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At least 145 records · Page 8Linked to original sources
PubMed2005

[Chlorogenic acid content comparison of different processed products of Ilex hainanensis Merr].

OBJECTIVE: To control different processed products of Ilex hainanensis Merr quality. METHODS: Using HPLC to determine chlorogenic acid of Ilex hainanensis Merr. Measure wavelength is 327 nm. RESULTS: The linear range of chlorogenic acid was good from 0.84 microg to 5.04 microg (r = 0.9996). The average recovery was 100.46% (RSD = 1.33%). CONCLUSION: This method is convenient, fast, accurate, can be applied to quality control of the different processed products of Ilex hainanensis Merr.

Chlorogenic Acid↗
PubMed2001

Identification and antioxidant activity of novel chlorogenic acid derivatives from bamboo (Phyllostachys edulis).

One known and two novel antioxidant compounds have been isolated from bamboo (Phyllostachys edulis). The butanol-soluble extract of the bamboo leaves was found to have a significant antioxidant activity, as measured by scavenging the stable 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical and the superoxide anion radical (O(2)(-)) in the xanthine/xanthine oxidase assay system. Antioxidant activity-directed fractionation of the extract led to the isolation and characterization of three structural isomeric chlorogenic acid derivatives: 3-O-(3'-methylcaffeoyl)quinic acid (1), 5-O-caffeoyl-4-methylquinic acid (2), and 3-O-caffeoyl-1-methylquinic acid (3). Compounds 2 and 3 were isolated and characterized for the first time from the natural products. In the DPPH scavenging assay as well as in the iron-induced rat microsomal lipid peroxidation system, compounds 2 (IC(50) = 8.8 and 19.2 microM) and 3 (IC(50) = 6.9 and 14.6 microM) showed approximately 2-4 times higher antioxidant activity than did chlorogenic acid (IC(50) = 12.3 and 28.3 microM) and other related hydroxycinnamates such as caffeic acid (IC(50) =13.7 and 25.5 microM) and ferulic acid (IC(50) = 36.5 and 56.9 microM). Among the three compounds, compound 1 yielded the weakest antioxidant activity, and the DPPH scavenging and lipid peroxidation inhibitory activity (IC(50) = 16.0 and 29.8 microM) was lower than those of chlorogenic and caffeic acids. All three compounds exhibited both superoxide scavenging activities and inhibitory effects on xanthine oxidase. Their superoxide anion (O(2)(-)) scavenging activities (IC(50) = 1, 4.3 microM; 2, 2.8 microM; and 3, 1.2 microM) were markedly stronger than those of ascorbic acid (IC(50) = 56.0 microM), alpha-tocopherol (IC(50) > 100 microM), and other test compounds, although their inhibition effects on xanthine oxidase may contribute to the potent scavenging activity. alpha-Tocopherol exerted a significant inhibitory effect (65.5% of the control) on superoxide generation in 12-O-tetradecanoylphorbol-13-acetate-induced human promyelocytic leukemia HL-60 cells, and compound 3 showed moderate activity (36.0%). On the other hand, other compounds including 1, 2, chlorogenic acid, and other antioxidants were weakly active (24.8-10.1%) in the suppression of superoxide generation.

Animals↗
PubMed2003

[Determination of chlorogenic acid and eriodictyol-7-O-beta-D-glucuronide in Pyrrosia by RP-HPLC].

AIM: To develop a method for determination of chlorogenic acid and eriodictyol-7-O-beta-D-glucuronide in Pyrrosia of different species and different places of origin by RP-HPLC. METHODS: Chromatography was performed using a C18 column with mobile phase of methanol-water-phosphoric acid (50:200:0.2). The monitoring wavelength was 284 nm. RESULTS: The linear ranges were 0.01-5.0 micrograms (r = 0.9997) and 0.004-5.0 micrograms (r = 0.9997), the recoveries were 97.1% (n = 8, RSD = 2.7%) and 98.8% (n = 9, RSD = 2.5%) for chlorogenic acid and eriodictyol-7-O-beta-D-glucuronide, respectively. CONCLUSION: The method was employed to the analysis of 21 samples of Pyrrosia. The contents of compounds vary greatly depending on the species used, place of collection and time of harvesting. The HPLC method is sensitive, rapid and can be used to control the quality of Pyrrosia and to guide reasonable season of harvesting.

