Analysis of pesticide residues in food using ethyl acetate extraction and detection with GC- MS/MS and LC-MS/MS (SweEt)
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1 Analysis of pesticide residues in food using ethyl acetate extraction and detection with GC- MS/MS and LC-MS/MS (SweEt) Tuija Pihlström National Food Agency LAPRW 2015 Santiago de Chile Sweden
2 Outlines of presentation SweEt an alternative method for analysis of pesticides in food Validation according to EU SNACO 12571/2013 Analytical Quality Control Procedures for Pesticide Residue Analysis i Food and Feed Example of reinforced import control (EC 669/2009) using the SweEt method LAPRW 2015 Santiago de Chile
3 Official control of pesticides at the National Food Agency (NFA) in Sweden How is it organized? Laboratories National Reference Laboratory (NRL) and one official laboratory (Eurofins), both accredited Method development Most of the method development at the NFA. Transfer of the methods to the official laboratory for validation and for monitoring of pesticides Analytical methods Mainly multi residue methods based on ethyl acetate extraction and determination using LC-MS/MS and GC-MS/MS Analysis 1800 of 2000 of the samples analysed by OfL (Eurofins)
4 history of the SweEt method Multi residue methods are a self-evident choice for analysis of pesticide residues in food Since 1989 multi residue method based on extraction with ethyl acetate method has been used At that time GC with various detectors was the main detection technique The method has since then continuously been improved including simplified sample preparation and faster analysis Introduction of animal product 2009 has further enlarged the scope of the method
5 The simplified NFA s MRM for FV (448 analytes; 145 GC, 303 LC) Extraction 10 g sample + 3 g NaHCO 3 20 ml ethyl acetate and 10 g Na 2 SO 4 Falcon tube SpexSample Prep 3 minutes Centrifugation in 3 min. (3800 g) Filtration Filtrate the crude extract 0.20 µm PTFE filter Inject to GC-MS/MS and UPLC-MS/MS Sample conc. 0.5g/ml
6 Fruit and vegetables, MRM Steps MIn Min Extraction 3 3 Centrifugation 3 Filtration 5 2 Concentration/redissolve 15 Clean up 45 Concentration/redissolve 10 Filtrate 2 2 Solvent change Ethyl acetate method Extraction 75 g sample+200 ml EtoAc Waring blendor 3 min Decant and filtrate through Na2 SO4 Concentration and redissolve GPC clean up Concentration and redissolve Filtration The simplified SweEt Extraction 10 g sample+20 ml EtoAc Falcon tube SpexShaker prep 3 min Centrifugation Filtration Solvent switch for LC Inject to GC- MS/MS 1.5 g/ml Inject to LC- MS/MS 2.5 g/ml Inject to GC- MS/MS 0.5 g/ml Inject to UPLC-MS/MS 0.5 g/ml
7 FV +honey Cereals AO<10%fat AO>10% fat Extraction 10 g sample 20 ml EtAc+NaHCO 3 3 min Spex shaker Na 2 SO 4 Extraction 5 g sample 10 ml water 10 ml EtAc (1 % Hac) 3 min Spex shaker Na 2 SO 4 Extraction 5 g sample PSA + C18 10 ml EtAc 3 min Spex shaker Na 2 SO 4 Fat determination Extraction 0.5 g fat 10 ml EtAc:cyhex (1+1) 3 min Spex shaker Na 2 SO 4 Centrifugation Centrifugation Centrifugation Centrifugation Filtration Filtration Filtration Filtration GC-MS/MS UPLC- MS/MS GC-MS/MS GC- MS/MS UPLC- MS/MS UPLC- MS/MS GPC SX-3 (1+1 EtOAc/cyklohexane) Evaporation Reconstitution in EtOAc GC-MS/MS UPLC-MS/MS
8 Advantages of the SweEt method Fast and non-laborious Negligible sample work up costs No evaporative concentration steps The extract is injected directly into the GC and LC The need of clean up has been eliminated (almost) Low amounts of matrix components as proteins and sugar which often interfere with the chromatographic are co extracted. National Food Agency, Sweden LAPRW 2015 Santiago de Chile
9 The study of different extraction solvents and the amount of co extracted matrix components J. Klein and L. Alder: Development of a Multi-Analyte / Multi-Matrix Method Based on LC-MS/MS; EPRW Rome Type of solvent Matrix Matrix type Amount of extracted sample Acetone /water 2+1 Acetonitrile /water 2+1 Methanol /water 2+1 Water Ethyl acetate Tomato Citrus High water content High acid and high water content 1.0g 38mg 36mg 34mg 33mg 8mg 1.0g 79mg 69mg 81mg - 3mg Raisins High sugar an low water content 1.0g 370mg 148mg 333mg 302mg 4mg Avocado High oil content 1.0g 33mg 40mg 30mg 43mg 332mg National Food Agency, Sweden LAPRW 2015 Santiago de Chile
