Qualitative and Quantitative Analysis of Cyanobacterial Toxins by LC-MS/MS. Workshop MS, Qualitative & Quantitative Analytik, Uni Hamburg
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1 Qualitative and Quantitative Analysis of Cyanobacterial Toxins by LCMS/MS Workshop MS, Qualitative & Quantitative Analytik, Uni amburg
2 utline 1. Relevance of cyanotoxins in food chemistry 2. What are cyanotoxins? Chemical classes 3. Qualitative detection of cyanotoxins by LCMS/MS 4. Quantitative analysis 5. Summary Workshop MS, Qualitative & Quantitative Analytik, Uni amburg
3 1. Relevance of cyanotoxins in food chemistry Relevance of cyanotoxins in food chemistry 1. potable water 2. dietary supplements algal preparations Workshop MS, Qualitative & Quantitative Analytik, Uni amburg
4 2. What are cyanotoxins? Chemical classes Cyanotoxins Classes Toxin class mode of action PSTs (paralytic shellfish toxins) Anatoxins Anatoxina(s) Cylindrospermopsins Microcystins odularins sodium channel inhibitors nicotinic acetylcholin receptor agonists acetylcholin esterase inhibitor inhibition of uridine monophosphate synthase complex hepatotoxins block of protein serine/threonine phosphatases PP1 and PP2A block of protein serine/threonine phosphatases PP1 and PP2A Workshop MS, Qualitative & Quantitative Analytik, Uni amburg
5 2. What are cyanotoxins? Chemical classes Paralytic Shellfish Toxins (PSTs) 2 2 Saxitoxin 2 Anabaena circinalis lemmermannii Aphanizomenon flosaquae Cylindrospermopsis raciborskii Lyngbya wollei Microcystis aeruginosa Aphanizomenon flosaquae Microcystis aeruginosa Anabaena circinalis Workshop MS, Qualitative & Quantitative Analytik, Uni amburg
6 2. What are cyanotoxins? Chemical classes Paralytic Shellfish Toxins (PSTs) Toxin R1 R2 R3 R4 R 4 R 1 STX E GTX1 S 3 GTX2 S 3 GTX3 S 3 C 2 (Carbamoyl) 2 GTX4 S 3 2 B1= GTX5 B2= GTX6 C3 S 3 C1 S 3 C2 S 3 CS 3 (Sulfocarbamoyl) C4 S 3 R 2 R 3 dcstx dce (Decarbamoyl) dcgtx1 S 3 STX = Saxitoxin E = eosaxitoxin GTX = Gonyautoxin dcgtx2 S 3 dcgtx3 S 3 dcgtx4 S 3 Workshop MS, Qualitative & Quantitative Analytik, Uni amburg
7 2. What are cyanotoxins? Chemical classes Anatoxina Anatoxina Anabaena circinalis Anabaena circinalis flosaquae Aphanizomenon flosaquae Planktothrix formosa Aphanizomenon flosaquae omoanatoxina Anabaena flosaquae Workshop MS, Qualitative & Quantitative Analytik, Uni amburg
8 2. What are cyanotoxins? Chemical classes Anatoxina(s) P Anabaena flosaquae lemmermannii Anatoxina(s) Anabaena flosaquae Anabaena lemmermannii Workshop MS, Qualitative & Quantitative Analytik, Uni amburg
9 2. What are cyanotoxins? Chemical classes Cylindrospermopsins 3 S Cylindrospermopsin 3 S Aphanizomenon flosaquae ovalisporum Cylindrospermopsis raciborskii Umezakia natans 7epiCylindrospermopsin 3 S Umezakia natans deoxycylindrospermopsin Cylindrospermopis raciborskii Workshop MS, Qualitative & Quantitative Analytik, Uni amburg
10 2. What are cyanotoxins? Chemical classes Microcystins (5) Adda C 3 (4) LZ (6) DGlu (iso)(7) methyldehydroala (Mdha) C R 2 C (1) DAla R 1 (2) LX (3) DerythroβmethylAsp (iso) Anabaena circinalis flosaquae Anabaenopsis milleri Aphanizomenon ovalisporum Microcystis aeruginosa botrys viridis Planktothrix agardhii mugeotii rubescens ostoc spp. Planktothrix agardhii Microcystis aeruginosa ostoc Workshop MS, Qualitative & Quantitative Analytik, Uni amburg
11 2. What are cyanotoxins? Chemical classes Microcystins (6) DGlu (iso) (7) methyldehydroala (Mdha) C (5) Adda C 3 (1) DAla (4) LZ R 2 C R 1 (2) LX (3) DerythroβmethylAsp (iso) AA 1 AA 2 AA 3 AA 4 AA 5 AA 6 AA 7 DAla LLeu DMeAsp LArg Adda DGlu Mdha DSer LAla DAsp LAib ADMAdda DMeGlu Dha LGlu LAla DMAdda C 2 3 (C 3 )Glu Dhb LGluMe LGlu (6Z)Adda LAla Lar LGluMe LMeSer Lil Lar LSer Lph Lph Mdhb Lty Lty MeLan LMet LLeu LMet() LMet LPhe LMet() LThTyr LPhe LTrp LTrp LTyr LTyr LVal Workshop MS, Qualitative & Quantitative Analytik, Uni amburg
12 2. What are cyanotoxins? Chemical classes odularins C 3 Adda DGlu (iso) Methyl C 2aminobutenic acid C odularia spumigena LArg DerythroβmethylisoAsp 2 odularia spumigena Workshop MS, Qualitative & Quantitative Analytik, Uni amburg
