RESUMEN
Polyphenolic compounds are common constituents of human and animal diets and undergo extensive metabolism by the gut microbiota before entering circulation. In order to compare the transformations of polyphenols from yerba mate, rosemary, and green tea extracts in the gastrointestinal tract, simulated gastrointestinal digestion coupled with colonic fermentation were used. For enhancing the comparative character of the investigation, colonic fermentation was performed with human, pig and rat intestinal microbiota. Chemical analysis was performed using a HPLC system coupled to a diode-array detector and mass spectrometer. Gastrointestinal digestion diminished the total amount of phenolics in the rosemary and green tea extracts by 27.5 and 59.2 %, respectively. These reductions occurred mainly at the expense of the major constituents of these extracts, namely rosmarinic acid (-45.7 %) and epigalocatechin gallate (-60.6 %). The yerba mate extract was practically not affected in terms of total phenolics, but several conversions and isomerizations occurred (e.g., 30 % of trans-3-O-caffeoylquinic acid was converted into the cis form). The polyphenolics of the yerba mate extract were also the least decomposed by the microbiota of all three species, especially in the case of the human one (-10.8 %). In contrast, the human microbiota transformed the polyphenolics of the rosemary and green extracts by 95.9 and 88.2 %, respectively. The yerba mate-extract had its contents in cis 3-O-caffeoylquinic acid diminished by 78 % by the human microbiota relative to the gastrointestinal digestion, but the content of 5-O-caffeoylquinic acid (also a chlorogenic acid), was increased by 22.2 %. The latter phenomenon did not occur with the rat and pig microbiota. The pronounced interspecies differences indicate the need for considerable caution when translating the results of experiments on the effects of polyphenolics performed in rats, or even pigs, to humans.
Asunto(s)
Colon , Depsidos , Digestión , Fermentación , Ilex paraguariensis , Extractos Vegetales , Polifenoles , Ácido Rosmarínico , Rosmarinus , Animales , Humanos , Extractos Vegetales/metabolismo , Rosmarinus/química , Ratas , Ilex paraguariensis/química , Porcinos , Depsidos/metabolismo , Depsidos/análisis , Polifenoles/metabolismo , Polifenoles/análisis , Colon/metabolismo , Colon/microbiología , Masculino , Cinamatos/metabolismo , Cinamatos/análisis , Microbioma Gastrointestinal , Té/química , Ácido Quínico/análogos & derivados , Ácido Quínico/metabolismo , Ácido Quínico/análisis , Catequina/análogos & derivados , Catequina/metabolismo , Catequina/análisis , Cromatografía Líquida de Alta Presión , Camellia sinensis/químicaRESUMEN
The present work carries out a quantitative analysis of the major bioactive compounds found in the native Mexican purple tomatoes. Total phenolic content ranged from 7.54 to 57.79 mg TPC/g DM, total flavonoid content ranged from 1.89 to 16.93 mg TFC/g DM, total anthocyanin content ranged from 0.29 to 2.56 mg TAC/g DM, and total carotenoid content ranged from 0.11 to 0.75 mg TCC/ g DM. In addition, 14 phenolic acids were identified, among which caffeoylquinic acid derivatives were the most abundant compounds with chlorogenic acid concentration up to 9.680 mg/g DM, together with flavonoids, such as rutin and quercetin-hexoxide. The qualitative analysis also showed the presence of 9 acylated anthocyanins and 2 carotenoids with significant functional features. As for anthocyanins, their chemical structures disclosed special structural features: glycosylated anthocyanins exhibited cis-trans hydroxycinnamic moieties and petunidin-3-(trans-p-coumaroyl)-rutinoside-5-glucoside was reported to be the main anthocyanin, whitin the range of concentrations between 0.160 and 1.143 mg/g DM.
