2-Hydroxyemodin, an active metabolite of emodin in the hepatic microsomes of rats

• Published in: Mutation research Vol. 149; no. 3; p. 327
• Main Authors: Masuda, T, Haraikawa, K, Morooka, N, Nakano, S, Ueno, Y
• Format: Journal Article
• Language: English
• Published: Netherlands 01.05.1985
• Subjects: Animals; Anthraquinones - metabolism; Biotransformation; Emodin - analogs & derivatives; Emodin - metabolism; Microsomes, Liver - metabolism; Mutagenicity Tests; Rats; Salmonella typhimurium - drug effects
• DOI: 10.1016/0027-5107(85)90148-4
• ISSN: 0027-5107

The hepatic microsomes derived from rats transformed emodin (1,3,8-trihydroxy-6-methyl-anthraquinone), an anthraquinone present in fungal metabolites and constituent of rhubarb, into at least 10 anthraquinoid metabolites. Metabolite d proved to be mutagenic to Salmonella typhimurium TA1537 in the absence of activation system. MS, NMR, UV and mutagenicity test analysis revealed that metabolite d was 2-hydroxyemodin (1,2,3,8-tetrahydroxy-6-methyl-anthraquinone) and exhibited mutagenicity in doses of 2-20 micrograms/plate. In addition to this active metabolite, TLC analysis revealed the formation of 4-hydroxyemodin (metabolite a), 5-hydroxyemodin (metabolite b), 7-hydroxyemodin (metabolite d') and others. No mutagenicity of these monohydroxyemodins was demonstrated in the absence of activation system.