Prenylated flavonoids from the heartwood of Artocarpus communis with inhibitory activity on lipopolysaccharide-induced nitric oxide production

A new prenylated chalcone, 3″,3″-dimethylpyrano[3′, 4′]2,4,2′-trihydroxychalcone (1), was isolated from the heartwood of Artocarpus communis. Two flavonoid derivatives, (-)-cycloartocarpin (9) and (-)-cudraflavone A (10), were isolated as new isomers. In addition, eight known flavonoids, isobacachalcone (2), morachalcone A (3), gemichalcones B (4) and C (5), artocarpin (6), cudraflavone C (7), licoflavone C (8), and (2S)-euchrenone a₇ (11), were isolated and identified from this plant for the first time. Compounds 1-4, 6, and 11 exhibited potent inhibitory activity on nitric oxide production in RAW264.7 LPS-activated mouse macrophage cells with IC ₅₀ values of 18.8, 6.4, 16.4, 9.3, 18.7, and 12.3, μM, respectively. The structure of compound 1 was elucidated by spectroscopic data analysis, including 1D and 2D NMR experiments.