chlorogenic-acid and caffeic-acid

Single servings of coffee beverage containing low (412 μmol), medium (635 μmol) and high (795 μmol) amounts of chlorogenic acids were administered to eleven healthy volunteers in a double-blind randomised controlled trial. Analysis of plasma and urine collected for 24 h revealed the presence of 12 metabolites in plasma and 16 metabolites in urine, principally in the form of sulphates, and to a lesser extent glucuronides of caffeic, ferulic, dihydrocaffeic and dihydroferulic acids, as well as intact feruloylquinic and caffeoylquinic acids, and sulphated caffeoylquinic acid lactones. Median values of peak plasma concentrations after increasing doses of chlorogenic acids were 1088, 1526 and 1352 nM. In urine the median amounts of metabolites excreted after 24 h following consumption of the three coffees were 101, 160 and 125 μmol, accounting for 24%, 25% and 16% of the doses ingested. Peak plasma concentration and urinary excretion values showed trends towards a reduced bioavailability of chlorogenic acids associated with the highest dose ingested, when expressed as percentages of intake. Potential biomarkers of coffee intake were identified as feruloylquinic acids and sulphated caffeoylquinic acid lactones in plasma and urine with positive moderate to strong coefficients of determination for peak plasma concentrations (0.60-0.81) and amounts excreted in urine (0.36-0.73) (P < 0.05).

Topics: Adult; Biological Availability; Caffeic Acids; Chlorogenic Acid; Chromatography, High Pressure Liquid; Coffee; Coumaric Acids; Cross-Over Studies; Dose-Response Relationship, Drug; Double-Blind Method; Female; Glucuronides; Healthy Volunteers; Humans; Male; Quinic Acid; Young Adult

Mume Fructus (MF) is processed from the near-ripe fruit of Prunus mume (Siebold) Siebold & Zucc by drying at low temperature until the color turns black. MF is often used in Chinese medicine for the treatment of chronic diarrhea and dysentery. Previous studies have shown that the active components of MF against Crohn's disease (CD) are mainly citrate and hydroxycinnamate derivatives, which can alleviate the CD-induced inflammatory response and intestinal barrier damage. However, their molecular mechanisms on CD still need further elucidation.. To investigate the protective effects and underlying mechanisms of citrate and hydroxycinnamate derivatives in MF on intestinal epithelial injury.. Network pharmacology technology was used to predict the anti-CD targets and molecular mechanisms of 4 citrate and 11 hydroxycinnamate derivative prototypes and 5 hydroxycinnamate derivative metabolites in the 40% ethanol fraction of MF (MFE40), the active anti-CD ingredient group of MF. Lipopolysaccharide (LPS)-treated IEC-6 cells were used to investigate the effects of the above components on the proliferation of damaged IEC-6 cells and to verify the molecular mechanism of their regulation on the FAK/PI3K/AKT signaling pathways for the promotion of the proliferation of IEC-6 cells.. A "compound-target-pathway" network was constructed based on network pharmacology analysis, including 20 citrate and hydroxycinnamate derivatives that target 316 core proteins and 36 CD-related pathways, of which PI3K-AKT pathway and focal adhesion were the most enriched pathways. Further cell validation experiments showed that 1 citric acid (CA) compound and 10 hydroxycinnamate derivatives, including 3-O-caffeoylquinic acid (3CQA), 4-O-caffeoylquinic acid (4CQA), 5-O-caffeoylquinic acid (5CQA), caffeic acid (CFA), p-coumaric acid (PCMA), m-coumaric acid (MCMA), ferulic acid (FUA), isoferulic acid (IFUA), 3-hydroxyphenylpropionic acid (3HPPA) and hippuric acid (HPP), could promote the proliferation of IEC-6 cells and inhibit the damage of LPS to IEC-6 cells. Ethyl caffeate (ECFA), a hydroxycinnamic acid derivative, had no effect on promoting the proliferation of IEC-6 cells and was weak in inhibiting the damage of IEC-6 cells caused by LPS. Further mechanistic verification experiments showed that 7 citrate and hydroxycinnamate derivatives (CA, CFA, 3CQA, MCMA, FUA, 3HPPA, and HPP) could upregulate the expression of p-FAK, p-PI3K, and p-AKT proteins. Among them, CA had the better effect on activating the FAK-PI3K-AKT signaling pathway.. Citrate and hydroxycinnamate derivatives in MF can ameliorate LPS-induced intestinal epithelial cell injury to demonstrate potential for Crohn's disease alleviation. This protective effect can be achieved by upregulating FAK/PI3K/AKT pathway.

Topics: Citric Acid; Crohn Disease; Epithelial Cells; Fruit; Lipopolysaccharides; Phosphatidylinositol 3-Kinases; Proto-Oncogene Proteins c-akt; Signal Transduction

3',4'-Dihydroxycinnamic acid (aka caffeic acid) is a common dietary component found in a variety of plant-derived food products either in a free form or esterified as in chlorogenic acids such as 5-

Topics: Caffeic Acids; Chlorogenic Acid; Colon; Feces; Fermentation; Humans; Hydroxybenzoates; Microbiota; Quinic Acid

Phytochemical investigations of

Topics: Antioxidants; Biosynthetic Pathways; Caffeic Acids; Chamomile; Chlorogenic Acid; Ethylenes; Matricaria; Phenols; Phenylalanine Ammonia-Lyase; Plant Extracts; Plant Leaves; Polyphenols; Quinic Acid; Stress, Physiological

This study aims to give an unprecedented contribution on the chemical composition and bioactivities of the most produced and appreciated Portuguese fig variety ("Pingo de Mel") with the view of expanding the knowledge on its potentialities. An advanced characterization of its peel and pulp parts was carried out. Four free sugars (glucose, fructose, trehalose and sucrose), 5 organic acids (oxalic, quinic, malic, citric, and succinic acids), tocopherols in all their 4 forms, besides 23 fatty acids were detected in the samples. Fifteen different phenolic components were found in the peel hydroethanolic extract; whereas 12 were detected in the pulp hydroethanolic extract. Quercetin-3-O-rutinoside (rutin) was the major constituent of the peel, accounting for 33.8% of its phenolic content, followed by 5-O-caffeoylquinic acid and vanillic acid malonyl di-deoxyhexoside. Caffeic acid derivatives, such as caffeic acid hexosides, were the major components of pulp, followed by vanillic acid derivatives and O-caffeoylquinic acid. Both extracts displayed promising antioxidant capacities in all methods used, namely the 2,2-diphenyl-1-picrylhydrazyl radical-scavenging, the reducing power, the inhibition of β-carotene bleaching assays, the thiobarbituric acid reactive substances assay and the oxidative haemolysis inhibition assay; however, the peel presented significantly lower IC

Topics: Anti-Bacterial Agents; Antioxidants; Caffeic Acids; Chlorogenic Acid; Chromatography, High Pressure Liquid; Ficus; Food Analysis; Fruit; Methicillin-Resistant Staphylococcus aureus; Microbial Sensitivity Tests; Nutritive Value; Phytochemicals; Polyphenols; Portugal; Quinic Acid; Rutin; Tocopherols

To characterise bioactive phenolics and confirm anti-inflammatory indicators in Porana sinensis stem, 23 phenolics were identified by UPLC-QTOF-MS/MS from crude extract (CE) prepared optimally with 80% methanol. Further fractionalisation using D101 macroporous resin resulted in predominant enrichment of total phenols and flavonoids into Fr.II. Correspondingly, the bioactive components-enriched Fr.II exhibited the lowest IC

