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In this work, the synthesis and characterization of a heterogeneous photocatalyst based on spherical silica nanoparticles superficially modified with anthraquinone 2-carboxylic acid (AQ-COOH) are presented. The nanomaterial was characterized by TEM, SEM, FT-IR, diffuse reflectance, fluorescence, NMR, DLS, XRD and XPS. These analyses confirm the covalent linking of AQ-COOH with the NH2 functionality in the nanomaterial and, more importantly, the photocatalyst retains its photophysical properties once bound. The heterogeneous photocatalyst was successfully employed in the aerobic hydroxylation of arylboronic acids to phenols under sustainable reaction conditions. Phenols were obtained in high yields (up to 100 %) with low catalyst loading (3.5 mol %), reaching TOF values of 3.7 h-1 . Using 2-propanol as solvent at room temperature, the visible light photocatalysis produced H2 O2 as a key intermediate to promote the aerobic hydroxylation of arylboronic acids. The heterogeneous photocatalyst was reused at least 5 times, without modification of the nanomaterial structure and morphology. This simple heterogeneous system showed great catalytic activity under sustainable reaction conditions.

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Respiratory viruses represent a world public health problem, giving rise to annual seasonal epidemics and several pandemics caused by some of these viruses, including the COVID-19 pandemic caused by the novel SARS-CoV-2, which continues to date. Some antiviral drugs have been licensed for the treatment of influenza, but they cause side effects and lead to resistant viral strains. Likewise, aerosolized ribavirin is the only drug approved for the therapy of infections by the respiratory syncytial virus, but it possesses various limitations. On the other hand, no specific drugs are licensed to treat other viral respiratory diseases. In this sense, natural products and their derivatives have appeared as promising alternatives in searching for new compounds with antiviral activity. Besides their chemical properties, quinones have demonstrated interesting biological activities, including activity against respiratory viruses. This review summarizes the activity against respiratory viruses and their molecular targets by the different types of quinones (both natural and synthetic). Thus, the present work offers a general overview of the importance of quinones as an option for the future pharmacological treatment of viral respiratory infections, subject to additional studies that support their effectiveness and safety.

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Five ternary copper(II) complexes, [Cu2(phen)2(L1)(ClO4)2] (1), [Cu2(phen)2(L1)(DMSO)2](PF6)2 (2), [Cu2(bpy)2(L1)(ClO4)2(H2O)2] (3), [Cu2(dmp)2(L1)(ClO4)2(H2O)2] (4), and [Cu(phen)(L2)]2(ClO4)2 (5), in which phen = 1,10-phenanthroline, bpy = 2,2'-bipyridine, dmp = 2,9-dimethyl-1,10-phenanthroline, H2L1 = 1,4-dihydroxyanthracene-9,10-dione and HL2 = 1-hydroxyanthracene-9,10-dione, DMSO = dimethylsulfoxide, were synthesized and fully characterized. Complex 2 was obtained through the substitution of perchlorate for DMSO. When two hydroxyquinone groups are present, L1 makes a bridge between two Cu(II) ions, which also bind two nitrogens of the respective diimine ligand. The compounds bind to calf thymus DNA and oxidatively cleave pUC19 DNA according to the following order of activity 1 > 4-5 > 3. Furthermore, complexes 1, 3, 4 and 5 inhibit topoisomerase-I activity and the growth of myelogenous leukemia cells with the IC50 values of 1.13, 10.60, 0.078, and 1.84 µmol L-1, respectively. Complexes 1 and 4 are the most active in cancer cells and in DNA cleavage.

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Rubiadin is identified as a bioactive anthraquinone that exists in some quinone rich plants. The current research was carried out to evaluate the potential anti-inflammatory impact of Rubiadin in acute and chronic inflammation test models in rodents. The anti-inflammatory activity of Rubiadin was examined in cotton pellet-induced granuloma and carrageenan-induced edema as chronic and acute inflammation models in rats. TNF-α level and histopathological changes were assessed using sampled foot tissue of rat in the acute model. Also, the IL-1β level was assessed in the chronic model. One-way ANOVA (post hoc Tukeys) analysis was used for comparing the groups. Rubiadin (0.5 mg/kg, i.p.) induced a significant reduction in TNF α level and the paw edema compared to the control group in carrageenan test. Also, it was observed that the anti-inflammatory activity of Rubiadin (0.5 mg/kg, i.p.) is comparable to mefenamic acid (30 mg/kg, i.p.) as the standard drug. Rubiadin was effective in granuloma induced by cotton pellet concerning the granuloma and transudate formation amount. Rubiadin's anti-inflammatory effects were associated with a significant IL-1β decrease in this model. The results suggest that Rubiadin as a natural compound can possess significant peripheral anti-inflammatory impacts.(AU)

