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Lc Qqq Marine Biotoxins LC QQQ MARINE BIOTOXINS Dr. Jerry Zweigenbaum Agilent Technologies Agilent Americas Food Group Breaking News...... Recently, legislation in the EU introduced liquid chromatography coupled to tandem mass spectrometry (LC-MS-MS) as the soon to be, reference method for the detection of lipophilic marine biotoxins in live bivalve molluscs, tunicates and echinoderms. Annex 1, SCoFCAH, 18-11-2010, SANCO/6831/2009 rev 7 amending EU Regulation 2074/2005. This change in legislation allows for significant developments in the area of mass spectrometric detection for phycotoxins. Marine Biotoxins: Why analyse for them? Marine biotoxin related illness can range from headaches, vomiting and diarrhoea to neurological problems, and in extreme cases can lead to death. Is it really an issue? Agilent FC 24 Website RASFF Alert notifications are sent when a food or feed presenting a serious health risk is on the market and when rapid action is required. The RASFF member that identifies the problem and takes the relevant actions (e.g. withdrawal of the product) triggers the alert and allows other countries to search there own outlets. Responsibilities for Producers of shell fish They must ensure their product must not contain marine biotoxins in quantities that exceed.... •800 micrograms per kilogram for paralytic shellfish poison (PSP), • 20 milligrams of domoic acid per kilogram for amnesic shellfish poison (ASP) •160 micrograms of okadaic acid equivalents per kilogram for okadaic acid, dinophysistoxins and pectenotoxins in combination, •1 milligram of yessotoxin equivalents per kilogram for yessotoxins, •160 micrograms of azaspiracid equivalents per kilogram for azaspiracids. The picture beforeSite Closuresharvesting 2005 – Ireland (locality) Assessment of Irish beds in 2005 Yellow: ASP Red: DSP Blue: AZP Green: DSP+AZP Courtesy of Dr. Philipp Hess, Ifremer Examples of shell fish poisoning incidents Examples of shellfish poisoning incidents. Note that no new toxin groups have been reported since the discovery of azaspiracids in 1995 (Hess et al., 2008). Large-scale poisoning events for okadaic acid group toxins have still occurred during the last decade despite the toxic algae and toxins involved being known for over 20 years. NO. OF SHELLFISH LOCATION POISONING REFERENCE CASES SPECIES OF ILLNESS MUSSELS AND DSP 164 JAPAN YASUMOTO ET AL., 1978 SCALLOPS BLUE MUSSELS (M. DSP > 300 NORWAY, SWEDEN UNDERDAHL ET AL., 1985 EDULIS) BLUE MUSSELS (M. ASP 107 CANADA PERL ET AL., 1990 EDULIS) CLAMS (A. PSP 187 GUATEMALA RODRIQUE ET AL., 1990 KINDERMANII) EASTERN OYSTER NSP 48 UNITED STATES MORRIS ET AL., 1991 (C. VIRGINICA) BLUE MUSSELS (M. AZP 24 IRELAND MCMAHON AND SILKE, 1998 EDULIS) BLUE MUSSELS (M. DSP > 300 BELGIUM DE SCHRIJVER ET AL., 2002 EDULIS) BROWN CRAB (C. DSP 200 NORWAY AUNE ET AL., 2006 PAGURUS) BLUE MUSSELS (M. DSP 159 UNITED KINGDOM UK COT, 2006 EDULIS) Provided courtesy of Dr. Philipp Hess, Ifremer During the last 2 years •EFSA publish scientific opinion that bioassay has shortcomings and is not considered an appropriate tool for control of some toxins in Shellfish because of the high variability in results, the insufficient detection capability and the limited specificity.....A key, dirty dozen is the key focus. •Ring trials take place across Europe. As a result an LCMSMS approach becomes effectively validated by the Union Reference Laboratory for marine biotoxins and is declared to be an approach which maintains and ensures a full protection of consumer health without the shortcomings of the biological test, such as the high variability in results, the insufficient detection capability and the limited specificity. •In November Member States endorsed the relevant European Commission proposal during meeting of the Standing Committee of the Food Chain and Animal Health (SCoFCAH). In Annex III to Regulation (EC) No 2074/2005, Chapter III to be replaced by .... LIPOPHILIC TOXIN DETECTION METHODS: Chemical methodology The EU-RL LC-MS/MS method shall be the reference method for the detection of marine toxins as referred to in Chapter V(2)(c), (d) and (e) of Section VII of Annex III, to Regulation (EC) No 853/2004. This method shall determine at least the following compounds: - okadaic acid group toxins : OA, DTX1, DTX2, including their esters - pectenotoxins group toxins : PTX1 and PTX2, - yessotoxins gp toxins: YTX, 45 OH YTX, homo YTX, and 45 OH homo YTX, -azaspiracids group toxins: AZA1, AZA2 and AZA3. Total toxicity equivalence shall be calculated using toxicity equivalent factors (TEFs) as recommended by EFSA. If new analogues of public health significance are discovered, they should be included in the analysis. Total toxicity equivalence shall be calculated using toxicity equivalent factors (TEFs) as recommended