Topics: Animals; Anti-Inflammatory Agents; Antioxidants; Caffeic Acids; Cell Line; Chromatography, High Pressure Liquid; Convolvulaceae; Flavonoids; Lipopolysaccharides; Mice; Phenols; Plant Extracts; Quinic Acid; RAW 264.7 Cells; Tandem Mass Spectrometry

A green and efficient microemulsion liquid chromatographic (MELC) method using fatty acid as co-surfactant and electrochemical detection was established and validated for the determination of four caffeoylquinic acid isomers and caffeic acid in honeysuckle samples. The influences of each individual component within the isocratic oil-in-water (O/W) microemulsion mobile phase were systematically investigated, such as the type and concentration of co-surfactant, concentration of sodium dodecyl sulphate (SDS), organic modifier addition, type and concentration of oil phase, pH and detection voltage. Results indicated that excellent resolution was achieved using 3.0% w/v of propionic acid, 0.5% w/v of ethyl acetate, 1.0% w/v of SDS, 5% w/v acetonitrile, 90.5% v/v of water and 25 mM sodium dihydrogen phosphate at pH = 3 as microemulsion mobile phase and 0.8 V as the optimal voltage value. Under the optimal condition, analytical performance of developed method was evaluated. The detection limits were below 17.3 ng/mL and intra-day and inter-day precisions by relative standard deviations (RSD%) were between 0.5% and 3.6%. Satisfactory recovery (in the range of 83.8-109.1%) with good repeatability lower than 4.7% (n = 3) was obtained. Therefore, the developed O/W MELC method was rapid, precise and accurate for simultaneous determination of neochlorogenic acid, chlorogenic acid, isochlorogenic acid A and isochlorogenic acid C in honeysuckle samples, with contents of 2.6, 28.7, 18.1 and 5.2 mg/g, respectively.

Topics: Caffeic Acids; Chromatography, Liquid; Emulsions; Fatty Acids; Isomerism; Limit of Detection; Lonicera; Molecular Structure; Quinic Acid; Surface-Active Agents

Topics: Caffeic Acids; Chlorogenic Acid; Chromatography, Liquid; Coffea; Coffee; Coumaric Acids; Emulsions; Hydrophobic and Hydrophilic Interactions; Magnetic Resonance Spectroscopy; Plant Oils; Quinic Acid; Surface Tension; Surface-Active Agents; Tandem Mass Spectrometry; Viscosity

We aim to determine the chemical constituents of Yinchen extract and Yinchen herbs using high-performance liquid chromatography coupled with diode array detection and high-resolution mass spectrometry. The method was developed to analyze of eight organic acid components of Yinchen extract (including neochlorogenic acid, chlorogenic acid, cryptochlorogenic acid, caffeic acid, 1,3-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid and 4,5-dicaffeoylquinic acid). The separation was conducted using an Agilent TC-C18 column with acetonitrile - 0.2% formic acid solution as the mobile phases under gradient elution. The analytical method was fully validated in terms of linearity, sensitivity, precision, repeatability as well as recovery, and subsequently the method was performed for the quantitative assessment of Yinchen extracts and Yinchen herbs. In addition, the changes of selected markers were studied when Yinchen herbs decocting in water and isomerization occurred between the chlorogenic acids. The proposed method enables both qualitative and quantitative analyses and could be developed as a new tool for the quality evaluation of Yinchen extract and Yinchen herbs. The changes of selected markers in water decoction process could give us some novel idea when studying the link between substances and drug efficacy.

Topics: Acids; Artemisia; Caffeic Acids; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Mass Spectrometry; Quinic Acid

Yerba maté is widely consumed in South America as different beverages, such as maté tea (roasted leaves) and chimarrão (green dried leaves), and linked to health benefits, mainly attributed to chlorogenic acids (CGAs). Health effects of CGAs depend on their bioavailability, but such data are scarce. The aim of this study was to investigate the distribution of CGAs and metabolites in tissues, hepatic and plasmatic kinetic profile and urinary excretion after ingestion of maté tea or 5-caffeoylquinic acid (5-CQA).. Wistar rats ingested maté tea (MT) or 5-CQA (ST) and were killed after 1.5 h for tissue distribution analysis (pilot study) or at 0.5, 1, 2, 4 and 8 h for liver and plasma kinetics (main experiment). Urine was collected in metabolic cages. Biological samples were analyzed by UPLC-DAD-MS with and without incubation with β-glucuronidase and sulfatase.. CGAs and metabolites were detected in all tissues. Caffeic acid was the main compound in plasma up to 2 h after ingestion of maté tea, while 5-CQA predominated in ST group. Concentration of microbial metabolites increased 4 h after gavage and reached higher amounts in MT plasma and liver, when compared to ST group. Approximately 4.0 % of compounds ingested by MT and 3.3 % by ST were recovered in urine up to 8 h after the gavage.. The study confirms that not only absorption, but also metabolization of CGAs begins in stomach. There were differences in compounds formed from maté tea or isolated 5-CQA, showing that CGAs profile in food may influence qualitatively and quantitatively the metabolites formed in the body.

Topics: Animals; Biological Availability; Caffeic Acids; Chlorogenic Acid; Ilex paraguariensis; Plant Extracts; Plant Leaves; Polyphenols; Quinic Acid; Rats; Rats, Wistar; South America; Teas, Herbal

Geigeria alata is a traditional plant used in Sudanese folk medicine for treatment of diabetes, cough, epilepsy and intestinal complaints.. To analyze phenolic acids in Geigeria alata roots and leaves and to evaluate their antioxidant and antimicrobial activities.. Phenolic acids in the aqueous-methanol extracts were identified by LC-MS. Major compounds were isolated using low-pressure liquid chromatography. The quantitative analysis of phenolic acids was performed by a validated HPLC-UV method with limits of detection ranging from 0.04 to 0.57 μg/mL. 2,2-Diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azinobis-(3-ethylbenzothiazine-6-sulphonic acid) (ABTS) and ferric reducing antioxidant power (FRAP) methods were used for antioxidant activity evaluation. In addition, the minimal inhibitory concentration and the minimal bactericidal concentration against a panel of pathogenic bacteria and fungi were determined by the broth microdilution test.. For the first time protocatechuic, caffeic, p-coumaroylquinic, caffeoylsinapoylquinic, caffeoylferuloylquinic, three feruloylquinic, six caffeoylquinic acids, and a caffeic acid hexoside were detected in Geigeria alata roots by LC-MS. HPLC-UV analyses showed that 3,5-dicaffeoylquinic acid (25.96 ± 2.08 mg/g dry weight (DW)) was the most abundant phenolic acid in roots, while 4,5-dicaffeoylquinic acid (8.99 ± 0.56 mg/g DW) was the main compound present in leaves. 3,5-Dicaffeoylquinic acid demonstrated stronger radical scavenging activity and reducing power compared with the crude extracts and the positive control 5-caffeoylquinic acid. 3,4,5-Tricaffeoylquinic acid revealed the highest antibacterial potential against the penicillin sensitive and resistant Staphylococcus aureus strains, as well as methicillin-resistant S. aureus.. The caffeoylquinic acids content of up to 6.22% in Geigeria alata roots establishes this species as a new source rich in these bioactive molecules. Copyright © 2016 John Wiley & Sons, Ltd.

