The incubation of 13α,17-dihydroxystemodane with Cephalosporium aphidicola.
The biotransformation of 13α,17-dihydroxystemodane (3) with the fungus Cephalosporium aphidicola afforded 13α,17,18-trihydroxystemodane (4), 3β,13α,17-tri-hydroxystemodane (5), 13α,17-dihydroxy-stemodan-18-oic acid (6), 3β,11β,13α,17-tetra-hydroxystemodane (7), 11β,13α,17,18-tetrahydroxystemodane (8) and 3β,13α,17,18-tetra-hydroxystemodane (9). The hydroxylation at C-18 of the substrate points to a biosynthetically-directed transformation, because aphidicolin (2) is hydroxylated at this carbon. However, the C-3(β) and C-11(β) hydroxylations seem to indicate a xenobiotic biotransformation.
Instituto de Productos Naturales y Agrobiología, C.S.I.C., Avda. Astrofísico F. Sánchez 3, La Laguna, Tenerife, Canary Islands, 38206, Spain. bmfraga@ipna.csic.es
Braulio M
BM
Fraga
Ricardo
R
Guillermo
Melchor G
MG
Hernández
María C
MC
Chamy
Juan A
JA
Garbarino
D000164:Acremonium / Q000378:metabolism*; D001711:Biotransformation; D004224:Diterpenes / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization
C572090:13alpha,17-dihydroxystemodane; D004224:Diterpenes