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Seafood and Freshwater Toxins: Pharmacology, Physiology, and Detection, Second Edition PDF

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Food Science and Technology Botana T h i r d E d i t i o n Seafood THIRD EDITION Seafood Freshwater Toxins and S and e PHARMACOLOGY, PHYSIOLOGY, AND DETECTION a Freshwater Toxins f The last few years have brought about many changes in the field of o marine and freshwater toxins, with advances in analytical technology and the realization that these toxins are a global issue. Offering a complete o reference guide, Seafood and Freshwater Toxins: Pharmacology, d Physiology, and Detection, Third Edition addresses all aspects of the a social and scientific influence of phytotoxins, from legislation and moni- n toring to new drug development. Covering many new topics, the book d examines three main aspects: monitoring of toxins; chemical, mechanis- F PHARMACOLOGY, PHYSIOLOGY, AND DETECTION tic, and toxicological diversity; and detection technologies. r New to this edition: e s • 35 new chapters and 5 updated chapters h • A focus on state-of-the-art methodology • Coverage of new technologies to cultivate algae and to identify, w isolate, and quantify toxins • Regulatory changes a • Climate change evidence t • Expanded information on toxicology e r Part I of the book includes an overview and reviews general issues related to toxin detection, ecology, and diversity, and effects of climate T change. Part II covers impacts of toxins regarding epidemiology, toxicol- ogy, economics, and surveillance. Part III explores available detection o technologies, such as functional assays, biosensors, mass spectrometry, x nanotechnology, and more. In addition, standard reference materials for i toxins are discussed. Parts IV to VI provide detailed descriptions of toxin n chemical diversity, biological sources, and modes of action. Part VII s addresses the use of toxins as starting points for therapeutic drugs for cancer, neurological disorders, and for novel antibiotics.. Luis M. Botana EDITED BY Third Edition K14551 T h i r d E d i t i o n Seafood and Freshwater Toxins PHARMACOLOGY, PHYSIOLOGY, AND DETECTION Luis M. Botana E D I T E D B Y Boca Raton London New York CRC Press is an imprint of the Taylor & Francis Group, an informa business CRC Press Taylor & Francis Group 6000 Broken Sound Parkway NW, Suite 300 Boca Raton, FL 33487-2742 © 2014 by Taylor & Francis Group, LLC CRC Press is an imprint of Taylor & Francis Group, an Informa business No claim to original U.S. Government works Version Date: 20140108 International Standard Book Number-13: 978-1-4665-0515-5 (eBook - PDF) This book contains information obtained from authentic and highly regarded sources. Reasonable efforts have been made to publish reliable data and information, but the author and publisher cannot assume responsibility for the validity of all materials or the consequences of their use. The authors and publishers have attempted to trace the copyright holders of all material repro- duced in this publication and apologize to copyright holders if permission to publish in this form has not been obtained. If any copyright material has not been acknowledged please write and let us know so we may rectify in any future reprint. Except as permitted under U.S. Copyright Law, no part of this book may be reprinted, reproduced, transmitted, or utilized in any form by any electronic, mechanical, or other means, now known or hereafter invented, including photocopying, microfilming, and recording, or in any information storage or retrieval system, without written permission from the publishers. For permission to photocopy or use material electronically from this work, please access www.copyright.com (http://www.copy- right.com/) or contact the Copyright Clearance Center, Inc. (CCC), 222 Rosewood Drive, Danvers, MA 01923, 978-750-8400. CCC is a not-for-profit organization that provides licenses and registration for a variety of users. For organizations that have been granted a photocopy license by the CCC, a separate system of payment has been arranged. Trademark Notice: Product or corporate names may be trademarks or registered trademarks, and are used only for identifica- tion and explanation without intent to infringe. Visit the Taylor & Francis Web site at http://www.taylorandfrancis.com and the CRC Press Web site at http://www.crcpress.com Contents Preface .....................................................................................................................................................vii Acknowledgments .....................................................................................................................................ix Editor ........................................................................................................................................................xi Contributors ............................................................................................................................................xiii Part I General Considerations 1. Dinoflagellate