RESUMO
Croton linearis Jacq. is an aromatic shrub that has been utilized in traditional medicine in the Bahamas, Jamaica, and Cuba. Recent studies have revealed the antiprotozoal potential of its leaves. The present work is aimed to identify the volatile constituents of essential oil from the stems of C. linearis (CLS-EO) and evaluate its in vitro antileishmanial activity. In addition, an in silico study of the molecular interactions was performed using molecular docking. A gas chromatographic-mass spectrometric analysis of CLS-EO identified 1,8-cineole (27.8%), α-pinene (11.1%), cis-sabinene (8.1%), p-cymene (5.7%), α-terpineol (4.4%), epi-γ-eudesmol (4.2%), linalool (3.9%), and terpinen-4-ol (2.6%) as major constituents. The evaluation of antileishmanial activity showed that CLS-EO has good activity on both parasite forms (IC50Promastigote = 21.4 ± 0.1 µg/mL; IC50Amastigote = 18.9 ± 0.3 µg/mL), with a CC50 of 49.0 ± 5.0 µg/mL on peritoneal macrophages from BALB/c mice (selectivity index = 2 and 3 using the promastigote and amastigote results). Molecular docking showed good binding of epi-γ-eudesmol with different target enzymes of Leishmania. This study is the first report of the chemical composition and anti-Leishmania evaluation of CLS-EO. These findings provide support for further studies of the antileishmanial effect of this product.
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Plectranthus neochilus Schltr. (Lamiaceae) is a plant recently introduced in Cuba. Worldwide, it is an ethnomedicinal alternative for its use against microbial infections, but the Cuban population use the extracts to treat sleep disorders. To address this apparent incongruity, four collections (from different seasonal conditions in the year) of Cuban P. neochilus cultivars were analyzed in terms of their pharmacognostic characteristics. Three extracts using fresh and dried leaves were chemically and biologically characterized. UPLC-DAD-MS/MS analysis was performed to determine their chemical composition, while a panel of nine microorganisms was used to evaluate their antimicrobial activity. Finally, cytotoxic effects of different fractions were measured in three cell lines by the resazurin viability assay. In contrast to previously reported micro and macromorphological properties of P. neochilus, the leaves from the Cuban cultivars did not present glandular trichomes, nor did they produce quantifiable levels of essential oils. Moreover, aqueous extracts used by the population revealed no significant antimicrobial activity and were not cytotoxic. The three extracts showed a similar phytochemical composition, i.e., eight flavonoids, seven abietane diterpenes, and rosmarinic acid as the major constituent, most of them reported for the first time in this species. The low yield of essential oil, the absence of glandular trichomes, compounds with a high level of oxidation, and a moderate antimicrobial activity detected were the most distinctive pharmacognostic and biological characteristics of P. neochilus grown in Cuba. These aspects could explain its non-use as an antimicrobial.
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Zanthoxylum pistaciifolium Griseb. is a tree endemic to Cuba, occasionally used in herbal medicine. Previously, the antitrypanosomal activity of a n-hexane-2-butanone extract of Z. pistaciifolium leaves and of its constituent skimmianine were published. In the current study a more thorough examination of the respective extract is performed, which led to the isolation and identification of three flavonoids, more specifically, the flavonol-3-O-methylethers kaempferol-3-O-methylether (1) and novel compounds kaempferol-3-O-methylether-5-O-ß-D-glucoside (2) and kaempferol-8-hydroxy-3,7-O-dimethylether-5-O-ß-D-glucoside (3). All compounds were screened for their antimicrobial and antiprotozoal activity and cytotoxicity towards MRC-5 SV2 cells. Compound 1 showed a moderate to weak activity against Trypanosoma cruzi (IC50 30.8 µM), T. brucei (IC50 15.4 µM) and Plasmodium falciparum (IC50 53.8 µM), but also showed cytotoxicity (CC50 19.0 µM). Compounds 2 and 3 did not display activity in any of the assays (IC50 and CC50 > 64 µM).[Formula: see text].
