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PubMed2004

Boron deficiency causes accumulation of chlorogenic acid and caffeoyl polyamine conjugates in tobacco leaves.

The effects of boron (B) deficiency on carbohydrate concentrations and the pattern of phenolic compounds were studied in leaves of tobacco plants (Nicotiana tabacum L.). Plants grown under B deficiency showed a notable increase in leaf carbohydrates and total phenolic compounds when compared to controls. The qualitative composition of phenolics was analyzed by HPLC-mass spectrometry. The level of caffeate conjugates (i.e., chlorogenic acid) increased in B-deficient plants. In addition, the accumulation of two caffeic acid amides (N-caffeoylputrescine and putative dicaffeoylspermidine) was observed.

Boron↗
PubMed1990

Inhibitory effects of chlorogenic acid, reserpine, polyprenoic acid (E-5166), or coffee on hepatocarcinogenesis in rats and hamsters.

Four different experiments were performed in order to examine the modifying effects of chlorogenic acid (CA), reserpine, polyprenoic acid (E-5166), and coffee on chemical carcinogenesis in rats or hamsters. Experiment 1: The numbers of hyperplastic liver cell foci and the incidence of colon tumors in male and female Syrian golden hamsters given a single intravenous injection of methylazoxymethanol (MAM) acetate and then fed the diet containing 0.025% CA for 24 wk were significantly lower than those of hamsters given MAM acetate alone. Experiment 2: The incidence of altered hepatocellular foci in female ACI/N rats given N-2-fluorenylacetamide (FAA, 0.02% in diet) for 10 wk and reserpine (weekly subcutaneous injections, 1 microgram/g body weight) during or after (17 wk) FAA exposure was significantly lower than that of rats given FAA alone. Experiment 3: The number of hepatocellular foci in male ACI/N rats given 0.02% FAA diet for 13 wk and E-5166 by gavage (40 mg/kg body weight, 3 times/wk) for 16 wk after the end of FAA exposure was significantly smaller than that in rats given FAA diet alone. Experiment 4: Incidences of liver tumors and hepatocellular foci of rats given concurrent dietary administration of aminopyrine (0.01%) and sodium nitrite (0.1%) and coffee solution as a drinking water for 630 da were significantly lower than those of rats given aminopyrine and sodium nitrite. Thus, the tested compounds had inhibitory effects on chemical carcinogenesis in liver or colon.

Animals↗
PubMed2004

Chlorogenic acid inhibits Bcr-Abl tyrosine kinase and triggers p38 mitogen-activated protein kinase-dependent apoptosis in chronic myelogenous leukemic cells.

We report that chlorogenic acid (Chl) induces apoptosis of several Bcr-Abl-positive chronic myelogenous leukemia (CML) cell lines and primary cells from CML patients in vitro and destroys Bcr-Abl-positive K562 cells in vivo. In contrast, this compound has no effect on the growth and viability of Bcr-Abl-negative lymphocytic and myeloid cell lines and primary CML cells. Sodium chlorogenate (NaChl) exhibits 2-fold higher efficiency in killing K562 cells compared with Chl. NaChl also induces growth inhibition of squamous cell carcinoma (HSC-2) and salivary gland tumor cells (HSG), although at 50-fold higher concentration. NaChl inhibits autophosphorylation of p210(Bcr-Abl) fusion protein rapidly. We demonstrate that p38 phosphorylation is increased in Bcr-Abl-positive cells after treatment with NaChl and closely paralleled the inhibition of Bcr-Abl phosphorylation. NaChl did not increase phosphorylation of p38 in Bcr-Abl-negative cells including HSC-2 and HSG that are responsive to this compound, indicating that p38 activation by NaChl is dependent on Bcr-Abl kinase inhibition. Inhibition of p38 activity by SB203580 significantly reduced NaChl-induced apoptosis of K562 cells, whereas activation of p38 by anisomycin augmented the apoptosis. These findings indicate that inhibition of Bcr-Abl kinase leading to activation of p38 mitogen-activated protein (MAP) kinase may play an important role in the anti-CML activity of Chl.

