Microbial transformation of (-)-isolongifolol and butyrylcholinesterase inhibitory activity of transformed products.
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.
Choudhary
M Iqbal
MI
HEJ Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Karachi 75270, Pakistan.
Musharraf
Syed Ghulam
SG
Nawaz
Sarfraz Ahmad
SA
Anjum
Shazia
S
Parvez
Masood
M
Fun
Hoong-Kun
HK
Atta-ur-Rahman
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
D002800:Cholinesterase Inhibitors; D012717:Sesquiterpenes; C502389:isolongifolol; D002091:Butyrylcholinesterase