Assuntos
Rutaceae , Zanthoxylum , Glucosídeos , Quempferóis , Extratos Vegetais/farmacologiaRESUMO
Estudios fitoquímicos sugieren que Gymnanthes lucida Sw. (aité) es un candidato con potencial antioxidante. Se cuantificó el contenido de fenoles y flavonoides totales, y se evaluó la actividad antioxidante de extractos, elagitaninos y cumarinas aisladas de la hoja y la corteza mediante los métodos de secuestro de los radicales 2,2-difenil-1-pricrilhidrazil (DPPH) y ácido 2,2´-azino-bis(3-etilbenzotiazolín)-6-sulfónico (ABTS) y del poder reductor. El extracto de la hoja mostró el mayor contenido de flavonoides y fenoles y la mejor actividad de los extractos DPPH (IC50=12,82 ± 0,12 µg/mL), ABTS (IC50=13,83 ± 3,45 µg/mL) y poder reductor (104% respecto al ácido ascórbico). El ácido elágico (AE) mostró la mayor actividad de las muestras DPPH (IC50=11,75 ± 0,53 µg/mL), ABTS (IC50=11,28 ± 0,28 µg/mL) y poder reductor (107% respecto al ácido ascórbico). Los resultados sugieren que G. lucida es una fuente de antioxidantes donde el AE es el principal responsable de la actividad de la hoja.
Phytochemical investigations suggest that Gymnanthes lucida Sw. (aité) is a potential candidate for obtaining antioxidant principles. Total phenolic and flavonoid content were quantified and in vitro antioxidant capacity was assessed in extracts, ellagitannins, and coumarins isolated from the leaf and bark by three methods: 2,2-diphenyl-1-pricrylhydrazyl (DPPH) and 2,2´-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) radicals scavenging activities and ferric reducing power. The highest phenolic and flavonoid content was observed in the leaf extract which also exhibited the highest activity among the extracts DPPH (IC50=12,82 ± 0,12 µg/mL), ABTS (IC50=13,83 ± 3,45 µg/mL), and reducing power (104% compared to ascorbic acid). Ellagic acid (EA) showed the highest activity, with DPPH (IC50=11,75 ± 0,53 µg/mL), ABTS (IC50=11,28 ± 0,28 µg/mL), and reducing power (107 % compared to ascorbic acid). Results suggest that G. lucida is a natural source of antioxidants where EA is the main secondary metabolite of the leaf responsible for the activity.
Assuntos
Euphorbiaceae , Antioxidantes , Fenóis , Flavonoides , Extratos VegetaisRESUMO
Chloroform extract (CE) and fractions obtained from Aldama arenaria roots were evaluated for their in vitro antiproliferative activity against 10 human tumor cell lines [leukemia (K-562), breast (MCF-7), ovary expressing a multidrug-resistant phenotype (NCI/ADR-RES), melanoma (UACC-62), lung (NCI-H460), prostate (PC-3), colon (HT29), ovary (OVCAR-3), glioma (U251), and kidney (786-0)]. CE presented weak to moderate antiproliferative activity (mean log GI50 1.07), whereas fractions 3 and 4, enriched with pimaranetype diterpenes [ent-pimara-8(14),15-dien-19-oic acid and ent-8(14),15-pimaradien-3ß-ol], presented moderate to potent activity for most cell lines, with mean log GI50 of 0.62 and 0.59, respectively. The results showed promising in vitro antiproliferative action of the samples obtained from A. arenaria, with the best results for NCI/ADR-RES, HT29, and OVCAR-3, and TGI values ranging from 5.95 to 28.71 µg.ml -1, demonstrating that compounds of this class may be potential prototypes for the discovery of new therapeutic agents.
