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PubMed2006

The effect of caffeic acid phenethyl ester on bacterial translocation and intestinal damage in cholestatic rats.

We investigated the effect of caffeic acid phenethyl ester in rat ileum injury induced by chronic biliary obstruction. Swiss albino rats were divided into three groups: Group 1, sham (n = 7); Group 2, common bile duct ligation (n = 7); and Group 3, common bile duct ligation plus caffeic acid phenethyl ester (n = 7). In the caffeic acid phenethyl ester-treated rats, ileum tissue levels of malondialdehyde and myeloperoxidase were significantly lower than those of the bile duct-ligated rats (P < 0.001). The levels of tumor necrosis factor-alpha, interleukin-6, and interleukin-1alpha in the caffeic acid phenethyl ester group were significantly lower than those in the bile duct ligation group (P < 0.03, P < 0.01, and P < 0.02 respectively). The present study demonstrates that intraperitoneal administration of caffeic acid phenethyl ester in bile duct-ligated rats reduces intestinal oxidative stress. This effect may be useful in the preservation of intestinal damage in cholestasis.

Animals↗
PubMed2005

Peroxidase-catalyzed in situ polymerization of surface orientated caffeic acid.

Nanoscale surface patterning and polymerization of caffeic acid on 4-aminothiophenol-functionalized gold surfaces has been demonstrated with dip pen nanolithography (DPN). The diphenolic moiety of caffeic acid can be polymerized by biocatalysis with laccase or horseradish peroxidase. In the present study, the DPN patterned features were polymerized in situ through the use of the peroxidase. Using samples prepared by DPN, microcontact printing, and adsorption on macroscopic substrates, the products were characterized by electrostatic force microscopy (EFM), MALDI-TOF, X-ray photoelectron spectroscopy (XPS), UV-vis, and FT-IR. The in situ surface polymerization resulted in the formation of a quinone structure, while the phenyl ester formed in bulk polymerization reactions was not detected. A different coupling site was observed when comparing the polymers obtained from solution (bulk) vs the surface DPN reactions. The structural differences were attributed to surface-induced pre-organization and orientation of the monomers prior to the enzymatic polymerization step. The results of this study expand the application of DPN technology to surface modification and surface chemistry reactions wherein stereo-regularity and regioselectivity can be exploited.

Alloys↗
PubMed2006

Caffeic acid attenuates the decrease in cortical BDNF mRNA expression induced by exposure to forced swimming stress in mice.

We previously reported that caffeic acid produces antidepressive-like effects in the forced swimming test in mice, an animal model of depression. Increased evidence suggests that brain-derived neurotrophic factor (BDNF), a member of the neurotrophin family that has high affinity for the tyrosine kinase receptor B (TrkB), plays an important role in the pathophysiology and treatment of depression. The present study examined whether caffeic acid affects the expression levels of BDNF and TrkB mRNA in brain regions of mice subjected to a forced swimming test. Caffeic acid (4 mg/kg, i.p.) reduced the duration of immobility of mice in the forced swimming test. The levels of BDNF mRNA in the frontal cortex as well as TrkB mRNA in the amygdala were significantly decreased after the forced swimming test, and the former reduction was significantly inhibited by caffeic acid (4 mg/kg, i.p.). Caffeic acid (4 mg/kg, i.p.) did not modify the levels of BDNF and TrkB mRNA in brain regions of naive mice. These results suggest that caffeic acid can attenuate the down-regulation of BDNF transcription that results from stressful conditions.

Animals↗
PubMed1992

Caffeic acid causes metal-dependent damage to cellular and isolated DNA through H2O2 formation.

Pulsed field gel electrophoresis showed that caffeic acid induced DNA strand breaks in cultured human cells in the presence of Mn(II). With alkali treatment, DNA single-strand breaks were observed. The strand breakage was increased by the treatment of buthionine sulphoximine (a GSH synthesis inhibitor) and 3-aminotriazol (a catalase inhibitor) and decreased by catalase, indicating the involvement of H2O2. The DNA damage was decreased by o-phenanthroline, indicating the involvement of transition metal ion. Damage to isolated DNA from c-Ha-ras-1 protooncogene was investigated by a DNA sequencing technique. Caffeic acid caused DNA damage in the presence of Cu(II) but not in the presence of either Mn(II) or Fe(III). Caffeic acid plus Cu(II) induced piperidine-labile sites frequently at thymine residues, especially of the 5'-GTC-3' and 5'-CTG-3' sequences. Typical OH scavengers showed no inhibitory effects. The inhibitory effects of bathocuproine and catalase on Cu(II)-mediated DNA damage suggest that Cu(I) and H2O2 have important roles in the production of active species causing DNA damage. The Cu(II)-mediated DNA damage was enhanced by pre-incubation of caffeic acid with Mn(II). Mn(II)- or Cu(II)-catalyzed autoxidation of caffeic acid produced H2O2 with efficiency of Mn(II) greater than Cu(II). These results suggest that in the presence of Mn(II) or Cu(II), caffeic acid produces H2O2, which is activated by transition metals to cause damage to DNA in vitro and probably in cultured cells.