Topics: Anti-Infective Agents; Antioxidants; Caffeic Acids; Chlorogenic Acid; Chromatography, High Pressure Liquid; Chromatography, Liquid; Flavonoids; Geigeria; Mass Spectrometry; Methicillin-Resistant Staphylococcus aureus; Microbial Sensitivity Tests; Plant Extracts; Plant Leaves; Plant Roots; Plants, Medicinal; Polyphenols; Quinic Acid

To investigate the chemical constituents from Xanthium mongolicum.. The constituents were isolated and purified by silicagel,Sephadex LH-20 column chromatography. Their structures were identified on the basis of spectral data and physiochemical characteristics.. Ten compounds were isolated and identified as hexadecanoic acid( 1), methyl 3, 4-dihydroxybenzoate ( 2), protocatechuic aldehyde( 3), caffeic acid methyl ester( 4), vanillic acid( 5), 4-hydroxybenzoic acid( 6), caffeic acid ethyl ester( 7), chlorogenic acid( 8), caffeic acid( 9), 3, 4-di-O-caffeoylquinic acid( 10).. Compounds 1 ~ 5,7 and 10 are isolated from this plant for the first time.

Topics: Caffeic Acids; Chlorogenic Acid; Hydroxybenzoates; Parabens; Quinic Acid; Vanillic Acid; Xanthium

Ilex paraguariensis (maté) is one of the best sources of chlorogenic acids (CGA) in nature. When leaves are toasted, some isomers are partly transformed into 1,5-γ-quinolactones (CGL). Both CGA and CGL are important contributors to the brew's flavor and are thought to contribute to human health. In this study, we quantified 9 CGA, 2 CGL, and caffeic acid in 20 samples of dried green and toasted maté that are commercially available in Brazil. Total CGA content in green maté varied from 8.7 to 13.2 g/100 g, dry weight (dw). Caffeic acid content varied from 10.8 to 13.5 mg/100 g dw, respectively. Content in toasted maté varied from 1.5 to 4.6 g/100 g and from 1.5 to 7.2 mg/100 g dw, respectively. Overall, caffeoylquinic acid isomers (CQA) were the most abundant CGA in both green and toasted maté, followed by dicaffeoylquinic acids (diCQA) and feruloylquinic acids (FQA). These classes accounted for 58.5%, 40.0%, and 1.5% of CGA, respectively, in green maté and 76.3%, 20.7%, and 3.0%, respectively, in toasted maté. Average contents of 3-caffeoylquinolactone (3-CQL) and 4-caffeoylquinolactone (4-CQL) in commercial toasted samples were 101.5 mg/100 g and 61.8 mg/100 g dw, respectively. These results show that, despite overall losses during the toasting process, CGA concentrations are still substantial in toasted leaves, compared to other food sources of CGA and phenolic compounds in general. In addition to evaluating commercial samples, investigation of changes in CGA profile and formation of 1,5-γ-quinolactones was performed in experimental maté toasting.

Topics: Brazil; Caffeic Acids; Chlorogenic Acid; Food Handling; Health Promotion; Hot Temperature; Humans; Ilex paraguariensis; Plant Leaves; Quinic Acid

Chlorogenic acid is a well known natural product with important bioactivities. It contains an ester bond formed between the COOH of caffeic acid and the 3-OH of quinic acid. We synthesized a chlorogenic acid analogue, 3α-caffeoylquinic acid amide, using caffeic and quinic acids as starting materials. The caffeoylquinc acid amide was found to be much more stable than chlorogenic acid and showed anti-Hepatitis C virus (anti-HCV) activity with a potency similar to chlorogenic acid. The caffeoylquinc acid amide potently protected HepG2 cells against oxidative stress induced by tert-butyl hydroperoxide.

Topics: Amides; Antioxidants; Caffeic Acids; Chlorogenic Acid; Esters; Hepatitis C; Humans; Oxidative Stress; Quinic Acid; Reactive Oxygen Species; tert-Butylhydroperoxide

Artichoke is a rich source of health promoting compounds such as polyphenols, important for their pharmaceutical and nutritional properties. In this study, the potential for bioavailability of the artichoke polyphenols was estimated by using both in vitro digestion and Caco-2 human intestinal cell models. In vitro digestive recoveries (bio-accessibility) were found to be 55.8% for total artichoke phenolics and in particular, 70.0% for chlorogenic acid, 41.3% for 3,5-O-dicaffeoylquinic acid, and 50.3% for 1,5-O-dicaffeoylquinic acid, highlighting potential sensitivity of these compounds to gastric and small intestinal digestive conditions. Uptake of artichoke polyphenols was rapid with peak accumulation occurring after 30 min with an efficiency of 0.16%, according to the poor uptake of dietary polyphenols. Some compounds, such as coumaric acid, caffeic acid and caffeic acid derivatives, were also detected in the basolateral side assuming extra and intracellular esterase activities on chlorogenic acid. Only apigenin-7-O-glucoside was transported through the Caco-2 monolayer demonstrating its bioavailability to the extent of 1.15% at 60 min. In addition, permeability coefficient (Papp = 2.29 × 10(-5) cm s(-1)), involving apical to basolateral transport of apigenin 7-O-glucoside, was calculated to facilitate estimation of transport through the Caco-2 monolayer. Finally, the mono and dicaffeoylquinic acids present in artichoke heads exert an antioxidant activity on the human low density lipoprotein system correlated to their chemical structure. In conclusion, the utilized in vitro models, although not fully responding to the morphological and physiological features of human in vivo conditions, could be a useful tool for investigating mechanistic effects of polyphenols released from the food matrix.

Topics: Antioxidants; Biological Availability; Caco-2 Cells; Caffeic Acids; Chlorogenic Acid; Coumaric Acids; Cynara scolymus; Gastrointestinal Tract; Humans; Intestinal Mucosa; Intestines; Lipid Metabolism; Plant Extracts; Polyphenols; Quinic Acid

Colorectal cancer is a major cause of morbidity and mortality throughout the world. Issues related to the role of diet in cancer prevention and treatment are featured each year, and, in this context, consumption of hydroxycinanmic acids is associated with reduced risk of chronic diseases including cancer. Therefore, the aim of this study was to evaluate the cellular uptake of caffeic and 5-caffeoylquinic acids and their effects on cell viability, cell cycle, and apoptosis in human colon adenocarcinoma cells (HT-29). HT-29 cells were incubated with different concentrations of caffeic and 5-caffeoylquinic acids (1.25 µM to 80.0 µM) from 0.5 to 96 h. Cellular uptake was analyzed by HPLC and LCMS. Cell viability, cell cycle, and apoptosis was measured, respectively, using MTT method and flow cytometry. Caffeic and 5-caffeoylquinic acids are absorbed, isomerized, and metabolized by HT-29 cells. Both compounds were able to reduce HT-29 cell viability, promoting specific changes in the cell cycle and increased the apoptosis rate. Caffeic acid and 5-caffeoylquinic acid showed inhibitory effects on cell growth, suggesting a modulation of the cell cycle with an increase in apoptosis in human colon adenocarcinoma cells.

