Isoprenylated Flavonoids with PTP1B Inhibition from Macaranga denticulata

ABSTRACT: Three new C-methylated and isoprenylated chalcone derivatives, dentichalcones A–C (1–3), together with six known compounds (4–9), were isolated from the twigs and leaves of Macaranga denticulata. Their structures were elucidated by spectroscopic analysis, including 1D, 2D NMR, and MS data. The known compounds, (2E)-1-(5,7-dihydroxy-2,2,6-trimethyl-2H-benzopyran-8-yl)-3-(4-methoxyphenyl)-2-propen-1-one (4), (2E)-1-(5,7-dihydroxy-2,2-dimethyl-2H-benzopyran-8-yl)-3-phenyl-2-propen-1-one (5), laxichalcone (6), macarangin (7), bonanniol A (8), and bonannione A (9), showed inhibitory activities against protein tyrosine phosphatase 1B (PTP1B) in vitro. GRAPHICAL ABSTRACT: Three new C-methylated and isoprenylated chalcone derivatives, dentichalcones A–C (1–3), together with six known compounds, were isolated from the twigs and leaves of Macaranga denticulata. Some compounds showed inhibitory activities against PTP1B in vitro. [Image: see text]