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Bioactive Compounds from Cyanobacteria
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Bioactive Compounds from Cyanobacteria

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (31 August 2020) | Viewed by 24961

Special Issue Editor

Prof. Dr. Tatsufumi Okino

E-Mail Website
Guest Editor
Faculty of Environmental Earth Science, HokkaidoUniversity, Sapporo 060-0810, Japan
Interests: cyanobacteria; enzyme inhibitor; antifouling; peptide; halogenase; cyototoxin

Special Issue Information

Dear Colleagues,

Cyanobacteria from terrestrial, freshwater, and marine environments are rich sources of bioactive compounds. The recent accumulation of genomic data of cyanobacteria has accelerated biosynthetic studies of their secondary metabolites. In addition, studies focusing on mechanisms of action have increased. Cytotoxins and enzyme inhibitors from cyanobacteria have been known for a long time and more detailed studies of these activities are increasing recently. The other type of activities including anti-protozoal and antifouling properties have been explored.

In this Special Issue, we will publish informative papers and reviews regarding all aspects of bioactive compounds from cyanobacteria. Potential topics include, but are not limited to, structure elucidation, total synthesis, biosynthesis, screening methods, mechanisms of action, analytical methods in relation to bioactive compounds from marine, freshwater, and terrestrial cyanobacteria.

Prof. Tatsufumi Okino
Guest Editor

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Keywords

  • cyanobacteria
  • polyketide
  • peptide
  • NRPS
  • PKS
  • anti-cancer
  • inhibitor
  • biosynthesis
  • toxin

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Published Papers (7 papers)

