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A High Performance Liquid Chromatography-Mass Spectrometry (HPLC-MS) Qualitative Detection Method Developed for In Vivo Analyses of Toxin Orellanine from the Cortinarius orellanus Fr.—Part II

DOI: 10.5402/2012/293830

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Abstract:

The high-performance liquid chromatography—mass spectrometry (HPLC-MS) qualitative analysis method in negative mode of detection was used to record the presence of orellanine in the stomach contents of rats after ingestion of Cortinarius orellanus. Intoxication with orellanine causes acute renal failure (ARF), which is characterized by sudden loss of the ability of the kidneys to excrete wastes. The detection method presented here can be used as a platform for future development of analytical procedures for detecting orellanine in cases of human intoxication by toadstools. The presence of orellanine in animal stomach contents was analytically recorded and compared with standard orellanine, which was donated by the R&D Department of Jupiter Ltd, Norway. The MS fragmentation described in the literature and the MS fragmentation of standard samples of isolated orellanine verified the presence of orellanine in the stomach contents of laboratory animals. The presence of a diglucoside of orellanine, which was described as part of the toxic orellanine complex by Spiteller et al., in the stomach contents of animals, was also verified using HPLC-MS. 1. Introduction In the last few decades, edible mushrooms have represented a growing segment in the diets of western European and north American populations, and these delicate-tasting and protein-rich vegetables have been grown on an industrial scale; however, forest mushrooms have also experienced increasing popularity at the dining table. A significant increase in the production and import of forest mushrooms from eastern Europe and Poland has been observed, but self-collection of forest mushrooms has also become more popular in recent decades. The possibility of mistaking nonedible for edible mushrooms is significant among amateur collectors. Epidemic outbreaks of mass intoxication by pseudoedible mushrooms were observed in Poland in 1952–1957. Later in 1957, the cause of these outbreaks was described by Grzymala as intoxication by a member of the Cortinarius family [1]. The toxin orellanine from Cortinarius orellanus was first isolated by Grzymala in 1962 as part of a mixture with other substances. The chemical structure of orellanine was defined as 3,3′,4,4′-tetrahydroxy-2,2′-bipyridine-N-N′-dioxide [2]. Several studies have been performed over the years to support the initial proposition of its chemical structure. The study performed by Holmdahl et al. supported the correctness of this chemical structure based on 1H-NMR and 13C-NMR spectra [3]. However, a doubt was expressed regarding the level of the toxic

References

[1]  S. Grzymala, “Massenvergiftungen durch den orangefuchsigen Hautkopf,” Zeitschrift für Pilzkunde, vol. 23, pp. 139–142, 1957.
[2]  W. Z. Antkowiak, R. Antkowiak, E. Wyrzykiewicz, and G. Czerwiński, “Mass spectral fragmentation of orellanine and its tetramethyl ether with regard to their facile thermal and photochemical deoxygenation,” Heterocycles, vol. 39, no. 2, pp. 477–484, 1994.
[3]  J. Holmdahl, J. Ahlmén, S. Bergek, S. Lundberg, and S.-A. Persson, “Isolation and nephrotoxic studies of orellanine from the mushroom Cortinarius speciosissmus,” Toxicon, vol. 25, no. 2, pp. 195–199, 1987.
[4]  J.-M. Richard, G. Taillandier, and J. L. Benoit-Guyod, “A quantitative structure-activity relationship study on substituted pyridines as a contribution to the knowledge of the toxic effects of orellanine, a toxin from the mushroom Cortinarius orellanus,” Toxicon, vol. 23, no. 5, pp. 815–824, 1985.
[5]  N. A. Klein, S. J. Siskind, W. H. Frishman, E. H. Sonnelblick, and T. H. LeJemtel, “Hemodynamic comparison of intravenous amrinone and dobutamine in patients with chronic congestive heart failure,” American Journal of Cardiology, vol. 48, no. 1, pp. 170–175, 1981.
[6]  Chevron Chemical Company, “Diquat herbicide h/a for aquatic plant treatment. Agricultural Chemicals Division,” Agricultural Chemicals Division. No. 8616 DIQ-45, Chevron Chemical Company, San Francisco, Calif, USA, 1986.
[7]  Occupational Health Services, Material Safety Data Sheets, OHS, Secaucus, NJ, USA, 1986.
[8]  WSSA Herbicide Handbook Committee, Herbicide Handbook of the Weed Science Society of America, WSSA, Champaign, Ill, USA, 6th edition, 1989.
[9]  Occupational Health Services, MSDS for Diquat, OHS, Secaucus, NJ, USA, 1991.
[10]  W. J. Hayes and E. R. Laws, Eds., Handbook of Pesticide Toxicology, vol. 3 of Classes of Pesticides, Academic Press, New York, NY, USA, 1990.
[11]  I. Brondz, E. Nevo, S. Wasser, K. H?iland, F. St?rmer, and A. Brondz, “Method development for in vivo analyses of toxin orellanine from the toad mushroom Cortinarius orellanus,” in Proceedings of the Separation Science Europe Conference, The Royal Institution, London, UK, October 2011.
[12]  I. Brondz, E. Nevo, S. Wasser, and A. Brondz, “A direct Gas Chromatography—Mass Spectrometry (GC-MS) method for the detection of orellanine present in stomach content. Part I,” Journal of Biophysical Chemistry, vol. 3, no. 1, 2012.
[13]  P. Spiteller, M. Spiteller, and W. Steglich, “Occurrence of the fungal toxin orellanine as a diglucoside and investigation of its biosynthesis,” Angewandte Chemie—International Edition, vol. 42, no. 25, pp. 2864–2867, 2003.
[14]  J.-M. Richard and J. Ulrich, “Mass spectrometry of orellanine, a mushroom toxin, and of related bipyridine-N-oxides,” Biomedical and Environmental Mass Spectrometry, vol. 18, no. 1, pp. 1–4, 1989.
[15]  I. Brondz, D. Ekeberg, K. H?iland, D. S. Bell, and A. R. Annino, “The real nature of the indole alkaloids in Cortinarius infractus: evaluation of artifact formation through solvent extraction method development,” Journal of Chromatography A, vol. 1148, no. 1, pp. 1–7, 2007.
[16]  H. Kürnsteiner and M. Moser, “Isolation of a lethal toxin from Cortinarius orellanus Fr,” Mycopathologia, vol. 74, no. 2, pp. 65–72, 1981.
[17]  J. W. Walker and V. K. Krieble, “CLIII.—the hydrolysis of amygdalin by acids. Part I,” Journal of the Chemical Society, vol. 95, pp. 1369–1377, 1909.

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