Taxines: A review of the mechanism and toxicity of yew (Taxus spp.) alkaloids

Toxicon

Volumn 39, Issue 2-3, 2001, Pages 175-185

  Wilson, Christina R ^a   Sauer, John Michael ^a   Hooser, Stephen B ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

Animal; Human; Physiology; Review; Taxine; Taxus; Toxicity; Yew

Indexed keywords

ACTIVATED CARBON; ALKALOID; ATROPINE; ELECTROLYTE; LIDOCAINE; MINERAL OIL; PACLITAXEL; PLANT TOXIN; TAXINE; TAXINE A; TAXINE B; UNCLASSIFIED DRUG;

BOVIDS; CARDIOTOXICITY; CARDIOVASCULAR SYSTEM; CONFERENCE PAPER; DEATH; DRUG MECHANISM; ELECTROPHYSIOLOGY; GASTROTOMY; HEART FAILURE; HEART MUSCLE CELL; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; INTOXICATION; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PLANT; PRIORITY JOURNAL; SCIENTIFIC LITERATURE; STOMACH LAVAGE;

ANIMALIA; TAXUS;

EID: 0034598635     PISSN: 00410101     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0041-0101(00)00146-X     Document Type: Conference Paper

References (60)

1. Adeline M.T., Wang X.P., Poupat C., Ahond A., Potier P. Evaluation of taxoids from Taxus spp. Crude extracts by high performance liquid chromatography. J. Liq. Chrom. Rel. Tech. 20:(19):1997;3135-3145.
2. Alden C.L., Fosnaugh C.J., Smith J.B., Mohan R. Japanese yew poisoning in large domestic animals in the midwest. J. Am. Vet. Med. Assoc. 170:(3):1977;314-316.
3. Alloatti G., Penna C., Levi R.C., Gallo M.P., Appendino G., Fenoglio I. Effects of yew alkaloids and related compounds on guinea-pig isolated perfused heart and papillary muscle. Life Sci. 58:(10):1996;845-854.
4. Appendino G., Özen H., Fenoglio I., Gariboldi P., Gabetta B., Bombardelli E. Pseudoalkaloid taxanes from Taxus baccata. Phytochem. 33:(6):1997;1521-1523.
5. Arai M., Stauber E., Shropshire C.M. Evaluation of selected plants for their toxic effects in canaries. J. Am. Vet. Med. Assoc. 200:(9):1992;1329-1331.
6. Arena J.M. Poisonous plants. Poisoning. Toxicology, Symptoms, Treatments. 4th ed. 1979;554 Charles C Thomas, Springfield, IL.
7. Bauereis V.R., Steiert W. Pharmakologische eigenschaften von taxin A und B. Arzneim.-Forschun. 9:1959;77-79.
8. Baxter J.N., Lythgoe B., Scales B., Scrowston R.M., Trippett S. Taxine. Part I: Isolation studies and the functional groups of o-Cinnamoyltaxicin-I. J. Chem. Soc. (C):1962;2964-2972.
9. Baxter, J.N., Lythgoe, B., Scales, B., Trippett, S., 1958. Taxine-I, the major alkaloid of the yew, T. baccata L. Proc. Chem. Soc., 9-10.
10. Blyth A.W. Taxine. Poisons: Their Effects and Detection. 1884;383-384 Charles Griffin, London.
11. Bryan-Brown T. The Pharmacological actions of taxine. Q. J. Pharm. and Pharmacol. 5:1932;205-219.
12. Casteel S.W., Cook W.O. Japanese yew poisoning in ruminants. Mod. Vet. Practice. 66:1985;875-876.
13. Clarke E.G.C., Clarke M.L. Poisonous plants, Taxaceae. Veterinary Toxicology. 3rd ed. 1988;276-277 Baillière, Tindall & Cassell, London.
14. Czerwek H., Fischer W. Tödlicher vergiftungsfall mit Taxus baccata. Archiv Toxikol. 18:1960;88-92.
15. Dukes M., Eyre D.H., Harrison J.W., Scrowston R.M., Lythgoe B. Taxine. Part V: The structure of taxicin-II. J. Chem. Soc. (C):1967;448-462.
