Unsaturated epoxy-C-glycosides. A new class of antitumor compounds with DNA cleavage properties

Abstract α,β-Unsaturated-epoxy-C-glycosides were synthesized by the condensation of 4-keto unsaturated C-glycosides with dimethyl sulfonium methylide. These compounds were testes for cytotoxic activity against Raji and LFC12a cells. Simple C-glycosides were found unreactive. However, the derivatives of fatty acids have shown a cytotoxic activity comparable to those of the most potent keto C-glycosides. An apoptosis study carried out with these compounds led to the conclusions that epoxy-C-glycosides possess DNA cleavage properties.