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Emodin (1,3,8-trihydroxy-6-methyl-9,10-anthraquinone) is a natural occurring anthraquinone formed in rhubarb and fungal metabolites. Emodin was transformed into 6 major metabolites by rat hepatic microsomes. The metabolites were identified as 2-hydroxyemodin, 4-hydroxyemodin, 5-hydroxyemodin, 7-hydroxyemodin, ω-hydroxyemodin, and emodic acid by comparison with the synthetic compounds using thin-layer chromatography. It was clear that 2-hydroxyemodin is a proximate mutagen as a synthetic compound by the Salmonella assay. Other metabolites, such as 5-hydroxyemodin and ω-hydroxyemodin, became active after metabolic activation, but 4-hydroxyemodin and emodic acid were inactive either in the presence or in the absence of the metabolic activation system.

The chemical structure and the mutagenicity of emodin metabolites.