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1-Methoxypyrene and 1,6-dimethoxypyrene: two novel metabolites in fungal metabolism of polycyclic aromatic hydrocarbons
Authors:Thomas Wunder  Jens Marr  S Kremer  Olov Sterner  Heidrun Anke
Institution:(1) Department of Biotechnology, University of Kaiserslautern, D-67663 Kaiserslautern, Germany Tel. +49-631-205-4267; Fax +49-631-205-2999 e-mail kremer@rhrk.uni-kl.de, DE;(2) Department of Organic Chemistry 2, Chemical Center, University of Lund, S-22100 Lund, Sweden, SE
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 1,8-dihydroxypyrene, 1,6- and 1,8-pyrenequinone, and 1-pyrenyl 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]S-adenosyl-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. Received: 27 August 1996 / Accepted: 8 January 1997
Keywords:Polycyclic aromatic hydrocarbons  Fungi  Biodegradation  Biotransformation  Methoxy-PAHs  Methyl conjugation  O-methylation  O-methyltransferase  Fungal secondary metabolism
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