RESUMEN

Maize (Zea mays L.) is an important crop in Argentina. Aspergillus section Flavi can infect this crop at the pre-harvest stage, and the harvested grains can be contaminated with aflatoxins (AFs). During the production of bioethanol from maize, AF levels can increase up to three times in the final co-products, known as, dry and wet distiller's grain with solubles (DDGS and WDGS), intended for animal feed. Fungal enzymes like laccases can be a useful tool for reducing AF contamination in the co-products obtained from this process. The aim of the present study was to evaluate the ability of laccase enzymes included in enzymatic extracts (EE) produced by different species in the Basidiomycota phylum to reduce AF (AFB1 and AFB2) accumulation under the conditions of in vitro assays. Four laccase activities (5, 10, 15, and 20 U/mL) exerted by nine isolates were evaluated in the absence and presence of vanillic acid (VA), serving as a laccase redox mediator for the degradation of total AFs. The enzymatic stability in maize steep liquor (MSL) was confirmed after a 60 h incubation period. The most effective EE in terms of reducing AF content in the buffer was selected for an additional assay carried out under the same conditions using maize steep liquor obtained after the saccharification stage during the bioethanol production process. The highest degradation percentages were observed at 20 U/mL of laccase enzymatic activity and 1 mM of VA, corresponding to 26% for AFB1 and 26.6% for AFB2. The present study provides valuable data for the development of an efficient tool based on fungal laccases for preventing AF accumulation in the co-products of bioethanol produced from maize used for animal feed.

Asunto(s)

Aflatoxinas , Basidiomycota , Animales , Zea mays , Descontaminación , Lacasa , Ácido Vanílico

RESUMEN

Phenolic phytochemicals are a group of organic compounds with potent antioxidant features but can also act as powerful pro-oxidants. These characteristics are effective in reducing metastatic potential in cancer cells, and this effect has been associated with reactive oxygen species (ROS). Methyl vanillate (MV) and its dimer, methyl divanillate (DMV), are potent antioxidants. In the present study, we investigated the effects of MV and DMV on breast cancer cell lines MCF-7 and MDA-MB-231 and compared the results using the non-tumor cell line HB4a. Our results indicated that the compounds performed a pro-oxidant action, increasing the generation of ROS. DMV decreased the viability cell, showing a higher apoptotic effect and inhibition of proliferation than MV on both cell lines, with significant differences between groups (p < 0.05). Some modulation of NOX4, NOX5, and DUOX were observed, but the results did not correlate with the intracellular production of ROS. The dimer showed more effectivity and pro-oxidant effect than MV, impacting cell line MCF-7 in higher extension than MDA-MB-231. In conclusion, and corroborating with reported works, the dimerization of natural phenolic compounds was associated with improved beneficial biological effects as a potential cytotoxic agent to tumor cells.

Asunto(s)

Neoplasias de la Mama , Antioxidantes/metabolismo , Antioxidantes/farmacología , Apoptosis , Neoplasias de la Mama/tratamiento farmacológico , Línea Celular Tumoral , Proliferación Celular , Dimerización , Femenino , Humanos , Células MCF-7 , Especies Reactivas de Oxígeno/metabolismo , Ácido Vanílico/análogos & derivados

RESUMEN

Morus nigra L. is a plant popularly known as 'amoreira preta', very used in folk medicine. Iron overload (hemochromatosis) is a clinical condition that causes damage to various tissues due to oxidative stress. Therapy to control iron overload is still unsatisfactory. The protective effect on oxidative stress induced by iron overload was verified. Phytochemical characterization was evaluated by UHPLC-MS/MS. The in silico toxicity predictions of the main phytochemicals were performed via computer simulation. To induce iron overload, the animals received iron dextran (50 mg/kg/day). The test groups received doses of 500 and 1000 mg/kg of M. nigra extract for six weeks. Body weight, organosomatic index, serum iron, hepatic markers, cytokines, interfering factors in iron metabolism, enzymatic and histopathological evaluations were analyzed. Vanillic acid, caffeic acid, 6-hydroxycoumarin, p-coumaric acid, ferulic acid, rutin, quercitrin, resveratrol, apigenin and kaempferol were identified in the extract. In addition, in silico toxic predictions showed that the main compounds presented a low probability of toxic risk. The extract of M. nigra showed to control the mediators of inflammation and to reduce iron overload in several tissues. Our findings illustrate a novel therapeutic action of M. nigra leaves on hemochromatosis caused by iron overload.

