Constituintes micromoleculares de Aristolochia melastoma Manso: compostos nitrados
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Data
2010-01-19
Autores
Nogueira, Cláudio Rodrigo [UNESP]
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Universidade Estadual Paulista (Unesp)
Resumo
O presente trabalho descreve o isolamento e identificação dos constituintes químicos de Aristolochia melastoma Manso. O extrato acetônico de caules e raízes foi fracionado por cromatografia em coluna de sílica gel, e as frações obtidas foram submetidas a outros fracionamentos cromatográficos (CCDP, Sephadex LH-20, CC de C-18 e CLAE) e/ou lavagens com solventes orgânicos, resultando no isolamento de vinte compostos conhecidos: aristolactama AII, 9,9'-diacetato-secoisolariciresinol dimetil éter, tirosol, ácido p-hidroxibenzóico, ácido vanilínico, ácidos aristolóquicos I e II, aristolocatos de sódio IIIa e IVa, 4,5-dioxodeidroasimilobíneo, aristolocato de sódio I, sitosterol 3-O-β-D-glucopiranosídeo, glicerol, talictosídeo, uridina, talictricosídeo, icarisídeo D2, adenosina, kaempferol 3-O-β-robinobiosídeo e isorhamnetina 3-O-β-robinobiosídeo. A lignana 9,9'-diacetato-secoisolariciresinol dimetil éter e talictricosídeo são relatados pela primeira vez na família Aristolochiaceae. As identificações desses compostos foram baseadas nas análises dos seus dados espectrométricos (RMN 1D e 2D, UV e EM). Além disso, a análise dos dados obtidos a partir de literatura especializada acerca da ocorrência e biogênese de derivados nitrofeniletílicos sugere que a família Aristolochiaceae pode ter evoluído no sentido de formação de compostos nitrados
This work describes the isolation and identification of the chemical constituents of A. melastoma Manso. The acetone extract from stems and roots was fractionated by CC over silica gel and the resultant fractions were subjected to other chromatographic methods (PTLC, Sephadex LH-20, CC RP-18, and HPLC) and/or washed with organic solvents to give twenty known compounds: aristolactam AII, secoisolariciresinol dimethyl ether diacetate, tyrosol, p-hydroxybenzoic acid, vanillic acid, sodium aristolochates I, IIIa, and IVa, 4,5-dioxodehydroasimilobine, aristolochic acids I and II, sitosterol-3-O-β-D-glucopyranoside, glycerol, uridine, thalictoside, icariside D2, adenosine, thalictricoside, kaempferol 3-O-β-robinobioside, and isorhamnetin 3-O-β-robinobioside. Among these, secoisolariciresinol dimethyl ether diacetate and thalictricoside have being reported for the first time in the Aristolochiaceae family. The identifications of these compounds were based on analyses of their spectroscopic data (1D- and 2D-NMR, UV, and MS). Furthermore, an analysis of data obtained from specialized literature on the occurrence and biogenesis of nitrophenylethyl derivatives suggests that the Aristolochiaceae family may have evolved towards nitro compounds
This work describes the isolation and identification of the chemical constituents of A. melastoma Manso. The acetone extract from stems and roots was fractionated by CC over silica gel and the resultant fractions were subjected to other chromatographic methods (PTLC, Sephadex LH-20, CC RP-18, and HPLC) and/or washed with organic solvents to give twenty known compounds: aristolactam AII, secoisolariciresinol dimethyl ether diacetate, tyrosol, p-hydroxybenzoic acid, vanillic acid, sodium aristolochates I, IIIa, and IVa, 4,5-dioxodehydroasimilobine, aristolochic acids I and II, sitosterol-3-O-β-D-glucopyranoside, glycerol, uridine, thalictoside, icariside D2, adenosine, thalictricoside, kaempferol 3-O-β-robinobioside, and isorhamnetin 3-O-β-robinobioside. Among these, secoisolariciresinol dimethyl ether diacetate and thalictricoside have being reported for the first time in the Aristolochiaceae family. The identifications of these compounds were based on analyses of their spectroscopic data (1D- and 2D-NMR, UV, and MS). Furthermore, an analysis of data obtained from specialized literature on the occurrence and biogenesis of nitrophenylethyl derivatives suggests that the Aristolochiaceae family may have evolved towards nitro compounds
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Palavras-chave
Produtos naturais, Ressonancia magnetica nuclear, Cromatografia liquida, Natural products, Nuclear magnetic resonance, Liquid cromatography
Como citar
NOGUEIRA, Cláudio Rodrigo. Constituintes micromoleculares de Aristolochia melastoma Manso: compostos nitrados. 2010. 125 f. Dissertação (mestrado) - Universidade Estadual Paulista, Instituto de Química, 2010.