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Compounds from Cyanobacteria II

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

Deadline for manuscript submissions: closed (31 August 2019) | Viewed by 64498

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Dr. Michele R. Prinsep

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Department of Chemistry, The University of Waikato, Te Whare Wānanga o Waikato, Gate 1 Knighton Road, Private Bag 3105, Hamilton 3240, New Zealand
Interests: natural products chemistry; application of spectral methods to structural determination; biologically active compounds and structure-activity relationships; chemical ecology
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Dear Colleagues,

Cyanobacteria (blue-green algae) are an ancient and successful group of organisms that are found in a wide range of marine and freshwater habitats and in conditions as extreme as the heat of volcanic regions to the colds of Antarctica. They have proven to be an excellent source of secondary metabolites, many of which possess biological activity. The most common class of compounds found in cyanobacteria are oligopeptides (predominantly cyclic peptides). These are synthesised by nonribosomal peptide synthetases and many contain unique or unusual amino acids. Some of the other compound classes that have been isolated from cyanobacteria include terpenes and alkaloids.

Many of the natural products produced by cyanobacteria may be ecologically significant and some of the toxic metabolites are a human health concern, especially when present in recreational water bodies or fisheries. Cyanobacteria often have the means to produce many more metabolites than are actually expressed, so an understanding of biosynthesis and genetics in these organisms is vitally important.

There is considerable overlap between metabolites produced by terrestrial and marine cyanobacteria, hence the scope of this Special Issue has been widened to include compounds from freshwater cyanobacteria, in addition to studies of marine species. However, manuscripts describing studies of freshwater cyanobacteria with no obvious relevance to marine species will not be considered.

Assoc. Prof. Michele R. Prinsep
Guest Editor

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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.

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Keywords

cyanobacteria
blue-green algae
algal bloom
oligopeptides
amino acids
non-ribosomal peptide synthesis
biological activity
biosynthesis
secondary metabolites
toxins

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Published Papers (10 papers)

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16 pages, 2582 KiB

Open AccessArticle

Cyanobacteria as Nanogold Factories II: Chemical Reactivity and anti-Myocardial Infraction Properties of Customized Gold Nanoparticles Biosynthesized by Cyanothece sp.

by Nancy S. Younis, Esam M. Bakir, Maged E. Mohamed and Nermin A. El Semary

Mar. Drugs 2019, 17(7), 402; https://doi.org/10.3390/md17070402 - 8 Jul 2019

Cited by 16 | Viewed by 3514

Abstract

Cyanothece sp., a coccoid, unicellular, nitrogen-fixing and hydrogen-producing cyanobacterium, has been used in this study to biosynthesize customized gold nanoparticles under certain chemical conditions. The produced gold nanoparticles had a characteristic absorption band at 525–535 nm. Two types of gold nanoparticle, the purple and blue, were formed according to the chemical environment in which the cyanobacterium was grown. Dynamic light scattering was implemented to estimate the size of the purple and blue nanoparticles, which ranged from 80 ± 30 nm and 129 ± 40 nm in diameter, respectively. The highest scattering of laser light was recorded for the blue gold nanoparticles, which was possibly due to their larger size and higher concentration. The appearance of anodic and cathodic peaks in cyclic voltammetric scans of the blue gold nanoparticles reflected the oxidation into gold oxide, followed by the subsequent reduction into the nano metal state. The two produced forms of gold nanoparticles were used to treat isoproterenol-induced myocardial infarction in experimental rats. Both forms of nanoparticles ameliorated myocardial infarction injury, with a slight difference in their curative activity with the purple being more effective. Mechanisms that might explain the curative effect of these nanoparticles on the myocardial infarction were proposed. The morphological, physiological, and biochemical attributes of the Cyanothece sp. cyanobacterium were fundamental for the successful production of “tailored” nanoparticles, and complemented the chemical conditions for the differential biosynthesis process. The present research represents a novel approach to manipulate cyanobacterial cells towards the production of different-sized gold nanoparticles whose curative impacts vary accordingly. This is the first report on that type of manipulated gold nanoparticles biosynthesis which will hopefully open doors for further investigations and biotechnological applications. Full article

