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Cyanobacterial Toxins: Identification and Structural Characterisation to Better Understand Their Distribution and Diversity

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Special Issue Information
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A special issue of Toxins (ISSN 2072-6651). This special issue belongs to the section "Marine and Freshwater Toxins".

Deadline for manuscript submissions: closed (31 August 2019) | Viewed by 37192

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Special Issue Editor

Dr. Jonathan Puddick

E-Mail Website
Guest Editor

Cawthron Institute, Private Bag 2, Nelson 7042, New Zealand
Interests: the identification of harmful and helpful bioactive compounds produced by cyanobacteria and algae; understanding their purpose for the producing organism and how they impact on the surrounding environment

Special Issue Information

Dear Colleagues,

Cyanobacteria and the toxins they produce (cyanotoxins) have become an increasing problem around the world as the eutrophication of waterways and global warming increases the frequency, severity and duration of cyanobacterial blooms in aquatic environments. To date, numerous cyanobacterial genera have been established as potential toxin-producers and many of the gene clusters responsible for cyanotoxin production have been characterised. The impressive structural diversity in different classes of cyanotoxins has sparked much interest in the fields of chemical ecology, evolutionary biology and molecular biology. On the other hand, the vast range of toxin structures poses challenges for their detection in the environment and their management. Better understanding of the diversity of cyanotoxins, the producing organisms and their global distribution will assist in overcoming these challenges and will help to answer fundamental questions relating to the evolution of toxin production in cyanobacteria.

In this Special Issue on Cyanobacterial Toxins we will publish new research on the structural characterisation of cyanotoxins, investigations into the diversity of cyanotoxins from different regions of the world and method development work that will accelerate the identification of cyanotoxins. Review articles that collate existing information on cyanotoxin diversity and identify valuable research avenues will also be considered.

Dr. Jonathan Puddick
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 double-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Toxins 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 2700 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

anatoxin
aplysiatoxin
β-methylamino-alanine
chemical ecology
cyanotoxin
cylindrospermopsin
lyngbyatoxin
microcystin
nodularin
saxitoxin

Published Papers (7 papers)

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Research

Jump to: Review

20 pages, 3028 KiB

Open AccessArticle

Analysis of Covalently Bound Microcystins in Sediments and Clam Tissue in the Sacramento–San Joaquin River Delta, California, USA

by Melissa Bolotaolo, Tomofumi Kurobe, Birgit Puschner, Bruce G Hammock, Matt J. Hengel, Sarah Lesmeister and Swee J. Teh

Toxins 2020, 12(3), 178; https://doi.org/10.3390/toxins12030178 - 13 Mar 2020

Cited by 7 | Viewed by 3974

Abstract

Harmful cyanobacterial blooms compromise human and environmental health, mainly due to the cyanotoxins they often produce. Microcystins (MCs) are the most commonly measured group of cyanotoxins and are hepatotoxic, neurotoxic, and cytotoxic. Due to MCs ability to covalently bind to proteins, quantification in complex matrices is difficult. To analyze bound and unbound MCs, analytical methods were optimized for analysis in sediment and clam tissues. A clean up step was incorporated to remove lipids, improving percent yield. This method was then applied to sediment and clam samples collected from the Sacramento–San Joaquin River Delta (Delta) in the spring and fall of 2017. Water samples were also tested for intracellular and extracellular MCs. These analyses were used to quantify the partitioning of MCs among sediment, clams, and water, and to examine whether MCs persist during non-summer months. Toxin analysis revealed that multiple sediment samples collected in the Delta were positive for MCs, with a majority of the positive samples from sites in the San Joaquin River, even while water samples from the same location were below detection limit. These data highlight the importance of analyzing MCs in complex matrices to accurately evaluate environmental risk. Full article

(This article belongs to the Special Issue Cyanobacterial Toxins: Identification and Structural Characterisation to Better Understand Their Distribution and Diversity)

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18 pages, 2996 KiB

Open AccessArticle

Metabolome Variation between Strains of Microcystis aeruginosa by Untargeted Mass Spectrometry

by Marianne Racine, Ammar Saleem and Frances R. Pick

Toxins 2019, 11(12), 723; https://doi.org/10.3390/toxins11120723 - 11 Dec 2019

Cited by 10 | Viewed by 3731

Abstract

Cyanobacteria are notorious for their potential to produce hepatotoxic microcystins (MCs), but other bioactive compounds synthesized in the cells could be as toxic, and thus present interest for characterization. Ultra performance liquid chromatography and high-resolution accurate mass spectrometry (UPLC-QTOF-MS/MS) combined with untargeted analysis was used to compare the metabolomes of five different strains of the common bloom-forming cyanobacterium, Microcystis aeruginosa. Even in microcystin-producing strains, other classes of oligopeptides including cyanopeptolins, aeruginosins, and aerucyclamides, were often the more dominant compounds. The distinct and large variation between strains of the same widespread species highlights the need to characterize the metabolome of a larger number of cyanobacteria, especially as several metabolites other than microcystins can affect ecological and human health. Full article

