Mechanism of antimutagenic action of (+)-catechin against the plant-activated aromatic amine 4-nitro-o-phenylenediamine

Toering, Stephanie J.; Gentile, Glenda J.; Gentile, James M.

doi:10.1016/s0165-1161(96)90242-3

Cited by 12 publications

(5 citation statements)

References 17 publications

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“…Wilson et al 42 and Toering et al 43 demonstrated that the NOP is a strong mutagen; its activation needs the action of peroxidases and=or cytochrome P450 (in plant cells). In S. typhimurium, the O-acetyltransferase activates the NOP to mutagen.…”

Section: Discussionmentioning

confidence: 99%

Phlomis mauritanica Extracts Reduce the Xanthine Oxidase Activity, Scavenge the Superoxide Anions, and Inhibit the Aflatoxin B1-, Sodium Azide-, and 4-Nitrophenyldiamine-Induced Mutagenicity in Bacteria

Limem

Bouhlel

Bouchemi

et al. 2010

Journal of Medicinal Food

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Four extracts were prepared from the leaves of Phlomis mauritanica: lyophilized infusion, total oligomer flavonoids, methanol, and ethyl acetate extracts. The antimutagenic properties of these extracts were investigated by assessing the inhibition of the mutagenic effects of direct-acting mutagens such as sodium azide and 4-nitrophenylenediamine and indirect-acting mutagens like aflatoxin B1 (AFB1) using the Ames assay. The four extracts prepared from P. mauritanica strongly inhibit the mutagenicity induced by AFB1 in both Salmonella typhimurium TA 100 and TA 98 assay systems. Lyophilized infusion and methanol extracts at the dose of 250 microg per plate reduced AFB1 mutagenicity by 93% and 91%, respectively, in S. typhymurium strain TA 100. We examined also the antioxidant effect of these extracts by the enzymatic xanthine/xanthine oxidase assay. Result indicated that total oligomer flavonoids and ethyl acetate and methanol extracts were potent inhibitors of xanthine oxidase activity. In contrast, lyophilized infusion, total oligomer flavonoids, and methanol extracts exhibited a high degree of superoxide anion scavenging. Our findings emphasize the potential of P. mauritanica extracts to prevent mutations and oxidant effects. Furthermore, the results presented here could be an additional argument to support the use of this species as a medicinal and dietary plant.

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Section: Discussionmentioning

confidence: 99%

Phlomis mauritanica Extracts Reduce the Xanthine Oxidase Activity, Scavenge the Superoxide Anions, and Inhibit the Aflatoxin B1-, Sodium Azide-, and 4-Nitrophenyldiamine-Induced Mutagenicity in Bacteria

Limem

Bouhlel

Bouchemi

et al. 2010

Journal of Medicinal Food

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“…Up to now, various methods including atomic absorption spectrometry, 14 mass spectrometry, 15,16 high-performance liquid chromatography, 17,18 etc. 19,20 have been developed. Although these techniques offered high sensitivity and selectivity, they suffered from high-throughput identification, large-scale scanning, and on-site emergency monitoring, which greatly limited their practical applications, especially in unexpected contaminant leakage events.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Upon being discharged, they probably coexist and accumulate in different extents in the environmental water systems, , which further threatens human health through activating antigen-specific T cells, binding with DNA and proteins, and finally leading to carcinogenicity. , Such carcinogenicity depends on the species of substituent groups appearing in phenylenediamine. − Therefore, accurately and simultaneously identifying these aromatic amines is imminent for environmental health risk warnings and occupational safety evaluation. Up to now, various methods including atomic absorption spectrometry, mass spectrometry, , high-performance liquid chromatography, , etc. , have been developed. Although these techniques offered high sensitivity and selectivity, they suffered from high-throughput identification, large-scale scanning, and on-site emergency monitoring, which greatly limited their practical applications, especially in unexpected contaminant leakage events.…”

Section: Introductionmentioning

confidence: 99%

Visual Sensor Array for Multiple Aromatic Amines via Specific Ascorbic Acid Oxidase Mimic Triggered Schiff-Base Chemistry

Zhang,

Gao,

et al. 2024

Anal. Chem.

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Redox nanozymes have exhibited various applications in recognizing environmental pollutants but not aromatic amines (a type of typical pollutant). Herein, with Cu 2+ as a node and tryptophan (Trp) as a linker, Cu-Trp as a specific ascorbic acid oxidase mimic was synthesized, which could catalyze ascorbic acid (AA) oxidation to dehydroascorbic acid (DHAA). Alternatively, with other natural amino acids as linkers to synthesize Cu-based nanozymes, such catalytic performances are also observed. The asproduced DHAA could react with o-phenylenediamine (OPD) and its derivatives (2,3-naphthalene diamine (NDA), 4-nitro-ophenylenediamine (4-NO 2 −OPD), 4-fluoro-o-phenylenediamine (4-F-OPD), 4-chloro-o-phenylenediamine(4-Cl-OPD), and 4bromo-o-phenylenediamine(4-Br-OPD)) to form a Schiff base and emit fluorescence. Based on the results, with Cu-Trp + AA and Cu-Arg (with arginine (Arg) as a linker) + AA as two sensing channels and extracted red, green, and blue (RGB) values from emitted fluorescence as read-out signals, a visual sensor array was constructed to efficiently distinguish OPD, NDA, 4-NO 2 −OPD, 4-F-OPD, 4-Cl-OPD, and 4-Br-OPD as low as 10 μM.Such detecting performance was further confirmed through discriminating binary, ternary, quinary, and senary mixtures with various concentration ratios, recognizing 18 unknown samples, and even quantitatively analyzing single aromatic amine. Finally, the discriminating ability was further validated in environmental waters, providing an efficient assay for large-scale scanning levels of multiple aromatic amines.

