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The Inga genus comprises approximately 300 species that can be found from Mexico to northern Argentina. In folk medicine, Inga species are used to treat various diseases. The species Inga laurina is widely found in the Brazilian flora; however, there are few studies about its biological activity and chemical composition. The main purpose of this study was to identify and isolate the chemical constituents of Inga laurina barks and to evaluate the antifungal and cytotoxic activities. The total content of phenolics, proanthocyanidins, and flavonoids from the barks of Inga laurina were performed by spectrophotometric methods and the ethyl acetate (EAF) and n-butanol (BF) fractions showed the best results. Eleven compounds were identified in EAF by HPLC-ESI(−)-MS/MS, which showed good antifungal activity with MIC values of 23.4 and 46.8 μg mL−1, evaluated by broth microdilution method. Five new compounds of the genus Inga were isolated for the first time. Three of these compounds were isolated and reported on the literature for the first time: a proanthocyanidin B-type, gallocatechin-(4α→8)-4’-O-methylgallocatechin (XI) and two proanthocyanidins A-type, gallocatechin-(2→O→7,4→8)-4’-O-methylgallocatechin (XII) and gallocatechin-3-O-galloyl-(2→O→7,4→8)-4’-O-methylgallocatechin (XIII). The chemical study of the plant bark showed that this species is rich in phenolic compounds and it has great potential for the discovery of new bioactive compounds.

Made available in DSpace on 2020-12-12T01:54:11Z (GMT). No. of bitstreams: 0 Previous issue date: 2020-01-28 Scheelea phalerata Mart. ex Spreng (Arecaceae) is a palm tree found in the Brazilian cerrado. There are no topics related to volatile oils from S. phalerata leaves in the literature. This work determines its chemical composition and evaluates the biological activity under two different seasonal conditions (dry and rainy seasons). The dry essential oil yield was 0.034 ± 0.001% and the rainy essential oil yield was 0.011 ± 0.003%. Both essential oils presented different qualitative and quantitative compositions (99.4 and 98.5%). The main constituents of the dry essential oil were phytol (36.7%), nonadecane (9.7%), linolenic acid (9.1%), (Z)-hex-3-en-1-ol (4.2%), and squalene (4.0%). The main constituents of the rainy essential oil were phytol (26.1%), palmitic acid (18.7%), hexan-1-ol (15.6%), (Z)-hex-3-en-1-ol (9.7%), and oleic acid (4.0%). The antileishmanial activity against promastigotes of Leishmania amazonensis was observed only for the rainy season essential oil (IC50 value of 165.05 ± 33.26 μg mL-1). A molecular docking study showed that alcohols exert a paramount efficacy and that the action of some essential oil compounds may be similar to that of amphotericin B. Still, only the essential oil from the dry season showed moderate antibacterial activity against S. sanguinis (MICs 200-400 μg mL-1). The cytotoxicity against Vero cells was identical (>512) for both essential oils. The novel data here for both chemical characterization and biological activity, in particular, evidence that the action of these compounds is similar to that of amphotericin B, provide valuable information to the drug-discovery field. Nucleus of Research in Natural Products (NuPPeN) Institute of Chemistry Federal University of Uberlândia Campus Santa Mônica, Av. João Naves de ávila, 2121 Institute of Biosciences of Botucatu Department of Microbiology and Immunology Unesp-São Paulo State University, 250 Distrito de Rubião Junior Institute of Biosciences of Botucatu Department of Physics and Biophysics Unesp-São Paulo State University, 250 Distrito de Rubião Junior Nucleus of Research in Sciences and Technology Laboratory of Research in Applied Microbiology (LaPeMA) University of Franca, 201 Parque Universitário Institute of Biomedical Sciences Laboratory of Trypanosomatids Federal University of Uberlândia Campus Umuarama, Av. Pará 1720 Bloco 2B Nucleus of Bioprospecting in Natural Products (NuBiProN) Chemistry Department Federal Institute of the Triângulo Mineiro, 4000 Distrito Industrial I Institute of Biosciences of Botucatu Department of Microbiology and Immunology Unesp-São Paulo State University, 250 Distrito de Rubião Junior Institute of Biosciences of Botucatu Department of Physics and Biophysics Unesp-São Paulo State University, 250 Distrito de Rubião Junior

As composicoes quimicas sazonais dos oleos das folhas de Banisteriopsis malifolia (Ness & Mart.) B. Gates foram determinadas. Terpenos (56%) e alcoois alifaticos (29,8%) estao presentes em grandes quantidades no oleo essencial da estacao chuvosa em comparacao com a estacao seca (20,93% e 20,48%, respectivamente). Por outro lado, o oleo essencial da estacao seca apresentou como compostos principais alcanos de cadeia longa (18,43%) e acidos graxos (16,03%), destacando-se o hexatriacontano (18,43%) e o acido palmitico (10,62%). O fitol foi o principal terpenoide presente em ambos os oleos essenciais (52,70% no oleo essencial das chuvas versus 15,80% no oleo essencial seco). Em geral, o oleo essencial da estacao chuvosa apresentou os melhores resultados antibacterianos (valores de MIC de 100 a 400 μg mL-1) para todas as bacterias testadas. Os efeitos sinergicos dos compostos presentes no oleo da estacao chuvosa podem ser responsaveis pelos melhores efeitos inibitorios observados. Ambos os oleos essenciais nao apresentaram nenhuma atividade anti-Candida promissora.

