State-of-the-Art Liquid Chromatography- Tandem Mass Spectrometry Detection Methods for Shellfish Toxins (ASP, DSP, PSP)

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1 State-of-the-Art Liquid Chromatography- Tandem Mass Spectrometry Detection Methods for Shellfish Toxins (ASP, DSP, PSP)

2 utline 1. Introduction 2. Toxins 3. Mass spectrometry - functional principle - ionization - mass analyzers - quadrupoles - triple quad scan modes 4. Algal toxin - spirolides MS/MS methods - yessotoxins - PSTs - multi toxin method 5. Conclusions

3 1. Introduction

4 1. Introduction Global Distribution of Paralytic Shellfish Poisoning Events

5 2. Toxins Toxins Diatoms Amnesic Shellfish Poisoning 8' 7 C 6 1' 8 C N 5 6' 5' 7' C Domoic acid Pseudo-Nitzschia pungens

6 2. Toxins Toxins Dinoflagellates Paralytic Shellfish Poisoning 2 N Diarrhetic Shellfish Poisoning N N N 2 A 10 B 1 13 C I N 37 G 28 Azaspiracid-1 32 F D E Me 2 3 Lingulodinium polyedrum 31 N 2 N N N Saxitoxin Neurotoxic Shellfish Poisoning Me - 3S - 3S Yessotoxin Me Me Me Me desmethyl spirolide C kadaic acid S3Na Brevetoxin Na 3S Maitotoxin

7 3. Mass spectrometry Functional Principle Mass spectrometry is the determination of mass to charge (m/z) ratio of any compound Process Instrumentation 1. Ionization Ion source 2. Acceleration Interface 3. Mass separation Mass analyzer 4. Ion detection Electron multiplier

8 3. Mass spectrometry Ionization Electrospray ion source

9 3. Mass spectrometry Mass Analyzers 2 categories: scanning and non-scanning analyzers Sector field Quadrupole Ion trap time-of-flight (TF) Fourier-transform ion cyclotron resonance (FT-ICR) Acurate quantitation Exact mass measurement Structural information cost

10 3. Mass spectrometry Quadrupole Quadrupoles m/z=100 m/z=10 m/z=1000 The magnetic frequencies of the quadrupole rods are modulated that way, that only a certain m/z value hits the detector at a time Advantage: robustness reproducible mass spectra linear response over several orders of magnitude

11 3. Mass spectrometry Triple Quad Scan Modes Product ion scan Q1 Q2 Q3 mass filter collision cell scan

12 3. Mass spectrometry 7,0 e 8 6,5 e 8 6,0 e 8 5,5 e 8 5,0 e 8 4,5 e 8 4,0 e 8 Triple Quad Scan Modes 1 1, min Sample A: Product ion scan chromatogram of m/z 650 3,5 e 8 3,0 e 8 2,5 e 8 2,0 e 8 1,5 e 8 1,0 e 8 5,0 e 7 0,0 2,8e7 1 2, T im e, m in 402,2 2,6e7 2,4e7 2,2e7 2,0e7 1,8e7 164,1 Product ion spectrum of min 632,4 1,6e7 1,4e7 1,2e7 384,2 614,3 1,0e7 8,0e6 6,0e6 4,0e6 17 7,1 206,2 366,3 2,0e6 220,2 302,2 147,1 356,2 59 6,3 119,0 157,1 18 7,1 24 8,2 258,2 412,3 43 0,3 480,3 51 6,3 570,4 65 0,4 208,2 298,2 37 2,2 304,3 53 4,2 586, m/z, amu

13 3. Mass spectrometry Triple Quad Scan Modes Multiple Reaction Monitoring (MRM) Q1 Q2 Q3 mass filter collision cell mass filter

14 3. Mass spectrometry 1,4 e 6 1,3 e 6 1,2 e 6 1,1 e 6 1,0 e 6 9,0 e 5 8,0 e 5 7,0 e 5 6,0 e 5 Triple Quad Scan Modes min 1 1, 5 3 Sample A: MRM chromatogram of the transition m/z 650 > 164 5,0 e 5 4,0 e 5 3,0 e 5 2,0 e 5 1,0 e 5 0,0 1 2, T i m e, m in 1,4 e 6 1,3 e 6 1,2 e 6 1,1 e 6 1,0 e 6 9,0 e 5 8,0 e 5 MRM spectrum of min 7,0 e 5 6,0 e 5 5,0 e 5 4,0 e 5 3,0 e 5 2,0 e 5 1,0 e 5 0, ,5 /1 6 4, ,5/164,1 Q 1 /Q 3 M asses, am u

15 4. Algal toxin MS/MS methods Example: Spirolides Alexandrium ostenfeldii Polarity: positive N desmethyl spirolide C

16 4. Algal toxin MS/MS methods Example: Spirolides Fragmentation pattern of 13-desmethyl spirolide C Sleno et al. (2004) Anal Bioanal Chem 378 :

17 4. Algal toxin MS/MS methods Example: Spirolides spirolide C Chromatography Luna C18 150x3 mm, 3 µm, 100 Å A: 2mM N 4 C, 50 mm C B: 2mM N 4 C, 50 mm C in 95% ACN Linear Gradient: 22%B 65%B (0-50 min) Flow rate: 200 µl/min Temperature: 35 C?? 20-Me spirolide G? API 4000 QTrap, positive, MRM CUR: 20 CAD: igh IS: 5500 TEM: 650 GS1: 40 GS2: 70 ihe: N DP: 121 EP: 10 CE: 57 CXP: 22?????

