Maydistacins A-G, Terpestacin-type Sesterterpenoids with Anti-inflammatory Activity from the Phytopathogenic Fungus Bipolaris maydis .

Seven undescribed terpestacin-type sesterterpenoids, maydistacins A-G ( 1 - 7 ), along with two known congeners ( 8 and 9 ), were isolated from the phytopathogenic fungus Bipolaris maydis collected from the leaves of Hypericum longistylum . The structures of 1 - 7 were elucidated based on extensive spectroscopic analysis, chemical methods, NMR calculations with DP4+ probability analysis, and comparison of experimental and calculated electronic circular dichroism (ECD) calculations. In vitro anti-inflammatory effects of these compounds were tested in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. Compound 1 exhibited inhibition of the production of nitric oxide in LPS-induced macrophages, with an IC 50 value of 19 ± 2 μM. A dexamethasone control displayed an IC 50 value of 6.7 ± 0.6 μM. Compound 1 is the first terpestacin-type sesterterpenoid reported to display anti-inflammatory activity and may provide a novel chemical scaffold for the discovery of new anti-inflammatory drugs.