67 results on '"Brandão GC"'
Search Results
2. Hydromethanolic fraction from Abatia americana (Salicaceae) inhibits T24 bladder cancer cell line and the bacterium Listeria monocytogenes with high selectivity.
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Silveira BM, Amparo TR, Seibert JB, Almeida TC, Silva GND, Santos ODHD, Brandão GC, Vieira PMA, Teixeira LFM, and Souza GHB
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Abatia americana is a Brazilian species that has yet to be the subject of scientific investigation. However, it represents a potential source of new antibacterial and anticancer drugs, given it belongs to the Salicaceae family. The objective of this study was to investigate the potential biological activities and chemical composition of this species. The chemical characterisation was conducted using UPLC-QTOF-MS/MS. The cytotoxicity was evaluated using the sulforhodamine B method and the antibacterial activity was determined through a microdilution assay. Within the fractions obtained, namely hexane (HF), ethyl acetate (EF), butyl alcohol (BF), and hydromethanolic (HMF), 37 compounds were identified. The fractions showed better antibacterial activity against Staphylococcus aureus and Listeria monocytogenes . Those with greater polarity (HMF; BF) showed better results, with lower minimum bactericidal concentration (MBC) and higher selectivity index. They also demonstrated cytotoxic and antiproliferative action for T24 tumour lineage. Among the fractions, the most promising is the HMF fraction, which showed satisfactory selectivity and did not inhibit normal cell proliferation. This is also the first time that biological effects have been reported for this species. more...
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- 2024
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3. Antihypertensive effect of a nanoemulsion of baccharis dracunculifolia leaves extract in sodium-dependent hypertensive rats.
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Carlos Batista MA, Dias Araujo Freitas FE, de Assis Braga DC, de Souza JA, Antunes VR, de Souza GHB, Dos Santos ODH, Brandão GC, Kohlhoff M, Ceron CS, de Moura SAL, and Cardoso LM
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Baccharis dracunculifolia (DC) is an important botanical source of Brazilian green propolis and have many compounds with potential antihypertensive activity. However, little is known about the specific antihypertensive properties of DC, or the mechanisms involved. Here we aimed to chemically characterise an ethanolic DC extract (eDC), test its antihypertensive properties and the involvement of neurogenic mechanisms using an animal model of salt-dependent hypertension. The chemical analysis of the eDC revealed the presence of many antihypertensive compounds. Administering the eDC in a nanoemulsion formulation (25 to 50 mg/kg) effectively normalised blood pressure in hypertensive rats. The result also suggested that neurogenic mechanisms are involved in the antihypertensive action of eDC. The treatment with p -coumaric acid (0.32 to 3 mg/kg), a polyphenol abundant in the eDC, produced no significant antihypertensive effect. The findings indicate that the eDC has antihypertensive properties, and that these effects may be mediated through neurogenic pressor mechanisms. more...
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- 2024
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4. Protium spruceanum Extract Enhances Mupirocin Activity When Combined with Nanoemulsion-Based Hydrogel: A Multi-Target Strategy for Treating Skin and Soft Tissue Infections.
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Amparo TR, Sousa LRD, Xavier VF, Seibert JB, Paiva DL, da Silva DDS, Teixeira LFM, Dos Santos ODH, Vieira PMA, de Souza GHB, and Brandão GC
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The treatment of skin and soft tissue infections (SSTIs) can be challenging due to bacterial resistance, particularly from strains like MRSA and biofilm formation. However, combining conventional antibiotics with natural products shows promise in treating SSTIs. The objective of this study is to develop a nanoemulsion-based hydrogel containing Protium spruceanum extract and mupirocin and evaluate its potential for the treatment of SSTIs. The nanoemulsion was obtained by phase inversion and subsequently characterized. The antibacterial activity was evaluated in vitro against S. aureus MRSA, including the synergism of the combination, changes in membrane permeability using flow cytometry, and the anti-biofilm effect. In addition, the irritative potential was evaluated by the HET-CAM assay. The combination exhibited synergistic antibacterial activity against S. aureus and MRSA due to the extract enhancing membrane permeability. The hydrogel demonstrated suitable physicochemical properties, inhibited biofilm formation, and exhibited low irritation. The formulation was nanometric (176.0 ± 1.656 nm) and monodisperse (polydispersity index 0.286 ± 0.011). It exhibited a controlled release profile at 48 h and high encapsulation efficacy (94.29 ± 4.54% for quercitrin and 94.20 ± 5.44% for mupirocin). Therefore, these findings suggest that the hydrogel developed could be a safe and effective option for treating SSTIs., Competing Interests: The authors declare no conflicts of interest. more...
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- 2024
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5. Identification, characterization and quantification of xanthones from Fridericia formosa leaves extract with antiviral activity.
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Vaz LBA, Amparo TR, Reis ACC, de Mello Silva B, de Brito Magalhães CL, Kohlhoff M, and Brandão GC
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- Taiwan, Plant Extracts chemistry, Ethanol, Antiviral Agents pharmacology, Xanthones pharmacology, Xanthones chemistry, Bignoniaceae, Zika Virus, Zika Virus Infection
- Abstract
Fridericia formosa (Bureau) L.G. Lohmann (Bignonaceae) is a neotropical liana species found in the Cerrado biome in Brazil. It has been of great interest to the scientific community due to its potential as a source of new antivirals, including xanthones derived from mangiferin. In this context, the present study aimed to characterize and quantify the xanthones present in the ethanol extract of this species using high performance liquid chromatography. Additionally, the antiviral activity against Chikungunya, Zika, and Mayaro viruses was evaluated. The chromatographic analyses partially identified twenty-six xanthones, among which only fourteen had already been described in the literature. The xanthones mangiferin, 2'-O-trans-caffeoylmangiferin, and 2'-O-trans-coumaroylmangiferin, are present in higher quantities in the extract, at concentrations of 9.65%, 10.68%, and 3.41% w/w, respectively. In antiviral assays, the extract inhibited the multiplication cycle only for the Mayaro virus with a CE
50 of 36.1 μg/mL. Among the isolated xanthones, 2'-O-trans-coumaroylmangiferin and 2'-O-trans-cinnamoylmangiferin inhibited the viral cytopathic effect with CE50 values of 180.6 and 149.4 μg/mL, respectively. Therefore, the extract from F. formosa leaves, which has a high content of xanthones, has antiviral potential and can be a source of new mangiferin derivatives., (© 2024. The Author(s).) more...- Published
- 2024
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6. 8-Methoxy-α-lapachone and lawsone: antiproliferative effects on bladder tumour cells.
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Ferreira GM, Lima APB, Sousa JAC, Pereira GR, da Silva GN, and Brandão GC
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Quinones are chemical compounds produced from the oxidation of phenols. Among the quinones, naphthoquinones stand out as potential antitumor agents. Bladder tumour is the tenth most diagnosed in the world. Based on this, using a urothelial carcinoma cell line (T24), two naphthoquinones had their cytotoxicity tested by the MTT colorimetric method and were submitted to assays of clonogenic survival, morphology, cell cycle, cell migration and species reactive oxygen. The results showed 8-methoxy-α-lapachone and lausone presented selectivity indexes (19.5 and 28.0, respectively) for T24 cells. Moreover, the two naphthoquinones reduced the cell viability, interfered with the process of cell migration, changed the cell cycle kinectics and induced the production of species reactive oxygen (ROS). Additionaly, 8-methoxy-α-lapachone altered the morphology of the cells. In conclusion, the studied naphthoquinones showed potential antiproliferative effects in bladder cancer cells, interfering in cellular processes, possibly through oxidative stress. more...
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- 2023
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7. Discovery of a new dihydroeugenol-chalcone hybrid with cytotoxic and anti-migratory potential: A dual-action hit for cancer therapeutics.
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Nakao IA, Almeida TC, Cardoso Reis AC, Coutinho GG, Hermenegildo AM, Cordeiro CF, da Silva GN, Dias DF, Brandão GC, Pinto Braga SF, and de Souza TB
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- Eugenol pharmacology, Cell Line, Tumor, Doxorubicin pharmacology, Isoxazoles pharmacology, Cell Proliferation, Molecular Structure, Drug Screening Assays, Antitumor, Molecular Docking Simulation, Structure-Activity Relationship, Chalcone pharmacology, Chalcone chemistry, Chalcones pharmacology, Chalcones chemistry, Antineoplastic Agents chemistry, Neoplasms
- Abstract
Cancer still represents a serious public health problem and one of the main problems related to the worsening of this disease is the ability of some tumors to develop metastasis. In this work, we synthesized a new series of chalcones and isoxazoles derived from eugenol and analogues as molecular hybrids and these compounds were evaluated against different tumor cell lines. This structural pattern was designed considering the cytotoxic potential already known for eugenol, chalcones and isoxazoles. Notably, chalcones 7, 9, 10, and 11 displayed significant activity (4.2-14.5 µM) against two cancer cell lines, surpassing the potency of the control drug doxorubicin. The reaction of chalcones with hydroxylamine hydrochloride provided the corresponding isoxazoles that were inactive against these cancer cells. The dihydroeugenol chalcone 7 showed the most promising results, demonstrating higher potency against HepG2 (CC
50 : 4.2 µM) and TOV-21G (CC50 : 7.2 µM). Chalcone 7 was also three times less toxic than doxorubicin considering HepG2 cells, with a selectivity index greater than 11. Further investigations including clonogenic survival, cell cycle progression and cell migration assays confirmed the compelling antitumoral potential of chalcone 7, as it reduced long-term survival due to DNA fragmentation, inducing cell death and inhibiting HepG2 cells migration. Moreover, in silico studies involving docking and molecular dynamics revealed a consistent binding mode of chalcone 7 with metalloproteinases, particularly MMP-9, shedding light on its potential mechanism of action related to anti-migratory effects. These significant findings suggest the inclusion of compound 7 as a promising candidate for future studies in the field of cancer therapeutics., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2023 Elsevier Ltd. All rights reserved.) more...- Published
- 2023
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8. Antinociceptive effect of Nephelium lappaceum L. fruit peel and the participation of nitric oxide, opioid receptors, and ATP-sensitive potassium channels.
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Oliveira AS, Biano LS, Palmeira DN, de Almeida DR, Lopes-Ferreira M, Kohlhoff M, Sousa JAC, Brandão GC, Silva AMOE, Grespan R, and Camargo EA
- Abstract
Introduction: Nephelium lappaceum L. (Sapindaceae) is a plant known as rambutan. It is used for various purposes in traditional medicine. Objective: We aimed to evaluate the antinociceptive effects of the ethanol extract of the fruit peel of N. lappaceum (EENL), the mechanisms involved in these effects, and the acute toxicity in zebrafish. Methods: We performed chromatography coupled to mass spectrometry, acute toxicity assay in zebrafish, and evaluation in mice submitted to models of nociception and locomotor activity. Results: We identified (epi)-catechin, procyanidin B, and ellagic acid and its derivatives in EENL. We did not find any toxicity in zebrafish embryos incubated with EENL. The locomotor activity of mice submitted to oral pretreatment with EENL was not changed, but it reduced the abdominal constrictions induced by acetic acid, the licking/biting time in both the first and second phase of formalin testing and capsaicin testing, and carrageenan-induced paw mechanical allodynia. Oral pretreatment with EENL increased latency time in the hot plate test. This antinociceptive effect was significantly reversed by naloxone, L-arginine, and glibenclamide respectively showing the participation of opioid receptors, nitric oxide, and KATP channels as mediators of EENL-induced antinociception. Conclusion: EENL causes antinociception with the participation of opioid receptors, nitric oxide, and KATP channels, and is not toxic to zebrafish., Competing Interests: The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest., (Copyright © 2023 Oliveira, Biano, Palmeira, Almeida, Lopes-Ferreira, Kohlhoff, Sousa, Brandão, Silva, Grespan and Camargo.) more...
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- 2023
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9. Design and synthesis of new 1,2,3-triazoles derived from eugenol and analogues with in vitro and in vivo activity against Trypanosoma cruzi.