Topics: Adenocarcinoma; Apoptosis; Caffeic Acids; Cell Cycle; Cell Survival; Colonic Neoplasms; HT29 Cells; Humans; Quinic Acid

The purpose of this study was to investigate the effect of repeated harvesting on the content of caffeic acid (CA) and seven species of caffeoylquinic acids (CQAs) in sweet potato leaves using a newly developed high-performance liquid chromatography method. Six cultivars and two breeding lines were used in this study. Leaves were collected at monthly intervals from 1st harvest (May) to 4th harvest (August) in 2011 and 2012. ANOVA analysis revealed that the contents of CQAs were significantly different among all cultivars and breeding lines, but no significant differences were found for CA. No annual variation was confirmed in CA and CQAs. Repeated harvest of sweet potato leaves affected the content of only 4-CQA and 5-CQA. Post-hoc comparisons using Tukey's method indicated that the contents of 4-CQA and 5-CQA in sweet potato leaves harvested at first time were significantly higher compared to those at the other harvest times.

Topics: Caffeic Acids; Ipomoea batatas; Plant Extracts; Plant Leaves; Quinic Acid

The study aims to develop a unified method to determine seven phenolic acids (neochlorogenic acid, chlorogenic acid, 4-caffeoylquinic acid, caffeic acid, isochlorogenic acid B, isochlorogenic acid A and isochlorogenic acid C) contained in honeysuckle flower that is the monarch drug of all the eight Yinqiao Jiedu serial preparations using quantitative analysis of multi-components by single-marker (QAMS). Firstly, chlorogenic acid was used as a reference to get the average relative correction factors (RCFs) of the other phenolic acids in ratios to the reference; columns and instruments from different companies were used to validate the durability of the achieved RCFs in different levels of standard solutions; and honeysuckle flower extract was used as the reference substance to fix the positions of chromatographic peaks. Secondly, the contents of seven phenolic acids in eight different Yinqiao Jiedu serial preparations samples were calculated based on the RCFs durability. Finally, the quantitative results were compared between QAMS and the external standard (ES) method. The results have showed that the durability of the achieved RCFs is good (RSD during 0.80% - 2.56%), and there are no differences between the quantitative results of QAMS and ES (the relative average deviation < 0.93%). So it can be successfully used to the quantitative control of honeysuckle flower principally prescribed in Yinqiao Jiedu serial preparations.

Topics: Caffeic Acids; Chlorogenic Acid; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Flowers; Hydroxybenzoates; Lonicera; Quinic Acid

The experiment's aim was to optimize the processing technology of Xanthii Fructus which through comparing the difference of UPLC fingerprint and contents of toxicity ingredient in water extract of 16 batches of processed sample. The determination condition of UPLC chromatographic and contents of toxicity ingredient were as follows. UPLC chromatographic: ACQUITY BEH C18 column (2.1 mm x 100 mm, 1.7 microm) eluted with the mobile phases of acetonitrile and 0.1% phosphoric acidwater in gradient mode, the flow rate was 0.25 mL x min(-1) and the detection wavelength was set at 327 nm. Contents of toxicity ingredient: Agilent TC-C18 column (4.6 mm x 250 mm, 5 microm), mobile phase was methanol-0.01 mol x L(-1) sodium dihydrogen phosphate (35: 65), flow rate was 1.0 mL x min(-1), and detection wavelength was 203 nm. The chromatographic fingerprints 16 batches of samples were analyzed in using the similarity evaluation system of chromatographic, fingerprint of traditional Chinese medicine, SPSS16.0 and SIMCA13.0 software, respectively. The similarity degrees of the 16 batches samples were more than 0.97, all the samples were classified into four categories, and the PCA showed that the peak area of chlorogenic acid, 3,5-dicaffeoylquinic acid and caffeic acid were significantly effect index in fingerprint of processed Xanthii Fructus sample. The outcome of determination showed that the toxicity ingredient contents of all samples reduced significantly after processing. This method can be used in optimizing the processing technology of Xanthii Fructus.

Topics: Caffeic Acids; Chemistry, Pharmaceutical; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Quinic Acid; Xanthium

A single-laboratory validation study was conducted on an HPLC method for the detection and quantification of caffeic acid (CA) and seven species of caffeoylquinic acids (CQAs) in lyophilized sweet potato leaves. The procedure for extraction of the analytes from the matrix and the HPLC conditions for the efficient separation of CA and CQAs were optimized. In the proposed method, a relative response factor to one of the CQAs (5-CQA) was used to quantify the others. The method performed well in terms of precision when carried out on five different days and demonstrated Horwitz ratio (HorRat) scores ranging from 0.5 to 1.0 for all analytes, which were well within the limits of performance acceptability. Accuracy testing at three levels showed an overall recovery of 94% when duplicated on five different days. Moreover, a stability study revealed that all analytes in both standard solution and sample extract were stable for 28 days.

Topics: Caffeic Acids; Chromatography, High Pressure Liquid; Flavonoids; Freeze Drying; Ipomoea batatas; Molecular Structure; Plant Extracts; Plant Leaves; Quinic Acid; Reference Standards; Reproducibility of Results; Sensitivity and Specificity

The metabolomic differences in phenolics from leaves derived from 3 artichoke cultivars (Cynara scolymus): American Green Globe, French Hyrious and Egyptian Baladi, collected at different developmental stages, were assessed using UHPLC-MS coupled to chemometrics. Ontogenic changes were considered as leaves were collected at four different time intervals and positions (top and basal) during artichoke development. Unsupervised principal component analysis (PCA) and supervised orthogonal projection to latent structures-discriminant analysis (O2PLS-DA) were used for comparing and classification of samples harvested from different cultivars at different time points and positions. A clear separation among the three investigated cultivars was revealed, with the American Green Globe samples found most enriched in caffeic acid conjugates and flavonoids vs. other cultivars. Furthermore, these metabolites also showed a marked effect on the discrimination between leaf samples from cultivars harvested at different positions, regardless of the plant age. Metabolite absolute quantifications further confirmed that discrimination was mostly influenced by phenolic compounds, namely caffeoylquinic acids and flavonoids. This study demonstrates an effect of artichoke leaf position, regardless of plant age, on its secondary metabolites composition. To the best of our knowledge, this is the first report for compositional differences among artichoke leaves, based on their positions, via a metabolomic approach and suggesting that top positioned artichoke leaves present a better source of caffeoylquinic acids, compared to basal ones.

Topics: Antioxidants; Caffeic Acids; Chromatography, High Pressure Liquid; Cynara scolymus; Egypt; Fatty Acids; Flavonoids; Nuclear Magnetic Resonance, Biomolecular; Plant Leaves; Quinic Acid; Saponins

The aim was to develop a high performance liquid chromatography method for simultaneous determination of five organic acids in Kudiezi injection. The Diamonsil C18 column (4.6 mm x 200 mm, 5 microm) was adopted with acetonitrile and water as the mobile phase at a gradient mode program. The flow rate was 1.0 mL min-1 , detection wavelength was 325 nm, and column temperature was 35 degree C. The linear range of monocaffeyltartaric acid, chlorogenic acid, caffeic acid, ferulic acid, and chicoric acid were 0. 64-81.60 (r =0. 999 9),0.09-11. 10 (r =0.999 8) ,0.09-11.30 (r =0. 999 8),0.10-12.80 (r =0.999 9),0.43-55. 50 mg L-1 (r = 0.999 8) , respectively. The average recoveries were 101.8% ,100. 9% ,99. 24% ,99. 83% ,101.9%, respectively, with RSD of less than 2.0%. The developed HPLC method was simple, sensitive and accurate with good repeatability. This work provided helpful information for comprehensive quality control of Kudiezi injection. [Key words] Kudiezi injection; organic acids; content determination; HPLC

Topics: Caffeic Acids; Chlorogenic Acid; Chromatography, High Pressure Liquid; Coumaric Acids; Drugs, Chinese Herbal; Quinic Acid; Succinates

The quality and grade of traditional Chinese medicinal herbs were assessed by their characteristics traditionally. According to traditional experience, the quality of the purple Flos Farfarae is better than that of yellow buds. NMR-based metabolomic approach combined with significant analysis of microarray (SAM) and Spearman rank correlation analysis were used to investigate the different metabolites of the Flos Farfarae with different color feature. Principal component analysis (PCA) showed clear distinction between the purple and yellow flower buds of Tussilago farfara. The S-plot of orthogonal PLS-DA (OPLS-DA) and t test revealed that the levels of threonine, proline, phosphatidylcholine, creatinine, 4, 5-dicaffeoylquinic acid, rutin, caffeic acid, kaempferol analogues, and tussilagone were higher in the purple flower buds than that in the yellow buds, in agreement with the results of SAM and Spearman rank correlation analysis. The results confirmed the traditional medication experience that "purple flower bud is better than the yellow ones", and provide a scientific basis for assessing the quality of Flos Farfarae by the color features.

