Naphthoquinone Derivatives from Diospyros maritima.

From the chloroform extract of the fresh fruits of Diospyros maritima BLUME (Ebenaceae), five new naphthoquinone derivatives, 2,7'-dimethyl-2',3-bijuglone (27), 2,7'-dimethyl-3,3'-bijuglone (28), 2,7'-dimethyl-6,8'-bijuglone (29), 7,7'-dimethyl-3,3'-ethylidenebijuglone (30), and 2',7-dimethyl-3,6'-ethylidenebijuglone (31), were isolated, in addition to twenty-one known naphthoquinone derivatives: plumbagin (4), droserone (5), 2,3-epoxyplumbagin (8), 3,3'-biplumbagin (9), chitranone (10), 3,8'-biplumbagin (11), elliptinone (12), maritinone (13), isozeylanone (14), methylene-3,3'-biplumbagin (15), ethylidene-3,3'-biplumbagin (16), ethylidene-3,6'-biplumbagin (17), ethylidene-6,6'-biplumbagin (18), 7-methyl-β-dihydrojuglone (19), 7-methyljuglone (20), 2,3-epoxy-7-methyljuglone (21), neodiospyrin (22), mamegakinone (23), ehretione (24), isoxylospyrin (25) and β-dihydroplumbagin (26). The structures of the new compounds were established by spectral analysis. The quinones obtained from the chloroform extract of the fruits were compared with previously reported quinones obtained from ethanol extracts. The quinones in the fruits were categorized in three groups: quinones from ethanol extract only, quinones from chloroform extract only, and quinones from both extracts. The six naphthoquinones, 19-21, 25, 26, and 29, were examined for their ichthyotoxic activity and germination inhibitory activity. Quinones 19-21, 26, and 29 showed ichthyotoxic activity against Japanese killifish (Oryzias latipes var.) at 10 ppm; quinones 19 to 21 and 26 showed germination inhibitory activity toward lettuce seeds (Lactuca sativa L. var. Great Lakes) at 100 ppm.