RESUMO
Natural pigments from haloarchaea are of great interest; bacterioruberin is the major pigment, it shows higher antioxidant power when compared with ß-carotene. However, characterization of bacterioruberin and its isomers along with its antioxidant and the matrix metallopeptidase 9 (MMP-9) inhibition activities in extracts from Natronoccoccus sp. TC6 and Halorubrum tebenquichense SU10 was not previously described, being the aim of this work. The carotenoids profile was performed by UV-Vis spectrophotometry, thin-layer chromatography, nuclear magnetic resonance spectroscopy, and high-resolution mass spectrometry (UPLC-ESI-MS/MS). Antioxidant capacity was determined for DPPH, ABTS, and FRAP. In addition, MMP-9 inhibition was studied using docking simulations. The carotenoid profile of studied strains was composed of bacterioruberin, some derivatives like mono, bis, and tris anhydrobacterioruberin, and also some bacterioruberin cis isomers. The carotenoid pools showed antioxidant capacity for DPPH > ABTS > FRAP; Natronococcus sp. TC6 carotenoid pool was better for ABTS and DPPH, while Halorubrum tebenquichense SU10 carotenoid pool was better for FRAP. Additionally, docking and molecular dynamics suggest that bacterioruberin inhibits MMP-9 through hydrophobic interactions near the catalytic site. Bacterioruberin shows the higher binding energy of -8.3 (kcal/mol). The carotenoids profile of both strains was elucidated, their antioxidant activity and singular participation of each carotenoid on MMP-9 in silico inhibition were evaluated.
RESUMO
Phenolic compounds in camu-camu (Myrciaria dubia) have received interest due to their health-promoting effects. However, these compounds have been poorly investigated in the different parts of the camu-camu fruit (pulp, peel, and seeds). This study aimed to optimize the solvent composition for extraction of phenolic compounds from pulp, peels, and seeds of camu-camu through a simplex-centroid mixture design. Then, the profile of phenolic compounds in samples of camu-camu pulp, peels, and seeds from different regions in Brazil and South America was determined by UPLC-ESI-MS/MS. Aqueous ethanol (80%, v/v) yielded the highest extraction for the pulp and peel, while aqueous methanol (50%, v/v) was selected for the seed. Camu-camu parts had p-coumaric acid, catechin, epicatechin, luteolin, rutin, and quercetin, with catechin as the major compound in the pulp, peels, and seeds of all the evaluated samples. The peel showed lower concentrations of these compounds compared with the pulp and the seed; the content of phenolic compounds also differed according to the geographic region. These results broaden the knowledge on phytochemical extraction and composition of camu-camu pulp, peel, and seed and may guide future applications of their extracts in the food industry.
Assuntos
Catequina , Myrtaceae , Brasil , Catequina/análise , Frutas/química , Myrtaceae/química , Fenóis/análise , Extratos Vegetais/química , Espectrometria de Massas em TandemRESUMO
Acremonium camptosporum, a fungus associated with the marine sponge Aplysina fulva, was collected from the isolated mid-Atlantic Saint Peter and Saint Paul Archipelago, Brazil, and was found to produce secondary metabolites that displayed antibacterial activities. Mass spectra data obtained by UPLC-ESI-MS/MS analyses of these extracts were compared to several databases and revealed the presence of several different cytotoxic acremonidins and acremoxanthones. The close association between the sponge and the fungi with its compounds could be of strategic importance in defending both from the high predation pressure and spatial competition in the warm-water scarps of the islands.
Assuntos
Acremonium , Poríferos , Animais , Brasil , Ilhas , Espectrometria de Massas em TandemRESUMO
Hancornia speciosa is a medicinal plant with proven antihypertensive activity. The cyclitol l-(+)-bornesitol is the main constituent of its leaves and is a potent inhibitor of the angiotensin-converting enzyme. We herein investigated the pharmacokinetic properties of bornesitol administered orally to Wistar rats, as well as bornesitol permeation in Caco-2 cells. Bornesitol was isolated and purified from an ethanol extract of H. speciosa leaves. An ultra-high performance liquid chromatography coupled with electrospray ionization mass spectrometry (UPLC-ESI-MS/MS) method was developed and validated to quantify bornesitol in rat plasma based on Multiple Reaction Monitoring, using pentaerythritol as an internal standard. Pharmacokinetics was evaluated by the administration of single doses via intravenous in bolus (3â¯mg/kg) and gavage (3, 15 and 25â¯mg/kg). Bornesitol permeation was assayed in a transwell Caco-2 cells model, tested alone, or combined with rutin, or as a constituent of H. speciosa extract, using a developed and validated UPLC-ESI-MS/MS method. All assayed validation parameters (selectivity, residual effect, matrix effect, linearity, precision, accuracy and stability of analyte in plasma and solution) for the bioanalytical method met the acceptance criteria established by regulatory guidelines. Bornestiol reached peak plasma concentration within approximately 60â¯min after oral administration with a half-life ranging from 72.15â¯min to 123.69â¯min. The peak concentration and area under the concentration-time curve of bornesitol did not rise proportionally with the increasing doses, suggesting a non-linear pharmacokinetics in rats and the oral bioavailability ranged from 28.5%-59.3%. Bornesitol showed low permeability in Caco-2 cells, but the permeability apparently increased when it was administered either combined with rutin or as a constituent of H. speciosa extract. In conclusion, bornesitol was rapidly absorbed after a single oral administration to rats and followed a non-linear pharmacokinetics. The obtained data will be useful to guide further pre-clinical development of bornesitol-containing herbal preparations of H. speciosa as an antihypertensive agent.
