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
Eleven new acyl-quinic acids (AQAs) 1a-9, and 18 known AQAs 10-27 were isolated from the root bark of Acanthopanax gracilistylus W. W. Smith (Acanthopanacis Cortex). The planar structures of 1a-9 were determined based on their HR-ESIMS, IR, and NMR data. The absolute configurations of 1a-6 were identified by comparing the experimental and the calculated electronic circular dichroism (ECD) spectra. This is the first report of the isolation of AQAs from Acanthopanacis Cortex. Notably, 1a-6 were determined as unusual oxyneolignan-(-)-quinic acids heterodimers, representing a new class of natural products. The inhibitory activities of 1a-27 on neutrophil elastase (NE) and cyclooxygenase-2 (COX-2) were studied in vitro, and the results indicated they possessed significant inhibitory activities on COX-2. Among them, the IC50 values of 1a-9 were 0.63±0.014, 0.75±0.028, 0.15±0.023, 0.63±0.016, 0.30±0.013, 35.63±4.600, 8.70±1.241, 16.51±0.480, 0.69±0.049, 0.39±0.017, and 0.26±0.080 µM, respectively. This study represents the inaugural disclosure of the anti-COX-2 constituents found in Acanthopanacis Cortex, thereby furnishing valuable insights into the exploration of novel COX-2 inhibitors derived from natural reservoirs.
Asunto(s)
Productos Biológicos , Eleutherococcus , Elastasa de Leucocito , Ciclooxigenasa 2 , Corteza de la Planta , Ácido QuínicoRESUMEN
Smilax brasiliensis Sprengel is a monocotyledon of the Smilacaceae family, native to the Brazilian Cerrado, popularly known as "salsaparrilha" or "japecanga". In this study, the ethanol extract (EE) and the hexane (HEXF), dichloromethane (DCMF), ethyl acetate (ACF), and hydroethanol (HEF) fractions of the stems were obtained. The chemical composition was determined, the contents of phenolic compounds and flavonoids were quantified, and the antioxidant potential and the cytotoxic effect on Artemia salina were evaluated. Fatty acid esters, hydrocarbons, and phytosterols were identified in the HEXF analyzed by gas chromatography - mass spectrometry (GC-MS). The EE and DCMF, ACF, and HEF were analyzed by liquid chromatography coupled to a diode array detector and mass spectrometer (LC-DAD-MS), and the identified constituents included glycosylated (rutin, 3-O-ß-galactopyranosyl quercetin, 3-O-ß-glucopyranosyl quercetin, O-deoxyhexosyl-hexosyl quercetin, O-deoxyhexosyl-hexosyl kaempferol, O-deoxyhexosyl-hexosyl O-methyl quercetin, and others), and non-glycosylated (quercetin) flavonoids, phenylpropanoids (3-O-E-caffeoyl quinic acid, 5-O-E-caffeoyl quinic acid, O-caffeoyl shikimic acid, and others), neolignan, steroidal saponin (dioscin), and N-feruloyltyramine. The EE, DCMF, and ACF showed high total contents of phenolic compounds (112.99, 175.71, and 524.02 µg of GAE/mg, respectively), and in the ACF and DCMF a great content of flavonoids was also quantified (50.08 and 31.49 µg of QE/mg, respectively). The EE, DCMF, ACF, and HEF exhibited great antioxidant potential by DPPH (IC50 1.71 - 32.83 µg/mL) and FRAP (IC50 0.63 - 6,71 µg/mL) assays. A maximum cytotoxic activity on A. salina of 60% was observed for the DCMF (LC50 = 856.17 µg/mL). This study contributes to the phytochemical study of S. brasiliensis since these compounds were identified for the first time in the stems of this species. The S. brasiliensis stems demonstrated to be a rich source of polyphenols compounds and exhibited high antioxidant potential without toxicity. Thus, extract and fractions obtained from the S. brasiliensis stems can be used in food supplements or as natural antioxidants in the food industry.
Asunto(s)
Smilacaceae , Smilax , Antioxidantes/análisis , Quercetina , Smilax/química , Ácido Quínico , Extractos Vegetales/química , Flavonoides/química , Fenoles/toxicidad , Fenoles/química , EtanolRESUMEN
BACKGROUND: Spent coffee grounds (SCGs) are a good source of chlorogenic acid (CGA), which can be hydrolyzed to quinic acid (QA) and caffeic acid (CA). These molecules have antioxidant and neuroprotective capacities, benefiting human health. The hydrolysis of CGA can be done by biotechnological processes, such as solid-state fermentation (SSF). This work evaluated the use of SSF with Aspergillus sp. for the joint release of the three molecules from SCGs. RESULTS: Hydroalcoholic extraction of the total phenolic compounds (TPCs) from SCGs was optimized, obtaining 28.9 ± 1.97 g gallic acid equivalent (GAE) kg-1 SCGs using 0.67 L ethanol per 1 L, a 1:9 solid/liquid ratio, and a 63 min extraction time. Subsequently, SSF was performed for 30 days, achieving the maximum yields for CGA, QA, and TPCs on the 16th day: 7.12 ± 0.01 g kg-1 , 4.68 ± 0.11 g kg-1 , and 54.96 ± 0.49 g GAE kg-1 respectively. CA reached its maximum value on the 23rd day, at 4.94 ± 0.04 g kg-1 . The maximum antioxidant capacity was 635.7 mmol Trolox equivalents kg-1 on the 14th day. Compared with unfermented SCGs extracts, TPCs and CGA increase their maximum values 2.3-fold, 18.6-fold for CA, 14.2 for QA, and 6.4-fold for antioxidant capacity. Additionally, different extracts' profiles were obtained throughout the SSF process, allowing us to adjust the type of enriched extract to be produced based on the SSF time. CONCLUSION: SSF represents an alternative to produce extracts with different compositions and, consequently, different antioxidant capacities, which is a potentially attractive fermentation process for different applications. © 2022 Society of Chemical Industry.
