Chemical constituents of açai berry pulp (Euterpe oleracea Mart.) by LC-UV-BPSU/NMR and LC-UV-SPE/NMR.

The techniques LC-UV-BPSU and LC-UV-SPE/NMR were applied for the first time in the analysis of açai berry (Euterpe oleracea Mart.) pulp extracts. Those techniques allowed the identification of twenty-three metabolites: Valine (1), citric acid (2), tachioside (3), isotachioside (4), α-guaiacylglycerol (5), syringylglycerol (6), uridine (7), adenosine (8), dimethoxy-1,4-benzoquinone (9), koaburaside (10), protocatechuic acid (11), eurycorymboside B (12), 7',8'-dihydroxy-dihydrodehydroconiferyl alcohol-9-O-ß-D-glucopyranoside (13), orientin (14), homoorientin (15), dihydrokaempferol-3-glucoside (16), isolariciresinol-9'-O-ß-D-glucopyranoside (17), 5'-methoxyisolariciresinol-9'-O-ß-D-glucopyranoside (18), cyanidin-3-O-glucoside (19), cyandin-3-O-rutenoside (20), 9,12-octadecadienoic acid (Z,Z)-2-hydroxy-1-(hydroxymethyl) ethyl ester (21), linolenic acid (22), and 1,2-di-O-α-linolenoyl-3-O-ß-D-galactopyranosyl-sn-glycerol (23). In this plant, compounds 3, 4, 5, 6, 8, 10, 12, 17, 18, 21, and 23 are reported for the first time. All the structures were determined through extensive analyses of 1D and 2D NMR data, mass spectrometry, and comparison with published data. This methodology has proven to be an efficient alternative to the analysis of complex extracts containing a large variety of compounds.

1H NMR spectroscopy applied to identify chemical aging markers in green coffee (Coffea arabica L.).

Nuclear magnetic resonance (NMR) was used to identify metabolic changes in green coffee beans stored in 3 different packages. Sensory and NMR analyses were performed at 0, 3, 6, 9, 12 and 18 months of storage. The decrease in the sensory quality of beverages by aging was more pronounced in the paper bags after 6 months of storage. High barrier bags and vacuum packs were able to maintain quality for 18 months of storage, regardless of the coffee processing method. The NMR technique allowed the differentiation of coffee packed in paper bags from the 3rd month of storage. These results indicate that it is possible to anticipate by up to 3 months the identification of changes that would otherwise only be noticed through sensory analysis after six months of storage. Choline and glycerophosphocholine are the main chemical compounds associated with the changes observed in the storage of green coffee in paper bags.

Monitoring Stimulated Darkening from UV-C Light on Different Bean Genotypes by NMR Spectroscopy.

The use of UV-C cool white light on bean (Phaseolus vulgaris L.) seeds significantly increases the biochemical seed coat post-harvest darkening process, whilst preserving seed germination. The aim of this work consists in monitoring the effect caused by the incidence of UV-C light on different bean genotypes using NMR spectroscopy. The genotype samples named IAC Alvorada; TAA Dama; BRS Estilo and BRS Pérola from the Agronomic Institute (IAC; Campinas; SP; Brazil) were evaluated. The following two methodologies were used: a prolonged darkening, in which the grain is placed in a room at a controlled temperature (298 K) and humidity for 90 days, simulating the supermarket shelf; an accelerated darkening, where the grains are exposed to UV-C light (254 nm) for 96 h. The experiments were performed using the following innovative time-domain (TD) NMR approaches: the RK-ROSE pulse sequence; one- and two-dimensional high resolution (HR) NMR experiments (1H; 1H-1H COSY and 1H-13C HSQC); chemometrics tools, such as PLS-DA and heat plots. The results suggest that the observed darkening occurs on the tegument after prolonged (90 days) and accelerated (96 h) conditions. In addition, the results indicate that phenylalanine is the relevant metabolite within this context, being able to participate in the chemical reactions accounted for by the darkening processes. Additionally, it is possible to confirm that a UV-C lamp accelerates oxidative enzymatic reactions and that the NMR methods used were a trustworthy approach to monitor and understand the darkening in bean seeds at metabolite level.

