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Sample records for polyphenolic caffeic acid

  1. Effect of high pressure on peanut allergens in the presence of polyphenol oxidase and caffeic acid

    Technology Transfer Automated Retrieval System (TEKTRAN)

    High pressure (HP) enhances enzymatic reactions. Because polyphenol oxidase (PPO) is an enzyme, and reduces IgE binding of peanut allergens in presence of caffeic acid (CA), we postulated that a further reduction in IgE binding can be achieved, using HP together with PPO and CA. Peanut extracts cont...

  2. Coffee polyphenol caffeic acid but not chlorogenic acid increases 5'AMP-activated protein kinase and insulin-independent glucose transport in rat skeletal muscle.

    PubMed

    Tsuda, Satoshi; Egawa, Tatsuro; Ma, Xiao; Oshima, Rieko; Kurogi, Eriko; Hayashi, Tatsuya

    2012-11-01

    Chlorogenic acid is an ester of caffeic and quinic acids, and is one of the most widely consumed polyphenols because it is abundant in foods, especially coffee. We explored whether chlorogenic acid and its metabolite, caffeic acid, act directly on skeletal muscle to stimulate 5'-adenosine monophosphate-activated protein kinase (AMPK). Incubation of rat epitrochlearis muscles with Krebs buffer containing caffeic acid (≥0.1 mM, ≥30 min) but not chlorogenic acid increased the phosphorylation of AMPKα Thr(172), an essential step for kinase activation, and acetyl CoA carboxylase Ser(79), a downstream target of AMPK, in a dose- and time-dependent manner. Analysis of isoform-specific AMPK activity revealed that AMPKα2 activity increased significantly, whereas AMPKα1 activity did not change. This enzyme activation was associated with a reduction in phosphocreatine content and an increased rate of 3-O-methyl-d-glucose transport activity in the absence of insulin. These results suggest that caffeic acid but not chlorogenic acid acutely stimulates skeletal muscle AMPK activity and insulin-independent glucose transport with a reduction of the intracellular energy status. PMID:22227267

  3. Inhibitory effect of caffeic acid phenethyl ester, a plant-derived polyphenolic compound, on rat intestinal contractility.

    PubMed

    Aviello, Gabriella; Scalisi, Caterina; Fileccia, Rosaria; Capasso, Raffaele; Romano, Barbara; Izzo, Angelo A; Borrelli, Francesca

    2010-08-25

    Caffeic acid phenethyl ester (CAPE) exerts pharmacological actions (e.g. anti-inflammatory, chemopreventive) which are relevant for potential clinical application in the digestive tract. However, no study has been published on its possible effects on intestinal motility, to date. In the present study, we investigated the effect of this plant-derived polyphenolic compound on the spontaneous contractions of the rat isolated ileum. CAPE reduced (in a tetrodotoxin-insensitive manner) spontaneous ileal contractions and this effect was reduced by the L-type Ca2+ channel blocker nifedipine and the chelant of calcium ethylenediaminetetraacetic acid. However, the effect of CAPE was not modified by a number of inhibitors/antagonists such as of phentolamine plus propranolol, atropine, tetrodotoxin, cyclopiazonic acid, omega-conotoxin, apamin, NG-nitro-L-arginine methyl ester, 3-isobutyl-1-methylxanthine, 9-(tetrahydro-2-furanyl)-9H-purin-6-amine, 1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one or a combination of SR 140333, SR48968 and SR142801. In conclusion our study shows that (i) CAPE relaxed myogenic contractions of rat ileum and that (ii) this effect occurs, at least in part, throughout a mechanism involving L-type Ca2+ channels. PMID:20451513

  4. Caffeic acid attenuates oxidative stress, learning and memory deficit in intra-cerebroventricular streptozotocin induced experimental dementia in rats.

    PubMed

    Deshmukh, Rahul; Kaundal, Madhu; Bansal, Vikas; Samardeep

    2016-07-01

    Oxidative stress has been implicated in cognitive decline as seen during normal aging and in sporadic Alzheimer's disease (AD). Caffeic acid, a polyphenolic compound, has been reported to possess potent antioxidant and neuroprotective properties. The role of caffeic acid in experimental dementia is not fully understood. Thus the present study was designed to investigate the therapeutic potential of caffeic acid in streptozotocin (STZ)-induced experimental dementia of Alzheimer's type in rats. Streptozotocin (STZ) was administered intracerebroventrically (ICV) on day 1 and 3 (3mg/kg, ICV bilaterally) in Wistar rats. Caffeic acid was administered (10, 20 and 40mg/kg/day p.o.) 1h following STZ infusion upto 21st day. Morris water maze and object recognition task were used to assess learning and memory in rats. Terminally, acetylcholinesterase (AChE) activity and the levels of oxido-nitrosative stress markers were determined in cortical and hippocampal brain regions of rats. STZ produced significant (p<0.001) learning and memory impairment, oxido-nitrosative stress and cholinergic deficit in rats. Whereas, caffeic acid treatment significantly (p<0.001) and dose dependently attenuated STZ induced behavioral and biochemical abnormalities in rats. The observed cognitive improvement following caffeic acid in STZ treated rats may be due to its antioxidant activity and restoration of cholinergic functions. Our results suggest the therapeutic potential of caffeic acid in cognitive disorders such as AD. PMID:27261577

  5. Heterologous production of caffeic acid from tyrosine in Escherichia coli.

    PubMed

    Rodrigues, J L; Araújo, R G; Prather, K L J; Kluskens, L D; Rodrigues, L R

    2015-04-01

    Caffeic acid is a plant secondary metabolite and its biological synthesis has attracted increased attention due to its beneficial effects on human health. In this study, Escherichia coli was engineered for the production of caffeic acid using tyrosine as the initial precursor of the pathway. The pathway design included tyrosine ammonia lyase (TAL) from Rhodotorula glutinis to convert tyrosine to p-coumaric acid and 4-coumarate 3-hydroxylase (C3H) from Saccharothrix espanaensis or cytochrome P450 CYP199A2 from Rhodopseudomonas palustris to convert p-coumaric acid to caffeic acid. The genes were codon-optimized and different combinations of plasmids were used to improve the titer of caffeic acid. TAL was able to efficiently convert 3mM of tyrosine to p-coumaric acid with the highest production obtained being 2.62mM (472mg/L). CYP199A2 exhibited higher catalytic activity towards p-coumaric acid than C3H. The highest caffeic acid production obtained using TAL and CYP199A2 and TAL and C3H was 1.56mM (280mg/L) and 1mM (180mg/L), respectively. This is the first study that shows caffeic acid production using CYP199A2 and tyrosine as the initial precursor. This study suggests the possibility of further producing more complex plant secondary metabolites like flavonoids and curcuminoids. PMID:25765308

  6. Engineering alfalfa to accumulate useful caffeic acid derivatives and characterization of hydroxycinnamoyl-CoA transferases from legumes

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Some forages crops, such as red clover, accumulate high levels of caffeic acid derivatives. Oxidation of these o-diphenols to quinones by endogenous polyphenol oxidases (PPOs) and the subsequent reactions of these quinones (probably with endogenous plant proteases) result in a significant reduction ...

  7. Caffeic acid derivatives in the roots of yacon (Smallanthus sonchifolius).

    PubMed

    Takenaka, Makiko; Yan, Xiaojun; Ono, Hiroshi; Yoshida, Mitsuru; Nagata, Tadahiro; Nakanishi, Tateo

    2003-01-29

    Five caffeic acid derivatives were found in the roots of yacon, Smallanthus sonchifolius (Poepp. and Endl.) H. Robinson, Asteraceae, as the major water-soluble phenolic compounds. The structures of these compounds were determined by analysis of spectroscopic data. Two of these were chlorogenic acid (3-caffeoylquinic acid) and 3,5-dicaffeoylquinic acid, common phenolic compounds in plants of the family Asteraceae. Three were esters of caffeic acid with the hydroxy groups of aldaric acid, derived from hexose. The structure of the aldaric moiety was determined by hydrolysis and comparison of NMR spectra with those of standard aldaric acids. The compounds were novel caffeic acid esters of altraric acid: 2,4- or 3,5-dicaffeoylaltraric acid, 2,5-dicaffeoylaltraric acid, and 2,3,5- or 2,4,5-tricaffeoylaltraric acid. PMID:12537459

  8. Evaluation of inhibitory effects of caffeic acid and quercetin on human liver cytochrome p450 activities.

    PubMed

    Rastogi, Himanshu; Jana, Snehasis

    2014-12-01

    When herbal drugs and conventional allopathic drugs are used together, they can interact in our body which can lead to the potential for herb-drug interactions. This work was conducted to evaluate the herb-drug interaction potential of caffeic acid and quercetin mediated by cytochrome P450 (CYP) inhibition. Human liver microsomes (HLMs) were added to each selective probe substrates of cytochrome P450 enzymes with or without of caffeic acid and quercetin. IC50 , Ki values, and the types of inhibition were determined. Both caffeic acid and quercetin were potent competitive inhibitors of CYP1A2 (Ki = 1.16 and 0.93 μM, respectively) and CYP2C9 (Ki = 0.95 and 1.67 μM, respectively). Caffeic acid was a potent competitive inhibitor of CYP2D6 (Ki = 1.10 μM) and a weak inhibitor of CYP2C19 and CYP3A4 (IC50  > 100 μM). Quercetin was a potent competitive inhibitor of CYP 2C19 and CYP3A4 (Ki = 1.74 and 4.12 μM, respectively) and a moderate competitive inhibitor of CYP2D6 (Ki = 18.72 μM). These findings might be helpful for safe and effective use of polyphenols in clinical practice. Our data indicated that it is necessary to study the in vivo interactions between drugs and pharmaceuticals with dietary polyphenols. PMID:25196644

  9. Adsorption of caffeic acid on titanium dioxide: A spectroscopic study

    NASA Astrophysics Data System (ADS)

    Barreto, Wagner José; Ando, Rômulo A.; Estevão, Bianca Martins; Zanoni, Kassio Papi da Silva

    2012-06-01

    Caffeic acid is an ortho-phenol found in vegetable tissues presenting important properties such as carcinogenesis inhibitor, anti-oxidant, anti-viral, anti-inflammatory and anti-rheumatic actions. It was observed that caffeic acid was not degraded in daylight during the adsorption on TiO2 at pH 4.8. The adsorption fit very well to a Brunauer-Emmett-Teller isotherm equation with a monolayer coverage of 68.15 mg gTiO-1 and saturation coverage of 195.4 mg gTiO-1. A strong adsorption of caffeic acid was verified on TiO2 for the dry solid obtained from the mixture. The Raman and IR spectroscopies revealed that the adsorption should occur through the interaction of the diphenol oxygens with contribution of CC double bond of the acrylic group, however, the carboxylic acid group did not have participation in the adsorption.

  10. Caffeic Acid Derivatives in Dried Lamiaceae and Echinacea purpurea Products

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The concentrations of caffeic acid derivatives within Lamiaceae and Echinacea (herb, spice, tea, and dietary supplement forms) readily available in the U.S. marketplace (n=72) were determined. After the first identification of chicoric acid in Ocimum basilicum (basil), the extent to which chicoric a...

  11. 5-Caffeoylquinic acid and caffeic acid orally administered suppresses P-selectin expression on mouse platelets

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Caffeic acid and 5-caffeoylquinic acid are a naturally occurring phenolic acid and its ester found in human diets. In this paper, potential effects of caffeic acid and 5-caffeoylquinic acid found in coffee and other plant sources on platelet activation were studied via investigating P-selectin expre...

  12. Can propolis and caffeic acid phenethyl ester be promising agents against cyclophosphamide toxicity?

    PubMed Central

    Akyol, Sumeyya; Gulec, Mehmet Akif; Erdemli, Haci Kemal; Akyol, Omer

    2016-01-01

    Propolis is a mixture having hundreds of polyphenols including caffeic acid phenethyl ester (CAPE). They have been using in several medical conditions/diseases in both in vitro and in vivo experimental setup. Cyclophosphamide (CP) has been used to treat a broad of malignancies including Hodgkin’s and non-Hodgkin’s lymphoma, Burkitt’s lymphoma, chronic lymphocytic leukemia, Ewing’s sarcoma, breast cancer, testicular cancer, etc. It may cause several side effects after treatment. In this mini review, the protective effects of propolis and CAPE were compared each other in terms of effectiveness against CP-induced injuries. PMID:27069732

  13. Can propolis and caffeic acid phenethyl ester be promising agents against cyclophosphamide toxicity?

    PubMed

    Akyol, Sumeyya; Gulec, Mehmet Akif; Erdemli, Haci Kemal; Akyol, Omer

    2016-01-01

    Propolis is a mixture having hundreds of polyphenols including caffeic acid phenethyl ester (CAPE). They have been using in several medical conditions/diseases in both in vitro and in vivo experimental setup. Cyclophosphamide (CP) has been used to treat a broad of malignancies including Hodgkin's and non-Hodgkin's lymphoma, Burkitt's lymphoma, chronic lymphocytic leukemia, Ewing's sarcoma, breast cancer, testicular cancer, etc. It may cause several side effects after treatment. In this mini review, the protective effects of propolis and CAPE were compared each other in terms of effectiveness against CP-induced injuries. PMID:27069732

  14. Photodynamics of potent antioxidants: ferulic and caffeic acids.

    PubMed

    Horbury, Michael D; Baker, Lewis A; Quan, Wen-Dong; Greenough, Simon E; Stavros, Vasilios G

    2016-07-14

    The dynamics of ferulic acid (3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid) and caffeic acid (3-(3,4-dihydroxyphenyl)-2-propenoic acid) in acetonitrile, dioxane and water at pH 2.2 following photoexcitation to the first excited singlet state are reported. These hydroxycinnamic acids display both strong ultraviolet absorption and potent antioxidant activity, making them promising sunscreen components. Ferulic and caffeic acids have previously been shown to undergo trans-cis photoisomerization via irradiation studies, yet time-resolved measurements were unable to observe formation of the cis-isomer. In the present study, we are able to observe the formation of the cis-isomer as well as provide timescales of relaxation following initial photoexcitation. PMID:27310931

  15. Synthesis, preliminary bioevaluation and computational analysis of caffeic acid analogues.

    PubMed

    Liu, Zhiqian; Fu, Jianjun; Shan, Lei; Sun, Qingyan; Zhang, Weidong

    2014-01-01

    A series of caffeic acid amides were designed, synthesized and evaluated for anti-inflammatory activity. Most of them exhibited promising anti-inflammatory activity against nitric oxide (NO) generation in murine macrophage RAW264.7 cells. A 3D pharmacophore model was created based on the biological results for further structural optimization. Moreover, predication of the potential targets was also carried out by the PharmMapper server. These amide analogues represent a promising class of anti-inflammatory scaffold for further exploration and target identification. PMID:24857914

  16. Synthesis, Preliminary Bioevaluation and Computational Analysis of Caffeic Acid Analogues

    PubMed Central

    Liu, Zhiqian; Fu, Jianjun; Shan, Lei; Sun, Qingyan; Zhang, Weidong

    2014-01-01

    A series of caffeic acid amides were designed, synthesized and evaluated for anti-inflammatory activity. Most of them exhibited promising anti-inflammatory activity against nitric oxide (NO) generation in murine macrophage RAW264.7 cells. A 3D pharmacophore model was created based on the biological results for further structural optimization. Moreover, predication of the potential targets was also carried out by the PharmMapper server. These amide analogues represent a promising class of anti-inflammatory scaffold for further exploration and target identification. PMID:24857914

  17. Effects of caffeic acid on learning deficits in a model of Alzheimer's disease.

    PubMed

    Wang, Yunliang; Wang, Yutong; Li, Jinfeng; Hua, Linlin; Han, Bing; Zhang, Yuzhen; Yang, Xiaopeng; Zeng, Zhilei; Bai, Hongying; Yin, Honglei; Lou, Jiyu

    2016-09-01

    Caffeic acid is a type of phenolic acid and organic acid. It is found in food (such as tomatoes, carrots, strawberries, blueberries and wheat), beverages (such as wine, tea, coffee and apple juice) as well as Chinese herbal medicines. In the present study, we examined the effects of caffeic acid on learning deficits in a rat model of Alzheimer's disease (AD). The rats were randomly divided into three groups: i) control group, ii) AD model group and iii) caffeic acid group. Caffeic acid significantly rescued learning deficits and increased cognitive function in the rats with AD as demonstrated by the Morris water maze task. Furthermore, caffeic acid administration resulted in a significant decrease in acetylcholinesterase activity and nitrite generation in the rats with AD compared with the AD model group. Furthermore, caffeic acid suppressed oxidative stress, inflammation, nuclear factor‑κB‑p65 protein expression and caspase‑3 activity as well as regulating the protein expression of p53 and phosphorylated (p-)p38 MAPK expression in the rats with AD. These experimental results indicate that the beneficial effects of caffeic acid on learning deficits in a model of AD were due to the suppression of oxidative stress and inflammation through the p38 MAPK signaling pathway. PMID:27430591

  18. A fluorometric assay platform for caffeic acid detection based on the G-quadruplex/hemin DNAzyme.

    PubMed

    Cai, Nan; Li, Yan; Chen, Shufan; Su, Xingguang

    2016-07-21

    In this paper, a fluorometric assay platform for fluorescence detection of caffeic acid was designed based on the peroxidase-mimicking activities of G-quadruplex/hemin DNAzyme. Under the catalysis of the formed G-quadruplex/hemin complex, H2O2 could be decomposed into hydroxyl radicals with strong oxidation properties. Then caffeic acid would be oxidized by the released hydroxyl radicals, resulting in the product caffeic acid-quinone. Normally, caffeic acid has no influence on the fluorescence of graphene quantum dots. But when mixed with the G-quadruplex/hemin complex and H2O2, the fluorescence of graphene quantum dots was obviously quenched by the oxidized caffeic acid. Under the optimized experimental conditions, the quenched fluorescence intensity was linearly correlated with the concentration of caffeic acid, ranging from 2 μM to 350 μM with a detection limit of 200 nM. The proposed method was applied to the determination of caffeic acid in human serum samples with satisfactory results. PMID:27220084

  19. Synthesis, Evaluation of Anticancer Activity and QSAR Study of Heterocyclic Esters of Caffeic Acid

    PubMed Central

    Hajmohamad Ebrahim Ketabforoosh, Shima; Amini, Mohsen; Vosooghi, Mohsen; Shafiee, Abbas; Azizi, Ebrahim; Kobarfard, Farzad

    2013-01-01

    Caffeic acid phenethyl ester (CAPE) suppresses the growth of transformed cells such as human breast cancer cells, hepatocarcinoma , myeloid leukemia, colorectal cancer cells, fibrosarcoma, glioma and melanoma. A group of heterocyclic esters of caffeic acid was synthesized using Mitsunobu reaction and the esters were subjected to further structural modification by electrooxidation of the catechol ring of caffeic acid esters in the presence of sodium benzenesulfinate and sodium toluensulfinate as nucleophiles. Both heterocyclic esters of caffeic acid and their arylsulfonyl derivatives were evaluated for their cytotoxic activity against HeLa, SK-OV-3, and HT-29 cancer cell lines. HeLa cells showed the highest sensitivity to the compounds and heterocyclic esters with no substituent on catechol ring showed better activity compared to their substituted counterparts. QSAR studies reemphasized the importance of molecular shape of the compounds for their cytotoxic activity. PMID:24523750

  20. The sonodegradation of caffeic acid under ultrasound treatment: relation to stability.

    PubMed

    Sun, Yujing; Qiao, Liping; Ye, Xingqian; Liu, Donghong; Zhang, Xianzhong; Huang, Haizhi

    2013-01-01

    The degradation of caffeic acid under ultrasound treatment in a model system was investigated. The type of solvent and temperature were important factors in determining the outcome of the degradation reactions. Liquid height, ultrasonic intensity and duty cycle only affected degradation rate, but did not change the nature of the degradation. The degradation rate of caffeic acid decreased with increasing temperature. Degradation kinetics of caffeic acid under ultrasound fitted a zero-order reaction from -5 to 25 °C. Caffeic acid underwent decomposition and oligomerization reactions under ultrasound. The degradation products were tentatively identified by FT-IR and HPLC-UV-ESIMS to include the corresponding decarboxylation products and their dimers. PMID:23292325

  1. Preparation and characterization of SPION functionalized via caffeic acid

    NASA Astrophysics Data System (ADS)

    Baykal, A.; Amir, Md.; Günerb, S.; Sözeri, H.

    2015-12-01

    Caffeic acid coated superparamagnetic iron oxide nanoparticles (SPION-CFA) was synthesized by reflux method. The structural, spectroscopic and magnetic properties were studied by X-ray diffraction (XRD), Transmission electron microscopy (TEM), Scanning electron microscopy (SEM), and Vibrating sample magnetometer (VSM) techniques. Thermal gravimetric analysis (TG) and Fourier transform infrared spectroscopy (FT-IR) confirmed the presence of CA on the surface of SPION. The theoretical analyzes performed on recorded room temperature VSM spectrum confirmed the formation of superparamagnetic nature of SPION-CFA. The particle size dependent Langevin function was applied to determine the average magnetic particle dimension (Dmag) around 11.93 nm. In accordance, the average crystallite and particle sizes were obtained as 11.40 nm and ~12.00 nm from XRD and TEM measurements. The extrapolated specific saturation magnetization (σs) is 44.11 emu/g and measured magnetic moment is 1.83 μB. These parameters assign small order of magnetization for NPs with respect to bulk Fe3O4. Magnetic anisotropy was offered as uniaxial and calculated effective anisotropy constant (Keff) is 34.82×104 Erg/g. The size-dependent saturation magnetization suggests the existence of a magnetically inactive layer as 1.035 nm for SPION-CFA.

  2. Production of low chlorogenic and caffeic acid containing sunflower meal protein isolate and its use in functional wheat bread making.

    PubMed

    Shchekoldina, Tatiana; Aider, Mohammed

    2014-10-01

    Sunflower meal protein isolate (SMPI) is a promising food additive in different matrices. However, the uses of SMPI are limited because of the presence of antinutritional compounds like polyphenolic substances. Chlorogenic and caffeic acids are the dominants polyphenolics in the SMPI. These substances cause significant changes of the colour of the meal, proteins and food matrices during their extraction and use as food additives. Moreover, these substances lower the nutritional value of the end product due to their interaction with some amino acids such as lysine and methionine. Thus, the removal of these substances is important to enable the use of the SMPI and meal in general in a greater extent in food applications and replacing more expensive protein sources such as soy proteins. The aim of this work was to study the production of functional bread by supplementing wheat flour with sunflower meal protein isolate (SMPI). SMPI with low content of chlorogenic and caffeic acid was usefully produced following alkaline extraction and purification with succinic acid. Purified SMPI showed well balanced amino acid profile and was characterized by high water and fat absorption capacities. It was incorporated to dough formula at 8-12 % of the total wheat flour. The results showed that production of bread supplemented with SMPI was technologically feasible. The supplemented bread had high mass volume and nutritional quality compared to the control bread. The optimal SMPI to incorporate into dough formula without significant alteration of the final bread colour was established at 10 %. This study will be helpful to find economic ways to enhance the nutritional quality of wheat bread and to improve the profitability of sunflower meal residue. PMID:25328173

  3. Modulation of Tamoxifen Cytotoxicity by Caffeic Acid Phenethyl Ester in MCF-7 Breast Cancer Cells.

    PubMed

    Motawi, Tarek K; Abdelazim, Samy A; Darwish, Hebatallah A; Elbaz, Eman M; Shouman, Samia A

    2016-01-01

    Although Tamoxifen (TAM) is one of the most widely used drugs in managing breast cancer, many women still relapse after long-term therapy. Caffeic acid phenethyl ester (CAPE) is a polyphenolic compound present in many medicinal plants and in propolis. The present study examined the effect of CAPE on TAM cytotoxicity in MCF-7 cells. MCF-7 cells were treated with different concentrations of TAM and/or CAPE for 48 h. This novel combination exerted synergistic cytotoxic effects against MCF-7 cells via induction of apoptotic machinery with activation of caspases and DNA fragmentation, along with downregulation of Bcl-2 and Beclin 1 expression levels. However, the mammalian microtubule-associated protein light chain LC 3-II level was unchanged. Vascular endothelial growth factor level was also decreased, whereas levels of glutathione and nitric oxide were increased. In conclusion, CAPE augmented TAM cytotoxicity via multiple mechanisms, providing a novel therapeutic approach for breast cancer treatment that can overcome resistance and lower toxicity. This effect provides a rationale for further investigation of this combination. PMID:26697130

  4. Modulation of Tamoxifen Cytotoxicity by Caffeic Acid Phenethyl Ester in MCF-7 Breast Cancer Cells

    PubMed Central

    Motawi, Tarek K.; Abdelazim, Samy A.; Darwish, Hebatallah A.; Elbaz, Eman M.; Shouman, Samia A.

    2016-01-01

    Although Tamoxifen (TAM) is one of the most widely used drugs in managing breast cancer, many women still relapse after long-term therapy. Caffeic acid phenethyl ester (CAPE) is a polyphenolic compound present in many medicinal plants and in propolis. The present study examined the effect of CAPE on TAM cytotoxicity in MCF-7 cells. MCF-7 cells were treated with different concentrations of TAM and/or CAPE for 48 h. This novel combination exerted synergistic cytotoxic effects against MCF-7 cells via induction of apoptotic machinery with activation of caspases and DNA fragmentation, along with downregulation of Bcl-2 and Beclin 1 expression levels. However, the mammalian microtubule-associated protein light chain LC 3-II level was unchanged. Vascular endothelial growth factor level was also decreased, whereas levels of glutathione and nitric oxide were increased. In conclusion, CAPE augmented TAM cytotoxicity via multiple mechanisms, providing a novel therapeutic approach for breast cancer treatment that can overcome resistance and lower toxicity. This effect provides a rationale for further investigation of this combination. PMID:26697130

  5. Protection of lipids from oxidation by epicatechin, trans-resveratrol, and gallic and caffeic acids in intestinal model systems.

    PubMed

    Kerem, Zohar; Chetrit, David; Shoseyov, Oded; Regev-Shoshani, Gilly

    2006-12-27

    Consumption of polyphenols is associated with health promotion through diet, although many are poorly absorbed in animals and humans alike. Lipid peroxides may reach the intestine and initiate deleterious oxidation. Here we measured inhibition of the oxidation of linoleic acid (LA) in authentic fluid from rat small intestine (RIF) by two dietary polyphenols, a flavonoid, epicatechin (EC), and a stilbene, resveratrol (RV), and by gallic (GA) and caffeic (CA) acids, and their partition coefficients. Both polyphenols inhibited 80%, and CA inhibited 65%, of the production of hexanal. GA was the weakest antioxidant in this assay. Interestingly, measuring peroxides production in RIF showed that only epicatechin inhibited the first stage of oxidation. The oxidizing agent, the antioxidant comound, the solution pH and lipophilicity are known to affect the total antioxidative activity. We suggest that the mechanism of this activity changes in accord with the environment: i.e., RV may act as a free radial scavenger, but here, in protecting lipids in intestinal fluid from oxidation, it acts as a hydrogen atom donor. Since the concentration of phenolics is much higher in the intestinal fluid than is ever achieved in plasma or other body tissues, it is suggested that their antioxidant activity could be exerted in the gastrointestinal tract (GIT), breaking the propagation of lipid peroxides oxidation and production of toxic compounds. PMID:17177572

  6. Nanomolar Caffeic Acid Decreases Glucose Uptake and the Effects of High Glucose in Endothelial Cells

    PubMed Central

    Natarelli, Lucia; Ranaldi, Giulia; Leoni, Guido; Roselli, Marianna; Guantario, Barbara; Comitato, Raffaella; Ambra, Roberto; Cimino, Francesco; Speciale, Antonio; Virgili, Fabio; Canali, Raffaella

    2015-01-01

    Epidemiological studies suggest that moderate and prolonged consumption of coffee is associated with a reduced risk of developing type 2 diabetes but the molecular mechanisms underlying this effect are not known. In this study, we report the effects of physiological concentrations of caffeic acid, easily achievable by normal dietary habits, in endothelial cells cultured in 25 mM of glucose (high glucose, HG). In HG, the presence of 10 nM caffeic acid was associated with a decrease of glucose uptake but not to changes of GLUT-1 membrane localization or mRNA levels. Moreover, caffeic acid countered HG-induced loss of barrier integrity, reducing actin rearrangement and FITC-dextran passage. The decreased flux of glucose associated to caffeic acid affected HG induced apoptosis by down-regulating the expression of initiator (caspase 8 and 9) and effector caspases (caspase 7 and 3) and by increasing the levels of phosphorylated Bcl-2. We also observed that caffeic acid in HG condition was associated to a reduction of p65 subunit nuclear levels with respect to HG alone. NF-κB activation has been shown to lead to apoptosis in HG treated cells and the analysis of the expression of a panel of about 90 genes related to NF-κB signaling pathway revealed that caffeic acid significantly influenced gene expression changes induced by HG. In conclusion, our results suggest that caffeic acid, decreasing the metabolic stress induced by HG, allows the activation of survival mechanisms mediated by a different modulation of NF-κB-related signaling pathways and to the activation of anti-apoptotic proteins. PMID:26544184

  7. Caffeic acid phenethyl ester inhibits liver fibrosis in rats

    PubMed Central

    Li, Mei; Wang, Xiu-Fang; Shi, Juan-Juan; Li, Ya-Ping; Yang, Ning; Zhai, Song; Dang, Shuang-Suo

    2015-01-01

    AIM: To investigate the hepatoprotective effects and antioxidant activity of caffeic acid phenethyl ester (CAPE) in rats with liver fibrosis. METHODS: A total of 75 male Sprague-Dawley rats were randomly assigned to seven experimental groups: a normal group (n = 10), a vehicle group (n = 10), a model group (n = 15), a vitamin E group (n = 10), and three CAPE groups (CAPE 3, 6 and 12 mg/kg, n = 10, respectively). Liver fibrosis was induced in rats by injecting CCl4 subcutaneously, feeding with high fat forage, and administering 30% alcohol orally for 10 wk. Concurrently, CAPE (3, 6 and 12 mg/kg) was intraperitoneally administered daily for 10 wk. After that, serum total bilirubin (TBil), aminotransferase (ALT) and aspartate aminotransferase (AST) levels were measured to assess hepatotoxicity. To investigate antioxidant activity of CAPE, malondialdehyde (MDA), glutathione (GSH) levels, catalase (CAT) and superoxide dismutase (SOD) activities in liver tissue were determined. Moreover, the effect of CAPE on α-smooth muscle actin (α-SMA), a characteristic hallmark of activated hepatic stellate cells (HSCs), and NF-E2-related factor 2 (Nrf2), a key transcription factor for antioxidant systems, was investigated by immunohistochemistry. RESULTS: Compared to the model group, intraperitoneal administration of CAPE decreased TBil, ALT, and AST levels in liver fibrosis rats (P < 0.05), while serum TBil was decreased by CAPE in a dose-dependent manner. In addition, the liver hydroxyproline contents in both the 6 and 12 mg/kg CAPE groups were markedly lower than that in the model group (P < 0.05 and P < 0.001, respectively). CAPE markedly decreased MDA levels and, in turn, increased GSH levels, as well as CAT and SOD activities in liver fibrosis rats compared to the model group (P < 0.05). Moreover, CAPE effectively inhibited α-SMA expression while increasing Nrf2 expression compared to the model group (P < 0.01). CONCLUSION: The protective effects of CAPE against liver

  8. Degradation of caffeic acid in subcritical water and online HPLC-DPPH assay of degradation products.

    PubMed

    Khuwijitjaru, Pramote; Suaylam, Boonyanuch; Adachi, Shuji

    2014-02-26

    Caffeic acid was subjected to degradation under subcritical water conditions within 160-240 °C and at a constant pressure of 5 MPa in a continuous tubular reactor. Caffeic acid degraded quickly at these temperatures; the main products identified by liquid chromatography-diode array detection/mass spectrometry were hydroxytyrosol, protocatechuic aldehyde, and 4-vinylcatechol. The reaction rates for the degradation of caffeic acid and the formation of products were evaluated. Online high-performance liquid chromatography/2,2-diphenyl-1-picryhydrazyl assay was used to determine the antioxidant activity of each product in the solution. It was found that the overall antioxidant activity of the treated solution did not change during the degradation process. This study showed a potential of formation of antioxidants from natural phenolic compounds under these subcritical water conditions, and this may lead to a discovering of novel antioxidants compounds during the extraction by this technique. PMID:24483598

  9. Terpenoids, flavonoids and caffeic acid derivatives from Salvia viridis L. cvar. Blue Jeans.

    PubMed

    Rungsimakan, Supattra; Rowan, Michael G

    2014-12-01

    Three diterpenoids, 1-oxomicrostegiol (1), viroxocin (2), viridoquinone (3), were isolated from the roots of Salvia viridis L. cvar. Blue Jeans. Five known diterpenoids, microstegiol (4), 7α-acetoxy-14-hydroxy-8,13-abietadiene-11,12-dione (5; 7-O-acetylhorminone tautomer), 7α,14-dihydroxy-8,13-abietadiene-11,12-dione (6; horminone tautomer), ferruginol and salvinolonyl 12-methyl ether (7) were also found in the roots together with 1-docosyl ferulate (8), and a mixture of 2-(4'-alkoxyphenyl) ethyl alkanoates (9). Two lupane triterpenoids, 2α-acetoxy-lup-20(29)-en-3β-ol (10), and 3β-acetoxy-lup-20(29)-en-2α-ol (11) were found in the aerial parts together with known compounds, lup-20(29)-ene-2α,3β-diol (12), ursolic acid, oleanolic acid, β-sitosterol and β-sitosterol glucoside. A known phenylpropanoid, trans-verbascoside (or acteoside; 13), was the main constituent in the polar fraction of the aerial part, and it is now reported in the genus Salvia for the first time. Other polyphenolic compounds were cis-verbascoside (14), leucosceptoside A (15), martynoside (16), caffeic acid, 6-O-caffeoyl-glucose (18), rosmarinic acid, salidroside, luteolin-7-O-α-rhamnopyranosyl-(1→6)-β-galactopyranoside, luteolin-7-O-β-galactopyranoside, luteolin-7-O-α-rhamnopyranosyl-(1→6)-β-glucopyranoside, luteolin-7-O-β-glucopyranoside, and apigenin-7-O-β-glucopyranoside. The structures were determined by 1D-, 2D-NMR and HR-ESI-MS techniques. Compounds 6, 10, ferruginol, ursolic acid and oleanolic acid exhibited antibacterial activity against Enterococcus faecalis (ATCC 775) with MIC 50 μM, 25 μM, 50 μM, 12.5 μM, 12.5 μM respectively. Ferruginol, ursolic acid and oleanolic acid were also active against Staphylococcus aureus (ATCC 6571), and Bacillus cereus (ATCC 2599) with MIC 12.5-50 μM. 4 was also active against S.aureus (ATCC 6571) with MIC 50 μM. These values are consistent with previous studies on the antimicrobial activity of Salvia diterpenoids. PMID:25256822

