Mutagenic potential of copper compounds and modification of effects of silver iodide]

Mutagenic potential of copper compounds and its alteration in case of the interaction with silver compounds were analyzed by use of plant test systems. As test systems, Crepis capillaris L., Tradescantia clone 02, and soybean (Glycine max (L.) Merrill) were used. Mutagenic properties of copper iodide and copper sulfate were not detected. CuI, being not a mutagen by itself, remarkably enhanced mutagenic potential of AgI.     

In vitro mutagenic,antimutagenic, and antioxidant activities evaluation and biotransformation of some bioactive 4‐substituted 1‐(2‐methoxyphenyl)piperazine derivatives

In vitro mutagenic, antimutagenic, and antioxidant potency evaluation and biotransformation of six novel 4‐substituted 1‐(2‐methoxyphenyl)piperazine derivatives demonstrating antidepressant‐like activity were investigated. Mutagenic and antimutagenic properties were assessed using the Ames test; free radical scavenging activity was evaluated with 2,2‐diphenyl‐1‐picrylhydrazyl radical scavenging assay and biotransformation was performed with liver microsomes. It was found that all tested compounds are not mutagenic in bacterial strains TA100 and TA1535 and exhibit antimutagenic effects in the Ames test. Noteworthy, compounds possessing propyl linker between phenoxyl and N‐(2‐methoxyphenyl)piperazine displayed more pronounced antimutagenic properties than derivatives with ethoxyethyl linker. Additionally, compounds 2 and 6 in vitro biotransformation showed that primarily their hydroxylated or O‐dealkylated metabolites are formed. Some of the compounds exhibited intrinsic clearance values lower than those reported previously for antidepressant imipramine. To sum up, the results of the present study might represent a valuable step in designing and planning future studies with piperazine derivatives.     

The main components of St John's Wort inhibit low-density lipoprotein atherogenic modification: A beneficial “side effect” of an OTC antidepressant drug?

Hypericin and pseudohypericin are polycyclic–phenolic structurally related compounds found in Hypericum perforatum L. (St John's wort). As hypericin has been found to bind to LDL one may assume that it can act as antioxidant of LDL lipid oxidation, a property which is of prophylactic/therapeutic interest regarding atherogenesis as LDL oxidation may play a pivotal role in the onset of atherosclerosis. Therefore, in the present paper hypericin, pseudohypericin and hyperforin, an other structurally unrelated constituent in St John's wort were tested in their ability to inhibit LDL oxidation. LDL was isolated by ultracentrifugation and oxidation was initiated either by transition metal ions (copper), tyrosyl radical (myeloperoxidase/hydrogen peroxide/tyrosine) or by endothelial cells (HUVEC). LDL modification was monitored by conjugated diene and malondialdehyde formation. The data show that all compounds (hypericin, pseudohypericin and hyperforin) at doses as low as 2.5 μmol/l are potent antioxidants in the LDL oxidation systems used. The results indicate that the derivatives found in Hypericum perforatum have possible antiatherogenic potential.     

Preponderance of Oxygenated Sesquiterpenes and Diterpenes in the Volatile Oil Constituents of Lactuca serriola L. Revealed Antioxidant and Allelopathic Activity

Using synthetic chemicals in industry and agriculture has led to several environmental problems. Thus, plant products derived from volatile oils (VOs) could be a potential green source for bioherbicides. Little is known about the VOs of Lactuca serriola. Hence, the present study aimed to characterize the VOs chemical composition from the aerial parts of L. serriola, assessment of antioxidant activity, and evaluate allelopathic potential against the noxious weed Bidens pilosa. The VOs were extracted by hydrodistillation and analyzed by GC/MS. The VOs from the Egyptian ecospecies of L. serriola were found to comprise 34 compounds mainly oxygenated sesquiterpenes and diterpenes. The major compounds were isoshyobunone (64.22 %), isocembrol (17.35 %), and alloaromadendrene oxide‐1 (7.32 %). So, L. serriola can be considered as a good source for isoshyobunone, considering that it has a much higher concentration than any other plants. Also, this plant has a high content of the oxygenated diterpene compound, isocembrol, which is rarely found in the VOs of most plants. The VOs expressed strong antioxidant activity. Also, for the first time, our results showed a strong allelopathic activity of VOs from L. serriola on germination and seedling growth of the noxious weed, B. pilosa. We suppose that the activity of the VOs from L. serriola could be attributed to these previously mentioned major compounds, as they represent about 89 % of the total identified oil constituents. Nevertheless, to evaluate these compounds as new allelochemicals, further study is needed to test the allelopathic activity of authenticated standard of these compounds either singular or in combination on several weeds as well as evaluate the safety, and improve the efficacy and stability at the field scale.     

