ABSTRACT
Objective: To investigate the lignans of the roots of Diphylleia sinensis. Methods: The chemical components were isolated and purified by chromatographic techniques (silica gel, sephadex LH-20 and semi preparative-HPLC) and the chemical structures were determined by spectral data analysis (1D/2D NMR, MS, and IR). Results: Seven lignans were obtained and identified as diphyllin A (1), (1S,2R,5S,6R)-2-(4-hydroxyphenyl)-6-(3-methoxy-4-hydroxyphenyl)-3,7-dioxabicyclo [3.3.0] octane (2), (7S,8R,7’S,8’R)-3,4,3’,4’-tetramethoxy-9,7-dihydroxy-8.8’,7.O.9’-lignan (3), (-)-lariciresinol (4), vladinol D (5), podophyllotoxone (6), and justicidin A (7). Conclusion: Diphyllin A (1) is a new compound and 2-4 are obtained from D. sinensis for the first time.
ABSTRACT
Podophyllotoxone (1) was isolated from the roots of Dysosma versipellis. The structure was determined by spectroscopic analysis in combination with single-crystal X-ray analysis. The absolute configuration of compound 1 was assigned based on the Flack parameter. It showed significant inhibitory activities against human prostate cancer cells PC3 and DU145 with IC50 values being 14.7 and 20.6 μmol·L(-1), respectively. It also arrested the cells at G2/M phase. Tubulin polymerization assay showed that it inhibited the tubulin polymerization in a dose-dependent manner, and molecular docking analysis revealed a different binding mode with tubulin as compared with those known tubulin inhibitors.