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New Approaches for Zearalenone Analysis

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New Approaches for Zearalenone Analysis TECHNISCHE UNIVERSITÄT MÜNCHEN Wissenschaftszentrum Weihenstephan für Ernährung, Landnutzung und Umwelt Lehrstuhl für Tierhygiene NEW APPROACHES FOR ZEARALENONE ANALYSIS Lea Pallaroni Vollständiger Abdruck der von der Fakultät Wissenschaftszentrum Weihenstephan für Ernährung, Landnutzung und Umwelt der Technischen Universität München zur Erlangung des akademischen Grades eines Doktors der Agrarwissenshaften (Dr. agr.) genehmigten Dissertation Vorsitzender: Univ.-Prof. Dr. H. H. D. Meyer Prüfer der Dissertation: Univ.-Prof. Dr. J. Bauer Univ.-Prof. Dr. K.-H. Engel Die Dissertation wurde am 22.12.2003 bei der Technischen Universität München eingereicht und durch die Fakultät Wissenschaftszentrum Weihenstephan für Ernährung, Landnutzung und Umwelt am 16.04.2004 angenommen. All substances are poisons; there is none which is not a poison. The right dose differentiates a poison and a remedy. Paracelsus (1493-1541) ACKNOWLEDGEMENT The results presented in this thesis were acquired between September 2000 and February 2003 in the laboratories of the Food Product Unit of the Institute for Health and Consumer Protection and the Food Safety and Quality Unit of the Institute for Reference Materials and Measurements of the Joint Research Centre, Directorate General of the European Commission set in Ispra (Italy). A grateful acknowledgment to Prof. Dr. Johann Bauer (Univ. TUM) for allowing me to present this thesis under his supervision and for the independence he has granted to me in choosing the subject. I am grateful to Prof. Dr. Elke Anklam for the possibility she has given to me to develop the project in the laboratories of the Unit she is leading. I would like to thank Dr. Christoph von Holst for his constant help during the development of this research project and in particular for the statistic support and for the scientific and fruitful discussion. I would like to thank Dr. Erland Björklund for teaching me to focus on experiment design and on summarising the results for publication. A friendly thank to Jan Wollgast for sharing satisfactions as well as troubles encountered using the LC-MS. A special thank to Pietro Violo for his constant presence. I am grateful to Dr. Ebrahim Razzazi-Fazeli (Univ. Wien) and to Dr. Keith Scudamore for their help in finding naturally contaminated corn samples. A sincere thank to Prof. Dr. Steve Safe (Texas A&M Univ.) for helping me in discovering the beauty of scientific research and to Lorna Safe for encouraging me to start my PhD. INTRODUCTION TABLE OF CONTENTS 1 INTRODUCTION 1 1.1 MYCOTOXINS 1 1.2 ZEARALENONE 1 1.2.1 CHEMICAL AND PHYSICAL PROPERTIES 1 1.2.2 PRODUCING ORGANISM 2 1.2.3 NATURAL OCCURRENCE OF ZEARALENONE 3 1.2.4 FATE OF ZEARALENONE 3 1.2.5 TOXICOKINETICS 4 1.2.6 TOXICITY 7 1.2.7 ZEARALENONE LEGAL LIMIT 10 1.3 ANALYTICAL METHODS FOR ZEARALENONE 12 1.3.1 EXTRACTION 12 1.3.2 CLEAN-UP 14 1.3.3 DETECTION AND DETERMINATION 16 2 OBJECTIVE OF THE STUDY 22 3 MATERIALS AND METHODS 23 3.1 SAMPLES 23 3.2 EQUIPMENT 23 3.2.1 EXTRACTION EQUIPMENT 23 3.2.2 HPLC-EQUIPMENT 24 3.3 DEVELOPMENT OF THE LC-MS METHOD 24 3.3.1 OPTIMISATION OF THE INTERFACE PARAMETERS 24 3.3.2 MATRIX EFFECT EVALUATION 25 3.3.3 