A rubiadina é identificada como uma antraquinona bioativa que existe em algumas plantas ricas em quinonas. A presente pesquisa foi realizada para avaliar o potencial impacto anti-inflamatório da rubiadina em modelos de teste de inflamação aguda e crônica em roedores. A atividade anti-inflamatória da rubiadina foi examinada em granuloma induzido por pellet de algodão e edema induzido por carragenina como modelos de inflamação crônica e aguda em ratos. O nível de TNF-α e as alterações histopatológicas foram avaliados usando amostra de tecido do pé de rato no modelo agudo. Além disso, o nível de IL-1β foi avaliado no modelo crônico. A análise ANOVA de uma via (post hoc de Tukey) foi usada para comparar os grupos. A rubiadina (0,5 mg / kg, i.p.) induziu uma redução significativa no nível de TNF α e no edema da pata em comparação com o grupo de controle no teste de carragenina. Além disso, foi observado que a atividade anti-inflamatória da rubiadina (0,5 mg / kg, i.p.) é comparável ao ácido mefenâmico (30 mg/kg, i.p.) como o fármaco padrão. A rubiadina foi eficaz no granuloma induzido por pellet de algodão no que diz respeito à quantidade de granuloma e formação de transudato. Os efeitos anti-inflamatórios da rubiadina foram associados a uma redução significativa de IL-1β nesse modelo. Os resultados sugerem que a rubiadina como um composto natural pode ter impactos anti-inflamatórios periféricos significativos.(AU)

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Increasing rates of bacterial resistance to antibiotics are a growing concern worldwide. The search for potential new antibiotics has included several natural products such as anthraquinones. However, comparatively less attention has been given to anthraquinones that exhibit functional groups that are uncommon in nature. In this work, 114 anthraquinones were evaluated using in silico methods to identify inhibitors of the enzyme phosphopantetheine adenylyltransferase (PPAT) of Staphylococcus aureus, Enterococcus faecalis, and Escherichia coli. Virtual screenings based on molecular docking and the pharmacophore model, molecular dynamics simulations, and free energy calculations pointed to 1,8-dihydroxy-4,5-dinitroanthraquinone (DHDNA) as the most promising inhibitor. In addition, these analyses highlighted the contribution of the nitro group to the affinity of this anthraquinone for the nucleotide-binding site of PPAT. Furthermore, DHDNA was active in vitro towards Gram-positive bacteria with minimum inhibitory concentration (MIC) values of 31.25 µg/mL for S. aureus and 62.5 µg/mL for E. faecalis against both antibiotic-resistant isolates and reference strains but was ineffective against E. coli. Experiments on kill-time kinetics indicated that, at the tested concentrations, DHDNA produced bacteriostatic effects on both Gram-positive bacteria. Overall, our results present DHDNA as a potential PPAT inhibitor, showing antibacterial activity against antibiotic-resistant isolates of S. aureus and E. faecalis, findings that point to nitro groups as key to explaining these results.

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Rubiadin is identified as a bioactive anthraquinone that exists in some quinone rich plants. The current research was carried out to evaluate the potential anti-inflammatory impact of Rubiadin in acute and chronic inflammation test models in rodents. The anti-inflammatory activity of Rubiadin was examined in cotton pellet-induced granuloma and carrageenan-induced edema as chronic and acute inflammation models in rats. TNF-α level and histopathological changes were assessed using sampled foot tissue of rat in the acute model. Also, the IL-1β level was assessed in the chronic model. One-way ANOVA (post hoc Tukey’s) analysis was used for comparing the groups. Rubiadin (0.5 mg/kg, i.p.) induced a significant reduction in TNF α level and the paw edema compared to the control group in carrageenan test. Also, it was observed that the anti-inflammatory activity of Rubiadin (0.5 mg/kg, i.p.) is comparable to mefenamic acid (30 mg/kg, i.p.) as the standard drug. Rubiadin was effective in granuloma induced by cotton pellet concerning the granuloma and transudate formation amount. Rubiadin's anti-inflammatory effects were associated with a significant IL-1β decrease in this model. The results suggest that Rubiadin as a natural compound can possess significant peripheral anti-inflammatory impacts.

