Crinine-type alkaloids from Hippeastrum aulicum and H. calyptratum

Crinine-type alkaloids from Hippeastrum aulicum and H. calyptratum

Crinine-, haemanthamine- and homolycorine-type alkaloids are described from the genus Hippeastrum by means of NMR, X-ray crystallography and CD spectroscopy. Crinine alkaloids are reported for the first time in this genus. •Twenty-three alkaloids were identified in Hippeastrum aulicum and H. calyptr...

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Bibliographic Details
Published in:Phytochemistry (Oxford) Vol. 103; pp. 188 - 195
Main Authors: de Andrade, Jean Paulo, Guo, Ying, Font-Bardia, Mercè, Calvet, Teresa, Dutilh, Jullie, Viladomat, Francesc, Codina, Carles, Nair, Jerald J., Zuanazzi, Jose A. Silveira, Bastida, Jaume
Format: Journal Article
Language:English
Published: England Elsevier Ltd 01-07-2014
Subjects:
Alkaloid
Alkaloids - chemistry
Amaryllidaceae
Amaryllidaceae Alkaloids - chemistry
Circular dichroism
Crinine-type
Crystallography, X-Ray
Hippeastrum
Liliaceae - chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Plant Extracts - chemistry
X-ray crystallography
Hippeastrum
X-ray crystallography
Alkaloid
Crinine-type
Amaryllidaceae
Circular dichroism
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Summary:Crinine-, haemanthamine- and homolycorine-type alkaloids are described from the genus Hippeastrum by means of NMR, X-ray crystallography and CD spectroscopy. Crinine alkaloids are reported for the first time in this genus. •Twenty-three alkaloids were identified in Hippeastrum aulicum and H. calyptratum.•X-ray and CD analysis confirmed that aulicine (1) is a crinine-type alkaloid.•CD analysis verified 3-O-methyl-epimacowine (2) as a crinine-type alkaloid.•Correct 1D and 2D NMR spectral data were assigned for the alkaloid 11-oxohaemanthamine (3).•Complete NMR data are presented for some trimethoxyaryl homolycorine-type alkaloids. 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.
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ISSN:0031-9422
1873-3700
DOI:10.1016/j.phytochem.2014.03.007