(This article belongs to the Special Issue Compounds from Cyanobacteria II)

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20 pages, 2527 KiB

Open AccessArticle

Solid Matrix-Supported Supercritical CO₂ Enhances Extraction of γ-Linolenic Acid from the Cyanobacterium Arthrospira (Spirulina) platensis and Bioactivity Evaluation of the Molecule in Zebrafish

by Xiaohong Yang, Yi Li, Yanhua Li, Ding Ye, Li Yuan, Yonghua Sun, Danxiang Han and Qiang Hu

Mar. Drugs 2019, 17(4), 203; https://doi.org/10.3390/md17040203 - 30 Mar 2019

Cited by 34 | Viewed by 4731

Abstract

Marine cyanobacteria represent a large untapped source of functional glycolipids enriched with polyunsaturated fatty acids (PUFAs) for human health. However, advanced methods for scalable isolation of diverse species containing high-purity PUFA-rich glycolipids will have to be developed and their possible pharmaceutical and nutraceutical functions identified. This paper introduces a novel solid matrix-supported supercritical CO₂ extraction method for scalable isolation of the PUFA γ-linolenic acid (GLA)-enriched glycolipids from the cyanobacterium Arthrospira (Spirulina) platensis, which has been the most widely used among microalgae in the nutraceutical and pharmaceutical industries. Of various porous materials studied, diatomite was the best to facilitate extraction of GLA-rich glycolipids, resulting in an extraction efficiency of 98%. Gamma-linolenic acid made up 35% of total fatty acids (TFAs) in the extracts, which was considerably greater than that obtained with ethanol (26%), Bligh and Dyer (24%), and in situ transesterification (24%) methods, respectively. Lipidomics analysis revealed that GLA was exclusively associated with galactolipids. Pharmaceutical functions of GLA-rich galactolipids were investigated on a zebrafish caudal fin regeneration model. The results suggested that GLA extracted from A. platensis possessed anti-oxidative, anti-inflammatory, and anti-allergic activities, which acted in a concerted manner to promote post-injury regeneration of zebrafish. Full article

(This article belongs to the Special Issue Compounds from Cyanobacteria II)

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19 pages, 1604 KiB

Open AccessArticle

A Multi-Bioassay Integrated Approach to Assess the Antifouling Potential of the Cyanobacterial Metabolites Portoamides

by Jorge Antunes, Sandra Pereira, Tiago Ribeiro, Jeffrey E. Plowman, Ancy Thomas, Stefan Clerens, Alexandre Campos, Vitor Vasconcelos and Joana R. Almeida

Mar. Drugs 2019, 17(2), 111; https://doi.org/10.3390/md17020111 - 12 Feb 2019

Cited by 30 | Viewed by 4967

Abstract

The cyclic peptides portoamides produced by the cyanobacterium Phormidium sp. LEGE 05292 were previously isolated and their ability to condition microcommunities by allelopathic effect was described. These interesting bioactive properties are, however, still underexplored as their biotechnological applications may be vast. This study aims to investigate the antifouling potential of portoamides, given that a challenge in the search for new environmentally friendly antifouling products is to find non-toxic natural alternatives with the ability to prevent colonization of different biofouling species, from bacteria to macroinvertebrates. A multi-bioassay approach was applied to assess portoamides antifouling properties, marine ecotoxicity and molecular mode of action. Results showed high effectiveness in the prevention of mussel larvae settlement (EC₅₀ = 3.16 µM), and also bioactivity towards growth and biofilm disruption of marine biofouling bacterial strains, while not showing toxicity towards both target and non-target species. Antifouling molecular targets in mussel larvae include energy metabolism modifications (failure in proton-transporting ATPases activity), structural alterations of the gills and protein and gene regulatory mechanisms. Overall, portoamides reveal a broad-spectrum bioactivity towards diverse biofouling species, including a non-toxic and reversible effect towards mussel larvae, showing potential to be incorporated as an active ingredient in antifouling coatings. Full article

(This article belongs to the Special Issue Compounds from Cyanobacteria II)

