RESUMO
The leaves of the aromatic neotropical shrub Hedyosmum brasiliense are employed popularly as a sedative, aphrodisiac and as a substitute for green tea. Sesquiterpene lactones and phenolic compounds were characterized as the main compounds of its aqueous extract, and some biological investigation demonstrated its anxiolytic, antidepressant and hypnotic effects. The quantification of podoandin, onoseriolide and rosmarinic acid in its infused tea was achieved by means of ultra high performance liquid chromatography coupled to a electronspray ionization interface and a high resolution mass detector. Quantification of the analytes was performed employing the areas of the extracted ion chromatograms of the analytes, negative ion mode for rosmarinic acid (1) and positive mode for podoandin (2) and onoseriolide (3). The method was validated by evaluating specificity, linearity, precision and accuracy and has been found to be sensitive, precise and accurate. When applied to analyze the hot water infusion extract of H. brasiliense, compounds 1, 2 and 3 were obtained to be 188 ± 1.45 mg/g, 1.9 ± 0.15 mg/g and 1.7 ± 0.02 mg/g of extract, respectively. The H. brasiliense tea was found to be a good source of the rosmarinic acid, also widely employed in the cosmetic industry.
Assuntos
4-Butirolactona/análogos & derivados , Cromatografia Líquida/métodos , Cinamatos/análise , Cicloeptanos/análise , Depsídeos/análise , Sesquiterpenos/análise , Traqueófitas/química , 4-Butirolactona/análise , Modelos Lineares , Extratos Vegetais/química , Reprodutibilidade dos Testes , Sensibilidade e Especificidade , Espectrometria de Massas em Tandem/métodos , Ácido RosmarínicoRESUMO
Currently, there is an increasing interest on the development of topical formulations containing rosmarinic acid (RA) due to its well-documented antioxidant activity. This study aimed to develop and validate a stability-indicating ultra-fast liquid chromatography (UFLC) method for the determination of RA in nanoemulsions, porcine skin and nasal mucosa intended to be applied in permeation/retention studies and for development of topical nanoemulsions. Chromatographic separation was carried out using a C18 column packed with 2.6⯵m particle size in isocratic conditions using as mobile phase water:acetonitrile (83:17, v/v), acidified with 0.1% trifluoracetic acid (v/v), with a total time of analysis of 3.5â¯min and detection at 330â¯nm. RA analysis was specific in the presence of both non-biological (blank nanoemulsion and receptor fluid) and biological matrices (porcine ear skin and porcine nasal mucosa). No interference of degradation products of RA was verified after different stress conditions such as acidic, alkaline, oxidative, light exposure (UV-A and UV-C) and thermal demonstrating the method stability-indicating property. The analytical (0.1-10.0⯵g·mL-1) and bioanalytical (0.5-10.0⯵g·mL-1) linearity was proved by analysis of the calibration curves of RA and no matrix effect was observed. The method was sensitive, precise and accurate, and showed recovery higher than 85%. The method was considered robust as evaluated by a Plackett-Burman experimental design. In the validated conditions, the RA was determined in the nanoemulsions obtained by spontaneous emulsification procedure (1.007⯱â¯0.040â¯mg·mL-1), porcine ear skin (1.13⯱â¯0.19⯵g·cm-2) and nasal mucosa (22.46⯱â¯3.99⯵g·cm-2) after retention/permeation studies. Thus, a highly sensitive, simple, fast and stability-indicating method was developed for RA analysis during the development of topical nanoemulsions and bioanalytical assays in complex matrices.
Assuntos
Cromatografia Líquida/métodos , Cinamatos/análise , Depsídeos/análise , Emulsões/química , Nanoestruturas/química , Mucosa Nasal/química , Pele/química , Animais , Cinamatos/química , Depsídeos/química , Estabilidade de Medicamentos , Ensaios de Triagem em Larga Escala/métodos , Limite de Detecção , Modelos Lineares , Reprodutibilidade dos Testes , Suínos , Ácido RosmarínicoRESUMO
The aim of this work was to assess the nutritional and functional components of powder obtained by lyophilization of whole fruits, seeds, pulp and skin from chilto (Solanum betaceum Cav) cultivated in the ecoregion of Yungas, Argentina. The powders have low carbohydrate and sodium content and are a source of vitamin C, carotenoid, phenolics, potassium and fiber. The HPLC-ESI-MS/MS analysis of the fractions enriched in phenolics allowed the identification of 12 caffeic acid derivatives and related phenolics, 10 rosmarinic acid derivatives and 7 flavonoids. The polyphenols enriched extracts before and after simulated gastroduodenal digestion inhibited enzymes associated with metabolic syndrome, including α-glucosidase, amylase and lipase and exhibited antioxidant activity by different mechanisms. None of the analyzed fruit powders showed acute toxicity or genotoxicity. The powders from the three parts of S. betaceum fruit may be a potential functional food and the polyphenol enriched extract of seed and skin may have nutraceutical properties.
