RESUMO
Bioactivity-guided isolation of the CHCl3-soluble fraction of the roots of Calotropis gigantea was carried out to obtain a new cardenolide glycoside, caloside G. Its absolute structure was elucidated based on NMR and ECD spectroscopic data interpretation. Caloside G showed noteworthy cytotoxicity against the PANC-1 human pancreatic and HeLa human cervical carcinoma cell lines, with the submicromolar IC50 values of 0.038 and 0.09 µM, respectively.
Assuntos
Antineoplásicos Fitogênicos , Calotropis , Antineoplásicos Fitogênicos/farmacologia , Cardenolídeos/farmacologia , Células HeLa , Humanos , Raízes de PlantasRESUMO
Phytochemical analysis of the roots of Calotropis gigantea led to the isolation of six new cardenolide glycosides, calosides A-F (1-6), and five known cardenolides (7-11). The structures of 1-6 were elucidated based on NMR and ECD spectroscopic data interpretation. Caloside D (4) is the first naturally occurring example of a cardenolide containing a C-8/C-19 oxygen bridge. In turn, calosides E (5) and F (6) represent the first naturally occurring 3-epi-cannogenol diglycosides having potent cytotoxicity against the PANC-1 cell line (IC50, 0.081 and 0.070 µM, respectively) and HeLa (IC50, both 0.17 µM) cells, under normoglycemic conditions.
Assuntos
Antineoplásicos Fitogênicos/química , Calotropis/química , Cardenolídeos/química , Glicosídeos/análise , Antineoplásicos Fitogênicos/farmacologia , Cardenolídeos/isolamento & purificação , Linhagem Celular Tumoral , Glicosídeos/química , Células HeLa , Humanos , Estrutura Molecular , Raízes de Plantas/químicaRESUMO
A new lignan, 9'-methoxypinoresinol (1), and two new glycosylated 5-hydroxymethylfurfurals, calofurfuralside A (2), and calofurfuralside B (3), together with nine known compounds (4-12) have been isolated from the active fractions, CHCl3 (IC50, 0.32µgmL-1) and EtOAc (IC50, 0.55µgmL-1) fractions of the leaves of Calotropis gigantea. Their structures were elucidated based on NMR and MS data. Among the isolated compounds, compounds 1 and 9 exhibited potent cytotoxicity against PANC-1 human pancreatic cancer cell line under the normoglycemic condition with IC50 values of 3.7 and 3.3µM, respectively. 9'-Methoxypinoresinol (1) significantly inhibited the colony formation of PANC-1 cells in a concentration-dependent manner.