A rubiadina é identificada como uma antraquinona bioativa que existe em algumas plantas ricas em quinonas. A presente pesquisa foi realizada para avaliar o potencial impacto anti-inflamatório da rubiadina em modelos de teste de inflamação aguda e crônica em roedores. A atividade anti-inflamatória da rubiadina foi examinada em granuloma induzido por pellet de algodão e edema induzido por carragenina como modelos de inflamação crônica e aguda em ratos. O nível de TNF-α e as alterações histopatológicas foram avaliados usando amostra de tecido do pé de rato no modelo agudo. Além disso, o nível de IL-1β foi avaliado no modelo crônico. A análise ANOVA de uma via (post hoc de Tukey) foi usada para comparar os grupos. A rubiadina (0,5 mg / kg, i.p.) induziu uma redução significativa no nível de TNF α e no edema da pata em comparação com o grupo de controle no teste de carragenina. Além disso, foi observado que a atividade anti-inflamatória da rubiadina (0,5 mg / kg, i.p.) é comparável ao ácido mefenâmico (30 mg/kg, i.p.) como o fármaco padrão. A rubiadina foi eficaz no granuloma induzido por pellet de algodão no que diz respeito à quantidade de granuloma e formação de transudato. Os efeitos anti-inflamatórios da rubiadina foram associados a uma redução significativa de IL-1β nesse modelo. Os resultados sugerem que a rubiadina como um composto natural pode ter impactos anti-inflamatórios periféricos significativos.

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Abstract: Rubiadin is identified as a bioactive anthraquinone that exists in some quinone rich plants. The current research was carried out to evaluate the potential anti-inflammatory impact of Rubiadin in acute and chronic inflammation test models in rodents. The anti-inflammatory activity of Rubiadin was examined in cotton pellet-induced granuloma and carrageenan-induced edema as chronic and acute inflammation models in rats. TNF- level and histopathological changes were assessed using sampled foot tissue of rat in the acute model. Also, the IL-1 level was assessed in the chronic model. One-way ANOVA (post hoc Tukeys) analysis was used for comparing the groups. Rubiadin (0.5 mg/kg, i.p.) induced a significant reduction in TNF level and the paw edema compared to the control group in carrageenan test. Also, it was observed that the anti-inflammatory activity of Rubiadin (0.5 mg/kg, i.p.) is comparable to mefenamic acid (30 mg/kg, i.p.) as the standard drug. Rubiadin was effective in granuloma induced by cotton pellet concerning the granuloma and transudate formation amount. Rubiadins anti-inflammatory effects were associated with a significant IL-1 decrease in this model. The results suggest that Rubiadin as a natural compound can possess significant peripheral anti-inflammatory impacts.

Resumo A rubiadina é identificada como uma antraquinona bioativa que existe em algumas plantas ricas em quinonas. A presente pesquisa foi realizada para avaliar o potencial impacto anti-inflamatório da rubiadina em modelos de teste de inflamação aguda e crônica em roedores. A atividade anti-inflamatória da rubiadina foi examinada em granuloma induzido por pellet de algodão e edema induzido por carragenina como modelos de inflamação crônica e aguda em ratos. O nível de TNF- e as alterações histopatológicas foram avaliados usando amostra de tecido do pé de rato no modelo agudo. Além disso, o nível de IL-1 foi avaliado no modelo crônico. A análise ANOVA de uma via (post hoc de Tukey) foi usada para comparar os grupos. A rubiadina (0,5 mg / kg, i.p.) induziu uma redução significativa no nível de TNF e no edema da pata em comparação com o grupo de controle no teste de carragenina. Além disso, foi observado que a atividade anti-inflamatória da rubiadina (0,5 mg / kg, i.p.) é comparável ao ácido mefenâmico (30 mg/kg, i.p.) como o fármaco padrão. A rubiadina foi eficaz no granuloma induzido por pellet de algodão no que diz respeito à quantidade de granuloma e formação de transudato. Os efeitos anti-inflamatórios da rubiadina foram associados a uma redução significativa de IL-1 nesse modelo. Os resultados sugerem que a rubiadina como um composto natural pode ter impactos anti-inflamatórios periféricos significativos.