16. Ettouati B., Ahond A., Poupat C., Potier P. Révision structurale de la taxine B, alcaloïde majoritaire des feuilles de L'if D'Europe, Taxus baccata. J. Nat. Prod. 54:(5):1991;1455-1458.
17. Evans K.L., Cook J.R. Japanese yew poisoning in a dog. J. Am. Animal Hosp. Assoc. 27:1991;300-302.
18. Evers R.A., Link R.P. Yews, Taxus species. Poisonous Plants of the Midwest and their Effects on Livestock. 1972;81-82 College of Agriculture, University of Illinois at Urbana-Champaign, IL.
19. Foster S., Duke J.A. American yew. Eastern/Central Medicinal Plants. 1990;226 Houghton Mifflin, Boston, MA.
20. Fröhne D., Pfänder J. Taxaceae, Taxus baccata L., yew. A Colour Atlas of Poisonous Plants. 2nd ed. 1984;223-225 Wolfe Publishing, London.
21. Fröhne D., Pribilla O. Tödliche vergiftung mit Taxus baccata. Arch. für Toxikologie. 21:1965;150-162.
22. Gianni L., Munzone E., Capri G., Fulfaro F., Tarenzi E., Villani F., Spreafico C., Laffranchi A., Caraceni A., Stefanelli M., Valagussa P., Bonadonna G. Paclitaxel by 3-h infusion in combination with bolus doxorubicin in women with untreated metastatic breast cancer: high antitumor efficacy and cardiac effects in a dose-finding and sequence-finding study. J. Clin. Oncology. 13:(11):1995;2688-2699.
23. Graf E. Zur chemie des taxins. Angew. Chem. 68:1956;249-250.
24. Graf E., Bertholdt H. Das amorphe taxin und das kristallisierte taxin A. Pharm. Zentralhalle. 96:1957;385-395.
25. Graf E., Boeddeker H. Zur kenntnis der β-dimethylamino-hydrozimtsäure. Archiv der Pharm. und Berichte der Deutsch. Pharmaz. Ges. 289:1956;364-370.
26. Graf, E., Boeddeker, H., Johannsen, B., Rosha, R., 1963. Stand der Kenntnis des Taxins. Abhand. Deutsch. Akad. Wis. Berlin, Klasse für Chem., Geol., Biol., 389-394.
27. Graf, E., Kirkel, A., Wolff, G.J., Breitmaier, E., 1982. Die Aufklärung von taxin A aus Taxus baccata L. Liebigs Ann. Chem., 376-381.
28. 13C-NMR-Untersuchung von taxin B aus Taxus baccata L. Liebigs Ann. Chem., 1147-1151.
29. Hartzell H. Yew and us: a brief history of the yew tree. Suffness M. Taxol: Science and Applications. 1995;27-34 CRC Press, Boca Raton, FL.
30. Hilger A., Brande F. Ueber taxin, das alkaloïd des eibenbaumes (Taxus baccata). Berichte Deutsch. Chem. Ges. 23:1890;464-468.
31. Jenniskens L.H.D., van Rozendaal E.L.M., van Beek T.A. Identification of six taxine alkaloids from Taxus baccata needles. J. Nat. Prod. 59:1996;117-123.
32. Karns P.A. Intoxication in horses due to ingestion of japanese yew (Taxus cuspidata). Equine Practice. 5:(1):1983;12-14.
33. Kingsbury J.M. Taxaceae. Poisonous Plants of the United States and Canada. 1964;121-123 Prentice-Hall, Englewood Cliffs, NJ.
34. Lucas H. Ueber ein in den Blätter von Taxus baccata L. enhaltenes Alkaloid (das Taxin). Archiv der Pharmaz. 135:1856;145-149.
35. Lythgoe B., Harrison J.W. Taxine. Part III: A revised structure for the neutral fragment from o-Cinnamoyltaxicin-I. J. Chem. Soc. (C):1966;1932-1945.
36. Matthew N., Elsner G., Purdy C., Zipes D.P. Wide QRS rhythm due to taxine toxicity. J. Cardiovascular Electrophys. 3:1993;59-61.
37. Ogden L. Taxus (yews) - a highly toxic plant. Vet. Human Toxic. 30:(6):1988;563-564.
38. Osweiler G.D. Toxicology. 1996;393 Williams & Wilkins, Philadelphia, PA.
