Abstract
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 (IC50 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 (IC50 16.1, 29.7 and > 100 μg/mL, respectively), and for the methanol extract of the stem bark (IC50 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.
Highlights
The genus Diospyros (Ebenaceae) comprises of approximately 500 species distributed in the tropical and subtropical regions of both hemispheres
Www.mdpi.com/journal/diseases mical information and bioactive compounds that may be of medicinal interest ed its stem and root barks constituents for radical scavenging and cytotoxic prop
In order to support its domestication and to avoid an unfortunate loss of phytochemical information and bioactive compounds that may be of medicinal interest, we have investigated its stem and root barks constituents for radical scavenging and cytotoxic properties
Summary
The genus Diospyros (Ebenaceae) comprises of approximately 500 species distributed in the tropical and subtropical regions of both hemispheres. The roots and leaves of D. usambarensis are used for the treatment of stomach pain, constipation, rashes, cervical prolapse, epilepsy, malaria, measles, psychiatric disorders, sterility, and joint pain, whereas those of D. verrucosa for the treatment of psychiatric disorders and its fruits against asthenia [9] This extensive traditional medicinal use of the Diospyros genus suggests its richness in bioactive secondary metabolites. Two carbonyl groups at δC 190.5 and δC 185.2, and eight aromatic carbons (Table 1) were observed in its 13 C-NMR spectrum, consistent with a 1,4-naphthoquinone skeleton. The quinonoid H-3/H-31 proton (δH 6.81) exhibited HMBC correlations to C-10/C-101 (δC 115.5), which carbon showed correlations to H-6/H-61 (δH 7.29), confirming the orientation of the rings of the naphthoquinone skeleton of 1. 1 H and 13 C-NMR data for 8,81 -oxo-biplumbagin (1) Based ontheir their spectroscopic features, compounds were (Supporting identified Information).
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