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PubMed2005

High performance liquid chromatography/electrospray ionization mass spectrometry for simultaneous analysis of alkamides and caffeic acid derivatives from Echinacea purpurea extracts.

Extracts of the plant Echinacea purpurea are widely used for medicinal purposes. Effective quality control of these extracts requires rapid methods to determine their chemical composition. A new method for analysis of caffeic acid derivatives and alkamides from Echinacea extracts has been developed. With this method, isomeric isobutylamides and 2-methylbutylamides can be distinguished, a capability that previously published methods have lacked. Quantitative analyses carried out with this method on E. purpurea extracts that have been stored for 18 months indicate that they contain caftaric acid, cichoric acid, and undeca-2Z,4E-diene-8,10-diynoic acid isobutylamide at concentrations of 0.7, 0.71 and 2.0mg/mL, respectively.

Amides↗
PubMed2004

Caffeic acid phenethyl ester exerts a neuroprotective effect on CNS against pentylenetetrazol-induced seizures in mice.

Since overexcitation of excitatory amino acid is an important mechanism in seizure genesis wherein free radicals have recently been suggested to play a critical role, we explored the effects of caffeic acid phenethyl ester (CAPE) administration in pentylenetetrazole (PTZ)-induced seizure in mice. CAPE prevents the oxidative damage in brain tissue induced by PTZ, scavenging reactive oxygen species (ROS). Our results demonstrate that CAPE treatment which prevents free radical production and ameliorates seizure severity may be useful at least as an adjunctive treatment of seizure disorders.

Animals↗
PubMed2001

The effect of caffeic acid phenethyl ester on ischemia-reperfusion injury in comparison with alpha-tocopherol in rat kidneys.

Oxygen-derived free radicals have been implicated in the pathogenesis of renal injury after ischemia-reperfusion. Caffeic acid phenethyl ester (CAPE), an active component of propolis extract, exhibits antioxidant and anti-inflammatory properties. To determine whether CAPE offers any advantage over alpha-tocopherol, we compared their effects on an in vivo model of renal ischemia-reperfusion injury in rats. CAPE at 10 micromol/kg or alpha-tocopherol at 10 mg/kg was administered intraperitoneally before reperfusion. Acute administration of CAPE suppressed ischemia-reperfusion induced renal lipid peroxidation and tissue injury more than alpha-tocopherol. CAPE may therefore offer a therapeutic advantage in acute injury settings.

Animals↗
PubMed2004

Caffeic acid phenethyl ester as a protective agent against doxorubicin nephrotoxicity in rats.

BACKGROUND: Nephrotoxicity is one of the important side effects of antracycline antibiotics. The aim of this study was to investigate the effects of caffeic acid phenethyl ester (CAPE), an antioxidant agent, against nephrotoxicity induced by doxorubicin (DXR). METHODS: The rats were divided into control, CAPE alone, doxorubicin (20 mg/kg, i.p.) and doxorubicin plus CAPE (10 micromol/kg/day, i.p.) groups. At the end of the 10th day, kidney tissues were removed for light microscopy and analysis. The levels of tissues protein carbonyl content (PC), malondialdehyde (MDA) and nitric oxide (NO) as well as the activities of superoxide dismutase (SOD), catalase (CAT), glutathione peroxidase (GSH-Px) and myeloperoxidase (MPO) were determined. Plasma oxidants and antioxidants were also measured. RESULTS: The activities of CAT and GSH-Px were decreased as well as myeloperoxidase, NO, MDA and PC were increased in renal tissue of doxorubicin group compared with the other groups. Plasma GSH-Px activity was higher in doxorubicin plus CAPE group than the others and plasma MDA level was higher in doxorubicin group than the other groups. There were glomerular vacuolization, tubular desquamation, loss of brush border, and adhesion to Bowman's in the light microscopy in the kidneys of doxorubicin group. The tubules and brush border were almost normal and some of the glomerulus was filled with fine vacuoles in CAPE treated rats. CONCLUSION: Doxorubicin caused renal injury and CAPE treatment prevented lipid peroxidation and protein oxidation in renal tissue and partially preserved glomerulus and tubules.