Toxins: An Overview ...............................................................................................3 Michael J. Holmes, Andreas Brust, and Richard J. Lewis 2. Guide to Phycotoxin Monitoring of Bivalve Mollusk-Harvesting Areas ..................................39 Luis M. Botana 3. Marker Compounds, Relative Response Factors, and Toxic Equivalent Factors ....................57 Paz Otero and Paula Rodríguez 4. Toxins from Marine Invertebrates ...............................................................................................77 Eva Ternon and Olivier P. Thomas 5. Emerging Toxic Cyanobacterial Issues in Freshwater Sources: Influence of Climate Change ...105 Arash Zamyadi Part II Impact 6. Epidemiology of Marine Toxins ..................................................................................................123 Juan Jesús Gestal Otero 7. Toxicology of Seafood Toxins: A Critical Review .....................................................................197 Rex Munday 8. World Production of Bivalve Mollusks and Socioeconomic Facts Related to the Impact of Marine Biotoxins .......................................................................................................................291 Martiña Ferreira, Jorge Lago, Juan Manuel Vieites, and Ana G. Cabado 9. Designing a Preharvest Monitoring and Management Plan for Marine Shellfish Toxins ....313 Joe Silke 10. Marine Toxin Monitoring in Asia ...............................................................................................323 Supanoi Subsinserm Part III Technology 11. Functional and Receptor-Based Assays for Marine Toxins ......................................................333 Natalia Vilariño, María Fraga, and Laura Pérez Rodríguez iii iv Contents 12. Surface Plasmon Resonance Biosensor Technology for Marine Toxin Analysis ...................347 Katrina Campbell 13. Validation of HPLC Detection Methods for Marine Toxins ....................................................367 Andrew Turner 14. Analysis of Marine Biotoxins by Liquid Chromatography Mass Spectrometric Detection .......409 Arjen Gerssen 15. Standards for Marine and Freshwater Toxins ..........................................................................429 Álvaro Antelo, Carmen Alfonso, and Mercedes Álvarez 16. Strategies on the Use of Antibodies as Binders for Marine Toxins ..........................................471 Edwina Stack and Richard O’Kennedy 17. Toxic Phytoplankton Detection ...................................................................................................497 Alberto Otero, María-José Chapela, Paula Fajardo, Alejandro Garrido, and Ana G. Cabado 18. Nanotechnology Applications in Aquatic Toxins .......................................................................521 Begoña Espiña, Verónica C. Martins, Manuel Bañobre-López, Paulo P. Freitas, and José Rivas 19. Culture of Microalgal Dinoflagellates .........................................................................................551 F. García-Camacho, A. Sánchez-Mirón, J. Gallardo-Rodríguez, L. López-Rosales, Y. Chisti, and E. Molina-Grima Part IV Nonneurotoxic Lipophilic Toxins 20. Ecobiology and Geographical Distribution of Potentially Toxic Marine Dinoflagellates .....569 Aristidis Vlamis and Panagiota Katikou 21. Lipophilic Toxins, Pectenotoxins, and Yessotoxins: Chemistry, Metabolism, and Detection ...627 Toshiyuki Suzuki 22. Yessotoxins and Pectenotoxins ....................................................................................................657 Amparo Alfonso, Araceli Tobío, and M. Carmen Louzao 23. Maitotoxin: An Enigmatic Toxic Molecule with Useful Applications in the Biomedical Sciences ...........................................................................................................677 Juan G. Reyes, Claudia Sánchez-Cárdenas, Waldo Acevedo-Castillo, Patricio Leyton, Ignacio López-González, Ricardo Felix, María A. Gandini, Marcela B. Treviño, and Claudia L. Treviño 24. Palytoxin and Analogs: Ecobiology and Origin, Chemistry, and Chemical Analysis ...........695 Panagiota Katikou and Aristidis Vlamis 25. Palytoxin and Analogues: Biological Effects and Detection .....................................................741 Aurelia Tubaro, Giorgia del Favero, Marco Pelin, Gary Bignami, and Mark Poli 26. AZA: The Producing Organisms—Biology and Trophic Transfer ........................................773 Urban Tillmann, Rafael Salas, Thierry Jauffrais, Philipp Hess, and Joe Silke Contents v 27. Azaspiracids: Chemistry, Biosynthesis, Metabolism, and Detection ......................................799 Philipp Hess, Pearse McCarron, Bernd Krock, Jane Kilcoyne, and Christopher O. Miles 28. Azaspiracids: Toxicology, Pharmacology, and Risk Assessment ............................................823 Michael J. Twiner, Philipp Hess, and Gregory J. Doucette 29. Polycavernosides and Other Scarce New Toxins .......................................................................857 M. Carmen Louzao, Natalia Vilariño, and Mari Yotsu-Yamashita Part V Marine Neurotoxins 30. Domoic