RESUMEN

Stingless bees belong to the Meliponini tribe and are widely distributed in the tropics and subtropics, where they perform important ecological services. Among the best distributed groups of stingless bees is the genus Scaptotrigona, which includes 22 species distributed throughout the neotropical region, including the area from Mexico to Argentina. Bees of this genus are responsible for the production of products such as honey, propolis, geopropolis and fermented pollen ("saburá"). This review aimed to provide an overview of the chemical composition and biological activities associated with derived products from stingless bees of the genus Scaptotrigona. The bibliographic review was carried out through searches in the Scopus, Web of Science, ScienceDirect and PubMed databases, including publications from 2003 to January 2023. The study of the chemodiversity of products derived from Scaptotrigona demonstrated the mainly presence of flavonoids, phenolic acids, terpenoids and alkaloids. It was also demonstrated that products derived from bees of the genus Scaptotrigona exhibit a wide range of biological effects, such as antibacterial, antioxidant, anti-inflammatory and antifungal activities, among other bioactivities. This review provides an overview of phytochemical and pharmacological investigations of the genus Scaptotrigona. However, it is essential to clarify the toxicity and food safety of these products.

Asunto(s)

Miel , Himenópteros , Própolis , Animales , Antibacterianos/farmacología , Abejas , México , Própolis/farmacología , Flavonoides/química , Flavonoides/aislamiento & purificación , Flavonoides/farmacología , Hidroxibenzoatos/química , Hidroxibenzoatos/aislamiento & purificación , Hidroxibenzoatos/farmacología , Terpenos/química , Terpenos/aislamiento & purificación , Terpenos/farmacología , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/farmacología

RESUMEN

Phenolic compounds, obtained from plants are important in the food, biomaterial and pharmaceutical industries; however current extraction methods, such as Soxhlet (solid-liquid) extraction, liquid-liquid extraction, microwave-assisted extraction, and ultrasonic extraction (USE), have the disadvantages of large processing times, contamination by solvents, and degradation of analytes. This study demonstrates that shock wave-assisted extraction can be used as a more efficient, eco-friendly and rapid method. Extraction of powdered samples of Eysenhardtia polystachia heartwood, a plant with high concentration of phenolic compounds, exposed to different doses of underwater shock waves, was compared with the conventional methods. Our results revealed that shock wave-assisted extraction (1500 shock waves with a peak positive pressure of approximately 88 MPa) produced 34.54% and 31.95% higher contents than Soxhlet and USE, respectively. Extraction times using shock waves were much shorter than with all other methods tested, proving that it is an attractive method to obtain both phenolic acids and flavonoids without the need for organic solvents. Furthermore, shock waves produced a significantly higher content of total reducing sugars than Soxhlet extraction and less phenolic acids which gives the insight of a more selective extraction of components.

Asunto(s)

Fabaceae/química , Flavonoides/aislamiento & purificación , Ondas Ultrasónicas , Hidroxibenzoatos/aislamiento & purificación , Extracción Líquido-Líquido , Extractos Vegetales/química

RESUMEN

A "green" analytical method is reported for the determination of phenolic acids in mushrooms. The sample preparation involves aqueous extraction based on acid hydrolysis, followed by analysis of extracts by capillary electrophoresis with diode array detector (CE-DAD). A central composite design was used to obtain the optimum conditions for the extraction of compounds from mushrooms, including the concentration of hydrochloric acid (2 mol·L-1), temperature (80 °C) and time (30 min). The proposed method avoids organic solvents such as methanol and acetonitrile commonly used as extraction solvent and/or mobile phase in studies on bioactive compounds in plant-based matrices by high-performance liquid chromatography, thus contributing to lower environmental impact. The validated CE-DAD method was applied to 42 samples of edible mushrooms, including the species Agaricus bisporus (white button mushroom and brown portobello), Lentinula edodes (shiitake), Pleurotus ostreatus (white oyster mushroom, hiratake and shimeji) and Pleurotus ostreatoroseus (pink oyster mushroom). The phenolic compounds homogentisic acid, cinnamic acid and p-coumaric acid were detected in the samples harvested in two seasons - summer and winter - with cinnamic acid reported as the major compound (levels between 53.88 and 440.42 mg·kg-1). Therefore, edible mushrooms have proved to be an alternative source of phenolic compounds.

