UNSATURATED EPOXY-C-GLYCOSIDES - A NEW CLASS OF ANTITUMOR COMPOUNDS WITH DNA CLEAVAGE PROPERTIES

alpha,beta-Unsaturated-epoxy-C-glycosides were synthesized by the cond ensation of 4-keto unsaturated C-glycosides with dimethyl sulfonium me thylide. These compounds were tested for cytotoxic activity against Ra ji and LFC12a cells. Simple C-glycosides were found unreactive. Howeve r, the derivatives of fatty acids have shown a cytotoxic activity comp arable to those of the most potent keto C-glycosides. An apoptosis stu dy carried out with these compounds led to the conclusions that epoxy- C-glycosides possess DNA cleavage properties.