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Research

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12 pages, 1362 KiB  
Communication
Determination of Volatile Organic Compounds and Antibacterial Activity of the Amazonian Cyanobacterium Synechococcus sp. Strain GFB01
by Samuel Cavalcante do Amaral, Agenor Valadares Santos, Maria Paula da Cruz Schneider, Joyce Kelly Rosário da Silva and Luciana Pereira Xavier
Molecules 2020, 25(20), 4744; https://doi.org/10.3390/molecules25204744 - 16 Oct 2020
Cited by 12 | Viewed by 2945
Abstract
Cyanobacteria exhibit great biotechnological potential due to their capacity to produce compounds with various applicability. Volatile organic compounds (VOCs) possess low molecular weight and high vapor pressure. Many volatiles produced by microorganisms have biotechnological potential, including antimicrobial activity. This study aimed to investigate [...] Read more.
Cyanobacteria exhibit great biotechnological potential due to their capacity to produce compounds with various applicability. Volatile organic compounds (VOCs) possess low molecular weight and high vapor pressure. Many volatiles produced by microorganisms have biotechnological potential, including antimicrobial activity. This study aimed to investigate the VOCs synthesized by cyanobacterium Synechococcus sp. strain GFB01, and the influence of nitrate and phosphate on its antibacterial potential. The strain was isolated from the surface of the freshwater lagoon Lagoa dos Índios, Amapá state, in Northern Brazil. After cultivation, the VOCs were extracted by a simultaneous distillation-extraction process, using a Likens-Nickerson apparatus (2 h), and then identified by GC-MS. The extracts did not display inhibitory activity against the Gram-positive bacteria tested by the disk-diffusion agar method. However, the anti-Salmonella property in both extracts (methanol and aqueous) was detected. The main VOCs identified were heptadecane (81.32%) and octadecyl acetate (11.71%). To the best of our knowledge, this is the first study of VOCs emitted by a cyanobacterium from the Amazon that reports the occurrence of 6-pentadecanol and octadecyl acetate in cyanobacteria. Full article
(This article belongs to the Special Issue Bioactive Compounds from Cyanobacteria)
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9 pages, 677 KiB  
Article
Bioactivities of Lyngbyabellins from Cyanobacteria of Moorea and Okeania Genera
by Imam Fathoni, Julie G. Petitbois, Walied M. Alarif, Ahmed Abdel-Lateff, Sultan S. Al-Lihaibi, Erina Yoshimura, Yasuyuki Nogata, Charles S. Vairappan, Eti Nurwening Sholikhah and Tatsufumi Okino
Molecules 2020, 25(17), 3986; https://doi.org/10.3390/molecules25173986 - 1 Sep 2020
Cited by 16 | Viewed by 3281
Abstract
Cyanobacteria are reported as rich sources of secondary metabolites that provide biological activities such as enzyme inhibition and cytotoxicity. Ten depsipeptide derivatives (lyngbyabellins) were isolated from a Malaysian Moorea bouillonii and a Red Sea Okeania sp.: lyngbyabellins G (1), O ( [...] Read more.
Cyanobacteria are reported as rich sources of secondary metabolites that provide biological activities such as enzyme inhibition and cytotoxicity. Ten depsipeptide derivatives (lyngbyabellins) were isolated from a Malaysian Moorea bouillonii and a Red Sea Okeania sp.: lyngbyabellins G (1), O (2), P (3), H (4), A (7), 27-deoxylyngbyabellin A (5), and homohydroxydolabellin (6). This study indicated that lyngbyabellins displayed cytotoxicity, antimalarial, and antifouling activities. The isolated compounds were tested for cytotoxic effect against human breast cancer cells (MCF7), for antifouling activity against Amphibalanus amphitrite barnacle larvae, and for antiplasmodial effect towards Plasmodium falciparum. Lyngbyabellins A and G displayed potent antiplasmodial effect against Plasmodium, whereas homohydroxydolabellin showed moderate effect. For antifouling activity, the side chain decreases the activity slightly, but the essential feature is the acyclic structure. As previously reported, the acyclic lyngbyabellins are less cytotoxic than the corresponding cyclic ones, and the side chain increases cytotoxicity. This study revealed that lyngbyabellins, despite being cytotoxic agents as previously reported, also exhibit antimalarial and antifouling activities. The unique chemical structures and functionalities of lyngbyabellin play an essential role in their biological activities. Full article
(This article belongs to the Special Issue Bioactive Compounds from Cyanobacteria)
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18 pages, 4995 KiB  
Article
Alternative Isolation Protocol for Desulfo and Zwitterionic Cylindrospermopsin Alkaloids and Comparison of Their Toxicity in HepG2 Cells
by Carlos González-Blanco, Felipe Augusto Dörr, Renata Albuquerque, Janice Onuki and Ernani Pinto
Molecules 2020, 25(13), 3027; https://doi.org/10.3390/molecules25133027 - 2 Jul 2020
Cited by 7 | Viewed by 2490
Abstract
The term cylindrospermopsins (CYNs) refers to a structurally related class of cyanobacterial metabolites comprised of a tricyclic guanidine group and a hydroxymethyluracil moiety. Most reports in environmental aquatic samples refer to cylindrospermopsin (CYN), and reports on other CYN alkaloids are scarce, due, in [...] Read more.