Asunto(s)

Hemocromatosis , Sobrecarga de Hierro , Morus , Animales , Morus/química , Morus/metabolismo , Quempferoles/análisis , Quempferoles/farmacología , Resveratrol/farmacología , Hemocromatosis/tratamiento farmacológico , Apigenina/análisis , Apigenina/farmacología , Ácido Vanílico/farmacología , Espectrometría de Masas en Tándem , Simulación por Computador , Dextranos/análisis , Dextranos/metabolismo , Dextranos/farmacología , Extractos Vegetales/uso terapéutico , Hojas de la Planta/química , Estrés Oxidativo , Sobrecarga de Hierro/prevención & control , Fitoquímicos/análisis , Rutina/farmacología , Hierro/toxicidad , Hierro/análisis , Citocinas/metabolismo , Mediadores de Inflamación/metabolismo

RESUMEN

Two of the most important Mexican plant-foods are tomato (Solanum lycopersicum L.) and husk tomato (Physalis ixocarpa Brot.). In this study three objectives were followed: i) to evaluate the bioaccessible phenolic compounds (PC) in T and HT during upper gastrointestinal digestion, ii) to in vitro ferment the indigestible fractions of the samples to evaluate the short-chain fatty acids (SCFA) production, iii) the microbial metabolites, bioconverted PC and volatile organic compounds (VOCs) generated during the fermentation. Vanillic acid was the most bioaccessible PC and after 48 h, 3-hydroxyphenylacetic acid was the most abundant microbial metabolite identified in both samples. The identification of VOCs belonging to terpenes (and derivatives) group in T and HT can be product of the microbial metabolism of carotenoids. The study shows new knowledge of the in vitro intestinal digestion and fermentation of T and HT final compounds with biological potential which should be evaluated in further studies.

Asunto(s)

Colon/microbiología , Ácidos Grasos Volátiles/metabolismo , Fermentación , Frutas/química , Microbioma Gastrointestinal , Fenoles/metabolismo , Disponibilidad Biológica , Carotenoides/metabolismo , Digestión , Solanum lycopersicum , Fenilacetatos/metabolismo , Physalis , Ácido Vanílico/metabolismo , Compuestos Orgánicos Volátiles/metabolismo

RESUMEN

Enzymatic inhibition by natural compounds may represent a valuable adjuvant in snakebite serum therapy. The objective in this work was to evaluate possible in vitro interactions between vanillic acid and enzymes from Bothrops spp. and Crotalus durissus terrificus venoms, and also suggest a theory as how they interact based on molecular docking. Vanillic acid inhibited the phospholipase activity induced by Bothrops alternatus (∼25% inhibition); the caseinolytic activity induced by Bothrops atrox (∼30%), Bothrops jararacussu (∼44%), and C. d. terrificus (∼33%); the fibrinogenolysis induced by B. jararacussu, B. atrox, and C. d. terrificus (100%); the serine protease activity induced by Bothrops moojeni (∼45%) and Bothrops jararaca (∼66%); the hemolytic activity induced by B. moojeni (∼26%); the thrombolysis activity induced by B. atrox (∼30%) and B. jararacussu (∼20%); and the thrombotic activity induced by C. d. terrificus (∼8%). The compound was also capable of delaying the coagulation time in citrated plasma by 60, 35, and 75 Sec, when incubated with B. moojeni, B. atrox, and B. jararaca, respectively. The results obtained expand the possibilities for future pharmaceutical use of vanillic acid, considering the high homology degree among human and snake venom phospholipases A2 and proteases (involved in chronic inflammatory diseases). Also, this compound can be used as adjuvant to improve currently available treatments for ophidism victims.

