Phenolic compounds of Eugenia involucrata (Myrtaceae) extracts and associated antioxidant and inhibitory effects on acetylcholinesterase and α-glucosidase.

Eugenia involucrata DC. (Myrtaceae), popularly known as "cereja-do-Rio-Grande", is a native tree from Brazil, popularly used as a hypoglycemiant. Crude hydroalcoholic extract (CHE) and fractions (insoluble (FI), dichloromethane (FDM), ethyl acetate (FEA) and butanol (FBu)) of leaves were assessed to determine the phenolic chemical composition by HPLC-ESI-MS/MS. 10 compounds were identified, being 7 new for this species: rutin, isoquercitrin, luteolin-7-O-rutinoside, mandelic acid, naringenin, luteolin-7-O-glucoside and salicylic acid. Extract and fractions showed inhibitory activity on acetylcholinesterase (AchE) enzyme (best result: IC50 = 44.19 µg mL-1, for FEA) and α-glucosidase (α-Glu) (best result: IC50 = 31.25 ± 0.15 µg mL-1, for CHE). The observed antioxidant and inhibitory activity on the AchE and α-Glu is due to, at least in part, the presence of phenolic compounds in the samples.

Phenolic profile by HPLC-ESI-MS/MS of six Brazilian Eugenia species and their potential as cholinesterase inhibitors.

Eugenia genus is known for its phenolic metabolites, which may influence the progression of the Alzheimer Disease. This study aimed to evaluate the anticholinesterase effects of six Eugenia species from Brazil. Leaves and stems were submitted to maceration (methanol) and partitioned with dichloromethane and ethyl acetate (EtOAc). Samples were screened (200 µg mL-1) for the inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). HPLC-ESI-MS/MS analysis allowed the identification of twenty-eight phenolic compounds. Regarding the enzymatic activity, EtOAc fraction of E. mattosii exhibited the best results. Chemical and pharmacological aspects of seasonal E. mattosii extracts were evaluated. The extract from leaves collected in the winter was the most effective for AChE, and the extract from leaves collected in the spring was the most effective for BuChE. Correlating the enzymatic results with the chemical data, it was possible to associate these effects to isoquercitrin, quercetin, catechin, epicatechin, procatecuic acid and myricitrin content.

Phenolic profile by HPLC-ESI-MS/MS and enzymatic inhibitory effect of Bryophyllum delagoense.

Bryophyllum delagoense (Eckl. & Zeyh.) Druce, native to Madagascar, is popularly known as "abyssian cactus" and popularly used in folk medicine as an analgesic and healing agent. The study methodology was divided into the phytochemical study: fractionation and identification of phenolic compounds by HLPC-ESI-MS/MS from the methanolic extract (ME), and fractions (DCMF and EAF) of leaves of B. delagoense, and biological activity with acetylcholinesterase and α-glucosidase inhibition of extracts and fractions by in vitro enzymatic techniques. Twenty-seven phenolic compounds were identified, being the highest concentration of syringic acid (87.848 mg g-1). The DCMF fraction showed the best biological activity for inhibition of α-glucosidase enzyme (0.125 mg mL-1).

Dataset about Southern-Brazilian geopropolis: Physical and chemical perspectives.

The dataset showed in this manuscript belongs to the investigation of the Southern-Brazilian geopropolis of stingless bees. Stingless bees are native species of insects from tropical areas; they produce honey, pollen and geopropolis that is composed of a mix of vegetal extracts, digestive enzymes, and mostly by soil. Used in folk medicine as antiseptic, antioxidant and antimicrobial agent, the composition is due to bee species, climate changes, local flora, and soil type. Moreover, the complex chemical content gives to the geopropolis a bioactive potential, with scavenging characteristics that is important to avoid free radical damages in the human health. Regarding the importance of exploring new natural matrices sources with bioactive potential, the first approach of chemical characterization of geopropolis is indispensable. Thus, ten samples of Southern-Brazilian geopropolis were analyzed and the bioactive responses obtained were discussed in the accompanying article titled "Southern-Brazilian geopropolis: A potential source of polyphenolic compounds and assessment of mineral composition". Furthermore, the physicochemical analysis of moisture and ash content, the yield of extraction, the reducing activity and free radical scavenging potential of ethanolic extracts, the antimicrobial activity, and the analysis of HPLC-ESI-MS/MS chromatograms are the main data presented in brief. The data can guide scientists in order to know methods and data for these samples.

Determination of acetylcholinesterase and α-glucosidase inhibition by electrophoretically-mediated microanalysis and phenolic profile by HPLC-ESI-MS/MS of fruit juices from Brazilian Myrtaceae Plinia cauliflora (Mart.) Kausel and Eugenia uniflora L.

