Studies on the photostability and phototoxicity of aloe-emodin, emodin and rhein.

Aloe-emodin (1), emodin (2) and rhein (3) were found to be photolabile by visible (390-500 nm) light under aerobic conditions. The drugs 1, 2 and 3 were phototoxic in vitro when examined by the photohemolysis test under both oxygen and argon atmospheres, although the photohemolysis rate was markedly lower under anaerobic conditions. The experiments were also carried out in the presence of butylated hydroxyanisole (BHA), reduced glutathione (GSH), sodium azide (NaN3) and superoxide dismutase (SOD). Based on the inhibition of this process on addition of BHA, GSH, SOD and NaN3, there would seem to be involvement of free radicals (type I mechanism) and singlet oxygen in the process (type II mechanism). The in vitro phototoxicity of this anthraquinone series was also verified in a lipid-photoperoxidation test with linoleic acid. In summary, this anthraquinone series is phototoxic in vitro. This behavior can be explained through the involvement of singlet oxygen and stable photoproducts.