Amitrole↗
PubMed1990

Oxidation products of caffeic acid as model substances for the antigonadotropic activity of plant extracts.

Phenolic plant constituents exert antigonadotropic activity following an oxidation. The resulting complex mixture of mostly instable products impedes the elucidation of the various oxidation steps as well as the mode of antigonadotropic action. Thus caffeic acid was chosen as a single model phenolic to facilitate the interpretation. The oxidation of caffeic acid with KMnO4 as well as with polyphenoloxidase leads to the instable caffeic acid o-quinone as the first oxidation product. Following the initial oxidation, a number of products was indicated via HPLC. Two of them were isolated and characterized as oligomers of caffeic acid, one of them with phenolic, acid and, quinoic structural components and a relative molecular mass similar to caffeic acid tetramer. It was shown that caffeic acid quinone cannot be the antigonadotropically active principle. Correspondingly, the isolated oxidation products exhibit pronounced antigonadotropic activity. It could be proved that oxidation products of caffeic acid bind to PMSG, forming PMSG-inhibitor-complexes. In such complexes the gonadotropic activity of PMSG is completely abolished.

Animals↗
PubMedDate not supplied

Chemosensitizing activity of caffeic acid in multidrug-resistant MCF-7/Dox human breast carcinoma cells.

The chemosensitizing activity of caffeic acid was examined in parent MCF-7 and multidrug-resistant MCF-7/Dox human breast carcinoma cells. In clonogenic assays, MCF-7/Dox cell was about 135-fold less sensitive to doxorubicin than MCF-7 cells. Caffeic acid (10 microM) slightly altered the colony-forming ability of MCF-7 cells, and markedly reduced the IC50 of doxorubicin (Dox) from 10.8 +/- 1.3 microM to 0.83 +/- 0.21 microM in MCF-7/Dox cells. When compared to MCF-7/Dox cells, intracellular accumulations of [14C] Dox in MCF-7 cells for 1 hour and 12 hours were elevated 2.3-fold and about 6.4-fold, respectively. Doxorubicin accumulations in MCF-7 and MCF-7/Dox cells were not altered in the presence of 10 microM caffeic acid. Both TGF beta 1 and TGF beta 2 isotypes were detected in MCF-7/Dox cells, while only TGF beta 1 was found in MCF-7 cells. The level of TGF beta 1 in MCF-7/Dox cells was about 3-fold greater than that in MCF-7 cells. In cells pretreated with caffeic acid (10 microM), TGF beta 1 and TGF beta 2 levels were overexpressed only in MCF-7/Dox cells by 90% and 60%, respectively. These results suggest that caffeic acid is potentially a chemosensitizing agent with greater selectivity to drug-resistant MCF-7/Dox cells over parent MCF-7 cells and that the chemosensitizing effect is not mediated by altered drug concentrations in the cells, but may be possibly correlated to the induction of TGF beta isotypes.

Biological Transport↗
PubMed2005

Synergistic antioxidative effects of alkamides, caffeic acid derivatives, and polysaccharide fractions from Echinacea purpurea on in vitro oxidation of human low-density lipoproteins.

