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LC-MS determination of Taxus alkaloids in biological specimens

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Abstract

A semi-quantitative LC-MS method was developed for the detection of the pseudo alkaloids of Taxus baccata (yew) from human body fluids and tissue samples. This method was used to examine the cause of death of a 43-year-old man who died several hours after he drank a decoction of taxus leaves. Autopsy and histology demonstrated early signs of myocardial hypoxia. Since investigation of the stomach content did not yield evidence of taxus ingestion, the taxus alkaloids were determined in blood, stomach content and tissue samples of the deceased by LC-MS. The samples were prepared by solid phase extraction on RP-18 columns. Chromatographic separation was achieved by HPLC on a RP-8 column, coupled to an ion trap mass spectrometer (Finnigan LCQ). An atmospheric pressure electrospray ionisation was performed. Spectra of the alkaloids were recorded in the single MS mode and in the MS-MS mode and compared with reference spectra obtained from an extract of yew leaves. In the stomach content, the kidneys, the liver and a heart blood sample of the deceased, alkaloids of Taxus baccata, predominantly taxine B and iso-taxine B, were identified. The semi-quantitative evaluation of the heart blood revealed a taxine concentration of 11 µg taxine/g. As far as we know this is the first case in which a semi-quantitative analysis of taxine alkaloids has been performed.

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References

  1. Friese W (1951) Beitrag zur Kenntnis der Eibe (Taxus baccata L.). Pharm Zentralh 90:259–262, 289–291

    CAS  Google Scholar 

  2. Frohne D, Pribilla O (1965) Tödliche Vergiftung mit Taxus baccata. Arch Toxikol 21:150–162

    CAS  PubMed  Google Scholar 

  3. Cummins RO, Haulman J, Quan L, Graves JR, Peterson D, Horan S (1990) Near-fatal yew berry intoxication treated with external cardiac pacing and digoxin-specific FAB antibody fragments. Ann Emerg Med 19:38–43

    CAS  PubMed  Google Scholar 

  4. Ritter S (1985) Vergiftungen durch Pflanzen. Dtsch Apoth Z 37:1834–1836

    Google Scholar 

  5. Janssen J, Peltenburg H (1985) En klassieke wijze van zelfoding: met Taxus baccata. Ned Tijdschr Geneeskd 13:603–605

    Google Scholar 

  6. Appendino G, Gariboldi P, Pisetta A, Bombardelli E, Gabetta B (1992) Taxanes from Taxus baccata. Phytochemistry 31:4253–4257

    Article  CAS  Google Scholar 

  7. Jenniskens L, Rozendaal E, Beek T van (1996) Identification of six taxine alkaloids from Taxus baccata needles. J Nat Prod 59:117–123

    Article  CAS  Google Scholar 

  8. Alloatti G, Penna C, Levi RC, Gallo MP, Appendino G, Fenoglio I (1995) Effects of yew alkaloids and related compounds on guinea-pig isolated perfused heart and papillary muscle. Life Sci 58:845–854

    Article  Google Scholar 

  9. Wilson CR, Sauer J, Hooser SB (2001) Taxines: a review of the mechanism and toxicity of yew (Taxus spp.) alkaloids. Toxicon 39:175–185

    Article  CAS  PubMed  Google Scholar 

  10. Ingen G van, Viesser R, Peltenburg H, Ark AM van der, Voortman M (1992) Sudden unexpected death due to Taxus poisoning. A report of five cases, with review of the literature. Forensic Sci Int 56:81–87

    PubMed  Google Scholar 

  11. Sinn LE, Porterfield JF (1991) Fatal poisoning from yew leaf ingestion. J Forensic Sci 36:599–601

    CAS  PubMed  Google Scholar 

  12. Lang DG, Smith RA, Miller RE (1997) Detecting Taxus poisonings using GC/MS. Vet Hum Toxicol 39:314

    CAS  PubMed  Google Scholar 

  13. Musshoff F, Jacob B, Fowinkel C, Daldrup T (1993) Suicidal yew leave ingestion—phloroglucindimethylether (3,5-dimethoxyphenol) as a marker for poisoning from Taxus baccata. Int J Legal Med 106:45–50

    CAS  PubMed  Google Scholar 

  14. Hoke SH, Wood JM, Cooks RG, Li XH, Chang CJ (1992) Rapid screening for taxanes by tandem mass spectrometry. Anal Chem 64:2313–2315

    CAS  PubMed  Google Scholar 

  15. Kerns EH, Volk KJ, Hill SE, Lee MS (1994) Profiling taxanes in Taxus extracts using LC/MS and LC/MS/MS techniques. J Nat Prod 57:1391–1403

    CAS  PubMed  Google Scholar 

  16. Hoke SH, Cooks RG, Chang CJ, Kelly RC, Qualls SJ, Alvarado B, McGuire MT, Snader KM (1994) Determination of taxanes in Taxus brevifolia extracts by tandem mass spectrometry and high-performance liquid chromatography. J Nat Prod 57:277–286

    CAS  PubMed  Google Scholar 

  17. Blay PKS, Thibault P, Thiberge N, Kiecken B, Lebrun A, Mercure C (1993) Analysis of taxol and related taxanes from Taxus canadensis using liquid chromatography combined with mass spectrometry or tandem mass spectrometry. Rapid Commun Mass Spectrom 7:626–634

    CAS  Google Scholar 

  18. Weinmann W, Bohnert M, Wiedemann A, Renz M, Lehmann N, Pollak S (2001) Post-mortem detection and identification of sildenafil (Viagra) and its metabolites by LC/MS and LC/MS/MS. Int J Legal Med 114:252–258

    Article  CAS  PubMed  Google Scholar 

  19. Kite C, Lawrence TJ, Dauncey EA (2000) Detecting Taxus poisoning in horse using liquid chromatography/mass spectrometry. Vet Hum Toxicol 42:151–154

    CAS  PubMed  Google Scholar 

  20. Sottani C, Minoia C, D’Incalci M, Paganini M, Zucchetti M (1998) High-performance liquid chromatography tandem mass spectrometry procedure with automated solid phase extraction sample preparation for the quantitative determination of paclitaxel (Taxol(R)) in human plasma. Rapid Commun Mass Spectrom 12:251–255

    Article  CAS  PubMed  Google Scholar 

  21. Bogusz MJ, Maier RD, Kruger KD, Kohls U (1998) Determination of common drugs of abuse in body fluids using one isolation procedure and liquid chromatography-atmospheric-pressure chemical-ionization-mass spectromery. J Anal Toxicol 22:549–558

    CAS  PubMed  Google Scholar 

  22. Graf E, Weinandy S, Koch B (1986)13C-NMR-Untersuchung von Taxin B aus Taxus baccata L. Liebigs Ann Chem 1147–1151

  23. Adeline MT, Wang C, Poupat A (1997) Evaluation of taxoids from Taxus sp. crude extracts by high performance liquid chromatography. J Liq Chrom Rel Technol 20:3135–3145

    CAS  Google Scholar 

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Beike, J., Karger, B., Meiners, T. et al. LC-MS determination of Taxus alkaloids in biological specimens. Int J Legal Med 117, 335–339 (2003). https://doi.org/10.1007/s00414-003-0399-y

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