New geranyl flavonoids from the leaves of Artocarpus communis

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Abstract

Four new geranyl flavonoids 1–4 and four known flavonoids 5–8 were obtained from the leaves of Artocarpus communis collected in Indonesia. The planar structures of flavonoids were elucidated by analyses of MS and NMR spectroscopic data. Absolute configurations of 1 and 2 were determined by ECD spectroscopy. Analyses by HPLC with a chiral-phase column and ECD spectra confirmed that 3 and 4 were stereoisomeric mixtures and 7 and 8 were racemic mixtures. The compounds obtained in this study inhibited the enzymatic activities of ubiquitin-specific protease 7 (USP7) and the chymotrypsin-like activity of the proteasome. Among the geranyl flavonoids tested in this experiment, the USP7 inhibitory activity of 6 (IC50 value, 0.094 μM) was 55 times more potent than the commercially available positive control, P5091 (IC50 value, 5.2 μM).

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