The "large sour plum" tree Ximenia caffra Sond. (Olacaceae) is the only African representative of the genus Ximenia L., with a distribution covering East Africa, from Tanzania in the north to South Africa, as well as parts of Botswana and Namibia. It has many uses in traditional medicine, including treatment of wounds and infections as well as diarrhea, which have been verified through various pharmacological studies. Furthermore, the plant is also known for its nutritional and cosmetic value. Its edible fruits are known to be high in protein, potassium and vitamin C, while the seed oil, also referred to as "Ximenia oil" is rich in long chain unsaturated fatty acids and finds use as a domestic biofuel, with characteristics amenable to cosmetic development as topical applicants. Extracts of the plants are also widely used for treating sexually transmitted infections (STIs), which has been verified through ethnobotanical surveys and pharmacological screens. Based on these observations, X. caffra var. caffra was examined for its phytochemical composition and activity against the gonorrheal pathogen Neisseria gonorrhoeae. Initially, the leaf ethanolic extract was seen to be active (43.9% inhibition). The DCM partition of this extract (with 78.8% inhibition) was subjected to bioassay guided fractionation leading to the identification of the bisnorsesquiterpene vomifoliol which exhibited significant activity (63.1%) against N. gonorrhoeae. Keywords: Antigonococcal, Neisseria gonorrhoeae, Olacaceae, Vomifoliol, Ximenia caffra.