RESUMEN

We present our results on the synthesis and preliminary in silico and in vitro studies of the toxicology and antioxidant properties of selenylated analogs of Tacrine. Initially, we synthesized 2-aminobenzonitriles containing an organic selenium moiety, resulting in sixteen compounds with various substituents linked to the portion derived from diorganyl diselenide. These compounds were then used as substrates in reactions with cyclic ketones, in the presence of 1.4 equivalents of trifluoroboroetherate as a Lewis acid, to synthesize selenylated analogs of Tacrine with yields ranging from 20 % to 87 %. In silico studies explored computational parameters related to antioxidant activity and hepatotoxicity. In vitro studies elucidated the antioxidant effects of Tacrine and its selenium hybrid (TSe) in neutralizing ABTS radicals, scavenging DPPH radicals, and reducing iron ions. Additionally, the acute oral toxicity of one synthesized compound was evaluated.

Asunto(s)

Antioxidantes , Compuestos de Bifenilo , Picratos , Tacrina , Antioxidantes/química , Antioxidantes/farmacología , Antioxidantes/síntesis química , Tacrina/química , Tacrina/farmacología , Tacrina/síntesis química , Animales , Picratos/antagonistas & inhibidores , Picratos/química , Compuestos de Bifenilo/antagonistas & inhibidores , Compuestos de Bifenilo/química , Estructura Molecular , Ratas , Masculino , Benzotiazoles/química , Benzotiazoles/síntesis química , Simulación por Computador , Ácidos Sulfónicos/química , Ácidos Sulfónicos/antagonistas & inhibidores , Compuestos de Organoselenio/química , Compuestos de Organoselenio/farmacología , Compuestos de Organoselenio/síntesis química , Compuestos de Organoselenio/toxicidad

RESUMEN

This study aimed to evaluate the chemical composition and antioxidant activity of phenolic extracts from monofloral and polyfloral honey samples obtained from different Brazilian regions. The chemical composition (total content of phenolic compounds and flavonoids) of extracts were measured by using colorimetric assays and analyzed by high performance liquid chromatographic (HPLC-DAD). The antioxidant activity was evaluated by chemical and biochemical assays (reducing power assay, 1,1-diphenyl-2-picrylhydrazyl (DPPH⋅) and 2,2-azino-bis(3-ethylbenzothiazoline-6-sulphonic) acid (ABTS⋅+) scavenger assays. It was also investigated the ability of extracts in attenuate lipid peroxidation induced by Fe2+ in phospholipids. The obtained results clearly demonstrated that the botanical origin and geographical region of honey collection influenced the chemical composition and antioxidant activity of extracts. Furthermore, the samples were constituted by phenolic acids and flavonoids, which p-coumaric acid was predominant among the compounds identified. All samples were able to scavenge free radicals and inhibit lipid peroxidation, and good correlations were obtained between the flavonoid content and honey color. In conclusion, the obtained extracts were constituted by antioxidant compounds, which reinforce the usage of honey in human diets, and demonstrated that the region of honey collection strong influenced in the chemical composition and, consequently, its biological effect.

Asunto(s)

Antioxidantes , Miel , Peroxidación de Lípido , Fenoles , Miel/análisis , Antioxidantes/farmacología , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Fenoles/farmacología , Fenoles/química , Fenoles/aislamiento & purificación , Fenoles/análisis , Brasil , Peroxidación de Lípido/efectos de los fármacos , Cromatografía Líquida de Alta Presión , Flavonoides/farmacología , Flavonoides/química , Flavonoides/análisis , Flavonoides/aislamiento & purificación , Compuestos de Bifenilo/antagonistas & inhibidores , Picratos/antagonistas & inhibidores , Flores/química , Benzotiazoles/antagonistas & inhibidores , Ácidos Sulfónicos/antagonistas & inhibidores

RESUMEN

In this work, the hexane, chloroform, and methanol extracts from Kalanchoe fedtschenkoi were utilized to green-synthesize silver nanoparticles (Kf1-, Kf2-, and Kf3-AgNPs). The Kf1-, Kf2-, and Kf3-AgNPs were characterized by spectroscopy and microscopy techniques. The antibacterial activity of AgNPs was studied against bacteria strains, utilizing the microdilution assay. The DPPH and H2O2 assays were considered to assess the antioxidant activity of AgNPs. The results revealed that Kf1-, Kf2-, and Kf3-AgNPs exhibit an average diameter of 39.9, 111, and 42 nm, respectively. The calculated ζ-potential of Kf1-, Kf2-, and Kf3-AgNPs were -20.5, -10.6, and -7.9 mV, respectively. The UV-vis analysis of the three samples demonstrated characteristic absorption bands within the range of 350-450 nm, which confirmed the formation of AgNPs. The FTIR analysis of AgNPs exhibited a series of bands from 3500 to 750 cm-1, related to the presence of extracts on their surfaces. SEM observations unveiled that Kf1- and Kf2-AgNPs adopted structural arrangements related to nano-popcorns and nanoflowers, whereas Kf3-AgNPs were spherical in shape. It was determined that treatment with Kf1-, Kf2-, and Kf3-AgNPs was demonstrated to inhibit the growth of E. coli, S. aureus, and P. aeruginosa in a dose-dependent manner (50-300 µg/mL). Within the same range, treatment with Kf1-, Kf2-, and Kf3-AgNPs decreased the generation of DPPH (IC50 57.02-2.09 µg/mL) and H2O2 (IC50 3.15-3.45 µg/mL) radicals. This study highlights the importance of using inorganic nanomaterials to improve the biological performance of plant extracts as an efficient nanotechnological approach.