Asunto(s)

Agaricales/química , Electroforesis Capilar/métodos , Hidroxibenzoatos/análisis , Hidroxibenzoatos/aislamiento & purificación , Fraccionamiento Químico , Límite de Detección , Modelos Lineales , Análisis Multivariante , Fenoles/análisis , Fenoles/aislamiento & purificación , Reproducibilidad de los Resultados

RESUMEN

Sequential extraction and purification stages are required to obtain extracts rich in specific polyphenols. However, both separation processes are often optimized independently and the effect of the integrated process on the global recovery of polyphenols has not been fully elucidated yet. We assessed the impact of hot-pressurized liquid extraction (HPLE) conditions (temperature: 90-150 °C; ethanol concentration: 15%-50%) on the global recovery of specific phenolic acids, flavanols, flavonols and stilbenes from Carménère grape pomace in an integrated HPLE/resin purification (RP) process. HPLE of phenolic acids, flavanols and stilbenes were favored when temperature and ethanol concentration increased, except for chlorogenic acid which showed an increment of its Gibbs free energy of solvation at higher ethanol contents. Ethanol concentration significantly impacted the global yield of the integrated HPLE/RP process. The lower the ethanol content of the HPLE extracts, the higher the recovery of phenolic acids, flavanols and stilbenes after RP, except for flavonols which present more polar functional groups. The best specific recovery conditions were 150 °C and ethanol concentrations of 15%, 32.5% and 50% for phenolic acids, flavanols and stilbenes, and flavonols, respectively. At 150 °C and 32.5% of ethanol, the extracts presented the highest total polyphenol content and antioxidant capacity. The integrated HPLE/RP process allows a selective separation of specific polyphenols and eliminates the interfering compounds, ensuring the safety of the extracts at all evaluated conditions.

Asunto(s)

Flavonoles/aislamiento & purificación , Hidroxibenzoatos/aislamiento & purificación , Extracción Líquido-Líquido/métodos , Polifenoles/aislamiento & purificación , Estilbenos/aislamiento & purificación , Vitis/química , Ácido Clorogénico/aislamiento & purificación , Etanol/química , Calor , Extractos Vegetales/química , Presión , Solventes/química , Termodinámica

RESUMEN

This study evaluated to determine the phenolic and flavonoids contents, and antioxidant, anti-inflammatory, and antiproliferative activity of the hydromethanolic extracts of the leaves, pulp, and seeds of Annona cacans. The isolation and structural identification of the constituent acetogenin, phenolic acid, and flavonoids were also reported. Antioxidant capacity was determined by the 2,2-diphenyl-1-picrylhydrazyl (DPPH), ethylbenzothiazoline-6-sulfonic acid (ABTS), and ß-carotene/linoleic acid methods. Cell proliferation was determined by spectrophotometric quantification of the cellular protein content using a sulforhodamine B assay. Anti-inflammatory activity was evaluated in paw edema model, to myeloperoxidase (MPO) activity induced by carrageenan in mice. Fractionation resulted in the isolation of one acetogenin (annoreticuin-9-one), two flavonoids (quercetin-3-O-ß-glucoside-6-O-α-rhamnoside and kaempferol-3-O-ß-glucoside), and one phenolic acid (p-coumaric acid). The pulp extract presented potent antioxidant activities by the DPPH (IC50 = 44.08 µg/mL) and ABTS (IC50 = 39.32 µg/mL) methods, as well as high contents of phenols (618.95 mg GA/g) and flavonoids (477.35 mg QE/g). The bioguided fractionation demonstrated that the ethyl acetate fraction of the pulp extract and annoreticuin-9-one showed potent antiproliferative activity against ovarian cancer (GI50 = 6.4 µg/mL). The anti-inflammatory activity demonstrated significant inhibition of edema compared to the control group in 2 and 4 h; in addition, the extracts inhibited the increase in MPO activity after 6 h, when compared to the DEX and control groups. For the first time, this study demonstrated antioxidant, anti-inflammatory, and antiproliferative activity, as well as compounds isolated, suggesting that A. cacans could also be potential sources for prevention of cancer and other diseases associated with oxidative stress.

