Two new 2-pyrone derivatives sydowiones A-B (1, 2), one new cyclopentenone derivative sydowione C (3), and one new sterigmatocystin derivative sydowione D (4) along with two known analogues paecilpyrone A (5) and austocystin A (6), were isolated from the marine-derived fungus Aspergillus sydowii SCSIO 00305. The structures of 1-4 were elucidated by extensive spectroscopic analysis. The absolute configuration of 1 was established by Mosher method, and further confirmed by calculation of the electronic circular dichroism (ECD) spectra. The absolute configuration of C-11 in 3 was also determined by calculation of ECD spectra. The absolute configuration of 6 was determined by a single-crystal X-ray diffraction experiment for the first time. Compounds 1-4 showed moderate toxicity towards brine shrine naupalii with LC 50 values of 19.5, 14.3, 8.3 and 2.9 μM, respectively. And 1 and 2 also showed antioxidant activity against 2,2-diphenyl-picrylhydrazyl (DPPH) radicals with IC 50 values of 46.0 and 46.6 μM, respectively.
Biofilm formation of Staphylococcus aureus is one of its mechanisms of drug resistance. Antibiofilm screening of 106 compounds from marine-derived fungi displayed that 12 compounds inhibited S. aureus biofilm formation by >50% at the concentration of 100 µg/ml, and only secalonic acid D (SAD) and B inhibited by >90% at 6.25 µg/ml without inhibiting cell growth after 24-h incubation. Meanwhile, it was found that the double bond between C-1 and C-10 of citrinin derivatives and the CC connection position of two chromone monomers may be important for their anti-biofilm activities. Moreover, SAD slightly facilitated biofilm eradication and influenced its architecture. Furthermore, SAD slowed the cell growth rate in the preceding 18-h incubation and differentially regulated transcriptional expression of several genes, such as agr, isaA, icaA, and icaD, associated with biofilm formation in planktonic and biofilm cells, which may be the reason for the anti-biofilm activity of SAD. Finally, SAD acted synergistically against S. aureus growth and biofilm formation with other antibiotics. These findings indicated that various natural products from marine-derived fungi, such as SAD, could be used as a potential biofilm inhibitor against S. aureus.
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