Asunto(s)

Antibacterianos , Antioxidantes , Tecnología Química Verde , Kalanchoe , Nanopartículas del Metal , Pruebas de Sensibilidad Microbiana , Extractos Vegetales , Plata , Nanopartículas del Metal/química , Plata/química , Plata/farmacología , Extractos Vegetales/química , Extractos Vegetales/farmacología , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/síntesis química , Kalanchoe/química , Antioxidantes/farmacología , Antioxidantes/química , Antioxidantes/síntesis química , Compuestos de Bifenilo/antagonistas & inhibidores , Compuestos de Bifenilo/química , Picratos/antagonistas & inhibidores , Picratos/química , Escherichia coli/efectos de los fármacos , Escherichia coli/crecimiento & desarrollo , Peróxido de Hidrógeno

RESUMEN

The use of plants for medicinal purposes has a long history, however it is desirable a continuous evaluation seeking for complementary scientific evidences for their safe application. Species within the Kalanchoe genus are often referred to as "miracle leaf" due to their remarkable healing properties. Traditionally, these plants have been used to treat infections, inflammation, and cancer. Despite their widespread use, the identification of their active components remains incomplete. This study aimed to differentiate K. crenata (KC), K. marmorata (KM), and K. pinnata (KP) by conducting detailed histochemical and phytochemical analyses, and to assess their antioxidant capabilities. The investigation revealed significant differences between the species, highlighting the variability in phenolic (PC) and flavonoid contents (FC) and their distinct antioxidant effects. The KM demonstrated the greatest results (PC: 59.26±1.53 mgEqGA/g; FC: 12.63±0.91 mgEqCQ/g; DPPH⋅ (IC50): 110.66 ug/mL; ABTS⋅+ (IC50): 26.81 ug/mL; ORAC: 9.65±0.75 mmolTE) when compared to KC and KP. These findings underscore a new reference for research within the Kalanchoe genus.

Asunto(s)

Antioxidantes , Kalanchoe , Fitoquímicos , Extractos Vegetales , Kalanchoe/química , Extractos Vegetales/química , Extractos Vegetales/farmacología , Extractos Vegetales/aislamiento & purificación , Fitoquímicos/química , Fitoquímicos/farmacología , Fitoquímicos/aislamiento & purificación , Antioxidantes/farmacología , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Fenoles/química , Fenoles/farmacología , Fenoles/aislamiento & purificación , Agua/química , Flavonoides/química , Flavonoides/farmacología , Flavonoides/aislamiento & purificación , Picratos/antagonistas & inhibidores , Compuestos de Bifenilo/antagonistas & inhibidores , Compuestos de Bifenilo/química , Hojas de la Planta/química

RESUMEN

Phenolic compounds from mango (M. indica) seed kernels (MSK) var. Sugar were obtained using supercritical CO2 and EtOH as an extraction solvent. For this purpose, a central composite design was carried out to evaluate the effect of extraction pressure (11-21 MPa), temperature (40-60 °C), and co-solvent contribution (5-15% w/w EtOH) on (i) extraction yield, (ii) oxidative stability (OS) of sunflower edible oil (SEO) with added extract using the Rancimat method, (iii) total phenolics content, (iv) total flavonoids content, and (v) DPPH radical assay. The most influential variable of the supercritical fluid extraction (SFE) process was the concentration of the co-solvent. The best OS of SEO was reached with the extract obtained at 21.0 MPa, 60 °C and 15% EtOH. Under these conditions, the extract increased the OS of SEO by up to 6.1 ± 0.2 h (OS of SEO without antioxidant, Control, was 3.5 h). The composition of the extract influenced the oxidative stability of the sunflower edible oil. By SFE it was possible to obtain extracts from mango seed kernels (MSK) var. Sugar that transfer OS to the SEO. These promissory extracts could be applied to foods and other products.

