title: Microbial transformation of (-)-isolongifolol and butyrylcholinesterase inhibitory activity of transformed products.
abstract: The microbial transformation of (-)-isolongifolol (1) by using the standard two-stage fermentation technique with Fusarium lini afforded polar oxygenated metabolites: 10-oxoisolongifolol (2), 10alpha-hydroxyisolongifolol (3), and 9alpha-hydroxyisolongifolol (4). Metabolites 3 and 4 were also formed with the incubation of 1 with Aspergillus niger. All three metabolites were found to be new. Compounds 3 and 4 inhibited butyrylcholinesterase enzyme in a concentration-dependent manner with IC50 values 13.6 and 299.5 microM, respectively. Compound 3 showed un-competitive mode of inhibition against butyrylcholinesterase with Ki value 15.0 microM. The structures of metabolites 2-4 were deduced on the basis of spectroscopic techniques and single-crystal X-ray diffraction techniques.
authors.affiliation: HEJ Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Karachi 75270, Pakistan.
authors.forename: M Iqbal
authors.initials: MI
authors.lastname: Choudhary
authors.forename: Syed Ghulam
authors.initials: SG
authors.lastname: Musharraf
authors.forename: Sarfraz Ahmad
authors.initials: SA
authors.lastname: Nawaz
authors.forename: Shazia
authors.initials: S
authors.lastname: Anjum
authors.forename: Masood
authors.initials: M
authors.lastname: Parvez
authors.forename: Hoong-Kun
authors.initials: HK
authors.lastname: Fun
authors.lastname: Atta-ur-Rahman
mesh_terms: D001234:Aspergillus niger / Q000378:metabolism*; D002091:Butyrylcholinesterase / Q000378:metabolism*; D002800:Cholinesterase Inhibitors / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology*; D005285:Fermentation; D005670:Fusarium / Q000378:metabolism*; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000737:chemistry* / Q000494:pharmacology*; D014162:Transfection; D014961:X-Ray Diffraction
chemical_list: D002800:Cholinesterase Inhibitors; D012717:Sesquiterpenes; C502389:isolongifolol; D002091:Butyrylcholinesterase