Mechanistic investigation of enolate/stabilized vinylogous carbanion-mediated organocatalytic azide (3 + 2) cycloaddition reactions for the synthesis of 1,2,3-triazoles.

Herein, we report a fully detailed mechanistic study involving an organocatalyzed 1,3-dipolar cycloaddition via enolate or stabilized vinylogous carbanion intermediates and azide for the synthesis of 1,2,3-triazoles. A detailed investigation of the elementary steps, intermediates, and transition states of the two organocatalyzed metal-free click reactions is supported by DFT calculations and 1H NMR monitoring experiments, providing detailed profiles for both reaction mechanisms. Distortion-interaction activation-strain (DIAS) analysis was also employed to further elucidate the regioselectivity in both reactions.

Lignans as new chemical markers of a certified Brazilian organic propolis.

Commercially certified organic propolis produced in areas of environmental conservation and reforestation forests of Southern Brazil are generally poor in flavonoids, although one of its variants - Brazilian certified organic propolis 1 (OP1) - has shown strong antioxidant activity. The objective was to identify active compounds from OP1 related to its strong antioxidant activity. OP1 ethanolic extracts were subjected to liquid-liquid fractionation, and the fractions presenting the strongest antioxidant activity were combined and purified into subfractions. Compounds isolated from the most active subfractions had their structure elucidated by Nuclear Magnetic Resonance (NMR). As a result, five lignans and two lignan-precursors were isolated, and four of them are herein reported for the very first time in propolis. Hence, these compounds may be used as chemical markers for product standardization and authentication purposes, since OP1 is only produced by honeybees in native forests and its botanical origins remain unknown.

NMR spectroscopy of wastewater: A review, case study, and future potential.

NMR spectroscopy is arguably the most powerful tool for the study of molecular structures and interactions, and is increasingly being applied to environmental research, such as the study of wastewater. With over 97% of the planet's water being saltwater, and two thirds of freshwater being frozen in the ice caps and glaciers, there is a significant need to maintain and reuse the remaining 1%, which is a precious resource, critical to the sustainability of most life on Earth. Sanitation and reutilization of wastewater is an important method of water conservation, especially in arid regions, making the understanding of wastewater itself, and of its treatment processes, a highly relevant area of environmental research. Here, the benefits, challenges and subtleties of using NMR spectroscopy for the analysis of wastewater are considered. First, the techniques available to overcome the specific challenges arising from the nature of wastewater (which is a complex and dilute matrix), including an examination of sample preparation and NMR techniques (such as solvent suppression), in both the solid and solution states, are discussed. Then, the arsenal of available NMR techniques for both structure elucidation (e.g., heteronuclear, multidimensional NMR, homonuclear scalar coupling-based experiments) and the study of intermolecular interactions (e.g., diffusion, nuclear Overhauser and saturation transfer-based techniques) in wastewater are examined. Examples of wastewater NMR studies from the literature are reviewed and potential areas for future research are identified. Organized by nucleus, this review includes the common heteronuclei (13C, 15N, 19F, 31P, 29Si) as well as other environmentally relevant nuclei and metals such as 27Al, 51V, 207Pb and 113Cd, among others. Further, the potential of additional NMR methods such as comprehensive multiphase NMR, NMR microscopy and hyphenated techniques (for example, LC-SPE-NMR-MS) for advancing the current understanding of wastewater are discussed. In addition, a case study that combines natural abundance (i.e. non-concentrated), targeted and non-targeted NMR to characterize wastewater, along with in vivo based NMR to understand its toxicity, is included. The study demonstrates that, when applied comprehensively, NMR can provide unique insights into not just the structure, but also potential impacts, of wastewater and wastewater treatment processes. Finally, low-field NMR, which holds considerable future potential for on-site wastewater monitoring, is briefly discussed. In summary, NMR spectroscopy is one of the most versatile tools in modern science, with abilities to study all phases (gases, liquids, gels and solids), chemical structures, interactions, interfaces, toxicity and much more. The authors hope this review will inspire more scientists to embrace NMR, given its huge potential for both wastewater analysis in particular and environmental research in general.

