Alkaloids of Zephyranthes citrina (Amaryllidaceae) and their implication to Alzheimer's disease: Isolation, structural elucidation and biological activity.

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 Chem

journal_title

Bioorganic chemistry

authors

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 L

doi

10.1016/j.bioorg.2020.104567

subject

Has Abstract

pub_date

2020-12-19 00:00:00

pages

104567

eissn

0045-2068

issn

1090-2120

pii

S0045-2068(20)31865-4

journal_volume

107

pub_type

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