Metabolism of phenanthrene by the marine cyanobacterium Agmenellum quadruplicatum PR-6.
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.
Narro
M L
ML
National Center for Toxicological Research, Food and Drug Administration, Jefferson, Arkansas 72079.
Cerniglia
C E
CE
Van Baalen
C
C
Gibson
D T
DT
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*
D010616:Phenanthrenes; C031181:phenanthrene; D010100:Oxygen