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Background: The gastrointestinal parasite Giardia lamblia causes giardiasis. Its treatment with standard drugs produces side effects and improper treatment can generate resistant strains. New antigiardial compounds are needed. An analysis was done to identify the antigiardial activity of Morinda royoc, a plant used in traditional Mayan medicine to treat stomach and bowel pain. We aimed to assess the efficacy of M. royoc roots against G. lamblia and their effect on cells viability. Methods: A methanol extract was done of the root and then fractionated. The extract and fractions were tested in vitro on G. lamblia trophozoites and their effect on cell viability was quantified by flow cytometry. The active extract and fractions were analyzed by gas chromatography-mass spectrometry and high-performance liquid chromatography. Results: The hexane fraction exhibited potent activity against G. lamblia (IC50 = 0.08 µg/mL). Its principal component was an anthraquinone-type compound. None of the fractions were toxic to human promyelocytic leukemia, chronic myelogenous leukemia and human mononuclear cells. Conclusion: The medicinal plant M. royoc contains promising bioactive agents with antigiardial activity and deserves further research.

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Polycyclic aromatic hydrocarbons (PAHs) are ubiquitous in astrochemical environments and are disbursed into planetary environments via meteorites and extraterrestrial infall where they may interact with mineral phases to produce quinones important for origins of life. In this study, we assessed the potential of the phyllosilicates montmorillonite (MONT) and kaolinite (KAO), and the enhanced Mojave Mars Simulant (MMS) to convert the PAH anthracene (ANTH) to the biologically important 9,10-anthraquinone (ANTHQ). All studied mineral substrates mediate conversion over the temperature range assessed (25-500°C). Apparent rate curves for conversion were sigmoidal for MONT and KAO, but quadratic for MMS. Conversion efficiency maxima for ANTHQ were 3.06% ± 0.42%, 1.15% ± 0.13%, and 0.56% ± 0.039% for MONT, KAO, and MMS, respectively. We hypothesized that differential substrate binding and compound loss account for the apparent conversion kinetics observed. Apparent loss rate curves for ANTH and ANTHQ were exponential for all substrates, suggesting a pathway for wide distribution of both compounds in warmer prebiotic environments. These findings improve upon our previously reported ANTHQ conversion efficiency on MONT and provide support for a plausible scenario in which PAH-mineral interactions could have produced prebiotically relevant quinones in early Earth environments.

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Photodynamic therapy has been applied for the treatment of many diseases, especially skin diseases. However, poor aqueous solubility and toxicity of some photosensitizer drugs are the main disadvantages for their direct clinical applications. Thus, biotechnology and nanotechnology are important tools in the development of new ways of obtaining photoactive compounds that are biocompatible. We investigated the potential of a new nanostructured photosensitizer, an anthraquinone derivative produced by biotechnological process; then we associated nanotechnology to obtain a nanostructured anthraquinone active molecule. For this, it was prepared a classical nanocapsule formulations containing poly(lactide-co-glycolide) (PLGA) coating for encapsulation of anthraquinone derivative. These formulations were characterized by their physicochemical, morphological, photophysical properties, and stability. We performed in vitro biocompatibility and photodynamic activity assays of free and nanostructured anthraquinone. Nanocapsule formulations containing anthraquinone derivative showed a nanometric profile with particle size around 250 nm, negative zeta potential around -30 mV, and partially monodisperse. Besides that, characteristic spherical morphology of nanocapsules and homogeneous particle surface were observed by AFM analyses. The in vitro biocompatibility assay showed absence of cytotoxicity for all tested RD/NC concentrations and also for unloaded/NC in NIH3T3 cells. In vitro photoactivation assay using NIH3T3 cells showed that nanocapsules promoted greater drug uptake by NIH3T3 cells, around of 87%, of cell death compared to free drug showed around 48% of cell death. The anthraquinone derivative showed potential for use in PDT. Besides the association with nanocapsules improved cell uptake of photosensitizer resulting in increased cell death compared to free anthraquinone.

