1-Methoxypyrene and 1,6-dimethoxypyrene: two novel metabolites in fungal metabolism of polycyclic aromatic hydrocarbons
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© Springer-Verlag 1997
O R I G I N A L PA P E R
Thomas Wunder · Jens Marr · Stefan Kremer · Olov Sterner · Heidrun Anke
1-Methoxypyrene and 1,6-dimethoxypyrene: two novel metabolites in fungal metabolism of polycyclic aromatic hydrocarbons Received: 27 August 1996 / Accepted: 8 January 1997
Abstract The metabolism of pyrene by Penicillium glabrum strain TW 9424, a strain isolated from a site contaminated with polycyclic aromatic hydrocarbons (PAHs) was investigated in submerged cultures. The metabolites formed were identified as 1-hydroxypyrene, 1,6- and 1,8dihydroxypyrene, 1,6- and 1,8-pyrenequinone, and 1pyrenyl sulfate. In addition, two new metabolites were isolated and identified by UV, 1H nuclear magnetic resonance, and mass spectroscopy as 1-methoxypyrene and 1,6-dimethoxypyrene. Experiments with [methyl-3H]Sadenosyl-L-methionine (SAM) revealed that SAM is the coenzyme that provides the methyl group for the methyltransferase involved. To our knowledge, this is the first time that methoxylated metabolites of PAHs have been isolated from fungal cultures. Key words Polycyclic aromatic hydrocarbons · Fungi · Biodegradation · Biotransformation · Methoxy-PAHs · Methyl conjugation · O-methylation · O-methyltransferase · Fungal secondary metabolism
Introduction Polycyclic aromatic hydrocarbons (PAHs) represent an important class of environmental pollutants since the compounds are among the most frequently found soil contaminants; several PAHs are known to be mutagenic and carcinogenic (Dipple 1976). Intensive studies of the microbial metabolism of PAHs have demonstrated that many species of bacteria and fungi are capable of oxidizing various PAHs (Cerniglia 1992).
White-rot fungi such as Phanerochaete chrysosporium are able to oxidize PAHs by extracellular peroxidases to quinones, which subsequently can be oxidized to CO2 (Hammel et al. 1986; Aust et al. 1994) Metabolism of PAHs by non-white-rot fungi involves cytochrome P-450 monooxygenase enzyme systems similar to those observed in mammals (Smith and Rosazza 1974). The first steps of PAH oxidation by non-white-rot fungi result in the formation of monophenols, diphenols, dihydrodiols, and quinones as reported, e.g., for the zygomycete Cunninghamella elegans (Cerniglia and Gibson 1979; Cerniglia et al. 1986), the basidiomycete Crinipellis stipitaria (Lambert et al. 1994; Lange et al. 1994), and deuteromycetes of the genera Aspergillus (Datta and Samanta 1988; Wunder et al. 1994) and Penicillium (Launen et al. 1995). In a second step, water-soluble conjugates, which are detoxification products in fungi as well as in mammals, can be formed (Cerniglia et al. 1982; Lambert et al. 1995; Thakker et al. 1985). Among fungal PAH conjugates, sulfates (Cerniglia and Gibson 1979; Cerniglia 1982; Cerniglia et al. 1982; Lange et al. 1994; Wunder et al. 1994), glucuronides (Cerniglia et al. 1982), glucosides (Cerniglia et al. 1986, 1989), and xylosides (Sutherland et al. 1992) have been reported. With the isolation and identification of two O-methyl conjugates of pyrene from cu
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