Metabolic profiling of complex biological matrices based on liquid chromatography-mass spectrometry (LC-MS) allows detecting a wide range of metabolites with distinct concentrations and physicochemical properties. Given the complexity of samples and the necessity of a comprehensive approach in untargeted metabolomics, quality control strategies are mandatory to obtain high-quality data. The LC-MS performance must be monitored and evaluated to guarantee data reliability. In this study, a test mixture (TM) was developed, systematically evaluated, and applied to untargeted metabolomics of urine samples from individuals suspected of inborn errors of metabolism. The TM was composed of fifteen analytes that eluted across the entire gradient in reversed-phase columns and ionized in positive/negative electrospray modes. It helped set the LC-MS conditions for urine analysis, from sample reconstitution solvent to selecting the MS ion source parameters. The TM quickly indicated column stationary phase degradation during the batch analysis when employed to monitor and evaluate the LC-MS system in an untargeted metabolomic analysis. Thus, in addition to pooled QC samples, a TM can be employed in untargeted metabolomics to rapidly assess the system performance avoiding unnecessary efforts for further data treatment and multivariate analysis of poor-quality data

Chronic hyperglycemia and hyperlipidemia are associated with excessive formation of reactive oxygen species and advanced glycation end-products. The present study aimed to evaluate the potential in vitro antidiabetic properties of Kielmeyera coriacea inner bark. The main phytochemical compounds were identified by UHPLC-ESI/MSn and the ethanol extract and its fractions were used to evaluate their antioxidant and anti-glycation capacities, as well as their inhibitory potential against glycoside and lipid hydrolases activities. The polar fractions, especially the n-butanol fraction, had free radical scavenging and quenching properties (ORAC and FRAP values>1800 and 1000 µmol trolox eq/g, respectively, and DPPH IC50

Soy production in Brazil is an important factor for the agro-industrial, economic, and social development of the country. The expansion of soy in the Brazilian territory is mainly due to the incorporation of new genetic characteristics into cultivars that granted resistance to the Cerrado conditions and to herbicides. Currently, Brazilian soy production is the result of genetically modified cultivars. Studies regarding the chemical composition of soybeans show that qualitative and quantitative variations can occur, depending on the region of production. This work aimed to investigate the chemical composition of soybeans produced in different cities of the Triângulo Mineiro region/MG, Brazil (Harvest 2017/2018) and stored in three warehouses located in the city of Uberaba/MG. The grain analysis was made by liquid chromatography coupled to electrospray ionization mass spectrometry (LC-MS-ESI). The classes of metabolites identified from methanolic extraction were organic acids, phenolic compounds, flavonoids, sugars, amino acids, dipeptides, nitrogenous bases, nucleosides, sphingolipids, and fatty acids. The isoflavones genistein, daidzein, glycitein, genistin, acetyldaidzin, and acetylgenistin were identified in soybeans from the three warehouses. The flavonoid eriodictyol-O-hexoside was also found. The Principal Component Analysis (PCA) from the mass spectrum data obtained by direct injection in the negative and positive modes evidenced the well-defined separation of three groups, indicating that there was variance among the soy samples from each warehouse. The samples from warehouses 1 and 3 showed greater similarity in the Hierarchical Cluster Analysis (HCA) in negative mode, while in positive mode, the samples from warehouses 2 and 3 presented greater similarity.

Objectives This work aimed to evaluate the antifungal and cytotoxic activity of the EtOH extract and fractions of Banisteriopsis argyrophylla leaves, and to perform the identification of these bioactive metabolites. Methods The EtOAc fraction (EAF) obtained from the ethanolic extract of B. argyrophylla leaves showed better antifungal potential against Candida spp. In this fraction, ten flavonoids have been identified by UHPLC-ESI-MSn. Then, EAF was submitted to column chromatography to give four new fractions (A1–A4). The cytotoxicity was determined against Vero cells. Key findings The EAF showed better antifungal potential against Candida spp. with minimum inhibitory concentrations (MICs) between 31.25 and 93.75 μg/ml. The (–)-catechin (fraction A1) showed a MIC of 2.83 μg/ml against Candida glabrata. Fractions A2, A3 and A4 were rich in quercetins and kaempferols and showed good inhibitory concentrations (5.86–46.87 μg/ml) against C. albicans, C. glabrata and C. tropicalis. Conclusions The EtOH extract, fractions and the isolated (–)-catechin showed lower toxicity to Vero cells than cisplatin, used as a positive control. Thus, the leaves of B. argyrophylla are a promising source of antifungal agents.

