title: Metabolism of phenanthrene by the marine cyanobacterium Agmenellum quadruplicatum PR-6.
abstract: Under photoautotrophic growth conditions, the marine cyanobacterium Agmenellum quadruplicatum PR-6 metabolized phenanthrene to form trans-9,10-dihydroxy-9,10-dihydrophenanthrene (phenanthrene trans-9,10-dihydrodiol) and 1-methoxyphenanthrene as the major ethyl acetate-extractable metabolites. Small amounts of phenanthrols were also formed. The metabolites were purified by high-pressure liquid chromatography and identified from their UV, infrared, mass, and proton magnetic resonance spectral properties. A. quadruplicatum PR-6 formed phenanthrene trans-9,10-dihydrodiol with a 22% enantiomeric excess of the (-)-9S,10S-enantiomer. Incorporation experiments with 18O2 showed that one atom of oxygen from O2 was incorporated into the dihydrodiol. Toxicity studies, using an algal lawn bioassay, indicated that 9-phenanthrol and 9,10-phenanthrenequinone inhibit the growth of A. quadruplicatum PR-6.
authors.affiliation: National Center for Toxicological Research, Food and Drug Administration, Jefferson, Arkansas 72079.
authors.forename: M L
authors.initials: ML
authors.lastname: Narro
authors.forename: C E
authors.initials: CE
authors.lastname: Cerniglia
authors.forename: C
authors.initials: C
authors.lastname: Van Baalen
authors.forename: D T
authors.initials: DT
authors.lastname: Gibson
mesh_terms: D001673:Biodegradation, Environmental; D002851:Chromatography, High Pressure Liquid; D000458:Cyanobacteria / Q000378:metabolism*; D013058:Mass Spectrometry; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry; D010616:Phenanthrenes / Q000378:metabolism*
chemical_list: D010616:Phenanthrenes; C031181:phenanthrene; D010100:Oxygen