Navegando por Autor "Reis, Adriana Cotta Cardoso"
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Item Anti-Zika virus activity and chemical characterization by ultra-high performance liquid chromatography (UPLC-DAD-UV-MS) of ethanol extracts in Tecoma species.(2020) Reis, Adriana Cotta Cardoso; Silva, Breno de Mello; Moura, Hélia Maria Marques de; Pereira, Guilherme Rocha; Brandão, Geraldo CélioBackground: 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 (EC50 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.Item Antiviral activity and chemical characterization of Cissus erosa (Vitaceae) ethanol extracts.(2020) Reis, Adriana Cotta Cardoso; Moura, Hélia Maria Marques de; Silva, Breno de Mello; Oliveira, Alaíde Braga de; Brandão, Geraldo CélioCissus erosa (Vitaceae), popularly known in Brazil as Cipó-fogo, is a medicinal plant used in the treatment of warts and external ulcers. The present study aimed to evaluate the activity of stems and leaves ethanol extracts of C. erosa against the Dengue and Zika virus by the MTT colorimetric method and to carry on the phytochemical characterization of active extracts by high performance liquid chromatography coupled to mass spectrometry (UPLC-MS). Only the leaves ethanol extract showed anti-Dengue virus activity EC50 18.2 μg/ml (SI > 27.5) and low cytotoxicity for LLCMK2 cells (CC50 > 500 mg/ml). Both extracts (stems and leaves) showed anti-Zika virus activity with EC50 of 45.8 mg/ml and 82.8 mg/ml, respectively. These extracts presented CC50 of 309.2 μg/ml (leaves) and 387.6 μg/ml (stems) to Vero cells. Analysis by CCD and HPLC-DAD detected the presence of triterpenes, steroids, flavonoids and tannins. UPLC-MS analyses of these extracts, allowed the identification of the majority of flavonoids present known as vitexin, isovitexin, orientin, isoorientin and two flavones derivatives, methoxyluteolin-6(8)-C-hexosyl and luteolin-7,4’-di-O-glycosylflavone. The results of the phytochemical studies here described suggest that flavonoids and terpenoids are the substances that contribute to the antiviral activity of the ethanol extracts within this species.Item Anti–zika virus activity and isolation of flavonoids from ethanol extracts of Curatella americana L. leaves.(2023) Lima, Lienne D’Auria; Reis, Adriana Cotta Cardoso; Sousa, Jordano Augusto Carvalho; Valente, Gabriel Mendonça; Silva, Breno de Mello; Magalhães, Cíntia Lopes de Brito; Kohlhoff, Markus; Teixeira, Luiz Fernando de Medeiros; Brandão, Geraldo CélioThe 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 (CC50 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.Item Anti–Zika virus activity and isolation of flavonoids from ethanol extracts of Curatella americana L. Leaves.(2023) Lima, Lienne D’Auria; Reis, Adriana Cotta Cardoso; Sousa, Jordano Augusto Carvalho; Valente, Gabriel Mendonça; Silva, Breno de Mello; Magalhães, Cíntia Lopes de Brito; Kohlhoff, Markus; Teixeira, Luiz Fernando de Medeiros; Brandão, Geraldo CélioThe 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 (CC50 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.Item Chromatographic profile of xanthones and flavonoids in the anti-dengue extracts of Fridericia samydoides (Cham.) L.G. Lohmann (Bignoniaceae).(2022) Fonseca, Juliane Morais da; Reis, Adriana Cotta Cardoso; Pereira, Guilherme Rocha; Moura, Hélia Maria Marques de; Souza Filho, José Dias de; Silva, Breno de Mello; Brandão, Geraldo CélioThe flavonoids and xanthones present in the ethanol extracts of leaves and stems of Fridericia samydoides showed that anti-dengue activities in vitro were investigated qualitatively by liquid chromatography–ultraviolet-mass spectrometry in series. Nineteen flavones and fifteen xanthones were detected and characterized on the basis of their fragmentation pattern in the positive and negative ion mode tandem mass spectrometry spectra and ultraviolet bands. Acacetin, chrysin, vitexin, isovitexin, orientin, isoorientin, mangiferin, 2’-O-trans-caffeoylmangiferin, 2’-O-trans-coumaroylmangiferin and 2’-O-trans-cinnamoylmangiferin were identified by comparison with authentic samples. The other compounds detected were tentatively assigned by analysis of the spectral data and by comparison with literature reports. In addition, it performed the fractionation of the leaves extract leading to the isolation of mangiferin, isovitexin and isoorientin. All extracts and isolated compounds inhibited the Dengue virus replication cycle with EC50 less than 25.0 μg/mL for extracts and 272.5, 85.6 and 79.3 μg/mL for mangiferin, isovitexin and isoorientin, respectively.Item Cytotoxic activity of extracts from Tecoma species and isolated lignans.