Asunto(s)

Simulación del Acoplamiento Molecular , Péptido Hidrolasas/metabolismo , Inhibidores de Fosfolipasa A2/farmacología , Fosfolipasas A2/metabolismo , Inhibidores de Proteasas/farmacología , Ácido Vanílico/farmacología , Animales , Humanos , Inhibidores de Fosfolipasa A2/química , Inhibidores de Proteasas/química , Serpientes , Ácido Vanílico/química

RESUMEN

AIMS: To study the individual and combined contribution of catechin, protocatechuic and vanillic acids to inhibit the adhesion of uropathogenic Escherichia coli (UPEC) on the surface of silicone catheters. METHODS AND RESULTS: The adhesion of UPEC to silicone catheters during the exposure to nonlethal concentrations of phenolic compounds was measured, as well as changes in motility, presence of fimbriae, extra-cellular polymeric substances, surface charge, hydrophobicity and membrane fluidity. The phenolic combination reduced 26-51% of motility, 1 log CFU per cm2 of adhered bacteria and 20-40% the carbohydrate and protein content in the biofilm matrix. Curli fimbriae, surface charge and cell hydrophobicity were affected to a greater extent by the phenolic combination. In the mixture, vanillic acid was the most effective for reducing bacterial adhesion, extra-polymeric substance production, motility, curli fimbriae and biofilm structure. Notwithstanding, protocatechuic acid caused major changes in the bacterial cell surface properties, whereas catechin affected the cell membrane functionality. CONCLUSION: Catechin, protocatechuic and vanillic acids have different bacterial cell targets, explaining the synergistic effect of their combination against uropathogenic E. coli. SIGNIFICANCE AND IMPACT OF STUDY: This study shows the contribution of catechin, protocatechuic and vanillic acids in producing a synergistic mixture against the adhesion of uropathogenic E. coli on silicone catheters. The action of catechin, vanillic and protocatechuic acids included specific contributions of each compound against the E. coli membrane's integrity, motility, surface properties and production of extracellular polymeric substances. Therefore, the studied mixture of phenolic compounds could be used as an antibiotic alternative to reduce urinary tract infections associated with silicone catheters.

Asunto(s)

Antibacterianos/farmacología , Adhesión Bacteriana/efectos de los fármacos , Biopelículas/efectos de los fármacos , Catequina/farmacología , Hidroxibenzoatos/farmacología , Infecciones Urinarias/microbiología , Escherichia coli Uropatógena/efectos de los fármacos , Ácido Vanílico/farmacología , Catéteres/microbiología , Sinergismo Farmacológico , Infecciones por Escherichia coli/microbiología , Fimbrias Bacterianas/efectos de los fármacos , Fimbrias Bacterianas/genética , Fimbrias Bacterianas/metabolismo , Humanos , Fenoles/farmacología , Siliconas/análisis , Escherichia coli Uropatógena/crecimiento & desarrollo , Escherichia coli Uropatógena/fisiología

RESUMEN

A series of amides derived from vanillic acid were obtained by coupling reactions using PyBOP ((Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate) and DCC (Dicyclohexylcarbodiimide) coupling reagents. These were submitted to biological evaluation for species of Candida, Staphylococcus, and Pseudomonas. The microdilution method in broth was used for the antimicrobial testing to determine the Minimum Inhibitory Concentration (MIC) and to verify the likely mechanism of action for antifungal activity. The ten amides were obtained with yields ranging from 28.81 to 86.44%, and three compounds were novel. In the antibacterial evaluation, the amides (in their greatest concentrations) were bioactive against Staphylococcus aureus strain ATCC 25925. Meanwhile, all of the tested amides presented antifungal activity against at least one strain. The amide with best antifungal profile was compound 7, which featured an MIC of 0.46 µmol/mL, and a mechanism of action involving the plasma membrane and fungal cell wall. The presence of a methyl group in the para position of the aromatic ring is suggested which enhances the activity of the compound against fungi. Docking studies of the ten compounds using the protein 14α-demethylase as a biological target were also performed. The biological results presented good correlation with molecular docking studies demonstrating that a possible site of antifungal action for bioactive amides is the enzyme 14α-demethylase.

Asunto(s)

Amidas/farmacología , Antibacterianos/farmacología , Simulación del Acoplamiento Molecular , Ácido Vanílico/química , Amidas/química , Bacterias/efectos de los fármacos , Candida/efectos de los fármacos , Pruebas de Sensibilidad Microbiana

