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«TAN THUAN CHEW MONITORING THE EFFECTIVENESS IN ELIMINATING THE TRACE PRESENCE OF AOZ (FURAZOLIDONE DERIVATIVE) RESIDUE IN PENAEUS MONODON AND ITS ...»

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MONITORING THE EFFECTIVENESS IN ELIMINATING THE TRACE

PRESENCE OF AOZ (FURAZOLIDONE DERIVATIVE) RESIDUE IN

PENAEUS MONODON AND ITS PRODUCTS UNDERGOING DIFFERENT

PROCESSING REGIMES

TAN THUAN CHEW

MONITORING THE EFFECTIVENESS IN ELIMINATING THE TRACE

PRESENCE OF AOZ (FURAZOLIDONE DERIVATIVE) RESIDUE IN

PENAEUS MONODON AND ITS PRODUCTS UNDERGOING DIFFERENT

PROCESSING REGIMES

by

TAN THUAN CHEW

Thesis submitted in fulfilment of the requirements for the degree of Master of Science JANUARY 2008

ACKNOWLEDGEMENTS

This study would not have been completed without the help and support of many people. First and foremost, I would like to thank my main supervisor, Associate Professor Dr. Noryati Ismail. Thank you for your patience, guidance and advice throughout this project. You have been a great help, an inspiration, and both a mentor and a dear friend to me. You were there to guide me whenever I was out of the track in achieving my objectives in this study.

I would like to extend my special thanks to Professor Aishah Latiff, my cosupervisor as well as the director of USM Doping Control Centre. Without the great support from you, I would believe that this project would not be able to complete.

Thanks for allowing me to use the equipments that are available in USM Doping Control Centre and more importantly, having the trust in allowing me handle the equipments personally. The facilities available in USM Doping Control Centre were tremendously essential in completing this study.

On top of that, my sincere gratitude to the staffs of USM Doping Control Centre, especially Kak Hayati, Kak Fazeha, Kak Eha, Kak Haira and Kak Rasidah for their gracious, and invaluable help during my laboratory work in USM Doping Control Centre. To Kak Hayati, I owed you so much because of all the time you spent to teach me how to operate, and maintain LCQ Advantage and also sharing experience and knowledge on the theoretical background on chromatographic separation. To Kak Fazeha, I’m so grateful for your helpful guidance and discussions and technical assistance on sample preparation. The working environment in USM Doping Control Centre is really the greatest experience I ever had in my life. The friendliness and the spirit of helping others really touch my heart. Thanks for the warmth hospitality.

ii This research was made possible in part due to some generous support in the form of materials and knowledge of five generous souls. I’m very grateful to Mr. Sunny Kam, Mr. Tan, and Mr. Lim for the generosity in supplying me with tiger prawns to be used throughout my whole research. The technical assistance of Mr. Loh in regards to tiger prawns rearing is highly appreciated. Besides the kind supply from both Mr. Sunny Kam and Mr. Loh, special thanks to Penang Fisheries Research Institute and particularly to Mr. Othman Muhamad for the kind supply of 2-NPAOZ.

I would like to thank both my father and mother for their unconditional support (both financially and mentally) and their care, understanding and believing in me that I can do it during the past three years. Not forgetting, I would like to thank all my beloved post-graduate friends (Li Choo, Wan Teck, Hooi Ling, Kim Siew, Joyce Yee, Weng Kee, Matthew and others) for always there for me whenever I needed some morale boost.

Finally, I would also like to take this opportunity to apologise to everyone if I have did or said something wrong in one way or another. I believe that I have had temper tantrums at times, especially when there’s no result in my research. Hope it didn’t really bother you and give you much trouble.

Tan Thuan Chew January, 2008

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Appendix C: Results from Tuning and Calibration LCQ Advantage 132 Appendix D: The Identification Points Table for Molecular Identification 136 Appendix E: Linearity: Peak Area and Area Ratio for transition ions of 2- 137 NPAOZ and 2-NPAOZ-d4.

Appendix F: One-Way ANOVA Test Results for the Stability of AOZ Residue 140 in Tiger Prawns Undergoing Processing

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Table 2.1 Characteristics of the base silica physical properties and 33 chemical modification for Inertsil! ODS-3.

(GL Science, 2001)

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Table 4.1 RRT of 2-NPAOZ (derivatised furazolidone metabolite) to its 79 internal standard counterpart (2-NPAOZ-d4).

Table 4.2 Diagnostic ions for 2-NPAOZ (derivatised furazolidone 80 metabolite) and its internal standard counterpart (2-NPAOZ-d4).

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Table 4.5 Extraction recovery of 2-NPAOZ from different tiger prawn 87 matrices; tail muscle, head, and exoskeleton.

