Handbook of Cyanobacterial Monitoring and Cyanotoxin Analysis
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Handbook of Cyanobacterial Monitoring and Cyanotoxin Analysis
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John Wiley and Sons Ltd
01/2017
576
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Inglês
9781119068686
15 a 20 dias
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List of Contributors xvii Preface xxvi Acknowledgements xxviii Section I Introduction 1 1 Introduction: Cyanobacteria, Cyanotoxins, Their Human Impact, and Risk Management 3 Geoffrey A. Codd, Jussi Meriluoto, and James S. Metcalf 1.1 Introduction 3 1.2 Cyanotoxins 4 1.3 Exposure Routes, Exposure Media, and At Risk Human Activities 6 1.4 Cyanobacterial Blooms and Cyanotoxins in Relation to Human Pressures on Water Resources and Climate Change 7 1.5 Aims of the Handbook 7 References 8 Section II Cyanobacteria 9 2 Ecology of Cyanobacteria 11 Jean Francois Humbert and Jutta Fastner 2.1 Introduction 11 2.2 Environmental Conditions Leading to Cyanobacterial Blooms 12 2.3 Population Dynamics of Cyanobacteria 13 2.4 Spatial Distribution of Cyanobacteria in Freshwater Ecosystems 15 2.5 Ecology of the Production of Toxins by Cyanobacteria 16 2.6 General Conclusions 17 References 17 3 Picocyanobacteria: The Smallest Cell Size Cyanobacteria 19 Iwona Jasser and Cristiana Callieri 3.1 Introduction 19 3.2 Records of Toxic Picocyanobacteria 21 3.3 Summary 25 References 26 4 Expansion of Alien and Invasive Cyanobacteria 28 Miko aj Kokoci ski, Reyhan Akcaalan, Nico Salmaso, Maya Petrova Stoyneva Gartner, and Assaf Sukenik 4.1 Introduction 28 4.2 Definition of Invasive/Alien Species: Nomenclature Problems 29 4.2.1 Invasive Species Concept in Cyanobacteria 29 4.3 Occurrence of Invasive and Alien Cyanobacteria 31 4.4 Factors Enhancing the Expansion of Alien Cyanobacteria 33 4.5 Impact of Cyanobacterial Invasion on Ecosystem 34 References 36 Section III Sampling, Monitoring and Risk Management 41 5 Health and Safety During Sampling and in the Laboratory 43 Roberta Congestri, James S. Metcalf , Luca Lucentini, and Federica Nigro Di Gregorio 5.1 Introduction 43 5.2 Sampling Safety 43 5.3 Laboratory Safety 44 5.4 Cyanotoxin Production and Application 45 5.5 Contamination due to Equipment, Glassware, and Accidents 45 References 45 6 Basic Guide to Detection and Monitoring of Potentially Toxic Cyanobacteria 46 Nico Salmaso, Cecile Bernard , Jean Francois Humbert, Reyhan Akcaalan, Meric Albay, Andreas Ballot , Arnaud Catherine, Jutta Fastner , Kerstin Haggqvist, Maria Horecka, Katarzyna Izydorczyk, Latife Koker , Ji i Komarek, Selma Maloufi, Joanna Mankiewicz Boczek, James S. Metcalf , Antonio Quesada, Catherine Quiblier , and Claude Yepremian 6.1 Introduction 47 6.2 Monitoring of Cyanobacteria: Sampling Strategies 48 6.3 Cyanobacterial Identification and Quantification 55 Appendix 6.1 Testing Phytoplankton Distributions: 2 Test (Pearson Goodness of Fit Test) 63 References 66 7 Case Studies of Environmental Sampling, Detection, and Monitoring of Potentially Toxic Cyanobacteria 70 Kerstin Haggqvist, Reyhan Akcaalan, Isidora Echenique Subiabre, Jutta Fastner , Maria Horecka, Jean Francois Humbert, Katarzyna Izydorczyk, Tomasz Jurczak, Miko aj Kokoci ski, Tore Lindholm, Joanna Mankiewicz Boczek, Antonio Quesada, Catherine Quiblier, and Nico Salmaso 7.1 Introduction 71 7.2 Shallow Lakes 71 7.3 Deep Lakes 74 7.4 Reservoirs 75 7.5 Rivers 77 7.6 The Baltic Sea 78 7.7 Waterbodies Used for Drinking Water Production 79 References 81 8 New Tools for the Monitoring of Cyanobacteria in Freshwater Ecosystems 84 Jean Francois Humbert and Andrea Torokne 8.1 Introduction 84 8.2 Use of Photosynthetic Pigments for the In Situ Quantification of Cyanobacteria and Other Phytoplankton in Water 85 8.3 Integration of Physicochemical and Fluorescence Sensors in Buoys 86 8.4 New Methods for Automatic Cell Counting in Water Samples 86 References 87 9 Remote Sensing of Cyanobacterial Blooms in Inland, Coastal, and Ocean Waters 89 Peter D. Hunter , Mark W. Matthews , Tiit Kutser , and Andrew N. Tyler 9.1 Introduction 89 9.2 Bio optical Properties of Marine and Inland Waters 90 9.3 Platforms and Sensors 91 9.4 Overview of Approaches 92 9.5 Case Study Examples 95 9.6 Future Prospects 96 References 98 10 The Italian System for Cyanobacterial Risk Management in Drinking Water Chains 100 Luca Lucentini, Liliana La Sala , Rossella Colagrossi , and Roberta Congestri 10.1 Introduction 100 10.2 Risk Assessment of Toxic Cyanobacterial Outbreaks in Water for Human Consumption in Italy 101 10.3 Framework of Risk Management of Toxic Cyanobacterial Outbreaks in Water for Human Consumption 