title: Metabolism of fluoranthene by Mycobacterium sp. strain AP1.
abstract: The pyrene-degrading Mycobacterium strain AP1 was found to utilize fluoranthene as a sole source of carbon and energy. Identification of metabolites formed from fluoranthene (by growing cells and washed-cell suspensions), the kinetics of metabolite accumulation, and metabolite-feeding studies all indicated that strain AP1 oxidizes fluoranthene using three alternative routes. The first route is initiated by dioxygenation at C-7 and C-8 and, following meta cleavage and pyruvate release, produces a hydroxyacenaphthoic acid that is decarboxylated to acenaphthenone (V). Monooxygenation of this ketone to the quinone and subsequent hydrolysis generates naphthalene-1,8-dicarboxylic acid (IV), which is further degraded via benzene-1,2,3-tricarboxylic acid (III). A second route involves dioxygenation at C-1 and C-2, followed by dehydrogenation and meta cleavage of the resulting diol. A two-carbon fragment excision of the meta cleavage product yields 9-fluorenone-1-carboxylic acid (II), which appears to undergo angular dioxygenation and further degradation to produce benzene-1,2,3-tricarboxylic acid (III), merging this route with the 7,8-dioxygenation route. Decarboxylation of benzene-1,2,3-tricarboxylic acid to phthalate (VIII), as well as further oxidation of the latter, would connect both routes with the central metabolism. The identification of Z-9-carboxymethylenefluorene-1-carboxylic acid (I) suggests a third route for fluoranthene degradation involving dioxygenation at C-2, C-3, and ortho cleavage. There is no evidence of any further degradation of this compound.
authors.affiliation: Departament de Microbiologia, Universitat de Barcelona, Diagonal 645, 08028, Barcelona, Spain.
authors.forename: Zaira
authors.initials: Z
authors.lastname: López
authors.forename: Joaquim
authors.initials: J
authors.lastname: Vila
authors.forename: Cristina
authors.initials: C
authors.lastname: Minguillón
authors.forename: Magdalena
authors.initials: M
authors.lastname: Grifoll
mesh_terms: D001673:Biodegradation, Environmental; D002851:Chromatography, High Pressure Liquid; D003470:Culture Media; D005449:Fluorenes / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D009161:Mycobacterium / Q000145:classification / Q000254:growth & development / Q000302:isolation & purification / Q000378:metabolism*; D010578:Petroleum / Q000378:metabolism; D010795:Phthalic Acids / Q000378:metabolism; D012988:Soil Microbiology; D012989:Soil Pollutants / Q000378:metabolism
chemical_list: D003470:Culture Media; D005449:Fluorenes; D010578:Petroleum; D010795:Phthalic Acids; D012989:Soil Pollutants; C007738:fluoranthene; C032279:phthalic acid