(±)-Heterocageflavone, anti-inflammatory isoprenylated flavonoids with a tricyclo[5.3.1.03,8]undecane moiety from Artocarpus heterophyllus

(+/-)-Heterocageflavone (1), a pair of enantiomeric isoprenylated flavonoids, were isolated from Artocarpus heterophyllus. Compound 1 incorporates an unusual tricyclo[5.3.1.0(3,8)]undecane moiety, forming a unique caged polycyclic system. The structures of the pair were determined by spectroscopic analysis, ECD calculations, and single-crystal X-ray diffraction. Compound 1 showed significant inhibitory activity against LPS-induced NO production in RAW264.7 cells with an IC50 value of 49.2 mu M.

Automated summary

In this study, a pair of enantiomeric isoprenylated flavonoids were isolated from Artocarpus heterophyllus, one of which exhibited a unique caged polycyclic structure. The structures of these compounds were determined through spectroscopic analysis, ECD calculations, and single-crystal X-ray diffraction. One of the compounds showed significant inhibitory activity against LPS-induced NO production in RAW264.7 cells.