Alzheimer's disease and diabetes mellitus are contemporary diseases of great concern. Phenolic compounds are linked to several health benefits and could lead to novel strategies to combat these ailments. The objective of this study was to evaluate by electrophoretically-mediated microanalysis the potential inhibitory activity of the fruit juices from Plinia cauliflora ("jaboticaba") and Eugenia uniflora ("pitanga") toward acetylcholinesterase (AChE) and α-glucosidase, target enzymes in strategies for the treatment of these diseases. The phenolic profiles of the samples were also investigated. Jaboticaba and pitanga juices inhibited 85.90 ± 1.73 and 52.67 ± 1.24% of AChE activity at 5 mg mL-1, and 57.91 ± 2.60 and 69.47 ± 2.89% of α-glucosidase activity at 1 mg mL-1, respectively. Total phenolic content of the juices were 303.54 ± 28.28 and 367.00 ± 11.42 mgGA L-1, respectively. The observed inhibitory activity can be explained, at least in part, by the presence of the phenolic compounds.

Sorocea guilleminiana Gaudich.: Wound healing activity, action mechanisms, and chemical characterization of the leaf infusion.

ETHNOPHARMACOLOGICAL RELEVANCE: Sorocea guilleminina Gaudich. is a tree or shrub endemic to Brazil. Its leaves are used in Brazilian folk medicine for the healing of wounds, stomach problems, inflammation and as diuretic. The present study evaluates the activity and action mechanisms of the healing properties of the aqueous extract of S. guilleminiana leaves (AESg), in experimental models in vivo and in vitro, as well as performs a phytochemical analysis of the extract. MATERIALS AND METHODS: The AESg was prepared by infusion: Ten g of dry leaves powder in 1 L hot water, soaked for 15 min, filtered, lyophilized, and stored at -30 °C. Phytochemical analyses were realized by colorimetry and HPLC/ESI/MS. Its' in vitro cytotoxicity was evaluated on fibroblastic N3T3 cells. The potential of the wound healing activity in vivo was evaluated using excision and incision wound rat models, by histopathology of the injured skin along with the determination of nitric oxide, cytokines (IL-1ß, IL-10, and TNF-α), and antioxidant parameters (GSH, MPO and CAT). In vitro wound healing activity was also demonstrated in scratched N3T3 cells, by measuring the proliferation/migration rate. RESULTS: The phytochemical analysis of the AESg revealed a strong presence of polar compounds, especially flavonoids (4 majoritarian), as well as terpenes and/or sterols (2 majoritarian). The AESg showed no toxicity in the N3T3 cell line (IC50 > 800 µg/mL). Topical treatment with the AESg showed an increase (p < 0.05) in wound contraction with 2 mg/g cream on days 5 and 9 (43.56% and 6.70% increase, respectively), and with 50 mg/g on days 7 and 9 (10.88% and 7.91%, respectively), compared to the vehicle (non-ionic neutral cream). Topical application of AESg (2 or 50 mg/g non-ionic cream) in incised wounds caused an increase in the force necessary for the rupture of the wound when compared to the vehicle group. No changes in cytokines (IL-1ß, IL-10, or TNF-α) or NO accumulation was found with up to 50 mg/g AESg treatment. For antioxidant activity on the incision wound, an increase in GSH levels was denoted with the AESg use, at the lowest and highest dose (2 and 50 mg/g) by 75.86% and 61.20% respectively, when compared to the vehicle. Also, the CAT activity was accentuated by AESg at the highest dose (50 mg/g) by 85.87%. Finally, the AESg at all doses attenuated MPO activity significantly in the incision wound by 71.35%, 73.21%, 78.08%, respectively. In the scratch test on N3T3 cells, the treatment with AESg resulted also in an increase in fibroblast proliferation/migration rate, compared to the vehicle. CONCLUSION: AESg is not cytotoxic. The results confirm the popular use of the leaf infusion of S. guilleminiana for the treatment of cutaneous wounds, possibly by stimulating the proliferation of fibroblasts with a consequent deposition of collagen, fastening rearrangement of collagen fibers, and greater transformation into myofibroblasts, essential in the healing process. Preliminary chemical analyzes of AESg revealed the presence mainly of phenolic compounds, being salicylic acid, gallic acid, pinocembrin and isoquercitrin the majoritarian ones.

Bauhinia forficata link, a Brazilian medicinal plant traditionally used to treat cardiovascular disorders, exerts endothelium-dependent and independent vasorelaxation in thoracic aorta of normotensive and hypertensive rats.

