Chemical-microbiological synthesis of ent-13-epi-manoyl oxides with biological activities.
The biotransformation of ent-13-epi-3-keto manoyl oxide, which possesses antileishmania activity, with Curvularia lunata produced ent-6 beta-hydroxy, ent-1 alpha-hydroxy, ent-11 beta-hydroxy and delta 1-derivatives, as well as a reduction product a C-3 (S-alcohol) with another hydroxyl group at C-6 (ent-6 beta) or C-11 (ent-11 beta). The ent-6 beta-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 beta-dihydroxy-13-epi-manoyl oxide gave ent-3 eta,12 beta-dihydroxy-13-epi-manoyl oxide and ent-3 beta,6 beta,12 beta-trihydroxy-13-epi-manoyl oxide (trimanoyl). Both products increased the activity of adenylatecyclase.
García-Grandos
A
A
Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada, Spain.
Jiménez
M B
MB
Martínez
A
A
Parra
A
A
Rivas
F
F
Arias
J M
JM
D000818:Animals; D000981:Antiprotozoal Agents / Q000138:chemical synthesis / Q000378:metabolism* / Q000494:pharmacology; D002240:Carbohydrate Sequence; D007893:Leishmania donovani / Q000187:drug effects / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D003904:Mitosporic Fungi / Q000378:metabolism*; D008969:Molecular Sequence Data; D010087:Oxides / Q000378:metabolism; D013055:Spectrophotometry, Infrared; D013729:Terpenes / Q000138:chemical synthesis / Q000378:metabolism* / Q000494:pharmacology
D000981:Antiprotozoal Agents; D010087:Oxides; D013729:Terpenes