WANG Yan-long, CHEN Jun-hui, LI Zhao-yong, WANG Shuai, ZHEN Xiao-ling, WANG Xiao-ru. Analysis of Typical Cyclic Imine Toxins by Atmospheric Pressure Chemical Ionization-Mass Spectrometry[J]. Journal of Chinese Mass Spectrometry Society, 2015, 36(6): 551-558. DOI: 10.7538/zpxb.youxian.2015.0028
Citation: WANG Yan-long, CHEN Jun-hui, LI Zhao-yong, WANG Shuai, ZHEN Xiao-ling, WANG Xiao-ru. Analysis of Typical Cyclic Imine Toxins by Atmospheric Pressure Chemical Ionization-Mass Spectrometry[J]. Journal of Chinese Mass Spectrometry Society, 2015, 36(6): 551-558. DOI: 10.7538/zpxb.youxian.2015.0028

Analysis of Typical Cyclic Imine Toxins by Atmospheric Pressure Chemical Ionization-Mass Spectrometry

More Information
  • The fragmentation characteristics of two typical cyclic imine toxins (GYM and SPX1) were analyzed by ion trap-atmospheric pressure chemical ionization-mass spectrometry (IT-APCI-MS). The results showed that quasi-molecular ion peak[M+H]+ (base peak) of GYM and SPX1 was detected by APCI-MS. Stability characteristic fragment ions were observed by the neutral loss of H2O from precursor ions [M+H]+ for APCI-MS2. Then, the fragmentation pathways of GYM and SPX1 were discussed based on APCI-MS3 analysis. Based on the comparison of two methods, the sensitivity of APCI-MS is better than ESI-MS for analysis of GYM and SPX1. The matrix interference resistance, specificity, repeatability and stability of the LC-APCI-MS2 method are better than LC-ESI-MS2 method for analysis of GYM and SPX1 in four different matix. In conclusion, APCI-MS is suitable for determination of cyclic imine toxins, and this study can provide a good reference and basis for qualitative and quantitative analysis of cyclic imine toxins in different complex matrix samples by LC-APCI-MS.
  • [1]
    OTERO A, CHAPELA M J, ATANASSOVA M, et al. Cyclic imines: Chemistry and mechanism of action: A review[J]. Chemical Research in Toxicology, 2011, 24(11): 1817-1829.
    [2]
    ALEXANDER J, BENFORD D, BOOBIS A, et al. Scientific opinion on marine biotoxins in shellfish-Cyclic imines (spirolides, gymnodimines, pinnatoxins and pteriatoxins)[J]. Journal of European Food Safety Authority, 2010, (8): 1628-1887.
    [3]
    TOUZET N, FRANCO J M, RAINE R. Morphogenetic diversity and biotoxin composition of Alexandrium (Dinophyceae) in Irish coastal waters[J]. Harmful Algae, 2008, 7(6): 782-797.
    [4]
    LVAREZ G, URIBE E, áVALOS P, et al. First identification of azaspiracid and spirolides in Mesodesma donacium and Mulinia edulis from Northern Chile[J]. Toxicon, 2010, 5(2/3): 638-641.
    [5]
    AMZIL Z, SIBAT M, ROYER F, et al. Report on the first detection of pectenotoxin-2, spirolide-A and their derivatives in French shellfish[J]. Marine Drugs, 2007, 5(4): 168-179.
    [6]
    MACKINNON S L, CEMBELLA A D, BURTON I W, et al. Biosynthesis of 13-desmethyl spirolide C by the dinoflagellate alexandrium ostenfeldii[J]. The Journal of Organic Chemistry, 2006, 71(23): 8724-8731.
    [7]
    KHARRAT R, SERVENT D, GIRARD E, et al. The marine phycotoxin gymnodimine targets muscular and neuronal nicotinic acetylcholine receptor subtypes with high affinity[J]. Journal of Neurochemistry, 2008, 107(4): 952-963.
    [8]
    BIR R, KRYS S, FRMY J M, et al. First evidence on occurrence of gymnodimine in clams from Tunisia[J]. Journal of Natural Toxins, 2002, 11(4): 269-275.
    [9]
    AASEN J, MACKINNON S L, LEBLANC P, et al. Detection and identification of spirolides in Norwegian shellfish and plankton[J]. Chemical Research in Toxicology, 2005, 18(3): 509-515.
    [10]
    MUNDAY R, TOWERS N R, MACKENZIE L, et al. Acute toxicity of gymnodimine to mice[J]. Toxicon, 2004, 44(2): 173-178.
    [11]
    MARROUCHI R, DZIRI F, BELAYOUNI N, et al. Quantitative determination of gymnodimine-A by high performance liquid chromatography in contaminated clams from Tunisia coastline[J]. Marine Biotechnology, 2010, 12(5): 579-585.
