Search PubMed⌕ Search

SEARCH · Search PubMed

Results for “CHLOROGENIC ACID”

Search indexed PubMed citations on genomics, clinical trials, systematic reviews and public health. Explore titles, authors and supplied subject terms, then open the PubMed record.

Quote a phrase for an exact phrase match. Source license links do not imply unrestricted reuse.

At least 685 records · Page 38Linked to original sources

[Acids in coffee. XI. The proportion of individual acids in the total titratable acid].

22 acids in ground roast coffees and instant coffees were determined by GLC of their silyl derivatives (after preseparation by gel electrophoresis) or isotachophoresis. The contribution to the total acidity (which was estimated by titration to pH 8 after cation exchange of the coffee solutions) was calculated for each individual acid. The mentioned acids contribute with 67% (roast coffee) and 72% (instant coffee) to the total acidity. In the first place citric acid (12.2% in roast coffee/10.7% in instant coffee), acetic acid (11.2%/8.8%) and the high molecular weight acids (8%/9%) contribute to the total acidity. Also to be mentioned are the shares of chlorogenic acids (9%/4.8%), formic acid (5.3%/4.6%), quinic acid (4.7%/5.9%), malic acid (3.9%/3%) and phosphoric acid (2.5%/5.2%). A notable difference in the contribution to total acidity between roast and instant coffee was found for phosphoric acid and pyrrolidonecarboxylic acid (0.7%/1.9%). It can be concluded that those two acids are formed or released from e.g. their esters in higher amounts than other acids during the production of instant coffee.

Acids↗

Anti-inflammatory activity of extract and fractions from Nepeta sibthorpii Bentham.

Several species of Nepeta genus are utilized in folk medicine for treatment of contusions, rheumatic pains, fever, cutaneous eruptions. Some species are employed for their anti-inflammatory properties. In this paper, we report the results of phytochemical studies on aerial parts of Nepeta sibthorpii Bentham (Lamiaceae), an endemic plant of Greece. The bioassay-guided fractionation of methanol extract led to the isolation of ursolic acid and polyphenol fraction. By HPLC, we determined some phenolics: chlorogenic acid (0.315 mg/g) and the flavonoids rutin (0.091 mg/g), luteolin-7-O-glucoside (0.387 mg/g) and a luteolin derivative. We assayed the radical scavenging activity of Nepeta sibthorpii methanol extract by the 1,1-diphenyl-2-picrylhydrazyl (DPPH) method. Moreover, we studied the anti-inflammatory activity of Nepeta sibthorpii methanol extract (50 mg/kg, os), ursolic acid and polyphenol fraction (dose corresponding to 50 mg/kg of methanol extract, os) in the carrageenan-induced paw oedema in rat. In this experimental model, we observed a significant inhibition of paw oedema. We suppose that the anti-inflammatory effect of methanol extract could be related to the free radical scavenging activity and that it depends on a synergic action of all the components of the methanol extract, even if ursolic acid can be considered the main responsible for this activity.

Animals↗

Phenolic acids, syringaldehyde, and juglone in fruits of different cultivars of Juglans regia L.

Phenolic acids (chlorogenic, caffeic, p-coumaric, ferulic, sinapic, ellagic, and syringic acid) as well as syringaldehyde and juglone were identified in ripe fruits of 10 walnut cultivars: Adams, Cisco, Chandler, Franquette, Lara, Fernor, Fernette, Alsoszentivani 117 (A-117), Rasna, and Elit. Analyses were done using a high-performance liquid chromatograph equipped with a diode array detector. Significant differences in the contents of identified phenolics were observed among cultivars. Phenolics were determined separately in the kernel and in the thin skin of the walnut, termed the pellicle. Not only in the kernel but also in the pellicle did syringic acid, juglone, and ellagic acid predominate (average values of 33.83, 11.75, and 5.90 mg/100 g of kernel; and 1003.24, 317.90, and 128.98 mg/100 g of pellicle, respectively), and the contents of ferulic and sinapic acid (average values of 0.06 and 0.05 mg/100 g of kernel and 2.93 and 2.17 mg/100 g of pellicle, respectively) were the lowest in all cultivars. The highest differences in the sum of all identified phenolics were observed between Rasna and Fernette fruits; in Rasna there were >2-fold higher contents of identified phenolics in both kernel and pellicle. It was found that the walnut pellicle is the most important source of walnut phenolics. The ratio between the contents in pellicle and kernel varied by at least 14.8-fold for caffeic acid (cv. Adams) and by up to 752.0-fold for p-coumaric acid (cv. Elit).

