Glass-Capillary-Gas Chromatography/Mass Spectrometry Data of Mono- and Poly-hydroxylated Benz[α]anthracene. Comparison with Benz[α]anthracene Metabolites from Rat Liver Microsomes

Abstract

By means of glass-capillary-gas chromatography all possible benz[a]anthracene metabolites formed by rat liver microsomes (phenols, dihydrodiols, dihydrodiol enols and tetrahydrotetrols) can be separated. Mass spectra of their trimethylsilyl ethers show intense molecule ions and, in most cases, characteristic fragments. K-Region diols and their secondary oxidation products can be recognized by the ratio (m/e 147)/(m/e 191) > 1, whereas the ratio is inverse in all other dihydrodiol trimethylsilyl ethers investigated. With the exception of 1,2-dihydrobenz[a]anthracene-1,2,3-triol all vicinal dihydrodiol enols investigated exhibit an intense elimination of the fragment +CH.dbd.CH.sbd.OSiME3 according to m/e 379. The conformation of vicinal tetrahydrobenz[a]anthracenetetrols possibly can be distinguished by the intensity of m/e 380 (M-204) since only in those possessing 2 or more subsequent Me3SiO groups in the same conformation intense elimination of Me3Si.sbd.O.sbd.CH.dbd.CH.sbd.O-SiMe3 is observed. Retention times and mass spectrometric data of a series of synthetic benz[a]anthracene derivatives are presented as a base for the identification of benz[a]anthracene metabolites in biological systems.