    [12]
    VILARIO N, FONFRA E S, MOLGO J, et al. Detection of gymnodimine-A and 13-desmethyl C spirolide phycotoxins by fluorescence polarization[J]. Analytical Chemistry, 2009, 81(7): 2708-2714.
    [13]
    RODRGUEZ L P, VILARIÑO N, MOLGO J, et al. Solid-phase receptor-based assay for the detection of cyclic imines by chemiluminescence, fluorescence, or colorimetry[J]. Analytical Chemistry, 2011, 83(15): 5857-5863.
    [14]
    GARCA-ALTARES M, CASANOVA A, BANE V, et al. Confirmation of pinnatoxins and spirolides in shellfish and passive samplers from catalonia (Spain) by liquid chromatography coupled with triple quadrupole and high-resolution hybrid tandem mass spectrometry[J]. Marine Drugs, 2014, 12(6): 3706-3732.
    [15]
    SCHUHMACHER J, ZIMMER D, TESCHE F, et al. Matrix effects during analysis of plasma samples by electrospray and atmospheric pressure chemical ionization mass spectrometry: Practical approaches to their elimination[J]. Rapid Communications in Mass Spectrometry, 2003, 17(17): 1 950-1 957.
    [16]
    ISMAIEL O A, HALQUIST M S, ELMAMLY M Y, et al. Monitoring phospholipids for assessment of ion enhancement and ion suppression in ESI and APCI LC/MS/MS for chlorpheniramine in human plasma and the importance of multiple source matrix effect evaluations[J]. Journal of Chromatography B, 2008, 875(2): 333-343.
    [17]
    MENDOZA W G, MEAD R N, BRAND L E, et al. Determination of brevetoxin in recent marine sediments[J]. Chemosphere, 2008, 73(8): 1373-1377.
    [18]
    LI X, LI Z Y, CHEN J H, et al. Detection, occurrence and monthly variations of typical lipophilic marine toxins associated with diarrhetic shellfish poisoning in the coastal seawater of Qingdao City, China[J]. Chemosphere, 2014, (111): 560-567.
    [19]
    SUZUKI T, BEUZENBERG V, MACKENZIE L, et al. Discovery of okadaic acid esters in the toxic dinoflagellate Dinophysis acuta from New Zealand using liquid chromatography/tandem mass spectrometry[J]. Rapid Communications in Mass Spectrometry, 2004, 18(10): 1131-1138.
    [20]
    母清林,方杰,万汉兴,等. 液相色谱-串联质谱法检测贝类产品中腹泻性贝类毒素[J]. 分析化学,2011, 39(1):111-114.MU Qinglin, FANG Jie, WAN Hanxing, et al. Determination of diarrhetic shell fish poisoning in shell fishes by liquid chromatography with tandem mass spectrometry[J]. Chinese Journal of Analytical Chemistry, 2011, 39(1): 111-114(in Chinese).
    [21]
    DOM NECH A, CORTS-FRANCISCO N, PALACIOS O, et al. Determination of lipophilic marine toxins in mussels. Quantification and confirmation criteria using high resolution mass spectrometry[J]. Journal of Chromatography A, 2014, (1 328): 16-25.
    [22]
    GERSSEN A, MULDER P P, MCELHINNEY M A, et al. Liquid chromatography-tandem mass spectrometry method for the detection of marine lipophilic toxins under alkaline conditions[J]. Journal of Chromatography A, 2009, 1 216(9): 1421-1430.
    [23]
    GERSSEN A, MCELHINNEY M A, MULDER P P, et al. Solid phase extraction for removal of matrix effects in lipophilic marine toxin analysis by liquid chromatography-tandem mass spectrometry[J]. Analytical and Bioanalytical Chemistry, 2009, 394(4): 1213-1226.
    [24]
    REGUEIRO J, ROSSIGNOLI A E, LVAREZ G, et al. Automated on-line solid-phase extraction coupled to liquid chromatography-tandem mass spectrometry for determination of lipophilic marine toxins in shellfish[J]. Food Chemistry, 2011, 129(2): 533-540.
    [25]
    KILCOYNE J, FUX E. Strategies for the elimination of matrix effects in the liquid chromatography tandem mass spectrometry analysis of the lipophilic toxins okadaic acid and azaspiracid-1 in molluscan shellfish[J]. Journal of Chromatography A, 2010, 1 217(45): 7123-7130.

Catalog

    Article views (959) PDF downloads (721) Cited by()

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return