Chemical-microbiological synthesis of ent-13- epi-manoyl oxides with biological activities

Abstract

The biotransformation of ent-13- epi-3-keto manoyl oxide, which possesses antileishmania activity, with Curvularia lunata produced ent-6β-hydroxy, ent-1βa-hydroxy, ent-11β-hydroxy and Δ 1- 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 Δ 1-derivatives inhibited growth ofthe pathogenic protozoa, Leishmania donovani. The biotransformation of ent- 12α-acetoxy-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.