title: Dehalogenation Activity of Selected Fungi Toward δ-Iodo-γ-Lactone Derived from trans,trans-Farnesol.
abstract: Time-course of biotransformation of racemic trans-4-((E)-4',8'-dimethylnona-3',7'-dien-1-yl)-5-iodomethyl-4-methyldihydrofuran-2-one (1) in fungal and yeast cultures was investigated. In these conditions, the substrate 1 was enantioselectively dehalogenated yielding 4-((E)-4',8'-dimethylnona-3',7'-dien-1-yl)-4-methyl-5-methylenedihydrofuran-2-one (2) and its structure was established based on the spectroscopic data. The most effective biocatalyst used was Didymosphaeria igniaria, which catalyzed the process with highest rate and enantioselectivity (ee of product = 76%). The antiproliferative activity of δ-iodo-γ-lactone 1, product of its biotransformation 2, and starting substrate (farnesol) were evaluated toward two cancer cell lines: A549 (human lung adenocarcinoma) and HL-60 (human promyelocytic leukemia).
authors.affiliation: Department of Chemistry, Wroclaw University of Environmental and Life Sciences, Norwida 25, PL-50-375, Wrocław.
authors.forename: Anna
authors.initials: A
authors.lastname: Gliszczyńska
authors.affiliation: Department of Chemistry, Wroclaw University of Environmental and Life Sciences, Norwida 25, PL-50-375, Wrocław.
authors.forename: Witold
authors.initials: W
authors.lastname: Gładkowski
authors.affiliation: Department of Experimental Oncology, Polish Academy of Sciences, Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Weigla 12, PL-53-114, Wrocław.
authors.forename: Marta
authors.initials: M
authors.lastname: Świtalska
authors.affiliation: Department of Experimental Oncology, Polish Academy of Sciences, Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Weigla 12, PL-53-114, Wrocław.
authors.forename: Joanna
authors.initials: J
authors.lastname: Wietrzyk
authors.affiliation: Department of Chemistry, Wroclaw University of Environmental and Life Sciences, Norwida 25, PL-50-375, Wrocław.
authors.forename: Antoni
authors.initials: A
authors.lastname: Szumny
authors.affiliation: Department of Plant Protection, Wroclaw University of Environmental and Life Sciences, Grunwaldzka 22A, PL-53-363, Wrocław.
authors.forename: Elżbieta
authors.initials: E
authors.lastname: Gębarowska
authors.affiliation: Department of Chemistry, Wroclaw University of Environmental and Life Sciences, Norwida 25, PL-50-375, Wrocław.
authors.forename: Czesław
authors.initials: C
authors.lastname: Wawrzeńczyk
mesh_terms: D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D005204:Farnesol / Q000378:metabolism*; D005658:Fungi / Q000378:metabolism*; D054879:Halogenation; D006801:Humans; D007783:Lactones / Q000378:metabolism* / Q000494:pharmacology
chemical_list: D007783:Lactones; D005204:Farnesol
keywords: Antiproliferative activity; Biotransformation; Dehalogenation; Fungi; Lactones