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A simple method for the simultaneous determination of mushroom toxins by liquid chromatography–time-of-flight mass spectrometry

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Abstract

A simple and rapid method for the determination of nine mushroom toxins, ibotenic acid, propargylglycine, choline, muscimol, muscarine, α-amanitin, β-amanitin, phalloidin, and phallacidin, in mushroom samples has been developed. Mushroom toxins were extracted with 0.5 % formic acid in methanol/water, purified with Oasis HLB cartridges, and analyzed by liquid chromatography–time-of-flight mass spectrometry. The separation was performed on a pentafluorophenylpropyl column, and the mass spectrometer was operated in positive ion mode with electrospray ionization. Calibration curves were linear over the range of 0.01–1 μg/ml (R 2 = 0.999). The detection limits for the toxins in mushroom samples were 0.0098–4.9 μg/g, which were low enough for the investigation of food poisoning cases. The intraday and interday recoveries for blank mushroom extracts fortified with mushroom toxins were 72.5–107 % and 75.9–108 %, and relative standard deviations were <7.9 and 8.2 %, respectively.

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References

  1. Gonmori K, Fujita H, Yokoyama K, Watanabe K, Suzuki O (2011) Mushroom toxins: a forensic toxicological review. Forensic Toxicol 29:85–94

    Article  CAS  Google Scholar 

  2. Kasahara Y, Wada A (2013) Current topics of food poisoning caused by toxic mushrooms and further problems (in Japanese). Clin Virol 41:108–115

    Google Scholar 

  3. Maki T, Takahashi K, Shibata S (1985) Isolation of vomiting principles from the mushroom Rhodophyllus rhodopolius. J Agric Food Chem 33:1204–1205

    Article  CAS  Google Scholar 

  4. Yamaura Y, Fukuhara M, Takabatake E, Ito N, Hashimoto T (1986) Hepatotoxic action of a poisonous mushroom, Amanita abrupta in mice and its toxic component. Toxicology 38:161–173

    Article  CAS  PubMed  Google Scholar 

  5. Komiyama S, Yamaura Y, Nakazawa H, Fujita M, Kabasawa Y (1985) Determination of ibotenic acid and muscimol in Amanita muscaria by high performance liquid chromatography (in Japanese with English abstract). Bunseki Kagaku 34:161–165

    Article  CAS  Google Scholar 

  6. Tsujikawa K, Kuwayama K, Miyaguchi H, Kanamori T, Iwata Y, Inoue H, Yoshida T, Kishi T (2007) Determination of muscimol and ibotenic acid in Amanita mushrooms by high-performance liquid chromatography and liquid chromatography-tandem mass spectrometry. J Chromatogr B 852:430–435

    Article  CAS  Google Scholar 

  7. Gonmori K, Hasegawa K, Fujita H, Kamijo Y, Nozawa H, Yamagishi I, Minakata K, Watanabe K, Suzuki O (2012) Analysis of ibotenic acid and muscimol in Amanita mushrooms by hydrophilic interaction liquid chromatography–tandem mass spectrometry. Forensic Toxicol 30:168–172

    Article  CAS  Google Scholar 

  8. Hasegawa K, Gonmori K, Fujita H, Kamijo Y, Nozawa H, Yamagishi I, Minakata K, Watanabe K, Suzuki O (2013) Determination of ibotenic acid and muscimol, the Amanita mushroom toxins, in human serum by liquid chromatography–tandem mass spectrometry. Forensic Toxicol 31:322–327

    Article  CAS  Google Scholar 

  9. Unger SE, Vincze A, Cooks RG, Chrisman R, Rothman LD (1981) Identification of quaternary alkaloids in mushroom by chromatography/secondary ion mass spectrometry. Anal Chem 53:976–981

    Article  CAS  Google Scholar 

  10. Caccialanza G, Gandini C, Ponci R (1985) Direct, simultaneous determination of α-amanitin, β-amanitin and phalloidine by high-performance liquid chromatography. J Pharm Biomed Anal 3:179–185

    Article  CAS  PubMed  Google Scholar 

  11. Maurer HH, Kraemer T, Ledvinka O, Schmitt CJ, Weber AA (1997) Gas chromatography–mass spectrometry (GC–MS) and liquid chromatography–mass spectrometry (LC–MS) in toxicological analysis. Studies on the detection of clobenzorex and its metabolites within a systematic toxicological analysis procedure by GC–MS and by immunoassay and studies on the detection of α- and β-amanitin in urine by atmospheric pressure ionization electrospray LC–MS. J Chromatogr B 689:81–89