(2022) Reis, Adriana Cotta Cardoso; Silva, Breno de Mello; Souza Filho, José Dias de; Pereira, Guilherme Rocha; Brandão, Geraldo CélioA phytochemical study of Tecoma genus (Bignoniaceae) was accomplished by antitumor activity of ethanolic extracts. Species of this genus are composed of small shrubs often used as ornamental plants. The Tecoma stans species is used in folk medicine for different purposes. Recent work shows in vitro anticancer activity against human breast cancer. The ethanolic extracts from leaves and trunks of Tecoma casneifolia, T. garrocha, T. stans var. angustata and T. stans var. stans were tested in vitro. The assays used were against line tumor cells by the MTT method and the most active extracts were further studied. In this way, the ethanolic extract from T. stans var. stans trunks presented the higher cytotoxicity against the tumor cell lines studied (CC50 0.02 to 0.55 μg/ml) when compared to the other extracts tested (CC50 0.08 to 200.0 μg/ml). Accordingly, this extract was selected for chromatographic fractionation from which five known lignans were isolated. Further, paulownin, paulownin acetate, sesamin, olivil and cycloolivil were identified using 13C and 1 H NMR, IR, UV and spectroscopy and spectrometric MS techniques. These isolated compounds were tested and exhibited CC50 ranging from 13.01 to100.0 μg/ml which is superior to the ethanolic extract of trunk of T. stans.Item Effects of experimental conditions on solubility measurements for BCS classification in order to improve the biowaiver guidelines.(2021) Monteiro, Patrícia Fernanda; Barcellos, Neila Marcia Silva; Caldeira, Tamires Guedes; Reis, Adriana Cotta Cardoso; Ribeiro, Amanda Santos; Souza, Jacqueline deAmong the methods described for determining the solubility, shake-flask is suitable to evaluate the equilibrium solubility according to the BCS. Nevertheless, experimental conditions related to the shake-flask method are not well described. Evaluating the effects of experimental conditions on solubility measurements by shake-flask method is important and contributes in biowaiver decision. For this work, propranolol hydrochloride and nimesulide were used as model compound of high and low solubility, respectively. Equilibrium solubility was evaluated at 37 oC, 100 rpm during 48 hours in buffer media. Effects of the rotation speed, temperature, substance in excess and aliquot withdrawn were evaluated. Small variations of temperature caused significant differences in the solubility and then this parameter must be controlled. Excess of raw material influenced the results of the nimesulide, then, little excess is recommended. Rotation speed did not cause differences in the equilibrium solubilities, but at 150 rpm the equilibrium was reached faster. Aliquot did not present significant differences, but excessive withdrawn should be avoided. Therefore, the evaluation of equilibrium solubility using shake-flask method must be performed in physiological pH conditions, 37 ± 1 oC, substance in excess 10% above saturation, 50, 100 or 150 rpm and aliquot withdrawn not more than 10% of the media volume.Item Estudo fitoquímico biomonitorado para atividade citotóxica de espécies do gênero Tecoma (Bignoniaceae) e síntese de derivados triazólicos.(2017) Reis, Adriana Cotta Cardoso; Brandão, Geraldo Célio; Brandão, Geraldo Célio; Souza, Gustavo Henrique Bianco de; Leite, João Paulo VianaPlantas Bignoniaceae são amplamente utilizadas na medicina tradicional devido à presença de substâncias bioativas que possuem atividades importantes em benefício da saúde humana, dentre às várias atividades inclui-se a antitumoral. Tecoma é um gênero com reduzido número de espécies, sendo a T. stans (L.) Juss. ex Kunth a principal espécie deste gênero. Tecoma stans possui algumas variedades, delas a var. stans e a var. angustata são consideradas categorias populacionais significativas. Extratos de folhas e de caules de T. castaneifolia, T. garrocha, T. stans var. angustata e T. stans var. stans (coleta 1 e coleta 2) foram preparados por percolação a frio com EtOH