Identification of a copper-responsive promoter and development of a copper biosensor in the soil bacterium <Emphasis Type="Italic">Achromobacter</Emphasis> sp. AO22

A number of human activities result in environmental contamination with copper compounds that can cause severe detrimental effects on the ecosystem as well as human health. The physico-chemical methods of metal detection have limitations such as inability to distinguish between total versus bio-available metals and differences in metal uptake in different organisms. The heavy metal resistance-encoding genetic systems of certain bacteria provide critical tools for development of biosensors for these purposes. This study reports a copper biosensor utilizing the cop operon of the heavy metal resistant bacterial isolate, Achromobacter sp. AO22, isolated from a contaminated site in Australia. A section located between the divergently transcribed putative response regulator gene copR and multicopper oxidase gene copA that included a palindromic cop box was identified as a copper-responsive promoter using a lacZ reporter construct, pCOPRP, in E. coli. The expression was found to be enhanced by inclusion of copR. Another engineered strain, AO22(pCOPRP), showed stronger induction, and the lacZ expression in both backgrounds was enhanced significantly (250–400 fold) by copper but minimally by other metals. The construct in Achromobacter sp. AO22 thus has a high potential as biosensor for detecting copper bioavailability (hence potential toxicity) in a soil bacterial background, while the construct in E. coli is ideal for laboratory-based testing.     

Characterization of Copper-Resistant Rhizosphere Bacteria from <Emphasis Type="Italic">Avena sativa</Emphasis> and <Emphasis Type="Italic">Plantago lanceolata</Emphasis> for Copper Bioreduction and Biosorption

Copper is a toxic heavy metal widely used to microbial control especially in agriculture. Consequently, high concentrations of copper residues remain in soils selecting copper-resistant organisms. In vineyards, copper is routinely used for fungi control. This work was undertaken to study copper resistance by rhizosphere microorganisms from two plants (Avena sativa L. and Plantago lanceolata L.) common in vineyard soils. Eleven rhizosphere microorganisms were isolated, and four displayed high resistance to copper. The isolates were identified by 16S rRNA gene sequence analysis as Pseudomonas putida (A1), Stenotrophomonas maltophilia (A2) and Acinetobacter sp. (A6), isolated from Avena sativa rhizosphere, and Acinetobacter sp. (T5), isolated from Plantago lanceolata rhizosphere. The isolates displayed high copper resistance in the temperature range from 25°C to 35°C and pH in the range from 5.0 to 9.0. Pseudomonas putida A1 resisted as much as 1,000 mg L⁻¹ of copper. The isolates showed similar behavior on copper removal from liquid medium, with a bioremoval rate of 30% at 500 mg L⁻¹ after 24 h of growth. Speciation of copper revealed high copper biotransformation, reducing Cu(II) to Cu(I), capacity. Results indicate that our isolates are potential agents for copper bioremoval and bacterial stimulation of copper biosorption by Avena sativa and Plantago lanceolata.     