Table 4.6 Precision of LC-MS/MS method for 2-NPAOZ for three different 89 tiger prawn matrices; tail muscle, head, and exoskeleton.





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Table 4.8 CC" and CC# (in ng/g) for the determination of AOZ in different 92 tiger prawn matrixes calculated using both the transition ions.

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Figure 2.1 External anatomy of a tiger prawn.

(http://www.disease- 6 watch.com/documents/CD/index/html/tc.htm) Figure 2.2 The life cycle of Panaeid shrimp. (Lankester et al., 2003) 6 Figure 2.3 The constructed cooking chart for large tiger shrimp (35 - 44 10 shrimps/kg). (Erdo!du et al., 2003) Figure 2.4 The constructed cooking chart for medium tiger shrimp (90 - 10 110 shrimps/kg). (Erdo!du et al., 2003) Figure 2.5 Structure of the nitrofuran antimicrobials and their free major 24 metabolites. (Leitner et al., 2001)

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Figure 3.1 Flow chart of pre-processing procedure for tiger prawns.

58 Figure 3.2 Flow chart of processing procedure for preparing frozen 59 peeled, deveined, headless tiger prawns.

Figure 3.3 Flow chart of processing procedure for preparing frozen 59 peeled, deveined, headless, cooked tiger prawns.

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LOQ Limits of quantification MAO Monoamine oxidase MRL Maximum residue limit MRPL Minimum required performance reporting limit NBA 2-nitrobenzaldehyde ODS Octadecylsilyl

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R Within-laboratory reproducibility RIC Reconstructed ion chromatogram RPC Reversed-phase chromatography RRT Relative retention time RSD Relative standard deviation RT Retention time SA Analytical limit standard SC Matrix-match calibrating standard SD Standard deviation SEM Semicarbazide S/N Sound-to-noise ratio SPE Solid-phase extraction SR Recovery standard SRM Selected reaction monitoring SV Validating standard TIC Total ion current chromatogram Tr1 Less intense transition ion Tr2 More intense transition ion UHQ Ultra high quality

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Appendix D The Identification Points Table for Molecular Identification 136 Appendix E Linearity: Peak Area and Area Ratio for transition ions of 2- 137 NPAOZ and 2-NPAOZ-d4.

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Pihak berkuasa Malaysia telah mengharamkan penggunaan furazolidon (salah satu daripada nitrofuran utama yang ada) dalam haiwan ternakan. Hal ini adalah berdasarkan risiko dari segi kesihatan yang boleh memudaratkan orang umum.

Penekanan diberi dalam mengesan kehadiran metabolit utama furazolidon, iaitu 3amino-2-oxazolidinona (AOZ). Metabolit ini adalah lebih stabil dan kekal lebih lama di dalam tisu haiwan berbanding dengan furazolidon. Oleh itu, pengesanan metabolit

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furazolidon. Kaedah pengesahan melibatkan penggunaan pengionan elektrosembur positif kromatografi cecair-spektrometri jisim tandem (ESI LC-MS/MS) untuk menentu paras AOZ dalam udang harimau (Penaeus monodon). Sebelum analisis LC-MS/MS

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penghomogenan, hidrolisis asid metabolit yang terangkai pada protein, dan derivatasasi dengan 2-nitrobenzaldehid (2-NBA). Pembersihan sampel dan penulenan analit dijalankan dengan melibatkan pengekstrakan berganda dengan etil asetat.

Pemisahan molekul dijalankan dengan menggunakan kromatografi cecair dengan kolum C18 (Inertsil! ODS-3 50.0 mm x 2.1 mm, 3 µm) pada suhu bilik. Kuantifikasi analit dijalankan berdasarkan garis panduan daripada EU dengan melibatkan pemantauan tindakbalas selektif (SRM) yang melibatkan satu ion prekursor dan dua ion produk sebagai penentu. Kuantifikasi yang lebih jitu dan sensitif diperoleh melalui penggunaan standard terdeturasi (AOZ-d4) sebagai standard dalaman (IS). Kaedah yang digunakan divalidasi berdasarkan garis panduan daripada Commission Decision 2002/657/EC dengan melibatkan penggunaan sampel blank dan standard matrik (ditambah dengan AOZ ataupun 2-NPAOZ, bersama-sama dengan AOZ-d4). Validasi