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Reis RCFM, Dos Santos EG, Benedetti MD, Reis ACC, Brandão GC, Silva GND, Diniz LA, Ferreira RS, Caldas IS, Braga SFP, and Souza TB
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- Mice, Rats, Animals, Eugenol pharmacology, Triazoles pharmacology, Triazoles therapeutic use, Parasitemia drug therapy, Trypanosoma cruzi, Trypanocidal Agents toxicity, Chagas Disease drug therapy
- Abstract
Chagas disease (CD) is a neglected tropical disease endemic in 21 countries and affects about 8 million people around the world. The pharmacotherapy for this disease is limited to two drugs (Benznidazole and Nifurtimox) and both are associated with important limitations, as low cure rate in the chronic phase of the disease, high toxicity and increasing resistance by Trypanosoma cruzi. Recently, we reported a bioactive 1,2,3-triazole (compound 35) active in vitro (IC
50 42.8 μM) and in vivo (100 mg/kg) against T. cruzi Y strains and preliminary in silico studies suggested the cysteine protease cruzain as a possible target. Considering these initial findings, we describe here the design and synthesis of new 1,2,3-triazoles derivatives of our hit compound (35). The triazoles were initially evaluated against healthy cells derived from neonatal rat cardiomyoblasts (H9c2 cells) to determine their cytotoxicity and against epimastigotes forms of T. cruzi Y strain. The most active triazoles were compounds 26 (IC50 19.7 μM) and 27 (IC50 7.3 μM), while benznidazole was active at 21.6 μM. Derivative 27 showed an interesting selectivity index considering healthy H9c2 cells (>77). Promising activities against trypomastigotes forms of the parasite were also observed for triazoles 26 (IC50 20.74 μM) and 27 (IC50 8.41 μM), mainly 27 which showed activity once again higher than that observed for benznidazole (IC50 12.72 μM). While docking results suggested cruzain as a potential target for these compounds, no significant enzyme inhibition was observed in vitro, indicating that their trypanocidal activity is related to another mode of action. Considering the promising in vitro results of triazoles 26 and 27, the in vivo toxicity was initially verified based on the evaluation of behavioral and physiological parameters, mortality, effect in body weight gain, and through the measurement of AST/ALT enzymes, which are markers of liver toxicity. All these evaluations pointed to a good tolerability of the animals, especially considering triazole 27. A reduction in parasitemia was observed among animals treated with triazole 27, but not among those treated with derivative 26. Regarding the dosage, derivative 27 (100 mg/kg) was the most active sample against T. cruzi infection, showing a 99.4% reduction in parasitemia peak. Triazole 27 at a dosage of 100 mg/kg influenced the humoral immune response and reduced myocarditis in the animals, bringing antibody levels closer to those observed among healthy mice. Altogether, our results indicate compound 27 as a new lead for the development of drug candidates to treat Chagas disease., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2023 Elsevier Masson SAS. All rights reserved.) more...- Published
- 2023
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10. Virucidal antiviral activity of Maytenus quadrangulata extract against Mayaro virus: Evidence for the presence of catechins.
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Nunes DAF, Lopes GFM, Nizer WSDC, Aguilar MG, Santos FRDS, Sousa GF, Ferraz AC, Duarte LP, Brandão GC, Vieira-Filho SA, Magalhães CLB, Ferreira JMS, and de Magalhães JC
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- Animals, Chlorocebus aethiops, Antiviral Agents pharmacology, Antiviral Agents chemistry, Vero Cells, Mammals, Catechin pharmacology, Maytenus, Alphavirus genetics
- Abstract
Ethnopharmacological Relevance: Mayaro virus (MAYV) is an arbovirus endemic to the Amazon region, which comprises the states of the North and Midwest region of Brazil and encompasses the largest tropical forest in the world, the Amazon Forest. The confirmation of its potential transmission by Aedes aegypti and recent cases in Brazil, mainly in large centers in the northern region, led to the classification of Mayaro fever as an emerging disease. Traditional medicine is commonly used to treat various diseases, mainly by local riverside populations. Some species of the genus Maytenus, which have similar morphologies, are popularly used to treat infections and inflammations. In this context, our research group has studied and confirmed the antiviral activity of several plant-derived compounds. However, several species of this same genus have not been studied and therefore deserve attention., Aim of the Study: This study aimed to demonstrate the effects of ethyl acetate extracts of leaves (LAE) and branches (TAE) of Maytenus quadrangulata against MAYV., Materials and Methods: Mammalian cells (Vero cells) were used to evaluate the cytotoxicity of the extracts. After cell infection by MAYV and the treatment with the extracts, we evaluated the selectivity index (SI), the virucidal effect, viral adsorption and internalization, and the effect on viral gene expression. The antiviral action was confirmed by quantifying the viral genome using RT-qPCR and by analyzing the effect on virus yield in infected cells. The treatment was performed based on the effective concentration protective for 50% of the infected cells (EC
50 )., Results: The leaves (LAE; EC50 12.0 μg/mL) and branches (TAE; EC50 101.0 μg/mL) extracts showed significative selectivity against the virus, with SI values of 79.21 and 9.91, respectively, which were considered safe. Phytochemical analysis revealed that the antiviral action was associated with the presence of catechins, mainly in LAE. This extract was chosen for the subsequent studies since it reduced the viral cytopathic effect and virus production, even at high viral loads [MOI (multiplicity of infection) 1 and 5]. The effects of LAE resulted in a marked reduction in viral gene expression. The viral title was drastically reduced when LAE was added to the virus before infection or during replication stages, reducing virus production up to 5-log units compared to infected and untreated cells., Conclusion: Through kinetic replication, MAYV was not detected in Vero cells treated with LAE throughout the viral cycle. The virucidal effect of LAE inactivates the viral particle and can intercept the virus at the end of the cycle when it gains the extracellular environment. Therefore, LAE is a promising source of antiviral agents., Competing Interests: Declaration of competing interest The authors declare no conflict of interest, financial or otherwise., (Copyright © 2023 Elsevier B.V. All rights reserved.) more...- Published
- 2023
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11. Synthesis, characterization and antiproliferative effects of naphtho [2,3- b ] thiophen-4,9-quinone on bladder tumor cells.
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Ferreira GM, Lima APB, Pereira GR, Silva GND, and Brandão GC
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- Humans, Urinary Bladder metabolism, Thiophenes, Reactive Oxygen Species metabolism, Cell Proliferation, Cell Line, Tumor, Apoptosis, Drug Screening Assays, Antitumor, Antineoplastic Agents chemistry, Urinary Bladder Neoplasms drug therapy, Naphthoquinones pharmacology, Naphthoquinones chemistry
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Naphthoquinones are natural plants products or synthesized compounds. They have α, β-cyclic aromatic dienones structure with a naphthalene skeleton. Little is known about naphthoquinone and nothing about naphtho [2,3-b] thiophen-4,9-quinone effects on bladder cancer. In this study, a naphthoquinone containing a hetero sulfur atom was synthesized using classical synthetic method. The molecular structure was elucidated by NMR techniques and the antitumor effects were evaluated on bladder tumor cell lines with different TP53 status using tripan blue and MTT cytotoxic method, quantification of reactive oxygen species (ROS), wound healing, cell morphology and cell cycle progression assays. The results showed selective cytotoxicity, colonies reduction, morphological change, inhibition of the cell migration process, induction of ROS production and cell cycle arrest. Naphtho [2,3- b ] thiophen-4,9-quinone presents antiproliferative activity regardless TP53 status and may be a promising agent in the treatment of bladder cancer, as they have an oxidizing effect and interfere with cell cycle. more...
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- 2023
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12. New flavone, and cytotoxicity activity of Rauia resinosa ethanolic extract and constituents.
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Sousa JAC, Reis ACC, Magalhães CLB, Silva BM, and Brandão GC
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- Humans, Tandem Mass Spectrometry, Plant Extracts chemistry, Plant Leaves chemistry, Flavones pharmacology, Flavones analysis, Rutaceae chemistry, Carcinoma
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The ethanolic extract from leaves of Rauia resinosa , Rutaceae, provided a new flavone, 5-hydroxy-5',6,7-trimethoxy-3',4'-methylenedioxyflavone (1) , in addition to four known compounds: 3',4',5,5',7-pentamethoxyflavone (2) , 5,7,8-trimethoxy-3'4'-methylenedioxyflavone (3) , 3',4',5,7,8-pentamethoxyflavone (4) and β-sitosterol (5) . The structures of all compounds were established on the basis of spectroscopic methods, mainly 1D and 2D NMR, UPLC-DAD-MS and UPLC-ESI-MS/MS, involving comparison with literature data. Cytotoxicity of leaves and stems extracts, their fractions and compounds ( 2) , (3) , (4) and (5) were evaluated against T24 (bladder carcinoma), TOV-21-G (ovarian adenocarcinoma) and HepG2 (liver carcinoma) cell lines. more...
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- 2023
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13. Evaluation of the antimicrobial activity of silver nanoparticles biosynthesized from the aqueous extract of Schinus terebinthifolius Raddi leaves.
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Ferreira MD, Neta LCS, Brandão GC, and Dos Santos WNL
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- Schinus, Silver pharmacology, Silver chemistry, Plant Extracts pharmacology, Plant Extracts chemistry, Anti-Bacterial Agents pharmacology, Candida albicans, Spectroscopy, Fourier Transform Infrared, Plant Leaves chemistry, Microbial Sensitivity Tests, X-Ray Diffraction, Metal Nanoparticles chemistry, Anti-Infective Agents pharmacology
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Silver nanoparticles (AgNPs) synthesized from green synthesis using medicinal plants are presented as an option for the development of new antimicrobial agents. In this context, this study aims to evaluate the antimicrobial activity of silver nanoparticles synthesized from the aqueous extract of Schinus terebinthifolius Raddi leaves, popularly known as "aroeira." A 2
3 factorial design was used to assess the statistical significance of the studied factors, and Box-Behnken design was used to define the optimal conditions for the green synthesis of AgNPs. The studied factors were significant for the synthesis of nanoparticles, and the optimal conditions were pH 9.5, reaction time of 180 min, and 10 g of S. terebinthifolius Raddi leaves. The samples were characterized using UV-Vis spectroscopy, Fourier transform infrared spectroscopy, X-ray diffraction, scanning electron microscopy, transmission electron microscopy, and dynamic light scattering. Antimicrobial activity was evaluated using the broth microdilution method and through the minimum microbicidal concentration. AgNPs showed greater antimicrobial efficacy compared to the extract, both for bacteria and fungi: bacteriostatic activity against all tested bacteria and bactericidal against Pseudomonas aeruginosa, besides fungistatic action against Candida albicans and Candida glabrata. Finally, the aqueous extract of "aroeira" leaves was effective in the synthesis of AgNPs, with greater antimicrobial potential than the extract., (© 2022 International Union of Biochemistry and Molecular Biology, Inc.) more...- Published
- 2023
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14. Anti-Zika Virus Activity and Isolation of Flavonoids from Ethanol Extracts of Curatella americana L. Leaves.
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Lima LD, Reis ACC, Sousa JAC, Valente GM, de Mello Silva B, Magalhães CLB, Kohlhoff M, Teixeira LFM, and Brandão GC
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- Humans, Flavonoids chemistry, Quercetin, Ethanol analysis, Plant Extracts chemistry, Plant Leaves chemistry, Dilleniaceae, Zika Virus, Zika Virus Infection drug therapy
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The ethnomedicinal plant Curatella americana L. (Dilleniaceae) is a common shrub in the Brazilian Cerrado, whose ethanolic extract showed significant in vitro anti-Zika virus activity by the MTT colorimetric method. Currently, there is no drug in clinical use specifically for the treatment of this virus; therefore, in this work, the antiviral and cytotoxic properties of the ethanolic extract, fractions, and compounds were evaluated. The ethanolic extract of the leaves showed no cytotoxicity for the human MRC-5 cell and was moderately cytotoxic for the Vero cell (CC
50 161.5 ± 2.01 µg/mL). This extract inhibited the Zika virus multiplication cycle with an EC50 of 85.2 ± 1.65 µg/mL. This extract was fractionated using the liquid-liquid partition technique, and the ethyl acetate fraction showed significant activity against the Zika virus with an EC50 of 40.7 ± 2.33 µg/mL. From the ethyl acetate fraction, the flavonoids quercetin-3- O -hexosylgallate ( 1 ), quercetin-3- O -glucoside ( 2 ), and quercetin ( 5 ) were isolated, and in addition to these compounds, a mixture of quercetin-3- O -rhamnoside ( 3 ) and quercetin-3- O -arabinoside ( 4 ) was also obtained. The isolated compounds quercetin and quercetin-3-O-hexosylgallate inhibited the viral cytopathic effect at an EC50 of 18.6 ± 2.8 and 152.8 ± 2.0, respectively. Additionally, analyses by liquid chromatography coupled to a mass spectrometer allowed the identification of another 24 minor phenolic constituents present in the ethanolic extract and in the ethyl acetate fraction of this species. more...- Published
- 2023
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15. Anti-arboviral activity and chemical characterization of hispidulin and ethanolic extracts from Millingtonia hortensis L.f. and Oroxylum indicum (L.) Kurz (Bignoniaceae).
