Acetylcholinesterase-inhibiting Alkaloids from Zephyranthes concolor

作者：Reyes Chilpa Ricardo^*; Berkov Strahil; Hernandez Ortega Simon; Jankowski Christopher K; Arseneau Sebastien; Clotet Codina Imma; Este Jose A; Codina Carles; Viladomat Francesc; Bastida Jaume

来源：Molecules, 2011, 16(11): 9520-9533.

DOI：10.3390/molecules16119520

• alkaloids
• chlidanthine
• Zephyranthes concolor
• amaryllidaceae

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 x 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.

• 出版日期2011-11