(This article belongs to the Special Issue Cyanobacterial Toxins: Identification and Structural Characterisation to Better Understand Their Distribution and Diversity)

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14 pages, 1156 KiB

Open AccessArticle

Dhb Microcystins Discovered in USA Using an Online Concentration LC–MS/MS Platform

by Johnna A. Birbeck, Nicholas J. Peraino, Grace M. O’Neill, Julia Coady and Judy A. Westrick

Toxins 2019, 11(11), 653; https://doi.org/10.3390/toxins11110653 - 10 Nov 2019

Cited by 11 | Viewed by 3287

Abstract

Based on current structural and statistical calculations, thousands of microcystins (MCs) can exist; yet, to date, only 246 MCs have been identified and only 12 commercial MC standards are available. Standard mass spectrometry workflows for known and unknown MCs need to be developed and validated for basic and applied harmful algal bloom research to advance. Our investigation focuses on samples taken in the spring of 2018 from an impoundment fed by Oser and Bischoff Reservoirs, Indiana, United States of America (USA). The dominant cyanobacterium found during sampling was Planktothrix agardhii. The goal of our study was to identify and quantify the MCs in the impoundment sample using chemical derivatization and mass spectrometry. Modifying these techniques to use online concentration liquid chromatography tandem mass spectrometry (LC–MS/MS), two untargeted MCs have been identified, [d-Asp³, Dhb⁷]-MC-LR and tentative [Dhb⁷]-MC-YR. [Dhb⁷]-MC-YR is not yet reported in the literature to date, and this was the first reported incidence of Dhb MCs in the United States. Furthermore, it was discovered that the commercially available [d-Asp³]-MC-RR standard was [d-Asp³, Dhb⁷]-MC-RR. This study highlights a workflow utilizing online concentration LC–MS/MS, high-resolution MS (HRMS), and chemical derivatization to identify isobaric MCs. Full article

(This article belongs to the Special Issue Cyanobacterial Toxins: Identification and Structural Characterisation to Better Understand Their Distribution and Diversity)

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21 pages, 2279 KiB

Open AccessEditor’s ChoiceArticle

A Data-Independent Methodology for the Structural Characterization of Microcystins and Anabaenopeptins Leading to the Identification of Four New Congeners

by Audrey Roy-Lachapelle, Morgan Solliec, Sébastien Sauvé and Christian Gagnon

Toxins 2019, 11(11), 619; https://doi.org/10.3390/toxins11110619 - 26 Oct 2019

Cited by 19 | Viewed by 3467

Abstract

Toxin-producing cyanobacteria are responsible for the presence of hundreds of bioactive compounds in aquatic environments undergoing increasing eutrophication. The identification of cyanotoxins is still emerging, due to the great diversity of potential congeners, yet high-resolution mass spectrometry (HRMS) has the potential to deepen this knowledge in aquatic environments. In this study, high-throughput and sensitive on-line solid-phase extraction ultra-high performance liquid chromatography (SPE-UHPLC) coupled to HRMS was applied to a data-independent acquisition (DIA) workflow for the suspect screening of cyanopeptides, including microcystin and anabaenopeptin toxin classes. The unambiguous characterization of 11 uncommon cyanopeptides was possible using a characterization workflow through extensive analysis of fragmentation patterns. This method also allowed the characterization of four unknown cyanotoxins ([Leu¹, Ser⁷] MC-HtyR, [Asp³]MC-RHar, AP731, and AP803). The quantification of 17 common cyanotoxins along with the semi-quantification of the characterized uncommon cyanopeptides resulted with the identification of 23 different cyanotoxins in 12 lakes in Canada, United Kingdom and France. The concentrations of the compounds varied between 39 and 41,000 ng L⁻¹. To our knowledge, this is the first DIA method applied for the suspect screening of two families of cyanopeptides simultaneously. Moreover, this study shows the great diversity of cyanotoxins in lake water cyanobacterial blooms, a growing concern in aquatic systems. Full article

(This article belongs to the Special Issue Cyanobacterial Toxins: Identification and Structural Characterisation to Better Understand Their Distribution and Diversity)

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9 pages, 805 KiB

Open AccessFeature PaperCommunication

In Situ Collection and Preservation of Intact Microcystis Colonies to Assess Population Diversity and Microcystin Quotas

by Jonathan Puddick, Eric O. Goodwin, Ian Hawes, David P. Hamilton and Susanna A. Wood