Preparations of Echinacea are widely used as alternative remedies to prevent the common cold and infections in the upper respiratory tract. After extraction, fractionation, and isolation, the antioxidant activity of three extracts, one alkamide fraction, four polysaccharide-containing fractions, and three caffeic acid derivatives from Echinacea purpurea root was evaluated by measuring their inhibition of in vitro Cu(II)-catalyzed oxidation of human low-density lipoprotein (LDL). The antioxidant activities of the isolated caffeic acid derivatives were compared to those of echinacoside, caffeic acid, and rosmarinic acid for reference. The order of antioxidant activity of the tested substances was cichoric acid > echinacoside > or = derivative II > or = caffeic acid > or = rosmarinic acid > derivative I. Among the extracts the 80% aqueous ethanolic extract exhibited a 10 times longer lag phase prolongation (LPP) than the 50% ethanolic extract, which in turn exhibited a longer LPP than the water extract. Following ion-exchange chromatography of the water extract, the majority of its antioxidant activity was found in the latest eluted fraction (H2O-acidic 3). The antioxidant activity of the tested Echinacea extracts, fractions, and isolated compounds was dose dependent. Synergistic antioxidant effects of Echinacea constituents were found when cichoric acid (major caffeic acid derivative in E. purpurea) or echinacoside (major caffeic acid derivative in Echinacea pallida and Echinacea angustifolia) were combined with a natural mixture of alkamides and/or a water extract containing the high molecular weight compounds. This contributes to the hypothesis that the physiologically beneficial effects of Echinacea are exerted by the multitude of constituents present in the preparations.

Amides↗
PubMed1995

[Lipophilic derivatives of caffeic acid as lipoxygenase inhibitors with antioxidant properties].

We have prepared two lipophilic derivatives of caffeic acid at the carboxylic function--caffeic acid phenethyl ester, an active component of propolis, and N,N'-dicyclohexyl-O-(3,4-dihydroxycinnamoyl)-isourea. Both substances inhibit barley 5-lipoxygenase and soybean 15-lipoxygenase at micromolar concentrations. The inhibition is uncompetitive, dose-dependent and reversible. The caffeic acid derivatives also exhibit antioxidant properties and at a concentration 5-10 microM completely block the production of the reactive oxygen species in human neutrophils and in the cell-free xanthine/xanthine oxidase system.

Antioxidants↗
PubMed2004

[High-performance capillary electrophoresis for determining caffeic acid content in Fujie enema and Taraxacum mongolicum Hand.-Mazz].

OBJECTIVE: To determine caffeic acid content in Fujie enema and the crude traditional Chinese herbal drug Taraxacum mongolicum Hand.-Mazz. for controlling the quality of the enema at the levels of both the crude drugs and the final product. METHODS: Caffeic acid content in both the enema and the crude drug was determined at 313 nm Using high-performance capillary electrophoresis (HPCE), under the optimized conditions achieved with a fused-silica capillary tube (75 micromx0 cm) and 20 mmol/L borate running buffer (pH=9.18) at a constant voltage of 12 kV and a sampling time of 5 s at 25 degrees Celsius. RESULTS: The calibration curve displayed good linear relationship within caffeic acid concentration range of 10 to 100 microg/ml (r=0.999 2). The regression equation was Y=1002.45X-327.87, and the average recovery was more than 95%. CONCLUSION: HPCE is simple, rapid and sensitive in separation and determination of caffeic acid in Fujie enema and the crude drug of Taraxacum mongolicum Hand.-Mazz.

Caffeic Acids↗
PubMed1975

Purification and properties of S-adenosyl-L-methionine: caffeic acid O-methyltransferase from leaves of spinach beet (Beta vulgaris L).

1. An enzyme catalysing the methylation of caffeic acid to ferulic acid, using S-adenosyl-L-methionine as methyl donor, has been extracted from leaves of spinach beet and purified 75-fold to obtain a stable preparation. 2. The enzyme showed optimum activity at pH 6.5, and did not require the addition of Mg2+ for maximum activity. 3. It was most active with caffeic acid, but showed some activity with catechol, protocatechuic acid and 3,4-dihydroxybenzaldehyde. The Km for caffeic acid was 68 muM. 4. 4. The Km for S-adenosyl-L-methionine was 12.5 muM. S-Adenosyl-L-homocystein (Ki = 4.4 muM) was a competitive inhibitor of S-adenosyl-L-methionine. 5. The synthesis of S-adenosyl-L-homocysteine from adenosine and L-homocysteine and its consequent effect on caffeic acid methylation were demonstrated with a partially-purified preparation from spinach-beet leaves, which possessed both S-adenosyl-L-homocysteine hydrolase (EC 3.3.1.1) and adenosine nucleosidase (EC 3.2.2.7) activities. This preparation was also able to catalyse the rapid breakdown of S-adenosyl-L-homocysteine to adenosine and adenine; the possible significance of this reaction in relieving the inhibition of caffeic acid methylation by S-adenosyl-L-homocystein is discussed.

Adenosine↗
PubMed2001

Plasma levels of caffeic acid and antioxidant status after red wine intake.

