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6. Phytochemical study of Magonia pubescens A. St.-Hil. and cytotoxicity of branches aqueous extract on breast cancer and leukemia cells.

Author

Moraes, Acácio R. A., Siqueira, Ezequias P., Kohlhoff, Markus, Evangelista, Fernanda C. G., Sabino, Adriano P., Vieira Filho, Sidney A., Alcântara, Antônio F. C., Duarte, Lucienir P., and Sousa, Grasiely F.

Subjects
CYTOTOXINS, BREAST cancer, CANCER cells, SEBORRHEIC dermatitis, FRUIT seeds
Abstract

Magonia pubescens is a natural species from the Brazilian cerrado biome. Its fruits and seeds are used in the treatment of seborrheic dermatitis, a common inflammatory skin disease. In this work, the known compounds lapachol, stigmasterol, maniladiol and scopoletin were isolated from hexane and dichloromethane extracts of M. pubescens branches. The aqueous extract of this material was fractioned through a liquid-liquid partition and the obtained fractions were analyzed by UHPLC-MS/MS. The results obtained were compared with data from three databases, leading to the putative identification of 51 compounds from different classes, including flavonoids, saponins and triterpenes. The cytotoxicity of aqueous fractions was assayed against breast cancer (MDA-MB-231) and leukemia (THP-1 and K562) cells. The best activity was observed for fraction AE3 against MDA-MB-231 cells (IC50 30.72 µg.mL−1). [ABSTRACT FROM AUTHOR]

Published
2024
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9. Phytochemical study of Magonia pubescens A. St.-Hil. and cytotoxicity of branches aqueous extract on breast cancer and leukemia cells

Author

Moraes, Acácio R. A., primary, Siqueira, Ezequias P., additional, Kohlhoff, Markus, additional, Evangelista, Fernanda C. G., additional, Sabino, Adriano P., additional, Vieira Filho, Sidney A., additional, Alcântara, Antônio F. C., additional, Duarte, Lucienir P., additional, and Sousa, Grasiely F., additional

Published
2023
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10. Evaluation of Magonia pubescens A. St.-Hill. Roots Extract against Phytopathogens: Searching for Eco-Friendly Crop Protection Products

Author

Moraes, Acácio R. A., primary, Sabina, Samuel R., additional, Expósito, Daniela G., additional, Giménez, Cristina, additional, Espinel, Guacimara, additional, Sousa, Grasiely F., additional, Duarte, Lucienir P., additional, Jiménez, Ignacio A., additional, Cabrera, Raimundo, additional, and Bazzocchi, Isabel L., additional

Published
2023
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12. Phytochemical study of Magonia pubescens A. St.-Hil. and cytotoxicity of branches aqueous extract on breast cancer and leukemia cells

Author

Moraes, Acácio R. A., Siqueira, Ezequias P., Kohlhoff, Markus, Evangelista, Fernanda C. G., Sabino, Adriano P., Filho, Sidney A. Vieira, Alcântara, Antônio F. C., Duarte, Lucienir P., and Sousa, Grasiely F.

Abstract

Magonia pubescens is a natural species from the Brazilian cerrado biome. Its fruits and seeds are used in the treatment of seborrheic dermatitis, a common inflammatory skin disease. In this work, the known compounds lapachol, stigmasterol, maniladiol and scopoletin were isolated from hexane and dichloromethane extracts of M. pubescens branches. The aqueous extract of this material was fractioned through a liquid-liquid partition and the obtained fractions were analyzed by UHPLC-MS/MS. The results obtained were compared with data from three databases, leading to the putative identification of 51 compounds from different classes, including flavonoids, saponins and triterpenes. The cytotoxicity of aqueous fractions was assayed against breast cancer (MDA-MB-231) and leukemia (THP-1 and K562) cells. The best activity was observed for fraction AE3 against MDA-MB-231 cells (IC50 30.72 µg.mL−1).

Published
2023
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13. Friedelane Triterpenes with Cytotoxic Activity from the Leaves of Maytenus quadrangulata (Celastraceae)

Author

Aguilar,Mariana G. de, Sousa,Grasiely F. de, Evangelista,Fernanda C. G., Sabino,Adriano P., Camargo,Karen C., Vieira Filho,Sidney A., Nunes,Yule R. F., and Duarte,Lucienir P.