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Cardoso Reis AC, Valente GM, Silva BM, de Brito Magalhães CL, Kohlhoff M, and Brandão GC
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- Plant Extracts pharmacology, Plant Extracts chemistry, Tandem Mass Spectrometry, Flavonoids chemistry, Ethanol, Bignoniaceae chemistry, Zika Virus, Zika Virus Infection
- Abstract
Millingtonia hortensis L.f. and Oroxylum indicum (L.) Kurz (Bignoniaceae) are native species from the Asian continent. They are popularly used in traditional medicine and their extracts are rich in flavonoids. In this work, ethanolic extracts of stems and leaves of these species were evaluated against the Chikungunya, Zika and Mayaro virus. The extracts were subjected to analysis by ultra-efficient liquid chromatography coupled to mass spectrometry. Additionally, M. hortensis leaves extract was fractionated, leading to the isolation of hispidulin. Anti-arboviral activity against the three viruses was detected for M. hortensis leaves extract with EC
50 ranging from 37.8 to 134.1 µg/mL and for O. indicum stems extract with EC50 ranging from 18.6 to 55.9 µg/mL. Hispidulin inhibited viral cytopathic effect of MAYV (EC50 value 32.2 µM) and CHIKV (EC50 value 78.8 µM). In LC-DAD-ESI-MS/MS analysis we characterized 25 flavonoids confirming once again the presence of these substances in extracts of these species. more...- Published
- 2023
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16. Withalutin, a new cytotoxic withanolide from Athenaea velutina (Sendtn.) D'Arcy.
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Almeida AA, Cota BB, Rodrigues LA, Dutra LL, Kohlhoff M, Bressan GC, Brandão GC, and Leite JPV
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- Lactones analysis, Plant Leaves chemistry, Withanolides chemistry, Solanaceae chemistry, Antineoplastic Agents analysis
- Abstract
Bioassay-guided fractionation of dichloromethane extract from Athenaea velutina leaves led to the isolation of three withanolides, all being reported for the first time in this species. They were identified as withacnistin ( 1 ), withacnistin acetate ( 2 ) and a new withanolide, designated as withalutin ( 3 ). The structures were established by spectral data analysis, including MS, 1D and 2D NMR. In addition, in silico ADMET studies were employed to understand the pharmacokinetic properties of these withanolides. The withanolides isolated from A. velutina reduced cancer cell viability with IC
50 values ranging from 1.52 to 5.39 µM. In silico prediction revealed that withanolides have good gastrointestinal absorption or oral bioavailability properties; and are not likely to be mutagenic or hepatotoxic. These findings revealed that A. velutina is an important source of cytotoxic withanolides. more...- Published
- 2022
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17. High-Resolution Mass Spectrometry Identification and Characterization of Flavonoids from Fridericia chica Leaves Extract with Anti-Arbovirus Activity.
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da Cruz AFG, Reis ACC, Sousa JAC, Vaz LBA, de Mello Silva B, de Brito Magalhães CL, Kohlhoff M, de Oliveira AB, and Brandão GC
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- Anthocyanins analysis, Antiviral Agents analysis, Antiviral Agents pharmacology, Flavonoids analysis, Flavonoids pharmacology, Mass Spectrometry, Plant Extracts chemistry, Plant Leaves chemistry, Bignoniaceae chemistry, Flavones analysis, Flavones pharmacology, Zika Virus, Zika Virus Infection
- Abstract
Plant extracts are complex mixtures that are difficult to characterize, and mass spectrometry is one of the main techniques currently used in dereplication processes. Fridericia chica is a species with medicinal uses in Latin American countries, used in the treatment of inflammatory and infectious diseases. Extracts of this plant species are characterized by the presence of anthocyanidins. In this study, using high-resolution mass spectrometry coupled with liquid chromatography, it was possible to determine the molecular formula of thirty-nine flavonoids. Fragmentation analysis, ultraviolet spectrum and nuclear magnetic resonance data allowed the partial characterization of the structures of these compounds. The spectral dataset allowed the identification of a series of flavones in addition to the desoxyanthocyanidins common in extracts of the species. The occurrence of some of the proposed structures is uncommon in extracts of species of the Bignoniaceae family, and they are reported for the first time in the extract of this species. Quantitative analyses of total flavonoids confirmed the high content of these constituents in the species, with 4.09 ± 0.34 mg/g of dry plant material. The extract under study showed low in vitro cytotoxicity with CC
50 ≥ 296.7 ± 1.4 µg/mL for Vero, LLC-MK2 and MRC-5 cell lines. In antiviral activity assays, inhibition of the cytopathic effects of Dengue, Zika and Mayaro viruses was observed, with EC50 values ranging between 30.1 and 40.9 µg/mL. The best result was observed against the Mayaro virus, with an EC50 of 30.1 µg/mL. more...- Published
- 2022
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18. Activity of alkaloids from Aspidosperma nitidum against Leishmania (Leishmania) amazonensis.
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do Socorro Silva da Veiga A, Silveira FT, da Silva EO, Júnior JAPD, Araújo SC, Campos MB, do Rosário Marinho AM, Brandão GC, Vale VV, Percário S, and Dolabela MF
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- Indole Alkaloids, Plant Extracts chemistry, Alkaloids pharmacology, Antiprotozoal Agents chemistry, Aspidosperma chemistry, Leishmania
- Abstract
This study evaluated the morphological changes caused by fractions and subfractions, obtained from barks of Aspidosperna nitidum, against L. (L.) amazonensis promastigotes. The ethanolic extract (EE) obtained through the maceration of trunk barks was subjected to an acid-base partition, resulting the neutral (FN) and the alkaloid (FA) fractions, and fractionation under reflux, yielded hexane (FrHEX), dichloromethane (FrDCL), ethyl acetate (FrACoET), and methanol (FrMEOH) fractions. The FA was fractionated and three subfractions (SF5-6, SF8, and SF9) were obtained and analyzed by HPLC-DAD and
1 H NMR. The antipromastigote activity of all samples was evaluated by MTT, after that, scanning electron microscopy (SEM) and transmission electron microscopy (TEM) for the active fractions were performed. Chromatographic analyzes suggest the presence of alkaloids in EE, FN, FA, and FrDCL. The fractionation of FA led to the isolation of the indole alkaloid dihydrocorynantheol (SF8 fractions). The SF5-6, dihydrocorynantheol and SF-9 samples were active against promastigotes, while FrDCL was moderately active. The SEM analysis revealed cell rounding and changes in the flagellum of the parasites. In the TEM analysis, the treated promastigotes showed changes in flagellar pocket and kinetoplast, and presence of lipid inclusions. These results suggest that alkaloids isolated from A. nitidum are promising as leishmanicidal., (© 2022. The Author(s).) more...- Published
- 2022
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19. Cytotoxic activity of butanolic extract from Sambucus nigra L. flowers in natura and vehiculated in micelles in bladder cancer cells and fibroblasts.
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Pereira DI, Amparo TR, Almeida TC, Costa FSF, Brandão GC, Santos ODHD, da Silva GN, and Bianco de Souza GH
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- Fibroblasts, Flowers, Humans, Micelles, Plant Extracts pharmacology, Tandem Mass Spectrometry, Urinary Bladder, Sambucus nigra, Urinary Bladder Neoplasms drug therapy
- Abstract
Bladder cancer has a high incidence and recurrence rate among patients worldwide. This study aimed to evaluate the cytotoxic activity of fractions of Sambucus nigra L. flower extracts on bladder carcinoma cells (T24 cells) and human fibroblast cells (MRC-5). The butanolic fraction (F-BuOH) was characterized by UPLC-DAD-MS/MS and nine flavonoids were identified. Rutin was the major compound. The cytotoxic activity of this fraction was observed in the T24 cells but not in MRC-5 cells, indicating selectivity. F-BuOH was incorporated in micellar solutions of Pluronic® F127 and cytotoxic effect for T24 cells was observed again. In vitro assay demonstrated a controlled release of the fraction from the micelles. The results obtained showed that flavonoids are the possible responsible for cytotoxic activity in bladder carcinoma cells. In addition, micellar solutions act together to increase the action of the butanolic fraction. more...
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- 2022
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20. Characterization of the chemical composition (mineral, lead and centesimal) in pine nut (Araucaria angustifolia (Bertol.) Kuntze) using exploratory data analysis.
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Silva EFR, da Silva Santos BR, Minho LAC, Brandão GC, de Jesus Silva M, Silva MVL, Dos Santos WNL, and Dos Santos AMP
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- Data Analysis, Minerals, Seeds, Araucaria, Nuts
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In this study, mineral composition, centesimal composition and lead were evaluated in pine nut seeds (raw and cooked) from five Brazilian states. Mineral composition was determined by ICP OES and lead by GF AAS. The results for minerals were evaluated by Boxplot, PCA and HCA, using the R software. Average minerals in raw and cooked samples (mg 100 g
-1 ) were: 15.2 and 10.8 (Ca), 0.168 and 0.113 (Cu), 0.506 and 0.330 (Fe), 536 and 420 (K), 51.3 and 40.6 (Mg), 0.373 and 0.208 (Mn), 132 and 102 (P) and 0.746 and 0.520 (Zn). The average centesimal composition (raw and cooked) was: 53.5 and 47.2% (moisture), 1.76 and 1.26% (ash), 3.90 and 3.53% (protein), 40.8 and 48.0% (carbohydrate) and 179 and 206 kcal/100 g (total caloric value) and Pb was not detected. The chemometric analysis showed a distinction of raw and cooked samples due to significant nutrient losses after thermal processing., (Copyright © 2021. Published by Elsevier Ltd.) more...- Published
- 2022
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21. Antibacterial screening of plants from the Brazilian Atlantic Forest led to the identification of active compounds in Miconia latecrenata (DC.) Naudin.
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Rodrigues LA, Almeida ADC, Gontijo DC, Salustiano IV, Almeida AA, Brandão GC, Ribon AOB, and Leite JPV
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- Anti-Bacterial Agents pharmacology, Forests, Microbial Sensitivity Tests, Plant Extracts pharmacology, Staphylococcus aureus, Tandem Mass Spectrometry, Melastomataceae
- Abstract
Antibiotic resistance is a serious global threat to public health. This has promoted the research for new drug targets, and the use of other approaches, such as antimicrobial combined therapy. The present study evaluated the antibacterial activity of 88 extracts from Brazilian Atlantic Forest trees. The organic extract from leaves of Miconia latecrenata (E Ml ) was the most promising for inhibiting the growth of Staphylococcus aureus (0.3 mg/mL) and Pseudomonas aeruginosa (2.5 mg/mL). After the bioguided fractionation of E Ml and metabolite profiling performed by UPLC-DAD-MS/MS, the ethyl acetate (AF Ml ) and aqueous (WF Ml ) fractions showed a mixture of phenolic compounds derived from ellagic acid and quercetin. The MIC value of AF Ml was two-times lower than E Ml for P. aeruginosa , suggesting that these phenolic compounds can perform bioactivity. Furthermore, E MI and AF Ml showed synergism with ampicillin and tetracycline for S. aureus and P. aeruginosa , respectively. These findings suggest that extract and fractions of the Miconia latecrenata leaves can be used as therapeutic antibacterial agents. more...
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- 2021
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22. In silico pharmacological prediction and cytotoxicity of flavonoids glycosides identified by UPLC-DAD-ESI-MS/MS in extracts of Humulus lupulus leaves cultivated in Brazil.
