Hemlock alkaloids from Socrates to poison aloes

Phytochemistry

Volumn 66, Issue 12, 2005, Pages 1399-1406

  Reynolds, Tom ^a  

^a JODRELL LABORATORY   (United Kingdom)

Author keywords

Aloes; Biosynthesis; Hemlock; Piperidine alkaloids; Poisons

Indexed keywords

ALOE; ALOES; APIACEAE; CONIUM; CONIUM MACULATUM; DICOTYLEDONEAE; LILIOPSIDA;

EID: 20444400854     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2005.04.039     Document Type: Short Survey

References (79)

1. F.B. Ahrens Ueber conium-alkaloide Ber. Deutsch. Chem. Ges. 35 1902 1330 1334
2. H.C. Beterman, M. van Leeuwen, J. Smidt, and A. van Veen γ-Coniceine of Conium maculatum L. - a revision of the generally accepted structure Recueil Trav. Chim. Pays-Bas 80 1961 513 525
3. F. Berger, M.H. Ramírez-Hernández, and M. Ziegler The new life of a centenarian: signalling functions of NAD(P) Trends Biochem. Sci. 29 2004 111 118
4. T. Blitzke, A. Porzel, M. Masaoud, and J. Schmidt A chlorinated amide and piperidine alkaloids from Aloe sabaea Phytochemistry 55 2000 979 982
5. J. Blyth On the composition of coniine and its products of decomposition Quart. J. Chem. Soc. London 1 1849 345 363
6. Budavari, S. (Ed.), 1996. The Merck Index, 12th ed. Merck & Co., Inc. New Jersey p. 424.
7. W.C. Bowman, and I.S. Sanghvi Pharmacological actions of hemlock (Conium maculatum) alkaloids J. Pharm. Pharmacol. 15 1963 1 25
8. R. Brandes Einige Bersuche uber den Schierling Arch. Apotheker-Vereins Nördl. Teutschl. 20 1826 111 114
9. R. Brandes, and A.L. Giseke (sic) Du principe actif de la grande ciguë, et des moyens d'obtenir le coniin J. Chim. Médicale Pharm. Toxicol. 5 1829 138 139
10. Brooks, D.E., 2001. Plant poisoning, hemlock. Available from: 〈www.emedicine.com/emerg/topic875.htm〉.
11. F. Chemnitius Zur darstellung des coniins und des conhydrins J. Prakt. Chem. 118 1928 25 28
12. R. Christison A treatise on poisons in relation to medical jurisprudence Physiology and the practice of physic 1829 Adam Black Edinburgh
13. R. Christison On the poisonous properties of hemlock and its alkaloid conia Trans. Roy. Soc. Edinburgh 13 1836 383 407
14. G. Corsi, and D. Biasci Secretory structures and localization of alkaloids in Conium maculatum L. (Apiaceae) Ann. Bot. 81 1998 157 162
15. B.T. Cromwell The separation, micro-estimation and distribution of the alkaloids of hemlock (Conium maculatum L.) Biochem. J. 64 1956 259 266
16. B.T. Cromwell, and M.F. Roberts The biogenesis of γ-coniceine in hemlock (Conium maculatum) Phytochemistry 3 1964 369 375
17. J. de Boer The death of Socrates. A historical and experimental study on the actions of coniine and Conium maculatum Arch. Int. Pharmacodynamie Therapie 83 1950 473 490
18. J.V. Dring, R.J. Nash, M.F. Roberts, and T. Reynolds Hemlock alkaloids in aloes. Occurrence and distribution of γ-coniceine Planta Med. 50 1984 442 443
19. R.B. Drummond, M. Gelfand, and S. Mavi Medicinal and other uses of succulents by the Rhodesian African Excelsa 5 1975 51 56
20. C. Engler, and A.. Kronstein Ueber Conhydrin und Pseudoconhydrin Ber. Deutsch. Chem. Ges. 27 1894 1779 1784
21. J.W. Fairbairn The alkaloids of hemlock (Conium maculatum L.) V.H. Heywood The biology and chemistry of the umbelliferae 1971 Academic Press London and New York 361 368
22. J.W. Fairbairn, and A.A.E.R. Ali The alkaloids of hemlock (Conium maculatum L.) - III The presence of bound forms in the plant Phytochemistry 7 1968 1593 1597
