1. Academic Validation
  2. Acetylcholinesterase-inhibiting alkaloids from Zephyranthes concolor

Acetylcholinesterase-inhibiting alkaloids from Zephyranthes concolor

  • Molecules. 2011 Nov 15;16(11):9520-33. doi: 10.3390/molecules16119520.
Ricardo Reyes-Chilpa 1 Strahil Berkov Simón Hernández-Ortega Christopher K Jankowski Sebastien Arseneau Imma Clotet-Codina José A Esté Carles Codina Francesc Viladomat Jaume Bastida
Affiliations

Affiliation

  • 1 Instituto de Química, Universidad Nacional Autónoma de México, Coyoacán, México, D.F., Mexico. chilpa@unam.mx
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 (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.

Figures
Products