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J Med Chem. 2008 Jun 26;51(12):3555-61. doi: 10.1021/jm800115x. Epub 2008 May 29.

Flavonoids for controlling starch digestion: structural requirements for inhibiting human alpha-amylase.

Author information

1
Nestlé Research Center, Vers-chez-les-Blanc, PO Box 44, CH-1000 Lausanne 26, Switzerland. elena.lopiparo@rdls.nestle.com

Abstract

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.

PMID:
18507367
DOI:
10.1021/jm800115x
[Indexed for MEDLINE]

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