Asunto(s)

Antioxidantes/farmacología , Mangifera/química , Fenoles/farmacología , Extractos Vegetales/farmacología , Aceites de Plantas/química , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Compuestos de Bifenilo/antagonistas & inhibidores , Cromatografía con Fluido Supercrítico , Fenoles/química , Fenoles/aislamiento & purificación , Picratos/antagonistas & inhibidores , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación

RESUMEN

Phenolic compounds present in common beans (Phaseolus vulgaris L.) have been reported to possess antimicrobial, anti-inflammatory and ultraviolet radiation (UVR) protective properties. UVR from sunlight, which consists of UV-B and UV-A radiations, induces reactive oxygen species (ROS) and free radical formation, consequently activating proteinases and enzymes such as elastase and tyrosinase, leading to premature skin aging. The objective of this work was to extract, characterize and evaluate the antioxidant and antiaging potential of polyphenols from a black bean endemic variety. The polyphenolic extract was obtained from black beans by supercritical fluid extraction (SFE) using CO2 with a mixture of water-ethanol as a cosolvent and conventional leaching with a mixture of water-ethanol as solvent. The polyphenolic extracts were purified and characterized, and antioxidant potential, tyrosinase and elastase inhibitory potentials were measured. The extract obtained using the SFE method using CO2 and H2O-Ethanol (50:50 v/v) as a cosolvent showed the highest total phenolic compounds yield, with 66.60 ± 7.41 mg GAE/g coat (p > 0.05) and 7.30 ± 0.64 mg C3GE/g coat (p < 0.05) of anthocyanins compared to conventional leaching. Nineteen tentative phenolic compounds were identified in leaching crude extract using ESI-QTOF. Quercetin-3-D-galactoside was identified in crude and purified extracts. The purified SFC extract showed IC50 0.05 ± 0.002 and IC50 0.21 ± 0.008 mg/mL for DPPH and ABTS, respectively. The lowest IC50 value of tyrosinase inhibition was 0.143 ± 0.02 mg/mL and 0.005 ± 0.003 mg/mL of elastase inhibition for leaching purified extract. Phenolic compounds presented theoretical free energy values ranging from -5.3 to -7.8 kcal/mol for tyrosinase and -2.5 to -6.8 kcal/mol for elastase in molecular docking (in silico) studies. The results suggest that the purified extracts obtained by SFE or conventional leaching extraction could act as antioxidant and antiaging ingredients for cosmeceutical applications.

Asunto(s)

Envejecimiento/efectos de los fármacos , Antioxidantes/farmacología , Phaseolus/química , Extractos Vegetales/farmacología , Polifenoles/farmacología , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Benzotiazoles/antagonistas & inhibidores , Compuestos de Bifenilo/antagonistas & inhibidores , Dióxido de Carbono/química , Cromatografía con Fluido Supercrítico , Etanol/química , Humanos , Simulación del Acoplamiento Molecular , Picratos/antagonistas & inhibidores , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Polifenoles/química , Polifenoles/aislamiento & purificación , Ácidos Sulfónicos/antagonistas & inhibidores , Rayos Ultravioleta , Agua/química

RESUMEN

The genus Nothofagus is one of the most abundant in the subantarctic Patagonian forests. Five species inhabit these ecosystems, three evergreen (Nothofagus betuloides, Nothofagus dombeyi, and Nothofagus nitida) and two deciduous (Nothofagus pumilio and Nothofagus antarctica). This is the first report on the levels of secondary metabolites and the antioxidant capacity of Patagonian tree species growing in natural environments. The aim of this work was to carry out a phytochemical screening, to determine the antioxidant capacity, the sun protection factor, and the α-glucosidase and tyrosinase inhibitory activity of foliar extracts of the five previous species. Besides, Aristotelia chilensis and Berberis microphylla, two species of Patagonian shrubs growing in the same forests, were used as reference. N. dombeyi was the Nothofagus with the best antioxidant capacity. B. microphylla differed from all studied species. Moreover, the Nothofagus was split into two groups. N. betuloides and N. dombeyi are the most similar species to A. chilensis. The α-glucosidase was completely inhibited by all studied extracts. Furthermore, N. antarctica, N.pumilio, and N. nitida inhibited about 70% of the tyrosinase activity. All the results found in this study for the species of the genus Nothofagus support further research on their potential beneficial properties for human health.

Asunto(s)

Antioxidantes/farmacología , Inhibidores Enzimáticos/farmacología , Fitoquímicos/farmacología , Árboles/química , Antioxidantes/química , Antioxidantes/metabolismo , Benzotiazoles/antagonistas & inhibidores , Compuestos de Bifenilo/antagonistas & inhibidores , Chile , Evaluación Preclínica de Medicamentos , Inhibidores Enzimáticos/química , Inhibidores Enzimáticos/metabolismo , Bosques , Humanos , Monofenol Monooxigenasa/antagonistas & inhibidores , Monofenol Monooxigenasa/metabolismo , Fitoquímicos/química , Fitoquímicos/metabolismo , Picratos/antagonistas & inhibidores , Especificidad de la Especie , Ácidos Sulfónicos/antagonistas & inhibidores , Árboles/metabolismo , alfa-Glucosidasas/metabolismo

