Planta Med 2001; 67(2): 191-193
DOI: 10.1055/s-2001-11495
Letter

© Georg Thieme Verlag Stuttgart · New York

Crinane and Lycorane Type Alkaloids from Zephyranthes citrina

María R. Herrera1 , Alex K. Machocho1 , Reto Brun2 , Francesc Viladomat1 , Carles Codina1 , Jaume Bastida1,*
  • 1 Departament de Productes Naturals, Facultat de Farmàcia, Universitat de Barcelona, Barcelona, Spain
  • 2 Swiss Tropical Institute, Protozoology Laboratory, Basel, Switzerland
Further Information

Publication History

March 30, 2000

May 13, 2000

Publication Date:
31 December 2001 (online)

Abstract

Eight alkaloids have been isolated from Zephyranthes citrina (Amaryllidaceae). The alkaloid oxomaritidine is reported here for the first time from a natural source. The structure and stereochemistry of the alkaloids were determined by physical and spectroscopic methods.

References

  • 1 Müller-Doblies D, Müller-Doblies U. Tribes, subtribes and some species combinations in Amaryllidaceae.  Feddes Repertorium. 1996;  107 1-9
  • 2 León Hno. Contribuciones Ocasionales del Museo de Historia Natural de Salle.  In: Flora de Cuba I. La Habana, Cuba; 1946: 441
  • 3 Watt J M, Breyer-Brandwijk M G. The medicinal and poisonous plants of southern and eastern Africa. Edinburgh, London; E. and S. Livingston, Ltd. 1962
  • 4 Trimiño Z, Castillo M, Spenglers I. Estudio Preliminar de Zephyranthes eggersiana Urban.  Revista Cubana de Farmacia. 1989;  23 147-50
  • 5 Keisuke K, Motoh M, Makoto I, Yukio O. Two alkaloids from Zephyranthes carinata .  Phytochemistry. 1998;  48 1199-202
  • 6 Boit H G, Döpke W, Stender W. Alkaloide aus Crinum, Zephyranthes, Leucojum und Clivia Arten.  Chemische Berichte. 1957;  90 2203-6
  • 7 Jiménez A, Santos A, Alonso G, Vázquez D. Inhibitors of protein synthesis in eukaryotic cells. Comparative effects of some Amaryllidaceae alkaloids.  Biochimica et Biophysica Acta. 1976;  425 342-8
  • 8 Weniger B, Italiano L, Beck J P, Bastida J, Bergoñón S, Codina C, Lobstein A, Anton R. Cytotoxic activity of Amaryllidaceae alkaloids.  Planta Medica. 1995;  61 77-9
  • 9 Antoun M D, Mendoza N T, Ríos Y R. Cytotoxicity of Hymenocallis expansa alkaloids.  Journal of Natural Products. 1993;  56 1423-5
  • 10 Evidente A, Cicala M R, Randazzo G, Riccio R, Calabrese G, Liso R, Arrigori O. Lycorine structure-activity relationships.  Phytochemistry. 1983;  22 2193-6
  • 11 Alarcón M, Cea G, Weigert G. Clastogenic effect of hippeastidine (HIPP) (1,2,3,4,4a,6-hexahydro-10-hydroxy-3,8,9-trimethoxy-5,10b- ethanophenanthridine).  Bulletin of Environmental Contamination and Toxicology. 1986;  37 508-12
  • 12 Wagner J, Pham H L, Döpke W. Alkaloids from Hippeastrum equestre Herb.-5. Circular Dichroism Studies.  Tetrahedron. 1996;  52 6591
  • 13 Ghosal S, Ashutosh. Razdan S. (+)-Epimaritidine, an alkaloid from Zephyranthes rosea .  Phytochemistry. 1985;  24 635-7
  • 14 Ali A A, El Sayed H M, Abdallah O M, Steglich W. Oxocrinine and other alkaloids from Crinum americanum .  Phytochemistry. 1986;  25 2399-401
  • 15 Bax A, Summers M F. 1H and 13C Assignments from sensitivity-enhanced detection of heteronuclear multiple-bond connectivity by 2D multiple quantum NMR.  Journal of the American Chemical Society. 1986;  108 2093-4
  • 16 Bastida J, Codina C, Viladomat F, Rubiralta M, Quirion J C, Husson H P, Ma G E. Narcissus alkaloids, XIII. Complete assignment of the NMR spectra of papyramine and 6-epi-papyramine by two-dimensional NMR spectroscopy.  Journal of Natural Products. 1990;  53 1456-62
  • 17 Frahm A W, Ali A A, Ramadan M A. 13C nuclear magnetic resonance spectra of Amaryllidacea alkaloids. I Alkaloids with the crinane skeleton.  Magnetic Resonance in Chemistry. 1985;  23 804-8
  • 18 Pabuççuoglu V, Richomme P, Gözler T, Kivçak B, Freyer A J, Shamma M. Four new crinine-type alkaloids from Sternbergia species.  Journal of Natural Products. 1989;  52 785-91
  • 19 Likhitwitayawuid K, Angerhofer C K, Chai H, Pezzuto J M, Cordell A G, Ruangrungsi N. Cytotoxic and antimalarial alkaloids from the bulbs of Crinum amabile .  Journal of Natural Products. 1993;  56 1331-8
  • 20 Kihara M, Ozak T, Kobayashi S, Shingu T. Alkaloidal constituents of Leucojum autumnale L. (Amaryllidaceae).  Chemical and Pharmaceutical Bulletin. 1995;  43 318-20

Dr. Jaume Bastida

Departament de Productes Naturals

Facultat de Farmàcia

Universitat de Barcelona

Avda. Diagonal 643

08028-Barcelona

Spain

Email: bastida@farmacia.far.ub.es

Fax: 34-93.402.90.43

Phone: Tel.: 34-93.402.44.93