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PubMed1986

Inhibition by chlorogenic acid of haematin-catalysed retinoic acid 5,6-epoxidation.

Chlorogenic acid (3-O-caffeoylquinic acid) inhibited haematin- and haemoglobin-catalysed retinoic acid 5,6-epoxidation. Some other phenol compounds (caffeic acid and 4-hydroxy-3-methoxybenzoic acid) also showed inhibitory effects on the haematin- and haemoglobin-catalysed epoxidation, but salicylic acid did not. Of the above compounds, caffeic acid and chlorogenic acid were potent inhibitors compared with the other two, suggesting that the o-hydroquinone moiety of chlorogenic acid and caffeic acid is essential to the inhibition of the epoxidation. Although caffeic acid inhibited retinoic acid 5,6-epoxidation requiring the consumption of O2, formation of retinoic acid radicals was not inhibited on the addition of caffeic acid to the incubation mixture. The above results suggest that caffeic acid does not inhibit the formation of retinoic acid radicals but does inhibit the step of conversion of retinoic acid radical into the 5,6-epoxide.

Caffeic Acids↗
PubMed2001

Chlorogenic acid and caffeic acid are absorbed in humans.

Chlorogenic acid, an ester of caffeic acid and quinic acid, is a major phenolic compound in coffee; daily intake in coffee drinkers is 0.5-1 g. Chlorogenic acid and caffeic acid are antioxidants in vitro and might therefore contribute to the prevention of cardiovascular disease. However, data on the absorption of chlorogenic acid and caffeic acid in humans are lacking. We determined the absorption of chlorogenic acid and caffeic acid in a cross-over study with 4 female and 3 male healthy ileostomy subjects. In such subjects, degradation by the colonic microflora is minimal and absorption can be calculated as the amount ingested minus the amount excreted in ileostomy effluent. The ileostomy subjects ingested 2.8 mmol chlorogenic acid and 2.8 mmol caffeic acid on separate days in random order and subsequently collected ileostomy fluid and urine for 24 h. Absorption of chlorogenic acid was 33 +/- 17% (mean +/- SD) and of caffeic acid 95 +/- 4%. Traces of the ingested chlorogenic acid and 11% of the ingested caffeic acid were excreted in urine. Thus, one third of chlorogenic acid and almost all of the caffeic acid were absorbed in the small intestine of humans. This implies that part of chlorogenic acid from foods will enter into the blood circulation, but most will reach the colon.

Absorption↗
PubMed2004

Application of preparative high-speed counter-current chromatography for separation of chlorogenic acid from Flos Lonicerae.

Chlorogenic acid, an ester formed between caffeic acid and quinic acid, is a major phenolic compound in the traditional Chinese medicinal herb Flos Lonicerae. The separation and purification of chlorogenic acid from the crude extract of Flos Lonicerae was achieved by high-speed counter-current chromatography (HSCCC). A high acid, highly polar two-phase solvent system containing n-butanol-acetic acid-water (4:1:5) was run on a preparative scale. The upper phase was used as the mobile phase in the head to tail elution mode. A 300-mg quantity of the crude extract containing 5.97% chlorogenic acid was loaded on a 342-ml HSCCC column. Double separations were performed with the same solvent system yielding 16.9 mg chlorogenic acid at 94.8% purity with approximately 90% recovery.

Chlorogenic Acid↗
PubMed1998

Iron chelation by chlorogenic acid as a natural antioxidant.

Chlorogenic acid, a dietary antioxidant, effectively inhibited the iron-induced lipid peroxidation of bovine liver microsomes in a concentration-dependent manner. In the Fenton-type reaction, chlorogenic acid inhibited the production of the hydroxyl radical by iron-EDTA or iron-ADP, while iron plus chlorogenic acid did not generate the hydroxyl radical. The formation of an iron complex with chlorogenic acid was demonstrated by UV/vis absorbance spectroscopic, ESR and 1H-NMR studies. The ferric complex with chlorogenic acid was in the ferric high-spin state near rhombicity, and had no radical scavenging activity. The results indicate that chlorogenic acid prevented the formation of the hydroxyl radical by forming a chelate with iron whose complex cannot catalyze the Fenton-type reaction.