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da Silva RG, Almeida TC, Reis ACC, Filho SAV, Brandão GC, da Silva GN, de Sousa HC, de Almeida VL, Lopes JCD, and de Souza GHB
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- Brazil, Chromatography, High Pressure Liquid, Flavonoids analysis, Glycosides, Plant Extracts pharmacology, Plant Leaves chemistry, Tandem Mass Spectrometry, Humulus
- Abstract
Ethanolic (EB) extract and hexanic (SH) and hydromethanolic (SEM) sub-extracts of Humulus lupulus leaves were submitted to cytotoxicity evaluation and to phytochemical methods. The effect of EB and SEM on cellular cycle was evaluated by propidium iodide method and the phases were quantified through flow cytometry. The cytotoxicity assessment was done using T24 and MRC5 cells, with EB and SEM (25-1200 µg/mL). By means of UPLC-DAD-MS/MS data were identified the flavonoids astragaline, nicotiflorin, kaempferol-7- O -rutinoside, robinin, hyperin, rutin, quercetin-7- O -rutinoside and manghaslin. EB (800 µg/mL) and SEM (1200 µg/mL) reduces the T24 cell viability. These extracts at 25 µg/mL stimulate the growth of MRC5 cells, evidencing a selective cytotoxicity. After 24 h of the treatment with extracts was not observed cycle arrest of T24 cells. The bioactivity prediction of the flavonoids was evaluated in silico through in house Active-IT software and PASSonline which indicated potential activity as antitumoral, cytotoxic, anti-inflammatory, antiparasitic, antimicrobial, antiviral and others. more...
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- 2021
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23. Novel lignan-based compounds via click chemistry: paulownin isolation, structural modifications and cytotoxic activity evaluations.
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Pereira GR, Ferreira ACG, Costa F, Munhoz V, Alvarenga D, Silva BM, Reis ACC, and Brandão GC
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- Alkynes, Bridged-Ring Compounds, Catalysis, Copper, Cycloaddition Reaction, Lignans, Podophyllotoxin, Azides, Click Chemistry
- Abstract
Paulownin, a natural compound obtained from the tree Tecoma stans var. stans , was chemically modified by alkylation of its hydroxyl position. Thirteen novel lignans derivatives synthesized via a copper-catalyzed cycloaddition (CuAAC), known as click reaction, using different organic azides and lignan terminal alkyne. Characterization by mass spectrometry, NMR (
1 H and13 C) and infrared spectroscopy. These novel molecules were submitted to biological tests, using the MTT colorimetric technique aiming at the verification of their antitumor properties with six different cells lines. Biological evaluation was satisfactory and one of compounds showed selectivity index ten times higher than podophyllotoxin. more...- Published
- 2021
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24. Glucosyl-1,2,3-triazoles derived from eugenol and analogues: Synthesis, anti-Candida activity, and molecular modeling studies in CYP-51.
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Magalhães LS, Reis ACC, Nakao IA, Péret VAC, Reis RCFM, Silva NC, Dias ALT, Carvalho DT, Dias DF, Brandão GC, Braga SFP, and Souza TB
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- Antifungal Agents pharmacology, Apoptosis drug effects, Candida drug effects, Cell Survival drug effects, Drug Evaluation, Preclinical, Fibroblasts cytology, Humans, Molecular Docking Simulation, Molecular Dynamics Simulation, Structure-Activity Relationship, Triazoles pharmacology, Antifungal Agents chemical synthesis, Eugenol chemistry, Triazoles chemical synthesis
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This work describes the synthesis, anti-Candida, and molecular modeling studies of eighteen new glucosyl-1,2,3-triazoles derived from eugenol and correlated phenols. The new compounds were characterized by combined Fourier Transform Infrared,
1 H and13 C nuclear magnetic resonance and spectroscopy of high-resolution mass spectrometry. The synthesized compounds did not show significant cytotoxicity against healthy fibroblast human cells (MCR-5) providing interesting selectivity indexes (SI) to active compounds. Considering the antifungal activity, nine compounds showed anti-Candida potential and the peracetylated triazoles 17 and 18 were the most promising ones. Eugenol derivative 17 was active against three species of Candida at 26.1-52.1 μM. This compound was four times more potent than fluconazole against Candida krusei and less toxic (SI > 6.6) against the MCR-5 cells than fluconazole (SI > 3.3) considering this strain. Dihydroeugenol derivative 18 showed similar activity to 17 and was four times more potent and less toxic than fluconazole against C. krusei. The deacetylated glucosides and non-glucosylated corresponding derivatives did not show considerable antifungal action, suggesting that the acetyl groups are essential for their anti-Candida activity. Molecular docking coupled with molecular dynamics showed that 14α-lanosterol demethylase is a feasible molecular target, since 17 and 18 could bind to this enzyme once deacetylated in vivo, thereby acting as prodrugs. Also, these studies demonstrated the importance of hydrophobic substituents at the phenyl ring., (© 2021 John Wiley & Sons Ltd.) more...- Published
- 2021
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25. In vitro antiplasmodial activity, targeted LC-MS metabolite profiling, and identification of major natural products in the bioactive extracts of Palicourea and Psychotria species from the Amazonia and Atlantic Forest biomes, Brazil.
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Gontijo DC, do Nascimento MFA, Rody HVS, Magalhães RA, Margalho LF, Brandão GC, and de Oliveira AB
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- Brazil, Chromatography, Liquid, Ecosystem, Ethanol, Forests, Plant Extracts pharmacology, Plant Leaves, Tandem Mass Spectrometry, Alkaloids pharmacology, Antimalarials pharmacology, Biological Products, Psychotria, Rubiaceae
- Abstract
Introduction: A great variety of bioactive natural products has been reported for different Palicourea and Psychotria species (Rubiaceae). However, few of them as well as few of species of these botanical genera have been evaluated for antiplasmodial activity., Objective: To assess the antiplasmodial activity of 24 extracts from Palicourea and Psychotria genera, along with the targeted LC-MS metabolite profiling, as well as identification of the main metabolites in the bioactive extracts., Methods: Twenty four ethanol and acid-base extracts from Palicourea and Psychotria genera collected in the Amazonia and Atlantic Forest, Brazil, were evaluated against chloroquine-resistant Plasmodium falciparum W2 strain by PfLDH. The metabolite profiling and putative identification of metabolites from bioactive extracts were determined by LC-DAD-ESI-MS and LC-HRMS, respectively., Results: The ethanol extracts disclosed low antiplasmodial activity (% GI < 50%). High antiplasmodial effect was observed for the acid-base extracts from Psychotria apoda and Psychotria colorata with 100% inhibition of parasite growth inhibition. Fragment ions related to pyrrolidinoindoline alkaloids were observed by LC-DAD-ESI-MS mainly in the most bioactive extracts. The results of the in vitro screening associated with the LC-DAD-ESI-MS and LC-HRMS
n data allowed to predict, for the first time, the pyrrolidinoindoline alkaloids as possible antiplasmodial representing, then, new potential natural antimalarial hits. In addition, other metabolite classes such as flavanones, lignans and chalcones were also putatively identified in the bioactive extracts of Psychotria apoda, Psychotria capitata, and Psychotria poeppigiana., Conclusion: The present results point to Palicourea and Psychotria species as sources of new antimalarial hits., (© 2021. The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature.) more...- Published
- 2021
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26. Himatanthus bracteatus stem extracts present anti-flavivirus activity while an isolated sesquiterpene glucoside present only anti-Zika virus activity in vitro .
- Author
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da Silva ML, Stehmann JR, Serafim MSM, Vale VV, Gontijo DC, Brandão GC, Kroon EG, and de Oliveira AB
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- Animals, Antiviral Agents isolation & purification, Chlorocebus aethiops, Glucosides isolation & purification, Phytochemicals isolation & purification, Phytochemicals pharmacology, Plant Extracts pharmacology, Plant Stems chemistry, Vero Cells, Antiviral Agents pharmacology, Apocynaceae chemistry, Glucosides pharmacology, Sesquiterpenes isolation & purification, Sesquiterpenes pharmacology, Zika Virus drug effects
- Abstract
The hexane and ethanol extracts from Himatanthus bracteatus (Apocynaceae) stems were evaluated for antiviral activity against Zika virus, yellow fever virus and dengue virus 2 and for cytotoxicity in Vero cells by MTT assay. The ethanol extract showed good antiviral activity against the three viruses with selective indexes (SI) > 10 and its fractionation led to the isolation of the known plumieride that was active only against Zika virus (SI of 15.97). more...
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- 2021
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27. Bioprospection for antiplasmodial activity, and identification of bioactive metabolites of native plants species from the Mata Atlântica biome, Brazil.
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Gontijo DC, Leite JPV, Nascimento MFAD, Brandão GC, and Oliveira AB
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- Animals, Brazil, Chemical Fractionation, Chromatography, Liquid, Flavonoids analysis, Humans, Plant Extracts chemistry, Plant Leaves chemistry, Plants drug effects, Tandem Mass Spectrometry, Tannins analysis, Antimalarials pharmacology, Bioprospecting, Ecosystem, Metabolome, Plants chemistry, Plasmodium falciparum drug effects
- Abstract
A total of 33 extracts of eleven different plants species from Mata Atlântica biome, Brazil, and different fractions of the bioactive extracts were evaluated against chloroquine-resistant Plasmodium falciparum W2 strain by Pf LDH method and cytotoxicity to HepG2 cells by the MTT assay, and chemically characterized by LC-DAD-ESI-MS/MS analysis. The results allowed the identification of Alchornea glandulosa, Miconia latecrenata, and Psychotria suterella as the most active plant species. Different flavonoids and tannins in Alchornea glandulosa and Miconia latecrenata besides alkaloids in Psychotria suterella were identified. Bioguided fractionation of A. glandulosa and M. latecrenata leaves extracts led to fractions exhibiting high parasite growth inhibition. Seven known alkaloids were identified in the P. suterella extract, and of these, only 5-carboxystrictosidine had been assayed for antiplasmodial activity what points to this species as the most promising among the eleven one assayed. more...
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- 2021
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28. Phytochemistry and antiplasmodial activity of Xylopia sericea leaves.
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Gontijo DC, Nascimento MFAD, Brandão GC, and Oliveira AB
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- Animals, Antimalarials chemistry, Antimalarials toxicity, Aporphines chemistry, Aporphines pharmacology, Chloroquine pharmacology, Chromatography, Gas, Chromatography, Liquid, Drug Evaluation, Preclinical, Drug Resistance, Microbial, Furans pharmacology, Hep G2 Cells, Humans, Lactones pharmacology, Oils, Volatile chemistry, Plant Extracts chemistry, Plant Extracts pharmacology, Plant Leaves chemistry, Antimalarials pharmacology, Plasmodium falciparum drug effects, Xylopia chemistry
- Abstract
Aiming to investigate the antiplasmodial activity and the phytochemical composition of Xylopia sericea leaves, the essential oil and dichloromethane extract were analyzed by gas and liquid chromatography, respectively, both of them coupled to mass spectrometry, and were evaluated against the chloroquine-resistant Plasmodium falciparum strain (W2) and for cytotoxicity to HepG2 cells. Low growth inhibition of P. falciparum as well as low cytotoxicity to HepG2 cells were observed for the essential oil. The leaves dichloromethane extract showed moderate growth inhibition of P. falciparum and low cytotoxicity to HepG2 cells. Bioguided chromatographic fractionation of this extract led to fractions with increased antiplasmodial activity from which liriodenine (IC
50 6.1 ± 0.1 μg/mL, CC50 > 1000.0 μg/mL, SI > 164), an aporphine alkaloid, and an acetogenin-rich fraction containing mainly isomers of annomontacin and 4-deoxy-annomontacin (IC50 22.7 ± 1.9 µg/mL, CC50 336.1 ± 15.5 µg/mL, SI = 15) might be highlighted for their antiplasmodial activity. more...- Published
- 2020
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29. Cytotoxic, Antitumor and Toxicological Profile of Passiflora alata Leaf Extract.