39. Panter K.E., Molyneux R.J., Smart R.A., Mitchell L., Hansen S. English yew poisoning in 43 cattle. J. Am. Vet. Med. Assoc. 202:(9):1993;1476-1477.
40. Potier C.R., Poujol H., Ahond A., Mourabit A.A., Chiaroni A., Poupat C. Taxoïdes: nouveaux analogues du 7-déshydroxydocétaxel préparés à partir des alcaloïdes de I'lf. Tetrahedron. 53:(14):1997;5169-5184.
41. Poupat C., Ahond A., Potier P. Nouveau Taxoïde Basique Isolé Des Feuilles d'if, Taxus Baccata: La 2-Désacétyltaxine A. J. Nat. Prod. 57:(10):1994;1468-1469.
42. Rooks J.S. Japanese yew toxicity. Vet. Medicine. 89:1994;950-951.
43. Rowinsky E.K., McGuire W.P., Guaneri T., Fisherman J.S., Christian M.C., Donehauer R.C. Cardiac disturbances during the administration of taxol. J. Clin. Oncology. 9:(9):1991;1704-1712.
44. Schulte T. Tödliche Vergiftung Mit Eibennadeln (Taxus baccata). Archiv. Toxikologie. 34:1975;153-158.
45. Sinn L.E., Porterfield J.F. Fatal taxine poisoning from yew leaf ingestion. J. Forensic Sci. 36:(2):1991;599-601.
46. Smythies J.R., Benington F., Morin R.D., Al-Zahid G., Schoepfle G. The action of the alkaloids from yew (Taxus baccata) on the action potential in the xenopus medullated axon. Experentia. 31:1975;337-338.
47. Spector W.S. Handbook of Biological Data. 1956;Wright-Patterson AFB, OH.
48. Stahr H.M., Hyde W., Kiesey J., Ross P.F. Alkaloids; extraction and qualitative identification. Analytical Methods in Toxicology. 1977;178-183 Iowa State University Press, Ames, IA.
49. Suffness M. Taxol: Science and Applications. 1995;7/8-311/312 CRC Press, Boca Raton, FL.
50. Tekol Y. Negative chronoptopic and atrioventricular blocking effects of taxine on isolated frog heart and its acute toxicity in mice. Planta Med. 5:1985;357-360.
51. Tekol Y. Acute toxicity of taxine in mice and rats. Vet. Human Toxic. 33:(4):1991;337-338.
52. Tekol Y., Gögüsten B. Comparative determination of the cardioselectivity of taxine and verapamil in the isolated aorta, atrium, and jejunum preparations of rabbits. Arzneim.-Forschung. 49:(8):1999;673-678.
53. Tekol Y., Kameyama M. Elektrophysiologische Untersuchungen über den Wirkungsmechanisms des Eibentoxins Taxin auf das Herz. Arzneim.-Forschun. 37:(4):1987;428-431.
54. Thuret-Carnahan J., Bossu J.L., Feltz A., Langley K., Aunis D. Effect of taxol on secretory cells: functional, morphological, and electrophysiological correlates. J. Cell Biol. 100:1985;1863-1874.
55. Touchstone J.C., Dobbins M.F. Visualization procedures. Practice of Thin-Layer Chromatography. 1978;212 Wiley, New York.
56. Tyler, V.E., 1960. Note on the occurrence of taxine in Taxus brevifolia. J. Am. Pharm. Assoc., 683-684.
57. Veatch J.K., Reid F.M., Kennedy G.A. Differentiating yew poisoning from other toxicoses. Vet. Medicine. 83:1988;298-300.
58. Vohora S.B. Studies on Taxus baccata. Planta Med. 22:(1):1972;59-65.
59. Watt J.M., Breyer-Brandwijk M.G. Taxaceae. The Medicinal and Poisonous Plants of Southern and Eastern Africa. 1962;1019-1022 E. & S. Livingstone, Edinburgh.
60. Wani M.C., Taylor H.L., Wall M.E., Coggon P., McPhail A.T. Plant antitumor agents. VI: the isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus Brevifolia. J. Am. Chem. Soc. 93:1971;2325-2327.