title: Oxidation of brefeldin A.
abstract: Oxidation of the macrolide antibiotic brefeldin A with pyridinium chlorochromate adsorbed on alumina afforded [6S, 10E, 11aS, 14E]-6-methyl-2,3,6,7,8,9,11a,12-octahydro-4 H-cyclopent[f]oxacyclotridecin-1,4,13-trione together with 13-oxobrefeldin. These compounds showed higher cytotoxic activity on P388 leukemia cells than brefeldin A, brefeldin A-1,13-diacetate, brefeldin A-13-acetate, tetrahydrobrefeldin or tetrahydrobrefeldin-1,13-dione. 13-Oxobrefeldin exceeded brefeldin A in antifungal activity on Candida albicans.
authors.affiliation: Institute of Chemistry, Slovak Academy of Sciences, Bratislava.
authors.forename: B
authors.initials: B
authors.lastname: Proksa
authors.forename: D
authors.initials: D
authors.lastname: Uhrin
authors.forename: J
authors.initials: J
authors.lastname: Adamcová
authors.forename: J
authors.initials: J
authors.lastname: Fuska
mesh_terms: D000818:Animals; D000903:Antibiotics, Antineoplastic / Q000627:therapeutic use*; D020126:Brefeldin A; D002176:Candida albicans / Q000187:drug effects*; D002470:Cell Survival / Q000187:drug effects; D003517:Cyclopentanes / Q000737:chemistry* / Q000627:therapeutic use; D007941:Leukemia P388 / Q000188:drug therapy*; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D010084:Oxidation-Reduction
chemical_list: D000903:Antibiotics, Antineoplastic; D003517:Cyclopentanes; D020126:Brefeldin A