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Laccases produced by Leucoagaricus gongylophorus act in lignocellulose degradation and detoxification processes. Therefore, the use of L. gongylophorus laccase (Lac1Lg) was proposed in this work for degradation of anthracene and others polycyclic aromatic hydrocarbons without the use of mediators. Degradation reactions were performed in buffer aqueous solution with 10 ppm of anthracene and other PAHs, Tween-20 in 0.25% v/v and a laccase preparation of 50 U. The optimum condition (pH 6.0 and 30 °C) was determined by response surface methodology with an excellent coefficient of determination (R2) of 0.97 and an adjusted coefficient of determination (R2adj) of 0.93. In addition, the employment of the mediator ABTS decreased the anthracene biodegradation from 44 ± 1% to 30 ± 1%. This optimum pH of 6.0 suggests that the reaction occurs by a hydrogen atom transfer mechanism. Additionally, in 24 h Lac1Lg biodegraded 72 ± 1% anthracene, 40 ± 3% fluorene and 25 ± 3% phenanthrene. The yellow laccase from L. gongylophorus biodegraded anthracene and produced anthrone and anthraquinone, which are interesting compounds for industrial applications. Moreover, this enzyme also biodegraded the PAHs phenanthrene and fluorene justifying the study of Lac1Lg for bioremediation of these compounds in the environment.

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The metal-organic framework (MOF) HKUST-1 was employed as an interaction matrix for fundamental loading studies of anthraquinone dyes. Chosen dyes were alizarin (A), alizarin S (AS), disperse blue 1 (B1), disperse blue 3 (B3), disperse blue 56 (B56) and purpurin (P). All materials were characterized by XRD, FTIR, TGA and SEM. Hence the interaction of dyes with the framework was characterized by theoretical-experimental differential analysis. One-pot loading strategy resulted in more efficient scavenging of dyes, and reached 100 % for B56 using 50 mg L-1 . SEM revealed important microstructural changes, the smaller crystals ranged 0.8-3 µm in size and almost all composite sizes were from this to higher values, reaching 70 µm, with varying shapes. Two composites were larger in size range (about 2500-1000 µm), and were shaped as rods, octahedrons and coffin lids. Indeed, the microstructure could be modulated depending on preparation conditions and type of loaded dye. For the higher loading series, N2 adsorption and XPS experiments were carried on to further evidence dye-MOF interactions. Ab initio prediction of structural properties for A@HKUST-1 and P@HKUST-1 were obtained by means of solid-state CRYSTAL14 code at the PBE0 level of theory. Computed findings evidenced two O→Cu coordinative bonds, one from O-ketone and the other from O-phenolate moiety as main interactions towards CuNET centers.

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Aloe vera is a crop of wide economic value of worldwide distribution, and a rich source of quinone components. Recently, antiviral aloe anthraquinones had been reported against human influenza virus. In the present work two anthraquinones, aloesaponarin-I (1) and aloesaponarin-II (2) were isolated from A. vera roots, and six derivatives were obtained by methylation (3), acetylation (4) and O-glycosyl (5-6) reactions starting from (1). Additionally, a new Tetra-O-acetyl-ß-d-glucopyranosyl derivative from 2 was also prepared. All compounds were evaluated against two strains of influenza virus AH1N1 by cytopathic effect reduction assay (CPE). The antiviral activity was determined by the ability of compounds to inhibit virus replication on Madin Darby Canine Kidney cells (MDCK). New derivatives 3-(2´,3´,4´,6´-Tetra-O-acetyl-ß-d-glucopyranosyl-aloesaponarin-I (5) and 3-(2´,3´,4´,6´-Tetra-O-acetyl-ß-d-glucopyranosyl- aloesaponarin-II (7) showed a cytopathic reduction effect against influenza strain A/Yucatán/2370/09 with IC50 of 30.77 and 13.70 µM, and against the virus A/Mexico/InDRE797/10 with IC50 of 62.28 and 19.47 µM, respectively. To assess the effect of derivatives 5 and 7 during one cycle of replication (0-10 h), a time-of-addition experiment was performed. As a result it was found that both compounds were most effective when added 6-10 h post-infection and significantly inhibited viral titre (> 70%) at the concentrations of 50 and 100 µM. Based on the structural analysis of the compounds, it was suggested that the Tetra-O-acetyl-ß-d-glucopyranosyl substituent at the C3 position of the anthraquinone might have an effect against the influenza AH1N1 virus.