Apoptosis↗
PubMed1998

Effect of dietary chlorogenic acid on multiple immune functions and formation of aberrant crypt foci in rats.

Adult male Sprague-Dawley rats were fed 70 mg/kg body weight chlorogenic acid (CHA) for 7 wk. One CHA-fed group was also given 2 injections of the colon carcinogen azoxymethane (AZO) on d 2 and 9 of CHA treatment. Three major types of immune responses were assessed: antibody production, specific cell-mediated immunity, and nonspecific cell-mediated immunity. The formation of AZO-induced aberrant crypt foci (ACF) in the colon were observed, as was colonic cell proliferation. There were no significant effects of CHA treatment on any of the immune parameters examined or on formation of preneoplastic lesions or cell proliferation in the colon. The overall nonsignificant trends in immune function, colon cell proliferation, and ACF development were, however, more consistent with immunosuppression and enhanced preneoplasia.

Animals↗
PubMed2006

Chlorogenic acid is poorly absorbed, independently of the food matrix: A Caco-2 cells and rat chronic absorption study.

According to epidemiologic studies, dietary phenolic antioxidants, such as chlorogenic acid (CQA), could prevent coronary heart diseases and some cancers. Coffee is the main source of CQA in the human diet. The aim of this study was to assess the effect of usual coffee consumption conditions, such as the addition of milk, on CQA bioavailability. Interactions between CQA and milk proteins were shown, using an ultrafiltration technique. These interactions proved to be slightly disrupted during an in vitro digestion process. CQA absorption and bioavailability were then studied in vitro using a Caco-2 cell model coupled with an in vitro digestion process, and in vivo, in a chronic supplementation study in which rats were fed daily coffee or coffee and milk for 3 weeks. Both experiments showed that CQA absorption under its native form is weak, but unmodified by the addition of milk proteins, and slightly reduced by the addition of Maillard reaction products. These data show that there are some interactions between coffee phenolics and milk proteins, but these have no significant effect on CQA bioavailability from coffee in the rat. CQA is poorly absorbed under its native form in the body, when ingested in a realistic food matrix.

Absorption↗
PubMed2001

Acute inhibition of hepatic glucose-6-phosphatase does not affect gluconeogenesis but directs gluconeogenic flux toward glycogen in fasted rats. A pharmacological study with the chlorogenic acid derivative S4048.

Effects of acute inhibition of glucose-6-phosphatase activity by the chlorogenic acid derivative S4048 on hepatic carbohydrate fluxes were examined in isolated rat hepatocytes and in vivo in rats. Fluxes were calculated using tracer dilution techniques and mass isotopomer distribution analysis in plasma glucose and urinary paracetamol-glucuronide after infusion of [U-(13)C]glucose, [2-(13)C]glycerol, [1-(2)H]galactose, and paracetamol. In hepatocytes, glucose-6-phosphate (Glc-6-P) content, net glycogen synthesis, and lactate production from glucose and dihydroxyacetone increased strongly in the presence of S4048 (10 microm). In livers of S4048-treated rats (0.5 mg kg(-1)min(-)); 8 h) Glc-6-P content increased strongly (+440%), and massive glycogen accumulation (+1260%) was observed in periportal areas. Total glucose production was diminished by 50%. The gluconeogenic flux to Glc-6-P was unaffected (i.e. 33.3 +/- 2.0 versus 33.2 +/- 2.9 micromol kg(-1)min(-1)in control and S4048-treated rats, respectively). Newly synthesized Glc-6-P was redistributed from glucose production (62 +/- 1 versus 38 +/- 1%; p < 0.001) to glycogen synthesis (35 +/- 5% versus 65 +/- 5%; p < 0.005) by S4048. This was associated with a strong inhibition (-82%) of the flux through glucokinase and an increase (+83%) of the flux through glycogen synthase, while the flux through glycogen phosphorylase remained unaffected. In livers from S4048-treated rats, mRNA levels of genes encoding Glc-6-P hydrolase (approximately 9-fold), Glc-6-P translocase (approximately 4-fold), glycogen synthase (approximately 7-fold) and L-type pyruvate kinase (approximately 4-fold) were increased, whereas glucokinase expression was almost abolished. In accordance with unaltered gluconeogenic flux, expression of the gene encoding phosphoenolpyruvate carboxykinase was unaffected in the S4048-treated rats. Thus, acute inhibition of glucose-6-phosphatase activity by S4048 elicited 1) a repartitioning of newly synthesized Glc-6-P from glucose production into glycogen synthesis without affecting the gluconeogenic flux to Glc-6-P and 2) a cellular response aimed at maintaining cellular Glc-6-P homeostasis.