Toxins 2019, 11(8), 435; https://doi.org/10.3390/toxins11080435 - 24 Jul 2019

Cited by 2 | Viewed by 2505

Abstract

Understanding of colony specific properties of cyanobacteria in the natural environment has been challenging because sampling methods disaggregate colonies and there are often delays before they can be isolated and preserved. Microcystis is a ubiquitous cyanobacteria that forms large colonies in situ and often produces microcystins, a potent hepatotoxin. In the present study a new cryo-sampling technique was used to collect intact Microcystis colonies in situ by embedding them in a sheet of ice. Thirty-two of these Microcystis colonies were investigated with image analysis, liquid chromatography-mass spectrometry, quantitative polymerase chain reaction and high-throughput sequencing to assess their volume, microcystin quota and internal transcribed spacer (ITS) genotype diversity. Microcystin quotas were positively correlated to colony volume (R² = 0.32; p = 0.004). Individual colonies had low Microcystis ITS genotype diversity and one ITS operational taxonomic unit predominated in all samples. This study demonstrates the utility of the cryo-sampling method to enhance the understanding of colony-specific properties of cyanobacteria with higher precision than previously possible. Full article

(This article belongs to the Special Issue Cyanobacterial Toxins: Identification and Structural Characterisation to Better Understand Their Distribution and Diversity)

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Review

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40 pages, 2280 KiB

Open AccessEditor’s ChoiceReview

Structural Diversity, Characterization and Toxicology of Microcystins

by Noureddine Bouaïcha, Christopher O. Miles, Daniel G. Beach, Zineb Labidi, Amina Djabri, Naila Yasmine Benayache and Tri Nguyen-Quang

Toxins 2019, 11(12), 714; https://doi.org/10.3390/toxins11120714 - 07 Dec 2019

Cited by 260 | Viewed by 11215

Abstract

Hepatotoxic microcystins (MCs) are the most widespread class of cyanotoxins and the one that has most often been implicated in cyanobacterial toxicosis. One of the main challenges in studying and monitoring MCs is the great structural diversity within the class. The full chemical structure of the first MC was elucidated in the early 1980s and since then, the number of reported structural analogues has grown steadily and continues to do so, thanks largely to advances in analytical methodology. The structures of some of these analogues have been definitively elucidated after chemical isolation using a combination of techniques including nuclear magnetic resonance, amino acid analysis, and tandem mass spectrometry (MS/MS). Others have only been tentatively identified using liquid chromatography-MS/MS without chemical isolation. An understanding of the structural diversity of MCs, the genetic and environmental controls for this diversity and the impact of structure on toxicity are all essential to the ongoing study of MCs across several scientific disciplines. However, because of the diversity of MCs and the range of approaches that have been taken for characterizing them, comprehensive information on the state of knowledge in each of these areas can be challenging to gather. We have conducted an in-depth review of the literature surrounding the identification and toxicity of known MCs and present here a concise review of these topics. At present, at least 279 MCs have been reported and are tabulated here. Among these, about 20% (55 of 279) appear to be the result of chemical or biochemical transformations of MCs that can occur in the environment or during sample handling and extraction of cyanobacteria, including oxidation products, methyl esters, or post-biosynthetic metabolites. The toxicity of many MCs has also been studied using a range of different approaches and a great deal of variability can be observed between reported toxicities, even for the same congener. This review will help clarify the current state of knowledge on the structural diversity of MCs as a class and the impacts of structure on toxicity, as well as to identify gaps in knowledge that should be addressed in future research. Full article

(This article belongs to the Special Issue Cyanobacterial Toxins: Identification and Structural Characterisation to Better Understand Their Distribution and Diversity)

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34 pages, 2898 KiB

Open AccessEditor’s ChoiceReview

The Diversity of Cyanobacterial Toxins on Structural Characterization, Distribution and Identification: A Systematic Review

by Xingde Du, Haohao Liu, Le Yuan, Yueqin Wang, Ya Ma, Rui Wang, Xinghai Chen, Michael D. Losiewicz, Hongxiang Guo and Huizhen Zhang

Toxins 2019, 11(9), 530; https://doi.org/10.3390/toxins11090530 - 12 Sep 2019

Cited by 95 | Viewed by 8405

Abstract

The widespread distribution of cyanobacteria in the aquatic environment is increasing the risk of water pollution caused by cyanotoxins, which poses a serious threat to human health. However, the structural characterization, distribution and identification techniques of cyanotoxins have not been comprehensively reviewed in previous studies. This paper aims to elaborate the existing information systematically on the diversity of cyanotoxins to identify valuable research avenues. According to the chemical structure, cyanotoxins are mainly classified into cyclic peptides, alkaloids, lipopeptides, nonprotein amino acids and lipoglycans. In terms of global distribution, the amount of cyanotoxins are unbalanced in different areas. The diversity of cyanotoxins is more obviously found in many developed countries than that in undeveloped countries. Moreover, the threat of cyanotoxins has promoted the development of identification and detection technology. Many emerging methods have been developed to detect cyanotoxins in the environment. This communication provides a comprehensive review of the diversity of cyanotoxins, and the detection and identification technology was discussed. This detailed information will be a valuable resource for identifying the various types of cyanotoxins which threaten the environment of different areas. The ability to accurately identify specific cyanotoxins is an obvious and essential aspect of cyanobacterial research. Full article

(This article belongs to the Special Issue Cyanobacterial Toxins: Identification and Structural Characterisation to Better Understand Their Distribution and Diversity)

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