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

    PubMed

    Hsu, F L; Chen, Y C; Cheng, J T

    2000-04-01

    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. PMID:10821047

  11. Antioxidant Activity of Caffeic Acid against Iron-Induced Free Radical Generation--A Chemical Approach.

    PubMed

    Genaro-Mattos, Thiago C; Maurício, Ângelo Q; Rettori, Daniel; Alonso, Antonio; Hermes-Lima, Marcelo

    2015-01-01

    Caffeic acid (CA) is a phenolic compound widely found in coffee beans with known beneficial effects in vivo. Many studies showed that CA has anti-inflammatory, anti-mutagenic, antibacterial and anti-carcinogenic properties, which could be linked to its antioxidant activity. Taking in consideration the reported in vitro antioxidant mechanism of other polyphenols, our working hypothesis was that the CA antioxidant activity could be related to its metal-chelating property. With that in mind, we sought to investigate the chemical antioxidant mechanism of CA against in vitro iron-induced oxidative damage under different assay conditions. CA was able to prevent hydroxyl radical formation promoted by the classical Fenton reaction, as determined by 2-deoxyribose (2-DR) oxidative degradation and DMPO hydroxylation. In addition to its ability to prevent hydroxyl radical formation, CA had a great inhibition of membrane lipid peroxidation. In the lipid peroxidation assays CA acted as both metal-chelator and as hydrogen donor, preventing the deleterious action promoted by lipid-derived peroxyl and alkoxyl radicals. Our results indicate that the observed antioxidant effects were mostly due to the formation of iron-CA complexes, which are able to prevent 2-DR oxidation and DMPO hydroxylation. Noteworthy, the formation of iron-CA complexes and prevention of oxidative damage was directly related to the pH of the medium, showing better antioxidant activity at higher pH values. Moreover, in the presence of lipid membranes the antioxidant potency of CA was much higher, indicating its enhanced effectiveness in a hydrophobic environment. Overall, our results show that CA acts as an antioxidant through an iron chelating mechanism, preventing the formation of free hydroxyl radicals and, therefore, inhibiting Fenton-induced oxidative damage. The chemical properties of CA described here--in association with its reported signaling effects--could be an explanation to its beneficial effects

  12. Antioxidant Activity of Caffeic Acid against Iron-Induced Free Radical Generation—A Chemical Approach

    PubMed Central

    Genaro-Mattos, Thiago C.; Maurício, Ângelo Q.; Rettori, Daniel; Alonso, Antonio; Hermes-Lima, Marcelo

    2015-01-01

    Caffeic acid (CA) is a phenolic compound widely found in coffee beans with known beneficial effects in vivo. Many studies showed that CA has anti-inflammatory, anti-mutagenic, antibacterial and anti-carcinogenic properties, which could be linked to its antioxidant activity. Taking in consideration the reported in vitro antioxidant mechanism of other polyphenols, our working hypothesis was that the CA antioxidant activity could be related to its metal-chelating property. With that in mind, we sought to investigate the chemical antioxidant mechanism of CA against in vitro iron-induced oxidative damage under different assay conditions. CA was able to prevent hydroxyl radical formation promoted by the classical Fenton reaction, as determined by 2-deoxyribose (2-DR) oxidative degradation and DMPO hydroxylation. In addition to its ability to prevent hydroxyl radical formation, CA had a great inhibition of membrane lipid peroxidation. In the lipid peroxidation assays CA acted as both metal-chelator and as hydrogen donor, preventing the deleterious action promoted by lipid-derived peroxyl and alkoxyl radicals. Our results indicate that the observed antioxidant effects were mostly due to the formation of iron-CA complexes, which are able to prevent 2-DR oxidation and DMPO hydroxylation. Noteworthy, the formation of iron-CA complexes and prevention of oxidative damage was directly related to the pH of the medium, showing better antioxidant activity at higher pH values. Moreover, in the presence of lipid membranes the antioxidant potency of CA was much higher, indicating its enhanced effectiveness in a hydrophobic environment. Overall, our results show that CA acts as an antioxidant through an iron chelating mechanism, preventing the formation of free hydroxyl radicals and, therefore, inhibiting Fenton-induced oxidative damage. The chemical properties of CA described here—in association with its reported signaling effects—could be an explanation to its beneficial effects

  13. Prooxidant DNA breakage induced by caffeic acid in human peripheral lymphocytes: Involvement of endogenous copper and a putative mechanism for anticancer properties

    SciTech Connect

    Bhat, S.H.; Azmi, A.S.; Hadi, S.M. . E-mail: smhadi@vsnl.com

    2007-02-01

    Plant-derived dietary material contains several classes of polyphenols such as flavonoids, curcuminoids, stilbenes and hydroxycinnamic acids. They are recognized as naturally occurring antioxidants but also act as prooxidants catalyzing cellular DNA degradation in the presence of transition metal ions such as copper. Earlier we have shown that the stilbene resveratrol is able to mobilize endogenous copper ions leading to oxidative breakage of cellular DNA. In this paper, we show that caffeic acid (a hydroxycinnamic acid), which is a major constituent of coffee, is also capable of DNA breakage in human peripheral lymphocytes. Incubation of lymphocytes with neocuproine inhibited the DNA degradation confirming that Cu(I) is an intermediate in the DNA cleavage reaction. Further, we have also shown that caffeic acid generates oxidative stress in lymphocytes, which is inhibited by scavengers of reactive oxygen species and neocuproine. These results are in further support of our hypothesis that anticancer mechanism of plant polyphenols involves mobilization of endogenous copper, possibly chromatin bound copper, and the consequent prooxidant action.

  14. A Continuous, Quantitative Fluorescent Assay for Plant Caffeic acid O-Methyltransferases

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Plant caffeic acid O-methyltransferases (COMTs) use s-adenosylmethionine (ado-met), as a methyl donor to transmethylate their preferred (phenolic) substrates in-vivo, and will generally utilize a range of phenolic compounds in-vitro. Collazo et al. (2005; Analytical Biochemistry 342: 86-92) have pu...

  15. Functional characterization of cinnamyl alcohol dehydrogenase and caffeic acid O-methyltransferase in Brachypodium distachyon.

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Lignin is a significant recalcitrant in the conversion of plant biomass to bioethanol. Cinnamyl alcohol dehydrogenase (CAD) and caffeic acid O-methyltransferase (COMT) catalyze key steps in the pathway of lignin monomer biosynthesis. Brown midrib mutants in Zea mays and Sorghum bicolor with impaired...

  16. Synthesis and bioactivity of novel caffeic acid esters from Zuccagnia punctata.

    PubMed

    Ramachandra, M S; Subbaraju, G V

    2006-12-01

    Synthesis of novel caffeic acid esters (1 and 2) was accomplished starting from appropriately substituted benzaldehydes (3 and 9). While compound 2 exhibited potent anti-oxidative activity in both the nitroblue tetrazolium and 1,1-diphenyl-2-picrylhydrazyl radical-scavenging models, compound 1 showed moderate 5-lipoxygenase inhibitory activity. PMID:17145655

  17. Inhibitory Effects of Caffeic Acid, a Coffee-Related Organic Acid, on the Propagation of Hepatitis C Virus.

    PubMed

    Tanida, Isei; Shirasago, Yoshitaka; Suzuki, Ryosuke; Abe, Ryo; Wakita, Takaji; Hanada, Kentaro; Fukasawa, Masayoshi

    2015-01-01

    Multipurpose cohort studies have demonstrated that coffee consumption reduces the risk of hepatocellular carcinoma (HCC). Given that one of the main causes of HCC is hepatitis C virus (HCV) infection, we examined the effect of caffeic acid, a major organic acid derived from coffee, on the propagation of HCV using an in vitro naïve HCV particle-infection and production system within human hepatoma-derived Huh-7.5.1-8 cells. When cells were treated with 1% coffee extract or 0.1% caffeic acid for 1-h post HCV infection, the amount of HCV particles released into the medium at 3 and 4 days post-infection considerably decreased. In addition, HCV-infected cells cultured with 0.001% caffeic acid for 4 days, also released less HCV particles into the medium. Caffeic acid treatment inhibited the initial stage of HCV infection (i.e., between virion entry and the translation of the RNA genome) in both HCV genotypes 1b and 2a. These results suggest that the treatment of cells with caffeic acid may inhibit HCV propagation. PMID:25672401

  18. Anti-apoptotic activity of caffeic acid, ellagic acid and ferulic acid in normal human peripheral blood mononuclear cells: a Bcl-2 independent mechanism.

    PubMed

    Khanduja, Krishan Lal; Avti, Pramod Kumar; Kumar, Surender; Mittal, Nidhi; Sohi, Kiranjit Kaur; Pathak, Chander Mohan

    2006-02-01

    Polyphenols have been shown to induce apoptosis in a variety of tumor cells including leukemia both in vitro and in vivo. However, their action on normal human peripheral blood mononuclear cells (PBMCs) during oxidative stress remains to be explored. In this study, we have evaluated the anti-apoptotic and radical scavenging activities of dietary phenolics, namely caffeic acid (CA), ellagic acid (EA) and ferulic acid (FA). H2O2-induced apoptosis in normal human PBMCs was assayed by phosphotidylserine externalization, nucleosomal damage and DNA fragmentation. Incubation of PBMCs with 5 mM H2O2 led to increased Annexin-V binding to externalized phosphatidyl serine (PS), an event of pre-apoptotic stage of the cell. Peripheral blood mononuclear cells pretreated with phenolics could resist H2O2-induced apoptotic damage. Caffeic acid (60 and 120 microM) and EA (100 and 200 microM) caused no change in externalization of PS, whereas FA (100 and 200 microM) increased externalization of PS in PBMCs treated with H2O2. The effects of phenolics were abolished to a large extent by culturing the PBMCs for 24 h after washing the phenolics from the medium. Inhibitory activities of these phenolics on lipid peroxidation were in the order of EA

  19. Biotechnological production of caffeic acid by bacterial cytochrome P450 CYP199A2.

    PubMed

    Furuya, Toshiki; Arai, Yuka; Kino, Kuniki

    2012-09-01

    Caffeic acid is a biologically active molecule that has various beneficial properties, including antioxidant, anticancer, and anti-inflammatory activities. In this study, we explored the catalytic potential of a bacterial cytochrome P450, CYP199A2, for the biotechnological production of caffeic acid. When the CYP199A2 enzyme was reacted with p-coumaric acid, it stoichiometrically produced caffeic acid. The crystal structure of CYP199A2 shows that Phe at position 185 is situated directly above, and only 6.35 Å from, the heme iron. This F185 residue was replaced with hydrophobic or hydroxylated amino acids using site-directed mutagenesis to create mutants with novel and improved catalytic properties. In whole-cell assays with the known substrate of CYP199A2, 2-naphthoic acid, only the wild-type enzyme hydroxylated 2-naphthoic acid at the C-7 and C-8 positions, whereas all of the active F185 mutants exhibited a preference for C-5 hydroxylation. Interestingly, several F185 mutants (F185V, F185L, F185I, F185G, and F185A mutants) also acquired the ability to hydroxylate cinnamic acid, which was not hydroxylated by the wild-type enzyme. These results demonstrate that F185 is an important residue that controls the regioselectivity and the substrate specificity of CYP199A2. Furthermore, Escherichia coli cells expressing the F185L mutant exhibited 5.5 times higher hydroxylation activity for p-coumaric acid than those expressing the wild-type enzyme. By using the F185L whole-cell catalyst, the production of caffeic acid reached 15 mM (2.8 g/liter), which is the highest level so far attained in biotechnological production of this compound. PMID:22729547

  20. Structural, thermal and quantum chemical studies of p-coumaric and caffeic acids

    NASA Astrophysics Data System (ADS)

    Kumar, Naresh; Pruthi, Vikas; Goel, Nidhi

    2015-04-01

    Two hydroxycinnamic acids viz., p-coumaric, and caffeic acids have been extracted and purified from Parthenium hysterophorus, subsequently characterized by elemental analysis, FT-IR, NMR, single crystal X-ray crystallography. The optimized structures of these acids were calculated in terms of density functional theory by Gaussian 09. The validation of experimental and theoretically obtained data for structural parameters such as bond lengths and bond angles has have been carried out to analyze the statistical significance by curve fitting analysis and the values of correlation coefficient found to be 0.985, 0.992, and 0.984, 0.975 in p-coumaric, and caffeic acids, respectively. The calculated HOMO and LUMO energies show the eventual charge transfer interaction within the molecule. Thermal studies were also carried out by thermogravimetry (TG), differential thermogravimetric analysis (DTA), and derivative thermogravimetry (DTG).

  1. Molecularly imprinted polymer for caffeic acid by precipitation polymerization and its application to extraction of caffeic acid and chlorogenic acid from Eucommia ulmodies leaves.

    PubMed

    Miura, Chitose; Matsunaga, Hisami; Haginaka, Jun

    2016-08-01

    Molecularly imprinted polymers (MIPs) for caffeic acid (CA) were prepared using 4-vinylpyridine and methacrylamide (MAM) as functional monomers, divinylbenzene as a crosslinker and acetonitrile-toluene (3:1, v/v) as a porogen by precipitation polymerization. The use of MAM as the co-monomer resulted in the formation of microsphere MIPs and non-imprinted polymers (NIPs) with ca. 3- and 5-μm particle diameters, respectively. Binding experiments and Scatchard analyses revealed that the binding capacity and affinity of the MIP to CA are higher than those of the NIP. The retention and molecular-recognition properties of the prepared MIPs were evaluated using water-acetonitrile and sodium phosphate buffer-acetonitrile as mobile phases in hydrophilic interaction chromatography (HILIC) and reversed-phase chromatography, respectively. In HILIC mode, the MIP showed higher molecular-recognition ability for CA than in reversed-phase mode. In addition to shape recognition, hydrophilic interactions seem to work for the recognition of CA on the MIP in HILIC mode, while hydrogen bonding and hydrophobic interactions seem to work for the recognition of CA in reversed-phase mode. The MIP had a specific molecular-recognition ability for CA in HILIC mode, while other structurally related compounds, such as chlorogenic acid (CGA), gallic acid, protocatechuic acid and vanillic acid, could not be recognized by the MIP. Furthermore, the MIP was successfully applied for extraction of CA and CGA in the leaves of Eucommia ulmodies in HILIC mode. PMID:26776340

  2. Caffeic acid-coated multifunctional magnetic nanoparticles for the treatment and bimodal imaging of tumours.

    PubMed

    Lee, Jun; Kim, Kyoung Sub; Na, Kun

    2016-07-01

    Accurate theragnosis of tumour is essential for improving the life rate of tumour patients. Superparamagnetic iron oxide nanoparticles (SPIONs) have been used as both diagnostic and therapeutic agents. However, their application is often limited because of a lack of water solubility, lack of cancer treatment efficacy, and ineffective targeting of tumour cells. In this report, a double ligand (caffeic acid-polyethylene glycol-folic acid; FA-PEG-CA, caffeic acid-polyethylene glycol-pheophorbide-a; PheoA-PEG-CA) coated iron oxide nanoparticle has been fabricated that overcomes the limitations of conventional SPION. Photosensitizer and tumour targeting ligands were coated on SPION using a ligand-substitution method. We confirmed the successful substitution of oleic acid ligands with FA-PEG-CA and PheoA-PEG-CA ligands by FT-IR spectroscopy. The caffeic acid coated iron oxide nanoparticles (CAMNPs) also demonstrated high water solubility in an aqueous environment and folate-mediated active tumour targeting. The water solubility of CAMNPs was evaluated by DLS measurement and TEM images. The cytotoxicity of CAMNPs increased two-fold in MDA-MB-231 cells at a laser irradiation condition. The fabricated CAMNPs retained their ability to function as both MRI diagnostic and tumour-selective therapeutic agents. These results suggest that these efficient characteristics of CAMNPs can be incorporated into applications, thus enhancing the efficacy of clinical cancer treatment. PMID:27107705

  3. Cold water fish gelatin modification by a natural phenolic cross-linker (ferulic acid and caffeic acid)

    PubMed Central

    Araghi, Maryam; Moslehi, Zeinab; Mohammadi Nafchi, Abdorreza; Mostahsan, Amir; Salamat, Nima; Daraei Garmakhany, Amir

    2015-01-01

    Nowadays use of edible films and coatings is increasing due to their biodegradability and environment friendly properties. Fish gelatin obtained from fish skin wastage can be used as an appropriate protein compound for replacing pork gelatin to produce edible film. In this study films were prepared by combination of fish gelatin and different concentration (0%, 1%, 3%, and 5%) of two phenolic compounds (caffeic acid and ferulic acid). The film was prepared at pH > 10 and temperature of 60˚c under continuous injection of O2 and addition of the plasticizer sorbitol/glycerol. Results showed that solubility, oxygen permeability, and water vapor permeability were decreased for caffeic acid and the highest effect was observed at concentration of 5%. Solubility had a linear relationship with concentration of phenolic compound in film containing ferulic acid, however, no significant change was observed in vapor and O2 permeability. A comparison between two phenolic compounds showed that caffeic acid had the highest effect in decreasing solubility, water vapor permeability, and oxygen permeability. Caffeic acid is more effective phenolic compound compared with Ferulic acid that can increase safety of biodegradable packaging by improving their barrier and physicochemical properties. PMID:26405523

  4. Regioselectivity of glucosylation of caffeic acid by a UDP-glucose:glucosyltransferase is maintained in planta.

    PubMed Central

    Lim, Eng-Kiat; Higgins, Gillian S; Li, Yi; Bowles, Dianna J

    2003-01-01

    Caffeic acid is a phenylpropanoid playing an important role in the pathways leading to lignin synthesis and the production of a wide variety of secondary metabolites. The compound is also an antioxidant and has potential utility as a general protectant against free radicals. Three glucosylated forms of caffeic acid are known to exist: the 3- O - and 4- O -glucosides and the glucose ester. This study describes for the first time a glucosyltransferase [UDP-glucose:glucosyltransferase (UGT)] that is specific for the 3-hydroxyl, and not the 4-hydroxyl, position of caffeic acid. The UGT sequence of Arabidopsis, UGT71C1, has been expressed as a recombinant fusion protein in Escherichia coli, purified and assayed against a range of substrates in vitro. The assay confirmed that caffeic acid as the preferred substrate when compared with other hydroxycinnamates, although UGT71C1 also exhibited substantial activity towards flavonoid substrates, known to have structural features that can be recognized by many different UGTs. The expression of UGT71C1 in transgenic Arabidopsis was driven by the constitutive cauliflower mosaic virus 35 S (CaMV35S) promoter. Nine independent transgenic lines were taken to homozygosity and characterized by Northern-blot analysis, assay of enzyme activity in leaf extracts and HPLC analysis of the glucosides. The level of expression of UGT71C1 was enhanced considerably in several lines, leading to a higher level of the corresponding enzyme activity and a higher level of caffeoyl-3- O -glucoside. The data are discussed in the context of the utility of UGTs for natural product biotransformations. PMID:12741958

  5. Bioactivity and chemical synthesis of caffeic acid phenethyl ester and its derivatives.

    PubMed

    Zhang, Pengxuan; Tang, Yuping; Li, Nian-Guang; Zhu, Yue; Duan, Jin-Ao

    2014-01-01

    Caffeic acid phenethyl ester (CAPE), as one of the main active ingredients of the natural product propolis, shows the unique biological activities such as anti-tumor, anti-oxidation, anti-inflammatory, immune regulation, and so on. These have attracted the attention of many researchers to explore the compound with potent biological activities. This review aims to summarize its bioactivities, synthetic methods and derivatives, which will be helpful for further study and development of CAPE and its derivatives. PMID:25314606

  6. Novel biomarkers of the metabolism of caffeic acid derivatives in vivo.

    PubMed

    Rechner, A R; Spencer, J P; Kuhnle, G; Hahn, U; Rice-Evans, C A

    2001-06-01

    The purpose of this study was to investigate biomarkers of the bioavailability and metabolism of hydroxycinnamate derivatives through the determination of the pharmacokinetics of their urinary elimination and identification of the metabolites excreted. Coffee was used as a rich source of caffeic acid derivatives and human supplementation was undertaken. The results show a highly significant increase in the excretion of ferulic, isoferulic, dihydroferulic acid (3-(4-hydroxy-3-methoxyphenyl)-propionic acid), and vanillic acid postsupplementation relative to the levels presupplementation. Thus, ferulic, isoferulic, and dihydroferulic acids are specific biomarkers for the bioavailability and metabolism of dietary caffeic acid esters. Isoferulic acid is a unique biomarker as it is not a dietary component, however, dihydroferulic acid may well derive from other flavonoids with a structurally related B-ring. 3-Hydroxyhippuric acid has also been identified as an indicator for bioavailability and metabolism of phenolic compounds, and shows a highly significant excretion increase postsupplementation. The results reveal isoferulic acid (and possibly dihydroferulic acid) as novel markers of caffeoyl quinic acid metabolism. PMID:11368919

  7. Au nanoparticles/poly(caffeic acid) composite modified glassy carbon electrode for voltammetric determination of acetaminophen.

    PubMed

    Li, Tianbao; Xu, Juan; Zhao, Lei; Shen, Shaofei; Yuan, Maosen; Liu, Wenming; Tu, Qin; Yu, Ruijin; Wang, Jinyi

    2016-10-01

    An Au nanoparticles/poly(caffeic acid) (AuNPs/PCA) composite modified glassy carbon (GC) electrode was prepared by successively potentiostatic technique in pH 7.4 phosphate buffer solution containing 0.02mM caffeic acid and 1.0mM HAuCl4. Electrochemical characterization of the AuNPs/PCA-GC electrode was investigated by electrochemical impedance spectroscopy and cyclic voltammetry. The electrochemical behavior of acetaminophen (AP) at the AuNPs/PCA-GC electrode was also studied by cyclic voltammetry. Compared with bare GC and poly(caffeic acid) modified GC electrode, the AuNPs/PCA-GC electrode was exhibited excellent electrocatalytic activity toward the oxidation of AP. The plot of catalytic current versus AP concentration showed two linear segments in the concentration ranges 0.2-20µM and 50-1000µM. The detection limit of 14 nM was obtained by using the first range of the calibration plot. The AuNPs/PCA-GC electrode has been successfully applied and validated by analyzing AP in blood, urine and pharmaceutical samples. PMID:27474318

  8. Visible light caffeic acid degradation by carbon-doped titanium dioxide.

    PubMed

    Venditti, Francesco; Cuomo, Francesca; Ceglie, Andrea; Avino, Pasquale; Russo, Mario Vincenzo; Lopez, Francesco

    2015-03-31

    The removal of the phenolic compound, caffeic acid, by photodegradation has been investigated using carbon-doped titanium dioxide particles as a photocatalyst under visible light. UV-vis absorption spectroscopy and gas chromatography-ion trap mass spectrometry analyses revealed a substrate concentration dependence of the removal of caffeic acid from a water solution. The k2 and t(0.5) parameters of each reaction were calculated by fitting kinetics data to a second-order kinetic adsorption model. To evaluate the photodegradation event, the effect of the adsorption process on the whole degradation was also monitored in the absence of light. Adsorption isotherm studies supported by ζ potential and scanning electron microscopy data demonstrated the pivotal role of the absorption mechanism. It was found that the whole photodegradation process is governed by a synergic mechanism in which adsorption and photodegradation are involved. This study, centered on the removal of caffeic acid from aqueous solutions, highlights the potential application of this technology for the elimination of phenolic compounds from olive mill wastewater, a fundamental goal in both the agronomical and environmental fields. PMID:25763603

  9. Optimized photocatalytic degradation of caffeic acid by sol-gel TiO₂.

    PubMed

    García-Montelongo, Xiomara L; Martínez-de la Cruz, Azael; Contreras, David; Mansilla, Héctor D

    2015-01-01

    TiO₂anatase powder was prepared by means of the sol-gel method with titanium(IV) butoxide as precursor. The formation of a tetragonal crystal structure of TiO₂anatase at 500 °C was confirmed by X-ray powder diffraction. The characterization of the samples synthesized was complemented by scanning electron microscopy, diffuse reflectance infrared Fourier transform spectroscopy, nitrogen adsorption-desorption isotherms (Brunauer-Emmett-Teller) and diffuse reflectance spectroscopy. The photocatalytic activity of the TiO₂anatase powder was evaluated in the degradation of caffeic acid in aqueous solution under ultraviolet radiation. A central composite circumscribed design was used to assess the weight of the experimental variables, pH and amount of catalyst in the percentage of caffeic acid degraded and the optimal conditions. The optimized conditions were found to be pH = 5.2 and a load of TiO₂of 1.1 g L⁻¹. Under these conditions more than 90% of caffeic acid degradation was achieved after 30 min of lamp irradiation. At this time the mineralization reached was almost 60%. PMID:25812097

  10. The Quality Changes of Postharvest Mulberry Fruit Treated by Chitosan-g-Caffeic Acid During Cold Storage.

    PubMed

    Yang, Caifeng; Han, Beibei; Zheng, Yu; Liu, Lili; Li, Changlong; Sheng, Sheng; Zhang, Jian; Wang, Jun; Wu, Fuan

    2016-04-01

    This study aimed to characterize the effects of chitosan-g-caffeic acid (CTS-g-CA) on improving the quality and extending the shelf life of postharvest mulberry fruit during storage at 4 °C for 18 d. CTS-g-CA was enzymatically synthesized using laccase from Pleurotus ostreatus as a catalyst. The synergistic effects of CTS-g-CA treatment on mulberry fruit were evaluated using a co-toxicity factor (cf). The results showed that the rotting rate of CTS-g-CA-treated fruit was 37.67% (compared with that of the control at 97.67%) on day 18. The weight loss and malondialdehyde (MDA) contents of the CTS-g-CA-treated mulberry fruit were significantly lower (P < 0.05) than those of the control, CA, CTS, and CA+CTS treatments. Moreover, the DPPH and ABTS radical scavenging activities of the CTS-g-CA treatment were both higher than those of the control. Furthermore, the CTS-g-CA treatment also maintained higher levels of main active substances, such as anthocyanins, ascorbic acid, polyphenols and flavones, in mulberry fruit than the other treatments. Therefore, CTS-g-CA could be used to improve the quality and extend the shelf life of postharvest mulberry fruit during cold storage. PMID:26992122

  11. Combined treatment with caffeic and ferulic acid from Baccharis uncinella C. DC. (Asteraceae) protects against metabolic syndrome in mice

    PubMed Central

    Bocco, B.M.; Fernandes, G.W.; Lorena, F.B.; Cysneiros, R.M.; Christoffolete, M.A.; Grecco, S.S.; Lancellotti, C.L.; Romoff, P.; Lago, J.H.G.; Bianco, A.C.; Ribeiro, M.O.

    2016-01-01

    Fractionation of the EtOH extract from aerial parts of Baccharis uncinella C. DC. (Asteraceae) led to isolation of caffeic and ferulic acids, which were identified from spectroscopic and spectrometric evidence. These compounds exhibit antioxidant and anti-inflammatory properties and have been shown to be effective in the prevention/treatment of metabolic syndrome. This study investigated whether the combined treatment of caffeic and ferulic acids exhibits a more significant beneficial effect in a mouse model with metabolic syndrome. The combination treatment with caffeic and ferulic acids was tested for 60 days in C57 mice kept on a high-fat (40%) diet. The data obtained indicated that treatment with caffeic and ferulic acids prevented gain in body weight induced by the high-fat diet and improved hyperglycemia, hypercholesterolemia and hypertriglyceridemia. The expression of a number of metabolically relevant genes was affected in the liver of these animals, showing that caffeic and ferulic acid treatment results in increased cholesterol uptake and reduced hepatic triglyceride synthesis in the liver, which is a likely explanation for the prevention of hepatic steatosis. In conclusion, the combined treatment of caffeic and ferulic acids displayed major positive effects towards prevention of multiple aspects of the metabolic syndrome and liver steatosis in an obese mouse model. PMID:26840707

  12. Combined treatment with caffeic and ferulic acid from Baccharis uncinella C. DC. (Asteraceae) protects against metabolic syndrome in mice.

    PubMed

    Bocco, B M; Fernandes, G W; Lorena, F B; Cysneiros, R M; Christoffolete, M A; Grecco, S S; Lancellotti, C L; Romoff, P; Lago, J H G; Bianco, A C; Ribeiro, M O

    2016-03-01

    Fractionation of the EtOH extract from aerial parts of Baccharis uncinella C. DC. (Asteraceae) led to isolation of caffeic and ferulic acids, which were identified from spectroscopic and spectrometric evidence. These compounds exhibit antioxidant and anti-inflammatory properties and have been shown to be effective in the prevention/treatment of metabolic syndrome. This study investigated whether the combined treatment of caffeic and ferulic acids exhibits a more significant beneficial effect in a mouse model with metabolic syndrome. The combination treatment with caffeic and ferulic acids was tested for 60 days in C57 mice kept on a high-fat (40%) diet. The data obtained indicated that treatment with caffeic and ferulic acids prevented gain in body weight induced by the high-fat diet and improved hyperglycemia, hypercholesterolemia and hypertriglyceridemia. The expression of a number of metabolically relevant genes was affected in the liver of these animals, showing that caffeic and ferulic acid treatment results in increased cholesterol uptake and reduced hepatic triglyceride synthesis in the liver, which is a likely explanation for the prevention of hepatic steatosis. In conclusion, the combined treatment of caffeic and ferulic acids displayed major positive effects towards prevention of multiple aspects of the metabolic syndrome and liver steatosis in an obese mouse model. PMID:26840707

  13. Reactions of reducing and oxidizing radicals with caffeic acid:. a pulse radiolysis and theoretical study

    NASA Astrophysics Data System (ADS)

    Li, Xifeng; Cai, Zhongli; Katsumura, Yosuke; Wu, Guozhong; Muroya, Yusa

    2001-01-01

    Molecular calculations coupled with pulse radiolysis studies are performed to understand the reactions of radicals with caffeic acid. From molecular calculation, we find that e aq- and ·OH tend to form adducts with caffeic acid, while N 3rad tends to abstract H from 4-hydroxyl group in benzene ring, generating a semi-quinoid radical. Based on comparison of the heat of formation, the most favorable radical attack sites and the most stable radical structures are predicted. The calculation results suggest that the stability of the electron adducts caffeic ions, in good agreement with their experimental second-order decay rate constants (2 k=(1.1±0.2)×10 9, (6.0±0.4)×10 7 and (2.0±0.2)×10 7 M -1 s -1, respectively), determined by pulse radiolysis. Molecular calculations seem to be a powerful tool to predict the stability and structures of transient radicals.

  14. Solvent effects on focused microwave assisted extraction of polyphenolic acids from Eucommia ulmodies.

    PubMed

    Li, Hui; Chen, Bo; Nie, Lihua; Yao, Shouzhuo

    2004-01-01

    An open microwave-assisted extraction system was used to extract gallic acid, protocatechuic acid, chlorogenic acid and caffeic acid from Eucommia ulmodies. The effect of extraction variables, especially solvent, on the recoveries of these polyphenolic compounds was investigated using factorial design. As extracting solvent for these compounds, methanol produced a higher recovery than pure water. For straight chain alcohol solvents, the lower the carbon number, the higher the recoveries of the polyphenolic acids. The optimal ratio of methanol:water:glacial acetic acid in the solvent mixture used in microwave-assisted extraction was 2:8:0.3 (v/v) and this solvent could be directly used as the mobile phase in HPLC separation without additional intermittent treatment as reported in literature. The extraction under the condition of 50% microwave power and 30 s irradiation at a solvent:sample ratio of 10 (mL/g) was found to be the most advantageous. The repeatability test of extraction and chromatographic analysis was satisfactory for the analysis of these polyphenolic compounds. PMID:15508835

  15. Production of curcuminoids from tyrosine by a metabolically engineered Escherichia coli using caffeic acid as an intermediate.

    PubMed

    Rodrigues, Joana L; Araújo, Rafael G; Prather, Kristala L J; Kluskens, Leon D; Rodrigues, Ligia R

    2015-04-01

    Curcuminoids are phenylpropanoids with high pharmaceutical potential. Herein, we report an engineered artificial pathway in Escherichia coli to produce natural curcuminoids through caffeic acid. Arabidopsis thaliana 4-coumaroyl-CoA ligase and Curcuma longa diketide-CoA synthase (DCS) and curcumin synthase (CURS1) were used to produce curcuminoids and 70 mg/L of curcumin was obtained from ferulic acid. Bisdemethoxycurcumin and demethoxycurcumin were also produced, but in lower concentrations, by feeding p-coumaric acid or a mixture of p-coumaric acid and ferulic acid, respectively. Additionally, curcuminoids were produced from tyrosine through the caffeic acid pathway. To produce caffeic acid, tyrosine ammonia lyase from Rhodotorula glutinis and 4-coumarate 3-hydroxylase from Saccharothrix espanaensis were used. Caffeoyl-CoA 3-O-methyltransferase from Medicago sativa was used to convert caffeoyl-CoA to feruloyl-CoA. Using caffeic acid, p-coumaric acid or tyrosine as a substrate, 3.9, 0.3, and 0.2 mg/L of curcumin were produced, respectively. This is the first time DCS and CURS1 were used in vivo to produce curcuminoids and that curcumin was produced by feeding tyrosine. We have shown that curcumin can be produced using a pathway involvoing caffeic acid. This alternative pathway represents a step forward in the heterologous production of curcumin using E. coli. PMID:25641677

  16. Analysis of Organic Acids, Deacetyl Asperulosidic Acid and Polyphenolic Compounds as a Potential Tool for Characterization of Noni (Morinda citrifolia) Products.