Animals↗
PubMed2002

Inhibitory Effects of Chlorogenic Acid on Azoxymethane-induced Colon Carcinogenesis in Male F344 Rats.

Modifying effects of chlorogenic acid (CA) on carcinogen-induced large bowel carcinogenesis was examined in rats. A total of 150 male F344 rats, 4 weeks old, were divided into 5 groups. At 6 weeks of age, groups 1-3 were given subcutaneous injections of AOM (15 mg/kg body weight) once a week for three weeks. Group 2 was given the diet mixed with CA at the dose of 250 ppm during the initiation phase (5 weeks), and group 3 was exposed to the same diet during the post-initiation phase (32 weeks). Group 4 received the diet with CA throughout the experiment. Group 5 was maintained on the basal diet alone and served as a control. At the termination of the experiment (36 weeks after the start), the incidence of colon tumors in group 2 and 3 demonstrated a tendency for decrease as compared with group 1 although this did not attain significance At this time, the multiplicity of colon tumors of group 2 was significantly smaller than in group 1. In this study, the anti-proliferating cell nuclear antigen (PCNA) indices for non-neoplastic cells of the colon mucosae in groups 2 and 3 were also smaller than in group 1. The data suggest that CA has chemopreventive potential against colon carcinogenesis in rats like that showen in a hamster model with use of methylazoxymethanol acetate.

Journal Article↗
PubMed2006

Determination and pharmacokinetic study of chlorogenic acid in rat dosed with Yin-Huang granules by RP-HPLC.

A reversed-phase high-performance liquid chromatographic (RP-HPLC) method was described for the determination of chlorogenic acid (CGA) in rat plasma using protocatechuic acid as internal standard (IS). CGA in plasma was extracted with acetonitrile, which also acted as deproteinization agent. Chromatographic separation was performed on a Kromasil C18 column with methanol-0.2 m acetic acid (pH 3.0, 25:75, v/v) as mobile phase at a flow-rate of 1.0 mL/min with an operating temperature of 30 degrees C and UV detection at 300 nm. The standard curve was found to be linear over the concentration ranges of 0.4-2.5 microg/mL and 2.5-40 microg/mL, and the limit of quantification (LOQ) was 0.4 microg/mL. The analytical precision and accuracy were validated by relative standard deviation (RSD) and relative error, which were in ranges 3.14-10.78% and -2.20-5.00%, respectively. The average recovery of CGA was 87.59%. The method was successfully applied to the pharmacokinetic study of CGA in Yin-Huang granules.

Animals↗
PubMed1984

Chromatographic separation and identification of naturally occurring chlorogenic acids by 1H nuclear magnetic resonance spectroscopy and mass spectrometry.

