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Two new polyketide compounds, asperulosins A and B ( 1 – 2 ), and one new prenylated small molecule, asperulosin C ( 3 ), along with nine known compounds ( 4 – 12 ), were isolated and identified from a fungus  Aspergillus rugulosa . Their structures were extensively elucidated  via  HRESIMS, 1D, and 2D NMR analysis. The absolute configurations of the new compounds were determined by the comparison of their electronic circular dichroism (ECD), calculated ECD spectra, and the detailed discussion with those in previous reports. Structurally, compounds  1  and  2  belonged to the polyketide family and were from different origins. Compound  2  was constructed by five continuous quaternary carbon atoms, which occur rarely in natural products. All of the isolates were evaluated for anti-inflammatory activity against the production of nitric oxide (NO) in lipopolysaccharide (LPS)-induced RAW264.7 cells. Among those, compounds  1  and  5  showed a significant inhibitory effect on NO production with IC 50  values of 1.49 ± 0.31 and 3.41 ± 0.85  μ M, respectively. Additionally, compounds  1  and  5  markedly increased the secretion of anti-inflammatory cytokine IL10 while suppressing the secretion of pro-inflammatory cytokines IL6, TNF-α, IFN-γ, MCP-1, and IL12. Besides,  1  and  5  inhibited the transcription level of pro-inflammatory macrophage markers IL6, IL1β, and TNF-α while remarkably elevating the anti-inflammatory factor IL10 and M2 macrophage markers ARG1 and CD206. Moreover,  1  and  5  restrained the expression and nuclear translocation of NF-κB, as well as its downstream signaling proteins COX-2 and iNOS. All these results suggest that  1  and  5  have potential as anti-inflammatory agents, with better or comparable activities than those of the positive control, dexamethasone.

New Polyketides With Anti-Inflammatory Activity From the Fungus Aspergillus rugulosa