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Title: Acetylcholinesterase-inhibiting alkaloids from Zephyranthes concolor
Author: Reyes-Chilpa, Ricardo
Berkov, Strahil
Hernández-Ortega, Simón
Jankowski, Christopher K.
Arseneau, Sebastien
Clotet-Codina, Imma
Esté, José A.
Codina Mahrer, Carles
Viladomat Meya, Francesc
Bastida Armengol, Jaume
Keywords: Alcaloides
Raigs X
VIH (Virus)
HIV (Viruses)
Issue Date: 15-Nov-2011
Publisher: MDPI
Abstract: 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 1H-NMR data for chlidanthine acetate are available, and none for chlidanthine, its 1D and 2D high resolution 1H- and 13C-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.
Note: Reproducció del document publicat a:
It is part of: Molecules, 2011, vol. 16, num. 11, p. 9520-9533
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ISSN: 1420-3049
Appears in Collections:Articles publicats en revistes (Biologia, Sanitat i Medi Ambient)

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