102 10.4 Risk Information and Communication 106 References 106 Section IV Toxins and Bioactive/Noxious Compounds from Cyanobacteria 107 11 Microcystins and Nodularins 109 Arnaud Catherine, Cecile Bernard, Lisa Spoof , and Milena Bruno 11.1 Chemical Characteristics and Diversity of Microcystins and Nodularins 109 11.2 Biosynthesis and Genetics of MC and NOD Production 110 11.3 Occurrence of MCs and NODs 112 11.4 Toxicological Effects and Associated Health Risk 113 11.5 Available Methods for the Analysis of MCs and NODs 117 References 118 12 Cylindrospermopsin and Congeners 127 Miko aj Kokoci ski, Ana Maria Camean, Shmuel Carmeli, Remedios Guzman Guillen, Angeles Jos, Joanna Mankiewicz Boczek , James S. Metcalf , Isabel Maria Moreno, Ana Isabel Prieto, and Assaf Sukenik 12.1 Chemical Characteristics of Cylindrospermopsin and Congeners 127 12.2 Genes Involved in CYN Biosynthesis 128 12.3 CYN Producers and Distribution 128 12.4 Toxicity of CYN 129 12.5 The Biological Role of CYN 132 12.6 Degradation of CYN 132 12.7 Available Methods for Determining CYN in Waters 132 References 133 13 Anatoxin a, Homoanatoxin a, and Natural Analogues 138 Milena Bruno, Olivier Ploux, James S. Metcalf , Annick Mejean, Barbara Pawlik Skowronska, and Ambrose Furey 13.1 Introduction 138 13.2 Chemical Structure, Synthesis, and Reactivity 138 13.3 Biosynthesis of ANTX, HANTX, and dihydroANTX 140 13.4 Occurrence and Producing Strains 140 13.5 Toxicity and Pharmacology 141 13.6 Analytical Methodologies 142 References 144 14 Saxitoxin and Analogues 148 Andreas Ballot, Cecile Bernard, and Jutta Fastner 14.1 Introduction 148 14.2 Toxicity of STXs 149 14.3 Occurrence 149 14.4 Genetics and Biosynthesis 150 14.5 Detection Methods 151 14.6 Guidance Values or National Regulations or Recommendations for Managing STXs 152 References 152 15 Anatoxin a(S) 155 James S. Metcalf and Milena Bruno 15.1 Chemical Structure of Anatoxin a(S) 155 15.2 Biosynthesis 155 15.3 Occurrence and Producing Strains 156 15.4 Toxicology and Pharmacology 156 15.5 Analytical Methods for Determination and Quantification 157 References 158 16 N Methylamino l Alanine and (S) 2,4 Diaminobutyric Acid 160 Olivier Ploux, Audrey Combes, Johan Eriksson, and James S. Metcalf 16.1 Historical Overview 160 16.2 Structure, Synthesis, and Molecular Properties 161 16.3 Neurotoxicity 161 16.4 Methods for Identification and Quantification 162 16.5 Occurrence in Cyanobacteria, Plants, and Animals 162 References 163 17 Lipopolysaccharide Endotoxins 165 Silvia Monteiro, Ricardo Santos, Lud k Blaha, and Geoffrey A. Codd 17.1 Lipopolysaccharide Endotoxins: Structure 165 17.2 Occurrence of LPS Endotoxins 167 17.3 Toxic Effects of LPS Endotoxins 168 17.4 Methods for Determination of LPS Endotoxins 169 References 170 18 Cyanobacterial Retinoids 173 Kunimitsu Kaya and Tomoharu Sano 18.1 Introduction 173 18.2 Detection of Retinoids Produced by Cyanobacteria 174 18.3 Chemistry and Analysis of Retinoids 175 18.4 Malformations by Cyanobacterial Retinoids 176 18.5 Concluding Remarks 176 References 176 19 Other Cyanobacterial Bioactive Substances 179 Tina Elersek, Lud k Blaha, Hanna Mazur Marzec, Wido Schmidt, and Shmuel Carmeli 19.1 Introduction 179 19.2 Aeruginosins and Spumigins 182 19.3 Anabaenopeptins 184 19.4 Biogenic Amines 185 19.5 Depsipeptides 186 19.6 Endocrine Disruptors and Novel Tumour Promoters 187 19.7 Lyngbyatoxins and Other Toxins Produced by Lyngbya majuscula 188 19.8 Microginins 189 19.9 Microviridins 189 References 190 20 Taste and Odour Compounds Produced by Cyanobacteria 196 Triantafyllos Kaloudis, Theodoros M. Triantis, and Anastasia Hiskia 20.1 Cyanobacterial Taste and Odour Compounds in Water Resources 196 20.2 Analytical Methods for Taste and Odour Compounds 197 References 199 Section V Screening and Trace Analysis of Cyanotoxins 203 21 Determination of Cyanotoxins by High Performance Liquid Chromatography with Photodiode Array 205 Anastasia Hiskia, Lisa Spoof , Triantafyllos Kaloudis, and Jussi Meriluoto 21.1 Introduction: Application of High Performance Liquid Chromatography for Different Classes of Cyanotoxins 205 21.2 HPLC of Microcystins and Nodularins 206 21.3 HPLC of Anatoxins 208 21.4 HPLC of Cylindrospermopsin 208 21.5 Advantages and Disadvantages of HPLC PDA 208 References 209 22 Determination of Cyanotoxins by High Performance Liquid Chromatography with Fluorescence Derivatization 212 James S. Metcalf and Paulo Baptista Pereira 22.1 Principle of the Technique and Why It Is Used for Cyanotoxins 212 22.2 Types of Reactions for Analysing Paralytic Shellfish Toxins Using High Performance Liquid Chromatography with Fluorescence Derivatization 213 22.3 Types of Reactions for Analysing