their possible molecular targets and associated therapeutic potential, establishing a pipeline that can be replicated in future studies. Full article

(This article belongs to the Special Issue Marine Drugs Research in Spain)

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17 pages, 1956 KiB

Open AccessArticle

Optimisation of Healthy-Lipid Content and Oxidative Stability during Oil Extraction from Squid (Illex argentinus) Viscera by Green Processing

by Alicia Rodríguez, Marcos Trigo, Santiago P. Aubourg and Isabel Medina

Mar. Drugs 2021, 19(11), 616; https://doi.org/10.3390/md19110616 - 30 Oct 2021

Cited by 10 | Viewed by 2449

Abstract

Green extraction was applied to Argentinean shortfin squid (Illex argentinus) viscera, consisting of a wet pressing method including a drying step, mechanic pressing, centrifugation of the resulting slurry, and oil collection. To maximise the oil yield and ω3 fatty acid content and to minimise the oil damage degree, a response surface methodology (RSM) design was developed focused on the drying temperature (45–85 °C) and time (30–90 min). In general, an increase of the drying time and temperature provided an increase in the lipid yield recovery from the viscera. The strongest drying conditions showed a higher recovery than 50% when compared with the traditional chemical method. The docosahexaenoic and eicosapentaenoic acid contents in the extracted oil revealed scarce dependence on drying conditions, showing valuable ranges (149.2–166.5 and 88.7–102.4 g·kg⁻¹ oil, respectively). Furthermore, the values of free fatty acids, peroxides, conjugated dienes, and ω3/ω6 ratio did not show extensive differences by comparing oils obtained from the different drying conditions. Contrary, a polyene index (PI) decrease was detected with increasing drying time and temperature. The RSM analysis indicated that optimised drying time (41.3 min) and temperature (85 °C) conditions would lead to 74.73 g·kg⁻¹ (oil yield), 1.87 (PI), and 6.72 (peroxide value) scores, with a 0.67 desirability value. Full article

(This article belongs to the Special Issue Marine Drugs Research in Spain)

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17 pages, 5926 KiB

Open AccessArticle

Isolation and Structural Elucidation of New Amphidinol Analogues from Amphidinium carterae Cultivated in a Pilot-Scale Photobioreactor

by Adrián Morales-Amador, Alejandro Molina-Miras, Lorenzo López-Rosales, Asterio Sánchez-Mirón, Francisco García-Camacho, María L. Souto and José J. Fernández

Mar. Drugs 2021, 19(8), 432; https://doi.org/10.3390/md19080432 - 29 Jul 2021

Cited by 8 | Viewed by 2985

Abstract

The demand for valuable products from dinoflagellate biotechnology has increased remarkably in recent years due to their many prospective applications. However, there remain many challenges that need to be addressed in order to make dinoflagellate bioactives a commercial reality. In this article, we describe the technical feasibility of producing and recovering amphidinol analogues (AMs) excreted into a culture broth of Amphidinium carterae ACRN03, successfully cultured in an LED-illuminated pilot-scale (80 L) bubble column photobioreactor operated in fed-batch mode with a pulse feeding strategy. We report on the isolation of new structurally related AMs, amphidinol 24 (1, AM24), amphidinol 25 (2, AM25) and amphidinol 26 (3, AM26), from a singular fraction resulting from the downstream processing. Their planar structures were elucidated by extensive NMR and HRMS analysis, whereas the relative configuration of the C-32→C-47 bis-tetrahydropyran core was confirmed to be antipodal in accord with the recently revised configuration of AM3. The hemolytic activities of the new metabolites and other related derivatives were evaluated, and structure–activity conclusions were established. Their isolation was based on a straightforward and high-performance bioprocess that could be suitable for the commercial development of AMs or other high-value compounds from shear sensitive dinoflagellates. Full article

(This article belongs to the Special Issue Marine Drugs Research in Spain)

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22 pages, 4580 KiB

Open AccessEditor’s ChoiceReview

The Development of the Bengamides as New Antibiotics against Drug-Resistant Bacteria

by Cristina Porras-Alcalá, Federico Moya-Utrera, Miguel García-Castro, Antonio Sánchez-Ruiz, Juan Manuel López-Romero, María Soledad Pino-González, Amelia Díaz-Morilla, Seiya Kitamura, Dennis W. Wolan, José Prados, Consolación Melguizo, Iván Cheng-Sánchez and Francisco Sarabia

