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Antiprotozoal and cytotoxic naphthalene derivatives from Diospyros assimilis

Ganapaty, S., Karagianis, G., Waterman, P.G., Brun, R.
Phytochemistry 2006 v.67 no.17 pp. 1950-1956
Diospyros, Ebenaceae, woody plants, shrubs, naphthalene, antiprotozoal agents, cytotoxicity, Trypanosoma, Trypanosoma rhodesiense, Trypanosoma cruzi, Leishmania donovani, Plasmodium falciparum, rats, cultured cells, naphthoquinones, India
Chemical investigation of the roots of Diospyros assimilis had led to the isolation and characterization of six naphthalene derivatives, two 2-naphthaldehyes, namely 4-hydroxy-3,5-dimethoxy-2-naphthaldehyde 1, 4-hydroxy-5-methoxy-2-naphthaldehye 2, its related isomer 5-hydroxy-4-methoxy-2-naphthaldehyde 3 and three commonly occurring naphthoquinones, diospyrin 4, 8'-hydroxyisodiospyrin 5 and the simple monomer, plumbagin 6. Their chemical structures were established by detailed NMR investigations including 1H and 13C NMR, HSQC, HMBC and NOESY experiments. In addition, the naphthalene derivatives 1-5 were evaluated for their in vitro antiprotozoal activity against protozoan parasites belonging to the genera Trypanosoma, Leishmania and Plasmodium. Among the tested compounds, naphthaldehyde 1 showed moderate inhibition of the growth of the parasites, T. brucei, T. cruzi, L. donovani with IC50 values of 19.82, 12.28 and 38.78 μM and displayed cytotoxicity towards rat skeletal myoblasts (L-6 cells) with IC50 of 174.94 μM, while 2 and 3 were found to be comparatively less active to 1. The dimeric quinones 4 and 5 exhibited good activity against T. brucei and L. donovani with IC50 of 1.12 and 8.82 μM and 12.94 and 16.66 μM respectively.