Phenylalanine and COVID-19: Tracking disease severity markers.

BACKGROUND: Although there are several severity predictors for COVID-19, none are specific. Serum levels of phenylalanine were recently associated with increased inflammation, higher SOFA scores, ICU admission, and mortality rates among non-COVID-19 patients. Here, we investigated the relationship between phenylalanine and inflammatory markers in adults with COVID-19. METHODS: We assessed adults with COVID-19 at hospital admission for clinical and laboratory data. Nuclear magnetic resonance spectroscopy measured serum levels of phenylalanine and other amino acids of its metabolomic pathway. Flow Cytometry measured serum levels of IL-2, IL-4, IL-6, Il-10, TNF-α, and IFN-γ. Linear regression models adjusted for potential confounders assessed the relationship between serum levels of phenylalanine and inflammatory cytokines. RESULTS: Phenylalanine and tyrosine were significantly lower in mild disease as compared to moderate and severe groups. Linear regression models showed that phenylalanine is independently and positively associated with disease severity regardless of the cytokine analyzed and after adjustment for potential confounders. In addition, mild cases showed consistently lower serum phenylalanine levels within the first ten days from disease onset to hospital admission. CONCLUSIONS: Phenylalanine is a marker of disease severity. This association is independent of the time between the onset of symptoms and the magnitude of the inflammatory state.

Octahedral ruthenium and magnesium naringenin 5-alkoxide complexes: NMR analysis of diastereoisomers and in-vivo antibacterial activity against Xylella fastidiosa.

Although many copper-based antimicrobial compounds have been developed to control pathogenic bacteria and fungi in plants and applied for crop protection, there is evidence that several plant pathogens have developed resistance to copper-based antimicrobial compounds, including some Xanthomonas species. Xylella is a bacterial genus belonging to the Xanthomonas family; and X. fastidiosa, which is responsible for citrus variegated chlorosis (CVC) in sweet orange, may develop resistance to one or more copper-based antimicrobials. Because of the time required for the development and approval of new antimicrobials for commercial use, the discovery of novel bactericidal compounds is essential before the development of resistance to the antimicrobials currently in use becomes widespread. Here, we explored the antimicrobial potential of two newly synthesized antimicrobials complexes and one natural compound against X. fastidiosa. Several nuclear magnetic resonance (NMR) assays with high resolution and sensitivity were developed to identify new diastereoisomers in the context of octahedral ruthenium - [Ru(narin)(phen)2]PF6-and magnesium naringenin 5-alkoxide - [Mg(narin)(phen)2]OAc - complexes, obtained in the present work. The NMR assays proved to be powerful tools for the identification of isomers in metal complexes. Moreover, a protocol for the in-vivo determination of the effects of these complexes against X. fastidiosa was developed. The main trunks of X. fastidiosa infected plants were injected with the two complexes as well as with the limonoid azadirachtin using a syringe; the number of bacterial cells in the plants following treatment was estimated via real-time quantitative PCR (qPCR). Importantly, the administration of both complexes and of azadirachtin drastically reduced the number of X. fastidiosa cells in vivo.

Multi-response optimization of alginate bleaching technology extracted from brown seaweeds by an eco-friendly agent.

