RESUMO
Three undescribed sesquiterpenes (1-3), two enantiomeric pairs of monoterpenes (4a/4b-5a/5b), one alkyne (6), two known alkynes (7-8) and eight known coumarins (9-16) were isolated from the aerial parts extracts of Artemisia scoparia. The structures of these compounds were fully elucidated by their 1D and 2D NMR, HRESIMS spectral data analyses, and comparison with literature. The absolute configurations of compounds were determined by single-crystal X-ray crystallography (1), a comparison of experimental and calculated electronic circular dichroism (ECD) data (2-6). 15 showed moderate inhibitory activity with the NO release in LPS-induced RAW264.7 cells. 9-16 showed varying degrees of promoting melanogenesis and tyrosinase activity in B16 cells.
Assuntos
Artemisia , Óxido Nítrico , Artemisia/química , Camundongos , Animais , Células RAW 264.7 , Óxido Nítrico/antagonistas & inibidores , Óxido Nítrico/biossíntese , Óxido Nítrico/metabolismo , Monofenol Mono-Oxigenase/antagonistas & inibidores , Monofenol Mono-Oxigenase/metabolismo , Lipopolissacarídeos/antagonistas & inibidores , Lipopolissacarídeos/farmacologia , Cristalografia por Raios X , Componentes Aéreos da Planta/química , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Sesquiterpenos/isolamento & purificação , Estrutura Molecular , Monoterpenos/química , Monoterpenos/isolamento & purificação , Monoterpenos/farmacologia , Cumarínicos/química , Cumarínicos/farmacologia , Cumarínicos/isolamento & purificação , Conformação Molecular , Melaninas/antagonistas & inibidores , Melaninas/metabolismo , Modelos Moleculares , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Extratos Vegetais/isolamento & purificaçãoRESUMO
Investigation on the chemical constituents of Artemisia scoparia resulted in the isolation of sixteen compounds, including undescribed six pairs of diprenylated phenolic enantiomers (±)-scopacoumaricin A-F, and two pairs of cis-trans isomers cis/trans-scopacoumaricin G and cis/trans-artepillin A. Trans-artepillin A was obtained from this plant for the first time. The structures of the isolates were proposed by analysis of their 1D, 2D-NMR and HRESIMS spectroscopic data. Their absolute configurations were determined by comparison of their experimental and calculated electronic circular dichroism spectra. Evaluations of the anti-inflammatory activity revealed that (-)-scopacoumaricin D, (+)-scopacoumaricin F and cis-scopacoumaricin G showed moderate anti-inflammatory activity on lipopolysaccharide-induced nitric oxide production in RAW264.7 cell.