    Article  CAS  Google Scholar 

  12. Rittgen J, Pütz M, Pyell U (2008) Identification of toxic oligopeptides in Amanita fungi employing capillary electrophoresis–electrospray ionization–mass spectrometry with positive and negative ion detection. Electrophoresis 29:2094–2100

    Article  CAS  PubMed  Google Scholar 

  13. Ahmed WHA, Gonmori K, Suzuki M, Watanabe K, Suzuki O (2010) Simultaneous analysis of α-amanitin, β-amanitin, and phalloidin in toxic mushrooms by liquid chromatography coupled to time-of-flight mass spectrometry. Forensic Toxicol 28:69–76

    Article  CAS  Google Scholar 

  14. Clarke DB, Lloyd AS, Robb P (2012) Application of liquid chromatography coupled to time-of-flight mass spectrometry separation for rapid assessment of toxins in Amanita mushrooms. Anal Methods 4:1298–1309

    Article  CAS  Google Scholar 

  15. Gonmori K, Minakata K, Suzuki M, Yamagishi I, Nozawa H, Hasegawa K, Wurita A, Watanabe K, Suzuki O (2012) MALDI-TOF mass spectrometric analysis of α-amanitin, β-amanitin, and phalloidin in urine. Forensic Toxicol 30:179–184

    Article  CAS  Google Scholar 

  16. Nomura M, Suzuki Y, Kaneko R, Ogawa T, Hattori H, Seno H, Ishii A (2012) Simple and rapid analysis of amatoxins using UPLC–MS–MS. Forensic Toxicol 30:185–192

    Article  CAS  Google Scholar 

  17. Chung WC, Tso SC, Sze ST (2007) Separation of polar mushroom toxins by mixed-mode hydrophilic and ionic interaction liquid chromatography–electrospray ionization–mass spectrometry. J Chromatogr Sci 45:104–111

    Article  CAS  PubMed  Google Scholar 

  18. Yoshioka N, Asano M, Kuse A, Mitsuhashi T, Nagasaki Y, Ueno Y (2011) Rapid determination of glyphosate, glufosinate, bialaphos, and their major metabolites in serum by liquid chromatography-tandem mass spectrometry using hydrophilic interaction chromatography. J Chromatogr A 1218:3675–3680

    Article  CAS  PubMed  Google Scholar 

  19. Tahara K, Yonemoto A, Yoshiyama Y, Nakamura T, Aizawa M, Fujita Y, Nishikawa T (2006) Determination of antihyperglycemic biguanides in serum and urine using an ion-pair solid-phase extraction technique followed by HPLC-UV on a pentafluorophenylpropyl column and on an octadecyl column. Biomed Chromatogr 20:1200–1205

    Article  CAS  PubMed  Google Scholar 

  20. Okayama A, Tahara S, Ujike E, Tanaka T, Aoki Y, Sasaki M (1996) Determination of muscarine for mushroom poisoning (in Japanese). Ann Rep Nara Prefect Inst Public Health 30:71–74

    Google Scholar 

  21. Zeisel SH, Mar MH, Howe JC, Holden JM (2003) Concentrations of choline-containing compounds and betaine in common foods. J Nutr 133:1302–1307

    CAS  PubMed  Google Scholar 

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Acknowledgments

This work was supported in part by a grant from the Daido Life Welfare Foundation, Japan.

Conflict of interest

There are no financial or other relations that could lead to a conflict of interest.

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Authors and Affiliations

  1. Hyogo Prefectural Institute of Public Health and Consumer Sciences, 2-1-29 Arata-cho, Hyogo-ku, Kobe, 652-0032, Japan

    Naoki Yoshioka, Shigeki Akamatsu & Takao Mitsuhashi

  2. Forestry Technology Institute, Hyogo Prefectural Technology Center for Agriculture, Forestry and Fisheries, Shiso, Hyogo, Japan

    Chikage Todo

  3. Department of Legal Medicine, Ehime University Graduate School of Medicine, Toon, Ehime, Japan

    Migiwa Asano

  4. Division of Legal Medicine, Department of Environmental Health and Safety, Kobe University Graduate School of Medicine, Kobe, Japan

    Yasuhiro Ueno

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  1. Naoki Yoshioka
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  2. Shigeki Akamatsu
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  3. Takao Mitsuhashi
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  4. Chikage Todo
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  5. Migiwa Asano
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  6. Yasuhiro Ueno
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Correspondence to Naoki Yoshioka.

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Yoshioka, N., Akamatsu, S., Mitsuhashi, T. et al. A simple method for the simultaneous determination of mushroom toxins by liquid chromatography–time-of-flight mass spectrometry. Forensic Toxicol 32, 89–96 (2014). https://doi.org/10.1007/s11419-013-0214-5

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  • DOI: https://doi.org/10.1007/s11419-013-0214-5

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