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As part of our search for natural products having antioxidant and anticancer properties, the phytochemical investigation of  Diospyros shimbaensis  (Ebenaceae), a plant belonging to a genus widely used in East African traditional medicine, was carried out. From its stem and root barks the new naphthoquinone 8,8′-oxo-biplumbagin ( 1 ) was isolated along with the known tetralones  trans -isoshinanolone ( 2 ) and  cis -isoshinanolone ( 3 ), and the naphthoquinones plumbagin ( 4 ) and 3,3′-biplumbagin ( 5 ). Compounds  2 ,  4 , and  5  showed cytotoxicity (IC 50  520–82.1 μM) against MDA-MB-231 breast cancer cells. Moderate to low cytotoxicity was observed for the hexane, dichloromethane, and methanol extracts of the root bark (IC 50  16.1, 29.7 and > 100 μg/mL, respectively), and for the methanol extract of the stem bark (IC 50  59.6 μg/mL). The radical scavenging activity of the isolated constituents ( 1 – 5 ) was evaluated on the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay. The applicability of the crude extracts and of the isolated constituents for controlling degenerative diseases is discussed.

Phytoconstituents with Radical Scavenging and Cytotoxic Activities from Diospyros shimbaensis