Asunto(s)
Antocianinas , Carotenoides , Flavonoides , Fenoles , Solanum lycopersicum , Solanum lycopersicum/química , Antocianinas/análisis , Carotenoides/análisis , México , Flavonoides/análisis , Fenoles/análisis , Frutas/química , Ácido Clorogénico/análisis , Ácido Quínico/análisis , Ácido Quínico/análogos & derivados , Hidroxibenzoatos/análisisRESUMEN
Few sclerophyllous plants from the central coast of Chile have been systematically studied. This work describes the phytochemical composition and antimicrobial properties of Baccharis concava Pers. (sin. B. macraei), a shrub found in the first line and near the Pacific coast. B. concava has been traditionally used by indigenous inhabitants of today's central Chile for its medicinal properties. Few reports exist regarding the phytochemistry characterization and biological activities of B. concava. A hydroalcoholic extract of B. concava was prepared from leaves and small branches. Qualitative phytochemical characterization indicated the presence of alkaloids, steroids, terpenoids, flavonoids, phenolic, and tannin compounds. The antimicrobial activity of this extract was assessed in a panel of microorganisms including Gram-positive bacteria, Gram-negative bacteria, and pathogenic yeasts. The extract displayed an important antimicrobial effect against Gram-positive bacteria, Candida albicans, and Cryptococcus neoformans but not against Gram-negatives, for which an intact Lipopolysaccharide is apparently the determinant of resistance to B. concava extracts. The hydroalcoholic extract was then fractionated through a Sephadex LH-20/methanol-ethyl acetate column. Afterward, the fractions were pooled according to a similar pattern visualized by TLC/UV analysis. Fractions obtained by this criterion were assessed for their antimicrobial activity against Staphylococcus aureus. The fraction presenting the most antimicrobial activity was HPLC-ESI-MS/MS, obtaining molecules related to caffeoylquinic acid, dicaffeoylquinic acid, and quercetin, among others. In conclusion, the extracts of B. concava showed strong antimicrobial activity, probably due to the presence of metabolites derived from phenolic acids, such as caffeoylquinic acid, and flavonoids, such as quercetin, which in turn could be responsible for helping with wound healing. In addition, the development of antimicrobial therapies based on the molecules found in B. concava could help to combat infection caused by pathogenic yeasts and Gram-positive bacteria, without affecting the Gram-negative microbiota.
Asunto(s)
Baccharis , Quercetina , Ácido Quínico/análogos & derivados , Chile , Espectrometría de Masas en Tándem , Fitoquímicos/farmacología , Flavonoides/farmacología , Extractos Vegetales/farmacologíaRESUMEN
Biochemical characterization of polyphenol oxidase (PPO) present in purple sweet potato (PSP) is a key step in developing efficient methodologies to control oxidative damage caused by this enzyme to the valuable components of PSP, such as caffeoylquinic acid derivatives and acylated anthocyanins. Thus, this work focused on the assessment of the effects of pH, temperature, and chemical agents on the PPO activity as well as characterization of the PPO substrate specificity towards major phenolic compounds found in PSP. The optimum conditions of enzyme activity were pH 7 and a temperature range of 20-30 °C at which phenolic substrates were oxidized with 72.5-99.8% yield. Zn2+ ions remarkably reduced PPO activity while Cu2+ ions improved enzyme performance. The highest substrate preference was shown for 3,4,5-tri-caffeoylquinic and 3,5-di-caffeoylquinic acid, followed by 5-caffeoylquinic and caffeic acid, 3,4- and 4,5-di-caffeoylquinic acids, peonidin-3-caffeoyl-p-hydroxybenzoyl-sophoroside-5-glucoside. The highest Km values were found for 4,5-feruloyl-caffeoylquinic acid and catechol.
Asunto(s)
Antocianinas/química , Antocianinas/metabolismo , Catecol Oxidasa/metabolismo , Ipomoea batatas/enzimología , Ácido Quínico/análogos & derivados , Acilación , Unión Proteica , Ácido Quínico/química , Ácido Quínico/metabolismoRESUMEN
Owing to their antioxidant properties, caffeoylquinic acid (CQA)-derivatives could potentially improve the impaired metabolism in hepatic cells, however, their effect on mitochondrial function has not been demonstrated yet. Here, we evaluated the impact of three CQA-derivatives extracted from purple sweet potato, namely 5-CQA, 3,4- and 4,5-diCQA, on mitochondrial activity in primary hepatocytes using an extracellular flux analyzer. Notably, an increase of maximal respiration and spare respiratory capacity were observed when 5-CQA and 3,4-diCQA were added to the system indicating the improved mitochondrial function. Moreover, 3,4-diCQA was shown to considerably increase glycolytic reserve which is a measure of cell capability to respond to an energy demand through glycolysis. Conversely, 4,5-diCQA did not modify mitochondrial activity but increased glycolysis at low concentration in primary hepatocytes. All compounds tested improved cellular capacity to oxidize fatty acids. Overall, our results demonstrated the potential of test CQA-derivatives to modify mitochondrial function in hepatic cells. It is especially relevant in case of dysfunctional mitochondria in hepatocytes linked to hepatic steatosis during obesity, diabetes, and metabolic syndrome.
