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Cyanobacterial Bioactive Molecules — an Overview of Their Toxic Properties
701 REVIEW / SYNTHE` SE Cyanobacterial bioactive molecules — an overview of their toxic properties Pranita Jaiswal, Pawan Kumar Singh, and Radha Prasanna Abstract: Allelopathic interactions involving cyanobacteria are being increasingly explored for the pharmaceutical and en- vironmental significance of the bioactive molecules. Among the toxic compounds produced by cyanobacteria, the biosyn- thetic pathways, regulatory mechanisms, and genes involved are well understood, in relation to biotoxins, whereas the cytotoxins are less investigated. A range of laboratory methods have been developed to detect and identify biotoxins in water as well as the causal organisms; these methods vary greatly in their degree of sophistication and the information they provide. Direct molecular probes are also available to detect and (or) differentiate toxic and nontoxic species from en- vironmental samples. This review collates the information available on the diverse types of toxic bioactive molecules pro- duced by cyanobacteria and provides pointers for effective exploitation of these biologically and industrially significant prokaryotes. Key words: cyanobacteria, bioactive molecules, cyanotoxins, NRP (non-ribosomal peptide), biocontrol agent. Re´sume´ : Les effets alle´lopathiques des cyoanobacte´ries sont de plus en explore´s pour identifier les mole´cules bioactives importantes d’un point de vue pharmaceutique ou environnemental. Parmi les compose´s toxiques produits par les cyano- bacte´ries, les biotoxines sont bien connues quant aux voies, aux me´canismes re´gulateurs et aux ge`nes implique´s dans leur biosynthe`se, alors que les cytotoxines sont moins e´tudie´es. Une varie´te´ de me´thodes de laboratoire ont e´te´ de´veloppe´es afin de de´tecter et d’identifier les biotoxines de l’eau et les agents qui en sont responsables; elles diffe`rent grandement quant a` leur degre´ de sophistication et a` l’information qu’elles ge´ne`rent. -
Suspect and Target Screening of Natural Toxins in the Ter River Catchment Area in NE Spain and Prioritisation by Their Toxicity
toxins Article Suspect and Target Screening of Natural Toxins in the Ter River Catchment Area in NE Spain and Prioritisation by Their Toxicity Massimo Picardo 1 , Oscar Núñez 2,3 and Marinella Farré 1,* 1 Department of Environmental Chemistry, IDAEA-CSIC, 08034 Barcelona, Spain; [email protected] 2 Department of Chemical Engineering and Analytical Chemistry, University of Barcelona, 08034 Barcelona, Spain; [email protected] 3 Serra Húnter Professor, Generalitat de Catalunya, 08034 Barcelona, Spain * Correspondence: [email protected] Received: 5 October 2020; Accepted: 26 November 2020; Published: 28 November 2020 Abstract: This study presents the application of a suspect screening approach to screen a wide range of natural toxins, including mycotoxins, bacterial toxins, and plant toxins, in surface waters. The method is based on a generic solid-phase extraction procedure, using three sorbent phases in two cartridges that are connected in series, hence covering a wide range of polarities, followed by liquid chromatography coupled to high-resolution mass spectrometry. The acquisition was performed in the full-scan and data-dependent modes while working under positive and negative ionisation conditions. This method was applied in order to assess the natural toxins in the Ter River water reservoirs, which are used to produce drinking water for Barcelona city (Spain). The study was carried out during a period of seven months, covering the expected prior, during, and post-peak blooming periods of the natural toxins. Fifty-three (53) compounds were tentatively identified, and nine of these were confirmed and quantified. Phytotoxins were identified as the most frequent group of natural toxins in the water, particularly the alkaloids group. -
Cyanobacterial Toxins: Saxitoxins