Animals↗
PubMed2003

Chlorogenic acid, quercetin-3-rutinoside and black tea phenols are extensively metabolized in humans.

Dietary phenols are antioxidants, and their consumption might contribute to the prevention of cardiovascular disease. Coffee and tea are major dietary sources of phenols. Dietary phenols are metabolized extensively in the body. Lack of quantitative data on their metabolites hinders a proper evaluation of the potential biological effects of dietary phenols in vivo. The aim of this study was to identify and quantify the phenolic acid metabolites of chlorogenic acid (major phenol in coffee), quercetin-3-rutinoside (major flavonol in tea) and black tea phenols in humans, and determine the site of metabolism. Healthy humans (n = 20) with an intact colon participated in a dietary controlled crossover study, and we identified and quantified approximately 60 potential phenolic acid metabolites in urine. Half of the ingested chlorogenic acid and 43% of the tea phenols were metabolized to hippuric acid. Quercetin-3-rutinoside was metabolized mainly to phenylacetic acids, i.e., 3-hydroxyphenylacetic acid (36%), 3-methoxy-4-hydroxyphenylacetic acid (8%) and 3,4-dihydroxyphenylacetic acid (5%). In contrast, in seven humans without a colon, we found only traces of phenolic acid metabolites in urine after they had ingested chlorogenic acid and quercetin-3-rutinoside. This implies that the colonic microflora convert most of these dietary phenols into metabolites that then reach the circulation. Metabolites of dietary phenols have lower antioxidant activity than their parent compounds; therefore, the contribution of dietary phenols to antioxidant activity in vivo might be lower than expected from in vitro tests.

Adult↗
PubMed1998

Use of citric acid for neutralizing polymerase chain reaction inhibition by chlorogenic acid in potato extracts.

Polyphenolics are a widely distributed class of plant constituents implicated in the inhibition of the polymerase chain reaction (PCR). Since chlorogenic acid forms the bulk of phenolics in the potato tuber, a range of chlorogenic acid concentrations were tested for inhibition of reverse transcription (RT) and PCR steps. The RT step was inhibited at chlorogenic acid concentrations of 6.0 to 7.5 microg, while the PCR step was inhibited at much lower concentrations of 1.2 to 1.8 microg. Incorporation of 1.2% citric acid at the nucleic acid extraction step prevented darkening of the extract and neutralized the inhibitory effect of chlorogenic acid.

Chlorogenic Acid↗
PubMed1998

Effects of 3-mercaptopicolinic acid and a derivative of chlorogenic acid (S-3483) on hepatic and islet glucose-6-phosphatase activity.

Glucose-6-phosphatase activity was measured in hepatic microsomes and in pancreatic islets from ob/ob mice. In hepatic microsomes vanadate, phlorizin, 3-mercaptopicolinic acid and a derivative of chlorogenic acid (S-3483) inhibited the translocase activity of the enzyme, vanadate in addition inhibited hydrolase activity. In islets, vanadate inhibited both components of the enzyme, phlorizin inhibited only hydrolase activity while 3-mercaptopicolinic acid and compound S-3483 were without effect. Similarly, when islets were incubated with 3H2O and unlabeled glucose, the incorporation of 3H into medium glucose was inhibited by vanadate and phlorizin, but not by 3-mercaptopicolinic acid and S-3483. These findings suggest that, as with glucokinase, different isoenzymes of glucose-6-phosphatase are present in islets and liver.

Animals↗
PubMed1995

The suppression of the N-nitrosating reaction by chlorogenic acid.