RESUMEN

Inflammation is the response of the body to noxious stimuli such as infections, trauma, or injury. Experimental studies have shown that vanillic acid has anti-inflammatory effects. The objective of this study was to investigate the anti-inflammatory and antipyretic properties of the derivative of vanillic acid, isopropyl vanillate (ISP-VT), in mice. The results of this study indicated that ISP-VT reduced paw edema induced by carrageenan, dextran sulfate (DEX), compound 48/80, serotonin, bradykinin (BK), histamine (HIST), and prostaglandin E2 (PGE2). Furthermore, ISP-VT reduced recruitment of leukocytes and neutrophils and reduced its adhesion and rolling, and decreased myeloperoxidase enzyme activity (MPO), cytokine levels (tumor necrosis factor-α and interleukin-6), and vascular permeability. ISP-VT also significantly reduced the expression of cyclooxygenase-2 (COX-2) in subplantar tissue of mice. ISP-VT inhibited COX-2 selectively compared to the standard drug. Our results showed that although ISP-VT binds to COX-1, it is less toxic than indomethacin, as evidenced by MPO analysis of gastric tissue. Treatment with the ISP-VT significantly reduced rectal temperature in yeast-induced hyperthermia in mice. Our results showed that the main mechanism ISP-VT-induced anti-inflammatory activity is by inhibition of COX-2. In conclusion, our results indicate that ISP-VT has potential as an anti-inflammatory and antipyretic therapeutic compound.

Asunto(s)

Antiinflamatorios/administración & dosificación , Carragenina/efectos adversos , Inhibidores de la Ciclooxigenasa/administración & dosificación , Inflamación/tratamiento farmacológico , Fenoles/efectos adversos , Ácido Vanílico/química , Animales , Antiinflamatorios/síntesis química , Antiinflamatorios/química , Antiinflamatorios/farmacología , Anticuerpos Monoclonales/efectos de los fármacos , Inhibidores de la Ciclooxigenasa/síntesis química , Inhibidores de la Ciclooxigenasa/química , Inhibidores de la Ciclooxigenasa/farmacología , Modelos Animales de Enfermedad , Femenino , Inflamación/inducido químicamente , Inflamación/metabolismo , Inyecciones Intraperitoneales , Masculino , Ratones , Modelos Moleculares , Fenoles/síntesis química , Fenoles/química , Fenoles/farmacología , Bibliotecas de Moléculas Pequeñas/administración & dosificación , Bibliotecas de Moléculas Pequeñas/síntesis química , Bibliotecas de Moléculas Pequeñas/química , Bibliotecas de Moléculas Pequeñas/farmacología

RESUMEN

Physicochemical properties, cooking time, and phenolics profile of two black rice genotypes grown at six different locations in Brazil were determined. The cultivar IAC 600 and the elite-line AE 153045 were used. The main growing locations for black rice were considered, as follows: Alegrete (ALG), Capão do Leão (CPL), Guaratinguetá (GUA), Roseira (ROS), Santa Vitória do Palmar (SVP), and Taubaté (TBT). Principal component analysis (PCA) and supervised partial least squares-discriminant analysis (PLS-DA) from liquid chromatography-mass spectrometry (LC-MS) data sets showed distinction among genotypes and locations. Quercetin-3-O-glucoside and vanillic acid were the most relevant compounds for discriminating genotypes. SVP location provided the most distinctive black rice, with greater total phenolics content. Characteristics of black rice from SVP location were associated to effects of latitude and wind conditions. Hesperetin, vanillic acid, quercetion-3-O-glucoside, and p-coumaric acid were the most relevant compounds for discriminating locations.

Asunto(s)

Cromatografía Líquida de Alta Presión , Espectrometría de Masas , Oryza/química , Fenoles/análisis , Amilosa/análisis , Análisis Discriminante , Genotipo , Glucósidos/química , Análisis de los Mínimos Cuadrados , Oryza/genética , Oryza/metabolismo , Fenoles/química , Extractos Vegetales/química , Análisis de Componente Principal , Quercetina/análogos & derivados , Quercetina/química , Ácido Vanílico/química

