Microbial transformation and butyrylcholinesterase inhibitory activity of (-)-caryophyllene oxide and its derivatives.
Microbial transformation of the sesquiterpene (-)-caryophyllene oxide (1) [(1R,4R,5R,9S)-4,5-epoxycaryophyllan-8(13)-ene] by a number of fungi, using a standard two-stage fermentation technique, has afforded as products (1R,4R,5R,9S)-4,5-dihydroxycaryophyllan-8(13)-ene (2), (1S,4R,5R,8S,9S)-clovane-5,9-diol (3), (1R,4R,5R,9S,11R)-4,5-epoxycaryophyllan-8(13)-en-15-ol (4), (1R,4R,5R,9S,11S)-4,5-epoxycaryophyllan-8(13)-en-14-ol (5), (1R,2S,4R,5R,9S)-4,5-epoxy-13-norcaryophyllan-8-one (6), (1R,4R,5R,8S,9S)-4,5-epoxycaryophyllan-13-ol (7), (1R,4R,5R,8S, 9S,13S)-caryolane-5,8,13-triol (8), (1R,3R,4R,5R,8S,9S)-4,5-epoxycaryophyllan-3,13-diol (9), and (1S,4R,5R,8S,9S)-clovane-5,9,12-triol (10). Metabolites 6 and 8-10 were found to be new compounds, as deduced on the basis of spectroscopic techniques. Compounds 1-10 were evaluated for butyrylcholinesterase inhibitory activity, and compound 5 exhibited an IC50 value of 10.9 +/- 0.2 microM.
Choudhary
Muhammad Iqbal
MI
H. E. J. Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Karachi-75270, Pakistan. hej@cyber.net.pk
Siddiqui
Zafar A
ZA
Nawaz
Sarfraz A
SA
Atta-ur-Rahman
D000818:Animals; D002091:Butyrylcholinesterase; D002800:Cholinesterase Inhibitors / Q000737:chemistry / Q000494:pharmacology*; D005658:Fungi / Q000378:metabolism*; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D010087:Oxides / Q000494:pharmacology; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism
D002800:Cholinesterase Inhibitors; D010087:Oxides; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; D002091:Butyrylcholinesterase; C515179:caryophyllene oxide