Comparative analysis of peroxiredoxin activation in the brown macroalgae Scytosiphon gracilis and Lessonia nigrescens (Phaeophyceae) under copper stress

Among thiol‐dependent peroxidases (TDPs) peroxiredoxins (PRXs) standout, since they are enzymes capable of reducing hydrogen peroxide, alkylhydroperoxides and peroxynitrite, and have been detected in a proteomic study of the copper‐tolerant species Scytosiphon gracilis. In order to determine the importance of these enzymes in copper‐stress tolerance, TDP activity and type II peroxiredoxin (II PRX) protein expression were compared between the opportunistic S. gracilis and the brown kelp Lessonia nigrescens, a species absent from copper‐impacted sites due to insufficient copper‐tolerance mechanisms. Individuals of both species were cultured with increasing copper concentrations (0–300 µg l^?1 Cu) for 96 h and TDP activity and lipoperoxides (LPXs) were determined together with II PRX expression by immunofluorescence and Western blot analysis. The results showed that TDP activity was higher in S. gracilis than L. nigrescens in all copper concentrations, independent of the reducing agent used (dithiothreitol, thioredoxin or glutaredoxin). This activity was copper inhibited in L. nigrescens at lower copper concentrations (20 µg l^?1 Cu) compared to S. gracilis (100 µg l^?1 Cu). The loss of activity coincided in both species with an increase in LPX, which suggests that TDP may control LPX production. Moreover, II PRX protein levels increased under copper stress only in S. gracilis. These results suggest that in S. gracilis TDP, particularly type II peroxiredoxin (II PRX), acts as an active antioxidant barrier attenuating the LPX levels generated by copper, which is not the case in L. nigrescens. Thus, from an ecological point of view these results help explaining the inability of L. nigrescens to flourish in copper‐enriched environments.     

Evaluation of the Allelopathic Potential of Leaf,Stem, and Root Extracts of Ocotea pulchella Nees et Mart

Despite the increase in recent decades in herbicide research on the potential of native plants, current knowledge is considered to be low. Very few studies have been carried out on the chemical profile or the biological activity of the Brazilian savanna (Cerrado) species. In the study reported here, the allelopathic activity of AcOEt and MeOH extracts of leaves, stems, and roots from Ocotea pulchella Nees was evaluated. The extracts were assayed on etiolated wheat coleoptiles. The AcOEt leaf extract was the most active and this was tested on standard target species (STS). Lycopersicon esculentum and Lactuca sativa were the most sensitive species in this test. A total of eleven compounds have been isolated and characterized. Compounds 1 , 2 , 4 , and 6 have not been identified previously from O. pulchella and ocoteol ( 9 ) is reported for the first time in the literature. Eight compounds were tested on wheat coleoptile growth, and spathulenol, benzyl salicylate, and benzyl benzoate showed the highest activities. These compounds showed inhibitory activity on L. esculentum. The values obtained correspond to the activity exhibited by the extract and these compounds may therefore be responsible for the allelopathic activity shown by O. pulchella.     

Biological cost of tolerance to heavy metals in the mosquito Anopheles gambiae

The global rate of heavy metal pollution is rapidly increasing in various habitats. Anopheles malaria vector species (Diptera: Culicidae) appear to tolerate many aquatic habitats with metal pollutants, despite their normal proclivity for ‘clean’ water (i.e. low levels of organic matter). Investigations were conducted to establish whether there are biological costs for tolerance to heavy metals in Anopheles gambiae Giles sensu stricto and to assess the potential impact of heavy metal pollution on mosquito ecology. Anopheles gambiae s.s. were selected for cadmium, copper or lead tolerance through chronic exposure of immature stages to solutions of the metals for three successive generations. Biological costs were assessed in the fourth generation by horizontal life table analysis. Tolerance in larvae to cadmium (as cadmium chloride, CdCl₂), copper [as copper II nitrate hydrate, Cu(NO₃)₂ 2.5 H₂O] and lead [as lead II nitrate, Pb(NO₃)₂], monitored by changes in LC₅₀ concentrations of the metals, changed from 6.07 µg/L, 12.42 µg/L and 493.32 µg/L to 4.45 µg/L, 25.02 µg/L and 516.69 µg/L, respectively, after three generations of exposure. The metal‐selected strains had a significantly lower magnitude of egg viability, larval and pupal survivorship, adult emergence, fecundity and net reproductive rate than the control strain. The population doubling times were significantly longer and the instantaneous birth rates lower in most metal‐selected strains relative to the control strain. Our results suggest that although An. gambiae s.s. displays the potential to develop tolerance to heavy metals, particularly copper, this may occur at a significant biological cost, which can adversely affect its ecological fitness.     