Assuntos
Frutas/química , Síndrome Metabólica/tratamento farmacológico , Estresse Oxidativo/efeitos dos fármacos , Preparações de Plantas/farmacologia , Sementes/química , Solanum/química , Antioxidantes/análise , Antioxidantes/farmacologia , Argentina , Ácido Ascórbico/análise , Carotenoides/análise , Cinamatos/análise , Depsídeos/análise , Fibras na Dieta/análise , Feminino , Flavonoides/análise , Flavonoides/farmacologia , Inibidores de Glicosídeo Hidrolases/análise , Inibidores de Glicosídeo Hidrolases/farmacologia , Humanos , Concentração Inibidora 50 , Lipase/antagonistas & inibidores , Lipase/metabolismo , Masculino , Compostos Fitoquímicos/análise , Compostos Fitoquímicos/farmacologia , Preparações de Plantas/química , Polifenóis/análise , Potássio na Dieta/análise , Pós/química , Recomendações Nutricionais , Espectrometria de Massas em Tandem , alfa-Amilases/antagonistas & inibidores , alfa-Amilases/metabolismo , alfa-Glucosidases/metabolismo , Ácido RosmarínicoRESUMO
A green solvent-based optimization for rosmarinic acid (RA), carnosol (COH), and carnosic acid (CA) extraction, the three main antioxidants from rosemary, was performed. The conventional solid-liquid extraction was optimized using a central composite design (CCD) followed by the desirability approach. In the CCD analysis the quantitative effects of extraction time (4.8-55.2min), liquid-to-solid ratio (4.6-21.4mLg(-1)), and ethanol content (44.8-95.2% v/v) were determined for the extracted amount of antioxidants, their concentrations in the extract, and the extraction yield. Samples were analyzed by HPLC and the antioxidants were identified by comparison with pure standard retention times and UV spectra. The desirability function that simultaneously maximizes the antioxidants extraction and their concentrations in the final product was validated. The extraction using a hydroalcoholic solution 70% v/v, at low liquid-to-solid ratio (5mLg(-1)), and after 55-min yielded an antioxidant recovery rate of 89.8%, and a final product 4.75 times richer in the main antioxidants than the raw material.
Assuntos
Abietanos/análise , Antioxidantes/análise , Cinamatos/análise , Depsídeos/análise , Extratos Vegetais/análise , Rosmarinus/química , Pós/química , Ácido RosmarínicoRESUMO
Vitex megapotamica (Sprengel) Moldenke belongs to the Verbenaceae family and is popularly known as "tarumã". The antioxidant capacity of fractions and crude extract from the leaves of V. megapotamica were determined in this study through the capacity to remove reactive species and phenolic compounds were quantified in the various fractions. The IC50 (DPPH) ranged from 14.17 ± 0.76 to 37.63 ± 0.98 µg/mL. The ethyl acetate fraction might contain the strongest lipid peroxidation inhibitory compounds with an IC50 of 16.36 ± 5.09 µg/mL, being also the one with the highest content of polyphenols (522.4 ± 1.12 mg/g), flavonoids (220.48 ± 0.30 mg/g) and condensed tannins (3.86 ± 0.53 mg/g). Compounds quantified by HPLC/DAD in the crude extract and fractions were chlorogenic and rosmarinic acids. Higher dosages of the extracts were more effective in reducing levels of plasma protein carbonyls and were also shown to be able to remove reactive species by a 2',7'-dichlorofluorescein diacetate assay, reducing oxidative stress in all tested fractions. Results obtained indicated that V. megapotamica exhibits good potential to prevent diseases caused by the overproduction of free radicals and it might also be used as a potential source of natural antioxidant agents.