El extracto de cloroformo (CE) y las fracciones obtenidas de las raíces de Aldama arenaria fueron evaluadas por su actividad antiproliferativa in vitro contra 10 líneas celulares tumorales humanas [leucemia (K-562), mama (MCF-7), ovario que expresa un fenotipo resistente a múltiples fármacos (NCI/ADR-RES), melanoma (UACC-62), pulmón (NCI-H460), próstata (PC-3), colon (HT29), ovario (OVCAR-3), glioma (U251) y riñón (786-0)]. CE presentó actividad antiproliferativa débil a moderada (log GI50 promedio de 1.07), mientras que las fracciones 3 y 4, enriquecidas con diterpenos de tipo pimarane [ent-pimara-8 (14), ácido 15-dien-19-oico y ent-8 (14), 15-pimaradien-3ß-ol], presentaron actividad moderada a potente para la mayoría de las líneas celulares, con un log GI50 promedio de 0.62 y 0.59, respectivamente. Los resultados mostraron una prometedora acción antiproliferativa in vitro de las muestras obtenidas de A. arenaria, con los mejores resultados para NCI/ADR-RES, HT29 y OVCAR-3, y valores de TGI que van desde 5.95 a 28.71 µg.ml -1, lo que demuestra que los compuestos de esta clase pueden ser prototipos potenciales para el descubrimiento de nuevos agentes terapéuticos.
Assuntos
Extratos Vegetais/farmacologia , Clorofórmio , Plectranthus/química , Linhagem Celular Tumoral/efeitos dos fármacos , Proliferação de Células/efeitos dos fármacos , Técnicas In Vitro , Extratos Vegetais/química , Etnobotânica , Cuba , Diterpenos/farmacologia , Diterpenos/químicaRESUMO
BACKGROUND: Excoecaria lucida Sw. (Euphorbiaceae) is a plant conventionally used throughout the Caribbean in the treatment of infectious diseases. OBJECTIVE: To evaluate, using bioassay-guided fractionation, the in vitro cytotoxicity and antimicrobial activity of E. lucida leaves. MATERIALS AND METHODS: A 95% ethanol crude extract was dried and fractionated by solid-liquid separation in four phases (hexane, dichloromethane, ethyl acetate, and butanol). Antimicrobial activity (3 bacteria, 6 yeasts, and 2 fungi) was evaluated by the dilution method with resazurin (2048, 512, 128, 32, and 8 µg/mL). The cytotoxicity assays were evaluated in two cell lines: MRC-5 and RAW 264.7; calculating the selectivity index. Assays were performed for the total extract, the isolated compound with the highest yield, and the ethyl acetate and butanol phases. Isolated compounds were characterized by nuclear magnetic resonance and mass spectrometry techniques. RESULTS: Fractionation process led to the isolation of ellagic acid (784.29 mg), 3,3',4'-tri-O-methyl ellagic 4-O-ß-D-glucopyranoside acid (6.1 mg), and corilagin (6.91 mg). The most active were ethyl acetate phase and ellagic acid with IC50= 128 µg/mL against seven and five different species of microorganisms, respectively. The total extract (IC50=512 µg/mL) and the ethyl acetate phase (IC50=128 µg/mL) were cytotoxic in both cell lines, while butanol phase and ellagic acid both with IC50>2048 µg/mL seemed to be safer. CONCLUSIONS: The results obtained indicate that the Excoecaria leaves can be conventionally used as antimicrobial, but it should be present that some cytotoxicity could appear. In addition, the three identified compounds were reported for the first time in the species. SUMMARY: Excoecaria lucida leaves (Euphorbiaceae) are used by the Cuban population due to their antimicrobial activity. This ethnopharmacological knowledge is confirmed by the integrated antibacterial and antifungal in vitro screening developed, using the bioassay-guided fractionation method.Abbreviations Used: MRC-5-SV2: Diploid human lung fibroblasts cells, RAW 264.7: Murine macrophages cells, IC50: Inhibitory Concentration 50%, ATCC: American Type Culture Collection, CCEBI: Culture Collection of Industrial Biotechnology Center, CECT: Spanish Culture Collection Type, CFU: Colony forming units, CC50: 50% cytotoxic concentration, CO2: Carbon dioxide, SI: Selectivity index, IR: Infrared spectroscopy, 1H NMR: Nuclear Magnetic Resonance of hydrogen, 13C NMR: Nuclear Magnetic Resonance of carbon, HMQC: Heteronuclear Multiple-Quantum Correlation, HMBC: Heteronuclear Multiple Bond Correlation, COSY: Correlation Spectroscopy, NOESY: Nuclear Overhauser Effect Spectroscopy, KBr: Potassium bromide, DMSO-D6: Deuterated dimethyl sulfoxide, LC.MS: Liquid Chromatography-Mass Spectrometry, [α]D: Optical rotation, EL1: ellagic acid, EL2: 3,3',4'-tri-O-methyl ellagic 4-O-ß-D-glucopyranoside acid, EL3: corilagin, Active (+), inactive (-).
