Planta Med 2009; 75(12): 1351-1355
DOI: 10.1055/s-0029-1185575
Natural Product Chemistry
Letter
© Georg Thieme Verlag KG Stuttgart · New York

Three New Alkaloids from Galanthus nivalis and Galanthus elwesii

Strahil Berkov1 , María Cuadrado1 , Edison Osorio1 , Francesc Viladomat1 , Carles Codina1 , Jaume Bastida1
  • 1Departament de Productes Naturals, Biologia Vegetal i Edafologia, Facultat de Farmàcia, Universitat de Barcelona, Barcelona, Spain
Weitere Informationen

Publikationsverlauf

received November 14, 2008 revised February 27, 2009

accepted March 9, 2009

Publikationsdatum:
20. April 2009 (online)

Abstract

Phytochemical studies on Galanthus species resulted in the isolation of three new compounds: 3,3′-O-(3′,3′′-dihydroxybutanoyl)hamayne and 11,3′-O-(3′,3′′-dihydroxybutanoyl)hamayne from G. nivalis and 2-O-(3′-hydroxybutanoyl)lycorine from G. elwesii. Additionally, 3,11-O-(3′,3′′-dihydroxybutanoyl)hamayne, 3,11,3′-O-(3′,3′′,3′′′-trihydroxybutanoyl)hamayne, 8-O-demethylvasconine, tazettine, epimacronine, and ismine from G. nivalis; 2-O-(3′-acetoxybutanoyl)lycorine and incartine from G. elwesii; and hamayne, 11-O-(3′-hydroxybutanoyl)hamayne and lycorine from both species were isolated. Their structures were determined by EI‐MS, HR‐MS, CD, and 1D and 2D NMR (COSY, NOESY, HMQC, and HMBC) experiments.

References

  • 1 Unver N. New skeletons and new concepts in Amaryllidaceae alkaloids.  Phytochem Rev. 2007;  6 125-135
  • 2 Kalashnikov I. Alkaloids from Galanthus nivalis.  Khim Prirod Soedin. 1970;  6 380
  • 3 Berkov S, Codina C, Viladomat F, Bastida J. Alkaloids from Galanthus nivalis.  Phytochemistry. 2007;  68 1791-1798
  • 4 Berkov S, Reyes-Chilpa R, Codina C, Viladomat F, Bastida J. A revised NMR data of incartine: an alkaloid from Galanthus elwesii. .  Molecules. 2007;  12 1430-1435
  • 5 Heinrich M, Teoh H. Galanthamine from snowdrop – the development of a modern drug against Alzheimer's disease from local Caucasian knowledge.  J Ethnopharmacol. 2004;  92 147-162
  • 6 Viladomat F, Bastida J, Codina C, Campbell W, Mathee S. Alkaloids from Brunsvigia josephinae.  Phytochemistry. 1994;  35 809-812
  • 7 De Angelis G, Wildman W. Identification of Amaryllidaceae alkaloids utilizing ORD and CD spectroscopy.  Tetrahedron Lett. 1969;  9 729-732
  • 8 Bastida J, Lavilla R, Viladomat F. Chemical and biological aspects of Narcissus alkaloids. Cordell GA The alkaloids, Vol. 63. Amsterdam; Elsevier Scientific Publishing 2006: 87-179
  • 9 Toriizuka Y, Kinoshita E, Kogure N, Kitajima M, Ishiyama A, Otoguro K, Yamada H, Omura S, Takayama H. New lycorine-type alkaloid from Lycoris traubii and evaluation of antitrypanosomal and antimalarial activities of lycorine derivatives.  Bioorg Med Chem. 2008;  16 10182-10189
  • 10 Bastida J, Codina C, Peeters P, Rubiralta M, Orozco M, Luque F, Chhabra S. Alkaloids from Crinum kirkii.  Phytochemistry. 1995;  40 1291-1293
  • 11 Viladomat F, Bastida J, Tribó G, Codina C, Rubiralta M. Alkaloids from Narcissus bicolor.  Phytochemistry. 1990;  29 1307-1310
  • 12 McNulty J, Nair J, Codina C, Bastida J, Pandey S, Gerasimoff J, Griffin C. Selective apoptosis-inducing activity of crinum-type Amaryllidaceae alkaloids.  Phytochemistry. 2007;  68 1068-1074

Prof. Dr. Jaume Bastida

Departament de Productes Naturals, Biologia Vegetal i Edafologia
Facultat de Farmàcia
Universitat de Barcelona

Av. Joan XXIII s/n

08028 Barcelona

Spain

Telefon: + 34 9 34 02 02 68

Fax: + 34 9 34 02 90 43

eMail: jaumebastida@ub.edu