    PubMed

    Bittová, Miroslava; Hladůkova, Dita; Roblová, Vendula; Krácmar, Stanislav; Kubán, Petr; Kubán, Vlastimil

    2015-11-01

    Organic acids, deacetyl asperulosidic acid (DAA) and polyphenolic compounds in various noni (Morinda citrifolia L.) products (4 juices, 4 dry fruit powders and 2 capsules with dry fruit powder) were analyzed. Reversed-phase high-performance liquid chromatography (RP-HPLC) coupled with a variable wavelength detector (VWD) and electrospray ionization time-of-flight mass spectrometer (ESI-TOF MS) was applied for simultaneous analysis of organic acids (malic, lactic, citric and succinic acid) and DAA. An RP-HPLC method with diode-array detector (DAD) was developed for the analysis of polyphenolic compound content (rutin, catechin, quercitrin, kaempferol, gallic acid, caffeic acid and p-coumaric acid). The developed methods can contribute to better characterization of available noni products that is required from the consumers. In our study, we discovered significant dissimilarities in the content of DAA, citric acid and several phenolic compounds in some samples. PMID:26749805

  17. Neuroprotective effect of caffeic acid phenethyl ester in 3-nitropropionic acid-induced striatal neurotoxicity.

    PubMed

    Bak, Jia; Kim, Hee Jung; Kim, Seong Yun; Choi, Yun-Sik

    2016-05-01

    Caffeic acid phenethyl ester (CAPE), derived from honeybee hives, is a bioactive compound with strong antioxidant activity. This study was designed to test the neuroprotective effect of CAPE in 3-nitropropionic acid (3NP)-induced striatal neurotoxicity, a chemical model of Huntington's disease (HD). Initially, to test CAPE's antioxidant activity, a 2,2'-azino-bis-3-ethylbenzthiazoline-6-sulfonic acid (ABTS) antioxidant assay was employed, and CAPE showed a strong direct radical-scavenging eff ect. In addition, CAPE provided protection from 3NP-induced neuronal cell death in cultured striatal neurons. Based on these observations, the in vivo therapeutic potential of CAPE in 3NP-induced HD was tested. For this purpose, male C57BL/6 mice were repeatedly given 3NP to induce HD-like pathogenesis, and 30 mg/kg of CAPE or vehicle (5% dimethyl sulfoxide and 95% peanut oil) was administered daily. CAPE did not cause changes in body weight, but it reduced mortality by 29%. In addition, compared to the vehicle-treated group, robustly reduced striatal damage was observed in the CAPE-treated animals, and the 3NP-induced behavioral defi cits on the rotarod test were signifi cantly rescued after the CAPE treatment. Furthermore, immunohistochemical data showed that immunoreactivity to glial fibrillary acidic protein (GFAP) and CD45, markers for astrocyte and microglia activation, respectively, were strikingly reduced. Combined, these data unequivocally indicate that CAPE has a strong antioxidant eff ect and can be used as a potential therapeutic agent against HD. PMID:27162482

  18. Neuroprotective effect of caffeic acid phenethyl ester in 3-nitropropionic acid-induced striatal neurotoxicity

    PubMed Central

    Bak, Jia; Kim, Hee Jung; Kim, Seong Yun

    2016-01-01

    Caffeic acid phenethyl ester (CAPE), derived from honeybee hives, is a bioactive compound with strong antioxidant activity. This study was designed to test the neuroprotective effect of CAPE in 3-nitropropionic acid (3NP)-induced striatal neurotoxicity, a chemical model of Huntington's disease (HD). Initially, to test CAPE's antioxidant activity, a 2,2'-azino-bis-3-ethylbenzthiazoline-6-sulfonic acid (ABTS) antioxidant assay was employed, and CAPE showed a strong direct radical-scavenging eff ect. In addition, CAPE provided protection from 3NP-induced neuronal cell death in cultured striatal neurons. Based on these observations, the in vivo therapeutic potential of CAPE in 3NP-induced HD was tested. For this purpose, male C57BL/6 mice were repeatedly given 3NP to induce HD-like pathogenesis, and 30 mg/kg of CAPE or vehicle (5% dimethyl sulfoxide and 95% peanut oil) was administered daily. CAPE did not cause changes in body weight, but it reduced mortality by 29%. In addition, compared to the vehicle-treated group, robustly reduced striatal damage was observed in the CAPE-treated animals, and the 3NP-induced behavioral defi cits on the rotarod test were signifi cantly rescued after the CAPE treatment. Furthermore, immunohistochemical data showed that immunoreactivity to glial fibrillary acidic protein (GFAP) and CD45, markers for astrocyte and microglia activation, respectively, were strikingly reduced. Combined, these data unequivocally indicate that CAPE has a strong antioxidant eff ect and can be used as a potential therapeutic agent against HD. PMID:27162482

  19. Synthesis and biological activity of arylspiroborate salts derived from caffeic Acid phenethyl ester.

    PubMed

    Hébert, Martin J G; Flewelling, Andrew J; Clark, Trevor N; Levesque, Natalie A; Jean-François, Jacques; Surette, Marc E; Gray, Christopher A; Vogels, Christopher M; Touaibia, Mohamed; Westcott, Stephen A

    2015-01-01

    Two novel boron compounds containing caffeic acid phenethyl ester (CAPE) derivatives have been prepared and characterized fully. These new compounds and CAPE have been investigated for potential antioxidant and antimicrobial properties and their ability to inhibit 5-lipoxygenase and whether chelation to boron improves their biological activity. Sodium salt 4 was generally more active than ammonium salt 5 in the biological assays and surpassed the radical scavenging ability of CAPE. Compounds 4 and 5 were more active than CAPE and Zileuton in human polymorphonuclear leukocytes. These results clearly show the effectiveness of the synthesized salts as transporter of CAPE. PMID:25834744

  20. Synthesis and Biological Activity of Arylspiroborate Salts Derived from Caffeic Acid Phenethyl Ester

    PubMed Central

    Hébert, Martin J. G.; Flewelling, Andrew J.; Clark, Trevor N.; Jean-François, Jacques; Surette, Marc E.; Gray, Christopher A.; Vogels, Christopher M.; Touaibia, Mohamed; Westcott, Stephen A.

    2015-01-01

    Two novel boron compounds containing caffeic acid phenethyl ester (CAPE) derivatives have been prepared and characterized fully. These new compounds and CAPE have been investigated for potential antioxidant and antimicrobial properties and their ability to inhibit 5-lipoxygenase and whether chelation to boron improves their biological activity. Sodium salt 4 was generally more active than ammonium salt 5 in the biological assays and surpassed the radical scavenging ability of CAPE. Compounds 4 and 5 were more active than CAPE and Zileuton in human polymorphonuclear leukocytes. These results clearly show the effectiveness of the synthesized salts as transporter of CAPE. PMID:25834744

  1. Comparative studies on the interaction of caffeic acid, chlorogenic acid and ferulic acid with bovine serum albumin

    NASA Astrophysics Data System (ADS)

    Li, Shuang; Huang, Kelong; Zhong, Ming; Guo, Jun; Wang, Wei-zheng; Zhu, Ronghua

    2010-10-01

    The substitution of the hydrogen on aromatic and esterification of carboxyl group of the phenol compounds plays an important role in their bio-activities. In this paper, caffeic acid (CaA), chlorogenic acid (ChA) and ferulic acid (FA) were selected to investigate the binding to bovine serum albumin (BSA) using UV absorption spectroscopy, fluorescence spectroscopy and synchronous fluorescence spectroscopy. It was found that the methoxyl group substituting for the 3-hydroxyl group of CaA decreased the affinity for BSA and the esterification of carboxyl group of CaA with quinic acid increased the affinities. The affinities of ChA and FA with BSA were more sensitive to the temperature than that of CaA with BSA. Synchronous fluorescence spectroscopy and time-resolved fluorescence indicated that the Stern-Volmer plots largely deviated from linearity at high concentrations and were caused by complete quenching of the tyrosine fluorescence of BSA.

  2. Antioxidant Properties of Caffeic acid Phenethyl Ester and 4-Vinylcatechol in Stripped Soybean Oil.

    PubMed

    Jia, Cai-Hua; Wang, Xiang-Yu; Qi, Jin-Feng; Hong, Soon-Taek; Lee, Ki-Teak

    2016-01-01

    Caffeic acid was used to synthesize 4-vinylcatechol (4-VC) by thermal decarboxylation and to prepare caffeic acid phenethyl ester (CAPE) by esterification reaction. The identities of synthesized products were confirmed by (1)H NMR. Antioxidative activities of 4-VC and CAPE were compared with α-tocopherol and BHT in stripped soybean oil at 60 °C under the dark. To evaluate the degrees of oxidation at different concentrations and combinations, peroxide value (PV) and (1)H NMR were performed. From the results of PV, the formation of primary oxidation products (i.e., hydroperoxides) in stripped soybean oil containing 200 ppm CAPE was the slowest. The relative oxidation degree of 200 ppm CAPE (9.5%) was lower than other samples on 9 d. Similar results were obtained by (1)H NMR analysis. After 15 d of storage, levels of conjugated diene forms and aldehydes of 200 ppm CAPE sample (57.3 and 0.9 mmol/mol oil) were also lower than other treatments. In addition, 4-VC and α-tocopherol were found to have a synergistic antioxidant effect. PMID:26641978

  3. Melatonin biosynthesis requires N-acetylserotonin methyltransferase activity of caffeic acid O-methyltransferase in rice

    PubMed Central

    Byeon, Yeong; Choi, Geun-Hee; Lee, Hyoung Yool; Back, Kyoungwhan

    2015-01-01

    Caffeic acid O-methyltransferase (COMT) methylates N-acetylserotonin into melatonin; that is, it has N-acetylserotonin O-methyltransferase (ASMT) activity. The ASMT activity of COMT was first detected in Arabidopsis thaliana COMT (AtCOMT). To confirm the involvement of COMT on melatonin synthesis in other plant species, the ASMT activity of a COMT from rice (Oryza sativa) (OsCOMT) was evaluated. Purified recombinant OsCOMT protein from Escherichia coli was used to validate the high ASMT activity of OsCOMT, similar to that of AtCOMT. The K m and V max values for the ASMT activity of OsCOMT were 243 µM and 2400 pmol min−1 mg protein−1, which were similar to those of AtCOMT. Similar to AtCOMT, OsCOMT was localized in the cytoplasm. In vitro ASMT activity was significantly inhibited by either caffeic acid or quercetin in a dose-dependent manner. Analogously, in vivo production of melatonin was significantly inhibited by quercetin in 4-week-old detached rice leaves. Lastly, the transgenic rice plants overexpressing rice COMT showed an increase in melatonin levels whereas transgenic rice plants suppressing the rice COMT had a significant decrease on melatonin levels, suggestive of the direct role of COMT in melatonin biosynthesis in plants. PMID:26276868

  4. Regulatory effects of caffeic acid phenethyl ester on neuroinflammation in microglial cells.

    PubMed

    Tsai, Cheng-Fang; Kuo, Yueh-Hsiung; Yeh, Wei-Lan; Wu, Caren Yu-Ju; Lin, Hsiao-Yun; Lai, Sheng-Wei; Liu, Yu-Shu; Wu, Ling-Hsuan; Lu, Jheng-Kun; Lu, Dah-Yuu

    2015-01-01

    Microglial activation has been widely demonstrated to mediate inflammatory processes that are crucial in several neurodegenerative disorders. Pharmaceuticals that can deliver direct inhibitory effects on microglia are therefore considered as a potential strategy to counter balance neurodegenerative progression. Caffeic acid phenethyl ester (CAPE), a natural phenol in honeybee propolis, is known to possess antioxidant, anti-inflammatory and anti-microbial properties. Accordingly, the current study intended to probe the effects of CAPE on microglia activation by using in vitro and in vivo models. Western blot and Griess reaction assay revealed CAPE significantly inhibited the expressions of inducible nitric oxide synthase (NOS), cyclooxygenase (COX)-2 and the production of nitric oxide (NO). Administration of CAPE resulted in increased expressions of hemeoxygenase (HO)-1and erythropoietin (EPO) in microglia. The phosphorylated adenosine monophosphate-activated protein kinase (AMPK)-α was further found to regulate the anti-inflammatory effects of caffeic acid. In vivo results from immunohistochemistry along with rotarod test also revealed the anti-neuroinflammatory effects of CAPE in microglia activation. The current study has evidenced several possible molecular determinants, AMPKα, EPO, and HO-1, in mediating anti-neuroinflammatory responses in microglial cells. PMID:25768341

  5. Regulatory Effects of Caffeic Acid Phenethyl Ester on Neuroinflammation in Microglial Cells

    PubMed Central

    Tsai, Cheng-Fang; Kuo, Yueh-Hsiung; Yeh, Wei-Lan; Wu, Caren Yu-Ju; Lin, Hsiao-Yun; Lai, Sheng-Wei; Liu, Yu-Shu; Wu, Ling-Hsuan; Lu, Jheng-Kun; Lu, Dah-Yuu

    2015-01-01

    Microglial activation has been widely demonstrated to mediate inflammatory processes that are crucial in several neurodegenerative disorders. Pharmaceuticals that can deliver direct inhibitory effects on microglia are therefore considered as a potential strategy to counter balance neurodegenerative progression. Caffeic acid phenethyl ester (CAPE), a natural phenol in honeybee propolis, is known to possess antioxidant, anti-inflammatory and anti-microbial properties. Accordingly, the current study intended to probe the effects of CAPE on microglia activation by using in vitro and in vivo models. Western blot and Griess reaction assay revealed CAPE significantly inhibited the expressions of inducible nitric oxide synthase (NOS), cyclooxygenase (COX)-2 and the production of nitric oxide (NO). Administration of CAPE resulted in increased expressions of hemeoxygenase (HO)-1and erythropoietin (EPO) in microglia. The phosphorylated adenosine monophosphate-activated protein kinase (AMPK)-α was further found to regulate the anti-inflammatory effects of caffeic acid. In vivo results from immunohistochemistry along with rotarod test also revealed the anti-neuroinflammatory effects of CAPE in microglia activation. The current study has evidenced several possible molecular determinants, AMPKα, EPO, and HO-1, in mediating anti-neuroinflammatory responses in microglial cells. PMID:25768341

  6. Homogeneous and heterogeneous degradation of caffeic acid using photocatalysis driven by UVA and solar light.

    PubMed

    Yáñez, Eliana; Santander, Paola; Contreras, David; Yáñez, Jorge; Cornejo, Lorena; Mansilla, Héctor D

    2016-01-01

    Waste water from the wine industry is characterized by a high concentration of dissolved organic matter and the presence of natural phenolic compounds with low biodegradability. High concentrations of phenolic compounds may cause environmental pollution and risks to human health. In this article caffeic acid (CA) was used as a model compound of wine effluent because it is refractory to the conventional wastewater treatments. The oxidation of caffeic acid in water solution (0.01 g L(-1)) by heterogeneous photocatalysis and photo-Fenton reaction was studied using UVA. The optimal conditions for each treatment were performed by multivariate experimental design. The optimal conditions for heterogeneous photocatalysis were pH 5.3 and 0.9 g L(-1) TiO2. In the case of photo-Fenton treatment, optimized variable were 82.4 μmol L(-1) of Fe(2+) and 558.6 μmol L(-1) of H2O2. The degradation profiles of CA were monitored by UV-Vis, HPLC, TOC and COD. To reach 90% of CA removal, 40 and 2 min of reaction, respectively, were required by heterogeneous and photo-Fenton processes, respectively. For comparison purposes, the reactions were also performed under solar light. The use of solar light does not change the efficiency of the photo-Fenton reaction, yet the performance of the heterogeneous process was significantly improved, reaching 90% of degradation in 15 min. PMID:26548918

  7. Preparation and spectral investigation of inclusion complex of caffeic acid with hydroxypropyl-β-cyclodextrin

    NASA Astrophysics Data System (ADS)

    Zhang, Min; Li, Jinxia; Zhang, Liwei; Chao, Jianbin

    2009-01-01

    The inclusion complexation behavior of caffeic acid (CA) with hydroxypropyl-β-cyclodextrin (HP-β-CD) was studied by UV-vis, fluorescence spectroscopy and nuclear magnetic resonance spectroscopy (NMR). Experimental conditions including the concentration of HP-β-CD and media acidity were investigated in detail. The result suggested HP-β-CD was more suitable for including CA in acidity solution. The binding contants ( K) of the inclusion complexes were determined by linear regression analysis and the inclusion ratio was found to be 1:1. The water solubility of CA was increased by inclusion with HP-β-CD according to the phase-solubility diagram. The spatial configuration of complex has been proposed based on 1H NMR and two-dimensional (2D) NMR, the result suggested that CA was entrapped inside the hydrophobic core of HP-β-CD with the lipophilic aromatic ring and the portion of ethylene.

  8. Structure of the photoactive yellow protein reconstituted with caffeic acid at 1.16 A resolution.

    PubMed

    van Aalten, Daan M F; Crielaard, Wim; Hellingwerf, Klaas J; Joshua-Tor, Leemor

    2002-04-01

    A structural study is described of the photoactive yellow protein (PYP) reconstituted with the chromophore derivative 3,4-dihydroxycinnamic acid. The crystal structure of PYP reconstituted with this chromophore at 1.16 A resolution is reported in space group P6(5). This is the first high-resolution structure of a photoreceptor containing a modified chromophore. The introduction of an extra hydroxyl group in the native chromophore (i.e. p-coumaric acid) appears to perturb the structure of the hybrid yellow protein only slightly. The chromophore is bound by the protein in two different conformations, separated by a rotation of 180 degrees of the catechol ring. In combination with available spectroscopic data, it is concluded that the caffeic acid chromophore binds to the protein in a strained conformation, which leads to a faster ejection from the chromophore-binding pocket upon pB formation. PMID:11914481

  9. Photoproduction of glyoxylic acid in model wine: Impact of sulfur dioxide, caffeic acid, pH and temperature.

    PubMed

    Grant-Preece, Paris; Schmidtke, Leigh M; Barril, Celia; Clark, Andrew C

    2017-01-15

    Glyoxylic acid is a tartaric acid degradation product formed in model wine solutions containing iron and its production is greatly increased by exposure to UV-visible light. In this study, the combined effect of sulfur dioxide, caffeic acid, pH and temperature on the light-induced (⩾300nm) production of glyoxylic acid in model wine containing tartaric acid and iron was investigated using a Box-Behnken experimental design and response surface methodology (RSM). Glyoxylic acid produced in the irradiated model wine was present in free and hydrogen sulfite adduct forms and the measured total, free and percentage free glyoxylic acid values were modeled using RSM. Sulfur dioxide significantly decreased the total amount of glyoxylic acid produced, but could not prevent its production, while caffeic acid showed no significant impact. The interaction between pH and temperature was significant, with low pH values and low temperatures giving rise to higher levels of total glyoxylic acid. PMID:27542478

  10. Thermal transformation of bioactive caffeic acid on fumed silica seen by UV-Vis spectroscopy, thermogravimetric analysis, temperature programmed desorption mass spectrometry and quantum chemical methods.

    PubMed

    Kulik, Tetiana V; Lipkovska, Natalia O; Barvinchenko, Valentyna M; Palyanytsya, Borys B; Kazakova, Olga A; Dudik, Olesia O; Menyhárd, Alfréd; László, Krisztina

    2016-05-15

    Thermochemical studies of hydroxycinnamic acid derivatives and their surface complexes are important for the pharmaceutical industry, medicine and for the development of technologies of heterogeneous biomass pyrolysis. In this study, structural and thermal transformations of caffeic acid complexes on silica surfaces were studied by UV-Vis spectroscopy, thermogravimetric analysis, temperature programmed desorption mass spectrometry (TPD MS) and quantum chemical methods. Two types of caffeic acid surface complexes are found to form through phenolic or carboxyl groups. The kinetic parameters of the chemical reactions of caffeic acid on silica surface are calculated. The mechanisms of thermal transformations of the caffeic chemisorbed surface complexes are proposed. Thermal decomposition of caffeic acid complex chemisorbed through grafted ester group proceeds via three parallel reactions, producing ketene, vinyl and acetylene derivatives of 1,2-dihydroxybenzene. Immobilization of phenolic acids on the silica surface improves greatly their thermal stability. PMID:26939077

  11. The role of the catecholic and the electrophilic moieties of caffeic acid in Nrf2/Keap1 pathway activation in ovarian carcinoma cell lines

    PubMed Central

    Sirota, R.; Gibson, D.; Kohen, R.

    2014-01-01

    In recent years, numerous studies have demonstrated the health benefits of polyphenols. A major portion of polyphenols in western diet are derived from coffee, which is one of the most consumed beverages in the world. It has been shown that many polyphenols gain their beneficial properties (e.g. cancer prevention) through the activation of the Nrf2/Keap1 pathway as well as their direct antioxidant activity. However, activation of Nrf2 in cancer cells might lead to resistance towards therapy through induction of phase II enzymes. In the present work we hypothesize that caffeic acid (CA), a coffee polyphenol, might act as an electrophile in addition to its nucleophilic properties and is capable of inducing the Nrf2/EpRE pathway in cancer cells. The results indicate that CA induces Nrf2 translocation into the nucleus and consequently its transcription. It has been demonstrated that generated hydrogen peroxide is involved in the induction process. It has also been found that this process is induced predominantly via the double bond in CA (Michael acceptor). However, surprisingly the presence of both nucleophilic and electrophilic moieties in CA resulted in a synergetic activation of Nrf2 and phase II enzymes. We also found that CA possesses a dual activity, although inducing GSTP1 and GSR, it inhibiting their enzymatic activity. In conclusion, the mechanism of induction of Nrf2 pathway and phase II enzymes by CA has been elucidated. The electrophilic moiety in CA is essential for the oxidation of the Keap1 protein. It should be noted that while the nucleophilic moiety (the catechol/quinone moiety) can provide scavenging ability, it cannot contribute directly to Nrf2 induction. It was found that this process may be induced by H2O2 produced by the catechol group. On the whole, it appears that CA might play a major role in the cancer cells by enhancing their resistance to treatment. PMID:25498967

  12. Molecular cloning, characterization and expression of the caffeic acid O-methyltransferase (COMT) ortholog from kenaf (Hibiscus cannabinus)

    Technology Transfer Automated Retrieval System (TEKTRAN)

    We cloned the full-length of the gene putatively encoding caffeic acid O-methyltransferase (COMT) from kenaf (Hibiscus cannabinus L.) using degenerate primers and the RACE (rapid amplification of cDNA ends) method. Kenaf is an herbaceous and rapidly growing dicotyledonous plant with great potential ...

  13. Protective Effects of Caffeic Acid Phenethyl Ester on Cyclophosphamide-Induced Hemorrhagic Cystitis in Rats.

    PubMed

    Uysal, Ersin; Yılmaz, H Ramazan; Ugan, Yunus; Altuntas, Atila; Dogru, Atalay; Kutlucan, Ali; Tunc, Sevket Ercan

    2015-12-01

    We investigated the protective effect of caffeic acid phenethyl ester (CAPE) on cyclophosphamide-induced hemorrhagic cystitis in rats in comparison with 2-mercaptoethane sulfonate (MESNA). Forty male rats were randomized into four groups: group 1 (control), group 2 (cyclophosphamide), group 3 (cyclophosphamide + MESNA), group 4 (cyclophosphamide + CAPE). Cyclophosphamide injection increased malondialdehyde levels indicating oxidative stress, whereas CAPE and MESNA ameliorated malondialdehyde levels in the bladder (p < 0.05). Only catalase activities were decreased significantly in both groups (cyclophosphamide + MESNA and cyclophosphamide + CAPE, p < 0.05). Pretreatment with CAPE (p < 0.01) resulted in a significant decrease in nitric oxide levels when compared with the cyclophosphamide group. When we consider the studies that show the critical importance of increased nitric oxide levels in pathogenesis of cyclophosphamide-induced hemorrhagic cystitis, we suggest that it would be more beneficial to use MESNA with CAPE to prevent histological damage. PMID:26207616

  14. Antiviral properties of caffeic acid phenethyl ester and its potential application.

    PubMed

    Erdemli, Hacı Kemal; Akyol, Sumeyya; Armutcu, Ferah; Akyol, Omer

    2015-01-01

    Caffeic acid phenethyl ester (CAPE) is found in a variety of plants and well-known the active ingredient of the honeybee propolis. CAPE showed anti-inflammatory, anticarcinogenic, antimitogenic, antiviral, and immunomodulatory properties in several studies. The beneficial effects of CAPE on different health issues attracted scientists to make more studies on CAPE. Specifically, the anti-viral effects of CAPE and its molecular mechanisms may reveal the important properties of virus-induced diseases. CAPE and its targets may have important roles to design new therapeutics and understand the molecular mechanisms of virus-related diseases. In this mini-review, we summarize the antiviral effects of CAPE under the light of medical and chemical literature. PMID:26649239

  15. Future opportunities in preventing ototoxicity: Caffeic acid phenethyl ester may be a candidate (Review).

    PubMed

    Akyol, Sumeyya; Isik, Bunyamin; Altuntas, Aynur; Erden, Gonul; Cakmak, Ozlem; Kurşunlu, S Fatih; Adam, Bahattin; Akyol, Omer

    2015-09-01

    Caffeic acid phenethyl ester (CAPE) is an important active component of propolis, which is derived from honeybee hives. It has received increasing attention in a variety of medical and pharmaceutical research, due to its anti‑oxidant, antiproliferative, anti‑inflammatory, antiviral and antifungal activity, in addition to its antineoplastic properties. Besides the use of CAPE as an antioxidant and anti‑inflammatory agent in a number of in vivo studies of ear disease, its beneficial effects have been reported in the treatment of cancer, arthritis, allergies, heart disease, diabetes, kidney disease, liver disease and neurological disease. CAPE influences a number of biochemical pathways, as well as several targets involved in ear diseases, in particular, in ototoxicity. The protective effects of CAPE in ototoxicity, which may be induced by a number factors, including lipopolysaccharides, hydrogen peroxide and streptomycin, are evaluated and discussed in the present review. PMID:25975288

  16. Stabilization effects of naringenin and caffeic acid on γ-irradiatedEPDM

    NASA Astrophysics Data System (ADS)

    Zaharescu, T.; Jipa, S.; Mantsch, A.; Henderson, D.

    2013-03-01

    The stabilization of ethylene-propylene diene rubber (EPDM) with naringenin and caffeic acid is studied. The selected concentrations were 0.25, 0.50 and 1 phr. The degradation was performed by γ-irradiation. The protective effect of these antioxidants was investigated by isothermal chemiluminescence at 170 °C and FTIR spectroscopy. The synergetic action of these compounds and metallic selenium was also revealed. The exceptional contribution provided by these phenolic stabilizers is characterized by three kinetic parameters: initial CL intensity, oxidation induction time and maximum period of degradation. The radiation stability of stabilized EPDM is efficiently depicted by induction periods which are the minimum 6times longer for unirradiated samples and 2-50 times longer for 50 kGy-irradiated specimens than pristineEPDM.

  17. Survey on the complexation character of p-sulfonatocalix[n]arenes and Caffeic acid

    NASA Astrophysics Data System (ADS)

    Chao, Jianbin; Liu, Yuhong; Zhang, Yan; Wang, Yu; Zhao, Wei; Zhang, Bingtai

    2014-11-01

    In this work the inclusion complex formation of Caffeic acid (CA) with p-sulfonatocalix[n]arenes (SCXn, n = 4, 6, 8) is reported aiming to improve the antioxidant activity, thermal stability and photostability properties of CA. Evidence for the formation was obtained using fluorescence spectroscopy, nuclear magnetic resonance spectroscopy (NMR), pulsed field gradient NMR (PFG-NMR), Fourier transform infrared spectroscopy (FT-IR), differential scanning calorimetry (DSC) and scanning electron microphotographs (SEM). Experimental conditions including concentrations of SCXn and pH were investigated for the inclusion formation in detail. The results showed that CA was able to form inclusion complexes with SCXn in a molar ratio of 1:1, and the formation constants were varied with the pH conditions. NMR spectroscopy indicated that both the aromatic ring and the vinyl group of CA were partially covered by SCXn.

  18. Caffeic acid phenethyl ester: its protective role against certain major eye diseases.

    PubMed

    Akyol, Sumeyya; Ugurcu, Veli; Balci, Mehmet; Gurel, Ayse; Erden, Gonul; Cakmak, Ozlem; Akyol, Omer

    2014-11-01

    As an effective compound found mainly in the honeybee product propolis, caffeic acid phenethyl ester (CAPE) has been commonly utilized as a medicine and remedial agent, in a number of countries. Specifically, it might inhibit nuclear factor kappa B at micromolar concentrations and demonstrate antioxidant, antineoplastic, antiproliferative, cytostatic, antiviral, antibacterial, antifungal, and anti-inflammatory features. This review article summarizes the recent progress regarding the favorable effects of CAPE on a number of eye disease models, including cataract and posterior capsule opacification, corneal diseases, retina and optic nerve-related diseases, ischemia/reperfusion injury of retina, inflammation and infection-related diseases. CAPE has been found to exhibit promising efficacy, with minimal adverse effects, in animal and cell culture studies of several eye diseases. PMID:25100535

  19. Antiviral properties of caffeic acid phenethyl ester and its potential application

    PubMed Central

    Erdemli, Hacı Kemal; Akyol, Sumeyya; Armutcu, Ferah; Akyol, Omer

    2015-01-01

    Caffeic acid phenethyl ester (CAPE) is found in a variety of plants and well-known the active ingredient of the honeybee propolis. CAPE showed anti-inflammatory, anticarcinogenic, antimitogenic, antiviral, and immunomodulatory properties in several studies. The beneficial effects of CAPE on different health issues attracted scientists to make more studies on CAPE. Specifically, the anti-viral effects of CAPE and its molecular mechanisms may reveal the important properties of virus-induced diseases. CAPE and its targets may have important roles to design new therapeutics and understand the molecular mechanisms of virus-related diseases. In this mini-review, we summarize the antiviral effects of CAPE under the light of medical and chemical literature. PMID:26649239

  20. Caffeic acid phenethyl ester suppresses monocyte adhesion to the endothelium by inhibiting NF-κB/NOX2-derived ROS signaling.

    PubMed

    Nakahara, Risa; Makino, Junya; Kamiya, Tetsuro; Hara, Hirokazu; Adachi, Tetsuo

    2016-05-01

    Caffeic acid phenethyl ester (CAPE), one of the major polyphenols, exhibits anti-oxidative, anti-bacterial, and anti-cancer properties. Atherosclerosis is a chronic inflammatory disease, the progression of which is closely related to the accumulated adhesion of inflammatory monocytes/macrophages to the endothelium. We herein determined whether CAPE and its derivatives suppressed THP-1 cell adhesion to human umbilical vein endothelial cells (HUVEC). Of the four polyphenols tested, CAPE significantly suppressed the 12-O-tetradecanoylphorbol 13-acetate (TPA)-elicited expression of cluster for differentiation (CD) 11b, 14, and 36, and this was accompanied by the inhibition of THP-1 cell adhesion to HUVEC. CAPE also suppressed the activation of TPA-elicited nuclear factor-κB (NF-κB) and accumulation of NADPH oxidase 2 (NOX2)-derived reactive oxygen species (ROS), but did not affect extracellular signal-regulated kinase (ERK) phosphorylation. Taken together, these results demonstrated that CAPE suppressed THP-1 cell adhesion to HUVEC through, at least in part, the NF-κB, NOX2, and ROS-derived signaling axis. PMID:27257341

  1. Caffeic acid phenethyl ester suppresses monocyte adhesion to the endothelium by inhibiting NF-κB/NOX2-derived ROS signaling

    PubMed Central

    Nakahara, Risa; Makino, Junya; Kamiya, Tetsuro; Hara, Hirokazu; Adachi, Tetsuo

    2016-01-01

    Caffeic acid phenethyl ester (CAPE), one of the major polyphenols, exhibits anti-oxidative, anti-bacterial, and anti-cancer properties. Atherosclerosis is a chronic inflammatory disease, the progression of which is closely related to the accumulated adhesion of inflammatory monocytes/macrophages to the endothelium. We herein determined whether CAPE and its derivatives suppressed THP-1 cell adhesion to human umbilical vein endothelial cells (HUVEC). Of the four polyphenols tested, CAPE significantly suppressed the 12-O-tetradecanoylphorbol 13-acetate (TPA)-elicited expression of cluster for differentiation (CD) 11b, 14, and 36, and this was accompanied by the inhibition of THP-1 cell adhesion to HUVEC. CAPE also suppressed the activation of TPA-elicited nuclear factor-κB (NF-κB) and accumulation of NADPH oxidase 2 (NOX2)-derived reactive oxygen species (ROS), but did not affect extracellular signal-regulated kinase (ERK) phosphorylation. Taken together, these results demonstrated that CAPE suppressed THP-1 cell adhesion to HUVEC through, at least in part, the NF-κB, NOX2, and ROS-derived signaling axis. PMID:27257341

  2. Fungal biotransformation of chlorogenic and caffeic acids by Fusarium graminearum: New insights in the contribution of phenolic acids to resistance to deoxynivalenol accumulation in cereals.

