ACETOPHENONES AND COUMARINS FROM STEM BARK AND LEAVES OF MELICOPE STIPITATA

Melicope stipitata has yielded six acetophenone derivatives; acronylin , evodionol methyl ether, evodionol and three novel compounds. The lat ter were identified as 5-acetyl-6-hydroxy-2-(2-hydroxyisopropyl methox ybenzofuran (furostipitol), (rel)-(+/-)-6-acetyl-3,4-dihydro-4 alpha-e thoxy- 3 hydroxy-5,7-dimethoxy-2,2-dimethyl-2H-1-benzopyran (3-hydroxy dihydropyranostipitol-4-ethyl ether) and (rel)-(+/-)-6-acetyl-3,4-dihy dro-3 beta,4 alpha-dihydroxy-5, 7-dimethoxy-2,2-dimethyl-2H-1-benzopyr an (3,4-dihydroxydihydropyranostipitol. hydroxy-2-(2-hydroxyisopropyl) -4-methoxybenzofuran was isolated together with a small quantity of an other compound, tentatively identified as its dihydrofuran analogue, n amely, dihydro-6-hydroxy-2-(2-hydroxyisopropyl)-4-methoxy benzofuran. The H-1 NMR spectra of 3,4-dihydroxydihydropyranostipitol in different solvents is discussed. In addition, the furocoumarins, bergapten, phe llopterin, isoimperatorin and isopimpinellin, the angular pyranocoumar in, seselin, the 8-prenylated coumarins, osthol, peroxyauraptenol and osthenon, the biscoumarin, phebalin, the lignan, sesamin, and the trit erpene, isobaurenol, were obtained.