N-Nitrosation of a model aromatic amine (2,3-diamino-naphthalene) by the N-nitrosating agent produced by nitrite in acidic solution was inhibited by a polyphenol, chlorogenic acid, which is an ester of caffeic acid quinic acid. Caffeic acid also inhibited the N-nitrosation, but quinic acid did not. 1,2-Benzenediols and 3,4-dihydroxybenzoic acid had inhibitory activities. Chlorogenic acid, caffeic acid, 1,2-benzenediols and 3,4-dihydroxybenzoic acid were able to scavenge the stable free radical, 1,1-diphenyl-2-picrylhydrazyl. Chlorogenic acid was found to be nitrated by acidic nitrite. The kinetic studies and the nitration observed only by bubbling of nitric oxide plus nitrogen dioxide gases indicated that the nitrating agent was nitrogen sesquioxide. The observations showed that the mechanism by which chlorogenic acid inhibited N-nitrosation of 2,3-diamino-naphthalene is due to its ability to scavenge the nitrosating agent, nitrogen sesquioxide. Chlorogenic acid may be effective not only in protecting against oxidative damage but also in inhibiting potentially mutagenic and carcinogenic reactions in vivo.

2-Naphthylamine↗
PubMed2001

Hepatic uptake of synthetic chlorogenic acid derivatives by the organic anion transport proteins.

Chlorogenic acid derivatives were recently identified as novel, potent, and specific inhibitors of the hepatic glucose 6-phosphate translocase. Inhibition of the glucose 6-phosphate translocase leads to a decrease in hepatic glucose production, rendering chlorogenic acid derivatives as potential novel therapeutics in patients with type 2 diabetes. The present study examines the hepatic uptake mechanism of the radiolabeled chlorogenic acid derivative S 1743 into freshly isolated rat hepatocytes. Initial uptake rates were Na(+)-independent and followed saturation kinetics with no superimposition of facilitated diffusion. Inhibition studies demonstrated that other chlorogenic acid derivatives inhibited uptake of the radiolabeled compound S 1743 into rat hepatocytes in the range of 1.1 to 11 microM, whereas the natural chlorogenic acid (up to 100 microM) had no effect at all. In addition, inhibition of S 1743 uptake into rat hepatocytes was found in the presence of sulfobromophthalein, sulfolithocholyltaurine, estrone-3-sulfate, cholyltaurine, verapamil, bumetanide, probenecide, phenol red, digoxin, and ouabain (in decreasing order) but not with N-methylnicotinamide, alpha-ketoglutarate, p-aminohippurate, geneticin sulfate, and 5-sulfosalicylate. The observed inhibition pattern suggested that members of the family of the organic anion transporting polypeptides (Oatps) could be involved in hepatic uptake of chlorogenic acid derivatives. Indeed, S 1743 uptake could be demonstrated in Oatp1- and Oatp2-expressing Xenopus laevis oocytes as well as in Oatp1-expressing Chinese hamster ovary cells. A comparison of the inhibition pattern obtained in hepatocytes compared with that obtained in Oatp1-expressing Chinese hamster ovary cells suggests that facilitated uptake by Oatp1 is a major contributor in total hepatic uptake of chlorogenic acid derivatives.

Animals↗
PubMed2003

Hierarchical scheme for LC-MSn identification of chlorogenic acids.

The fragmentation behavior of 18 chlorogenic acids that are not substituted at position 1 has been investigated using LC-MS(4) applied to a methanolic coffee bean extract and commercial cider (hard cider). Using LC-MS(3), it is possible to discriminate between each of the three isomers of p-coumaroylquinic acid, caffeoylquinic acid, feruloylquinic acid, and dicaffeoylquinic acid, and a hierarchical key has been prepared to facilitate this process when standards are not available. MS(4) fragmentations further support these assignments, but were not essential in reaching them. The distinctive behavior of 4-acyl and 3-acyl chlorogenic acids compared with the 5-acyl chlorogenic acids is a key factor permitting these assignments. The fragmentation patterns are dependent upon the particular stereochemical relationships between the individual substituents on the quinic acid moiety. Fragmentation is facilitated by 1,2-acyl participation and proceeds through quinic acid conformers in which the relevant substituents transiently adopt a 1,3-syn-diaxial relationship. Selected ion monitoring at m/z 529 clearly indicated the presence in coffee of six caffeoylferuloylquinic acid isomers, whereas previously only two or three had been demonstrated. The hierarchical key permitted specific structures to be assigned to each of the six isomers. These assignments are internally consistent and consistent with the limited data previously available.