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INTRODUCCIÓN: excoecaria lucida Sw. (Aité), es una especie que crece en Cuba y en la región del Caribe. La misma ha sido poco estudiada por científicos a pesar de que la población la utiliza con fines medicinales, en lo principal como antiasmático, antimicrobiano y para el dolor dental. OBJETIVOS: determinar la composición química de las hojas, así como aislar e identificar estructuralmente metabolitos secundarios. MÉTODOS: las hojas secas y molidas, se maceraron 72 horas con etanol al 95 % y se repitió el procedimiento en 4 ocasiones. Al extracto total se le determinó su composición química cualitativa y posterior se fraccionó con solventes. La fase de mayor rendimiento fue estudiada por Cromatografía Líquida de Alta Resolución y aislada la sustancia mayoritaria, la cual fue caracterizada por espectroscopía infrarroja y de Resonancia Magnética Nuclear 1H y 13C a 500 MHz (HMQC, HMBC, COSY y NOESY). RESULTADOS: se determinó la presencia cualitativa de alcaloides, triterpenos y esteroides, quinonas, flavonoides, cumarinas, lactonas sesquiterpénicas, fenoles y taninos. De la fase de mayor rendimiento (butanólica= 23,48 g) se logró aislar e identificar el compuesto mayoritario perteneciente a un hemiterpenoide. CONCLUSIONES: los metabolitos secundarios detectados coinciden con los reportes para otras especies del género. Se informa por primera vez para el género y la especie el aislamiento e identificación del hemiterpenoide (2E)-2-metil-2-buten-1,4-diol-1-O-ß-D-glucopiranósido.
INTRODUCTION: excoecaria lucida Sw. (Aité), it is a species that grow in Cuba and at the Caribbean region. It has been scientifically quite a little studied, in spite of the fact that the population utilizes it due to their medicinal properties as antiasthmatic, antimicrobial, and for the toothache treatment. OBJECTIVES: to determine the chemical composition of leaves, as well as the isolation and identification of their secondary metabolites. METHODS: dried and milled leaves were macerated 72 hours with ethanol 95 %, repeating the procedure in 4 occasions. Total extract was determined in his chemical qualitative composition and afterwards it was fragmented with solvents. The phase with greater yield was studied by High Performance Liquid Chromatography and isolated the main substance, which was characterized by infrared and Nuclear Magnetic Resonance spectroscopy: uni-dimensional 1H and 13C at 500 MHz and bi-dimensional HMQC, HMBC, COSY and NOESY. RESULTS: the identification of Alkaloids, triterpenes and steroids, quinone, flavonoids, coumarins, sesqiterpenic lactones, tannins and phenols were accomplished. From the greater yield phase (butanol= 23.48 g) was isolated and identified the main compound, a hemiterpenoid. CONCLUSIONS: the identified secondary metabolites are in coincidence with other reports related to the genera. For first time the hemiterpene (2E)-2-methyl-2- buten-1,4-di-hydroxyl-1-O-ß-D-glucopyranoside is informed in this genera and specie.