The term cylindrospermopsins (CYNs) refers to a structurally related class of cyanobacterial metabolites comprised of a tricyclic guanidine group and a hydroxymethyluracil moiety. Most reports in environmental aquatic samples refer to cylindrospermopsin (CYN), and reports on other CYN alkaloids are scarce, due, in part, to a lack of versatile isolation protocols. Thus, using commercially available solid phase extraction (SPE) cartridges, we optimized an isolation protocol for the complete recovery of CYN, 7-deoxy-cylindrospermopsin (7D-CYN) and 7-deoxy-desulfo-cylindrospermopsin (7D-desulfo-CYN) from the same aliquot. The isolation protocol was adaptable depending on the nature of the sample (solid biomass, culture broth or environmental water sample) and tolerates up to 4 L of dense culture broth or 400 mg of lyophilized biomass. To quantitate the CYN alkaloids, we validated an LC-DAD-MS2 method, which takes advantage of the UV absorption of the uracil group (λ 262 nm). Using electrospray ionization (ESI) in a positive ion mode, the high-resolution MS1 data confirms the presence of the protonated alkaloids, and the MS2 fragment assignment is reported as complementary proof of the molecular structure of the CYNs. We isolated three CYN alkaloids with different water solubility using the same lyophilized sample, with a purity that ranged from 95% to 99%. The biological activity of the purified CYNs, along with a synthetic degradation product of CYN (desulfo-cylindrospermopsin), was evaluated by assessing necrosis and apoptosis in vitro using flow cytometry. CYN’s lethal potency in HepG2 cells was greater than the other analogs, due to the presence of all four functional groups: guanidine, uracil, C-7 hydroxyl and the sulfate residue. Full article
(This article belongs to the Special Issue Bioactive Compounds from Cyanobacteria)
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10 pages, 1273 KiB  
Article
Analytical Technique Optimization on the Detection of β-cyclocitral in Microcystis Species
by Ryuji Yamashita, Beata Bober, Keisuke Kanei, Suzue Arii, Kiyomi Tsuji and Ken-ichi Harada
Molecules 2020, 25(4), 832; https://doi.org/10.3390/molecules25040832 - 14 Feb 2020
Cited by 5 | Viewed by 2438
Abstract
β-Cyclocitral, specifically produced by Microcystis, is one of the volatile organic compounds (VOCs) derived from cyanobacteria and has a lytic activity. It is postulated that β-cyclocitral is a key compound for regulating the occurrence of cyanobacteria and related microorganisms in an aquatic [...] Read more.
β-Cyclocitral, specifically produced by Microcystis, is one of the volatile organic compounds (VOCs) derived from cyanobacteria and has a lytic activity. It is postulated that β-cyclocitral is a key compound for regulating the occurrence of cyanobacteria and related microorganisms in an aquatic environment. β-Cyclocitral is sensitively detected when a high density of the cells is achieved from late summer to autumn. Moreover, it is expected to be involved in changes in the species composition of cyanobacteria in a lake. Although several analysis methods for β-cyclocitral have already been reported, β-cyclocitral could be detected using only solid phase micro-extraction (SPME), whereas it could not be found at all using the solvent extraction method in a previous study. In this study, we investigated why β-cyclocitral was detected using only SPME GC/MS. Particularly, three operations in SPME, i.e., extraction temperature, sample stirring rate, and the effect of salt, were examined for the production of β-cyclocitral. Among these, heating (60 °C) was critical for the β-cyclocitral formation. Furthermore, acidification with a 1-h storage was more effective than heating when comparing the obtained amounts. The present results indicated that β-cyclocitral did not exist as the intact form in cells, because it was formed by heating or acidification of the resulting intermediates during the analysis by SPME. The obtained results would be helpful to understand the formation and role of β-cyclocitral in an aquatic environment. Full article
(This article belongs to the Special Issue Bioactive Compounds from Cyanobacteria)
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7 pages, 895 KiB  
Communication
Neo-Aplysiatoxin A Isolated from Okinawan Cyanobacterium Moorea Producens
by Mioko Kawaguchi, Masayuki Satake, Bo-Tao Zhang, Yue-Yun Xiao, Masayuki Fukuoka, Hajime Uchida and Hiroshi Nagai
Molecules 2020, 25(3), 457; https://doi.org/10.3390/molecules25030457 - 22 Jan 2020
Cited by 20 | Viewed by 3223
Abstract
A new aplysiatoxin derivative, neo-aplysiatoxin A (1), along with seven known compounds, neo-debromoaplysiatoxin A (2), dolastatin 3 (3), lyngbic acid (4), malyngamide M (5), hermitamide A (6), (−)-loliolide (7), [...] Read more.
A new aplysiatoxin derivative, neo-aplysiatoxin A (1), along with seven known compounds, neo-debromoaplysiatoxin A (2), dolastatin 3 (3), lyngbic acid (4), malyngamide M (5), hermitamide A (6), (−)-loliolide (7), and (+)-epiloliolide (8), was isolated from the Okinawan cyanobacterium Moorea producens. Their structures were elucidated on the basis of spectroscopic data, including high-resolution mass spectrometry and nuclear magnetic resonance. The compounds were evaluated for cytotoxic and diatom growth inhibition activities. Full article
(This article belongs to the Special Issue Bioactive Compounds from Cyanobacteria)
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Review