Asunto(s)
Hepatocitos/efectos de los fármacos , Ipomoea batatas/química , Mitocondrias/efectos de los fármacos , Extractos Vegetales/farmacología , Ácido Quínico/análogos & derivados , Animales , Células Cultivadas , Relación Dosis-Respuesta a Droga , Hepatocitos/metabolismo , Masculino , Ratones , Ratones Endogámicos C57BL , Mitocondrias/metabolismo , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Ácido Quínico/química , Ácido Quínico/aislamiento & purificación , Ácido Quínico/farmacologíaRESUMEN
OBJECTIVE: The aim of this study was to investigate the anti-inflammatory effects of the crude extract (CE), derived fraction, and isolated compounds from Calea pinnatifida leaves in a mouse model of pulmonary neutrophilia. METHODS: The CE and derived fractions, hexane, ethyl acetate, and methanol, were obtained from C. pinnatifida leaves. The compounds 3,5- and 4,5-di-O-E-caffeoylquinic acids were isolated from the EtOAc fraction using chromatography and were identified using infrared spectroscopic data and nuclear magnetic resonance (1H and 13C NMR). Leukocytes count, protein concentration of the exudate, myeloperoxidase (MPO) and adenosine deaminase (ADA), and nitrate/nitrite (NO x ), tumor necrosis factor-alpha (TNF-α), interleukin-1-beta (IL-1ß), and interleukin-17A (IL-17A) levels were determined in the pleural fluid leakage after 4 h of pleurisy induction. We also analyzed the effects of isolated compounds on the phosphorylation of both p65 and p38 in the lung tissue. RESULTS: The CE, its fractions, and isolated compounds inhibited leukocyte activation, protein concentration of the exudate, and MPO, ADA, NO x , TNF-α, IL-1ß, and IL-17A levels. 3,5- and 4,5-di-O-E-caffeoylquinic acids also inhibited phosphorylation of both p65 and p38 (P < 0.05). CONCLUSION: This study demonstrated that C. pinnatifida presents important anti-inflammatory properties by inhibiting activated leukocytes and protein concentration of the exudate. These effects were related to the inhibition of proinflammatory mediators. The dicaffeoylquinic acids may be partially responsible for these anti-inflammatory properties through the inhibition of nuclear transcription factor kappa B and mitogen-activated protein kinase pathways.
Asunto(s)
Asteraceae/química , Inflamación/tratamiento farmacológico , Trastornos Leucocíticos/tratamiento farmacológico , Enfermedades Pulmonares/tratamiento farmacológico , Neutrófilos/efectos de los fármacos , Extractos Vegetales/farmacología , Adenosina Desaminasa/metabolismo , Animales , Antiinflamatorios/farmacología , Carragenina , Modelos Animales de Enfermedad , Femenino , Inflamación/inducido químicamente , Interleucina-17/metabolismo , Interleucina-1beta/metabolismo , Trastornos Leucocíticos/inducido químicamente , Pulmón/efectos de los fármacos , Pulmón/metabolismo , Pulmón/patología , Enfermedades Pulmonares/inducido químicamente , Ratones , Nitratos/química , Nitritos/química , Peroxidasa/metabolismo , Fosforilación , Pleuresia/tratamiento farmacológico , Ácido Quínico/análogos & derivados , Ácido Quínico/química , Factor de Transcripción ReIA/metabolismo , Factor de Necrosis Tumoral alfa/metabolismo , Proteínas Quinasas p38 Activadas por Mitógenos/metabolismoRESUMEN
BACKGROUND: Lung adenocarcinoma (LAC) is a major worldwide cause of death by cancer, it shows high aggressiveness, functional decline, systemic compromise and severe cachexia, which might be counteracted by dietary redox-active phytochemicals. Therefore, our aim was to establish the anticancer effects of the oral intake of quercetin and 5 caffeoylquinic acid. METHODS: LAC-1-bearing male Balb/c mice received quercetin (0-25 µg/kg/d) and 5 caffeoylquinic acid (0-120 µg/kg/d) for three weeks, with different organic and biochemical variables being then compared with ANOVA and the Fisher Test (p <0.05). RESULTS: Quercetin delayed 1.18 fold tumour appearance and increased 8.87 fold non-neoplastic body weight gain, whereas 5 caffeoylquinic acid did it in a lesser extent (1.17 and 2.48 fold, respectively), with tumour weight being consequent with the evolution time. Quercetin induced >1.15 fold tumour hydroperoxides and lipoperoxides, whereas 5 caffeoylquinic acid induced only lipoperoxides. Although both phytochemicals reduced <0.85 fold hydroperoxides and lipoperoxides in the kidney, only quercetin was also antioxidant in the liver. Additionally, 5 caffeoylquinic acid increased >1.15 fold hepatic and renal weights. Although these phytochemicals did not modify telencephalic interleukin 6 production, quercetin augmented 2.51 fold interleukin 6 in the diencephalon, whereas 5 caffeoylquinic acid decreased it 0.43 fold. CONCLUSIONS: Quercetin delayed lung adenocarcinoma appearance and increased the non-neoplastic body weight gain in mice with tumour oxidative stress, without brain interleukin 6 participation. 