Studies on Phytoremediation of Copper Using Pteridium Aquilinum (Bracken Fern) In the Presence of Biostimulants and Bioassay Using Clarias Gariepinus Juveniles

A study was carried out to evaluate the uptake of copper from water containing 10 mg/L copper by Pteridium aquilinum (bracken fern) and Clarias gariepinus in the presence of five plant growth stimulants: Nitrogen: phosphorus: potassium (15-15-15: an inorganic fertilizer), pig, cattle, poultry, and a mixture of pig/cattle manures. A plant growth stimulant differentiated each treatment. A 96-hour bioassay using C. gariepinus was carried out at the end of the experiment to test the efficacy of the clean up by P. aquilinum. The control experiment contained no copper or plant growth stimulant. Fish survival, uptake of copper by P. aquilinum, C. gariepinus, concentration of copper in water, hematology and histopathology of the fish were assessed. Higher concentrations of copper were reported in P. aquilinum than in water or C. gariepinus. Low fish mortality was reported with the highest being 20% in the cattle manure–containing treatment.     

Identification of attractant and repellent plants to coffee berry borer,Hypothenemus hampei

Colombia is one of the world's largest producers of coffee [Coffea arabica L. (Rubiaceae)]. The coffee berry borer (CBB), Hypothenemus hampei (Ferrari) (Coleoptera: Curculionidae: Scolytinae), is the main pest of coffee. This insect is controlled through an integrated pest management program that includes cultural, biological, and chemical control strategies. Despite research seeking CBB attractants and repellents, these potential management tools have not been successfully incorporated into control programs. This work proposes the use of plant functional diversity for CBB management, for which a number of plants related to coffee and weeds were selected. CBB preference to these plants was determined by olfactometry and volatile compounds emitted by them were identified. Field trials were performed to test CBB preference under field conditions. These trials determined the olfactory preference of CBB to coffee berries accompanied by material of the plants Crotalaria micans Link (Fabaceae), Lantana camara L. (Verbenaceae), Nicotiana tabacum L. (Solanaceae), Artemisia vulgaris L., Calendula officinalis L., Stevia rebaudiana (Bertoni) Bertoni, and Emilia sonchifolia (L.) DC. (all four Asteraceae). Under laboratory conditions N. tabacum, L. camara, and C. officinalis were identified as repellents for CBB in olfactometer assays, whereas E. sonchifolia functioned as attractant. Controlled field trials corroborated CBB repellency of N. tabacum and L. camara; both release volatile sesquiterpenes. Selected candidate attractants included E. sonchifolia plants, for showing attraction in the laboratory. The potential use of these plants in agroecological management of coffee plantations is discussed.     

Locus specificity of mutagenicity of 2,4-diaminotoluene in both L5178Y mouse lymphoma and AT3-2 Chinese hamster ovary cells

2,4-Diaminotoluene, a hepatocarcinogenic aromatic amine, was tested for mutagenic potential at both the autosomal tk locus and the sex-linked hgprt locus of both L5178Y 3.7.2C mouse lymphoma cells and Chinese hamster ovary (CHO) AT3-2 cells. This compound was mutagenic in both cell types at the tk locus but not at the hgprt locus. Mutagenic activity was observed in L5178Y cells only in the absence of exogenous metabolic activation, but was observed in CHO-AT3-2 cells both with and without activation.     

Metal complexes of carboxamidrazone analogs as antitubercular agents: 1. Synthesis, X-ray crystal-structures, spectroscopic properties and antimycobacterial activity against Mycobacterium tuberculosis H37Rv

N¹-Benzylidene-pyridine carboxamidrazones and their metal conjugates have emerged as a new class of potential antimycobacterial agents. Nine such carboxamidrazone analogs (L₁–L₉) along with their Cu(II) (MC₁–MC₉) and Fe(III) (MC₁₀–MC₁₈) complexes were synthesized. Single crystal X-ray structures of copper complexes MC₁ and MC₅ were determined which suggest slightly distorted square planer geometries for copper complexes and octahedral geometries for ferric compounds. All compounds were evaluated for their in vitro antimycobacterial activity against Mycobacterium tuberculosis H₃₇Rv. The results show 32–64-fold enhancement in antitubercular activity upon copper complexation.     

