Phycotoxins E-Book

• Herausgeber: John Wiley & Sons
• Kategorie: Fachliteratur
• Sprache: Englisch

Seitenzahl: 1217

Veröffentlichungsjahr: 2015

Beschreibung

Phycotoxins are a diverse group of poisonous substances produced by certain seaweed and algae in marine and fresh waters and are important to the scientific community for many reasons, the most obvious being that they pose food safety issues which requires a large investment to regularly monitor the presence of these compounds in foods. Phycotoxins: Chemistry and Biochemistry, second edition presents the most updated information available on phycotoxins. Major emphases are given to chemistry and biochemistry, while origins, mechanism of action, toxicology, and analytical methodology are also covered. Since the publication of the first edition, there have been major advances in the science of marine and aquatic toxins, as well as advances in toxicology, analytical chemistry and pharmacology. This fully revised and updated edition includes several new chapters, including those on ciguatoxins, pinnatoxin, ichthyotoxins, as well as new chapters on food safety control of marine toxins, climate change and water toxins, and microalgae as a source of nutraceuticals. The book will be of interest to toxicologists, marine, food, and plant scientists, as well as researchers and academics in the areas of food science, medicine, public health, toxicology, pharmacology and marine biology.

Leseprobe

Table of Contents

Cover

Title Page

Copyright

List of contributors

Preface

Chapter 1: Analysis of marine toxins: gaps on food safety control of marine toxins

Analysis of marine toxins and gaps on food safety control

Gaps on food safety control for marine toxins by chemical methods

Use of standards

New risks in the EU

References

Chapter 2: Pharmacology of ciguatoxins

Chemical structure of ciguatoxins

Voltage-gated sodium channels

Neurological symptoms of ciguatera

Physiological effects of ciguatoxin

Ciguatoxin neurotoxicity

Ciguatoxins, neurological perspectives

References

Chapter 3: Chemistry of pinnatoxins

Introduction

Isolation

Bioactivity

Detection

Total chemical synthesis

Chemical stability

Conclusions

References

Chapter 4: Chemistry and analysis of PSP toxins

Introduction

Methods of analysis

Chemical methods

References

Chapter 5: Chemistry of palytoxin and its analogues

Introduction

Palytoxin

Palytoxin's analogues from

Ostreopsis

spp

Ostreocins from

O. siamensis

References

Chapter 6: Pharmacology of palytoxins and ostreocins

Introduction

Origin and producing organisms

Toxin distribution and ecological aspects

Pharmacological target of PLTXs

Palytoxin toxicology

Detection methods

Future perspectives

References

Chapter 7: Recent insights into anatoxin-a chemical synthesis, biomolecular targets, mechanisms of action and LC-MS detection

Anatoxin-

a

and analogues

Anatoxins' biomolecular targets and mechanisms of action

LC-MS detection

Conclusions and perspectives

Acknowledgements

References

Chapter 8: Therapeutics of marine toxins

Introduction

Marine toxins as a source of therapeutic compounds

Present marine toxins and derived compound uses

Future of marine toxins and derived compounds uses

Problems and advancements in drug discovery from the seas

Conclusions

References

Chapter 9: Marine toxins as modulators of apoptosis

Introduction

Phycotoxins involved in apoptotic processes

Non-apoptotic cytotoxicity of phycotoxins

References

Chapter 10: Cyanobacterial toxins

Introduction

Chemistry of cyanotoxins

Distribution of cyanotoxins

Acknowledgments

References

Chapter 11: Marine toxins and climate change: the case of PSP from cyanobacteria in coastal lagoons

Introduction

Definition of coastal lagoons and main ecosystem characteristics

Ecosystem goods and services and human exploitation of coastal lagoons

Eutrophication and climate change in coastal lagoons

Cyanobacteria in coastal lagoons

Paralytic shellfish poisoning and cyanobacteria in coastal lagoons

Conclusions

References

Chapter 12: Microalgae as a source of nutraceuticals

Introduction

Microalgal taxa

World biodiversity of microalgae

Microalgae in culture collections and under commercial cultivation

Commercial use of microalgae as nutraceuticals

Categories of nutraceuticals from microalgae

Cholesterol-lowering activity

Potential upcoming microalgae or their alternate use

Genetically modified (GM) microalgae

Concluding remarks

Acknowledgments

References

Chapter 13: The marine origin of drugs

Introduction

Marine chemical ecology and the origin of marine drugs

Marine or marine-derived drugs sources

From marine origin to therapeutics use: the success stories of Cytarabine, Ziconotide and Eribulin Mesilate

