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A phytochemical investigation of the leaves and twigs of <i>Glycosmis pentaphylla</i> (Rutaceae), collected in Vietnam, yielded three new compounds named glyfuran (<b>1</b>), glyphyllamide (<b>2</b>), and glyphyllazole (<b>3</b>), along with twenty-five known compounds (<b>4</b>–<b>28</b>). The structures of isolates were determined by IR, MS, NMR, and UV data analyses. In the anti-diabetic activity screening, (+)-isoaltholacton (<b>4</b>), glycoborinine (<b>17</b>), 2′,4′-dihydroxy-4,6′-dimethoxychalcone (<b>24</b>), and flavokawain A (<b>25</b>) simultaneously exhibited inhibition of dipeptidyl peptidase-4 (DPP4) and stimulation of the glucagon-like peptide-1 (GLP-1) secretion on the murine intestinal secretin tumor cell line (STC-1).