Abstract:
:Twenty known Amaryllidaceae alkaloids of various structural types, and one undescribed alkaloid of narcikachnine-type, named narcieliine (3), have been isolated from fresh bulbs of Zephyranthes citrina. The chemical structures of the isolated alkaloids were elucidated by a combination of MS, HRMS, 1D and 2D NMR, and CD spectroscopic techniques, and by comparison with literature data. The absolute configuration of narcieliine (3) has also been determined. Compounds isolated in a sufficient quantity were evaluated for their in vitro acetylcholinesterase (AChE; E.C. 3.1.1.7), butyrylcholinesterase (BuChE; E.C. 3.1.1.8), and prolyl oligopeptidase (POP; E.C. 3.4.21.26) inhibition activities. Significant human AChE/BuChE (hAChE/hBuChE) inhibitory activity was demonstrated by the newly described alkaloid narcieliine (3), with IC50 values of 18.7 ± 2.3 µM and 1.34 ± 0.31 µM, respectively. This compound is also predicted to cross the blood-brain barrier (BBB) through passive diffusion. The in vitro data were further supported by in silico studies of 3 in the active site of hAChE/hBuChE.
journal_name
Bioorg Chemjournal_title
Bioorganic chemistryauthors
Kohelová E,Maříková J,Korábečný J,Hulcová D,Kučera T,Jun D,Chlebek J,Jenčo J,Šafratová M,Hrabinová M,Ritomská A,Malaník M,Peřinová R,Breiterová K,Kuneš J,Nováková L,Opletal L,Cahlíková Ldoi
10.1016/j.bioorg.2020.104567subject
Has Abstractpub_date
2020-12-19 00:00:00pages
104567eissn
0045-2068issn
1090-2120pii
S0045-2068(20)31865-4journal_volume
107pub_type
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