RESUMO
A phytochemical investigation on crude extract of Gentianella azurea led to the isolation of ten new (1-10) and one known (11) secoiridoid glycosides. Their structures were unambiguously elucidated by analysis of 1D and 2D NMR. Compounds 2, 5 and 11 were found to inhibit nitric oxide (NO) production in RAW 264.7 macrophages with IC50 values of 52.78 ± 8.61, 0.69 ± 0.23 and 5.18 ± 1.33, respectively, while indomethacin, the positive control, showed an IC50 value of 1.25 ± 0.52 µM.
Assuntos
Anti-Inflamatórios/química , Gentianella/química , Glicosídeos Iridoides/química , Animais , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Linhagem Celular , Gentianella/metabolismo , Humanos , Glicosídeos Iridoides/isolamento & purificação , Glicosídeos Iridoides/farmacologia , Macrófagos/citologia , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Espectroscopia de Ressonância Magnética , Camundongos , Conformação Molecular , Óxido Nítrico/metabolismoRESUMO
Thirteen new dammarane-type triterpenoids (1-13) and four known analogues, gentirigenic acid (14) and the gentirigeosides A, B, and E (15-17), were isolated from Gentianella azurea. Their structures were elucidated by detailed analysis of the NMR, MS, and X-ray crystallographic data. This is the first report of dammarane-type triterpenoids in the Gentianella genus. In addition, the known structures of gentirigenic acid (14) and the gentirigeosides A, B, and E (15-17) were revised based on the X-ray diffraction analysis. Gentirigeoside A (15) was found to inhibit nitric oxide production in RAW 264.7 macrophages with an IC50 value of 6.6 ± 2.1 µM.