10 Even the sun has spots.
11 Limitations Distorted or split peak shapes Solvent composition solvent effect The injection solvent is stronger than the mobile phase (MP) EtOAc not diluted immediately with MP, some of the analyte molecules are diluted and migrated with the MP resulting in split peaks Early Peaks (low k) most affected (2-5 min) It is important to keep the injection volume low 2 µl is recommended to avoid the peak split. National Agency, Sweden LAPRW 2015 Santiago de Chile
12 Oxydemetonmethyl in MeOH MP: Buffert/MeOH (90/10) Oxydemetonmethyl in EtOAc National Food Agency Sweden National Food Agency, Sweden LAPRW 2015 Santiago de Chile
13 Validation in multi residue methods
14 Requirements for official laboratories 1. Implementation of Guidance document on analytical quality control and validation procedures for pesticide residues analysis in food an feed SANCO12571/ Accredited according to the ISO/IEC standard 1. Participation in EU Proficiency tests
15
16 Guidance document on analytical quality control and validation procedures for pesticide residues analysis in food an feed SANCO12571/2013 Why do we need the guidelines? To reach a complete harmonization of quality assurance measures for pesticide residue analysis within Europe To help monitoring laboratories achieve an acceptable standard The reported results are reliable and consistent with other similar results
17 The key objectives of the guidelines To harmonize cost effective AQC in the EU (to find an optimum between cost and output (efficiency/quality) To ensure false positives or false negatives are not reported To support compliance with ISO/IEC accreditation standard
18 Guidance in The whole analytical chain (from sampling to reporting results) To define minimum criteria for validation and analysis (allows free choice of method)
19 Table of contents Accreditation Sampling, transport, processing and storage of samples Pesticide standards, calibration solutions, etc. Extraction and concentration Contamination and interference Analytical calibration, representative analytes Analytical methods and analytical performance Method validation Routine recovery determination Proficiency testing and analysis of reference materials Confirmation of results Reporting of results
20 Example of representative commodities fruit vegetables Commodity Categories Commodities included in this category Typical representative commodities 1.High water content 2.High acid content and high water content Pome fruit Stone fruit Citrus fruit Apples, pears Apricots, carrots Lemon, mandarin, orange 3.High sugar and low water content 4a. High oil content and very low water content 4b. High oil content and intermediate water content Honey, dried fruit Tree nuts Honey, raisins, dried apricots, dried plums, fruit jams Walnuts, hazelnuts, chestnuts Oily fruits and products Olives, avocados and pastes thereof
21 Example of validation according to the SANCO 12571/2013 Full validation in three different commodity groups high water and high acid content, e.g. orange high water content, e.g. cucumber or carrot high sugar and low water content, e.g. raisins Recovery study: 5 spiked samples at target LOQ (0,01 mg/kg) 5 spiked samples at 2-10 * target LOQ (0,05 mg/kg)