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“…99-56-9 and 5307-14-2, respectively) are widely applied as important intermediates in many chemistry-related industries. As an initial raw material, 2-nitro- p -phenylenediamine can be used to prepare dye that is used in semipermanent and permanent hair dye formulations and to synthesize ilaprazole and ezogabine. − 4-Nitro- o -phenylenediamine is also widely used in the field of fine chemicals such as dyes, herbicides, pesticides, pharmaceuticals, and pigments. − Especially for 4-nitro- o -phenylenediamine, as an important intermediate of reaction in industry, the annual consumption is increasing. Nevertheless, it is inevitably accompanied by the formation of the isomeric mixture of 4-nitro- o -phenylenediamine and 2-nitro- p -phenylenediamine. − ,− Moreover, the boiling points of these two target compounds are all higher than 410 K. Therefore, if the isomer mixture is separated by distillation, it will consume a lot of heat energy, and the operation is tedious.…”

Section: Introductionmentioning

confidence: 99%

“…According to refs , , and , pure 4-nitro- o -phenylenediamine or 2-nitro- p -phenylenediamine can be separated from the crude mixture by repeated recrystallization from solvents. During the process of our study, we noticed that N -methyl-2-pyrrolidone is a suitable solvent in separating the two products.…”

Section: Introductionmentioning

confidence: 99%

Experiment and Application of the Solid–Liquid Phase Equilibrium for Ternary 2-Nitro-p-phenylenediamine + Ethyl Acetate + Isopropanol and 2-Nitro-p-phenylenediamine + 4-Nitro-o-phenylenediamine + N-Methyl-2-pyrrolidone systems

2019

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This work was to construct isothermal binary and ternary solid−liquid phase diagrams based on the measured mutual solubility data of mixtures of 2-nitro-pphenylenediamine + ethyl acetate + isopropanol and 2-nitro-pphenylenediamine + 4-nitro-o-phenylenediamine + N-methyl-2-pyrrolidone systems. The solubility obtained for 2-nitro-pphenylenediamine in mixtures of (ethyl acetate + isopropanol) increased with the increase in composition of ethyl acetate in mixed solvents and temperature studied. In ternary phase diagram of 2-nitro-p-phenylenediamine + 4-nitro-o-phenylenediamine + N-methyl-2-pyrrolidone, it is mainly composed of two boundary curves, three crystalline regions, and one cosaturated point. The solids formed in ternary phase diagrams were confirmed via the Schreinemakers' wet residue method. The crystallization region of 4-nitro-o-phenylenediamine was smaller than that of 2-nitro-p-phenylenediamine at each temperature. The obtained solubility data in (ethyl acetate + isopropanol) were correlated with Jouyban−Acree model. Meanwhile, two activity coefficient equations (NRTL model and Wilson model) were applied to calculate the results obtained of 4-nitro-o-phenylenediamine in N-methyl-2-pyrrolidone and the mutual solubility for the ternary 2-nitro-p-phenylenediamine + 4-nitro-o-phenylenediamine + N-methyl-2-pyrrolidone system. In binary and ternary systems, the values of relative average deviation and root-mean-square deviation were no more than 4.67.00 × 10 −2 and 7.10 × 10 −3 , respectively. The calculated results via these models were all acceptable for the binary and ternary solid−liquid phase equilibrium. Moreover, the application of ternary phase diagram was discussed for separation of these mixed products of structural isomerism.

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Mechanism of antimutagenic action of (+)-catechin against the plant-activated aromatic amine 4-nitro-o-phenylenediamine

Cited by 12 publications

References 17 publications

Phlomis mauritanica Extracts Reduce the Xanthine Oxidase Activity, Scavenge the Superoxide Anions, and Inhibit the Aflatoxin B1-, Sodium Azide-, and 4-Nitrophenyldiamine-Induced Mutagenicity in Bacteria

Phlomis mauritanica Extracts Reduce the Xanthine Oxidase Activity, Scavenge the Superoxide Anions, and Inhibit the Aflatoxin B1-, Sodium Azide-, and 4-Nitrophenyldiamine-Induced Mutagenicity in Bacteria

Visual Sensor Array for Multiple Aromatic Amines via Specific Ascorbic Acid Oxidase Mimic Triggered Schiff-Base Chemistry

Experiment and Application of the Solid–Liquid Phase Equilibrium for Ternary 2-Nitro-p-phenylenediamine + Ethyl Acetate + Isopropanol and 2-Nitro-p-phenylenediamine + 4-Nitro-o-phenylenediamine + N-Methyl-2-pyrrolidone systems

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