The antimicrobial potential of extracts of bark and leaves of Cassia bakeriana Craib, Fabaceae, against aerobic and anaerobic oral bacteria was evaluated by the microdilution broth method. For crude ethanol extracts and organic fractions tested, the bark dichloromethane phase showed a significant antibacterial effect, with MIC values ranging from 12.5 to 100 μg/ml for most of the microorganisms tested. Thus, a bioassay-guided fractionation of this fraction was performed. This fractionation led to isolation of the 1,8-dihydroxy-anthraquinone-3-carboxylic acid, also known as cassic acid or rhein. It is the first time that this bioactive anthraquinone has been isolated from this plant. Rhein exhibited good selectivity and high activity against anaerobic microorganisms, with MIC values ranging between 3.12 μg/ml (11.0 μM) and 25 μg/ml (88.0 μM). These results were considered very promising since the most active samples and rhein showed greater selectivity against oral microorganisms than toxicity to Vero cells. Keywords: Antimicrobial activity, Cassia bakeriana, Cassic acid, Cytotoxicity, 1,8-Dihydroxy-anthraquinone-3-carboxylic acid, Rhein

The species Inga laurina is native to the Brazilian Cerrado. There are no studies about the chemical composition and biological activities of extracts of this endangered species. The ethanolic extract and its successive fractions are rich in phenolic compounds and presented good antifungal activities. HPLC/MS-MS/MS and H1/C13 analysis led to the identification of seventeen compounds, most of which are gallic acid derivatives, myricetin and quercetin glycosides. The ethyl acetate fraction (EAF) contained high levels of total phenolics, expressed in milligrams of gallic acid equivalents per gram of extract (475.3 ± 1.9 mg GAE gextract-1) and flavonoids expressed in milligrams of quercetin equivalents per gram of extract (359.3 ± 10.6 mg QE gextract-1). This fraction was active against fungi of the Candida genus. The EAF showed MIC value 11.7 μg mL−1 against C. glabrata and a selectivity index of 1.6 against Vero cells. The flavonol glycoside myricetin-3-O-rhamnoside was isolated for the first time from the Inga laurina. These results make I. laurina a promising plant as a source of pharmaceutical and biological active antifungal compounds.

In Mozambique, a large part of the population depends on plants for the treatment of various diseases. However, some of them have been little studied in relation to chemical and biological aspects. Among these species, Ozoroa obovata is widely used in traditional medicine in Mozambique. The factors that influence the use of medicinal plants in developing countries are mainly cultural habits, the inefficiency of the health system and the high cost of medicines. This work aimed to study the chemical composition and evaluate the antimicrobial activity of the twigs of O. obovata. Through the analysis by liquid chromatography coupled to mass spectrometry with electrospray ionization (HPLC-MS-ESI), it was possible to propose that in the ethanolic extract of the twigs, most of the constituents belong to the classes of phenolic acids and flavonoid. The phenolic compounds were represented by quinic, gallic and protocatechuic acids and five anacardic acids, whereas flavonoids were represented by mangiferin, taxifolin and quercetin mono and dihexoside. The extract was evaluated against bacteria in the oral cavity and showed moderate activity against Streptococcus mutans, S. mitis and Porphyromonas gingivalis (minimum inhibitory concentration - MIC 400 µg mL –1 ). In relation antifungal test, the extract showed activity against Candida albicans with MIC of 3000 µg mL –1 . The biological results indicated that the twigs of O. obovata have bioactive metabolites with antimicrobial potential.

Banisteriopsis laevifolia (A. Juss.) B. Gates (Malpighiaceae) is largely distributed in the cerrado Brazilian biome. In this study, phytochemical screening, antimicrobial and antifungal activities of leaves extract and partitions were evaluated. Phytochemical screening tests indicated the presence of flavonoids, terpenoids, phenols, sugar, steroids, triterpenoids, and tannins compounds. No alkaloids or nitrogenated compounds were found. Antioxidant, antimicrobial and antifungal activities were tested. The extract and partitions from the B. laevifolia leaves demonstrated relevant scavenging free radical DPPH effect. The crude extract and partitions inhibit bacteria growth with minimum inhibitory concentrations (MIC) below 400 mg L −1 for most oral microorganisms tested. Meanwhile, the antifungal activity proved to be very promising for the ethanolic extract and partitions (31–375 μg mL −1 ) against all yeasts tested. The antimicrobial activities results are very promising since the ethanol extract and the more active n -buthanol partition showed great selectivity (0.9–1.2; 0.1–0.7, respectively) against microorganisms and relatively low toxicity to Vero cells. Analysis by UHPLC-ESI–MS n from the most bioactive fractions (ethyl acetate and n -buthanol) permitted to identify ten phenolic compounds reported in the Banisteriopsis family that exert recognized antioxidant, antimicrobial and antifungal activity. Main secondary metabolites found were phenolic acids and flavonoid glycosides, mainly derivatives from quercetin and rutin. The biological activity results and MS analysis for the B.laevifolia leaves revealed that they have efficient antimicrobial agents, and contributed to knowledge of the genus.