Assuntos
Antioxidantes/análise , Flavonoides/análise , Polifenóis/análise , Taninos/análise , Vitex/química , Antioxidantes/química , Antioxidantes/farmacologia , Ácido Clorogênico/análise , Cromatografia Líquida de Alta Pressão , Cinamatos/análise , Depsídeos/análise , Flavonoides/química , Flavonoides/farmacologia , Extratos Vegetais/química , Extratos Vegetais/farmacocinética , Folhas de Planta/química , Polifenóis/química , Polifenóis/farmacologia , Espécies Reativas de Oxigênio/metabolismo , Taninos/química , Taninos/farmacologia , Ácido RosmarínicoRESUMO
Jaboticaba (Myrciaria cauliflora) and false jaboticaba (Myrciaria vexator) fruits are two pleasant-tasting, dark-colored fruits, native to Brazil. They are rich sources of phenolic compounds, including anthocyanins, flavonoids, phenolic acids, and tannins, as well as less well known polyphenols such as depsides. These two fruits are very similar in morphology, but their taste profiles differ markedly. This study was focused on identifying the marker compounds between them using HPLC-PDA and LC-TOF-MS, combined with principal component analysis. As a result, cyanidin-3-O-glucoside was found as the major anthocyanin in Myrciaria fruits. Delphinidin-3-O-glucoside was found to be the marker compound for jaboticaba, while cyanidin-3-O-galactoside and cyanidin-3-O-arabinose were two marker compounds distinguishing false jaboticaba. In addition, two ellagitannins, iso-oenothein C and oenothein C, were isolated and identified from both of these fruits for the first time. Jaboticabin, a minor bioactive depside, occurred in both fruits and, because of its potential to treat chronic obstructive pulmonary disease, was successfully synthesized in the laboratory.
Assuntos
Frutas/química , Hidroxibenzoatos/análise , Myrtaceae/química , Antocianinas/análise , Brasil , Cromatografia Líquida de Alta Pressão , Depsídeos/análise , Glucosídeos/análise , Taninos Hidrolisáveis/análise , Hidroxibenzoatos/síntese química , Extratos Vegetais/análise , Polifenóis/análise , Análise de Componente Principal , Espectrometria de Massas por Ionização por Electrospray , Taninos/análiseRESUMO
In this paper we investigated the antibacterial activity of a methanolic extract of Rosmarinus officinalis L. and their main constituents, carnosic acid and rosmarinic acid, against 37 nosocomial strains of multidrug-resistant bacteria. Results obtained showed that both the rosemary extract and carnosic acid inhibited all clinical isolates of Staphylococcus aureus methicillin-resistant and Enterococcus faecalis gentamicin and streptomycin-resistant bacteria examined (MICs 60 ug/mL vs. 200 ug/mL, respectively). Rosemary extract showed MIC values between 400 and 1600 ug/ml against the Gram-negative multidrug-resistant bacteria: Escherichia coli, Proteus mirabilis, Enterobacter cloacae, Pseudomonas aeruginosa, Morganella morganii and Providencia stuartii, while carnosic acid showed MIC of 120 to 240 ug/mL. Bactericidal effect of carnosic acid against S. aureus and E. faecalis was observed at their MIC value, while 2 x MIC to 4 x MIC were needed to kill Gram-negative bacteria. Rosmarinic acid showed a narrow spectrum of action against a few Gram-negative clinical isolates. Our findings suggest that carnosic acid would be a good lead candidate useful in counteracting drug-resistant infections.
En este trabajo evaluamos la actividad antibacteriana de un extracto metanólico de Rosmarinus officinalis L. y sus principales componentes el ácido carnósico y ácido rosmarínico, contra 37 cepas de bacterias multirresistentes nosocomiales. Los resultados muestran que el extracto de romero y el ácido carnósico, inhibieron las bacterias Gram-positivas Staphylococcus aureus resistentes a meticilina y Enterococcus faecalis resistentes a gentamicina y estreptomicina (CIM 200 ug/mL y 60 ug/mL, respectivamente). El extracto de romero inhibió los Gram negativos multirresistentes: Escherichia coli, Proteus mirabilis, Enterobacter cloacae, Pseudomonas aeruginosa, Morganella morganii y Providencia stuartii (CIM 400 a 1600 ug/mL), mientras que el ácido carnósico mostró valores de CIM entre 120 a 240 ug/mL. El ácido carnósico mostró actividad bactericida contra S. aureus y E. faecalis a su CIM, mientras que 2 a 4 X CIM se requirieron para matar las bacterias Gram-negativas. El ácido rosmarínico mostró inhibió unos pocos aislados clínicos Gram-negativos. Estos hallazgos sugieren que el ácido carnósico puede ser de utilidad contra infecciones bacterianas multirresistentes a antibióticos.
