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Plumbagin, a plant-derived bioactive naphthoquinonoid compound, was converted to a hydroquinonoid derivative, which was studied for its tumour-inhibitory and antileishmanial activities for the first time. A similar chemical transformation was undertaken on an analogous dimeric compound, diospyrin, and its bioassay results were compared with those of the plumbagin derivative. Synthesis of the derivative of plumbagin did not result in a marked enhancement of the tumour-inhibitory activity, whereas the improvement was obvious in the case of diospyrin vis à vis its hydroquinonoid analogue. The conversion of diospyrin to the hydroquinonoid compound also led to a substantial increase in the antileishmanial activity, while a similar conversion of plumbagin failed to do so.

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