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Special Issue "Bioactive Marine Natural Compounds with Heterocyclic Motifs in their Structure"

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

Deadline for manuscript submissions: closed (30 September 2017)

Special Issue Editor

Guest Editor
Prof. Dr. Mercedes Álvarez

Dept of Pharmacology, Toxicology and Therapeutic Chemistry, University of Barcelona, Barcelona Science Park, Baldiri Reixac 10-12, 08028 Barcelona, Spain
Website | E-Mail
Fax: +34 93 403 71 26
Interests: marine natural products; bioactive natural products; alkaloids; synthesis; heterocycles

Special Issue Information

Dear Colleagues,

Natural marine compounds have interesting and diverse biological profiles, including bioactive properties, such as anti-tumor, anti-microtubule, anti-proliferative, anti-hypertensive, anti-inflammatory, anti-virus, anti-fungal, cytotoxic, and antibiotic activity.

Heterocyclic motives are present in the structures of a large number of small molecules that constitute the active principle of our pharmaceutic arsenal. Many of these compounds are naturally occurring.

This Special Issue will be focused on marine compounds that are potentially useful as lead compounds for the development of new drugs or biological tools. As the Guest Editor, I invite scientists to present their recent advances in the isolation, structural elucidation, biological activity evaluation and total synthesis of marine natural compounds possessing one or more heterocycle in the structure. The synthesis of analogues to improve the bioactivity, as well as the data of biological activity and mechanisms of action will be considered.

Prof. Dr. Mercedes Álvarez
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.

Keywords

  • marine natural product
  • analog
  • synthesis
  • cytotoxic
  • anticancer
  • anti-inflammatory
  • antibacterial
  • antimalarial
  • antiviral
  • indole
  • imidazole
  • pyrrole
  • oxazole
  • thiazole
  • pyridine
  • carboline
  • quinoline
  • isoquinoline
  • carbazole
  • pyrroloquinoline
  • quinone
  • pyrroloquinone
  • pyrroloiminoquino

Published Papers (8 papers)