Marine phycotoxin as a tool for signal transduction pathways analysis: the success story of okadaic acid

Conclusions

References

Chapter 14: Pharmacology of cylindrospermopsin

Introduction

Chemical and physical properties

Producing genera/species

Cylindrospermopsin biosynthesis

Distribution and bioaccumulation

Human and animal intoxications

Cylindrospermopsin toxicity

Mechanism of action

Detection methods

Cylindrospermopsin elimination

Legislation

References

Chapter 15: Pharmacology of the cyclic imines

Introduction

Overview of cyclic imine chemical structure

In vivo

effects of cyclic imines

Pharmacodynamics:

in vitro

evidence of spirolides, pinnatoxins and gymnodimines targeting nicotinic acetylcholine receptors

Structure-activity relationship of cyclic imines

Involvement of nAChR antagonism in

in vivo

and

in vitro

effects of cyclic imines

Pharmacokinetics of cyclic imines

Conclusions

References

Chapter 16: Diversity of organic structures of marine microbial origin with drug potential

Introduction

Marine bacterial natural products

Marine bacterial natural products with anticancer drug potential

Marine actinomycete natural products with antimicrobial drug potential

Marine fungal natural products

Modifying marine microbial natural products

Conclusions

References

Chapter 17: Polyketides as a source of chemical diversity

Introduction

Biosynthesis of polyketides

Structural diversity of polyketides among phycotoxins produced by dinoflagellates and cyanobacteria

