Amaryllidaceae alkaloids from Narcissus pseudonarcissus L. cv. Dutch Master as potential drugs in treatment of Alzheimer's disease.

Acetylcholinesterase / metabolism Alzheimer Disease / drug therapy Amaryllidaceae Alkaloids / chemistry Butyrylcholinesterase / metabolism Cholinesterase Inhibitors / chemistry Dose-Response Relationship, Drug Glycogen Synthase Kinase 3 beta / antagonists & inhibitors Humans Molecular Structure Narcissus / chemistry Neuroprotective Agents / chemistry Prolyl Oligopeptidases Serine Endopeptidases / metabolism Structure-Activity Relationship
Alkaloids Alzheimer's disease Amaryllidaceae Cholinesterase inhibition Glycogen synthase kinase-3β inhibition Narcimatuline Narcissus pseudonarcissus L. cv. Dutch master Prolyl oligopeptidase

Journal

Phytochemistry
ISSN: 1873-3700
Titre abrégé: Phytochemistry
Pays: England
ID NLM: 0151434

Informations de publication

Date de publication:
Sep 2019
Historique:
received: 07 03 2019
revised: 27 05 2019
accepted: 23 06 2019
pubmed: 2 7 2019
medline: 16 8 2019
entrez: 2 7 2019
Statut: ppublish

Résumé

Twenty-one known Amaryllidaceae alkaloids of various structural types and one undescribed alkaloid, named narcimatuline, have been isolated from fresh bulbs of Narcissus pseudonarcissus L. cv. Dutch Master. The chemical structures were elucidated by combination of MS, HRMS, 1D and 2D NMR spectroscopic techniques, and by comparison with literature data. Narcimatuline amalgamates two basic scaffolds of Amaryllidaceae alkaloids in its core, namely galanthamine and galanthindole. All isolated compounds were evaluated for their in vitro acetylcholinesterase (AChE), butyrylcholinesterase (BuChE), prolyl oligopeptidase (POP), and glycogen synthase kinase-3β (GSK-3β) inhibitory activities. The most interesting biological profile was demonstrated by newly isolated alkaloid narcimatuline.

Identifiants

DOI: 10.1016/j.phytochem.2019.112055 PMID: 31261031
pubmed: 31261031
pii: S0031-9422(19)30197-9
doi: 10.1016/j.phytochem.2019.112055
pii:
doi:

Substances chimiques

Amaryllidaceae Alkaloids 0
Cholinesterase Inhibitors 0
Neuroprotective Agents 0
Glycogen Synthase Kinase 3 beta EC 2.7.11.1
Acetylcholinesterase EC 3.1.1.7
Butyrylcholinesterase EC 3.1.1.8
Serine Endopeptidases EC 3.4.21.-
PREPL protein, human EC 3.4.21.26
Prolyl Oligopeptidases EC 3.4.21.26

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

112055

Informations de copyright

Copyright © 2019 Elsevier Ltd. All rights reserved.

Auteurs

Daniela Hulcová (D)

ADINACO Research Group, Department of Pharmaceutical Botany, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic; Department of Pharmacognosy, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic.

Jana Maříková (J)

Department of Organic and Bioorganic Chemistry, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic.

Jan Korábečný (J)

Department of Toxicoloxy and Military Pharmacy, Faculty of Military Health Sciences, University of Defence, Třebešská 1575, 500 05, Hradec Králové, Czech Republic; Department Biomedical Research Centre, University Hospital Hradec Kralove, Sokolska 581, 500 05, Hradec Králové, Czech Republic.

Anna Hošťálková (A)

ADINACO Research Group, Department of Pharmaceutical Botany, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic.

Daniel Jun (D)

Department of Toxicoloxy and Military Pharmacy, Faculty of Military Health Sciences, University of Defence, Třebešská 1575, 500 05, Hradec Králové, Czech Republic.

Jiří Kuneš (J)

Department of Organic and Bioorganic Chemistry, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic.