5 caffeoylquinic acid showed similar effects, although they were weaker. Additionally, quercetin acted as a hepatic and renal antioxidant, whereas 5 caffeoylquinic acid only exerted this effect in the kidney. Therefore, safe oral doses of this flavonoid are promissory to modulate lung cancer progression, with further studies being encouraged.
Asunto(s)
Adenocarcinoma del Pulmón/tratamiento farmacológico , Neoplasias Pulmonares/tratamiento farmacológico , Quercetina/administración & dosificación , Ácido Quínico/análogos & derivados , Adenocarcinoma del Pulmón/metabolismo , Adenocarcinoma del Pulmón/patología , Administración Oral , Animales , Antioxidantes/administración & dosificación , Antioxidantes/metabolismo , Antioxidantes/farmacología , Peso Corporal/efectos de los fármacos , Caquexia/tratamiento farmacológico , Caquexia/metabolismo , Caquexia/patología , Progresión de la Enfermedad , Interleucina-6/sangre , Hígado/efectos de los fármacos , Hígado/metabolismo , Hígado/patología , Neoplasias Pulmonares/metabolismo , Neoplasias Pulmonares/patología , Masculino , Ratones , Ratones Endogámicos BALB C , Oxidación-Reducción , Estrés Oxidativo/efectos de los fármacos , Quercetina/farmacología , Ácido Quínico/administración & dosificación , Ácido Quínico/farmacologíaRESUMEN
Sweet potato peels are rich in chlorogenic acids. In this work, we applied ultrasound technology to extract the main compounds from sweet potato peel and used multivariate analysis and principal component analysis (PCA) to evaluate the effects of different extraction conditions on the extraction of chlorogenic acids. The extraction was studied varying ultrasonic power density (20, 35 and 50 W/L) and processing time (5, 10, 20 and 40 min) using an ultrasonic bath operating at 25 kHz. The chemical analysis was carried out by UPLC-qTOF-MS, and the results were evaluated by PCA and PLS-DA chemometric analysis. Results show that both ultrasonic power density and processing time influences in the extraction of different chlorogenic acid, and that different extraction conditions can be used to selectively extract specific caffeoylquinic acids and feruloylquinic acids in higher amounts. Ultrasound promoted the hydrolysis of tricaffeoylquinic acid when subjected to ultrasonic waves (20-50 W/L), and of 3,4-caffeyolquinic acid at high ultrasonic power density (50 W/L).
Asunto(s)
Ácido Clorogénico/aislamiento & purificación , Tecnología Química Verde , Ipomoea batatas/química , Ácido Quínico/análogos & derivados , Sonicación , Hidrólisis , Análisis de Componente Principal , Ácido Quínico/química , Reproducibilidad de los ResultadosRESUMEN
The study of Brazilian Conilon coffee genotypes with unknown chemical composition and sensory quality is extremely important since these data may contribute to the launching of new coffee cultivars in the international market with high cup quality. The present study aimed to investigate the metabolic profile of 3 genotypes of Conilon and compared them to Robusta Tropical and Arabica coffees, all collected at 3 different levels of ripeness. The extracts were analysed by ESI-LTQ-ORBITRAP, and 11 attributes were evaluated by sensory analysis. To correlate sensory, composition and maturation, chemometric analysis was used. The metabolites trigonelline, caffeine, caffeoylquinic acid and sugars revealed higher concentrations in genotypes 105 and 108. According to the sensorial analysis, genotype 108 showed the highest final score (82), which was even higher than the Arabica coffees. Among the new coffees studied, genotype 108 presented promising characteristics, sparking interest in its national and international commercialization.