Response of Gram-positive bacteria to copper stress

The Gram-positive bacteria Enterococcus hirae, Lactococcus lactis, and Bacillus subtilis have received wide attention in the study of copper homeostasis. Consequently, copper extrusion by ATPases, gene regulation by copper, and intracellular copper chaperoning are understood in some detail. This has provided profound insight into basic principles of how organisms handle copper. It also emerged that many bacterial species may not require copper for life, making copper homeostatic systems pure defense mechanisms. Structural work on copper homeostatic proteins has given insight into copper coordination and bonding and has started to give molecular insight into copper handling in biological systems. Finally, recent biochemical work has shed new light on the mechanism of copper toxicity, which may not primarily be mediated by reactive oxygen radicals.     

3种百合鳞茎中多酚类物质的抗氧化活性分析

以野生百合渥丹、山丹和传统食用的兰州百合为研究对象,对其鳞茎中多酚类物质、11种单体酚的含量及抗氧化活性(ABTS自由基、超氧阴离子、羟自由基的清除能力,铜离子还原能力以及抑制脂质过氧化活性)进行了分析。结果表明:两种野生百合鳞茎中的多酚类物质含量及抗氧化活性均显著高于兰州百合。3种百合鳞茎中单体酚的种类也有所不同,但均含有没食子酸、矢车菊素-3-芸香糖苷、儿茶素、表儿茶素、杨梅酮、芦丁、对香豆酸、山奈酚。相关性分析显示,除对羟自由基的清除力外,各酚类物质总量与不同抗氧化指标之间呈显著正相关关系。试验结果认为,野生百合鳞茎可作为天然抗氧化资源应用于食品和医药业,具有一定的开发应用前景。     

Validation of the Salmonella (SV50)/arabinose-resistant forward mutation assay system with 26 compounds

Mutagenic sensitivity of the Salmonella/arabinose-resistant (Ara^r) assay system using the tester strain SV50 was evaluated with 26 compounds both by the preincubation and the standard plate incorporation tests. The mutagenic activity of all 26 compounds was also tested with TA98 and/or TA100 of the Ames Salmonella/microsome assay system. The results indicate that 13 and 10 of 26 compounds were mutagenic and nonmutagenic, respectively, in both assay systems. PR toxin and hydrogen peroxide were mutagenic only in the Ara^r assay, while 2-nitrofluorene was mutagenic only in the Ames assay. The results also show that the mutagenic response of SV50 to 13 of 15 mutagenic compounds was much higher (2.1–154-fold) if the compounds were tested with the preincubation rather than the plate incorporation test. The mutagenic activity of 4 compounds (diethyl sulfate, niridazole, PR toxin and hydrogen peroxide) in the Ara^r assay was detected only with the preincubation test.Since the Ara^r assay using tester strain SV50 has similar mutagenic sensitivity as the Ames assay to chemicals with different modes of action and since it requires only one tester strain, we find this assay system to be useful for screening environmental mutagens. Based on the effectiveness of the preincubation test in this study, it is recommended that the preincubation test instead of the plate incorporation test be used for the Ara^r assay system with tester strain SV50.     

Antifungal Activity,Structure-Activity Relationship and Molecular Docking Studies of 1,2,4-Triazole Schiff Base Derivatives