Chlorogenic Acid↗
PubMed2003

Simultaneous determination of chlorogenic acid, forsythin and arctiin in Chinese traditional medicines preparation by reversed phase-HPLC.

A reversed phase (RP)-HPLC method was established for simultaneous determination of chlorogenic acid, arctiin and forsythin in Yinqiao Jiedu Granules, which was a commonly used Chinese herbal medical preparation for treatment of rheum ailments. The determination was based on a gradient elution (A: 1% acetic acid, pH=3.0, B: methanol) on a C18 column and an automatic wavelength switching program, where 325 nm was used for chlorogenic acid and 280 nm for arctiin and forsythin, respectively. Good linearities were obtained over the range of 2-200 mg.l(-1) for the 3 objective compounds. The spike recoveries were within 96.0-97.9%.

Bridged Bicyclo Compounds, Heterocyclic↗
PubMed2006

A gradient HPLC method for the quality control of chlorogenic acid, linarin and luteolin in Flos Chrysanthemi Indici suppository.

The Flos Chrysanthemi Indici suppository, a famous traditional Chinese medicine, is marketed for the treatment of prostatitis and chronic pelvic inflammation. A simple, relatively rapid and accurate high-performance liquid chromatographic (HPLC) method was applied to the simultaneous determination of chlorogenic acid, linarin and luteolin in Flos Chrysanthemi Indici suppository. The good separation was achieved on a Hypersil ODS column by a gradient elution using the mixture of acetonitrile and aqueous 1.0% acetic acid as mobile phase within 23 min. The method was validated for three active phenolic compounds with the relative standard deviations (R.S.D.) of intra- and inter-day precision below 3.0%, and the detection limits (S/N=3) of chlorogenic acid, linarin and luteolin were 0.32, 0.08 and 0.05 microg ml(-1), respectively. This assay was successfully applied to the determination of three active phenolic compounds in Flos Chrysanthemi Indici suppository samples with the quantitative recoveries in the range of 94.7-101.8%. The results indicate that the developed HPLC method can be readily utilized as a quality control method for Flos Chrysanthemi Indici suppository and its related traditional Chinese medicinal preparations.

Acetic Acid↗
PubMedDate not supplied

Mutagenicity studies on irradiated potatoes and chlorogenic acid; micronucleus test in rats.

The micronucleus test was used to study possible mutagenic effects of (1) Irradiated potatoes extracted (a) immediately and (b) after 24-h storage following irradiation; (2) Irradiated and unirradiated chlorogenic acid; and (3) Trenimon. It was observed that irradiated potatoes (groups 1 a, b) and chlorogenic acid (group 2) did not cause mutagenic effects in the bone-marrow cells of rats. The Trenimon group (group 3), which was used as the positive control group, did show significant mutagenic effects.

Animals↗
PubMed2004

Transepithelial transport of chlorogenic acid, caffeic acid, and their colonic metabolites in intestinal caco-2 cell monolayers.

Both chlorogenic and caffeic acids exhibited nonsaturable transport in Caco-2 cells, whereas caffeic acid also showed proton-coupled polarized absorption. Thus, the absorption efficiency of caffeic acid was greater than that of chlorogenic acid. Polarized transport of caffeic acid was inhibited by substrates of MCT such as benzoic and acetic acids. Almost all of the apically loaded chlorogenic and caffeic acid was retained on the apical side, and the transepithelial flux was inversely correlated with the paracellular permeability of Caco-2 cells. These results indicate that transport was mainly via paracellular diffusion, although caffeic acid was absorbed to a lesser extent by the monocarboxylic acid transporter (MCT). Furthermore, m-coumaric acid and 3-(m-hydroxyphenyl)propionic acid, the main metabolites of chlorogenic and caffeic acid by colonic microflora, competitively inhibited the transport of fluorescein, a known substrate of MCT. This suggests that their absorption could also be mediated by MCT. These findings have exemplified the physiological importance of MCT-mediated absorption in both phenolic acids per se and their colonic metabolites.

Biological Transport↗
PubMed2000

Induction of cytotoxicity by chlorogenic acid in human oral tumor cell lines.