Asunto(s)
Coffea/química , Genotipo , Alcaloides/análisis , Brasil , Cafeína/análisis , Coffea/genética , Genes de Plantas , Ácido Quínico/análogos & derivados , Ácido Quínico/análisis , Semillas/química , Espectrometría de Masa por Ionización de ElectrosprayRESUMEN
Sweet potato is one of the oldest crops cultivated in Mexico, and Mesoamerica is considered as a region with the greatest diversity of this species. Therefore, the present study focused on the evaluation of biologically active compounds, such as caffeoylquinic acid derivatives and flavonoid compounds, in sweet potato leaves of 200 accessions of the main producing regions of Mexico. The analysis of total phenol content (TPC) showed a great variability of concentrations among the examined accessions (54.41 to 284.64 mgTPC/g DW). Likewise, total flavonoid content (TFC) was determined and ranged from 10.01 to 40.17 mgTFC /g DW. Finally, total anthocyanin content (TAC) was evaluated and concentrations obtained varied from 0.05 to 0.98 mgTAC/g DW. Additionally, HPLC analysis of all 200 accessions demonstrated the presence of caffeic acid (CA), 5-caffeoylquinic acid (5-CQA), three isomers of di-caffeoylquinic acid (di-CCA) and 4-feruloyl-5-caffeoylquinic acid (4F-5CQA) in all test samples. Only 21 accessions tested showed the quantitative amount of 3,4,5-tri-caffeoylquinic acid (3,4,5-tri-CQA) with concentrations ranging from 44.73 to 193.22 mg/100 g DW and high content of 4F-5CQA (139.46 to 419.99 mg/100 g DW). The gathered data indicate that leaves of Mexican sweet potatoes are a promising source of phenolic compounds with remarkable nutraceutical potential.
Asunto(s)
Ipomoea batatas , Antocianinas , Flavonoides , México , Fenoles , Hojas de la Planta , Ácido Quínico/análogos & derivadosRESUMEN
Twelve chlorogenic acid derivatives and two flavones were isolated from Moquiniastrum floribundum (Asteraceae, other name: Gochnatia floribunda). Compounds were evaluated in relation to their cytotoxicity and antiradical properties. Cytotoxicity was not observed for compounds, however, chlorogenic acid derivatives showed antiradical activity and were more active than the Trolox standard. Quinic acid esterified with caffeoyl group at C-4 position showed higher antiradical activity compared to acylation at C-3 or C-5 positions. Additional caffeoyl groups esterified in quinic acid increase the antiradical activity observed for 4-caffeoylquinic acid. Excepted to 3,4-dicaffeoylquinic acid methyl ester, methyl ester derivatives show higher capacity of trapping radicals than their respective acids. Consequently, the presence of caffeoyl group at C-4 position of quinic acid is suggested as fundamental to obtain the highest antiradical activity.
Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Antioxidantes/farmacología , Asteraceae/química , Compuestos de Bifenilo/antagonistas & inhibidores , Picratos/antagonistas & inhibidores , Ácido Quínico/análogos & derivados , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Proliferación Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Células HCT116 , Humanos , Estructura Molecular , Ácido Quínico/química , Ácido Quínico/aislamiento & purificación , Ácido Quínico/farmacología , Relación Estructura-ActividadRESUMEN
Phenolic and nitrogenous compounds from different styles craft beers were identified by high performance liquid chromatography and mass spectrometry in order to stratify beer samples according to their style. For this, an exploratory assessment relying on Linear Discriminant Analysis was performed. Fifty-seven phenolic compounds were reported and twelve of them were found for the first time in beer: benzoic acids, 2,4-dihydroxybenzoic acid, 2,3-dihydroxybenzoic acid, dimethoxybenzoic acid; phenolic acid conjugates, 3-p-coumaroylquinic acid, 4-p-coumaroylquinic acid, 3-feruloylquinic acid, 4-feruloylquinic acid, 5-feruloylquinic acid; flavonoids, taxifolin hexoside, quercetin dihexoside, apigenin-6,8-dipentoside, and isofraxidin hexoside. Additionally, 11 nitrogenous compounds belonging to the phenolamide class were found. Two discriminant functions were generated and allowed a satisfactory separation among all beer styles. 3-Caffeoylquinic acid, 3-p-coumaroylquinic acid, 4-p-coumaroylquinic acid, 5-caffeoylquinic acid, coumaric acid, kaempferol-3-O-rutinoside, proanthocyanidin B dimer III and proanthocyanidin B dimer V were the compounds that showed the highest capacity of discriminate the beer styles (IPA, Lager and Weiss).
