RESUMEN
One new 1,4-bis-phenyl-1,4-butanedione glycoside (14), one new eudesmane-type sesquiterpenoid (16), and 16 known compounds were isolated from the leaves and stems of Nelumbo nucifera Gaertn. The structures of the isolated compounds were elucidated by interpretation of their 1D and 2D NMR spectroscopic and HRESIMS data. Time-dependent density functional theory calculations and Electronic Circular Dichroism (ECD) spectroscopy was used to determine absolute configurations of the new eudesmane-type sesquiterpenoid (16). All the isolated compounds were examined for their antiosteoclastogenic activity. Preliminarily results of the TRAP staining on RAW 264.7 cells indicated that compounds 1 and 11 possess potential inhibitory effects on RANKL-induced osteoclast formation. Further bioassay investigation was carried out to reveal that compounds 1 and 11 suppressed RANKL-induced osteoclast formation in a concentration-dependent manner with the inhibition up to 55% and 78% at the concentration of 10 µM, respectively. In addition, the structure-activity relationship analysis showed that the 1,3-dioxole substitute and the double bond at C-6a/C-7 in the aporphine skeleton may be responsible for the antiosteoclastogenic activity. The findings provided valuable insights for the discovery and structural modification of aporphine alkaloids as the antiosteoclastogenic lead compounds.
Asunto(s)
Alcaloides , Aporfinas , Lotus , Nelumbo , Sesquiterpenos de Eudesmano , Alcaloides/farmacología , Aporfinas/farmacología , Dioxoles , Glicósidos/análisis , Estructura Molecular , Nelumbo/química , Hojas de la Planta/químicaRESUMEN
Eleven previously undescribed glycosylated compounds with phenolic (abeoside A-F), monoterpenyl (abeoside G and H), or 2-heptanyl (abeoside I-K) aglycone, and twenty one reported compounds were isolated from the trunk of Abies holophylla. The structures of the previously undescribed compounds were elucidated on the basis of the conventional NMR and HRMS data analysis, and the absolute configuration of sugar units were assigned by chiral derivatization and LC-MS analysis. All the isolated compounds were evaluated for their anti-neuroinflammatory and neurotrophic activities. Among the evaluated compounds, twelve compounds including abeoside A, B, E, G, H, J, and K exhibited strong anti-neuroinflammatory activities with IC50 values of 4.6-18.2 µM by inhibiting production of LPS-induced NO levels, and abeoside C and 1-O-[(S)-oleuropeyl]-ß-D-glucoside showed powerful effects on the stimulation of NGF secretion levels with 157.09 ± 8.53% and 154.74 ± 1.24%, respectively.