N Methylamino l Alanine and Isomers by HPLC FLD 216 22.4 Need for Confirmatory Techniques with HPLC FLD 216 References 216 23 Liquid Chromatography Mass Spectrometry 218 Josep Caixach, Cintia Flores, Lisa Spoof , Jussi Meriluoto, Wido Schmidt, Hanna Mazur Marzec, Anastasia Hiskia, Triantafyllos Kaloudis, and Ambrose Furey 23.1 Introduction 218 23.2 Ion Sources 220 23.3 Types of Mass Analysers 225 23.4 Application of LC MS in Cyanotoxin Analyses 233 23.5 Overview of Quantitation: Cyanobacterial Toxins 235 23.6 Ion Suppression/Enhancement Considerations 237 23.7 High Resolution Mass Spectrometry (HRMS) 239 23.8 MS Experiments for the Detection of Unknown Cyanotoxins 242 23.9 Performance Criteria of LC MS Methods for Identification and Quantification of Cyanotoxins 249 References 251 24 Capillary Electrophoresis of Cyanobacterial Toxins 258 Gabor Vasas 24.1 Basic Theory and Introduction of Capillary Electrophoresis 258 24.2 Selection of Separation Methods 259 24.3 Detection Methods 259 24.4 CE Methods of Cyanobacterial Toxins 260 24.5 Future Perspectives 262 References 262 25 Immunoassays and Other Antibody Applications 263 James S. Metcalf and Geoffrey A. Codd 25.1 Introduction 263 25.2 Production of Antibodies versus Cyanotoxins 264 25.3 Applications of Cyanotoxin Antibodies 264 25.4 Cyanotoxin Localisation and Quantification Using Antibodies 265 25.5 Other Cyanotoxin Antibody Related Technologies 265 References 266 26 Protein Phosphatase Inhibition Assays 267 James S. Metcalf , Anastasia Hiskia, and Triantafyllos Kaloudis 26.1 Background and Molecular Mechanism of Protein Phosphatase Inhibition 267 26.2 Classes of Compounds that Inhibit Protein Phosphatases 268 26.3 Effects of Microcystins on Cyanobacterial Protein Phosphatases 268 26.4 The Basis of the PPIA Assay for Microcystins and Its Evolution 268 26.5 Comparison of PPIA with Other Analytical Methods for Microcystins 268 26.6 Commercially Available Kits for Microcystins 269 26.7 Improvements to the PPIA Assay to Make It More Specific to Microcystins 269 26.8 Conclusions about the Effectiveness of the PPIA Assay for Microcystins and Nodularins in Different Matrices 269 References 270 27 Bioassay Use in the Field of Toxic Cyanobacteria 272 Lud k Blaha, Ana Maria Camean , Valerie Fessard , Daniel Gutierrez Praena , Angeles Jos , Benjamin Marie , James S. Metcalf , Silvia Pichardo , Maria Puerto , Andrea Torokne , Gabor Vasas, and Bojana egura 27.1 Introduction 272 27.2 Drivers and Objectives for Bioassay Use 273 27.3 Classification and Terminology 274 27.4 Bioassays for the Effect Evaluation 275 27.5 Bioassays for Monitoring 276 27.6 Conclusions and Future Perspectives 278 References 278 28 Molecular Tools for the Detection of Toxigenic Cyanobacteria in Natural Ecosystems 280 Jean Francois Humbert 28.1 Introduction 280 28.2 Molecular Methods for the Monitoring of Potentially Toxic Cyanobacteria 281 28.3 Strengths and Limitation of These Molecular Approaches 282 28.4 Conclusions 282 References 283 Section VI Methodological Considerations 285 29 Method Validation Guidelines for the Analysis of Cyanotoxins 287 Theodoros M. Triantis, Triantafyllos Kaloudis, and Anastasia Hiskia 29.1 Introduction: Method Validation as a Requirement for Laboratory Accreditation 287 29.2 Performance Criteria and Validation Protocols for the Analysis of Cyanotoxins in Environmental Studies 288 29.3 Validation Issues Concerning the Analysis of Cyanotoxins 290 References 291 30 Interpretation, Significance, and Reporting of Results 292 Geoffrey A. Codd, Jutta Fastner , Tore Lindholm, Jussi Meriluoto, and James S. Metcalf 30.1 Introduction 292 30.2 Interpretation and Significance of Results 293 30.3 Reporting of Results and Maximization of Benefits 294 30.4 Examples, Debriefing 294 References 296 31 Lessons from the U ice Case: How to Complement Analytical Data 298 Zorica Svir ev , Damjana Drobac , Nada Tokodi , Dunja eni , Jelica Simeunovi , Anastasia Hiskia , Triantafyllos Kaloudis , Biljana Mijovi , Stamenko u ak , Mla an Proti , Milka Vidovi , Antonije Onjia , Sonja Nybom , Tamara Va i , Tamara Palana ki Male evi , Tamara Duli , Dijana Panteli , Marina Vuka inovi , and Jussi Meriluoto 31.1 Introduction 299 31.2 Vrutci Reservoir and the Cyanobacterial Bloom Detected in December 2013 299 31.3 Analytical Work: Toxin Analyses of Water, Cyanobacterial Biomass, and Fish from Reservoir Vrutci 301 31.4 Complementary Data on Toxicity and Observed Health Problems 302 31.5 Analytical and Supplementary Results Combined: A Plausible Reconstruction of Events in Vrutci Reservoir and the City of U ice 306 31.6 Conclusions from the U ice Case 306 References 307 32 Selection of Analytical Methodology