环己烷环上带有甲基的双环卤代内酯向羟基内酯的生物转化及其生物活性

Biotransformation of Bicyclic Halolactones with a Methyl Group in the Cyclohexane Ring into Hydroxylactones and Their Biological Activity.

作者信息

Wińska Katarzyna, Grabarczyk Małgorzata, Mączka Wanda, Żarowska Barbara, Maciejewska Gabriela, Dancewicz Katarzyna, Gabryś Beata, Szumny Antoni, Anioł Mirosław

机构信息

Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland.

Department of Biotechnology and Food Microbiology, Wrocław University of Environmental and Life Sciences, Chełmońskiego 37/41, 51-630 Wrocław, Poland.

出版信息

Molecules. 2016 Oct 31;21(11):1453. doi: 10.3390/molecules21111453.

DOI:10.3390/molecules21111453

PMID:27809258

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6273801/

Abstract

The aim of this study was the chemical synthesis of a series of halo- and unsaturated lactones, as well as their microbial transformation products. Finally some of their biological activities were assessed. Three bicyclic halolactones with a methyl group in the cyclohexane ring were obtained from the corresponding γ,δ-unsaturated ester during a two-step synthesis. These lactones were subjected to screening biotransformation using twenty two fungal strains. These strains were tested on their ability to transform halolactones into new hydroxylactones. Among the six strains able to catalyze hydrolytic dehalogenation, only two (, AM22 and , AM71) gave a product in a high yield. Moreover, one strain (, AM30) introduced the hydroxy group on the cyclohexane ring without removing the halogen atom. The biological activity of five of the obtained lactones was tested. Some of these compounds exhibited growth inhibition against bacteria, yeasts and fungi and deterrent activity against peach-potato aphid.

摘要

本研究的目的是化学合成一系列卤代和不饱和内酯及其微生物转化产物。最后评估了它们的一些生物活性。在两步合成过程中，从相应的γ,δ-不饱和酯中获得了三种在环己烷环上带有甲基的双环卤代内酯。使用二十二种真菌菌株对这些内酯进行筛选生物转化。测试了这些菌株将卤代内酯转化为新的羟基内酯的能力。在能够催化水解脱卤的六种菌株中，只有两种（AM22和AM71）以高产率得到了产物。此外，一种菌株（AM30）在环己烷环上引入了羟基而没有去除卤原子。测试了所获得的五种内酯的生物活性。其中一些化合物对细菌、酵母和真菌表现出生长抑制作用，对桃蚜具有驱避活性。