22 Table 1. Validation parameters criteria. Parameter What/how Criterion Linearity Through calibration curve Residuals < ±20% Matrix effect LOQ Specificity Comparison of response from solvent standards and matrixmatched standards By definition: lowest level for which it has been demonstrated that criteria for trueness and precision have been met Response in reagent blank and control samples 20% small effect MRL < 30% of LOQ Precision (RSD r ) Determine repeatability RSD r, determine for both spike levels Precision* (RSD wr ) Robustness Trueness (bias) Determine within-laboratory reproducibility* Can be derived from on-going method validation / verification through establishing average recovery and RSD wr? Determine the average recovery for spike levels 20% 20% See above %
23 Validation results of fruit and vegetables GC analytes 145, LC ES+/ES- analytes 303 Matrix group Detection Spiking level (mg/kg) Mean recovery (%) Mean RSD (%) Number of results High acid content and high water content GC-MS/MS 0, , High acid content and high water content GC-MS/MS 0, , High acid content and high water content LC-MS/MS ES- 0, ,59 25 High acid content and high water content LC-MS/MS ES- 0, ,32 26 High acid content and high water content LC-MS/MS ES+ 0, , High acid content and high water content LC-MS/MS ES+ 0, , High sugar and low water content GC-MS/MS 0, , High sugar and low water content GC-MS/MS 0, , High sugar and low water content LC-MS/MS ES- 0, ,4 11 High sugar and low water content LC-MS/MS ES- 0, ,91 13 High sugar and low water content LC-MS/MS ES+ 0, , High sugar and low water content LC-MS/MS ES+ 0, , High Water Content GC-MS/MS 0, , High Water Content GC-MS/MS 0, , High Water Content LC-MS/MS ES- 0, ,13 23 High Water Content LC-MS/MS ES- 0, ,64 23 High Water Content LC-MS/MS ES+ 0, , High Water Content LC-MS/MS ES+ 0, ,34 262
24 Matrix effect (%) Matrix effects Orange, LC-MS/MS 60,0 40,0 20,0 0,0-20,0-40,0-60,0 Pesticide Only 24 of 219 pesticides have >20 % matrix effect. in samples were those are found, true matrix-matching is used. Standard in blank carrot extract. Tested at 0.05 mg/kg. Agilent 6460.
25 Matrix effect (%) Matrix effects Orange, GC-MS/MS 30,0 20,0 10,0 0,0-10,0-20,0-30,0 Pesticide Only 1 of 129 analyte has >20 % matrix effect (Tetrachloroaniline-2,3,5,6, +27 %). in samples were found, true matrix-matching is used. Standard in blank cucumber extract. Tested at 0.05 mg/kg. Thermo TSQ Quantum XLS.
26 Matrix effect (%) Matrix effects Raisins, LC-MS/MS 60,0 40,0 20,0 0,0-20,0-40,0-60,0 Pesticide Only 17 of 219 pesticides have >20 % matrix effect. in samples were those are found, matrix-matching is used for quantification. Standard in blank carrot extract. Tested at 0.05 mg/kg. Agilent 6460.
27 Matrix effect (%) Matrix effects Raisins, GC-MS/MS Pesticide 26 of 129 pesticides have a matrix effects >20 %) - in samples were those are found, matrix-matching is used. Standard in blank cucumber extract. Tested at 0.05 mg/kg. Thermo TSQ Quantum XLS.