Asunto(s)
Cerveza/análisis , Análisis de los Alimentos/métodos , Compuestos de Nitrógeno/análisis , Fenoles/análisis , Ácido Clorogénico/análisis , Cromatografía Líquida de Alta Presión/métodos , Flavonoides/análisis , Hidroxibenzoatos/análisis , Peso Molecular , Compuestos de Nitrógeno/química , Fenoles/química , Ácido Quínico/análogos & derivados , Ácido Quínico/análisis , Espectrometría de Masa por Ionización de Electrospray/métodos , Espectrometría de Masas en Tándem/métodosRESUMEN
Coffee is one of the most consumed non-alcoholic beverages in the world. It is well known that some compounds present in coffee beans have important biological activities. In this study, evidence was turned to ßN-alkanoyl-5-hydroxytryptamides (C-5HTs) and to the furokaurane diterpenes cafestol and kahweol, associated with gastric irritation and increasing of blood cholesterol, respectively. Fermentation in coffee post-harvest wet process was induced by three Saccharomyces cerevisiae yeasts (for bakery, white and sparkling wines) as starter cultures. Variations in mass, time, temperature and pH (56 experiments under fractional factorial and mixture experimental designs) were tested. Substantial reductions for C-5HTs (up to 38% reduction for C20-5HT and 26% for C22-5HT) as well as for diterpenes (54% for cafestol and 53% for kahweol) were obtained after treating green coffee beans with 0.6â¯g of a 1:1:1 mixture the three yeasts for 12â¯h at 15⯰C and pHâ¯4. Caffeine and 5-CQA content, monitored in the green coffee beans, did not change. Therefore, the use of starter cultures during coffee post-harvest wet process has influence on the amount of some important compounds related to health and improves the sensory quality of the beverage.
Asunto(s)
Café/metabolismo , Diterpenos/química , Diterpenos/metabolismo , Manipulación de Alimentos/métodos , Saccharomyces cerevisiae/metabolismo , Bebidas , Cafeína , Café/química , Café/microbiología , Fermentación , Concentración de Iones de Hidrógeno , Ácido Quínico/análogos & derivados , Ácido Quínico/química , Temperatura , Factores de TiempoRESUMEN
The acidity and antioxidant activity of cold brew coffee were investigated using light roast coffees from Brazil, two regions of Ethiopia, Columbia, Myanmar, and Mexico. The concentrations of three caffeoylquinic acid (CQA) isomers were also determined. Cold brew coffee chemistry was compared to that of hot brew coffee prepared with the same grind-to-coffee ratio. The pH values of the cold and hot brew samples were found to be comparable, ranging from 4.85 to 5.13. The hot brew coffees were found to have higher concentrations of total titratable acids, as well as higher antioxidant activity, than that of their cold brew counterparts. It was also noted that both the concentration of total titratable acids and antioxidant activity correlated poorly with total CQA concentration in hot brew coffee. This work suggests that the hot brew method tends to extract more non-deprotonated acids than the cold brew method. These acids may be responsible for the higher antioxidant activities observed in the hot brew coffee samples.
Asunto(s)
Ácidos/química , Antioxidantes/química , Café/química , Ácido Quínico/análogos & derivados , Antioxidantes/aislamiento & purificación , Brasil , Ácido Clorogénico/química , Etiopía , Calor , Humanos , Concentración de Iones de Hidrógeno , México , Mianmar , Ácido Quínico/química , Ácido Quínico/aislamiento & purificación , Semillas/químicaRESUMEN
The present non-targeted 1H NMR-based fingerprinting approach along with multivariate analysis established differences between representative aqueous extracts of commercial ground roasted coffee (GRC) and instant (soluble) coffee (IC) samples. The latter were prepared either by spray drying or freeze drying. When comparing a total of 33 compounds between GRC and IC, the latter product contained a remarkable increase in 5-(hydroxymethyl)furfural and carbohydrates, as well as a clear decrease in trigonelline, N-methylpyridinium, caffeine, caffeoylquinic acids and 2-furylmethanol. Furthermore, the current protocol was able to detect the subtle chemical differences between spray-dried and freeze-dried IC. The aforementioned metabolites could serve as target molecules in the attempt to preserve, as much as possible, the organoleptic and nutraceutical properties of GRC during the industrial drying processes used in the production of the two commercial types of IC.