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14 pages, 2419 KiB

Open AccessFeature PaperArticle

Isolation, Structure Elucidation and Biological Evaluation of Lagunamide D: A New Cytotoxic Macrocyclic Depsipeptide from Marine Cyanobacteria

by Danmeng Luo, Masteria Y. Putra, Tao Ye, Valerie J. Paul and Hendrik Luesch

Mar. Drugs 2019, 17(2), 83; https://doi.org/10.3390/md17020083 - 1 Feb 2019

Cited by 22 | Viewed by 5689

Abstract

Lagunamide D, a new cytotoxic macrocyclic depsipeptide, was discovered from a collection of marine cyanobacteria from Loggerhead Key in the Dry Tortugas, Florida. An intramolecular ester exchange was observed, where the 26-membered macrocycle could contract to a 24-membered compound via acyl migration at the 1,3-diol unit, and the transformation product was named lagunamide D’. The planar structures of both compounds were elucidated using a combination of nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectroscopy (HRMS). The absolute configurations were determined on the basis of enantioselective analysis, modified Mosher’s analysis, Kishi NMR database, and direct comparison with lagunamide A, a structure closely resembling lagunamide D. Lagunamides A and D displayed low-nanomolar antiproliferative activity against A549 human lung adenocarcinoma cells, while the structural transformation from the 26-membered lagunamide D macrocycle to the 24-membered ring structure for lagunamide D’ led to a 9.6-fold decrease in activity. Lagunamide D also displayed potent activity in triggering apoptosis in a dose- and time-dependent manner. Further investigation on the mechanism of action of the lagunamide scaffold is needed to fully explore its therapeutic potential as an anticancer agent. Full article

(This article belongs to the Special Issue Compounds from Cyanobacteria II)

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21 pages, 3859 KiB

Open AccessArticle

Cyanobacteria as Nanogold Factories: Chemical and Anti-Myocardial Infarction Properties of Gold Nanoparticles Synthesized by Lyngbya majuscula

by Esam M. Bakir, Nancy S. Younis, Maged E. Mohamed and Nermin A. El Semary

Mar. Drugs 2018, 16(6), 217; https://doi.org/10.3390/md16060217 - 20 Jun 2018

Cited by 80 | Viewed by 6142

Abstract

To the best of our knowledge, cyanobacterial strains from the Arabian Gulf have never been investigated with respect to their potential for nanoparticle production. Lyngbya majuscula was isolated from the AlOqair area, Al-Ahsa Government, Eastern Province, Kingdom of Saudi Arabia. The cyanobacterium was initially incubated with 1500 mg/mL of HAuCl₄ for two days. The blue-green strain turned purple, which indicated the intracellular formation of gold nanoparticles. Prolonged incubation for over two months triggered the extracellular production of nanogold particles. UV-visible spectroscopy measurements indicated the presence of a resonance plasmon band at ~535 nm, whereas electron microscopy scanning indicated the presence of gold nanoparticles with an average diameter of 41.7 ± 0.2 nm. The antioxidant and anti-myocardial infarction activities of the cyanobacterial extract, the gold nanoparticle solution, and a combination of both were investigated in animal models. Isoproterenol (100 mg/kg, SC (sub cutaneous)) was injected into experimental rats for three days to induce a state of myocardial infarction; then the animals were given cyanobacterial extract (200 mg/kg/day, IP (intra peritoneal)), gold nanoparticles (200 mg/kg/day, IP), ora mixture of both for 14 days. Cardiac biomarkers, electrocardiogram (ECG), blood pressure, and antioxidant enzymes were determined as indicators of myocardial infarction. The results showed that isoproterenol elevates ST and QT segments and increases heart rate and serum activities of creatine phosphokinase (CPK), creatine kinase-myocardial bound (CP-MB), and cardiac troponin T (cTnT). It also reduces heart tissue content of glutathione peroxidase (GRx) and superoxide dismutase (SOD), and the arterial pressure indices of systolic arterial pressure (SAP), diastolic arterial pressure (DAP), and mean arterial pressure (MAP). Gold nanoparticles alone or in combination with cyanobacterial extract produced an inhibitory effect on isoproterenol-induced changes in serum cardiac injury markers, ECG, arterial pressure indices, and antioxidant capabilities of the heart. Full article