Assuntos
Humanos , Plantas Medicinais/efeitos dos fármacos , Espectroscopia de Ressonância Magnética/métodos , Euphorbiaceae/efeitos dos fármacosRESUMO
Introducción: excoecaria lucida Sw. (Aité), es una especie que crece en Cuba y en la región del Caribe. La misma ha sido poco estudiada por científicos a pesar de que la población la utiliza con fines medicinales, en lo principal como antiasmático, antimicrobiano y para el dolor dental. Objetivos: determinar la composición química de las hojas, así como aislar e identificar estructuralmente metabolitos secundarios. Métodos: las hojas secas y molidas, se maceraron 72 horas con etanol al 95 por ciento y se repitió el procedimiento en 4 ocasiones. Al extracto total se le determinó su composición química cualitativa y posterior se fraccionó con solventes. La fase de mayor rendimiento fue estudiada por Cromatografía Líquida de Alta Resolución y aislada la sustancia mayoritaria, la cual fue caracterizada por espectroscopía infrarroja y de Resonancia Magnética Nuclear 1H y 13C a 500 MHz (HMQC, HMBC, COSY y NOESY). Resultados: se determinó la presencia cualitativa de alcaloides, triterpenos y esteroides, quinonas, flavonoides, cumarinas, lactonas sesquiterpénicas, fenoles y taninos. De la fase de mayor rendimiento (butanólica= 23,48 g) se logró aislar e identificar el compuesto mayoritario perteneciente a un hemiterpenoide. Conclusiones: los metabolitos secundarios detectados coinciden con los reportes para otras especies del género. Se informa por primera vez para el género y la especie el aislamiento e identificación del hemiterpenoide (2E)-2-metil-2-buten-1,4-diol-1-O-β-D-glucopiranósido(AU)
Introduction: excoecaria lucida Sw. (Aité), it is a species that grow in Cuba and at the Caribbean region. It has been scientifically quite a little studied, in spite of the fact that the population utilizes it due to their medicinal properties as antiasthmatic, antimicrobial, and for the toothache treatment. Objectives: to determine the chemical composition of leaves, as well as the isolation and identification of their secondary metabolites. Methods: dried and milled leaves were macerated 72 hours with ethanol 95 percent, repeating the procedure in 4 occasions. Total extract was determined in his chemical qualitative composition and afterwards it was fragmented with solvents. The phase with greater yield was studied by High Performance Liquid Chromatography and isolated the main substance, which was characterized by infrared and Nuclear Magnetic Resonance spectroscopy: uni-dimensional 1H and 13C at 500 MHz and bi-dimensional HMQC, HMBC, COSY and NOESY. Results: the identification of Alkaloids, triterpenes and steroids, quinone, flavonoids, coumarins, sesqiterpenic lactones, tannins and phenols were accomplished. From the greater yield phase (butanol= 23.48 g) was isolated and identified the main compound, a hemiterpenoid. Conclusions: the identified secondary metabolites are in coincidence with other reports related to the genera. For first time the hemiterpene (2E)-2-methyl-2- buten-1,4-di-hydroxyl-1-O-β-D-glucopyranoside is informed in this genera and specie(AU)
Assuntos
Espectroscopia de Ressonância Magnética/métodos , Plantas Medicinais , EuphorbiaceaeRESUMO
The antimicrobial activity of 13 total extracts was evaluated, 10 soft extracts (B) and 3 blended extracts (E) prepared from dry and fresh leaves of Petiveria alliacea L. Various solvents were used for their preparation: hydroalcoholic solution at 30%, 80% and isopropyl alcohol. The antimicrobial effect of the extracts was tested by means of the method of Kirby-Bauer, using four bacterial strains from the ATCC collection (Escherichia coli, Staphylococcus aureus, Enterococcus faecalis and Pseudomonas aeruginosa) and a leveduriform fungus (Candida albicans). The following quality control parameters were determined for most active extracts: physical, physical-chemical and chemical parameters. The results were: nine extracts showed antibacterial activity, being the most concentrated (B8 and E3), the ones with the highest activity in the presence of the bacteria tested; the effect of blended extracts (E1, E2 and E3) was greater in the presence of P. aeruginosa. Blended extracts are considered more potent and active than soft extracts. No antifungal activity was obtained for both types of extracts. The Minimum Inhibitory Concentration (MIC) and Minimum Bactericidal Concentration (MBC) were determined for both extracts, with the following results: MIC-soft extracts (>100 mg/mL), blended extracts (>50 mg/mL); MBC-soft extracts (≥400 mg/mL), blended extracts (≥200 mg/mL) based on fresh leaves.