Fourteen novel Schiff base compounds ( AS-1 ∼ AS-14 ) containing 5-amino-1H-1,2,4-triazole-3-carboxylic acid and substituted benzaldehyde were successfully synthesized, and their structures were verified by melting point, elemental analysis (EA) and spectroscopic techniques (Fourier Transform Infra-Red (FT-IR) and Nuclear Magnetic Resonance (NMR)). In vitro hyphal measurements were used to investigate the antifungal activities of the synthesised compounds against Wheat gibberellic, Maize rough dwarf and Glomerella cingulate. The preliminary studies indicated that all compounds had good inhibitory effect on Wheat gibberellic and Maize rough dwarf, among which the compounds of AS-1 (7.44 mg/L, 7.27 mg/L), AS-4 (6.80 mg/L, 9.57 mg/L) and AS-14 (5.33 mg/L, 6.53 mg/L) showed better antifungal activity than that of the standard drug fluconazole (7.66 mg/L, 6.72 mg/L); while inhibitory effect against Glomerella cingulate was poor, only AS-14 (5.67 mg/L) was superior to that of fluconazole (6.27 mg/L). The research of structure-activity relationship exhibited that the introduction of halogen elements on the benzene ring and electron withdrawing groups at the 2,4,5 positions on the benzene ring was beneficial to the improvement of the activity against Wheat gibberellic, while the large steric hindrance was not conducive to the improvement of the activity. Additionally, except for AS-1 , AS-3 and AS-10 , the other compounds had one or several ratio systems to achieve synergistic effect after recombination with pyrimethamine, among which AS-7 had significant synergistic effect and was expected to be a combinated agent with application prospects. Finally, the molecular docking results of isocitrate lyase with Wheat gibberellic displayed that the presence of hydrogen bonds enabled stable binding of compounds to receptor proteins, and the residues of ARG A: 252, ASN A: 432, CYS A: 215, SER A: 436 and SER A: 434 were the key residues for their binding. Comparing the docking binding energy and biological activity results, it was revealed that the lower the docking binding energy was, the stronger the inhibitory ability of the Wheat gibberellic, when the same position on the benzene ring was substituted.     

Decomposition of Lipid Hydroperoxide by Choline and Ethanolamine

The leaves of thyme (Thymus vulgaris L.) were found to contain new compounds, 4′-hydroxy-5,5′-diisopropyl-2,2′-dimethyIbiphenyl-3,4-dione (1), 5,5′-diisopropyl-2,2′-dimethylbiphenyl-3,4,3′,4^/-tetraone (2), and 4,4′-dihydroxy-5,5′-disopropyl-2,2′-dimethylbiphenyl-3,6-dione (3a). These structures were determined by chemical and spectroscopic methods. The deodorant activity of compound 1 against methyl mercaptan was more effective than that of rosmanol, carnosol and sodium copper chlorophylline.     

IN SITU ALLELOPATHIC POTENTIAL OF MYRIOPHYLLUM VERTICILLATUM (HALORAGACEAE) AGAINST SELECTED PHYTOPLANKTON SPECIES1

The potential allelopathic impact of Myriophyllum verticillatum L. under in situ conditions was determined in a series of field and laboratory experiments. Coexistence experiments were performed in a lake dominated by M. verticillatum (Van Goor) Meffert where we exposed three unialgal phytoplankton cultures in dialysis tubes to macrophyte exudates regularly during the vegetated period. Plant content and exudation of polyphenolic compounds were determined, and the inhibitory activity of polyphenol‐containing extracts was tested in bioassays with cyanobacteria. To account for possible resource interference, we monitored growth and photosynthesis of phosphorus‐limited and unlimited cyanobacterium Limnothrix redekei in dialysis tubes exposed to M. verticillatum in aquaria. A high allelopathic potential of M. verticillatum was concluded from high tissue concentrations of total phenolic compounds of 6%–12% of dry matter, the demonstrated release of bioactive polyphenols into the surrounding medium, and the inhibition of cyanobacteria by extracts. We could not unambiguously demonstrate the exudation of polyphenols by M. verticillatum in situ due to interference with allochthonous humic compounds. In laboratory experiments, L. redekei exhibited significantly reduced maximum relative electron transport rates when co‐cultivated in dialysis tubes with M. verticillatum. The field dialysis tube experiment confirmed this result, accompanied by a decline of chl a and PSII activity for L. redekei and the diatom Stephanodiscus minutulus (Kütz.) Greve et Möller, but not for the green alga Scenedesmus armatus Chodat in August. At other times, either no effects or stimulatory effects were observed with all species. Nutrient limitation of the target species may have masked allelopathic effects, and M. verticillatum may have enhanced phytoplankton growth due to phosphorus leakage.