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Amaral RG, Gomes SVF, Andrade LN, Dos Santos SA, Severino P, de Albuquerque Júnior RLC, Souto EB, Brandão GC, Santos SL, David JM, and Carvalho AA
- Subjects
- Animals, Antineoplastic Agents chemistry, Antineoplastic Agents pharmacology, Brazil, Cell Line, Tumor, Cell Proliferation drug effects, Flavonoids chemistry, Heterografts, Humans, Mice, Neoplasms pathology, Peru, Plant Extracts chemistry, Plant Leaves chemistry, Flavonoids pharmacology, Neoplasms drug therapy, Passiflora chemistry, Plant Extracts pharmacology
- Abstract
Passiflora alata or passion fruit is a native flowering plant from Amazon, geographically spread from Peru to Brazil. The plant has long been used in folks medicine for its pharmacological properties and is included in the Brazilian Pharmacopoeia since 1929. The aim of this study was to evaluate the potential cytotoxic and antitumor activities of Passiflora alata leaf extract (P a LE) in S180-tumor bearing mice. The percentage of cell proliferation inhibition (% CPI) and IC
50 in relation to 4 tumor cell lines were determined in PC3, K-562, HepG2 and S180 cell lines using the MTT assay. P a LE showed a CPI > 75% and greater potency (IC50 < 30 µg/mL) against PC3 and S180 cell lines. Pa LE showed antitumor activity in treatments intraperitoneally (36.75% and 44.99% at doses of 100 and 150 mg/kg/day, respectively). Toxicological changes were shown in the reduced body mass associated with reduced food consumption, increased spleen mass associated with histopathological increase in the white pulp of the spleen and increased number of total leukocytes with changes in the percentage relationship between lymphocytes and neutrophils. Our outcomes corroborate the conclusion that Pa LE has antitumor activity in vitro and in vivo with low toxicity. more...- Published
- 2020
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30. Multi-element composition, physicochemical and pollen attributes of honeys from the Paraguaçu River (Bahia, Brazil) by inductively coupled plasma-optical emission spectrometry (ICP OES).
- Author
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Santos JÚnior AF, BrandÃo GC, Santos JÚnior MC, Santos FARD, MagalhÃes HIF, and Korn MGA
- Subjects
- Brazil, Pollen chemistry, Rivers, Spectrum Analysis, Honey analysis, Trace Elements analysis
- Abstract
Honey is a food of nutritional, medicinal and commercial importance. The physicochemical characteristics, pollen spectrum and mineral composition of eighteen honey samples obtained from regions (Cachoeira, Coqueiros, Maragojipe and Santiago do Iguape) near the Paraguaçu River, Bahia, Brazil were evaluated. Botanical families Asteraceae, Leguminosae, Malvaceae, Myrtaceae and Palmae were most frequently found. Five samples had water contents above the maximum limit established by the Brazilian legislation (> 20%). The mineral composition was determined by ICP OES, after microwave digestion. Ca, K, Mg and Na were measured (mg Kg-1) in the range from: 18.85 to 79.61; 366.74 to 1214.98; 12.46 to 44.59 and 11.56 to 85.39, respectively. Cu, Fe, Mn and Zn had variable concentration ranges, between 0.05 and 6.13 mg Kg-1. Al, Ba, Cd, Co, Cr, Ni, Pb, Se and V showed values below the LOD. Principal component analysis (PCA) and hierarchical cluster analysis (HCA) demonstrated that there are no similarities of mineral composition among honey samples. more...
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- 2020
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31. Ethnopharmacology of Fruit Plants: A Literature Review on the Toxicological, Phytochemical, Cultural Aspects, and a Mechanistic Approach to the Pharmacological Effects of Four Widely Used Species.
- Author
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de Carvalho AT, Paes MM, Cunha MS, Brandão GC, Mapeli AM, Rescia VC, Oesterreich SA, and Villas-Boas GR
- Subjects
- Humans, Anti-Inflammatory Agents chemistry, Anti-Inflammatory Agents therapeutic use, Antineoplastic Agents, Phytogenic chemistry, Antineoplastic Agents, Phytogenic therapeutic use, Bromelia chemistry, Moraceae chemistry, Photosensitizing Agents chemistry, Photosensitizing Agents therapeutic use, Phytochemicals chemistry, Phytochemicals therapeutic use, Sapindaceae chemistry
- Abstract
Fruit plants have been widely used by the population as a source of food, income and in the treatment of various diseases due to their nutritional and pharmacological properties. The aim of this study was to review information from the most current research about the phytochemical composition, biological and toxicological properties of four fruit species widely used by the world population in order to support the safe medicinal use of these species and encourage further studies on their therapeutic properties. The reviewed species are: Talisia esculenta, Brosimum gaudichaudii, Genipa americana, and Bromelia antiacantha . The review presents the botanical description of these species, their geographical distribution, forms of use in popular medicine, phytochemical studies and molecules isolated from different plant organs. The description of the pharmacological mechanism of action of secondary metabolites isolated from these species was detailed and toxicity studies related to them were reviewed. The present study demonstrates the significant concentration of phenolic compounds in these species and their anti-inflammatory, anti-tumor, photosensitizing properties, among others. Such species provide important molecules with pharmacological activity that serve as raw materials for the development of new drugs, making further studies necessary to elucidate mechanisms of action not yet understood and prove the safety for use in humans. more...
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- 2020
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32. Anti-Zika virus activity and chemical characterization by ultra-high performance liquid chromatography (UPLC-DAD-UV-MS) of ethanol extracts in Tecoma species.
- Author
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Reis ACC, Silva BM, de Moura HMM, Pereira GR, and Brandão GC
- Subjects
- Animals, Brazil, Chlorocebus aethiops, Chromatography, High Pressure Liquid, Mass Spectrometry, Plant Leaves, Vero Cells, Antiviral Agents chemistry, Antiviral Agents pharmacology, Bignoniaceae chemistry, Plant Extracts chemistry, Plant Extracts pharmacology, Zika Virus drug effects
- Abstract
Background: Plant species from the genus Tecoma are found in tropical and subtropical regions around the world. Some of them are grown as ornamental plants and others can be used as medicinal plants. In the present study, ethanolic extracts from trunks and leaves of Tecoma species were tested in vitro using assays against the Zika virus., Methods: There was a total of 8 extracts obtained from different anatomical parts of three Tecoma species. The Tecoma castaneifolia, T. garrocha, T. stans var. angustata and T. stans var. stans were prepared by percolation with ethanol. The antiviral activity was assayed in vitro against the Zika virus by the MTT colorimetric method (n = 3). The UPLC-DAD-MS analysis of ethanolic extracts was performed from all the studied species. The biofractionation of T. stans var. stans trunk extract using different separation techniques led to the isolation of crenatoside compound., Results: Ethanolic extract from Tecoma species leaves were more active against the Zika virus (EC
50 149.90 to 61.25 μg/mL) when compared to the trunk extracts tested (EC50 131.0 to 66.79 μg/mL and two were not active). The ethyl acetate and aqueous fractions obtained from T. stans var. stans trunk were active against the Zika virus with EC50 values of 149.90 and 78.98 μg/mL, respectively. Crenatoside is a phenylethanoid glycoside isolated from the ethyl acetate of T. stans var. stans trunk extract. This compound was tested and exhibited EC50 34.78 μM (21.64 μg/mL), thus demonstrating a better result than the original ethanolic extracts as well as others extracts of Tecoma species, and it was more active than the positive control, ribavirin (386.84 μM). Furthermore, its selectivity index was at least 2.5 times higher than the tested ethanolic extracts and 11.1 times more potent than ribavirin., Conclusion: The Tecoma species demonstrated interesting in vitro activity against the Zika virus. The crenatoside, phenylethanoid glycoside that was for the first time isolated from Tecoma stans var. stans, exhibited a potent and relevant anti-Zika virus activity, being more active than ribavirin (positive control). The data show that crenatoside, was a promising compound with in vitro antiviral activity against the Zika virus. more...- Published
- 2020
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33. Antinociceptive and anti-inflammatory effect of Poincianella pyramidalis (Tul.) L.P. Queiroz.
- Author
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Zelice da Cruz de Moraes S, Shan AYKV, Oliveira Melo MA, Pereira da Silva J, Rocha Santos Passos F, de Souza Graça A, Araújo BS, Quintans JSS, Quintans Júnior LJ, Oliveira Barreto E, Brandão GC, and Estevam CDS more...
- Subjects
- Analgesics chemistry, Animals, Anti-Inflammatory Agents chemistry, Antioxidants chemistry, Carrageenan antagonists & inhibitors, Dose-Response Relationship, Drug, Male, Mice, Pain Measurement drug effects, Phenols analysis, Plant Bark chemistry, Plant Extracts chemistry, Plant Extracts pharmacology, Acetates chemistry, Analgesics pharmacology, Anti-Inflammatory Agents pharmacology, Antioxidants pharmacology, Fabaceae chemistry
- Abstract
Ethnopharmacology Relevance: Poncianella pyramidalis (Leguminosae) is a Caatinga plant used in folk medicine because of its pharmacological properties, which include anti-inflammatory action. However, chemical compounds responsible for this effect have not yet been identified., Aim of the Study: This study aimed to evaluate the antioxidant, antinociceptive and anti-inflammatory effects of the ethyl acetate fraction from the inner bark of P. pyramidalis., Material and Methods: Total phenol content (TP) was estimated using the Folin-Ciocalteu reagent, while in vitro antioxidant activity was determined by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging assay. Chemical identification was done using LC-PDA/MS and LC-ESI/MS/MS. In vivo antinociceptive and anti-inflammatory properties were investigated using formalin, mechanical hypernociception and carrageenan-induced pleurisy assays in mice., Results: TP was 525.08 ± 17.49 μg mg
-1 gallic acid equivalent. The ethyl acetate fraction (EAF) inhibited 87.76% of the DPPH radical with an EC50 of 22.94 μg mL-1 and Antioxidant Activity Index of 1.74. LC-PDA/MS and LC-ESI/MS/MS identified 15 compounds that are mostly derived from gallic and ellagic acids. Regarding in vivo antinociceptive and anti-inflammatory activity, EAF (100 mg kg-1) significantly reduced the nociceptive response in the second phase of the formalin assay by 50% (p < 0.01) compared with the control group. In the hypernociception test, a significant (p < 0.001) anti-hyperalgesic effect of EAF (100 mg kg-1) was observed up to the third hour of evaluation (p < 0.001). In the carrageenan assay, EAF (100 mg kg-1) was shown to inhibit protein extravasation, increase total leukocytes and neutrophils, and inhibit mononuclear cells., Conclusion: These results demonstrate EAF from the inner bark of P. pyramidalis has strong in vitro antioxidant effect as well as in vivo antinociceptive and anti-inflammatory activities, which may be attributed to the bark being rich in phenolic compounds derived from gallic acid., (Copyright © 2020 Elsevier B.V. All rights reserved.) more...- Published
- 2020
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34. A chloroquinoline derivate presents effective in vitro and in vivo antileishmanial activity against Leishmania species that cause tegumentary and visceral leishmaniasis.
- Author
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Sousa JKT, Antinarelli LMR, Mendonça DVC, Lage DP, Tavares GSV, Dias DS, Ribeiro PAF, Ludolf F, Coelho VTS, Oliveira-da-Silva JA, Perin L, Oliveira BA, Alvarenga DF, Chávez-Fumagalli MA, Brandão GC, Nobre V, Pereira GR, Coimbra ES, and Coelho EAF more...
- Subjects
- Animals, Female, Mice, Mice, Inbred BALB C, Species Specificity, Antiprotozoal Agents pharmacology, Leishmania drug effects, Leishmaniasis drug therapy, Quinolines pharmacology
- Abstract
The identification of new therapeutics to treat leishmaniasis is desirable, since available drugs are toxic and present high cost and/or poor availability. Therefore, the discovery of safer, more effective and selective pharmaceutical options is of utmost importance. Efforts towards the development of new candidates based on molecule analogs with known biological functions have been an interesting and cost-effective strategy. In this context, quinoline derivatives have proven to be effective biological activities against distinct diseases. In the present study, a new chloroquinoline derivate, AM1009, was in vitro tested against two Leishmania species that cause leishmaniasis. The present study analyzed the necessary inhibitory concentration to preclude 50% of the Leishmania promastigotes and axenic amastigotes (EC
50 value), as well as the inhibitory concentrations to preclude 50% of the murine macrophages and human red blood cells (CC50 and RBC50 values, respectively). In addition, the treatment of infected macrophages and the inhibition of infection using pre-treated parasites were also investigated, as was the mechanism of action of the molecule in L. amazonensis. To investigate the in vivo therapeutic effect, BALB/c mice were infected with L. amazonensis and later treated with AM1009. Parasitological and immunological parameters were also evaluated. Clioquinol, a known antileishmanial quinoline derivate, and amphotericin B (AmpB), were used as molecule and drug controls, respectively. Results in both in vitro and in vivo experiments showed a better and more selective action of AM1009 to kill the in vitro parasites, as well as in treating infected mice, when compared to results obtained using clioquinol or AmpB. AM1009-treated animals presented significantly lower average lesion diameter and parasite burden in the infected tissue and organs evaluated in this study, as well as a more polarized antileishmanial Th1 immune response and low renal and hepatic toxicity. This result suggests that AM1009 should be considered a possible therapeutic target to be evaluated in future studies for treatment against leishmaniasis., (Copyright © 2019 Elsevier B.V. All rights reserved.) more...- Published
- 2019
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35. Anti-inflammatory activity of Protium spruceanum (Benth.) Engler is associated to immunomodulation and enzymes inhibition.