Acids, Carbocyclic↗

Qualitative and quantitative analysis of phenolic acids in Asclepias syriaca L.

TLC and HPLC was applied to qualitative and quantitative determination of phenolic acids free and liberated by acid and alkaline hydrolysis in common milkweed. The presence of phenolic acids, namely p-hydroxybenzoic, p-coumaric, protocatechuic and caffeic acids, was confirmed in the leaves and flowers. Moreover, the flowers contained gallic acid, and the leaves contained alpha-resorcylic, vanilic and chlorogenic acids. Conjugated forms of phenolic acids predominate in the plant. They hydrolyse mainly to coffeic, p-coumaric, ferulic and p-hydroxybenzoic acids.

Chromatography, High Pressure Liquid↗

Flavonoids as antioxidants evaluated by in vitro and in situ liver chemiluminescence.

Administration of eriodyctiol and (+)-catechin (10 mg/100 g of body weight) to mice inhibited the enhancement of in situ liver chemiluminescence produced by CCl4 (0.5 ml/100 g) by 32 and 38% respectively. 3,4-Dicaffeoylquinic acid was less effective (13%), and cynarin had no effect. Previously, these compounds and other polyphenols were assayed as in vitro antioxidants by their abilities to inhibit the tert-butyl hydroperoxide (t-BOOH)-initiated chemiluminescence of mouse liver homogenates, and the IC50 (microM) values were as follows: (+)-catechin, 3; eriodyctiol, 9; myricetin and 4,2',4'-trihydroxy-6'-metoxychalcone, 15; 3,4-dicaffeoylquinic acid, 20; isochlorogenic acid, 30; caffeic acid, 5,6,3'-trihydroxy-7,4'-dimethoxyflavone and cynarin, 50; chlorogenic acid and apigenin, 150; quercetin, pedalitin, sylimarin and quercetin-3-methyl ester, 200; 7,4'-dihydroxy-5-methoxyflavonone and kaempferol-3,7-dirhamnoside, 500; quercitrin, 900; and galangin-3-methyl ether, genkwanin, hesperidin, ombuoside, phloridzin, quinic acid, rhoifolin, rutin and sophoricoside, greater than 1 mM. The in vitro and in vivo effects of these flavonoids and polyphenols may be related to their antioxidant abilities, making them promising substances to be investigated as water-soluble protectors against lipid peroxidation and other free radical-mediated cell injury.

Animals↗

[Comparison of the in vitro activities of ammonium humate and of enzymically oxidized chlorogenic and caffeic acids against type 1 and type 2 human herpes virus (author's transl)].

Ammonium humate (prepared from marsh water humic acids) as well as enzymically oxidized diphenolic compounds such as the oxidation products of chlorogenic and caffeic acids have strong antiviral activities in vitro. The effective concentrations lie considerably outside the cytotoxic range of the compounds mentioned.

Adsorption↗

Reactivity of dietary phenolic acids with peroxyl radicals: antioxidant activity upon low density lipoprotein peroxidation.

The interaction of four phenolic acids, representative of three chemical groups present in human diet, with peroxyl radicals was studied in vitro in a low density lipoprotein (LDL) oxidation model. The controlled oxidation of LDL was initiated by free radicals generated from a hydrophilic azo initiator and followed by monitoring the oxygen consumption and the fluorescence quenching of cis-parinaric acid previously incorporated into LDL. The hydroxycinnamic acid derivatives, chlorogenic and caffeic acids, have high stoichiometric numbers and reactivity with peroxyl radicals as compared with trolox, the water-soluble analogue of vitamin E, whereas ellagic acid (a tannic compound) compares with trolox effects. Protocatechuic acid (a hydroxybenzoic acid derivative) exhibits a complex reaction with peroxyl radicals, as indicated by UV spectroscopy, resulting in undefined inhibition periods of LDL oxidation and low reactivity with peroxyl radicals. Presumably, secondary radicals of these compounds are unable to initiate LDL oxidation. The antioxidant activity of the various phenolic compounds is discussed in terms of structure-activity relationships.

Amidines↗

The effects of caffeic acid and its related catechols on hydroxyl radical formation by 3-hydroxyanthranilic acid, ferric chloride, and hydrogen peroxide.