The high-performance liquid chromatographic separation and identification of the phenolic compounds in extracts from coffee bean are described. The system consists of Fine SIL C18-5 analytical and preparative columns and gradient elution (solvent A, 10 mM H3PO4; solvent B, methanol). The seven chlorogenic acids isolated were identified by mass spectrometry and nuclear magnetic resonance spectroscopy. The isolated and identified compounds are 3-O-caffeoylquinic acid, 4-O-caffeoylquinic acid, 5-O-caffeoylquinic acid, 3,4-O-dicaffeoylquinic acid, 3,5-O-dicaffeoylquinic acid, 4,5-O-dicaffeoylquinic acid and 3-O-feruloylquinic acid.

Chlorogenic Acid↗
PubMed1993

Protective effects of chlorogenic acid, curcumin and beta-carotene against gamma-radiation-induced in vivo chromosomal damage.

The mouse bone marrow micronucleus test was carried out to evaluate the possible role of the dietary constituents chlorogenic acid (CGA), curcumin (CR) and beta-carotene (BC) in modulating the in vivo chromosomal damage induced by gamma-radiation. The results obtained suggest that oral administration of CGA (50, 100 and 200 mg/kg b.w.), CR (5, 10 and 20 mg/kg b.w.) and BC (0.5 and 2.5 mg/kg b.w.) to mice can significantly reduce the frequencies of micronucleated polychromatic erythrocytes (Mn PCEs) induced by whole body exposure to gamma-radiation (1.15 Gy; 0.05 Gy/s). With CGA and CR, this effect was observed after a single administration either 2 h before or immediately after irradiation. However, with BC a 7-day feeding before irradiation was necessary to obtain a significant reduction in the incidence of Mn PCEs. The protective effects of CGA, CR and BC were observed in bone marrow cells sampled 24, 30 and 48 h after exposure to radiation.

Animals↗
PubMed2006

Chlorogenic acids and lactones in regular and water-decaffeinated arabica coffees.

The market for decaffeinated coffees has been increasingly expanding over the years. Caffeine extraction may result in losses of other compounds such as chlorogenic acids (CGA) and, consequently, their 1,5-gamma-quinolactones (CGL) in roasted coffee. These phenolic compounds are important for flavor formation as well as the health effects of coffee; therefore, losses due to decaffeination need to be investigated. The present study evaluates the impact of decaffeination processing on CGA and CGL levels of green and roasted arabica coffees. Decaffeination produced a 16% average increase in the levels of total CGA in green coffee (dry matter), along with a 237% increase in CGL direct precursors. Different degrees of roasting showed average increments of 5.5-18% in CGL levels of decaffeinated coffee, compared to regular, a change more consistent with observed levels of total CGA than with those of CGL direct precursors in green samples. On the other hand, CGA levels in roasted coffee were 3-9% lower in decaffeinated coffee compared to regular coffee. Although differences in CGA and CGL contents of regular and decaffeinated roasted coffees appear to be relatively small, they may be enough to affect flavor characteristics as well as the biopharmacological properties of the final beverage, suggesting the need for further study.

Caffeine↗
PubMed1996

Thermospray-LC-MS analysis of various groups of polyphenols in tea. II: Chlorogenic acids, theaflavins and thearubigins.

An account is given of the application of thermospray LC-MS in the analysis of caffeoyl- and p-coumaroylquinic acids, theaflavins and thearubigins in black tea. All compounds, except for the thearubigens, could be detected as the pseudo-molecular ion [M + H]+. In addition to [M + H]+, other species such as adducts with sodium, ammonium and potassium, as well as solvent clusters were observed. The formation of those adducts depended upon on the structure of the compound. A fragmentation of chlorogenic acids occurred at elevated temperatures yielding the constituents of the molecules (caffeic, p-coumaric and quinic acids).

Biflavonoids↗
PubMed2006

Evaluation of the anti-inflammatory, analgesic and antipyretic activities of the natural polyphenol chlorogenic acid.