Asunto(s)

Annona/química , Antiinflamatorios/farmacología , Antineoplásicos Fitogénicos/farmacología , Antioxidantes/farmacología , Acetogeninas/aislamiento & purificación , Animales , Antiinflamatorios/aislamiento & purificación , Antineoplásicos Fitogénicos/aislamiento & purificación , Antioxidantes/aislamiento & purificación , Carragenina , Línea Celular Tumoral , Edema/inducido químicamente , Edema/tratamiento farmacológico , Flavonoides/aislamiento & purificación , Humanos , Hidroxibenzoatos/aislamiento & purificación , Masculino , Ratones , Estructura Molecular , Peroxidasa/metabolismo , Fenoles/aislamiento & purificación , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Hojas de la Planta/química , Semillas/química

RESUMEN

Myrciaria cauliflora (jaboticaba) is an edible fruit common in Brazil that has been used for treating respiratory diseases, including chronic tonsillitis and asthma. This study explores the distribution of an anti-inflammatory depside, jaboticabin, in different parts of the jaboticaba plant as well as major polyphenols from the wood of jaboticaba, some with biological activity similar to jaboticabin. The peel of the fruit was found to be the major source of jaboticabin. This is the first phytochemical study of the wood of M. cauliflora. The antioxidant-activity-guided fractionation strategy successfully identified 3,3'-dimethylellagic acid-4- O-sulfate from jaboticaba wood. This ellagic acid derivative, in a manner similar to jaboticabin, showed antiradical activity and inhibited the production of the chemokine interleukin-8 after treating the human small airway epithelial cells with cigarette smoke extract. The human intestinal Caco-2 cell studies demonstrated the jaboticabin transport in vitro. The polyphenols, jaboticabin and 3,3'-dimethyellagic acid-4- O-sulfate, from jaboticaba were both found to exhibit anti-inflammatory activities, thus suggesting the potential use of these compounds or even the fruits themselves for chronic obstructive pulmonary disease.

Asunto(s)

Antiinflamatorios/farmacología , Hidroxibenzoatos/farmacología , Myrtaceae/química , Extractos Vegetales/farmacología , Polifenoles/farmacología , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Brasil , Células CACO-2 , Frutas/química , Humanos , Hidroxibenzoatos/química , Hidroxibenzoatos/aislamiento & purificación , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Polifenoles/química , Polifenoles/aislamiento & purificación , Enfermedad Pulmonar Obstructiva Crónica/tratamiento farmacológico , Enfermedad Pulmonar Obstructiva Crónica/inmunología

RESUMEN

UHPLC/ESI/MS identification of organic compounds is the first step in the majority of screening techniques for the characterization of biologically active metabolites in natural sources. This paper describes a method for the fast identification and characterisation of secondary metabolites in Leptocarpha rivularis DC. (Palo negro) extracts by HPLC/UV (DAD)-Mass Spectrometry (HPLC/MS). The plant is used for the treatment of several diseases since pre-hispanic Mapuche times. Thirty-seven compounds were detected in the aqueous edible extract for the first time including 4 sesquiterpenes, 10 flavonoids, 9 oxylipins, 2 organic acids, and 11 phenolic acids. In addition, phenolic content antioxidant and cholinesterase inhibitory activities were measured for the first time using the edible infusion. The total polyphenol content of the infusion was 230.76 ± 2.5 mmol GAE/kg dry weight, while the antioxidant activity was 176.51 ± 28.84; 195.28 ± 4.83; and 223.92 ± 2.95 mmol TE/kg dry weight, for the DPPH, ABTS, and FRAP assays, respectively. The cholinesterase inhibitory activity was 7.38 ± 0.03 and 5.74 ± 0.06 mmol GALAE/kg, for the inhibition of acetylcholinesterase AChE and BChE, respectively, showing that this plant is a candidate for the isolation of compounds that can be useful for the treatment of neurodegenerative diseases. Furthermore, this plant could serve also as a raw material for the production of dietary supplements, due to its content of polyphenolic compounds.

Asunto(s)

Antioxidantes/farmacología , Asteraceae/química , Productos Biológicos/farmacología , Compuestos de Bifenilo/antagonistas & inhibidores , Inhibidores de la Colinesterasa/farmacología , Picratos/antagonistas & inhibidores , Acetilcolinesterasa/metabolismo , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Productos Biológicos/química , Productos Biológicos/aislamiento & purificación , Butirilcolinesterasa/metabolismo , Inhibidores de la Colinesterasa/química , Inhibidores de la Colinesterasa/aislamiento & purificación , Cromatografía Líquida de Alta Presión , Relación Dosis-Respuesta a Droga , Flavonoides/química , Flavonoides/aislamiento & purificación , Flavonoides/farmacología , Hidroxibenzoatos/química , Hidroxibenzoatos/aislamiento & purificación , Hidroxibenzoatos/farmacología , Estructura Molecular , Oxilipinas/química , Oxilipinas/aislamiento & purificación , Oxilipinas/farmacología , Sesquiterpenos/química , Sesquiterpenos/aislamiento & purificación , Sesquiterpenos/farmacología , Espectrometría de Masa por Ionización de Electrospray , Relación Estructura-Actividad