The effect of caffeic acid on hydroxyl radical formation through a reaction, which contained 0.22 M carbonate buffer (pH 7.4), 0.22 mM 3-hydroxyanthranilic acid, 87 mM 5,5-dimethyl-1-pyrroline-N-oxide (DMPO), 2.9 mM hydrogen peroxide, and 14 microM FeCl3, was investigated. The addition of 30 microM caffeic acid resulted in the decrease of hydroxyl radical formation in the reaction mixture. Chlorogenic acid, 3,4-dihydroxy-phenylalanine noradrenaline, gallic acid, dopamine, epicatechin, and D-(+)-catechin also suppressed the hydroxyl radical formation. In regard to the positional isomers of benzenediol, o-benzenediol inhibited the hydroxyl radical formation, but m and p-benzenediol did not. The inhibitory effect of the hydroxyl radical formation seems to be due to the chelation of iron ions by the catechols. Supporting evidence includes the diminished effect of catechols in the presence of EDTA (a potent iron ion chelator) and the observation of a visible band at 450 nm caused by the interaction between caffeic acid and iron ions. Additionally, the visible band (506 nm) was observed in the solution of o-benzenediol and ferric chloride but not in the solution of m- or p-benzenediol and ferric chloride. Thus compounds with adjacent hydroxyl groups on aromatic rings might inhibit hydroxyl radical formation.

3-Hydroxyanthranilic Acid↗

Modification of the mutagenicity of aflatoxin B1 and N-methyl-N'-nitro-N-nitrosoguanidine by certain phenolic compounds.

Five natural and two synthetic phenolic compounds were tested for their ability to suppress mutagenicity of aflatoxin B1 (AFB1) and N-methyl-N'-nitro-N-nitrosoguanidine (MNNG) in Salmonella typhimurium tester strain TA100. Caffeic acid and eugenol were observed to inhibit mutagenicity of both the carcinogens, while chlorogenic acid was effective in the case of AFB1 alone and ellagic acid and butylated hydroxytoluene were found to be antimutagenic only for MNNG. These differential activities of the phenolic compounds appeared to be due to their different modes of action towards direct and indirect acting carcinogens.

Aflatoxin B1↗

Contribution of periderm material and blanching time to the quality of pasteurized peach puree.

Fresh peaches were blanched for either a long (20 min) or short (2 min) time, with and without periderm material. Samples were then macerated into purees and pasteurized in boiling water for 30 min. Samples were subsequently stored at 40 degrees C for 4 weeks to determine physicochemical and sensory changes affecting overall quality and nutritional content. Purees containing periderm had higher antioxidant activity (AOX) and individual phenolic acid content after processing and storage, with good correlation to AOX observed with chlorogenic acid (r = 0.82). Long blanch times resulted in increased levels of extraction and retention of both total soluble phenolics and ascorbic acid. Quantitative descriptive analysis demonstrated increased aromatic perception of skin in samples containing periderm material, but the remaining sensory attributes were indistinguishable between treatments. Macerating peaches without periderm removal was demonstrated to increase levels of bioactive phytochemicals and increase the processing yield by 7. 6%, without significantly impacting product quality, color, or sensory attributes.

Antioxidants↗

Effects of native and oxidized phenolic compounds on sucrase activity in rat brush border membrane vesicles.

The effects of dietary phenolic compounds on intestinal sucrase were investigated in brush border membrane vesicles purified from rat small intestine. Screening experiments were conducted with different classes of phenolic compounds in both oxidized and native forms. The most potent inhibitor was native tannic acid at 0.1 mg/ml, resulting in an 80% loss of activity. Oxidized tannic acid had no effect. Significant decreases were also observed in vesicles treated with 0.1 mg/ml of catechol or epicatechin, yielding activity losses of 30-50%, regardless of oxidation state. With gallic acid, maximal (40%) inhibition occurred only in the oxidized form. Other phenolic compounds, such as ferulic, p-coumaric and caffeic acids, tended to be slightly inhibitory, while no inhibition was observed with vanillin or chlorogenic acid at the concentrations tested. These results confirm the enzyme inhibitory action of tannic acid, a polyphenolic compound, and also demonstrate that some individual dietary phenolic monomers have the potential to modulate enzyme activity in a brush border membrane vesicle model system.

Animals↗

Drug-nitrite interactions in human saliva: effects of food constituents on carcinogenic N-nitrosamine formation.

