Two Pyranocoumarins from the Seeds of Calophyllum polyanthum

Two new pyranocoumarin diastereoisomers, calopolyanolides C (1) and D (2), were isolated from the ethanolic extract of the seeds of Calophyllum polyanthum, along with calopolyanolide A (3), calopolyanolide B (4), calanolide E2 (5), 5,7,3‘,4‘-tetrahydroxyisoflavone (6), 3,4-dihydroxybenzoic acid (7), 3,4,5-trihydroxybenzoic acid (8), 2-hydroxy-4-methoxybenzoic acid (9), β-sitosterol (10), β-daucosterol (11), 3,5-dihydroxy-4-methoxybenzoic acid (12), 3,5-dimethoxybenzoic acid (13), and ursolic acid (14). 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 1.