RESUMEN

The agroindustrial residues have been recognized as important sources of some prominent chemical compounds and hence a viable strategy of obtaining bioactive compounds could be applied to them. The present study was aimed to investigate the presence of bioactive compounds and the antioxidant activity of some Brazilian exotic fruits (achachairu, araçá-boi, bacaba) residues. The antioxidant capacity of fruit residues was evaluated by ORAC, FRAP and ABTS assays. The contents of total phenolic compounds, flavonoids, chlorophylls and carotenoids were determined. The identification and quantification of the phenolic compounds were performed by using the UHPLC-QqQ-MS/MS system. The compounds cinnamic acid, p-coumaric acid, epicatechin and quercetin were identified and quantified in all fruits residues. The residue with the highest antioxidant capacity was bacaba for ORAC (15,285.51±20.38µmolTE/100g) and FRAP (16,916.37±10.01µmolTE/100g) assays, as well as total phenolic compounds in its methanolic extract (1537.45±73.35mgGAE/100g).

Asunto(s)

Antioxidantes/aislamiento & purificación , Arecaceae/química , Carotenoides/aislamiento & purificación , Eugenia/química , Flavonoides/aislamiento & purificación , Frutas/química , Garcinia/química , Hidroxibenzoatos/aislamiento & purificación , Antioxidantes/farmacología , Benzotiazoles/química , Brasil , Carotenoides/farmacología , Cloruros/química , Cromatografía Líquida de Alta Presión , Compuestos Férricos/química , Flavonoides/farmacología , Hidroxibenzoatos/farmacología , Capacidad de Absorbancia de Radicales de Oxígeno , Ácidos Sulfónicos/química , Espectrometría de Masas en Tándem

RESUMEN

Carya illinoensis is a widespread species, belonging to the Juglandaceae family, commonly known as Pecan. Popularly, the leaves have been used in the treatment of smoking as a hypoglycemic, cleansing, astringent, keratolytic, antioxidant, and antimicrobial agent. The following research aimed to identify for the first time the phytochemical compounds present in the leaves of C. illinoensis and carry out the determination of antimicrobial activity of aqueous and ethanolic extracts. The antimicrobial activity was tested against 20 microorganisms by determining the minimum inhibitory concentration (MIC). Phenolic acids (gallic acid and ellagic acid), flavonoids (rutin), and tannins (catechins and epicatechins) were identified by HPLC-DAD and may be partially responsible for the antimicrobial activity against Gram-positive, Gram-negative, and yeast. The results showed MIC values between 25 mg/mL and 0.78 mg/mL. The extracts were also able to inhibit the production of germ tubes by Candida albicans.

Asunto(s)

Antifúngicos/análisis , Antifúngicos/farmacología , Bacterias/efectos de los fármacos , Carya/química , Fitoquímicos/análisis , Fitoquímicos/farmacología , Levaduras/efectos de los fármacos , Antifúngicos/aislamiento & purificación , Cromatografía Líquida de Alta Presión , Flavonoides/análisis , Flavonoides/aislamiento & purificación , Flavonoides/farmacología , Hidroxibenzoatos/análisis , Hidroxibenzoatos/aislamiento & purificación , Hidroxibenzoatos/farmacología , Pruebas de Sensibilidad Microbiana , Fitoquímicos/aislamiento & purificación , Hojas de la Planta/química , Taninos/análisis , Taninos/aislamiento & purificación , Taninos/farmacología

