Diarilpropanóides de Yryanthera laevis

Abstract

The plant that furnished the material for the present work was collected in the environment of Manaus-Amazonas and classified by Dr. William A. Rodrigues of the Instituto Nacional de Pesquisas da Amazônia. From the ethanolic extract of the trunk wood of Iryanthera laevis (family Myristicaceae) have been isolated four virolans: the new 1-(2'-hydroxy-4'-methoxy-5'-methylphenyl)-3-(2' '-hydroxy-4'', 5''-methylenedioxyphenyl)-propane and the three known 1-(2',4'-dihydroxy-3',5'-dimethylphenyl)- 3-)2''-hydroxy-4'',5''methylenedioxyphenyl)-propane, 1-(2',4'-dihydroxyphenyl)-3-(2"-methoxy- 4",5"-methylenedioxyphenyl)-propane and 1-(2',4'-dihydroxy-3'-methylphenyl)-3 - (2''-methoxy-4' ',5''-methylenedioxyphenyl)- propane; three new flavans: 2',?'-dihydroxy-4',5'-methylenedioxy-6,B-dimethylflavan, 2', 7-dihydroxy-4',5'- methylenedioxy-5,8-dimethylflavan and 2',5-dihydroxy-7-methoxy-4 ',5'-methylenedioxy-6,8-dimethyl,fl-avan; one new chalcone: 2',4'-dihydroxy-4,6'-dimethoxydihydrochalcone; and sitosterol. The structures were elucidated on the basis of the interpretation of the spectral data of the compounds and of their derivatives obtained by acetylation and methylation. The probable course of biogenesis leading to dihydrochalcones, flavans and virolans is discussed.