Inhibitory Effects of Novel 7-Substituted 6-iodo-3-<i>O</i>-Flavonol Glycosides against Cholinesterases and β-secretase Activities, and Evaluation for Potential Antioxidant Properties
A series of 7-halogeno- (X = F, Cl, Br) and 7-methoxy-substituted acetylated 6-iodo-3-<i>O</i>-flavonol glycosides were prepared, and evaluated for inhibitory effect in vitro against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) activities. 7-Bromo-2-(4-chlorophenyl)-6-iod...
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doaj-e42c9e1dd99f40bd8f513ba998a4351d2020-11-25T01:43:55ZengMDPI AGMolecules1420-30492019-09-012419350010.3390/molecules24193500molecules24193500Inhibitory Effects of Novel 7-Substituted 6-iodo-3-<i>O</i>-Flavonol Glycosides against Cholinesterases and β-secretase Activities, and Evaluation for Potential Antioxidant PropertiesEmmanuel N. Agbo0Samantha Gildenhuys1Malose J. Mphahlele2Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, Private Bag X06, Florida 1710, South AfricaDepartment of Life & Consumer Sciences, College of Agriculture and Environmental Sciences, University of South Africa, Private Bag X06, Florida 1710, South AfricaDepartment of Chemistry, College of Science, Engineering and Technology, University of South Africa, Private Bag X06, Florida 1710, South AfricaA series of 7-halogeno- (X = F, Cl, Br) and 7-methoxy-substituted acetylated 6-iodo-3-<i>O</i>-flavonol glycosides were prepared, and evaluated for inhibitory effect in vitro against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) activities. 7-Bromo-2-(4-chlorophenyl)-6-iodo-4<i>H</i>-chromen-4-one-3-<i>O</i>-2,3,4,6<i>-O</i>-tetraacetyl-β-<i>d</i>-glucopyranoside (<b>2k</b>) and 7-bromo-6-iodo-2-(4-methoxyphenyl)-4<i>H</i>-chromen-4-one-3-<i>O</i>-2,3,4,6-<i>O</i>-tetraacetyl-β-<i>d</i>-glucopyranoside (<b>2l</b>) exhibited significant inhibitory effect against AChE activity when compared to the activity of the reference standard, donepezil. Compound <b>2k</b> was found to be selective against AChE and to exhibit reduced inhibitory effect against BChE activity. 6-Iodo-7-methoxy-2-(4-methoxyphenyl)-4<i>H</i>-chromen-4-one-3-<i>O</i>-2,3,4,6-<i>O</i>-tetraacetyl-β-<i>d</i>-glucopyranoside (<b>2p</b>) was found to exhibit increased activity against BChE, more so than the activity of donepezil. The most active compounds were also evaluated for inhibitory effect against β-secretase activity and for potential radical scavenging activities. The experimental data were complemented with molecular docking (in silico) studies of the most active compounds into the active sites of these enzymes.https://www.mdpi.com/1420-3049/24/19/35003-<i>o</i>-flavonol glycosidesx-rayacetylcholinesterasebutyrylcholinesteraseβ-secretasekinetic studiesmolecular dockingantioxidant assay |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Emmanuel N. Agbo Samantha Gildenhuys Malose J. Mphahlele |
spellingShingle |
Emmanuel N. Agbo Samantha Gildenhuys Malose J. Mphahlele Inhibitory Effects of Novel 7-Substituted 6-iodo-3-<i>O</i>-Flavonol Glycosides against Cholinesterases and β-secretase Activities, and Evaluation for Potential Antioxidant Properties Molecules 3-<i>o</i>-flavonol glycosides x-ray acetylcholinesterase butyrylcholinesterase β-secretase kinetic studies molecular docking antioxidant assay |
author_facet |
Emmanuel N. Agbo Samantha Gildenhuys Malose J. Mphahlele |
author_sort |
Emmanuel N. Agbo |