comercial (92,8° GL) e os perfis cromatográficos foram obtidos por cromatografia liquida de ultra eficiência em fase reversa acoplada ao detector de ultravioleta (DAD) e ao espectrômetro de massas (CLUE-FR-DAD-EM). Os extratos de caules de T. stans var. stans (coleta 1 e coleta 2) foram submetidos a fracionamento por partição líquidolíquido, utilizando solventes de polaridade crescente. As frações diclorometano (FD), acetato de etila (FA) e a hidrometanólica obtidas foram avaliadas quanto à presença de lignanas, utilizando padrões previamente isolados. FD e FA da coleta 1 e a FA da coleta 2 foram fracionadas em coluna de sílica gel. O sólido isolado denominado de TSC–1 foi submetido a modificações moleculares, via reação “Click”, com a finalidade de obter derivados triazólicos mais ativos. A atividade citotóxica in vitro de extratos etanólicos de espécies do gênero Tecoma, bem como das substâncias isoladas e sintetizadas, foram avaliadas frente às linhagens celulares de carcinoma hepático, carcinoma de bexiga e adenocarcinoma de ovário, pelo método colorimétrico do MTT. Dos perfis cromatográficos dos extratos obtidos por CLUE-FR-DAD-EM foram identificados compostos fenólicos, dentre eles derivados de feniletanoides, lignanas e flavonoides. Cinco lignanas foram isoladas: paulownina (TSC–1), acetato de paulownina (TSC–2), sesamina (TSC–3), olivil (TSC–4) e cicloolivil (TSC–5), e um derivado feniletanoide, denominado de TSC–6. Os extratos de caules demonstraram maior atividade citotóxica do que os extratos de folhas, dentre eles, o extrato de caules de T. stans var. stans foi o mais citotóxico frente às três linhagens celulares. TSC–1 e TSC–2 apresentaram atividades citotóxicas frente às três linhagens celulares. Os derivados triazólicos: AC1015A, AC1019A, AC1024A, MC1071A, MC1068B, MC1070B e MC1072B apresentaram maior atividade citotóxica que TSC–1.Item Glucosyl-1,2,3-triazoles derived from eugenol and analogues : synthesis, anti-Candida activity, and molecular modeling studies in CYP-51.(2021) Magalhães, Lorena Severiano de; Reis, Adriana Cotta Cardoso; Nakao, Izadora Amaral; Péret, Vinícius Augusto Campos; Reis, Rúbia Castro Fernandes Melo; Silva, Naiara Chaves; Dias, Amanda Latercia Tranches; Carvalho, Diogo Teixeira; Dias, Danielle Ferreira; Brandão, Geraldo Célio; Braga, Saulo Fehelberg Pinto; Souza, Thiago Belarmino deThis work describes the synthesis, anti-Candida, and molecular modeling stud- ies of eighteen new glucosyl-1,2,3-triazoles derived from eugenol and corre- lated phenols. The new compounds were characterized by combined Fourier Transform Infrared, 1 H and 13C 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 antifun- gal activity, nine compounds showed anti-Candida potential and the peracety- lated 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 deacety- lated 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 dynam- ics 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 sub- stituents at the phenyl ring.Item High-resolution mass spectrometry identification and characterization of flavonoids from Fridericia chica leaves extract with anti-arbovirus activity.(2022) Cruz, Ana Flávia Gomes da; Reis, Adriana Cotta Cardoso; Sousa, Jordano Augusto Carvalho; Vaz, Luana Beatriz Araújo; Silva, Breno de Mello; Magalhães, Cíntia Lopes de Brito; Kohlhoff, Markus; Oliveira, Alaíde Braga de; Brandão, Geraldo CélioPlant 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 CC50 ≥ 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.Item 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.(2020) Silva, Regislainy Gomes da; Almeida, Tamires Cunha; Reis, Adriana Cotta Cardoso; Vieira Filho, Sidney Augusto; Brandão, Geraldo Célio; Silva, Glenda Nicioli da; Sousa, Hildeberto Caldas de; Almeida, Vera Lúcia de; Lopes, Júlio César Dias; Souza, Gustavo Henrique Bianco deEthanolic (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 mg/mL). By means of UPLC-DADMS/MS data were identified the flavonoids astragaline, nicotiflorin, kaempferol-7-O-rutinoside, robinin, hyperin, rutin, quercetin-7-Orutinoside and manghaslin. EB (800 mg/mL) and SEM (1200 mg/mL) reduces the T24 cell viability. These extracts at 25 mg/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.Item Novel lignan-based compounds via click chemistry : paulownin isolation, structural modifications and cytotoxic activity evaluations.