Inhibition of human monoamine oxidase A and B by flavonoids isolated from two Algerian medicinal plants
- Publication type:
- Journal article
- Metadata:
-
- Autoren
- Farida Larit
- Khaled M Elokely
- Narayan D Chaurasiya
- Samira Benyahia
- Manal A Nael
- Francisco Leon
- Mohammad Sanad Abu-Darwish
- Thomas Efferth
- Yan-Hong Wang
- Djamila Belouahem-Abed
- Samir Benayache
- Babu L Tekwani
- Stephen J Cutler
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000426182000004&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1016/j.phymed.2017.12.032
- eISSN
- 1618-095X
- Externe Identifier
- Clarivate Analytics Document Solution ID: FX6GQ
- PubMed Identifier: 29496172
- ISSN
- 0944-7113
- Zeitschrift
- PHYTOMEDICINE
- Schlüsselwörter
- Antidepressant
- Bioassay-guided fractionation
- HR-ESI-MS
- Molecular docking
- Monoamine oxidase
- NMR
- Paginierung
- 27 - 36
- Datum der Veröffentlichung
- 2018
- Status
- Published
- Titel
- Inhibition of human monoamine oxidase A and B by flavonoids isolated from two Algerian medicinal plants
- Sub types
- Article
- Ausgabe der Zeitschrift
- 40
Data source: Web of Science (Lite)
- Other metadata sources:
-
- Autoren
- Farida Larit
- Khaled M Elokely
- Narayan D Chaurasiya
- Samira Benyahia
- Manal A Nael
- Francisco León
- Mohammad Sanad Abu-Darwish
- Thomas Efferth
- Yan-Hong Wang
- Djamila Belouahem-Abed
- Samir Benayache
- Babu L Tekwani
- Stephen J Cutler
- DOI
- 10.1016/j.phymed.2017.12.032
- ISSN
- 0944-7113
- Zeitschrift
- Phytomedicine
- Sprache
- en
- Paginierung
- 27 - 36
- Datum der Veröffentlichung
- 2018
- Status
- Published
- Herausgeber
- Elsevier BV
- Herausgeber URL
- http://dx.doi.org/10.1016/j.phymed.2017.12.032
- Datum der Datenerfassung
- 2021
- Titel
- Inhibition of human monoamine oxidase A and B by flavonoids isolated from two Algerian medicinal plants
- Ausgabe der Zeitschrift
- 40
Data source: Crossref
- Abstract
- <h4>Background</h4>Monoamine oxidases (MAOs) are outer mitochondrial membrane flavoenzymes. They catalyze the oxidative deamination of a variety of neurotransmitters. MAO-A and MAO-B may be considered as targets for inhibitors to treat neurodegenerative diseases and depression and for managing symptoms associated with Parkinson's and Alzheimer's diseases.<h4>Purpose</h4>The objective was to evaluate the inhibitory effect of Hypericum afrum and Cytisus villosus against MAO-A and B and to isolate the compounds responsible for the MAO-inhibitory activity.<h4>Methods</h4>The inhibitory effect of extracts and purified constituents of H. afrum and C. villosus were investigated in vitro using recombinant human MAO-A and B, and through bioassay-guided fractionation of ethyl acetate fractions of areal parts of the two plants collected in northeastern Algeria. In addition, computational protein-ligand docking and molecular dynamics simulations were carried out to explain the MAO binding at the molecular level.<h4>Results</h4>The ethyl acetate (EtOAc) fractions of H. afrum and C. villosus showed the highest MAO inhibition activity against MAO A and B with IC<sub>50</sub> values of 3.37 µg/ml and 13.50 µg/ml as well as 5.62 and 1.87 µg/ml, respectively. Bioassay-guided fractionation of the EtOAc fractions resulted in the purification and identification of the known flavonoids quercetin, myricetin, genistein and chrysin as the principal MAO-inhibitory constituents. Their structures were established by extensive 1 and 2D NMR studies and mass spectrometry. Quercetin, myricetin and chrysin showed potent inhibitory activity towards MAO-A with IC<sub>50</sub> values of 1.52, 9.93 and 0.25 µM, respectively, while genistein more efficiently inhibited MAO-B (IC<sub>50</sub> value: 0.65 µM). The kinetics of the inhibition and the study of dialysis dissociation of the complex of quercetin and myricetin and the isoenzyme MAO-A showed competitive and mixed inhibition, respectively. Both compounds showed reversible binding. Molecular docking experiments and molecular dynamics simulations allowed to estimate the binding poses and to identify the most important residues involved in the selective recognition of molecules in the MAOs enzymatic clefts.<h4>Conclusion</h4>Quercetin and myricetin isolated from H. afrum together with genistein and chrysin isolated from C. villosus have been identified as potent MAO-A and -B inhibitors. H. afrum and C. villosus have properties indicative of potential neuroprotective ability and may be new candidates for selective MAO-A and B inhibitors.
- Addresses
- Department of BioMolecular Sciences, School of Pharmacy, The University of Mississippi, University, MS 38677, United States; Département de Chimie, Faculté des Sciences Exactes, Université des Frères Mentouri, Constantine, Route d'Aine El Bey 25000, Constantine, Algeria. Electronic address: laritfarida@umc.edu.dz.