RESUMEN

BACKGROUND: This study characterized the flavonoid and nonflavonoid phenolic composition of Carménère and Cabernet Sauvignon wines that were in contact with barrels, chips, and staves during a 12 month aging period. The wines were evaluated by spectrophotometric (for total phenols, anthocyanins and tannins, colorant intensity, hue, CIELab parameters, and fractionation into mono-, oligo-, and polymers of proanthocyanidins) and high-performance liquid chromatography diode array detection analyses (for ellagitannins, gallotannins, anthocyanins, and low molecular weight phenols). RESULTS: Wines in contact with oak wood presented a strong enrichment with nonflavonoid compounds, such as caffeic, gallic, and ellagic acids and ellagitannins. Wines in contact with staves stood out for the increased presence of total phenols, vanillic acid, and higher color intensity, whereas wines aged in contact with chips showed large contents of proanthocyanidin gallates. Wines aged in barrels exhibited high contents of ellagitannins and ethyl gallates. The effect of wood on the phenolic composition was mostly associated with the original and intrinsic characteristics of each grape variety. CONCLUSION: Extraction of phenolic compounds from oak wood during wine aging is closely related to the wood format, grape variety (Carménère or Cabernet Sauvignon), and aging time. The final effect of wood on wine would be related not just to the transference of polyphenols from wood, but also to structural modifications of grape polyphenols. © 2018 Society of Chemical Industry.

Asunto(s)

Embalaje de Alimentos/instrumentación , Fenoles/química , Quercus/química , Vitis/química , Vino/análisis , Madera/química , Color , Manipulación de Alimentos , Factores de Tiempo , Ácido Vanílico/análisis

RESUMEN

The objective of this study was to evaluate the effect of combining catechin, protocatechuic, and vanillic acids against planktonic growing, adhesion, and biofilm eradication of uropathogenic Escherichia coli (UPEC), as well as antioxidant agents. The minimum inhibitory concentrations (MIC) of protocatechuic, vanillic acids and catechin against the growth of planktonic bacteria were 12.98, 11.80, and 13.78 mM, respectively. Mixing 1.62 mM protocatechuic acid + 0.74 mM vanillic acid + 0.05 mM catechin resulted in a synergistic effect acting as an MIC. Similarly, the minimum concentrations of phenolic compounds to prevent UPEC adhesion and biofilm formation (MBIC) were 11.03 and 7.13 mM of protocatechuic and vanillic acids, respectively, whereas no MBIC of catechin was found. However, combinations of 1.62 mM protocatechuic acid + 0.74 mM vanillic acid + 0.05 mM catechin showed a synergistic effect acting as MBIC. On the other hand, the minimum concentrations to eradicate biofilms (MBEC) were 25.95 and 23.78 mM, respectively. The combination of 3.20 mM protocatechuic acid, 2.97 mM vanillic acid, and 1.72 mM catechin eradicated pre-formed biofilms. The antioxidant capacity of the combination of phenolics was higher than the expected theoretical values, indicating synergism by the DPPH•, ABTS, and FRAP assays. Effective concentrations of catechin, protocatechuic, and vanillic acids were reduced from 8 to 1378 times when combined. In contrast, the antibiotic nitrofurantoin was not effective in eradicating biofilms from silicone surfaces. In conclusion, the mixture of phenolic compounds was more effective in preventing cell adhesion and eradicating pre-formed biofilms of uropathogenic E. coli than single compounds and nitrofurantoin, and showed antioxidant synergy.

Asunto(s)

Antibacterianos/farmacología , Catequina/farmacología , Hidroxibenzoatos/farmacología , Ácido Vanílico/farmacología , Antibacterianos/química , Antioxidantes/química , Antioxidantes/farmacología , Biopelículas/efectos de los fármacos , Catequina/química , Humanos , Hidroxibenzoatos/química , Pruebas de Sensibilidad Microbiana , Plancton/efectos de los fármacos , Escherichia coli Uropatógena/efectos de los fármacos , Escherichia coli Uropatógena/patogenicidad , Ácido Vanílico/química

RESUMEN

Colon cancer is the second most common cause of cancer deaths in the USA and Europe. Despite aggressive therapies, many tumors are resistant to current treatment protocols and epidemiological data suggest that diet is a major factor in the etiology of colon cancer. This study aimed to evaluate the antioxidant activity and the influence of 3,4-dihydroxyphenylacetic (3,4-DHPAA), p-coumaric (p-CoA), vanillic (VA) and ferulic (FA) acids on cell viability, cell cycle progression, and rate of apoptosis in human colon adenocarcinoma cells (HT-29). The results showed that all compounds tested reduce cell viability in human colon cancer cells. 3,4-DHPAA promoted the highest effect antiproliferative with an increase in the percentage of cells in G0/G1 phase, accompanied by a reduction of cells in G2/M phase. Cell cycle analysis of VA and FA showed a decrease in the proportion of cells in G0/G1 phase (10.0 µM and 100.0 µM). p-CoA and FA acids increased the percentage of apoptotic cells and non-apoptotic cells. 3,4-DHPAA seems to be the substance with the greatest potential for in vivo studies, opening thus a series of perspectives on the use of these compounds in the prevention and treatment of colon cancer.