Animals↗
PubMed1999

The effects of caffeic acid phenethyl ester (CAPE) on spinal cord ischemia/reperfusion injury in rabbits.

OBJECTIVE: Oxygen-derived free radicals have been implicated in the pathogenesis of spinal cord neuronal injury after both trauma and ischemia-reperfusion. Caffeic acid phenethyl ester (CAPE), an active component of propolis extract, exhibits antioxidant properties. This experimental study was designed to determine the effect of CAPE on ischemia-reperfusion of spinal cord in rabbits. METHODS: Forty-one New Zealand white rabbits were used in the study. The animals undergone aortic occlusion were divided into three groups each consisting of 11 rabbits: methylprednisolone (MP), CAPE, and control. CAPE 10 micromol/kg, methyl prednisolone (MP) 30 mg/kg or similar dose saline were injected intraperitoneally before surgical intervention. Animals were subjected to 21 min of cross-clamp time. At the end of occlusion time, the clamps were removed and restoration of the blood flow was verified visually. Animals in sham group (n = 8) underwent a surgical procedure similar to the other groups but the aorta was not occluded. Neurological status was scored by assessment of hindlimb motor function deficit. RESULTS: The scores in CAPE group was different from control groups at 48 h (3.91+/-0.5 vs. 2.91+/-0.7; P = 0.0013). Spinal cord specimens were obtained to determine the tissue levels of malondialdehyde, superoxide dismutase, catalase, and histological changes. Malondialdehyde levels in control group were increased significantly when compared to sham group (124.22+/-24.36 and 41.92+/-10.08 nmol/g wet tissue, P = 0.0003). MDA levels in the CAPE group were lower than MP group and differences between the two groups were statistically significant (56.77+/-15.265 and 107.74+/-19.31 nmol/g wet tissue, P = 0.0001). We did not observe additional tissue injury in CAPE group when compared to control group. SOD and CAT activities were not concordant in all the groups. CONCLUSIONS: These results suggest that CAPE may be an available agent to protect the spinal cord from ischemia-reperfusion injury.

Animals↗
PubMed2006

Protective effects of melatonin and caffeic acid phenethyl ester against retinal oxidative stress in long-term use of mobile phone: a comparative study.

There are numerous reports on the effects of electromagnetic radiation (EMR) in various cellular systems. Melatonin and caffeic acid phenethyl ester (CAPE), a component of honeybee propolis, were recently found to be potent free radical scavengers and antioxidants. Mechanisms of adverse effects of EMR indicate that reactive oxygen species may play a role in the biological effects of this radiation. The present study was carried out to compare the efficacy of the protective effects of melatonin and CAPE against retinal oxidative stress due to long-term exposure to 900 MHz EMR emitting mobile phones. Melatonin and CAPE were administered daily for 60 days to the rats prior to their EMR exposure during our study. Nitric oxide (NO, an oxidant product) levels and malondialdehyde (MDA, an index of lipid peroxidation), were used as markers of retinal oxidative stress in rats following to use of EMR. Superoxide dismutase (SOD), catalase (CAT), and glutathione peroxidase (GSH-Px) activities were studied to evaluate the changes of antioxidant status in retinal tissue. Retinal levels of NO and MDA increased in EMR exposed rats while both melatonin and CAPE caused a significant reduction in the levels of NO and MDA. Likewise, retinal SOD, GSH-Px and CAT activities decreased in EMR exposed animals while melatonin and CAPE caused a significant increase in the activities of these antioxidant enzymes. Treatment of EMR exposed rats with melatonin or CAPE increased the activities of SOD, GSH-Px and CAT to higher levels than those of control rats. In conclusion, melatonin and CAPE reduce retinal oxidative stress after long-term exposure to 900 MHz emitting mobile phone. Nevertheless, there was no statistically significant difference between the efficacies of these two antioxidants against to EMR induced oxidative stress in rat retina. The difference was in only GSH-Px activity in rat retina. Melatonin stimulated the retinal GSH-Px activity more efficiently than CAPE did.

Animals↗
PubMed2004

Caffeic acid phenethyl ester prevents neonatal hypoxic-ischaemic brain injury.

