title: Biodegradation of 1-allyloxy-4-propoxybenzene by selected strains of Pseudomonas putida.
abstract: Dialkoxybenzenes constitute a class of organic compounds with anti feeding and oviposition effects on the cabbage looper, Trichoplusia ni. Among them, 1-allyloxy-4-propoxybenzene has the highest feeding deterrence activity and potential for development as commercial insect control agent. To develop this compound, its fate in the environment needs to be studied. The fate of organic compounds in the environment depends on their biodegradability in the soil. We present results of laboratory biodegradation experiments of 1-allyloxy-4-propoxybenzene with three strains of Pseudomonas putida. Two of the three strains of P. putida tested were able to metabolize 1-allyloxy-4-propoxybenzene. Both strains required induction of the catabolic pathway. Specifically, strain ATCC 17453 (which contains the CAM plasmid) metabolized 1-allyloxy-4-propoxybenzene by first dealkylating. This gave both possible monoalkoxy phenols after five days, followed by dihydroquinone after 8 days. In vitro tests with CYP101A1 (cytochrome P450cam, a camphor hydroxylase), revealed that the dealkylation is catalyzed by this enzyme.
authors.affiliation: Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, BC, V5A 1S6, Canada, pebrahim@sfu.ca.
authors.forename: Parisa
authors.initials: P
authors.lastname: Ebrahimi
authors.forename: Erika
authors.initials: E
authors.lastname: Plettner
mesh_terms: D000818:Animals; D001426:Bacterial Proteins / Q000302:isolation & purification / Q000378:metabolism*; D001555:Benzene Derivatives / Q000378:metabolism*; D001673:Biodegradation, Environmental; D001937:Brassica / Q000469:parasitology; D019475:Camphor 5-Monooxygenase / Q000302:isolation & purification / Q000378:metabolism*; D003470:Culture Media; D005260:Female; D007302:Insect Repellents / Q000378:metabolism*; D007700:Kinetics; D007915:Lepidoptera / Q000187:drug effects / Q000502:physiology; D062105:Molecular Docking Simulation; D010058:Oviposition / Q000187:drug effects / Q000502:physiology; D016958:Pseudomonas putida / Q000201:enzymology* / Q000302:isolation & purification; D012988:Soil Microbiology; D012989:Soil Pollutants / Q000378:metabolism*; D013379:Substrate Specificity
chemical_list: D001426:Bacterial Proteins; D001555:Benzene Derivatives; D003470:Culture Media; D007302:Insect Repellents; D012989:Soil Pollutants; D019475:Camphor 5-Monooxygenase