The aim of this study was to evaluate the bioavailability of caffeic acid and the modification of plasma antioxidant status following red wine intake. Five healthy male volunteers consumed 100, 200, and 300 mL of red wine corresponding to approximately 0.9, 1.8, and 2.7 mg of caffeic acid, respectively. Plasma samples collected at different times (0-300 min) were evaluated for their content of caffeic acid and their total antioxidant status. Both these parameters, i.e., plasma concentration of caffeic acid and antioxidant potential, were dose-dependent and the C(max) was reached at about 60 min after red wine intake. The results indicate that caffeic acid is bioavailable and it may be correlated with the antioxidant potential of plasma.

Adult↗
PubMed1992

Influence of caffeic acid and other o-dihydroxybenzene derivatives on N-methyl-N'-nitro-N-nitrosoguanidine-initiated rat forestomach carcinogenesis.

Promotion effects of the o-dihydroxybenzene derivatives, protocatechuic acid (PCA), dopamine hydrochloride (DAH), dl-dopa and caffeic acid on forestomach and glandular stomach carcinogenesis were investigated in rats pretreated with N-methyl-N'-nitro-N-nitrosoguanidine (MNNG). Groups of 20 male F344 rats were given a single intragastric administration of 150 mg/kg body wt MNNG and starting 1 week later than received diet containing 1.5% PCA, 1.5% DAH, 1.5% dl-dopa or 1% caffeic acid or basal diet alone for 51 weeks and then killed. Other groups of 10-15 rats were given PCA, DAH, dl-dopa or basal diet alone without the MNNG pretreatment. On histological assessment, the incidences of forestomach papillomas and squamous cell carcinomas were significantly enhanced in the group treated with caffeic acid (95 and 100%) as compared with the control values (35 and 10%). Although the incidence was not different, the number of papillomas per rat in the group given DAH (0.79 +/- 0.79) was also significantly increased (0.35 +/- 0.49). PCA and dl-dopa treatments did not modify the development of neoplastic lesions in the forestomach epithelium to any significant extent. None of the four chemicals enhanced glandular stomach carcinogenesis. The results thus demonstrated that whereas caffeic acid and DAH respectively, exert strong and weak promotion activity for rat forestomach carcinogenesis this promotion potential is not shared by all dihydroxybenzene derivatives. An influence of substituents in the para position in addition to the o-dihydroxy moiety is indicated.

Adenocarcinoma↗
PubMed2006

Caffeic acid attenuates neuronal damage, astrogliosis and glial scar formation in mouse brain with cryoinjury.

Traumatic brain injury induces neuron damage in early phase, and astrogliosis and the formation of the glial scar in late phase. Caffeic acid (3, 4-dihydroxycinnamic acid), one of the natural phenolic compounds, exerts neuroprotective effects against ischemic brain injuries with anti-oxidant and anti-inflammatory properties, and by scavenging reactive species. However, whether caffeic acid has protective effects against traumatic brain injury is unknown. Therefore, we determined the effect of caffeic acid on the lesion in the early (1 day) and late phases (7 to 28 days) of cryoinjury in mice. We found that caffeic acid (10 and 50 mg/kg, i.p., for 7 days after cryoinjury) reduced the lesion area and attenuated the neuron loss around the lesion core 1 to 28 days, but attenuated the neuron loss in the lesion core only 1 day after cryoinjury. Moreover, caffeic acid attenuated astrocyte proliferation, glial scar wall formation and glial fibrillary acidic protein (GFAP) protein expression in the late phase of cryoinjury (7 to 28 days). Caffeic acid also inhibited the reduction of superoxide dismutase activity and the increase in malondialdehyde content in the brain 1 day after cryoinjury. These results indicate that caffeic acid exerts a protective effect in traumatic brain injury, especially on glial scar formation in the late phase, which at least is associated with its anti-oxidant ability.

Animals↗
PubMed2000

Caffeic acid as active principle from the fruit of Xanthium strumarium to lower plasma glucose in diabetic rats.

The antihyperglycemic effect of caffeic acid, one of the phenolic compounds contained in the fruit of Xanthium strumarium, was investigated. After an intravenous injection of caffeic acid into diabetic rats of both streptozotocin-induced and insulin-resistant models, a dose-dependent decrease of plasma glucose was observed. However, a similar effect was not produced in normal rats. An insulin-independent action of caffeic acid can thus be considered. Otherwise, this compound reduced the elevation of plasma glucose level in insulin-resistant rats receiving a glucose challenge test. Also, glucose uptake into the isolated adipocytes was raised by caffeic acid in a concentration-dependent manner. Increase of glucose utilization by caffeic acid seems to be responsible for the lowering of plasma glucose.