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Trichomoniasis, caused by the protozoan parasite Trichomonas vaginalis, is the most common nonviral sexually transmitted infection worldwide. Although drug treatment is available, unpleasant side effects and increased resistance to the nitroimidazole family have been documented. Hence, there is a need for the identification of new and safe therapeutic agents against T. vaginalis. Antimicrobial activity of anthraquinone compounds has been reported by a number of authors. The genus Morinda is well known for the diversity of anthraquinones with numerous biological activities. A new anthraquinone, lucidin-ω-isopropyl ether, was isolated from the roots of Morinda panamensis Seem. The structure of the compound was determined by 1 H and 13 C Nuclear Magnetic Resonance (NMR) analyses, in addition to comparison with literature reports. Using in vitro susceptibility assay, the half inhibitory concentration (IC50 ) of lucidin-ω-isopropyl ether for T. vaginalis (1.32 µg/mL) was found similar to that of metronidazole concentration tested (6 µM = 1.03 µg/mL). In addition, this anthraquinone was capable of inhibiting the parasite's ability to kill HeLa cells and decreased proteolytic activity of the proteinase TvMP50 from T. vaginalis. This was associated with the decreased expression of the mp50 gene. These results demonstrate the trichomonicidal potential by lucidin-ω-isopropyl ether. Further action-mode studies are necessary to elucidate the antiparasitic mechanism of this new anthraquinone to develop a more potent antitrichomonal agent.

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(1) Background: In this study, the effects of different pH values ​​(2.4, 3.2, 4.4 and 5.0), temperatures (30, 35, 40, 45 and 50°C) and agitation (100 rpm) on the enzymatic decolourisation of twenty-two dyes belonging to the chromophore groups anthraquinone, azo and triphenylmethane were assessed. (2) Methods: In all conditions, it was used a crude enzyme broth containing 30 U mL-1 laccases produced by Pleurotus sajor-caju PS-2001 in submerged process. (3) Results: Regarding the effects of pH values, the best results were obtained at pH 3.2 and 30°C, in which bleaching was observed for all dyes evaluated. In assays conducted at different temperatures, highest levels of decolourisation were observed at 35°C and pH 3.2 for nineteen of the dyes assessed. Thirteen dyes presented colour reduction exceeding 50% after the enzymatic treatment, including all acid and all disperse dyes evaluated. The reciprocal agitation of 100 rpm promoted negative effect on decolourisation. (4) Conclusion: From the results achieved, one can conclude that the laccase-containing preparation of P. sajor-caju PS-2001 has potential for the decolourisation of some dyes widely used in different industrial sectors, especially in the textile industry, and therefore could be used in future strategies for the biotreatment of coloured wastes.

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Various bird pests caused severe economic losses to valuable crops and fruit orchards all over the world. Among the birds, house sparrow is also considered to cause heavy plunder, not only to seeds of crops but also seedlings especially in organic farming. In present study two bird repellents, methylanthranilate and anthraquinone tested against house sparrows on maize seeds and seedlings in aviary conditions. Trial group in aviary-I, the treated maize seeds and seedlings with different doses of both bird repellents, control group in aviary-II, untreated seeds and seedlings were provided for three hours in the early morning. In each aviary, two closed circuit cameras were also installed to monitor the behavioral responses against different concentrations of both chemical repellents. Statistical analysis showed that there existed highly significant (P<0.01) variations among the trial and control groups for seeds and seedlings. By comparing both repellents, significant (P<0.05) differences were detected and anthraquinone showed better efficacy when compared to methylanthranilate, but in maize seedlings both repellents equal repellent properties. Non-significant (P>0.05) differences were observed in different grading of both natural chemical repellents for maize seeds while significant (P<0.05) variations were noticed for maize seedlings when provided to sparrows. By videotaped behavior sparrows presented manifest head juddering and feather upsetting activities by consumption of treated seeds and seedlings with higher concentrations of both natural bird repellents.(AU)

Várias pragas de aves causaram graves perdas econômicas para cultivos valiosos e pomares de frutas em todo o mundo. Entre os pássaros, o pardal da casa também é considerado um grande saqueo, não só para as sementes das culturas, mas também para as mudas, especialmente na agricultura orgânica. No presente estudo, dois repelentes de aves, metilantranilato e antraquinona testados contra pardais de casa em sementes de milho e mudas em condições de aviário. O grupo de ensaio em aviary-I, as sementes de milho tratadas e as mudas com diferentes doses de repelentes de aves, grupo de controle em aviary-II, sementes não tratadas e mudas foram fornecidas por três horas no início da manhã. Em cada aviário, duas câmeras de circuito fechado também foram instaladas para monitorar as respostas comportamentais contra diferentes concentrações de ambos os repelentes químicos. A análise estatística mostrou que existiam variações altamente significativas (P<0,01) entre os grupos de teste e controle para sementes e mudas. Ao comparar os dois repelentes, detectaram-se diferenças significativas (P<0,05) e a antraquinona apresentou maior eficácia quando comparada ao metilantranilato, mas em mudas de milho, ambos os repelentes são iguais às propriedades repelentes. As diferenças não significantes (P>0,05) foram observadas em diferentes classificações de repelentes químicos naturais para sementes de milho, enquanto as variações significativas (P<0,05) foram observadas para as mudas de milho quando fornecidas aos pardais. Por um comportamento gravado em video, os pardais apresentaram manifestações de cabeça e vibrações de penas por consumo de sementes tratadas e mudas com maiores concentrações de repelentes de aves naturais.(AU)

