Biotransformation of (-)-ambrox by cell suspension cultures of Actinidia deliciosa.
Biotransformation of (-)-ambrox (1) with cell suspension cultures of Actinidia deliciosa (Kiwifruit) yielded the regio- and stereospecific oxygenated products 3-oxoambrox (2), 3beta-hydroxyambrox (3), 1alpha-hydroxyambrox (4), 3beta,6beta-dihydroxyambrox (5), 1alpha,6beta-dihydroxyambrox (6), and 1alpha,3beta-dihydroxyambrox (7). Metabolites 6 and 7 were found to be new compounds. These metabolites were structurally characterized on the basis of spectroscopic studies. The structure of compound 6 was unambiguously deduced by single-crystal X-ray diffraction techniques. Metabolites 2-7 were evaluated for in vitro inhibitory activity against the thymidine phosphorylase enzyme.
Nasib
Asma
A
H. E. J. Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Karachi-75270, Pakistan.
Musharraf
Syed Ghulam
SG
Hussain
Sajjad
S
Khan
Saifullah
S
Anjum
Shazia
S
Ali
Shamsher
S
Atta-Ur-Rahman
Atta-ur-Rahman
AU
Choudhary
M Iqbal
MI
D029042:Actinidia / Q000737:chemistry / Q000378:metabolism*; D001711:Biotransformation; D018360:Crystallography, X-Ray; D004791:Enzyme Inhibitors / Q000494:pharmacology; D004926:Escherichia coli / Q000201:enzymology; D005663:Furans / Q000737:chemistry / Q000378:metabolism*; D008968:Molecular Conformation; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry / Q000378:metabolism*; D013237:Stereoisomerism; D013939:Thymidine Phosphorylase / Q000037:antagonists & inhibitors
D004791:Enzyme Inhibitors; D005663:Furans; D009281:Naphthalenes; C413580:ambrox; D013939:Thymidine Phosphorylase