RESUMEN

Mass spectrometry has become a method of choice to characterize bioactive compounds in biological samples because of its sensitivity and selectivity. Hybrid ultra-HPLC hyphenated with Orbitrap mass analyzer is an innovative state of the art technology that allows fast and accurate metabolomic analyses. In this work the metabolites of a Chilean mistletoe endemic to the VIII region of Chile were investigated for the first time using UHPLC mass analysis (UHPLC-PDA-HESI-Orbitrap MS(n)). The anthocyanins, together with the non-pigmented phenolics were fingerprinted and correlated with the antioxidant capacities measured by the bleaching of the DPPH radical, the ferric reducing antioxidant power (FRAP), the superoxide anion scavenging activity assay (SA), and total content of phenolics, flavonoids and anthocyanins measured by spectroscopic methods. Six anthocyanins were identified, and among them, the 3-O-glycosides of delphinidin and cyanidin were the major ones. In addition, several phenolic acids (including feruloylquinic acid, feruloyl glucose, chlorogenic acid) and several flavonols (luteolin, quercetin, apigenin, isorhamnetin and glycoside derivatives) were also identified. The mistletoe leaves showed the highest antioxidant activity as measured by the DPPH radical bleaching, ferric reducing antioxidant power and superoxide anion scavenging activity tests (13.38 ± 0.47 µg/mL, 125.32 ± 5.96 µmolTE/g DW and 84.06 ± 4.59 at 100 µg/mL, respectively).

Asunto(s)

Antocianinas/química , Antioxidantes/química , Flavonoides/química , Flavonoles/química , Hidroxibenzoatos/química , Muérdago/química , Antocianinas/aislamiento & purificación , Antioxidantes/aislamiento & purificación , Compuestos de Bifenilo/antagonistas & inhibidores , Chile , Cromatografía Líquida de Alta Presión/métodos , Flavonoides/aislamiento & purificación , Flavonoles/aislamiento & purificación , Hidroxibenzoatos/aislamiento & purificación , Picratos/antagonistas & inhibidores , Extractos Vegetales/química , Hojas de la Planta/química , Espectrometría de Masas en Tándem/métodos

RESUMEN

The antioxidant features, polyphenolic composition and chromatographic fingerprints of the aerial parts from three Chilean endemic plants from the Paposo Valley located on the cost of the Atacama Desert were investigated for the first time using high pressure liquid chromatography coupled with photodiode array detector and electrospray ionization mass analysis (HPLC-PDA-ESI-MS) and spectroscopic methods. The phenolic fingerprints obtained for the plants were compared and correlated with the antioxidant capacities measured by the bleaching of the DPPH radical, the ferric reducing antioxidant power (FRAP) and quantification of the total content of phenolics and flavonoids measured by spectroscopic methods. Thirty phenolics were identified for the first time for these species, mostly phenolic acids, flavanones, flavonols and some of their glycoside derivatives, together with three saturated fatty acids (stearic, palmitic and arachidic acids). Nolana ramosissima showed the highest antioxidant activity (26.35 ± 1.02 µg/mL, 116.07 ± 3.42 µM Trolox equivalents/g dry weight and 81.23% ± 3.77% of inhibition in the DPPH, FRAP and scavenging activity (SA) assays, respectively), followed by  N. aplocaryoides (85.19 ± 1.64 µg/mL, 65.87 ± 2.33 µM TE/g DW and 53.27% ± 3.07%) and N. leptophylla (124.71 ± 3.01, 44.23 ± 5.18 µM TE/g DW and 38.63% ± 1.85%).

Asunto(s)

Antioxidantes/química , Flavonoides/química , Fenoles/química , Extractos Vegetales/química , Solanaceae/química , Antioxidantes/aislamiento & purificación , Chile , Cromatografía Líquida de Alta Presión , Flavonoides/aislamiento & purificación , Frutas/química , Hidroxibenzoatos/química , Hidroxibenzoatos/aislamiento & purificación , Espectrometría de Masas , Fenoles/aislamiento & purificación

RESUMEN

BACKGROUND: Tribolium castaneum (Herbst) is a harmful pest of stored grain and flour-based products in tropical and subtropical region. In the present study, rhizome of Drynaria quercifolia (J. Smith) was evaluated for pesticidal and pest repellency activities against T. castaneum, using surface film method and filter paper disc method, respectively. In addition, activity of the isolated compound 3,4-dihydroxybenzoic acid was evaluated against the pest. RESULTS: Chloroform soluble fraction of ethanol extract of rhizome of D. quercifolia showed significant pesticidal activity at doses 0.88 to 1.77 mg/cm(2) and significant pest repellency activity at doses 0.94 to 0.23 mg/cm(2). No pesticidal and pest repellency activity was found for petroleum ether, ethyl acetate and methanol soluble fractions of ethanol extract as well as for 3,4-dihydroxybenzoic acid. CONCLUSION: Considering our findings it can be concluded that chloroform soluble fraction of rhizome of D. quercifolia is useful in controlling T. castaneum of stored grain and flour-based products.