Topics: Caffeic Acids; Color; Creatinine; Flowers; Kaempferols; Magnetic Resonance Spectroscopy; Metabolomics; Phosphatidylcholines; Plants, Medicinal; Principal Component Analysis; Proline; Quinic Acid; Rutin; Sesquiterpenes; Threonine; Tussilago

5-Caffeoylquinic acid (5-CQA) is generally referred to as chlorogenic acid and exhibits various biological activities such as antioxidant activity and porcine pancreas α-amylase inhibitory activities. 5-CQA may be useful as an antioxidant for food and to prevent diabetes and obesity. The degradation of 5-CQA and caffeic acid (CA) in an aqueous solution at 37 °C and pH 5.0-9.0 was studied. The degradation of 5-CQA and CA, demonstrating time and pH dependence (i.e., the rate constant, k, was higher at higher pH), was satisfactorily described by the Weibull equation. The stability of 5-CQA at pH 7.4 and 9.0 was improved by adding (-)-epigallocatechin gallate (EGCG) and ascorbic acid (AA). Moreover, the degradation of 5-CQA in the presence of EGCG or AA could be described by the Weibull equation. The k value in the presence of EGCG or AA was dependent on their concentration.

Topics: Ascorbic Acid; Caffeic Acids; Catechin; Chlorogenic Acid; Drug Stability; Hydrogen-Ion Concentration; Kinetics; Quinic Acid

In our previous paper, we reported that rosmarinic acid (1) of Argusia argentea could neutralize snake venom induced hemorrhagic action. Rosmarinic acid (1) consists of two phenylpropanoids: caffeic acid (2) and 3-(3,4-dihydroxyphenyl)lactic acid (3). In this study, we investigated the structural requirements necessary for inhibition of snake venom activity through the use of compounds, which are structurally related to rosmarinic acid (1). By examining anti-hemorrhagic activity of cinnamic acid analogs against Protobothrops flavoviridis (Habu) venom, it was revealed that the presence of the E-enoic acid moiety (-CH=CH-COOH) was critical. Furthermore, among the compound tested, it was concluded that rosmarinic acid (1) (IC(50) 0.15 μM) was the most potent inhibitor against the venom.

Topics: Animals; Antivenins; Caffeic Acids; Cinnamates; Crotalid Venoms; Depsides; Hemorrhage; Humans; Male; Mice; Rosmarinic Acid; Snakes; Structure-Activity Relationship

Apples are the most widely consumed fruits in Germany and various other countries. Positive health effects of apple-derived polyphenols in vivo depend on their absorption, metabolism, distribution, and elimination from the body after consumption. Data on the metabolism of these polyphenols in humans are scarce. In order to study the intestinal transit and metabolism of apple polyphenols in humans, a variety of experiments were carried out.. Polyphenols were incubated with saliva (for 5 min), simulated gastric or duodenal juice (4 or 10 h, respectively), or rat hepatocytes (4 h) under aerobic conditions, and with ileostomy fluid under aerobic conditions for 10 h. The polyphenol profile in human serum (8 h later) and renal elimination in urine (24 h later) were also investigated after consumption of 1 L apple juice. Polyphenols and their metabolites were identified and quantified by high-performance liquid chromatography with diode array detection (HPLC-DAD), HPLC-electrospray ionization-tandem mass spectrometry (ESI-MS/MS), and gas chromatography (GC)-MS.. In the presence of native saliva or ileostomy fluid, β-glycosides of phloretin and quercetin were hydrolyzed, to varying degrees depending on the sugar moiety, and to much lesser degrees in the presence of antibiotics. In the gastric milieu, almost complete degradation of procyanidin B(2) to (-)-epicatechin was observed. In the presence of artificial duodenal juice flavan-3-ol epimerization occurred. Quercetin was completely converted to phloroglucinol, 3,4-dihydroxybenzoic acid, and 2,4,6-trihydroxybenzoic acid. Formation of isomeric products of hydroxycinnamic acid esters and their corresponding methyl esters was also observed, and similar results were obtained after incubation with rat hepatocytes. Products of phase II metabolism, two phloretin O-glucuronides and eight (methyl) quercetin O-glucuronides, were identified in the hepatocyte samples. Following enzymatic hydrolysis, 5-caffeoylquinic acid, 4-p-coumaroylquinic acid, caffeic acid, (-)-epicatechin, phloretin, and quercetin were recovered in both serum and urine (5.3% and 3.5% of the amounts consumed, respectively). In addition, 19.5% of the polyphenols consumed were identified in the urine in the form of hydroxylated phenolic and hippuric acids.. The findings relating to the absorption, metabolism, and systemic availability of polyphenols in vivo should contribute to our understanding of their biological effects, and the characterization of newly formed metabolites should facilitate further studies.

Topics: Adult; Animals; Beverages; Biflavonoids; Caffeic Acids; Catechin; Chromatography, Gas; Chromatography, High Pressure Liquid; Coumaric Acids; Female; Gastrointestinal Transit; Hepatocytes; Humans; Ileostomy; Intestinal Mucosa; Male; Malus; Phloretin; Polyphenols; Proanthocyanidins; Quercetin; Quinic Acid; Rats; Rats, Wistar; Saliva; Tandem Mass Spectrometry; Young Adult

The infusion of aerial parts of Ilex paraguariensis is widely consumed. Its antioxidant activity suggests an important role of this plant in the treatment/prevention of oxidative stress related diseases. Plant extract active compounds are frequently found in esterified form that may be poorly absorbed. Hydrolysis of the extract is a possible approach to increase its bioavailability. The aim of this study was to perform a phytochemical analysis and evaluate in rats the plasma concentration and tissue distribution of antioxidant compounds in the hydroethanolic extract of Ilex paraguariensis, before and after enzymatic hydrolysis. Both extracts presented high antioxidant activity and phenolic content. Rats given single or repeated doses of the hydrolyzed extract showed increased plasma antioxidant activity and higher plasma levels of caffeic acid. However, no changes of endogenous antioxidants were observed. In conclusion, hydrolysis of the extract of Ilex paraguariensis is a strategy to improve its bioavailability and in vivo antioxidant activity.