Banisteriopsis argyrophylla belongs to the Malpighiaceae family, which is a species from Cerrado, also known as “cipo-prata” or “cipo-folha-de-prata.” Several species of this family present biological potential. This work reports the chemical identification of the ethanol extract (EE) and its fractions from B. argyrophylla leaves and shows the analysis of the antioxidant activity and inhibitory effects on activities of α-amylase, α-glucosidase and lipase, and non-enzymatic glycation. The ethyl acetate fraction (EAF) and n-butanol fraction (BF) showed antioxidant activity, with IC50 values of 4.1 ± 0.1 and 4.8 ± 0.1 μg mL−1, respectively, by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) method, and IC50 values of 6046.3 ± 174.2 and 6264.2 ± 32.2 µmol Trolox eq g−1 by the oxygen radical absorbance capacity (ORAC) method. Furthermore, the DPPH method with these fractions presented electroactive species with antioxidant potential, as shown by the differential pulse voltammetry (DPV) method. The inhibitory effects of the EAF and BF were demonstrated by the following results: IC50 of 5.1 ± 0.3 and 2.5 ± 0.2 μg mL−1 for α-amylase, IC50 of 1093.5 ± 26.0 and 1250.8 ± 21.9 μg mL−1 for α-glucosidase, IC50 of 8.3 ± 4.1 and 4.4 ± 1.0 μg mL−1 for lipase, and IC50 of 1.3 ± 0.1 and 0.9 ± 0.1 μg mL−1 for glycation. Some bioactive compounds were identified by (–)-ESI-MS/MS, such as catechin, procyanidins, glycosylated flavonoids, kaempferol, and megastigmane glucosides. The antidiabetic activity of B. argyrophylla has been reported for the first time.

The essential oil (EO) from leaves of Eugenia calycina Cambess. was analysed by Gas Chromatography coupled to Mass Spectrometry (GC–MS). Thirty-nine compounds accounting for 88.09% of the EO composition were identified. The EO was rich in sesquiterpene hydrocarbons and oxygenated sesquiterpenes, and the major components were spathulenol (21.36%), bicyclogermacrene (19.30%), β-caryophyllene (8.57%), viridiflorol (3.43%), allo-aromadendrene (3.34%), and a mixture of the caryophyllene oxide, gleenol, and globulol (7.71%). The EO was fractioned in four fractions and the first fraction (F1) contained only sesquiterpene hydrocarbons; the second one (F2) contained one sesquiterpene hydrocarbon (1.95%) and 96.98% of oxygenated sesquiterpenes; and the other fractions (F3 and F4) contained mostly oxygenated sesquiterpenes. The antimicrobial activity of the EO and its fractions were evaluated against aerobic and anaerobic oral bacteria by microdilution method. The EO showed strong antimicrobial activity against anaerobic bacteria as Prevotella nigrescens and Porphyromonas gingivalis . Fractions F2–F4 showed values of Minimum Inhibitory Concentration (MIC) ranging between 50 and 100 μg mL −1 for most oral microorganisms tested and presented higher activity than EO and F1. The EO and its fractions presented low toxicity to HeLa cells at concentrations with strong antimicrobial activity.

Many essential oils (EOs) of different plant species possess interesting antimicrobial effects on buccal microorganisms and cytotoxic properties. EOs ofKielmeyera coriaceaMart. & Zucc. were analyzed by gas chromatography coupled to mass spectrometry (GC-MS). The EO from leaves is rich in sesquiterpenes hydrocarbons and oxygenated sesquiterpenes. The three major compounds identified were germacrene-D (24.2%), (E)-caryophyllene (15.5%), and bicyclogermacrene (11.6%). The inner bark EO is composed mainly of sesquiterpenes hydrocarbons and the major components are alpha-copaene (14.9%) and alpha-(E)-bergamotene (13.0%). The outer bark EO is composed mainly of oxygenated sesquiterpenes and long-chain alkanes, and the major components are alpha-eudesmol (4.2%) and nonacosane (5.8%). The wood EO is mainly composed of long-chain alkanes and fatty acids, and the major components are nonacosane (9.7%) and palmitic acid (16.2%). The inner bark EO showed the strongest antimicrobial activity against the anaerobic bacteriaPrevotella nigrescens(minimum inhibitory concentration-MIC of 50 µg mL−1). The outer bark and wood EOs showed MICs of 100 µg mL−1for all aerobic microorganisms tested. The EOs presented low toxicity to Vero cells. These results suggest thatK. coriacea, a Brazilian plant, provide initial evidence of a new and alternative source of substances with medicinal interest.

