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Acetylcholinesterase-inhibiting Alkaloids from Zephyranthes concolor
Instituto de Química, Universidad Nacional Autónoma de México, Coyoacán, 04510, México, D.F., Mexico
AgroBioInstitute, 8 Dragan Tzankov Blvd., 1164 Sofia, Bulgaria
Département de Chimie et Biochimie, Université de Moncton, Moncton, NB E1A 3E9, Canada
Laboratori de Retrovirologia, Fundació Irsi Caixa, Hospital Universitari Germans Trias i Pujol. 08916-Badalona, Barcelona, Spain
Departament de Productes Naturals, Biología Vegetal i Edafologia, Facultat de Farmàcia, Universitat de Barcelona. Av. Diagonal 643, E-08028 Barcelona, Spain
* Authors to whom correspondence should be addressed.
Received: 17 October 2011; in revised form: 27 October 2011 / Accepted: 7 November 2011 / Published: 15 November 2011
(This article belongs to the Special Issue Alkaloids
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.
Keywords: alkaloids; chlidanthine; Zephyranthes concolor; amaryllidaceae
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Reyes-Chilpa, R.; Berkov, S.; Hernández-Ortega, S.; Jankowski, C.K.; Arseneau, S.; Clotet-Codina, I.; Esté, J.A.; Codina, C.; Viladomat, F.; Bastida, J. Acetylcholinesterase-inhibiting Alkaloids from Zephyranthes concolor. Molecules 2011, 16, 9520-9533.
Reyes-Chilpa R, Berkov S, Hernández-Ortega S, Jankowski CK, Arseneau S, Clotet-Codina I, Esté JA, Codina C, Viladomat F, Bastida J. Acetylcholinesterase-inhibiting Alkaloids from Zephyranthes concolor. Molecules. 2011; 16(11):9520-9533.
Reyes-Chilpa, Ricardo; Berkov, Strahil; Hernández-Ortega, Simón; Jankowski, Christopher K.; Arseneau, Sebastien; Clotet-Codina, Imma; Esté, José A.; Codina, Carles; Viladomat, Francesc; Bastida, Jaume. 2011. "Acetylcholinesterase-inhibiting Alkaloids from Zephyranthes concolor." Molecules 16, no. 11: 9520-9533.