WHO/SDE/WSH/xxxxx English only Cyanobacterial toxins: Saxitoxins Background document for development of WHO Guidelines for Drinking-water Quality and Guidelines for Safe Recreational Water Environments Version for Public Review Nov 2019 © World Health Organization 20XX Preface Information on cyanobacterial toxins, including saxitoxins, is comprehensively reviewed in a recent volume to be published by the World Health Organization, “Toxic Cyanobacteria in Water” (TCiW; Chorus & Welker, in press). This covers chemical properties of the toxins and information on the cyanobacteria producing them as well as guidance on assessing the risks of their occurrence, monitoring and management. In contrast, this background document focuses on reviewing the toxicological information available for guideline value derivation and the considerations for deriving the guideline values for saxitoxin in water. Sections 1-3 and 8 are largely summaries of respective chapters in TCiW and references to original studies can be found therein. To be written by WHO Secretariat Acknowledgements To be written by WHO Secretariat 5 Abbreviations used in text ARfD Acute Reference Dose bw body weight C Volume of drinking water assumed to be consumed daily by an adult GTX Gonyautoxin i.p. intraperitoneal i.v. intravenous LOAEL Lowest Observed Adverse Effect Level neoSTX Neosaxitoxin NOAEL No Observed Adverse Effect Level P Proportion of exposure assumed to be due to drinking water PSP Paralytic Shellfish Poisoning PST paralytic shellfish toxin STX saxitoxin STXOL saxitoxinol -
Occurrence of a Cyanobacterial Neurotoxin, Anatoxin-A, in New
OCCURRENCE OF THE CYANOBACTERIAL NEUROTOXIN, ANATOXIN-A, IN NEW YORK STATE WATERS by Xingye Yang A dissertation submitted in partial fulfillment of the requirements for the Doctor of Philosophy Degree State University of New York College of Environmental Science and Forestry Syracuse, New York January 2007 Approved: Faculty of Chemistry ---------------------------------------------- ------------------------------------------------ Gregory L. Boyer, Major Professor William Shields, Chairperson, Examination Committee ------------------------------------------------ ------------------------------------------------- John P. Hassett, Faculty Chair Dudley J. Raynal, Dean, Instruction and Graduate Studies UMI Number: 3290535 Copyright 2008 by Yang, Xingye All rights reserved. UMI Microform 3290535 Copyright 2008 by ProQuest Information and Learning Company. All rights reserved. This microform edition is protected against unauthorized copying under Title 17, United States Code. ProQuest Information and Learning Company 300 North Zeeb Road P.O. Box 1346 Ann Arbor, MI 48106-1346 Acknowledgements I would like to express my sincerest gratitude to Dr. Gregory L. Boyer, my major professor and academic advisor for his guidance, support, and assistance over the past years. He has provided me with invaluable knowledge and skills. I thank Dr. David J. Kieber for his advice and instrument support. I acknowledge Dr. John P. Hassett for his support on both my research and my career. I appreciate Dr. Francis X. Webster for his help on chemical characterization. I thank Dr. James P. Nakas for advice on my career development. Thanks are also due to Dr. William Shields for serving as chairman of this examination committee. I appreciate critical reviews and comments on the thesis from all the examiners on this committee. I would like to thank Dr. Israel Cabasso and Dr. -
Western Lake Erie Harmful Algal Blooms
Harmful Algal Bloom Research Initiative Thomas Bridgeman, PhD University of Toledo Nov 30, 2016 Toledo Water Crisis, August 2014 Algal toxin in treated Toledo water exceeded 1.0 ug/L limit recommended by the WHO ‘Do not drink’ advisory Aug 2-4 500,000 residents temporarily without potable water Lake Erie Water Intake Toledo Blade CBS News Ohio Department of Higher Education Response Major algal groups in Lakes Diatoms Greens Blue-greens (Cyanobacteria) Common Harmful “Algae” (Cyanobacteria) Anabaena Aphanizomenon Microcystis (Dolichospermum) Planktothrix Lyngbya Lyngbya wollei and Microcystis sp. D. Hartsen T. Crail Why are harmful algae harmful? Microcystis toxins Planktothrix toxins Microcystin (FDF) Anatoxin Lyngbyatoxin Aplysiatoxin Anabaena toxins Lyngbya toxins Microcystin Saxitoxin Cylindrospermopsin Lyngbyatoxin Anatoxin (VFDF) Aplysiatoxin Saxitoxin Aphanizomenon toxins Cylindrospermopsin Anatoxin Saxitoxin Freshwater HABs are increasing worldwide Lake Taihu, China Lake Winnipeg Baltic Sea Lake Erie and Grand Lake St. Marys 13-Year Record of HABs August 2002 August 2003 Microcystis HABs in Lake Erie Western Lake Erie Harmful Algal Blooms 40000 35000 Catastrophic 30000 25000 20000 15000 Unacceptable 10000 5000 (ml/m2/y) Biovolume Microcystis Microcystis Biovolume (ml/m2/y) Biovolume Microcystis Acceptable 0 2002 2003 2004 2005 2006 2007 2008 2009 2010 2011 2012 2013 2014 2011 bloom from the International Space Station 2003 Michalak et al. 2013 2014: Winds and water currents concentrated the bloom along the Ohio shore Toledo Water Intake Not a Lake Problem, it’s a LAND problem Ohio Drainage Not just a Northern Ohio Problem Cincinnati Water Intake (H. Raymond, OEPA) The Greening of Lake Erie (Eutrophication) • Between1920 and 1964 Lake Erie algae biomass increased nearly 6 fold. -
