Investigação da composição química de espécies de Aristolochia do Cerrado: estudo dos caules de Aristolochia urupaensis e de flores de Aristolochia trulliformis
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Data
2018-04-26
Autores
Holzbach, Juliana Cristina [UNESP]
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Editor
Universidade Estadual Paulista (Unesp)
Resumo
Este trabalho descreve a elucidação estrutural dos constituintes químicos de duas espécies presentes no Cerrado: Aristolochia urupaensis Hoehne e Aristolochia trulliformis Mast. Os extratos etanólico e etanólico Soxhlet dos caules de A. urupaensis foram submetidos a processos cromatográficos, resultando no isolamento e identificação de 36 substâncias, entre as quais uma nova piranona, (2S)-2-[2'-(4-hidroxifenil)etil]-6-metil-2,3-diidro-4H-piran-4-ona, e três novos derivados de ácido aristolóquico (ácido 7-O-metil-aristolóquico F, aristolocato de sódio F e 7-O-metil-aristolocato de sódio F); além de outras cinco substâncias que estão sendo descritas pela primeira vez na família Aristolochiaceae: tirosol-1-O-β-glicopiranosil-(6→1)-O-β-xilopiranosideo, a lignana (-)-9,9'-O-di-(E)-feruloil-secoisolariciresinol e os flavonoides quercetina-3-O-β-glicopiranosil-(6->1)-β-glicopiranosídeo, isoquercitrina e kaempferol-3-O-gentiobiosideo. O extrato metanólico das flores de A. trulliformis foi submetido a processos cromatográficos e resultou no isolamento de doze substâncias, sendo sete flavonoides. Destaca-se o isolamento e elucidação estrutural do flavonoide kaempferol-3-O-β-glicopiranosil-(6''->1''')-O-a-ramnopiranosil-(4'''->1'''')-O-β-glicopiranosídeo descrito pela primeira vez na literatura. Todas as estruturas foram determinadas por análises espectroscópicas (RMN 1D e 2D, IV, UV, DC e [a]D e espectrométricas (EM).
This work describes the structural elucidation of the chemical constituents of two species present in the Cerrado: Aristolochia urupaensis Hoehne and Aristolochia trulliformis Mast. The ethanolic and ethanolic Soxhlet extracts from the stems of A. urupaensis were submitted to chromatographic processes, resulting in 36 compounds, including a new pyranone, (S)-2-(4-hydroxyphenylethyl)-6-methyl-2,3-dihydro-4H-pyran-4-one, and three new aristolochic acid derivatives (7-O-methylaristolochic acid F, sodium 7-O-methylaristolochate F and sodium aristolochate F); in addition to five other compounds that were first reported in the Aristolochiaceae family: tyrosol-1-O-β-xylopyranosyl-(1→6)-O-β-glucopyranoside, the lignan (-)-9,9′-di-[O-(E)-feruloyl]secoisolariciresinol, and the flavonoids quercetin-3-O-β-glucopyranosyl-(1→6)-β-glucopyranoside, isoquercitrin and kaempferol-3-O-β-glucopyranosyl-(1→6)-β-glucopyranoside. Mast. were also studied. The methanolic extract of Aristolochia trulliformis flowers was submitted to chromatographic processes, resulting in the isolation of twelve compounds, including seven flavonoids. The flavonoid kaempferol-3-O-β-glucopyranosyl-(1→4)-a-rhamnopyranosyl-(1→6)-β-glucopyranoside is being described for the first time in the literature. All chemical structures were determined by spectroscopic (NMR 1D and 2D, IR, UV, CD and [a]D and spectrometric analyzes (MS).
This work describes the structural elucidation of the chemical constituents of two species present in the Cerrado: Aristolochia urupaensis Hoehne and Aristolochia trulliformis Mast. The ethanolic and ethanolic Soxhlet extracts from the stems of A. urupaensis were submitted to chromatographic processes, resulting in 36 compounds, including a new pyranone, (S)-2-(4-hydroxyphenylethyl)-6-methyl-2,3-dihydro-4H-pyran-4-one, and three new aristolochic acid derivatives (7-O-methylaristolochic acid F, sodium 7-O-methylaristolochate F and sodium aristolochate F); in addition to five other compounds that were first reported in the Aristolochiaceae family: tyrosol-1-O-β-xylopyranosyl-(1→6)-O-β-glucopyranoside, the lignan (-)-9,9′-di-[O-(E)-feruloyl]secoisolariciresinol, and the flavonoids quercetin-3-O-β-glucopyranosyl-(1→6)-β-glucopyranoside, isoquercitrin and kaempferol-3-O-β-glucopyranosyl-(1→6)-β-glucopyranoside. Mast. were also studied. The methanolic extract of Aristolochia trulliformis flowers was submitted to chromatographic processes, resulting in the isolation of twelve compounds, including seven flavonoids. The flavonoid kaempferol-3-O-β-glucopyranosyl-(1→4)-a-rhamnopyranosyl-(1→6)-β-glucopyranoside is being described for the first time in the literature. All chemical structures were determined by spectroscopic (NMR 1D and 2D, IR, UV, CD and [a]D and spectrometric analyzes (MS).
Descrição
Palavras-chave
Aristolochia urupaensis, Aristolochia trulliformis, Aristolochiaceae, Piranona, Ácido aristolóquico, Flavonoide