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Uncarialins A-I, Monoterpenoid Indole Alkaloids from Uncaria rhynchophylla as Natural Agonists of the 5-HT 1A Receptor.
- Source :
-
Journal of natural products [J Nat Prod] 2019 Dec 27; Vol. 82 (12), pp. 3302-3310. Date of Electronic Publication: 2019 Dec 02. - Publication Year :
- 2019
-
Abstract
- Nine new monoterpenoid indole alkaloids, uncarialins A-I ( 1 - 9 ), were isolated from Uncaria rhynchophylla as well as 14 known analogues ( 10 - 23 ). Their structures were determined by HRESIMS, 1D and 2D NMR, and experimental and calculated electronic circular dichroism data. Compounds 5 , 7 , 15 , and 22 displayed significant agonistic effects against the 5-HT <subscript>1A</subscript> receptor with EC <subscript>50</subscript> values of 2.2 ± 0.1, 0.1 ± 0.1, 1.6 ± 0.3, and 2.0 ± 0.5 μM, respectively. The mechanisms of action of these four compounds with the 5-HT <subscript>1A</subscript> receptor were investigated by molecular docking, and the results suggested that amino acid residues Asp116, Thr196, Asn386, and Tyr390 played critical roles in the observed activity of the above-mentioned compounds.
- Subjects :
- Animals
CHO Cells
Cricetulus
Molecular Docking Simulation
Molecular Structure
Secologanin Tryptamine Alkaloids chemistry
Secologanin Tryptamine Alkaloids isolation & purification
Serotonin Receptor Agonists chemistry
Serotonin Receptor Agonists isolation & purification
Spectrum Analysis methods
Receptor, Serotonin, 5-HT1A drug effects
Secologanin Tryptamine Alkaloids pharmacology
Serotonin Receptor Agonists pharmacology
Uncaria chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1520-6025
- Volume :
- 82
- Issue :
- 12
- Database :
- MEDLINE
- Journal :
- Journal of natural products
- Publication Type :
- Academic Journal
- Accession number :
- 31789520
- Full Text :
- https://doi.org/10.1021/acs.jnatprod.9b00532