    PubMed

    Gauthier, Léa; Bonnin-Verdal, Marie-Noelle; Marchegay, Gisèle; Pinson-Gadais, Laetitia; Ducos, Christine; Richard-Forget, Florence; Atanasova-Penichon, Vessela

    2016-03-16

    Fusarium Head Blight and Gibberella Ear Rot, mainly caused by the fungi Fusarium graminearum and Fusarium culmorum, are two of the most devastating diseases of small-grain cereals and maize. In addition to yield loss, these diseases frequently result in contamination of kernels with toxic type B trichothecenes. The potential involvement of chlorogenic acid in cereal resistance to Fusarium Head Blight and Gibberella Ear Rot and to trichothecene accumulation was the focus of this study. The effects of chlorogenic acid and one of its hydrolyzed products, caffeic acid, on fungal growth and type B trichothecenes biosynthesis were studied using concentrations close to physiological amounts quantified in kernels and a set of F. graminearum and F. culmorum strains. Both chlorogenic and caffeic acids negatively impact fungal growth and mycotoxin production, with caffeic acid being significantly more toxic. Inhibitory efficiencies of both phenolic acids were strain-dependent. To further investigate the antifungal and anti "mycotoxin" effect of chlorogenic and caffeic acids, the metabolic fate of these two phenolic acids was characterized in supplemented F. graminearum broths. For the first time, our results demonstrated the ability of F. graminearum to degrade chlorogenic acid into caffeic, hydroxychlorogenic and protocatechuic acids and caffeic acid into protocatechuic and hydroxycaffeic acids. Some of these metabolic products can contribute to the inhibitory efficiency of chlorogenic acid that, therefore, can be compared as a "pro-drug". As a whole, our data corroborate the contribution of chlorogenic acid to the chemical defense that cereals employ to counteract F. graminearum and its production of mycotoxins. PMID:26812586

  3. Synthesis and biological properties of caffeic acid-PNA dimers containing guanine.

    PubMed

    Gaglione, Maria; Malgieri, Gaetano; Pacifico, Severina; Severino, Valeria; D'Abrosca, Brigida; Russo, Luigi; Fiorentino, Antonio; Messere, Anna

    2013-01-01

    Caffeic acid (CA; 3,4-dihydroxycinnamic acid) is endowed with high antioxidant activity. CA derivatives (such as amides) have gained a lot of attention due to their antioxidative, antitumor and antimicrobial properties as well as stable characteristics. Caffeoyl-peptide derivatives showed different antioxidant activity depending on the type and the sequence of amino acid used. For these reasons, we decided to combine CA with Peptide Nucleic Acid (PNA) to test whether the new PNA-CA amide derivatives would result in an improvement or gain of CA's biological (i.e., antioxidant, cytotoxic, cytoprotective) properties. We performed the synthesis and characterization of seven dimer conjugates with various combinations of nucleic acid bases and focused NMR studies on the model compound ga-CA dimer. We demonstrate that PNA dimers containing guanine conjugated to CA exhibited different biological activities depending on composition and sequence of the nucleobases. The dimer ag-CA protected HepG2, SK-B-NE(2), and C6 cells from a cytotoxic dose of hydrogen peroxide (H₂O₂). PMID:23912270

  4. Caffeic Acid-PLGA Conjugate to Design Protein Drug Delivery Systems Stable to Irradiation

    PubMed Central

    Selmin, Francesca; Puoci, Francesco; Parisi, Ortensia I.; Franzé, Silvia; Musazzi, Umberto M.; Cilurzo, Francesco

    2015-01-01

    This work reports the feasibility of caffeic acid grafted PLGA (g-CA-PLGA) to design biodegradable sterile microspheres for the delivery of proteins. Ovalbumin (OVA) was selected as model compound because of its sensitiveness of γ-radiation. The adopted grafting procedure allowed us to obtain a material with good free radical scavenging properties, without a significant modification of Mw and Tg of the starting PLGA (Mw PLGA = 26.3 ± 1.3 kDa vs. Mw g-CA-PLGA = 22.8 ± 0.7 kDa; Tg PLGA = 47.7 ± 0.8 °C vs. Tg g-CA-PLGA = 47.4 ± 0.2 °C). By using a W1/O/W2 technique, g-CA-PLGA improved the encapsulation efficiency (EE), suggesting that the presence of caffeic residues improved the compatibility between components (EEPLGA = 35.0% ± 0.7% vs. EEg-CA-PLGA = 95.6% ± 2.7%). Microspheres particle size distribution ranged from 15 to 50 µm. The zeta-potential values of placebo and loaded microspheres were −25 mV and −15 mV, respectively. The irradiation of g-CA-PLGA at the dose of 25 kGy caused a less than 1% variation of Mw and the degradation patterns of the non-irradiated and irradiated microspheres were superimposable. The OVA content in g-CA-PLGA microspheres decreased to a lower extent with respect to PLGA microspheres. These results suggest that g-CA-PLGA is a promising biodegradable material to microencapsulate biological drugs. PMID:25569163

  5. Polyphenols protect against protein glycoxidation.

    PubMed

    Sadowska-Bartosz, Izabela; Galiniak, Sabina; Bartosz, Grzegorz

    2014-10-01

    Glycoxidation belongs to posttranslational protein modifications which underlie pathological sequelae of diabetes and other diseases, and contribute to aging. Search for efficient inhibitors of glycoxidation is therefore of considerable importance. We studied the effect of various polyphenols on the glycoxidation of bovine serum albumin (90 uM) incubated in vitro with glucose, fructose or ribose (100mM) for 6 days in 0.1M phosphate buffer, pH 7.4. Polyphenols have multiple biological actions including antioxidant activity and chelation of transition metal ions. The extent of glycoxidation was evaluated using fluorimetic parameters reflecting formation of Advanced Glycoxidation End Products (AGEs: 325/440nm), dityrosine (330/415nm), formylkynurenine (325/434nm) and kynurenine (365/480nm) and confirmed by estimation of AGEs using an ELISA kit. The results confirmed reliability of easily measurable fluorimetric parameters such as AGEs, dityrosine and formylkynurenine level for estimation of the extent of glycoxidation.All the polyphenols used (caffeic acid, ferulic acid, gallic acid, genistein, naringin, propyl gallate, quercitrin and rutin) decreased the extent of albumin glycoxidation. The extent of protection varied for different sugars (e. g. 1mM genistein: 24.4±1.7 for glucose, 44.5±0.2 for fructose 51.4±0.3 for ribose) The sequence of protective effect was: ferulic acid>caffeic acid>propyl gallate>naringin>quercitrin>genistein for glucose, caffeic acid>ferulic acid>propyl gallate>genistein>quercitrin>rutin>naringin for fructose and genistein>ferulic acid>caffeic acid>rutin>propyl gallate>naringin>quercitrin>gallic acid. These results confirm that polyphenols, natural components of human diet, protect against protein glycation in a model in vitro system. This study was performed within the framework of COSTCM1001 action and was sponsored by Grant 2011/01/M/N23-02065 of the National Science Center of Poland. PMID:26461390

  6. Comparative study of the antioxidative activities of caffeoylquinic and caffeic acids.

    PubMed

    Marković, Svetlana; Tošović, Jelena

    2016-11-01

    A detailed conformational analysis was performed to determine the most stable conformers of chlorogenic, cryptochlorogenic, and neochlorogenic acids. The simulated and experimental NMR spectra of caffeoylquinic acids are in excellent agreement. The bond dissociation enthalpies, proton affinities, electron transfer enthalpies, ionisation potentials, and proton dissociation enthalpies for these compounds and caffeic acid in benzene, methanol, and water were used for thermodynamic consideration of the major antioxidative mechanisms: HAT (Hydrogen Atom Transfer), SPLET (Sequential Proton-Loss Electron-Transfer), and SET-PT (Single Electron Transfer - Proton Transfer). All compounds are characterised with very similar values of each enthalpy, suggesting that they will exhibit comparable antioxidative activities. This assumption is in perfect accord with the experimental findings. It was suggested that HAT may be the predominant mechanism in nonpolar solvents, while HAT and SPLET are competitive pathways in polar media. All calculations were performed using the B3LYP-D2/6-311++G(d,p) and M06-2X/6-311++G(d,p) levels of theory and CPCM solvation model. PMID:27211685

  7. Potential in vitro Protective Effect of Quercetin, Catechin, Caffeic Acid and Phytic Acid against Ethanol-Induced Oxidative Stress in SK-Hep-1 Cells

    PubMed Central

    Lee, Ki-Mo; Kang, Hyung-Sik; Yun, Chul-Ho; Kwak, Hahn-Shik

    2012-01-01

    Phytochemicals have been known to exhibit potent antioxidant activity. This study examined cytoprotective effects of phytochemicals including quercetin, catechin, caffeic acid, and phytic acid against oxidative damage in SK-Hep-1 cells induced by the oxidative and non-oxidative metabolism of ethanol. Exposure of the cells to excess ethanol resulted in a significant increase in cytotoxicity, reactive oxygen species (ROS) production, lipid hydroperoxide (LPO), and antioxidant enzyme activity. Excess ethanol also caused a reduction in mitochondrial membrane potential (MMP) and the quantity of reduced glutathione (GSH). Co-treatment of cells with ethanol and quercetin, catechin, caffeic acid and phytic acid significantly inhibited oxidative ethanol metabolism-induced cytotoxicity by blocking ROS production. When the cells were treated with ethanol after pretreatment of 4-methylpyrazole (4-MP), increased cytotoxicity, ROS production, antioxidant enzyme activity, and loss of MMP were observed. The addition of quercetin, catechin, caffeic acid and phytic acid to these cells showed suppression of non-oxidative ethanol metabolism-induced cytotoxicity, similar to oxidative ethanol metabolism. These results suggest that quercetin, catechin, caffeic acid and phytic acid have protective effects against ethanol metabolism-induced oxidative insult in SK-Hep-1 cells by blocking ROS production and elevating antioxidant potentials. PMID:24009840

  8. Caffeic Acid Phenethyl Ester inhibit Hepatic Fibrosis by Nitric Oxide Synthase and Cystathionine Gamma-Lyase in Rats

    PubMed Central

    Shi, Yan; Guo, Li; Shi, Lu; Yu, Jinyang; Song, Min; Li, Yana

    2015-01-01

    Background Our aim was to study the effect of caffeic acid phenethyl ester (CAPE) on iNOS and cystathionine gamma-lyase (CSE) of hepatic fibrosis rat, and discuss the anti-hepatic fibrosis mechanism of caffeic acid phenethyl ester. Material/Methods We observed changes of NO and H2S in serum of hepatic fibrosis rats. Enzyme-linked immunosorbent assay was used to test OD value of iNOS and CSE in serum of each. The expressions of iNOS and CSE protein in the liver were also detected by immunohistochemistry. Results Compared with the model group, the expression of NO and iNOS was decreased obviously and the level of H2S and CSE was increased in the CAPE group. Conclusions CAPE has the effect of anti-hepatic fibrosis, which can be realized through adjusting the expression level of iNOS and CSE. PMID:26378818

  9. Effect of repeated harvesting on the content of caffeic acid and seven species of caffeoylquinic acids in sweet potato leaves.

    PubMed

    Sasaki, Kazunori; Oki, Tomoyuki; Kai, Yumi; Nishiba, Yoichi; Okuno, Shigenori

    2015-01-01

    The purpose of this study was to investigate the effect of repeated harvesting on the content of caffeic acid (CA) and seven species of caffeoylquinic acids (CQAs) in sweet potato leaves using a newly developed high-performance liquid chromatography method. Six cultivars and two breeding lines were used in this study. Leaves were collected at monthly intervals from 1st harvest (May) to 4th harvest (August) in 2011 and 2012. ANOVA analysis revealed that the contents of CQAs were significantly different among all cultivars and breeding lines, but no significant differences were found for CA. No annual variation was confirmed in CA and CQAs. Repeated harvest of sweet potato leaves affected the content of only 4-CQA and 5-CQA. Post-hoc comparisons using Tukey's method indicated that the contents of 4-CQA and 5-CQA in sweet potato leaves harvested at first time were significantly higher compared to those at the other harvest times. PMID:25971339

  10. Caffeic acid phenethyl ester: Inhibition of metastatic cell behaviours via voltage-gated sodium channel in human breast cancer in vitro.

    PubMed

    Fraser, Scott P; Hemsley, Faye; Djamgoz, Mustafa B A

    2016-02-01

    Caffeic acid phenethyl ester, derived from natural propolis, has been reported to have anti-cancer properties. Voltage-gated sodium channels are upregulated in many cancers where they promote metastatic cell behaviours, including invasiveness. We found that micromolar concentrations of caffeic acid phenethyl ester blocked voltage-gated sodium channel activity in several invasive cell lines from different cancers, including breast (MDA-MB-231 and MDA-MB-468), colon (SW620) and non-small cell lung cancer (H460). In the MDA-MB-231 cell line, which was adopted as a 'model', long-term (48 h) treatment with 18 μM caffeic acid phenethyl ester reduced the peak current density by 91% and shifted steady-state inactivation to more hyperpolarized potentials and slowed recovery from inactivation. The effects of long-term treatment were also dose-dependent, 1 μM caffeic acid phenethyl ester reducing current density by only 65%. The effects of caffeic acid phenethyl ester on metastatic cell behaviours were tested on the MDA-MB-231 cell line at a working concentration (1 μM) that did not affect proliferative activity. Lateral motility and Matrigel invasion were reduced by up to 14% and 51%, respectively. Co-treatment of caffeic acid phenethyl ester with tetrodotoxin suggested that the voltage-gated sodium channel inhibition played a significant intermediary role in these effects. We conclude, first, that caffeic acid phenethyl ester does possess anti-metastatic properties. Second, the voltage-gated sodium channels, commonly expressed in strongly metastatic cancers, are a novel target for caffeic acid phenethyl ester. Third, more generally, ion channel inhibition can be a significant mode of action of nutraceutical compounds. PMID:26724521

  11. Survival of Escherichia coli O157:H7 ATCC 43895 in a Model Apple Juice Medium with Different Concentrations of Proline and Caffeic Acid

    PubMed Central

    Reinders, Robert D.; Biesterveld, Steef; Bijker, Peter G. H.

    2001-01-01

    The effects of proline and caffeic acid on the survival of Shiga toxin-producing Escherichia coli (STEC) O157:H7 strain ATCC 43895 in a model apple juice medium were studied. It is hypothesized that the inhibitory effect of caffeic acid may explain why almost all outbreaks of STEC O157:H7 infections linked to apple juice or cider have occurred in October or November. PMID:11375209

  12. Molecularly imprinted polymers combination with deep eutectic solvents for solid-phase extraction of caffeic acid from hawthorn.

    PubMed

    Li, Guizhen; Tang, Weiyang; Cao, Weimin; Wang, Qian; Zhu, Tao

    2015-08-01

    Molecularly imprinted polymers (MIPs) with caffeic acid as template and non-imprinted polymers (NIPs) materials were prepared in the same procedure. Field emission scanning electron microscopy (FE-SEM) and adsorption capacity test were used to evaluate characteristic of the new materials. MIPs, NIPs and C18 were used for rapid purification of caffeic acid from hawthorn with solid-phase extraction ( SPE) , and extract yields of caffeic acid with the proposed materials were 3.46 µg/g, 1.01 µg/g and 1.17 µg/g, respectively. To optimize the MIPs-SPE procedures, different kinds of elution solutions were studied. Deep eutectic solvents (DESs) were prepared by choline chloride (ChCl)-glycerol (1/2, n/n) and choline chloride-urea (1/ 2, n/n). Methanol was mixed with the two kinds of DESs (glycerol-based DESs, urea-based DESs) in different ratios (0.5:1, 1:1, 2:1, 3:1, 4:1, 5:1, v/v), and they were used to investigated as elution solutions in the above MIPs-SPE procedures. The results showed that MIPs were potential SPE materials, and methanol/ glycerol-based DESs (3 :1, v/v) had the best elution capability with the recovery of 82.32%. PMID:26749853

  13. Biocatalytic properties of a peroxidase-active cell-free extract from onion solid wastes: caffeic acid oxidation.

    PubMed

    El Agha, Ayman; Abbeddou, Souheila; Makris, Dimitris P; Kefalas, Panagiotis

    2009-04-01

    The exploitation of food residual sources consists of a major factor in reducing the polluting load of food industry wastes and developing novel added-value products. Plant food residues including trimmings and peels might contain a range of enzymes capable of transforming bio-organic molecules with potential phytotoxicity, including hydrolases, peroxidases and polyphenoloxidases. Although the use of bacterial and fungal enzymes has gained interest in studies pertaining to bioremediation applications, plant enzymes have been given less attention or even disregarded. In this view, this study aimed at the investigating the use of a crude peroxidase preparation from onion solid by-products for oxidising caffeic acid, a widespread o-diphenol, whose various derivatives may occur in food industry wastes, such as olive mill waste waters. Increased enzyme activity was observed at a pH value of 5, but considerable activity was also retained for pH up to 7. Favourable temperatures for increased activity varied between 20 degrees C and 40 degrees C, 30 degrees C being the optimal. Liquid chromatography-mass spectrometry analysis of a homogenate/H(2)O(2)-treated caffeic acid solution revealed the existence of a tetramer as major oxidation product. Based on the data generated, a putative pathway for the formation of the peroxidase-mediated caffeic acid tetramer was proposed. PMID:18670892

  14. Caffeic acid phenethyl ester lessens disease symptoms in an experimental autoimmune uveoretinitis mouse model.

    PubMed

    Choi, Jae-Hyeog; Roh, Kug-Hwan; Oh, Hana; Park, Sol-Ji; Ha, Sung-Min; Kang, Mi Seon; Lee, Ji-Hyun; Jung, So Young; Song, Hyunkeun; Yang, Jae Wook; Park, SaeGwang

    2015-05-01

    Experimental autoimmune uveoretinitis (EAU) is an autoimmune disease that models human uveitis. Caffeic acid phenethyl ester (CAPE), a phenolic compound isolated from propolis, possesses anti-inflammatory and immunomodulatory properties. CAPE demonstrates therapeutic potential in several animal disease models through its ability to inhibit NF-κB activity. To evaluate these therapeutic effects in EAU, we administered CAPE in a model of EAU that develops after immunization with interphotoreceptor retinal-binding protein (IRBP) in B10.RIII and C57BL/6 mice. Importantly, we found that CAPE lessened the severity of EAU symptoms in both mouse strains. Notably, treated mice exhibited a decrease in the ocular infiltration of immune cell populations into the retina; reduced TNF-α, IL-6, and IFN-γ serum levels: and inhibited TNF-α mRNA expression in retinal tissues. Although CAPE failed to inhibit IRBP-specific T cell proliferation, it was sufficient to suppress cytokine, chemokine, and IRBP-specific antibody production. In addition, retinal tissues isolated from CAPE-treated EAU mice revealed a decrease in NF-κB p65 and phospho-IκBα. The data identify CAPE as a potential therapeutic agent for autoimmune uveitis that acts by inhibiting cellular infiltration into the retina, reducing the levels of pro-inflammatory cytokines, chemokine, and IRBP-specific antibody and blocking NF-κB pathway activation. PMID:25795054

  15. The effects of caffeic acid phenethyl ester on streptozotocin-induced diabetic liver injury.

    PubMed

    Taslidere, E; Gul, M; Elbe, H; Cetin, A; Vardi, N; Ozyalin, F; Turkoz, Y

    2016-01-01

    The aim of the present study was to clarify the role of oxidative stress in streptozotocin induced liver injury and the possible protective effect of caffeic acid phenethyl ester (CAPE) using histological and biochemical parameters. 32 male Wistar rats were divided into 4 groups as follows: Group 1: Control animals, Group 2: Control animals given CAPE Group 3: STZ-induced diabetic animals (DM group), Group 4: STZ-induced diabetic rats given CAPE (DM+CAPE group). All the injections started on the same day of single-dose STZ injection and continued for 20 days. At the end of this period, livers were removed and processed for routine histological procedures. Biochemical parameters and morphological changes were examined. In DM group, blood glucose levels were significantly increased compared with the control group. Significant increases in tissue malondialdehyde (MDA) level and decreases in superoxide dismutase (SOD) and total glutathione (GSH) activities were detected in DM group. Administration of CAPE significantly reduced these values. STZ-induced histopathological alterations including inflammatory cell infiltration around portal triad, congestion, loss of glycogen in the hepatocytes. Additionally, degenerative cellular alterations, such as numerous vacuolizations including myelinic figure formation, pyknotic nuclei with peripheral localization of heterochromatin condensation and mitochondrial elongation were observed in cytoplasm of hepatocytes. CAPE significantly reduced these histopathological changes. Our results indicate that CAPE should be considered in the prevention of oxidative stress in diabetic liver. PMID:27215964

  16. Could Caffeic Acid Phenethyl Ester Expand the Antitumor Effect of Tamoxifen in Breast Carcinoma?

    PubMed

    Motawi, Tarek K; Abdelazim, Samy A; Darwish, Hebatallah A; Elbaz, Eman M; Shouman, Samia A

    2016-01-01

    Despite tamoxifen (TAM) is beneficial in treating a significant proportion of patients with breast cancer, many women still relapse after long-term therapy. Caffeic acid phenethyl ester (CAPE) is a component of honeybee propolis, with a plethora of important biological actions including anticancer activity. This study aimed to explore the cytotoxicity, the type of drugs interaction as well as the apoptotic and autophagic pathways of the combined treatment of TAM and CAPE in MCF-7 cells. Their antitumor activity and effect on survival of mice bearing Ehrlich tumor were also analyzed. The results showed synergistic cytotoxic effects, manifested by significant activation of apoptotic machinery, along with downregulation of protein levels of Bcl-2 and beclin-1, upon using the combination regimen. However, the ratio between microtubule-associated protein light chain 3-II and -I was not altered. Moreover, a decrease in vascular endothelial growth factor level was detected. Similarly, TAM + CAPE increased the life span of tumor-bearing animals and caused a marked regression in their tumor size and weight compared with those treated with either TAM or CAPE alone. In conclusion, CAPE relatively improved the anticancer activity of TAM in both in vitro and in vivo models via its apoptotic and angiostatic potentials. PMID:27007181

  17. Caffeic Acid phenethyl ester is a potential therapeutic agent for oral cancer.

    PubMed

    Kuo, Ying-Yu; Jim, Wai-Tim; Su, Liang-Cheng; Chung, Chi-Jung; Lin, Ching-Yu; Huo, Chieh; Tseng, Jen-Chih; Huang, Shih-Han; Lai, Chih-Jen; Chen, Bo-Chih; Wang, Bi-Juan; Chan, Tzu-Min; Lin, Hui-Ping; Chang, Wun-Shaing Wayne; Chang, Chuang-Rung; Chuu, Chih-Pin

    2015-01-01

    Head and neck cancers, which affect 650,000 people and cause 350,000 deaths per year, is the sixth leading cancer by cancer incidence and eighth by cancer-related death worldwide. Oral cancer is the most common type of head and neck cancer. More than 90% of oral cancers are oral and oropharyngeal squamous cell carcinoma (OSCC). The overall five-year survival rate of OSCC patients is approximately 63%, which is due to the low response rate to current therapeutic drugs. In this review we discuss the possibility of using caffeic acid phenethyl ester (CAPE) as an alternative treatment for oral cancer. CAPE is a strong antioxidant extracted from honeybee hive propolis. Recent studies indicate that CAPE treatment can effectively suppress the proliferation, survival, and metastasis of oral cancer cells. CAPE treatment inhibits Akt signaling, cell cycle regulatory proteins, NF-κB function, as well as activity of matrix metalloproteinase (MMPs), epidermal growth factor receptor (EGFR), and Cyclooxygenase-2 (COX-2). Therefore, CAPE treatment induces cell cycle arrest and apoptosis in oral cancer cells. According to the evidence that aberrations in the EGFR/phosphoinositide 3-kinase (PI3K)/protein kinase B (Akt) signaling, NF-κB function, COX-2 activity, and MMPs activity are frequently found in oral cancers, and that the phosphorylation of Akt, EGFR, and COX-2 correlates to oral cancer patient survival and clinical progression, we believe that CAPE treatment will be useful for treatment of advanced oral cancer patients. PMID:25984601

  18. Protective Effects of Intralipid and Caffeic Acid Phenethyl Ester on Nephrotoxicity Caused by Dichlorvos in Rats.

    PubMed

    Celik, Muhammet Murat; Alp, Ayse; Dokuyucu, Recep; Zemheri, Ebru; Ozkanli, Seyma; Ertekin, Filiz; Yaldiz, Mehmet; Akdag, Abdurrahman; Ipci, Ozlem; Toprak, Serhat

    2015-01-01

    The protective effects of Caffeic Acid Phenethyl Ester (CAPE) and intralipid (IL) on nephrotoxicity caused by acute Dichlorvos (D) toxicity were investigated in this study. Forty-eight Wistar Albino rats were divided into 7 groups as follows: Control, D, CAPE, intralipid, D + CAPE, D + IL, and D + CAPE + IL. When compared to D group, the oxidative stress index (OSI) values were significantly lower in Control, CAPE, and D + IL + CAPE groups. When compared to D + IL + CAPE group, the TOS and OSI values were significantly higher in D group (P < 0.05). When mitotic cell counts were assessed in the renal tissues, it was found that mitotic cell count was significantly higher in the D group while it was lower in the D + CAPE, D + IL, and D + IL + CAPE groups when compared to the control group (P < 0.05). Also, immune reactivity showed increased apoptosis in D group and low profile of apoptosis in the D + CAPE group when compared to the Control group. The apoptosis level was significantly lower in D + IL + CAPE compared to D group (P < 0.05) in the kidneys. As a result, we concluded that Dichlorvos can be used either alone or in combination with CAPE and IL as supportive therapy or as facilitator for the therapeutic effect of the routine treatment in the patients presenting with pesticide poisoning. PMID:26504614

  19. Caffeic Acid Phenethyl Ester Regulates PPAR's Levels in Stem Cells-Derived Adipocytes.

    PubMed

    Vanella, Luca; Tibullo, Daniele; Godos, Justyna; Pluchinotta, Francesca Romana; Di Giacomo, Claudia; Sorrenti, Valeria; Acquaviva, Rosaria; Russo, Alessandra; Li Volti, Giovanni; Barbagallo, Ignazio

    2016-01-01

    Hypertrophic obesity inhibits activation of peroxisome proliferators-activated receptor gamma (PPARγ), considered the key mediator of the fully differentiated and insulin sensitive adipocyte phenotype. We examined the effects of Caffeic Acid Phenethyl Ester (Cape), isolated from propolis, a honeybee hive product, on Adipose Stem Cells (ASCs) differentiation to the adipocyte lineage. Finally we tested the effects of Cape on insulin-resistant adipocytes. Quantification of Oil Red O-stained cells showed that lipid droplets decreased following Cape treatment as well as radical oxygen species formation. Additionally, exposure of ASC to high glucose levels decreased adiponectin and increased proinflammatory cytokines mRNA levels, which were reversed by Cape-mediated increase of insulin sensitivity. Cape treatment resulted in decreased triglycerides synthesis and increased beta-oxidation. Exposure of ASCs to Lipopolysaccharide (LPS) induced a reduction of PPARγ, an increase of IL-6 levels associated with a well-known stimulation of lipolysis; Cape partially attenuated the LPS-mediated effects. These observations reveal the main role of PPARγ in the adipocyte function and during ASC differentiation. As there is now substantial interest in functional food and nutraceutical products, the observed therapeutic value of Cape in insulin-resistance related diseases should be taken into consideration. PMID:26904104

  20. Phenolic Profiling of Caffeic Acid O-Methyltransferase-Deficient Poplar Reveals Novel Benzodioxane Oligolignols1

    PubMed Central

    Morreel, Kris; Ralph, John; Lu, Fachuang; Goeminne, Geert; Busson, Roger; Herdewijn, Piet; Goeman, Jan L.; Van der Eycken, Johan; Boerjan, Wout; Messens, Eric

    2004-01-01

    Caffeic acid O-methyltransferase (COMT) catalyzes preferentially the methylation of 5-hydroxyconiferaldehyde to sinapaldehyde in monolignol biosynthesis. Here, we have compared HPLC profiles of the methanol-soluble phenolics fraction of xylem tissue from COMT-deficient and control poplars (Populus spp.), using statistical analysis of the peak heights. COMT down-regulation results in significant concentration differences for 25 of the 91 analyzed peaks. Eight peaks were exclusively detected in COMT-deficient poplar, of which four could be purified for further identification using mass spectrometry/mass spectrometry, nuclear magnetic resonance, and spiking of synthesized reference compounds. These new compounds were derived from 5-hydroxyconiferyl alcohol or 5-hydroxyconiferaldehyde and were characterized by benzodioxane moieties, a structural type that is also increased in the lignins of COMT-deficient plants. One of these four benzodioxanes amounted to the most abundant oligolignol in the HPLC profile. Furthermore, all of the differentially accumulating oligolignols involving sinapyl units were either reduced in abundance or undetectable. The concentration levels of all identified oligolignols were in agreement with the relative supply of monolignols and with their chemical coupling propensities, which supports the random coupling hypothesis. Chiral HPLC analysis of the most abundant benzodioxane dimer revealed the presence of both enantiomers in equal amounts, indicating that they were formed by radical coupling reactions under simple chemical control rather than guided by dirigent proteins. PMID:15563622

  1. Caffeic acid attenuates rat liver reperfusion injury through sirtuin 3-dependent regulation of mitochondrial respiratory chain.

    PubMed

    Mu, Hong-Na; Li, Quan; Pan, Chun-Shui; Liu, Yu-Ying; Yan, Li; Hu, Bai-He; Sun, Kai; Chang, Xin; Zhao, Xin-Rong; Fan, Jing-Yu; Han, Jing-Yan

    2015-08-01

    Sirtuin 3 (Sirt3) plays critical roles in regulating mitochondrial oxidative metabolism. However, whether Sirt3 is involved in liver ischemia and reperfusion (I/R) injury remains elusive. Caffeic acid (CA) is a natural antioxidant derived from Salvia miltiorrhiza. Whether CA protects against liver I/R injury through regulating Sirt3 and the mitochondrial respiratory chain (MRC) is unclear. This study investigated the effect of CA on liver I/R injury, microcirculatory disturbance, and potential mechanisms, particularly focusing on Sirt3-dependent MRC. Liver I/R of male Sprague-Dawley rats was established by occlusion of portal area vessels for 30 min followed by 120 min of reperfusion. CA (15 mg/kg/h) was continuously infused via the femoral vein starting 30 min before ischemia. After I/R, Sirt3 expression, and MRC activity decreased, acetylation of NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 9 and succinate dehydrogenase complex, subunit A, flavoprotein variant provoked, and the liver microcirculatory disturbance and injury were observed. Treatment with CA attenuated liver injury, inhibited Sirt3 down-expression, and up-regulated MRC activity. CA attenuated rat liver microcirculatory disturbance and oxidative injury through regulation of Sirt3 and the mitochondrial respiratory chain. PMID:25960048

  2. Caffeic acid phenethyl ester improves burn healing in rats through anti-inflammatory and antioxidant effects.

    PubMed

    dos Santos, Jeanine Salles; Monte-Alto-Costa, Andréa

    2013-01-01

    Although caffeic acid phenethyl ester (CAPE) has beneficial properties, its anti-inflammatory and antioxidant effects on healing burn injury have not been investigated as yet. Female Wistar rats were divided in two groups: burn and burn + CAPE. A scald injury (burn) was performed. CAPE treatment (10 µmol kg) began immediately after the burn and lasted for 14 days. Euthanasia was performed 14 or 70 days after burning. Seven, 21, and 70 days after burning, burn + CAPE group presented smaller wound area. Increase in reepithelialization was observed in burn + CAPE group 28 and 63 days after burning. Fourteen days after wounding, burn + CAPE group presented diminished myeloperoxidase activity and nitrite levels, reduced CD68 and platelet endothelial cell adhesion molecule 1 protein expression, and less oxidative damage (decrease in malondialdehyde (MDA) and carbonyl levels in plasma and lesion extracts). Seventy days after burning, the amount of myofibroblasts and macrophages (CD68 positive) was decreased and the amount of hydroxyproline was increased in burn + CAPE group. Treatment with CAPE improved burn wound healing, showing decrease in inflammatory parameters and in oxidative damage. PMID:23511289

  3. Protective Effects of Caffeic Acid Phenethyl Ester on Fluoxetine-Induced Hepatotoxicity: An Experimental Study

    PubMed Central

    Yılmaz, Ahmet; Elbey, Bilal; Yazgan, Ümit Can; Dönder, Ahmet; Arslan, Necmi; Arslan, Serkan; Alabalık, Ulaş; Aslanhan, Hamza

    2016-01-01

    Background. The aim of the study was to analyse the effect of caffeic acid phenethyl ester (CAPE) on fluoxetine-induced hepatotoxicity in rats. Materials and Methods. Group I served as control. Group II received CAPE intraperitoneally. Group III received fluoxetine per orally. Group IV received fluoxetine and CAPE. The total antioxidant capacity (TAC), total oxidant status (TOS), oxidative stress index (OSI), and liver enzymes including paraoxonase-1 (PON-1), aspartate transaminase, and alanine transaminase levels were measured. Liver tissues were processed histopathologically for evaluation of liver injury and to validate the serum enzyme levels. Results. An increase in TOS and OSI and a decrease in TAC and PON-1 levels in serum and liver tissues of Group III were observed compared to Groups I and II. After treatment with CAPE, the level of TOS and OSI decreased while TAC and PON-1 increased in serum and liver in Group IV. Histopathological examination of the liver revealed hepatic injury after fluoxetine treatment and reduction of injury with CAPE treatment. Conclusion. Our results suggested that CAPE treatment provided protection against fluoxetine toxicity. Following CAPE treatment with fluoxetine-induced hepatotoxicity, TOS and OSI levels decreased, whereas PON-1 and TAC increased in the serum and liver. PMID:27144157

  4. Probing the interaction of caffeic acid with ZnO nanoparticles.

    PubMed

    Belay, Abebe; Kim, Hyung Kook; Hwang, Yoon-Hwae

    2016-05-01

    The binding of ZnO nanoparticles (NPs) and caffeic acid (CFA) was investigated using fluorescence quenching, UV/vis absorption spectrscopy, Fourier transform infrared (FTIR) spectroscopy, transmission electron microscopy (TEM) and dynamic light scattering (DLS) at different temperatures. The study results indicated fluorescence quenching between ZnO NPs and CFA rationalized in terms of a static quenching mechanism or the formation of non-fluorescent CFA-ZnO. From fluorescence quenching spectral analysis, the binding constant (Ka ), number of binding sites (n) and thermodynamic properties were determined. Values of the quenching (KSV ) and binding (Ka ) constants decrease with increasing temperature and the number of binding sites n = 2. The thermodynamic parameters determined using Van't Hoff equation indicated that binding occurs spontaneously involving the hydrogen bond, and van der Waal's forces played a major role in the reaction of ZnO NPs with CFA. The FTIR, TEM and DLS measurements also indicated differences in the structure, morphology and size of CFA, ZnO NPs and their corresponding CFA-ZnO. Copyright © 2015 John Wiley & Sons, Ltd. PMID:27037967

  5. Caffeic Acid Phenethyl Ester Is a Potential Therapeutic Agent for Oral Cancer

    PubMed Central

    Kuo, Ying-Yu; Jim, Wai-Tim; Su, Liang-Cheng; Chung, Chi-Jung; Lin, Ching-Yu; Huo, Chieh; Tseng, Jen-Chih; Huang, Shih-Han; Lai, Chih-Jen; Chen, Bo-Chih; Wang, Bi-Juan; Chan, Tzu-Min; Lin, Hui-Ping; Chang, Wun-Shaing Wayne; Chang, Chuang-Rung; Chuu, Chih-Pin

    2015-01-01

    Head and neck cancers, which affect 650,000 people and cause 350,000 deaths per year, is the sixth leading cancer by cancer incidence and eighth by cancer-related death worldwide. Oral cancer is the most common type of head and neck cancer. More than 90% of oral cancers are oral and oropharyngeal squamous cell carcinoma (OSCC). The overall five-year survival rate of OSCC patients is approximately 63%, which is due to the low response rate to current therapeutic drugs. In this review we discuss the possibility of using caffeic acid phenethyl ester (CAPE) as an alternative treatment for oral cancer. CAPE is a strong antioxidant extracted from honeybee hive propolis. Recent studies indicate that CAPE treatment can effectively suppress the proliferation, survival, and metastasis of oral cancer cells. CAPE treatment inhibits Akt signaling, cell cycle regulatory proteins, NF-κB function, as well as activity of matrix metalloproteinase (MMPs), epidermal growth factor receptor (EGFR), and Cyclooxygenase-2 (COX-2). Therefore, CAPE treatment induces cell cycle arrest and apoptosis in oral cancer cells. According to the evidence that aberrations in the EGFR/phosphoinositide 3-kinase (PI3K)/protein kinase B (Akt) signaling, NF-κB function, COX-2 activity, and MMPs activity are frequently found in oral cancers, and that the phosphorylation of Akt, EGFR, and COX-2 correlates to oral cancer patient survival and clinical progression, we believe that CAPE treatment will be useful for treatment of advanced oral cancer patients. PMID:25984601

  6. Protective Effects of Caffeic Acid Phenethyl Ester on Fluoxetine-Induced Hepatotoxicity: An Experimental Study.

    PubMed

    Yılmaz, Ahmet; Elbey, Bilal; Yazgan, Ümit Can; Dönder, Ahmet; Arslan, Necmi; Arslan, Serkan; Alabalık, Ulaş; Aslanhan, Hamza

    2016-01-01

    Background. The aim of the study was to analyse the effect of caffeic acid phenethyl ester (CAPE) on fluoxetine-induced hepatotoxicity in rats. Materials and Methods. Group I served as control. Group II received CAPE intraperitoneally. Group III received fluoxetine per orally. Group IV received fluoxetine and CAPE. The total antioxidant capacity (TAC), total oxidant status (TOS), oxidative stress index (OSI), and liver enzymes including paraoxonase-1 (PON-1), aspartate transaminase, and alanine transaminase levels were measured. Liver tissues were processed histopathologically for evaluation of liver injury and to validate the serum enzyme levels. Results. An increase in TOS and OSI and a decrease in TAC and PON-1 levels in serum and liver tissues of Group III were observed compared to Groups I and II. After treatment with CAPE, the level of TOS and OSI decreased while TAC and PON-1 increased in serum and liver in Group IV. Histopathological examination of the liver revealed hepatic injury after fluoxetine treatment and reduction of injury with CAPE treatment. Conclusion. Our results suggested that CAPE treatment provided protection against fluoxetine toxicity. Following CAPE treatment with fluoxetine-induced hepatotoxicity, TOS and OSI levels decreased, whereas PON-1 and TAC increased in the serum and liver. PMID:27144157

  7. Caffeic Acid Phenethyl Ester Regulates PPAR's Levels in Stem Cells-Derived Adipocytes

    PubMed Central

    Vanella, Luca; Tibullo, Daniele; Godos, Justyna; Pluchinotta, Francesca Romana; Di Giacomo, Claudia; Sorrenti, Valeria; Acquaviva, Rosaria; Russo, Alessandra; Li Volti, Giovanni; Barbagallo, Ignazio

    2016-01-01

    Hypertrophic obesity inhibits activation of peroxisome proliferators-activated receptor gamma (PPARγ), considered the key mediator of the fully differentiated and insulin sensitive adipocyte phenotype. We examined the effects of Caffeic Acid Phenethyl Ester (Cape), isolated from propolis, a honeybee hive product, on Adipose Stem Cells (ASCs) differentiation to the adipocyte lineage. Finally we tested the effects of Cape on insulin-resistant adipocytes. Quantification of Oil Red O-stained cells showed that lipid droplets decreased following Cape treatment as well as radical oxygen species formation. Additionally, exposure of ASC to high glucose levels decreased adiponectin and increased proinflammatory cytokines mRNA levels, which were reversed by Cape-mediated increase of insulin sensitivity. Cape treatment resulted in decreased triglycerides synthesis and increased beta-oxidation. Exposure of ASCs to Lipopolysaccharide (LPS) induced a reduction of PPARγ, an increase of IL-6 levels associated with a well-known stimulation of lipolysis; Cape partially attenuated the LPS-mediated effects. These observations reveal the main role of PPARγ in the adipocyte function and during ASC differentiation. As there is now substantial interest in functional food and nutraceutical products, the observed therapeutic value of Cape in insulin-resistance related diseases should be taken into consideration. PMID:26904104

  8. Caffeic acid phenethyl ester (CAPE), an active component of propolis, inhibits Helicobacter pylori peptide deformylase activity.

