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2 Pyrrolizidine Alkaloids Uses Educational For http://sites.google.com/site/irdadeh/ ,09126599985,[email protected], Center Data Data Center ,09126599985,[email protected], For Educational Uses BLUK145-Gilbert March 5, 2008 22:30 Bioactive Compounds in Foods Bioactive Compounds in Foods Edited by John Gilbert and Hamide Z. Senyuva. © 2008 Blackwell Publishing Ltd, ISBN: 978-1-4051-5875-6 i Data Center ,09126599985,[email protected], For Educational Uses BLUK145-Gilbert March 5, 2008 22:30 Bioactive Compounds in Foods Edited by John Gilbert Central Science Laboratory, Sand Hutton, York, UK Hamide Z. S¸enyuva Scientific and Technological Research Council of Turkey (TUB¨ ITAK),˙ Ankara Test and Analysis Laboratory (ATAL), Ankara, Turkey iii Data Center ,09126599985,[email protected], For Educational Uses BLUK145-Gilbert March 5, 2008 22:30 This edition first published 2008 C 2008 by Blackwell Publishing Ltd Blackwell Publishing was acquired by John Wiley & Sons in February 2007. Blackwell’s publishing programme has been merged with Wiley’s global Scientific, Technical, and Medical business to form Wiley-Blackwell. Registered office John Wiley & Sons Ltd, The Atrium, Southern Gate, Chichester, West Sussex, PO19 8SQ, United Kingdom Editorial office 9600 Garsington Road, Oxford, OX4 2DQ, United Kingdom For details of our global editorial offices, for customer services and for information about how to apply for permission to reuse the copyright material in this book please see our website at www.wiley.com/wiley-blackwell. The right of the author to be identified as the author of this work has been asserted in accordance with the Copyright, Designs and Patents Act 1988. All rights reserved. No part of this publication may be reproduced, stored in a retrieval system, or transmitted, in any form or by any means, electronic, mechanical, photocopying, recording or otherwise, except as permitted by the UK Copyright, Designs and Patents Act 1988, without the prior permission of the publisher. Wiley also publishes its books in a variety of electronic formats. Some content that appears in print may not be available in electronic books. Designations used by companies to distinguish their products are often claimed as trademarks. All brand names and product names used in this book are trade names, service marks, trademarks or registered trademarks of their respective owners. The publisher is not associated with any product or vendor mentioned in this book. This publication is designed to provide accurate and authoritative information in regard to the subject matter covered. It is sold on the understanding that the publisher is not engaged in rendering professional services. If professional advice or other expert assistance is required, the services of a competent professional should be sought. Library of Congress Cataloging-in-Publication Data Bioactive compounds in foods/edited by John Gilbert, Hamide Z. S¸enyuva. p. cm. Includes bibliographical references and index. ISBN-13: 978-1-4051-5875-6 (hardback : alk. paper) ISBN-10: 1-4051-5875-1 (hardback : alk. paper) 1. Food–Analysis. 2. Food–Toxicology. 3. Food contamination. 4. Bioactive compounds I. Gilbert, John. II. Senyuva, Hamide Z. TX545.B56 2008 664.07–dc22 2007038437 A catalogue record for this book is available from the British Library. Set in 10/12 pt, Times by Aptara Inc., New Delhi, India Printed in Singapore by Markono Print Media Pte Ltd 1 2008 For the cover: Brown mushrooms photo c Alan Dunlop-Walters – Fotolia.com French fries photo c Anette Linnea Ras mussen – Fotolia.com Golden maize photo c AGphotographer – Fotolia.com Mixed vegetables photo c Michelle Marsan – Fotolia.com Mussels photo c Alison Bowden – Fotolia.com iv Data Center ,09126599985,[email protected], For Educational Uses BLUK145-Gilbert March 5, 2008 22:30 Contents Contributors xv PART ONE: NATURAL TOXICANTS 1 1 Introduction 3 John Gilbert and Hamide Z. S¸enyuva 1.1 Different perceptions of chemicals in food 3 1.2 Residues and contaminants in foods 4 1.3 Natural toxicants in foods 5 1.4 Developments in analytical methodology 6 1.5 Emerging risks 7 1.6 Bioactive compounds in foods 8 2 Pyrrolizidine Alkaloids 10 Colin Crews and Rudolf Krska Summary 10 2.1 Introduction 10 2.2 The pyrrolizidine alkaloids 11 2.3 Occurrence 12 2.3.1 Formation and function 13 2.4 Exposure 13 2.4.1 Contamination of foods 14 2.4.2 Pyrrolizidines in herbal preparations 15 2.5 Regulations 17 2.6 Toxicity and metabolism 17 2.6.1 General toxicity 17 2.6.2 Metabolism 18 2.6.3 Carcinogenicity and mutagenicity 18 2.7 Analytical methods 19 2.7.1 Extraction 20 2.7.2 Gas chromatography 20 2.7.3 High performance liquid chromatography 21 2.7.4 Other methods 22 Conclusions 24 References 24 Data Center ,09126599985,[email protected], For