Topics: Animals; Antioxidants; Caffeic Acids; Ethanol; Hydrolysis; Ilex paraguariensis; Male; Phenols; Plant Extracts; Plant Leaves; Quinic Acid; Rats; Rats, Wistar; Water

New derivatives of caffeic acid and quinic acid were synthesized and their anti-fungal and inhibitory activities on fungal 1,3-β-glucan synthase were determined in comparison with those of the corresponding chlorogenic acid derivatives. All the chlorogenic, quinic and caffeic acid derivatives that were coupled with an H(2)N-orn-4-(octyloxy) aniline group (1, 1b and 1c) displayed potent activities in both anti-fungal and inhibition of 1,3-glucan synthase assays. Compounds 1 and 1c inhibited the fungal membrane enzyme with the potency comparable to that of a known 1,3-β-D-glucan synthase inhibitor, aculeacin A. The results revealed that the anti-fungal activity of the chlorogenic acid derivative with a free amino group was at least partly due to inhibition of the fungal 1,3-β-glucan synthase. These results suggest that further investigation on caffeic acid derivatives may lead to the discovery of novel anti-fungal agents with drug-like properties.

Topics: Antifungal Agents; Caffeic Acids; Candida albicans; Enzyme Inhibitors; Glucosyltransferases; Microbial Sensitivity Tests; Molecular Structure; Quinic Acid; Stereoisomerism; Structure-Activity Relationship

In this work the bioactive metabolic profile, the antioxidant activity and total phenolic content of burdock (Arctium lappa) seeds, leaves and roots were obtained. TEAC values and total phenolic content for hydro-alcoholic extracts of burdock ranged from 67.39 to 1.63 micromol Trolox equivalent/100g dry weight (DW), and from 2.87 to 45 g of gallic acid equivalent/100g DW, respectively. Phytochemical compounds were analyzed by liquid chromatography coupled to electrospray tandem mass spectrometry (LC/MS/MS) in negative mode. The main compounds of burdock extracts were caffeoylquinic acid derivatives, lignans (mainly arctiin) and various flavonoids. The occurrence of some phenolic acids (caffeic acid, chlorogenic acid and cynarin) in burdock seeds; arctiin, luteolin and quercetin rhamnoside in burdock roots; phenolic acids, quercetin, quercitrin and luteolin in burdock leaves was reported for the first time.

Topics: Antioxidants; Arctium; Caffeic Acids; Chlorogenic Acid; Chromatography, Liquid; Cinnamates; Furans; Glucosides; Luteolin; Phenols; Plant Extracts; Plant Leaves; Plant Roots; Quercetin; Quinic Acid; Seeds; Spectrometry, Mass, Electrospray Ionization; Tandem Mass Spectrometry

Epidemiological studies suggest that coffee can reduce the risk of degenerative diseases such as diabetes type 2, cardiovascular disease and cancer. These beneficial effects have partly been attributed to the antioxidant activity of coffee. We determined composition and antioxidant potential of differentially roasted coffee extracts and investigated the impact of selected original constituents and roast products.. Parameters studied were direct antioxidant activity (trolox equivalent antioxidant capacity/oxygen radical absorbing capacity), cellular reactive oxygen species (ROS) level, DNA damage and protein expression of NAD(P)H: quinone oxidoreductase, γ-glutamylcysteine ligase and glutathione reductase in HT-29/Caco-2 cells at 24-h incubation. All extracts showed distinct direct antioxidant activity: medium roasts>light roast AB1 (caffeoylquinic acid (CQA)-rich Arabica Brazil extract); dark roast AB2 (N-methylpyridinium (NMP)-rich Arabica Brazil extract), and diminished t-butylhydroperoxide-induced ROS level in HT-29 cells (AB2>medium roasts>AB1). NAD(P)H:quinone oxidoreductase 1 expression and γ-glutamylcysteine ligase expression were distinctly induced by AB1 and 5-CQA, but not by AB2 and NMP. 5-CQA and caffeic acid exhibited highest trolox equivalent antioxidant capacity/oxygen radical absorbing capacity values (5-CQA: 1.3/3.5 mM and caffeic acid: 1.3/3.9 mM trolox); ROS level was distinctly diminished by 5-CQA (≥3 μM), catechol (30 μM) and trigonelline (≥30 μM), whereas menadione-induced DNA damage in Caco-2 cells was reduced by NMP compounds (1-30 μM).. The results emphasize that both original constituents and roast products contribute to the cellular antioxidant effectiveness of coffee.

Topics: Antioxidants; Caco-2 Cells; Caffeic Acids; Cell-Free System; Coffee; Colon; DNA Damage; Glutamate-Cysteine Ligase; Glutathione Reductase; HT29 Cells; Humans; NAD(P)H Dehydrogenase (Quinone); Plant Extracts; Pyridinium Compounds; Quinic Acid; Reactive Oxygen Species; tert-Butylhydroperoxide

In the light of known HDAC inhibitors, 33 carboxylic acid derivatives were tested to understand the structural requirements for HDAC inhibition activity. Several modifications were applied to develop the structure-activity relationships of carboxylic acid HDAC inhibitors. HDAC inhibition activities were investigated in vitro by using HeLa nuclear extract in a fluorimetric assay. Molecular docking was also carried out for the human HDAC8 enzyme in order to predict inhibition activity and the 3D poses of inhibitor-enzyme complexes. Of these compounds, caffeic acid derivatives such as chlorogenic acid and curcumin were found to be highly potent compared to sodium butyrate, which is a well-known HDAC inhibitor.

Topics: Caffeic Acids; Carboxylic Acids; Catalytic Domain; Chlorogenic Acid; Curcumin; Enzyme Inhibitors; HeLa Cells; Histone Deacetylase Inhibitors; Histone Deacetylases; Humans; Models, Molecular; Molecular Structure; Protein Binding

Caffeic acid and 5-caffeoylquinic acid are naturally occurring phenolic acid and its quinic acid ester found in plants. In this article, potential effects of 5-caffeoylquinic acid and caffeic acid on P-selectin expression were investigated due to its significant involvement in platelet activation. First, the effects of 5-caffeoylquinic acid and caffeic acid on cyclooxygenase (COX) enzymes were determined due to their profound involvement in regulating P-selectin expression on platelets. At the concentration of 0.05 microM, 5-caffeoylquinic acid and caffeic acid were both able to inhibit COX-I enzyme activity by 60% (P<.013) and 57% (P<.017), respectively. At the same concentration, 5-caffeoylquinic acid and caffeic acid were also able to inhibit COX-II enzyme activity by 59% (P<.012) and 56% (P<.015), respectively. As expected, 5-caffeoylquinic acid and caffeic acid were correspondingly able to inhibit P-selectin expression on the platelets by 33% (P<.011) and 35% (P<.018), at the concentration of 0.05 microM. In animal studies, 5-caffeoylquinic acid and caffeic acid orally administered to mice were detected as intact forms in the plasma. Also, P-selectin expression was respectively reduced by 21% (P<.016) and 44% (P<.019) in the plasma samples from mice orally administered 5-caffeoylquinic acid (400 microg per 30 g body weight) and caffeic acid (50 microg per 30 g body weight). These data suggest that both 5-caffeoylquinic acid and caffeic acid orally administered can be absorbed and suppress P-selectin expression on mouse platelets.