(2020) Pereira, Guilherme Rocha; Ferreira, Andreza Cristina Gomes; Costa, Flávia; Munhoz, Victor Hugo; Alvarenga, Denis Fernando; Silva, Breno de Mello; Reis, Adriana Cotta Cardoso; Brandão, Geraldo CélioPaulownin, 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 and 13C) 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.Item Synthesis and structural characterization of new benzylidene glycosides, cytotoxicity against cancer cell lines and molecular modeling studies.(2021) Péret, Vinícius Augusto Campos; Reis, Adriana Cotta Cardoso; Silva, Naiara Chaves; Dias, Amanda Latercia Tranches; Carvalho, Diogo Teixeira; Dias, Danielle Ferreira; Braga, Saulo Fehelberg Pinto; Brandão, Geraldo Célio; Souza, Thiago Belarmino deThis work describes the synthesis, structural characterization (by combined Fourier Transform Infrared - FTIR, 1H and 13C Nuclear Magnetic Resonance - NMR spectroscopy and High Resolution Mass Spectrometry - HRMS) and biological evaluation of a new series of glycosides designed from a benzylidene glucoside derived from eugenol (23) active against Candida glabrata. The mass accuracy between the calculated and found values observed in HRMS analyses were lower than 5 ppm, which are acceptable for proposing a molecular formula using this technique. We decided to keep the benzylidene group of 23, while changing either the saccharide unit (glucose or galactose) or the natural aglycone (eugenol, isoeugenol, dihydroeugenol or guaiacol) to check their influence in antifungal activity. Since the chemical modifications performed did not contribute to enhance the antifungal activity, the synthesized compounds (23– 30) were further screened against four cancer cell lines (HeLa: cervix carcinoma; MDA-MB-231: breast carcinoma; T-24: urinary bladder carcinoma; and TOV-21G: ovarian carcinoma). The glucoside 27 showed promising activities (IC50 10.08–59.91 μM) against all the assayed cancer cell lines and higher values of selectivity index than doxorubicin, the control drug. The galactoside 28 demonstrated interesting results against HeLa, MDA-MB-231 and T-24 cells. This compound was active at 17.41 μM with a selectivity index greater than 13.7 against the HeLa cells, while doxorubicin was active at 10.01 μM with a selectivity index close to 1.5 considering this cell line. Further, we performed docking studies of these compounds with type II topoisomerase-DNA complex (TOP2) in order to try to explain their mechanism of action.Item Synthesis, chemical characterization and antimicrobial activity of new acylhydrazones derived from carbohydrates.(2019) Guilherme, Fernanda Dias; Simonetti, Julia Évelin; Folquitto, Laís Regina dos Santos; Reis, Adriana Cotta Cardoso; Oliver, Josidel Conceição; Dias, Amanda Latercia Tranches; Dias, Danielle Ferreira; Carvalho, Diogo Teixeira; Brandão, Geraldo Célio; Souza, Thiago Belarmino deA new series of glycosylated acylhydrazones was synthesized and all the chemical structures were confirmed by High Resolution Mass Spectrometry (HRMS), 1 H and 13C Nuclear Magnetic Resonance (1 HNMR; 13C-NMR) and Fourier Transform Infrared (FTIR) spectroscopy methods. The mass accuracy between the calculated and found values observed in HRMS analyses were near or lower than 5 ppm, which are acceptable for proposing a molecular formula using this technique. All of the synthesized compounds were screened for their antibacterial, antifungal and antiviral activities. Five compounds (12, 13, 14, 16 and 19) exerted a modest antifungal activity against the strains evaluated. Derivative 14 showed fungicidal activity against Candida glabrata at 173.8 mM and saccharide unit contributed to the increase of the antifungal potential against this strain. New chemical manipulation of derivative 14 can make it possible to obtain new potentially antimicrobial agents.Item Synthesis, trypanocidal and cytotoxic activities of α,β-unsaturated ketones derived from eugenol and analogues.