Asunto(s)

Adenocarcinoma/tratamiento farmacológico , Proliferación Celular/efectos de los fármacos , Neoplasias del Colon/tratamiento farmacológico , Hidroxibenzoatos/farmacología , Ácido 3,4-Dihidroxifenilacético/farmacocinética , Ácido 3,4-Dihidroxifenilacético/farmacología , Adenocarcinoma/patología , Apoptosis/efectos de los fármacos , División Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Neoplasias del Colon/patología , Simulación por Computador , Ácidos Cumáricos/farmacocinética , Ácidos Cumáricos/farmacología , Células HT29 , Humanos , Hidroxibenzoatos/clasificación , Hidroxibenzoatos/farmacocinética , Propionatos/farmacocinética , Propionatos/farmacología , Ácido Vanílico/farmacocinética , Ácido Vanílico/farmacología

RESUMEN

Human phospholipase A2 (hPLA2) of the IIA group (HGIIA) catalyzes the hydrolysis of membrane phospholipids, producing arachidonic acid and originating potent inflammatory mediators. Therefore, molecules that can inhibit this enzyme are a source of potential anti-inflammatory drugs, with different action mechanisms of known anti-inflammatory agents. For the study and development of new anti-inflammatory drugs with this action mechanism, snake venom PLA2 (svPLA2) can be employed, since the svPLA2 has high similarity with the human PLA2 HGIIA. Despite the high similarity between these secretory PLA2s, it is still not clear if these toxins can really be employed as an experimental model to predict the interactions that occur with the human PLA2 HGIIA and its inhibitors. Thus, the present study aims to compare and evaluate, by means of theoretical calculations, docking and molecular dynamics simulations, as well as experimental studies, the interactions of human PLA2 HGIIA and two svPLA2s,Bothrops toxin II and Crotoxin B (BthTX-II and CB, respectively). Our theoretical findings corroborate experimental data and point out that the human PLA2 HGIIA and svPLA2 BthTX-II lead to similar interactions with the studied compounds. From our results, the svPLA2 BthTX-II can be used as an experimental model for the development of anti-inflammatory drugs for therapy in humans.

Asunto(s)

Antiinflamatorios/química , Venenos de Crotálidos/enzimología , Crotoxina/metabolismo , Inhibidores de Fosfolipasa A2/química , Fosfolipasas A2/química , Ácido Vanílico/química , Secuencia de Aminoácidos , Fosfolipasas A2 Grupo II , Humanos , Enlace de Hidrógeno , Simulación del Acoplamiento Molecular

RESUMEN

The aim of the present study was to determine the contents of bioactive compounds present in brown, green and red species of propolis cultivated in the Brazilian northeast states of Alagoas and Sergipe. The contents of phenolic compounds, flavonoids and antioxidant activity (DPPH, ABTS+, FRAP, ORAC) were determined. Identification and quantification of phenolic and flavonoid compounds were performed by using UHPLC-QqQ-MS/MS system. The results revealed high contents of total phenolics and flavonoids. Among the three species, the antioxidant potential had higher capacity in the red propolis. The presence of some of bioactive compounds viz. acacetin, artepellin C, eriodictyol, gallic acid, isorhamnetin, protocatechuic acid, vanillin and vanillic acid in Brazilian red propolis is reported for the first time in this work. Positive correlation between total phenolics versus the FRAP and ORAC methods was established which led to conclusion that antioxidant activity of propolis is mainly due to its phenolic compounds.