Asunto(s)

Hidroxibenzoatos/farmacología , Repelentes de Insectos/farmacología , Control de Plagas/métodos , Plaguicidas , Polypodiaceae/química , Rizoma/química , Tribolium/efectos de los fármacos , Acetatos , Alcanos , Animales , Cloroformo , Etanol , Hidroxibenzoatos/aislamiento & purificación , Dosificación Letal Mediana , Metanol , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación

RESUMEN

Bioactivity-guided fractionation of EtOH extract from the leaves of Piper aduncum L. (Piperaceae) afforded a new dihydrochalcone, named adunchalcone. Its structure was elucidated on the basis of their spectroscopic data, primarily NMR and MS. Adunchalcone was evaluated against promastigote forms of Leishmania (L.) amazonensis, L. (V.) braziliensis, L. (V.) shawi, and L. (L.) chagasi and displayed 50% effective concentrations (EC50) of 11.03, 26.70, and 11.26 µM, as well as selective indexes of 4.86, 2.01, 4.76 and 0.50, respectively. This compound was also tested against intracellular forms of L. (L.) amazonensis, displaying weak activity, in comparison to reference drug amphotericin B. However, despite reduced effect of adunchalcone against amastigotes of L. (L.) amazonensis, this work opens the perspective to use this particular molecule as a scaffold for the design of novel and selective drug candidates for neglected diseases, mainly leishmaniasis.

Asunto(s)

Antiparasitarios/aislamiento & purificación , Chalconas/aislamiento & purificación , Hidroxibenzoatos/aislamiento & purificación , Leishmania/efectos de los fármacos , Piper/química , Animales , Antiparasitarios/química , Antiparasitarios/farmacología , Chalconas/química , Chalconas/farmacología , Hidroxibenzoatos/química , Hidroxibenzoatos/farmacología , Ratones Endogámicos BALB C , Pruebas de Sensibilidad Microbiana

RESUMEN

BACKGROUND: Tribolium castaneum (Herbst) is a harmful pest of stored grain and flour-based products in tropical and subtropical region. In the present study, rhizome of Drynaria quercifolia (J. Smith) was evaluated for pesticidal and pest repellency activities against T. castaneum, using surface film method and filter paper disc method, respectively. In addition, activity of the isolated compound 3,4-dihydroxybenzoic acid was evaluated against the pest. RESULTS: Chloroform soluble fraction of ethanol extract of rhizome of D. quercifolia showed significant pesticidal activity at doses 0.88 to 1.77 mg/cm² and significant pest repellency activity at doses 0.94 to 0.23 mg/cm². No pesticidal and pest repellency activity was found for petroleum ether, ethyl acetate and methanol soluble fractions of ethanol extract as well as for 3,4-dihydroxybenzoic acid. CONCLUSION: Considering our findings it can be concluded that chloroform soluble fraction of rhizome of D. quercifoliais useful in controlling T. castaneum of stored grain and flour-based products.

Asunto(s)

Animales , Plaguicidas , Tribolium/efectos de los fármacos , Control de Plagas/métodos , Polypodiaceae/química , Rizoma/química , Hidroxibenzoatos/farmacología , Repelentes de Insectos/farmacología , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/química , Cloroformo , Etanol , Metanol , Alcanos , Hidroxibenzoatos/aislamiento & purificación , Dosificación Letal Mediana , Acetatos

RESUMEN

Bioassay-guided fractionation of the bio-active organic extract obtained from solid-media culture of MEXU 27095, an endophytic fungus isolated from the Mexican medicinal plant Hintonia latiflora (Rubiaceae), led to separation of three tridepsides which were identified as thielavins A, J and K. All three compounds inhibited Saccharomyces cerevisieae α-glucosidase (αGHY) in a concentration-dependent manner with IC50 values of 23.8, 15.8, and 22.1µM, respectively. Their inhibitory action was higher than that of acarbose (IC50=545µM), used as a positive control. Kinetic analysis established that the three compounds acted as non-competitive inhibitors with ki values of 27.8, 66.2 and 55.4µM, respectively (α=1.0, 1.2, 0.7, respectively); acarbose behaved as competitive inhibitor with a ki value of 156.1µM. Thielavin J inhibited the activity of α-glucosidase from Bacillus stearothermophilus (αGHBs) with an IC50 of 30.5µM, being less active than acarbose (IC50=0. 015µM); in this case, compound (2) (ki=20.0µM and α=2.9) and acarbose (ki=0.008µM and α=1.9) behaved as non-competitive inhibitors. Docking analysis predicted that all three thielavins and acarbose bind to homologated αGHBs and to αGHY (PDB: 3A4A) in a pocket close to the catalytic site for maltose and isomaltose, respectively. The α-glucosidase inhibitory properties of thielavin K (3) were corroborated in vivo since it induced a noted antihyperglycemic action during an oral sucrose tolerance test (3.1, 10.0 and 31.6mg/kg) in normal and nicotinamide-streptozotocin diabetic mice. In addition, at a dose of 10mg/kg, it provoked a moderate hypoglycemic activity in diabetic mice.