Alginate only finds industrial applicability after undergoing a bleaching process to improve its visual appearance. Box-Behnken Design was used to optimize bleaching parameters (time, oxygen flow and temperature) for sodium alginate (SA) extracted from seaweeds using ozone as the bleaching agent. The optimal conditions (oxygen flow 2 L/min for 35 min at 25 °C) resulted in an ozone-bleached SA with a mannuronic/guluronic acids ratio of 0.70, viscosity-average molecular weight of 66.30 kDa and dynamic viscosity of 1.39 mPa.s, aligned to strong and brittle gels formation, which are potentially suitable for hydrogels and bioink application. Results indicated that ozonation caused depolymerization of the SA chain. Colorimetric parameters showed that ozone has a great bleaching efficacy. The bleached sample presented high antioxidant capacity, highlighting that discoloration by ozone might have minimal effects on the bioactive compounds which are valuable ingredients for food-based products.

Preclinical validation of occupational and environmental safety of an isolation system for noninvasive ventilation in COVID-19 and other aerosol-transmitted infections.

Background: The current SARS-CoV-2 pandemic has provoked the collapse of some health systems due to insufficient intensive care unit capacity. The use of continuous positive airway pressure (CPAP) and high-flow nasal oxygen (HFNO) therapies has been limited in consideration of the risk of occupational infection in health-care professionals. Aims: In preclinical experimental simulations, evaluate occupational and environmental safety of the newly developed isolation system for aerosol-transmitted infections (ISATI). Method: Simulations were conducted to test ISATI's capability to isolate aerosolized molecular (caffeine), and biological (SARS-CoV-2 synthetic RNA) markers. Caffeine deposition was analyzed on nitrocellulose sensor discs by proton nuclear magnetic resonance spectroscopy. Synthetic SARS-CoV-2 detection was performed by reverse transcription-polymerase chain reaction. Results: ISATI demonstrated efficacy in isolating molecular and biological markers within the enclosed environment in simulated conditions of CPAP, HFNO and mechanical ventilation therapy. Neither the molecular marker nor substantial amounts of synthetic SARS-CoV-2 RNA were detected in the surrounding environment, outside ISATI, indicating appropriate occupational safety for health-care professionals. Conclusion: Aerosolized markers were successfully contained within ISATI in all experimental simulations, offering occupational and environmental protection against the dissemination of aerosolized microparticles under CPAP or HFNO therapy conditions, which are indicated for patients with acute respiratory infections.

Metabolite Profiling by UPLC-MSE, NMR, and Antioxidant Properties of Amazonian Fruits: Mamey Apple (Mammea Americana), Camapu (Physalis Angulata), and Uxi (Endopleura Uchi).

The metabolite profiling associated with the antioxidant potential of Amazonian fruits represents an important step to the bioactive compound's characterization due to the large biodiversity in this region. The comprehensive bioactive compounds profile and antioxidant capacities of mamey apple (Mammea americana), camapu (Physalis angulata), and uxi (Endopleura uchi) was determined for the first time. Bioactive compounds were characterized by ultra-performance liquid chromatography coupled to high resolution mass spectrometry (UPLC-MSE) in aqueous and ethanolic extracts. Globally, a total of 293 metabolites were tentatively identified in mamey apple, campau, and uxi extracts. The main classes of compounds in the three species were terpenoids (61), phenolic acids (58), and flavonoids (53). Ethanolic extracts of fruits showed higher antioxidant activity and total ion abundance of bioactive compounds than aqueous. Uxi had the highest values of phenolic content (701.84 mg GAE/100 g), ABTS (1602.7 µmol Trolox g-1), and ORAC (15.04 µmol Trolox g-1). Mamey apple had the highest results for DPPH (1168.42 µmol TE g-1) and FRAP (1381.13 µmol FSE g-1). Nuclear magnetic resonance (NMR) spectroscopy results showed that sugars and lipids were the substances with the highest amounts in mamey apple and camapu. Data referring to chemical characteristics and antioxidant capacity of these fruits can contribute to their economic exploitation.

New antifungal ent-labdane diterpenes against Candida glabrata produced by microbial transformation of ent-polyalthic acid.