Recognition of samples of coffee adulterated with their own husks has been a challenging task. The quite similar physical aspect of roasted grinded coffee husk when compared to ground coffee hampers a prompt visual distinction among both types of products. Several methodologies that make use of distinct analytical techniques have been developed for the authentication of coffee quality. In the present work, we demonstrate that direct infusion electrospray ionization mass spectrometry (ESI-MS) can be applied to detect counterfeit samples of roasted coffee adulterated by the addition of coffee husks (at a level of 10% w/w) in a quick and reliable way. The ESI-MS fingerprints (in both the negative and positive modes) revealed the presence of diagnostic markers, such as carbohydrates (for instance, saccharose), chlorogenic acids, caffeine, and other components related to the coffee flavor, that characterize each type of sample (coffee and rusk). Furthermore, the PCA (principal component analysis) methodology, applied to the whole set of the ESI-MS data (in the negative mode), grouped the samples into three clearly distinct categories: coffees, husks and blends. The results presented herein describe therefore an innovative and rapid methodology potentially useful in the diagnosis of such hardly-detectable type of adulteration.

The seasonal chemical composition of essential oils from Inga laurina was determined by GC/MS. In the stem bark’s essential oil extracted during the dry season, the presence of terpenoids (30.05%) stood out, and phytol (9.76%) was the major compound identified. For the stem bark oil obtained during the rainy season, in addition to terpenoids (26.63%), a large amount of fatty acids (46.84%) were identified, in particular palmitic acid (25.40%). Regarding the leaves’ essential oil obtained in the dry season, esters (42.35%) were the main components. The main ester present was (Z)-hex-3-enyl benzoate (10.15%) and the major compound of this oil was (Z)-hex-3-en-1-ol (14.23%). Terpenoids (33.84%), long-chain alkanes (27.04%) and fatty acids (21.72%) were the main components of the essential oil from leaves in the rainy season. Phytol (33.21%), nonacosane (21.95%) and palmitic acid (15.20%) were the major compounds identified. The antimicrobial activity against aerobic and anaerobic oral bacteria was evaluated by the microdilution broth method and cytotoxic activity was carried out with Vero cells. The essential oils from the rainy season showed a better inhibition of the bacterial growth with Minimal Inhibitory Concentrations (MIC) values of 25 or 50 µg·mL−1 for aerobic bacteria, and high selectivity against bacteria was observed. The large amount of fatty acids in rainy season oils may be related to the better inhibitory effects observed.

The chemical composition of the essential oils from leaves, bark and wood of Cassia bakeriana Craib. was determined by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). Alcohols, aldehydes and fatty acids were the major components in leaf and bark oil, while wood essential oil was rich in fatty acids. Terpenes such as linalool, (E)-nerolidol and phytol were present in low concentrations. The antimicrobial activity against aerobic and anaerobic oral bacteria was evaluated using the microdilution method, as was the cell viability test carried out with Vero cells. The oils from leaves and bark showed high antimicrobial activity, with minimum inhibitory concentrations between 62.5 and 125 µg·mL⁻¹ for most of the tested bacteria, including Streptococcus mutans, the main etiological agent of dental caries. Leaves oil displayed the lowest cytotoxic effect (EC₅₀ of 153 µg·mL⁻¹), while wood oil exhibited the highest toxicity to Vero cells. C. bakeriana oils are thus a source of biologically active compounds against aerobic and anaerobic oral microorganisms. This study is the first report on the chemical composition, antimicrobial activity and cytotoxicity of C. bakeriana.

This work reports the results of the investigation of bioactive compounds (chlorogenic acids, trigonelline, caffeine, total phenolics, and proanthocyanidins), total acid groups, and the antioxidant activity of the Arabian coffee (Coffea arabica) from the Brazilian cerrado (vast tropical savannah) (Minas Gerais state) and its defective beans (Black, green, and sour beans). The samples were prepared using three roasting degrees: light (180 ± 10 °C; 6,0 ± 1,0 minutes), medium (180 ± 10 °C; 8,0 ± 1,0 minutos), and dark (180 ± 10 °C; 10,0 ± 1,0 minutes). Considering the average of the three roasts per coffee and defective beans, the difference observed for the content of all constituents listed above was not significant (p > 0,05). Exceptions are the content of acid hydroxyl groups, which were slightly greater in the coffee defective beans and the content of caffeine, calculated using the semi-quantitative method, which was higher in the coffee itself. Both the coffee and its defective beans presented scavenging activity against DPPH . radical; however, the coffee antioxidant activity was always higher. The variations observed in the content of caffeine, total phenols, proanthocyanidins, phenolic acid groups, trigonelline, and chlorogenic acid levels can not explain the higher antioxidant activity observed for the medium roasted coffee (EC50 of 2,3 mg.mg –1 of DPPH . ).