for Cyanotoxin Analysis 309 Jussi Meriluoto , James S. Metcalf and Geoffrey A. Codd 32.1 Introduction 309 32.2 General Comparison of Physicochemical Analyses, Biochemical Methods, and Bioassays 309 32.3 Guidance for Selecting and Using Standard Operating Procedures Found in this Handbook 310 32.4 Methodology versus Required Response Time 311 32.5 Influence of Waterbody History on the Choice of Methods 312 32.6 Integration of the Results Obtained: Making Sense 312 Section VII Standard Operating Procedures (SOPs) 313 SOP 1 Cyanobacterial Samples: Preservation, Enumeration, and Biovolume Measurements 315 Arnaud Catherine, Selma Maloufi, Roberta Congestri, Emanuela Viaggiu, and Renata Pilkaityte SOP 2 Chlorophyll a Extraction and Determination 331 Claude Yepremian, Arnaud Catherine, Cecile Bernard, Roberta Congestri, Tina Elersek, and Renata Pilkaityte SOP 3 Phycocyanin Extraction and Determination 335 Claude Yepremian, Arnaud Catherine, Cecile Bernard, Roberta Congestri, Tina Elersek, and Renata Pilkaityte SOP 4 Analysis of Picocyanobacteria Abundance in Epifluorescence Microscopy 339 Iwona Jasser and Cristiana Callieri SOP 5 Estimation of Cyanobacteria Biomass by Marker Pigment Analysis 343 Jean Pierre Descy SOP 6 Extraction of Cyanotoxins from Cyanobacterial Biomass 350 Leonardo Cerasino, Jussi Meriluoto, Lud k Blaha, Shmuel Carmeli, Triantafyllos Kaloudis, and Hanna Mazur Marzec SOP 7 Solid Phase Extraction of Microcystins and Nodularin from Drinking Water 354 Theodoros M. Triantis, Triantafyllos Kaloudis, Sevasti-Kiriaki Zervou, and Anastasia Hiskia SOP 8 Extraction of Microcystins from Animal Tissues 358 Ond ej Adamovsky and Lud k Blaha SOP 9 Analysis of Microcystins by Online Solid Phase Extraction Liquid Chromatography Tandem Mass Spectrometry 362 Cintia Flores and Josep Caixach SOP 10 Determination of Microcystins and Nodularin in Filtered and Drinking Water by LC MS/MS 372 Theodoros M. Triantis, Triantafyllos Kaloudis, Sevasti-Kiriaki Zervou, and Anastasia Hiskia SOP 11 Analysis of Microcystins and Nodularin by Ultra High Performance Liquid Chromatography Tandem Mass Spectrometry 379 Leonardo Cerasino SOP 12 Analysis of Microcystins in Animal Tissues Using LC MS/MS 385 Ji i Kohoutek and Lud k Blaha SOP 13 Quantitative Screening of Microcystins and Nodularin in Water Samples with Commercially Available ELISA Kits 390 Triantafyllos Kaloudis, Theodoros M. Triantis, and Anastasia Hiskia SOP 14 Quantitative Screening of Microcystins and Nodularin in Water Samples with Commercially Available PPIA Kits 393 Triantafyllos Kaloudis, Theodoros M. Triantis, and Anastasia Hiskia SOP 15 Solid Phase Extraction of Cylindrospermopsin from Filtered and Drinking Water 396 Theodoros M. Triantis, Triantafyllos Kaloudis, and Anastasia Hiskia SOP 16 Determination of Cylindrospermopsin in Filtered and Drinking Water by LC MS/MS 399 Theodoros M. Triantis, Triantafyllos Kaloudis, and Anastasia Hiskia SOP 17 Solid Phase Extraction of Anatoxin a from Filtered and Drinking Water 405 Theodoros M. Triantis, Triantafyllos Kaloudis, and Anastasia Hiskia SOP 18 Determination of Anatoxin a in Filtered and Drinking Water by LC MS/MS 408 Theodoros M. Triantis, Triantafyllos Kaloudis, and Anastasia Hiskia SOP 19 Analysis of Anatoxin a and Cylindrospermopsin by Ultra High-Performance Liquid Chromatography Tandem Mass Spectrometry 413 Leonardo Cerasino SOP 20 Extraction and Chemical Analysis of Saxitoxin and Analogues in Water 418 Lutz Imhof and Wido Schmidt SOP 21 Extraction of BMAA from Cyanobacteria 432 James S. Metcalf, Sandra A. Banack, and Paul A. Cox SOP 22 Analysis of -N Methylamino l Alanine by UHPLC MS/MS 435 James S. Metcalf, William B. Glover, Sandra A. Banack, and Paul A. Cox SOP 23 Extraction and LC MS/MS Analysis of Underivatised BMAA 439 Elisabeth J. Faassen SOP 24 Extraction, Purification, and Testing of LPS from Cyanobacterial Samples 447 Lucie Blahova and Lud k Blaha SOP 25 Extraction and Chemical Analysis of Planktopeptin and Anabaenopeptins 452 Hanna Mazur Marzec, Tina Elersek, and Agata B aszczyk SOP 26 Thamnocephalus Test 462 Andrea Torokne SOP 27 Determination of Geosmin and 2 Methylisoborneol in Water by HS SPME GC/MS 469 Triantafyllos Kaloudis, Theodoros M. Triantis, and Anastasia Hiskia SOP 28 Rapid Analysis of Geosmin and 2 Methylisoborneol from Aqueous Samples Using Solid Phase Extraction and GC MS 475 Christine Edwards, Craig McKenzie, Carlos Joao Pestana, Kyari Yates, and Linda A. Lawton SOP 29 Basic Validation Protocol for the Analysis of Cyanotoxins in Environmental Samples 481 Triantafyllos Kaloudis, Theodoros M. Triantis, and Anastasia Hiskia Section VIII Appendices 487 Appendix 1 Cyanobacterial Species and Recent Synonyms 489 Appendix 2 Cyanobacteria Associated With the Production of Cyanotoxins 501 Appendix 3 Tables of Microcystins and Nodularins 526 Index 538