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Research

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Open AccessArticle Pinnatifidenyne-Derived Ethynyl Oxirane Acetogenins from Laurencia viridis
Mar. Drugs 2018, 16(1), 5; https://doi.org/10.3390/md16010005
Received: 2 October 2017 / Revised: 5 December 2017 / Accepted: 13 December 2017 / Published: 29 December 2017
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Abstract
Red algae of Laurencia continue to provide wide structural diversity and complexity of halogenated C15 acetogenin medium-ring ethers. Here, we described the isolation of three new C15 acetogenins (35), and one truncated derivative (6) from
[...] Read more.
Red algae of Laurencia continue to provide wide structural diversity and complexity of halogenated C15 acetogenin medium-ring ethers. Here, we described the isolation of three new C15 acetogenins (35), and one truncated derivative (6) from Laurencia viridis collected on the Canary Islands. These compounds are interesting variations on the pinnatifidenyne structure that included the first examples of ethynyl oxirane derivatives (34). The structures were elucidated by extensive study of NMR (Nuclear Magnetic Resonance) data, J-based configuration analysis and DFT (Density Functional Theory) calculations. Their antiproliferative activity against six human solid tumor cell lines was evaluated. Full article
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Open AccessFeature PaperArticle Computer-Aided Drug Design Applied to Marine Drug Discovery: Meridianins as Alzheimer’s Disease Therapeutic Agents
Mar. Drugs 2017, 15(12), 366; https://doi.org/10.3390/md15120366
Received: 6 October 2017 / Revised: 10 November 2017 / Accepted: 14 November 2017 / Published: 27 November 2017
Cited by 2 | PDF Full-text (5888 KB) | HTML Full-text | XML Full-text
Abstract
Computer-aided drug discovery/design (CADD) techniques allow the identification of natural products that are capable of modulating protein functions in pathogenesis-related pathways, constituting one of the most promising lines followed in drug discovery. In this paper, we computationally evaluated and reported the inhibitory activity
[...] Read more.
Computer-aided drug discovery/design (CADD) techniques allow the identification of natural products that are capable of modulating protein functions in pathogenesis-related pathways, constituting one of the most promising lines followed in drug discovery. In this paper, we computationally evaluated and reported the inhibitory activity found in meridianins A–G, a group of marine indole alkaloids isolated from the marine tunicate Aplidium, against various protein kinases involved in Alzheimer’s disease (AD), a neurodegenerative pathology characterized by the presence of neurofibrillary tangles (NFT). Balance splitting between tau kinase and phosphate activities caused tau hyperphosphorylation and, thereby, its aggregation and NTF formation. Inhibition of specific kinases involved in its phosphorylation pathway could be one of the key strategies to reverse tau hyperphosphorylation and would represent an approach to develop drugs to palliate AD symptoms. Meridianins bind to the adenosine triphosphate (ATP) binding site of certain protein kinases, acting as ATP competitive inhibitors. These compounds show very promising scaffolds to design new drugs against AD, which could act over tau protein kinases Glycogen synthetase kinase-3 Beta (GSK3β) and Casein kinase 1 delta (CK1δ, CK1D or KC1D), and dual specificity kinases as dual specificity tyrosine phosphorylation regulated kinase 1 (DYRK1A) and cdc2-like kinases (CLK1). This work is aimed to highlight the role of CADD techniques in marine drug discovery and to provide precise information regarding the binding mode and strength of meridianins against several protein kinases that could help in the future development of anti-AD drugs. Full article
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Open AccessArticle Palladium-Catalyzed Dehydrogenative Coupling: An Efficient Synthetic Strategy for the Construction of the Quinoline Core
Mar. Drugs 2017, 15(9), 276; https://doi.org/10.3390/md15090276
Received: 19 July 2017 / Revised: 4 August 2017 / Accepted: 24 August 2017 / Published: 30 August 2017
Cited by 1 | PDF Full-text (1384 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Palladium-catalyzed dehydrogenative coupling is an efficient synthetic strategy for the construction of quinoline scaffolds, a privileged structure and prevalent motif in many natural and biologically active products, in particular in marine alkaloids. Thus, quinolines and 1,2-dihydroquinolines can be selectively obtained in moderate-to-good yields
[...] Read more.
Palladium-catalyzed dehydrogenative coupling is an efficient synthetic strategy for the construction of quinoline scaffolds, a privileged structure and prevalent motif in many natural and biologically active products, in particular in marine alkaloids. Thus, quinolines and 1,2-dihydroquinolines can be selectively obtained in moderate-to-good yields via intramolecular C–H alkenylation reactions, by choosing the reaction conditions. This methodology provides a direct method for the construction of this type of quinoline through an efficient and atom economical procedure, and constitutes significant advance over the existing procedures that require preactivated reaction partners. Full article
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Open AccessArticle Bistratamides M and N, Oxazole-Thiazole Containing Cyclic Hexapeptides Isolated from Lissoclinum bistratum Interaction of Zinc (II) with Bistratamide K
Mar. Drugs 2017, 15(7), 209; https://doi.org/10.3390/md15070209
Received: 24 May 2017 / Revised: 17 June 2017 / Accepted: 26 June 2017 / Published: 1 July 2017
Cited by 2 | PDF Full-text (1231 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Two novel oxazole-thiazole containing cyclic hexapeptides, bistratamides M (1) and N (2) have been isolated from the marine ascidian Lissoclinum bistratum (L. bistratum) collected in Raja Ampat (Papua Bar, Indonesia). The planar structure of 1 and 2 was assigned
[...] Read more.
Two novel oxazole-thiazole containing cyclic hexapeptides, bistratamides M (1) and N (2) have been isolated from the marine ascidian Lissoclinum bistratum (L. bistratum) collected in Raja Ampat (Papua Bar, Indonesia). The planar structure of 1 and 2 was assigned on the basis of extensive 1D and 2D NMR spectroscopy and mass spectrometry. The absolute configuration of the amino acid residues in 1 and 2 was determined by the application of the Marfey’s and advanced Marfey’s methods after ozonolysis followed by acid-catalyzed hydrolysis. The interaction between zinc (II) and the naturally known bistratamide K (3), a cyclic hexapeptide isolated from a different specimen of Lissoclinum bistratum, was monitored by 1H and 13C NMR. The results obtained are consistent with the proposal that these peptides are biosynthesized for binding to metal ions. Compounds 1 and 2 display moderate cytotoxicity against four human tumor cell lines with GI50 values in the micromolar range. Full article
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Open AccessArticle The Roles of Spinochromes in Four Shallow Water Tropical Sea Urchins and Their Potential as Bioactive Pharmacological Agents
Mar. Drugs 2017, 15(6), 179; https://doi.org/10.3390/md15060179
Received: 10 May 2017 / Revised: 6 June 2017 / Accepted: 12 June 2017 / Published: 16 June 2017
Cited by 3 | PDF Full-text (1342 KB) | HTML Full-text | XML Full-text
Abstract
Spinochromes are principally known to be involved in sea urchin pigmentation as well as for their potentially interesting pharmacological properties. To assess their biological role in sea urchin physiology, experiments are undertaken on crude extracts from four species and on four isolated spinochromes
[...] Read more.
Spinochromes are principally known to be involved in sea urchin pigmentation as well as for their potentially interesting pharmacological properties. To assess their biological role in sea urchin physiology, experiments are undertaken on crude extracts from four species and on four isolated spinochromes in order to test their antibacterial, antioxidant, inflammatory and cytotoxic activities. First, the antibacterial assays show that the use of crude extracts as representatives of antibacterial effects of spinochromes are inaccurate. The assays on purified spinochromes showed a decrease in the growth of four strains with an intensity depending on the spinochromes/bacteria system, revealing the participation of spinochromes in the defense system against microorganisms. Secondly, in the 2,2-diphenyl-1-picrylhydrazyl antioxidant assays, spinochromes show an enhanced activity compared to the positive control. This latter observation suggests their involvement in ultraviolet radiation protection. Third, spinochromes present a pro-inflammatory effect on lipopolysaccharide-stimulated macrophages, highlighting their possible implication in the sea urchin immune system. Finally, cytotoxicity assays based on Trypan blue exclusion, performed in view of their possible future applications as drugs, show a weak cytotoxicity of these compounds against human cells. In conclusion, all results confirm the implication of spinochromes in sea urchin defense mechanisms against their external environment and reveal their potential for pharmacological and agronomical industries. Full article
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Open AccessFeature PaperArticle Four Aromatic Sulfates with an Inhibitory Effect against HCV NS3 Helicase from the Crinoid Alloeocomatella polycladia
Mar. Drugs 2017, 15(4), 117; https://doi.org/10.3390/md15040117
Received: 6 March 2017 / Revised: 4 April 2017 / Accepted: 6 April 2017 / Published: 11 April 2017
PDF Full-text (1638 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Bioassay-guided separation of a lipophilic extract of the crinoid Alloeocomatella polycladia, inhibiting the activity of HCV NS3 helicase, yielded two groups of molecules: cholesterol sulfate and four new aromatic sulfates 14. The structures of the aromatics were elucidated by
[...] Read more.
Bioassay-guided separation of a lipophilic extract of the crinoid Alloeocomatella polycladia, inhibiting the activity of HCV NS3 helicase, yielded two groups of molecules: cholesterol sulfate and four new aromatic sulfates 14. The structures of the aromatics were elucidated by spectroscopic analysis in addition to theoretical studies. The aromatic sulfates 14 showed moderate inhibition against NS3 helicase with IC50 values of 71, 95, 7, and 5 μM, respectively. Full article
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Review