ZEARALENONE ANALYSIS 26 3.4 EXTRACTION TECHNIQUES 27 3.4.1 DEVELOPMENT OF THE EXTRACTION METHOD 27 3.4.2 MICROWAVE ASSISTED EXTRACTION (MAE) 27 3.4.3 PRESSURIZED LIQUID EXTRACTION (PLE) 27 3.4.4 COMPARISON OF CONVENTIONAL VERSUS ALTERNATIVE EXTRACTION METHODS 28 3.4.5 REDUCTION OF ORGANIC SOLVENTS FOR ZEARALENONE EXTRACTION 28 3.5 DATA EVALUATION 28 4 RESULT AND DISCUSSION 30 4.1 DEVELOPMENT OF THE LC-MS METHOD 30 4.1.1 OPTIMISATION OF THE INTERFACE PARAMETERS 30 4.1.2 MATRIX EFFECT EVALUATION 30 4.1.2.1 Evaluation of the matrix effect using a linear gradient elution 30 4.1.2.2 Evaluation of the matrix effect when working in isocratic mode 33 I INTRODUCTION 4.1.3 ZEARALENONE ANALYSIS 42 4.2 EXTRACTION TECHNIQUES 43 4.2.1 MICROWAVE ASSISTED EXTRACTION (MAE) 43 4.2.2 PRESSURIZED LIQUID EXTRACTION (PLE) 45 4.2.3 COMPARISON OF CONVENTIONAL VERSUS ALTERNATIVE EXTRACTION METHODS 46 4.2.4 REDUCTION OF ORGANIC SOLVENT FOR ZEARALENONE EXTRACTION 53 5 ABSTRACT 55 5.1 ZUSAMMENFASSUNG 57 5.2 RIASSUNTO 59 6 REFERENCES 61 7 CURRICULUM VITAE 69 8 LIST OF PUBLICATIONS 72 8.1 REFEREED PUBLICATION 72 9 APPENDIX A - PUBLICATIONS 75 9.1 APPENDIX I 75 9.2 APPENDIX II 91 9.3 APPENDIX III 99 9.4 APPENDIX IV 107 9.5 APPEDIX V 113 ABSTRACT 115 CHEMICAL AND REAGENTS 117 TEST MATERIAL 117 EQUIPMENT 117 STABILITY STUDY 118 PROCEDURE 118 SIMPLEX 119 STABILITY STUDY 120 SIMPLEX OPTIMISATION 121 10 APPENDIX B 127 10.1 LC-MS 127 10.1.1 MS INTERFACE 127 10.1.2 MS-ANALYSER 127 10.2 ALTERNATIVE EXTRACTION TECHNIQUES 128 10.2.1 MICROWAVE ASSISTED EXTRACTION 129 10.2.2 PRESSURISED LIQUID EXTRACTION 131 II INTRODUCTION 10.3 METHODS OPTIMIZATION 134 10.3.1 FACTORIAL DESIGN 134 10.3.2 SIMPLEX 135 10.3.3 COMPARISON OF DIFFERENT EXTRACTION METHOD 136 III INTRODUCTION LIST OF ABBREVIATIONS APCI Atmospheric Pressure Chemical Ionization API Atmospheric Pressure Interface ASE Accelerated Solvent Extraction BLE Blending bw Body Weight °C Celsius degree Conc Concentration DAD Diode Array Detector DON Deoxynivalenol E2 17β-estradiol ELISA Enzyme Linked ImmunoSorbent Assay ER Estrogen Receptor ESI Electrospray Ionization FAO Food and Agriculture Organization of the United Nations FAPAS® Food Analysis Performance Assessment Scheme FLD Fluorimetry Detector GC Gas Chromatography hER Human Estrogen Receptor HPLC High Performance Liquid Chromatography IA Immunoaffinity IARC International Agency for Research on Cancer Ig Immuno globuline ISTD Internal Standard LC-MS Liquid Chromatography - Mass Spectrometry LD50 Lethal Dose 50 LOD Limit of Detection LOQ Limit of Quantification MAE Microwave Assisted Extraction min minute MRM Multiple Reaction Monitoring MS Mass Spectrometer MW Molecular Weight NIV Nivalenol NOEL No Observed Effect Level PCA Principal Component Analysis PLE Pressurized Liquid Extraction PMTDI Provisional Maximum Tolerable Daily Intake R2 Correlation coefficient RP Reversed Phase S/N Signal-to-Noise SHA Shaking SIM Single Ion Monitoring SPE Solid Phase Extraction TAL Taleranol (β-Zearalanol) TEA Triethylamine TIC Total Ion Chromatogram IV INTRODUCTION TDI Tolerable Daily Intake TLC Thin Layer Chromatography UE Ultrasonic Extraction UV Ultraviolet v/v volume / volume ZAL Zeranol (α-Zearalanol) ZAN Zearalanone ZOL Zearalenol ZOLs α-Zearalenol and β-Zearalenol ZON Zearalenone V INTRODUCTION 1 INTRODUCTION 1.1 Mycotoxins Mycotoxins are low molecular weight