CHEMICAL-MICROBIOLOGICAL SYNTHESIS OF ENT-13-EPI-MANOYL OXIDES WITH BILOGICAL ACTIVITIES

Article abstract of DOI:10.1016/S0031-9422(00)90350-9

The biotransformation of ent-13-epi-3-keto manoyl oxide, which possesses antileishmania activity, with Curvularia lunata produced ent-6β-hydroxy, ent-1α-hydroxy, ent-11β-hydroxy and Δ¹-derivatives, as well as a reduction product at C-3 (S-alcohol) with another hydroxyl group at C-6 (ent-6β) or C-11 (ent-11β).The ent-6β-hydroxy and Δ¹-derivatives inhibited growth of the pathogenic protozoa, Leishmania donovoni.The biotransformation of ent-12α-hydroxy-3β-hydroxy-13-epi-manoyl oxide and ent-3β-acetoxy-12-oxo-13-epi-manoyl oxide gave the ent-6β-hydroxyl derivatives.The incubation of ent-3β-acetoxy-12β-dihydroxy-13-epi-manoyl oxide gave ent-3β,12β-dihydroxy-13-epi-manoyl oxide and ent-3β,6β,12β-trihydroxy-13-epi-manoyl oxide (trimanoyl).Both products increased the activity of adenylatecyclase. - Key words: Curvularia lunata; biotransformation; ent-13-epi-manoyl oxides; antileishmanic activity; adenylatecyclase activator.