Oxygenation mechanism in conversion of aldehyde to carboxylic acid catalyzed by a cytochrome P-450 isozyme.
The oxygenation of an aldehyde, 11-oxo-delta 8-tetrahydrocannabinol to a carboxylic acid, delta 8-tetrahydrocannabinol-11-oic acid was catalyzed by cytochrome P-450 MUT-2 purified from hepatic microsomes of male ddN mice. The oxygenation mechanism was confirmed by the incorporation of oxygen-18 from molecular oxygen into the carboxylic acid formed. An aldehyde form but not a hydrated form of 11-oxo-delta 8-tetrahydrocannabinol may be a substrate for the cytochrome P-450. The oxygenation of aldehyde catalyzed by cytochrome P-450 might be a common metabolic reaction in biological systems, and should be considered as an additional role of cytochrome P-450 in biotransformation of endogenous compounds and xenobiotics.
Watanabe
K
K
Department of Hygienic Chemistry, Faculty of Pharmaceutical Sciences, Hokuriku University, Kanazawa, Japan.
Narimatsu
S
S
Yamamoto
I
I
Yoshimura
H
H
D000447:Aldehydes / Q000737:chemistry*; D000595:Amino Acid Sequence; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D003577:Cytochrome P-450 Enzyme System / Q000235:genetics / Q000378:metabolism*; D013759:Dronabinol / Q000031:analogs & derivatives* / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D007527:Isoenzymes / Q000235:genetics / Q000378:metabolism*; D008969:Molecular Sequence Data; D010100:Oxygen / Q000378:metabolism
D000447:Aldehydes; D002264:Carboxylic Acids; D007527:Isoenzymes; C020443:11-oxo-delta(8)-tetrahydrocannabinol; D013759:Dronabinol; D003577:Cytochrome P-450 Enzyme System; D010100:Oxygen