RESUMEN

The aim of this study was to evaluate the phytochemical composition, antioxidant, and antimicrobial potential of crude extract and fractions of Punica granatum leaves. The extract was produced by turbo extraction, after which hexanic, ethyl acetate, and aqueous fractions were obtained by partitioning. The chemical analyses were performed by thin layer chromatography and high-performance liquid chromatography, and the antioxidant activities were assayed by DPPH. and ABTS.+ . Minimal inhibitory and bactericidal concentrations (MIC/MBC) were applied to twenty-two bacteria. Most strains susceptible to extract/fractions and resistant to antibiotics were selected, and ampicillin, azithromycin, ciprofloxacin, and gentamicin were associated with the ethyl acetate fraction (EAF) against multidrug-resistant strains in modulatory and checkboard models. The data from chromatographic analyses showed flavonoids and tannins in the extract, as well as the enrichment of EAF in phenols, mainly flavonoids. The flavonoids were connected to the electron transfer activity demonstrated in the DPPH. and ABTS.+ assays. Gram-positive strains are more susceptible to EAF. The subinhibitory concentrations of P. granatum enhanced the antimicrobial activity of the agents and reduced the EAF individual MIC, and the combination of EAF and antibiotics demonstrated a synergistic effect. These results present a promising approach for developing a therapy in which antioxidant extracts and fractions can be used in combination with antibiotics.

Asunto(s)

Antibacterianos/farmacología , Antioxidantes/farmacología , Farmacorresistencia Bacteriana Múltiple/efectos de los fármacos , Lythraceae/química , Extractos Vegetales/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Benzotiazoles/antagonistas & inhibidores , Compuestos de Bifenilo/antagonistas & inhibidores , Escherichia coli/efectos de los fármacos , Klebsiella pneumoniae/efectos de los fármacos , Pruebas de Sensibilidad Microbiana , Picratos/antagonistas & inhibidores , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Hojas de la Planta/química , Pseudomonas aeruginosa/efectos de los fármacos , Ácidos Sulfónicos/antagonistas & inhibidores

RESUMEN

Croton ferrugineus Kunth is an endemic species of Ecuador used in traditional medicine both for wound healing and as an antiseptic. In this study, fresh Croton ferrugineus leaves were collected and subjected to hydrodistillation for extraction of the essential oil. The chemical composition of the essential oil was determined by gas chromatography equipped with a flame ionization detector and gas chromatography coupled to a mass spectrometer using a non-polar and a polar chromatographic column. The antibacterial activity was assayed against three Gram-positive bacteria, one Gram-negative bacterium and one dermatophyte fungus. The radical scavenging properties of the essential oil was evaluated by means of DPPH and ABTS assays. The chemical analysis allowed us to identify thirty-five compounds representing more than 99.95% of the total composition. Aliphatic sesquiterpene hydrocarbon trans-caryophyllene was the main constituent with 20.47 ± 1.25%. Other main compounds were myrcene (11.47 ± 1.56%), ß-phellandrene (10.55 ± 0.02%), germacrene D (7.60 ± 0.60%), and α-humulene (5.49 ± 0.38%). The essential oil from Croton ferrugineus presented moderate activity against Candida albicans (ATCC 10231) with an MIC of 1000 µg/mL, a scavenging capacity SC50 of 901 ± 20 µg/mL with the ABTS method, and very strong antiglucosidase activity with an IC50 of 146 ± 20 µg/mL.

Asunto(s)

Antiinfecciosos/química , Antioxidantes/química , Croton/química , Inhibidores Enzimáticos/química , Aceites Volátiles/química , Hojas de la Planta/química , Monoterpenos Acíclicos/química , Monoterpenos Acíclicos/aislamiento & purificación , Alquenos/química , Alquenos/aislamiento & purificación , Antiinfecciosos/aislamiento & purificación , Antiinfecciosos/farmacología , Antioxidantes/aislamiento & purificación , Antioxidantes/farmacología , Benzotiazoles/antagonistas & inhibidores , Compuestos de Bifenilo/antagonistas & inhibidores , Candida albicans/efectos de los fármacos , Candida albicans/crecimiento & desarrollo , Monoterpenos Ciclohexánicos/química , Monoterpenos Ciclohexánicos/aislamiento & purificación , Inhibidores Enzimáticos/aislamiento & purificación , Inhibidores Enzimáticos/farmacología , Escherichia coli/efectos de los fármacos , Escherichia coli/crecimiento & desarrollo , Bacterias Grampositivas/efectos de los fármacos , Bacterias Grampositivas/crecimiento & desarrollo , Pruebas de Sensibilidad Microbiana , Sesquiterpenos Monocíclicos/química , Sesquiterpenos Monocíclicos/aislamiento & purificación , Picratos/antagonistas & inhibidores , Sesquiterpenos Policíclicos/química , Sesquiterpenos Policíclicos/aislamiento & purificación , Sesquiterpenos de Germacrano/química , Sesquiterpenos de Germacrano/aislamiento & purificación , Ácidos Sulfónicos/antagonistas & inhibidores , alfa-Glucosidasas/química

