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JOURNAL OF CHROMATOGRAPHY LIBRARY- volume 54 chromatography of mycotoxins techniques and applications This Page Intentionally Left Blank JOURNAL OF CHROMATOGRAPHY LIBRARY- volume 54 chromatography of mycotoxins techniques and applications edited by Vladimir Betina Department of Microbiology, Biochemistry and Biology, Slovak Technical University, Brat islava, Slovakia ELSEVIER - - Amsterdam London New York -Tokyo 1993 ELSEVIER SCIENCE PUBLISHERS B.V. Sara Burgerhartstraat 25 P.O. Box 21 1,1000AE Amsterdam,The Netherlands ISBN 0-444-81521-X 0 1993 Elsevier Science Publishers B.V. 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, without the prior written permission of the publisher, Elsevier Science Publishers B.V., Copyright & Permissions Department, P.O. Box 521,1000AM Amsterdam,The Netherlands. Special regulations for readers in the U.S.A. - This publication has been registered with the Copyright Clearance Center Inc. (CCC), Salem, Massachusetts. Information can be obtained from the CCC about conditions under which photocopies of parts of this publication may be made in the U.S.A. All other copyright questions, including photocopying outside of the U.S.A., should be referred to the copyright owner, Elsevier Science Publishers B.V., unless otherwise specified. No responsibility is assumed by the publisher for any injury and/or damage to persons or property as a matter of products liability, negligence or otherwise, or from any use or operation of any methods, products, instructions or ideas contained in the material herein. This book is printed on acid-free paper. Printed in the Netherlands V CONTENTS ..................................... List of contributors xii .................................................. Preface xiii . Part A Techniques . Chapter 1 Sampling. sample preparation. extraction and clean-up . ........................................ V Betina 3 ............................................ 1.1 Introduction 3 ......................... 1.2 Sampling and sample preparation 3 .......................... 1.3 Sample extraction and clean-up 4 .................................... 1.4 Illustrative example 7 ............................................. 1.5 Conclusions 9 .................................................. References 9 . Chapter 2 Techniques of thin layer chromatography ............. R.D. Coker. A.E. John and J.A. Gibbs 12 ............................................ 2.1 Introduction 12 ........................................ 2.2 Clean-up methods 12 ........................................ 2.3 Normal phase TLC 16 ........................................ 2.3.1 Principles 16 .......................... 2.3.2 Practical considerations 17 ............................... 2.4 Reverse-phase TLC (RPTLC) 20 ........................................ 2.4.1 Principles 20 .......................... 2.4.2 Practical considerations 20 ...... 2.5 High performance thin layer chromatography (HPTLC) 21 ........................................ 2.5.1 Principles 21 .......................... 2.5.2 Practical considerations 22 ......................................... 2.6 Preparative TLC 23 ........................................ 2.6.1 Principles 23 .......................... 2.6.2 Practical considerations 25 ............................................... 2.7 Detection 27 ............................ 2.7.1 Fluorescence detection 27 ........................... 2.7.2 Chemical derivatisation 21 ............................ 2.7.3 Bioautographic methods 28 ........... 2.8 Quantitative and semi-quantitative evaluation 28 ................................... 2.9 Illustrative examples 30 ............................................ 2.10 Conclusions 31 .................................................. References 32 vi . Chapter 3 Techniques of liquid column chromatography ........................................ P. Kuronen 36 ............................................. 3.1 Introduction 36 ...................................... 3.2 Sample pretreatment 37 .................................... 3.3 Column chromatography 40 ....................................... 3.3.1 Introduction 40 .......................................... 3.3.2 Procedure 40 ............................... 3.4 Mini-column chromatography 44 .......................................... 3.4.1 Procedure 45 ............................... 3.4.2 Illustrative example 46 ................... 3.5 High-performance liquid chromatography 46 ....................................... 3.5.1 Introduction 46 ....................... 3.5.2 Instrumentation and practice 48 ............................................... 3.6 Conclusion 71 ................................................... References 72 . Chapter 4 Techniques of gas chromatography ....................................... R.W. Beaver 78 ............................................. 4.1 Introduction 78 ......................... 4.2 Resolution in gas chromatography 79 ........................... 4.2.1 Definition of resolution 79 ......................................... 4.2.2 Efficiency 79 .......................................... 4.2.3 Retention 83 ........................................ 4.2.4 Selectivity 84 ................................... 4.3 Extracolumn resolution 86 ................. 4.3.1 Resolution through sample clean-up 87 ............................ 4.3.2 Chemical derivatization 91 ....................... 4.3.3 Resolution through detection 91 .............................................. 4.4 Conclusions 96 ................................................... References 96 . Chapter 5 Emerging techniques: immunoaffinity chromatography .................. A.A.G. Candlish and W.H. Stimson 99 ............................................. 5.1 Introduction 99 .................... 5.2 Immunoaffinity chromatography theory 101 ................... 5.3 Practical aspects and instrumentation 103 ...................................... 5.4 Sample preparation 111 ................................... 5.5 Illustrative examples 116 .................................................. References 122 vii . Chapter 6 Emerging techniques: enzyme-linked immunosorbent assay (ELISA) as alternatives to chromatographic methods ..... C.M. Ward. A.P. Wilkinson and M.R.A. Morgan 124 ........................................... 6.1 Introduction 124 .................................... 6.2 Principles of ELISA 124 .... 6.2.1 The immune response and polyclonal antibodies 124 ............................ 6.2.2 Monoclonal antibodies 125 .......................................... 6.2.3 Haptens 125 ............ 6.2.4 Specificity of anti-hapten antibodies 125 ........................ 