Leishmanicidal activity and cytotoxicity of compounds from two Annonacea species cultivated in Northeastern Brazil

INTRODUCTION: Visceral leishmaniasis is endemic in 88 countries, with a total of 12 million people infected and 350 million at risk. In the search for new leishmanicidal agents, alkaloids and acetogenins isolated from leaves of Annona squamosa and seeds of Annona muricata were tested against promastigote and amastigote forms of Leishmania chagasi. METHODS: Methanol-water (80:20) extracts of A. squamosa leaves and A. muricata seeds were extracted with 10% phosphoric acid and organic solvents to obtain the alkaloid and acetogenin-rich extracts. These extracts were chromatographed on a silica gel column and eluted with a mixture of several solvents in crescent order of polarity. The compounds were identified by spectroscopic analysis. The isolated compounds were tested against Leishmania chagasi, which is responsible for American visceral leishmaniasis, using the MTT test assay. The cytotoxicity assay was evaluated for all isolated compounds, and for this assay, RAW 264.7 cells were used. RESULTS: O-methylarmepavine, a benzylisoquinolinic alkaloid, and a C37 trihydroxy adjacent bistetrahydrofuran acetogenin were isolated from A. squamosa, while two acetogenins, annonacinone and corossolone, were isolated from A. muricata. Against promastigotes, the alkaloid showed an IC50 of 23.3 µg/mL, and the acetogenins showed an IC50 ranging from 25.9 to 37.6 µg/mL; in the amastigote assay, the IC50 values ranged from 13.5 to 28.7 µg/mL. The cytotoxicity assay showed results ranging from 43.5 to 79.9 µg/mL. CONCLUSIONS: These results characterize A. squamosa and A. muricata as potential sources of leishmanicidal agents. Plants from Annonaceae are rich sources of natural compounds and an important tool in the search for new leishmanicidal therapies.

Antioxidant, cytotoxic and UVB-absorbing activity of Maytenus guyanensis Klotzch. (Celastraceae) bark extracts

Maytenus guyanensis Klotzch. is an Amazonian medicinal tree species known in Brazil by the common name chichuá and in Peru and Colombia by the name chuchuhuasi. It is used in traditional medicine as stimulant, tonic, and muscle relaxant, for the relief of arthritis, rheumatism, hemorrhoids, swollen kidney, skin eruptions, and skin cancer prevention, among others. Initially, different extraction solvents and methods were applied to dried, ground bark which made possible the preparation of extracts having both significant lethality to brine shrimp larvae (Artemia franciscana Leach) as well as antioxidant activity in vitro based on tests involving reactions with 2,2,-diphenyl-1-picrylhydrazyl (DPPH). Analysis of fractions from serial extractions with solvents of increasing polarity supports the notion that antioxidant activity is associated with compounds of intermediate polarity and cytotoxicity is associated with compounds of low to intermediate polarity. Variation of extraction time and conditions revealed that hot, continuous ethanol extraction provided good yields of bark extract in several hours. Hot extraction also provided ethanol extracts having greater lethality to brine shrimp and antioxidant activity (compared to the flavonoid rutin in semi-quantitative methods based on DPPH) than extracts obtained from maceration at room temperature. Freeze-dried ethanol extracts were prepared by: 1) maceration at room temperature and 2) hot extraction (eight hours) on several hundred gram scales and the latter extract was shown to have partial screening effects on UVB light. In this work, cytotoxic, antioxidant and potential sun-screening activity are shown for the first time in M. guyanensis.

Genetic and biological characterization of a densovirus isolate that affects dengue virus infection

Brevidensoviruses have an encapsidated, single-stranded DNA genome that predominantly has a negative polarity. In recent years, they have received particular attention due to their potential role in the biological control of pathogenic arboviruses and to their unnoticed presence in cell cultures as contaminants. In addition, brevidensoviruses may also be useful as viral vectors. This study describes the first genetic and biological characterization of a mosquito densovirus that was isolated in Brazil; moreover, we examined the phylogenetic relationship between this isolate and the other brevidensoviruses. We further demonstrate that this densovirus has the potential to be used to biologically control dengue virus (DENV) infection with in vitro co-infection experiments. The present study provides evidence that this densovirus isolate is a fast-spreading virus that affects cell growth and DENV infection.

