Formation of naphthoquinones and anthraquinones by carbonyl-hydroquinone/benzoquinone reactions: A potential route for the origin of 9,10-anthraquinone in tea

Abstract

The reaction of 2-alkenals (crotonaldehyde and 2-pentenal) with hydroquinones (hydroquinone and tert-butylhydroquinone) and benzoquinones (benzoquinone, methylbenzoquinone, and methoxybenzoquinone) was studied as a potential route for the endogenous formation of naphthoquinones and anthraquinones in foods. Polycyclic quinones were produced at a low water activity, within a wide pH range, and in the presence of air. 9,10-Anthraquinone formation had an activation energy of 46.1 ± 0.1 kJ·mol−1, and a reaction pathway for the formation of the different naphthoquinones and anthraquinones is proposed. These reactions also took place in tea, therefore suggesting that the common tea pollutant 9,10-anthraquinone is also a process-induced contaminant. In fact, when four commercial teas (from a total of eight studied teas) were heated at 60 °C for 72 h, they significantly (p < 0.05) increased the amount of this toxicant. Reduction of 9,10-anthraquinone formation in teas is suggested to be carried out by reducing/scavenging its precursors.