(2022) Reis, Rúbia Castro Fernandes Melo; Reis, Adriana Cotta Cardoso; Torchelsen, Fernanda Karoline Vieira da Silva; Lana, Marta de; Sales Júnior, Policarpo Ademar; Brandão, Geraldo Célio; Braga, Saulo Fehelberg Pinto; Souza, Thiago Belarmino deThis work describes the synthesis, structural characterization, trypanocide and cytotoxic evaluation of α,β-unsaturated ketones derived from eugenol and analogues. Among the synthesized compounds, the cyclopentanonic/dihydroeugenol derivative 12 was active against amastigote forms of Trypanosoma cruzi at 5.2 nM (700 times more potent than benznidazole) and represents a potential hit for future structural optimizations to reduce its toxicity. All the compounds were also evaluated against a healthy human and four cancer cell lines and the derivative 10 was more active than doxorubicin against three cancer cells (IC50 values between 2.03–23.51 μM) and showed the higher selectivity index considering the human cells. Derivative 14 was also more potent and selective than doxorubicin against two cancer cells (IC50 values between 4.71–8.86 μM).Item Triagem de atividade antiviral in vitro frente a arbovírus de extratos etanólicos de espécies da família Bignoniaceae, Cissus erosa (Vitaceae) e substâncias isoladas.(2021) Reis, Adriana Cotta Cardoso; Brandão, Geraldo Célio; Brandão, Geraldo Célio; Rocha, Leandro Machado; Dolabela, Maria Fâni; Magalhães, Cíntia Lopes de Brito; Santos, Orlando David Henrique dosArboviroses são doenças causada por vírus transmitidos aos seres humanos por artrópodes hematófagos cronicamente infectados. Dentre as arboviroses de importância em saúde pública destacam-se as causadas pelos vírus do gênero Alphavirus, como Chikungunya virus e Mayaro virus, e do gênero Flavivirus, como dengue virus e Zika virus. Até o momento não existe tratamento específico para estas arboviroses, logo a busca por fármacos antivirais é urgente devido à rápida expansão destes vírus nos países tropicais e subtropicais, bem como sua emergência e reemergência. Plantas das famílias Bignoniaceae e Vitaceae são utilizadas na medicina tradicional popular devido à presença de bioativos que possuem atividades importantes em benefício da saúde humana e dentre elas inclui-se atividade antiviral. No presente trabalho, foi realizada uma triagem de 51 extratos para atividade antiviral in vitro frente aos arbovírus: Zika virus, Chikungunya virus e Mayaro virus pelo método colorimétrico do MTT. Destes, 49 foram obtidos de espécies da família Bignoniaceae e 2 da espécie Cissus erosa (Vitaceae). Os resultados foram expressos em termos de concentração efetiva média (CE50) e índice de seletividade (IS). Além disso, foram determinados os perfis cromatográficos dos extratos ativos por UPLC-DAD-EM, bem como foi realizado fracionamento biomonitorado de extratos ativos e promissores. Da triagem inicial da atividade antiviral a partir de 51 extratos, 29 foram ativos contra os arbovírus exibindo atividade promissora e seletiva (CE50 ≤ 50,0 μg/mL e IS ≥ 2,0), e de forma geral, inibiram, principalmente, o ciclo de multiplicação dos alfavírus. Os perfis cromatográficos de 9 espécies foram determinados e compostos fenólicos, como feniletanoides, e, principalmente, flavonoides foram caracterizados, diversos deles foram pela primeira vez descritos nas espécies em estudo. Além disso, foi realizado fracionamento biomonitorado de 6 extratos ativos. Destas frações obtidas, foi pela primeira vez isolado um feniletanoide a partir da fração acetato de etila do extrato de caules de Tecoma stans var. stans, identificado como crenatosideo e apresentou potencial atividade anti-Zika virus com CE50 de 34,78 μM e IS de 4,25, sendo 11,12 vezes mais ativo que o controle positivo, ribavirina (CE50 = 386,84 μM). Também foi isolado um flavonoide durante fracionamento do extrato de folhas de Millingtonia hortensis que foi identificado como hispidulina e exibiu inédita atividade frente o Mayaro virus com CE50 de 32,20 μM e IS de 6,47, esta foi 3,7 vezes mais ativa que a ribavirina, e contra o Chikungunya vírus com CE50 de 78,83 μM e IS de 2,65, sendo 5,3 vezes mais ativa que o controle positivo, amantadina (CE50 = 418,98 μM). Adicionalmente, um éster de cadeia longa de um ácido orgânico foi pela primeira vez isolado da fração em diclorometano do extrato de caules de Tecoma castaneifolia, este foi parcialmente identificado, denominado de TC01, e exibiu potente atividade frente os três arbovírus com CE50 variando de 6,16 a 10,51 μg/mL e IS entre 4,33 e 7,39. Os resultados obtidos neste trabalho demonstram que a família Bignoniaceae e os seus metabólitos secundários, como compostos fenólicos, flavonoides e feniletanoides, são promissoras fontes de substâncias com potencial atividade antiviral contra os arbovírus Zika virus, Chikungunya virus e Mayaro virus.