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20 pages, 1755 KiB  
Review
Advances in the Biotechnological Potential of Brazilian Marine Microalgae and Cyanobacteria
by Deborah Terra de Oliveira, Ana Alice Farias da Costa, Fabíola Fernandes Costa, Geraldo Narciso da Rocha Filho and Luís Adriano Santos do Nascimento
Molecules 2020, 25(12), 2908; https://doi.org/10.3390/molecules25122908 - 24 Jun 2020
Cited by 11 | Viewed by 4002
Abstract
Due the worldwide need to improve care for the environment and people, there is a great demand for the development of new renewable, sustainable, and less polluting technologies for food, health, and environmental industries. The marine environment is one of the main areas [...] Read more.
Due the worldwide need to improve care for the environment and people, there is a great demand for the development of new renewable, sustainable, and less polluting technologies for food, health, and environmental industries. The marine environment is one of the main areas investigated in the search for alternatives to the raw materials currently used. Thereby, cyanobacteria and marine microalgae are microorganisms that are capable of producing a diverse range of metabolites useful for their cellular maintenance, but that also represent a great biotechnological potential. Due its great potential, they have an enormous appeal in the scientific research where, the biological activity of metabolites produced by these microorganisms, such as the antioxidant action of sterols are, some examples of biotechnological applications investigated around the world. Thereby, Brazil due to its extensive biodiversity, has high potential as a raw material supplier of marine waters, researching cyanobacteria and microalgae metabolites and their applications. Thus, this rapid review intends to present some important contributions and advances from Brazilian researchers, using the biomass of Brazilian cyanobacteria and marine microalgae, in order to illustrate the value of what has already been discovered and the enormous potential of what remains unexplored so far. Full article
(This article belongs to the Special Issue Bioactive Compounds from Cyanobacteria)
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30 pages, 3025 KiB  
Review
Marine Cyanobacteria: A Source of Lead Compounds and their Clinically-Relevant Molecular Targets
by Lik Tong Tan and Ma Yadanar Phyo
Molecules 2020, 25(9), 2197; https://doi.org/10.3390/molecules25092197 - 8 May 2020
Cited by 43 | Viewed by 5996
Abstract
The prokaryotic filamentous marine cyanobacteria are photosynthetic microbes that are found in diverse marine habitats, ranging from epiphytic to endolithic communities. Their successful colonization in nature is largely attributed to genetic diversity as well as the production of ecologically important natural products. These [...] Read more.
The prokaryotic filamentous marine cyanobacteria are photosynthetic microbes that are found in diverse marine habitats, ranging from epiphytic to endolithic communities. Their successful colonization in nature is largely attributed to genetic diversity as well as the production of ecologically important natural products. These cyanobacterial natural products are also a source of potential drug leads for the development of therapeutic agents used in the treatment of diseases, such as cancer, parasitic infections and inflammation. Major sources of these biomedically important natural compounds are found predominately from marine cyanobacterial orders Oscillatoriales, Nostocales, Chroococcales and Synechococcales. Moreover, technological advances in genomic and metabolomics approaches, such as mass spectrometry and NMR spectroscopy, revealed that marine cyanobacteria are a treasure trove of structurally unique natural products. The high potency of a number of natural products are due to their specific interference with validated drug targets, such as proteasomes, proteases, histone deacetylases, microtubules, actin filaments and membrane receptors/channels. In this review, the chemistry and biology of selected potent cyanobacterial compounds as well as their synthetic analogues are presented based on their molecular targets. These molecules are discussed to reflect current research trends in drug discovery from marine cyanobacterial natural products. Full article
(This article belongs to the Special Issue Bioactive Compounds from Cyanobacteria)
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