Neonatal hypoxic-ischaemic (HI) brain injury resulting in encephalopathy is a leading cause of morbidity and mortality with no effective treatment. Here we show that caffeic acid phenethyl ester (CAPE), an active component of propolis, administered either before or after an HI insult, significantly prevents HI-induced neonatal rat brain damage in the cortex, hippocampus and thalamus. In addition to blocking HI-induced caspase 3 activation, CAPE also inhibits HI-mediated expression of inducible nitric oxide synthase and caspase 1 in vivo and potently blocks nitric oxide-induced neurotoxicity in vitro. Furthermore, CAPE directly inhibits Ca2+-induced cytochrome c release from isolated brain mitochondria. Thus, CAPE induces neuroprotection against HI-induced neuronal death, possibly by blocking HI-induced inflammation and/or directly inhibiting the HI-induced neuronal death pathway. CAPE may therefore be a novel effective therapy for preventing neonatal HI injury.

Animals↗
PubMed2003

Tyrolobibenzyls E and F from Scorzonera humilis and distribution of caffeic acid derivatives, lignans and tyrolobibenzyls in European taxa of the subtribe Scorzonerinae (Lactuceae, Asteraceae).

A chemosystematic study of the subtribe Scorzonerinae, a subtribe of the Lactuceae tribe of the Asteraceae family was performed, using the recently discovered tyrolobibenzyls as well as lignans and caffeic acid derivatives as diagnostic characters. In addition to the known compounds two new tyrolobibenzyls (E and F) were isolated and their structures were established by mass spectrometry and 1D and 2D NMR spectroscopy. Twenty four samples from rootstocks of seventeen different Scorzonerinae taxa, comprising members of three genera (Podospermum, Scorzonera, and Tragopogon), were analyzed. Tyrolobibenzyls A (1), B (2), C (5), D (3), E (6), and F (4) were identified in crude extracts by means of HPLC retention times, on-line UV spectra and on-line MS/MS spectra. Quantification of these compounds was performed by HPLC, using 2,2-bis-(4-hydroxyphenyl)-propane as an internal standard. Tyrolobibenzyls A-F were only detected in samples from Scorzonera humilis, while chlorogenic acid and 3,5-dicaffeoylquinic acid were detected in all samples investigated. In contrast, caffeoyl tartaric acid and cichoric acid were not detectable in any member of the subtribe Scorzonerinae.

Asteraceae↗
PubMed2001

Caffeic acid phenethyl ester changes the indices of oxidative stress in serum of rats with renal ischaemia-reperfusion injury.

Oxygen-derived free radicals have been implicated in the pathogenesis of renal injury after ischaemia-reperfusion. Caffeic acid phenethyl ester (CAPE), an active component of propolis extract, exhibits antioxidant properties. To investigate whether treatment with either CAPE or alpha-tocopherol modifies the levels of the endogenous indices of oxidant stress, we examined their effects on an in vivo model of renal ischaemia-reperfusion injury in rats. CAPE at 10 micromol kg(-1) or alpha-tocopherol at 10 mg kg(-1) was administered intraperitoneally before reperfusion. Acute administration of both CAPE and alpha-tocopherol altered the indices of oxidative stress differently in renal ischaemia-reperfusion injury.

Adenosine Deaminase↗
PubMed2002

The protective role of caffeic acid phenethyl ester (CAPE) on testicular tissue after testicular torsion and detorsion.

Testicular artery occlusion causes an enhanced formation of reactive oxygen species, which contributes to the pathophysiology of tissue damage. Here, we have investigated the effects of caffeic acid phenethyl ester (CAPE), a new antioxidant and antiinflammatory agent, in rats subjected to testicular torsion/detorsion (T/D). Thirty-five male rats were divided into four groups: sham operation group ( n=8), torsion group ( n=9), T/D+saline group ( n=9) and T/D+CAPE group ( n=9). Rats, except the sham operation group, were subjected to left unilateral torsion (720 degrees rotation in the clockwise direction) without including the epididymis. After torsion (2 h) and detorsion (4 h) periods, rats were sacrificed and bilateral orchidectomy was performed. Testis tissues were washed with cold saline solution, cut into small pieces with scissors, placed into glass bottles and homogenised in four volumes of ice-cold Tris-HCl buffer. Clear supernatant fluid was used for biochemical analyses. Treating rats with CAPE (applied at 10 micro mol/kg, 30 min prior to T/D) attenuated the testicular injury, as well as the increase in the tissue levels of myeloperoxidase and thiobarbituric acid-reactant substances (TBARS) caused by T/D in the testis. Testis tissues showed a significant increase in glutathione peroxidase (GSH-Px) activity compared to the torsion group when CAPE was applied. Taken together, our results clearly demonstrate that CAPE treatment exerts a protective effect on testicular T/D, and part of this effect may be due to inhibiting the neutrophil-mediated cellular injury.