Subjects
pentacyclic triterpenes, cytotoxicity, Celastraceae, Maytenus
Abstract

Three new triterpenes, 3,4-seco-3,11β-epoxyfriedel-4(23)-en-3β-ol (1), friedelan-3α,11β diol (2), 7β,26-epoxyfriedelan-3a,7a-diol (3), a mixture of two new triterpenes 3α-hydroxyfriedelan-29-yl palmitate (4) and 3α-hydroxyfriedelan-29-yl stearate (5) and eleven known compounds were obtained from the hexane extract of Maytenus quadrangulata leaves. The structures and the relative stereochemistry of the new triterpenes were established through 1D/2D nuclear magnetic resonance (NMR), high resolution mass spectrometry (HRMS), and Fourier transform infrared (FTIR) spectral data. The hexane extract and isolated compounds were submitted to the cytotoxicity assays against leukemia (THP-1 and K562), ovarian (TOV-21G) and breast cancer (MDA-MB-231) cell lines. Compounds 1, 2 and 11β-hydroxyfriedelan-3-one (15) displayed high cytotoxicity and selectivity against leukemic cells when compared to positive control cytarabine (for THP-1) and imatinib (for K562). Furthermore, compound 2 showed similar cytotoxicity and an enhanced selectivity towards ovarian and breast cells in comparison to positive control etoposide.

Published
2022

19. Chemodiversity of Essential Oils from Nine Species of Celastraceae

Author

Camargo, Karen C., primary, Duarte, Lucienir P., additional, Vidal, Diogo M., additional, Pereira, Hebert V., additional, Pereira, Rafael C. G., additional, Aguilar, Mariana G., additional, Sousa, Grasiely F., additional, Filho, Sidney A. Vieira, additional, Mercadante‐Simões, Maria O., additional, Messias, Maria Cristina T. B., additional, and Oliveira, Djalma M., additional

Published
2020
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20. Influence of Environmental Factors and Cultural Methods on the Content of N,N-Dimethyltryptamine in Psychotriaviridis (Rubiaceae)

Author

Cavalcante,André D., Cardoso,Gabriele A., Oliveira,Fernando L. P.de, Bearzoti,Eduardo, Okuma,Adriana A., Duarte,Lucienir P., and Vieira-Filho,Sidney A.

Subjects
DMT, secondary metabolite, chacrona, ayahuasca
Abstract

Psychotria viridis is one of the species that produces N,N-dimethyltryptamine. Its decoction together with other species, such as Banisteriopsis caapi, produces ayahuasca, a beverage used for ritualistic and medicinal purposes. The goal of this study was to understand how environmental factors and cultivation methods influenced the content of N,N-dimethyltryptamine in P. viridis. Over all four seasons, leaf samples were collected from 25 different locations in 14 Brazilian states, and Federal District. Environmental parameters, micro and macronutrients, plant characteristics, information on farming methods were correlated with N,N-dimethyltryptamine content, determined by gas chromatography coupled to mass spectrometry (GC-MS). Greatest effects on the N,N-dimethyltryptamine amount were associated with seasonality, altitude, latitude and biome type. A positive correlation between N and Mg content and N,N-dimethyltryptamine levels was statistically established. By regression analysis, the adequate foliar nutrient levels that would result in the concentration of N,N-dimethyltryptamine in cultivated plants similar to that of Amazonian P. viridis were equated.

Published
2018

22. Cannabinoid CB2 receptors and spinal microglia are implicated in tingenonemediated antinociception in mice.

Author

Moura, Clarice C. V., dos Santos, Rafaela S., Duarte, Lucienir P., and Galdino, Giovane

Subjects
CANNABINOID receptors, MICROGLIA, LABORATORY mice, SYNTHETIC marijuana, CANNABINOIDS, SPINAL cord, FACIAL pain, VISCERAL pain
Abstract

