Synthesis, spectroscopy, and cytotoxicity of glycosylated acetogenin derivatives as promising molecules for cancer therapy

Several glycosyl derivatives of squamocin (1) have been synthesized by glyc osylation under Lewis acid catalysis with two different 1-O-acetyl sugars. Separation of these compounds has been achieved by HPLC and centrifugal par tition chromatography (CPC). A detailed NMR, ESIMS, and LSIMS study allowed complete structural elucidations. The cytotoxic activity of the glycosyl d erivatives was investigated and compared with that of squamocin and drosqua mocin against human epidermoid carcinoma cells (KB), African green monkey ( Cercopithecus aethiops) kidney epithelial cells (VERO), and mouse lymphocyt ic leukemia cells (L1210). The antiproliferative effects of some derivative s were studied on cell cycles in mouse lymphocytic leukemia cells (L1210).