Special Issue "Advances in Marine Alkaloids"

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

Deadline for manuscript submissions: 31 January 2020.

Special Issue Editors

Prof. Dr. Paula B. Andrade
E-Mail Website
Guest Editor
Laboratory of Pharmacognosy, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira 228, Porto 4050-313, Portugal
Interests: metabolite profiling of natural matrices; natural agents for inflammation and cancer; neurodegenerative disorders
Special Issues and Collections in MDPI journals
Prof. Dr. Patrícia Valentão
E-Mail Website
Guest Editor
Laboratory of Pharmacognosy, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira 228, Porto 4050-313, Portugal
Interests: metabolite profiling of natural matrices; evaluation of bioactive agents from natural sources
Special Issues and Collections in MDPI journals

Special Issue Information

Dear Colleagues,

The extreme environmental conditions found in the sea (e.g., low temperature, high pressure, reduced light, and the presence of predators) have led marine organisms to develop machinery translated in a diversity of compounds superior to those found in land-based systems. Nevertheless, the marine environment is still considered a rich underexploited source of compounds.

Alkaloids are among the most challenging compounds found in nature, because of the diversity of structural scaffolds arising from distinct amino acids, but also because of their biological effects. These basic nitrogen-bearing secondary metabolites are among the most active molecules, and it is not unusual to find them in various phases of human clinical trials for the treatment of different conditions. This Special Issue will address the advances in the chemistry, distribution, and application of alkaloids from marine organisms, covering well-characterized extracts to isolated compounds, the optimization of processes for the preparation of analogues using medicinal chemistry strategies, bioavailability, mechanisms of action, and toxicological features, to provide recent developments in marine alkaloids.

Prof. Dr. Paula B. Andrade
Prof. Dr. Patrícia Valentão
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 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 2000 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

  • alkaloids
  • marine products
  • plants
  • invertebrates
  • seaweeds
  • extraction
  • structural elucidation
  • drug discovery

Published Papers (8 papers)