Millimolar concentrations of chlorogenic acid (CGA) showed higher cytotoxic activity against human oral squamous cell carcinoma (HSC-2) and salivary gland tumor (HSG) cell lines, as compared with that against human gingival fibroblast (HGF). The cytotoxic activity of CGA was significantly reduced by catalase or CoCl2, but not affected by FeCl3 or CuCl2. ESR spectroscopy showed that higher (millimolar) concentrations of CGA produced radicals under alkaline conditions, acting as a prooxidant, whereas lower concentrations of CGA scavenged superoxide and hydroxyl radical. CGA produced large DNA fragments (as identified by slightly faster migrating band of DNA on agarose gel electrophoresis) and nuclear condensation (as demonstrated by Hoechst (No. 33258) staining) in tumor cell lines. Activation of caspase was demonstrated by staining with M30 monoclonal antibody, which reacts with degradation products of cytokeratin 18. Contact with CGA for at least 6 h was necessary for irreversible cytotoxicity induction. Pretreatment of the cells with caspase 3 inhibitor partially inhibited the cytotoxic action of CGA. These date suggest that CGA induces cytotoxicity in oral tumor cell lines, possibly by hydrogen peroxide-mediated oxidation mechanism.

Anticarcinogenic Agents↗
PubMed2003

Coffee acutely modifies gastrointestinal hormone secretion and glucose tolerance in humans: glycemic effects of chlorogenic acid and caffeine.

BACKGROUND: Accumulating evidence suggests that certain dietary polyphenols have biological effects in the small intestine that alter the pattern of glucose uptake. Their effects, however, on glucose tolerance in humans are unknown. OBJECTIVE: The objective was to investigate whether chlorogenic acids in coffee modulate glucose uptake and gastrointestinal hormone and insulin secretion in humans. DESIGN: In a 3-way, randomized, crossover study, 9 healthy fasted volunteers consumed 25 g glucose in either 400 mL water (control) or 400 mL caffeinated or decaffeinated coffee (equivalent to 2.5 mmol chlorogenic acid/L). Blood samples were taken frequently over the following 3 h. RESULTS: Glucose and insulin concentrations tended to be higher in the first 30 min after caffeinated coffee consumption than after consumption of decaffeinated coffee or the control (P < 0.05 for total and incremental area under the curve for glucose and insulin). Glucose-dependent insulinotropic polypeptide secretion decreased throughout the experimental period (P < 0.005), and glucagon-like peptide 1 secretion increased 0-120 min postprandially (P < 0.01) after decaffeinated coffee consumption compared with the control. Glucose and insulin profiles were consistent with the known metabolic effects of caffeine. However, the gastrointestinal hormone profiles were consistent with delayed intestinal glucose absorption. CONCLUSIONS: Differences in plasma glucose, insulin, and gastrointestinal hormone profiles further confirm the potent biological action of caffeine and suggest that chlorogenic acid might have an antagonistic effect on glucose transport. Therefore, a novel function of some dietary phenols in humans may be to attenuate intestinal glucose absorption rates and shift the site of glucose absorption to more distal parts of the intestine.

Adult↗
PubMed1982

Catalysis of nitrosation in vitro and in vivo in rats by catechin and resorcinol and inhibition by chlorogenic acid.

Measurements were made of the effects of phenolic compounds, some of which are present in the human diet, on the nitrosation of proline by nitrite to give N-nitrosoproline (NPRO). In vitro, resorcinol, catechin, p-nitrosophenol and phenol were catalysts and chlorogenic acid an inhibitor; guaiacol showed a marginal catalytic effect. Both the catalytic and the inhibiting effects were dependent on pH and on the concentration of phenolic compounds; catalysis by resorcinol and catechin was increased at optimal ratios of [nitrite]: [phenolic compound]. Endogenous nitrosation was examined in vivo by co-administration of nitrite, proline and a phenolic compound to rats and by monitoring the amount of NPRO excreted in the urine. Under similar experimental conditions, the catalytic effects observed in vivo decreased in the same order as those observed in vitro: resorcinol greater than p-nitroso-phenol greater than catechin greater than phenol greater than or equal to guaiacol; chlorogenic acid acted as an inhibitor. Catalysis and inhibition of N-nitrosation in rats in vivo appears to occur via mechanisms similar to those in vitro, although the effects in vivo were smaller. The implications of our findings for the endogenous formation of N-nitroso compounds and for variations in exposure due to different dietary constituents in humans are discussed.

Animals↗
PubMed2004

Simultaneous analysis of theanine, chlorogenic acid, purine alkaloids and catechins in tea samples with the help of multi-dimension information of on-line high performance liquid chromatography/electrospray-mass spectrometry.