13 3. Qualitative detection of cyanotoxins by LCMS/MS Qualitative detection of cyanotoxins Aim: Survey method for the qualitative detection of cyanobacterial freshwater toxins Prerequisites: All toxinssolublein thesameextractionsolvent Characteristic fragment for each toxin group Toxin group (not single compound!) separation Workshop MS, Qualitative & Quantitative Analytik, Uni amburg
14 3. Qualitative detection of cyanotoxins by LCMS/MS Qualitative detection of cyanotoxins 3,6e7 3,4e7 3,2e7 3,0e7 2,8e7 2,6e7 2,4e7 2,2e7 2,0e7 1,8e7 1,6e7 1,4e7 1,2e7 1,0e7 8,0e6 6,0e6 4,0e6 2,0e6 0,0 Period 1: PSP & Anatoxina(s) 5,28 5,04 6,12 Period 2: Anatoxins & Cylindrospermopsins Period 3: odularins & Microcystins Time, min Workshop MS, Qualitative & Quantitative Analytik, Uni amburg ,47 15,09 odularia spumigena, Baltic Sea Phenomenex Luna C18 150x3 mm, 3 µm, 100 Å A: 2mM 4 C, 50 mm C B: 2mM 4 C, 50 mm C in 95% Me Gradient: initial: 100% A 1 min 50% A 5 min 50% A 15 min 10% A 20 min 10% A 21 min 100% A Flow rate: 400 µl/min Temperature: 20 C iller et al. (2007) J. Mass Spectrom. 42(9),
15 3. Qualitative detection of cyanotoxins by LCMS/MS Period 1: PSP & Anatoxina(s) R 1 2 R R 2 R 3 PSPtoxins 2 o characteristic fragment Mass transtions: / (GTX1, GTX4, C3, C4) / (GTX2/3, B2, C1, C2) / (B1) (dcgtx1/4) (dcgtx2/3) (E, GTX2/3, B2, C1, C2) (E) / (STX, B1) (dce, dcgtx2, dcgtx3) (dcstx ) / (AAS) P Anatoxina(s) nly one toxin known API 4000 QTrap, positive, MRM: IS: 5000 V CAD: high level TEM.: 550 C GS 1: 50 L h1 GS 2: 70 L h1 CUR: 25 L h1 CE: 30 ev DP: 40 ev Workshop MS, Qualitative & Quantitative Analytik, Uni amburg
16 3. Qualitative detection of cyanotoxins by LCMS/MS Period 2: Anatoxins & Cylindrospermopsins Experiment 1 Anatoxina Experiment 2 3 S Cylindrospermopsin characteristic fragment: m/z 91 + characteristic fragment: m/z API 4000 QTrap, positive precursor ion (m/z): 91.0 scan range (m/z): amu CUR: 25 CAD: igh IS: 5200 TEM: 550 GS1: 50 GS2: 70 ihe: FF DP: 80 EP: 10 CE: 30 CXP: 12 API 4000 QTrap, positive precursor ion (m/z): scan range (m/z): amu CUR: 25 CAD: igh IS: 5200 TEM: 550 GS 1: 50 GS 2: 70 CE: 50 DP: 80 Workshop MS, Qualitative & Quantitative Analytik, Uni amburg
17 3. Qualitative detection of cyanotoxins by LCMS/MS Period 3: Microcystins & odularins characteristic fragment: m/z 135 C 3 C R 1 C 3 + R 2 C experiment 1 experiment 2 experiment 3 experiment 4 scan range (m/z) protonated fragment ions [M+] + / [M+2] 2+ [M+2] 2+ [M+2] 2+ [M+] + [M+] + collision energy (ev) declustering potential (V) cyanobacterial toxins: microcystins / nodularins microcystins microcystins microcystins nodularins number of Arg residues within the microcystin peptide 1, exceptional Workshop MS, Qualitative & Quantitative Analytik, Uni amburg
18 3. Qualitative detection of cyanotoxins by LCMS/MS Microcystins precursor mode Microcystis aeruginosa MCLR dmmclr Workshop MS, Qualitative & Quantitative Analytik, Uni amburg
19 3. Qualitative detection of cyanotoxins by LCMS/MS C Microcystins product ion mode C 3 C 3 C C 2 2 C C C C 2 2 [MdhaAlaLeuMeAspArg + ] + C 3 2 C 2 Workshop MS, Qualitative & Quantitative Analytik, Uni amburg
20 4. Quantitative analysis Quantitation product ion mode Workshop MS, Qualitative & Quantitative Analytik, Uni amburg
21 5. Summary Take home messages 1. precursor ion mode is a powerful tool to detect known and unknown structural variants of cyanotoxins 2. the presented method covers all to date known limnic cyanotoxin classes 3. putative cyanotoxins have to be confirmed by independent methods (product ion spectra, immuno assays, etc.) 4. Quantitative analysis in the precursor ion mode is in good agreement with MRM for microcystins and nodularins, but understimates values for anatoxins and cylindrospermopsins Workshop MS, Qualitative & Quantitative Analytik, Uni amburg
22 Thanks to Susann iller, FriedrichSchillerUniversität Jena and for your attention! Workshop MS, Qualitative & Quantitative Analytik, Uni amburg
23 Workshop MS, Qualitative & Quantitative Analytik, Uni amburg
Detection Techniques used for Microcystin Quantification
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