title: Acetylcholinesterase-inhibiting alkaloids from Zephyranthes concolor.
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.
authors.affiliation: Instituto de Química, Universidad Nacional Autónoma de México, Coyoacán, México, D.F., Mexico. chilpa@unam.mx
authors.forename: Ricardo
authors.initials: R
authors.lastname: Reyes-Chilpa
authors.forename: Strahil
authors.initials: S
authors.lastname: Berkov
authors.forename: Simón
authors.initials: S
authors.lastname: Hernández-Ortega
authors.forename: Christopher K
authors.initials: CK
authors.lastname: Jankowski
authors.forename: Sebastien
authors.initials: S
authors.lastname: Arseneau
authors.forename: Imma
authors.initials: I
authors.lastname: Clotet-Codina
authors.forename: José A
authors.initials: JA
authors.lastname: Esté
authors.forename: Carles
authors.initials: C
authors.lastname: Codina
authors.forename: Francesc
authors.initials: F
authors.lastname: Viladomat
authors.forename: Jaume
authors.initials: J
authors.lastname: Bastida
mesh_terms: D000110:Acetylcholinesterase / Q000378:metabolism*; D000470:Alkaloids / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D047151:Amaryllidaceae Alkaloids / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D000818:Animals; D000998:Antiviral Agents / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D002460:Cell Line; D002800:Cholinesterase Inhibitors / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D004593:Electrophorus; D005702:Galantamine / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D015497:HIV-1 / Q000187:drug effects; D006801:Humans; D006860:Hydrogen Bonding; D019668:Liliaceae / Q000033:anatomy & histology / Q000737:chemistry*; D008969:Molecular Sequence Data; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010936:Plant Extracts / Q000737:chemistry*; D014961:X-Ray Diffraction
chemical_list: D000470:Alkaloids; D047151:Amaryllidaceae Alkaloids; D000998:Antiviral Agents; D002800:Cholinesterase Inhibitors; D010936:Plant Extracts; C570765:chlidanthine; D005702:Galantamine; D000110:Acetylcholinesterase
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