Objective: To investigate the antinociceptive effect of tingenone on inflammatory pain, as well as and the involvement of the cannabinoid receptors type 2 (CB2) and spinal microglia in this process. Methods: Male Swiss mice were subjected to inflammatory pain induced by intraplantar injection of carrageenan. The nociceptive threshold was measured by von Frey filaments test. Tingenone was administered orally 60 min before carrageenan injection. To evaluate the involvement of CB2 receptor, endocannabinoids, and microglia, AM630 (a CB2 receptor antagonist), MAFP (an inhibitor of an enzyme that hydrolyses endocannabinoids), and minocycline (a microglial inhibitor) were given intrathecally 20 min before tingenone administration. In addition, an immunofluorescence assay was used to evaluate CB2 receptor and CD11B (a microglial marker) expression in the spinal cord dorsal horn. Results: Tingenone significantly reduced carrageenan-induced hyperalgesia, which was reversed by pretreatment with AM630. MAFP and minocycline potentiated and prolonged the tingenoneinduced antinociception. CD11B expression was increased in the spinal cord dorsal horn of mice with inflammatory pain pretreated with tingenone, which was reduced by AM630, MAFP, and minocycline. Conclusions: CB2 receptors and endocannabinoids participate in the tingenone-induced antinociception which may involve the inhibition of microglia at spinal level. [ABSTRACT FROM AUTHOR]

Published
2021
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23. Imines and lactones derived from friedelanes and their cytotoxic activity.

Author

Aguilar, Mariana G., Sousa, Grasiely F., Evangelista, Fernanda C. G., Sabino, Adriano P., Vieira Filho, Sidney A., and Duarte, Lucienir P.

Subjects
BAEYER-Villiger rearrangement, LACTONES, CELL lines, IMINES, CARBONYL group
Abstract

Friedelan-3-one (1) and friedelane-3,16-dione (2) isolated from leaves and branches of Maytenus robusta Reissek were subjected to structural modifications via nucleophilic addition to the carbonyl group and Baeyer-Villiger oxidation in order to synthesize potential cytotoxic compounds. The oximes friedelane-3-hydroxyimino (3) and 3-hydroxyiminofriedelan-16-one (4) together with the lactones friedelane-3,4-lactone (5) and 3,4-lactonefriedelan-16-one (6) were characterized by IR and NMR spectroscopic analyses. Compounds 4 and 6 are reported for the first time. Cytotoxic screening via MTT assay in human leukemia cell lines (THP-1 and K562) demonstrated no significant improvement of compounds 3-6 when compared to the starting materials. Only compounds 3 and 5 demonstrated an improvement against K562 cells. However, the same assay on ovarian and breast cancer cell lines (TOV-21G and MDA-MB-231) showed a reduction in the IC50 for compounds 4-6, indicating that ring A modifications may enhance the biological potential. [ABSTRACT FROM AUTHOR]

Published
2020
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26. Antidiarrheal activity of extracts from Maytenus gonoclada and inhibition of Dengue virus by lupeol

Author

SILVA, FERNANDO C., primary, RODRIGUES, VANESSA G., additional, DUARTE, LUCIENIR P., additional, LULA, IVANA S., additional, SINISTERRA, RUBEN D., additional, VIEIRA-FILHO, SIDNEY A., additional, RODRIGUES, RODRIGO A.L., additional, KROON, ERNA G., additional, OLIVEIRA, PATRÍCIA L., additional, FARIAS, LUIZ M., additional, MAGALHÃES, PAULA P., additional, and SILVA, GRÁCIA D.F., additional

Published
2017
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29. Antioxidant activity of Maytenus imbricata Mart., Celastraceae

Author

Silva, Grácia D. F., Silva, Silvia R. S., Barbosa, Luiz C. A., Duarte, Lucienir P., Ribeiro, Sonia M. R., Queiroz, José H., Vieira Filho, Sidney A., and Oliveira, Márcio L. R.

Subjects
Atividade antioxidante, poder redutor, Antioxidant activity, reducer power, Celastraceae, Maytenus imbricata
Abstract

