Antimicrobial Furancarboxylic Acids from a Penicillium sp.
journal contributionposted on 14.12.2020, 14:35 by Jin-Ling Chang, Hong-Zhe Xu, Jia Zhou, Ming Zhou, Xuke Zhang, Yuanqiang Guo, Han-Li Ruan
Ten novel (1, 2, 3a, 3b, 4a, 4b, 5a, 5b, 6a, and 6b) furancarboxylic acids including four pairs of epimers (3a, 3b; 4a, 4b; 5a, 5b; 6a, 6b), together with seven known analogues (7a, 7b, 8a, 8b, 9a, 9b, and 10), were isolated from the fermentation of the soil-derived fungus Penicillium sp. sb62. Their structures were established on the basis of spectroscopic data analysis, and the absolute configurations were determined by time-dependent density functional theory electronic circular dichroism calculations, comparison of the specific optical rotation values, and modified Mosher’s method. Compounds 1–4 represent the first class of natural furancarboxylic acids featuring a thiophene moiety. Compounds 1–7 showed antimicrobial inhibitory activities against Escherichia coli, Staphylococcus aureus, and Candida albicans with MIC values ranging from 0.9 to 7.0 μg/mL, from 1.7 to 3.5 μg/mL, and from 3.3 to 7.0 μg/mL, respectively.
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spectroscopic data analysisalbicansMIC7.0colianaloguedensity4 bepimerrotationEscherichia3.5soil-derived fungus Penicillium spthiophenemoietyCompoundmethodfurancarboxylic acidsconfigurationtime-dependentAntimicrobial Furancarboxylic Acids62.basisStaphylococcu3 bCandida5 bMosher22.214.171.124calculationdichroismantimicrobialaureussb