Table Of ContentFood 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
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PHARMACOLOGY, PHYSIOLOGY, AND DETECTION
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Freshwater Toxins
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The last few years have brought about many changes in the field of
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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
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social and scientific influence of phytotoxins, from legislation and moni-
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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.
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New to this edition: e
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• 35 new chapters and 5 updated chapters
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• 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
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Part I of the book includes an overview and reviews general issues
related to toxin detection, ecology, and diversity, and effects of climate
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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,
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nanotechnology, and more. In addition, standard reference materials for
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toxins are discussed. Parts IV to VI provide detailed descriptions of toxin
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chemical diversity, biological sources, and modes of action. Part VII
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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
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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.
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