RESUMEN

Hedyosmum racemosum (Ruiz & Pav.) G. is a native species of Ecuador used in traditional medicine for treatment of rheumatism, bronchitis, cold, cough, asthma, bone pain, and stomach pain. In this study, fresh H. racemosum leaves of male and female specimens were collected and subjected to hydrodistillation for the extraction of the essential oil. The chemical composition of male and female essential oil was determined by gas chromatography-gas chromatography equipped with a flame ionization detector and coupled to a mass spectrometer using a non-polar and a polar chromatographic column. The antibacterial activity was assayed against five Gram-positive and two Gram-negative bacteria, and two dermatophytes fungi. The scavenging radical properties of the essential oil were evaluated by DPPH and ABTS assays. The chemical analysis allowed us to identify forty-three compounds that represent more than 98% of the total composition. In the non-polar and polar column, α-phellandrene was the principal constituent in male (28.24 and 25.90%) and female (26.47 and 23.90%) essential oil. Other main compounds were methyl chavicol, germacrene D, methyl eugenol, and α-pinene. Female essential oil presented a strong activity against Klebsiella pneumoniae (ATCC 9997) with an minimum inhibitory concentration (MIC) of 500 µg/mL and a scavenging capacity SC50 of 800 µg/mL.

Asunto(s)

Antibacterianos/química , Antioxidantes/química , Monoterpenos Ciclohexánicos/química , Magnoliopsida/química , Aceites Volátiles/química , Derivados de Alilbenceno/química , Derivados de Alilbenceno/aislamiento & purificación , Anisoles/química , Anisoles/aislamiento & purificación , Antibacterianos/aislamiento & purificación , Antibacterianos/farmacología , Antioxidantes/aislamiento & purificación , Antioxidantes/farmacología , Arthrodermataceae/efectos de los fármacos , Arthrodermataceae/crecimiento & desarrollo , Benzotiazoles/antagonistas & inhibidores , Monoterpenos Bicíclicos/química , Monoterpenos Bicíclicos/aislamiento & purificación , Compuestos de Bifenilo/antagonistas & inhibidores , Monoterpenos Ciclohexánicos/aislamiento & purificación , Ecuador , Eugenol/análogos & derivados , Eugenol/química , Eugenol/aislamiento & purificación , Femenino , Bacterias Gramnegativas/efectos de los fármacos , Bacterias Gramnegativas/crecimiento & desarrollo , Bacterias Grampositivas/efectos de los fármacos , Bacterias Grampositivas/crecimiento & desarrollo , Humanos , Magnoliopsida/metabolismo , Masculino , Pruebas de Sensibilidad Microbiana , Picratos/antagonistas & inhibidores , Hojas de la Planta/química , Plantas Medicinales , Sesquiterpenos de Germacrano/química , Sesquiterpenos de Germacrano/aislamiento & purificación , Factores Sexuales , Ácidos Sulfónicos/antagonistas & inhibidores

RESUMEN

In Brazil, there is a large diversity of species of small edible fruits that are considered sources of nutrients and functional properties. They present a high innovation domain for the pharmaceutical, cosmetic and food industries due to their health-promoting properties. Edible fruits from Brosimum gaudichaudii (Moraceae) are widely consumed and used in folk medicine and in feed by the population of the Brazilian Cerrado. Nevertheless, detailed information on the chemical fingerprint, antiradical activity and safety aspects of these fruits is still unknown. Thus, the aim of this work was to investigate the bioactive compounds of hydroethanolic extracts of fruits from Brosimum gaudichaudii using high-performance liquid chromatography combined with mass spectrometry using electrospray ionization (HPLC ESI-MS). Eighteen different compounds, including flavonoids, coumarins, arylbenzofurans, terpenoids, stilbenes, xanthones and esters, were detected. Moreover, the study indicated that the hydroethanolic extract of fruits from B. gaudichaudii presented low scavenging activity against 2,2-diphenyl-1-picrylhydrazyl radicals (IC50 >800 µg mL-1 ) and was cytotoxic (IC50 <30 µg mL-1 ) in Chinese hamster ovary cells (CHO-K1) by an in vitro assay. This is the first report of the chemical profile, antioxidant activity and cytotoxic properties of the hydroethanolic extract of fruits from B. gaudichaudii.

Asunto(s)

Antineoplásicos Fitogénicos/farmacología , Antioxidantes/farmacología , Moraceae/química , Extractos Vegetales/farmacología , Animales , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Compuestos de Bifenilo/antagonistas & inhibidores , Brasil , Línea Celular , Supervivencia Celular/efectos de los fármacos , Cricetulus , Frutas/química , Humanos , Estructura Molecular , Picratos/antagonistas & inhibidores , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Plantas Comestibles/química

RESUMEN

Eugenia copacabanensis and Myrciaria tenella are present in restingas of the Atlantic Forest, but little information is available about their chemical and biological potential. In this context, the hexane, dichloromethane, ethyl acetate and butanol fractions from the leaves of methanolic extract were analyzed by GC/MS and HPLC-DAD and the antioxidant potential was determined by DPPH and ABTS assays and using a Saccharomyces cerevisiae model. Dereplication allowed the identification of 68 compounds, 42 and 41 of which, respectively, are first reported here for E. copacabanensis and M. tenella. In vivo results revealed that the ethyl acetate and butanol fractions showed expressive antioxidant protection in the BY4741 and Δgsh1 strains, with greater impact on glutathione-deficient cells. With a high diversity of phenolic compounds, these polar fractions of E. copacabanensis and M. tenella leaves are potential protectors against intracellular oxidative stress.