Chemical and Biological Study of Aplysiatoxin Derivatives Showing Inhibition of Potassium Cite This: RSC Adv.,2019,9,7594 Channel Kv1.5†
RSC Advances View Article Online PAPER View Journal | View Issue Chemical and biological study of aplysiatoxin derivatives showing inhibition of potassium Cite this: RSC Adv.,2019,9,7594 channel Kv1.5† Yang-Hua Tang,‡ab Jing Wu,‡c Ting-Ting Fan,a Hui-Hui Zhang,a Xiao-Xia Gong,a Zheng-Yu Cao,e Jian Zhang,*c Hou-Wen Lin *d and Bing-Nan Han *a Three new aplysiatoxins, neo-debromoaplysiatoxin D (1), oscillatoxin E (2) and oscillatoxin F (3), accompanied by four known analogues (4–7), were identified from the marine cyanobacterium Lyngbya sp. Structural frames differ amongst these metabolites, and therefore we classified compounds 1 and 4– 6 as aplysiatoxins as they possess 6/12/6 and 6/10/6 tricyclic ring systems featuring a macrolactone ring, and compounds 2, 3 and 7 as oscillatoxins that feature a hexane-tetrahydropyran in a spirobicyclic system. Bioactivity experiments showed that compounds 1 and 4–6 presented significant expression of phosphor-PKCd whereas compounds 2, 5 and 7 showed the most potent blocking activity against Received 5th February 2019 Creative Commons Attribution-NonCommercial 3.0 Unported Licence. potassium channel Kv1.5 with IC values of 0.79 Æ 0.032 mM, 1.28 Æ 0.080 mM and 1.47 Æ 0.138 mM, Accepted 25th February 2019 50 respectively. Molecular docking analysis supplementing the binding interaction of oscillatoxin E (2) and DOI: 10.1039/c9ra00965e oscillatoxin F (3) with Kv1.5 showed oscillatoxin E (2) with a strong binding affinity of À37.645 kcal molÀ1 À rsc.li/rsc-advances and oscillatoxin F (3) with a weaker affinity of À32.217 kcal mol 1, further supporting the experimental data. -
Electrochemical Biosensors for Tracing Cyanotoxins in Food and Environmental Matrices
biosensors Review Electrochemical Biosensors for Tracing Cyanotoxins in Food and Environmental Matrices Antonella Miglione 1 , Maria Napoletano 1 and Stefano Cinti 1,2,* 1 Department of Pharmacy, University Naples Federico II, Via Domenico Montesano 49, 80131 Naples, Italy; [email protected] (A.M.); [email protected] (M.N.) 2 BAT Center–Interuniversity Center for Studies on Bioinspired Agro-Environmental Technology, University Naples Federico II, 80055 Naples, Italy * Correspondence: [email protected] Abstract: The adoption of electrochemical principles to realize on-field analytical tools for detecting pollutants represents a great possibility for food safety and environmental applications. With respect to the existing transduction mechanisms, i.e., colorimetric, fluorescence, piezoelectric etc., electrochemical mechanisms offer the tremendous advantage of being easily miniaturized, connected with low cost (commercially available) readers and unaffected by the color/turbidity of real matrices. In particular, their versatility represents a powerful approach for detecting traces of emerging pollutants such as cyanotoxins. The combination of electrochemical platforms with nanomaterials, synthetic receptors and microfabrication makes electroanalysis a strong starting point towards decentralized monitoring of toxins in diverse matrices. This review gives an overview of the electrochemical biosensors that have been developed to detect four common cyanotoxins, namely microcystin-LR, anatoxin-a, saxitoxin and cylindrospermopsin. The manuscript provides the readers a quick guide to understand the main electrochemical platforms that have been realized so far, and the presence of a comprehensive table provides a perspective at a glance. Keywords: electroanalysis; screen printed electrodes; voltammetry; impedance; aptamer; Citation: Miglione, A.; Napoletano, microcystin-LR; anatoxin-a; saxitoxin; cylindrospermopsin M.; Cinti, S. Electrochemical Biosensors for Tracing Cyanotoxins in Food and Environmental Matrices. -
Development and Validation of a Novel Approach for the Analysis of Marine Biotoxins
