New polyoxygenated ent-manoyl oxides obtained by biotransformation with filamentous fungi.
Incubation of methyl (13R)-ent-16-hydroxy-8 alpha,13-epoxylabd-14-en-18-oate [4] with Curvularia lunata yielded ent-1 beta-hydroxy [6] and ent-6 beta-hydroxy [7] derivatives, and that of methyl (13S)-ent-16-dihydroxy-8 alpha,13-epoxylabd-14-en-18-oate [5] with the same organism gave ent-11 beta-hydroxy [8], ent-6 beta-hydroxy [9], and ent-6 beta,11 beta-dihydroxy [10] derivatives. The incubation of substrates 4 and 5 with Fusarium moniliforme afforded ent-1 beta-hydroxy derivatives (6 and 14, respectively). Cunninghamella elegans produced ent-3 beta-hydroxy, ent-1 beta-hydroxy and ent-1 beta,3 beta-dihydroxy derivatives, and led to epoxidation of the double bond of the substrates. In addition, ent-3 beta,11 alpha-dihydroxy (as the acetoxy derivative 17) and ent-3 beta,11 beta-dihydroxy [12] derivatives were isolated from incubations of substrates 4 and 5, respectively. Compounds 7, 9-11, 14, 16-18, and 21 were characterized as new polyoxygenated ent-manoyl oxides.
García-Granados
A
A
Departamento de Química Orgánica, Universidad de Granada, Spain.
Liñán
E
E
Martínez
A
A
Onorato
M E
ME
Arias
J M
JM
D001711:Biotransformation; D005576:Colforsin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism; D003470:Culture Media / Q000737:chemistry; D005670:Fusarium / Q000737:chemistry / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D009090:Mucorales / Q000737:chemistry / Q000378:metabolism*
D003470:Culture Media; D005576:Colforsin