ETHNOPHARMACOLOGICAL RELEVANCE: Bauhinia forficata Link, commonly known as "cow's paw", is a native plant from South America. Its leaves are widely used in Brazilian folk medicine to treat diabetes and cardiovascular disorders. Although this species' biological potential has been extensively proven as an antidiabetic, anti-inflammatory and antioxidant agent, there is a lack of studies to evidence its action on the cardiovascular system. AIM OF THE STUDY: This study was designed to investigate the vascular effects of B. forficata leaves preparations and its majority compound kaempferitrin, as well as its aglycone form kaempferol, in rat aortic rings of normotensive (NTR) and hypertensive (SHR) rats. MATERIALS AND METHODS: Aorta rings from NTR and SHR precontracted with phenylephrine were exposed to cumulative concentrations of B. forficata extract, fractions (1-50 µg/mL) and compounds (0.001-0.3 µg/mL). The mechanisms involved in the vasorelaxant effect of ethyl-acetate plus butanol fraction (EAButF) were also evaluated. RESULTS: Although kaempferitrin is the most abundant compound found in both methanolic extract and EAButF, 24 minor phenolic compounds were identified in B. forficata leaves, including kaempferol. EAButF was the only with endothelium-dependent and independent vasorelaxant properties in both NTR and SHR. The incubation with L-NAME or ODQ completely blocked EAButF-induced vasorelaxation. On the other hand, the incubation with propranolol, atropine, indomethacin, glibenclamide or barium chloride did not change the vasorelaxant activity of EAButF (50 µg/mL). Nevertheless, the incubation with tetraethylammonium and 4-aminopyridine significantly influenced the EAButF activity. It was also shown that Ca2+ influx or efflux is not related to EAButF vasorelaxation potential. Kaempferitrin and kaempferol were also able to relax the rat aortic rings in 34.70% and 40.54%, respectively. CONCLUSIONS: This study shows, for the first time, the vasorelaxant effect of EAButF from B. forficata leaves, an effect that may be attributed to the modulation of vascular tone through nitric oxide/soluble guanylate cyclase pathway, and potassium channels. The bioactive kaempferitrin and kaempferol seem to be important for the effects observed with the fraction. Finally, preparations obtained from the leaves of B. forficata may be interesting candidates for new or complementary strategies regarding cardiovascular diseases.

Optimization of green PLE method applied for the recovery of antioxidant compounds from buriti (Mauritia flexuosa L.) shell.

Buriti fruit, with high content in carotenoids and antioxidant compounds, is well appreciated for its organoleptic characteristics. However, its shell, an agroindustrial residue, is mostly discarded. Therefore, to verify the technological potential of the buriti shells, the aim of this this study was to evaluated the antioxidant potential of the extracts from buriti shell obtained by pressurized liquid extraction (PLE) with ethanol/water mixtures. PLE optimization was performed by response surface methodology, with all results maximized at the conditions of 71.21 °C and with 91.58% of ethanol. The yields values varied from 16.82 to 25.16%, total carotenoids from 23.38 to 1056.59 µg ß-carotene equivalent g-1, total phenolic content from 143.37 to 172.02 mg Gallic acid equivalent g-1, DPPH from 31.04 to 48.62 µg.mL-1, and ABTS from 1.87 to 2.70 mmol TEAC. g-1. Therefore, considering the lack of studies about buriti shell, the present work provides valuable results that confirm the PLE relevance to enhance the value of this neglected material.

Neuroprotective effect of juçara (Euterpe edulis Martius) fruits extracts against glutamate-induced oxytosis in HT22 hippocampal cells.

This study investigated the neuroprotective effect of juçara fruit extracts against glutamate-induced oxytosis in HT22 cells. Potential relationships between the extracts' polyphenolic composition and their protective/antioxidant capacities were also investigated. Experiments with the addition of either the crude methanolic extract or hexane, dichloromethane, ethyl acetate and butanol fractions 24 h before glutamate (pretreatment) and together with glutamate (co-treatment) were performed. At the concentration of 10 µg ml-1, the hexane and dichloromethane fractions were able to protect cells, both in pretreatment and co-treatment. These fractions presented the highest number of quantified polyphenolics (24 and 21, respectively) although the total levels were 63-fold higher in the dichloromethane fraction. Syringaldehyde, vanillin and 4-aminobenzoic, cinnamic, salicylic and syringic acids were found only in these fractions. The dichloromethane fraction presented higher 2,2-diphenyl-1-picrylhydrazyl radical-scavenging activity, while the butanol and ethyl acetate fractions showed higher ferric reducing antioxidant power. These results suggest juçara fruits extracts as promising for the reduction of the risk of neurodegenerative diseases.

May the superfruit red guava and its processing waste be a potential ingredient in functional foods?