    PubMed

    Cui, Kunqiang; Lu, Weiqiang; Zhu, Lili; Shen, Xu; Huang, Jin

    2013-05-31

    Helicobacter pylori (H. pylori) is a major causative factor for gastrointestinal illnesses, H. pylori peptide deformylase (HpPDF) catalyzes the removal of formyl group from the N-terminus of nascent polypeptide chains, which is essential for H. pylori survival and is considered as a promising drug target for anti-H. pylori therapy. Propolis, a natural antibiotic from honeybees, is reported to have an inhibitory effect on the growth of H. pylori in vitro. In addition, previous studies suggest that the main active constituents in the propolis are phenolic compounds. Therefore, we evaluated a collection of phenolic compounds derived from propolis for enzyme inhibition against HpPDF. Our study results show that Caffeic acid phenethyl ester (CAPE), one of the main medicinal components of propolis, is a competitive inhibitor against HpPDF, with an IC50 value of 4.02 μM. Furthermore, absorption spectra and crystal structural characterization revealed that different from most well known PDF inhibitors, CAPE block the substrate entrance, preventing substrate from approaching the active site, but CAPE does not have chelate interaction with HpPDF and does not disrupt the metal-dependent catalysis. Our study provides valuable information for understanding the potential anti-H. pylori mechanism of propolis, and CAPE could be served as a lead compound for further anti-H. pylori drug discovery. PMID:23611786

  9. Effect of caffeic acid phenethyl ester on bone formation in the expanded inter-premaxillary suture

    PubMed Central

    Kazancioglu, Hakki Oguz; Aksakalli, Sertac; Ezirganli, Seref; Birlik, Muhammet; Esrefoglu, Mukaddes; Acar, Ahmet Hüseyin

    2015-01-01

    Background Narrow maxilla is a common problem in orthodontics and dentofacial orthopedics. To solve this problem, a procedure called rapid maxillary expansion (RME) has been used. However, relapse tendency is a major problem of RME. Although relapse tendency is not clearly understood, various treatment procedures and new applications have been investigated. The present study aimed to investigate the possible effectiveness of caffeic acid phenethyl ester (CAPE) on new bone formation in rat midpalatal suture after RME. Materials and methods Twenty male Sprague Dawley rats were used in this study. The animals were randomly divided into two groups as control and CAPE group. In the CAPE group, CAPE was administered systemically via intraperitoneal injection. RME procedure was performed on all animals. For this purpose, the springs were placed on the maxillary incisors of rats and activated for 5 days. After then, the springs were removed and replaced with short lengths of rectangular retaining wire for consolidation period of 15 days. At the end of the study, histomorphometric analysis was carried out to assess new bone formation. Results New bone formation was significantly greater in the CAPE group than the control group (P<0.05). CAPE enhances new bone formation in midpalatal suture after RME. Conclusion These results show that CAPE may decrease the time needed for retention. PMID:26730181

  10. Protective effects of ferulic acid and related polyphenols against glyoxal- or methylglyoxal-induced cytotoxicity and oxidative stress in isolated rat hepatocytes.

    PubMed

    Maruf, Abdullah Al; Lip, HoYin; Wong, Horace; O'Brien, Peter J

    2015-06-01

    Glyoxal (GO) and methylglyoxal (MGO) cause protein and nucleic acid carbonylation and oxidative stress by forming reactive oxygen and carbonyl species which have been associated with toxic effects that may contribute to cardiovascular disease, complications associated with diabetes mellitus, Alzheimer's and Parkinson's disease. GO and MGO can be formed through oxidation of commonly used reducing sugars e.g., fructose under chronic hyperglycemic conditions. GO and MGO form advanced glycation end products which lead to an increased potential for developing inflammatory diseases. In the current study, we have investigated the protective effects of ferulic acid and related polyphenols e.g., caffeic acid, p-coumaric acid, methyl ferulate, ethyl ferulate, and ferulaldehyde on GO- or MGO-induced cytotoxicity and oxidative stress (ROS formation, protein carbonylation and mitochondrial membrane potential maintenance) in freshly isolated rat hepatocytes. To investigate and compare the protective effects of ferulic acid and related polyphenols against GO- or MGO-induced toxicity, five hepatocyte models were used: (a) control hepatocytes, (b) GSH-depleted hepatocytes, (c) catalase-inhibited hepatocytes, (d) aldehyde dehydrogenase (ALDH2)-inhibited hepatocytes, and (e) hepatocyte inflammation system (a non-toxic H2O2-generating system). All of the polyphenols tested significantly decreased GO- or MGO-induced cytotoxicity, ROS formation and improved mitochondrial membrane potential in these models. The rank order of their effectiveness was caffeic acid∼ferulaldehyde>ferulic acid>ethyl ferulate>methyl ferulate>p-coumaric acid. Ferulic acid was found to decrease protein carbonylation in GSH-depleted hepatocytes. This study suggests that ferulic acid and related polyphenols can be used therapeutically to inhibit or decrease GO- or MGO-induced hepatotoxicity. PMID:25446858

  11. Detoxification Processes from Vanadate at the Root Apoplasm Activated by Caffeic and Polygalacturonic Acids.

    PubMed

    Garau, Giovanni; Palma, Amedeo; Lauro, Gian Paolo; Mele, Elena; Senette, Caterina; Manunza, Bruno; Deiana, Salvatore

    2015-01-01

    In the root apoplasm, V(V) and V(IV) toxicity can be alleviated through redox and complexation reactions involving phenolic substances and the polyuronic components. In such context we report the role of polygalacturonic acid (PGA) on the reducing activity of caffeic acid (CAF) towards V(V). The redox reaction was particularly effective at pH 2.8 leading to the formation of oxidation products with redox activity towards V(V). An o-quinone was identified as the first product of the reaction which is further involved in the formation of CAF dimers. At pH ≥ 3.6 the redox activity decreased and a yield in V(IV) equal to 38, 31, 21 and 14% was found at pH 3.6, 4.0. 5.0 and 6.0 respectively compared with that obtained at pH 2.8. The redox reaction was faster in the presence of PGA and a higher yield of V(IV) was found in the 4.0-6.0 pH range with respect to the CAF-V(V) binary system. The higher efficiency of the redox reaction in the presence of PGA was related with the ability of PGA to bind V(IV). The biological significance of the redox reaction between CAF and V(V), as well as the role of PGA in such reaction, was established "in vivo" using triticale plants. Results showed that PGA reduced significantly the phytotoxic effects of the V(V)-CAF system. PMID:26484667

  12. Detoxification Processes from Vanadate at the Root Apoplasm Activated by Caffeic and Polygalacturonic Acids

    PubMed Central

    Garau, Giovanni; Palma, Amedeo; Lauro, Gian Paolo; Mele, Elena; Senette, Caterina; Manunza, Bruno; Deiana, Salvatore

    2015-01-01

    In the root apoplasm, V(V) and V(IV) toxicity can be alleviated through redox and complexation reactions involving phenolic substances and the polyuronic components. In such context we report the role of polygalacturonic acid (PGA) on the reducing activity of caffeic acid (CAF) towards V(V). The redox reaction was particularly effective at pH 2.8 leading to the formation of oxidation products with redox activity towards V(V). An o-quinone was identified as the first product of the reaction which is further involved in the formation of CAF dimers. At pH ≥ 3.6 the redox activity decreased and a yield in V(IV) equal to 38, 31, 21 and 14% was found at pH 3.6, 4.0. 5.0 and 6.0 respectively compared with that obtained at pH 2.8. The redox reaction was faster in the presence of PGA and a higher yield of V(IV) was found in the 4.0–6.0 pH range with respect to the CAF-V(V) binary system. The higher efficiency of the redox reaction in the presence of PGA was related with the ability of PGA to bind V(IV). The biological significance of the redox reaction between CAF and V(V), as well as the role of PGA in such reaction, was established “in vivo” using triticale plants. Results showed that PGA reduced significantly the phytotoxic effects of the V(V)-CAF system. PMID:26484667

  13. Nitrogen Limited Red and Green Leaf Lettuce Accumulate Flavonoid Glycosides, Caffeic Acid Derivatives, and Sucrose while Losing Chlorophylls, Β-Carotene and Xanthophylls

    PubMed Central

    Becker, Christine; Urlić, Branimir; Jukić Špika, Maja; Kläring, Hans-Peter; Krumbein, Angelika; Baldermann, Susanne; Goreta Ban, Smiljana; Perica, Slavko; Schwarz, Dietmar

    2015-01-01

    Reduction of nitrogen application in crop production is desirable for ecological and health-related reasons. Interestingly, nitrogen deficiency can lead to enhanced concentrations of polyphenols in plants. The reason for this is still under discussion. The plants’ response to low nitrogen concentration can interact with other factors, for example radiation intensity. We cultivated red and green leaf lettuce hydroponically in a Mediterranean greenhouse, supplying three different levels of nitrogen (12 mM, 3 mM, 0.75 mM), either in full or reduced (-50%) radiation intensity. In both red and green lettuce, we found clear effects of the nitrogen treatments on growth characteristics, phenolic and photosynthetic compounds, nitrogen, nitrate and carbon concentration of the plants. Interestingly, the concentrations of all main flavonoid glycosides, caffeic acid derivatives, and sucrose increased with decreasing nitrogen concentration, whereas those of chlorophylls, β-carotene, neoxanthin, lactucaxanthin, all trans- and cis-violaxanthin decreased. The constitutive concentrations of polyphenols were lower in the green cultivar, but their relative increase was more pronounced than in the red cultivar. The constitutive concentrations of chlorophylls, β-carotene, neoxanthin, all trans- and cis-violaxanthin were similar in red and green lettuce and with decreasing nitrogen concentration they declined to a similar extent in both cultivars. We only detected little influence of the radiation treatments, e.g. on anthocyanin concentration, and hardly any interaction between radiation and nitrogen concentration. Our results imply a greater physiological plasticity of green compared to the red lettuce regarding its phenolic compounds. They support the photoprotection theory regarding anthocyanins as well as the theory that the deamination activity of phenylalanine ammonia-lyase drives phenylpropanoid synthesis. PMID:26569488

  14. Caffeic Acid Phenethyl Ester: A Review of Its Antioxidant Activity, Protective Effects against Ischemia-reperfusion Injury and Drug Adverse Reactions.

    PubMed

    Tolba, Mai F; Omar, Hany A; Azab, Samar S; Khalifa, Amani E; Abdel-Naim, Ashraf B; Abdel-Rahman, Sherif Z

    2016-10-01

    Propolis, a honey bee product, has been used in folk medicine for centuries for the treatment of abscesses, canker sores and for wound healing. Caffeic acid phenethyl ester (CAPE) is one of the most extensively investigated active components of propolis which possess many biological activities, including antibacterial, antiviral, antioxidant, anti-inflammatory, and anti-cancer effects. CAPE is a polyphenolic compound characterized by potent antioxidant and cytoprotective activities and protective effects against ischemia-reperfusion (I/R)-induced injury in multiple tissues such as brain, retina, heart, skeletal muscles, testis, ovaries, intestine, colon, and liver. Furthermore, several studies indicated the protective effects of CAPE against chemotherapy-induced adverse drug reactions (ADRs) including several antibiotics (streptomycin, vancomycin, isoniazid, ethambutol) and chemotherapeutic agents (mitomycin, doxorubicin, cisplatin, methotrexate). Due to the broad spectrum of pharmacological activities of CAPE, this review makes a special focus on the recently published data about CAPE antioxidant activity as well as its protective effects against I/R-induced injury and many adverse drug reactions. PMID:25365228

  15. Caffeic acid protects mice from memory deficits induced by focal cerebral ischemia.

    PubMed

    Pinheiro Fernandes, Francisco Diego; Fontenele Menezes, Ana Paula; de Sousa Neves, Julliana Catharina; Fonteles, Analu Aragão; da Silva, Ana Thais Araújo; de Araújo Rodrigues, Patrícia; Santos do Carmo, Marta Regina; de Souza, Carolina Melo; de Andrade, Geanne Matos

    2014-10-01

    Brain ischemia pathophysiology involves a complex cascade of events such as inflammation and oxidative stress that lead to neuronal loss and cognitive deficits. Caffeic acid (CA) is a natural phenolic compound with antioxidant and anti-inflammatory properties. To evaluate the neuroprotective efficacy of this compound in mice subjected to a permanent middle cerebral artery occlusion, animals were pretreated and post-treated with CA, 2, 20, and 60 mg/kg/day, intraperitoneally, at 24, 48, 72, 96, or 120 h after ischemia. Animals were evaluated at 24 h after the permanent middle cerebral artery occlusion for brain infarction and neurological deficit score. At 72 h after the occlusion, animals were evaluated for locomotor activity, working memory, and short-term aversive memory; long-term aversive memory was evaluated 24 h after the evaluation of short-term aversive memory. Finally, at 120 h after the event, spatial memory and the expression levels of synaptophysin (SYP), SNAP-25, and caspase 3 were evaluated. The treatment with CA reduced the infarcted area and improved neurological deficit scores. There was no difference in locomotor activity between groups. The working, spatial, and long-term aversive memory deficits improved with CA. Furthermore, western blotting data showed that the expression of SYP, which correlates with synaptic formation and function, decreased after ischemic insult, and CA inhibited the reduction of SYP expression. Ischemia also increased, and CA treatment decreased, caspase 3 expression. These results suggest that CA exerts neuroprotective and antidementia effects, at least in part, by preventing the loss of neural cells and synapses in ischemic brain injury. PMID:25171077

  16. Oxidative stress, polarization of macrophages and tumour angiogenesis: Efficacy of caffeic acid.

    PubMed

    Oršolić, Nada; Kunštić, Martina; Kukolj, Marina; Gračan, Romana; Nemrava, Johann

    2016-08-25

    Macrophage polarization is a process when macrophage expresses different functional programs in response to microenvironmental signals and two extreme forms exist; M1 and M2 macrophages. M1 macrophages are highly microbicidal and anticancer with enhanced ability to kill and phagocytose pathogens, upregulate pro-inflammatory cytokines and reactive molecular species, and present antigens; M2 macrophages and the related tumour associated macrophages (TAMs) regulate tissue remodelling and promote tissue repair and angiogenesis and can amplification of metabolic pathways that can suppress adaptive immune responses. It is demonstrated that ROS production, critical for the activation and functions of M1 macrophages, is necessary for the differentiation of M2 macrophages and TAMs, and that antioxidant therapy blocks TAMs differentiation and tumorigenesis in mouse models of cancer. In order to study how caffeic acid (CA), a natural antioxidant, affects macrophage function, polarization, angiogenesis and tumour growth we injected mice with Ehrlich ascites tumour (EAT) cells and treated them for 10 days with CA in a dose of 40 and/or 80 mg kg(-1.) Macrophage polarization was further characterized by quantifying secreted pro- and anti-inflammatory cytokines, nitric oxide and arginase 1 activity. CA may increase the cytotoxic actions of M1 macrophages and inhibit tumour growth; inhibitory activity on TAMs may be mediated through its antioxidative activity. Taken together, we conclude that the antitumour activity of CA was the result of the synergistic activities of different mechanisms by which CA acts on proliferation, angiogenesis, immunomodulation and survival. The continuous administration of CA efficiently blocked the occurrence of TAMs and markedly suppressed tumorigenesis in mouse cancer models. Targeting TAMs by antioxidants can be a potentially effective method for cancer treatment. PMID:27378625

  17. Effects of novel hybrids of caffeic acid phenethyl ester and NSAIDs on experimental ocular inflammation.

    PubMed

    Pittalà, Valeria; Salerno, Loredana; Romeo, Giuseppe; Siracusa, Maria Angela; Modica, Maria Nunziata; Romano, Giovanni Luca; Salomone, Salvatore; Drago, Filippo; Bucolo, Claudio

    2015-04-01

    In this study, we report the design and synthesis of novel hybrids of caffeic acid phenetyl ester (CAPE) and non-steroidal anti-inflammatory drugs (NSAIDs). We assessed their effects on an experimental ocular inflammation in New Zealand rabbits. The formulations of CAPE-aspirin and CAPE-indomethacin hybrids were topical instilled in the rabbit׳s eye. Afterwards, the anti-inflammatory activity was evaluated by grading the clinical signs and by assessing the inflammatory cell count, protein, PGE2 and TNFα levels in the aqueous humor. Furthermore, ocular tolerability of hybrids formulations was evaluated in a separate set of animals by using a modified Draize test. The ocular inflammation in the control group was significantly higher than in both the hybrid-treated groups, as indicated by clinical grading and biomarkers assessment. However, only the CAPE-aspirin hybrid reduced, in a significant dose-dependent manner, the ocular inflammation elicited by paracentesis. CAPE-indomethacin hybrid was able to significantly attenuate the clinical grading and the PGE2 aqueous levels only at the highest dose (0.1%). CAPE-aspirin significantly reduced PGE2 and TNFα levels in the aqueous humor as well as proteins and PMNs. Finally, all formulations showed no ocular irritation compared with vehicle-treated group. In conclusion, CAPE-aspirin shows full anti-inflammatory efficacy in experimental model of ocular inflammation demonstrating an optimal pharmacological and safety profile. Taken together these data indicate that CAPE-aspirin hybrid represents a valid and safe new chemical entity potentially useful for the treatment of ocular inflammation. PMID:25704612

  18. Genomic study of the absorption mechanism of p-coumaric acid and caffeic acid of extract of Ananas comosus L. leaves.

    PubMed

    Dang, Yun-jie; Zhu, Chun-yan

    2015-03-01

    Cardiac disease has emerged as the leading cause of death worldwide, and food rich in phenolic acids has drawn much attention as sources of active substances of hypolipidemic drug. Ananas comosus L. (pineapple) is one of the most popular tropical and subtropical fruits. Isolated from pineapple leaves, EAL(Extract of Ananas Comosus L. Leaves) is rich in phenolic acids, such as p-coumaric acid, caffeic acid, and other phenolics, highly relevant to the putative cardiovascular-protective effects, which suggests its potential to be a new plant medicine for treatment of cardiac disease, but little is known about absorption, distribution, metabolism, and excretion of EAL in animals or human beings. In this study, we employed cDNA microarray, Caco-2 cell lines, and rat intestinal model to explore the absorption behavior of p-coumaric acid and caffeic acid in EAL. The permeation of 2 substances was concentration and time dependent. Results also indicated that monocarboxylic acid transporter was involved in the transepithelial transport of p-coumaric acid and caffeic acid. PMID:25678210

  19. Caffeic Acid Phenethyl Ester: Consequences of Its Hydrophobicity in the Oxidative Functions and Cytokine Release by Leukocytes

    PubMed Central

    Paracatu, Luana Chiquetto; Faria, Carolina Maria Quinello Gomes; Rennó, Camila; Palmeira, Patricia; da Fonseca, Luiz Marcos; Ximenes, Valdecir Farias

    2014-01-01

    Numerous anti-inflammatory properties have been attributed to caffeic acid phenethyl ester (CAPE), an active component of propolis. NADPH oxidases are multienzymatic complexes involved in many inflammatory diseases. Here, we studied the importance of the CAPE hydrophobicity on cell-free antioxidant capacity, inhibition of the NADPH oxidase and hypochlorous acid production, and release of TNF-α and IL-10 by activated leukocytes. The comparison was made with the related, but less hydrophobic, caffeic and chlorogenic acids. Cell-free studies such as superoxide anion scavenging assay, triene degradation, and anodic peak potential (Epa) measurements showed that the alterations in the hydrophobicity did not provoke significant changes in the oxidation potential and antiradical potency of the tested compounds. However, only CAPE was able to inhibit the production of superoxide anion by activated leukocytes. The inhibition of the NADPH oxidase resulted in the blockage of production of hypochlorous acid. Similarly, CAPE was the more effective inhibitor of the release of TNF-α and IL-10 by Staphylococcus aureus stimulated cells. In conclusion, the presence of the catechol moiety and the higher hydrophobicity were essential for the biological effects. Considering the involvement of NADPH oxidases in the genesis and progression of inflammatory diseases, CAPE should be considered as a promising anti-inflammatory drug. PMID:25254058

  20. Caffeic acid: potential applications in nanotechnology as a green reducing agent for sustainable synthesis of gold nanoparticles.

    PubMed

    Seo, Yu Seon; Cha, Song-Hyun; Yoon, Hye-Ran; Kang, Young-Hwa; Park, Youmie

    2015-04-01

    The sustainable synthesis of gold nanoparticles from gold ions was conducted with caffeic acid as a green reducing agent. The formation of gold nanoparticles was confirmed by spectroscopic and microscopic methods. Spherical nanoparticles with an average diameter of 29.99 ± 7.43 nm were observed in high- resolution transmission electron microscopy and atomic force microscopy images. The newly prepared gold nanoparticles exhibited catalytic activity toward the reduction of 4-nitrophenol to 4-aminophenol in the presence of sodium borohydride. This system enables the preparation of green catalysts using plant natural products as reducing agents, which fulfills the growing need for sustainability initiatives. PMID:25973494

  1. Modulation of phenytoin teratogenicity and embryonic covalent binding by acetylsalicylic acid, caffeic acid, and alpha-phenyl-N-t-butylnitrone: implications for bioactivation by prostaglandin synthetase

    SciTech Connect

    Wells, P.G.; Zubovits, J.T.; Wong, S.T.; Molinari, L.M.; Ali, S.

    1989-02-01

    Teratogenicity of the anticonvulsant drug phenytoin is thought to involve its bioactivation by cytochromes P-450 to a reactive arene oxide intermediate. We hypothesized that phenytoin also may be bioactivated to a teratogenic free radical intermediate by another enzymatic system, prostaglandin synthetase. To evaluate the teratogenic contribution of this latter pathway, an irreversible inhibitor of prostaglandin synthetase, acetylsalicylic acid (ASA), 10 mg/kg intraperitoneally (ip), was administered to pregnant CD-1 mice at 9:00 AM on Gestational Days 12 and 13, 2 hr before phenytoin, 65 mg/kg ip. Other groups were pretreated 2 hr prior to phenytoin administration with either the antioxidant caffeic acid or the free radical spin trapping agent alpha-phenyl-N-t-butylnitrone (PBN). Caffeic acid and PBN were given ip in doses that respectively were up to 1.0 to 0.05 molar equivalents to the dose of phenytoin. Dams were killed on Day 19 and the fetuses were assessed for teratologic anomalies. A similar study evaluated the effect of ASA on the in vivo covalent binding of radiolabeled phenytoin administered on Day 12, in which case dams were killed 24 hr later on Day 13. ASA pretreatment produced a 50% reduction in the incidence of fetal cleft palates induced by phenytoin (p less than 0.05), without significantly altering the incidence of resorptions or mean fetal body weight. Pretreatment with either caffeic acid or PBN resulted in dose-related decreases in the incidence of fetal cleft palates produced by phenytoin, with maximal respective reductions of 71 and 82% at the highest doses of caffeic acid and PBN (p less than 0.05).

  2. Melatonin and caffeic acid phenethyl ester in the regulation of mitochondrial function and apoptosis: The basis for future medical approaches.

    PubMed

    Erdemli, Haci Kemal; Akyol, Sumeyya; Armutcu, Ferah; Gulec, Mehmet Akif; Canbal, Metin; Akyol, Omer

    2016-03-01

    The aim of this review article is to summarize and compare the effects of melatonin and caffeic acid phenethyl ester (CAPE) on the relationship between mitochondrial functioning and apoptosis. References in this article were selected with an approach based on a comprehensive literature review by using MEDLINE/PubMed and Google Scholar databases which were scanned in the last six months without any restrictions. For each database, the review terms used are 'melatonin', 'caffeic acid phenethyl ester, both together and associated with other key words such as apoptosis and mitochondria. Evidential mitochondrial molecular backgrounds for diseases make these two molecule competitors, since both of them use the same pathways to cope with fundamentals of the diseases such as nuclear factor κ-light-chain-enhancer of activated B (NF-κB inhibition, induction of mitochondrial apoptosis in cancer cells, free radical scavenging effects, and antioxidant activities. The data reviewed in this paper provide a useful background for the understanding of some molecular details of melatonin and CAPE on several medical situation and diseases. Mutual usage of these two tremendous molecules might have a capacity to open new therapeutic approaches in near future. PMID:26784848

  3. Application of multivariate curve resolution alternating least squares method for determination of caffeic acid in the presence of catechin interference.

    PubMed

    Meshki, Marzieh; Behpour, Mohsen; Masoum, Saeed

    2015-03-15

    In the current article, preparation and application of a graphene oxide nanosheets-based sensor for electrochemical determination of caffeic acid (CA) in the presence of catechin is described. This measurement was performed using the differential pulse voltammetry (DPV) technique and chemometric methods such as multivariate curve resolution-alternating least squares (MCR-ALS). The modified sensor was characterized by various techniques such as Fourier transform infrared spectroscopy (FTIR), Raman spectroscopy, ultraviolet-visible, X-ray diffraction (XRD), and scanning electron microscopy (SEM). Operating conditions and influencing variables (involving several chemical and instrumental variables) were optimized with central composite rotatable design and response surface methodology. The second-order electrochemical data were generated by changing the pulse height in DPV, and after potential shift correction MCR-ALS was applied. Under the optimized conditions, the dynamic range for CA was from 0.5 to 100.0 μM and the detection limit was found to be 1.1×10(-9) M. The results revealed that the modified electrode shows an improvement in anodic oxidation activity of CA due to a marked enhancement in the current response compared with the bare carbon paste electrode. The modified electrode demonstrated good sensitivity, selectivity, and stability. The proposed method was successfully applied in determination of caffeic acid in the presence of unexpected electroactive interferences with a very high degree of overlapping such as catechin in real samples. PMID:25432066

  4. Anti-tyrosinase kinetics and antibacterial process of caffeic acid N-nonyl ester in Chinese Olive (Canarium album) postharvest.

    PubMed

    Jia, Yu-Long; Zheng, Jing; Yu, Feng; Cai, Yi-Xiang; Zhan, Xi-Lan; Wang, Hui-Fang; Chen, Qing-Xi

    2016-10-01

    Enzymatic browning and bacterial putrefaction are mainly responsible for quality losses of Chinese Olive (Canarium album) postharvest and lead to very short shelf life on average. Screening anti-browning and anti-bacterial agents is important for preservation of Chinese Olive. Caffeic acid N-nonyl ester (C-9) and caffeic acid N- Heptyl ester (C-7) was synthesized as inhibitors of tyrosinase, which is a key enzyme in browning process. The compound of C-9 could inhibit the activity of tyrosinase strongly and its IC50 value was determined to be 37.5μM, while the compound of C-7 had no inhibitory ability. Kinetic analyses showed that compound of C-9 has been a reversible inhibitory mechanism below 50μM and been irreversible mechanisms above 50μM. For the reversible inhibitory mechanism, the values of inhibitory constants (KI and KIS) were determined to be 24.6 and 37.4μM, respectively. The results of Chinese Olive fruit postharvest showed that the compound of C-9 could effectively anti-browning and anti-bacterial putrefaction. In addition, this compound had strong antibacterial activities against Staphylococcus aureus, Escherichia coli, Bacillus subtilis and Salmonella. Therefore, C-9 could be a potential anti-browning and anti-bacterial reagent. PMID:27246378

  5. Cytoprotection of human endothelial cells from menadione cytotoxicity by caffeic acid phenethyl ester: the role of heme oxygenase-1.

    PubMed

    Wang, Xinyu; Stavchansky, Salomon; Zhao, Baiteng; Bynum, James A; Kerwin, Sean M; Bowman, Phillip D

    2008-09-01

    Caffeic acid phenethyl ester (CAPE), derived from various plant sources, has been shown to ameliorate ischemia/reperfusion injury in vivo, and this has been attributed to its ability to reduce oxidative stress. Here we investigated the cytoprotection of CAPE against menadione-induced oxidative stress in human umbilical vein endothelial cells (HUVEC) to evaluate potential gene expression involvement. CAPE exhibited dose-dependent cytoprotection of HUVEC. A gene screen with microarrays was performed to identify the potential cytoprotective gene(s) induced by CAPE. Heme oxygenase-1 (HO-1) was highly upregulated by CAPE and this was confirmed with reverse transcriptase polymerase chain reaction (RT-PCR) and western blotting. Inhibition of HO-1 activity using the HO-1 inhibitor tin protoporphyrin IX (SnPPIX), resulted in loss of cytoprotection. Carbon monoxide, one of HO-1 catabolic products appeared to play a small role in CAPE protection. Caffeic acid, a potential metabolite of CAPE with similar free radical scavenging ability, however, didn't show any cytoprotective effect nor induce HO-1. These findings suggest an important role of HO-1 induction in CAPE cytoprotection against oxidant stress, which may not relate to CAPE structural antioxidant activity nor to its traditional enzymatic activity in decomposing heme but to a yet to be determined activity. PMID:18573251

  6. Design, synthesis and evaluation of semi-synthetic triazole-containing caffeic acid analogues as 5-lipoxygenase inhibitors.

    PubMed

    De Lucia, Daniela; Lucio, Oscar Méndez; Musio, Biagia; Bender, Andreas; Listing, Monika; Dennhardt, Sophie; Koeberle, Andreas; Garscha, Ulrike; Rizzo, Roberta; Manfredini, Stefano; Werz, Oliver; Ley, Steven V

    2015-08-28

    In this work the synthesis, structure-activity relationship (SAR) and biological evaluation of a novel series of triazole-containing 5-lipoxygenase (5-LO) inhibitors are described. The use of structure-guided drug design techniques provided compounds that demonstrated excellent 5-LO inhibition with IC50 of 0.2 and 3.2 μm in cell-based and cell-free assays, respectively. Optimization of binding and functional potencies resulted in the identification of compound 13d, which showed an enhanced activity compared to the parent bioactive compound caffeic acid 5 and the clinically approved zileuton 3. Compounds 15 and 16 were identified as lead compounds in inhibiting 5-LO products formation in neutrophils. Their interference with other targets on the arachidonic acid pathway was also assessed. Cytotoxicity tests were performed to exclude a relationship between cytotoxicity and the increased activity observed after structure optimization. PMID:26197161

  7. Inhibitory activities of propolis and its promising component, caffeic acid phenethyl ester, against amyloidogenesis of human transthyretin.

    PubMed

    Yokoyama, Takeshi; Kosaka, Yuto; Mizuguchi, Mineyuki

    2014-11-13

    Transthyretin (TTR) is a homotetrameric serum protein associated with amyloidoses such as familial amyloid polyneuropathy and senile systemic amyloidosis. The amyloid fibril formation of TTR can be inhibited through stabilization of the TTR tetramer by the binding of small molecules. In this study, we examined the inhibitory potency of caffeic acid phenethyl ester (CAPE) and its derivatives. Thioflavin T assay showed that CAPE suppressed the amyloid fibril formation of TTR. Comparative analysis of the inhibitory potencies revealed that phenethyl ferulate was the most potent among the CAPE derivatives. The binding of phenethyl ferulate and the selected compounds to TTR were confirmed by the 8-anilino-1-naphthalenesulfonic acid displacement and X-ray crystallography. It was also demonstrated that Bio 30, which is a CAPE-rich commercially available New Zealand propolis, inhibited TTR amyloidogenesis and stabilized the TTR tetramer. These results suggested that a propolis may be efficient for preventing TTR amyloidosis. PMID:25314129

  8. Caffeic Acid Phenethyl Ester Increases Radiosensitivity of Estrogen Receptor-Positive and -Negative Breast Cancer Cells by Prolonging Radiation-Induced DNA Damage

    PubMed Central

    Khoram, Nastaran Masoudi; Bigdeli, Bahareh; Nikoofar, Alireza

    2016-01-01

    Purpose Breast cancer is an important cause of death among women. The development of radioresistance in breast cancer leads to recurrence after radiotherapy. Caffeic acid phenethyl ester (CAPE), a polyphenolic compound of honeybee propolis, is known to have anticancer properties. In this study, we examined whether CAPE enhanced the radiation sensitivity of MDA-MB-231 (estrogen receptor-negative) and T47D (estrogen receptor-positive) cell lines. Methods The cytotoxic effect of CAPE on MDA-MB-231 and T47D breast cancer cells was evaluated by performing an 3-(4,5-dimethylthiazol-2-yl)-2,5 diphenyltetrazolium bromide (MTT) assay. To assess clonogenic ability, MDA-MB-231 and T47D cells were treated with CAPE (1 µM) for 72 hours before irradiation, and then, a colony assay was performed. A comet assay was used to determine the number of DNA strand breaks at four different times. Results CAPE decreased the viability of both cell lines in a dose- and time-dependent manner. In the clonogenic assay, pretreatment of cells with CAPE before irradiation significantly reduced the surviving fraction of MDA-MB-231 cells at doses of 6 and 8 Gy. A reduction in the surviving fraction of T47D cells was observed relative to MDA-MB-231 at lower doses of radiation. Additionally, CAPE maintained radiation-induced DNA damage in T47D cells for a longer period than in MDA-MB-231 cells. Conclusion Our results indicate that CAPE impairs DNA damage repair immediately after irradiation. The induction of radiosensitivity by CAPE in radioresistant breast cancer cells may be caused by prolonged DNA damage. PMID:27066092

  9. Redox intermediates of flavonoids and caffeic acid esters from propolis: an EPR spectroscopy and cyclic voltammetry study.

