Acetylcholinesterase-inhibiting Alkaloids from Zephyranthes concolor

Molecules

Ricardo Reyes-Chilpa¹  Strahil Berkov¹  Simón Hernández-Ortega¹  Christopher K. Jankowski¹  Sebastien Arseneau¹  Imma Clotet-Codina¹  José A. Esté¹  Carles Codina¹  Francesc Viladomat¹ 

[1] ¹Instituto de Química, Universidad Nacional Autónoma de México, Coyoacán, 04510, México, D.F., Mexico

关键词: alkaloids;    chlidanthine;    Zephyranthes concolor;    amaryllidaceae;   

DOI  :  10.3390/molecules16119520

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
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.