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List of Contributors xvii Preface xxvi Acknowledgements xxviii Section I Introduction 1 1 Introduction: Cyanobacteria, Cyanotoxins, Their Human Impact, and Risk Management 3 Geoffrey A. Codd, Jussi Meriluoto, and James S. Metcalf 1.1 Introduction 3 1.2 Cyanotoxins 4 1.3 Exposure Routes, Exposure Media, and At Risk Human Activities 6 1.4 Cyanobacterial Blooms and Cyanotoxins in Relation to Human Pressures on Water Resources and Climate Change 7 1.5 Aims of the Handbook 7 References 8 Section II Cyanobacteria 9 2 Ecology of Cyanobacteria 11 Jean Francois Humbert and Jutta Fastner 2.1 Introduction 11 2.2 Environmental Conditions Leading to Cyanobacterial Blooms 12 2.3 Population Dynamics of Cyanobacteria 13 2.4 Spatial Distribution of Cyanobacteria in Freshwater Ecosystems 15 2.5 Ecology of the Production of Toxins by Cyanobacteria 16 2.6 General Conclusions 17 References 17 3 Picocyanobacteria: The Smallest Cell Size Cyanobacteria 19 Iwona Jasser and Cristiana Callieri 3.1 Introduction 19 3.2 Records of Toxic Picocyanobacteria 21 3.3 Summary 25 References 26 4 Expansion of Alien and Invasive Cyanobacteria 28 Miko aj Kokoci ski, Reyhan Akcaalan, Nico Salmaso, Maya Petrova Stoyneva Gartner, and Assaf Sukenik 4.1 Introduction 28 4.2 Definition of Invasive/Alien Species: Nomenclature Problems 29 4.2.1 Invasive Species Concept in Cyanobacteria 29 4.3 Occurrence of Invasive and Alien Cyanobacteria 31 4.4 Factors Enhancing the Expansion of Alien Cyanobacteria 33 4.5 Impact of Cyanobacterial Invasion on Ecosystem 34 References 36 Section III Sampling, Monitoring and Risk Management 41 5 Health and Safety During Sampling and in the Laboratory 43 Roberta Congestri, James S. Metcalf , Luca Lucentini, and Federica Nigro Di Gregorio 5.1 Introduction 43 5.2 Sampling Safety 43 5.3 Laboratory Safety 44 5.4 Cyanotoxin Production and Application 45 5.5 Contamination due to Equipment, Glassware, and Accidents 45 References 45 6 Basic Guide to Detection and Monitoring of Potentially Toxic Cyanobacteria 46 Nico Salmaso, Cecile Bernard , Jean Francois Humbert, Reyhan Akcaalan, Meric Albay, Andreas Ballot , Arnaud Catherine, Jutta Fastner , Kerstin Haggqvist, Maria Horecka, Katarzyna Izydorczyk, Latife Koker , Ji i Komarek, Selma Maloufi, Joanna Mankiewicz Boczek, James S. Metcalf , Antonio Quesada, Catherine Quiblier , and Claude Yepremian 6.1 Introduction 47 6.2 Monitoring of Cyanobacteria: Sampling Strategies 48 6.3 Cyanobacterial Identification and Quantification 55 Appendix 6.1 Testing Phytoplankton Distributions: 2 Test (Pearson Goodness of Fit Test) 63 References 66 7 Case Studies of Environmental Sampling, Detection, and Monitoring of Potentially Toxic Cyanobacteria 70 Kerstin Haggqvist, Reyhan Akcaalan, Isidora Echenique Subiabre, Jutta Fastner , Maria Horecka, Jean Francois Humbert, Katarzyna Izydorczyk, Tomasz Jurczak, Miko aj Kokoci ski, Tore Lindholm, Joanna Mankiewicz Boczek, Antonio Quesada, Catherine Quiblier, and Nico Salmaso 7.1 Introduction 71 7.2 Shallow Lakes 71 7.3 Deep Lakes 74 7.4 Reservoirs 75 7.5 Rivers 77 7.6 The Baltic Sea 78 7.7 Waterbodies Used for Drinking Water Production 79 References 81 8 New Tools for the Monitoring of Cyanobacteria in Freshwater Ecosystems 84 Jean Francois Humbert and Andrea Torokne 8.1 Introduction 84 8.2 Use of Photosynthetic Pigments for the In Situ Quantification of Cyanobacteria and Other Phytoplankton in Water 85 8.3 Integration of Physicochemical and Fluorescence Sensors in Buoys 86 8.4 New Methods for Automatic Cell Counting in Water Samples 86 References 87 9 Remote Sensing of Cyanobacterial Blooms in Inland, Coastal, and Ocean Waters 89 Peter D. Hunter , Mark W. Matthews , Tiit Kutser , and Andrew N. Tyler 9.1 Introduction 89 9.2 Bio optical Properties of Marine and Inland Waters 90 9.3 Platforms and Sensors 91 9.4 Overview of Approaches 92 9.5 Case Study Examples 95 9.6 Future Prospects 96 References 98 10 The Italian System for Cyanobacterial Risk Management in Drinking Water Chains 100 Luca Lucentini, Liliana La Sala , Rossella Colagrossi , and Roberta Congestri 10.1 Introduction 100 10.2 Risk Assessment of Toxic Cyanobacterial Outbreaks in Water for Human Consumption in Italy 101 10.3 Framework of Risk Management of Toxic Cyanobacterial Outbreaks in Water for Human Consumption 102 10.4 Risk Information and Communication 106 References 106 Section IV Toxins and Bioactive/Noxious Compounds from Cyanobacteria 107 11 Microcystins and Nodularins 109 Arnaud Catherine, Cecile