A técnica da reflectância difusa aplicada ao estudo da fluorescência de 2,3-naftalimidas n-substituídas com grupos alquila incluídas em b-ciclodextrina e adsorvidas em celulose microcristalina

The solution fluorescence of N-alkyl-2,3-naphthalimides (1-4) in polar protic and aprotic solvents was compared to the emission from solid samples resulting from the imide complexation with b-cyclodextrin or adsorption on the surface of microcrystalline cellulose. Solid samples of the inclusion complex 2,3-naphthalimides/b-cyclodextrin show maximum for fluorescence emission significantly different to the observed in methanolic solution. Beside this, a clear effect on the alkyl chain length could be observed for these samples which is probably due to differences in probe location inside the cyclodextrin cavity. The constancy for fluorescence quantum yield and fluorescence lifetime for the imides 1 - 4 adsorbed on microcrystalline cellulose suggests that, independently of the polarity of the solvent used for sample preparation, the probe is preferentially located on the cellulose surface. An increase of fluorescence quantum yield and fluorescence lifetime for solid samples, when compared to the values obtained in solution for the different solvents employed in this study (acetonitrile, methanol and water), is fully in accordance with a decrease of the probe mobility due to inclusion in b-cyclodextrin or to adsorption on cellulose.

Análise de ácidos graxos por eletroforese capilar utilizando detecção condutométrica sem contato

This article describes a novel approach to the separation of fatty acids ranging from 8 to 20 carbons using capillary electrophoresis with contactless conductivity detection. Complete separation of nine linear chain fatty acids (from C8:0 to C20:0) was achieved in 15 min under normal polarity operation. Limits of detection ranged from 35 to 319 µmol L-1 for C20:0 to C8:0, respectively. The optimized running electrolyte composition was 5.0 mmol L-1 phosphate buffer at pH 7, 4.0 mmol L-1 dimethyl-b-cyclodextrin, 2.0 mmol L-1 trimethyl-b-cyclodextrin, acetonitrile 50% (v/v), and methanol 20% (v/v). The applicability of the separation system was demonstrated by the analysis of coconut vegetable oil.

Tratamento de efluente da indústria de processamento de coco utilizando eletroflotação

Electroflotation (EF) with aluminum electrodes was applied in the treatment of Brazilian industrial coconut wastewater. The results show that EF with polarity inversion is a very good treatment when compared to others. The removal of pollutants in the wastewater after EF with polarity inversion was 96.3% of oils and grease, 99% of color and 66% of total organic carbon. Also, metal concentrations, turbidity and total solids were reduced.

Imobilização de lipases em filme de caseinato de sódio/glicerol: aplicação na síntese de ésteres

Lipases from different sources were immobilized in sodium caseinate/glycerol film and used in the esterification reactions of aliphatic acids with alcohols in the presence of organic solvents. Lipases from Pseudomonas sp and Rhizopus oryzae were selected and the influence of several parameters was analyzed, including: lipase loading, organic solvent polarity, reaction temperature, chain length of alcohol and acid and enzyme/support reuse. For comparison, free enzymes were used under similar experimental conditions.

Composição fenólica, atividade antibacteriana e antioxidante da própolis vermelha brasileira

Propolis is a resinous hive product collected by honeybees from various plant sources. It has a complex chemical composition, constituted by various phenolic compounds. Extracts of increasing polarity (n-hexane, chloroform, and ethanol) were obtained from a sample of red propolis from the state of Alagoas. Assays were carried out for determination of contents of phenolics, along with antibacterial and antioxidant activities. The EEP, fractions and sub-fractions showed strong biological activities and were related with phenolic the content compounds contents. The sub-fractions were more bioactive than the EEP and fractions, demonstrating that the antioxidant and antibacterial activities are not a result of synergistic effect between the various chemical compounds in propolis.

Aplicações de cromatografia líquida de alta eficiência para o estudo de poluentes orgânicos emergentes

Emerging organic pollutants (EOP) include many environmental contaminants based on commercial products such as pharmaceuticals, personal care products, detergents, gasoline, polymers, etc. EOP may be candidates for future regulation as they offer potential risk to environmental and human health due to their continual entrance into the environment and to the fact that even the most modern wastewater treatment plants are not able to totally transform / remove these compounds. High performance liquid chromatography is recommended to separate emerging organic pollutants with characteristics of high polarity and low volatility, especially pharmaceuticals, from environmental matrices.

Investigando cinza da casca do arroz como fase estacionária em cromatografia: uma proposta de aula experimental nos cursos de graduação

This article describes an experiment that involves the extraction and separation of the pigments of spinach extract by column chromatography using the silica obtained from rice husk ash as a stationary phase. The experimental procedure is very simple to apply in the chemistry laboratory, and allowed to illustrate some concepts of organic chemistry: structure of organic molecules, solubility, polarity, extraction, partition coefficient, adsorption and retention factor (Rf), as well as objectives and fundamentals of chromatographic methods. The experiment can be carried out in a 4 h period.

