Acetylcholinesterase-inhibiting Alkaloids from Zephyranthes concolor
Por:
Reyes-Chilpa, R, Berkov, S, Hernandez-Ortega, S, Jankowski, CK, Arseneau, S, Clotet-Codina, I, Este, JA, Codina, C, Viladomat, F and Bastida, J
Publicada:
1 nov 2011
Resumen:
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.
Filiaciones:
Reyes-Chilpa, R:
Univ Nacl Autonoma Mexico, Inst Quim, Mexico City 04510, DF, Mexico
Berkov, S:
AgroBioInstitute, Sofia 1164, Bulgaria
Hernandez-Ortega, S:
Univ Nacl Autonoma Mexico, Inst Quim, Mexico City 04510, DF, Mexico
Jankowski, CK:
Univ Moncton, Dept Chim & Biochim, Moncton, NB E1A 3E9, Canada
Arseneau, S:
Univ Moncton, Dept Chim & Biochim, Moncton, NB E1A 3E9, Canada
Clotet-Codina, I:
Hosp Badalona Germans Trias & Pujol, Fundacio Irsi Caixa, Lab Retrovirol, Barcelona 08916, Spain
:
Hosp Badalona Germans Trias & Pujol, Fundacio Irsi Caixa, Lab Retrovirol, Barcelona 08916, Spain
Codina, C:
Univ Barcelona, Fac Farm, Dept Prod Nat Biol Vegetal & Edafol, E-08028 Barcelona, Spain
Viladomat, F:
Univ Barcelona, Fac Farm, Dept Prod Nat Biol Vegetal & Edafol, E-08028 Barcelona, Spain
Bastida, J:
Univ Barcelona, Fac Farm, Dept Prod Nat Biol Vegetal & Edafol, E-08028 Barcelona, Spain
Green Submitted, Green Published, gold
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