Asunto(s)

Ascomicetos/química , Inhibidores Enzimáticos/farmacología , Inhibidores de Glicósido Hidrolasas , Hidroxibenzoatos/farmacología , Rubiaceae/microbiología , Acarbosa/farmacología , Animales , Glucemia/metabolismo , Diabetes Mellitus Experimental/sangre , Diabetes Mellitus Experimental/tratamiento farmacológico , Diabetes Mellitus Tipo 2/sangre , Diabetes Mellitus Tipo 2/tratamiento farmacológico , Relación Dosis-Respuesta a Droga , Inhibidores Enzimáticos/química , Inhibidores Enzimáticos/aislamiento & purificación , Hidroxibenzoatos/química , Hidroxibenzoatos/aislamiento & purificación , Hipoglucemiantes/química , Hipoglucemiantes/farmacología , Cinética , Masculino , México , Ratones Endogámicos ICR , Modelos Moleculares , Estructura Molecular , Fitoterapia , Plantas Medicinales/microbiología , Unión Proteica , Estructura Terciaria de Proteína , Saccharomyces cerevisiae/enzimología , Resultado del Tratamiento , alfa-Glucosidasas/química , alfa-Glucosidasas/metabolismo

RESUMEN

This study developed and validated a method for the extraction and determination of 11 phenolic acids in rat plasma, urine, and liver by ultraperformance liquid chromatography-mass spectrometry (UPLC-MS). A system suitability test (instrumental linearity, area, and retention time precision) was performed and recovery, intraday and between-day precisions, detection limits (LOD), and quantification limits (LOQ) were determined for all compounds in each biological matrix. Recoveries varied between 88 and 117% in plasma, between 87 and 102% in urine, and between 38 and 100% in liver. Precision was higher than 13.7% intraday and 14.0% interday in all matrices, at three concentration levels. To demonstrate the applicability, the method was used to estimate the concentrations of phenolic acids in samples from animals that received 5-caffeoylquinic acid (5-CQA) by gavage. The excellent validation results and the applicability of the method to real samples confirmed the suitability for studies on absorption, bioavailability, and pharmacokinetics of phenolic acids derived from foods rich in phenolic compounds.

Asunto(s)

Cromatografía Líquida de Alta Presión/métodos , Hidroxibenzoatos/análisis , Hígado/química , Extracción en Fase Sólida/métodos , Espectrometría de Masas en Tándem/métodos , Animales , Hidroxibenzoatos/sangre , Hidroxibenzoatos/aislamiento & purificación , Hidroxibenzoatos/orina , Límite de Detección , Masculino , Ratas , Ratas Wistar

RESUMEN

Prenylhydroxybenzoic acid derivatives and other two analogues previously reported were isolated from Piper arieianum leaves. The structures of the compounds were assigned from detailed spectroscopical analysis (NMR 1D and 2D and HR ESI TOF MS) data and by comparison with data from the literature. These molecules posses pungent activity different to that of capsaicin and their activity is related to their structure and their mechanism of action can involve interactions with TRPV1 channel.