A reverse phase high performance liquid chromatography (RP-HPLC) separation coupled with photo diode array detection (DAD) and electrospray ionization mass spectrometry (ESI-MS) detection was established for the analyzing of multiple bioactive compounds in tea and tea extracts. Theanine, chlorogenic acid, purine alkaloids and catechins were identified with authentic standard compounds and with MS-spectra. The content of theanine and catechins was measured by employing DAD and caffeine, chlorogenic acid, theobromine and theopylline by protonated molecular ion on selective ion recording (SIR) mode. The unity of LC/ESI-MS provides more qualitative and quantitative information comparing with general HPLC in the analysis of multi-components in tea, and complex extraction or sample pretreatment is unnecessary. The chromatogram acquired by using this method can be used as a bioactive components fingerprint for the quality control of tea and its extracts. With the help of multi-dimension information of HPLC-DAD-ESIMS, the compounds owning different chemical structure such as amino acid, catechins, etc. in tea and its extracts could be identified and determined in one run successfully.

Alkaloids↗
PubMed2001

Discrimination of Brazilian arabica green coffee samples by chlorogenic acid composition.

Coffee is basically consumed for the pleasure given by its taste and aroma, that is, the quality and acceptance of the coffee beverage are directly related to its sensorial characteristics. Thus, nowadays coffee quality is basically evaluated by sensorial analysis. However, together with this kind of analysis, it should be important to have available more objective chemical methods to assess coffee quality. One possible approach could be based on the analysis of chlorogenic acids (CGA), since they are considered precursors of coffee flavour and pigments during roasting. In the present work, high performance liquid chromatography (HPLC) analysis of chlorogenic acids was applied to six different Brazilian arabica green coffee samples which were previously characterised by sensorial analysis. The results showed the potential to correlate the chemical data, evaluated by the Principal Components Analysis (PCA) statistical method, with sensorial analysis in order to discriminate the quality of the samples. It was observed that the 3,4-dicaffeoylquinic (3,4-diCQA) and 3,5-dicaffeoylquinic (3,5-diCQA) isomers are very important for grouping the coffees into good and bad samples.

Brazil↗
PubMed2005

Contribution of chlorogenic acids to the iron-reducing activity of coffee beverages.

The iron-reducing activity of coffee beverages was determined by the ferric reducing antioxidant power (FRAP) assay. The influence on FRAP due to the degree of roasting (light, medium, and dark), species (Coffea arabica and Coffea robusta), and caffeine content (regular and decaffeinated) was investigated using ground and soluble coffee samples. The concentration of specific chlorogenic acids and caffeine in the beverages was determined by high-performance liquid chromatography and related to FRAP using Pearson correlation coefficients. All measurements were expressed per unit of soluble solids. Beverages prepared with ground coffee had, on average, 27% higher FRAP values than those prepared with soluble coffee (p < 0.05). In the former beverages, FRAP of C. robusta samples was significantly higher (on average, 50.3%) when compared to that of C. arabica samples, and FRAP values decreased with increasing degree of roasting (p < 0.05). A strong correlation (r > 0.91) was found between FRAP and the total content of chlorogenic acids, particularly that of the caffeoylquinic acid isomers. The iron-reducing activity of coffee beverages was not influenced by caffeine.

Antioxidants↗
PubMed1996

Polymerized cyclomaltoheptaose (beta-cyclodextrin, beta-CDn) inclusion complex formation with chlorogenic acid: solvent effects on thermochemistry and enthalpy-entropy compensation.

