Crinine-type alkaloids from Hippeastrum aulicum and H. calyptratum

An ongoing search for alkaloids in the Amaryllidaceae species using GC MS resulted in the identification of two crinine-type alkaloids, aulicine (1) and 3-O-methyl-epimacowine, (2) from the indigenous Brazilian species Hippeastrum aulicum and Hippeastrum calyptratum, respectively. In addition, two a...

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Detalles Bibliográficos
Autores: de Andrade, Jean Paulo, Guo, Y., Font Bardia, Ma. Mercedes, Calvet Pallàs, Maria Teresa, Dutilh, J. H., Viladomat Meya, Francesc, Codina Mahrer, Carles, Nair, Jerald J., Zuanazzi, José Ângelo Silveira, Bastida Armengol, Jaume
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2014
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2445/169248
Acceso en línea:https://hdl.handle.net/2445/169248
Access Level:acceso abierto
Palabra clave:Alcaloides
Radiocristal·lografia
Alkaloids
X-ray crystallography
Descripción
Sumario:An ongoing search for alkaloids in the Amaryllidaceae species using GC MS resulted in the identification of two crinine-type alkaloids, aulicine (1) and 3-O-methyl-epimacowine, (2) from the indigenous Brazilian species Hippeastrum aulicum and Hippeastrum calyptratum, respectively. In addition, two alkaloids, 11-oxohaemanthamine (3) and 7-methoxy-O-methyllycorenine (4) were both isolated from H. aulicum. Furthermore, we provide here complete NMR spectroscopic data for the homolycorine analogues nerinine (5) and albomaculine (6). The absolute stereochemistry of the 5,10b-ethano bridge in the crinine variants was determined by circular dichroism and X-ray crystallographic analysis, thus presenting the first direct evidence for the presence of crinine-type alkaloids in the genus Hippeastrum.