Chemical properties of thymoquinone, a monoterpene isolated from the seeds of Nigella sativa Linn.

Thymoquinone is the main ingredient of the essential oil extracted from the seeds of Nigella sativa L. (Ranunculaceae). The monoterpene is considered to be the active pharmaceutical ingredient in the seeds, which have traditionally been highly prized for their medicinal properties. The compound has been the focus of a considerable number of pharmacological investigations and has been reviewed regularly for its action against a variety of inflammatory diseases, its effect on metabolic syndrome, and its potential anticancer properties. While discussing the chemical and pharmacological properties of thymoquinone, recent reviews have reflected on the keto-enol tautomerism of thymoquinone. Specifically, thymoquinone is described as a tautomeric compound, where the keto-form is said to be the major configuration that is responsible for its pharmacological properties [1, 2]. In both reviews, reference is made to a 2005 review by Salem [3]. The latter review discusses a range of activities of thymoquinone, mainly on cell signalling and antioxidant (scavenging) molecular mediators involved in the process of inflammation. However, no mention is made in this review of keto- or enol forms of thymoquinone. Moreover, the chemical structure of thymoquinone does not allow keto-enol tautomerism.