Mutagenicity of substituted anthraquinones in the Ames/Salmonella microsome system. 1992

S Krivobok, and F Seigle-Murandi, and R Steiman, and D R Marzin, and V Betina
Laboratoire de Botanique, Cryptogamie, Biologie Cellulaire et Génétique Université Joseph Fourier, Meylan, France.

Unsubstituted anthraquinone, 4 substituted anthraquinones (emodin, danthron, physcion, a new compound M-108-C) and 3 dimers (skyrin, rugulosin, rugulin) were tested using the Ames/Salmonella assay (strains TA98, TA100, TA1537 and TA102). Danthron and emodin were found to be mutagenic for TA1537 with or without metabolic activation, physcion only with metabolic activation. A significant difference was found between the mutagenic activities of emodin (16.2 His+/nmole) and danthron (6.5 His+/nmole) as well as a high specific mutagenic activity for physcion (11.6 His+/nmole). These results on structure-mutagenic activity relationships suggest that the 6-methyl group plays an important role in the mutagenic activity after metabolic activation. Furthermore, and contrary to emodin, physcion exhibited a weak mutagenic activity for TA102, probably due to the formation of a different metabolite. Such information is necessary to evaluate the potential carcinogenic hazard of these compounds.

UI MeSH Term Description Entries
D008861 Microsomes Artifactual vesicles formed from the endoplasmic reticulum when cells are disrupted. They are isolated by differential centrifugation and are composed of three structural features: rough vesicles, smooth vesicles, and ribosomes. Numerous enzyme activities are associated with the microsomal fraction. (Glick, Glossary of Biochemistry and Molecular Biology, 1990; from Rieger et al., Glossary of Genetics: Classical and Molecular, 5th ed) Microsome
D009152 Mutagenicity Tests Tests of chemical substances and physical agents for mutagenic potential. They include microbial, insect, mammalian cell, and whole animal tests. Genetic Toxicity Tests,Genotoxicity Tests,Mutagen Screening,Tests, Genetic Toxicity,Toxicity Tests, Genetic,Genetic Toxicity Test,Genotoxicity Test,Mutagen Screenings,Mutagenicity Test,Screening, Mutagen,Screenings, Mutagen,Test, Genotoxicity,Tests, Genotoxicity,Toxicity Test, Genetic
D009153 Mutagens Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes. Clastogen,Clastogens,Genotoxin,Genotoxins,Mutagen
D009285 Naphthoquinones Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups. Naphthalenediones,Naphthazarins,Naphthoquinone
D004642 Emodin Purgative anthraquinone found in several plants, especially RHAMNUS PURSHIANA. It was formerly used as a laxative, but is now used mainly as a tool in toxicity studies. Casanthranol,Frangula Emodin,Peristim,Rheum Emodin,Archin,Frangulic Acid,Emodin, Frangula,Emodin, Rheum
D000880 Anthraquinones Compounds based on ANTHRACENES which contain two KETONES in any position. Substitutions can be in any position except on the ketone groups. Anthracenedione,Anthracenediones,Anthranoid,Anthraquinone,Anthraquinone Compound,Anthraquinone Derivative,Dianthraquinones,Dianthrones,Anthranoids,Anthraquinone Compounds,Anthraquinone Derivatives,Compound, Anthraquinone,Derivative, Anthraquinone
D012486 Salmonella typhimurium A serotype of Salmonella enterica that is a frequent agent of Salmonella gastroenteritis in humans. It also causes PARATYPHOID FEVER. Salmonella typhimurium LT2
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular

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