3-Prenyl luteolin, a new prenylated flavone with melanin biosynthesis inhibitory activity from wood of Artocarpus heterophyllus

In our efforts to find new whitening agent from natural resources, we focused on wood of Artocarpus heterophyllus which shows anti-melanogenesis activity. By activity-guided fractionation of A. heterophyllus wood extract, a new prenylated flavonoid, 3-prenyl luteolin (1) was isolated. The IC50 of mushroom tyrosinase inhibitotry activity of 1 was 76.3 µM. The results of the comparison with that of luteolin showed the prenyl substituent at C-3 position of 1 play an important role for revealing tyrosinase inhibition. In melanin formation inhibition on B16 melanoma cells, IC50 of 1 was 56.7 µM with less cytotoxicity.

Graphical abstractA new prenylated flavonoid, 3-prenyl luteolin (1) was isolated from wood of Artocarpus heterophyllus which shows anti-melanogenesis. The prenylated moiety at C-3 position plays an important role for tyrosinase inhibitor.Figure optionsDownload full-size imageDownload as PowerPoint slide