Two new isoquinoline alkaloids, named fumaranine (2) and fumarostrejdine (10), along with 18 known alkaloids were isolated from aerial parts of Fumaria officinalis. The structures of the isolated compounds were elucidated on the basis of spectroscopic analyses and by comparison with literature data. The absolute configuration of the new compound 2 was determined by comparing its circular dichroism spectra with those of known analogs. Compounds isolated in sufficient amounts were evaluated for their acetylcholinesterase, butyrylcholinesterase, prolyl oligopeptidase (POP), and glycogen synthase kinase-3β inhibitory activities. Parfumidine (8) and sinactine (15) exhibited potent POP inhibition activities (IC50 99±5 and 53±2 μM, resp.).
- MeSH
- acetylcholinesterasa metabolismus MeSH
- alkaloidy chemie izolace a purifikace farmakologie MeSH
- Alzheimerova nemoc farmakoterapie enzymologie MeSH
- butyrylcholinesterasa metabolismus MeSH
- Fumaria chemie MeSH
- inhibitory enzymů chemie izolace a purifikace farmakologie MeSH
- isochinoliny chemie izolace a purifikace farmakologie MeSH
- kinasa 3 glykogensynthasy antagonisté a inhibitory metabolismus MeSH
- lidé MeSH
- molekulární struktura MeSH
- serinové endopeptidasy metabolismus MeSH
- vztah mezi dávkou a účinkem léčiva MeSH
- vztahy mezi strukturou a aktivitou MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
Alzheimer's disease is the most common cause of dementia. Currently, acetylcholinesterase (AChE) inhibition is the most widely used therapeutic treatment. A large number of naturally occurring compounds have been found to inhibit AChE. In this report the mechanism of AChE inhibition of two Amaryllidaceae alkaloids, 8-O-demethylmaritidine (1) and undulatine (2), and their possible penetration across the blood-brain barrier have been studied. Both compounds act via a mixed inhibition mechanism. Based on the parallel artificial permeation assay (PAMPA) for the prediction of blood-brain barrier (BBB) penetration, only 2 should be able to cross the BBB by passive permeation.
- MeSH
- acetylcholinesterasa metabolismus MeSH
- alkaloidy amarylkovitých farmakologie MeSH
- Alzheimerova nemoc farmakoterapie MeSH
- biologický transport účinky léků MeSH
- cholinesterasové inhibitory farmakologie MeSH
- hematoencefalická bariéra účinky léků MeSH
- lidé MeSH
- molekulární struktura MeSH
- techniky in vitro MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
A new isoquinoline-isoquinolone alkaloid was isolated from the root bark of Berberis vulgaris and named berbanine. The structure was established by spectroscopic methods (including 2D NMR, HR-EI-MS).
The genera Eschscholtzia and Argemone (Papaveraceae) represent a rich source of pavinane alkaloids, the identification of which in alkaloid extracts is generally problematic without standards. The alkaloid extracts of three Argemone and four Eschscholtzia species were analyzed using GC-MS. The alkaloids were identified based on comparison of their mass spectra with commercial libraries, with reported data in the literature and with spectra of reference compounds. A total of 23 alkaloids of six structural types (pavinane, protopine, benzylisoquinoline, benzophenanthridine, aporphine and protoberberine) were identified. The fragmentation pathway of pavinane alkaloids was used for their identification. O-Methylneocaryachine has been reported for the first time from a natural sources and the alkaloid pattern of Eschscholzia pulchella has been analyzed and described for the first time.
- MeSH
- alkaloidy analýza izolace a purifikace MeSH
- Argemone chemie MeSH
- benzylisochinoliny analýza izolace a purifikace MeSH
- Eschscholzia chemie MeSH
- listy rostlin chemie MeSH
- plynová chromatografie s hmotnostně spektrometrickou detekcí MeSH
- referenční standardy MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
Amaryllidaceae species are known as ornamental plants. Some contain galanthamine, an acetylcholinesterase inhibitor. The chemical composition of the alkaloid extract of bulbs of Nerine bowdenii Watson has been analyzed by means of GC/MS. Twenty-two compounds were detected and nineteen of them identified, one of which was belladine. The alkaloid extract showed promising cholinesterase inhibitory activities against human blood acetylcholinesterase (HuAChE; IC50 = 87.9 +/- 3.5 microg/mL) and human plasma butyrylcholinesterase (HuBuChE; IC50 = 14.8 +/- 1.1 microg/mL). Belladine inhibited HuAChE and HuBuChE in a dose-dependent manner with IC50 values of 781 +/- 12.5 microM and 284.8 +/-4.2 microM, respectively.
- MeSH
- alkaloidy chemie izolace a purifikace farmakologie MeSH
- cholinesterasové inhibitory chemie izolace a purifikace farmakologie MeSH
- lidé MeSH
- liliovité chemie MeSH
- plynová chromatografie s hmotnostně spektrometrickou detekcí MeSH
- rostlinné extrakty analýza MeSH
- vztah mezi dávkou a účinkem léčiva MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
