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), 10α-hydroxyisolongifolol (3), and 9α-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 μM, respectively. Compound 3 showed un-competitive mode of inhibition against butyrylcholinesterase with Ki value 15.0 μM. The structures of metabolites 2–4 were deduced on the basis of spectroscopic techniques and single-crystal X-ray diffraction techniques.

This paper describes the microbial transformation of (−)-isolongifolol (1) and butyrylcholinesterase inhibitory activity of the transformed products 2–4. The structures of transformed products were determined by spectroscopic and single crystal X-ray diffraction techniques.Figure optionsDownload as PowerPoint slide