Isoprenoid-substituted flavonoids from wood of Artocarpus heterophyllus on B16 melanoma cells: Cytotoxicity and structural criteria

As a result of cytotoxicity-guided fractionation, nine flavonoids, artocarpin (1), cudraflavone C (2), 6-prenylapigenin (3), kuwanon C (4), norartocarpin (5), albanin A (6), cudraflavone B (7), brosimone I (8) and artocarpanone (9) were identified from the methanol extract of the wood of Artocarpus heterophyllus, known commonly as Nangka in Indonesia. A structure–activity investigation of the effect of these isolated compounds (1–9) and structurally related compounds on B16 melanoma cells indicated that isoprenoid moiety substitutions in flavonoids enhance their cytotoxicity, and that the position of attachment and the number of isoprenoid-substituent moieties per molecule influence flavonoid cytotoxicity.

Graphical abstractStructure–cytotoxic activity investigation on B16 melanoma cells using the isolated compounds (1–9) from Artocarpus heterophyllus and structurally related compounds indicated that the isoprenoid-substituted moiety of flavonoids enhanced their cytotoxicity and, its attached position and the number of the isoprenoid-substituted moiety per molecule influence their cytotoxicity.Figure optionsDownload full-size imageDownload as PowerPoint slide