Asunto(s)

Antioxidantes/química , Própolis/química , Benzaldehídos , Brasil , Cromatografía Líquida de Alta Presión , Color , Flavanonas , Flavonas , Flavonoides/análisis , Ácido Gálico , Hidroxibenzoatos , Fenoles/análisis , Fenilpropionatos , Quercetina/análogos & derivados , Espectrometría de Masas en Tándem , Ácido Vanílico

RESUMEN

This study aims to identify special metabolites in polar extracts from Urochloa humidicola (synonym Brachiaria humidicola) that have allelopathic effects and induce secondary photosensitization in ruminants. The compounds were isolated and identified via chromatographic and spectroscopic techniques. The compounds 4-hydroxy-3-methoxy-benzoic acid, trans-4-hydroxycinnamic acid, and p-hydroxy-benzoic acid; the flavonols isorhamnetin-3-O-ß-d-glucopyranoside and methyl quercetin-3-O-ß-d-glucuronate; and kaempferitrin, quercetin-3-O-α-l-rhamnopyranoside, and tricin were identified in the extract from the leaves of Urochloa humidicola. Two furostanic saponins, namely, dioscin and 3-O-α-l-rhamnopyranosyl-(1-4)-[α-l-rhamnopyranosyl-(1-2)]-ß-d-glucopyranosyl-penogenin, as well as catechin-7-O-ß-d-glucopyranoside were identified in the methanolic extract obtained from the roots of this plant. This species features a range of metabolites that may be toxic for animals if used in food and may interfere with the growth medium, thereby inhibiting the development of other species.

Asunto(s)

Brachiaria/química , Flavonoides/aislamiento & purificación , Extractos Vegetales/química , Cromatografía en Capa Delgada , Crotonatos/química , Crotonatos/aislamiento & purificación , Flavonoides/química , Glicósidos/química , Glicósidos/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Estructura Molecular , Parabenos/química , Parabenos/aislamiento & purificación , Hojas de la Planta/química , Raíces de Plantas/química , Quercetina/análogos & derivados , Quercetina/química , Quercetina/aislamiento & purificación , Saponinas/química , Saponinas/aislamiento & purificación , Ácido Vanílico/química , Ácido Vanílico/aislamiento & purificación

RESUMEN

ABSTRACT This study aims to identify special metabolites in polar extracts from Urochloa humidicola (synonym Brachiaria humidicola) that have allelopathic effects and induce secondary photosensitization in ruminants. The compounds were isolated and identified via chromatographic and spectroscopic techniques. The compounds 4-hydroxy-3-methoxy-benzoic acid, trans-4-hydroxycinnamic acid, and p-hydroxy-benzoic acid; the flavonols isorhamnetin-3-O-β-d-glucopyranoside and methyl quercetin-3-O-β-d-glucuronate; and kaempferitrin, quercetin-3-O-α-l-rhamnopyranoside, and tricin were identified in the extract from the leaves of Urochloa humidicola. Two furostanic saponins, namely, dioscin and 3-O-α-l-rhamnopyranosyl-(1-4)-[α-l-rhamnopyranosyl-(1-2)]-β-d-glucopyranosyl-penogenin, as well as catechin-7-O-β-d-glucopyranoside were identified in the methanolic extract obtained from the roots of this plant. This species features a range of metabolites that may be toxic for animals if used in food and may interfere with the growth medium, thereby inhibiting the development of other species.

Asunto(s)

Flavonoides/aislamiento & purificación , Extractos Vegetales/química , Brachiaria/química , Parabenos/aislamiento & purificación , Parabenos/química , Saponinas/química , Ácido Vanílico/química , Flavonoides/química , Crotonatos/aislamiento & purificación , Crotonatos/química , Espectroscopía de Resonancia Magnética , Estructura Molecular , Cromatografía en Capa Delgada , Glicósidos/aislamiento & purificación , Glicósidos/química

RESUMEN

Bioactivity-guided fractionation of antileishmanial active extract from leaves of Casearia arborea led to isolation of three metabolites: tricin (1), 1',6'-di-O-ß-d-vanilloyl glucopyranoside (2) and vanillic acid (3). Compound 1 demonstrated the highest activity against the intracellular amastigotes of Leishmania infantum, with an IC50 value of 56 µm. Tricin (1) demonstrated selectivity in mammalian cells (SI > 7) and elicited immunomodulatory effect on host cells. The present work suggests that tricin modulated the respiratory burst of macrophages to a leishmanicidal state, contributing to the parasite elimination. Therefore, the natural compound tricin could be further explored in drug design studies for leishmaniasis treatment.