Topics: Administration, Oral; Animals; Blood Platelets; Caffeic Acids; Cyclooxygenase Inhibitors; Mice; P-Selectin; Quinic Acid

Bee products (including propolis, royal jelly, and bee pollen) are popular, traditional health foods. We compared antioxidant effects among water and ethanol extracts of Brazilian green propolis (WEP or EEP), its main constituents, water-soluble royal jelly (RJ), and an ethanol extract of bee pollen.. The hydrogen peroxide (H2O2)-, superoxide anion (O2.-)-, and hydroxyl radical (HO.)- scavenging capacities of bee products were measured using antioxidant capacity assays that employed the reactive oxygen species (ROS)-sensitive probe 5-(and-6)-chloromethyl-2',7'-dichlorodihydrofluorescein diacetate, acetyl ester (CM-H2DCFDA) or aminophenyl fluorescein (APF).. The rank order of antioxidant potencies was as follows: WEP > EEP > pollen, but neither RJ nor 10-hydroxy-2-decenoic acid (10-HDA) had any effects. Concerning the main constituents of WEP, the rank order of antioxidant effects was: caffeic acid > artepillin C > drupanin, but neither baccharin nor coumaric acid had any effects. The scavenging effects of caffeic acid were as powerful as those of trolox, but stronger than those of N-acetyl cysteine (NAC) or vitamin C.. On the basis of the present assays, propolis is the most powerful antioxidant of all the bee product examined, and its effect may be partly due to the various caffeic acids it contains. Pollen, too, exhibited strong antioxidant effects.

Topics: Acetylcysteine; Animals; Ascorbic Acid; Bees; Caffeic Acids; Chromans; Cinnamates; Coumaric Acids; Fatty Acids; Fatty Acids, Monounsaturated; Free Radical Scavengers; Phenylpropionates; Plant Extracts; Pollen; Propolis; Quinic Acid; Trichothecenes

The medical mechanism against type I allergies is to block the release or production of chemical mediators from mast cells or to block the H(1)-receptor signaling. We previously reported that the anti-allergic action of the dry powder from Bidens pilosa L. var. radiata SCHERFF treated with the enzyme cellulosine (eMMBP) was dependent on the inhibition of histamine release from mast cells. Here, we investigate that the effect of fractions in eMMBP on the histamine-induced contraction in guinea pig ileum and on the release of histamine in rat peritoneal mast cells. The histamine-induced contraction in guinea pig ileum is dose-dependently inhibited by ketotifen, an antagonist of H(1)-receptor. Fractions contained caffeic acid, caffeoylquinic acid and fractions contained flavonoids such as hyperin and isoquercitrin in eMMBP inhibit histamine release from mast cells, but only flavonoids such as hyperin, isoquercitrin and rutin suppress the histamine-induced contraction in guinea pig ileum. Moreover, the histamine-induced contraction was not affected by caffeic acid, however, such contraction was significantly inhibited by rutin. These results suggest that the primary antagonists of H(1)- receptor are different from the components in eMMBP that inhibit histamine release, and that these components participate in the anti-allergic activity of eMMBP.

Topics: Animals; Anti-Allergic Agents; Bidens; Caffeic Acids; Cells, Cultured; Drugs, Chinese Herbal; Flavonoids; Guinea Pigs; Histamine H1 Antagonists; Histamine Release; Ileum; In Vitro Techniques; Male; Mast Cells; Muscle Contraction; Muscle, Smooth; Quinic Acid; Rats; Rats, Wistar

To establish a method for determination of chlorogenic acid, caffeic acid, caffeoylquinic acid and ScuteIlarin in Dengzhan Xixin injection.. The HPLC method was carried out on Agilent Zorbax SB-C18 column (150 mm x 4. 6 mm, 5 pim) evaluated with acetonitrile-0.1% formic acid as mobile phase, gradient elution; the flow rate was 1.0 mL x min(-1); the temperatue of column was at 35 degrees C; the detection wavelength was at 335 nm for UV detection.. The calibration curves were linear in the range of 0.025 to 0.800 microg (r = 0.9990) for chlorogenic acid, 0.027 to 0.850 microg (r = 0.9999) for caffeic acid, 0.062 to 1.978 microg (r = 0.9997) for caffeoylquinic acid and 0.118 to 3.770 microg (r = 0.9999) for scutellarin,respectilely. The average recoveries were 97.19% with RSD 1.16%; 100.45% with RSD 1.16%; 97.32% with RSD 1.43% and 103.81% with RSD 0.70%, respectively.. The assay demonstrated that the method was simple, it had adequate accuracy and selectivity to quantify the four active components in Dengzhan Xixin injection.

Topics: Apigenin; Caffeic Acids; Chlorogenic Acid; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Glucuronates; Quinic Acid; Reproducibility of Results

Chlorogenic acids (CGA) are cinnamic acid derivatives with biological effects mostly related to their antioxidant and antiinflammatory activities. Caffeoylquinic acids (CQA) and dicaffeoylquinic acids (diCQA) are the main CGA found in nature. Because green coffee is a major source of CGA, it has been used for production of nutraceuticals. However, data on the bioavailability of CGA from green coffee in humans are inexistent. The present study evaluated the pharmacokinetic profile and apparent bioavailability of CGA in plasma and urine of 10 healthy adults for 8 h after the consumption of a decaffeinated green coffee extract containing 170 mg of CGA. Three CQA, 3 diCQA, and caffeic, ferulic, isoferulic, and p-coumaric acids were identified in plasma by HPLC-Diode Array Detector-MS after treatment. Over 30% (33.1 +/- 23.1%) of the ingested cinnamic acid moieties were recovered in plasma, including metabolites, with peak levels from 0.5 to 8 h after treatment. CGA and metabolites identified in urine after treatment were 4-CQA, 5-CQA, and sinapic, p-hydroxybenzoic, gallic, vanillic, dihydrocaffeic, caffeic, ferulic, isoferulic, and p-coumaric acids, totaling 5.5 +/- 10.6% urinary recovery of the ingested cinnamic and quinic acid moiteties. This study shows that the major CGA compounds present in green coffee are highly absorbed and metabolized in humans.

Topics: Adult; Biological Availability; Caffeic Acids; Caffeine; Chlorogenic Acid; Cinnamates; Coffee; Coumaric Acids; Female; Humans; Male; Middle Aged; Propionates; Quinic Acid; Young Adult

The incorporation of chlorogenic acids (CGAs) and their subunits quinic and caffeic acids (QA and CA) in coffee brew melanoidins was studied. Fractions with different molecular weights, ionic charges, and ethanol solubilities were isolated from coffee brew. Fractions were saponified, and the released QA and CA were quantified. For all melanoidin fractions, it was found that more QA than CA was released. QA levels correlated with melanoidin levels, indicating that QA is incorporated in melanoidins. The QA level was correlated with increasing ionic charge of the melanoidin populations, suggesting that QA may contribute to the negative charge and consequently is, most likely, not linked via its carboxyl group. The QA level correlated with the phenolic acid group level, as determined by Folin-Ciocalteu, indicating that QA was incorporated to a similar extent as the polyphenolic moiety from CGA. The QA and CA released from brew fractions by enzymes confirmed the incorporation of intact CGAs. Intact CGAs are proposed to be incorporated in melanoidins upon roasting via CA through mainly nonester linkages. This complex can be written as Mel=CA-QA, in which Mel represents the melanoidin backbone, =CA represents CA nonester-linked to the melanoidin backbone, and -QA represents QA ester-linked to CA. Additionally, a total of 12% of QA was identified in coffee brew, whereas only 6% was reported in the literature so far. The relevance of the additional QA on coffee brew stability is discussed.

