Dehalogenation Activity of Selected Fungi Toward δ ‐Iodo‐ γ ‐Lactone Derived from trans , trans ‐Farnesol

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).