Premium
Dehalogenation Activity of Selected Fungi Toward δ ‐Iodo‐ γ ‐Lactone Derived from trans , trans ‐Farnesol
Author(s) -
Gliszczyńska Anna,
Gładkowski Witold,
Świtalska Marta,
Wietrzyk Joanna,
Szumny Antoni,
Gębarowska Elżbieta,
Wawrzeńczyk Czesław
Publication year - 2016
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201500127
Subject(s) - chemistry , farnesol , halogenation , lactone , stereochemistry , cis–trans isomerism , organic chemistry
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).