Candida glabrata, the most common non-albicans Candida species and one of the primary causes of candidemia, exhibits decreased susceptibility to azoles and more recently to echinocandins. Polyalthic acid 1, a furan diterpene, has been shown promising biological potential and in this study ent-polyalthic acid derivatives with antifungal activity against Candida glabrata were produced by microbial transformation. Incubation of 1 with Aspergillus brasiliensis afforded two known (compounds 5 and 10) and eight new derivatives (compounds 2-4, 6-9 and 11). The most common reaction was hydroxylation, but isomerization of the double bond and acetylation were also detected. None of the tested compounds showed cytotoxicity against HeLa, MCF-7 and MCF-10A cell lines showing IC50 values ranging from 62.6 µM to > 500 µM. Compounds 1, 5, 6, 8 and 11 showed fungistatic effects (ranging from 34.1 µM to 39.5 µM) on C. glabrata at lower concentrations than fluconazole (163.2 µM). Compounds 1, 6 and 8 were more potent fungicides (ranging from 79.0 to 143.6 µM) than fluconazole, which showed fungicidal effect at concentrations higher than 163.2 µM. These results suggest that ent-polyalthic acid and some of its derivatives could be used as lead compounds to develop new antifungal agents.

A Supramolecular Interaction of a Ruthenium Complex With Calf-Thymus DNA: A Ligand Binding Approach by NMR Spectroscopy.

Lawsone itself exhibits interesting biological activities, and its complexation with a metal center can improve the potency. In this context a cytotoxic Ru-complex, [Ru(law)(dppb)(bipy)] (law = lawsone, dppb = 1,4-bis(diphenylphosphino)butane and bipy = 2,2'-bipyridine), named as CBLAU, was prepared as reported. In this work, NMR binding-target studies were performed to bring to light the most accessible interaction sites of this Ru-complex toward Calf-Thymus DNA (CT-DNA, used as a model), in a similar approach used for other metallic complexes with anti-cancer activity, such as cisplatin and carboplatin. Advanced and robust NMR binding-target studies, among them Saturation Transfer Difference (STD)-NMR and longitudinal relaxometry (T1), were explored. The 1H and 31P -NMR data indicate that the structure of Ru-complex remains preserved in the presence of CT-DNA, and some linewidth broadening is also observed for all the signals, pointing out some interaction. Looking at the binding efficiency, the T1 values are highly influenced by the formation of the CBLAU-DNA adduct, decreasing from 11.4 s (without DNA) to 1.4 s (with DNA), where the difference is bigger for the lawsone protons. Besides, the STD-NMR titration experiments revealed a stronger interaction (KD = 5.9 mM) for CBLAU-DNA in comparison to non-complexed lawsone-DNA (KD = 34.0 mM). The epitope map, obtained by STD-NMR, shows that aromatic protons from the complexed lawsone exhibits higher saturation transfer, in comparison to other Ru-ligands (DPPB and bipy), suggesting the supramolecular contact with CT-DNA takes place by the lawsone face of the Ru-complex, possibly by a spatial π-π stacking involving π-bonds on nucleic acids segments of the DNA chain and the naphthoquinone group.

Gloeosporiocide, a new antifungal cyclic peptide from Streptomyces morookaense AM25 isolated from the Amazon bulk soil.

Actinobacteria are known by their ability to produce several antimicrobial compounds of biotechnological interest. Thus, in this study, we isolated and identified by partial 16S RNA sequencing ∼100 actinobacteria isolates from guarana (Paullinia cupana) bulk soil. Besides, we isolated from the actinobacteria Streptomyces morookaense AM25 a novel cyclic peptide, named gloeosporiocide, molecular formula C44H48N11O7S3 (calculated 938.2901), and characterized by the presence of cyclized cysteins to form three thiazols. The novel compound had activity against the plant pathogen Colletotrichum gloeosporioides, assayed by the paper disk diffusion method (42.7% inhibition, 0.1 mg disk-1) and by the microdilution assay (1.25 g L-1). Our results reveal the potential of the actinobacteria from the Amazon rhizospheric soils as biocontrol agents as well as producers of new compounds with antifungal activity. Thus, this work constitutes a step forward in the development of the biotechnology of actinobacteria in the production of compounds of agronomic interest.