The inclusion of chlorogenic acid (CA) by epichlorohydrin-polymerized cyclomaltoheptaose (beta-cyclodextrin, beta-CDn) was studied with regard to temperature, solvent, and water activity aH2O approximately mole fraction = XH2O = 0.8-1 using MeOH as the diluent; 0.1 M sodium phosphate buffer). We discovered that the extreme convex curvature in K (the apparent stability constant) as a function of temperature was nearly eliminated at the lowest XH2O. The latter finding argues that this unusual CD behavior in aqueous media was due to perturbations in beta-CD's spatial organization in the polymeric matrix with temperature. Related to this we found, from the dependence of K on XH2O (K = K'XzH2O), that the beta-CDn.CA complex's stoichiometric coefficient, z, for water, varied between 5 and 8, depending on the temperature of the solution (K' = 400-800 M-1; T approximately 295-315 K). Our determinations of z were similar to those reported previously for beta-CD.(+)-limonene (z approximately 7), soluble beta-CD.CA (z approximately 6) or obtained by molecular dynamics calculations for beta-CD.CA reported herein (z approximately 5). However, beta-CDn.CA's z values did show a significant positive correlation with temperature not evident in equivalent solution experiments. Calculations of delta H and delta S at various XH2O values show linear enthalpy-entropy compensation (delta H plotted against delta S) but with a slope (Tc = theta delta H/theta delta S approximately 228 K) significantly less than Tc values determined from either standard aqueous thermodynamic experiments (Tc approximately 305 K on either beta-CD or beta-CDn) or variable XH2O (Tc approximately 272 K) experiments. To the best of our knowledge, this is the smallest Tc value detected in a multitude of CD.guest studies. This evident solvent effect on Tc strongly argues that the chemical part process of inclusion complex formation involves changes in the solvation of the beta-CDn's binding site.

Carbohydrate Conformation↗
PubMed2004

Effects of benzyl glucoside and chlorogenic acid from Prunus mume on adrenocorticotropic hormone (ACTH) and catecholamine levels in plasma of experimental menopausal model rats.

To investigate the effectiveness of benzyl beta-D-glucopyranoside (BG) and chlorogenic acid (CA), the constituents of the fruit of Prunus mume, for relieving tension in experimental menopausal model rats (M-rats) caused by ether stress, the effects of BG and CA on adrenocorticotropic hormone (ACTH) and catecholamine (adrenaline, noradrenaline, and dopamine) levels were examined in the plasma of M-rats. Caffeic acid, quinic acid, and rosmarinic acid, which are compounds structurally related to CA, were also examined. BG obviously recovered catecholamine levels decreased by ether stress and increased dopamine to high levels. On the other hand, CA significantly decreased the ACTH level increased by ether stress and showed the greatest effect of all compounds. These results suggest that BG and CA may contribute to relieving the tension in M-rats caused by ether stress.

Adrenocorticotropic Hormone↗
PubMed2003

Oxidative conjugation of chlorogenic acid with glutathione. Structural characterization of addition products and a new nitrite-Promoted pathway.

Chlorogenic acid (1), a cancer chemopreventive agent widely found in fruits, tea and coffee, undergoes efficient conjugation with glutathione (GSH), in the presence of horseradish peroxidase/H(2)O(2) or tyrosinase at pH 7.4, to yield three main adducts that have been isolated and identified as 2-S-glutathionylchlorogenic acid (3), 2,5-di-S-glutathionylchlorogenic acid (4) and 2,5,6-tri-S-glutathionylchlorogenic acid (5) by extensive NMR analysis. The same pattern of products could be obtained by reaction of 1 with GSH in the presence of nitrite ions in acetate buffer at pH 4. Mechanistic experiments suggested that oxidative conjugation reactions proceed by sequential nucleophilic attack of GSH on ortho-quinone intermediates. Overall, these results provide the first complete spectral characterization of the adducts generated by biomimetic oxidation of 1 in the presence of GSH, and disclose a new possible nitrite-mediated conjugation pathway of 1 with GSH at acidic pH of physiological relevance.

Chlorogenic Acid↗
PubMed2004

Simultaneous determination of chlorogenic acid, caffeic acid, ferulic acid, protocatechuic acid and protocatechuic aldehyde in Chinese herbal preparation by RP-HPLC.

In the present study, a reversed phase high performance liquid chromatographic (RP-HPLC) method was established for simultaneous determination of chlorogenic acid, caffeic acid, ferulic acid, protocatechuic acid and protocatechuic aldehyde in a Chinese herbal preparation (Fufang-Pugongying-Mixture). The separation was performed on a Hypersil ODS-2 column by isocratic elution with methanol and 0.2 M acetate buffer (pH 3.6) (15 : 85, v/v) as the mobile phase at the flow-rate of 1.0 ml/min with operating temperature of 30 degrees C, and detection wavelength of 300 nm. A good linear regression relationship between peak-areas and concentrations was obtained over the range of 2-200 microg/ml for the five marker compounds mentioned above. The spike recoveries were within 96.72-104.07%. The variation coefficient (CV) values of the precision were in the range of 0.89-4.50%. Moreover the developed method has reference value for quantitative analysis of Taraxacum, Lonicera and Angelica.

Angelica↗