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Abstract Various bird pests caused severe economic losses to valuable crops and fruit orchards all over the world. Among the birds, house sparrow is also considered to cause heavy plunder, not only to seeds of crops but also seedlings especially in organic farming. In present study two bird repellents, methylanthranilate and anthraquinone tested against house sparrows on maize seeds and seedlings in aviary conditions. Trial group in aviary-I, the treated maize seeds and seedlings with different doses of both bird repellents, control group in aviary-II, untreated seeds and seedlings were provided for three hours in the early morning. In each aviary, two closed circuit cameras were also installed to monitor the behavioral responses against different concentrations of both chemical repellents. Statistical analysis showed that there existed highly significant (P<0.01) variations among the trial and control groups for seeds and seedlings. By comparing both repellents, significant (P<0.05) differences were detected and anthraquinone showed better efficacy when compared to methylanthranilate, but in maize seedlings both repellents equal repellent properties. Non-significant (P>0.05) differences were observed in different grading of both natural chemical repellents for maize seeds while significant (P<0.05) variations were noticed for maize seedlings when provided to sparrows. By videotaped behavior sparrows presented manifest head juddering and feather upsetting activities by consumption of treated seeds and seedlings with higher concentrations of both natural bird repellents.

Resumo Várias pragas de aves causaram graves perdas econômicas para cultivos valiosos e pomares de frutas em todo o mundo. Entre os pássaros, o pardal da casa também é considerado um grande saqueo, não só para as sementes das culturas, mas também para as mudas, especialmente na agricultura orgânica. No presente estudo, dois repelentes de aves, metilantranilato e antraquinona testados contra pardais de casa em sementes de milho e mudas em condições de aviário. O grupo de ensaio em aviary-I, as sementes de milho tratadas e as mudas com diferentes doses de repelentes de aves, grupo de controle em aviary-II, sementes não tratadas e mudas foram fornecidas por três horas no início da manhã. Em cada aviário, duas câmeras de circuito fechado também foram instaladas para monitorar as respostas comportamentais contra diferentes concentrações de ambos os repelentes químicos. A análise estatística mostrou que existiam variações altamente significativas (P<0,01) entre os grupos de teste e controle para sementes e mudas. Ao comparar os dois repelentes, detectaram-se diferenças significativas (P<0,05) e a antraquinona apresentou maior eficácia quando comparada ao metilantranilato, mas em mudas de milho, ambos os repelentes são iguais às propriedades repelentes. As diferenças não significantes (P>0,05) foram observadas em diferentes classificações de repelentes químicos naturais para sementes de milho, enquanto as variações significativas (P<0,05) foram observadas para as mudas de milho quando fornecidas aos pardais. Por um comportamento gravado em video, os pardais apresentaram manifestações de cabeça e vibrações de penas por consumo de sementes tratadas e mudas com maiores concentrações de repelentes de aves naturais.

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Dithianon is a broad-spectrum anthraquinone fungicide used to control several diseases of grapes, apples, and other fruits and vegetables. Its mode of action is described as multi-site and associated to thiol-reactivity. As other fungicides can affect non-phytopathogenic organisms as yeasts and bacteria, with impact on microbial population, diversity, and fermentation processes. In this context, we study the effect of dithianon on the model organism and fermentative yeast Saccharomyces cerevisiae in order to elucidate the mechanisms involved in yeast cell death., and explain its interference on wine fermentation kinetics. Thus for, we analyzed cellular protein and non-protein thiols, membrane and cell wall integrity, reactive oxygen species accumulation, mitochondrial membrane potential, and phosphatidylserine externalization. The results showed that when exponentially aerobic growing cells of S. cerevisiae are submitted to acute dithianon treatment they loss cell wall and membrane integrity, dying by necrosis, and this behavior is associated to a depletion of reduced proteic and non-proteic thiol groups. We also detected an important increase of cellular reactive oxygen species (ROS) associated to mitochondrial membrane potential modifications on dithianon treated cells. ROS accumulation was not associated to apoptotic cell death, but can be responsible for intracellular damages. Moreover, necrotic cell death induced by dithianon explains its effect on the kinetics of wine fermentations.