28 SweEt in EU RL Proficiency tests:
29
30 Proficiency Test 1-4 for cereals
31 Fat content in selected food Ref. The Food Database. NFA Product *Total fat % Triglycerides % Milk 3 % Egg Liver Butter *Phospholipid. Triglycerides, stereols National Food Agency, Sweden LAPRW 2015 Santiago de Chile
32 Analysis of pesticides in products with animal products Extraction 5 g sample g PSA and 0.2 g C ml ethyl acetate Spex SamplePrep 3 min 0.5 g Na 2 SO 4 Centrifugation and filtration In 3 min. (3800 g). filtrate the crude extract with 0.20 µm PTFE filter Inject to GC-MS/MS and UPLC-MS/MS Sample conc. 0.5g/ml National Food Agency, Sweden LAPRW 2015 Santiago de Chile
33 Results EU PT AO 9 Test material: Liquid Whole Egg Pesticide Conc mg/kg Conc mg/kg Conc mg/kg NFA Eurofins Spiked Assigned Found Z score Z score Dieldrin 0, ,6 0,8 Endosulfansulfat 0, ,9 1 Endrin 0, ,9 2 gamma-hch (Lindane) 0, ,2 0,9 Trans- Heptachlorepoxid 0, nd -3,5 0,9 Diazinon 0, ,2 0,6 Parathion 0, ,5 1 Phoxim 0, ,6 0,4 Deltamethrin 0, ,6 1,1 Permethrin 0, ,4 0,8 National Food Administration. Sweden LAPRW AOAC2015 Santiago de Chile
34 Multi method for analysis of pesticides in products with high fat content Fat determination Gravimetrical determination after extraction with EtOAc:Cyhe (1+1) Extraction Amount of fresh sample that corresponds to 0.5 g of fat (2.5 g cream) 10 ml ethyl acetate + cyclohexane (1 + 1) 2.5g Na 2 SO 4 Centrifugation & Filtration 3 min. 3800g Filtrate crude extract 0.2 µm PFTE filter Clean up 5.0 ml to GPC SX-3 Ethyl acetate + cyclohexane (1 + 1) 76 analytes Evaporation To dryness with N 2 Re-dissolve in 0.5 ml ethyl acetate Inject into GC-MS/MS and LC-MS/MS Matrix conc. 0.5 g/ml LAPRW 2015 Santiago de Chile
35 Butter our challenge (slide from Heidi Pekar) GPC Fat Profile 0.5 g butter Residue (mg) Pesticide Fraction Start Pesticide Fraction End Time (min) National Food Agency, Sweden LAPRW 2015 Santiago de Chile
36 EU PT AO7 results liquid cream NFA. Sweden (GPC) Fat Content: 29% Pesticide Z-scores Bifentrin -0.2 cis-chlordane -0.6 trans-chlordane -0.2 DDE -1.0 Diazinon -0.5 Deltamethrin -0.1 Endosulfansulfate -0.5 Hexachlorbenzene -0.8 alfa-endosulfan -0.1 alfa-hch -0.6 beta-hch -0.4 Lindane -0.9 Parathion-ethyl -0.1 Boscalid -0.5 Tetraconazole -0.4 Thiachloprid -1.3 National Food Agency, Sweden Eurofins, Sweden Mandatory pesticides (GPC) Fat Content: 29% Pesticide Z-scores Bifentrin -0.8 cis-chlordane -0.4 trans-chlordane -0.6 DDE -1.6 Diazinon -1.3 Deltamethrin -0.2 Endosulfansulfate -1.0 Hexachlorbenzene -1.4 alfa-endosulfan -0.7 alfa-hch -0.9 beta-hch -0.9 Lindane -1.1 Paration-ethyl -1.0 LAPRW 2015 Santiago de Chile
37 The presented method available: NMKL Pesticide residues. Analysis in foods with ethyl acetate extraction using gas and liquid chromatography with tandem mass spectrometric determination EU RL website (fruit and vegetables only) Proposal at CEN level (animal products) LAPRW 2015 Santiago de Chile National Food Administration. Sweden National Food Agency, Sweden LAPRW 2015 Santiago de Chile
