warangalone and auriculasin

While osajin and pomiferin are known for their anticancer, antibacterial and antidiabetic properties, scandenone and auriculasin have been proposed as anti-inflammatory and antinociceptive agents. Curiously, these two couples of molecules are, from a chemical point of view, structural isomers which can all be extracted from Maclura pomifera. Although previous works described, separately, the isolation in reasonable amounts of the sole osajin/pomiferin couple or of scandenone/auriculasin, we report the extraction and characterization using direct spectral and chromatographical comparison of the four compounds. 2D NMR allowed to unambiguously assign the correct structures to the isomers. The compounds were screened in silico against PDE5 and their interaction pattern with the protein was compared with that of icarisid II, a natural PDE5 inhibitor.

Topics: Benzopyrans; Computer Simulation; Cyclic Nucleotide Phosphodiesterases, Type 5; Isoflavones; Isomerism; Maclura; Molecular Docking Simulation; Molecular Structure

The aqueous, ethanolic and chloroform extracts and two prenylated isoflavones: scandenone (I) and auriculasin (II), isolated from the fruits of Maclura pomifera (Rafin.) Schneider, were investigated for their in vivo anti-inflammatory and antinociceptive activity. For the anti-inflammatory activity, both carrageenan-induced hind paw edema and 12-O-tetradecanoyl-13-acetate (TPA)-induced mouse ear edema models and for the antinociceptive activity, p-benzoquinone-induced abdominal constriction test were used. Scandenone, the chloroform and the ethanolic extracts were shown to possess antinociceptive activity and anti-inflammatory activity on carrageenan-induced hind paw edema model at 100 mg/kg dose. The same compound and the extract were also found to be highly active in (TPA)-induced mouse ear edema model whereas auriculasin and the H(2)O extract showed to be inactive in all of the assays.

Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Disease Models, Animal; Edema; Flavonoids; Fruit; Isoflavones; Maclura; Male; Mice; Molecular Structure; Pain; Plant Extracts; Solvents; Stomach Ulcer