10228-40-7Relevant articles and documents
Chemical Reactivity of Emodin and Its Oxidative Metabolites to Thiols
Qin, Boyang,Xu, Yang,Chen, Jiaming,Huang, Wenlin,Peng, Ying,Zheng, Jiang
, p. 2114 - 2124 (2016)
Polygonum multiflorum is an herbal medicine widely employed in China. Hepatotoxicity of the herbal medicine has been well documented, but the mechanisms of the toxicity remain unknown. Emodin (EM) is a major constituent of the herb and has been reported to be hepatotoxic. The main purpose of this study was to define the metabolic pathways of EM in order to characterize the potential reactive intermediates. EM was incubated with rat liver microsomes or human liver microsomes, followed by LC-MS/MS analysis to investigate the in vitro and in vivo metabolism of EM. As a result, three monohydroxylation metabolites (M1-M3) were detected after exposure to EM: -hydroxyemodin, 2-hydroxyemodin, and 5-hydroxyemodin. Urinary M1 and M2 were detected in rats administered EM. Three mercapturic acids (M4-M6) were found in microsomal incubations containing EM, NADPH, and N-acetylcysteine. It appears that M4 originated from parent compound EM, and M5 and M6 originated from M1 and M2, respectively. Two biliary EM-derived GSH conjugates were found in EM-treated rats. One arose from direct adduction of EM with GSH, and the other was derived from M1. Cytochrome P450's 1A2, 2C19, and 3A4 were the predominant P450 enzymes to oxidize EM. The findings helped us to understand the mechanisms of EM-induced hepatotoxicity.
The Chemical Structure and the Mutagenicity of Emodin Metabolites
Morooka, Nobuhisa,Nakano, Sonoko,Itoi, Noriko,Ueno, Yoshio
, p. 1247 - 1252 (2007/10/02)
Emodin (1,3,8-trihydroxy-6-methyl-9,10-anthraquinone) is a natural occuring 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.
Reactions of Ketene Acetals. 13. Synthesis of Contiguously Trihydroxylated Naphto- and Anthraquinones
Roberge, Guy,Brassard, Paul
, p. 4161 - 4166 (2007/10/02)
A regiospecific method of obtaining various quinones bearing at least three adjacent hydroxyl groups has been devised by using a new vinylketene acetal, 2-methoxy-1,1,3-tris(trimethylsiloxy)-1,3-butadiene (9b).In this way the first total syntheses of dermoglaucin (50) and ceroalbolinic acid, as its pentamethyl derivative 49, have been achieved.The structure of another natural product, capareolatin dimethyl ether, was established indirectly by the unambiguous formation of one of the two possible isomers.Advantageous preparations of "7-hydroxyemodin", copareolatin, and isoerythrolaccin derivatives 32,38, and 2, as well as those of useful intermediates such as 2- and 3-chloro-5,7-dihydroxy-6-methoxynaphthoquinones or their dimethyl ethers, are described.