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Research

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Open AccessArticle
Penicamide A, A Unique N,N′-Ketal Quinazolinone Alkaloid from Ascidian-Derived Fungus Penicillium sp. 4829
Mar. Drugs 2019, 17(9), 522; https://doi.org/10.3390/md17090522 - 05 Sep 2019
Cited by 1
Abstract
Previously unreported N,N′-ketal quinazolinone enantiomers [(−)-1 and (+)-1] and a new biogenetically related compound (2), along with six known compounds, 2-pyrovoylaminobenzamide (3), N-(2-hydroxypropanoyl)-2 amino benzoic acid amide (4), pseurotin A [...] Read more.
Previously unreported N,N′-ketal quinazolinone enantiomers [(−)-1 and (+)-1] and a new biogenetically related compound (2), along with six known compounds, 2-pyrovoylaminobenzamide (3), N-(2-hydroxypropanoyl)-2 amino benzoic acid amide (4), pseurotin A (5), niacinamide (6), citreohybridonol (7), citreohybridone C (8) were isolated from the ascidian-derived fungus Penicillium sp. 4829 in wheat solid-substrate medium culture. Their structures were elucidated by a combination of spectroscopic analyses (1D and 2D NMR and Electron Circular Dichroism data) and X-ray crystallography. The enantiomeric pair of 1 is the first example of naturally occurring N,N′-ketal quinazolinone possessing a unique tetracyclic system having 4-quinazolinone fused with tetrahydroisoquinoline moiety. The enantiomeric mixtures of 1 displayed an inhibitory effect on NO production in lipopolysaccharide-activated RAW264.7 cells, while the optically pure (–)-1 showed better inhibitory effect than (+)-1. Full article
(This article belongs to the Special Issue Advances in Marine Alkaloids)
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Open AccessCommunication
Total Syntheses and Preliminary Biological Evaluation of Brominated Fascaplysin and Reticulatine Alkaloids and Their Analogues
Mar. Drugs 2019, 17(9), 496; https://doi.org/10.3390/md17090496 - 25 Aug 2019
Abstract
A simple approach toward the synthesis of the marine sponge derived pigment fascaplysin was used to obtain the marine alkaloids 3-bromofascaplysin and 3,10-dibromofascaplysin. These compounds were used for first syntheses of the alkaloids 14-bromoreticulatate and 14-bromoreticulatine. Preliminary bioassays showed that 14-bromoreticulatine has a [...] Read more.
A simple approach toward the synthesis of the marine sponge derived pigment fascaplysin was used to obtain the marine alkaloids 3-bromofascaplysin and 3,10-dibromofascaplysin. These compounds were used for first syntheses of the alkaloids 14-bromoreticulatate and 14-bromoreticulatine. Preliminary bioassays showed that 14-bromoreticulatine has a selective antibiotic (to Pseudomonas aeruginosa) activity and reveals cytotoxicity toward human melanoma, colon, and prostate cancer cells. 3,10-Dibromofascaplysin was able to target metabolic activity of the prostate cancer cells, without disrupting cell membrane’s integrity and had a wide therapeutic window amongst the fascaplysin alkaloids. Full article
(This article belongs to the Special Issue Advances in Marine Alkaloids)
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Open AccessArticle
α-Conotoxin TxIB: A Uniquely Selective Ligand for α6/α3β2β3 Nicotinic Acetylcholine Receptor Attenuates Nicotine-Induced Conditioned Place Preference in Mice
Mar. Drugs 2019, 17(9), 490; https://doi.org/10.3390/md17090490 - 22 Aug 2019
Cited by 1
Abstract
α-Conotoxin TxIB is a specific antagonist of α6/α3β2β3(α6β2*) nicotinic acetylcholine receptor (nAChR) with an IC50 of 28 nM. Previous studies have shown that α6β2* nAChRs are abundantly expressed in midbrain dopaminergic neurons and play an important role in mediating the mechanism of [...] Read more.
α-Conotoxin TxIB is a specific antagonist of α6/α3β2β3(α6β2*) nicotinic acetylcholine receptor (nAChR) with an IC50 of 28 nM. Previous studies have shown that α6β2* nAChRs are abundantly expressed in midbrain dopaminergic neurons and play an important role in mediating the mechanism of nicotine and other drugs reward effect. It provided important targets for the development of anti-addiction drugs. The present study evaluated the pharmacological activity of TxIB in vivo with conditioned place preference (CPP) model, which were induced by subcutaneous injection (s.c.) of nicotine (NIC, 0.5 mg/kg). α-Conotoxin TxIB inhibited the expression and reinstatement of CPP in mice dose-dependently, but had no significant effect on locomotor activity. The concentrations of dopamine (DA), γ-aminobutyric acid (GABA) and noradrenaline (NE) in different brain regions were measured by enzyme-linked immunosorbent assay (ELISA). We found that TxIB could inhibit the concentrations of DA, GABA and NE in different brain regions (such as nucleus accumbens (NAc), hippocampus (HIP) and prefrontal cortex (PFC)) in NIC-induced mice. The concentrations of DA and NE were decreased in ventral tegmental area (VTA), while GABA had little change. The current work described the inhibition activity of TxIB in NIC-induced CPP, suggesting that α6β2* nAChR-targeted compound may be a promising drug for nicotine addiction treatment. Full article
(This article belongs to the Special Issue Advances in Marine Alkaloids)
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Open AccessArticle
Tersone A-G, New Pyridone Alkaloids from the Deep-Sea Fungus Phomopsis tersa
Mar. Drugs 2019, 17(7), 394; https://doi.org/10.3390/md17070394 - 03 Jul 2019
Cited by 1
Abstract
Four phenylfuropyridone racemates, (±)-tersones A-C and E (13, 5), one phenylpyridone racemate, (±)-tersone D (4), one new pyridine alkaloid, tersone F (6), single new phenylfuropyridone, tersone G (7) and two known analogs [...] Read more.
Four phenylfuropyridone racemates, (±)-tersones A-C and E (13, 5), one phenylpyridone racemate, (±)-tersone D (4), one new pyridine alkaloid, tersone F (6), single new phenylfuropyridone, tersone G (7) and two known analogs 8 and 9 were isolated from the deep-sea fungus Phomopsis tersa. Their structures and absolute configurations were characterized on the basis of comprehensive spectroscopic analyses, single-crystal X-ray diffraction experiments, and electronic circular dichroism (ECD) calculations. Moreover, compounds 19 were evaluated for in vitro antimicrobial and cytotoxic activity. Compounds 5b and 8b exhibited antibacterial activity against S. aureus with the MIC value of 31.5 μg/mL, while compound 5b showed cytoxic activities against SF-268, MCF-7, HepG-2 and A549 cell lines with IC50 values of 32.0, 29.5, 39.5 and 33.2 μM, respectively. Full article
(This article belongs to the Special Issue Advances in Marine Alkaloids)
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Open AccessFeature PaperArticle
Bromotryptamine and Bromotyramine Derivatives from the Tropical Southwestern Pacific Sponge Narrabeena nigra
Mar. Drugs 2019, 17(6), 319; https://doi.org/10.3390/md17060319 - 30 May 2019
Abstract
So far, the Futuna Islands located in the Central Indo-Pacific Ocean have not been inventoried for their diversity in marine sponges and associated chemical diversity. As part of the Tara Pacific expedition, the first chemical investigation of the sponge Narrabeena nigra collected around [...] Read more.
So far, the Futuna Islands located in the Central Indo-Pacific Ocean have not been inventoried for their diversity in marine sponges and associated chemical diversity. As part of the Tara Pacific expedition, the first chemical investigation of the sponge Narrabeena nigra collected around the Futuna Islands yielded 18 brominated alkaloids: seven new bromotryptamine derivatives 17 and one new bromotyramine derivative 8 together with 10 known metabolites of both families 918. Their structures were deduced from extensive analyses of nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS) data. In silico metabolite anticipation using the online tool MetWork revealed the presence of a key and minor biosynthetic intermediates. These 18 compounds showed almost no cytotoxic effect up to 10 µM on human neuroblastoma SH-SY5Y and microglia BV2 cells, and some of them exhibited an interesting neuroprotective activity by reducing oxidative damage. Full article
(This article belongs to the Special Issue Advances in Marine Alkaloids)
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Open AccessArticle
Synergistic Anti-Candida Activity of Bengazole A in the Presence of Bengamide A
Mar. Drugs 2019, 17(2), 102; https://doi.org/10.3390/md17020102 - 07 Feb 2019
Abstract
Bengazoles A–G from the marine sponge Jaspis sp. exhibit potent in vitro antifungal activity against Candida spp. and other pathogenic fungi. The mechanism of action (MOA) of bengazole A was explored in Candida albicans under both liquid culture and surface culture on Mueller-Hinton [...] Read more.
Bengazoles A–G from the marine sponge Jaspis sp. exhibit potent in vitro antifungal activity against Candida spp. and other pathogenic fungi. The mechanism of action (MOA) of bengazole A was explored in Candida albicans under both liquid culture and surface culture on Mueller-Hinton agar. Pronounced dose-dependent synergistic antifungal activity was observed with bengazole A in the presence of bengamide A, which is also a natural product from Jaspis sp. The MOA of bengazole A was further explored by monitoring the sterol composition of C. albicans in the presence of sub-lethal concentrations of bengazole A. The GCMS of solvent extracts prepared from liquid cultures of C. albicans in the presence of clotrimazole―a clinically approved azole antifungal drug that suppresses ergosterol biosynthesis by the inhibition of 14α-demethylase―showed reduced cellular ergosterol content and increased concentrations of lanosterol and 24-methylenedihydrolanosterol (a shunt metabolite of ergosterol biosynthesis). No change in relative sterol composition was observed when C. albicans was cultured with bengazole A. These results eliminate an azole-like MOA for the bengazoles, and suggest that another as-yet unidentified mechanism is operative. Full article
(This article belongs to the Special Issue Advances in Marine Alkaloids)
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Review