Mar. Drugs 2022, 20(6), 373; https://doi.org/10.3390/md20060373 - 31 May 2022

Cited by 9 | Viewed by 3965

Abstract

The bengamides comprise an interesting family of natural products isolated from sponges belonging to the prolific Jaspidae family. Their outstanding antitumor properties, coupled with their unique mechanism of action and unprecedented molecular structures, have prompted an intense research activity directed towards their total syntheses, analogue design, and biological evaluations for their development as new anticancer agents. Together with these biological studies in cancer research, in recent years, the bengamides have been identified as potential antibiotics by their impressive biological activities against various drug-resistant bacteria such as Mycobacterium tuberculosis and Staphylococcus aureus. This review reports on the new advances in the chemistry and biology of the bengamides during the last years, paying special attention to their development as promising new antibiotics. Thus, the evolution of the bengamides from their initial exploration as antitumor agents up to their current status as antibiotics is described in detail, highlighting the manifold value of these marine natural products as valid hits in medicinal chemistry. Full article

(This article belongs to the Special Issue Marine Drugs Research in Spain)

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34 pages, 10079 KiB

Open AccessFeature PaperReview

Cryptic Metabolites from Marine-Derived Microorganisms Using OSMAC and Epigenetic Approaches

by Cristina Pinedo-Rivilla, Josefina Aleu and Rosa Durán-Patrón

Mar. Drugs 2022, 20(2), 84; https://doi.org/10.3390/md20020084 - 18 Jan 2022

Cited by 36 | Viewed by 5502

Abstract

Marine microorganisms have proven to be a source of new natural products with a wide spectrum of biological activities relevant in different industrial sectors. The ever-increasing number of sequenced microbial genomes has highlighted a discrepancy between the number of gene clusters potentially encoding the production of natural products and the actual number of chemically characterized metabolites for a given microorganism. Homologous and heterologous expression of these biosynthetic genes, which are often silent under experimental laboratory culture conditions, may lead to the discovery of new cryptic natural products of medical and biotechnological interest. Several new genetic and cultivation-based strategies have been developed to meet this challenge. The OSMAC approach (one strain—many compounds), based on modification of growth conditions, has proven to be a powerful strategy for the discovery of new cryptic natural products. As a direct extension of this approach, the addition of chemical elicitors or epigenetic modifiers have also been used to activate silent genes. This review looks at the structures and biological activities of new cryptic metabolites from marine-derived microorganisms obtained using the OSMAC approach, the addition of chemical elicitors, and enzymatic inhibitors and epigenetic modifiers. It covers works published up to June 2021. Full article

(This article belongs to the Special Issue Marine Drugs Research in Spain)

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26 pages, 3735 KiB

Open AccessReview

Marine Terpenic Endoperoxides

by Irene Torres-García, Josefa L. López-Martínez, Manuel Muñoz-Dorado, Ignacio Rodríguez-García and Miriam Álvarez-Corral

Mar. Drugs 2021, 19(12), 661; https://doi.org/10.3390/md19120661 - 25 Nov 2021

Cited by 6 | Viewed by 2620

Abstract

Organic extracts of marine invertebrates, mainly sponges, from seas all over the world are well known for their high in vitro anticancer and antibiotic activities which make them promising sources of compounds with potential use as pharmaceutical leads. Most of the structures discovered so far have a peculiar structural feature in common: a 1,2-dioxane ring. This is a highly reactive heterocycle that can be considered as an endoperoxide function. Together with other structural features, this group could be responsible for the strong biological activities of the substances present in the extracts. Numerous research programs have focused on their structural elucidation and total synthesis since the seventies. As a consequence, the number of established chiral centres and the similarity between different naturally occurring substances is increasingly higher. Most of these compounds have a terpenoid nature, mainly diterpene and sesterterpene, with several peculiar structural features, such as the loss of one carbon atom. Although there are many reviews dealing with the occurrence of marine peroxides, their activities, or potential pharmaceutical uses, no one has focused on those having a terpene origin and the endoperoxide function. We present here a comprehensive review of these compounds paying special attention to their structural features and their biological activity. Full article

(This article belongs to the Special Issue Marine Drugs Research in Spain)

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