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Marine Drugs
Special Issues
Synthesis of Marine-Derived Compounds
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Synthesis of Marine-Derived Compounds

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

Deadline for manuscript submissions: closed (15 October 2018) | Viewed by 23641

Special Issue Editor

Dr. Lyndon West

E-Mail Website
Guest Editor
Department of Chemistry and Biochemistry, Florida Atlantic University, Boca Raton, FL 33431, USA
Interests: synthesis of marine natural products
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

The chemical complexity and diverse biological activities of marine natural products have been a source of inspiration, and the challenge of mimicking distinctive three-dimensional structures presents unique research opportunities that push the boundaries of organic chemistry. Natural Product synthesis, both total and partial (semi-synthesis), provides the confirmation of structure, allows the ability to carry-out structure–activity relationship (SAR) studies, lead optimization, together with providing a potential solution to the supply issue that has curtailed the development of many marine natural products. The aim of this Special Issue is to highlight the chemical and biological discoveries resulting from the total synthesis or semi-synthesis of marine-derived natural products. As the Guest Editor, I invite scientists in the fields of chemistry, biochemistry, pharmacology, and toxicology to submit review papers or original articles where synthesis has contributed to the field of marine natural products drug discovery.

Assoc. Prof. Dr. Lyndon West
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 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

  • Marine natural product
  • Total synthesis
  • Biomimetic synthesis
  • Semi-synthesis
  • Chemical transformation
  • Structure-activity relationship
  • Lead optimization
  • Pharmacology

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Published Papers (4 papers)