6.2.5 Principles of immunoassay 126 .............................. 6.2.6 Enzyme immunoassays 126 ....... 6.2.7 Enzyme-linked immunosorbent assays (ELISAS) 127 ..................................... 6.3 Sample preparation 127 ....................................... 6.3.1 Extraction 127 ........................... 6.4 Instrumentation and practice 128 .................................. 6.4.1 Instrumentation 128 ......................................... 6.4.2 Practice 129 .................................. 6.5 Illustrative examples 132 ....................................... 6.5.1 Aflatoxins 132 ................................. 6.5.2 Other mycotoxins 133 ............................................ 6.6 Conclusions 134 ................................................. References 135 . Part B Applications . Chapter 7 Thin-layer chromatography of mycotoxins . ....................................... V Betina 141 ........................................... 7.1 Introduction 141 ............................................. 7.2 Aflatoxins 143 .................. 7.2.1 Sampling and sample preparation 143 .......................... 7.2.2 Extraction and clean-up 144 ................... 7.2.3 Adsorbents and solvent systems 149 ........................................ 7.2.4 Detection 152 ............................ 7.2.5 Selected applications 153 ................. 7.3 Sterigmatocystin and related compounds 162 .......................... 7.3.1 Extraction and clean-up 162 ................... 7.3.2 Adsorbents and solvent systems 164 ........................................ 7.3.3 Detection 166 ............................ 1.3.4 Selected applications 166 ......................................... 7.4 Trichothecenes 168 .......................... 7.4.1 Extraction and clean-up 169 viii ................... 7.4.2 Adsorbents and solvent systems 169 ........................................ 7.4.3 Detection 170 ............................ 7.4.4 Selected applications 173 ......................................... 7.5 Small lactones 178 .......................................... 7.5.1 Patulin 178 .................................. 7.5.2 Penicillic acid 181 ................................ 7.5.3 Mycophenolic acid 183 ....................................... 7.5.4 Butenolide 184 .................................... 7.5.5 Citreoviridin 184 ................................... 7.6 Macrocyclic lactones 186 ...................................... 7.6.1 Zearalenone 186 .................................... 7.6.2 Cytochalasans 191 ............................................ 7.7 Ochratoxins 196 .......................... 7.7.1 Extraction and clean-up 196 ................... 7.7.2 Adsorbents and solvent systems 196 ........................................ 7.7.3 Detection 197 ............................ 7.7.4 Selected applications 198 ............................................ 7.8 Rubratoxins 199 .......................... 7.8.1 Extraction and clean-up 199 ................... 7.8.2 Adsorbents and solvent systems 199 ........................................ 7.8.3 Detection 199 ............................ 7.8.4 Selected applications 200 .................................. 7.9 Hydroxyanthraquinones 200 ....................................... 7.9.1 Extraction 201 ................... 7.9.2 Adsorbents and solvent systems 201 ........................................ 7.9.3 Detection 201 ............................ 7.9.4 Selected applications 201 ...................... 7.10 Epipolythiopiperazine-3. 6.diones 203 ......................... 7.10.1 Extraction and clean-up 203 ....... 7.10.2 Adsorbents. solvent systems and detection 204 ........................... 7.10.3 Selected applications 204 ................................ 7.11 Tremorgenic mycotoxins 205 .................. 7.11.1 Adsorbents and solvent systems 205 ....................................... 7.11.2 Detection 205 ........................... 7.11.3 Selected applications 207 ..................................... 7.12 Alternaria toxins 209 ......................... 7.12.1 Extraction and clean-up 209 .................. 7.12.2 Adsorbents and solvent systems 209 ....................................... 7.12.3 Detection 210 ........................... 7.12.4 Selected applications 210 ix ............................................. 7.13 Citrinin 210 ........................ 7.13.1 Extraction and clean-up 211 ................. 7.13.2 Adsorbents and solvent systems 212 ...................................... 7.13.3 Detection 212 .......................... 7.13.4 Selected applications 213 ................................ 7.14 a-Cyclopiazonic acid 214 ........................ 7.14.1 Extraction and clean-up 214 ................. 7.14.2 Adsorbents and solvent systems 215 ...................................... 7.14.3 Detection 215 .......................... 7.14.4 Selected applications 216 ............................ 7.15 PR toxin and roquefortine 217 ........................ 7.15.1 Extraction and clean-up 217 ................. 7.15.2 Adsorbents and solvent systems 217 ...................................... 7.15.3 Detection 217 .............. 7.16 Xanthomegnin. viomellein and vioxanthin 218 ........................ 7.16.1 Extraction and clean-up 218 ................. 7.16.2 Adsorbents and solvent systems 218 ...................................... 7.16.3 Detection 218 .......................... 7.16.4 Selected applications 218 ................................... 7.17 Naphtho- y -pyrones 219 ...................................... 7.18 Secalonic acids 219 .......................... 7.19 TLC of miscellaneous toxins 220 .................................. 7.20 Multi-mycotoxin TLC 222 ..... 7.21 TLC in chemotaxonomic studies of toxigenic fungi 230 .......................................... 7.22 Conclusions 231 ................................................ References 233 . Chapter 8 Liquid column chromatography of mycotoxins . ..................... J.C. Frisvad and U Thrane 253 .......................................... 8.1 Introduction 253 ................................. 8.2 Column chromatography 287 ............................ 8.3 Mini-column chromatography 289 ................ 8.4 High performance liquid chromatography 290 ...................................... 8.4.1 Aflatoxins 290 .......... 8.4.2 Sterigmatocystin and related compounds 295 .................................. 8.4.3 Trichothecenes 296 .................................. 8.4.4 Small lactones 299 ............................ 8.4.5 Macrocyclic lactones 302 ............... 8.4.6 Ochratoxins and related compounds 303 ..................................... 8.4.7 Rubratoxins 306 ............. 8.4.8 Hydroxyanthraquinones and xanthones 307

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