Asunto(s)
Coffea/química , Café/química , Manipulación de Alimentos/métodos , Espectroscopía de Resonancia Magnética/métodos , Metabolómica/métodos , Semillas/química , Alcaloides/análisis , Cafeína/análisis , Carbohidratos/análisis , Desecación/métodos , Liofilización , Furaldehído/análogos & derivados , Furaldehído/análisis , Calor , Ácido Quínico/análogos & derivados , Ácido Quínico/análisisRESUMEN
The plant metabolite 3,4,5-tri-O-galloylquinic acid methyl ester (TGAME, compound 6) was synthesized, and its potential effect on calcium oxalate monohydrate (COM) crystal binding to the surface of Madin-Darby canine kidney cells type I (MDCKI) and crystal growth in a Drosophila melanogaster Malpighian tubule (MT) model were investigated. Membrane, cytosolic, and total annexin A1 (AxA1), α-enolase, and heat shock protein 90 (HSP90) amounts were examined by Western blot analysis after subcellular fractionation, then confirmed by immunofluorescence staining of cultured cells. Pretreatment of MDCKI cells with TGAME for up to 6 h significantly diminished COM crystal binding in a concentration-dependent manner. TGAME significantly inhibited AxA1 surface expression by immunofluorescence microscopy, whereas intracellular AxA1 increased. Western blot analysis confirmed AxA1 expression changes in the membrane and cytosolic fractions of compound-treated cells, whereas whole cell AxA1 remained unchanged. TGAME also significantly decreased the size, number, and growth of calcium oxalate (CaOx) crystals induced in a Drosophila melanogaster MT model and possessed a potent antioxidant activity in a DPPH assay.
Asunto(s)
Anexina A1/efectos de los fármacos , Oxalato de Calcio/química , Adhesión Celular/efectos de los fármacos , Ácido Gálico/análogos & derivados , Ácido Quínico/análogos & derivados , Animales , Anexina A1/metabolismo , Antioxidantes , Línea Celular , Cristalización , Perros , Drosophila melanogaster , Ácido Gálico/síntesis química , Ácido Gálico/química , Ácido Gálico/farmacología , Células de Riñón Canino Madin Darby/efectos de los fármacos , Células de Riñón Canino Madin Darby/metabolismo , Túbulos de Malpighi/química , Ácido Quínico/síntesis química , Ácido Quínico/química , Ácido Quínico/farmacología , Fracciones Subcelulares/química , Fracciones Subcelulares/metabolismoRESUMEN
Copaifera langsdorffii Desf. (Fabaceae, Caesalpinioideae), popularly known as "copaiba" or "pau d'óleo", is a species of tree that is found throughout Brazil. The leaves of this tree are used in folk medicine to treat kidney stones. Galloylquinic acid derivatives and flavonoids are the main secondary metabolites found in C. langsdorffii leaves and are likely to be responsible for the effectiveness of this treatment. As an attempt to produce a phytotherapic, we have developed a reliable HPLC-UV method for the quality control of C. langsdorffii leaves. Phenolic compounds were extracted from C. langsdorffii leaves using 70% aqueous ethanol as the extraction solvent. HPLC-UV analyses were carried out on a Synergi Polar-RP column (100×3.0mm, 2.5µm), and the mobile phase was made up of formic acid-water (0.1:99.9, solvent A), and isopropanol-methanol-acetonitrile (5:40:60, solvent B). The elution gradient was A:B (90:10 to 85:15) in 8.0min, followed by A:B (85:15 to 64:36) up to 30.0min, using a flow rate of 0.7mL/min, and UV detection at 280nm. This method was used to quantify nine galloylquinic acid derivatives and two flavonoids, which gave a good detection response and linearity in the range of 1.88-110.0µg/mL. Furthermore, the detection and quantification limits ranged from 0.070 to 0.752µg/mL, and 0.211-2.278µg/mL respectively, with a maximum RSD of 4.18%. The method is reliable for the quality control of C. langsdorffii raw material, its hydroethanolic extract, and could potentially be used to quantify these compounds in other Copaifera species.