Asunto(s)

Antifúngicos/farmacología , Antioxidantes/farmacología , Eugenia/química , Myrtaceae/química , Fitoquímicos/farmacología , Hojas de la Planta/química , Antifúngicos/análisis , Antioxidantes/análisis , Benzotiazoles/antagonistas & inhibidores , Compuestos de Bifenilo/antagonistas & inhibidores , Pruebas de Sensibilidad Microbiana , Modelos Biológicos , Fitoquímicos/análisis , Picratos/antagonistas & inhibidores , Saccharomyces cerevisiae/efectos de los fármacos , Saccharomyces cerevisiae/crecimiento & desarrollo , Ácidos Sulfónicos/antagonistas & inhibidores

RESUMEN

This study describes the physicochemical properties of soybean asolectin (ASO) liposomes loaded with phycocyanin (Phy) extracted from Spirulina sp. LEB 18. The effects of Phy in the liposomes' properties were investigated by Fourier transform infrared spectroscopy (FTIR), 1H and 31P nuclear magnetic resonance (NMR), zeta (ζ)-potential, dynamic light scattering (DLS) and ultraviolet-visible (UV-vis) techniques. Phy restricted the motion of ASO polar and interface groups and disrupted the package arrangement of the lipid hydrophobic regions, as a likely effect of dipolar and π interactions related to its amino acid residues and pyrrole portions. These interactions were correlated to antiradical/antioxidant Phy responses obtained by 2,2-diphenyl-1-picrylhidrazil (DPPH) assay, thiobarbituric acid reactive substances (TBARS) and ferric reducing antioxidant power (FRAP) methods, and discussed to bring new chemical perspectives about Phy-loaded liposomes-related nutraceutical applications in inflammatory and viral infection processes.

Asunto(s)

Antioxidantes/farmacología , Ficocianina/farmacología , Spirulina/química , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Compuestos de Bifenilo/antagonistas & inhibidores , Recuperación de Fluorescencia tras Fotoblanqueo , Liposomas/química , Ficocianina/química , Ficocianina/aislamiento & purificación , Picratos/antagonistas & inhibidores

RESUMEN

Alzheimer's Disease (AD) is a complex neurodegenerative disorder associated in some instances with dyshomeostasis of redox-active metal ions, such as copper and iron. In this work, we investigated whether the conjugation of various aromatic amines would improve the pharmacological efficacy of the iron chelator desferrioxamine (DFO). Conjugates of DFO with aniline (DFOANI), benzosulfanylamide (DFOBAN), 2-naphthalenamine (DFONAF) and 6-quinolinamine (DFOQUN) were obtained and their properties examined. DFOQUN had good chelating activity, promoted a significant increase in the inhibition of ß-amyloid peptide aggregation when compared to DFO, and also inhibited acetylcholinesterase (AChE) activity both in vitro and in vivo (Caenorhabditis elegans). These data indicate that the covalent conjugation of a strong iron chelator to an AChE inhibitor offers a powerful approach for the amelioration of iron-induced neurotoxicity symptoms.

Asunto(s)

Aminas/farmacología , Antioxidantes/farmacología , Caenorhabditis elegans/efectos de los fármacos , Inhibidores de la Colinesterasa/farmacología , Deferoxamina/farmacología , Quelantes del Hierro/farmacología , Acetilcolinesterasa/metabolismo , Aminas/química , Péptidos beta-Amiloides/antagonistas & inhibidores , Péptidos beta-Amiloides/metabolismo , Animales , Antioxidantes/síntesis química , Antioxidantes/química , Compuestos de Bifenilo/antagonistas & inhibidores , Caenorhabditis elegans/enzimología , Inhibidores de la Colinesterasa/síntesis química , Inhibidores de la Colinesterasa/química , Deferoxamina/química , Humanos , Quelantes del Hierro/síntesis química , Quelantes del Hierro/química , Estructura Molecular , Picratos/antagonistas & inhibidores , Agregado de Proteínas/efectos de los fármacos

RESUMEN

Octyltrimethylammonium tetrathiotungstate salt (ATT-C8) was synthesized and its ability to chelate copper was evaluated. The biological and toxic aspects were evaluated by in vitro and in vivo assays, using bovine aorta endothelial cells (BAEC) and zebrafish (Danio rerio) embryos. The obtained results suggest that ATT-C8 has better biocompatibility, showing a significantly lower lethal concentration 50 (LC50) value in comparison to ammonium tetrathiotungstate (ATT). Zebrafish embryos assay results indicate that both tetrathiotungstate salts at the studied concentrations increase the hatching time. Even more, an in vivo assay showed that synthesized materials behave as copper antagonists and have the ability to inhibit its toxicological effects. Also, both materials were found to be active for the in vitro 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. The characterization of the materials was carried out using the following spectroscopic techniques: Ultraviolet-Visible (UV-Vis), Fourier Transform Infrared (FTIR) and proton nuclear magnetic resonance (1H-NRM).

