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A methanol extract of everlasting flowers of <i>Helichrysum arenarium</i> L. Moench (Asteraceae) was found to inhibit the increase in blood glucose elevation in sucrose-loaded mice at 500 mg/kg p.o. The methanol extract also inhibited the enzymatic activity against dipeptidyl peptidase-IV (DPP-IV, IC<sub>50</sub> = 41.2 μg/ml), but did not show intestinal <i>α</i>-glucosidase inhibitory activities. From the extract, three new dimeric dihydrochalcone glycosides, arenariumosides V-VII (<i>2</i>-<i>4</i>), were isolated, and the stereostructures were elucidated based on their spectroscopic properties and chemical evidence. Of the constituents, several flavonoid constituents, including <i>2</i>-<i>4</i>, were isolated, and these isolated constituents were investigated for their DPP-IV inhibitory effects. Among them, chalconaringenin 2′-<i>O</i>-<i>β</i>-D-glucopyranoside (<i>16</i>, IC<sub>50</sub> = 23.1 μM) and aureusidin 6-<i>O</i>-<i>β</i>-D-glucopyranoside (<i>35</i>, 24.3 μM) showed relatively strong inhibitory activities.