18 4. Algal toxin MS/MS methods Example: Yessotoxins Me Lingulodinium polyedrum Protoceratium reticulatum Me Polarity: negative Gonyaulax spinifera - 3 S - 3 S Me Me Me yessotoxin Me Gonyaulax spinifera Lingulodinium polyedrum Protoceratium reticulatum

19 4. Algal toxin MS/MS methods Example: Yessotoxins The most abundant fragment of all YTXs is the loss of S 3 from the sulfate groups Miles et al. (2005) armful Algae 4 :

20 4. Algal toxin MS/MS methods Example: Yessotoxins 2,8e5 2,6e5 2,4e5 2,2e5 2,0e5 1,8e5 LC-MS/MS MRM Chromatogram of a Protoceratium reticulatum isolate from the Benguela Current, South Africa 7, > > > > > ,6e5 1,4e5 1,2e5 1,0e5 8,0e4 6,0e4 4,0e4 2,0e4 0,0 5,0 5,5 6,0 6,5 7,0 7,5 8,0 8,5 9,0 9,5 10,0 Time, min

21 4. Algal toxin MS/MS methods 2 N 2 N N N N N Alexandrium andersonii catenella fundyense minutum peruvianum tamarense tamiyavanichii Pyrodinium bahamense Gymnodinium catenatum N 2 Anabaena Alexandrium tamarense circinalis lemmermannii Aphanizomenon flos-aquae Cylindrospermopsis raciborskii Lyngbya wollei Microcystis Microcystis aeruginosa aeruginosa Pyrodinium bahamense Alexandrium catenella Example: PSP

22 4. Algal toxin MS/MS methods Example: PSP Toxin R1 R2 R3 R4 MW Ions formed STX C-N [M- + ] + = 300 NE (Carbamoyl-) 317 [M- + ] + = 316 GTX1 S M + = 412 GTX2 S M + = 396 GTX3 S M + = 396 GTX4 S M + = 412 B1= GTX5 C-N-S M + = 380 B2= GTX6 (N-Sulfocarbamoyl-) 396 M + = 396 C3 S [M-S - 3 ] + = 412 C1 S [M-S - 3 ] + = 396 C2 S [M-S - 3 ] + = 396 C4 S [M-S - 3 ] + = 412 dc-stx 258 [M- + ] + = 257 dc-ne (Decarbamoyl-) 274 [M- + ] + = 273 dc-gtx1 S M + = 369 dc-gtx2 S M + = 353 dc-gtx3 S M + = 353 dc-gtx4 S M + = 369

23 4. Algal toxin MS/MS methods Example: PSP ILIC-LC-MS/MS MRM Chromatogram of Paralytic Shellfish Toxins

24 4. Algal toxin MS/MS methods Multi Method Definition: Prerequisites: Problems: Limitations: Summary: Multi methods aim to analyze toxins of as many as possible different classes extractability under same conditions elution with same solvent system each compound class requires individual MS parameters: (curtain gas, ion source temperature, ionization voltage, auxiliary gas flows, ion polarity, quadrupol voltages, fragmentation energy) limited amount single compounds group elution of every toxin class required Multimethods are a compromise between a number of toxins to be analyzed and sensivity

25 4. Algal toxin MS/MS methods Multi Method 1. ASP 2. Gymnodimine 3. Spirolides I A N B 13 C G 28 D 26 E 21? 4. Azaspiracids 32 F Protoperidinium crassipes 5. Dinophysistoxins 6. Pectenotoxins 7. Yessotoxins F A 7 B C E 14 D Prorocentrum lima Dinophysis acuminata

26 4. Algal toxin MS/MS methods Multi Method 1,7e4 1,6e4 1,5e4 1,4e4 LC-MS/MS MRM multi period chromatogram of a field sample from Alfacs Bay, Catalonia, Spain 7,36 Period 2: cyclic imino toxins (spirolides, gymnodimine) 1,3e4 1,2e4 9,61 1,1e4 1,0e4 9000,0 8000,0 7000,0 Period 1: Domoic acid (ASP) Period 3: Polyether toxins (DTX, PTX, YTX, AZP) 6000,0 8, ,0 4000,0 3000,0 8,15 8, ,0 1000,0 0,84 0,71 7,07 9,02 11,71 12,25 0, Time, min

