Estudo químico de Annona dioica (St. Hill Annonaceae)

Abstract

Following review of the published results on the pharmacological activity, of extracts from the Annonaceae family, we decided to indutake the chemical investigation of Annona dioica St. HilI.Substance (4) is reported for the first time as a natural Product. The ethanolic extract from trunk and roots of this species furnished: 1-aza-4- methyl-anthraquinone(1),3,4,5,6,7,8,9,10-octahydro-12-hydroxy-14-methoxy-3- methyl-1H-2-benzoxacyclododecin-1-one (lasiodiplodine,2), 1,2-methylenedioxy- 4,5,6,6a-tetradehydro-7-oxo aporphine (liriodenine=spermatheridine, 3), 1,2- m e t h y l e n e d i o x y - 6 a , 7 - d e h y d r o a p h o r p h i n e - [ N , 7 - e ] - 4 - ( 4 - h y d r o x y - 3 , 5 - dimethoxyphenyl)-dihydro-2(3H-pyranone (4), a mixture of 1-aza-5,9,10-trimethoxy- 4-methyl(-2-oxo-1,2-dihydroanthracene (5a)+ 1-aza-8,9,10-trimethoxy-4-methyl-2- oxo-1,2-dihydroanthracene (Geovanine, 5b) and a mixture of N-[3-hydroxy-4- methoxy cinnamoyl]-2-[p-hydroxyphenyl]-1-ethylamine (6) + N-[3-hydroxy-4,5- dimethoxycinnamoyl]-2-[p-hydroxyphenyl]-1-ethylamine(7). The isolation of these constituints involved column and thin layer chromatography. Structural elucidation was based on the usual epectrometric methods, mainly modern techniques of NMR such as one-(NOE difference spectra) and twodimensional (1Hx 1H-COSY, 1H x13C-COSY-1JCH) spectra. XXIV