    PubMed

    Rapta, P; Misík, V; Stasko, A; Vrábel, I

    1995-05-01

    The redox properties of flavonoids: chrysin (1), tectochrysin (2), galangin (3), isalpinin (4), pinostrobin (5), pinobanksin (6), pinobanksin-3-acetate (7), and of caffeic acid ester (8) and diacetylcaffeic acid ester (9), all isolated from propolis, were investigated by cyclic voltammetry in acetonitrile. The choice of aprotic solvent lowered the reactivity of the radical intermediates and made possible to identify redox steps and intermediates not detected so far. The oxidation potentials (vs. saturated calomel electrode) of the investigated compounds were in the region of 1.5 V for 3 and 4; 1.9 V for 1, 2, and 5; 2.0 V for 6 and 7; 1.29 V for 8; and 2.3 V for 9. These oxidation potentials were mainly influenced by the presence of a double bond in 2,3-position and substituent R1 in position 3. Comparison with our earlier data revealed that flavonoids, 1-4, and caffeic acid ester 8 with lower oxidation potentials showed the maximal lipid antioxidant activity, whereas those with higher potentials (5, 6, 7, and 9) are less active. On reduction of 1-9 several one-electron-steps were typically observed in the potential regions: -1.5 V, -1.8 V, and -2 V. where in simultaneous EPR experiments anion radicals of 1 and 3 were observed with the center of unpaired spin density on ring A. Upon oxidation of flavonoids 1-4 carbonyl carbon-centered radicals, .C(O)R, were identified as consecutive products using the EPR spin trapping technique. PMID:7797098

  10. Biotransformation of polyphenols in a dynamic multistage gastrointestinal model.

    PubMed

    Sadeghi Ekbatan, Shima; Sleno, Lekha; Sabally, Kebba; Khairallah, Joelle; Azadi, Behnam; Rodes, Laetitia; Prakash, Satya; Donnelly, Danielle J; Kubow, Stan

    2016-08-01

    A multi-reactor gastrointestinal model was used to digest a mixture of pure polyphenol compounds, including non-flavonoid phenolic acids (chlorogenic acid, caffeic acid, ferulic acid) and a flavonoid (rutin) to identify phenolic metabolites and short chain fatty acids (SCFAs) and compare relative antioxidant capacities following a 24h digestion. Biotransformation of these polyphenols occurred in the colonic compartments generating phenylpropionic, benzoic, phenylacetic and cinnamic acids. Total SCFAs increased in all colonic vessels with a rise in the proportion of propionic to acetic acid. Antioxidant capacity increased significantly in all compartments, but first in the stomach, small intestine and ascending colon. After 24h, the colonic vessels without parent polyphenols, but containing new metabolites, had antioxidant capacities similar to the stomach and small intestine, containing parent compounds. Biotransformation of pure polyphenols resulted in different phenolic metabolite and SCFAs profiles in each colonic segment, with important health implications for these colonic compartments. PMID:26988524

  11. Determination of the structure and catalytic mechanism of Sorghum bicolor caffeic acid O-methyltransferase and the structural impact of three brown midrib12 mutations

    Technology Transfer Automated Retrieval System (TEKTRAN)

    With S-adenosylmethionine (SAM) acting as the methyl donor, caffeic acid O-methyltransferase from Sorghum bicolor (SbCOMT) methylates the 5-hydroxyl group of its preferred substrate, 5-hydroxyconiferaldehyde, to form sinapaldehyde. In order to determine the mechanism of SbCOMT and understand the red...

  12. Amine-modified SBA-15 and MCF mesoporous molecular sieves as promising sorbents for natural antioxidant. Modeling of caffeic acid adsorption.

    PubMed

    Moritz, Michał; Geszke-Moritz, Małgorzata

    2016-04-01

    This work presents a detailed study of caffeic acid adsorption on mesoporous SBA-15 and MCF silicas functionalized with (3-aminopropyl)triethoxysilane (APTES) and 3-[2-(aminoethylamino)propyl]trimethoxysilane (AEAPTMS). Synthesized mesoporous adsorbents were characterized using different analytical techniques such as N2 sorption, XRD, TEM, SEM and FT-IR. The adsorption studies of caffeic acid were conducted in various organic solvents. Moreover, the effect of water content in 2-propanol-water mixture on adsorption efficiency was investigated. The experimental data were best fitted to the Langmuir equation, followed by the Temkin, Dubinin-Radushkevich and Freundlich models. The maximum adsorption capacity values calculated from the Langmuir model demonstrated that SBA-15 and MCF silicas modified with AEAPTMS revealed better adsorption properties toward caffeic acid (192.3 and 161.3mg/g, respectively) as compared to the materials modified with APTES (125.0 and 113.6 mg/g, respectively). The obtained results indicate that both SBA-15 and MCF silicas functionalized with AEAPTMS and APTES are promising materials for the entrapment of caffeic acid. PMID:26838867

  13. Caffeic acid phenethyl ester as a remedial agent for reproductive functions and oxidative stress-based pathologies of gonads.

    PubMed

    Akyol, Sumeyya; Akbas, Ali; Butun, Ilknur; Toktas, Muhsin; Ozyurt, Huseyin; Sahin, Semsettin; Akyol, Omer

    2015-01-01

    In recent years, the studies on the roles of caffeic acid phenethyl ester (CAPE) in several disease models and cell cultures are tremendously growing. It is such a great molecule that was used by ancient times to ameliorate some diseases and nowadays, it is used by modern medicine to test the effectiveness. In this mini-review article, the protection capability of CAPE, as a liposoluble antioxidant and a potent nuclear factor kappa B inhibitor, on oxidative and non-oxidative ovary, and testis damages has been summarized. In view of our laboratory findings/experience and those reported in the hitherto literature, we suggest that CAPE possesses protective effects for pathologies of the reproductive organs induced by untoward effects of harmful molecules such as free oxygen radicals, pesticides, methotrexate, and MK-801 (dizocilpine). PMID:26401405

  14. Photoinduced coupling and adsorption of caffeic acid on silver surface studied by surface-enhanced Raman spectroscopy

    NASA Astrophysics Data System (ADS)

    Sánchez-Cortés, S.; García-Ramos, J. V.

    1999-12-01

    The effect of light on the caffeic acid (CA) oxidative coupling is studied in aqueous solution and on silver by surface-enhanced Raman spectroscopy (SERS). CA can polymerize in aqueous solution or on a metal surface through an oxidative mechanism involving the formation of the corresponding quinone giving rise to characteristic Raman features in each case. We show here that the effect of light in relation to this oxidative coupling is crucial taking place mainly in the solution bulk. The products derived from such polymerization can then adsorb on the silver surface employed for SERS measurements, thus allowing its detection by Raman spectroscopy. The influence of irradiation time and the wavelength of the light employed for the photoinduced coupling was investigated.

  15. Quantum dots-based label-free fluorescence sensor for sensitive and non-enzymatic detection of caffeic acid.

    PubMed

    Xiang, Xia; Shi, Jianbin; Huang, Fenghong; Zheng, Mingming; Deng, Qianchun

    2015-08-15

    We have developed a label-free fluorescence sensor for caffeic acid (CA) by the use of CdTe:Zn(2+) quantum dots (CdTe:Zn(2+) QDs) as an output signal. The principle of sensor is based on the fluorescence quenching and binding properties of Fe(2+) toward QDs and CA, respectively. To provide a fluorescence turn-on mode for CA detection, Fe(2+) is first mixed with QDs solution, leading to a low fluorescence emission. With the addition of CA, the fluorescence of QDs is recovered due to the strong binding interaction between CA and Fe(2+). Thus, a QDs-based label-free fluorescence sensor, designed in a simple mix-and-detect format, is established for CA detection. This study demonstrated here not only offers simple, sensitive and non-enzymatic detection method for CA, but also brings to light a new application of QDs in the food analysis. PMID:25966400

  16. Caffeic Acid Phenethyl Ester as a Protective Agent against Nephrotoxicity and/or Oxidative Kidney Damage: A Detailed Systematic Review

    PubMed Central

    Akyol, Sumeyya; Ugurcu, Veli; Altuntas, Aynur; Hasgul, Rukiye; Cakmak, Ozlem

    2014-01-01

    Caffeic acid phenethyl ester (CAPE), an active component of propolis, has been attracting the attention of different medical and pharmaceutical disciplines in recent years because of its antioxidant, anti-inflammatory, antiproliferative, cytotoxic, antiviral, antifungal, and antineoplastic properties. One of the most studied organs for the effects of CAPE is the kidney, particularly in the capacity of this ester to decrease the nephrotoxicity induced by several drugs and the oxidative injury after ischemia/reperfusion (I/R). In this review, we summarized and critically evaluated the current knowledge regarding the protective effect of CAPE in nephrotoxicity induced by several special medicines such as cisplatin, doxorubicin, cyclosporine, gentamycin, methotrexate, and other causes leading to oxidative renal injury, namely, I/R models and senility. PMID:25003138

  17. CO₂ enrichment can produce high red leaf lettuce yield while increasing most flavonoid glycoside and some caffeic acid derivative concentrations.

    PubMed

    Becker, Christine; Kläring, Hans-Peter

    2016-05-15

    Carbon dioxide (CO2) enrichment is a common practice in greenhouses to increase crop yields up to 30%. Yet, reports on the effect on foliar phenolic compounds vary. We studied the effect on two red leaf lettuce cultivars, grown for 25 days in growth chambers at CO2 concentrations of 200 or 1,000 ppm, with some plants exchanged between treatments after 11 days. As expected, head mass increased with higher CO2 concentration. Regression analysis, corrected for head mass, showed increased concentrations of most flavonoid glycosides at high CO2 concentrations while only some caffeic acid derivatives were increased, and not uniformly in both cultivars. Sugar concentrations increased with CO2 concentration. Generally, conditions in the 10 days before harvest determined concentrations. We suspect that phenolic compounds were mainly accumulated because plenty of precursors were available. The results indicate that CO2 enrichment can result in high yields of red leaf lettuce rich in phenolic compounds. PMID:26776031

  18. Protective effects of p-nitro caffeic acid phenethyl ester on acute myocardial ischemia-reperfusion injury in rats

    PubMed Central

    DU, QIN; HAO, CHUNZHI; GOU, JING; LI, XIAOLI; ZOU, KAILI; HE, XIAOYAN; LI, ZHUBO

    2016-01-01

    Myocardial ischemia-reperfusion (IR) causes widespread cardiomyocyte dysfunction, including apoptosis and necrosis. The present study aimed to investigate the possible cardioprotective effects of p-nitro caffeic acid phenethyl ester (CAPE-NO2) on myocardial IR-induced injury in vivo. To generate a rat model of myocardial IR, the left anterior descending coronary artery was occluded for 30 min, followed by reperfusion for 2 h. The rats were administered either the sham treatment (the sham and IR control groups) or the therapeutic agents [the caffeic acid phenethyl ester (CAPE) and CAPE-NO2 groups] 10 min prior to the occlusion. Myocardial IR-induced injury is characterized by: A significant increase in the levels of myocardial enzymes, including creatine kinase, lactate dehydrogenase and aspartate transaminase; a marked increase in intercellular adhesion molecule 1 expression levels, lipid peroxidation products and inflammatory mediators; and a significant decrease in myocardial antioxidants, including catalase, total superoxide dismutase and glutathione peroxidase. In the present study, pretreatment with CAPE-NO2 significantly ameliorated these changes, and decreased the infarct size, as compared with the IR control group (10.32±3.8 vs. 35.65±5.4%). Furthermore, western blotting demonstrated that pretreatment with CAPE-NO2 downregulated the myocardial IR-induced protein expression levels of B-cell lymphoma-2 (Bcl-2)-associated X protein (Bax), cleaved caspase-3, P38 and the Bax/Bcl-2 ratio. CAPE-NO2 also upregulated the myocardial IR-induced expression levels of Bcl-2, phosphoinositide-3-kinase, phosphorylated Akt and mammalian target of rapamycin. In conclusion, the results of the present study indicated that CAPE-NO2 demonstrated improved cardioprotective effects, as compared with CAPE; therefore, CAPE-NO2 may represent a novel approach to pharmacological cardioprotection. PMID:27073461

  19. Caffeic Acid Reduces the Viability and Migration Rate of Oral Carcinoma Cells (SCC-25) Exposed to Low Concentrations of Ethanol

    PubMed Central

    Dziedzic, Arkadiusz; Kubina, Robert; Kabała-Dzik, Agata; Wojtyczka, Robert D.; Morawiec, Tadeusz; Bułdak, Rafał J.

    2014-01-01

    Alcohol increases the risk of carcinoma originated from oral epithelium, but the biological effects of ultra-low doses of ethanol on existing carcinoma cells in combination with natural substances are still unclear. A role for ethanol (EtOH), taken in small amounts as an ingredient of some beverages or mouthwashes to change the growth behavior of established squamous cell carcinoma, has still not been examined sufficiently. We designed an in vitro study to determine the effect of caffeic acid (CFA) on viability and migration ability of malignant oral epithelial keratinocytes, exposed to ultra-low concentrations (maximum 100 mmol/L) EtOH. MTT (3-[4,5-dimethylthiazol-2-yl]-2,5-dimethyltetrazolium bromide) and LDH (lactate dehydrogenase) assays were used to assess the cytotoxic effect of EtOH/CFA and the viability of squamous carcinoma SCC-25 cells (ATCC CRL-1628, mobile part of the tongue). Tested EtOH concentrations were: 2.5, 5, 10, 25, 50, and 100 mmol/L, along with an equal CFA concentration of 50 μmol/L. Carcinoma cells’ migration was investigated by monolayer “wound” healing assay. We demonstrated that very low concentrations of EtOH ranging between 2.5 and 10 mmol/L may induce the viability of oral squamous cell carcinoma cells, while the results following addition of CFA reveal an antagonistic effect, attenuating pro-proliferative EtOH activity. The migration rate of oral squamous carcinoma cells can be significantly inhibited by the biological activity of caffeic acid. PMID:25329614

  20. Down-regulation of the Caffeic acid O-methyltransferase Gene in Switchgrass Reveals a Novel Monolignol Analog

    SciTech Connect

    Tschaplinski, Timothy J; Standaert, Robert F; Engle, Nancy L; Martin, Madhavi Z; Sangha, Amandeep K; Parks, Jerry M; Smith, Jeremy C; Samuel, Reichel; Pu, Yunqiao; Ragauskas, A J; Hamilton, Choo Yieng; Fu, Chunxiang; Wang, Zeng-Yu; Davison, Brian H; Dixon, Richard A; Mielenz, Jonathan R

    2012-01-01

    Down-regulation of the caffeic acid 3-O-methyltransferase (COMT) gene in the lignin biosynthetic pathway of switchgrass (Panicum virgatum) resulted in cell walls of transgenic plants releasing more constituent sugars after pretreatment by dilute acid and treatment with glycosyl hydrolases from an added enzyme preparation and from Clostridium thermocellum. Fermentation of both wild-type and transgenic switchgrass after milder hot water pretreatment with no water washing showed that only the transgenic switchgrass inhibited C. thermocellum. Gas chromatography-mass spectrometry-based metabolomics were undertaken on cell wall aqueous extracts to determine the nature of the microbial inhibitors, confirming the increased concentration of a number of phenolic acids and aldehydes that are known inhibitors of fermentation. Metabolomic analyses of the transgenic biomass additionally revealed the presence of a novel monolignol-like metabolite, identified as trans-3, 4-dimethoxy-5-hydroxycinnamyl alcohol (iso-sinapyl alcohol) in both non-pretreated, as well as hot water pretreated samples. Although there was no indication that iso-sinapyl alcohol was integrated into the cell wall, diversion of substrates from sinapyl alcohol to free iso-sinapyl alcohol, its glucoside, and associated upstream lignin pathway changes, including increased phenolic aldehydes and acids, are associated with more facile cell wall deconstruction, and to the observed inhibitory effect on microbial growth.

  1. Evaluation of chemical constituents and antioxidant activity of coconut water (Cocus nucifera L.) and caffeic acid in cell culture.

    PubMed

    Santos, João L A; Bispo, Vanderson S; Filho, Adriano B C; Pinto, Isabella F D; Dantas, Lucas S; Vasconcelos, Daiane F; Abreu, Fabíula F; Melo, Danilo A; Matos, Isaac A; Freitas, Florêncio P; Gomes, Osmar F; Medeiros, Marisa H G; Matos, Humberto R

    2013-01-01

    Coconut water contains several uncharacterized substances and is widely used in the human consumption. In this paper we detected and quantified ascorbic acid and caffeic acid and total phenolics in several varieties of coconut using HPLS/MS/MS (25.8 ± 0.6 µg/mL and 1.078 ± 0.013 µg/mL and 99.7 µg/mL, respectively, in the green dwarf coconut water, or 10 mg and 539 µg and 39.8 mg for units of coconut consumed, 500 ± 50 mL). The antioxidant potential of four coconut varieties (green dwarf, yellow dwarf, red dwarf and yellow Malaysian) was compared with two industrialized coconut waters and the lyophilized water of the green dwarf variety. All varieties were effective in scavenging the DPPH radical (IC₅₀=73 µL) and oxide nitric (0.1 mL with an IP of 29.9%) as well as in inhibiting the in vitro production of thiobarbituric acid reactive substances (1 mL with an IP of 34.4%), highlighting the antioxidant properties of the green dwarf which it is the most common used. In cell culture, the green dwarf water was efficient in protecting against oxidative damages induced by hydrogen peroxide. PMID:24141413

  2. Antiproliferative Effects of Honey and of Its Polyphenols: A Review

    PubMed Central

    Jaganathan, Saravana Kumar; Mandal, Mahitosh

    2009-01-01

    Honey has been used since long time both in medical and domestic needs, but only recently the antioxidant property of it came to limelight. The fact that antioxidants have several preventative effects against different diseases, such as cancer, coronary diseases, inflammatory disorders, neurological degeneration, and aging, led to search for food rich in antioxidants. Chemoprevention uses various dietary agents rich in phytochemicals which serve as antioxidants. With increasing demand for antioxidant supply in the food, honey had gained vitality since it is rich in phenolic compounds and other antioxidants like ascorbic acid, amino acids, and proteins. Some simple and polyphenols found in honey, namely, caffeic acid (CA), caffeic acid phenyl esters (CAPE), Chrysin (CR), Galangin (GA), Quercetin (QU), Kaempferol (KP), Acacetin (AC), Pinocembrin (PC), Pinobanksin (PB), and Apigenin (AP), have evolved as promising pharmacological agents in treatment of cancer. In this review, we reviewed the antiproliferative and molecular mechanisms of honey and above-mentioned polyphenols in various cancer cell lines. PMID:19636435

  3. Regulation of osteoclastogenesis by Simon extracts composed of caffeic acid and related compounds: successful suppression of bone destruction accompanied with adjuvant-induced arthritis in rats.

    PubMed

    Tang, Quan Yong; Kukita, Toshio; Ushijima, Yuki; Kukita, Akiko; Nagata, Kengo; Sandra, Ferry; Watanabe, Toshiyuki; Toh, Kazuko; Okuma, Yutaka; Kawasaki, Sadamichi; Rasubala, Linda; Teramachi, Junpei; Miyamoto, Ichiko; Wu, Zhou; Iijima, Tadahiko

    2006-03-01

    Simon extracts are vitamin K(1)-rich food materials extracted from the leaves of the Simon sweet potato. Although vitamin K is known to stimulate bone formation, we postulated that Simon extracts also contain unknown biological compounds having the ability to regulate bone resorption. Here we prepared the vitamin K-free fraction from the Simon extracts and investigated the ability of this fraction on the differentiation of osteoclasts. A remarkable inhibitory effect of osteoclastogenesis was observed when osteoclast precursors were treated with this fraction in rat bone marrow culture systems as well as in a pure differentiation system using murine osteoclast precursor cell line. The vitamin K-free Simon extracts markedly suppressed severe bone destruction mediated by abundant osteoclasts associated with adjuvant-induced arthritis in rats. High performance liquid chromatography (HPLC) analysis revealed that the vitamin K-free Simon extracts contained three types of low molecular weight inhibitors for osteoclastogenesis; caffeic acid, chlorogenic acids and isochlorogenic acids. Among these substances, caffeic acid showed the most powerful inhibitory effects on osteoclastogenesis. Caffeic acid significantly suppressed expression of NFATc1, a key transcription factor for the induction of osteoclastogenesis. Our current study enlightened a high utility of the Simon extracts and their chemical components as effective regulators for bone resorption accompanied with inflammation and metabolic bone diseases. PMID:16205940

  4. Caffeic acid phenethyl ester downregulates phospholipase D1 via direct binding and inhibition of NFκB transactivation

    SciTech Connect

    Park, Mi Hee; Kang, Dong Woo; Jung, Yunjin; Choi, Kang-Yell; Min, Do Sik

    2013-12-06

    Highlights: •We found CAFÉ, a natural product that suppresses expression and activity of PLD1. •CAPE decreased PLD1 expression by inhibiting NFκB transactivation. •CAPE rapidly inhibited PLD activity via its binding to a Cys837 of PLD1. •PLD1 downregulation by CAPE inhibited invasion and proliferation of glioma cells. -- Abstract: Upregulation of phospholipase D (PLD) is functionally linked with oncogenic signals and tumorigenesis. Caffeic acid phenethyl ester (CAPE) is an active compound of propolis extract that exhibits anti-proliferative, anti-inflammatory, anti-oxidant, and antineoplastic properties. In this study, we demonstrated that CAPE suppressed the expression of PLD1 at the transcriptional level via inhibition of binding of NFκB to PLD1 promoter. Moreover, CAPE, but not its analogs, bound to a Cys837 residue of PLD1 and inhibited enzymatic activity of PLD. CAPE also decreased activation of matrix metalloproteinases-2 induced by phosphatidic acid, a product of PLD activity. Ultimately, CAPE-induced downregulation of PLD1 suppressed invasion and proliferation of glioma cells. Taken together, the results of this study indicate that CAPE might contribute to anti-neoplastic effect by targeting PLD1.

  5. Caffeic Acid Derivatives in Market Available Lamiaceae and Echinacea purpurea Products

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Fresh basil leaves contain chicoric acid, the principal phenolic compound of Echinacea purpurea and purportedly the active ingredient in its dietary supplements. Our group discovered and first reported chicoric acid in basil. This following study examined the distribution of chicoric acid within the...

  6. Preparative separation of polyphenols from water-soluble fraction of Chinese propolis using macroporous absorptive resin coupled with preparative high performance liquid chromatography.

    PubMed

    Li, Aifeng; Xuan, Hongzhuan; Sun, Ailing; Liu, Renmin; Cui, Jichun

    2016-02-15

    In this study, a preparative separation method was developed for isolation of eleven polyphenols from water-soluble fraction of Chinese propolis using macroporous absorptive resin (MAR) coupled with preparative high performance liquid chromatography (PHPLC). Water-soluble fraction of Chinese propolis was first "prefractioned" using MAR, which yielded four subfractions. The four subfractions were then isolated by PHPLC with an isocratic elution of methanol-water. Finally, eleven polyphenols were purified from Chinese propolis including caffeic acid, ferulic acid, isoferulic acid, 3,4-dimethoxy cinnamic acid, pinobanksin, caffeic acid benzyl ester, caffeic acid phenethyl ester, apigenin, pinocembrin, chrysin and galangin. The purities of the compounds were determined by HPLC and the chemical structures were confirmed by UV and NMR analysis. The method developed was simple, effective, rapid, scalable and economical, and it was a promising basis for large-scale preparation of multiple components from natural products. PMID:26807704

  7. Caffeic acid phenethyl ester exhibiting distinctive binding interaction with human serum albumin implies the pharmacokinetic basis of propolis bioactive components.

    PubMed

    Li, Hongliang; Wu, Fan; Tan, Jing; Wang, Kai; Zhang, Cuiping; Zheng, Huoqing; Hu, Fuliang

    2016-04-15

    Caffeic acid phenethyl ester (CAPE), as one of the major bioactive components present in propolis, exhibits versatile bioactivities, especially for its potent cytotoxic effects on several cancer cell models. To understand the pharmacokinetic characteristics of CAPE, the binding interaction between CAPE and human serum albumin (HSA) was investigated in vitro using multiple spectroscopic methods and molecular docking. The results reveal that CAPE exhibits a distinctive binding interaction with HSA comparing with other propolis components. The association constant K(A) (L mol(-1)) of the binding reaches 10(6) order of magnitude, which is significantly stronger than the other components of propolis. Based on the theory of fluorescence resonance energy transfer, the binding distance was calculated as 5.7 nm, which is longer than that of the other components of propolis. The thermodynamic results indicate that the binding is mainly driven by hydrogen bonds and van der Waals force. The docking and drugs (warfarin and ibuprofen) competitive results show that CAPE is located in the subdomain IIA (Sudlow's site I, FA7) of HSA, and Gln196 and Lys199 contribute to the hydrogen bonds. Circular dichroism spectra suggest an alteration of the secondary structure of HSA due to its partial unfolding in the presence of CAPE. PMID:26829518

  8. Inhibitory effect of caffeic acid on ADP-induced thrombus formation and platelet activation involves mitogen-activated protein kinases

    PubMed Central

    Lu, Yu; Li, Quan; Liu, Yu-Ying; Sun, Kai; Fan, Jing-Yu; Wang, Chuan-She; Han, Jing-Yan

    2015-01-01

    Caffeic acid (CA), one of the active constituents of Radix Salvia miltiorrhizae, exhibits antioxidant and anti-inflammatory activities. However, few studies have assessed the ability of CA to inhibit platelet mediated thrombus generation in vivo. In this study, we investigated the antithrombotic effect of CA in mouse cerebral arterioles and venules using intravital microscopy. The antiplatelet activity of CA in ADP stimulated mouse platelets in vitro was also examined in attempt to explore the underlying mechanism. Our results demonstrated that CA (1.25–5 mg/kg) significantly inhibited thrombus formation in vivo. In vitro, CA (25–100 μM) inhibited ADP-induced platelet aggregation, P-selectin expression, ATP release, Ca2+ mobilization, and integrin αIIbβ3 activation. Additionally, CA attenuated p38, ERK, and JNK activation, and enhanced cAMP levels. Taken together, these data provide evidence for the inhibition of CA on platelet-mediated thrombosis in vivo, which is, at least partly, mediated by interference in phosphorylation of ERK, p38, and JNK leading to elevation of cAMP and down-regulation of P-selectin expression and αIIbβ3 activation. These results suggest that CA may have potential for the treatment of aberrant platelet activation-related diseases. PMID:26345207

  9. Comparison of the chronic effects of ribavirin and caffeic acid phenethyl ester (CAPE) on pancreatic damage and hepatotoxicity

    PubMed Central

    Motor, Sedat; Alp, Harun; Şenol, Serkan; Pınar, Neslihan; Motor, Vicdan Köksaldı; Kaplan, İbrahim; Alp, Ayşe; Gökçe, Cumali

    2014-01-01

    This study was aimed to comparison of the effects of the chronic use of the Ribavirin and caffeic acid phenethyl ester (CAPE) on the pancreatic damage and hepatotoxicity in rats. Methods: The rats were given orally 30 mg/kg/day doses of Ribavirin for 30 days, and intraperitoneally 10 μmol/kg doses of CAPE. The 37 rats were divided into 4 groups: (I) Control (n=7), (II) Ribavirin (R) (n=10), (III) CAPE (n=10), and (IV) R+CAPE (n=10). Results: Ribavirin and CAPE yielded similar results in terms of Serum, total antioxidant status (TAS), total oxidant status (TOS), amylase, lipase, and insulin compared to the control group. However, while Ribavirin provided similar results with the control group in terms of aspartate aminotransferase (AST) and alanine aminotransferase (ALT) enzymes, the CAPE group had elevated AST and ALT levels compared to the control group. Histopathologic evaluations revealed that CAPE or Ribavirin had no degenerative effects on both the pancreas and liver tissues. In this way, the biochemical results were confirmed by the histopathologic results. Conclusion: It can be concluded that Ribavirin does not lead to any pancreatic damage and hepatotoxicity, and has more beneficial effects than CAPE on especially liver tissue. PMID:24955174

  10. Sequencing around 5-Hydroxyconiferyl Alcohol-Derived Units in Caffeic Acid O-Methyltransferase-Deficient Poplar Lignins1[OA

    PubMed Central

    Lu, Fachuang; Marita, Jane M.; Lapierre, Catherine; Jouanin, Lise; Morreel, Kris; Boerjan, Wout; Ralph, John

    2010-01-01

    Caffeic acid O-methyltransferase (COMT) is a bifunctional enzyme that methylates the 5- and 3-hydroxyl positions on the aromatic ring of monolignol precursors, with a preference for 5-hydroxyconiferaldehyde, on the way to producing sinapyl alcohol. Lignins in COMT-deficient plants contain benzodioxane substructures due to the incorporation of 5-hydroxyconiferyl alcohol (5-OH-CA), as a monomer, into the lignin polymer. The derivatization followed by reductive cleavage method can be used to detect and determine benzodioxane structures because of their total survival under this degradation method. Moreover, partial sequencing information for 5-OH-CA incorporation into lignin can be derived from detection or isolation and structural analysis of the resulting benzodioxane products. Results from a modified derivatization followed by reductive cleavage analysis of COMT-deficient lignins provide evidence that 5-OH-CA cross couples (at its β-position) with syringyl and guaiacyl units (at their O-4-positions) in the growing lignin polymer and then either coniferyl or sinapyl alcohol, or another 5-hydroxyconiferyl monomer, adds to the resulting 5-hydroxyguaiacyl terminus, producing the benzodioxane. This new terminus may also become etherified by coupling with further monolignols, incorporating the 5-OH-CA integrally into the lignin structure. PMID:20427467

  11. Caffeic Acid Inhibits Chronic UVB-Induced Cellular Proliferation Through JAK-STAT3 Signaling in Mouse Skin.

    PubMed

    Agilan, Balupillai; Rajendra Prasad, N; Kanimozhi, Govindasamy; Karthikeyan, Ramasamy; Ganesan, Muthusamy; Mohana, Shanmugam; Velmurugan, Devadasan; Ananthakrishnan, Dhanapalan

    2016-05-01

    Signal transducers and activators of transcription 3 (STAT3) play a critical role in inflammation, proliferation and carcinogenesis. Inhibition of JAK-STAT3 signaling is proved to be a novel target for prevention of UVB-induced skin carcinogenesis. In this study, chronic UVB irradiation (180 mJ cm(-2) ; weekly thrice for 30 weeks) induces the expression of IL-10 and JAK1 that eventually activates the STAT3 which leads to the transcription of proliferative and antiapoptotic markers such as PCNA, Cyclin-D1, Bcl2 and Bcl-xl, respectively. Caffeic acid (CA) inhibits JAK-STAT3 signaling, thereby induces apoptotic cell death by upregulating Bax, Cytochrome-C, Caspase-9 and Caspase-3 expression in mouse skin. Furthermore, TSP-1 is an antiangiogeneic protein, which is involved in the inhibition of angiogenesis and proliferation. Chronic UVB exposure decreased the expression of TSP-1 and pretreatment with CA prevented the UVB-induced loss of TSP-1 in UVB-irradiated mouse skin. Thus, CA offers protection against UVB-induced photocarcinogenesis probably through modulating the JAK-STAT3 in the mouse skin. PMID:27029485

  12. Evaluation of anti-allergic properties of caffeic acid phenethyl ester in a murine model of systemic anaphylaxis

    SciTech Connect

    Park, Sae-Gwang; Lee, Da-Young; Seo, Su-Kil; Lee, Soo-Woong; Kim, Se-Kwon; Jung, Won-Kyo; Kang, Mi-Seon; Choi, Yung Hyun; Yea, Sung Su; Choi, Inhak Choi, Il-Whan

    2008-01-01

    Caffeic acid phenethyl ester (CAPE) is an active component of honeybee propolis extracts. It has several positive effects, including anti-inflammatory, anti-oxidation, anti-cancer, anti-bacterial, anti-viral, anti-fungal, and immunomodulatory effects. In particular, the suppressive effect of NF-{kappa}B may disrupt a component of allergic induction. The principal objective of this experimental study was to evaluate the effects of CAPE on the active systemic anaphylaxis induced by ovalbumin (OVA) challenge in mice. Mice were intraperitoneally sensitized and intravenously challenged with OVA. Histopathological analysis, nuclear factor (NF)-{kappa}B activation, and the plasma levels of histamine and total IgE after allergen challenge were evaluated. After challenges, all of the sham-treated mice developed anaphylactic symptoms, increased plasma levels of histamine and OVA-specific IgE, marked vascular leakage, NF-{kappa}B activation, platelet-activating factor (PAF) production, and histological changes including pulmonary edema and hemorrhage in the renal medullae within 20 min. By way of contrast, a reduction in the plasma levels of histamine and OVA-specific IgE and an inhibition of NF-{kappa}B activation and PAF release were observed in the CAPE-treated mice. In addition, a significant prevention of hemoconcentration and OVA-induced pathological changes were noted. These results indicate that CAPE demonstrates an anti-allergic effect, which may be the result of its protective effects against IgE-mediated allergy.

  13. Synthesis and antiproliferative activity of two diastereomeric lignan amides serving as dimeric caffeic acid-l-DOPA hybrids.

