<i>Glycyrrhiza uralensis</i> (liquorice) is a well-known medicinal plant. Its roots and rhizomes are used as the popular Chinese herbal medicine Gan-Cao. An ethanol extract of the aerial parts of <i>G. uralensis</i> showed antidiabetic effects on db/db mice. It decreased the blood glucose level by 30.3% and increased the serum insulin level by 41.8% compared to the control group. Eighty-six phenolic compounds (<b>1</b>-<b>86</b>) were obtained from the aerial parts, including the new prenylated isoflavanones (<b>1</b>-<b>5</b>), isoflavans (<b>6</b>-<b>9</b>), and a 2-phenylbenzofuran (<b>10</b>). The structures were identified by NMR and HRESIMS data analyses, and the absolute configurations were established by comparing the calculated and experimental ECD spectroscopic data. Compounds <b>2</b>, <b>6</b>, and <b>10</b> inhibited PTP1B with IC<sub>50</sub> values of 5.9, 6.7, and 5.3 μM, respectively. Compound <b>2</b> and the known compounds glycycoumarin (<b>76</b>) and glyurallin A (<b>79</b>) inhibited α-glucosidase with IC<sub>50</sub> values of 20.1, 0.1, and 0.3 μM, respectively. Compound <b>4</b> at 10 μM increased the glucose uptake rate to 95% in an insulin resistance HepG2 cell model (<i>p</i> < 0.01).