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Open AccessReview
Recent Discovery of Heterocyclic Alkaloids from Marine-Derived Aspergillus Species
Mar. Drugs 2020, 18(1), 54; https://doi.org/10.3390/md18010054 - 14 Jan 2020
Abstract
Nitrogen heterocycles have drawn considerable attention due to of their significant biological activities. The marine fungi residing in extreme environments are among the richest sources of these basic nitrogen-containing secondary metabolites. As one of the most well-known universal groups of filamentous fungi, marine-derived [...] Read more.
Nitrogen heterocycles have drawn considerable attention due to of their significant biological activities. The marine fungi residing in extreme environments are among the richest sources of these basic nitrogen-containing secondary metabolites. As one of the most well-known universal groups of filamentous fungi, marine-derived Aspergillus species produce a large number of structurally unique heterocyclic alkaloids. This review attempts to provide a comprehensive summary of the structural diversity and biological activities of heterocyclic alkaloids that are produced by marine-derived Aspergillus species. Herein, a total of 130 such structures that were reported from the beginning of 2014 through the end of 2018 are included, and 75 references are cited in this review, which will benefit future drug development and innovation. Full article
(This article belongs to the Special Issue Advances in Marine Alkaloids)
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Open AccessReview
Bioactive Nitrogenous Secondary Metabolites from the Marine Sponge Genus Haliclona
Mar. Drugs 2019, 17(12), 682; https://doi.org/10.3390/md17120682 - 03 Dec 2019
Abstract
Marine sponge genus Haliclona, one of the most prolific sources of natural products, contains over 600 species but only a small part of them had been classified and chemically investigated. On the basis of extensive literature search, this review firstly summarizes 112 [...] Read more.
Marine sponge genus Haliclona, one of the most prolific sources of natural products, contains over 600 species but only a small part of them had been classified and chemically investigated. On the basis of extensive literature search, this review firstly summarizes 112 nitrogenous secondary metabolites from classified and unclassified Haliclona sponges as well as from their symbiotic microorganisms. Most of these substances have only been found in Haliclona sponges, and display diverse bioactive properties with potential applications in new drug discovery. Full article
(This article belongs to the Special Issue Advances in Marine Alkaloids)
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