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Cromatografía Líquida de Alta Presión/métodos , Fabaceae/química , Flavonoides/análisis , Extractos Vegetales/química , Ácido Quínico/análisis , Flavonoides/química , Límite de Detección , Modelos Lineales , Hojas de la Planta/química , Ácido Quínico/análogos & derivados , Ácido Quínico/química , Reproducibilidad de los ResultadosRESUMEN
Brazilian green propolis is known as an appreciable natural antioxidant with abundant polyphenolic compounds. For quality control, a fingerprint-efficacy study of Brazilian green propolis was carried out in this work. Chemical fingerprints of Brazilian green propolis from 22 different sources were determined by HPLC and investigated by similarity analysis. The fingerprint-efficacy relationships between chemical fingerprint and DPPH radical-scavenging activity were established. The results showed that 14 characteristic common peaks were identified, and 9 compounds were discovered with free radical-scavenging activities. Caffeoylquinic acids and artepillin C might be the major effective components for quality control of Brazilian green propolis due to their specificity and strong antioxidant activity. This study provides new markers for the quality assessment of Brazilian green propolis and its derived products.
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Cromatografía Líquida de Alta Presión , Depuradores de Radicales Libres/análisis , Própolis/química , Brasil , Fenilpropionatos/análisis , Polifenoles/análisis , Ácido Quínico/análogos & derivados , Ácido Quínico/análisisRESUMEN
The beverage obtained from the yerba mate tea, besides being the most consumed in Brazil, has high concentrations of chlorogenic acids. In this study, a central composite design was employed to establish the best infusion time, temperature and water volume to maximize the extraction of chlorogenic acids 5-caffeoylquinic (5CQ), 3.4-dicaffeoylquinic (3.4 DQ), 3.5-dicaffeoylquinic (3.5 DQ) and 4.5-dicaffeoylquinic (4.5 DQ), from the leaves and stems of yerba mate tea (beverage ready for consumption). Analyses were performed by high-performance liquid chromatography and the optimum conditions were obtained through the use of the desirability function of Derringer and Suich. The maximum chlorogenic acids content in the beverage was obtained when the infusion was prepared with 2 g of mate tea, in 300 mL of water at 95 °C, under infusion for 16 min. The optimal conditions were applied for the preparation of beverages from 15 commercial samples of yerba mate tea, and it was observed that the sum of the concentration of the four compounds showed variation of up to 79 times between the average of the samples, which can be attributed to climatic conditions of cultivation of the plant and/or of processing.
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Ácido Clorogénico/aislamiento & purificación , Ilex paraguariensis/química , Ácido Quínico/análogos & derivados , Brasil , Ácido Clorogénico/análisis , Cromatografía Líquida de Alta Presión , Metanol , Hojas de la Planta/química , Tallos de la Planta/química , Ácido Quínico/análisis , Ácido Quínico/aislamiento & purificación , Tés de HierbasRESUMEN
Chlorogenic acid (5-O-caffeoylquinic acid) is a phenolic compound from thehydroxycinnamic acid family. This polyphenol possesses many health-promoting properties, mostof them related to the treatment of metabolic syndrome, including anti-oxidant, anti-inflammatory,antilipidemic, antidiabetic, and antihypertensive activities. The first part of this review will discussthe role of chlorogenic acid as a nutraceutical for the prevention and treatment of metabolicsyndrome and associated disorders, including in vivo studies, clinical trials, and mechanisms ofaction. The second part of the review will be dealing with the role of chlorogenic acid as a foodadditive. Chlorogenic acid has shown antimicrobial activity against a wide range of organisms,including bacteria, yeasts, molds, viruses, and amoebas. These antimicrobial properties can beuseful for the food industry in its constant search for new and natural molecules for thepreservation of food products. In addition, chlorogenic acid has antioxidant activity, particularlyagainst lipid oxidation; protective properties against degradation of other bioactive compoundspresent in food, and prebiotic activity. The combination of these properties makes chlorogenic acidan excellent candidate for the formulation of dietary supplements and functional foods.