O presente trabalho estudou os compostos bioativos (ácidos clorogênicos, trigonelina, cafeína, fenóis totais e proantocianidinas), grupos hidroxila ácidos e atividade antioxidante de um café arábica proveniente do Cerrado Mineiro e de seu PVA (grãos pretos, verdes e ardidos). As amostras foram preparadas nas torras clara (180 ± 10 °C; 6,0 ± 1,0 minutos), média (180 ± 10 °C; 8,0 ± 1,0 minutos) e escura (180 ± 10 °C; 10,0 ± 1,0 minutos). Considerando-se a média das três torras do café e do PVA, a diferença observada no teor de todos os constituintes acima não foi significativa (p > 0,05), exceto com o teor de grupos hidroxila ácidos que foi ligeiramente superior no PVA e cafeína calculada pelo método semiquantitativo que foi superior no café. Portanto, dentre esses constituintes, os compostos com grupos ácidos seriam os únicos que poderiam contribuir para explicar a grande diferença de sabor existente entre o café de grãos sadios e o de PVA. Tanto o café como o PVA apresentaram atividade seqüestradora do radical DPPH. nas três torras, sendo a atividade do café sempre superior. Analisando-se as variações dos teores de cafeína, fenóis totais, proantocianidinas, grupos hidroxila ácidos, trigonelina e ácidos clorogênicos, não foi possível explicar a atividade antioxidante superior apresentada pelo café da torra média (CE50 de 2,3 mg.mg-1 de DPPH.).This work reports the results of the investigation of bioactive compounds (chlorogenic acids, trigonelline, caffeine, total phenolics, and proanthocyanidins), total acid groups, and the antioxidant activity of the Arabian coffee (Coffea arabica) from the Brazilian cerrado (vast tropical savannah) (Minas Gerais state) and its defective beans (Black, green, and sour beans). The samples were prepared using three roasting degrees: light (180 ± 10 °C; 6,0 ± 1,0 minutes), medium (180 ± 10 °C; 8,0 ± 1,0 minutos), and dark (180 ± 10 °C; 10,0 ± 1,0 minutes). Considering the average of the three roasts per coffee and defective beans, the difference observed for the content of all constituents listed above was not significant (p > 0,05). Exceptions are the content of acid hydroxyl groups, which were slightly greater in the coffee defective beans and the content of caffeine, calculated using the semi-quantitative method, which was higher in the coffee itself. Both the coffee and its defective beans presented scavenging activity against DPPH. radical; however, the coffee antioxidant activity was always higher. The variations observed in the content of caffeine, total phenols, proanthocyanidins, phenolic acid groups, trigonelline, and chlorogenic acid levels can not explain the higher antioxidant activity observed for the medium roasted coffee (EC50 of 2,3 mg.mg-1 of DPPH.).

The advent of organocatalysis brought the prospect of a complementary mode of catalysis, with the potential for savings in cost, time and energy. 1 In this work p-sulfonic acid calix[4]arene (CX4SO3H) was employed as a organocatalyst to promote a threecomponent Povarov reaction, for the preparation of julolidines. 2 Julolidines and derivatives are endowed with interesting scientific and industrial applications. 3

A diastereoselective three-component cascade reaction, catalyzed by 4-sulfonic acid calix[4]arene, provides a new access to diverse julolidine derivatives (IV) in high yields.

A diastereoselective three-component cascade reaction, catalyzed by p-sulfonic acid calix[4]arene, provides a unique method to access diverse julolidine derivatives in high yields. Additionally, the reaction was also monitored by mass spectrometry and the mechanistic pathway uncovered.

Organosolv and kraft lignins were treated with ozone both in basic and acid media and the reaction was studied kinetically. In contrast to reported studies, ozone was more efective in basic medium. Kraft lignin was degraded faster than organosolv lignin in both media but in the basic medium the rate of reaction was very much faster than in the acid one: for kraft lignin, the observed degradation was 93% for 2 min of reaction in the basic medium and 56% for 10 min of reaction in the acid medium; for organosolv lignin, 47% and 25%, respectively, in the same times. Higher phenolic hydroxyl groups contents increase the reaction rate.

CNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico FAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas Gerais CAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível Superior Reações de acoplamento Carbono-Carbono (C-C), catalisadas por paládio, estão entre as metodologias sintéticas mais importantes e usadas para a construção de estruturas moleculares orgânicas. A importância e relevância dessas metodologias foi reconhecida pela atribuição do prêmio Nobel de Química de 2010, aos pesquisadores, Heck, Negishi e Suzuki, que muito contribuíram nessa área. Estas reações normalmente são realizadas em solventes orgânicos anidros, alguns tóxicos, inflamáveis e caros. Na contramão dessas condições, tem surgido muitas alternativas, ambientalmente corretas, utilizando meios atóxicos e baratos como a água, dentro dos preceitos da Química Verde. O uso da água como solvente em reações catalisadas por paládio, para o acoplamento C-C, talvez seja umas das mais bem-vindas metodologias catalíticas em síntese orgânica, aliando eficiência, consciência ambiental e custo reduzido. Neste trabalho foram sintetizados catorze aldeídos iônicos, sendo dois com grupos de caráter aniônico (sulfonato e ácido carboxílico) e doze com grupos catiônicos, sendo seis com sítio imidazólio e seis com o sítio trifenilfosfônio, com rendimentos entre 65% e 99%. Obtido os aldeídos, estes foram submetidos a reação de condensação com a o-fenilenodiamina, obtendo-se catorze iminas com rendimentos entre 65 e 95%. Essas iminas foram utilizadas como ligantes para a obtenção de complexos iônicos de paládio(II), utilizando acetato de paládio(II) como fonte de paládio, com rendimentos que variaram entre 67% e 92%. Feita a síntese desses complexos, a próxima etapa foi a avaliação dos mesmos como catalisadores do acoplamento de Heck utilizando água como solvente. Inicialmente parâmetros como natureza da base, tipo de surfactante, temperatura e tempo de reação foram avaliados com o intuito de estabelecer a melhor condição reacional para a reação de Heck em água utilizando o bromobenzeno e estireno como substratos. Feito isso, os complexos sintetizados foram aplicados como catalisadores na reação de acoplamento e todos os complexos apresentaram uma atividade catalítica satisfatória com rendimentos variando de 54 a 100% na obtenção do produto de acoplamento. Quatro complexos de paládio(II) das bis-aminas iônicas, análogos reduzidos das bis-iminas iônicas foram obtidos com rendimentos entre 73 e 85%. Os testes de catálise do acoplamento de Heck com esses complexos como catalisadores forneceram rendimentos entre 48 e 85%, resultados próximos aos obtidos utilizando os análogos das bis-iminas. Carbon-Carbon coupling reactions catalyzed by palladium are among the most important and used synthetic methodologies for the construction of organic molecular structures. The importance and relevance of these methodologies was recognized by the award of the 2010 Nobel Prize in Chemistry to the researchers, Heck, Negishi and Suzuki, who contributed greatly in this area. These reactions are usually carried out in anhydrous organic solvents, some of which are toxic, flammable and expensive. Contrary to these conditions, many alternatives have emerged, environmentally correct, using non-toxic and cheap means such as water, within the precepts of Green Chemistry. The use of water as a solvent in palladium-catalyzed reactions for C-C coupling is perhaps one of the most welcome catalytic methodologies in organic synthesis, combining efficiency, environmental awareness and reduced cost. In this work, fourteen ionic aldehydes were synthesized, two of them with anionic groups (sulfonate and carboxylic acid) and twelve with cationic groups, six with imidazolium site and six with triphenylphosphonium site, with yields between 65 and 99%. Once the aldehydes were obtained, they were subjected to a condensation reaction with o-phenylenediamine, obtaining fourteen imines with yields between 65 and 95%. These imines, in turn, were used as binders to obtain ionic palladium(II) complexes, using palladium(II) acetate as palladium source, with yields ranging between 67 and 92%. The obtained palladium(II) complexes were used as catalysts in Heck coupling, using water as solvent. Initially parameters such as base, surfactant, temperature and time were evaluated in order to establish the best reaction condition for the Heck reaction in water using bromobenzene and styrene as substrate. After that, the synthesized complexes were applied as catalysts in the coupling reaction and all the complexes showed a satisfactory catalytic activity of 54 to 100% of yield in obtaining the coupling product. Four palladium(II) complexes of ionic bis-amines, reduced analogues of ionic bis-imines were obtained with yield between 73 and 85%. Heck coupling catalysis tests with these complexes as catalysts provided yields between 48 and 85%, results close to those obtained using the bis-imine analogues.

