Bisabolane-Type Sesquiterpenoids with a Tetrahydrofuran or Tetrahydropyran Ring from Vernonia solanifolia

Phytochemical investigation of the aerial parts of Vernonia solanifolia resulted in the isolation of 23 new highly oxidized bisabolane-type sesquiterpenoids (1–23). Structures were determined by interpretation of spectroscopic data, single-crystal X-ray diffraction analysis, and time-dependent density functional theory electronic circular dichroism calculations. Most compounds possess a rare tetrahydrofuran (1–17) or tetrahydropyran ring (18–21). Compounds 1/2 and 11/12 are pairs of epimers isomerized at C-10, while compounds 9/10 and 15/16 are isomerized at C-11 and C-2, respectively. The anti-inflammatory effect in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages was evaluated for pure compounds. Compound 9 inhibited LPS-stimulated NO production at the concentration of 80 μM. It showed an anti-inflammatory effect by suppressing the activation of the NF-κB signaling pathway.