(This article belongs to the Special Issue Compounds from Cyanobacteria II)

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1153 KiB

Open AccessArticle

Inhibitors of Serine Proteases from a Microcystis sp. Bloom Material Collected from Timurim Reservoir, Israel

by Rawan Hasan-Amer and Shmuel Carmeli

Mar. Drugs 2017, 15(12), 371; https://doi.org/10.3390/md15120371 - 1 Dec 2017

Cited by 10 | Viewed by 4525

Abstract

Two new natural products, micropeptin TR1058 (1) and aeruginosin TR642 (2), were isolated from the hydrophilic extract of bloom material of Microcystis sp. collected from the Timurim water reservoir in Israel. The structures of compounds 1 and 2 were determined using 1D and 2D NMR spectroscopy and HR ESI MS and MS/MS techniques. Micropeptin TR1058 (1) was extremely unstable under the isolation conditions, and several degradation products were identified. NMR analysis of aeruginosin TR642 (2) revealed a mixture of eight isomers, and elucidation of its structure was challenging. Aeruginosin TR642 contains a 4,5-didehydroaraginal subunit that has not been described before. Micropeptin TR1058 (1) inhibited chymotrypsin with an IC₅₀ of 6.78 µM, and aeruginosin TR642 (2) inhibited trypsin and thrombin with inhibition concentration (IC₅₀) values of 3.80 and 0.85 µM, respectively. The structures and biological activities of the new compounds are discussed. Full article

(This article belongs to the Special Issue Compounds from Cyanobacteria II)

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828 KiB

Open AccessArticle

Tricholides A and B and Unnarmicin D: New Hybrid PKS-NRPS Macrocycles Isolated from an Environmental Collection of Trichodesmium thiebautii

by Matthew J. Bertin, Alexandre F. Roduit, Jiadong Sun, Gabriella E. Alves, Christopher W. Via, Miguel A. Gonzalez, Paul V. Zimba and Peter D. R. Moeller

Mar. Drugs 2017, 15(7), 206; https://doi.org/10.3390/md15070206 - 30 Jun 2017

Cited by 16 | Viewed by 6065

Abstract

Bioassay-guided isolation of the lipophilic extract of Trichodesmium thiebautii bloom material led to the purification and structure characterization of two new hybrid polyketide-non-ribosomal peptide (PKS-NRPS) macrocyclic compounds, tricholides A and B (1 and 2). A third macrocyclic compound, unnarmicin D (3), was identified as a new depsipeptide in the unnarmicin family, given its structural similarity to the existing compounds in this group. The planar structures of 1–3 were determined using 1D and 2D NMR spectra and complementary spectroscopic and spectrometric procedures. The absolute configurations of the amino acid components of 1–3 were determined via acid hydrolysis, derivitization with Marfey’s reagent and HPLC-UV comparison to authentic amino acid standards. The absolute configuration of the 3-hydroxydodecanoic acid moiety in 3 was determined using a modified Mosher’s esterification procedure on a linear derivative of tricharmicin (4) and additionally by a comparison of ¹³C NMR shifts of 3 to known depsipeptides with β-hydroxy acid subunits. Tricholide B (2) showed moderate cytotoxicity to Neuro-2A murine neuroblastoma cells (EC₅₀: 14.5 ± 6.2 μM). Full article

(This article belongs to the Special Issue Compounds from Cyanobacteria II)

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Review

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16 pages, 1538 KiB

Open AccessReview

Bioactive Peptides Produced by Cyanobacteria of the Genus Nostoc: A Review

by Anna Fidor, Robert Konkel and Hanna Mazur-Marzec

Mar. Drugs 2019, 17(10), 561; https://doi.org/10.3390/md17100561 - 29 Sep 2019

Cited by 47 | Viewed by 6654

Abstract

Cyanobacteria of the genus Nostoc are widespread in all kinds of habitats. They occur in a free-living state or in association with other organisms. Members of this genus belong to prolific producers of bioactive metabolites, some of which have been recognized as potential therapeutic agents. Of these, peptides and peptide-like structures show the most promising properties and are of a particular interest for both research laboratories and pharmaceutical companies. Nostoc is a sole source of some lead compounds such as cytotoxic cryptophycins, antiviral cyanovirin-N, or the antitoxic nostocyclopeptides. Nostoc also produces the same bioactive peptides as other cyanobacterial genera, but they frequently have some unique modifications in the structure. This includes hepatotoxic microcystins and potent proteases inhibitors such as cyanopeptolins, anabaenopeptins, and microginins. In this review, we described the most studied peptides produced by Nostoc, focusing especially on the structure, the activity, and a potential application of the compounds. Full article

