RESUMO
Chemical examination of the methanolic extract from the stem bark of Daphne aurantiaca led to the isolation of two innovanoside dimers (1 and 2) with an unusual four-membered cyclobutane ring, together with the isoinnovanoside 3. Their chemical structures and configurations were elucidated by extensive spectral analysis and synthesis.
Assuntos
Ciclobutanos/síntese química , Daphne/química , Glucosídeos/síntese química , Extratos Vegetais/síntese química , Pironas/síntese química , Cristalografia por Raios X , Ciclobutanos/química , Ciclobutanos/isolamento & purificação , Dimerização , Glucosídeos/química , Glucosídeos/isolamento & purificação , Modelos Moleculares , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Pironas/química , Pironas/isolamento & purificaçãoRESUMO
The inhibitory activity of 4,4'-dihydroxy-α-truxillic acid and its derivatives (5-1a-5-35a) on nitric oxide (NO) release was evaluated in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages. Compounds 5-3a, 5-4a, 5-5a, 5-10a, 5-24a, 5-26a and 5-30a exhibited significant inhibitory effects on NO production, with IC50 values of 19.8, 21.1, 16.4, 17.5, 20.8, 22.6 and 17.6 µM, respectively. Their cytotoxicities were also estimated using a CCK-8 assay. Among them, compound 5-10a showed no cytotoxic effect on cells up to a concentration of 50 µM. The structure-activity relationships of the compounds are also discussed.