Asunto(s)

Antiprotozoarios/aislamiento & purificación , Casearia/química , Flavonoides/farmacología , Animales , Antiprotozoarios/farmacología , Flavonoides/aislamiento & purificación , Factores Inmunológicos/aislamiento & purificación , Factores Inmunológicos/farmacología , Leishmania infantum/efectos de los fármacos , Macrófagos Peritoneales/parasitología , Ratones , Ratones Endogámicos BALB C , Estructura Molecular , Extractos Vegetales/química , Extractos Vegetales/farmacología , Hojas de la Planta/química , Salicaceae , Ácido Vanílico/aislamiento & purificación , Ácido Vanílico/farmacología

RESUMEN

The consumption of healthy and natural foods has increased over the last few years, primarily because these foods are rich in substances with biological properties of interest, such as exerting anticancer effects and decreasing oxidative stress in living tissues. These foods support adequate nutrition, maintain health, and improve quality of life. Vanillic acid (VA) is a phenolic compound used widely in the food industry as a flavoring, preservative, and food additive. VA can be found in various cereals, whole grains, fruits, herbs, green tea, juices, beers, and wines and possesses antioxidant, hepatoprotective, cardioprotective, and antiapoptotic activities. Studying the cytotoxicity as well as the mutagenic and antimutagenic effects of different concentrations of VA in Rattus norvegicus hepatoma cells (HTC) can identify new cellular activities of this substance. Concentrations up to 100 µM VA are not cytotoxic to HTC cells in a MTT [3-(4,5-dimethilthiazol-2-yl)-2,5-diphenil tetrazolium bromide] assay after 96-h exposure; therefore, VA does not compromise mitochondrial activity. Similarly, concentrations up to 500 µM do not compromise plasma membrane integrity. VA at 10 and 50 µM showed no mutagenic/clastogenic effects, as no significant micronuclei induction was observed. VA 10 µM presented no antiproliferative activity and reduced the cytotoxicity induced by benzo[a]pyrene. The antimutagenic activity of 10 µM VA was observed by the simultaneous, pre-, and post-treatments, as the phenolic compound significantly reduced the frequency of micronuclei induced by the mutagen. These results indicate that VA exerts different responses in HTC cells. Low concentrations present no cytotoxic, mutagenic, or antiproliferative effects and protect cells from DNA damage.

Asunto(s)

Antimutagênicos/farmacología , Ácido Vanílico/farmacología , Animales , Línea Celular , Proliferación Celular/efectos de los fármacos , Daño del ADN/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Extractos Vegetales/farmacología , Ratas

Asunto(s)

Animales , Masculino , Ácido Vanílico , Abejas/crecimiento & desarrollo , Eugenol , Cinamatos , Aminoácidos Aromáticos , Eucaliptol

RESUMEN

To monitor capsaicinoids in serum on-site, three new monoclonal antibodies (mAbs) were firstly proposed using a conjugate of 4-[(4-hydroxy-3-methoxybenzyl) amino]-4-oxobutanoic acid as the immunogen. Among them, the YQQD8 mAb showed the highest sensitivity and cross-reactivity to major capsaicinoids, such as capsaicin, dihydrocapsaicin and N-vanillylnonanamide. A competitive indirect enzyme-linked immunosorbent assay (icELISA) and a time-resolved fluorescent immunochromatographic assay (TRFICA) were established based on this mAb. The linear range was 1.1-27.0ngmL(-1) for icELISA and 1.9-62.5ngmL(-1) for TRFICA and the limit of detection (LOD) of TRFICA was 1.5ngmL(-1). To decrease the interference of sample components and increase accuracy, serum samples were diluted four times before assays. As a result, the linear range of serum samples was 4.6-107.9ngmL(-1) for icELISA and 7.6-250.0ngmL(-1) for TRFICA. Both icELISA and TRFICA showed good recoveries (91.0-112.8% for icELISA and 87.6-111.5% for TRFICA) and concordant results in spiked experiments. Overall, this is the first report of immunoassay based on the mAbs for quantitative determination of major capsaicinoids, and the results demonstrate that both methods can meet the demands of rapid on-site assay for capsaicinoids in serum samples.

Asunto(s)

Capsaicina/análogos & derivados , Cromatografía de Afinidad/métodos , Ensayo de Inmunoadsorción Enzimática/métodos , Ácido Vanílico/análogos & derivados , Animales , Anticuerpos Monoclonales/química , Técnicas Biosensibles/métodos , Capsaicina/sangre , Femenino , Fluorescencia , Técnica del Anticuerpo Fluorescente/métodos , Humanos , Límite de Detección , Ratones Endogámicos BALB C , Conejos , Ratas , Ácido Vanílico/análisis