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Abstract Various bird pests caused severe economic losses to valuable crops and fruit orchards all over the world. Among the birds, house sparrow is also considered to cause heavy plunder, not only to seeds of crops but also seedlings especially in organic farming. In present study two bird repellents, methylanthranilate and anthraquinone tested against house sparrows on maize seeds and seedlings in aviary conditions. Trial group in aviary-I, the treated maize seeds and seedlings with different doses of both bird repellents, control group in aviary-II, untreated seeds and seedlings were provided for three hours in the early morning. In each aviary, two closed circuit cameras were also installed to monitor the behavioral responses against different concentrations of both chemical repellents. Statistical analysis showed that there existed highly significant (P 0.01) variations among the trial and control groups for seeds and seedlings. By comparing both repellents, significant (P 0.05) differences were detected and anthraquinone showed better efficacy when compared to methylanthranilate, but in maize seedlings both repellents equal repellent properties. Non-significant (P>0.05) differences were observed in different grading of both natural chemical repellents for maize seeds while significant (P 0.05) variations were noticed for maize seedlings when provided to sparrows. By videotaped behavior sparrows presented manifest head juddering and feather upsetting activities by consumption of treated seeds and seedlings with higher concentrations of both natural bird repellents.

Resumo Várias pragas de aves causaram graves perdas econômicas para cultivos valiosos e pomares de frutas em todo o mundo. Entre os pássaros, o pardal da casa também é considerado um grande saqueo, não só para as sementes das culturas, mas também para as mudas, especialmente na agricultura orgânica. No presente estudo, dois repelentes de aves, metilantranilato e antraquinona testados contra pardais de casa em sementes de milho e mudas em condições de aviário. O grupo de ensaio em aviary-I, as sementes de milho tratadas e as mudas com diferentes doses de repelentes de aves, grupo de controle em aviary-II, sementes não tratadas e mudas foram fornecidas por três horas no início da manhã. Em cada aviário, duas câmeras de circuito fechado também foram instaladas para monitorar as respostas comportamentais contra diferentes concentrações de ambos os repelentes químicos. A análise estatística mostrou que existiam variações altamente significativas (P 0,01) entre os grupos de teste e controle para sementes e mudas. Ao comparar os dois repelentes, detectaram-se diferenças significativas (P 0,05) e a antraquinona apresentou maior eficácia quando comparada ao metilantranilato, mas em mudas de milho, ambos os repelentes são iguais às propriedades repelentes. As diferenças não significantes (P>0,05) foram observadas em diferentes classificações de repelentes químicos naturais para sementes de milho, enquanto as variações significativas (P 0,05) foram observadas para as mudas de milho quando fornecidas aos pardais. Por um comportamento gravado em video, os pardais apresentaram manifestações de cabeça e vibrações de penas por consumo de sementes tratadas e mudas com maiores concentrações de repelentes de aves naturais.

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ABSTRACT The antimicrobial potential of extracts of bark and leaves of Cassia bakeriana Craib, Fabaceae, against aerobic and anaerobic oral bacteria was evaluated by the microdilution broth method. For crude ethanol extracts and organic fractions tested, the bark dichloromethane phase showed a significant antibacterial effect, with MIC values ranging from 12.5 to 100 µg/ml for most of the microorganisms tested. Thus, a bioassay-guided fractionation of this fraction was performed. This fractionation led to isolation of the 1,8-dihydroxy-anthraquinone-3-carboxylic acid, also known as cassic acid or rhein. It is the first time that this bioactive anthraquinone has been isolated from this plant. Rhein exhibited good selectivity and high activity against anaerobic microorganisms, with MIC values ranging between 3.12 µg/ml (11.0 µM) and 25 µg/ml (88.0 µM). These results were considered very promising since the most active samples and rhein showed greater selectivity against oral microorganisms than toxicity to Vero cells.