<jats:title>Abstract</jats:title><jats:p>One new flavanone, 4′‐hydroxyisorottlerin (<jats:bold>2</jats:bold>), and two new chalcone derivatives, kamalachalcones C (<jats:bold>3</jats:bold>) and D (<jats:bold>4</jats:bold>), were isolated from <jats:italic>Mallotus philippensis</jats:italic> (kamala tree). The largest compound (<jats:bold>4</jats:bold>; <jats:italic>M</jats:italic><jats:sub>r</jats:sub> 1098 g/mol) was shown to possess a unique, fused‐ring system made of two hydroxy‐chalcone units, giving rise to eight fused benzene/pyran units. From the same plant, the following six known compounds were also isolated: kamalachalcone A (<jats:bold>5</jats:bold>) and B (<jats:bold>6</jats:bold>), isoallorottlerin (<jats:bold>7</jats:bold>), isorottlerin (<jats:bold>8</jats:bold>), 5,7‐dihydroxy‐8‐methyl‐6‐prenylflavanone (<jats:bold>9</jats:bold>); 6,6‐dimethylpyrano(2″,3″: 7,6)‐5‐hydroxy‐8‐methylflavanone (<jats:bold>10</jats:bold>), and rottlerin (<jats:bold>1</jats:bold>). The structures of the new compounds were confirmed by in‐depth spectral analyses, including 2D‐NMR techniques, and the full <jats:sup>13</jats:sup>C‐NMR assignments of the known flavanones <jats:bold>1</jats:bold> and <jats:bold>7</jats:bold>–<jats:bold>10</jats:bold> are published for the first time.