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In our ongoing search for new bioactive fungal metabolites, four previously undescribed oxazole carboxylic acid derivatives ( 1 - 4 ) for which we proposed the trivial names macrooxazoles A-D together with two known tetramic acids ( 5 - 6 ) were isolated from the plant pathogenic fungus Phoma macrostoma . Their structures were elucidated based on high-resolution mass spectrometry (HR-MS) and nuclear magnetic resonance (NMR) spectroscopy. The hitherto unclear structure of macrocidin Z ( 6 ) was also confirmed by its first total synthesis. The isolated compounds were evaluated for their antimicrobial activities against a panel of bacteria and fungi. Cytotoxic and anti-biofilm activities of the isolates are also reported herein. The new compound 3 exhibited weak-to-moderate antimicrobial activity as well as the known macrocidins 5 and 6 . Only the mixture of compounds 2 and 4 (ratio 1:2) showed weak cytotoxic activity against the tested cancer cell lines with an IC 50 of 23 µg/mL. Moreover, the new compounds 2 and 3 , as well as the known compounds 5 and 6 , interfered with the biofilm formation of Staphylococcus aureus , inhibiting 65%, 75%, 79%, and 76% of biofilm at 250 µg/mL, respectively. Compounds 5 and 6 also exhibited moderate activity against S. aureus preformed biofilm with the highest inhibition percentage of 75% and 73% at 250 µg/mL, respectively.

Macrooxazoles A–D, New 2,5-Disubstituted Oxazole-4-Carboxylic Acid Derivatives from the Plant Pathogenic Fungus Phoma macrostoma