compounds produced by many fungal species. Mycotoxins are “secondary metabolites”; this definition refers to the distinction that these metabolites are not essential for the survival and the growth of the fungi (primary metabolism). Generally speaking, secondary metabolites play an important economical role, being either useful as antibiotics, or harmful as mycotoxins. Over 300 mycotoxins synthesized by about 350 different fungi species are known (Cole and Cox, 1981). Among the mycotoxin producers the most important ones belong to the genera Aspergillus, Penicillium and Fusarium (Betina, 1989). 1.2 Zearalenone Zearalenone (ZON) was isolated in 1962 by Stob (1962) and derives its name from the fungus Giberella zeae (perfect state of Fusarium graminearum) from whose mycelia contaminating maize (Zea mays) was first isolated. Its structure (Figure 1-1) was elucidated in 1966 by Urry (1966), who named the discovered compound F-2, later on re-named ZON. OH O CH3 O HO O Figure 1-1: Chemical structure of zearalenone. 1.2.1 Chemical and physical properties ZON can be identified with the systematic name 3,4,5,6,9,10-hexahydro-14,16- dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione or 6-(10-hydroxy-6- 1 INTRODUCTION oxo-trans-1-un-decenyl)-β-resorcyclic-acid-lactone or by the CAS number 17924-92-4. Together with other compounds it belongs to the group of resorcyclic acid lactone (RALs) (Budavari, 1989). ZON, C18H22O5, has a molecular weight (MW) of 318.36, and is a white crystalline compound with a melting point of 164-165 °C. ZON is naturally fluorescent under ultraviolet (UV) light, its spectrum is characterised by three maxima at UVmax 236, 274 and 316 nm with an extinction coefficient in methanol of 29,700, 13,900 and 6,020, respectively. This mycotoxin is practically insoluble in water, while it is soluble in aqueous alkaline solutions, ethyl acetate, acetonitrile, alcohols, diethyl ether, benzene, chloroform and methylene chloride (Betina, 1989; Budavari, 1989). 1.2.2 Producing organism ZON has been isolated from strains of several species belonging to the genus Fusarium such as: F. graminearum, F. culmorum, F. cerealis, F. equiseti, F. nivale, F. roseum, F. tricinctum, F. sporotrichioides, F. oxysporum, F. verticilloides (moniliforme), F. gibbosum, F. avenaceum, F. semitectum and the teleomorphic states (sexual state) Giberella zeae and G. fujikuroi (Betina, 1989, Logrieco et al, 2002). Fusarium genus is characterised by the production of macroconidia, which are septate and fusiform; this genus produces fast growing colonies with felty aerial pale or brightly coloured mycelium (Pitt and Hocking, 1985). Fusarium species are widely spread in soil, especially if cultivated, and are able to decompose cellulosed plant materials leading to plant diseases of major interest such as Fusarium head blight (FHB) in wheat and ear rot in maize (Bottalico and Perrone, 2002; Logrieco et al, 2002). Fusarium colonise cereals in the field (flowering is the optimal phenological phase), but are able to continue their toxic activity during the storage period. The production of mycotoxins during this period is influenced by the interaction of several factors, such as moisture level of the seeds, air temperature and humidity, fungal strains, extent of infection (Moss, 1984).
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