Characterization of flours from the aroeira leaf (Schinus terebinthifolius Raddi), obtained by different drying methods.

The present work aimed at the development and characterization of aroeira leaf flour (Schinus terebinthifolius Raddi), obtained by lyophilization and drying in an air circulation oven. The technological, physical, physico-chemical, morphological, functional, and microbiological aspects were analyzed. Physico-chemical analysis identified the following properties with values provided respectively for fresh leaves (FOin) and flours (FES and FLIO): low water activity (0.984, 0.370, 0.387 g/100 g), moisture (64.52, 5.37, 7.97 g /100 g), ash (2.69, 6.51, and 6.89 g/100 g), pH (0.89, 4.45, 4.48 g/100 g), lipids (0.84, 1.67, 5.23 g/100 g), protein (3.29, 8.23, 14.12 g/100 g), carbohydrates (17.02, 53.12, 33.02 g/100 g), ascorbic acid (19.70, 34.20, 36.90 mg/100 g). Sources of fiber from plant leaves and flours (11.64, 25.1, 32.89 g/100 g) showed increased levels of luminosity. For NMR, the presence of aliphatic and aromatic compounds with olefinic hydrogens and a derivative of gallic acid were detected. The most abundant minerals detected were potassium and calcium. Micrographs identified the presence of irregular, non-uniform, and sponge-like particles. The main sugars detected were: fructose, glucose, and maltose. Malic, succinic, citric, lactic, and formic acids were found. Fifteen phenolic compounds were identified in the samples, highlighting: kaempferol, catechin, and caffeic acid. The values ​​found for phenolics were (447, 716.66, 493.31 mg EAG/100 g), flavonoids (267.60, 267.60, 286.26 EC/100 g). Antioxidant activity was higher using the ABTS method rather than FRAP for analysis of FOin, FES, and FLIO. Since the flours of the aroeira leaf have an abundant matrix of nutrients with bioactive properties and antioxidant activity, they have a potential for technological and functional use when added to food.

Nutraceutical formulations combining Limosilactobacillus fermentum, quercetin, and or resveratrol with beneficial impacts on the abundance of intestinal bacterial populations, metabolite production, and antioxidant capacity during colonic fermentation.

This study evaluated the impacts of different nutraceutical formulations combining Limosilactobacillus fermentum 296 (∼10 log CFU/mL), quercetin (QUE, 160 mg), and or resveratrol (RES, 150 mg) on the relative abundance of various intestinal bacterial populations, production of microbial metabolites, and antioxidant capacity during 48 h of in vitro colonic fermentation. The nutraceutical formulations increased the relative abundance of Lactobacillus spp./Enterococcus spp. and Bifidobacterium spp. and decreased the relative abundance of Bacteroides spp./Prevotella spp., Clostridium histolyticum, and E. rectale/C. coccoides during the colonic fermentation. Medium with the formulation containing L. fermentum, QUE, and RES had the highest prebiotic indexes, indicating synergistic or additive interaction between QUE and RES to modulate the intestinal microbiota. The nutraceutical formulations increased the production of bioactive metabolites and antioxidant capacity in the colonic fermentation media. The results indicate the capability of the tested nutraceutical formulations to beneficially modulate the composition and metabolite production of human intestinal microbiota and increase the antioxidant capacity in the intestinal environment.

Seasonal Variations of Polyphenols Content, Sun Protection Factor and Antioxidant Activity of Two Lamiaceae Species.

Secondary metabolite production by plants is influenced by external environmental factors that can change depending on the seasons, which makes it important to know how the plant, through its metabolism, is able to adapt to these variations. Mentha x villosa and Plectranthus amboinicus present in their chemical composition polyphenols, and through previous studies, it has been seen that these two species present promising in vitro photoprotective activity. The aim of this study was to evaluate seasonal alterations in photoprotective and antioxidant activities and the influence of factors such as precipitation levels and sun radiation incidence. Thus, polyphenol quantification, cromatographics (HPLC-DAD) and multivariate (PCA) analyses of extracts of the two species through twelve months were done. It was observed that the best months for photoprotective and antioxidant activities were September for M. villosa and July for P. amboinicus (SPF = 14.79). It was possible to conclude that solar radiation more clearly influences the production of phenolics and the increase of SPF in M. villosa, in addition to favoring the antioxidant activity of the two species, while precipitation seems to have no influence.

Psychopharmacological effects of riparin III from Aniba riparia (Nees) Mez. (Lauraceae) supported by metabolic approach and multivariate data analysis.

BACKGROUND: Currently there is a high prevalence of humor disorders such as anxiety and depression throughout the world, especially concerning advanced age patients. Aniba riparia (Nees) Mez. (Lauraceae), popular known as "louro", can be found from the Amazon through Guianas until the Andes. Previous studies have already reported the isolation of alkamide-type alkaloids such as riparin III (O-methyl-N-2,6-dyhydroxy-benzoyl tyramine) which has demonstrated anxiolytic and antidepressant-like effects in high doses by intraperitoneal administration. METHODS: Experimental protocol was conducted in order to analyze the anxiolytic-like effect of riparin III at lower doses by intravenous administration to Wistar rats (Rattus norvegicus) (n = 5). The experimental approach was designed to last 15 days, divided in 3 distinct periods of five days: control, anxiogenic and treatment periods. The anxiolytic-like effect was evaluated by experimental behavior tests such as open field and elevated plus-maze test, combined with urine metabolic footprint analysis. The urine was collected daily and analyzed by 1H NMR. Generated data were statistically treated by Principal Component Analysis in order to detect patterns among the distinct periods evaluated as well as biomarkers responsible for its distinction. RESULTS: It was observed on treatment group that cortisol, biomarker related to physiological stress was reduced, indicating anxiolytic-like effect of riparin III, probably through activation of 5-HT2A receptors, which was corroborated by behavioral tests. CONCLUSION: 1H NMR urine metabolic footprint combined with multivariate data analysis have demonstrated to be an important diagnostic tool to prove the anxiolytic-like effect of riparin III in a more efficient and pragmatic way.