    PubMed

    Magoulas, George E; Rigopoulos, Andreas; Piperigkou, Zoi; Gialeli, Chrysostomi; Karamanos, Nikos K; Takis, Panteleimon G; Troganis, Anastassios N; Chrissanthopoulos, Athanassios; Maroulis, George; Papaioannou, Dionissios

    2016-06-01

    Two new diastereomeric lignan amides (4 and 5) serving as dimeric caffeic acid-l-DOPA hybrids were synthesized. The synthesis involved the FeCl3-mediated phenol oxidative coupling of methyl caffeate to afford trans-diester 1a as a mixture of enantiomers, protection of the catechol units, regioselective saponification, coupling with a suitably protected l-DOPA derivative, separation of the two diastereomers thus obtained by flash column chromatography and finally global chemoselective deprotection of the catechol units. The effect of hybrids 4 and 5 and related compounds on the proliferation of two breast cancer cell lines with different metastatic potential and estrogen receptor status (MDA-MB-231 and MCF-7) and of one epithelial lung cancer cell line, namely A-549, was evaluated for concentrations ranging from 1 to 256μM and periods of treatment of 24, 48 and 72h. Both hybrids showed interesting and almost equipotent antiproliferative activities (IC50 64-70μM) for the MDA-MB-231 cell line after 24-48h of treatment, but they were more selective and much more potent (IC50 4-16μM) for the MCF-7 cells after 48h of treatment. The highest activity for both hybrids and both breast cancer lines was observed after 72h of treatment (IC50 1-2μM), probably as the result of slow hydrolysis of their methyl ester functions. PMID:27155809

  14. Effect of Caffeic Acid Phenethyl Ester on Vascular Damage Caused by Consumption of High Fructose Corn Syrup in Rats.

    PubMed

    Gun, Aburrahman; Ozer, Mehmet Kaya; Bilgic, Sedat; Kocaman, Nevin; Ozan, Gonca

    2016-01-01

    Fructose corn syrup is cheap sweetener and prolongs the shelf life of products, but fructose intake causes hyperinsulinemia, hypertriglyceridemia, and hypertension. All of them are referred to as metabolic syndrome and they are risk factors for cardiovascular diseases. Hence, the harmful effects of increased fructose intake on health and their prevention should take greater consideration. Caffeic Acid Phenethyl Ester (CAPE) has beneficial effects on metabolic syndrome and vascular function which is important in the prevention of cardiovascular disease. However, there are no known studies about the effect of CAPE on fructose-induced vascular dysfunction. In this study, we examined the effect of CAPE on vascular dysfunction due to high fructose corn syrup (HFCS). HFCS (6 weeks, 30% fed with drinking water) caused vascular dysfunction, but treatment with CAPE (50 micromol/kg i.p. for the last two weeks) effectively restored this problem. Additionally, hypertension in HFCS-fed rats was also decreased in CAPE supplemented rats. CAPE supplements lowered HFCS consumption-induced raise in blood glucose, homocysteine, and cholesterol levels. The aorta tissue endothelial nitric oxide synthase (eNOS) production was decreased in rats given HFCS and in contrast CAPE supplementation efficiently increased its production. The presented results showed that HFCS-induced cardiovascular abnormalities could be prevented by CAPE treatment. PMID:27042260

  15. Effect of Caffeic Acid Phenethyl Ester on Vascular Damage Caused by Consumption of High Fructose Corn Syrup in Rats

    PubMed Central

    Gun, Aburrahman; Bilgic, Sedat; Kocaman, Nevin; Ozan, Gonca

    2016-01-01

    Fructose corn syrup is cheap sweetener and prolongs the shelf life of products, but fructose intake causes hyperinsulinemia, hypertriglyceridemia, and hypertension. All of them are referred to as metabolic syndrome and they are risk factors for cardiovascular diseases. Hence, the harmful effects of increased fructose intake on health and their prevention should take greater consideration. Caffeic Acid Phenethyl Ester (CAPE) has beneficial effects on metabolic syndrome and vascular function which is important in the prevention of cardiovascular disease. However, there are no known studies about the effect of CAPE on fructose-induced vascular dysfunction. In this study, we examined the effect of CAPE on vascular dysfunction due to high fructose corn syrup (HFCS). HFCS (6 weeks, 30% fed with drinking water) caused vascular dysfunction, but treatment with CAPE (50 micromol/kg i.p. for the last two weeks) effectively restored this problem. Additionally, hypertension in HFCS-fed rats was also decreased in CAPE supplemented rats. CAPE supplements lowered HFCS consumption-induced raise in blood glucose, homocysteine, and cholesterol levels. The aorta tissue endothelial nitric oxide synthase (eNOS) production was decreased in rats given HFCS and in contrast CAPE supplementation efficiently increased its production. The presented results showed that HFCS-induced cardiovascular abnormalities could be prevented by CAPE treatment. PMID:27042260

  16. Fibrinolytic Activity and Dose-Dependent Effect of Incubating Human Blood Clots in Caffeic Acid Phenethyl Ester: In Vitro Assays

    PubMed Central

    Elnager, Abuzar; Hassan, Rosline; Idris, Zamzuri; Mustafa, Zulkifli; Wan-Arfah, Nadiah; Sulaiman, S. A.; Gan, Siew Hua; Abdullah, Wan Zaidah

    2015-01-01

    Background. Caffeic acid phenethyl ester (CAPE) has been reported to possess time-dependent fibrinolytic activity by in vitro assay. This study is aimed at investigating fibrinolytic dose-dependent activity of CAPE using in vitro assays. Methods. Standardized human whole blood (WB) clots were incubated in either blank controls or different concentrations of CAPE (3.75, 7.50, 15.00, 22.50, and 30.00 mM). After 3 hours, D-dimer (DD) levels and WB clot weights were measured for each concentration. Thromboelastography (TEG) parameters were recorded following CAPE incubation, and fibrin morphology was examined under a confocal microscope. Results. Overall, mean DD (μg/mL) levels were significantly different across samples incubated with different CAPE concentrations, and the median pre- and postincubation WB clot weights (grams) were significantly decreased for each CAPE concentration. Fibrin removal was observed microscopically and indicated dose-dependent effects. Based on the TEG test, the Ly30 fibrinolytic parameter was significantly different between samples incubated with two different CAPE concentrations (15.0 and 22.50 mM). The 50% effective dose (ED50) of CAPE (based on DD) was 1.99 mg/mL. Conclusions. This study suggests that CAPE possesses fibrinolytic activity following in vitro incubation and that it has dose-dependent activities. Therefore, further investigation into CAPE as a potential alternative thrombolytic agent should be conducted. PMID:25664321

  17. Caffeic acid phenethyl ester suppresses the proliferation of human prostate cancer cells through inhibition of AMPK and Akt signaling networks

    PubMed Central

    Chuu, Chih-Pin; Lin, Hui-Ping; Ciaccio, Mark F.; Kokontis, John M.; Hause, Ronald J.; Hiipakka, Richard A.; Liao, Shutsung; Jones, Richard Baker

    2016-01-01

    Caffeic acid phenethyl ester (CAPE) is a bioactive component derived from honeybee hive propolis. CAPE has been shown to have anti-mitogenic, anti-carcinogenic, and other beneficial medicinal properties. Many of its effects have been shown to be mediated through its inhibition of NF-κB signaling pathways. We took a systematic approach to uncover CAPE’s effects from hours to days on the signaling networks in human prostate cancer cells. We observed that CAPE dosage-dependently suppressed the proliferation of LNCaP, DU-145, and PC-3 human prostate cancer cells. Administration of CAPE by gavage significantly inhibited the tumor growth of LNCaP xenografts in nude mice. Using LNCaP cells as a model system, we examined CAPE’s effect on gene expression, protein signaling, and transcriptional regulatory networks using Micro-Western Arrays and PCR arrays. We built a model of CAPE’s impact on cell signaling which suggested that it acted through inhibition of Akt-related protein signaling networks. Over-expression of Akt1 or cMyc, a downstream target of Akt signaling, significantly blocked the anti-proliferative effects of CAPE. In summary, our results suggest that CAPE administration may be useful as an adjuvant therapy for prostate and potentially other types of cancers that are driven by the AMPK and Akt signaling networks. PMID:22562408

  18. Melatonin production in Escherichia coli by dual expression of serotonin N-acetyltransferase and caffeic acid O-methyltransferase.

    PubMed

    Byeon, Yeong; Back, Kyoungwhan

    2016-08-01

    Melatonin is a well-known bioactive molecule produced in animals and plants and a well-studied natural compound. Two enzymatic steps are required for the biosynthesis of melatonin from serotonin. First, serotonin N-acetyltransferase (SNAT) catalyzes serotonin to N-acetylserotonin (NAS) followed by the action of N-acetylserotonin O-methyltransferase (ASMT), resulting in the synthesis of O-methylated NAS, also known as melatonin. Attempts to document melatonin production in Escherichia coli have been unsuccessful to date due to either low enzyme activity or inactive ASMT expression. Here, we employed caffeic acid O-methyltransferase (COMT) instead of ASMT, as COMT is a multifunctional enzyme that has ASMT activity as well. Among several combinations of dual expression cassettes, recombinant E. coli that expressed sheep SNAT with rice COMT produced a high quantity of melatonin, which was measured in a culture medium (1.46 mg/L in response to 1 mM serotonin). This level was several orders of magnitude higher than that produced in transgenic rice and tomato overexpressing sheep SNAT and ASMT, respectively. This heterologous expression system can be widely employed to screen various putative SNAT or ASMT genes from animals and plants as well as to overproduce melatonin in various useful microorganisms. PMID:27005412

  19. Sequencing around 5-hydroxyconiferyl alcohol-derived units in caffeic acid O-methyltransferase-deficient poplar lignins.

    PubMed

    Lu, Fachuang; Marita, Jane M; Lapierre, Catherine; Jouanin, Lise; Morreel, Kris; Boerjan, Wout; Ralph, John

    2010-06-01

    Caffeic acid O-methyltransferase (COMT) is a bifunctional enzyme that methylates the 5- and 3-hydroxyl positions on the aromatic ring of monolignol precursors, with a preference for 5-hydroxyconiferaldehyde, on the way to producing sinapyl alcohol. Lignins in COMT-deficient plants contain benzodioxane substructures due to the incorporation of 5-hydroxyconiferyl alcohol (5-OH-CA), as a monomer, into the lignin polymer. The derivatization followed by reductive cleavage method can be used to detect and determine benzodioxane structures because of their total survival under this degradation method. Moreover, partial sequencing information for 5-OH-CA incorporation into lignin can be derived from detection or isolation and structural analysis of the resulting benzodioxane products. Results from a modified derivatization followed by reductive cleavage analysis of COMT-deficient lignins provide evidence that 5-OH-CA cross couples (at its beta-position) with syringyl and guaiacyl units (at their O-4-positions) in the growing lignin polymer and then either coniferyl or sinapyl alcohol, or another 5-hydroxyconiferyl monomer, adds to the resulting 5-hydroxyguaiacyl terminus, producing the benzodioxane. This new terminus may also become etherified by coupling with further monolignols, incorporating the 5-OH-CA integrally into the lignin structure. PMID:20427467

  20. Caffeic acid phenethyl ester abrogates bone resorption in a murine calvarial model of polyethylene particle-induced osteolysis.

    PubMed

    Zawawi, M S F; Perilli, E; Stansborough, R L; Marino, V; Cantley, M D; Xu, J; Dharmapatni, A A S S K; Haynes, D R; Gibson, R J; Crotti, T N

    2015-06-01

    Particle-induced bone loss by osteoclasts is a common cause of aseptic loosening around implants. This study investigates whether caffeic acid phenethyl ester (CAPE), a potent and specific inhibitor of nuclear factor of activated T cells, cytoplasmic, calcineurin-dependent 1 and nuclear factor kappa B, at a low dose reduces bone resorption in a murine calvarial model of polyethylene (PE) particle-induced osteolysis. The effects of particles and CAPE treatment on gastrointestinal tract (GIT) histopathology were also evaluated. Mice were scanned using in vivo animal micro-computed tomography (μCT) as a baseline measurement. PE particles (2.82 × 10(9) particles/mL) were implanted over the calvariae on day 0. CAPE was administered subcutaneously (1 mg/kg/day) at days 0, 4, 7 and 10. Mice were killed at day 14 and serum was analysed for Type-1 carboxyterminal collagen crosslinks (CTX)-1 and osteoclast-associated receptor (OSCAR) levels. Ex vivo μCT scans were conducted to assess bone volume (BV) change and percentage area of calvarial surface resorbed. Calvarial and GIT tissue was processed for histopathology. By day 14, PE particles significantly induced calvarial bone loss compared with control animals as evidenced by resorption areas adjacent to the implanted PE in three-dimensional μCT images, an increase in percentage of resorbed area (p = 0.0022), reduction in BV (p = 0.0012) and increased Tartrate-resistant acid phosphatase positive cells. Serum CTX-1 (p = 0.0495) and OSCAR levels (p = 0.0006) significantly increased in the PE implant group. CAPE significantly inhibited PE particle-induced calvarial osteolysis, as evidenced by a significant reduction in surface bone resorption (p = 0.0012) and volumetric change (p = 0.0154) compared with PE only, but had no effect on systemic CTX-1. Neither particles nor CAPE had an effect on GIT histopathology. PMID:25804981

  1. Down-regulation of the caffeic acid O-methyltransferase gene in switchgrass reveals a novel monolignol analog

    PubMed Central

    2012-01-01

    Background Down-regulation of the caffeic acid 3-O-methyltransferase EC 2.1.1.68 (COMT) gene in the lignin biosynthetic pathway of switchgrass (Panicum virgatum) resulted in cell walls of transgenic plants releasing more constituent sugars after pretreatment by dilute acid and treatment with glycosyl hydrolases from an added enzyme preparation and from Clostridium thermocellum. Fermentation of both wild-type and transgenic switchgrass after milder hot water pretreatment with no water washing showed that only the transgenic switchgrass inhibited C. thermocellum. Gas chromatography–mass spectrometry (GCMS)-based metabolomics were undertaken on cell wall aqueous extracts to determine the nature of the microbial inhibitors. Results GCMS confirmed the increased concentration of a number of phenolic acids and aldehydes that are known inhibitors of microbial fermentation. Metabolomic analyses of the transgenic biomass additionally revealed the presence of a novel monolignol-like metabolite, identified as trans-3, 4-dimethoxy-5-hydroxycinnamyl alcohol (iso-sinapyl alcohol) in both non-pretreated, as well as hot water pretreated samples. iso-Sinapyl alcohol and its glucoside were subsequently generated by organic synthesis and the identity of natural and synthetic materials were confirmed by mass spectrometric and NMR analyses. The additional novel presence of iso-sinapic acid, iso-sinapyl aldehyde, and iso-syringin suggest the increased activity of a para-methyltransferase, concomitant with the reduced COMT activity, a strict meta-methyltransferase. Quantum chemical calculations were used to predict the most likely homodimeric lignans generated from dehydration reactions, but these products were not evident in plant samples. Conclusions Down-regulation of COMT activity in switchgrass resulted in the accumulation of previously undetected metabolites resembling sinapyl alcohol and its related metabolites, but that are derived from para-methylation of 5-hydroxyconiferyl

  2. The Effect of Caffeic Acid Phenethyl Ester (CAPE) Fortification on the Liver Element Distribution that Occurs After Exercise.

    PubMed

    Akil, Mustafa; Coban, Funda Karabag; Yalcinkaya, Ozcan

    2016-08-01

    The purpose of this study is to examine the effect of the caffeic acid phenethyl ester (CAPE) fortification applied to the rats, which were made to exercise, on the liver elements. The study was conducted on 32 Sprague-Dawley male rats. The experimental animals were divided into 4 groups in equal numbers. Group 1 is the group which was applied 10 μmol/kg/day CAPE as intraperitoneal (IP) for 4 weeks, and they were not made to exercise at the end of the application. Group 2 is the group which was applied 10 μmol/kg/day CAPE as IP for 4 weeks, and they were made to exercise at the end of the 4th week. Group 3 is the general control group. Group 4 is the swimming control group. A 10 mmol/kg CAPE application dissolved in ethyl alcohol of 10 % was applied to the CAPE group. Sodium (Na), zinc (Zn), calcium (Ca), iron (Fe), chrome (Cr), magnesium (Mg), potassium (K), copper (Cu) and cadmium (Cd) levels were identified in the liver samples at the end of the application. The results of the study suggest that exercise and CAPE fortification in rats cause changes in the Na, Zn, Ca, Fe and Cr parameters in liver tissues, and it does not affect Cd, Cu, Mg and K element distribution. It is thought that CAPE fortification would be helpful for preserving those parameters whose levels are known to be changing with exercise. PMID:26743862

  3. Modification of Caffeic Acid with Pyrrolidine Enhances Antioxidant Ability by Activating AKT/HO-1 Pathway in Heart

    PubMed Central

    Ku, Hui-Chun; Lee, Shih-Yi; Yang, Kai-Chien; Kuo, Yueh-Hsiung; Su, Ming-Jai

    2016-01-01

    Overproduction of free radicals during ischemia/reperfusion (I/R) injury leads to an interest in using antioxidant therapy. Activating an endogenous antioxidant signaling pathway is more important due to the fact that the free radical scavenging behavior in vitro does not always correlate with a cytoprotection effect in vivo. Caffeic acid (CA), an antioxidant, is a major phenolic constituent in nature. Pyrrolidinyl caffeamide (PLCA), a derivative of CA, was compared with CA for their antioxidant and cytoprotective effects. Our results indicate that CA and PLCA exert the same ability to scavenge DPPH in vitro. In response to myocardial I/R stress, PLCA was shown to attenuate lipid peroxydation and troponin release more than CA. These responses were accompanied with a prominent elevation in AKT and HO-1 expression and a preservation of mnSOD expression and catalase activity. PLCA also improved cell viability and alleviated the intracellular ROS level more than CA in cardiomyocytes exposed to H2O2. When inhibiting the AKT or HO-1 pathways, PLCA lost its ability to recover mnSOD expression and catalase activity to counteract with oxidative stress, suggesting AKT/HO-1 pathway activation by PLCA plays an important role. In addition, inhibition of AKT signaling further abolished HO-1 activity, while inhibition of HO-1 signaling attenuated AKT expression, indicating cross-talk between the AKT and HO-1 pathways. These protective effects may contribute to the cardiac function improvement by PLCA. These findings provide new insight into therapeutic approaches using a modified natural compound against oxidative stress from myocardial injuries. PMID:26845693

  4. Caffeic acid phenethyl ester decreases cholangiocarcinoma growth by inhibition of NF-κB and induction of apoptosis

    PubMed Central

    Onori, Paolo; DeMorrow, Sharon; Gaudio, Eugenio; Franchitto, Antonio; Mancinelli, Romina; Venter, Julie; Kopriva, Shelley; Ueno, Yoshiyuki; Alvaro, Domenico; Savage, Jennifer; Alpini, Gianfranco; Francis, Heather

    2011-01-01

    Caffeic acid phenethyl ester (CAPE) inhibits the growth of tumor cells and is a known inhibitor of NF-κB that is constitutively active in cholangiocarcinoma (CCH) cells. We evaluated the effects of CAPE on CCH growth both in vitro and in vivo. Inhibition of NF-κB DNA-binding activity was confirmed in nuclear extracts treated with CAPE at 50, 40 and 20 μM. CAPE decreases the expression of NF-κB1 (p50) and RelA (p65). CAPE decreased the growth of a number of CCH cells but not normal cholangiocytes. Cell cycle decrease was seen by a decrease in PCNA protein expression and the number of BrdU-positive cells treated with CAPE at 20 μM compared to vehicle. Inhibition of growth and increased cell cycle arrest of Mz-ChA-1 cells by CAPE were coupled with increased apoptosis. Bax expression was increased, whereas Bcl-2 was decreased in cells treated with CAPE compared to vehicle. In vivo studies were performed in BALB/c nude (nu/nu) mice implanted subcutaneously with Mz-ChA-1 cells and treated with daily IP injections of DMSO or CAPE (10 mg/kg body weight in DMSO) for 77 days. Tumor growth was decreased and tumor latency was increased 2-fold in CAPE compared to vehicle-treated nude mice. In tumor samples, decreased CCH growth by CAPE was coupled with increased apoptosis. CAPE both in vivo and in vitro decreases the growth of cholangiocarcinoma cells by increasing apoptosis. These results demonstrate that CAPE might be an important therapeutic tool in the treatment of CCH. PMID:19358267

  5. Modification of Caffeic Acid with Pyrrolidine Enhances Antioxidant Ability by Activating AKT/HO-1 Pathway in Heart.

    PubMed

    Ku, Hui-Chun; Lee, Shih-Yi; Yang, Kai-Chien; Kuo, Yueh-Hsiung; Su, Ming-Jai

    2016-01-01

    Overproduction of free radicals during ischemia/reperfusion (I/R) injury leads to an interest in using antioxidant therapy. Activating an endogenous antioxidant signaling pathway is more important due to the fact that the free radical scavenging behavior in vitro does not always correlate with a cytoprotection effect in vivo. Caffeic acid (CA), an antioxidant, is a major phenolic constituent in nature. Pyrrolidinyl caffeamide (PLCA), a derivative of CA, was compared with CA for their antioxidant and cytoprotective effects. Our results indicate that CA and PLCA exert the same ability to scavenge DPPH in vitro. In response to myocardial I/R stress, PLCA was shown to attenuate lipid peroxydation and troponin release more than CA. These responses were accompanied with a prominent elevation in AKT and HO-1 expression and a preservation of mnSOD expression and catalase activity. PLCA also improved cell viability and alleviated the intracellular ROS level more than CA in cardiomyocytes exposed to H2O2. When inhibiting the AKT or HO-1 pathways, PLCA lost its ability to recover mnSOD expression and catalase activity to counteract with oxidative stress, suggesting AKT/HO-1 pathway activation by PLCA plays an important role. In addition, inhibition of AKT signaling further abolished HO-1 activity, while inhibition of HO-1 signaling attenuated AKT expression, indicating cross-talk between the AKT and HO-1 pathways. These protective effects may contribute to the cardiac function improvement by PLCA. These findings provide new insight into therapeutic approaches using a modified natural compound against oxidative stress from myocardial injuries. PMID:26845693

  6. Caffeic acid phenethyl ester preferentially sensitizes CT26 colorectal adenocarcinoma to ionizing radiation without affecting bone marrow radioresponse

    SciTech Connect

    Chen, Y.-J.; Liao, H.-F.; Tsai, T.-H.; Wang, S.-Y.; Shiao, M.-S. . E-mail: msshiao@vghtpe.gov.tw

    2005-11-15

    Purpose: Caffeic acid phenethyl ester (CAPE), a component of propolis, was reported capable of depleting glutathione (GSH). We subsequently examined the radiosensitizing effect of CAPE and its toxicity. Methods and Materials: The effects of CAPE on GSH level, GSH metabolism enzyme activities, NF-{kappa}B activity, and radiosensitivity in mouse CT26 colorectal adenocarcinoma cells were determined. BALB/c mouse with CT26 cells implantation was used as a syngeneic in vivo model for evaluation of treatment and toxicity end points. Results: CAPE entered CT26 cells rapidly and depleted intracellular GSH in CT26 cells, but not in bone marrow cells. Pretreatment with nontoxic doses of CAPE significantly enhanced cell killing by ionizing radiation (IR) with sensitizer enhancement ratios up to 2.2. Pretreatment of CT26 cells with N-acetyl-L-cysteine reversed the GSH depletion activity and partially blocked the radiosensitizing effect of CAPE. CAPE treatment in CT26 cells increased glutathione peroxidase, decreased glutathione reductase, and did not affect glutathione S-transferase or {gamma}-glutamyl transpeptidase activity. Radiation activated NF-{kappa}B was reversed by CAPE pretreatment. In vivo study revealed that pretreatment with CAPE before IR resulted in greater inhibition of tumor growth and prolongation of survival in comparison with IR alone. Pretreatment with CAPE neither affected body weights nor produced hepatic, renal, or hematopoietic toxicity. Conclusions: CAPE sensitizes CT26 colorectal adenocarcinoma to IR, which may be via depleting GSH and inhibiting NF-{kappa}B activity, without toxicity to bone marrow, liver, and kidney.

  7. Effect of different polyphenol sources on the efficiency of ellagic acid release by Aspergillus niger.

    PubMed

    Sepúlveda, Leonardo; de la Cruz, Reynaldo; Buenrostro, José Juan; Ascacio-Valdés, Juan Alberto; Aguilera-Carbó, Antonio Francisco; Prado, Arely; Rodríguez-Herrera, Raúl; Aguilar, Cristóbal Noé

    2016-01-01

    Fungal hydrolysis of ellagitannins produces hexahydroxydiphenic acid, which is considered an intermediate molecule in ellagic acid release. Ellagic acid has important and desirable beneficial health properties. The aim of this work was to identify the effect of different sources of ellagitannins on the efficiency of ellagic acid release by Aspergillus niger. Three strains of A. niger (GH1, PSH and HT4) were assessed for ellagic acid release from different polyphenol sources: cranberry, creosote bush, and pomegranate used as substrate. Polyurethane foam was used as support for solid-state culture in column reactors. Ellagitannase activity was measured for each of the treatments. Ellagic acid was quantified by high performance liquid chromatography. When pomegranate polyphenols were used, a maximum value of ellagic acid (350.21 mg/g) was reached with A. niger HT4 in solid-state culture. The highest amount of ellagitannase (5176.81 U/l) was obtained at 8h of culture when cranberry polyphenols and strain A. niger PSH were used. Results demonstrated the effect of different polyphenol sources and A. niger strains on ellagic acid release. It was observed that the best source for releasing ellagic acid was pomegranate polyphenols and A. niger HT4 strain, which has the ability to degrade these compounds for obtaining a potent bioactive molecule such as ellagic acid. PMID:26916811

  8. Polyphenol levels in human urine after intake of six different polyphenol-rich beverages.

    PubMed

    Ito, Hideyuki; Gonthier, Marie-Paule; Manach, Claudine; Morand, Christine; Mennen, Louise; Rémésy, Christian; Scalbert, Augustin

    2005-10-01

    Dietary polyphenols are suggested to participate in the prevention of CVD and cancer. It is essential for epidemiological studies to be able to compare intake of the main dietary polyphenols in populations. The present paper describes a fast method suitable for the analysis of polyphenols in urine, selected as potential biomarkers of intake. This method is applied to the estimation of polyphenol recovery after ingestion of six different polyphenol-rich beverages. Fifteen polyphenols including mammalian lignans (enterodiol and enterolactone), several phenolic acids (chlorogenic, caffeic, m-coumaric, gallic, and 4-O-methylgallic acids), phloretin and various flavonoids (catechin, epicatechin, quercetin, isorhamnetin, kaempferol, hesperetin, and naringenin) were simultaneously quantified in human urine by HPLC coupled with electrospray ionisation mass-MS (HPLC-electrospray-tandem mass spectrometry) with a run time of 6 min per sample. The method has been validated with regard to linearity, precision, and accuracy in intra- and inter-day assays. It was applied to urine samples collected from nine volunteers in the 24 h following consumption of either green tea, a grape-skin extract, cocoa beverage, coffee, grapefruit juice or orange juice. Levels of urinary excretion suggest that chlorogenic acid, gallic acid, epicatechin, naringenin or hesperetin could be used as specific biomarkers to evaluate the consumption of coffee, wine, tea or cocoa, and citrus juices respectively. PMID:16197573

  9. Interactions between prebiotics, probiotics, polyunsaturated fatty acids and polyphenols: diet or supplementation for metabolic syndrome prevention?

    PubMed

    Peluso, Ilaria; Romanelli, Luca; Palmery, Maura

    2014-05-01

    The metabolic syndrome can be prevented by the Mediterranean diet, characterized by fiber, omega-3 polyunsaturated fatty acids and polyphenols. However, the composition of the Mediterranean diet, which can be viewed as a natural multiple supplement, is poorly controlled, and its beneficial effects poorly predictable. The metabolic syndrome is associated with intestinal dysbiosis and the gut microbioma seems to be the main target and player in the interactions occurring between probiotics, prebiotics, omega 3 polyunsaturated fatty acids, and polyphenols. From the reviewed evidence, it is reasonable to manage growth and metabolism of gut microflora with specific prebiotics and polyphenols. Even though the healthy properties of functional foods and nutraceuticals still need to be fully elucidated, available data suggest that well-designed supplements, containing the better ratio of omega-3 polyunsaturated fatty acids and antioxidants, specific probiotic strains, and selected polyphenols and prebiotics, could be useful in metabolic syndrome prevention and treatment. PMID:24467635

  10. Interactions between polyphenols in thinned young apples and porcine pancreatic α-amylase: Inhibition, detailed kinetics and fluorescence quenching.

    PubMed

    Sun, Lijun; Chen, Weiqi; Meng, Yonghong; Yang, Xingbin; Yuan, Li; Guo, Yurong

    2016-10-01

    Young apple polyphenols (YAP) and nine types of phenolic compounds were investigated regarding the inhibitory activity against porcine pancreatic α-amylase (PPA) in vitro. Tannic acid, chlorogenic acid and caffeic acid in YAP showed relatively high inhibition with the IC50 values of 0.30, 1.96 and 3.69mg/mL, respectively. A detailed kinetics of inhibition study revealed that YAP and tannic acid were competitive inhibitors of PPA, whereas chlorogenic acid and caffeic acid were mixed inhibitors, exhibiting both competitive and uncompetitive characteristics. The fluorescence of PPA could be significantly quenched by YAP and the three polyphenols, and their quenching constants were determined. The results showed that for the polyphenols investigated, the order of the apparent static quenching constants (KFQ) was in agreement with that of the reciprocal competitive inhibition constants (1/Kic) (tannic acid>chlorogenic acid>caffeic acid>epicatechin); both of the parameters were contrary to the order of the IC50 values. Thus, combining detailed kinetics and fluorescence quenching studies can be applied to characterise the interactions between polyphenols in young apples and α-amylase. PMID:27132823

  11. The impact of hop bitter acid and polyphenol profiles on the perceived bitterness of beer.

    PubMed

    Oladokun, Olayide; Tarrega, Amparo; James, Sue; Smart, Katherine; Hort, Joanne; Cook, David

    2016-08-15

    Thirty-four commercial lager beers were analysed for their hop bitter acid, phenolic acid and polyphenol contents. Based on analytical data, it was evident that the beers had been produced using a range of different raw materials and hopping practices. Principal Components Analysis was used to select a sub-set of 10 beers that contained diverse concentrations of the analysed bitter compounds. These beers were appraised sensorially to determine the impacts of varying hop acid and polyphenolic profiles on perceived bitterness character. Beers high in polyphenol and hop acid contents were perceived as having 'harsh' and 'progressive' bitterness, whilst beers that had evidently been conventionally hopped were 'sharp' and 'instant' in their bitterness. Beers containing light-stable hop products (tetrahydro-iso-α-acids) were perceived as 'diminishing', 'rounded' and 'acidic' in bitterness. The hopping strategy adopted by brewers impacts on the nature, temporal profile and intensity of bitterness perception in beer. PMID:27006233

  12. Modulation of neurotrophic signaling pathways by polyphenols

    PubMed Central

    Moosavi, Fatemeh; Hosseini, Razieh; Saso, Luciano; Firuzi, Omidreza

    2016-01-01

    Polyphenols are an important class of phytochemicals, and several lines of evidence have demonstrated their beneficial effects in the context of a number of pathologies including neurodegenerative disorders such as Alzheimer’s and Parkinson’s disease. In this report, we review the studies on the effects of polyphenols on neuronal survival, growth, proliferation and differentiation, and the signaling pathways involved in these neurotrophic actions. Several polyphenols including flavonoids such as baicalein, daidzein, luteolin, and nobiletin as well as nonflavonoid polyphenols such as auraptene, carnosic acid, curcuminoids, and hydroxycinnamic acid derivatives including caffeic acid phentyl ester enhance neuronal survival and promote neurite outgrowth in vitro, a hallmark of neuronal differentiation. Assessment of underlying mechanisms, especially in PC12 neuronal-like cells, reveals that direct agonistic effect on tropomyosin receptor kinase (Trk) receptors, the main receptors of neurotrophic factors including nerve growth factor (NGF) and brain-derived neurotrophic factor (BDNF) explains the action of few polyphenols such as 7,8-dihydroxyflavone. However, several other polyphenolic compounds activate extracellular signal-regulated kinase (ERK) and phosphoinositide 3-kinase (PI3K)/Akt pathways. Increased expression of neurotrophic factors in vitro and in vivo is the mechanism of neurotrophic action of flavonoids such as scutellarin, daidzein, genistein, and fisetin, while compounds like apigenin and ferulic acid increase cyclic adenosine monophosphate response element-binding protein (CREB) phosphorylation. Finally, the antioxidant activity of polyphenols reflected in the activation of Nrf2 pathway and the consequent upregulation of detoxification enzymes such as heme oxygenase-1 as well as the contribution of these effects to the neurotrophic activity have also been discussed. In conclusion, a better understanding of the neurotrophic effects of polyphenols and

  13. Extraction, spectrophotometric and atomic absorption spectrophotometric determination of molybdenum with caffeic acid and application in high purity grade steel and environmental samples

    SciTech Connect

    Shah, N.; Desai, M.N. ); Menon, S.K.; Agrawal, Y.K. )

    1989-06-01

    A new selective and sensitive method for extraction of yellow Mo(VI)-caffeic acid complex with a liquid ion exchanger, Aliquat 336 from 4.0 pH, and spectrophotometric determination of molybdenum in trace amounts is described. The molar absorptivity of the complex is 1.1 {times} 10{sup 5} 1 mol{sup {minus}1} cm{sup {minus}1} at 340 nm and the color system obeys Beers law in the range 0.04-0.99 ppm of Mo(VI). The molybdenum is also determined with AAS and the method is applied for its determination in steel and environmental samples.

  14. Acid detergent lignin, lodging resistance index, and expression of the caffeic acid O-methyltransferase gene in brown midrib-12 sudangrass

    PubMed Central

    Li, Yuan; Liu, Guibo; Li, Jun; You, Yongliang; Zhao, Haiming; Liang, Huan; Mao, Peisheng

    2015-01-01

    Understanding the relationship between acid detergent lignin (ADL) and lodging resistance index (LRI) is essential for breeding new varieties of brown midrib (bmr) sudangrass (Sorghum sudanense (Piper) Stapf.). In this study, bmr-12 near isogenic lines and their wild-types obtained by back cross breeding were used to compare relevant forage yield and quality traits, and to analyze expression of the caffeic acid O-methyltransferase (COMT) gene using quantitative real time-PCR. The research showed that the mean ADL content of bmr-12 mutants (20.94 g kg−1) was significantly (P < 0.05) lower than measured in N-12 lines (43.45 g kg−1), whereas the LRI of bmr-12 mutants (0.29) was significantly (P < 0.05) higher than in N-12 lines (0.22). There was no significant correlation between the two indexes in bmr-12 materials (r = −0.44, P > 0.05). Sequence comparison of the COMT gene revealed two point mutations present in bmr-12 but not in the wild-type, the second mutation changed amino acid 129 of the protein from Gln (CAG) to a stop codon (UAG). The relative expression level of COMT gene was significantly reduced, which likely led to the decreased ADL content observed in the bmr-12 mutant. PMID:26366111

  15. Synthesis of caffeic acid molecularly imprinted polymer microspheres and high-performance liquid chromatography evaluation of their sorption properties.

