Document Detail


Flavonoids for controlling starch digestion: structural requirements for inhibiting human alpha-amylase.
MedLine Citation:
PMID:  18507367     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
In this study we investigated the structural requirements for inhibition of human salivary alpha-amylase by flavonoids. Four flavonols and three flavones, out of the 19 flavonoids tested, exhibited IC50 values less than 100 microM against human salivary alpha-amylase activity. Structure-activity relationships of these inhibitors by computational ligand docking showed that the inhibitory activity of flavonols and flavones depends on (i) hydrogen bonds between the hydroxyl groups of the polyphenol ligands and the catalytic residues of the binding site and (ii) formation of a conjugated pi-system that stabilizes the interaction with the active site. Our findings show that certain naturally occurring flavonoids act as inhibitors of human alpha-amylase, which makes them promising candidates for controlling the digestion of starch and postprandial glycemia.
Authors:
Elena Lo Piparo; Holger Scheib; Nathalie Frei; Gary Williamson; Martin Grigorov; Chieh Jason Chou
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Publication Detail:
Type:  Journal Article     Date:  2008-05-29
Journal Detail:
Title:  Journal of medicinal chemistry     Volume:  51     ISSN:  0022-2623     ISO Abbreviation:  J. Med. Chem.     Publication Date:  2008 Jun 
Date Detail:
Created Date:  2008-06-19     Completed Date:  2008-09-05     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  9716531     Medline TA:  J Med Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  3555-61     Citation Subset:  IM    
Affiliation:
Nestlé Research Center, Vers-chez-les-Blanc, PO Box 44, CH-1000 Lausanne 26, Switzerland. elena.lopiparo@rdls.nestle.com
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MeSH Terms
Descriptor/Qualifier:
Catalytic Domain
Digestion
Flavones / chemistry*
Flavonols / chemistry*
Humans
Hydrogen Bonding
Ligands
Models, Molecular*
Protein Conformation
Saliva / enzymology
Starch / metabolism*
Structure-Activity Relationship
alpha-Amylases / antagonists & inhibitors*,  chemistry
Chemical
Reg. No./Substance:
0/Flavones; 0/Flavonols; 0/Ligands; 9005-25-8/Starch; EC 3.2.1.1/alpha-Amylases

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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