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Molecules ; 16(11): 9520-33, 2011 Nov 15.
Artículo en Inglés | MEDLINE | ID: mdl-22086403

RESUMEN

The bulbs and aerial parts of Zephyranthes concolor (Lindl.) Benth. & Hook. f. (Amaryllidaceae), an endemic species to Mexico, were found to contain the alkaloids chlidanthine, galanthamine, galanthamine N-oxide, lycorine, galwesine, and epinorgalanthamine. Since currently only partial and low resolution (1)H-NMR data for chlidanthine acetate are available, and none for chlidanthine, its 1D and 2D high resolution (1)H- and (13)C-NMR spectra were recorded. Unambiguous assignations were achieved with HMBC, and HSQC experiments, and its structure was corroborated by X-ray diffraction. Minimum energy conformation for structures of chlidanthine, and its positional isomer galanthamine, were calculated by molecular modelling. Galanthamine is a well known acetylcholinesterase inhibitor; therefore, the isolated alkaloids were tested for this activity. Chlidanthine and galanthamine N-oxide inhibited electric eel acetylcholinesterase (2.4 and 2.6 × 10(-5) M, respectively), indicating they are about five times less potent than galanthamine, while galwesine was inactive at 10(-3) M. Inhibitory activity of HIV-1 replication, and cytotoxicity of the isolated alkaloids were evaluated in human MT-4 cells; however, the alkaloids showed poor activity as compared with standard anti-HIV drugs, but most of them were not cytotoxic.


Asunto(s)
Acetilcolinesterasa/metabolismo , Alcaloides/química , Inhibidores de la Colinesterasa/química , Liliaceae/química , Extractos Vegetales/química , Alcaloides/metabolismo , Alcaloides/farmacología , Alcaloides de Amaryllidaceae/química , Alcaloides de Amaryllidaceae/metabolismo , Alcaloides de Amaryllidaceae/farmacología , Animales , Antivirales/química , Antivirales/metabolismo , Antivirales/farmacología , Línea Celular , Inhibidores de la Colinesterasa/metabolismo , Inhibidores de la Colinesterasa/farmacología , Electrophorus , Galantamina/química , Galantamina/metabolismo , Galantamina/farmacología , VIH-1/efectos de los fármacos , Humanos , Enlace de Hidrógeno , Liliaceae/anatomía & histología , Datos de Secuencia Molecular , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Difracción de Rayos X
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