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Research

18 pages, 2987 KiB  
Article
Antitumor Activity of Quinazolinone Alkaloids Inspired by Marine Natural Products
by Solida Long, Diana I. S. P. Resende, Anake Kijjoa, Artur M. S. Silva, André Pina, Tamara Fernández-Marcelo, M. Helena Vasconcelos, Emília Sousa and Madalena M. M. Pinto
Mar. Drugs 2018, 16(8), 261; https://doi.org/10.3390/md16080261 - 31 Jul 2018
Cited by 38 | Viewed by 6630
Abstract
Many fungal quinazolinone metabolites, which contain the methyl-indole pyrazino [1,2-b]quinazoline-3,6-dione core, have been found to possess promising antitumor activity. The purpose of this work was to synthesize the enantiomeric pairs of two members of this quinazolinone family, to explore their potential [...] Read more.
Many fungal quinazolinone metabolites, which contain the methyl-indole pyrazino [1,2-b]quinazoline-3,6-dione core, have been found to possess promising antitumor activity. The purpose of this work was to synthesize the enantiomeric pairs of two members of this quinazolinone family, to explore their potential as antitumor and their ability to revert multidrug resistance. The marine natural product fiscalin B (4c), and antienantiomers (4b, 5b, and 5c) were synthesized via a one-pot approach, while the syn enantiomers (4a, 4d, 5a, and 5d) were synthetized by a multi-step procedure. These strategies used anthranilic acid (i), chiral N-protected α-amino acids (ii), and tryptophan methyl esters (iii) to form the core ring of pyrazino[2,1-b]quinazoline-3,6-dione scaffold. Four enantiomeric pairs, with different enantiomeric purities, were obtained with overall yields ranging from 7 to 40%. Compounds 4a–d and 5a–d were evaluated for their growth inhibitory effect against two tumor cell lines. Differences between enantiomeric pairs were noted and 5a–d displayed GI50 values ranging from 31 to 52 μM, which are lower than those of 4a–d. Nevertheless, no effect on P-glycoprotein (P-gp) modulation was observed for all compounds. This study disclosed new data for fiscalin B (4c), as well as for its analogues for a future development of novel anticancer drug leads. Full article
(This article belongs to the Special Issue Synthesis of Marine-Derived Compounds)
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15 pages, 1868 KiB  
Article
Synthesis of Alkyl-Glycerolipids Standards for Gas Chromatography Analysis: Application for Chimera and Shark Liver Oils
by Michelle Pinault, Cyrille Guimaraes, Hélène Couthon, Jérôme Thibonnet, Delphine Fontaine, Aurélie Chantôme, Stephan Chevalier, Pierre Besson, Paul-Alain Jaffrès and Christophe Vandier
Mar. Drugs 2018, 16(4), 101; https://doi.org/10.3390/md16040101 - 23 Mar 2018
Cited by 8 | Viewed by 5156
Abstract
Natural O-alkyl-glycerolipids, also known as alkyl-ether-lipids (AEL), feature a long fatty alkyl chain linked to the glycerol unit by an ether bond. AEL are ubiquitously found in different tissues but, are abundant in shark liver oil, breast milk, red blood cells, blood [...] Read more.
Natural O-alkyl-glycerolipids, also known as alkyl-ether-lipids (AEL), feature a long fatty alkyl chain linked to the glycerol unit by an ether bond. AEL are ubiquitously found in different tissues but, are abundant in shark liver oil, breast milk, red blood cells, blood plasma, and bone marrow. Only a few AEL are commercially available, while many others with saturated or mono-unsaturated alkyl chains of variable length are not available. These compounds are, however, necessary as standards for analytical methods. Here, we investigated different reported procedures and we adapted some of them to prepare a series of 1-O-alkyl-glycerols featuring mainly saturated alkyl chains of various lengths (14:0, 16:0, 17:0, 19:0, 20:0, 22:0) and two monounsaturated chains (16:1, 18:1). All of these standards were fully characterized by NMR and GC-MS. Finally, we used these standards to identify the AEL subtypes in shark and chimera liver oils. The distribution of the identified AEL were: 14:0 (20–24%), 16:0 (42–54%) and 18:1 (6–16%) and, to a lesser extent, (0.2–2%) for each of the following: 16:1, 17:0, 18:0, and 20:0. These standards open the possibilities to identify AEL subtypes in tumours and compare their composition to those of non-tumour tissues. Full article
(This article belongs to the Special Issue Synthesis of Marine-Derived Compounds)
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4119 KiB  
Article
Discovery of Novel Bromophenol Hybrids as Potential Anticancer Agents through the Ros-Mediated Apoptotic Pathway: Design, Synthesis and Biological Evaluation
by Li-Jun Wang, Chuan-Long Guo, Xiang-Qian Li, Shuai-Yu Wang, Bo Jiang, Yue Zhao, Jiao Luo, Kuo Xu, Hua Liu, Shu-Ju Guo, Ning Wu and Da-Yong Shi
Mar. Drugs 2017, 15(11), 343; https://doi.org/10.3390/md15110343 - 1 Nov 2017
Cited by 24 | Viewed by 4655
Abstract
A series of bromophenol hybrids with N-containing heterocyclic moieties were designed, and their anticancer activities against a panel of five human cancer cell lines (A549, Bel7402, HepG2, HCT116 and Caco2) using MTT assay in vitro were explored. Among them, thirteen compounds (17a [...] Read more.
A series of bromophenol hybrids with N-containing heterocyclic moieties were designed, and their anticancer activities against a panel of five human cancer cell lines (A549, Bel7402, HepG2, HCT116 and Caco2) using MTT assay in vitro were explored. Among them, thirteen compounds (17a, 17b, 18a, 19a, 19b, 20a, 20b, 21a, 21b, 22a, 22b, 23a, and 23b) exhibited significant inhibitory activity against the tested cancer cell lines. The structure-activity relationships (SARs) of bromophenol derivatives were discussed. The promising candidate compound 17a could induce cell cycle arrest at G0/G1 phase and induce apoptosis in A549 cells, as well as caused DNA fragmentations, morphological changes and ROS generation by the mechanism studies. Furthermore, compound 17a suppression of Bcl-2 levels (decrease in the expression of the anti-apoptotic proteins Bcl-2 and down-regulation in the expression levels of Bcl-2) in A549 cells were observed, along with activation caspase-3 and PARP, which indicated that compound 17a induced A549 cells apoptosis in vitro through the ROS-mediated apoptotic pathway. These results might be useful for bromophenol derivatives to be explored and developed as novel anticancer drugs. Full article
(This article belongs to the Special Issue Synthesis of Marine-Derived Compounds)
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2745 KiB  
Article
Marine Inspired 2-(5-Halo-1H-indol-3-yl)-N,N-dimethylethanamines as Modulators of Serotonin Receptors: An Example Illustrating the Power of Bromine as Part of the Uniquely Marine Chemical Space
by Mohamed A. Ibrahim, Abir T. El-Alfy, Kelly Ezel, Mohamed O. Radwan, Abbas G. Shilabin, Anna J. Kochanowska-Karamyan, Howaida I. Abd-Alla, Masami Otsuka and Mark T. Hamann
Mar. Drugs 2017, 15(8), 248; https://doi.org/10.3390/md15080248 - 9 Aug 2017
Cited by 18 | Viewed by 6594
Abstract
In previous studies, we have isolated several marine indole alkaloids and evaluated them in the forced swim test (FST) and locomotor activity test, revealing their potential as antidepressant and sedative drug leads. Amongst the reported metabolites to display such activities was 5-bromo-N [...] Read more.
In previous studies, we have isolated several marine indole alkaloids and evaluated them in the forced swim test (FST) and locomotor activity test, revealing their potential as antidepressant and sedative drug leads. Amongst the reported metabolites to display such activities was 5-bromo-N,N-dimethyltryptamine. Owing to the importance of the judicious introduction of halogens into drug candidates, we synthesized two series built on a 2-(1H-indol-3-yl)-N,N-dimethylethanamine scaffold with different halogen substitutions. The synthesized compounds were evaluated for their in vitro and in vivo antidepressant and sedative activities using the mouse forced swim and locomotor activity tests. Receptor binding studies of these compounds to serotonin (5-HT) receptors were conducted. Amongst the prepared compounds, 2-(1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide (1a), 2-(5-bromo-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide (1d), 2-(1H-indol-3-yl)-N,N-dimethylethanamine (2a), 2-(5-chloro-1H-indol-3-yl)-N,N-dimethylethanamine (2c), 2-(5-bromo-1H-indol-3-yl)-N,N-dimethylethanamine (2d), and 2-(5-iodo-1H-indol-3-yl)-N,N-dimethylethanamine (2e) have been shown to possess significant antidepressant-like action, while compounds 2c, 2d, and 2e exhibited potent sedative activity. Compounds 2a, 2c, 2d, and 2e showed nanomolar affinities to serotonin receptors 5-HT1A and 5-HT7. The in vitro data indicates that the antidepressant action exerted by these compounds in vivo is mediated, at least in part, via interaction with serotonin receptors. The data presented here shows the valuable role that bromine plays in providing novel chemical space and electrostatic interactions. Bromine is ubiquitous in the marine environment and a common element of marine natural products. Full article
(This article belongs to the Special Issue Synthesis of Marine-Derived Compounds)
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