title: A soluble Bacillus cereus cytochrome P-450cin system catalyzes 1,4-cineole hydroxylations.
abstract: A cytochrome P-450-dependent monooxygenase system that catalyzes the stereospecific hydroxylation of the monoterpene substrate 1,4-cineole was demonstrated in cell-free preparations of Bacillus cereus UI-1477. 1,4-Cineole hydroxylations were catalyzed by a 100,000 x g (1-h)-centrifuging soluble, hexane-inducible enzyme that activated and incorporated molecular oxygen into hydroxylated products; required NADH; was inhibited by SKF-525A, imidazole, metyrapone, and octylamine; and displayed a 452-nm peak in the carbon monoxide difference absorption spectrum. The constant 7:1 ratio of endo/exo alcohol products formed when 1,4-cineole was hydroxylated by normal cells, hexane-induced cells, and cell extracts suggested that a single enzyme designated cytochrome P-450cin was responsible for both reactions.
authors.affiliation: Division of Medicinal and Natural Product Chemistry, University of Iowa, Iowa City 52242.
authors.forename: W
authors.initials: W
authors.lastname: Liu
authors.forename: J P
authors.initials: JP
authors.lastname: Rosazza
mesh_terms: D000588:Amines / Q000494:pharmacology; D001409:Bacillus cereus / Q000201:enzymology*; D000081005:Cyclohexane Monoterpenes; D065607:Cytochrome P-450 Enzyme Inhibitors; D003577:Cytochrome P-450 Enzyme System / Q000096:biosynthesis / Q000378:metabolism*; D004790:Enzyme Induction / Q000187:drug effects; D006586:Hexanes / Q000494:pharmacology; D006900:Hydroxylation; D007093:Imidazoles / Q000494:pharmacology; D008797:Metyrapone / Q000494:pharmacology; D039821:Monoterpenes; D009243:NAD / Q000378:metabolism; D010100:Oxygen / Q000378:metabolism; D010105:Oxygenases / Q000037:antagonists & inhibitors / Q000096:biosynthesis / Q000378:metabolism*; D011335:Proadifen / Q000494:pharmacology; D012995:Solubility; D013729:Terpenes / Q000378:metabolism*
chemical_list: D000588:Amines; D000081005:Cyclohexane Monoterpenes; D065607:Cytochrome P-450 Enzyme Inhibitors; D006586:Hexanes; D007093:Imidazoles; D039821:Monoterpenes; D013729:Terpenes; D009243:NAD; C029899:imidazole; D003577:Cytochrome P-450 Enzyme System; D011335:Proadifen; C058951:1,4-cineole; D010105:Oxygenases; D010100:Oxygen; C008699:octylamine; D008797:Metyrapone