27 1, 7 e 4 1, 6 e 4 1, 5 e 4 1, 4 e 4 1, 3 e 4 1, 2 e 4 1, 1 e 4 1, 0 e , , , , , , , , , 0 0, 0 0, 7 1 0, 8 4 7, 0 7 7, 3 6 8, T i m e, m i n 8, 3 3 8, 5 0 9, 0 2 9, , , Algal toxin MS/MS methods Multi Method LC-MS/MS MRM multi period chromatogram of a field sample from Alfacs Bay, Catalonia, Spain 1, 1 5 e 4 1, 1 0 e 4 1, 0 5 e 4 1, 0 0 e , , , , , , , , , , , , , , , , , , , min 9, 6 1 Period 2: cyclic imino toxins (spirolides, gymnodimine) 0, 0 0 8, 8 8, 9 9, 0 9, 1 9, 2 9, 3 9, 4 9, 5 9, 6 9, 7 9, 8 9, 9 1 0, 0 1 0, 1 1 0, 2 1 0, 3 1 0, 4 1 0, 5 1 0, 6 1 0, 7 1 0, 8 1 0, 9 1 1, 0 1 1, 1 T i m e, m i n 5000,00 gymnodimine 4500, ,00 spectrum of 9.61 min 3500, , , , ,00 13-desmethyl spirolide C 13-desmethyl spirolide D 1000,00 500,00 0,00 Spirolide A Spirolide B Spirolide C Spirolide D 508,3 /4 90,1 692,6/164,1 692,6/150,1 694,6/164,1 6 94,6/15 0,1 7 06,6/16 4,1 70 8,6/164,1 Q1 /Q 3 M asses, am u

28 1, 7 e 4 1, 6 e 4 1, 5 e 4 1, 4 e 4 1, 3 e 4 1, 2 e 4 1, 1 e 4 1, 0 e , , , , , , , , , 0 0, 0 0, 7 1 0, 8 4 7, 0 7 7, 3 6 8, T i m e, m i n 8, 3 3 8, 5 0 9, 0 2 9, , , Algal toxin MS/MS methods Multi Method LC-MS/MS MRM multi period chromatogram of a field sample from Alfacs Bay, Catalonia, Spain , min 1 1, , 2 5 Period 3: polyether toxins (DTX, PTX, YTX, AZP) , , , , , , , , 4 1 1, 6 1 1, 8 1 2, 0 1 2, 2 1 2, 4 1 2, 6 1 2, 8 1 3, 0 1 3, 2 1 3, 4 1 3, 6 1 3, 8 1 4, 0 1 4, 2 1 4, 4 1 4, 6 1 4, 8 1 5, 0 1 5, 2 1 5, 4 1 5, 6 1 5, 8 T i m e, m i n okadaic acid Spectrum of min okadaic acid C8 diol ester pectenotoxin-12 pectenotoxin dinophysistoxin-1 pectenotoxin-2 pectenotoxin-2 seco acid azaspiracid , 6 / 2 2 3, , 6 / 2 3 7, , 6 / 2 2 3, , 6 / 2 1 3, , 6 / 2 1 3, , 6 / 2 1 3, , 6 / 2 1 3, , 6 / 8 2 4, , 6 / 9 6 5, 6 Q 1 / Q 3 M a s s e s, a m u

29 1, 7 e 4 1, 6 e 4 1, 5 e 4 1, 4 e 4 1, 3 e 4 1, 2 e 4 1, 1 e 4 1, 0 e , , , , , , , , , 0 0, 0 0, 7 1 0, 8 4 7, 0 7 7, 3 6 8, T i m e, m i n 8, 3 3 8, 5 0 9, 0 2 9, , , Algal toxin MS/MS methods Multi Method LC-MS/MS MRM multi period chromatogram of a field sample from Alfacs Bay, Catalonia, Spain min 1 2, , , 7 7 Period 3: polyether toxins (DTX, PTX, YTX, AZP) , , , , , , , , 4 1 1, 6 1 1, 8 1 2, 0 1 2, 2 1 2, 4 1 2, 6 1 2, 8 1 3, 0 1 3, 2 1 3, 4 1 3, 6 1 3, 8 1 4, 0 1 4, 2 1 4, 4 1 4, 6 1 4, 8 1 5, 0 1 5, 2 1 5, 4 1 5, 6 1 5, 8 T i m e, m i n Spectrum of min pectenotoxin dinophysistoxin-1 pectenotoxin-12 pectenotoxin-11 yessotoxin okadaic acid okadaic acid C8 diol ester pectenotoxin-2 seco acid azaspiracid ,6/223,1 836,6/237,1 946,6/223,1 876,6 /213,1 87 4,6/213,1 89 4,6/213,1 89 2,6/213,1 84 2,6/824, ,6/96 5,6

30 5. Conclusions 1. The mass analyzer of choice for quantitation of algal toxins by LC-MS is the quadrupole (or better: triple quad) 2. Ionization of algal toxins is best achieved by electrospray ionization (ESI) with acidic and basic modifiers (formic acid and ammonium formate, respectively) in the mobile phase 3. Most toxin classes can be identified by characteristic group fragments of the individual components 4. ydrophilic Interaction (ILIC) stationary phases for the first time allow to analyze very polar PSTs by LC-MS 5. Multi methods are a good tool for screening a defined amount of different toxins, but do not give an overall toxin response

31 Thanks to Wolfgang Drebing, AWI and for your attention!

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