Jakub Chlebek (J)

ADINACO Research Group, Department of Pharmaceutical Botany, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic.

Lubomír Opletal (L)

ADINACO Research Group, Department of Pharmaceutical Botany, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic.

Angela De Simone (A)

Department for Life Quality Studies, University of Bologna, Corso D'Augusto 237, 47921, Rimini, Italy.

Lucie Nováková (L)

Department of Analytical Chemistry, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic.

Vincenza Andrisano (V)

Department for Life Quality Studies, University of Bologna, Corso D'Augusto 237, 47921, Rimini, Italy.

Aleš Růžička (A)

Department of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, Studentská 95, 532 10, Pardubice, Czech Republic.

Lucie Cahlíková (L)

ADINACO Research Group, Department of Pharmaceutical Botany, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05, Hradec Králové, Czech Republic. Electronic address: cahlikova@faf.cuni.cz.

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Classifications MeSH

questionsmedicales.fr › Enzymes et coenzymes › Enzymes › Hydrolases › Esterases › Carboxylic ester hydrolases › Cholinesterases › Acetylcholinesterase › Amaryllidaceae alkaloids from Narcissus...
questionsmedicales.fr › Troubles mentaux › Troubles neurocognitifs › Démence › Maladie d'Alzheimer › Amaryllidaceae alkaloids from Narcissus...
questionsmedicales.fr › Composés hétérocycliques › Alcaloïdes › Alcaloïdes des Amaryllidaceae › Amaryllidaceae alkaloids from Narcissus...
questionsmedicales.fr › Enzymes et coenzymes › Enzymes › Hydrolases › Esterases › Carboxylic ester hydrolases › Cholinesterases › Butyrylcholine esterase › Amaryllidaceae alkaloids from Narcissus...
questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Effets physiologiques des médicaments › Agents neuromédiateurs › Agents cholinergiques › Anticholinestérasiques › Amaryllidaceae alkaloids from Narcissus...
questionsmedicales.fr › Phénomènes physiologiques › Phénomènes pharmacologiques et toxicologiques › Phénomènes toxicologiques › Relation dose-effet des médicaments › Amaryllidaceae alkaloids from Narcissus...
questionsmedicales.fr › Acides aminés, peptides et protéines › Protéines › Protéines et peptides de signalisation intracellulaire › Protein-Serine-Threonine Kinases › Proline-directed protein kinases › Glycogen Synthase Kinase 3 › Glycogen synthase kinase 3 beta › Amaryllidaceae alkaloids from Narcissus...
questionsmedicales.fr › Eucaryotes › Animaux › Chordés › Vertébrés › Mammifères › Eutheria › Primates › Haplorhini › Catarrhini › Hominidae › Humains › Amaryllidaceae alkaloids from Narcissus...
questionsmedicales.fr › Phénomènes chimiques › Structure moléculaire › Amaryllidaceae alkaloids from Narcissus...
questionsmedicales.fr › Eucaryotes › Viridiplantae › Streptophyta › Embryophyta › Tracheobionta › Magnoliopsida › Lilianae › Asparagales › Amaryllidaceae › Narcissus › Amaryllidaceae alkaloids from Narcissus...
questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Utilisations thérapeutiques › Agents du système nerveux central › Neuroprotecteurs › Amaryllidaceae alkaloids from Narcissus...
questionsmedicales.fr › Enzymes et coenzymes › Enzymes › Hydrolases › Peptide hydrolases › Endopeptidases › Prolyl-oligopeptidases › Amaryllidaceae alkaloids from Narcissus...
questionsmedicales.fr › Enzymes et coenzymes › Enzymes › Hydrolases › Peptide hydrolases › Protéases à sérine › Serine endopeptidases › Amaryllidaceae alkaloids from Narcissus...
questionsmedicales.fr › Phénomènes physiologiques › Phénomènes pharmacologiques et toxicologiques › Phénomènes pharmacologiques › Relation structure-activité › Amaryllidaceae alkaloids from Narcissus...