Microbial Transformation Of Oleanolic Acid

Five funges which can transformate oleanolic acid were screened of 25 kinds of fungu, and two of them were chosen to accumulate.Night transformation products were gained Microbial transformation of oleanolic acid(1) by two fungus. Alternaria longipes AL3.2875 gave six metabolites(1-6), compound 1 (oleanolic acid 28-O-β-D-glucopyranosyl ester), compound2 (2a,3a,19a-trihydroxy-ursolic acid-28-O-β-D-glucoside),compound 3(oleanolic acid-3-O-β-D-glucopy ranoside),compound 4(2β,3β,19α-trihydroxy-oleanolic acid-28-O-β-D-glucoside), compound 5(2α,3β,19a-trihydroxy-ursolic acid-28-O-β-D-glucoside)and compound 6 (3-0-(β-D-Glucuronopyranosyl)-oleanolic acid-28-O-β-D-glucopyranosyl))respectively.While, microbial transformation of oleanolic acid by Penicillium adametzi AS 3.447 afforded three metabolites(7-9), compound 7*(7β,21β- dihydroxyloleanolic acid),compound 8 (21β-hydroxyloleanolic acid-28 -O-β-D-glucopyranoside) and compound 9 (21β-hydroxyloleanolic acid).The structures of the compounds were assigned by NMR and MS spectroscopic methods,compound 7* was a new compound.Observingly,compound 2,compound 5 were changed ursane by oleanane,which are formed by participation of "retro-biosynthetic" methyl migration from C-20 to C-19. The in vitro cytotoxic activities of metabolites against one human cancer cell lines were determined by the MTT method; compound 3, compound 8and compound 9 had more potent inhibitory effects against Hela cell line than the substrate.