Two Pyranocoumarins from the Seeds of <i>Calophyllum polyanthum</i>

Two new pyranocoumarin diastereoisomers, calopolyanolides C (<b>1</b>) and D (<b>2</b>), were isolated from the ethanolic extract of the seeds of <i>Calophyllum polyanthum</i>, along with calopolyanolide A (<b>3</b>), calopolyanolide B (<b>4</b>), calanolide E2 (<b>5</b>), 5,7,3‘,4‘-tetrahydroxyisoflavone (<b>6</b>), 3,4-dihydroxybenzoic acid (<b>7</b>), 3,4,5-trihydroxybenzoic acid (<b>8</b>), 2-hydroxy-4-methoxybenzoic acid (<b>9</b>), β-sitosterol (<b>10</b>), β-daucosterol (<b>11</b>), 3,5-dihydroxy-4-methoxybenzoic acid (<b>12</b>), 3,5-dimethoxybenzoic acid (<b>13</b>), and ursolic acid (<b>14</b>). Their structures were determined by MS, UV, and IR data and HMQC, HMBC, and NOESY experiments or by comparing them with authentic samples. X-ray crystallographic analysis confirmed the structure and relative configuration of <b>1</b>.