Dehalogenation Activity of Selected Fungi Toward δ‐Iodo‐γ‐Lactone Derived from trans,trans‐Farnesol |
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| Authors: | Anna Gliszczyńska Witold G?adkowski Marta ?witalska Joanna Wietrzyk Antoni Szumny El?bieta G?barowska Czes?aw Wawrzeńczyk |
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| Affiliation: | 1. Department of Chemistry, Wroclaw University of Environmental and Life Sciences, Wroc?aw;2. Department of Experimental Oncology, Polish Academy of Sciences, Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Wroc?aw;3. Department of Plant Protection, Wroclaw University of Environmental and Life Sciences, Wroc?aw |
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| 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). |
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| Keywords: | Dehalogenation Biotransformation Lactones Fungi Antiproliferative activity |
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