Assuntos
Antibacterianos/farmacologia , Bactérias , Cinamatos/farmacologia , Abietanos/farmacologia , Extratos Vegetais/farmacologia , Rosmarinus/química , Bactérias/isolamento & purificação , Cinamatos/análise , Depsídeos/análise , Depsídeos/farmacologia , Abietanos/análise , Extratos Vegetais/química , Farmacorresistência Bacteriana Múltipla , Testes de Sensibilidade Microbiana , RosmarinusRESUMO
Prunella vulgaris L. (Labiatae) contains a variety of structurally diverse natural products, primarily rosmarinic acid (RA), ursolic acid (UA) and oleanolic acid (OA), which possess a wide array of biological properties. In the present study, P. vulgaris was harvested at three developmental stages (vegetative, full-flowering and mature-fruiting stages), dissected into stem and leaf tissues and assayed for chemical contents using high performance liquid chromatography. Significant changes in the concentrations of the major secondary metabolites (RA, UA and OA) were observed at the different development stages. The highest concentrations of RA, UA and OA were found at the full-flowering stage (15.83 mg/g dry weight (DW) RA, 1.77 mg/g DW UA and 0.65 mg/g DW OA). Among the different aerial parts of the plant, the concentrations of RA, UA and OA were higher in the leaves than in the stems at the different developmental stages. These results suggest that the full-flowering stage is characterized by the highest concentrations of bioactive compounds. Therefore, this stage may be the optimum point for harvesting P. vulgaris plants. In additional, the leaves of P. vulgaris demonstrated higher RA, UA and OA concentrations than the stems, suggesting higher utilization potential.
Assuntos
Cinamatos/análise , Depsídeos/análise , Ácido Oleanólico/análise , Extratos Vegetais/química , Prunella/química , Triterpenos/análise , Cromatografia Líquida de Alta Pressão , Frutas/química , Folhas de Planta/química , Caules de Planta/química , Ácido Rosmarínico , Ácido UrsólicoRESUMO
Many dark-colored fruit juices, rich in anthocyanins, are thought to be important for human health. Joboticaba (Myrciaria cauliflora) fruits, native to Brazil, have phenolics including anthocyanins and are processed into juice and other products. The phenolic constituents in the fruits of jaboticaba were studied by high-performance liquid chromatography coupled with electrospray ionization time-of-flight mass spectrometry. Twenty-two compounds were identified or tentatively determined by detailed analysis of their mass spectral fragmentation patterns; 11 compounds including 7 gallotannins, 2 ellagic acid derivatives, syringin, and its glucoside were detected for the first time in the fruit. The compositional differences among the fruit extracts and their commercial products were also compared by principal component analysis; two anthocyanins, delphinidin 3-O-glucoside and cyanidin-3-O-glucoside, as well as two depsides, jaboticabin and 2-O-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxyphenylacetic acid, present in the fruit extracts were not detected unexpectedly in commercial jaboticaba juice or jam. Therefore, the stability of anthocyanins in jaboticaba fresh fruits and products has been compared directly with that of other dark-colored fruit products made from blueberry and Concord grape, and the same trend of decreasing amounts of anthocyanins was observed in all tested products. The antioxidant activities (DPPH(â¢) and ABTS(â¢+)) of jaboticaba fresh fruit extract and commercial samples were also compared. Principal component analysis proved to be a useful way to discern changes between fresh and processed fruits. Jaboticaba is a promising fruit with antioxidant capacity similar to those of other so-called superfruits; however, during processing the levels of some of anthocyanins and other polyphenols decrease significantly, and therefore the capacity of these products to affect human health may vary significantly from that of the fresh fruit.
Assuntos
Bebidas/análise , Frutas/química , Myrtaceae/química , Antocianinas/análise , Antioxidantes/análise , Mirtilos Azuis (Planta)/química , Brasil , Cromatografia Líquida de Alta Pressão/métodos , Depsídeos/análise , Ácido Elágico/análise , Ácido Gálico/análise , Glucosídeos/análise , Taninos Hidrolisáveis/análise , Hidroxibenzoatos/análise , Fenilpropionatos/análise , Polifenóis/análise , Análise de Componente Principal , Vitis/químicaRESUMO
INTRODUCTION: Official assays for the quality control of Melissa officinalis L. (Lamiaceae) leaves establish the quantification of total hydroxycinnamic derivatives expressed as rosmarinic acid. OBJECTIVE: The goal of this work was to develop a simple, fast and reliable method for monitoring the phenolic composition in herbs from the Lamiaceae family and for rapidly detecting M. officinalis adulteration or substitution in commercial medicinal samples in Argentina. METHODOLOGY: A capillary zone electrophoresis (CZE) method was performed under the following conditions: the background electrolyte (BGE) consisted of 20 m m sodium tetraborate buffer, pH 9.2; the applied voltage was 25 kV; the capillary and sample temperatures were kept at 25 °C; the hydrodynamic mode was selected for the sample injection (3.45 kPa during 5 s). RESULTS: A CZE method that achieved the separation and simultaneous determination of eight related phenolic compounds in less than 11 min was optimised for application to control quality analysis of M. officinalis-based products. The method was validated according to the US Federal Drug Agency requirements and offers advantages in terms of analysis time, cost and operation. CONCLUSIONS: The proposed methodology can be applied to the standardisation and quality control of plant material and phytopharmaceutical products derived from the Lamiaceae family, as indicated by the results obtained in the analysis of commercial medicinal products in Argentina.