Mutagenicity of substituted anthraquinones in the Ames/Salmonella microsome system.
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.
Krivobok
S
S
Laboratoire de Botanique, Cryptogamie, Biologie Cellulaire et Génétique Université Joseph Fourier, Meylan, France.
Seigle-Murandi
F
F
Steiman
R
R
Marzin
D R
DR
Betina
V
V
D000880:Anthraquinones / Q000737:chemistry / Q000633:toxicity*; D004642:Emodin / Q000031:analogs & derivatives / Q000633:toxicity; D008861:Microsomes / Q000187:drug effects; D015394:Molecular Structure; D009152:Mutagenicity Tests; D009153:Mutagens / Q000737:chemistry / Q000633:toxicity*; D009285:Naphthoquinones / Q000633:toxicity; D012486:Salmonella typhimurium / Q000187:drug effects / Q000235:genetics
D000880:Anthraquinones; D009153:Mutagens; D009285:Naphthoquinones; C029548:rugulosin; C015829:rugulin; C008905:physcione; D004642:Emodin; C009274:skyrin; C004315:danthron