Beverages↗
PubMed1992

Purification and some properties of chlorogenic acid oxidase from apple (Malus pumila).

Chlorogenic acid oxidase was extensively purified to homogeneity from apple flesh (Malus pumila cv. Fuji). The enzyme was purified 470-fold, with a total yield close to 70% from the plastid fraction by ammonium sulfate precipitation, gel filtration and ion-exchange chromatography. The molecular weight was determined to be 65,000 by both SDS-PAGE and gel filtration chromatography. The optimum pH for the enzyme activity was around 4.0, and the enzyme was stable in the range of pH 6-8. The pI obtained by isoelectrofocusing was 5.4, and the N-terminal amino acid sequence was N-Asp-Pro-Leu-Ala-Pro-Pro-. The reaction rate of the purified enzyme was much larger for chlorogenic acid than for other o-diphenols such as (+)-catechin, (-)-epicatechin and 4-methylcatechol, and the enzyme lacked both cresolase activity and p-diphenol oxidase activity. The Km value for the enzyme was found to be 122 microM toward chlorogenic acid. The purified enzyme had far less thermal stability than the enzyme of the plastid fraction. Diethyl-dithiocarbamate, sodium azide, o-phenanthroline and sodium fluoride markedly inhibited the enzyme activity.

Amino Acid Sequence↗
PubMed2002

Chlorogenic acid modifies plasma and liver concentrations of: cholesterol, triacylglycerol, and minerals in (fa/fa) Zucker rats.

Chlorogenic acid, a phenolic compound found ubiquitously in plants, is an in vitro antioxidant and metal chelator. Some derivatives of chlorogenic acid are hypoglycemic agents and may affect lipid metabolism. Concentrations of cholesterol and triacylglycerols are of interest due to their association with diseases such as non-insulin-dependent-diabetes- mellitus and obese insulin resistance. As little is known about the effects of chlorogenic acid in vivo, studies using obese, hyperlipidemic, and insulin resistant (fa/fa) Zucker rats were conducted to test the effect of chlorogenic acid on fasting plasma glucose, plasma and liver triacylglycerols and cholesterol concentrations. Aditionally, the effects of chlorogenic acid on selected mineral concentrations in plasma, spleen, and liver were determined. Rats were implanted with jugular vein catheters. Chlorogenic acid was infused (5 mg/Kg body weight/day) for 3 weeks via intravenous infusion. Chlorogenic acid did not promote sustained hypoglycemia and significantly lowered the postprandial peak response to a glucose challenge when compared to the same group of rats before Chlorogenic acid treatment. In Chlorogenic acid-treated rats, fasting plasma cholesterol and triacylglycerols concentrations significantly decreased by 44% and 58% respectively, as did in liver triacylglycerols concentrations (24%). We did not find differences (p > 0.05) in adipose triacylglycerols concentration. Significant differences (p < 0.05) in the plasma, liver, and spleen concentration of selected minerals were found in chlorogenic acid-treated rats. In vivo, chlorogenic acid was found to improve glucose tolerance, decreased some plasma and liver lipids, and improve mineral pool distribution under the conditions of this study.

Journal Article↗
PubMed2003

[Study on stability of beta-cyclodextrin to chlorogenic acid].

To investigate the stabilizing effect of chlorogenic acid against beta-cyclodextrin, beta-cyclodextrin inclusion compound of chlorogenic acid was prepared by liquid phase method, and affirmed by UV and different thermal analysis. Stability in solution was contrasted between chlorogenic acid and its inclusion complex with beta-cyclodextrin, and the stability of the latter was increased.

Chlorogenic Acid↗
PubMed2003

[Studies on stability of chlorogenic acid in extract of Flos lonicerae].