by EFSA. In Annex III to Regulation (EC) No 2074/2005, Chapter III to be replaced by .... LIPOPHILIC TOXIN DETECTION METHODS: Biological methods A series of mouse bioassay procedures, may be still used until 31 December 2014 for detecting marine toxins. After that period, the mouse bioassay shall be used only during the periodic monitoring of production areas and relaying areas for detecting new or unknown marine toxins on the basis of the national control programmes elaborated by the Member States. Dirty Dozen lipophilic toxins: Compound Compound Toxicity Compound Compound Toxicity class factor class factor OA DSP 1 PTX1 DSP 1 DTX1 DSP 1 PTX2 DSP 1 DTX2 DSP 0.6 YTX DSP 1 AZA1 AZP 1 homo-YTX DSP 1 AZA2 AZP 1.8 OH-YTX DSP 1 AZA3 AZP 1.4 OH-homo-YTX DSP 0.5 Determination of lipophilic marine biotoxins in shellfish using Triple Quadrupole LC/MS/MS Experimental Work and Data provided by: Oliver Keuth Chemical and Veterinary Analytical Institute Münsterland-Emscher-Lippe, Münster, Germany Dr. Begoña Ben Gigirey, Prof. Ana Gago-Martinez European Union Reference Labatory for Marine Biotoxins (EU-RL-MB) and Dept. Analytical and Food Chemistry, Faculty of Chemistry, University of Vigo Review of lipophilic marine biotoxin analysis: • There are 2 LC-MS/MS methods proposed for the analysis of lipophilic marine biotoxins and both methods are currently evaluated in ring trials: • Acidic method (based on McNabb et al., 2005) – Reverse phase conditions – Acidic mobile phases – Electrospray ionization with polarity switching – Multiple reaction monitoring • Alkaline method (based on Gerssen et al., 2009) – Reverse phase conditions – Basic mobile phases (pH 11) – Electrospray ionization with negative and positive time segment – Multiple reaction monitoring Influence of pH value of mobile phase: DTX-1: O O CH3 CH CH 3 O 3 CH3 O O O H H O + H H HO +H O HO O H H O O H H O H C - 3 OH H3C O H3C OH O H3C HO OH O H HO H CH2 H C O CH O 3 H 2 H3C OH H OH Gerssen et al., J. Chromatogr. A, 1216 (2009) 1421-1430 Reaction Monitoring Quad Mass Filter (Q1) Quad Mass Filter (Q3) Collision Cell Spectrum with Q1 lets only Collision cell Q3 monitors only background target ion 210 breaks ion 210 characteristic ions (from ESI) pass through apart fragments 158 210 210 from ion 210 for 222 quant 158 268 280 158 165 191 210 170 210 250 290 190 210 150 170 190 210 160 Chromatogram High background Low background Ionization of lipophilic toxins in electrospray AZA1 Compound class Formula ESI mode Precursor ion Okadaic acid group - OA C44H68O13 negative [M-H] = 803.5 positive [M+Na]+ = 827.5 - DTX1 C45H70O13 negative [M-H] = 817.6 positive [M+Na]+ = 841.5 - DTX2 C44H68O13 negative [M-H] = 803.5 positive [M+Na]+ = 827.5 Azaspiracids + PTX2 AZA1 C47H71NO12 positive [M+H] = 842.6 + AZA2 C48H73NO12 positive [M+H] = 856.5 + AZA3 C46H69NO12 positive [M+H] = 828.5 Pectenotoxins + PTX1 C47H70O15 positive [M+NH4] = 892.5 positive [M+Na]+ = 897.5 + PTX2 C47H70O14 positive [M+NH4] = 876.6 positive [M+Na]+ = 881.5 Yessotoxin group - YTX YTX C55H82O21S2 negative [M-H] = 1141.5 negative [M-2H]2- = 570.3 - homo-YTX C56H84O21S2 negative [M-H] = 1155.4 negative [M-2H]2- = 577.4 - OH-YTX C55H82O22S2 negative [M-H] = 1157.4 negative [M-2H]2- = 578.4 - OH-homo-YTX C56H84O22S2 negative [M-H] = 1171.4 negative [M-2H]2- = 585.4 Collisionally induced dissociation of OA positive CE 45 V negative CE 60 V Application Number 1: Acidic Method Single polarity Methodology – Sample preparation: 2 g cooked and grinded mussel tissue Extraction with aqueous solvent (80 % methanol) Shaking or blending mixture and centrifugation Repeat extraction, supernatants decanted into volumetric flask, filled up to 50 ml Filter extract, using 0.45 µm membrane filter Inject 10 µl LC-MS/MS Methodology – HPLC conditions: Column: C-18, 150 x 2 mm, 5 µm (positive mode) Agilent ZORBAX Eclipse Plus C-8, 75 x 4.6 mm, 3.5 µm (negative mode) Flow rate: 0.2 mL/min Column temp: 30°C Injection volume: 10 μL (needle wash in flushport 5 seconds) Solvent Channel A: 0.1% formic acid (positive mode) 2 mM ammonium acetate (negative mode) Solvent Channel B: methanol Gradient: Time (min) A (%) B (%) 0.0 90 10 10.0 10 90 22.0 10 90 23.0 90 10 30.0 90 10 Overall Cycle Time: 30.0 min Methodology – Agilent Jet Stream conditions: Drying gas temp: 300°C Gas flow rate: 5 L/min LC flow Super-heated N2 Nebulizer pressure: 45 psi sheath gas Nebulizer N2 gas (near sonic Sheath gas temp: 250°C velocity) Sheath gas flow: 11 L/min Nozzle Voltage: +/- 500 V Thermal focusing delta EMV: 400 V Electrospray Capillary voltage: +/- 3500 V Methodology – MRM transition parameters: Analyte Polarity Prec Ion Prod Ion Frag CE Quantifier m/z m/z [V] [eV] OA and DTX2 pos 827.5 723.4 220 55 X pos 827.5 809.2 220 45 DTX1 pos 841.5 737.2 220 55 X pos 841.5 823.2 220
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