Conclusions

References

Chapter 18: Ichthyotoxins

Introduction

Anatoxins and homoanatoxin

Brevetoxins

Ciguatoxins

Karlotoxins

Microcystins

Prymnesins

Saxitoxins

The special case of

Pfiesteria

Ichthyotoxins of less widespread significance

Reactive oxygen species and physical/mechanical damage

The unknown nature of ichthyotoxicity

References

Chapter 19: Pathological clues of phycotoxin ingestion

Introduction

Paralytic shellfish poisoning

Diarrhetic shellfish poisoning

Amnesic shellfish poisoning

Neurotoxic shellfish poisoning

Azaspiracid shellfish poisoning

Ciguatera shellfish poisoning

References

Index

End User License Agreement

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Guide

cover

Table of Contents

Preface

Begin Reading

List of Illustrations

Figure 1.1

Figure 1.2

Figure 1.3

Figure 2.1

Figure 2.2

Figure 2.3

Figure 2.4

Figure 2.5

Figure 2.6

Figure 3.1

Scheme 3.1

Scheme 3.2

Scheme 3.3

Scheme 3.4

Scheme 3.5

Scheme 3.6

Scheme 3.7

Scheme 3.8

Scheme 3.9

Scheme 3.10

Scheme 3.11

Scheme 3.12

Scheme 3.13

Scheme 3.14

Scheme 3.15

Figure 4.1

Figure 4.2

Figure 4.3

Figure 5.1

Figure 5.2

Figure 5.3

Figure 5.4

Figure 6.1

Figure 6.2

Figure 7.1

Figure 7.2

Figure 7.3

Figure 7.4

Figure 7.5

Figure 7.6

Figure 7.7

Figure 7.8

Figure 7.9

Figure 7.10

Figure 7.11

Figure 7.12

Figure 7.13

Figure 7.14

Figure 7.15

Figure 7.16

Figure 7.17

Figure 7.18

Figure 7.19

Figure 7.20

Figure 7.21

Figure 7.22

Figure 7.23

Figure 7.24

Figure 7.25

Figure 7.26

Figure 7.27

Figure 7.28

Figure 7.29

Figure 8.1

Figure 8.2

Schemes 9.1

Figure 9.2

Figure 9.1

Scheme 9.3

Figure 10.1

Figure 10.2

Figure 10.3

Figure 10.4

Figure 10.5

Figure 10.6

Figure 10.7

Figure 10.8

Figure 10.9

Figure 10.10

Figure 11.1

Figure 11.2

Figure 12.1

Figure 13.1

Figure 13.2

Figure 14.1

Figure 14.2

Figure 15.1

Figure 15.2

Figure 15.3

Figure 16.1

Figure 17.1

Figure 17.2

Figure 17.3

Figure 17.4

Figure 17.5

Figure 17.6

Figure 17.7

Figure 17.8

Figure 17.9

Figure 17.10

Figure 17.11

Figure 17.12

Figure 17.13

Figure 17.14

Figure 17.15

Figure 19.1

Figure 19.2

Figure 19.3

Figure 19.4

Figure 19.5

Figure 19.6

Figure 19.7

Figure 19.8

Figure 19.9

List of Tables

Table 1.1

Table 1.2

Table 1.3

Table 2.1

Table 2.2

Table 4.1

Table 4.2

Table 5.1

Table 5.2

Table 5.3

Table 5.4

Table 6.1

Table 7.1

Table 7.2

Table 7.3

Table 8.1

Table 10.1

Table 11.1

Table 11.2

Table 12.1

Table 12.2

Table 12.3

Table 12.4

Table 12.5

Table 13.1

Table 15.1

Table 15.2

Table 15.3

Table 18.1

Table 18.2

Table 18.3

Table 18.4

Table 18.5

Table 18.6

Table 18.7

Table 18.8

Table 18.9

Table 18.10

Table 18.11

Table 18.12

Table 18.13

Table 18.14

Phycotoxins

Chemistry and Biochemistry

EDITED BY

Luis M. Botana and Amparo Alfonso

University of Santiago de Compostela, Department of Pharmacology, Veterinary Faculty, Lugo-Spain

SECOND EDITION

This edition first published 2015 ©2015 by John Wiley & Sons, Ltd.

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Library of Congress Cataloging-in-Publication Data

Phycotoxins: chemistry and biochemistry. – 2nd edition / Luis M Botana and Amparo Alfonso [editors].

pages cm

Includes bibliographical references and index.

ISBN 978-1-118-50036-1 (cloth)

1. Algal toxins. I. Botana, Luis M. II. Alfonso, Amparo, 1965-

RA1242.A36P48 2015

615.9′45–dc23

2014037287

A catalogue record for this book is available from the British Library.

Wiley also publishes its books in a variety of electronic formats. Some content that appears in print may not be available in electronic books.

Cover image: Prorocentrum minimum image (Scanning Electron Microscope (SEM) Leica, S440, ×7500). Picture from Editors.

List of contributors

Feras Abbas

Mass Spectrometry Research Centre (MSRC) and PRTOEOBIO Research groups, Department of Chemistry, Cork Institute of Technology (CIT), Bishopstown, Cork, Ireland.

Amparo Alfonso

Department Pharmacology, Veterinary School, Campus de Lugo, University of Santiago de Compostela, 27002 Lugo, Spain.

Carmen Alfonso

Cifga Laboratory, Campus Universitario, Pl. Santo Domingo, 20, 5a, 27001 Lugo, Spain.

Eva Alonso

Department of Pharmacology, Veterinary School, Campus de Lugo, University of Santiago de Compostela, 27002 Lugo, Spain.

Celso Alves

Grupo de Investigação em Recursos Marinhos, Escola Superior de Turismo e Tecnologia do Mar, Instituto Politécnico de Leiria, Campus 4 – Santuário N.a Sra. dos Remédios, 2520–641 Peniche, Portugal.

Álvaro Antenlo

Cifga Laboratory, Campus Universitario, Pl. Santo Domingo, 20, 5a, 27001 Lugo, Spain.

Manuel Aureliano

Department of Biological Sciences and Bioengineering, Marine Science Center, Faculty of Science and Technology, Algarve University, Faro 8005–139 Portugal.

Tanya Beletskaya

Shannon Applied Biotechnology Centre, Limerick Institute of Technology, Moylish Park, Limerick, Ireland.

Roberto Bermúdez

Department of Anatomy and Animal Production, University of Santiago de Compostela, Lugo 27002, Spain.

Ana M. Botana López

Department of Analytical Chemistry, Faculty of Sciences, University of Santiago de Compostela. C/ Alfonso X s/n, 27002 Lugo, Spain.

Milena Bruno

Istituto Superiore di Sanità, Department of Environment and Primary Prevention, V.le Regina Elena 299, 00161 Rome, Italy.

Alexandre Campos

Interdisciplinary Center of Marine and Environmental Research, CIIMAR, and Faculty of Sciences, University of Porto, Porto, Portugal.

Manuel Cifuentes

Department of Anatomy and Animal Production, University of Santiago de Compostela, Lugo 27002, Spain.

Patrizia Ciminiello

Department of Pharmacy, University of Napoli Federico II, Via Domenico Montesano 49, Napoli 80131, Italy.

John W. La Claire II

University of Texas at Austin, Department of Molecular Biosciences, 205 W. 24th St., Austin, TX 78712-1240, USA.

Catherine Collins

Shannon Applied Biotechnology Centre, Limerick Institute of Technology, Moylish Park, Limerick, Ireland.

