title: New compounds, 6-hydroxykarahanaenone and 10-hydroxykarahanaenone, from biotransformation of karahanaenone by CYP2A6.
abstract: The in vitro biotransformation of karahanaenone was examined in cytochrome P450 (CYP) 2A6. The biotransformation of karahanaenone by CYP2A6 was investigated by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). Karahanaenone was found to be oxidized to two metabolites by CYP2A6. In order to produce large quantity of metabolites by CYP2A6, the biotransformation of karahanaenone by Salmonella typhimurium OY1002/2A6 was investigated. Similarly, two metabolites were confirmed by GC and GC-MS. The structure of metabolites was determined by 1D NMR, 2D NMR, and infrared, as a result there were new compounds, (6R)-hydroxykarahanaenone and 10-hydroxykarahanaenone.
authors.affiliation: a Department of Applied Chemistry , Faculty of Science and Engineering, Kinki University , Osaka 577-8502 , Japan.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Nakahashi
authors.forename: Nobuo
authors.initials: N
authors.lastname: Yagi
authors.forename: Mitsuo
authors.initials: M
authors.lastname: Miyazawa
mesh_terms: D001711:Biotransformation; D003508:Cycloheptanes / Q000737:chemistry / Q000302:isolation & purification*; D065637:Cytochrome P-450 CYP2A6 / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D008862:Microsomes, Liver / Q000378:metabolism*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012486:Salmonella typhimurium / Q000201:enzymology*
chemical_list: C000593157:10-hydroxykarahanaenone; C000593156:6-hydroxykarahanaenone; D003508:Cycloheptanes; D065637:Cytochrome P-450 CYP2A6
keywords: (6R)-hydroxykarahanaenone; 10-hydroxykarahanaenone; CYP2A6; S. typhimurium OY1002/2A6; biotransformation