- Author
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Amparo TR, Seibert JB, Mathias FAS, Vieira JFP, Soares RDOA, Freitas KM, Cabral VAR, Brandão GC, Santos ODHD, de Souza GHB, and Vieira PMA
- Subjects
- Acetylglucosaminidase metabolism, Animals, Cell Line, Cyclooxygenase 2 metabolism, Cytokines metabolism, Immunomodulation drug effects, Matrix Metalloproteinase 9 metabolism, Mice, Nitric Oxide metabolism, Nitric Oxide Synthase Type II metabolism, Plant Leaves, Plant Stems, Reactive Oxygen Species metabolism, Anti-Inflammatory Agents pharmacology, Burseraceae, Plant Extracts pharmacology
- Abstract
Ethnopharmacological Relevance: Protium spruceanum (Burseraceae) is used in Brazilian traditional medicine as anti-inflammatory, but the factors involved in this activity were not yet characterized., Aims of the Study: analyze the aspects involved in the anti-inflammatory activity of polar fractions obtained from extracts of leaves and branches., Materials and Methods: Hydromethanolic fraction was obtained by liquid-liquid partition from crude ethanolic extract and its compounds were identified by LC-DAD-MS. Activity tests were performed using LPS + IFN-γ stimulated J774A.1 macrophages. Cytokines were evaluated by CBA kit, NO by Griess method, ROS by DCFH-DA, N-acetylglucosaminidase (NAG) activity by spectrophotometric method, matrix-metalloproteinase (MMP-9) activity by zymography, inducible nitric oxide synthase (iNOS) expression by immunofluorescence and cyclooxygenase (COX-2) expression by Western blot., Results: Fractions induced an increase of IL-6 and IL-10 which leads to the control of pro-inflammatory cytokines levels. The treatment with the fractions also reduced NO production at all concentrations tested in all evaluated periods. ROS production by the macrophages was inhibited by the treatment and the leaves fraction showed the best results with a lower concentration than that observed for the branches. The enzymes assays showed that leaves fraction inhibited NAG and MMP-9 activities, as well as, iNOS and COX-2 expression. These activities can be associated with the presence of procyanidin, catechin, rutin, quercitrin, isoquercitrin and kaempferol-3-O-rhamnoside, major compounds that were identified in the fraction., Conclusions: Anti-inflammatory activity of P. spruceanum is associated to an immunomodulatory effect that leads to inhibition of ROS, NO, NAG, MMP-9, COX-2 and iNOS., (Copyright © 2019. Published by Elsevier B.V.) more...
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- 2019
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36. Development of propolis nanoemulsion with antioxidant and antimicrobial activity for use as a potential natural preservative.
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Seibert JB, Bautista-Silva JP, Amparo TR, Petit A, Pervier P, Dos Santos Almeida JC, Azevedo MC, Silveira BM, Brandão GC, de Souza GHB, de Medeiros Teixeira LF, and Dos Santos ODH
- Subjects
- Emulsions analysis, Emulsions chemistry, Nanotechnology, Anti-Infective Agents analysis, Anti-Infective Agents chemistry, Antioxidants analysis, Antioxidants chemistry, Food Preservatives analysis, Food Preservatives chemistry, Propolis analysis, Propolis chemistry
- Abstract
Propolis has demonstrated potential use as food preservative but it presents strong and unpleasant flavor that alters the sensory characteristics foods. A nanoemulsion was proposed to carry the Brazilian propolis extracts for use as natural food preservative. Antimicrobial and antioxidant activities and chemical constituents of the extracts were investigated. The latter were made by sequential extraction using different solvents (hexane, ethyl acetate and ethanol). Antimicrobial activity was evaluated by agar diffusion and microdilution methods and antioxidant activity by DPPH and ABTS assays. Extracts showed antibacterial and antioxidant activity, highlighting the ethanolic which contained artepillin-C, kaempferide, drupanin and p-coumaric acid as main compounds by LC-MS analysis. The nanoemulsion developed by phase inversion method was characterized and stable under thermal-stress and centrifugation conditions. Biological properties evaluated were effectively maintained by the formulation. It was concluded that the nanoemulsion can be used as a food preservative, preventing degradation and masking the propolis off-flavor., (Copyright © 2019 Elsevier Ltd. All rights reserved.) more...
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- 2019
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37. Prenylated flavonoid-enriched fraction from Maclura tinctoria shows biological activity against Staphylococcus aureus and protects Galleria mellonella larvae from bacterial infection.
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das Chagas Almeida A, Azevedo Rodrigues L, Dos Santos Paulino G, Pereira Aguilar A, Andrade Almeida A, Olavo Ferreira S, Brandão GC, Viana Leite JP, and de Oliveira Barros Ribon A
- Subjects
- Animals, Anti-Bacterial Agents chemistry, Brazil, Disease Models, Animal, Flavonoids chemistry, Humans, Larva growth & development, Larva microbiology, Microbial Sensitivity Tests, Moths growth & development, Plant Extracts chemistry, Protective Agents chemistry, Staphylococcal Infections microbiology, Anti-Bacterial Agents administration & dosage, Flavonoids administration & dosage, Maclura chemistry, Moths microbiology, Plant Extracts administration & dosage, Protective Agents administration & dosage, Staphylococcal Infections prevention & control, Staphylococcus aureus drug effects
- Abstract
Background: The Atlantic Forest biome extends along the entire Brazilian coast and is home to approximately 20,000 plant species, many of which are endemic; it is considered one of the hotspot regions of the planet. Several of these species are sources of natural products with biological activities that are still unknown. In this study, we evaluated the antimicrobial activity of 90 extracts derived from native Atlantic Forest tree species against Staphylococcus aureus, an important human and veterinary pathogen., Methods: Extracts from native Atlantic Forest tree species were evaluated for their antimicrobial activity against S. aureus by in vitro standard methods. Phytochemical fractionation of the extract from Maclura tinctoria was performed by liquid-liquid partitioning. LC-DAD-ESI-MS was used for identification of constituents in the most active fraction. Damage of cells and alterations in the permeability of cell membrane were determined by atomic force microscopy (AFM) and crystal violet uptake assay, respectively. In vivo antimicrobial activity was evaluated using Galleria mellonella larvae infected with S. aureus with survival data collected using the Kaplan-Meier method., Results: Among the organic or aqueous extracts tested here, 26 showed biological activity. Eight species showed relevant results, with a minimum inhibitory concentration (MIC) below 1 mg/mL. Antibacterial activity was registered for three species for the first time. An organic extract from Maclura tinctoria leaves showed the lowest MIC (0.08 mg/mL). Fractionation of this extract by liquid-liquid partitioning led to obtaining fraction 11FO d with a MIC of 0.04 mg/mL. This fraction showed strong activity against veterinary S. aureus isolates and contributed to the increased survival of Galleria mellonella larvae infected with S. aureus ATCC 29213. The bacterial surface was not altered by the presence of 11FO d, and no cell membrane damage was detected. The LC-DAD-ESI/MS analyses identified prenylated flavonoids as the major constituents responsible for the antibacterial activity of this active extract., Conclusion: A fraction enriched in prenylated isoflavones and flavanones from M. tinctoria showed in vitro and in vivo efficacy as antistaphylococcal agents. These findings justify the need for further research to elucidate the mechanisms of action of these compounds. more...
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- 2019
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38. Assessment of cadmium and lead in commercial coconut water and industrialized coconut milk employing HR-CS GF AAS.
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Paixão LB, Brandão GC, Araujo RGO, and Korn MGA
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- Brazil, Cocos metabolism, Graphite chemistry, Limit of Detection, Reproducibility of Results, Wastewater analysis, Cadmium analysis, Cocos chemistry, Fruit and Vegetable Juices analysis, Lead analysis, Spectrophotometry, Atomic methods
- Abstract
In this work, an analytical method for the determination of Cd and Pb in natural coconut water samples, industrialized coconut water samples and coconut milk using high-resolution continuum source graphite furnace atomic absorption spectrometry (HR-CS GF AAS), after minimum treatment of the sample was developed. The analytical method was applied to 46 samples collected in Salvador, Bahia (Brazil). The ranges of concentrations obtained were: 0.42-18.72 μg L
-1 Cd and <0.70-36.32 μg L-1 Pb for natural coconut water samples (n = 14); <0.06-1.49 μg L-1 Cd and 6.57-29.02 μg L-1 Pb for industrialized water coconut samples (n = 16); and <0.10-5.93 ng g-1 Cd and <0.85-22.41 ng g-1 Pb for coconut milk samples (n = 16). For all samples, Cd and Pb concentrations were below the maximum tolerated values recommended by Brazilian Health Surveillance Agency (Agência Nacional de Vigilância Sanitária, ANVISA)., (Copyright © 2019 Elsevier Ltd. All rights reserved.) more...- Published
- 2019
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39. Antioxidant study indicative of antibacterial and antimutagenic activities of an ellagitannin-rich aqueous extract from the leaves of Miconia latecrenata.
- Author
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Gontijo DC, Gontijo PC, Brandão GC, Diaz MAN, de Oliveira AB, Fietto LG, and Leite JPV
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- Anti-Bacterial Agents isolation & purification, Antimutagenic Agents isolation & purification, Antioxidants isolation & purification, Biphenyl Compounds chemistry, Escherichia coli drug effects, Picrates chemistry, Plant Extracts isolation & purification, Plant Leaves chemistry, Salmonella typhimurium drug effects, Salmonella typhimurium genetics, Staphylococcus aureus drug effects, Anti-Bacterial Agents pharmacology, Antimutagenic Agents pharmacology, Antioxidants pharmacology, Hydrolyzable Tannins isolation & purification, Melastomataceae chemistry, Plant Extracts pharmacology
- Abstract
Ethnopharmacological relevance; Several plant species of Miconia genus are commonly used in Brazilian folk medicine as anti-inflammatory agents and for the treatment of infectious diseases. Infusions and extracts of Miconia species are also reported as analgesic, antimicrobial, antimalarial, antioxidant, anti-inflammatory, antinociceptive, antimutagenic, and antitumoral. Aim of the study; To determine the phytochemical composition of an aqueous extract of Miconia latecrenata leaves and to evaluate its antioxidant, antibacterial, antimutagenic and antigenotoxic activities. Materials and Methods; The following methods were used for the different effects: I) antioxidant - β-carotene/linoleic acid, lipid peroxidation, and DPPH• radical scavenging; II) antibacterial - agar well diffusion and MIC methods); III) antimutagenic assays - Ames Test; and IV) antigenotoxic - Plasmid cleavage test. The phytochemical analysis and phenolic quantification were carried out by UPLC-DAD-ESI-MS/MS and colorimetry, respectively. In addition, statistical correlation analysis was performed aiming to evaluate the Pearson correlation between phenolic compounds and biological assays. Results; A high content of tannins was observed and the ellagitannin isomers of 1,2,3,5-tris-galloyl-4,6-HHDP-glucose were identified as the main constituents of the leaves aqueous extract. High antioxidant effect, in different tests, high antibacterial activity to gram-positive and negative strains, as well as high antimutagenic activity were observed. Statistical analysis showed a high Pearson correlation for the tannin content in relation to the results of the antioxidant and antibacterial tests. In general, the antioxidant action of the aqueous extract showed low correlation with the antimutagenic activity. Conclusions; The present results confirmed the expectations regarding the pharmacological profile of M. latecrenata supporting its therapeutic potential in relation to ROS/RNS related disorders. Furthermore, the phenolic compounds of M. latecrenata can act, in turn, minimizing or inhibiting the biological macromolecules damage, especially DNA., (Copyright © 2019 Elsevier B.V. All rights reserved.) more...
