Monoterpene indole alkaloids from Vinca minor L. (Apocynaceae): Identification of new structural scaffold for treatment of Alzheimer's disease
Language English Country Great Britain, England Media print-electronic
Document type Journal Article
PubMed
34798410
DOI
10.1016/j.phytochem.2021.113017
PII: S0031-9422(21)00366-6
Knihovny.cz E-resources
- Keywords
- (−)-2-ethyl-3[2-(3-ethylpiperidinyl)-ethyl]-1H-indole, Alkaloids, Alzheimer's disease, Apocynaceae, Butyrylcholinesterase, Docking studies, Vinca minor, Vincaminorudeine,
- MeSH
- Acetylcholinesterase MeSH
- Alzheimer Disease * drug therapy MeSH
- Butyrylcholinesterase MeSH
- Phytochemicals pharmacology MeSH
- Indole Alkaloids pharmacology MeSH
- Glycogen Synthase Kinase 3 beta MeSH
- Monoterpenes pharmacology MeSH
- Plant Components, Aerial chemistry MeSH
- Vinca * chemistry MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- Acetylcholinesterase MeSH
- Butyrylcholinesterase MeSH
- Phytochemicals MeSH
- Indole Alkaloids MeSH
- Glycogen Synthase Kinase 3 beta MeSH
- Monoterpenes MeSH
One undescribed indole alkaloid together with twenty-two known compounds have been isolated from aerial parts of Vinca minor L. (Apocynaceae). The chemical structures of the isolated alkaloids were determined by a combination of MS, HRMS, 1D, and 2D NMR techniques, and by comparison with literature data. The NMR data of several alkaloids have been revised, corrected, and missing data have been supplemented. Alkaloids isolated in sufficient quantity were screened for their in vitro acetylcholinesterase (AChE; E.C. 3.1.1.7) and butyrylcholinesterase (BuChE; E.C. 3.1.1.8) inhibitory activity. Selected compounds were also evaluated for prolyl oligopeptidase (POP; E.C. 3.4.21.26), and glycogen synthase 3β-kinase (GSK-3β; E.C. 2.7.11.26) inhibition potential. Significant hBuChE inhibition activity has been shown by (-)-2-ethyl-3[2-(3-ethylpiperidinyl)-ethyl]-1H-indole with an IC50 value of 0.65 ± 0.16 μM. This compound was further studied by enzyme kinetics, along with in silico techniques, to reveal the mode of inhibition. This compound is also predicted to cross the blood-brain barrier (BBB) through passive diffusion.
Department for Life Quality Studies University of Bologna 47921 Rimini Italy
Department of Toxicology and Military Pharmacy Trebesska 1575 500 05 Hradec Kralove Czech Republic
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