Novel metabolite structures from biotransformation of a sesquiterpenoid ketone by selected fungal strains.
The sesquiterpenoid ketone, 1,4,4-trimethyltricyclo[5.4.0.0(3.5)]undec-7-en-9-one (1), was subjected to microbial transformation by six fungal strains: Aspergillus niger ATCC 9142, Aspergillus ochraceus DSM 824, Beauveria bassiana ATCC 7159, Cunninghamella echinulata ATCC 9244, Rhizopus arrhizus ATCC 11.145, and Absidia blakesleeana ATCC 10.148. Four main metabolites were formed from 1: 10(R)- and 10(S)-hydroxy-1,4,4-trimethyltricyclo-[5.4.0.0(3.5)]undec-7- en- 9-one (2 and 3, respectively), besides 4(R)- and 4(S)-(hydroxymethyl)-1,4-dimethyltricyclo[5.4.0.0(3.5)]undec -7-en-9-one (4 and 5, respectively). Compounds 2-5 were isolated with varying percentages from the respective transformations, and their structures established unequivocally by a combination of spectroscopic methods. Metabolites 2 and 3 are products of hydroxylation at C-10, in either R- or S-position; in 4 and 5, one geminal CH3 group each on the cyclopropane ring has been transformed into a CH2OH function.
Hebda
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Instytut Chemii Organicznej i Fizycznej, Politechnika Wroławska.
Szykula
J
J
Orpiszewski
J
J
Fischer
P
P
D001230:Aspergillus / Q000378:metabolism*; D001711:Biotransformation; D002849:Chromatography, Gas; D005658:Fungi / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D006900:Hydroxylation; D007659:Ketones / Q000493:pharmacokinetics*; D009682:Magnetic Resonance Spectroscopy; D012233:Rhizopus / Q000378:metabolism*; D012717:Sesquiterpenes / Q000493:pharmacokinetics*
D007659:Ketones; D012717:Sesquiterpenes; C070416:1,4,4-trimethyltricyclo(5.4.0.0(3,5))undec-7-en-9-one