Bernard, Lisa Spoof , and Milena Bruno 11.1 Chemical Characteristics and Diversity of Microcystins and Nodularins 109 11.2 Biosynthesis and Genetics of MC and NOD Production 110 11.3 Occurrence of MCs and NODs 112 11.4 Toxicological Effects and Associated Health Risk 113 11.5 Available Methods for the Analysis of MCs and NODs 117 References 118 12 Cylindrospermopsin and Congeners 127 Miko aj Kokoci ski, Ana Maria Camean, Shmuel Carmeli, Remedios Guzman Guillen, Angeles Jos, Joanna Mankiewicz Boczek , James S. Metcalf , Isabel Maria Moreno, Ana Isabel Prieto, and Assaf Sukenik 12.1 Chemical Characteristics of Cylindrospermopsin and Congeners 127 12.2 Genes Involved in CYN Biosynthesis 128 12.3 CYN Producers and Distribution 128 12.4 Toxicity of CYN 129 12.5 The Biological Role of CYN 132 12.6 Degradation of CYN 132 12.7 Available Methods for Determining CYN in Waters 132 References 133 13 Anatoxin a, Homoanatoxin a, and Natural Analogues 138 Milena Bruno, Olivier Ploux, James S. Metcalf , Annick Mejean, Barbara Pawlik Skowronska, and Ambrose Furey 13.1 Introduction 138 13.2 Chemical Structure, Synthesis, and Reactivity 138 13.3 Biosynthesis of ANTX, HANTX, and dihydroANTX 140 13.4 Occurrence and Producing Strains 140 13.5 Toxicity and Pharmacology 141 13.6 Analytical Methodologies 142 References 144 14 Saxitoxin and Analogues 148 Andreas Ballot, Cecile Bernard, and Jutta Fastner 14.1 Introduction 148 14.2 Toxicity of STXs 149 14.3 Occurrence 149 14.4 Genetics and Biosynthesis 150 14.5 Detection Methods 151 14.6 Guidance Values or National Regulations or Recommendations for Managing STXs 152 References 152 15 Anatoxin a(S) 155 James S. Metcalf and Milena Bruno 15.1 Chemical Structure of Anatoxin a(S) 155 15.2 Biosynthesis 155 15.3 Occurrence and Producing Strains 156 15.4 Toxicology and Pharmacology 156 15.5 Analytical Methods for Determination and Quantification 157 References 158 16 N Methylamino l Alanine and (S) 2,4 Diaminobutyric Acid 160 Olivier Ploux, Audrey Combes, Johan Eriksson, and James S. Metcalf 16.1 Historical Overview 160 16.2 Structure, Synthesis, and Molecular Properties 161 16.3 Neurotoxicity 161 16.4 Methods for Identification and Quantification 162 16.5 Occurrence in Cyanobacteria, Plants, and Animals 162 References 163 17 Lipopolysaccharide Endotoxins 165 Silvia Monteiro, Ricardo Santos, Lud k Blaha, and Geoffrey A. Codd 17.1 Lipopolysaccharide Endotoxins: Structure 165 17.2 Occurrence of LPS Endotoxins 167 17.3 Toxic Effects of LPS Endotoxins 168 17.4 Methods for Determination of LPS Endotoxins 169 References 170 18 Cyanobacterial Retinoids 173 Kunimitsu Kaya and Tomoharu Sano 18.1 Introduction 173 18.2 Detection of Retinoids Produced by Cyanobacteria 174 18.3 Chemistry and Analysis of Retinoids 175 18.4 Malformations by Cyanobacterial Retinoids 176 18.5 Concluding Remarks 176 References 176 19 Other Cyanobacterial Bioactive Substances 179 Tina Elersek, Lud k Blaha, Hanna Mazur Marzec, Wido Schmidt, and Shmuel Carmeli 19.1 Introduction 179 19.2 Aeruginosins and Spumigins 182 19.3 Anabaenopeptins 184 19.4 Biogenic Amines 185 19.5 Depsipeptides 186 19.6 Endocrine Disruptors and Novel Tumour Promoters 187 19.7 Lyngbyatoxins and Other Toxins Produced by Lyngbya majuscula 188 19.8 Microginins 189 19.9 Microviridins 189 References 190 20 Taste and Odour Compounds Produced by Cyanobacteria 196 Triantafyllos Kaloudis, Theodoros M. Triantis, and Anastasia Hiskia 20.1 Cyanobacterial Taste and Odour Compounds in Water Resources 196 20.2 Analytical Methods for Taste and Odour Compounds 197 References 199 Section V Screening and Trace Analysis of Cyanotoxins 203 21 Determination of Cyanotoxins by High Performance Liquid Chromatography with Photodiode Array 205 Anastasia Hiskia, Lisa Spoof , Triantafyllos Kaloudis, and Jussi Meriluoto 21.1 Introduction: Application of High Performance Liquid Chromatography for Different Classes of Cyanotoxins 205 21.2 HPLC of Microcystins and Nodularins 206 21.3 HPLC of Anatoxins 208 21.4 HPLC of Cylindrospermopsin 208 21.5 Advantages and Disadvantages of HPLC PDA 208 References 209 22 Determination of Cyanotoxins by High Performance Liquid Chromatography with Fluorescence Derivatization 212 James S. Metcalf and Paulo Baptista Pereira 22.1 Principle of the Technique and Why It Is Used for Cyanotoxins 212 22.2 Types of Reactions for Analysing Paralytic Shellfish Toxins Using High Performance Liquid Chromatography with Fluorescence Derivatization 213 22.3 Types of Reactions for Analysing N Methylamino l Alanine and Isomers by HPLC FLD 216 22.4 Need for Confirmatory Techniques with HPLC FLD 216 References 216 23 Liquid Chromatography Mass Spectrometry 218 Josep Caixach, Cintia Flores, Lisa