Acid: Chemistry and Pharmacology ............................................................................875 Carmen Vale 31. Gambierol: Synthetic Aspects .....................................................................................................895 Haruhiko Fuwa 32. Ciguatera Toxins: Pharmacology, Toxicology, and Detection .................................................925 Irina Vetter, Katharina Zimmermann, and Richard J. Lewis 33. Cyclic Imine Toxins: Chemistry, Origin, Metabolism, Pharmacology, Toxicology, and Detection .................................................................................................................................951 Jordi Molgó, Rómulo Aráoz, Evelyne Benoit, and Bogdan I. Iorga 34. Saxitoxin and Analogs: Ecobiology, Origin, Chemistry, and Detection .................................991 Paulo Vale Part VI Cyanobacterial Toxins 35. Cyanobacterial Toxins in Aquaculture .....................................................................................1015 Paul T. Smith 36. Cylindrospermopsin: Chemistry, Origin, Metabolism, Effects, and Detection ...................1031 Ambrose Furey, Vaishali P. Bane, Mary Lehane, Christopher T. Elliott, and Clare H. Redshaw 37. Anatoxin: Chemistry, Effects, Source, Metabolism, and Detection .......................................1061 Justine Dauphard, Mary Lehane, Frank van Pelt, John O’Halloran, and Ambrose Furey 38. Marine Cyanobacterial Toxins: Source, Chemistry, Toxicology, Pharmacology, and Detection ...............................................................................................................................1073 Vitor Vasconcelos and Pedro Leão 39. Calcium Channels for Exocytosis and Endocytosis: Pharmacological Modulation .............1091 Antonio M.G. de Diego, Luis Gandía, Fernando Padín, and Antonio G. García Part VII Toxins as Drugs 40. Marine Compounds as a Starting Point to Drugs ...................................................................1141 Juan A. Rubiolo, Eva Alonso, and Eva Cagide Preface When the first edition of this title was published, I felt the need to gather all the information regarding pharmacology and toxicology of marine toxins. At the time, the available information was limited, as evidenced by the second edition, which has shown how fast the discovery and identification of new toxins are progressing. The publication of a third edition of this book about marine and freshwater toxins indicates not only that scientists and technicians demand this type of information, but also that there are new topics to discuss. And this is so because the last few years have brought about many changes in this field. These changes were mainly due to the advance of analytical technology, most notably mass spectrometry, that allowed the identification of small amounts of toxins, tracking of old samples back in time, and the realization that most of the toxins are present everywhere, making it a global problem. If the second edition provided a clear picture of the increase in the number of toxin groups and analogs in each group, this edition is mostly influenced by the changes in regulatory aspects, climate change evidences, new technologies, and toxicology. What we know now is that the chemical diversity of toxins is very high, that their profile is changing as a consequence of human or climatic interference, and that many new technologies can be used to cultivate the algae, identify the toxins, and isolate and quantify them. There is much information about the potential use of marine compounds as lead structures for drug develop- ment, and yet we do not know why they are being synthesized by the microorganisms that produce them. We still have the same old problems: scarcity of available compounds, although new players have entered the marine toxin standard arena, and unclear toxicological information, which was an actual limitation for the European Food Safety working group. Therefore, there is still much to be done. The book chapters cover several aspects of toxins. Part I includes an overview and covers general issues related to their detection, ecology, diversity, and climate change. Part II refers to impact, in terms of epidemiology, toxicology, economy, and surveillance. Part III is focused on technology available for the detection (biosensors and functional assays, mass spectrometry, nanotechnology and biotechnology, and standards) of toxins. Finally, Parts IV to VII give detailed descriptions of the chemical diversity of the groups and their biological sources, their modes of action, and the use of marine and freshwater toxins as lead structures in drug development. vii Acknowledgments All the contributing authors are leading experts in their fields. I would like to acknowledge the time and effort that they have put into this work. Without their collaboration, this book would never have been possible. I also thank all the readers of this book. They allowed the publication of this third edition and helped consolidate the title as a reference in the field. ix

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