A simple and rapid high-pressure liquid chromatographic assay for monitoring N-nitrosodimethylamine (NDMA) in human saliva was developed. The method was used to study in vitro the effects of common food constituents on NDMA formation in saliva from the interaction of salivary nitrite with aminopyrine and oxytetracycline. Natural phenolic compounds, caffeic acid, and tannic acid, and synthetic additives, erythorbic acid, sorbic acid, propyl gallate, and butylated hydroxytoluene--all inhibited NDMA formation (20-80%). With ascorbic acid, up to 90% inhibition of NDMA synthesis in saliva was observed. In contrast, chlorogenic acid (a phenolic component of coffee) acted as a catalyst (up to 48% increase) of the nitrosamine formation under identical experimental conditions.

Adult↗

Identification of caffeoylquinic acid derivatives from Brazilian propolis as constituents involved in induction of granulocytic differentiation of HL-60 cells.

We have previously reported that Brazilian propolis extracts inhibited growth of HL-60 human myeloid leukemia cells, which is partly attributed to the induction of apoptosis associated with granulocytic differentiation. In this study, we isolated three compounds which induce granulocytic differentiation evaluated by nitroblue tetrazolium (NBT)-reducing assays from the water extract of propolis and identified as 4,5-di-O-caffeoylquinic, 3,5-di-O-caffeoylquinic, and 3,4-di-O-caffeoylquinic acids by NMR analysis. Cell growth inhibitory activity of these caffeoylquinic acids was found in HL-60 cell, which was mainly attributed to the induction of apoptosis. Furthermore, the potency of caffeoylquinic acid derivatives to induce granulocytic differentiation was examined in HL-60 cells. Caffeic, quinic, and chlorogenic acids had no effects on the NBT-reducing activity, while 3,4,5-tri-O-caffeoylquinic acid induced more than 30% of NBT-positive cells. These results suggest that the number of the caffeoyl groups bound to quinic acid plays an important role in the potency of the caffeoylquinic acid derivatives to induce granulocytic differentiation. This is the first report demonstrating that the caffeoylquinic acid derivatives induce granulocytic differentiation of HL-60 cells.

Cell Differentiation↗

A monophenol oxidase activity in extracts of sorghum.

A p-hydroxycinnamic acid oxidase activity was present in enzyme preparations from first internodes of Sorghum vulgare variety Wheatland milo when incubated in phosphate buffer at pH 7.5. This preparation had no classical polyphenolase activity but had both peroxidase and catalase activities. Since horseradish preparations catalyzed the same reaction, the oxidation probably is another example of a peroxidase-oxidase reaction. A second substrate was p-hydroxyphenylpyruvic acid. Ferulic acid was slightly active at low concentrations and inhibitory at higher ones. Diphenols such as caffeic and chlorogenic acids were inactive and inhibitory to p-hydroxycinnamic acid oxidation. A variety of monophenols such as tyrosine and cinnamic acid were inactive. An active substrate must have a free monophenolic group and para to this a C(3) side chain with a double bond and probably a free terminal acid group. A sulfhydryl reducing agent at the 5 millimolar level such as mercaptoethanol, reduced glutathione, or dithiothreitol was obligatory. Products were varied and were found in both the ethyl acetate-soluble and insoluble fractions after acidification of the incubation mixtures. With internode extracts, about 1 micromole of O(2) was consumed per micromole of p-hydroxycinnamic acid that disappeared in the presence of mercaptoethanol. Tetrahydrafolic acid plus mercaptoethanol were required for a second step oxidation or a parallel reaction; about 2 micromoles of O(2) were consumed per micromole of p-hydroxycinnamic acid that disappeared. Potassium cyanide, diethyldithiocarbamate, ascorbic acid, and ethylenediaminetetraacetate were inhibitory. A similar mercaptoethanol-dependent monophenol oxidase was present in preparations from green shoots that also contained a classical polyphenolase activity. The activity was present in both soluble and particulate (500 to 100,000 gravity) fractions of internodes. Preliminary studies were made of enzyme complexes in the particulate fractions capable of converting phenylalanine and tyrosine to the level of ferulic acid when the above p-hydroxycinnamic acid oxidase was blocked with ascorbic acid. The ratelimiting step was the hydroxylation of p-hydroxycinnamic acid.

