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-...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2006-10, Vol.69 (10), p.1429-1434
Main Authors: Choudhary, Muhammad Iqbal, Siddiqui, Zafar A, Nawaz, Sarfraz A, Atta-ur-Rahman
Format: Article
Language:English
Subjects:
Animals
Aspergillus niger
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
biotransformation
Butyrylcholinesterase
caryophyllene oxide
Cephalosporium aphidicola
chemical structure
cholinesterase inhibitors
Cholinesterase Inhibitors - chemistry
Cholinesterase Inhibitors - pharmacology
Fabaceae
Fundamental and applied biological sciences. Psychology
Fungi - metabolism
Fusarium lini
Gibberella fujikuroi
Inhibitory Concentration 50
Macrophomina phaseolina
Medical sciences
medicinal plants
Methods. Procedures. Technologies
Molecular Structure
Neuropharmacology
Oxides - pharmacology
Pharmacology. Drug treatments
Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer..., (alzheimer disease)
Psychology. Psychoanalysis. Psychiatry
Psychopharmacology
Rhizopus stolonifer
Sesquiterpenes - chemistry
Sesquiterpenes - pharmacology
sesquiterpenoids
Sindora
Sindora sumatrana
spectral analysis
Stereoisomerism
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Summary: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 μM.
ISSN:0163-3864
1520-6025
DOI:10.1021/np0680174