Wińska Katarzyna, Grabarczyk Małgorzata, Mączka Wanda, Żarowska Barbara, Maciejewska Gabriela, Anioł Mirosław
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.
Z Naturforsch C J Biosci. 2017 May 1;72(5-6):209-217. doi: 10.1515/znc-2016-0188.
The aim of this article is influence of the structure of lactones with the methylcyclohexene and dimethylcyclohexene ring on their biotransformation and antimicrobial activity. This work was based on the general remark that even the smallest change in the structure of a compound can affect its biological properties. The results of the biotransformation of four bicyclic unsaturated lactones with one or two methyl groups in the cyclohexene ring was tested using fifteen fungal strains (Fusarium species, Penicillium species, Absidia species, Cunninghamella japonica, and Pleurotus ostreatus) and five yeast strains (Yarrowia lipolytica, Rhodorula marina, Rhodorula rubra, Candida viswanathii, and Saccharomyces cerevisiae). During these transformations, new epoxylactone and hydroxylactone were obtained. The relationship between the substrate structure and the ability of the microorganisms to transform them were analysed. Only compounds with C-O bond of lactone ring in the equatorial position were transformed by fungus. All presented here lactones were examined also for their antimicrobial activity. It turned out that these compounds exhibited growth inhibition of bacteria and fungi, mainly Bacillus subtilis, Candida albicans, Aspergillus niger, and Penicillium expansum.
本文的目的是研究带有甲基环己烯和二甲基环己烯环的内酯结构对其生物转化及抗菌活性的影响。这项工作基于一个普遍的观点，即化合物结构中即使是最小的变化也可能影响其生物学性质。使用15种真菌菌株（镰刀菌属、青霉属、犁头霉属、日本被孢霉和平菇）和5种酵母菌株（解脂耶氏酵母、海红酵母、红酵母、维斯瓦纳蒂念珠菌和酿酒酵母）测试了四种在环己烯环上带有一个或两个甲基的双环不饱和内酯的生物转化结果。在这些转化过程中，获得了新的环氧内酯和羟基内酯。分析了底物结构与微生物转化它们的能力之间的关系。只有内酯环中C-O键处于平伏位置的化合物才能被真菌转化。本文还对所有呈现的内酯进行了抗菌活性检测。结果表明，这些化合物对细菌和真菌具有生长抑制作用，主要是枯草芽孢杆菌、白色念珠菌、黑曲霉和扩展青霉。
