Transformation of 1- and 2-methylnaphthalene by Cunninghamella elegans

Journal Article · Sun Jan 01 04:00:00 EST 1984 · Appl. Environ. Microbiol.; (United States)

OSTI ID:6680244

Cerniglia, C E; Lambert, K J; Miller, D W; Freeman, J P

Cunninghamella elegans metabolized 1- and 2-methylnaphthalene primarily at the methyl group to form 1- and 2-hydroxymethylnaphthalene, respectively. Other compounds isolated and identified were 1- and 2-naphthoic acids, 5-hydroxy-1-naphthoic acid, 5-hydroxy-2-naphthoic acid, 6-hydroxy-2-naphthoic acid, and phenolic derivatives of 1- and 2-methylnaphthalene. The metabolites were isolated by thin-layer and reverse-phase high-presure liquid chromatography and characterized by the application of UV-visible absorption, /sup 1/H nuclear magnetic resonance, and mass spectral techniques. Experiments with (8-/sup 14/C)2-methylnaphthalene indicated that over a 72-h period, 9.8% of 2-methylnaphthalene was oxidized to metabolic products. The ratio of organic-soluble to water-soluble metabolites at 2 h was 92:8, and at 72 h it was 41:59. Enzymatic treatment of the 48-h aqueous phase with either ..beta..-glucuronidase or arylsufatase released 60% of the metabolites of 2-methylnaphthalene that were extractable with ethyl acetate. In both cases, the major conjugates released were 5-hydroxy-2-naphthoic acid and 6-hydroxy-2-naphthoic acid. The ratio of the water-soluble glucuronide conjugates to sulfate conjugates was 1:1. Incubation of C. elegans with 2-methylnaphthalene under an /sup 18/O/sub 2/ atmosphere and subsequent mass spectral analysis of 2-hydroxymethylnaphthalene indicated that hydroxylation of the methyl group is catalyzed by a monooxygenase. 23 references.

• Research Organization: Food and Drug Administration, Jefferson, AR
• OSTI ID: 6680244
• Journal Information: Appl. Environ. Microbiol.; (United States), Journal Name: Appl. Environ. Microbiol.; (United States) Vol. 47:1; ISSN AEMID
• Country of Publication: United States
• Language: English

Related Subjects

550701* -- Microbiology-- Tracer Techniques
59 BASIC BIOLOGICAL SCIENCES
AROMATICS
BIOCHEMICAL REACTION KINETICS
BIODEGRADATION
CARBON 14 COMPOUNDS
CATALYSIS
CHEMICAL REACTIONS
CHROMATOGRAPHY
CONDENSED AROMATICS
DECOMPOSITION
ENZYME ACTIVITY
ENZYMES
EVEN-EVEN NUCLEI
FUNGI
HYDROCARBONS
ISOTOPES
KINETICS
LABELLED COMPOUNDS
LIGHT NUCLEI
LIQUID COLUMN CHROMATOGRAPHY
MAGNETIC RESONANCE
MASS SPECTROSCOPY
METABOLISM
METABOLITES
NAPHTHALENE
NUCLEAR MAGNETIC RESONANCE
NUCLEI
ORGANIC COMPOUNDS
OXIDOREDUCTASES
OXYGEN 18
OXYGEN ISOTOPES
OXYGENASES
PLANTS
REACTION KINETICS
RESONANCE
SEPARATION PROCESSES
SPECTRA
SPECTROSCOPY
STABLE ISOTOPES
THIN-LAYER CHROMATOGRAPHY
ULTRAVIOLET SPECTRA