OBJECTIVE: To investigate the stability of chlorogenic acid in extract of flos lonicerae in different conditions. METHOD: The stability of chlorogenic acid in extract of flos lonicerae in phosptat buffe with different pH values, methanol, ethanol and different base solutions(Ca(OH)2 and NaOH) was investigated by the classical isothermal method. RESULT: The experiments showed the chlorogenic acid in extract of flos lonicerae was more stable in acidic water than in basic water. It was stable in these organic solutions and base solution[Ca(OH)2]. CONCLUSION: In different conditions, the stability of chlorogenic acid in extract of flos lonicerae was different. It provided a reference to the extraction and analysis of chlorogenic acid and production of chlorogenic acid preparation.

Calcium Hydroxide↗
PubMedDate not supplied

Interaction between chlorogenic acid and antioxidants.

The interaction between chlorogenic acid (CGA) and antioxidants was investigated by two different parameters: radical intensity and cytotoxicity induction. ESR spectroscopy shows that CGA produced radicals under alkaline condition. The CGA radical was scavenged by 100-300-fold lower concentrations of sodium ascorbate or N-acetyl-l-cysteine (NAC), whereas the ascorbate radical was not completely scavenged by CGA. The cytotoxic activity of CGA against human oral tumor cells (HSC-2, HSG) was completely eliminated by lower concentrations of sodium ascorbate or NAC, whereas that of sodium ascorbate or NAC was only slightly reduced by CGA. The present study demonstrated that CGA induces cytotoxicity by its radical-mediated oxidation mechanism and suggests the applicability of ESR spectroscopy for the screening of drug to drug interaction.

Acetylcysteine↗
PubMed1981

Evidence against the reported antithiamine effect of caffeic and chlorogenic acids.

Contrary to earlier literature reports, chlorogenic acid (I) is shown to have little or no deleterious effect on thiamine (II) when the 2 compounds are codissolved in aqueous solution. Evidence from nmr spectroscopy and from t. l. c. determination demonstrate that when II is heated at 60 degrees C and at pH 7.8 for 24h, about 10% is destroyed. This result is the same whether I is present or not. Incubating II with I or with caffeic acid (III) in a phosphate buffer at pH 7 or in thiamine assay medium at pH 6 for up to 24h at 37 degrees C did not reduce the growth activity of II or Lactobacillus viridescens. We conclude that I and III are not antithiamine agents.

Caffeic Acids↗
PubMed1995

Chlorogenic acid as a natural scavenger for hypochlorous acid.

The effect of chlorogenic acid (CGA) on the killing of Escherichia coli by hypochlorous acid (HOCI) was examined. CGA prevented E. coli from bactericidal action of HOCI in a concentration-dependent manner. HOCI reacted rapidly with CGA. By comparison with the one- and two-electron oxidation products produced by peroxidase and phenolase reactions, respectively, the main product was identified as o-quinone of CGA via the formation of o-semiquinone of CGA as an intermediate The quinone form of CGA reacted further with HOCI to yield unstable product(s).

Blood Bactericidal Activity↗
PubMed2003

Effect of chlorogenic acid on hydroxyl radical.

Chlorogenic acid (CGA) is considered to act as an antioxidant. However, the inhibitory effects of CGA on specific radical species are not well understood. Electron spin resonance (ESR) in combination with spin trapping techniques was utilized to detect free radicals. 5,5-Dimethyl-1-pyrroline-N-oxide (DMPO) was used as a spin trapping reagent while the Fenton reaction was used as a source of hydroxyl radical (*OH). We found that CGA scavenges *OH in a dose-dependent manner. The kinetic parameters, IC50 and Vmax, for CGA scavenging of *OH were 110 and 1.27 microM/sec, respectively. The rate constant for the scavenging of *OH by CGA was 7.73 x 10(9) M(-1) sec(-1). Our studies suggest that the antioxidant properties of CGA may involve a direct scavenging effect of CGA on *OH.

Chlorogenic Acid↗