Educational Uses BLUK145-Gilbert March 5, 2008 22:30 vi Contents 3 Glucosinolates 31 Ruud Verkerk and Matthijs Dekker Summary 31 3.1 Introduction 31 3.2 Nature and occurrence 32 3.3 Biosynthesis 33 3.3.1 Amino acid modification 34 3.3.2 Conversion of amino acids 34 3.3.3 Secondary transformations 35 3.4 Hydrolysis 35 3.4.1 Myrosinase 35 3.4.2 Hydrolysis products 36 3.5 Analytical methods 38 3.5.1 Total glucosinolates 38 3.5.2 Individual glucosinolates 38 3.5.3 Breakdown products 40 3.6 Biological effects 40 3.6.1 Anticarcinogenicity 40 3.6.2 Toxicity 42 3.7 Taste versus health 43 3.8 Responses to stress factors 44 3.9 Effects of processing 44 Conclusions 47 References 47 4 Phycotoxins in Seafood 52 John W. Leftley and Fiona Hannah Summary 52 4.1 Introduction 52 4.2 Causative and vector organisms 52 4.3 Classification of phycotoxins 55 4.4 The saxitoxin (STX) group (PSP) 55 4.4.1 The toxins causing PSP: the saxitoxin family 58 4.4.2 Toxic effects 60 4.5 The okadaic acid (OA) group (DSP) 61 4.5.1 The toxins causing DSP: okadaic acid and the dinophysistoxins 64 4.5.2 Toxic effects 66 4.6 The domoic acid (DA) group (ASP) 68 4.6.1 The toxins causing ASP (DAP): domoic acid and its isomers 69 4.6.2 Toxic effects 69 4.7 The azaspiracid (AZA) group (AZP) 69 4.7.1 The toxins causing AZP: the azaspiracids 70 4.7.2 Toxic effects 71 4.8 The brevetoxin (BTX) group (NSP) 74 4.8.1 The toxins causing NSP: the brevetoxins 74 4.8.2 Toxic effects 75 Data Center ,09126599985,[email protected], For Educational Uses BLUK145-Gilbert March 5, 2008 22:30 Contents vii 4.9 The ciguatera toxin (CTX) group (CFP) 75 4.9.1 The toxins causing CFP 76 4.9.2 Toxic effects of CTXs 77 4.10 Other phycotoxins 77 4.10.1 The pectenotoxin group 77 4.10.2 The yessotoxin group 78 4.10.3 The cyclic imine group 80 4.10.4 The cyanobacterial toxins 82 4.10.5 Miscellaneous phycotoxins 83 4.11 Detection of phycotoxins in seafood and algae 83 4.11.1 Assays and analyses 84 4.11.2 Mammalian bioassays 85 4.11.3 Instrumental (physico-chemical) analysis 86 4.11.4 In vitro assays 87 4.12 Depuration of phycotoxins 88 4.12.1 Natural depuration 88 4.12.2 Studies on cooking as a method of depuration 89 4.12.3 The effects of freezing and chilling 91 4.13 Monitoring and regulation 92 4.13.1 Phytoplankton monitoring 92 4.13.2 Monitoring of shellfish tissues for toxicity 93 4.13.3 Risk analysis 93 4.14 Future prospects 96 4.15 A note on the IOC harmful algal bloom programme 96 Acknowledgements 97 References 97 5 Mushroom Toxins 110 Jana Hajslov´aand Vera Schulzova Summary 110 5.1 Introduction 110 5.2 Poisonous mushrooms 112 5.2.1 Amatoxins, phallotoxins and virotoxins 112 5.2.2 Orellanine 116 5.2.3 Muscarine 117 5.2.4 Ibotenic acid and muscimol 118 5.2.5 Psilocybin, psilocin 119 5.2.6 Coprine 121 5.3 Edible mushrooms 122 5.3.1 Gyromitrin 122 5.3.2 Agaritine and other phenylhydrazines 125 References 129 6 Mycotoxins 134 Keith A. Scudamore Summary 134 Data Center ,09126599985,[email protected], For Educational Uses BLUK145-Gilbert March 5, 2008 22:30 viii Contents 6.1 Introduction 134 6.1.1 Mycotoxins and their study 134 6.1.2 Mycotoxins and fungi 136 6.1.3 Sampling and detection 137 6.1.4 Significance and control 142 6.2 Aflatoxins 142 6.2.1 Chemical properties 142 6.2.2 Analytical methods 143 6.2.3 Occurrence in raw materials and processed foods 144 6.2.4 Toxicology 145 6.2.5 Regulation and control 146 6.3 Ochratoxin A 146 6.3.1 Chemical properties 146 6.3.2 Analytical methods 147 6.3.3 Occurrence in raw materials and processed foods 147 6.3.4 Toxicology 148 6.3.5 Regulation and control 148 6.4 Deoxynivalenol and the trichothecenes 149 6.4.1 Chemical properties 149 6.4.2 Analytical methods 150 6.4.3 Occurrence in raw materials and processed foods 151 6.4.4 Toxicology 151 6.4.5 Regulation and control 152 6.5 Zearalenone 153 6.5.1 Chemical properties 153 6.5.2 Analytical methods 153 6.5.3 Occurrence in raw materials and processed foods 154 6.5.4 Toxicology 154 6.5.5 Regulation and control 154 6.6 Fumonisins 155 6.6.1 Chemical properties 155 6.6.2 Analytical methods 155 6.6.3 Occurrence in raw materials and processed foods 156 6.6.4 Toxicology 156 6.6.5 Regulation and control 157 6.7 Patulin 157 6.7.1 Chemical properties 157 6.7.2 Analytical methods 157 6.7.3 Occurrence in raw materials and processed foods 158 6.7.4 Toxicology 158 6.7.5 Regulation and control 159 6.8 Other mycotoxins 159 6.8.1 Citrinin 159 6.8.2 Sterigmatocystin 160 6.8.3 Cyclopiazonic acid 160 6.8.4 Moniliformin 161 6.8.5 Alternaria toxins 161 References 162 Data Center ,09126599985,[email protected], For Educational Uses BLUK145-Gilbert March 5, 2008 22:30 Contents ix 7 Phytoestrogens 173 Don Clarke and Helen Wiseman Summary 173 7.1 Introduction 173 7.2 The structure of phytoestrogens 173 7.3 Occurrence
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