title: Cometabolic oxidation of phenanthrene to phenanthrene trans-9,10-dihydrodiol by Mycobacterium strain S1 growing on anthracene in the presence of phenanthrene.
abstract: Mycobacterium strain S1, originally described as Rhodococcus strain S1 by chemotaxonomic criteria, was isolated by growth on anthracene, and is unable to use any of nine other polycyclic aromatic compounds as carbon source. Metabolism of phenanthrene during growth on anthracene as sole carbon source results in the accumulation of traces of a dihydrodiol metabolite in the growth medium, which, by comparison with authentic standards, has been tentatively identified as phenanthrene trans-9,10-dihydrodiol. Anthracene metabolites were ruled out on the basis of comparisons with authentic anthracene dihydrodiols from Pseudomonas fluorescens D1 and chemically synthesized anthrols. The original source of phenanthrene for dihydrodiol production was phenanthrene present as a < 1% contaminant in the anthracene used as carbon source. However, addition of further phenanthrene to the anthracene growth medium increased the level of phenanthrene trans-9,10-dihydrodiol formed. Mycobacterium strain S1 also produced phenanthrene trans-9,10-dihydrodiol when grown in a glucose-salts medium in the presence of phenanthrene. This dihydrodiol is a dead-end metabolite, and neither it nor its parent hydrocarbon are able to support the growth of Mycobacterium strain S1. Studies with metyrapone and ancimidol, which did not inhibit growth on anthracene but did inhibit formation of phenanthrene trans-9,10-dihydrodiol, suggest it is likely the product of a cytochrome P450 monooxygenase-like activity.
authors.affiliation: Department of Microbiology, University of Khon Kaen, Thailand.
authors.forename: S
authors.initials: S
authors.lastname: Tongpim
authors.forename: M A
authors.initials: MA
authors.lastname: Pickard
mesh_terms: D000873:Anthracenes / Q000378:metabolism*; D002849:Chromatography, Gas; D008797:Metyrapone / Q000494:pharmacology; D009161:Mycobacterium / Q000254:growth & development / Q000378:metabolism*; D010084:Oxidation-Reduction; D010616:Phenanthrenes / Q000378:metabolism*; D011551:Pseudomonas fluorescens / Q000378:metabolism; D011743:Pyrimidines / Q000494:pharmacology
chemical_list: D000873:Anthracenes; D010616:Phenanthrenes; D011743:Pyrimidines; C053577:ancymidol; C034020:anthracene; D008797:Metyrapone