Modulation of drug resistance in Staphylococcus aureus by 132-hydroxy-(132-R/S)-pheophytin isolated from Sargassum polyceratium.

Efflux pumps are integral parts of the bacterial plasma membrane that are responsible for many cases of antibiotic resistance. Modulators of drug resistance are regarded as the most suitable new antibacterial therapies. We evaluated the extracts of Sargassum polyceratium and the isolated compound pheophytin (Sp-1) for antibiotic modifying activity in strains of Staphylococcus aureus with efflux pump. The minimum inhibitory concentrations (MICs) for norfloxacin, tetracycline and erythromycin were determined by the microdilution broth method, in the absence and presence of the extract at a sub-inhibitory concentration (MIC/4). The extracts and isolated compounds showed no significant antimicrobial activity, but they changed the antibiotic activity, decreasing bacterial resistance by 2 to 4x. Using a checkerboard method, it was also possible to observe the synergistic effect (ΣFIC ≤ 0.5) between Sp-1 and the antibiotics erythromycin and norfloxacin. The results indicate that the seaweed Sargassum polyceratium and pheophytin are potential sources of an antibiotic adjuvant that modulates bacterial resistance, acting as a putative efflux pump inhibitor.

Computer-Aided Chemotaxonomy and Bioprospecting Study of Diterpenes of the Lamiaceae Family.

Lamiaceae is one of the largest families of angiosperms and is classified into 12 subfamilies that are composed of 295 genera and 7775 species. It presents a variety of secondary metabolites such as diterpenes that are commonly found in their species, and some of them are known to be chemotaxonomic markers. The aim of this work was to construct a database of diterpenes and to use it to perform a chemotaxonomic analysis among the subfamilies of Lamiaceae, using molecular descriptors and self-organizing maps (SOMs). The 4115 different diterpenes corresponding to 6386 botanical occurrences, which are distributed in eight subfamilies, 66 genera, 639 different species and 4880 geographical locations, were added to SistematX. Molecular descriptors of diterpenes and their respective botanical occurrences were used to generate the SOMs. In all obtained maps, a match rate higher than 80% was observed, demonstrating a separation of the Lamiaceae subfamilies, corroborating with the morphological and molecular data proposed by Li et al. Therefore, through this chemotaxonomic study, we can predict the localization of a diterpene in a subfamily and assist in the search for secondary metabolites with specific structural characteristics, such as compounds with potential biological activity.

Fluorescent Canthin-6-one Alkaloids from Simaba bahiensis: Isolation, Identification, and Cell-Labeling Properties.

Canthin-6-one alkaloids, which are present in plants of the genus Simaba, are natural compounds that are capable of acting as fluorescent probes. However, the chemical composition and fluorescent properties of most species of this genus have not been analyzed. The objective of this study was to characterize the fluorescent properties of an extract of S. bahiensis and identify the chemical entities responsible for these properties. In addition, the cell-labeling properties of the fluorescent dye from A and of the isolated compounds were characterized by confocal fluorescence microscopy and flow cytometry. One quassinoid and three fluorescent alkaloids were isolated from S. bahiensis, all compounds were identified by using NMR spectroscopy and high-resolution mass spectrometry. Staining experiments and HPLC-FL analysis shown that canthin-6-one alkaloids are the main green fluorescent compounds in the analyzed dyes. All compounds evaluated showed a cytoplasmic marker with a residence time of 24 h. The present study is the first to describe the presence of canthin-6-one alkaloids in S. bahiensis, in addition to demonstrating promising cell-labeling properties of fluorescent compounds from S. bahiensis with broad emission wavelengths.

Evaluación fitoquímica de hojas de Excoecaria lucida Sw. (Aité) (Euphorbiaceae) y Aislamiento e Identificación de un hemiterpenoide / Fitochemistry evaluation of leaves of Excoecaria lucida Sw. (Aité) (Euphorbiaceae) and isolation e identification of a hemiterpenoid

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)

Evaluación fitoquímica de hojas de Excoecaria lucida Sw. (Aité) (Euphorbiaceae) y Aislamiento e Identificación de un hemiterpenoide / Fitochemistry evaluation of leaves of Excoecaria lucida Sw. (Aité) (Euphorbiaceae) and isolation e identification of a hemiterpenoid

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.

Experimental methodologies and evaluations of computer-aided drug design methodologies applied to a series of 2-aminothiophene derivatives with antifungal activities.

Fifty 2-[(arylidene)amino]-4,5-cycloalkyl[b]thiophene-3-carbonitrile derivatives were screened for their in vitro antifungal activities against Candida krusei and Cryptococcus neoformans. Based on experimentally determined minimum inhibitory concentration (MIC) values, we conducted computer-aided drug design studies [molecular modelling, chemometric tools (CPCA, PCA, PLS) and QSAR-3D] that enable the prediction of three-dimensional structural characteristics that influence the antifungal activities of these derivatives. These predictions provide direction with regard to the syntheses of new derivatives with improved biological activities, which can be used as therapeutic alternatives for the treatment of fungal infections.