Optimization of wood flour acetylation by factorial design and partial least squares regression

Acetylation was performed to reduce the polarity of wood and increase its compatibility with polymer matrices for the production of composites. These reactions were performed first as a function of acetic acid and anhydride concentration in a mixture catalyzed by sulfuric acid. A concentration of 50%/50% (v/v) of acetic acid and anhydride was found to produced the highest conversion rate between the functional groups. After these reactions, the kinetics were investigated by varying times and temperatures using a 3² factorial design, and showed time was the most relevant parameter in determining the conversion of hydroxyl into carbonyl groups.

Solubilidade das substâncias orgânicas

The solubility of organic compounds is a topic of great importance in chemistry and of interest in several areas, such as materials, drugs and the environment. In this paper, the solubility of these species is discussed in terms of their properties, such as the predominant type of chemical bond, molecular structure, polarity and types of intermolecular interactions. Examples of biological processes fundamental for sustainability of life and related with the solubility of chemical species are presented and discussed.

Autoagregação da 5,10,15,20-tetrakis(4-metoxifenil)porfirina (tmpp): estudos espectroscópicos e análises multivariadas

In this work, the spectroscopic properties of 5,10,15,20-tetrakis(4-methoxyphenyl)porphyrin (TMPP) in solvents of different polarities and water/ethanol mixtures were studied by electronic absorption spectroscopy and resonance light scattering associated with statistical analysis. The molar absorption coefficient and emission maximum of TMPP were dependent on solvent polarity. In the water/ethanol mixture, TMPP remained monomeric up to 25% of water, when it reaches its critical aggregation percentage. Oblique head-to-tail aggregate was found at intermediate water content (35 - 55%), while formation of a J-type aggregate was observed at higher water content (> 60%).

AVALIAÇÃO DO RADICAL N,N-DIETIL-1,4-FENILENODIAMINO (DEPD•+) COMO SONDA ESPECTROFOTOMÉTRICA PARA DETERMINAÇÃO DA CAPACIDADE ANTIOXIDANTE EM BEBIDAS

AbstractMany well-established methods for determining the antioxidant capacities in several samples have been described in literature. However, DPPH (2,2-diphenyl-1-picrylhydrazyl) and ABTS (2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid)) are the main two methods that utilize radicals as spectrophotometric probes for analysis. Nevertheless, these methods have certain limitations because of their slower kinetics, solvent polarity effects, the hydrophilicity and lipophilicity of the compounds, chemical costs, etc. In this study, a spectrophotometric method for determining the antioxidant capacity in beverages was developed based on an exploration of the cation radical derived from DEPD. This method was based on the oxidation of aromatic amines with Fe(III) ions at pH 4.0, which leads to their corresponding purple cation radicals (DEPD•+) with λmax values at 500 and 540 nm. The addition of an antioxidant after the formation of the radical leads to a reduction in color intensity that is proportional to the antioxidant concentration in the medium. Results obtained using this method were compared with the Folin-Ciocalteau, ABTS and DPPH methods in terms of applications in wines, teas, and infusions samples. Linear correlation analysis at a 95% confidence level was employed to compare the results, which were in good agreement with a correlation coefficient of r > 0.9000. Thus, the developed method was simple, accurate, and consistent with other assays for the determination of the total amount of phenolic compounds and antioxidant capacity.

COMPARISON BETWEEN ASPHALTENES (SUB)FRACTIONS EXTRACTED FROM TWO DIFFERENT ASPHALTIC RESIDUES: CHEMICAL CHARACTERIZATION AND PHASE BEHAVIOR

Asphaltenes are blamed for various problems in the petroleum industry, especially formation of solid deposits and stabilization of water-in-oil emulsions. Many studies have been conducted to characterize chemical structures of asphaltenes and assess their phase behavior in crude oil or in model-systems of asphaltenes extracted from oil or asphaltic residues from refineries. However, due to the diversity and complexity of these structures, there is still much to be investigated. In this study, asphaltene (sub)fractions were extracted from an asphaltic residue (AR02), characterized by NMR, elemental analysis, X-ray fluorescence and MS-TOF, and compared to asphaltene subfractions obtained from another asphaltic residue (AR01) described in a previous article. The (sub)fractions obtained from the two residues were used to prepare model-systems containing 1 wt% of asphaltenes in toluene and their phase behavior was evaluated by measuring asphaltene precipitation onset using optical microscopy. The results obtained indicated minor differences between the asphaltene fractions obtained from the asphaltic residues of distinct origins, with respect to aromaticity, elemental composition (CHN), presence and content of heteroelements and average molar mass. Regarding stability, minor differences in molecule polarity appear to promote major differences in the phase behavior of each of the asphaltene fractions isolated.