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Phytoconstituents with Radical Scavenging and Cytotoxic Activities from Diospyros shimbaensis

Journal article
Authors Per Aronsson
Joan J. E. Munissi
Amra Gruhonjic
Paul A. Fitzpatrick
Göran Landberg
Stephen S. Nyandoro
Mate Erdelyi
Published in Diseases
Volume 4
Issue 1
ISSN 2079-9721
Publication year 2016
Published at Swedish NMR Centre at Göteborg University
Sahlgrenska Cancer Center
Department of Chemistry and Molecular Biology
Language en
Links dx.doi.org/10.3390/diseases4010003
Keywords Diospyros shimbaensis; Ebenaceae; tetralones; naphthoquinoes; radical scavenging; cytotoxicity; MDA-MB-231; DPPH
Subject categories Botany, Chemistry, Pharmaceutical chemistry, Medicinal Chemistry, Bioorganic chemistry

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

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