23. J.W. Fairbairn, and A.A.E.R. Ali The alkaloids of hemlock (Conium maculatum L.) - IV Isotopic studies of the bound forms of alkaloids in the plant Phytochemistry 7 1968 1599 1603
24. J.W. Fairbairn, and S.B. Challen The alkaloids of hemlock (Conium maculatum L.). Distribution in relation to the development of the fruit Biochem. J. 72 1959 556 561
25. J.W. Fairbairn, and P.N. Suwal The alkaloids of hemlock (Conium maculatum L.). - II Evidence for a rapid turnover of the major alkaloids Phytochemistry 1 1961 38 46
26. S. Gabriel Synthese des γ-Coniceins Ber. Deutsch. Chem. Ges. 42 1909 4059 4062
27. P.L. Geiger Versuche mit Conium maculatum Mag. Pharm. 35 1831 75 85 259-286
28. A.L. Giseke (sic) Ueber das wirksame Princip des Schierlings Conium maculatum Arch. Apotheker-Vereins Nördl. Teutschl. 20 1826 97 111
29. A.L. Giseke (sic) Extract from several notebooks of the Archives of the Society of Pharmacy of Northern Germany J. Pharm. Sci. Accessoires 13 1827 366 367
30. Grieve, M., 1995-2004. Hemlock. In Botanical.com - A Modern Herbal. Available from: 〈www.botanical.com/botanical/mgmh/h/hemloc18.html〉.
31. R.N. Gupta Biosynthesis of the piperidine alkaloids Lloydia 31 1968 318 326
32. A. Hébert, and F. Heim Recherches sur les principes actifs de quelques aroïdées Bull. Soc. Chim. 17 1898 664 669
33. T.A. Henry The plant alkaloids 1913 J. & A Churchill London pp. 23-34
34. T. Heresztyn Formation of substituted tetrahydropyridines by species of Brettanomyces and Lactobacillus isolated from mousy wines Am. J. Enol. Vitic. 37 1986 127 132
35. A.W. Hofmann Einwirkung dre Wärmeauf die Ammoniumbasen Ber. Deutsch. Chem. Ges. 14 1881 705 713
36. Huggins, J., 2002. Coniine and the hemlock alkaloids. Available from: 〈www.chm.bris.ac.uk/motm/hemlock〉.
37. R.F. Keeler Coniine, a teratogenic principle from Conium maculatum producing congenital malformations in calves Clin. Toxicol. 7 1974 195 206
38. R.F. Keeler R.F. Keeler A.T. Tu Handbook of natural toxins vol. 1 1983 Marcel Dekker Inc. New York and Basel 161 199
39. A. Ladenburg Veruche zur Synthese des Coniin Ber. Deutsch. Chem. Ges. 19 1886 439 441
40. A. Ladenburg, and G. Adam Ueber ein neues Alkaloid aus Conium maculatum, seine Constitution und Versuche zu seiner Synthese Ber. Deutsch. Chem. Ges. 24 1891 1671 1676
41. Lambert, G., 1879. Ann. Séance Acad. Sci. Paris. 88, 185: quoted by Mody, 1976.
42. E. Leete The biosynthesis of coniine from four acetate units J. Am. Chem. Soc. 85 1963 3523 3574
43. 14 into coniine and conhydrine J. Am. Chem. Soc. 86 1964 2509 2513
44. E. Leete The biosynthesis of coniine from octanoic acid in hemlock plants (Conium maculatum) J. Am. Chem. Soc. 92 1970 3835
45. E. Leete, and N. Adityachaudhury Biosynthesis of hemlock alkaloids II Conversion of γ-coniceine to coniine and ψ-conhydrine Phytochemistry 6 1967 219 223
46. E. Leete, and J.O. Olson 5-Oxo-octanoic acid and 5-oxo-octanal, precursors of coniine J. Chem. Soc. D 1970 1651
47. E. Leete, and J.O. Olson Biosynthesis and metabolism of the hemlock alkaloids J. Am. Chem. Soc. 94 1972 5472 5477
48. K. Löffler Über die Konstitution des Pseudoconhydrins Ber. Deutsch. Chem. Ges. 42 1909 116 125
49. T.A. López, M.S. Cid, and M.L. Bianchini Biochemistry of hemlock (Conium maculatum L.) alkaloids and their acute and chronic toxicity in livestock. A review Toxicon 37 1999 841 865
