Microbial transformation of (-)-isolongifolol and butyrylcholinesterase inhibitory activity of transformed products

Bioorg Med Chem. 2005 Mar 15;13(6):1939-44. doi: 10.1016/j.bmc.2005.01.015.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aspergillus niger / metabolism*
  • Butyrylcholinesterase / metabolism*
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / metabolism*
  • Cholinesterase Inhibitors / pharmacology*
  • Fermentation
  • Fusarium / metabolism*
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Structure
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / pharmacology*
  • Transfection
  • X-Ray Diffraction

Substances

  • Cholinesterase Inhibitors
  • Sesquiterpenes
  • isolongifolol
  • Butyrylcholinesterase