Crinine-type alkaloids from Hippeastrum aulicum and H-calyptratum

Paulo de Andrade, Jean; Guo, Ying; Font-Bardia, Merce; Calvet, Teresa; Dutilh, Jullie; Viladomat, Francesc; Codina, Carles; Nair, Jerald J.; Silveira Zuanazzi, Jose A.; Bastida, Jaume

Abstract

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. (c) 2014 Elsevier Ltd. All rights reserved.

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Título según WOS: ID WOS:000337777800023 Not found in local WOS DB
Título de la Revista: PHYTOCHEMISTRY
Volumen: 103
Editorial: Elsevier BV
Fecha de publicación: 2014
Página de inicio: 188
Página final: 195
DOI:

10.1016/j.phytochem.2014.03.007

Notas: ISI