38 EU reinforced import control Case: Vine leaves Specific framework for the official feed and food controls Regulation (EC) No 882/2004 includes requirements for the official control of vegetables being imported from third countries. Article 15(5) provides a list of certain products on the basis of known or emerging risks and be subject to increased controls at points of entry into the EU. The consignments may not be placed on the market before the analysis is complete. Regulation 669/2009 implementing Regulation 882/2004 sets out rules for the increased level of official controls. National Food Agency, Sweden LAPRW 2015 Santiago de Chile
39 Sample- vine leaves Dolma is a family of stuffed vegetable dishes originating from Ottoman Empire. The most-well known type is stuffed vine leaves. A lot of kg vine leaves from Turkey was subjected to the increased control. The results originates from a 4.5 kg composite (bulk) sample containing 10 bags of wine leaves á 450 g National Food Agency, Sweden LAPRW 2015 Santiago de Chile
40 Table 1 Results in vine leaves 40 analytes Analyte Found residue MRL Analyte Found residue MRL mg/kg mg/kg Acetamiprid * Imidacloprid ,00 Azoxystrobin 2, * Indoxacarb * Bifenthrin * Iprodion 0.86 Boscalid * Kresoxim-methyl * Carbendazim 0.1 Lambda-cyhalothrin * Chlorantraniliprole ,0 Mandipropamid * Chlorpyrifos * Metalaxyl Cyflufenamid * Methoxyfenozide * Cymoxanil * Metrafenone 0.82 Cypermethrin Myclobutanil * Deltamethrin Penconazole * Difenoconazole * Propargite Dimethomorph * Proquinazid * Dithiocarbamates * Pyrimethanil 0.92 Emamectin * Quinalphos * Ethirimol * Tebuconazole * Famoxadone * Tebufenpyrad * Fenbutatin Oxide * Tetraconazole * Fluopyram * Triadimefon (sum) Hexythiazox Trifloxystrobin * LAPRW 2015 Santiago de Chile
41 Results In total 40 residues were found thereof one pesticide using the single residue method. In 26 cases the MRL was exceeded. Taking into account the 50% measurement uncertainty, 17 pesticides (analytes) fulfilled the criteria for enforcement. However, none of the detected quantities of residues exceeded the acute reference dose (ArfD). Preliminary results from further analysis of the same lot (bulk sample) carried out by EURL FV, Almeria University (ES) NVWA (NL) Fera Science Ltd (U.K.) EURL SRM; CVUA (DE) EU RL CER, DTU (DK) (pending) gave similar, consistent results (taking into account the inhomogeneity in the bulk sample) LAPRW 2015 Santiago de Chile
42 Analysis of vine leaves Pesticide Homogenate of same sample NFA / Eurofins, Sweden mg/kg EURL-FV, Spain mg/kg Other individual sample NVWA, NL mg/kg Fera Science Ltd U.K. mg/kg CVUA DE mg/kg Pesticide Homogenate of same sample NFA / Eurofins, Sweden mg/kg EURL-FV, Spain mg/kg Other individual sample NVWA, NL mg/kg Fera Science Ltd U.K. mg/kg CVUA DE mg/kg Acetamiprid 0,014 0,019 n.d. n.d 0,001 Hexythiazox 0,061 0,095 0,010 n.d 0,006 Azoxystrobin 2,0 3,24 1,32 0,35 0,83 Imidacloprid 0,063 0,065 0,060 0,019 0,060 Bifenthrin 0,052 0,045 n.d. n.d 0,024 Indoxacarb 0,065 0,092 0,010 0,059 0,12 Boscalid 1,4 1,90 0,92 1,2 5.6 Iprodion 0,86 1,12 n.d. 0,22 0,015 Carbendazim 0,10 0,14 0,040 0,025 0,014 Kresoxim-methyl 0,15 0,25 0,13 0,15 0,41 Chlorantraniliprole 0,019 0,045 0,015 0,010 n.d Mandipropamid 0,005 0,018 n.d. n.d <0,001 Chlorpyrifos-ethyl 0,30 0,41 0,25 1,30 0,63 Metalaxyl 0,017 0,024 0,017 0,027 0,023 Cyflufenamid 0,019 0,022 0,040 0,007 0,014 Methoxyfenozie 0,50 0,832 0,44 0,33 0,46 Cyhalothrin-lambda 0,046 0,059 0,005 n.d 0,021 Metrafenone 0,82 n.a 1,13 0,5 2,2 Cymoxanil 0,013 0,014 n.d. n.d n.d Myclobutanil 