Acetophenones and coumarins from stem bark and leaves of Melicope stipitata

Phytochemistry
1994.0

Abstract

Melicope stipitata has yielded six acetophenone derivatives; acronylin, evodionol methyl ether, evodionol and three novel compounds. The latter were identified as S-acetyl-6-hydroxy-2-(2-hydroxyisopropyl) methoxybenzofuran (furostipitol), (rel)-( +)-6-acctyl-3,4-dihydro-4acthoxy-3~-hydroxy-5,7-dimethoxy-2,2-dimethyl-2H-1-benzopyran (3-hydroxydihydropyranostipitol+ethyl ether) and (rel)-( f)&acetyl-3,4-dihydro-3/?&x-dihydroxy-5,7dimethoxy-2,2-dimethyl-2H-1-benzopyran (3,4_dihydroxydihydropyranostipitol). S-Acetyl-6-hydroxy-2-(2 hydroxyisopropyl)&methoxybenzofuran was isolated together with a small quantity of another compound, tentatively identified as its dihydrofuran analogue, namely, 5-acetyl-2,3-dihydro-6-hydroxy-2-(2-hydroxyisopropyl)-4 methoxy benzofuran. The 'H NMR spectra of 3,4-dihydroxydihydropyranostipitol in different solvents is discussed. In addition, the furocoumarins, bergapten, phellopterin, isoimperatorin and isopimpinellin, the angular pyranocoumarin, seselin, the 8-prenylated coumarins, osthol, peroxyauraptenol and osthenon, the biscoumarin, phebalin, the lignan, sesamin, and the triterpene, isobaurenol, were obtained.

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