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Four new dammarane triterpenoid saponins cypaliurusides <b>Z₁</b>–<b>Z₄</b> (<b>1</b>–<b>4</b>) and eight known analogs (<b>5</b>–<b>12</b>) were isolated from the leaves of <i>Cyclocarya paliurus</i>. The structures of the isolated compounds were determined using a comprehensive analysis of 1D and 2D NMR and HRESIMS data. The docking study demonstrated that compound 10 strongly bonded with PTP1B (a potential drug target for the treatment of type-II diabetes and obesity), hydrogen bonds, and hydrophobic interactions, verifying the importance of sugar unit. The effects of the isolates on insulin-stimulated glucose uptake in 3T3-L1 adipocytes were evaluated and three dammarane triterpenoid saponins (<b>6</b>, <b>7</b> and <b>10</b>) were found to enhance insulin-stimulated glucose uptake in 3T3-L1 adipocytes. Furthermore, compounds <b>6</b>, <b>7,</b> and <b>10</b> exhibited potent abilities to promote insulin-stimulated glucose uptake in 3T3-L1 adipocytes in a dose-dependent manner. Thus, the abundant dammarane triterpenoid saponins from <i>C. paliurus</i> leaves exhibited stimulatory effects on glucose uptake with application potential as a antidiabetic treatment.