Asunto(s)

Hidroxibenzoatos/aislamiento & purificación , Hidroxibenzoatos/farmacología , Piper/química , Benzoatos , Hidroxibenzoatos/química , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Hojas de la Planta/química , Prenilación

RESUMEN

Phenolic compounds are found in seaweed species together with other substances presenting antioxidant activity. The objective of this work was to evaluate the antioxidant activity of the free phenolic acids (FPA) fraction from the seaweed Halimeda monile, and its activity to protect the expression of hepatic enzymes in rats, under experimental CCl4 injury. The antioxidant activity was measured by the DPPH method. The FPA fraction (80 mg/kg, p.o.) was administered during 20 consecutive days to rats. The peroxidation was performed by thiobarbituric acid reactive substances (TBARS). The SOD and CAT enzymatic expressions were measured by RT/PCR. The histology technique was used to evaluate liver injuries. The expression of both, CAT and SOD genes, was more preserved by FPA. Only partial injury could be observed by histology in the liver of rats receiving FPA as compared with the control group; and CCl4 administration induced 60% more peroxidation as compared with the rats receiving FPA. These data suggest that FPA could modulate the antioxidant enzymes and oxidative status in the liver through protection against adverse effects induced by chemical agents.

Asunto(s)

Antioxidantes/farmacología , Hepatopatías/prevención & control , Hígado/efectos de los fármacos , Algas Marinas/química , Animales , Antioxidantes/aislamiento & purificación , Secuencia de Bases , Catalasa/metabolismo , Cartilla de ADN , Hidroxibenzoatos/aislamiento & purificación , Hidroxibenzoatos/farmacología , Hígado/enzimología , Masculino , Ratas , Ratas Wistar , Reacción en Cadena de la Polimerasa de Transcriptasa Inversa , Superóxido Dismutasa/metabolismo , Sustancias Reactivas al Ácido Tiobarbitúrico

RESUMEN

The hydroalcohol extracts of Achillea millefolium L. (AM) and Artemisia vulgaris L. (AV), both belonging to the Asteraceae family, were evaluated by the hot plate, writhing, formalin and intestinal transit tests in an attempt to confirm their folk use as analgesic, antiinflammatory and antispasmodic agents. AM 500 and 1000 mg/kg significantly inhibited abdominal contortions by 65% and 23%, respectively, whereas AV 500 and 1000 mg/kg inhibited them by 48% and 59%, respectively. None of the extracts produced differences in the intestinal transit in mice, nor in the response time in the hot plate or in the immediate or late responses in the formalin test. In HPLC/DAD analyses 'fingerprint', monitored at 360 and 270 nm, both hydroalcohol extracts showed the same flavonoid glycoside as a principal constituent, which was identified as rutin. A high content of caffeic acid derivatives were also found in both extracts. The main differences were observed at 240 nm: AM had a higher content of rutin, while in AV the hydroxybenzoic acid derivative was the major component.

Asunto(s)

Achillea/química , Analgésicos/farmacología , Artemisia/química , Extractos Vegetales/farmacología , Animales , Antiinflamatorios/farmacología , Ácidos Cafeicos/aislamiento & purificación , Cromatografía Líquida de Alta Presión , Tránsito Gastrointestinal/efectos de los fármacos , Hidroxibenzoatos/aislamiento & purificación , Masculino , Ratones , Parasimpatolíticos/farmacología , Rutina/aislamiento & purificación

RESUMEN

Lichens and their secondary metabolites have attracted the interest of many researchers. Some species have been shown to contain substances with remarkable biologic activity, as antimicrobial, mainly against Gram positive bacteria; antineoplasic acting on solid and ascetic tumors, or in culture cells; antiviral; hypotensive; and spasmolytic effects. The aim of this study was to isolate and characterize atranorin, one of the major constituents which presents in Cladina kalbii (DES ABB.) AHTI., and analyze its antinociceptive effect. The antinociceptive activity was verified in acetic acid-induced writhing test and formalin test with mice. In this work it was observed that atranorin was effective in significant reducing (p<0.05) abdominal writhing at doses of 200 and 400 mg/kg (p.o.) by 52.6 and 61.3%, respectively, when compared to control group (vehicle). The formalin test showed in 200 and 400 mg/kg (p.o.) that atranorin injection was able to inhibit the inflammatory processes (second phase) dose dependently.

Asunto(s)

Analgésicos/química , Analgésicos/farmacología , Ascomicetos/química , Hidroxibenzoatos/química , Hidroxibenzoatos/farmacología , Líquenes/química , Ácido Acético , Analgésicos/aislamiento & purificación , Animales , Aspirina/farmacología , Rastreo Diferencial de Calorimetría , Fenómenos Químicos , Química Física , Análisis Diferencial Térmico , Formaldehído , Hidroxibenzoatos/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Masculino , Ratones , Dimensión del Dolor/efectos de los fármacos , Espectrofotometría Infrarroja , Difracción de Rayos X