Spoof , Jussi Meriluoto, Wido Schmidt, Hanna Mazur Marzec, Anastasia Hiskia, Triantafyllos Kaloudis, and Ambrose Furey 23.1 Introduction 218 23.2 Ion Sources 220 23.3 Types of Mass Analysers 225 23.4 Application of LC MS in Cyanotoxin Analyses 233 23.5 Overview of Quantitation: Cyanobacterial Toxins 235 23.6 Ion Suppression/Enhancement Considerations 237 23.7 High Resolution Mass Spectrometry (HRMS) 239 23.8 MS Experiments for the Detection of Unknown Cyanotoxins 242 23.9 Performance Criteria of LC MS Methods for Identification and Quantification of Cyanotoxins 249 References 251 24 Capillary Electrophoresis of Cyanobacterial Toxins 258 Gabor Vasas 24.1 Basic Theory and Introduction of Capillary Electrophoresis 258 24.2 Selection of Separation Methods 259 24.3 Detection Methods 259 24.4 CE Methods of Cyanobacterial Toxins 260 24.5 Future Perspectives 262 References 262 25 Immunoassays and Other Antibody Applications 263 James S. Metcalf and Geoffrey A. Codd 25.1 Introduction 263 25.2 Production of Antibodies versus Cyanotoxins 264 25.3 Applications of Cyanotoxin Antibodies 264 25.4 Cyanotoxin Localisation and Quantification Using Antibodies 265 25.5 Other Cyanotoxin Antibody Related Technologies 265 References 266 26 Protein Phosphatase Inhibition Assays 267 James S. Metcalf , Anastasia Hiskia, and Triantafyllos Kaloudis 26.1 Background and Molecular Mechanism of Protein Phosphatase Inhibition 267 26.2 Classes of Compounds that Inhibit Protein Phosphatases 268 26.3 Effects of Microcystins on Cyanobacterial Protein Phosphatases 268 26.4 The Basis of the PPIA Assay for Microcystins and Its Evolution 268 26.5 Comparison of PPIA with Other Analytical Methods for Microcystins 268 26.6 Commercially Available Kits for Microcystins 269 26.7 Improvements to the PPIA Assay to Make It More Specific to Microcystins 269 26.8 Conclusions about the Effectiveness of the PPIA Assay for Microcystins and Nodularins in Different Matrices 269 References 270 27 Bioassay Use in the Field of Toxic Cyanobacteria 272 Lud k Blaha, Ana Maria Camean , Valerie Fessard , Daniel Gutierrez Praena , Angeles Jos , Benjamin Marie , James S. Metcalf , Silvia Pichardo , Maria Puerto , Andrea Torokne , Gabor Vasas, and Bojana egura 27.1 Introduction 272 27.2 Drivers and Objectives for Bioassay Use 273 27.3 Classification and Terminology 274 27.4 Bioassays for the Effect Evaluation 275 27.5 Bioassays for Monitoring 276 27.6 Conclusions and Future Perspectives 278 References 278 28 Molecular Tools for the Detection of Toxigenic Cyanobacteria in Natural Ecosystems 280 Jean Francois Humbert 28.1 Introduction 280 28.2 Molecular Methods for the Monitoring of Potentially Toxic Cyanobacteria 281 28.3 Strengths and Limitation of These Molecular Approaches 282 28.4 Conclusions 282 References 283 Section VI Methodological Considerations 285 29 Method Validation Guidelines for the Analysis of Cyanotoxins 287 Theodoros M. Triantis, Triantafyllos Kaloudis, and Anastasia Hiskia 29.1 Introduction: Method Validation as a Requirement for Laboratory Accreditation 287 29.2 Performance Criteria and Validation Protocols for the Analysis of Cyanotoxins in Environmental Studies 288 29.3 Validation Issues Concerning the Analysis of Cyanotoxins 290 References 291 30 Interpretation, Significance, and Reporting of Results 292 Geoffrey A. Codd, Jutta Fastner , Tore Lindholm, Jussi Meriluoto, and James S. Metcalf 30.1 Introduction 292 30.2 Interpretation and Significance of Results 293 30.3 Reporting of Results and Maximization of Benefits 294 30.4 Examples, Debriefing 294 References 296 31 Lessons from the U ice Case: How to Complement Analytical Data 298 Zorica Svir ev , Damjana Drobac , Nada Tokodi , Dunja eni , Jelica Simeunovi , Anastasia Hiskia , Triantafyllos Kaloudis , Biljana Mijovi , Stamenko u ak , Mla an Proti , Milka Vidovi , Antonije Onjia , Sonja Nybom , Tamara Va i , Tamara Palana ki Male evi , Tamara Duli , Dijana Panteli , Marina Vuka inovi , and Jussi Meriluoto 31.1 Introduction 299 31.2 Vrutci Reservoir and the Cyanobacterial Bloom Detected in December 2013 299 31.3 Analytical Work: Toxin Analyses of Water, Cyanobacterial Biomass, and Fish from Reservoir Vrutci 301 31.4 Complementary Data on Toxicity and Observed Health Problems 302 31.5 Analytical and Supplementary Results Combined: A Plausible Reconstruction of Events in Vrutci Reservoir and the City of U ice 306 31.6 Conclusions from the U ice Case 306 References 307 32 Selection of Analytical Methodology for Cyanotoxin Analysis 309 Jussi Meriluoto , James S. Metcalf and Geoffrey A. Codd 32.1 Introduction 309 32.2 General Comparison of Physicochemical Analyses, Biochemical Methods, and Bioassays 309 32.3 