Eight new limonoids, toononoids A-H (<b>1</b>-<b>8</b>), eight new B-<i>seco</i>-29-norlimonoids, toonanoronoids A-H (<b>9</b>-<b>16</b>), and seven known analogues were obtained from the EtOAc extract of the twigs and leaves of <i>Toona ciliata</i>. Compounds <b>2</b>, <b>4</b>, <b>8</b>, and <b>16</b> are rare lactam-bearing limonoids. Compounds <b>1</b>, <b>14</b>, and <b>15</b> possess an unusual γ-methoxybutenolide moiety at C-17, while compounds <b>9</b>, <b>10</b>, and <b>15</b> have a rare 3β-hydroxy group. Their 2D structure and relative configurations were identified using spectroscopic data. The absolute configurations of <b>1</b>, <b>9</b>, <b>14</b>, and <b>15</b> were established via X-ray diffraction crystallography or comparison of experimental and calculated ECD data. The cytotoxicity of the compounds was assessed toward five human tumor cell lines, and their anti-inflammatory activity was assessed based on NO production using LPS-stimulated RAW264.7 macrophages. Compounds <b>11</b> and <b>12</b> exerted inhibition toward two tumor cell lines (MCF-7, SW-480) with IC<sub>50</sub> values between 2.1 and 3.7 μM, while <b>18</b>-<b>22</b> inhibited the proliferation of HL-60, MCF-7, and SW-480 cells (IC<sub>50</sub> 0.6-4.0 μM). Only compound <b>4</b> exhibited weak anti-inflammatory activity with an IC<sub>50</sub> value of 28.3 μM.