Guava (Psidium guajava L.), a popular fruit in tropical countries, can be consumed in natura or transformed into many products. Guava's processing waste (seed, peel, and pulp leftovers) can represent up to 30% of the fruit's volume. Evidence indicates that this fraction still holds a significant amount of antioxidant substances, such as phenolic compounds. Therefore, the objective of this study was to investigate the phytochemical composition (total phenolics, flavonoids, flavonols, and condensed tannins), phenolic profile, and antioxidant activity (DPPH, modified DPPH, ABTS, and FRAP) of guava's pulp and waste extracts (GPE and GWE) obtained from guava's pulp and waste powders (GPP and GWP). The extraction was performed using a probe-type ultrasound for 2 min at 25 °C, using ethanol:water (30:70, v/v) as the solvent (15 mL for 1 g of sample). The phenolic profile of guava's powders and extracts was performed by LC-ESI-MS/MS analysis. GPE showed the highest concentration of total phenolics (2348.3 mg GAE 100 g-1 by Folin-Ciocalteu and 518.00 mg GAE 100 g-1 by Prussian Blue), and the greater in vitro antioxidant activity among all the assays tested. On the other hand, GWE was found to hold a higher amount of flavonoids (1006.08 mg QE 100 g-1), flavonols (352.59 mg QE 100 g-1), and condensed tannins (1466.9 mg g-1). Overall, 37 phenolic compounds were identified among all the samples, with 14 compounds being reported for the first time for red guava. Ellagic acid was the major phenolic present in all samples. The results showed that guava's pulp and waste are a rich source of phenolics compounds and may be used as an ingredient for the development of functional foods.

Simultaneous determination of free and total glycerol in biodiesel by capillary electrophoresis using multiple short-end injection.

A rapid method for the simultaneous determination of free glycerol (FG) and total glycerol (TG) in biodiesel by CE using a short-end multiple injection (SE/MI) configuration system is described. The sample preparation for FG involves the extraction of glycerol with water and for TG a saponification reaction is carried out followed by extraction as in the case of FG. The glycerol extracted in both cases is submitted to periodate oxidation and the iodate ions formed are measured on a CE-SE/MI system. The relevance of this study lies in the fact that no analytical procedure has been previously reported for the determination of TG (or of FG and TG simultaneously) by CE. The optimum conditions for the saponification/extraction process were 1.25% KOH and 25°C, with a time of only 5 min, and biodiesel mass in the range of 50.0-200.0 mg can be used. Multiple injections were performed hydrodynamically with negative pressure as follows: 50 mbar/3s (FG sample); 50 mbar/6s (electrolyte spacer); 50 mbar/3s (TG sample). The linear range obtained was 1.55-46.5 mg/L with R(2) > 0.99. The LOD and LOQ were 0.16 mg/L and 0.47 mg/L, respectively for TG. The method provides acceptable throughput for application in quality control and monitoring biodiesel synthesis process. In addition, it offers simple sample preparation (saponification process), it can be applied to a variety biodiesel samples (soybean, castor, and waste cooking oils) and it can be used for the determination of two key parameters related to the biodiesel quality with a fast separation (less than 30 s) using an optimized CE-SE/MI system.

Increasing the instrumental throughput of gas chromatography method using multiple injections in a single experimental run: application in determination of friedelan-3-ol and friedelin in Maytenus ilicifolia.

The aim of this study was to develop a separation method using multiple injections in a single experimental run (MISER) employing gas chromatography with flame ionization detection (GC-FID) for the first time, without instrument modification, to increase the instrumental throughput. The method was applied to the determination of the triterpenes friedelan-3-ol and friedelin in a plant extract obtained from Maytenus ilicifolia leaves. The column used in the chromatography system was a ZB-50 (30 m × 0.25 mm × 0.15 µm) with 50% phenyl-50% methyl-polysiloxane. The samples (1.0 µL) were injected using the split mode (1:90), with the injector at 280 °C and FID detector at 320 °C. The column temperature was programmed to isothermal mode at 300°C. Helium was used as the carrier gas with a constant flow of 1.5 mL min(-1). It was possible to perform three injections in the same run using the MISER method. An increase in the instrumental throughput by a factor of around 2.6 was observed when the use of multiple injections was compared with the single injection method. This method showed good linearity for both analytes with R(2)>0.99 and the values for the limit of detection were 0.24 mg L(-1) and 0.44 mg L(-1), for friedelan-3-ol and friedelin, respectively. Furthermore, the values for the limits of quantification were 0.79 mg L(-1) for friedelan-3-ol and 1.16 mg L(-1) for friedelin. The proposed method has potential for other GC applications, allowing an increase in the instrumental throughput of the methods by applying this separation technique.