Secondary metabolites produced by endophytic fungi: novel antifungal activity of fumiquinone B

Fungi are present in the most diverse environments including the interior of plant tissues, living as endophytes without causing apparent damage. These endophytes are producers of secondary metabolites, also known as natural products, such as fungicides. Here, we evaluated the ethyl acetate fractions obtained from endophytic fungiisolated from plants in the genus Begonia. The fractions were submitted to inhibitorytest against the plant pathogens Diaporthe phaseolorum and Colletotrichum gloeosporioides. From the 88 ethyl acetate fractions evaluated, 14.7 % inhibited C. gloeosporioidesand 11.3 %inhibited D. phaseolorum. One fungal isolate displaying an active fraction was selected for chemical investigation. The fungus identified as Neopestalotiopsissp., produced a compound that was active against D. phaseolorum, with a MIC of 312 μg mL-1(1,695.3 μM). The compound was identified by mass spectrometry and 1H NMR as the known compound fumiquinone B. The results highlight that the endophytes are capable of producing compounds that may be used to control plant pathogens. The compound fumiquinone B is reported for the first time as an antifungal agent against D. phaseolorum, a relevant plant pathogen worldwide. This is also the first report of the production of fumiquinone B by the genus Neopestalotiopsis.

Biological and Chemical Control of Sclerotinia sclerotiorum using Stachybotrys levispora and Its Secondary Metabolite Griseofulvin.

Sclerotinia sclerotiorum is responsible for the white mold of soybeans, and the difficulty to control the disease in Brazil is causing million-dollar damages. Stachybotrys levispora has shown activity against S. sclerotiorum. In our present investigation, we analyzed the chemical basis of this inhibition. Eight compounds were isolated, and using spectroscopic methods, we identified their structures as the known substances 7-dechlorogriseofulvin, 7-dechlorodehydrogriseofulvin, griseofulvin, dehydrogriseofulvin, 3,13-dihydroxy-5,9,11-trimethoxy-1-methylbenzophenone, griseophenone A, 13-hydroxy-3,5,9,11-tetramethoxy-1-methylbenzophenone, and 12-chloro-13-hydroxy-3,5,9,11-tetramethoxy-1-methylbenzophenone. Griseofulvin inhibited the mycelial growth of S. sclerotiorum at 2 µg mL-1. Thus, the antagonistic effect of S. levispora to S. sclerotiorum may well be due to the presence of griseofulvins. Our results stimulate new work on the biosynthesis of griseofulvins, to locate genes that encode key enzymes in these routes and use them to increase the production of these compounds and thus potentiate the fungicide effect of this fungus. S. levispora represents an agent for biocontrol, and griseofulvin represents a fungicide to S. sclerotiorum.

Synthetic acylsugars and their effects on the control of arthropod pests / Acilaçúcares sintéticos e seu efeito no controle de artrópodes-praga

ABSTRACT One of the main problems facing agriculture is the loss of production as a result of the attack of agricultural pests. Alternative ways to work around this problem are being sought. There are substances called acylsugars that are naturally produced by the wild tomato species S. pennellii and affect arthropod pests. The objectives of this work were to synthesize two acylsugars and assess the biological effect of these on the arthropod pests Bemissia tabaci and Tetranycus urticae. The syntheses were performed via the reactions of glucose and sucrose (saccharose) with acetic anhydride using sodium acetate as the catalyst. The products of these reactions were sucrose octa-acetate and glucose penta-acetate, the structures of which were confirmed by spectroscopic techniques. In a resistance test against the mite, a linear correlation between the concentration of the synthesized substances, and the dislocation of the mite was obtained. A delay in the hatching of the arthropod eggs was observed, causing a mortality rate of approximately 95% in the 1st instar larvae of mites that was confirmed in adults. In the biological tests with Bemisia tabaci, there was a low rate of hatching and emergence, and the effect on the nymphs was the deformation of the emergent adults.

