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

The biotransformation of ent-13-epi-3-keto manoyl oxide, which possess es antileishmania activity, with Curvularia lunata produced ent-6 beta -hydroxy, ent-1 alpha-hydroxy, ent-11 beta-hydroxy and Delta(1)-deriva tives, as well as a reduction product at C-3 (S-alcohol) with another hydroxyl group at C-6 (ent-6 beta) or C-11 tent-11 beta). The ent-6 be ta-hydroxy and Delta(1)-derivatives inhibited growth of the pathogenic protozoa, Leishmania donovani. The biotransformation of ent-12 alpha- acetoxy-3 beta-hydroxy-13-epi-manoyl oxide and ent-3 beta-acetoxy-12-o xo-13-epi-manoyl oxide gave the ent-6 beta-hydroxyl derivatives. The i ncubation of ent-3 beta-acetoxy-12 beta-dihydroxy-13-epi-manoyl oxide gave ent-3 beta,12 beta-dihydroxy-13-epi-manoyl oxide and ent-3 beta,6 beta,12 beta-trihydroxy-13-epi-manoyl oxide (trimanoyl). Both product s increased the activity of adenylatecyclase.