Animals↗
PubMed2005

Determination of the chelating site preferentially involved in the complex of lead(II) with caffeic acid: a spectroscopic and structural study.

The complexation of lead(II) with mono-deprotonated caffeic acid in aqueous solution (pH = 6.50) has been investigated by UV-visible, fluorescence, and vibrational spectroscopies combined with quantum chemical calculations (DFT). The caffeate ion presents two chelating sites in competition: the carboxylate and the catechol functions. Electronic spectroscopies highlighted two different complexed forms with, respectively, 1:1 and 2:1 stoichiometry. The 1:1 complex predominates for low lead concentrations, even if the second complexed form appears before the first chelating site is fully occupied. Both spectroscopic data and calculations reveal that Pb(II) preferentially coordinates with the carboxylate function, in opposition with previous results found for the Al(III) complexation, where the catechol group presents the greater complexing power. The structural and vibrational modifications between the mono-deprotonated ligand and 1:1 complex engendered by the chelation are discussed. Water molecules have been added on the Pb ion to modify its coordination, and structures of Pb(H(2)CA)(H(2)O)(n)(+) with n = 0-4 were optimized. Calculations of theoretical frequencies have permitted us to propose a tentative assignment of infrared and Raman spectra of complexed species.

Journal Article↗
PubMedDate not supplied

The protective effects of caffeic acid phenethyl ester (CAPE) against liver damage induced by cigarette smoke inhalation in rats.

The aim of this study was to investigate the histological and biochemical changes in liver of rats exposed to cigarette smoke and effects of caffeic acid phenetyl ester (CAPE) on these changes. For this purpose, 21 male Wistar rats were divided into three groups. Animals in Group I were used as control. Rats in Group II were exposed to cigarette smoke and rats in Group III were exposed to cigarette smoke and injected daily with CAPE. At the end of the 60-days experimental period, all rats were killed by decapitation and blood samples were obtained. Serum alanine aminotransferase (ALT), aspartate aminotransferase (AST), total bilirubin levels and hepatic superoxide dismutase (SOD) and glutathione peroxidase (GSH-Px ), malondialdehyde (MDA) contents were determined. Following routine histological procedures, liver tissue specimens were examined under a light microscope. The levels of ALT, AST, total bilirubin, SOD, GSH-Px and MDA were significantly increased in rats exposed to cigarette smoke compared with those of the controls. Light microscopic examination of liver specimens from rats exposed to cigarette smoke revealed mononuclear cell infiltration and that some of the hepatocytes had a hyperchromatic nucleus and enlarged sinusoids. The rats which were treated with CAPE along with cigarettes had partially attenuated histological changes associated with cigarette exposure. In conclusion, the damage inflicted by cigarette in the rat liver can be partially prevented by CAPE administration.

Alanine Transaminase↗
PubMed2005

Caffeic acid phenethyl ester decreases acute pneumonitis after irradiation in vitro and in vivo.

