title: Metabolism of 3-hydroxychrysene by rat liver microsomal preparations.
abstract: 3-Hydroxychrysene, a metabolite of the polycyclic aromatic hydrocarbon (PAH) chrysene, was metabolised by rat liver microsomal preparations obtained from Arochlor 1254-pretreated rats. Eight major metabolites were isolated by high performance liquid chromatography and characterised by u.v. spectroscopy and a variety of mass spectrometric techniques. The metabolites were unambiguously identified as 9-hydroxy-trans-1,2-dihydroxy-1,2-dihydrochrysene and 9-hydroxy-r-1,t-2,t-3,c-4-tetrahydroxy-1,2,3,4-tetrahydrochrysene and tentatively identified as 3-hydroxy-trans-5,6-dihydroxy-5,6-dihydrochrysene (since chrysene is a symmetrical molecule the 3- and 9-positions are equivalent), 9-hydroxy-trans-3,4-dihydroxy-3,4-dihydrochrysene, 1,2,3-trihydroxy-1,2,3,4-tetrahydrochrysene, an oxidised phenol and two diphenols. These results indicate that 3-hydroxychrysene can be further metabolised via a number of different pathways including those involving the formation of phenol- and triol-epoxides.
authors.affiliation: Chester Beatty Laboratories, Institute of Cancer Research, Royal Cancer Hospital, London, U.K.
authors.forename: M S
authors.initials: MS
authors.lastname: Masento
authors.forename: G W
authors.initials: GW
authors.lastname: Taylor
authors.forename: D
authors.initials: D
authors.lastname: Watson
authors.forename: A
authors.initials: A
authors.lastname: Seidel
authors.forename: W
authors.initials: W
authors.lastname: Bochnitschek
authors.forename: F
authors.initials: F
authors.lastname: Oesch
authors.forename: P L
authors.initials: PL
authors.lastname: Grover
mesh_terms: D000818:Animals; D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid; D002911:Chrysenes / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D008297:Male; D013058:Mass Spectrometry; D008862:Microsomes, Liver / Q000378:metabolism*; D015394:Molecular Structure; D010616:Phenanthrenes / Q000378:metabolism*; D051381:Rats; D011919:Rats, Inbred Strains; D013056:Spectrophotometry, Ultraviolet
chemical_list: D002911:Chrysenes; D010616:Phenanthrenes; C063661:3-hydroxychrysene