(±)-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[5.3.1.03,8]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 µM.

N-[(E)-4-Bromo-benzyl-idene]-2,3-di-methyl-aniline.

The title compound, C15H14BrN, has an E conformation about the C=N bond and the dihedral angle between the benzene rings is 50.7 (2)°. In the crystal, mol-ecules are linked via C-H⋯π inter-actions, forming columns propagating along [010].

N-[(E)-4-Bromo-benzyl-idene]-3,4-di-methyl-aniline.

In the title compound, C15H14BrN, the dihedral angle between the benzene rings is 6.4 (2)° and the mol-ecule has an E conformation about the C=N bond. In the crystal, mol-ecules are linked by C-H⋯π inter-actions, forming two-dimensional networks lying parallel to (001).