BACKGROUND: Lung cancer is relatively resistant to radiation treatment and radiation pneumonitis is a major obstacle to increasing the radiation dose. We previously showed that Caffeic acid phenethyl ester (CAPE) induces apoptosis and increases radiosensitivity in lung cancer. To determine whether CAPE, an antioxidant and an inhibitor of NF-kappa B, could be a useful adjuvant agent for lung cancer treatment, we examine the effects of CAPE on irradiated normal lung tissue in this study. METHODS: We compared the effects of CAPE on cytotoxicity and intracellular oxidative stress in normal lung fibroblast and a lung cancer cell line. For in vivo analysis, whole thorax radiation (single dose 10 Gy and 20 Gy) was delivered to BALB/c male mice with or without CAPE pretreatment. NF- kappaB activation and the expression levels of acute inflammatory cytokines were evaluated in mice after irradiation. RESULTS: The in vitro studies showed that CAPE cause no significant cytotoxicity in normal lung as compared to lung cancer cells. This is probably due to the differential effect on the expression of NF-kappa B between normal and malignant lung cells. The results from in vivo study showed that CAPE treatment decreased the expression of inflammatory cytokines including IL-1 alpha and beta, IL-6, TNF-alpha and TGF- beta, after irradiation. Moreover, histological and immunochemical data revealed that CAPE decreased radiation- induced interstitial pneumonitis and TGF-beta expression. CONCLUSION: This study suggests that CAPE decreases the cascade of inflammatory responses induced by thoracic irradiation without causing toxicity in normal lung tissue. This provides a rationale for combining CAPE and thoracic radiotherapy for lung cancer treatment in further clinical studies.

Animals↗
PubMed2006

Protective effects of caffeic acid phenethyl ester on skeletal muscle ischemia-reperfusion injury in rats.

There is a great evidence that reactive oxygen species (ROS) play an important role in the pathophysiology of ischemia-reperfusion (I/R) injury in skeletal muscle. Caffeic acid phenethyl ester (CAPE) is a component of honeybee propolis. It has antioxidant, anti-inflammatory and free radical scavenger properties. The aim of this study is to determine the protective effects of CAPE against I/R injury in respect of protein oxidation, neutrophil in filtration, and the activities of xanthine oxidase (XO) and adenosine deaminase (AD) on an in vivo model of skeletal muscle I/R injury. Rats were divided into three equal groups each consisting of six rats: Sham operation, I/R, and I/R plus CAPE (I/R+CAPE) groups. CAPE was administered intraperitoneally 60 min before the beginning of the reperfusion. At the end of experimental procedure, blood and gastrocnemius muscle tissues were used for biochemical analyses. Tissue protein carbonyl (PC) levels and the activities of XO, myeloperoxidase (MPO) and AD in I/R group were significantly higher than that of control (p < 0.01, p < 0.05, p < 0.01, p < 0.005, respectively). Administration of CAPE significantly decreased tissue PC levels, MPO and XO activities in skeletal muscle compared to I/R group (p < 0.01, p < 0.05, p < 0.05, respectively). In addition, plasma creatine phosphokinase (CPK), XO and AD activities were decreased in I/R+CAPE group compared to I/R group (p < 0.05, p < 0.05, p < 0.001). The results of this study revealed that free radical attacks may play an important role in the pathogenesis of skeletal muscle I/R injury. Also, the potent free radical scavenger compound, CAPE, may have protective potential in this process. Therefore, it can be speculated that CAPE or other antioxidant agents may be useful in the treatment of I/R injury as well as diffused traumatic injury of skeletal muscle.

Adenosine Deaminase↗
PubMed2003

Stimulation by caffeic acid, coumalic acid, and corilagin of the germination of resting spores of the clubroot pathogen Plasmodiophora brassicae.

Some chemicals were examined for their effects on the germination of resting spores of the clubroot pathogen Plasmodiophora brassicae, and on the control of clubroots in Chinese cabbage. Caffeic acid, coumalic acid, and corilagin stimulated the germination of Plasmodiophora spores and prevented the formation of clubroots in Chinese cabbage. Clubroot might be controlled by agents with germination-stimulating effects.

Brassica↗
PubMedDate not supplied

Protective effects of caffeic acid phenethyl ester on doxorubicin-induced cardiotoxicity in rats.

