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.
Bioorg Chem. 2020 Nov;104:104250. doi: 10.1016/j.bioorg.2020.104250. Epub 2020 Sep 1.
The aim of this research was to test the ability of cultures of edible fungi to biotransform three bicyclic halolactones. The substrates (2-chloro-, 2-bromo- and 2-iodo-4,4,6,7-tetramethyl-9-oxabicyclo[4.3.0]nonan-8-one) received by means of synthesis were transformed by oyster mushroom Pleurotus ostreatus and edible mushrooms of the genus Armillaria mellea, Marasmius scorodonius and Laetiporus sulfureus. The substrates were converted to hydroxyl derivatives only by the cultures of oyster mushroom. Out of seven strains of Pleurotus ostreatus - three were capable of hydroxylation of all substrates with the most effective conversion of chlorolactone. Bromo- and iodolactone were transformed to a small extent. Four new chloro-hydroxylactones were obtained as biotransformation products. The structures of substrates and products were established on the basis of spectroscopic data. Studies of antimicrobial activity performed on reference strains of pathogenic microorganisms showed that halolactones caused complete inhibition of growth of A. alternata and F. linii strains. On the other hand, chloro-hydroxylactones were able to completely inhibit the growth of A. alternata and F. linii strains and also C. albicans strain.
本研究旨在测试食用真菌培养物对三种双环卤内酯的生物转化能力。通过合成获得的底物（2-氯、2-溴和 2-碘-4,4,6,7-四甲基-9-氧杂双环[4.3.0]壬烷-8-酮）被牡蛎菇（Pleurotus ostreatus）和食用菇属（Armillaria mellea、Marasmius scorodonius 和 Laetiporus sulfureus）的培养物转化。只有牡蛎菇的培养物将底物转化为羟基衍生物。在七种牡蛎菇菌株中，有三种能够将所有底物羟化，其中氯内酯的转化率最高。溴内酯和碘内酯的转化率较低。作为生物转化产物，得到了四个新的氯-羟基内酯。基于光谱数据确定了底物和产物的结构。对病原菌参考菌株进行的抗菌活性研究表明，卤内酯完全抑制了Alternaria alternata 和 F. lini 菌株的生长。另一方面，氯-羟基内酯能够完全抑制 Alternaria alternata 和 F. lini 菌株以及 C. albicans 菌株的生长。
