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This study reports on the antioxidant activity and α-glucosidase inhibitory activity of five cycloartane-type triterpenes isolated from Indonesian stingless bee ( Tetragonula sapiens Cockerell) propolis and their structure-activity relationships. The structure of the triterpenes was determined to include mangiferolic acid ( 1 ), Cycloartenol ( 2 ), ambonic acid ( 3 ), mangiferonic acid ( 4 ), and ambolic acid ( 5 ). The inhibitory test results of all isolated triterpenes against α-glucosidase showed a high potential for inhibitory activity with an IC 50 range between 2.46 and 10.72 µM. Among the compounds tested, mangiferonic acid (4) was the strongest α-glucosidase inhibitor with IC 50 2.46 µM compared to the standard (-)-epicatechin (1991.1 µM), and also had antioxidant activities with IC 50 values of 37.74 ± 6.55 µM. The study on the structure-activity relationships among the compounds showed that the ketone group at C-3 and the double bonds at C-24 and C-25 are needed to increase the α-glucosidase inhibitory activity. The carboxylic group at C-26 is also more important for increasing the inhibitory activity compared with the methyl group. This study provides an approach to help consider the structural requirements of cycloartane-type triterpenes from propolis as α-glucosidase inhibitors. An understanding of these requirements is deemed necessary to find a new type of α-glucosidase inhibitor from the cycloartane-type triterpenes or to improve those inhibitors that are known to help in the treatment of diabetes.

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α-Glucosidase Inhibitory Activity of Cycloartane-Type Triterpenes Isolated from Indonesian Stingless Bee Propolis and Their Structure–Activity Relationship