Alkaloids from Nerine filifolia

The alkaloids N-demethylbelladine, 6α-methoxybuphanidrine and filifoline are described for the first time from bulbs of Nerine filifolia (Amaryllidaceae). The nicotinate ester in filifoline was observed to reverse molecular ellipticity as expressed in the shape of the CD curve. The novel compounds N...

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Bibliographic Details
Published in:Phytochemistry (Oxford) 2005-02, Vol.66 (3), p.373-382
Main Authors: Nair, Jerald J., Campbell, William E., Brun, Reto, Viladomat, Francesc, Codina, Carles, Bastida, Jaume
Format: Article
Language:English
Subjects:
11- O-Acetylambelline
6α-Hydroxybuphanidrine
6α-Methoxybuphanidrine
Alkaloids
Amaryllidaceae
Amaryllidaceae Alkaloids - chemistry
Amaryllidaceae Alkaloids - isolation & purification
Ambelline
Belladine
Biological and medical sciences
Bulbs
Chemical constitution
chemical structure
Circular Dichroism
Filifoline
Fundamental and applied biological sciences. Psychology
General pharmacology
Leishmania donovani
Liliaceae
Liliaceae - chemistry
Magnetic Resonance Spectroscopy
Medical sciences
Molecular Structure
N-Demethylbelladine
Nerine filifolia
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Phenol
phytochemicals
plant extracts
Plant physiology and development
Plasmodium falciparum
spectral analysis
Trypanosoma cruzi
Trypanosoma rhodesiense
Undulatine
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Summary:The alkaloids N-demethylbelladine, 6α-methoxybuphanidrine and filifoline are described for the first time from bulbs of Nerine filifolia (Amaryllidaceae). The nicotinate ester in filifoline was observed to reverse molecular ellipticity as expressed in the shape of the CD curve. The novel compounds N-demethylbelladine, 6α-methoxybuphanidrine and filifoline, in addition to five known alkaloids, and phenol have been isolated from fresh bulbs of Nerine filifolia (Amaryllidaceae). The structure and stereochemistry of the compounds were determined by physical and spectroscopic methods, including 1D and 2D NMR and mass spectroscopic techniques. An unusual circular dichroism response from filifoline has required a semi-synthetic derivatisation strategy towards key C-11 endo analogues of the β-crinane representative ambelline in which the nature of substituents was observed to have a profound effect on molecular ellipticity. Filifoline was not cytotoxic to myoblast (L6) cells and exhibited no anti-protozoal activity in an in vitro screen against four different parasitic protozoa.
ISSN:0031-9422
1873-3700
DOI:10.1016/j.phytochem.2004.12.009