Phenolic compounds are numerous and ubiquitous in the plant kingdom, being particularly present in health-promoting foods. Epidemiological evidences suggest that the consumption of polyphenol-rich foods reduces the incidence of cancer, coronary heart disease and inflammation. Chlorogenic acid (CGA) is one of the most abundant polyphenol compounds in human diet. Data obtained from in vivo and in vitro experiments show that CGA mostly presents antioxidant and anti-carcinogenic activities. However, the effects of CGA on the inflammatory reaction and on the related pain and fever processes have been explored less so far. Therefore, this study was designed to evaluate the anti-inflammatory, antinociceptive and antipyretic activities of CGA in rats. In comparison to control, CGA at doses 50 and 100 mg/kg inhibited carrageenin-induced paw edema beginning at the 2nd hour of the experimental procedure. Furthermore, at doses 50 and 100 mg/kg CGA also inhibited the number of flinches in the late phase of formalin-induced pain test. Such activities may be derived from the inhibitory action of CGA in the peripheral synthesis/release of inflammatory mediators involved in these responses. On the other hand, even at the highest tested dose (200 mg/kg), CGA did not inhibit the febrile response induced by lipopolysaccharide (LPS) in rats. Additional experiments are necessary in order to clarify the true target for the anti-inflammatory and analgesic effects of CGA.

Administration, Oral↗
PubMed2006

Reactions of chlorogenic acid and quercetin with a soy protein isolate--influence on the in vivo food protein quality in rats.

Plant phenolic compounds are known to interact with proteins producing changes in the food (e. g., biological value (BV), color, taste). Therefore, the in vivo relevance, especially, of covalent phenol-protein reactions on protein quality was studied in a rat bioassay. The rats were fed protein derivatives at a 10% protein level. Soy proteins were derivatized with chlorogenic acid and quercetin (derivatization levels: 0.056 and 0.28 mmol phenolic compound/gram protein). Analysis of nitrogen in diets, urine, and fecal samples as well as the distribution of amino acids were determined. Depending on the degree of derivatization, the rats fed with soy-protein derivatives showed an increased excretion of fecal and urinary nitrogen. As a result, true nitrogen digestibility, BV, and net protein utilization were adversely affected. Protein digestibility corrected amino acid score was decreased for lysine, tryptophan, and sulfur containing amino acids.

Amino Acids↗
PubMed2005

Protective effects of ellagic and chlorogenic acids against oxidative stress in PC12 cells.

Following exposure of differentiated neuronal PC12 cells to either t-BHP, hydrogen peroxide (H2O2) or FeSO4 various kinds of reactive oxygen species (ROS) are generated leading to oxidative injury. The protective effects of two plant polyphenols, ellagic (EC) and chlorogenic acid (CGA), as well as of two metabolites, caffeic acid (CA) and ferulic acid (FA), were investigated in preincubation and coincubation experiments with respect to the following parameters: prevention of cell death, GSH depletion, lipid peroxidation and ROS formation. The polyphenols more efficiently suppressed cytotoxicity and loss of GSH caused by peroxides than by iron, particularly in preincubation. Lipid peroxidation which increased much stronger in response to FeSO4 was counteracted completely by the polyphenols. In case of iron, however, only coincubation was effective. EA and CGA and the metabolites CA and FA showed excellent elimination of ROS induced by all stressors. These findings suggest that two dietary antioxidants, EA and CGA, may have protective properties against oxidative stress induced in CNS.

Animals↗
PubMed2000

Rapid determination of chlorogenic acid and related compounds in sunflower seeds by high-performance liquid chromatography/atmospheric pressure chemical ionization mass spectrometry.

High-performance liquid chromatography (HPLC) in combination with atmospheric pressure chemical ionization mass spectrometry (APcI-MS) was applied to the determination of the phenolic fraction found in methanolic extracts of sunflower seeds (mainly chlorogenic acid and derived compounds). These extracts were directly separated by HPLC and detected by both negative and positive APcI-MS. Abundant structural information about these compounds can be obtained even at low extraction cone voltages. This method has been shown to be a rapid and effective method for the analysis of crude extracts from sunflower seeds.

Atmospheric Pressure↗