Alkaloids of Datura ferox from Argentina
Chromatographic procedures (HPLC, GC-MS) are outlined in this paper for the analysis of alkaloids in poisonous Datura ferox seeds of Argentina, from which previously only quantitative analysis for scopolamine was known. Five additional tropane alkaloids are now identified as 3α-tigloyloxytropane (ti...
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1995
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| Sumario: | Chromatographic procedures (HPLC, GC-MS) are outlined in this paper for the analysis of alkaloids in poisonous Datura ferox seeds of Argentina, from which previously only quantitative analysis for scopolamine was known. Five additional tropane alkaloids are now identified as 3α-tigloyloxytropane (tigloyltropeine), 3-phenylacetoxy-6β,7β-epoxytropane (3-phenylacetoxyscopine), aposcopolamine (apohyoscine), 7β-hydroxy-6β-propenyloxy-3α-tropoyloxytropane, traces of 7β-hydroxy-6β-isovaleroyloxy-3α-tigloyloxytropane and a pyrrolidine alkaloid, hygrine. Two new structures, 3-phenylacetoxy-6β,7β-epoxytropane (3-phenylacetoxyscopine) and 7β-hydroxy-6β-propenyloxy-3α-tropoyloxytropane, are proposed on the basis of their spectra. Hyoscyamine, nicotine and tropane N-oxides were not detected in all samples studied. © 1995. |
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| Bibliografía: | Al-Said, Evans, Grout, Alkaloids of the genus Erythroxylum Part 5 Erythroxylum hypericifolium Lam root-bark (1986) Journal of the Chemical Society, Perkin Transactions 1, 1, pp. 957-959 Belton, Gibbons, Datura intoxication in West Cornwall (1979) British Medical Journal, 1, pp. 585-586 Blossey, Budzikiewicz, Ohashi, Fodor, Djerassi, Mass spectrometry in structural and stereochemical problems-XXXIX. Tropane alkaloids (1964) Tetrahedron, 20, pp. 585-595 Cabrera, Solanaceae (1965) Colección Científica de INTA, 4, pp. 235-237. , A.L. Cabrera, Flora de la Provincia de Buenos Aires, Part 5, Buenos Aires Carpano, Spegazzini, Najera, Parameters for the micrographic characterization of Solanaceae used to prepare psychoactive infusions and fumatories (1990) Acta Farmacéutica Bonaerense, 9, pp. 101-109 Clissold, Heel, Transdermal hyoscine (scopolamine): preliminary review of its pharmacodynamic properties and therapeutic efficacy (1985) Drugs, 29, pp. 189-207 Dewhurst, Kaminski, Supple, Mass spectra of some tropane and tropinidine derivatives (1972) Journal of Heterocyclic Chemistry, 9, pp. 507-511 Domínguez, (1928) Contribuciones a la Materia Médica Argentina, p. 120. , (1st. Contribution). Buenos Aires Domínguez, (1928) Contribuciones a la Materia Médica Argentina, pp. 194-196. , (1st. Contribution). Buenos Aires Ethier, Neville, Quadrupole EI and CI mass spectra of some principal tropane alkaloids (1986) Canadian Journal of Spectroscopy, 31, pp. 81-88 Evans, Major, The alkaloids of the genus Datura. Part V. Alkaloids of Datura sanguinea R. and P. and related esters of tropane-3α,6β,7β-triol (1968) Journal of the Chemical Society, 100, pp. 2775-2778 Evans, Lampard, Alkaloids of the genus Datura section Brugmansia. VIII. Alkaloids of Datura suaveolens (1972) Phytochemistry, 11, pp. 3293-3298 Evans, Tropane Alkaloids of the Solanaceae (1979) The Biology