- Autoren
- Farida Larit
- Khaled M Elokely
- Narayan D Chaurasiya
- Samira Benyahia
- Manal A Nael
- Francisco León
- Mohammad Sanad Abu-Darwish
- Thomas Efferth
- Thomas Efferth
- Yan-Hong Wang
- Djamila Belouahem-Abed
- Samir Benayache
- Babu L Tekwani
- Stephen J Cutler
- DOI
- 10.1016/j.phymed.2017.12.032
- eISSN
- 1618-095X
- Externe Identifier
- PubMed Identifier: 29496172
- PubMed Central ID: PMC5947877
- Funding acknowledgements
- National Institute of General Medical Sciences (NIGMS): P20GM104932
- NCRR NIH HHS: C06 RR014503
- NIGMS NIH HHS: P20 GM104932
- Open access
- false
- ISSN
- 0944-7113
- Zeitschrift
- Phytomedicine : international journal of phytotherapy and phytopharmacology
- Schlüsselwörter
- Humans
- Cytisus
- Hypericum
- Plants, Medicinal
- Flavonoids
- Quercetin
- Monoamine Oxidase
- Monoamine Oxidase Inhibitors
- Drug Evaluation, Preclinical
- Inhibitory Concentration 50
- Algeria
- Mass Spectrometry
- Molecular Docking Simulation
- Sprache
- eng
- Medium
- Print-Electronic
- Online publication date
- 2017
- Paginierung
- 27 - 36
- Datum der Veröffentlichung
- 2018
- Status
- Published
- Datum der Datenerfassung
- 2018
- Titel
- Inhibition of human monoamine oxidase A and B by flavonoids isolated from two Algerian medicinal plants.
- Sub types
- research-article
- Journal Article
- Ausgabe der Zeitschrift
- 40
Files
http://manuscript.elsevier.com/S0944711317302064/pdf/S0944711317302064.pdf https://europepmc.org/articles/PMC5947877?pdf=render
Data source: Europe PubMed Central
- Abstract
- BACKGROUND: Monoamine oxidases (MAOs) are outer mitochondrial membrane flavoenzymes. They catalyze the oxidative deamination of a variety of neurotransmitters. MAO-A and MAO-B may be considered as targets for inhibitors to treat neurodegenerative diseases and depression and for managing symptoms associated with Parkinson's and Alzheimer's diseases. PURPOSE: The objective was to evaluate the inhibitory effect of Hypericum afrum and Cytisus villosus against MAO-A and B and to isolate the compounds responsible for the MAO-inhibitory activity. METHODS: The inhibitory effect of extracts and purified constituents of H. afrum and C. villosus were investigated in vitro using recombinant human MAO-A and B, and through bioassay-guided fractionation of ethyl acetate fractions of areal parts of the two plants collected in northeastern Algeria. In addition, computational protein-ligand docking and molecular dynamics simulations were carried out to explain the MAO binding at the molecular level. RESULTS: The ethyl acetate (EtOAc) fractions of H. afrum and C. villosus showed the highest MAO inhibition activity against MAO A and B with IC50 values of 3.37 µg/ml and 13.50 µg/ml as well as 5.62 and 1.87 µg/ml, respectively. Bioassay-guided fractionation of the EtOAc fractions resulted in the purification and identification of the known flavonoids quercetin, myricetin, genistein and chrysin as the principal MAO-inhibitory constituents. Their structures were established by extensive 1 and 2D NMR studies and mass spectrometry. Quercetin, myricetin and chrysin showed potent inhibitory activity towards MAO-A with IC50 values of 1.52, 9.93 and 0.25 µM, respectively, while genistein more efficiently inhibited MAO-B (IC50 value: 0.65 µM). The kinetics of the inhibition and the study of dialysis dissociation of the complex of quercetin and myricetin and the isoenzyme MAO-A showed competitive and mixed inhibition, respectively. Both compounds showed reversible binding. Molecular docking experiments and molecular dynamics simulations allowed to estimate the binding poses and to identify the most important residues involved in the selective recognition of molecules in the MAOs enzymatic clefts. CONCLUSION: Quercetin and myricetin isolated from H. afrum together with genistein and chrysin isolated from C. villosus have been identified as potent MAO-A and -B inhibitors. H. afrum and C. villosus have properties indicative of potential neuroprotective ability and may be new candidates for selective MAO-A and B inhibitors.
- Date of acceptance
- 2017
- Autoren
- Farida Larit
- Khaled M Elokely
- Narayan D Chaurasiya
- Samira Benyahia
- Manal A Nael
- Francisco León
- Mohammad Sanad Abu-Darwish
- Thomas Efferth
- Yan-Hong Wang
- Djamila Belouahem-Abed
- Samir Benayache
- Babu L Tekwani
- Stephen J Cutler
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/29496172
- DOI
- 10.1016/j.phymed.2017.12.032
- eISSN
- 1618-095X
- Externe Identifier
- NIH Manuscript Submission ID: NIHMS935358
- PubMed Central ID: PMC5947877
- Funding acknowledgements
- NCRR NIH HHS: C06 RR014503
- NIGMS NIH HHS: P20 GM104932
- Zeitschrift
- Phytomedicine
- Schlüsselwörter
- Antidepressant
- Bioassay-guided fractionation
- HR-ESI-MS
- Molecular docking
- Monoamine oxidase
- NMR
- Algeria
- Cytisus
- Drug Evaluation, Preclinical
- Flavonoids
- Humans
- Hypericum
- Inhibitory Concentration 50
- Mass Spectrometry
- Molecular Docking Simulation
- Monoamine Oxidase
- Monoamine Oxidase Inhibitors
- Plants, Medicinal
- Quercetin
- Sprache
- eng
- Country
- Germany
- Paginierung
- 27 - 36
- PII
- S0944-7113(17)30206-4
- Datum der Veröffentlichung
- 2018
- Status
- Published
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2018
- Titel
- Inhibition of human monoamine oxidase A and B by flavonoids isolated from two Algerian medicinal plants.
- Sub types
- Journal Article
- Ausgabe der Zeitschrift
- 40
Data source: PubMed
- Beziehungen:
- Property of