Biotransformations of ent-18-acetoxy-6-ketomanoyl oxides epimers at C-13 with filamentous fungi.
Two ent-18-acetoxy-6-oxomanoyl oxides, epimers at C-13, have been prepared from ent-6alpha,8alpha,18-trihydroxylabda-13(16),14-diene (andalusol), isolated from Sideritis foetens, by means of several chemical pathways and a regioselective acylation with Candida cylindracea lipase (CCL). Biotransformation of these 13-epimeric ent-manoyl oxides by Fusarium moniliforme and Neurospora crassa produced mainly ent-1beta- or ent-11alpha-hydroxylations, as well as their deacetylated derivatives, in both epimers. In addition, with the 13-epi substrate N. crassa originated other minor hydroxylations by the ent-alpha face at C-1 or at C-12, whereas an ent-11beta-hydroxyl group, probably originated by reduction of an 11-oxo derivative also isolated, was achieved with the 13-normal substrate.
Ghoumari
Hanae
H
Faculté des Sciences, Universite Abdelmalek Essaadi, Tetouan, Morocco.
Benajiba
Mohamed-Hassan
MH
García-Granados
Andrés
A
Fernández
Antonia
A
Martínez
Antonio
A
Rivas
Francisco
F
Arias
José M
JM
D001711:Biotransformation; D002244:Carbon / Q000737:chemistry / Q000378:metabolism*; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D005670:Fusarium / Q000378:metabolism*; D006900:Hydroxylation; D009492:Neurospora crassa / Q000378:metabolism*; D010087:Oxides / Q000378:metabolism*; D031365:Sideritis / Q000737:chemistry; D013237:Stereoisomerism
D004224:Diterpenes; D010087:Oxides; C110596:ent-13(16),14-labdadiene-6,8,18-triol; D002244:Carbon