and Taxonomy of the Solanaceae, pp. 241-254. , J.G. Hawkes et al., Linnean Society Symposium Series No. 7, Academic Press, London Evans, Hybridization and secondary metabolites in the Solanaceae (1986) Solanaceae. Biology and Systematics, pp. 179-180. , W.G. D'Arcy, Columbia University Press, New York Evans, Datura, a commercial source of hyoscine (1990) Pharm. Journal, 244, pp. 651-653 Gallo, (1987) Plantas Tóxicas para el Ganado en el Cono Sur de América, p. 87. , Ed. Hemisferio Sur, Buenos Aires Gordon, Shupak, Doweck, Spitzer, Allergic contact dermatitis caused by transdermal hyoscine (1989) British Medical Journal, 298, pp. 1220-1221 Gowdy, Stramonium intoxication: review of symptomatology in 212 cases (1972) Journal of the American Medical Association, 221, pp. 585-587 Hall, McHenry, Popkin, Angel's Trumpet psychosis: central nervous system anticholinergic syndrome (1977) American Journal of Psychiatry, 134, pp. 312-314 Hegnauer, (1973) Chemotaxonomie der Pflanzen, 6, pp. 407-408. , Birkhäuser Verlag, Basel and Stuttgart Hegnauer, (1973) Chemotaxonomie der Pflanzen, 6, p. 443. , Birkhäuser Verlag, Basel and Stuttgart Hegnauer, (1973) Chemotaxonomie der Pflanzen, 6, p. 788. , Birkhäuser Verlag, Basel and Stuttgart Hegnauer, (1973) Chemotaxonomie der Pflanzen, 6, p. 795. , Birkhäuser Verlag, Basel and Stuttgart Hegnauer, (1990) Chemotaxonomie der Pflanzen, 9, pp. 567-571. , Birkhäuser Verlag, Basel, Boston and Berlin Hegnauer, (1990) Chemotaxonomie der Pflanzen, 9, p. 577. , Birkhäuser Verlag, Basel, Boston and Berlin Hegnauer, (1990) Chemotaxonomie der Pflanzen, 9, p. 587. , Birkhäuser Verlag, Basel, Boston and Berlin Hegnauer, (1990) Chemotaxonomie der Pflanzen, 9, p. 589. , Birkhäuser Verlag, Basel, Boston and Berlin Janowsky, El-Yousef, Davis, Sekerke, Cholinergic-adrenergic hypothesis of mania and depression (1972) Lancet, 2, pp. 632-635 Kagei, Ikeda, Sato, Ogata, Kunii, Toyoshima, Matsuura, Studies on Duboisia species. IV. Minor alkaloids in leaves of Duboisia leichhardtii (1980) Yakugaku Zashi, 100, pp. 216-220 (1980) Chemical Abstracts, 92, p. 194445s Lewis, Elvin-Lewis, (1977) Medical Botany, p. 54. , John Wiley & Sons, New York Lewis, Elvin-Lewis, (1977) Medical Botany, p. 86. , John Wiley & Sons, New York Lewis, Elvin-Lewis, (1977) Medical Botany, p. 98. , John Wiley & Sons, New York Lewis, Elvin-Lewis, (1977) Medical Botany, p. 167. , John Wiley & Sons, New York Lewis, Elvin-Lewis, (1977) Medical Botany, p. 223. , John Wiley & Sons, New York Lewis, Elvin-Lewis, (1977) Medical Botany, p. 276. , John Wiley & Sons, New York Lewis, Elvin-Lewis, (1977) Medical Botany, p. 296. , John Wiley & Sons, New York Lewis, Elvin-Lewis, (1977) Medical Botany, p. 300. , John Wiley & Sons, New York Lewis, Elvin-Lewis, (1977) Medical Botany, p. 330. , John Wiley & Sons, New York Lounasmaa, The Tropane Alkaloids (1988) The Alkaloids, 33, pp. 1-81. , A. Brossi, Academic Press, San Diego Mahler, Jimson weed high (1975) Journal of the American Medical Association, 231, p. 138 Padula, Bandoni, Rondina, Coussio, Quantitative determination of total alkaloids and scopolamine in Datura ferox growing in Argentina (1976) Planta Medica, 29, pp. 357-360 Parello, Longevialle, Vetter, McCloskey, Structure