Asunto(s)

Antioxidantes/farmacología , Compuestos de Amonio Cuaternario/farmacología , Compuestos de Tungsteno/farmacología , Antioxidantes/síntesis química , Antioxidantes/química , Compuestos de Bifenilo/antagonistas & inhibidores , Estructura Molecular , Picratos/antagonistas & inhibidores , Compuestos de Amonio Cuaternario/síntesis química , Compuestos de Amonio Cuaternario/química , Compuestos de Tungsteno/síntesis química , Compuestos de Tungsteno/química

RESUMEN

In the last decade, green chemistry has been attracting great interest in many contexts, including, among others, natural antioxidants. However, only a few works deal with natural residue extracts and biowaste, which could be an efficient, economical and environmentally friendly source for the production of useful compounds. In this study, we look for antioxidant activity in Araucaria araucana seeds, an iconic pine species of the Argentine and Chilean Patagonia commonly known as "pehuén". Piñones are the edible pehuén seeds, and it is estimated that approximately 40 tons of piñones are harvested annually in Argentina and Chile. The chemical composition, antioxidants, metal corrosion-inhibiting properties and biological activity of edible and discarded piñón tissues were determined. Acute toxicity was discarded by in vitro testing and double fluorescent staining. Biological activity was evaluated in vivo by determining redox markers in salivary glands from rats treated with Cyclophosphamide (an oncological drug). All piñón tissues had antioxidants and antioxidant activity, with the coats showing the highest levels (up to 404 µg ascorbic acid equivalent per mg). The coats, in particular, had high gallic acid, catechin, quercetin and tannin contents, and more antioxidant activity, polyphenols and flavonoids than berries from the region. Results by X-ray fluorescence spectrometry showed that Na, Mg, P, S, Cl, K, and Ca were majority elements in the coat, embryo and endosperm. Furthermore, coat extract also showed significant anti-corrosion activity and in vivo protection against oxidative damage. The results indicate that piñón biowaste is a low-cost attractive source of natural antioxidants with potential nutraceutical, medical and metal corrosion protection applications.

Asunto(s)

Antioxidantes/farmacología , Araucaria araucana/química , Productos Biológicos/farmacología , Suplementos Dietéticos , Sustancias Protectoras/farmacología , Semillas/química , Animales , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Productos Biológicos/química , Productos Biológicos/aislamiento & purificación , Compuestos de Bifenilo/antagonistas & inhibidores , Chlorocebus aethiops , Corrosión , Relación Dosis-Respuesta a Droga , Masculino , Estructura Molecular , Picratos/antagonistas & inhibidores , Sustancias Protectoras/química , Sustancias Protectoras/aislamiento & purificación , Ratas , Ratas Wistar , Relación Estructura-Actividad , Células Vero

RESUMEN

Ligaria cuneifolia (Ruiz & Pav.) Tiegh. (Loranthaceae), the 'Argentine mistletoe', is a hemiparasite species largely used in folk medicine. The aim of this study was to evaluate the antioxidant activity using in vitro, ex vivo, and in vivo methods. A screening of phenolics was performed by UV spectroscopy on different fractions. The antioxidant capacity was evaluated in vitro by the 1,1-diphenyl-2-picrylhydrazyl radical (DPPH. ) assay on a crude extract (CE), ethyl acetate fraction (EAF), and aqueous fraction (AF). The results suggest that EAF concentrates the antioxidant capacity and was selected for further analysis. Capillary electrophoresis was employed to monitor the individual antioxidant capacity and the potential contributors to this effect. Ex vivo assays showed an efficient inhibition of tert-butyl hydroperoxide-induced rat liver phospholipid oxidation, as well as rat brain autoxidation, and H2 O2 -induced DNA damage in blood monocytes. In vivo, the topical application of EAF significantly decreased skin chemiluminescence in a mice model.

Asunto(s)

Antioxidantes/farmacología , Flavonoides/farmacología , Loranthaceae/química , Fosfolípidos/antagonistas & inhibidores , Extractos Vegetales/farmacología , Animales , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Argentina , Compuestos de Bifenilo/antagonistas & inhibidores , Daño del ADN , Femenino , Flavonoides/química , Flavonoides/aislamiento & purificación , Hígado/efectos de los fármacos , Hígado/metabolismo , Ratones , Oxidación-Reducción , Fosfolípidos/metabolismo , Picratos/antagonistas & inhibidores , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Ratas , Ratas Sprague-Dawley , terc-Butilhidroperóxido/antagonistas & inhibidores , terc-Butilhidroperóxido/farmacología

RESUMEN

Background: Dihydropyrimidin-2-thiones (DHPMs) are a class of heterocyclic compound which have been intensively investigated mainly due to their anticancer activity as kinesin Eg5 inhibitors. Materials & methods: A library of N1 aryl substituted DHPMs were tested against glioma and bladder cancer cell lines. Quantitative structure-activity relationship (QSAR) investigation was performed in order to identify key elements of DHPMs linked with their antiproliferative effect. The toxicity of most active compounds was investigated using Caenorhabditis elegans as the model. Results & conclusion: DHPMs 9, 13 and 17 have been identified as having improved activity against glioma and bladder cell lines as compared with monastrol. Flow cytometry investigations showed that the new compounds induce cell cycle arrest in phase G2/M and cell death by apoptosis. In addition, compound 13 was able to modulate the reactive oxygen species production in vivo in C. elegans. The biphenyl dihydropyrimidinthiones provided a safety profile in C. elegans.