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pengesahan, nisbah S/N, dan nisbah ion transisi), kelinearan, pengekstrakan perolehan, persisi (termasuk kebolehulangan, dan kebolehulangan intra-makmal), dan had analitikal (termasuk LOD, LOQ, CC", and CC#) untuk menentukan kesuaian keadah ini. Had analitikal untuk semua matrik udang berada di bawah paras MRPL untuk nitrofuran (1 ng/g). Kurva piawai berada dalam bentuk linear untuk julat kepekatan AOZ dari 0 hingga 2,000 ng/g untuk semua matrik udang. Udang harimau dirawat dengan furazolidon melalui kaedah rawatan mandi dengan kepekatan 30 mg furazolidon/L air garam untuk 10 hari berturut-turut. Residu AOZ dalam otot, kepala dan eksoskeleton udang mencapai paras maksimum, iaitu pada kepekatan 8,671.08 ±

628.80 ng/g, 9820.14 ± 4,15.47 ng/g, and 11,025.12 ± 730.76 ng/g, masing-masing sebaik sahaja selepas rawatan furazolidone. AOZ adalah sangat susah untuk disingkirkan. Oleh demikian, AOZ masih boleh dikesan selepas 2 bulan dari rawatan terakhir. Tiga jenis produk udang dipilih, iaitu udang beku tanpa kulit, urat and kepala, udang masak beku tanpa kulit, urat and kepala, dan udang jeruk. Proses yang terlibat dalam penghasilan produk-produk yang terpilih tidak berjaya dalam menyingkirkan kesemua residu AOZ dalam udang yang dirawat dengan furazolidon. Penyingkiran AOZ yang terbanyak boleh diperoleh melalui proses yang terlibat dalam penyediaan udang masak beku tanpa kulit, urat dan kepala yang melibatkan penggunaan 1 % asid laktik, iaitu sedikit kurang daripada 50 % (termasuk peratusan penyingkiran daripada pra-pemprosesan).

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Due to its risk showered upon public health, Malaysia authorities has prohibited the use of furazolidone (one of the main nitrofurans available), in food-producing animals.

Monitoring compliance with the ban has focused on the detection of its main metabolite, 3-amino-2-oxazolidinone (AOZ), which is more stable and persists in the animal tissues with comparison to the parent compound. Thus it’s the best approach to evaluate their utilization. A confirmatory method based on positive electrospray ionization liquid chromatography-tandem mass spectrometry (ESI LC-MS/MS) has been utilised for the trace level determination of AOZ in tiger prawns (Penaeus monodon). Prior to LC-MS/MS analysis, samples undergo various preparation, which entails homogenisation, acid hydrolysis of the protein-bound metabolites and derivatisation with 2-nitrobenzaldehyde (2-NBA). Sample clean-up and analyte enrichment was performed by a double liquid-liquid extraction with ethyl acetate.

Separation of the molecules was performed by liquid chromatography in a C18 column (Inertsil! ODS-3 50.0 mm x 2.1 mm, 3 µm) at room temperature. Analyte quantification was performed according to EU guidelines, using selective reaction monitoring (SRM) with one precursor ion and two product ions as identifiers. A reliable and more sensitive quantitation is obtained by using deuterated standard (AOZ-d4) as internal standard (IS). The “in-house” validation of this method has been performed taking into account the Commission Decision 2002/657/EC. The performance characteristics of the method were established by in-house validation procedures employing assays with sample blanks, matrix-match standards (spiked with AOZ or 2-NPAOZ, with AOZ-d4). Analyte specificity, molecular identification (including RRT, identification points, S/N ratios, and transition ion ratios), linearity, extraction recovery, precision (including repeatability,

–  –  –

and CC#) were validated. The fitness for purpose of this method was assessed based on its performance characteristics. The analytical limits obtained for all the three type of tiger prawn matrices were below the MRPL for nitrofuran, which is 1 ng/g. Linear standard curves were obtained in the ranges 0–2,000 ng/g for all types of tiger prawn matrices. Results showed that after furazolidone treatment, via bath treatment, of 10 mg furazolidone/L salt water for 10 consecutive days, AOZ residue in tail muscle, head, and exoskeleton reached its maximum, 8,671.08 ± 628.80 ng/g, 9820.14 ± 4,15.47 ng/g, and 11,025.12 ± 730.76 ng/g, respectively, right after stopping treatment. AOZ was very difficult to eliminate in vivo, thus AOZ is still detectable even after 2 month from the last furazolidone treatment. Three types of prawn product were selected, which are frozen peeled, deveined, headless prawn, frozen peeled, deveined, cooked, headless prawn, and marinated prawn. None of the processing methods used were able to eliminate all the AOZ residues in the incurred tiger prawns, with the most reduction, slightly less than 50 %, was observed in the incurred tiger prawns undergoing pre-processing coupled with frozen peeled, deveined headless cooked tiger prawn processing (utilising 1 % lactic acid dipping).

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