Animals↗
PubMed1996

Inhibitory effect of caffeic acid phenethyl ester on human leukemia HL-60 cells.

Caffeic acid phenethyl ester (CAPE) was synthesized from caffeic acid and phenethyl alcohol (ratio 1:5) at room temperature with dicyclohexyl carbodiimide (DCC) as a condensing reagent. The yield was about 38%. CAPE was found to arrest the growth of human leukemia HL-60 cells. It also inhibits DNA, RNA and protein synthesis in HL-60 cells with IC50 of 1.0 microM, 5.0 microM and 1.5 microM, respectively.

Anticarcinogenic Agents↗
PubMed2004

Caffeic acid esters activate TREK-1 potassium channels and inhibit depolarization-dependent secretion.

In whole-cell and single-channel patch-clamp recordings from bovine adrenal fasciculata cells, it was discovered that selected caffeic acid derivatives dramatically enhanced the activity of background TREK-1 K+ channels. Cinnamyl 1-3,4-dihydroxy-alpha-cyanocinnamate (CDC), activated TREK-1 when this agent was applied externally to cells or outside-out patches at concentrations of 5 to 10 microM. Structure/activity studies showed that native bTREK-1 channels were also activated by other caffeic acid esters, including caffeic acid phenethyl ester (CAPE), which contain a benzene or furan ring in the ester side chain. The activation of bTREK-1 by caffeic acid derivatives did not occur through inhibition of lipoxygenases because other potent lipoxygenase inhibitors failed to activate bTREK-1. In bovine adrenal zona fasciculata (AZF) cells, bTREK-1 K+ channels set the resting membrane potential. Inhibition of these channels by corticotropin leads to depolarization-dependent Ca2+ entry and cortisol secretion. CDC, which activates up to thousands of dormant bTREK-1 channels in AZF cells, was found to overwhelm the inhibition of bTREK-1 by corticotropin, reverse the membrane depolarization, and inhibit corticotropin-stimulated cortisol secretion. These results identify selected caffeic acid derivatives as novel K+ channel openers that activate TREK-1 background K+ channels. Because of their ability to stabilize the resting membrane potential and oppose electrical activity and depolarization-dependent Ca2+ entry, these compounds may have therapeutic potential as neuroprotective or cardioprotective agents.

Animals↗
PubMed1999

Measurement of unbound caffeic acid in rat blood by on-line microdialysis coupled with liquid chromatography and its application to pharmacokinetic study.

To monitor the levels of caffeic acid in rat blood, an on-line microdialysis system coupled with liquid chromatography was developed. The microdialysis probe was inserted into the jugular vein/right atrium of male Sprague-Dawley rats. Caffeic acid (100 mg/kg, i.v.) was then administered via the femoral vein. Dialysates were automatically injected onto a liquid chromatographic system via an on-line injector. Samples were eluted with a mobile phase containing methanol-100 mM monosodium phosphoric acid (35:65, v/v, pH 2.5). The UV detector wavelength was set at 320 nm. The detection limit of caffeic acid was 20 ng/ml. The in vivo recoveries of the microdialysis probe for caffeic acid at 0.5 and 1 microg/ml were 48.34+/-2.68 and 47.64+/-3.43%, respectively (n=6). Intra- and inter-assay accuracy and precision of the analyses were < or = 10% in the range of 0.05 to 10 microg/ml. Pharmacokinetics analysis of results obtained using such a microdialysis-chromatographic method indicated that unbound caffeic acid in the rat fitted best to a biexponential decay model.

Animals↗
PubMed1995

Anti-AIDS agents, 18. Sodium and potassium salts of caffeic acid tetramers from Arnebia euchroma as anti-HIV agents.

Monosodium and monopotassium salts [2-4] of isomeric caffeic acid tetramers were isolated from Arnebia euchroma as anti-HIV agents. Mixtures of dipotassium and disodium salts [1] of a caffeic acid tetramer and dipotassium and potassium-sodium salts [5] of a caffeic acid tetramer glucoside were also isolated from the active fraction. The structures of 1-5 were characterized by chemical and spectral evidence. Compounds 2-4 demonstrated potent anti-HIV activity with EC50 values of 2.8, 4.0, and 1.5 micrograms/ml, respectively. Treatment of 1-4 with dilute HCl yielded known caffeic acid tetramers [8 and 9], which were found to be less active, indicating the importance of the sodium and potassium salts to the enhanced anti-HIV activity.

Antiviral Agents↗