Asunto(s)

Antineoplásicos/farmacología , Antioxidantes/farmacología , Cinesinas/antagonistas & inhibidores , Animales , Antineoplásicos/química , Antioxidantes/química , Compuestos de Bifenilo/antagonistas & inhibidores , Caenorhabditis elegans/efectos de los fármacos , Caenorhabditis elegans/metabolismo , Puntos de Control del Ciclo Celular/efectos de los fármacos , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Cinesinas/metabolismo , Ligandos , Estructura Molecular , Picratos/antagonistas & inhibidores , Relación Estructura-Actividad Cuantitativa , Especies Reactivas de Oxígeno/metabolismo

RESUMEN

Acylhydrazones 1a-o, derived from isoniazid, were synthesized and evaluated for Myeloperoxidase (MPO) and Acetylcholinesterase (AChE) inhibition, as well as their antioxidant and metal chelating activities, with the purpose of investigating potential multi-target profiles for the treatment of Alzheimer's disease. Synthesized compounds were tested using the 2,2-diphenyl-2-picrylhydrazyl (DPPH) method and 1i, 1j and 1 m showed radical scavenging ability. Compounds 1b, 1 h, 1i, 1 m and 1o inhibited MPO activity (10 µM) at 96.1 ± 5.5%, 90 ± 2.1%, 100.3 ± 1.7%, 80.1 ± 9.4% and 82.2 ± 10.6%, respectively, and only compound 1 m was able to inhibit 54.2 ± 1.7% of AChE activity (100 µM). Docking studies of the most potent compound 1 m were carried out, and the computational results provided the theoretical basis of enzyme inhibition. Furthermore, compound 1 m was able to form complexes with Fe2+ and Zn2+ ions in a 2:1 ligand:metal ratio according to the Job Plot method.

Asunto(s)

Enfermedad de Alzheimer/tratamiento farmacológico , Antioxidantes/farmacología , Quelantes/farmacología , Inhibidores de la Colinesterasa/farmacología , Hidrazonas/farmacología , Fármacos Neuroprotectores/farmacología , Acetilcolinesterasa/metabolismo , Enfermedad de Alzheimer/metabolismo , Animales , Antioxidantes/síntesis química , Antioxidantes/química , Compuestos de Bifenilo/antagonistas & inhibidores , Quelantes/síntesis química , Quelantes/química , Inhibidores de la Colinesterasa/síntesis química , Inhibidores de la Colinesterasa/química , Relación Dosis-Respuesta a Droga , Electrophorus , Humanos , Hidrazonas/síntesis química , Hidrazonas/química , Simulación del Acoplamiento Molecular , Estructura Molecular , Fármacos Neuroprotectores/síntesis química , Fármacos Neuroprotectores/química , Peroxidasa/antagonistas & inhibidores , Peroxidasa/metabolismo , Picratos/antagonistas & inhibidores , Relación Estructura-Actividad

RESUMEN

Imidazoline derivatives with different exocyclic substituents were simply prepared from common starting materials. The procedures were carried out in an eco-friendly manner. The antioxidant activity of these derivatives was explored by different experimental assays, such as ABTS.+ and DPPH. scavenging assay, as well as reducing power assay. The structural differences are discussed in terms of the results. Sulfur analogs showed higher antioxidant activity than their oxygenated counterparts. The same tendency was observed in microbiological studies, in which the same imidazoline compounds were assayed for light-mediated activity against of Staphylococcus aureus and Escherichia coli strains. A light-enhanced activity was observed for almost all the sulfated imidazolines after exposure to UV-A (400-320 nm) light.

Asunto(s)

Antibacterianos/farmacología , Antioxidantes/farmacología , Escherichia coli/efectos de los fármacos , Imidazolinas/farmacología , Luz , Staphylococcus aureus/efectos de los fármacos , Antibacterianos/síntesis química , Antibacterianos/química , Antioxidantes/síntesis química , Antioxidantes/química , Benzotiazoles/antagonistas & inhibidores , Compuestos de Bifenilo/antagonistas & inhibidores , Relación Dosis-Respuesta a Droga , Imidazolinas/síntesis química , Imidazolinas/química , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Picratos/antagonistas & inhibidores , Relación Estructura-Actividad , Ácidos Sulfónicos/antagonistas & inhibidores