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Open AccessReview Marine Alkylpurines: A Promising Group of Bioactive Marine Natural Products
Mar. Drugs 2018, 16(1), 6; https://doi.org/10.3390/md16010006
Received: 30 November 2017 / Revised: 16 December 2017 / Accepted: 19 December 2017 / Published: 1 January 2018
Cited by 2 | PDF Full-text (7672 KB) | HTML Full-text | XML Full-text
Abstract
Marine secondary metabolites with a purine motif in their structure are presented in this review. The alkylpurines are grouped according to the size of the alkyl substituents and their location on the purine ring. Aspects related to the marine source, chemical structure and
[...] Read more.
Marine secondary metabolites with a purine motif in their structure are presented in this review. The alkylpurines are grouped according to the size of the alkyl substituents and their location on the purine ring. Aspects related to the marine source, chemical structure and biological properties are considered together with synthetic approaches towards the natural products and bioactive analogues. This review contributes to studies of structure–activity relationships for these metabolites and highlights the potential of the sea as a source of new lead compounds in diverse therapeutic fields. Full article
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Open AccessFeature PaperReview The Oxepane Motif in Marine Drugs
Mar. Drugs 2017, 15(11), 361; https://doi.org/10.3390/md15110361
Received: 29 September 2017 / Revised: 3 November 2017 / Accepted: 8 November 2017 / Published: 15 November 2017
PDF Full-text (6814 KB) | HTML Full-text | XML Full-text
Abstract
Oceans have shown to be a remarkable source of natural products. The biological properties of many of these compounds have helped to produce great advances in medicinal chemistry. Within them, marine natural products containing an oxepanyl ring are present in a great variety
[...] Read more.
Oceans have shown to be a remarkable source of natural products. The biological properties of many of these compounds have helped to produce great advances in medicinal chemistry. Within them, marine natural products containing an oxepanyl ring are present in a great variety of algae, sponges, fungus and corals and show very important biological activities, many of them possessing remarkable cytotoxic properties against a wide range of cancer cell lines. Their rich chemical structures have attracted the attention of many researchers who have reported interesting synthetic approaches to these targets. This review covers the most prominent examples of these types of compounds, focusing the discussion on the isolation, structure determination, medicinal properties and total synthesis of these products. Full article
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