Microbial hydroxylation of pregnenolone derivatives.
Pregnenolone and pregnenolone acetate were incubated with the fungi Cunninghamella elegans, Rhizopus stolonifer and Gibberella fujikuroi. Incubation of with C. elegans yielded metabolites, 3beta,7beta,11alpha-trihydroxypreg-5-en-20-one, 3beta,6alpha,11alpha,12beta,15beta-pentahydroxypreg-4-en-20-one and 3beta,6beta,11alpha-trihydroxypreg-4-en-20-one, while incubation with G. fujikuroi yielded two known metabolites, 3beta,7beta-dihydroxypregn-5-en-20-one and 6beta,15beta-dihydroxypreg-4-ene-3,20-dione. Metabolites and were found to be new. Fermentation of by C. elegans yielded four known oxidative metabolites, androsta-1,4-diene-3,17-dione, 6beta,15beta-dihydroxyandrost-4-ene-3,17-dione and 11alpha,15beta-dihydroxypreg-4-ene-3,20-dione. Fermentation of with R. stolonifer yielded two known metabolites, 11alpha-hydroxypreg-4-ene-3,20-dione and. Compounds were screened for their cholinesterase inhibitory activity in a mechanism-based assay.
Choudhary
Muhammad Iqbal
MI
H.E.J. Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Pakistan. hej@cyber.net.pk
Batool
Iffat
I
Shah
Syed Adnan Ali
SA
Nawaz
Sarfraz Ahmad
SA
Atta-ur-Rahman
D000818:Animals; D001711:Biotransformation; D002800:Cholinesterase Inhibitors / Q000494:pharmacology; D002802:Cholinesterases / Q000737:chemistry; D004593:Electrophorus; D005285:Fermentation; D005658:Fungi / Q000378:metabolism*; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D011284:Pregnenolone / Q000378:metabolism* / Q000494:pharmacology; D021241:Spectrometry, Mass, Electrospray Ionization; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
D002800:Cholinesterase Inhibitors; D011284:Pregnenolone; D002802:Cholinesterases