Topics: Caffeic Acids; Chlorogenic Acid; Chromatography, Ion Exchange; Coffea; Coffee; Coumaric Acids; Hot Temperature; Molecular Weight; Polymers; Quinic Acid; Seeds

Although chlorogenic acid (CHA) easily reaches a millimolar level in the gastrointestinal tract because of its high concentration in coffee and fruits, its effects on intestinal epithelial cells have been little reported. We investigated in this study the down-regulative effects of 5-caffeoylquinic acid (CQA), the predominant isomer of CHA, on the H(2)O(2-) or TNF-alpha-induced secretion of interleukin (IL)-8, a central pro-inflammatory chemokine involved in the pathogenesis of inflammatory bowel diseases, in human intestinal epithelial Caco-2 cells. After the cells had been pre- and simultaneously treated with CQA, the oversecretion of IL-8 and overexpression of its mRNA induced by H(2)O(2) were significantly suppressed in a dose-dependent manner in the range of 0.25-2.00 mmol/L. We further found that a metabolite of CQA, caffeic acid (CA), but not quinic acid, significantly inhibited the H(2)O(2)-induced IL-8 secretion and its mRNA expression in the same dose-dependent manner. Both CQA and CA suppressed the TNF-alpha-induced IL-8 secretion as well. Caffeic acid at 2.00 mmol/l was able to absolutely block the H(2)O(2)- or TNF-alpha-induced oversecretion of IL-8 in Caco-2 cells. However, CQA and CA did not suppress the TNF-alpha-induced increase in the IL-8 mRNA expression, indicating that the suppressive mechanisms are different between TNF-alpha-induced and H(2)O(2)-induced IL-8 production models. These results suggest that the habit of drinking coffee and/or eating fruits with a high CHA content may be beneficial to humans in preventing the genesis of inflammatory bowel diseases.

Topics: Caco-2 Cells; Caffeic Acids; Gene Expression; Humans; Hydrogen Peroxide; Interleukin-8; Intestinal Mucosa; Intestines; Oxidative Stress; Quinic Acid; RNA, Messenger; Tumor Necrosis Factor-alpha

The methanol extract from Dipsacus asper Wall (Dipsacaceae) was found to show antioxidant activity against free radical and Cu(2+)-mediated LDL oxidation. In further study, to identify active constituents from the plant, six caffeoyl quinic acid derivatives: 3,4-di-O-caffeoylquinic acid (1), methyl 3,4-di-O-caffeoyl quinate (2), 3,5-di-O-caffeoylquinic acid (3), methyl 3,5-di-O-caffeoyl quinate (4), 4,5-di-O-caffeoylquinic acid (5) and methyl 4,5-di-O-caffeoyl quinate (6) were isolated. Their structures were identified by spectroscopic methods including 2D-NMR. The isolated compounds, 1-6, were found to be potent scavengers of the free radical 1,1-diphenyl-2-picrylhydrazyl (DPPH), and are more potent than butylated hydroxyl toluene (BHT) used as a positive control. The compounds 1-6 also inhibited Cu(2+)-mediated low-density lipoprotein (LDL) oxidation. They increased the lag time of conjugated dienes formation and inhibited the generation of thiobarbituric acid reactive substances (TBARS) in a dose-dependent manner. These results suggested that Dipsacus asper due to its antioxidant constituents, 1-6, may have a role to play in preventing the development and progression of atherosclerotic disease.

Topics: alpha-Tocopherol; Antioxidants; Biphenyl Compounds; Butylated Hydroxytoluene; Caffeic Acids; Chlorogenic Acid; Copper; Dipsacaceae; Dose-Response Relationship, Drug; Free Radical Scavengers; Gallic Acid; Humans; Hydrazines; Lipid Peroxidation; Lipoproteins, LDL; Malondialdehyde; Methanol; Molecular Structure; Monosaccharides; Picrates; Plant Extracts; Plant Roots; Plants, Medicinal; Quinic Acid; Thiobarbituric Acid Reactive Substances

The fragmentation behavior of all six dicaffeoylquinic acids (diCQA) has been investigated using LC-MS(4). It is possible to discriminate between each of the isomers including those for which commercial standards are not available. For diCQA, the ease of removal of the caffeoyl residue during fragmentation is 1 approximately = 5 > 3 > 4. The distinctive fragmentation observed for the little-studied 1,4-dicaffeoylquinic acid involves elimination of the C1 caffeoyl residue, repeated dehydrations leading to the aromatization of the quinic acid moiety, and its decarboxylation. It is suggested that this process is initiated by the C1 carboxyl protonating the C5 hydroxyl in the inverted chair conformer, followed by its protonating the C1 caffeoyl residue in the favored chair conformation. The fragmentation of 1-caffeoylquinic acid is indistinguishable from that of the commercially available 5-caffeoylquinic acid, but these two isomers can be distinguished easily by their facile chromatographic resolution on reversed phase packings. The hierarchical key previously developed for characterizing chlorogenic acids has been extended to accommodate 1-caffeoylquinic acid and the 1-acyl dicaffeoylquinic acids.

Topics: Caffeic Acids; Chromatography, Liquid; Isomerism; Magnetic Resonance Spectroscopy; Mass Spectrometry; Molecular Conformation; Molecular Structure; Quinic Acid

The effect of a koji (Aspergillus awamori mut.) extract on the caffeoylquinic acid derivatives purified from sweetpotato (Ipomoea batatas L.) leaves was examined to develop the mass production of caffeic acid. A koji extract hydrolyzed the caffeoylquinic acid derivatives, chlorogenic acid, 3,4-di-O-caffeoylquinic acid, 3,5-di-O-caffeoylquinic acid, 4,5-di-O-caffeoylquinic acid and 3,4,5-tri-O-caffeoylquinic acid, to caffeic acid. Furthermore, the koji extract also converted the major polyphenolic components from sweetpotato, burdock (Arctium lappa L.), and mugwort (Artemisia indica var. maximowiczii) leaves to caffeic acid. These results suggest that the production of caffeic acid from plant resources containing caffeoylquinic acid derivatives is possible.

Topics: Aspergillus; Caffeic Acids; Hydrolysis; Ipomoea batatas; Plant Leaves; Quinic Acid

Specific antioxidant activity (SAA) (i.e., activity related to the molar or gallic acid equivalent amount of antioxidant) of natural polyphenolic mixtures or pure phenolic compounds was studied using their capacity to delay the conjugated diene production brought about by in vitro LDL copper-mediated or AAPH-mediated oxidation. The cinnamic acid series (caffeic, sinapic, ferulic acids) displayed a constant SAA over a large range of concentrations, whereas the benzoic acid series (gallic and protocatechuic acids) showed much higher SAA at low concentrations. The natural phenolic mixtures had a constant SAA. The highest SAA was obtained with caffeoyl esters (caffeoylquinic, rosmarinic, and caffeoyltartaric acids) and catechin for the copper-oxidation and the AAPH-oxidation system, respectively. Phenolic mixtures and acids delayed vitamin E depletion and decreased proinflammatory lysophosphatidylcholine production. As with polyphenols, probucol delayed lysophosphatidylcholine and conjugated dienes production, at higher concentrations, but was not effective at preventing vitamin E depletion. Polyphenols prevent the oxidation of LDL and its constituents (vitamin E, phosphatidylcholine), which is compatible with an antiinflammatory and antiatherosclerotic role in pathophysiological conditions.

Topics: Antioxidants; Caffeic Acids; Humans; Inflammation Mediators; Lipoproteins, LDL; Lysophosphatidylcholines; Oxidation-Reduction; Phenols