A espécie Justicia acuminatissima (Acanthaceae) é uma planta medicinal conhecida popularmente como "sara-tudo". As folhas são utilizadas amplamente na Região Amazônica para alívio de processos inflamatórios. A partir dessas informações, este trabalho teve como objetivo realizar estudos químicos e ensaios farmacológicos para comprovar cientificamente seu uso. Para isso, folhas e galhos foram coletados no Município de Itacoatiara-AM. Após secagem e moagem procedeu-se à maceração separadamente em etanol e etanol a 70% do material botânico coletado. Os extratos brutos obtidos em etanol foram fracionados com solventes em ordem crescente de polaridade, utilizando como elutentes hexano, DCM, AcOEt e MeOH. Dessa forma foram obtidas quatro frações a partir das folhas e o mesmo foi realizado com os galhos. Um extrato aquoso foi também preparado a partir do decocto das folhas. A investigação fitoquímica das frações obtidas das folhas e galhos de J. acuminatissima proporcionou o isolamento dos esteroides sitosterol e mistura de sitosterol com estigmasterol, além dos triterpenos lupeol, acil-lupeol, friedelina, friedelinol, mistura de lupeol com a-amirina e ß-amirina, mistura de betulina e eritrodiol e ácido betulínico, isolados a partir das frações em hexano e diclorometano das folhas e galhos. As frações em acetato de etila das folhas e galhos proporcionaram o isolamento dos esteroides glicosilados sitosterol e estigmasterol em mistura, além do ácido phidroxibenzóico e de um alcaloide inédito (3-etil-8-oxa-3-azabiciclo[3,2,1]octano-1,6,7-triol). A mistura de a-glucose e ß-glucose, além da sacarose foram isoladas a partir do extrato em metanol das folhas. O estudo fitoquímico do extrato aquoso das folhas de J. acuminatissima foi realizado por meio de análises em CLAE preparativa. Como resultado, um novo derivado de luteolina glicosilada foi isolado: luteolina-3'-O-ß-xilofuranosídeo. Além disso, três outros derivados de luteolina glicosilada foram descritos pela primeira vez no gênero Justicia: luteolina-5-O- ß-rutinosídeo, luteolina-7-O- ß-rutinosídeo e luteolina-7-O-ß-glicosídeo. Estudos teóricos foram realizados para os flavonoides obtidos. Essas análises auxiliaram a elucidação desses compostos. Em relação aos estudos farmacológicos, extratos apolares da folha e alguns triterpenos mostraram atividades antimicrobiana e anti-inflamatória. Além disso, a fração em AcOEt das folhas mostrou ação antimicrobiana significativa contra E. coli e C. albicans, as frações em DCM exibiram ação maior do que 60% para todos os microorganismos testados na concentração de 250 µg.mL-1. As frações FAF, FDF, FMF e FF, além do lupeol, luteolina-3'-O-xilofuranosídeo e da mistura de ß-sitosterol e estigmasterol mostraram redução no quadro inflamatório das patas de ratos. É importante salientar que, durante os estudos com J. acuminatissima, realizaram-se análises em CLAE para verificar possíveis alterações químicas após utilização de raios gama como método de descontaminação dessa espécie. Como resultados, percebeu-se que a incidência de radiação gama até 20 kGy não interfere na integridade química de J. acuminatissima. Além disso, estes estudos mostram que doses de 3,0 kGy são suficientes para a eliminação de Aspergillus aculeatus, espécie de fungo predominante nas folhas da espécie estudada. Justicia acuminatissima (Acanthaceae) is a medicinal plant, popularly known as "sara-tudo". This species is widely used in the Amazon region to relief inflammatory processes. The literature does not describe chemical and biological studies for this species. This study aimed to conduct chemical and pharmacological studies that prove their scientific use. Leaves and twigs were collected in Itacoatiara city - Amazonas state.After drying and grinding the material (separately) was performed the maceration with ethanol and ethanol 70% (v/v), yielding the respective crude extract. The leaf and twigs extracts obtained in ethanol were fractionated with solvents in an order of increasing polarity, such as hexane, dichloromethane, ethyl acetate, and methanol. Thus fourfractions from the leaves and four fractions from the twig were obtained.Phytochemical studies of the hexane fractions of leaves and twigs of J.acuminatissima provided sitosterol, a mixture of stigmasterol with sitosterol, lupeol, acyl-lupeol, friedelin, friedelinol, mixture of á-amyrin and lupeol, betulinic acid and the mixture of erythrodiol with betulin. The fractions of ethyl acetate from the leaves and twigs provided the isolation of a mixture of stigmasterol and sitosterol glucoside, besides the 4-hydroxy-benzoic acid and new alkaloid (3-ethyl-8-oxa-3-azabicyclo [3,2,1] octane- 1,6,7-triol. A mixture of á-glucose and â-glucose, sucrose was isolated from the methanol extract of the leaves. Study of aqueous extract of leaves of J. acuminatissima was performed by HPLCanalysis. As a result, a new derivative of luteolin glycosides was isolated: luteolin-3'-Oxylofuranoside. In addition, three other luteolin glycoside derivatives were obtained for the first time for the Justicia: luteolin-5-O-rutinoside, luteolin-7-O-rutinoside, and luteolin-7-O-glucoside. Theoretical studies were performed to flavonoids. These analyzes allowed the elucidation of these compounds.The polar extract, nonpolar extract and some triterpenes and flavonoids exhibited antimicrobial and anti-inflammatory activities. Furthermore, the ethyl acetate fraction showed a expressive antimicrobial activity against E. coli and C. albicans. The dichloromethane fraction of leaves presented a 60% higher activity against all microorganisms tested using the same concentration of 250 ìg.mL-1. The fractions FAF, FDF, FMF, FF, lupeol, luteolin-3'-O-xylofuranoside, and the mixture of â- sitosterol/stigmasterol showed a significative reduction in the inflammatory process ofrats paws. It is worth highlighting that during the studies with J. acuminatissima was performed HPLC analysis to check for possible chemical changes after use of gamma rays as a decontamination method of this species. As a result, it was found that thegamma radiation up to 20 kGy did not interfere in the chemical integrity of J. acuminatissima. Furthermore, it was observed that a dose of 3.0 kGy was enough for the elimination of Aspergillus aculeatus, predominant fungi on the leaves of the species studied.