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In the present study, 14 structurally unique flavonoids were screened to systematically investigate structural requirements for selectively inhibiting human α-amylase versus α-glucosidase to obtain a slow but complete starch digestion for health benefit. The selective inhibition property of three flavonoids chosen against the two classes of starch digestive enzymes was confirmed through various analytical techniques - in vitro inhibition assay, fluorescence quenching, kinetic study, and molecular modeling. Considering the chemical structure of