RESUMO Um dos grandes problemas que a agricultura enfrenta é a perda de produção causada pelo ataque de pragas agrícolas. Assim, buscam-se maneiras alternativas de contornar esse problema. Dentre esses, encontram-se substâncias, denominadas de acilaçúcars, que são produzidas naturalmente por espécies selvagens do tomate S. pennellii e que apresentam efeito sobre artrópodes-praga. Os objetivos desse trabalho foram sintetizar dois compostos de acilaçúcares e avaliar o efeito biológico destas sobre os artrópodes-praga Bemissia tabaci e Tetranycus urticae. A síntese foi feita via as reações de glicose e sacarose com anidrido acético, utilizando acetato de sódio como catalisador. Os produtos dessas reações foram o octa-acetato de sacarose e o penta-acetato de glicose, cujas estruturas foram confirmadas por técnicas espectroscópicas. No teste de resistência do ácaro, foi possível obter um ajuste linear entre a concentração das substâncias sintetizadas e o deslocamento do ácaro. Ambas as substâncias obtidas apresentaram um atraso na eclosão dos ovos do artrópode, ocasionando uma mortalidade de aproximadamente 95% em ácaros de 1º ínstar que foram confirmadas em adultos. Nos testes biológicos com Bemisia tabaci, verificou-se uma baixa taxa de eclosão e emergência, sendo que o efeito sobre as ninfas foi a má formação para adultos emergidos.

Neurobehavioral and Antioxidant Effects of Ethanolic Extract of Yellow Propolis.

Propolis is a resin produced by bees from raw material collected from plants, salivary secretions, and beeswax. New therapeutic properties for the Central Nervous System have emerged. We explored the neurobehavioral and antioxidant effects of an ethanolic extract of yellow propolis (EEYP) rich in triterpenoids, primarily lupeol and ß-amyrin. Male Wistar rats, 3 months old, were intraperitoneally treated with Tween 5% (control), EEYP (1, 3, 10, and 30 mg/kg), or diazepam, fluoxetine, and caffeine (positive controls) 30 min before the assays. Animals were submitted to open field, elevated plus maze, forced swimming, and inhibitory avoidance tests. After behavioral tasks, blood samples were collected through intracardiac pathway, to evaluate the oxidative balance. The results obtained in the open field and in the elevated plus maze assay showed spontaneous locomotion preserved and anxiolytic-like activity. In the forced swimming test, EEYP demonstrated antidepressant-like activity. In the inhibitory avoidance test, EEYP showed mnemonic activity at 30 mg/kg. In the evaluation of oxidative biochemistry, the extract reduced the production of nitric oxide and malondialdehyde without changing level of total antioxidant, catalase, and superoxide dismutase, induced by behavioral stress. Our results highlight that EEYP emerges as a promising anxiolytic, antidepressant, mnemonic, and antioxidant natural product.

Comparative Study of Chemical Composition and Biological Activity of Yellow, Green, Brown, and Red Brazilian Propolis.

The chemical composition and biological activity of a sample of yellow propolis from Mato Grosso do Sul, Brazil (EEP-Y MS), were investigated for the first time and compared with green, brown, and red types of Brazilian propolis and with a sample of yellow propolis from Cuba. Overall, EEP-Y MS had different qualitative chemical profiles, as well as different cytotoxic and antimicrobial activities when compared to the other types of propolis assessed in this study and it is a different chemotype of Brazilian propolis. Absence of phenolic compounds and the presence of mixtures of aliphatic compounds in yellow propolis were determined by analysing (1)H-NMR spectra and fifteen terpenes were identified by GC-MS. EEP-Y MS showed cytotoxic activity against human tumour strain OVCAR-8 but was not active against Gram-negative or Gram-positive bacteria. Our results confirm the difficulty of establishing a uniform quality standard for propolis from diverse geographical origins. The most appropriate pharmacological applications of yellow types of propolis must be further investigated.