Journal Article↗

Direct characterization of caffeoyl esters with antihyaluronidase activity in crude extracts from Echinacea angustifolia roots by fast atom bombardment tandem mass spectrometry.

Fast atom bombardment (FAB-MS) and fast atom bombardment tandem mass spectrometry (FAB-MS/MS) techniques (negative ions) have been successfully applied for identification of the constituents responsible for the antihyaluronidase activity of Echinacea angustifolia roots, whose extracts are widely employed for the adjuvant therapy of chronic inflammatory diseases. Crude extracts from different solvents were tested for antihyaluronidase activity, and those with the greatest inhibitory action (the ethylacetate, butylacetate and chloroform fractions, IC50 0.44, 0.50 e 0.62 mg/ml) were directly analyzed by MS. Full scan mass spectra produced intense molecular anions: collisional activation of these resulted in tandem mass spectra rich in significant product ions. Four main caffeoyl conjugates were detected and identified by tandem mass spectrometry (daughter and parent ion mode): 2,3-O-dicaffeoyltartaric acid (chicoric acid) and 5-O-dicaffeoylquinic acid (cynarine) and 2-O-caffeoyltartaric acid (caffaric acid) in the ethylacetate fraction. Among these caffeoyl conjugates, chicoric and caftaric acids had the greatest antihyaluronidase activity: IC50 = 0.42 and 0.61 mM, while the IC50 of cynarine and chlorogenic acid were 1.85 and 2.25 mM.

Acetates↗

Inhibition of human immunodeficiency virus type-1 integrase by curcumin.

Curcumin (diferuloylmethane) is the yellow pigment in turmeric (Curcuma longa L.) that is widely used as a spice, food coloring (curry) and preservative. Curcumin exhibits a variety of pharmacological effects including antitumor, anti-inflammatory, and anti-infectious activities and is currently in clinical trials for AIDS patients. The effects of curcumin have been determined on purified human immunodeficiency virus type 1 (HIV-1) integrase. Curcumin has an inhibitory concentration50 (IC50) for strand transfer of 40 microM. Inhibition of an integrase deletion mutant containing only amino acids 50-212 suggests that curcumin interacts with the integrase catalytic core. Two structural analogs, methyl cinnamate and chlorogenic acid, were inactive. Energy minimization studies suggest that the anti-integrase activity of curcumin could be due to an intramolecular stacking of two phenyl rings that brings the hydroxyl groups into close proximity. The present data suggest that HIV-1 integrase inhibition may contribute to the antiviral activity of curcumin. These observations suggest new strategies for antiviral drug development that could be based upon curcumin as a lead compound for the development of inhibitors of HIV-1 integrase.

Antiviral Agents↗

Effects of phenolic acids on human phenolsulfotransferases in relation to their antioxidant activity.

Sulfate conjugation by phenolsulfotransferase (PST) enzyme is an important process in the detoxification of xenobiotics and endogenous compounds. There are two forms of PST that are specific for the sulfation of small phenols (PST-P) and monoamines (PST-M). Phenoilc acids have been reported to have important biological and pharmacological properties and may have benefits to human health. In the present study, human platelets were used as a model to investigate the influence of 13 phenolic acids on human PST activity and to evaluate the relationship to their antioxidant activity. The results showed that chlorogenic acid, syringic acid, protocatechuic acid, vanillic acid, sinapic acid, and caffeic acid significantly (p < 0.05) inhibited the activities of both forms of PST by 21-30% at a concentration of 6.7 microM. The activity of PST-P was enhanced (p < 0.05) by p-hydroxybenzoic acid, gallic acid, gentisic acid, o-coumaric acid, p-coumaric acid, and m-coumaric acid at a concentration of 6.7 microM, whereas the activity of PST-M was enhanced by gentisic acid, gallic acid, p-hydroxybenzoic acid, and ferulic acid. The phenolic acids exhibited antioxidant activity as determined by the oxygen radical absorbance capacity (ORAC) assay and Trolox equivalent antioxidant capacity (TEAC) assay, especially gallic acid, p-hydroxybenzoic acid, gentisic acid, and coumaric acid, which had strong activity. The overall effect of phenolic acids tested on the activity of PST-P and PST-M was well correlated to their antioxidant activity of ORAC value (r = 0.71, p < 0.01; and r = 0.66, p < 0.01). These observations suggest that antioxidant phenolic acids might alter sulfate conjugation.

Adult↗