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Mutagenicity of anthraquinones in the Salmonella preincubation test
Abstract:
The mutagenicities of 15 naturally occurring anthraquinones were examined in Salmonella typhimurium strains TA98, TA100 and TA2637 by the preincubation method. 7 of the 15 compounds tested, i.e., chrysazin, emodin, islandicin, alizarin, chrysophanol, 2-hydroxyanthraquinone and emodic acid, were strong mutagens in strain TA2637 with metabolic activation. All of these compounds contain 1-3 hydroxyl groups, and some also have methyl groups. Cynodontin, an anthraquinone with 4 hydroxyl groups and 1 methyl group, was only slightly mutagenic in strain TA2637. 2-Hydroxyanthraquinone, alizarin, emodin, islandicin and chrysazin were also mutagenic in strain TA100 with S9 mix. All the bisanthraquinones tested, i.e., skyrin, (+)rugulosin, (-)luteoskyrin, (-)rubroskyrin and sennoside A, were non-mutagenic in this test system with or without metabolic activation. Unsubstituted anthraquinone and anthrone were also non-mutagenic. These results show that hydroxyl substituents are necessary for the mutagenicity of anthraquinones, the optimal substitutions being 1-3 hydroxyl groups per molecule. The 4th hydroxyl group, in the compound cynodontin reduces the mutagenicity considerably.
Insights
Naturally occurring anthraquinones with 1-3 hydroxyl groups are potent mutagens in Salmonella typhimurium strains TA2637 and TA100, especially with metabolic activation. Additional hydroxyl groups reduce mutagenicity.
Area of Science:
- Toxicology
- Natural Products Chemistry
- Genetics
Background:
- Anthraquinones are a diverse class of naturally occurring compounds with various biological activities.
- Understanding the mutagenic potential of these compounds is crucial for assessing their safety and potential applications.
Purpose of the Study:
- To evaluate the mutagenicity of 15 naturally occurring anthraquinones using bacterial assays.
- To identify structural features of anthraquinones that correlate with mutagenic activity.
Main Methods:
- Bacterial mutagenicity testing using Salmonella typhimurium strains TA98, TA100, and TA2637.
- Preincubation method with and without metabolic activation (S9 mix).
Main Results:
- Seven anthraquinones (chrysazin, emodin, islandicin, alizarin, chrysophanol, 2-hydroxyanthraquinone, emodic acid) showed strong mutagenicity in TA2637 with metabolic activation.
- Mutagenicity was associated with 1-3 hydroxyl groups; cynodontin (4 hydroxyls) was weakly mutagenic.
- Certain compounds were also mutagenic in TA100 with S9 mix.
- Bisanthraquinones and unsubstituted anthraquinone/anthrone were non-mutagenic.
Conclusions:
- Hydroxyl group substitution is essential for anthraquinone mutagenicity.
- Optimal mutagenicity is observed with 1-3 hydroxyl groups per molecule.
- A fourth hydroxyl group significantly reduces mutagenic potential.