title |
Inhibitory Effects of Novel 7-Substituted 6-iodo-3-<i>O</i>-Flavonol Glycosides against Cholinesterases and β-secretase Activities, and Evaluation for Potential Antioxidant Properties |
title_short |
Inhibitory Effects of Novel 7-Substituted 6-iodo-3-<i>O</i>-Flavonol Glycosides against Cholinesterases and β-secretase Activities, and Evaluation for Potential Antioxidant Properties |
title_full |
Inhibitory Effects of Novel 7-Substituted 6-iodo-3-<i>O</i>-Flavonol Glycosides against Cholinesterases and β-secretase Activities, and Evaluation for Potential Antioxidant Properties |
title_fullStr |
Inhibitory Effects of Novel 7-Substituted 6-iodo-3-<i>O</i>-Flavonol Glycosides against Cholinesterases and β-secretase Activities, and Evaluation for Potential Antioxidant Properties |
title_full_unstemmed |
Inhibitory Effects of Novel 7-Substituted 6-iodo-3-<i>O</i>-Flavonol Glycosides against Cholinesterases and β-secretase Activities, and Evaluation for Potential Antioxidant Properties |
title_sort |
inhibitory effects of novel 7-substituted 6-iodo-3-<i>o</i>-flavonol glycosides against cholinesterases and β-secretase activities, and evaluation for potential antioxidant properties |
publisher |
MDPI AG |
series |
Molecules |
issn |
1420-3049 |
publishDate |
2019-09-01 |
description |
A series of 7-halogeno- (X = F, Cl, Br) and 7-methoxy-substituted acetylated 6-iodo-3-<i>O</i>-flavonol glycosides were prepared, and evaluated for inhibitory effect in vitro against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) activities. 7-Bromo-2-(4-chlorophenyl)-6-iodo-4<i>H</i>-chromen-4-one-3-<i>O</i>-2,3,4,6<i>-O</i>-tetraacetyl-β-<i>d</i>-glucopyranoside (<b>2k</b>) and 7-bromo-6-iodo-2-(4-methoxyphenyl)-4<i>H</i>-chromen-4-one-3-<i>O</i>-2,3,4,6-<i>O</i>-tetraacetyl-β-<i>d</i>-glucopyranoside (<b>2l</b>) exhibited significant inhibitory effect against AChE activity when compared to the activity of the reference standard, donepezil. Compound <b>2k</b> was found to be selective against AChE and to exhibit reduced inhibitory effect against BChE activity. 6-Iodo-7-methoxy-2-(4-methoxyphenyl)-4<i>H</i>-chromen-4-one-3-<i>O</i>-2,3,4,6-<i>O</i>-tetraacetyl-β-<i>d</i>-glucopyranoside (<b>2p</b>) was found to exhibit increased activity against BChE, more so than the activity of donepezil. The most active compounds were also evaluated for inhibitory effect against β-secretase activity and for potential radical scavenging activities. The experimental data were complemented with molecular docking (in silico) studies of the most active compounds into the active sites of these enzymes. |
topic |
3-<i>o</i>-flavonol glycosides x-ray acetylcholinesterase butyrylcholinesterase β-secretase kinetic studies molecular docking antioxidant assay |
url |
https://www.mdpi.com/1420-3049/24/19/3500 |
work_keys_str_mv |
AT emmanuelnagbo inhibitoryeffectsofnovel7substituted6iodo3ioiflavonolglycosidesagainstcholinesterasesandbsecretaseactivitiesandevaluationforpotentialantioxidantproperties AT samanthagildenhuys inhibitoryeffectsofnovel7substituted6iodo3ioiflavonolglycosidesagainstcholinesterasesandbsecretaseactivitiesandevaluationforpotentialantioxidantproperties AT malosejmphahlele inhibitoryeffectsofnovel7substituted6iodo3ioiflavonolglycosidesagainstcholinesterasesandbsecretaseactivitiesandevaluationforpotentialantioxidantproperties |
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