50. E. Merck Reported as "pseudoconhydrine" Pharm. J. 21 1891 662
51. N.V. Mody, R. Henson, P.A. Hedin, and D.H. Kokpol Isolation of the insect paralysing agent coniine from Sarracenia flava Experientia 32 1976 829 830
52. C.J. Moody, A.P. Lightfoot, and P.T. Gallagher Asymmetric synthesis of 2-substituted piperidines. Synthesis of the alkaloids (-)-coniine and (±)-pseudoconhydrine J. Org. Chem. 62 1997 746 748
53. R.J. Nash, J. Beaumont, N.C. Veitch, T. Reynolds, J. Benner, C.N.G. Hughes, J.V. Dring, R.N. Bennett, and J.E. Dellar Phenyethylamine and piperidine alkaloids in Aloe species Planta Med. 58 1992 84 86
54. N.Z. Nyazema Poisoning due to traditional remedies Centr. African J. Med. 30 1984 80 83
55. V. Ortigosa Zusammensetzung des Coniins Ann. Chem. Pharm. 42 1842 313 315
56. K.E. Panter Toxicoses in livestock from the hemlocks (Conium and Cicuta spp.) J. Animal Sci. 66 1988 2407 2413
57. O. Parry, and C. Matambo Some pharmacological actions of aloe extracts and Cassia abbreviata on rats and mice Centr. African J. Med. 38 1992 409 414
58. O. Parry, and J. Wenyika The uterine effect of Aloe chabaudii Fitoterapia 65 1994 253 259
59. C.W. Pennington Tarahumar fish stupefaction plants Econ. Bot. 12 1958 95 102
60. F.B. Power, and F. Tutin Chemical examination of Aethusa cynapium J. Am. Chem. Soc. 27 1905 1461 1476
61. R.F. Raffauf A handbook of alkaloids and alkaloid-containing plants 1970 Wiley New York, London, Sydney, Toronto
62. G.W. Reynolds The Aloes of tropical Africa and Madagascar 1966 The Aloes Book Fund Mbane, Swaziland
63. T. Reynolds Observations on the phytochemistry of the Aloe leaf-exudate compounds Bot. J. Linn. Soc. 90 1985 179 199
64. T. Reynolds T. Reynolds Aloes - the genus Aloe 2004 CRC Press Boca Raton 39 74
65. M.F. Roberts The formation of γ-coniceine from 5-ketooctanal by a transaminase of Conium maculatum Phytochemistry 10 1971 3057 3060
66. M.F. Roberts Origin of the methyl carbon of methylconiine in Conium maculatum Phytochemistry 13 1974 1841 1845
67. M.F. Roberts S-adenosyl-l-methionine-coniine methyl transferase from Conium maculatum Phytochemistry 13 1974 1847 1851
68. M.F. Roberts γ-coniceine reductase in Conium maculatum Phytochemistry 14 1975 2393 2397
69. M.F. Roberts Purification and properties of l-alanine-4-ketooctanal aminotransferase from Conium maculatum Phytochemistry 16 1977 1381 1386
70. M.F. Roberts Separation of formation of γ-coniceine and aliphatic amines from GOT activity in Conium maculatum Phytochemistry 17 1978 107 112
71. M.F. Roberts An alkaloid from Conium maculatum Planta Med. 39 1980 216
72. M.F. Roberts, and R.T. Brown A new alkaloid from South African Conium species Phytochemistry 20 1981 447 449
73. V.W. Rodwell Pipecolic acid H. Tabor C.W. Tabor Methods in enzymology vol. 17B 1971 Academic Press New York 174 199
74. J. von Braun Ueber die Trennung der Coniumalkaloïde Ber. Deutsch. Chem. Ges. 38 1905 3108 3112
75. A. von Planta, and A. Kekulé Beiträge zur Kenntnifs einiger flüchtigen Basen Ann. Chem. Pharm. 89 1854 129 155
76. T. Wertheim Ueber ein neues alkaloïd in Conium maculatum Justus Liebig's Ann. Chem. Pharm. 100 1856 328 339
77. R. Wolffenstein Ueber Conium-Alkaloïde Ber. Deutsch. Chem. Ges. 27 1894 2611 2615
78. R. Wolffenstein Ueber coniumalkaloide Ber. Deutsch. Chem. Ges. 28 1895 302 305
79. H.S. Yanai, and W.N. Lipscomb The structure of ψ-conhydrine Tetrahedron 6 1959 103 108