(This article belongs to the Special Issue Compounds from Cyanobacteria II)

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49 pages, 2382 KiB

Open AccessFeature PaperReview

Natural Products from Cyanobacteria: Focus on Beneficial Activities

by Justine Demay, Cécile Bernard, Anita Reinhardt and Benjamin Marie

Mar. Drugs 2019, 17(6), 320; https://doi.org/10.3390/md17060320 - 30 May 2019

Cited by 205 | Viewed by 13824

Abstract

Cyanobacteria are photosynthetic microorganisms that colonize diverse environments worldwide, ranging from ocean to freshwaters, soils, and extreme environments. Their adaptation capacities and the diversity of natural products that they synthesize, support cyanobacterial success in colonization of their respective ecological niches. Although cyanobacteria are well-known for their toxin production and their relative deleterious consequences, they also produce a large variety of molecules that exhibit beneficial properties with high potential in various fields (e.g., a synthetic analog of dolastatin 10 is used against Hodgkin’s lymphoma). The present review focuses on the beneficial activities of cyanobacterial molecules described so far. Based on an analysis of 670 papers, it appears that more than 90 genera of cyanobacteria have been observed to produce compounds with potentially beneficial activities in which most of them belong to the orders Oscillatoriales, Nostocales, Chroococcales, and Synechococcales. The rest of the cyanobacterial orders (i.e., Pleurocapsales, Chroococcidiopsales, and Gloeobacterales) remain poorly explored in terms of their molecular diversity and relative bioactivity. The diverse cyanobacterial metabolites possessing beneficial bioactivities belong to 10 different chemical classes (alkaloids, depsipeptides, lipopeptides, macrolides/lactones, peptides, terpenes, polysaccharides, lipids, polyketides, and others) that exhibit 14 major kinds of bioactivity. However, no direct relationship between the chemical class and the respective bioactivity of these molecules has been demonstrated. We further selected and specifically described 47 molecule families according to their respective bioactivities and their potential uses in pharmacology, cosmetology, agriculture, or other specific fields of interest. With this up-to-date review, we attempt to present new perspectives for the rational discovery of novel cyanobacterial metabolites with beneficial bioactivity. Full article

(This article belongs to the Special Issue Compounds from Cyanobacteria II)

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19 pages, 2723 KiB

Open AccessReview

Cyanobacterial Siderophores—Physiology, Structure, Biosynthesis, and Applications

by Erland Årstøl and Martin F. Hohmann-Marriott

Mar. Drugs 2019, 17(5), 281; https://doi.org/10.3390/md17050281 - 10 May 2019

Cited by 60 | Viewed by 7131

Abstract

Siderophores are low-molecular-weight metal chelators that function in microbial iron uptake. As iron limits primary productivity in many environments, siderophores are of great ecological importance. Additionally, their metal binding properties have attracted interest for uses in medicine and bioremediation. Here, we review the current state of knowledge concerning the siderophores produced by cyanobacteria. We give an overview of all cyanobacterial species with known siderophore production, finding siderophores produced in all but the most basal clades, and in a wide variety of environments. We explore what is known about the structure, biosynthesis, and cycling of the cyanobacterial siderophores that have been characterized: Synechobactin, schizokinen and anachelin. We also highlight alternative siderophore functionality and technological potential, finding allelopathic effects on competing phytoplankton and likely roles in limiting heavy-metal toxicity. Methodological improvements in siderophore characterization and detection are briefly described. Since most known cyanobacterial siderophores have not been structurally characterized, the application of mass spectrometry techniques will likely reveal a breadth of variation within these important molecules. Full article

(This article belongs to the Special Issue Compounds from Cyanobacteria II)

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