Guidance for Selecting and Using Standard Operating Procedures Found in this Handbook 310 32.4 Methodology versus Required Response Time 311 32.5 Influence of Waterbody History on the Choice of Methods 312 32.6 Integration of the Results Obtained: Making Sense 312 Section VII Standard Operating Procedures (SOPs) 313 SOP 1 Cyanobacterial Samples: Preservation, Enumeration, and Biovolume Measurements 315 Arnaud Catherine, Selma Maloufi, Roberta Congestri, Emanuela Viaggiu, and Renata Pilkaityte SOP 2 Chlorophyll a Extraction and Determination 331 Claude Yepremian, Arnaud Catherine, Cecile Bernard, Roberta Congestri, Tina Elersek, and Renata Pilkaityte SOP 3 Phycocyanin Extraction and Determination 335 Claude Yepremian, Arnaud Catherine, Cecile Bernard, Roberta Congestri, Tina Elersek, and Renata Pilkaityte SOP 4 Analysis of Picocyanobacteria Abundance in Epifluorescence Microscopy 339 Iwona Jasser and Cristiana Callieri SOP 5 Estimation of Cyanobacteria Biomass by Marker Pigment Analysis 343 Jean Pierre Descy SOP 6 Extraction of Cyanotoxins from Cyanobacterial Biomass 350 Leonardo Cerasino, Jussi Meriluoto, Lud k Blaha, Shmuel Carmeli, Triantafyllos Kaloudis, and Hanna Mazur Marzec SOP 7 Solid Phase Extraction of Microcystins and Nodularin from Drinking Water 354 Theodoros M. Triantis, Triantafyllos Kaloudis, Sevasti-Kiriaki Zervou, and Anastasia Hiskia SOP 8 Extraction of Microcystins from Animal Tissues 358 Ond ej Adamovsky and Lud k Blaha SOP 9 Analysis of Microcystins by Online Solid Phase Extraction Liquid Chromatography Tandem Mass Spectrometry 362 Cintia Flores and Josep Caixach SOP 10 Determination of Microcystins and Nodularin in Filtered and Drinking Water by LC MS/MS 372 Theodoros M. Triantis, Triantafyllos Kaloudis, Sevasti-Kiriaki Zervou, and Anastasia Hiskia SOP 11 Analysis of Microcystins and Nodularin by Ultra High Performance Liquid Chromatography Tandem Mass Spectrometry 379 Leonardo Cerasino SOP 12 Analysis of Microcystins in Animal Tissues Using LC MS/MS 385 Ji i Kohoutek and Lud k Blaha SOP 13 Quantitative Screening of Microcystins and Nodularin in Water Samples with Commercially Available ELISA Kits 390 Triantafyllos Kaloudis, Theodoros M. Triantis, and Anastasia Hiskia SOP 14 Quantitative Screening of Microcystins and Nodularin in Water Samples with Commercially Available PPIA Kits 393 Triantafyllos Kaloudis, Theodoros M. Triantis, and Anastasia Hiskia SOP 15 Solid Phase Extraction of Cylindrospermopsin from Filtered and Drinking Water 396 Theodoros M. Triantis, Triantafyllos Kaloudis, and Anastasia Hiskia SOP 16 Determination of Cylindrospermopsin in Filtered and Drinking Water by LC MS/MS 399 Theodoros M. Triantis, Triantafyllos Kaloudis, and Anastasia Hiskia SOP 17 Solid Phase Extraction of Anatoxin a from Filtered and Drinking Water 405 Theodoros M. Triantis, Triantafyllos Kaloudis, and Anastasia Hiskia SOP 18 Determination of Anatoxin a in Filtered and Drinking Water by LC MS/MS 408 Theodoros M. Triantis, Triantafyllos Kaloudis, and Anastasia Hiskia SOP 19 Analysis of Anatoxin a and Cylindrospermopsin by Ultra High-Performance Liquid Chromatography Tandem Mass Spectrometry 413 Leonardo Cerasino SOP 20 Extraction and Chemical Analysis of Saxitoxin and Analogues in Water 418 Lutz Imhof and Wido Schmidt SOP 21 Extraction of BMAA from Cyanobacteria 432 James S. Metcalf, Sandra A. Banack, and Paul A. Cox SOP 22 Analysis of -N Methylamino l Alanine by UHPLC MS/MS 435 James S. Metcalf, William B. Glover, Sandra A. Banack, and Paul A. Cox SOP 23 Extraction and LC MS/MS Analysis of Underivatised BMAA 439 Elisabeth J. Faassen SOP 24 Extraction, Purification, and Testing of LPS from Cyanobacterial Samples 447 Lucie Blahova and Lud k Blaha SOP 25 Extraction and Chemical Analysis of Planktopeptin and Anabaenopeptins 452 Hanna Mazur Marzec, Tina Elersek, and Agata B aszczyk SOP 26 Thamnocephalus Test 462 Andrea Torokne SOP 27 Determination of Geosmin and 2 Methylisoborneol in Water by HS SPME GC/MS 469 Triantafyllos Kaloudis, Theodoros M. Triantis, and Anastasia Hiskia SOP 28 Rapid Analysis of Geosmin and 2 Methylisoborneol from Aqueous Samples Using Solid Phase Extraction and GC MS 475 Christine Edwards, Craig McKenzie, Carlos Joao Pestana, Kyari Yates, and Linda A. Lawton SOP 29 Basic Validation Protocol for the Analysis of Cyanotoxins in Environmental Samples 481 Triantafyllos Kaloudis, Theodoros M. Triantis, and Anastasia Hiskia Section VIII Appendices 487 Appendix 1 Cyanobacterial Species and Recent Synonyms 489 Appendix 2 Cyanobacteria Associated With the Production of Cyanotoxins 501 Appendix 3 Tables of Microcystins and Nodularins 526 Index 538
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