0,03 0,046 0,018 n.d 0,015 Cypermethrin I-IV 0,016 n.d 0,012 n.d 0,013 Penconazole 0,08 0,11 0,10 0,04 0,084 Deltamethrin 0,035 0,03 <0,001 n.d 0,013 Propragite 0,016 0,041 n.d. n.d. 0,007 Difenoconazole I + II 0,036 0,072 0,033 0,008 0,002 Proquinazid 0,011 n.a 0,045 0,009 0,020 Dimetomorf 0,13 0,19 n.d n.d 0,008 Pyrimethanil ,72 0,72 0,88 1,00 DITHIOCARBAMATES 10,4 n.a n.a 11 Quinalphos 0,013 0,008 n.d. n.d n.d Emamectin 0,014 0,03 n.d. n.d 0,006 Tebuconazole 0,42 0,446 0,46 0,26 0,54 Ethirimol 0,018 0,009 0,009 0,022 0,009 Tebufenpyrad 0,066 0,088 0,073 0,005 0,061 Famoxadone 0,037 n.a n.d. n.d n.d Tetraconazole ,076 n.d. 0,072 0,026 Fenbutatin-oxide 10,9 11,5 n.a Triadimenol 0,15 0,11 0,12 0,56 0,172 LAPRW 2015 Santiago de Chile Fluopyram 0,084 0,14 0,18 0,02 n.d Trfloxystrobin 0,082 0,18 n.d. n.d 0,003
43
44 No Additional pesticides EURL-FV, Spain NVWA, Netherlands Fera Science Ltd U.K. CVUA Stuttgart mg/kg mg/kg mg/kg mg/kg 1 Cyprodinil 0,011 0,004 <0,005 0,006 2 Dicofol degr. (Chlorobenzilate) <0,001 3 Dicofol degr. (Dichlorobenzophenone-4,4) 0, Flusilazole 0,088 0,11 0,26 5 Folpet degr. (Phthalimide) 0,008 6 Procymidone 0,008 0,002 7 Pyraclostrobin 0,046 <0,005 8 Sulfur (S8) Spirodiclofen 0,014 0,031 0, Cyfluneamid 0, Flufenoxuron 0,041 0, Methyldinocap 0, Spirotetramat 0,034 0, Daminozide detected 15 Diniconazole 0,0058 0, Fenpropimorph < Fenzox detected 18 Fludioxnil < , Foramsulfuron detected 20 Forchlorfenuron detected 0,10 21 Imidacloprid-olefin detected 22 Iprodione 0,22 23 Mebendazole detected 24 Ofurace LAPRW 2015 Santiago de Chile <0,005
45 No Additional pesticides EURL-FV, Spain NVWA, Netherlands Fera Science Ltd U.K. CVUA Stuttgart mg/kg mg/kg mg/kg mg/kg 25 Cabaryl 0, Diflubenzuron 0, Dodine 0, Etofenprox 0, Fenarimol 0, Imazalil 0, Spinetoram 0, Tebufenozid 0,008 LAPRW 2015 Santiago de Chile
46 Results in vine leaves (subsequent sampling) 26 analytes Analyte Found residue MRL Analyte Found residue MRL mg/kg mg/kg Acetamiprid * Imidacloprid Azoxystrobin * Indoxacarb * Boscalid * Iprodion * Carbaryl * Kresoxim-methyl * Carbendazim * Lambda-cyhalothrin * Chlorantraniliprole Methoxyfenozide * Chlorpyrifos * Metrafenone * Cymoxanil * Myclobutanil * Difenoconazole * Penconazole * Dimethomorph * Pyraclostrobin * Emamectin * Pyrimethanil * Esfenvalerate (sum) * Tebuconazole * Ethirimol * Tetraconazole * Famoxadone * Triadimefon (sum) Fenbutatin Oxide * Prokvinazid * Fluopyram * National Food Agency, Sweden LAPRW 2015 Santiago de Chile
47 Results in vine leaves (subsequent sampling) Analyte Found residue MRL Analyte Found residue MRL mg/kg mg/kg Acetamiprid * Imidacloprid Azoxystrobin * Indoxacarb * Boscalid * Iprodion * Carbaryl * Kresoxim-methyl * Carbendazim * Lambda-cyhalothrin * Chlorantraniliprole Methoxyfenozide * Chlorpyrifos * Metrafenone * Cymoxanil * Myclobutanil * Difenoconazole * Penconazole * Dimethomorph * Pyraclostrobin * Emamectin * Pyrimethanil * Esfenvalerate (sum) * Tebuconazole * Ethirimol * Tetraconazole * Famoxadone * Triadimefon (sum) Fenbutatin Oxide * Prokvinazid * Fluopyram * National Food Agency, Sweden LAPRW 2015 Santiago de Chile
48 National Food Agency, Sweden LAPRW 2015 Santiago de Chile
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50 WS Tbilisi Georgien
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