Asunto(s)
Antioxidantes , Café , Humanos , Café/química , Fermentación , Antioxidantes/química , Ácidos Cafeicos/química , Ácido Clorogénico/análisis , Ácido Quínico/análisis , Ácido Quínico/química , Fenoles , Extractos VegetalesRESUMEN
INTRODUCTION: Coffea arabica L. leaves are considered a by-product of the coffee industry however they are sources of several bioactive compounds. OBJECTIVES: This study aimed to evaluate the chemical composition and the in vitro antibacterial activity of the lyophilised ethanol extract of arabica coffee leaves (EE-CaL). MATERIAL AND METHODS: The chemical characterisation of EE-CaL was performed using ultra-performance liquid chromatography coupled to quadrupole time-of-flight mass spectrometry (UPLC-Q-ToF-MS/MS). The in vitro antibacterial effect of EE-CaL was evaluated using the broth microdilution method and the adapted drop plate agar method to determine the minimum inhibitory concentration (MIC) and the minimum bactericidal concentration (MBC), respectively. RESULTS: The chemical analysis of EE-CaL revealed the presence of compounds from the alkaloid class, such as trigonelline and caffeine, in addition to the phenolic compounds such as quinic acid, 5-caffeoylquinic acid, caffeic acid-O-hexoside, mangiferin, (epi)catechin, (epi)catechin monoglucoside and procyanidin trimer. Regarding the antibacterial potential, EE-CaL was active against Gram-positive and Gram-negative bacteria, being more effective against Escherichia coli (ATCC 25922) (MIC = 2500 µg/mL and bactericidal effect). CONCLUSION: The results of this research suggest that coffee leaves, a by-product, possess compounds with antibacterial properties. Thus, further studies with coffee leaf extracts must be carried out to relate the compounds present in the extract with the antibacterial activity and find the mechanisms of action of this extract against bacteria.
Asunto(s)
Alcaloides , Catequina , Coffea , Proantocianidinas , Agar/farmacología , Alcaloides/farmacología , Antibacterianos/análisis , Antibacterianos/farmacología , Cafeína/análisis , Cafeína/farmacología , Coffea/química , Etanol , Cromatografía de Gases y Espectrometría de Masas , Bacterias Gramnegativas , Bacterias Grampositivas , Extractos Vegetales/química , Ácido Quínico/análisis , Espectrometría de Masas en TándemRESUMEN
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
Copaifera langsdorffii L. is one of the most known medicinal species in Brazil. Its leaves are rich in phenolic compounds with potential biological activities as an antioxidant and chelating agent. This paper reports the isolation of four compounds from the hydroalcoholic extract of the leaves of C. langsdorffii and the investigation of their possible cytoprotective effects against heavy metal poisoning. Quercitrin (1), afzelin (2), 3,5-di-O-(3-O-methyl galloyl) quinic acid (3) and 4,5-di-O-(3-O-methyl galloyl) quinic acid (4), were associated with toxic doses of methylmercury and lead and evaluated by Alamar blue cell viability assays in HepG2 and PC12. The compounds displayed significant cytoprotective effect for the HepG2 cell line against both metals. Compounds 1-4 did not protect PC12 cells against methylmercury induced-cytotoxicity, but at lower concentrations, they protected against lead induced-cytotoxicity. The evaluated compounds showed a promising cytoprotection effect against exposure to heavy metals and should be further investigated as protective agents.
Asunto(s)
Fabaceae/química , Intoxicación por Metales Pesados/tratamiento farmacológico , Compuestos de Metilmercurio/antagonistas & inhibidores , Extractos Vegetales/farmacología , Sustancias Protectoras/aislamiento & purificación , Animales , Antioxidantes , Brasil , Línea Celular , Intoxicación por Metales Pesados/prevención & control , Humanos , Plomo/toxicidad , Intoxicación por Plomo/tratamiento farmacológico , Intoxicación por Plomo/prevención & control , Manósidos , Intoxicación por Mercurio/tratamiento farmacológico , Intoxicación por Mercurio/prevención & control , Compuestos de Metilmercurio/toxicidad , Fenoles , Hojas de la Planta/química , Proantocianidinas , Sustancias Protectoras/farmacología , Quercetina/análogos & derivados , Ácido Quínico , RatasRESUMEN
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 Bromeliaceae Puya chilensis Mol. is a native monocotyledonous food plant that can be found in central Chile. It is traditionally known as chagual. The tender basal part of the leaves, just starting from the meristem, are consumed as a salad. The aim of this work was to describe the phenolic content and composition of the meristem and leaves of chagual, as well as their antioxidant capacity and inhibitory activity against metabolic syndrome-associated enzymes. Samples of chagual, including two cultivated and three wild growing plants, were analyzed and compared for composition and bioactivity. From the phenolic enriched extract of the plant (PEE), 26 compounds were tentatively identified by HPLC-DAD-ESI-MSn, including 12 hydroxycinnamic acids and 14 flavonoids. The main compounds were identified as diferuloyl hexaric acid isomers and 5-p-Coumaroylquinic acid. The compounds were quantified in both meristem and leaves. The PEE content was up to ten times higher in the meristem than in the leaves, ranging from 0.18 to 124.08â¯mg/g PEE. The samples inhibited α-glucosidase, but did not show effect on α-amylase and pancreatic lipase. This is the first report on the polyphenol composition and bioactivity of the edible components of the chagual food plant.