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Molecules 2011, 16(11), 9520-9533; doi:10.3390/molecules16119520

Acetylcholinesterase-inhibiting Alkaloids from Zephyranthes concolor

1,* , 2
1 Instituto de Química, Universidad Nacional Autónoma de México, Coyoacán, 04510, México, D.F., Mexico 2 AgroBioInstitute, 8 Dragan Tzankov Blvd., 1164 Sofia, Bulgaria 3 Département de Chimie et Biochimie, Université de Moncton, Moncton, NB E1A 3E9, Canada 4 Laboratori de Retrovirologia, Fundació Irsi Caixa, Hospital Universitari Germans Trias i Pujol. 08916-Badalona, Barcelona, Spain 5 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 / Revised: 27 October 2011 / Accepted: 7 November 2011 / Published: 15 November 2011
(This article belongs to the Special Issue Alkaloids: Novel Therapeutic Perspectives)
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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 alkaloids; chlidanthine; Zephyranthes concolor; amaryllidaceae
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

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