The prevention of doxorubicin (DXR)-induced cardiotoxicity may be helpful to improve future DXR therapy. The aim of this study was to investigate the cardio-protective effects of caffeic acid phenethyl ester (CAPE), an antioxidant agent, on DXR-induced cardiotoxicity. Rats were divided into three groups and treated with saline, DXR and DXR + CAPE. Rats were treated with CAPE (10 micromol x kg(-1) day(-1) i.p.) or saline starting 2 days before a single dose of DXR (20 mg x kg(-1) i.p.). Ten days later, haemodynamic measurements were performed and the hearts were excised for biochemical analyses and microscopic examination. The heart rate and mean blood pressure were higher and the pulse pressure was lower in the DXR group than in the other two groups. The administration of DXR alone resulted in higher myeloperoxidase activity, lipid peroxidation and protein carbonyl content than in the other groups. The activities of superoxide dismutase and catalase were higher in DXR and DXR + CAPE groups than in the saline group. Rats in the DXR + CAPE group had increased catalase activity in comparison with the DXR group and high glutathione peroxidase activity in comparison with the other two groups. There was severe disruption of mitochondrial fi ne structure in the electron microscopy of the DXR group. In contrast, myocardial microscopy appeared nearly normal in the DXR + CAPE group (as de fi ned at the electron microscopic level). In light of these in vivo haemodynamic, enzymatic and morphological results, we conclude that CAPE pretreatment significantly attenuated DXR-induced cardiac injury, possibly with its antioxidant effects.

Animals↗
PubMed2005

The activity of adenosine deaminase and the level of nitric oxide in spinal cord of methotrexate administered rats: protective effect of caffeic acid phenethyl ester.

The aim of this experimental study was to investigate the possible role of nitric oxide (NO) levels and activity of adenosine deaminase (ADA) in the pathogenesis of methotrexate (MTX)-induced neurotoxicity, to demonstrate the effect of caffeic acid phenethyl ester (CAPE), the potent antioxidant, in decreasing the toxicity. A total of 19 adult male rats were divided into three experimental groups, as follows: group I, control group; group II, MTX-treated group; group III, MTX+CAPE-treated group. In the second day of experiment, MTX was administered intraperitoneally (i.p.) with a single dose of 20mg/kg to group II and group III. CAPE was administered i.p. with a dose of 10 micromol/kg once daily for 7 days to group III. Histopathological findings of the inflammatory reaction were observed in spinal cord of MTX administered rats, compared with control rats. All parameters of inflammatory reaction were significantly decreased in MTX plus CAPE administered rats, compared with MTX administered rats. The injection of MTX caused significant increase in the activity of ADA and in levels NO levels in spinal cord of rats (p=0.007 and p=0.0001, respectively). Co-treatment with CAPE caused a significant decrease in activity of ADA and the levels of NO in spinal cord (p=0.024 and p=0.0001, respectively). Study indicate that NO and ADA may play an important role in the pathogenesis of MTX-induced oxidative spinal cord damage. CAPE may have protective aspects in this process by antioxidant and anti-inflammatory effect and it will become a promising drug in the prevention of undesired side effect of MTX.

Adenosine Deaminase↗
PubMed2003

Sulindac sulfide and caffeic acid phenethyl ester suppress the motility of lung adenocarcinoma cells promoted by transforming growth factor-beta through Akt inhibition.

Cell migration is essential for invasive and metastatic phenotypes of cancer cells. Potential chemopreventive agents of cancer-sulindac sulfide, caffeic acid phenethyl ester (CAPE), curcumin, and (+)-catechin-have been reported to interfere with several types of intracellular signaling. In this study, we examined the effects of these agents on transforming growth factor-beta(TGF-beta)-induced motility and Akt phosphorylation in A549 cells. Judged by gold particle phagokinesis assay, sulindac sulfide, CAPE, and curcumin suppressed the motility of A549 cells promoted by TGF-beta. LY294002, a specific inhibitor of phosphatidylinositol 3-kinase(PI3K)/Akt signaling, also suppressed TGF-beta-induced motility and Akt phosphorylation. Sulindac sulfide and CAPE, but not curcumin, suppressed TGF-beta-induced Akt phosphorylation. We conclude that sulindac sulfide and CAPE suppress the motility promoted by TGF-beta in lung adenocarcinoma cells through the suppression of Akt. Our observations raise the possibility that these agents, except for (+)-catechin, can be applied not only as chemopreventive agents but also as anti-metastatic therapy.

Adenocarcinoma↗