Subscribe to RSS
DOI: 10.1055/s-0029-1185575
© Georg Thieme Verlag KG Stuttgart · New York
Three New Alkaloids from Galanthus nivalis and Galanthus elwesii
Publication History
received November 14, 2008
revised February 27, 2009
accepted March 9, 2009
Publication Date:
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.
Key words
Galanthus nivalis - Galanthus elwesii - Amaryllidaceae - alkaloids - 3,3′‐O‐(3′,3′′‐dihydroxybutanoyl)hamayne - 11,3′‐O‐(3′,3′′‐dihydroxybutanoyl)hamayne - 2‐O‐(3′‐hydroxybutanoyl)lycorine
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
Phone: + 34 9 34 02 02 68
Fax: + 34 9 34 02 90 43
Email: jaumebastida@ub.edu