DEVELOPMENT AND VALIDATION OF A NOVEL APPROACH FOR THE ANALYSIS OF MARINE BIOTOXINS Bing Cheng Chai College of Engineering and Science Victoria University Submitted in fulfilment of the requirements of the degree of Doctor of Philosophy June 2017 ABSTRACT Harmful algal blooms (HABs) which can produce a variety of marine biotoxins are a prevalent and growing risk to public safety. The aim of this research was to investigate, evaluate, develop and validate an analytical method for the detection and quantitation of five important groups of marine biotoxins in shellfish tissue. These groups included paralytic shellfish toxins (PST), amnesic shellfish toxins (AST), diarrheic shellfish toxins (DST), azaspiracids (AZA) and neurotoxic shellfish toxins (NST). A novel tandem liquid chromatographic (LC) approach using hydrophilic interaction chromatography (HILIC), aqueous normal phase (ANP), reversed phase (RP) chromatography, tandem mass spectrometry (MSMS) and fluorescence spectroscopic detection (FLD) was designed and tested. During method development of the tandem LC setup, it was found that HILIC and ANP columns were unsuitable for the PSTs because of the lack of chromatographic separation power, precluding them from being used with MSMS detection. In addition, sensitivity for the PSTs at regulatory limits could not be achieved with MSMS detection, which led to a RP-FLD combination. The technique of RP-MSMS was found to be suitable for the remaining four groups of biotoxins. The final method was a combination of two RP columns coupled with FLD and MSMS detectors, with a valve switching program and injection program. A novel sample preparation method was also developed for the extraction and clean-up of biotoxins from mussels. -
SAXITOXIN ELISA a Competitive Enzyme Immunoassay For
SAXITOXIN ELISA (5191SAXI[5]04.20) A competitive enzyme immunoassay for screening and quantitative analysis of Saxitoxin in various matrices EUROPROXIMA SAXITOXIN ELISA A competitive enzyme immunoassay for screening and quantitative analysis of Saxitoxin in various matrices TABLE OF CONTENTS PAGE: Brief Information .............................................................. 2 1. Introduction ...................................................................... 2 2. Principle of Saxitoxin ELISA ............................................ 3 3. Specificity and Sensitivity ................................................ 4 4. Handling and Storage ...................................................... 5 5. Kit contents ...................................................................... 6 6. Equipment required but not provided .............................. 7 7. Precautions ...................................................................... 7 8. Sample preparation ......................................................... 8 9. Preparation of reagents ................................................... 8 10. Assay Procedure ............................................................. 10 11. Interpretation of results .................................................... 12 12. Literature .......................................................................... 13 13. Ordering information ........................................................ 13 14. Revision history ............................................................... -
Author's Personal Copy
Author's personal copy Provided for non-commercial research and educational use only. Not for reproduction, distribution or commercial use. This chapter was originally published in the book Encyclopedia of Toxicology. The copy attached is provided by Elsevier for the author's benefit and for the benefit of the author's institution, for non-commercial research, and educational use. This includes without limitation use in instruction at your institution, distribution to specific colleagues, and providing a copy to your institution's administrator. All other uses, reproduction and distribution, including without limitation commercial reprints, selling or licensing copies or access, or posting on open internet sites, your personal or institution’s website or repository, are prohibited. For exceptions, permission may be sought for such use through Elsevier’s permissions site at: http://www.elsevier.com/locate/permissionusematerial From Hambright, K.D., Zamor, R.M., Easton, J.D., Allison, B., 2014. Algae. In: Wexler, P. (Ed.), Encyclopedia of Toxicology, 3rd edition vol 1. Elsevier Inc., Academic Press, pp. 130–141. ISBN: 9780123864543 Copyright © 2014 Elsevier, Inc. unless otherwise stated. All rights reserved. Academic Press Author's personal copy Algae KD Hambright and RM Zamor, Plankton Ecology and Limnology Laboratory, University of Oklahoma Biological Station, and Program in Ecology and Evolutionary Biology, University of Oklahoma, Norman, OK, USA JD Easton and B Allison, Plankton Ecology and Limnology Laboratory, University of Oklahoma Biological Station, University of Oklahoma, Kingston, OK, USA Ó 2014 Elsevier Inc. All rights reserved. This article is a revision of the previous edition article by Keiko Okamoto and Lora E. Fleming, volume 1, pp 68–76, Ó 2005, Elsevier Inc. -