The free radical scavenging activity (FRS) using 2,2-diphenyl-1-picrylhydrazyl (DPPH), the reducer power and the total phenolic concentration of extracts and compounds isolated from leaves, branches and roots of Maytenus imbricata Mart. (Celastraceae) were evaluated. Some extracts, a mixture of phenolic compounds (MPC) and epicatechin showed higher RP and FRS (DPPH) activities in comparison with the standard butylhydroxyanisole (BHA) and galic acid (GA) used in assays. The ethyl acetate extract from leaves showed higher total phenolic content and also higher RP and FRS (DPPH) than the other extracts. These facts indicate that there are some relations between phenolic concentration in the extract and the antioxidant activity and the reducer power. The solvent used in the extraction process influences the chemical composition of the extracts and consequently its antioxidant and reducer power activities. A atividade antioxidante, poder redutor (RP) e a atividade coletora de radicais livres (FRS) usando 2,2-difenil-1-picrilhidrazil (DPPH), e a concentração de substâncias fenólicas totais dos extratos e substâncias isoladas das folhas, caules e raízes de Maytenus imbricata Mart. (Celastraceae) foram avaliados. Alguns extratos, a mistura de compostos fenólicos e epicatequina mostraram alto poder redutor e atividade antioxidante (DPPH) em comparação com o padrão butilhidroxianisol (BHA) e ácido gálhico (GA) utilizados no ensaio. O extrato acetato de etila das folhas mosraram alto teor de substâncias fenólicas e alto poder redutor e atividade antioxidante em relação aos outros extratos. Este fato indica haver alguma relação entre a concentração de substâncias fenólicas e o poder redutor. O solvente usado no processo de extração influencia a composição química dos extratos e, consequentemente, as atividades redutoras e antioxidantes.

Published
2009

49. Algistatic effect of a quinonamethide triterpene on Microcystis novacekii.

Author

Silva, Fernando C., Guedes, Fernanda A. F., Franco, Maione W., Barbosa, Francisco A. R., Marra, Camila A., Duarte, Lucienir P., Silva, Grácia D. F., and Vieira-Filho, Sidney A.

Abstract

Cyanobacteria proliferation represents a problem to water treatment for human consumption supply. Species of the genus Microcystis, commonly found in continental waters, can bloom and produce microcystine and other toxic compounds associated to human and animal poisoning, depending on the nutrient levels present in the water. The use of natural products to control cyanobacteria blooms is promising since they are less harmful to the environment than compounds obtained by organic syntheses. Triterpenes, which are associated with several biological activities, have been isolated from species of the genus Maytenus (Celastraceae), commonly found in Cerrado regions of Brazil. Tingenone is a pentacyclic triterpene that has cytotoxic properties and induces growth inhibition in some microorganisms. In this study, the effects of tingenone isolated from Maytenus gonoclada at distinct concentrations (e.g., 50, 150, 500, 1,500, and 4,500 μg  L −1) on the growth rates of Microcystis novacekii was investigated. The algicide activity was verified using M. novacekii cultures growing in ASM1 culture medium at 23 °C and continuous illumination for 96 h. Growth inhibition was monitored by light microscopy and optical density (OD 680 nm). The median effective concentration associated to the M. novacekii inhibition growth induced by tingenone was 12.2 μg  L −1. The result indicates that tingenone has algicide effect and can be potentially applied in water management for public supply, replacing synthetic algicides. [ABSTRACT FROM AUTHOR]

Published
2013
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50. Salicassin, an Unprecedented ChalconeDiterpene Adduct and a Quinone Methide Triterpenoid from Maytenus salicifolia.

Author

Magalhães, Cássia G., de Fátima Silva, Grácia D., Duarte, Lucienir P., Bazzocchi, Isabel L., Diaz, Antonio J., Moujir, Laila, López, Manuel R., Figueiredo, Rute C., and Vieira Filho, Sidney A.

Abstract

In continuation of our work on Maytenus salicifolia, we report herein the isolation and structural elucidation of two new compounds, salicassin ( 1), a diterpene-chalcone adduct with an unprecedented C-framework, and (16 β)-16-hydroxypristimerin ( 2), a quinone methide triterpenoid. Their structures were elucidated on the basis of spectroscopic analysis, including 1D- and 2D-NMR techniques (COSY, ROESY, HSQC, and HMBC). In addition, 22 known compounds were isolated and characterized by comparison of their spectra with reported data. Compound 2, structurally related to the well known cytotoxic quinone methide triterpenoids, exhibited an antiproliferative effect on HeLa, A-549, and HL-60 human cell lines, with IC50 values of 2.2, 3.2, and 2.7 μ M, respectively. [ABSTRACT FROM AUTHOR]

Published
2013
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