Assuntos
Anti-Hipertensivos/farmacocinética , Apocynaceae , Cromatografia Líquida de Alta Pressão , Ciclitóis/farmacocinética , Extratos Vegetais/farmacocinética , Espectrometria de Massas por Ionização por Electrospray , Espectrometria de Massas em Tandem , Administração Oral , Animais , Anti-Hipertensivos/administração & dosagem , Anti-Hipertensivos/sangue , Anti-Hipertensivos/isolamento & purificação , Apocynaceae/química , Disponibilidade Biológica , Células CACO-2 , Ciclitóis/administração & dosagem , Ciclitóis/sangue , Ciclitóis/isolamento & purificação , Humanos , Injeções Intravenosas , Absorção Intestinal , Mucosa Intestinal/metabolismo , Masculino , Modelos Biológicos , Dinâmica não Linear , Permeabilidade , Extratos Vegetais/administração & dosagem , Extratos Vegetais/sangue , Extratos Vegetais/isolamento & purificação , Ratos WistarRESUMO
Ageratina havanensis (Kunth) R. M. King & H. Robinson is a species of flowering shrub in the family Asteraceae, native to the Caribbean and Texas. The aim of this work was to compare the quantitative chemical composition of extracts obtained from Ageratina havanensis in its flowering and vegetative stages with the antioxidant potential and to determine the effects on P-glycoprotein (P-gp) function. The quantitative chemical composition of the extracts was determined quantifying their major flavonoids by UPLC-ESI-MS/MS and by PCA analysis. The effects of the extracts on P-gp activity was evaluated by Rhodamine 123 assay; antioxidant properties were determined by DPPH, FRAP and inhibition of lipid peroxidation methods. The obtained results show that major flavonoids were present in higher concentrations in vegetative stage than flowering stage. In particular, the extracts obtained in the flowering season showed a significantly higher ability to sequester free radicals compared to those of the vegetative season, meanwhile, the extracts obtained during the vegetative stage showed a significant inhibitory effect against brain lipid peroxidation and a strong reductive capacity. This study also showed the inhibitory effects of all ethanolic extracts on P-gp function in 4T1 cell line; these effects were unrelated to the phenological stage. This work shows, therefore, the first evidence on: the inhibition of P-gp function, the antioxidant effects and the content of major flavonoids of Ageratina havanensis. According to the obtained results, the species Ageratina havanensis (Kunth) R. M. King & H. Robinson could be a source of new potential inhibitors of drug efflux mediated by P-gp. A special focus on all these aspects must be taking into account for future studies.
Assuntos
Membro 1 da Subfamília B de Cassetes de Ligação de ATP/metabolismo , Ageratina/química , Antioxidantes/química , Antioxidantes/farmacologia , Ativação do Canal Iônico/efeitos dos fármacos , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Cromatografia Líquida de Alta Pressão , Relação Dose-Resposta a Droga , Estrutura Molecular , Reprodutibilidade dos Testes , Sensibilidade e Especificidade , Espectrometria de Massas por Ionização por Electrospray , Espectrometria de Massas em TandemRESUMO
The byproducts (seeds and peels) of an avocado cultivated in the south of Colombia were extracted with aqueous acetone and their antioxidant properties were measured with ABTS (2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) and DPPH (2,2-diphenyl-1-picrylhydrazyl) assays, and total polyphenol content was determined by Folin-Ciocalteu method. A bioguided fractionation was performed, first by SPE (solid phase extraction) on Amberlite XAD-7, and then by size exclusion chromatography on Sephadex LH-20. The polyphenolic-rich extracts and their fractions were analyzed by ultra-performance liquid chromatography-electrospray ionization-mass spectrometry (UPLC-ESI-MS/MS), finding the presence of organic acids, hydroxycinnamic acids, catechins, free and glycosylated flavonoids, and dimeric and trimeric procyanidins. Catechin, epicatechin, six quercetin derivatives, four dimeric procyanidins (three type B and one type A), and three trimeric procyanidins (two type B and one type A) were detected in the most active fractions of avocado peel and seeds. The most antioxidant fractions contain the higher molecular weight phenolic compounds (condensed tannins).
Assuntos
Persea/química , Polifenóis/química , Sementes/química , Espectrometria de Massas em Tandem/métodos , Catequina/química , Colômbia , Ácidos Cumáricos/química , Fenóis/química , Proantocianidinas/químicaRESUMO
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 IC50 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.