Running Head: CYANOBACTERIA, Β-METHYLAMINO-L-ALANINE
Running head: CYANOBACTERIA, b-METHYLAMINO-L-ALANINE, AND NEURODEGENERATION Cyanobacteria, β-Methylamino-L-Alanine, and Neurodegeneration Jonathan Hunyadi Lourdes University CYANOBACTERIA, b-METHYLAMINO-L-ALANINE, AND NEURODEGENERATION 2 ABSTRACT Research has found a potential link between the non-proteinogenic amino acid b-methylamino-L-alanine (BMAA) and neurodegenerative diseases. First identified on the island of Guam with a rare form of amyotrophic lateral sclerosis (ALS) commonly called “Guam disease”, the source of BMAA was identified to be cyanobacteria. Due primarily to eutrophication, cyanobacteria can form large “algal blooms” within water bodies. A major concern during cyanobacterial blooms is the production of high concentrations of cyanotoxins such as BMAA. Cyanotoxin biosynthesis is dependent on the presence of specific genes as well as environmental regulating factors. Numerous techniques are capable of analyzing cyanobacteria and cyanotoxins which include: microscopy, pigment spectroscopy, polymerase chain reaction, microarrays, enzyme-linked immunosorbent assays, and liquid chromatography. Liquid chromatography is the primary technique used to analyze BMAA, however, there has been controversy regarding its detection within nervous tissue samples. While BMAAs role in neurodegeneration is unclear, dietary intake has been demonstrated to produce both b-amyloid plaques and tau tangles within Vervet monkeys, hallmarks of both Alzheimer’s disease and Guam disease. Two of the dominant hypothesized mechanisms of BMAA neurotoxicity are glutamate excitotoxicity, by which BMAA functions as a glutamate agonist causing endoplasmic reticulum stress and initiates a cascade leading to tau hyperphosphorylation, and protein incorporation, by which BMAA enters neurons and becomes mis-incorporated within proteins, leading to misfolding and aggregation. As a result of this research, alanine supplements have entered clinical trials for both Alzheimer’s disease and ALS to compete with BMAA in protein incorporation. -
Debromoaplysiatoxin in Lyngbya-Dominated Mats on Manatees (Trichechus Manatus Latirostris) in the Florida King's Bay Ecosyst
Toxicon 52 (2008) 385–388 Contents lists available at ScienceDirect Toxicon journal homepage: www.elsevier.com/locate/toxicon Short communication Debromoaplysiatoxin in Lyngbya-dominated mats on manatees (Trichechus manatus latirostris) in the Florida King’s Bay ecosystem Kendal E. Harr a,*, Nancy J. Szabo b, Mary Cichra c, Edward J. Phlips c a FVP Consultants, Inc., 7805 SW 19th Place, Gainesville, FL 32607, USA b Analytical Toxicology Core Laboratory, Center for Environmental & Human Toxicology, University of Florida, Box 110885, Gainesville, FL 32611, USA c Department of Fisheries and Aquatic Sciences, University of Florida, 7922 NW 71st Street, Gainesville, FL 32653, USA article info abstract Article history: Proliferation of the potentially toxic cyanobacterium, Lyngbya, in Florida lakes and rivers Received 10 March 2008 has raised concerns about ecosystem and human health. Debromoaplysiatoxin (DAT) Received in revised form 14 May 2008 was measured in concentrations up to 6.31 mg/g wet weight lyngbyatoxin A equivalents Accepted 15 May 2008 (WWLAE) in Lyngbya-dominated mats collected from natural substrates. DAT was also Available online 5 June 2008 detected (up to 1.19 mg/g WWLAE) in Lyngbya-dominated mats collected from manatee dorsa. Ulcerative dermatitis found on manatees is associated with, but has not been proven Keywords: to be caused by DAT. Debromoaplysiatoxin Dermatitis Ó 2008 Elsevier Ltd. All rights reserved. Lyngbya Manatee Florida Over the past century, widespread increases in Although the majority of research has focused on eutrophication rates have led to a global magnification of L. majuscula, two freshwater Lyngbya species are known harmful algal blooms in aquatic ecosystems (Hallegraeff, to be toxigenic, Lyngbya wollei (Carmichael et al., 1997) 1993; Phlips, 2002).