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- 2019
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40. In vitro and in vivo antileishmanial activity of a fluoroquinoline derivate against Leishmania infantum and Leishmania amazonensis species.
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Tavares GSV, Mendonça DVC, Lage DP, Antinarelli LMR, Soyer TG, Senna AJS, Matos GF, Dias DS, Ribeiro PAF, Batista JPT, Poletto JM, Brandão GC, Chávez-Fumagalli MA, Pereira GR, Coimbra ES, and Coelho EAF more...
- Subjects
- Animals, Leishmaniasis parasitology, Liver parasitology, Macrophages drug effects, Membrane Potential, Mitochondrial drug effects, Mice, Mice, Inbred BALB C, Models, Animal, Parasite Load, Reactive Oxygen Species, Spleen parasitology, Amphotericin B pharmacology, Antiprotozoal Agents pharmacology, Antiprotozoal Agents therapeutic use, Fluoroquinolones therapeutic use, Leishmania infantum drug effects, Leishmania mexicana drug effects, Leishmaniasis drug therapy
- Abstract
New therapeutics against leishmaniasis are desirable, since the current drugs applied against this disease complex presents problems, such as the toxicity, high cost and/or parasite resistance. In the present study, a new fluoroquinoline derivate, namely 7-chloro-N-(4-fluorophenethyl)quinolin-4-amine or GF1061, was evaluated regarding to its in vitro antileishmanial action against Leishmania infantum and L. amazonensis species, as well as by its toxicity in mammalian cells and efficacy in the treatment of infected macrophages. The mechanism of action of this molecule in L. amazonensis and the therapeutic efficacy in infected BALB/c mice were also evaluated. Results showed that GF1061 was effective against both parasite species, showing selectivity index (SI) of 38.7 and 42.7 against L. infantum and L. amazonensis promastigotes, respectively, and of 45.0 and 48.9 against the amastigotes, respectively. Amphotericin B (AmpB), used as control, showed SI values of 6.6 and 8.8 against L. infantum and L. amazonensis promastigotes, respectively, and of 2.2 and 2.7 against the amastigotes, respectively. The molecule was effective in treat infected macrophages, as well as it induced alterations in the mitochondrial membrane potential, increase in the reactive oxygen species production, and in the cell integrity of the parasites. Regarding to the in vivo experiments, BALB/c mice (n = 8 per group) were subcutaneously infected with 10
6 L. amazonensis stationary promastigotes and, 60 days post-infection, they received saline or were treated during 10 days, once a day, with AmpB (1 mg/kg body weight) or GF1061 (5 mg/kg body weight). One day after the treatment, the infected tissue, spleen, liver, and draining lymph node (dLN) of the animals were collected, and the parasite load was evaluated. GF1061-treated mice, as compared to the saline and AmpB groups, showed significant reductions in the parasitism in the infected tissue (66% and 62%, respectively), liver (69% and 44%, respectively), spleen (71% and 38%, respectively), and dLN (72% and 48%, respectively). In conclusion, results suggested that GF1061 may be considered as a possible therapeutic target to be evaluated against leishmaniasis in other mammalian hosts., (Copyright © 2018 Elsevier B.V. All rights reserved.) more...- Published
- 2019
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41. Antiplasmodial activity and cytotoxicity, isolation of active alkaloids, and dereplication of Xylopia sericea leaves ethanol extract by UPLC-DAD-ESI-MS/MS.
- Author
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Gontijo DC, Brandão GC, Nascimento MFAD, and Oliveira AB
- Subjects
- Alkaloids isolation & purification, Alkaloids toxicity, Antimalarials isolation & purification, Antimalarials toxicity, Aporphines isolation & purification, Aporphines pharmacology, Chromatography, High Pressure Liquid methods, Dioxoles isolation & purification, Dioxoles pharmacology, Ethanol chemistry, Hep G2 Cells, Humans, Inhibitory Concentration 50, Plant Extracts administration & dosage, Plant Extracts toxicity, Plant Leaves, Plasmodium falciparum drug effects, Tandem Mass Spectrometry methods, Alkaloids pharmacology, Antimalarials pharmacology, Plant Extracts pharmacology, Xylopia chemistry
- Abstract
Objectives: To assess the antiplasmodial activity of the ethanol extract of Xylopia sericea leaves, Annonaceae, often associated with antimalarial use and to perform a bioguided isolation of active compounds., Methods: Dereplication of ethanol extract by the UPLC-DAD-ESI-MS/MS technique allowed the identification of the major constituents, isolation and identification of alkaloids. The antiplasmodial and cytotoxic activity of the extract, fractions and isolated compounds was evaluated against the chloroquine-resistant W2 strain Plasmodium falciparum and HepG2 cells, respectively., Key Findings: Ethanol extract showed high reduction of parasitemia as well as moderate cytotoxicity (86.5 ± 3.0% growth inhibition at 50 μg/ml and CC
50 72.1 ± 5.1 μg/ml, respectively). A total of eight flavonoids were identified, and two aporphine alkaloids, anonaine and O-methylmoschatoline, were isolated. Anonaine disclosed significant antiplasmodial effect and moderate cytotoxicity (IC50 23.2 ± 2.7 μg/ml, CC50 38.3 ± 2.3 μg/ml, SI 1.6) while O-methylmoschatoline was not active against P. falciparum and showed a low cytotoxicity (33.5 ± 1.9% growth inhibition at 50 μg/ml, CC50 274.4 ± 0.5 μg/ml)., Conclusions: Characterization of Xylopia sericea leaves ethanol extract by UPLC-DAD-ESI-MS/MS as well as its antiplasmodial activity and the occurrence of anonaine and O-methylmoschatoline in this Xylopia species are reported by the first time., (© 2018 Royal Pharmaceutical Society.) more...- Published
- 2019
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42. Multivariate optimization of ultrasound-assisted extraction using Doehlert matrix for simultaneous determination of Fe and Ni in vegetable oils by high-resolution continuum source graphite furnace atomic absorption spectrometry.
- Author
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Almeida JS, Santos GL, Brandão GC, Korn MGA, and Teixeira LSG
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- Chemical Fractionation instrumentation, Food Analysis instrumentation, Food Contamination analysis, Graphite chemistry, Multivariate Analysis, Plant Oils chemistry, Spectrophotometry, Atomic instrumentation, Spectrophotometry, Atomic methods, Temperature, Ultrasonics, Chemical Fractionation methods, Food Analysis methods, Iron analysis, Nickel analysis, Plant Oils analysis
- Abstract
A method for simultaneous determination of Fe (232.036 nm) and Ni (232.195 nm) in vegetable oil samples by high-resolution continuum source graphite furnace atomic absorption spectrometry (HR-CS GF AAS) after an acid extraction of the analytes is proposed. In the extraction step, hydrochloric, nitric and acetic acid solutions were tested. The optimization of the procedure was performed by applying Doehlert matrix, and multiple response was used for simultaneous evaluation of the performance of the extraction. The optimum conditions were: extraction time of 17 min, extraction temperature of 39 °C and sonication amplitude of 42%, employing 0.5 mol L
-1 HCl as the extracting solvent. The limits of quantification were 60 and 160 ng g-1 for Fe and Ni, respectively. The method was applied to the analysis of vegetable oil samples and the results were compared with a method employing inductively coupled plasma optical emission spectrometry (ICP OES)., (Copyright © 2018 Elsevier Ltd. All rights reserved.) more...- Published
- 2019
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43. In vitro antiplasmodial activity and identification, using tandem LC-MS, of alkaloids from Aspidosperma excelsum, a plant used to treat malaria in Amazonia.
- Author
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do Nascimento MS, Pina NDPV, da Silva ASB, Gomes LFDS, de Vasconcellos F, Brandão GC, do Nascimento MFA, de Oliveira AB, and Barbosa WLR
- Subjects
- Antimalarials analysis, Brazil, Chloroquine, Chromatography, Liquid, Drug Resistance, Microbial, Erythrocytes microbiology, Hep G2 Cells, Humans, Indole Alkaloids analysis, Medicine, Traditional, Plant Bark, Tandem Mass Spectrometry, Antimalarials pharmacology, Aspidosperma, Indole Alkaloids pharmacology, Plasmodium falciparum drug effects
- Abstract
Ethnopharmacological Relevance: Aspidosperma excelsum Benth. (Apocynaceae), a native tree in the Brazilian Amazonia, is traditionally used to treat various diseases, including malaria., Aim of Study: To investigate the chemical constitution, antiplasmodial activity and cytotoxicity of samples obtained from A. excelsum trunk bark by different procedures aiming to evaluate their potential as an antimalarial phytomedicine., Materials and Methods: A hydroethanolic extract and alkaloid extracts were prepared and assayed for antiplasmodial activity and cytotoxicity against chloroquine-resistant Plasmodium falciparum (W2 strain) and HepG2 cells, respectively. Taking into account the known occurrence and antimalarial activity of Aspidosperma monoterpene indole alkaloids (MIA), acid-base extractions were carried out and the fractions were assayed for antiplasmodial activity and cytotoxicity. All the samples were analysed by hyphenated chromatographic techniques, such as UPLC-DAD-ESI-MS/MS and HRMS (HPLC-MS MicroTOF), comparing their chemical composition to the literature data., Results: The hydroethanolic extract disclosed a moderate in vitro activity against chloroquine-resistant Plasmodium falciparum (W2 strain) with IC
50 23.68 ± 3.08 µg/mL), low cytotoxicity to HepG2 cells (> 250 µg/mL) and good SI (> 10.56). A total of 20 known monoterpene indole alkaloids were identified, seven of which are here firstly described for A. excelsum. Known highly active alkaloids, namely demethylaspidospermine, aspidocarpine, and ochrolifuanine are present in active alkaloid fractions and might contribute to their observed antiplasmodial effect. An alkaloid fraction (Ae-Alk2), obtained directly from trunk bark by extraction with dil. aqueous HCl, pointed out for its activity (IC50 8.75±2.26 µg/mL, CC50 185.14±1.97 µg/mL, SI 21.16) and should be highlighted as the most promising out of the assayed samples., Conclusion: The present results represent a preliminary support to the alleged antimalarial use of A. excelsum trunk bark and allowed to highlight alkaloid fractions as promising phytomedicines., (Copyright © 2018 Elsevier B.V. All rights reserved.) more...- Published
- 2019
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44. Anti-Inflammatory and Antioxidant Properties of Black Mulberry ( Morus nigra L.) in a Model of LPS-Induced Sepsis.
- Author
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de Pádua Lúcio K, Rabelo ACS, Araújo CM, Brandão GC, de Souza GHB, da Silva RG, de Souza DMS, Talvani A, Bezerra FS, Cruz Calsavara AJ, and Costa DC
- Subjects
- Animals, Disease Models, Animal, Male, Mice, Mice, Inbred C57BL, Sepsis chemically induced, Sepsis metabolism, Sepsis pathology, Anti-Inflammatory Agents pharmacology, Antioxidants pharmacology, Fruit chemistry, Lipopolysaccharides toxicity, Morus chemistry, Plant Extracts pharmacology, Sepsis drug therapy
- Abstract
Sepsis is a complex disease and is the cause of many deaths worldwide. Sepsis pathogenesis involves a dysregulated inflammatory response with consequent production of inflammatory mediators and reactive species. The production and excessive release of these substances into the systemic circulation trigger various cellular and metabolic alterations that are observed during the disease evolution. Thus, more studies have been carried out to investigate the therapeutic potential of plants such as Morus nigra L., popularly known as black mulberry. Studies have shown that plants belonging to the Morus genus are rich in secondary metabolites such as flavonoids which are associated with important biological activities as antioxidant and anti-inflammatory actions. Based on this context, the objective of our study was to evaluate the anti-inflammatory and antioxidant properties of Morus nigra L. in a sepsis model induced by LPS. Male C57BL/6 mice were distributed in four groups: control, sepsis, sepsis treated with leaf extract of mulberry, and sepsis treated with mulberry pulp. The animals were treated with 100 μ L of their respective treatments for twenty-one days. Sepsis was induced at the 21st day with lipopolysaccharide (LPS) by intraperitoneal injection. The animals were euthanized 24 hours after receiving the LPS injection. The data obtained were analyzed in GraphPad Prism 6.0 software. Our results showed that treatment with either extract significantly decreased the number of leukocytes in the bronchoalveolar lavage fluid and serum levels of TNF in septic animals. Regarding the redox status, the treatments significantly decreased the antioxidant activity of the enzyme glutathione peroxidase. Regarding metalloproteinase type 2, it was observed that the treatment with black mulberry pulp was able to significantly reduce the activity of this enzyme concerning the sepsis group. Finally, these results together promoted an increase in the animal's survival that received the black mulberry leaf or pulp extract. more...