Avaliou-se a atividade antimicrobiana de 13 extratos totais, 10 brandos (B) e 3 batidos (E) elaborados a partir da folha seca e fresca da Petiveria alliacea L. Para sua preparação se empregaram vários solventes: solução hidroalcoólica 30%, 80% e álcool isopropílico. O efeito antimicrobiano dos extratos foi comprovado pelo método do Kirby-Bauer, usando para isso quatro cepas bacterianas da coleção ATCC (Escherichia coli, Staphylococcus aureus, Enterococcus faecalis e Pseudomonas aeruginosa) e um fungo leveduriforme (Candida albicans). Determinaram-se parâmetros de controle da qualidade físicos, físico-químicos e químicos dos extratos mais ativos. Obtiveram-se como resultados: que 9 extratos mostraram atividade antibacteriana, sendo os mais concentrados (B8 e E3) os de maior espectro de ação frente às bactérias provadas; o efeito dos extratos batidos (E1, E2 e E3) foi maior frente a P. aeruginosa; os extratos batidos se consideram mais ativos que os brandos e não se obteve atividade antifúngica caso algum. Determinou-se a Concentração Mínima Inhibitoria e Bactericida para ambos os extratos, resultando a primeira para os extratos brandos maior a 100 mg/mL e para as batidos maior a 50 mg/mL; a segunda para os extratos brandos maior ou igual a 400 mg/mL e para as batidos maior ou igual a 200 mg/mL, em relação à droga fresca.
Assuntos
Técnicas In Vitro/classificação , Extratos Vegetais/análise , Phytolaccaceae/fisiologia , Testes de Sensibilidade Microbiana , Anti-InfecciososRESUMO
Se informa sobre las reacciones adversas de 10 plantas medicinales, sus interacciones con medicamentos y el impacto producido. A los efectos se realizó una amplia revisión bibliográfica, para lo cual se seleccionaron aquellas especies vegetales muy bien documentadas en literaturas científicas. Se halló que muchas plantas medicinales provocan efectos indeseables e interactúan con medicamentos, de modo que en algunos casos atentan contra la vida del paciente o afectan la farmacocinética y farmacodinamia; ello justifica tener especial cuidado cuando se trata de niños, ancianos y embarazadas. Dichas interacciones se producen con medicamentos anticoagulantes, antihipertensivos, sedantes, antidepresivos, hipoglucemiantes y digitálicos. La divulgación de esta información es importante para los profesionales de la salud y la comunidad, dado que el consumo actual de las especies vegetales con fines terapéuticos se encuentra muy extendido en todas partes del mundo y muchas personas se automedican con estas, desconociendo sus acciones y convencidas de que resultan totalmente inocuas
Assuntos
Incompatibilidade de Medicamentos , Plantas MedicinaisRESUMO
Se informa sobre las reacciones adversas de 10 plantas medicinales, sus interacciones con medicamentos y el impacto producido. A los efectos se realizó una amplia revisión bibliográfica, para lo cual se seleccionaron aquellas especies vegetales muy bien documentadas en literaturas científicas. Se halló que muchas plantas medicinales provocan efectos indeseables e interactúan con medicamentos, de modo que en algunos casos atentan contra la vida del paciente o afectan la farmacocinética y farmacodinamia; ello justifica tener especial cuidado cuando se trata de niños, ancianos y embarazadas. Dichas interacciones se producen con medicamentos anticoagulantes, antihipertensivos, sedantes, antidepresivos, hipoglucemiantes y digitálicos. La divulgación de esta información es importante para los profesionales de la salud y la comunidad, dado que el consumo actual de las especies vegetales con fines terapéuticos se encuentra muy extendido en todas partes del mundo y muchas personas se automedican con estas, desconociendo sus acciones y convencidas de que resultan totalmente inocuas