A series of diphyllin glycosides were synthesized from diphyllin by phase transfer catalysis glycosylation, deprotection, and etherification, and the structures were established by (1) H NMR, (13) C NMR, and HRMS. These glycosides were evaluated for their in vitro cytotoxicity against HCT-116, A549, and A549T cancer cell lines by MTT assay, and most of them were cytotoxic at submicromolar concentrations. They were also effective against the paclitaxel-resistant cell line A549T. The kDNA decatenation assay indicated that most of these compounds inhibited topoisomerase IIα-mediated kDNA decatenation. In addition, the in vitro tubulin polymerization study showed that compounds 5 and 6 had antimicrotubule activity with a paclitaxel-like mode of action. Taken together, these results suggest that these diphyllin glycosides act on both TopoII and tubulin.
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