Antiproliferative activity of dibenzoylmethanes from root bark of Muellera filipes (Benth) M.J. Silva & A.M.G. Azevedo

Abstract

Three new dibenzoylmethane derivatives, (E)-3,4-methylenedioxy-2′-methoxy-2″,2″-dimethylpyrano-(5″,6″:3′,4′)-7-methoxychalcone, 2′-hydroxy-5′(3″″,3″″-dimethylallyl)-8-(α,α-dimethylallyl)-furano-(4″,5″:3′4′)-dibenzoylmethane and 2′-O-(3″,3″-dimethylallyl)-8-(α,α-dimethylallyl)-furano-(4″,5″:3′4′)-dibenzoylmethane, were isolated from a dichloromethane extract from the root bark of Muellera filipes (Benth.) M.J. Silva & A.M.G. Azevedo, along with two dibenzoylmethane derivatives, 2′-methoxy-8-(α,α-dimethylallyl)-furano-(4″,5″:3′,4′)-dibenzoylmethane and 2′-hydroxy-8-(α,α-dimethylallyl)-2”,2”-dimethylpyrano-(5”,6”:3’,4’)-dibenzoylmethane; one flavanone, isolonchocarpin and one flavone, pongaglabrone, which had been previously isolated from other sources. The molecular structures of the new dibenzoylmethane derivatives were determined by analysis of their spectral data (1H and 13C nuclear magnetic resonance (NMR), 2D-NMR, NOE (nuclear Overhauser effect) and HRMS (high resolution mass spectrometry). The known compounds were identified using 1D experiments and comparison with spectral data from the literature. 2′-O-(3″,3″-Dimethylallyl)-8-(α,α-dimethylallyl)-furano-(4″,5″:3’4’)-dibenzoylmethane displayed strong activity against the human cancer cell line OVCAR-3 (ovarian), and 2’-methoxy-8-(α,α-dimethylallyl)-furano-(4″,5″:3′,4′)-dibenzoylmethane showed high selectivity for cell lines NCI-H460 (lung) and UACC-62 (melanoma).