Andrés Crespo Vieira

Department of Pharmacology, Veterinary School, University of Santiago de Compostela, 27002 Lugo, Spain.

Sara F. Ferreiro

Department of Pharmacology, Veterinary School, University of Santiago de Compostela, 27002 Lugo, Spain.

Rainer Ebel

Marine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Old Aberdeen, AB24 3UE, Scotland, UK.

Hai Deng

Marine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Old Aberdeen, AB24 3UE, Scotland, UK.

Carmela Dell'Aversano

Department of Pharmacy, University of Napoli Federico II, Via Domenico Montesano 49, Napoli 80131, Italy.

Diego Alberto Fernández

Department of Pharmacology, Veterinary School, Campus de Lugo, University of Santiago de Compostela 27002 Lugo, Spain.

Andrea Fernández-Araujo

Department of Pharmacology, Veterinary School, Campus de Lugo, University of Santiago de Compostela, 27002 Lugo, Spain.

Custódia Fonseca

Department of Chemistry and Pharmacy, Marine Science Center, Faculty of Science and Technology, Algarve University, Faro 8005–139 Portugal.

Martino Forino

Department of Pharmacy, University of Napoli Federico II, Via Domenico Montesano 49, Napoli 80131, Italy.

María Fraga

Department of Pharmacology, University of Santiago de Compostela, Spain.

Ambrose Furey

Mass Spectrometry Research Centre (MSRC) and PRTOEOBIO Research groups, Department of Chemistry, Cork Institute of Technology (CIT), Bishopstown, Cork, Ireland.

José Gil

Department of Pharmacology, School of Pharmacy, University of Santiago de Compostela, Campus Sur, Praza Seminario de Estudos Galegos, s/n., 1782 Santiago de Compostela, Spain.

André Horta

Grupo de Investigação em Recursos Marinhos, Escola Superior de Turismo e Tecnologia do Mar, Instituto Politécnico de Leiria, Campus 4 - Santuário N.a Sra. dos Remédios, 2520 – 641 Peniche, Portugal.

Marcel Jaspars

Marine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Old Aberdeen, AB24 3UE, Scotland, UK.

Sushanta Kumar Saha

Shannon Applied Biotechnology Centre, Limerick Institute of Technology, Moylish Park, Limerick, Ireland (ROI).

Pedro Leão

Interdisciplinary Center of Marine and Environmental Research, CIIMAR, University of Porto, Porto, Portugal.

Henar López Alonso

Department of Pharmacology, Veterinary School, Campus de Lugo, University of Santiago de Compostela, 27002 Lugo, Spain.

M Carmen Louzao

Department of Pharmacology, Veterinary School, Campus de Lugo, University of Santiago de Compostela, 27002 Lugo, Spain.

Antonella Lugliè

University of Sassari, Department of Sciences for Nature and Environmental Resources, Via Piandanna 4, 07100 Sassari, Italy.

Phillip Mabe

Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA 93106, USA.

Schonna R. Manning

University of Texas at Austin, Department of Molecular Biosciences, 205 W. 24th St., Austin, TX 78712-1240, USA.

Víctor Martín

Department of Pharmacology, Veterinary School, University of Santiago de Compostela, Campus Universitario, 27002 Lugo, Spain.

Edward McHugh

Algae Health Ltd., Rooaunmore Lodge, Rooaunmore, Claregalway, Galway, Ireland (ROI).

Patrick Murray

Shannon Applied Biotechnology Centre, Limerick Institute of Technology, Moylish Park, Limerick, Ireland (ROI).

Alexei Novikov

Department of Chemistry, University of North Dakota, Grand Forks, ND 58201.

Paz Otero

Department of Pharmacology, Veterinary School, University of Santiago de Compostela, 27002 Lugo, Spain.

Susete Pinteus

Grupo de Investigação em Recursos Marinhos, Escola Superior de Turismo e Tecnologia do Mar, Instituto Politécnico de Leiria, Campus 4 - Santuário N.a Sra. dos Remédios, 2520 – 641 Peniche, Portugal.

Bachisio Mario Padedda

University of Sassari, Department of Sciences for Nature and Environmental Resources, Via Piandanna 4, 07100 Sassari, Italy.

Rui Pedrosa

Grupo de Investigação em Recursos Marinhos, Escola Superior de Turismo e Tecnologia do Mar, Instituto Politécnico de Leiria, Campus 4 - Santuário N.a Sra. dos Remédios, 2520 – 641 Peniche, Portugal.