de la phyllalbine (1963) Application de la résonance magnétique nucléaire et de la spectrométrie de masse à l'étude des dérivés du tropane, pp. 2787-2793. , Bulletin de la Societé Chimique de la France Parodi, Descripción de las plantas cultivadas (1959) Enciclopedia Argentina de Agricultura y Jardineria, 1, p. 761. , Ed. ACME SACI, Buenos Aires Phillipson, Handa, N-oxides of hyoscyamine and hyoscine in the Solanaceae (1975) Phytochemistry, 14, pp. 999-1003 Ragonese, Milano, Part 8-2: Vegetales y Sustancias Tóxicas de la Flora Argentina (1984) Enciclopedia Argentina de Agricultura y Jardinería, 2, p. 20. , Ed. ACME SACI, Buenos Aires Ragonese, Milano, Part 8-2: Vegetales y Sustancias Tóxicas de la Flora Argentina (1984) Enciclopedia Argentina de Agricultura y Jardinería, 2, pp. 268-270. , Ed. ACME SACI, Buenos Aires Ratera, (1973) Guía Bibliográfica de las Plantas Tóxicas para el Ganado en la República Argentina, pp. 54-56. , Ed. Cesarini Hnos, Buenos Aires Romeike, Zur Frage der Alkaloidumwandlung im Spross (1955) Naturwissenschaften, 42, pp. 631-632 Romeike, Uber Mitwirkung des Sprosses bei der Ausbildung des Alkaloids Spektrums (1956) Epoxydbildung beim Hyoscyamin durch Datura ferox, 143, pp. 67-86. , Flora (Jena) Romeike, Hyoscyamin-Epoxydierung bei einer Artkreuzung von Datura (1958) Planta Medica, 6, pp. 426-427 Romeike, Zur Biogenese des Skopolamins (1959) Naturwissenschaften, 46, pp. 492-493 Romeike, Uber Mitwirkung des Sprosses bei der Ausbildung des Alkaloids Spektrums. II Bildungsstätte und Biogenese des Scopolamins in Datura ferox L. (1959) Flora (Jena), 148, pp. 306-320 Romeike, Scopolaminbildung in der Artkreuzung Datura ferox L. × Datura stramonium L. (1961) Die Kulturpflanze, 9, pp. 171-180 Romeike, Ein Modell für die Entstehungsweise chemischer Rassen (1966) Die Kulturpflanze, 14, pp. 129-135 Safer, Allen, Central effects of scopolamine in man (1971) Biological Psychiatry, 3, pp. 347-355 Safford, Daturas of the Old World and New: an Account of their Narcotic Properties and their use in oracular and initiatory ceremonies (1922) Annual Reports of the Smithsonian Institute, 1920, pp. 537-567 Sastry, (1972) Biochemical Applications of Mass Spectrometry, p. 655. , G.R. Waller, Wiley Interscience, New York Schultes, Hofmann, (1973) The Botany and Chemistry of Hallucinogens, pp. 166-171. , Charles C. Thomas Publisher, Springfield, Illinois Schultes, Hofmann, (1973) The Botany and Chemistry of Hallucinogens, p. 176. , Charles C. Thomas Publisher, Springfield, Illinois Schultes, Hofmann, (1973) The Botany and Chemistry of Hallucinogens, p. 177. , Charles C. Thomas Publisher, Springfield, Illinois Sennhauser, Schwarz, Toxic psychosis from transdermal scopolamine in a child (1986) Lancet, 2, p. 1033 Shervette, Schydlower, Lampe, Fearnow, Jimson “loco” weed abuse in adolescents (1979) Pediatrics, 63, pp. 520-523 Shupak, Gordon, Spitzer, Mendelowitz, Melamed, Three-years' experience of transdermal scopolamine: long-term effectiveness and side effects (1989) Pharmatherapeutica, 5, pp. 365-370 Tétényi, A chemotaxonomic classification of the Solanaceae (1987) Annals of the Missouri Botanical Garden, 74, pp. 600-608 |
| ISSN: | 03788741 |
| DOI: | 10.1016/0378-8741(95)90035-7 |