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- 2018
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45. Antibacterial activity of extract and fractions from branches of Protium spruceanum and cytotoxicity on fibroblasts.
- Author
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Amparo TR, Rodrigues IV, Seibert JB, Souza RHZ, Oliveira AR, Cabral VAR, Vieira PMA, Brandão GC, Okuma AA, Filho SAV, Teixeira LFM, and Souza GHB
- Subjects
- Animals, Bacteria drug effects, Burseraceae toxicity, Fibroblasts drug effects, Mice, Microbial Sensitivity Tests, Plant Extracts toxicity, Staphylococcus saprophyticus drug effects, Anti-Bacterial Agents pharmacology, Burseraceae chemistry, Plant Extracts pharmacology
- Abstract
The crude ethanol extract (CEE) and fractions from branches of Protium spruceanum were subjected to antibacterial and cytotoxicity assays. Compounds of the most active fraction were identified by GC-MS and LC-MS. CEE was active against 19 bacteria and the ethyl acetate fraction (EAF) showed the lowest minimum bactericidal concentration (MBC 0.3-80.0 mg/mL). Through time-kill assay was observed that EAF induced rapid bactericidal effect against Staphylococcus saprophyticus. The cytotoxicity tests against L929 fibroblasts showed great potential of EAF on the treatment of infections caused by five bacteria (MBC < IC
50 ). The results provide in vitro scientific support to the possible application of branches of P. spruceanum as antimicrobial agent that may contribute for treatment of infections. more...- Published
- 2018
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46. Detection of the antiviral activity of epicatechin isolated from Salacia crassifolia (Celastraceae) against Mayaro virus based on protein C homology modelling and virtual screening.
- Author
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Ferreira PG, Ferraz AC, Figueiredo JE, Lima CF, Rodrigues VG, Taranto AG, Ferreira JMS, Brandão GC, Vieira-Filho SA, Duarte LP, de Brito Magalhães CL, and de Magalhães JC
- Subjects
- Alphavirus metabolism, Animals, Antigens, Viral metabolism, Antiviral Agents chemistry, Antiviral Agents isolation & purification, Binding Sites, Catechin chemistry, Catechin isolation & purification, Chlorocebus aethiops, High-Throughput Screening Assays, Humans, Inhibitory Concentration 50, Molecular Docking Simulation, Protein Binding, Protein Conformation, alpha-Helical, Protein Conformation, beta-Strand, Protein Interaction Domains and Motifs, Ribavirin chemistry, Ribavirin pharmacology, Structural Homology, Protein, User-Computer Interface, Vero Cells, Viral Proteins antagonists & inhibitors, Viral Proteins metabolism, Virus Replication drug effects, Alphavirus chemistry, Antigens, Viral chemistry, Antiviral Agents pharmacology, Catechin pharmacology, Salacia chemistry, Viral Proteins chemistry
- Abstract
Mayaro fever, caused by Mayaro virus (MAYV) is a sub-lethal disease with symptoms that are easily confused with those of dengue fever, except for polyarthralgia, which may culminate in physical incapacitation. Recently, outbreaks of MAYV have been documented in metropolitan areas, and to date, there is no therapy or vaccine available. Moreover, there is no information regarding the three-dimensional structure of the viral proteins of MAYV, which is important in the search for antivirals. In this work, we constructed a three-dimensional model of protein C of MAYV by homology modelling, and this was employed in a manner similar to that of receptors in virtual screening studies to evaluate 590 molecules as prospective antiviral agents. In vitro bioassays were utilized to confirm the potential antiviral activity of the flavonoid epicatechin isolated from Salacia crassifolia (Celastraceae). The virtual screening showed that six flavonoids were promising ligands for protein C. The bioassays showed potent antiviral action of epicatechin, which protected the cells from almost all of the effects of viral infection. An effective concentration (EC
50 ) of 0.247 μmol/mL was observed with a selectivity index (SI) of 7. The cytotoxicity assay showed that epicatechin has low toxicity, with a 50% cytotoxic concentration (CC50 ) greater than 1.723 µmol/mL. Epicatechin was found to be twice as potent as the reference antiviral ribavirin. Furthermore, a replication kinetics assay showed a strong inhibitory effect of epicatechin on MAYV growth, with a reduction of at least four logs in virus production. Our results indicate that epicatechin is a promising candidate for further testing as an antiviral agent against Mayaro virus and other alphaviruses. more...- Published
- 2018
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47. Antimalarial naphthoquinones. Synthesis via click chemistry, in vitro activity, docking to PfDHODH and SAR of lapachol-based compounds.
- Author
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Brandão GC, Rocha Missias FC, Arantes LM, Soares LF, Roy KK, Doerksen RJ, Braga de Oliveira A, and Pereira GR
- Subjects
- Antimalarials chemical synthesis, Antimalarials chemistry, Cell Survival drug effects, Chloroquine pharmacology, Click Chemistry, Dose-Response Relationship, Drug, Drug Resistance drug effects, Hep G2 Cells, Humans, Models, Molecular, Molecular Structure, Naphthoquinones chemistry, Parasitic Sensitivity Tests, Structure-Activity Relationship, Antimalarials pharmacology, Naphthoquinones pharmacology, Plasmodium falciparum drug effects
- Abstract
Lapachol is an abundant prenyl naphthoquinone occurring in Brazilian Bignoniaceae that was clinically used, in former times, as an antimalarial drug, despite its moderate effect. Aiming to search for potentially better antimalarials, a series of 1,2,3-triazole derivatives was synthesized by chemical modification of lapachol. Alkylation of the hydroxyl group gave its propargyl ether which, via copper-catalyzed cycloaddition (CuAAC) click chemistry with different organic azides, afforded 17 naphthoquinonolyl triazole derivatives. All the synthetic compounds were evaluated for their in vitro activity against chloroquine resistant Plasmodium falciparum (W2) and for cytotoxicity to HepG2 cells. Compounds containing the naphthoquinolyl triazole moieties showed higher antimalarial activity than lapachol (IC
50 123.5 μM) and selectivity index (SI) values in the range of 4.5-197.7. Molecular docking simulations of lapachol, atovaquone and all the newly synthesized compounds were carried out for interactions with PfDHODH, a mitochondrial enzyme of the parasite respiratory chain that is essential for de novo pyrimidine biosynthesis. Docking of the naphthoquinonolyl triazole derivatives to PfDHODH yielded scores between -9.375 and -14.55 units, compared to -9.137 for lapachol and -12.95 for atovaquone and disclosed the derivative 17 as a lead compound. Therefore, the study results show the enhancement of DHODH binding affinity correlated with improvement of SI values and in vitro activities of the lapachol derivatives., (Copyright © 2017 Elsevier Masson SAS. All rights reserved.) more...- Published
- 2018
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48. Phytochemical characterization and antioxidant, antibacterial and antimutagenic activities of aqueous extract from leaves of Alchornea glandulosa.
- Author
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Gontijo DC, Diaz MAN, Brandão GC, Gontijo PC, Oliveira AB, Fietto LG, and Leite JPV
- Subjects
- Plant Leaves chemistry, Staphylococcus aureus drug effects, Anti-Bacterial Agents pharmacology, Antimutagenic Agents pharmacology, Antioxidants pharmacology, Euphorbiaceae chemistry, Plant Extracts pharmacology
- Abstract
Plant extracts exist as a complex matrix which serves as a source of numerous bioactive metabolites. The ultra performance liquid chromatography with diode-array detection-coupled electrospray ionization-mass spectrometry/mass spectrometry technique was used to characterize the aqueous extract from leaves of Alchornea glandulosa (EAG), a species popularly used to treat gastrointestinal problems as an antiulcer agent. Quantification of phenolic derivatives was determined using Folin-Ciocalteu and aluminum trichloride (AlCl
3 ) methods. In addition, antioxidant (2,2-diphenyl-1-picrylhydrazyl [DPPH• ] radical scavenging, β-carotene-linoleic acid, and lipid peroxidation), antibacterial (agar well diffusion method and minimum inhibitory concentration), antimutagenic (Ames test), and antigenotoxic (plasmid cleavage) assays were also performed on this plant extract. The ellagitannin tris-galloyl-hexahydroxydiphenic acid-glucose was identified as the predominant compound along with tannins as majority metabolites. EAG showed high antioxidant activity accompanied by moderate antibacterial activity against Staphylococcus aureus. The highest antimutagenic activity was observed for TA97 strain without metabolic activation (S9) and with metabolic activation, TA100 and TA102 were completely inhibited. In addition, EAG exhibited potential signs of antigenotoxic action. The high antioxidant and antimutagenic activity observed for EAG suggests important therapeutic uses that still need to be verified in future studies. more...- Published
- 2018
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49. Identification of phenolic compounds and biologically related activities from Ocotea odorifera aqueous extract leaves.
- Author
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Gontijo DC, Brandão GC, Gontijo PC, de Oliveira AB, Diaz MAN, Fietto LG, and Leite JPV
- Subjects
- Antioxidants chemistry, Phytochemicals analysis, Flavonoids chemistry, Ocotea chemistry, Plant Extracts chemistry, Plant Leaves chemistry, Tannins chemistry
- Abstract
Ocotea odorifera (Vell.) Rohwer is popularly used as food and flavoring. The aim of this study was to determine the chemical composition of the aqueous extract from O. odorifera leaves and evaluate the correlation of their phytochemical composition and biological activities. The antioxidant effect was determined by DPPH radical scavenging, β-carotene-linoleic acid and lipid peroxidation assays; the antibacterial activity was evaluated by the hole plate and MIC techniques and the antimutagenic activity was evaluated by the Ames test. Identification of phytochemicals was performed by LC-ESI/MS and the correlation between the phytochemical composition of the extract and the evaluated activities. The results allowed the identification of 13 phenolic compounds in the extract that exhibited high antioxidant activity and moderate antibacterial and antimutagenic action. Statistical analyses showed correlation of the total phenolic content with biologically related activities. The phytochemical analyses, together with the biological results, support the popular use of O. odorifera., (Copyright © 2017 Elsevier Ltd. All rights reserved.) more...
- Published
- 2017
- Full Text
- View/download PDF
50. Determination of phospholipids in soybean lecithin samples via the phosphorus monoxide molecule by high-resolution continuum source graphite furnace molecular absorption spectrometry.
- Author
-
Pires LN, Brandão GC, and Teixeira LS
- Subjects
- Graphite, Temperature, Lecithins analysis, Phospholipids analysis, Phosphorus analysis, Glycine max chemistry, Spectrophotometry, Atomic methods
- Abstract
This paper presents a method for determining phospholipids in soybean lecithin samples by phosphorus determination using high-resolution continuum source graphite furnace molecular absorption spectrometry (HR-CS GF MAS) via molecular absorption of phosphorus monoxide. Samples were diluted in methyl isobutyl ketone. The best conditions were found to be 213.561nm with a pyrolysis temperature of 1300°C, a volatilization temperature of 2300°C and Mg as a chemical modifier. To increase the analytical sensitivity, measurement of the absorbance signal was obtained by summing molecular transition lines for PO surrounding 213nm: 213.561, 213.526, 213.617 and 213.637nm. The limit of detection was 2.35mgg
-1 and the precision, evaluated as relative standard deviation (RSD), was 2.47% (n=10) for a sample containing 2.2% (w/v) phosphorus. The developed method was applied for the analysis of commercial samples of soybean lecithin. The determined concentrations of phospholipids in the samples varied between 38.1 and 45% (w/v)., (Copyright © 2017 Elsevier Ltd. All rights reserved.) more...- Published
- 2017
- Full Text
- View/download PDF
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