Silvia Pulina

University of Sassari, Department of Sciences for Nature and Environmental Resources, Via Piandanna 4, 07100 Sassari, Italy.

Cecilia Teodora Satta

University of Sassari, Department of Sciences for Nature and Environmental Resources, Via Piandanna 4, 07100 Sassari, Italy.

Verónica Rey López

Department of Analytical Chemistry, Faculty of Sciences, University of Santiago de Compostela. C/ Alfonso X s/n, 27002 Lugo, Spain.

Juan A. Rubiolo

Department of Pharmacology, Veterinary School, Campus de Lugo, University of Santiago de Compostela, 27002 Lugo, Spain.

Nicola Sechi

University of Sassari, Department of Sciences for Nature and Environmental Resources, Via Piandanna 4, 07100 Sassari, Italy.

Carmen Vale

Department of Pharmacology, Veterinary School, University of Santiago de Compostela, Campus Universitario, 27002, Lugo, Spain.

Vitor Vasconcelos

Interdisciplinary Center of Marine and Environmental Research, CIIMAR, and Faculty of Sciences, University of Porto, Porto, Portugal.

Mercedes R. Vieytes

Department of Physiology, Veterinary School, Campus de Lugo, University of Santiago de Compostela, 27002 Lugo, Spain.

Natalia Vilariño

Department of Pharmacology, Veterinary School, University of Santiago de Compostela, 27002 Lugo, Spain.

Daniel J. Walsh

Shannon Applied Biotechnology Centre, Limerick Institute of Technology, Moylish Park, Limerick, Ireland (ROI).

Armen Zakarian

Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA 93106, USA.

Preface

The reason for this second edition of Phycotoxins: Chemistry and Biochemistry is to update the information that relates to the field of marine toxins and marine compounds. Although marine toxins are usually associated with risks in food safety, there is much more to the subject than this. On the one hand, marine toxins are an excellent source of drug leads, since their structures are very diverse, ranging from very simple (domoic acid) to extremely complex (maitotoxin), and they are also a growing indicator of ecological changes caused by a changing climate. A third aspect of marine compounds and marine toxins is the vast number of physiological targets they have, which makes their study extremely interesting for research purposes once their mechanism of action is understood.

With the intention of offering a wide view of all these aspects, this book covers several topics which are of growing concern in several fields of research. Chapter 1 describes the current technical situation of the analysis of marine toxins for their control and monitoring as a food risk. Chapters 2 to 6, 14 and 15 describe mechanistic and chemical aspects of toxins of particular interest, as their presence and chemical profile may not be not well understood, or is changing in certain geographical areas. Chapters 7, 10 and 11 describe interesting aspects of toxins from freshwater, in some cases with equivalencies to marine toxins, and possible influence of climate.

The chemical diversity of marine compounds, and their mechanism of action, as well as their diversity as possible drug leads, is covered in chapters 8, 12, 13, 16 and 17. Specifically, chapter 17 describes how the elaboration of these toxins (and their stereochemistry) is so complex. Finally, chapters 18 and 19 describe special toxins in fish, and how to identify the damage caused by the marine toxins.

This book could not have been written without the generosity, talent and dedication of specialists in each field who contributed enthusiastically, giving up a large number of days to prepare each of the chapters. As editors, we wish to acknowledge their efforts and give thanks for the support they have given to this book. Without their generosity, this type of book would not be possible. So we offer a sincere ‘thank you’ to them all.

Finally, we wish to thank Wiley-Blackwell for believing in this project.

Amparo Alfonso and Luis M Botana

Chapter 1Analysis of marine toxins: gaps on food safety control of marine toxins

Paz Otero1 & Carmen Alfonso2

1Department of Pharmacology, University of Santiago de Compostela, Spain

2Cifga Laboratory, Pl. Santo Domingo, Spain

Analysis of marine toxins and gaps on food safety control

The field of marine toxins has been deeply studied in recent decades, but there are a lot of variables that need to be understood. These relate to the occurrence of harmful algal blooms, the production of different analogues of the same group of toxins, their accumulation and biotransformation in shellfish or in fish, and the associated hazards for human consumers, both from acute and long-term exposure.

Different factors are related to the proliferation of a determined alga in a zone: physical considerations, such as temperature or light, chemical parameters like nutrients, oxygen or pollutants, and biological relationships between kinds of algae and shellfish. These proliferations can develop suddenly, due to the germination of cysts from ocean sediments under appropriate environmental conditions, (Camacho ., 2007) and are referred to as harmful algal blooms (HABs) if marine toxins are detected during them.