    PubMed

    Valero-Navarro, Angel; Gómez-Romero, María; Fernández-Sánchez, Jorge F; Cormack, Peter A G; Segura-Carretero, Antonio; Fernández-Gutiérrez, Alberto

    2011-10-14

    In the current work, a molecularly imprinted polymer (MIP) has been synthesised and used to enable the extraction of a naturally-occurring antioxidant from complex media. More specifically, we describe the first example of a caffeic acid (CA) MIP which has been synthesised in the form of well-defined polymer microspheres, and its use for the extraction of CA from fruit juice sample. The CA MIP was synthesised by precipitation polymerisation using 4-vinylpyridine as functional monomer, divinylbenzene-80 as crosslinker and acetonitrile:toluene (75/25, v/v) as porogen. The particle sizing and morphological characterisation of the polymers was carried out by means of scanning electron microscopy (narrow particle size distribution; ∼5 and 1.5 μm particle diameters for the MIP and NIP [non-imprinted polymer], respectively) and nitrogen sorption porosimetry (specific surface areas of 340 and 350 m(2)g(-1), and specific pore volumes of 0.17 and 0.19 cm(3)g(-1) for the MIP and NIP, respectively). The polymers were evaluated further by batch rebinding experiments, and from the derived isotherms their binding capacity and binding strength were determined (number of binding sites (N(K))=0.6 and 0.3 mmol g(-1) for the MIP and NIP, respectively, and apparent average adsorption constant (K(N))=10.0 and 1.6L mmol(-1) for the MIP and NIP, respectively). To evaluate the molecular recognition character of the MIP it was packed into a stainless steel column (50 mm × 4.6 mm i.d.) and evaluated as an HPLC-stationary phase. The mobile phase composition, flow rate, and the elution profile were then optimised in order to improve the peak shape without negatively affecting the imprinting factor (IF). Very interesting, promising properties were revealed. The imprinting factor (IF) under the optimised conditions was 11.9. Finally, when the imprinted LC column was used for the selective recognition of CA over eight related compounds, very good selectivity was obtained. This outcome enabled

  16. Caffeic acid phenethyl amide improves glucose homeostasis and attenuates the progression of vascular dysfunction in Streptozotocin-induced diabetic rats

    PubMed Central

    2013-01-01

    Background Glucose intolerance and cardiovascular complications are major symptoms in patients with diabetes. Many therapies have proven beneficial in treating diabetes in animals by protecting the cardiovascular system and increasing glucose utilization. In this study, we evaluated the effects of caffeic acid phenethyl amide (CAPA) on glucose homeostasis and vascular function in streptozotocin (STZ)-induced type 1 diabetic rats. Methods Diabetes (blood glucose levels > 350 mg/dL), was induced in Wistar rats by a single intravenous injection of 60 mg/kg STZ. Hypoglycemic effects were then assessed in normal and type 1 diabetic rats. In addition, coronary blood flow in Langendorff-perfused hearts was evaluated in the presence or absence of nitric oxide synthase (NOS) inhibitor. The thoracic aorta was used to measure vascular response to phenylephrine. Finally, the effect of chronic treatment of CAPA and insulin on coronary artery flow and vascular response to phenylephrine were analyzed in diabetic rats. Results Oral administration of 0.1 mg/kg CAPA decreased plasma glucose in normal (32.9 ± 2.3% decrease, P < 0.05) and diabetic rats (11.8 ± 5.5% decrease, P < 0.05). In normal and diabetic rat hearts, 1–10 μM CAPA increased coronary flow rate, and this increase was abolished by 10 μM NOS inhibitor. In the thoracic aorta, the concentration/response curve of phenylephrine was right-shifted by administration of 100 μM CAPA. Coronary flow rate was reduced to 7.2 ± 0.2 mL/min at 8 weeks after STZ-induction. However, 4 weeks of treatment with CAPA (3 mg/kg, intraperitoneal, twice daily) started at 4 weeks after STZ induction increased flow rate to 11.2 ± 0.5 mL/min (P < 0.05). In addition, the contractile response induced by 1 μM phenylephrine increased from 6.8 ± 0.6 mN to 11.4 ± 0.4 mN (P < 0.05) and 14.9 ± 1.4 mN (P < 0.05) by insulin (1 IU/kg, intraperitoneal) or CAPA treatment, respectively. Conclusions CAPA induced hypoglycemic activity, increased

  17. Application of a new high-performance liquid chromatographic method for measuring selected polyphenols in human plasma.

    PubMed

    Maiani, G; Serafini, M; Salucci, M; Azzini, E; Ferro-Luzzi, A

    1997-05-01

    We developed a method to measure plasma levels of selected polyphenols before and after ingestion of green tea. Blood samples were obtained from four healthy women before and 30 and 50 min after the ingestion of 300 ml of green tea infusion. A 1-ml volume of plasma was hydrolysed with 0.5 M HCl-methanol (1:1, v/v) for 30 min at room temperature, extracted with ethyl acetate and separated by reversed-phase chromatography. Polyphenols were identified on the basis of their retention times and by spectrum analysis. Green tea caffeine has the same retention times as caffeic acid. Consumption of green tea produces a notable increase in the plasma levels of caffeine plus caffeic acid and the appearance of measurable levels of epigallocatechingallate. In conclusion, the method was found to have the requisite features of specificity and sensitivity for monitoring plasma levels of selected tea polyphenols. PMID:9188819

  18. Enhancement of caffeic acid phenethyl ester on all-trans retinoic acid-induced differentiation in human leukemia HL-60 cells

    SciTech Connect

    Kuo, H.-C.; Kuo, W.-H.; Lee, Y.-J.; Wang, C.-J.; Tseng, T.-H. . E-mail: tht@csmu.edu.tw

    2006-10-01

    All-trans retinoic acid (ATRA) induces complete remission in a high proportion of patients with acute promyelocytic leukemia (APL); however, the response is sometimes very slow. Furthermore, relapse and resistance to treatment often occur despite continued treatment with ATRA. Thereafter, combination treatment strategies have been suggested to circumvent these problems. The present study demonstrates that caffeic acid phenethyl ester (CAPE), a major component of honeybee propolis, enhanced ATRA-induced granulocytic differentiation in HL-60, a human promyelocytic cell line. The differentiation was assessed by Wright-Giemsa stain, nitroblue tetrazolium reduction, and membrane differentiation marker CD11b. In addition, CAPE enhanced ATRA-induced cell cycle arrest at the G1 phase by decreasing the association of cdk2-cyclin E complex. Finally, it was demonstrated that CAPE promoted the ATRA-mediated nuclear transcription activation of RAR{alpha} assessed by EMSA assay and enhanced the expression of target genes including RAR{alpha}, C/EBP{epsilon}, and p21 protein resulting in the differentiation development of leukemia. It is suggested that CAPE possesses the potential to enhance the efficiency of ATRA in the differentiation therapy of APL.

  19. Cells Deficient in the Fanconi Anemia Protein FANCD2 are Hypersensitive to the Cytotoxicity and DNA Damage Induced by Coffee and Caffeic Acid.

    PubMed

    Burgos-Morón, Estefanía; Calderón-Montaño, José Manuel; Orta, Manuel Luis; Guillén-Mancina, Emilio; Mateos, Santiago; López-Lázaro, Miguel

    2016-01-01

    Epidemiological studies have found a positive association between coffee consumption and a lower risk of cardiovascular disorders, some cancers, diabetes, Parkinson and Alzheimer disease. Coffee consumption, however, has also been linked to an increased risk of developing some types of cancer, including bladder cancer in adults and leukemia in children of mothers who drink coffee during pregnancy. Since cancer is driven by the accumulation of DNA alterations, the ability of the coffee constituent caffeic acid to induce DNA damage in cells may play a role in the carcinogenic potential of this beverage. This carcinogenic potential may be exacerbated in cells with DNA repair defects. People with the genetic disease Fanconi Anemia have DNA repair deficiencies and are predisposed to several cancers, particularly acute myeloid leukemia. Defects in the DNA repair protein Fanconi Anemia D2 (FANCD2) also play an important role in the development of a variety of cancers (e.g., bladder cancer) in people without this genetic disease. This communication shows that cells deficient in FANCD2 are hypersensitive to the cytotoxicity (clonogenic assay) and DNA damage (γ-H2AX and 53BP1 focus assay) induced by caffeic acid and by a commercial lyophilized coffee extract. These data suggest that people with Fanconi Anemia, or healthy people who develop sporadic mutations in FANCD2, may be hypersensitive to the carcinogenic activity of coffee. PMID:27399778

  20. Cells Deficient in the Fanconi Anemia Protein FANCD2 are Hypersensitive to the Cytotoxicity and DNA Damage Induced by Coffee and Caffeic Acid

    PubMed Central

    Burgos-Morón, Estefanía; Calderón-Montaño, José Manuel; Orta, Manuel Luis; Guillén-Mancina, Emilio; Mateos, Santiago; López-Lázaro, Miguel

    2016-01-01

    Epidemiological studies have found a positive association between coffee consumption and a lower risk of cardiovascular disorders, some cancers, diabetes, Parkinson and Alzheimer disease. Coffee consumption, however, has also been linked to an increased risk of developing some types of cancer, including bladder cancer in adults and leukemia in children of mothers who drink coffee during pregnancy. Since cancer is driven by the accumulation of DNA alterations, the ability of the coffee constituent caffeic acid to induce DNA damage in cells may play a role in the carcinogenic potential of this beverage. This carcinogenic potential may be exacerbated in cells with DNA repair defects. People with the genetic disease Fanconi Anemia have DNA repair deficiencies and are predisposed to several cancers, particularly acute myeloid leukemia. Defects in the DNA repair protein Fanconi Anemia D2 (FANCD2) also play an important role in the development of a variety of cancers (e.g., bladder cancer) in people without this genetic disease. This communication shows that cells deficient in FANCD2 are hypersensitive to the cytotoxicity (clonogenic assay) and DNA damage (γ-H2AX and 53BP1 focus assay) induced by caffeic acid and by a commercial lyophilized coffee extract. These data suggest that people with Fanconi Anemia, or healthy people who develop sporadic mutations in FANCD2, may be hypersensitive to the carcinogenic activity of coffee. PMID:27399778

  1. Plasma concentrations of coffee polyphenols and plasma biomarkers of diabetes risk in healthy Japanese women

    PubMed Central

    Lee, A H; Tan, L 'B; Hiramatsu, N; Ishisaka, A; Alfonso, H; Tanaka, A; Uemura, N; Fujiwara, Y; Takechi, R

    2016-01-01

    Coffee consumption has been reported to reduce the risk of type 2 diabetes in experimental and epidemiological studies. This anti-diabetic effect of coffee may be attributed to its high content in polyphenols especially caffeic acid and chlorogenic acid. However, the association between plasma coffee polyphenols and diabetic risks has never been investigated in the literature. In this study, fasting plasma samples were collected from 57 generally healthy females aged 38–73 (mean 52, s.d. 8) years recruited in Himeji, Japan. The concentrations of plasma coffee polyphenols were determined by liquid chromatography coupled with mass tandem spectrometer. Diabetes biomarkers in the plasma/serum samples were analysed by a commercial diagnostic laboratory. Statistical associations were assessed using Spearman's correlation coefficients. The results showed that plasma chlorogenic acid exhibited negative associations with fasting blood glucose, glycated hemoglobin and C-reactive protein, whereas plasma total coffee polyphenol and plasma caffeic acid were weakly associated with these biomarkers. Our preliminary data support previous findings that coffee polyphenols have anti-diabetic effects but further replications with large samples of both genders are recommended. PMID:27270110

  2. Efficacy of various naturally occurring caffeic acid derivatives in preventing post-harvest protein losses in forages

    Technology Transfer Automated Retrieval System (TEKTRAN)

    In red clover, oxidation of endogenous o-diphenols by polyphenol oxidase (PPO) inhibits post-harvest proteolyis. This system is transferable to alfalfa by providing PPO (via a transgene) and o-diphenol PPO substrates (via exogenous application). To exploit the PPO system for protein protection, it w...

  3. The role of natural polyphenols in cell signaling and cytoprotection against cancer development.

    PubMed

    Lewandowska, Hanna; Kalinowska, Monika; Lewandowski, Włodzimierz; Stępkowski, Tomasz M; Brzóska, Kamil

    2016-06-01

    The cytoprotective and anticancer action of dietary in-taken natural polyphenols has for long been attributed only to their direct radical scavenging activities. Currently it is well supported that those compounds display a broad spectrum of biological and pharmacological outcomes mediated by their complex metabolism, interaction with gut microbiota as well as direct interactions of their metabolites with key cellular signaling proteins. The beneficial effects of natural polyphenols and their synthetic derivatives are extensively studied in context of cancer prophylaxis and therapy. Herein we focus on cell signaling to explain the beneficial role of polyphenols at the three stages of cancer development: we review the recent proceedings about the impact of polyphenols on the cytoprotective antioxidant response and their proapoptotic action at the premalignant stage, and finally we present data showing how phenolic acids (e.g., caffeic, chlorogenic acids) and flavonols (e.g., quercetin) hamper the development of metastatic cancer. PMID:27142731

  4. Enhanced anti-oxidative effect of fermented Korean mistletoe is originated from an increase in the contents of caffeic acid and lyoniresinol.

    PubMed

    Kim, Se-Yong; Yang, Eun-Ju; Son, Youn Kyoung; Yeo, Joo-Hong; Song, Kyung-Sik

    2016-05-18

    Viscum album var. coloratum (Korean mistletoe; KM) is an herbal medicine that is used worldwide for the treatment of various immunological disorders and cancers. KM extract showed enhanced anti-oxidative effects in 2,2-diphenyl-1-picrylhydrazyl, Trolox equivalent antioxidant capacity, and 5-(and-6)-chloromethyl-2',7'-dichlorodihydrofluorescein diacetate acetyl ester assays after being fermented with a crude enzyme extract from a soybean paste fungus, Aspergillus kawachii. High-performance liquid chromatography analysis showed four increased peaks in enzyme treated KM. The increased peaks were isolated and identified as caffeic acid (1), hesperetin (2), syringaldehyde (3), and lyoniresinol (4). Among the four compounds, only 1 and 4 showed strong anti-oxidative activity. Therefore, the fermentation increased the contents of 1 and 4, which consequently increased the anti-oxidative activity of KM. PMID:27072079

  5. Caffeic Acid Phenethyl Ester Causes p21Cip1 Induction, Akt Signaling Reduction, and Growth Inhibition in PC-3 Human Prostate Cancer Cells

    PubMed Central

    Lin, Hui-Ping; Jiang, Shih Sheng; Chuu, Chih-Pin

    2012-01-01

    Caffeic acid phenethyl ester (CAPE) treatment suppressed proliferation, colony formation, and cell cycle progression in PC-3 human prostate cancer cells. CAPE decreased protein expression of cyclin D1, cyclin E, SKP2, c-Myc, Akt1, Akt2, Akt3, total Akt, mTOR, Bcl-2, Rb, as well as phosphorylation of Rb, ERK1/2, Akt, mTOR, GSK3α, GSK3β, PDK1; but increased protein expression of KLF6 and p21Cip1. Microarray analysis indicated that pathways involved in cellular movement, cell death, proliferation, and cell cycle were affected by CAPE. Co-treatment of CAPE with chemotherapeutic drugs vinblastine, paclitaxol, and estramustine indicated synergistic suppression effect. CAPE administration may serve as a potential adjuvant therapy for prostate cancer. PMID:22347457

  6. Humic substances can modulate the allelopathic potential of caffeic, ferulic, and salicylic acids for seedlings of lettuce (Lactuca sativa L.) and tomato (Lycopersicon esculentum Mill.).

    PubMed

    Loffredo, Elisabetta; Monaci, Linda; Senesi, Nicola

    2005-11-30

    The capacity of a leonardite humic acid (LHA), a soil humic acid (SHA), and a soil fulvic acid (SFA) in modulating the allelopathic potential of caffeic acid (CA), ferulic acid (FA), and salicylic acid (SA) on seedlings of lettuce (Lactuca sativa L.) and tomato (Lycopersicon esculentum Mill.) was investigated. Lettuce showed a sensitivity greater than that of tomato to CA, FA, and SA phytotoxicity, which was significantly reduced or even suppressed in the presence of SHA or SFA, especially at the highest dose, but not LHA. In general, SFA was slightly more active than SHA, and the efficiency of the action depended on their concentration, the plant species and the organ examined, and the allelochemical. The daily measured residual concentration of CA and FA decreased drastically and that of SA slightly in the presence of germinating seeds of lettuce, which were thus able to absorb and/or enhance the degradation of CA and FA. The adsorption capacity of SHA for the three allelochemicals was small and decreased in the order FA > CA > SA, thus suggesting that adsorption could be a relevant mechanism, but not the only one, involved in the "antiallelopathic" action. PMID:16302757

  7. The impact of polyphenols on Bifidobacterium growth.

    PubMed

    Gwiazdowska, Daniela; Juś, Krzysztof; Jasnowska-Małecka, Joanna; Kluczyńska, Katarzyna

    2015-01-01

    Polyphenols are a common group of plant based bioactive compounds, that can affect human health because of their antioxidant and antimicrobial properties as well as free-radical scavenging activity. An increasing interest is observed in the interaction between polyphenols and microbiota occurring in food and the human gut. The aim of the work presented here, was to evaluate the effect of some polyphenolic compounds on the growth of two strains of Bifidobacterium: B. adolescentis and B. bifidum. The influence of some flavonoids: naringinin, hesperidin, rutin, quercetin as well as phenolic acids: gallic, caffeic, p-coumaric, ferulic, chlorogenic, vanillic and sinapic was determined by a 96-well microtiter plate assay. In the experiments the effect of three different concentrations of polyphenols: 2, 20 and 100 µg/ml on the growth of Bifidobacterium strains was investigated. All tested compounds influenced the growth of the examined bacteria. Both stimulatory and inhibitory effects were observed in comparison to the positive control. The strongest impact on the growth of bifidobacteria was observed during the first hours of incubation. The constant inhibitory effect was observed for hesperidin and quercetin addition and was dose-dependent. B. bifidum showed a stronger dependence on phenolic acids content in the medium than B. adolescentis during the first hours of incubation. PMID:26619254

  8. Interaction between Tea Polyphenols and Bile Acid Inhibits Micellar Cholesterol Solubility.

    PubMed

    Ogawa, Kazuki; Hirose, Sayumi; Nagaoka, Satoshi; Yanase, Emiko

    2016-01-13

    The molecular mechanism by which tea polyphenols decrease the micellar solubility of cholesterol is not completely clear. To clarify this mechanism, this study investigated the interaction between tea polyphenols (catechins and oolongtheanins) and cholesterol micelles. A nuclear magnetic resonance (NMR) study was performed on a micellar solution containing taurocholic acid and epigallocatechin gallate (EGCg), and high-performance liquid chromatography (HPLC) analysis was carried out on the precipitate and the supernatant that formed when EGCg was added to a cholesterol-micelle solution. The data indicated a regiospecific interaction of EGCg with taurocholic acid. Therefore, the ability of EGCg to lower the solubility of phosphatidylcholine (PC) and cholesterol in micellar solutions can be attributed to their elimination from the micelles due to interaction between taurocholic acids and EGCg. PMID:26651358

  9. Comparative polyphenolic content and antioxidant activities of Genista tinctoria L. and Genistella sagittalis (L.) Gams (Fabaceae).

    PubMed

    Hanganu, Daniela; Olah, Neli Kinga; Benedec, Daniela; Mocan, Andrei; Crisan, Gianina; Vlase, Laurian; Popica, Iulia; Oniga, Ilioara

    2016-01-01

    The aim of this study was focused on the polyphenolic composition and antioxidant capacity of Genista tinctoria L. and Genistella sagittalis (L.) Gams. A qualitative and quantitative characterization of the main phenolic compounds from the extracts were carried out using a HPLC-MS method. The total polyphenolic and flavonoid content was spectrophotometrically determined. The antioxidant activity towards various radicals generated in different systems was evaluated usingDPPH bleaching method, Trolox equivalent antioxidant capacity assay (TEAC) and Oxygen radical absorbance capacity (ORAC), and all indicated that G. tinctoria extract was more antioxidant than G. sagittalis extract.That was in good agreement with the total polyphenolic and flavonoidic content.Chlorogenic acid, p-coumaric acid, isoquercitrin and apigenin were identified in bothspecies. Caffeic acid, ferulic acid, hyperoside, rutin, quercitrin and luteolin were found only in G. tinctoria, while quercetin was determined in G. sagittalis. PMID:27005507

  10. Structure-Function Analyses of a Caffeic Acid O-Methyltransferase from Perennial Ryegrass Reveal the Molecular Basis for Substrate Preference[W][OA

    PubMed Central

    Louie, Gordon V.; Bowman, Marianne E.; Tu, Yi; Mouradov, Aidyn; Spangenberg, German; Noel, Joseph P.

    2010-01-01

    Lignin forms from the polymerization of phenylpropanoid-derived building blocks (the monolignols), whose modification through hydroxylation and O-methylation modulates the chemical and physical properties of the lignin polymer. The enzyme caffeic acid O-methyltransferase (COMT) is central to lignin biosynthesis. It is often targeted in attempts to engineer the lignin composition of transgenic plants for improved forage digestibility, pulping efficiency, or utility in biofuel production. Despite intensive investigation, the structural determinants of the regiospecificity and substrate selectivity of COMT remain poorly defined. Reported here are x-ray crystallographic structures of perennial ryegrass (Lolium perenne) COMT (Lp OMT1) in open conformational state, apo- and holoenzyme forms and, most significantly, in a closed conformational state complexed with the products S-adenosyl-l-homocysteine and sinapaldehyde. The product-bound complex reveals the post-methyl-transfer organization of COMT’s catalytic groups with reactant molecules and the fully formed phenolic-ligand binding site. The core scaffold of the phenolic ligand forges a hydrogen-bonding network involving the 4-hydroxy group that anchors the aromatic ring and thereby permits only metahydroxyl groups to be positioned for transmethylation. While distal from the site of transmethylation, the propanoid tail substituent governs the kinetic preference of ryegrass COMT for aldehydes over alcohols and acids due to a single hydrogen bond donor for the C9 oxygenated moiety dictating the preference for an aldehyde. PMID:21177481

  11. Stability and biological activity of wild blueberry (Vaccinium angustifolium) polyphenols during simulated in vitro gastrointestinal digestion.

    PubMed

    Correa-Betanzo, J; Allen-Vercoe, E; McDonald, J; Schroeter, K; Corredig, M; Paliyath, G

    2014-12-15

    Wild blueberries are rich in polyphenols and have several potential health benefits. Understanding the factors that affect the bioaccessibility and bioavailability of polyphenols is important for evaluating their biological significance and efficacy as functional food ingredients. Since the bioavailability of polyphenols such as anthocyanins is generally low, it has been proposed that metabolites resulting during colonic fermentation may be the components that exert health benefits. In this study, an in vitro gastrointestinal model comprising sequential chemostat fermentation steps that simulate digestive conditions in the stomach, small intestine and colon was used to investigate the breakdown of blueberry polyphenols. The catabolic products were isolated and biological effects tested using a normal human colonic epithelial cell line (CRL 1790) and a human colorectal cancer cell line (HT 29). The results showed a high stability of total polyphenols and anthocyanins during simulated gastric digestion step with approximately 93% and 99% of recovery, respectively. Intestinal digestion decreased polyphenol- and anthocyanin- contents by 49% and 15%, respectively, by comparison to the non-digested samples. During chemostat fermentation that simulates colonic digestion, the complex polyphenol mixture was degraded to a limited number of phenolic compounds such as syringic, cinnamic, caffeic, and protocatechuic acids. Only acetylated anthocyanins were detected in low amounts after chemostat fermentation. The catabolites showed lowered antioxidant activity and cell growth inhibition potential. Results suggest that colonic fermentation may alter the biological activity of blueberry polyphenols. PMID:25038707

  12. The pro-fibrotic properties of transforming growth factor on human fibroblasts are counteracted by caffeic acid by inhibiting myofibroblast formation and collagen synthesis.

    PubMed

    Mia, Masum M; Bank, Ruud A

    2016-03-01

    Fibrosis is a chronic disorder affecting many organs. A universal process in fibrosis is the formation of myofibroblasts and the subsequent collagen deposition by these cells. Transforming growth factor beta1 (TGFβ1) plays a major role in the formation of myofibroblasts, e.g. by activating fibroblasts. Currently, no treatments are available to circumvent fibrosis. Caffeic acid phenethyl ester (CAPE) shows a broad spectrum of biological activities, including anti-fibrotic properties in vivo in mice and rats. However, little is known about the direct effects of CAPE on fibroblasts. We have tested whether CAPE is able to suppress myofibroblast formation and collagen formation of human dermal and lung fibroblasts exposed to TGFβ1, and found that this was indeed the case. In fact, the formation of myofibroblasts by TGFβ1 and subsequent collagen formation was completely abolished by CAPE. The same was observed for fibronectin and tenascin C. The lack of myofibroblast formation is likely due to the suppression of GLI1 and GLI2 expression by CAPE because of diminished nuclear SMAD2/3 levels. Post-treatment with CAPE after myofibroblast formation even resulted in a partial reversal of myofibroblasts into fibroblasts and/or reduction in collagen formation. Major discrepancies were seen between mRNA levels of collagen type I and cells stained positive for collagen, underlining the need for protein data in fibrosis studies to make reliable conclusions. PMID:26453399

  13. Caffeic acid phenethyl ester inhibits 3-MC-induced CYP1A1 expression through induction of hypoxia-inducible factor-1α.

    PubMed

    Kim, Hyung Gyun; Han, Eun Hee; Im, Ji Hye; Lee, Eun Ji; Jin, Sun Woo; Jeong, Hye Gwang

    2015-09-25

    Caffeic acid phenethyl ester (CAPE), a natural component of propolis, is reported to have anticarcinogenic properties, although its precise chemopreventive mechanism remains unclear. In this study, we examined the effects of CAPE on 3-methylcholanthrene (3-MC)-induced CYP1A1 expression and activities. CAPE reduced the formation of the benzo[a]pyrene-DNA adduct. Moreover, CAPE inhibited 3-MC-induced CYP1A1 activity, mRNA expression, protein level, and promoter activity. CAPE treatment also decreased 3-MC-inducible xenobiotic-response element (XRE)-linked luciferase, aryl hydrocarbons receptor (AhR) transactivation and nuclear localization. CAPE induced hypoxia inducible factor-1α (HIF-1α) protein level and HIF-1α responsible element (HRE) transcriptional activity. CAPE-mediated HIF-1α reduced 3-MC-inducible CYP1A1 protein expression. Taken together, CAPE decreases 3-MC-mediated CYP1A1 expression, and this inhibitory response is associated with inhibition of AhR and HIF-1α induction. PMID:26296470

  14. Caffeic Acid phenethyl ester and ethanol extract of propolis induce the complementary cytotoxic effect on triple-negative breast cancer cell lines.

    PubMed

    Rzepecka-Stojko, Anna; Kabała-Dzik, Agata; Moździerz, Aleksandra; Kubina, Robert; Wojtyczka, Robert D; Stojko, Rafał; Dziedzic, Arkadiusz; Jastrzębska-Stojko, Żaneta; Jurzak, Magdalena; Buszman, Ewa; Stojko, Jerzy

    2015-01-01

    Chemotherapy of breast cancer could be improved by bioactive natural substances, which may potentially sensitize the carcinoma cells' susceptibility to drugs. Numerous phytochemicals, including propolis, have been reported to interfere with the viability of carcinoma cells. We evaluated the in vitro cytotoxic activity of ethanol extract of propolis (EEP) and its derivative caffeic acid phenethyl ester (CAPE) towards two triple-negative breast cancer (TNBC) cell lines, MDA-MB-231 and Hs578T, by implementation of the MTT and lactate dehydrogenase (LDH) assays. The morphological changes of breast carcinoma cells were observed following exposure to EEP and CAPE. The IC50 of EEP was 48.35 µg∙mL-1 for MDA-MB-23 cells and 33.68 µg∙mL-1 for Hs578T cells, whereas the CAPE IC50 was 14.08 µM and 8.01 µM for the MDA-MB-231 and Hs578T cell line, respectively. Here, we report that propolis and CAPE inhibited the growth of the MDA-MB-231 and Hs578T lines in a dose-dependent and exposure time-dependent manner. EEP showed less cytotoxic activity against both types of TNBC cells. EEP and, particularly, CAPE may markedly affect the viability of breast cancer cells, suggesting the potential role of bioactive compounds in chemoprevention/chemotherapy by potentiating the action of standard anti-cancer drugs. PMID:26007182

  15. Caffeic acid phenethyl ester activates pro-apoptotic and epithelial-mesenchymal transition-related genes in ovarian cancer cells A2780 and A2780cis.

    PubMed

    Gherman, Claudia; Braicu, Ovidiu Leonard; Zanoaga, Oana; Jurj, Anca; Pileczki, Valentina; Maralani, Mahafarin; Drigla, Flaviu; Braicu, Cornelia; Budisan, Liviuta; Achimas-Cadariu, Patriciu; Berindan-Neagoe, Ioana

    2016-02-01

    Ovarian cancer is a highly aggressive pathology, displaying a poor prognosis and chemoresistance to classical therapy. The present study was conducted to evaluate the effect of caffeic acid phenethyl ester (CAPE) on survival of ovarian cancer cell lines, A2780 (sensitive to cisplatin) and A2780cis (resistant to cisplatin). MTT assay was used to evaluate cell viability, while the apoptotic processes were examined by flow cytometry and qRT-PCR. A reduction of cell proliferation and activation of the apoptosis was observed in both cell lines. qRT-PCR evaluation demonstrated the activation of the pro-apoptotic genes (BAD, CASP8, FAS, FADD, p53) in both cell lines. The limited therapeutic effect in A2780 cells is explained by the activation of epithelial-mesenchymal transition-related genes (ZEB1, ZEB2, or TGFBB1) as displayed by Ingenuity Network analysis. Overall data suggest that CAPE can be used as an alternative in sensitizing cells to chemotherapy. PMID:26838168

  16. Caffeic acid phenethyl ester attenuates ionize radiation-induced intestinal injury through modulation of oxidative stress, apoptosis and p38MAPK in rats.

    PubMed

    Jin, Liu-Gen; Chu, Jian-Jun; Pang, Qing-Feng; Zhang, Fu-Zheng; Wu, Gang; Zhou, Le-Yuan; Zhang, Xiao-Jun; Xing, Chun-Gen

    2015-07-01

    Caffeic acid phenyl ester (CAPE) is a potent anti-inflammatory agent and it can eliminate the free radicals. This study aimed to investigate the radioprotective effects of CAPE on X-ray irradiation induced intestinal injury in rats. Rats were intragastrically administered with 10 μmol/kg/d CAPE for 7 consecutive days before exposing them to a single dose of X-ray irradiation (9Gy) to abdomen. Rats were sacrificed 72 h after exposure to radiation. We found that pretreatment with CAPE effectively attenuated intestinal pathology changes, apoptosis, oxidative stress, bacterial translocation, the content of nitric oxide and myeloperoxidase as well as the concentration of plasma tumor necrosis factor-α. Pretreatment with CAPE also reversed the activation of p38MAPK and the increased expression of intercellular cell adhesion molecule-1 induced by radiation in intestinal mucosa. Taken together, these results suggest that pretreatment with CAPE could be a promising candidate for treating radiation-induced intestinal injury. PMID:26122083

  17. Antileishmanial lead structures from nature: analysis of structure-activity relationships of a compound library derived from caffeic Acid bornyl ester.

    PubMed

    Glaser, Jan; Schultheis, Martina; Hazra, Sudipta; Hazra, Banasri; Moll, Heidrun; Schurigt, Uta; Holzgrabe, Ulrike

    2014-01-01

    Bioassay-guided fractionation of a chloroform extract of Valeriana wallichii (V. wallichii) rhizomes lead to the isolation and identification of caffeic acid bornyl ester (1) as the active component against Leishmania major (L. major) promastigotes (IC50 = 48.8 µM). To investigate the structure-activity relationship (SAR), a library of compounds based on 1 was synthesized and tested in vitro against L. major and L. donovani promastigotes, and L. major amastigotes. Cytotoxicity was determined using a murine J774.1 cell line and bone marrow derived macrophages (BMDM). Some compounds showed antileishmanial activity in the concentration range of pentamidine and miltefosine which are the standard drugs in use. In the L. major amastigote assay compounds 15, 19 and 20 showed good activity with relatively low cytotoxicity against BMDM, resulting in acceptable selectivity indices. Molecules with adjacent phenolic hydroxyl groups exhibited elevated cytotoxicity against murine cell lines J774.1 and BMDM. The Michael system seems not to be essential for antileishmanial activity. Based on the results compound 27 can be regarded as new lead structure for further structure optimization. PMID:24473204

  18. Polygonum aviculare L. and its active compounds, quercitrin hydrate, caffeic acid, and rutin, activate the Wnt/β-catenin pathway and induce cutaneous wound healing.

    PubMed

    Seo, Seol Hwa; Lee, Soung-Hoon; Cha, Pu-Hyeon; Kim, Mi-Yeon; Min, Do Sik; Choi, Kang-Yell

    2016-05-01

    Polygonum aviculare L. is a member of the Polygonaceae family of plants, which has been known for its antioxidant and anti-obesity effects. However, the wound healing function of P. aviculare extract has not been assessed. In this study, we identified a novel property of P. aviculare extract as a Wnt/β-catenin pathway activator based on a screen of 350 plant extracts using HEK293-TOP cells retaining the Wnt/β-catenin signaling reporter gene. P. aviculare extract accelerated the migration of HaCaT keratinocytes without showing significant cytotoxicity. Moreover, P. aviculare extract efficiently re-epithelized wounds generated on mice. Additionally, ingredients of P. aviculare extract, such as quercitrin hydrate, caffeic acid, and rutin, also accelerated the motility of HaCaT keratinocytes with the activation of Wnt/β-catenin signaling. Therefore, based on our findings, P. aviculare extract and its active ingredients could be potential therapeutic agents for wound healing. Copyright © 2016 John Wiley & Sons, Ltd. PMID:26929003

  19. Mutation in Brachypodium caffeic acid O-methyltransferase 6 alters stem and grain lignins and improves straw saccharification without deteriorating grain quality

    PubMed Central

    Ho-Yue-Kuang, Séverine; Alvarado, Camille; Antelme, Sébastien; Bouchet, Brigitte; Cézard, Laurent; Le Bris, Philippe; Legée, Frédéric; Maia-Grondard, Alessandra; Yoshinaga, Arata; Saulnier, Luc; Guillon, Fabienne; Sibout, Richard; Lapierre, Catherine; Chateigner-Boutin, Anne-Laure

    2016-01-01

    Cereal crop by-products are a promising source of renewable raw material for the production of biofuel from lignocellulose. However, their enzymatic conversion to fermentable sugars is detrimentally affected by lignins. Here the characterization of the Brachypodium Bd5139 mutant provided with a single nucleotide mutation in the caffeic acid O-methyltransferase BdCOMT6 gene is reported. This BdCOMT6-deficient mutant displayed a moderately altered lignification in mature stems. The lignin-related BdCOMT6 gene was also found to be expressed in grains, and the alterations of Bd5139 grain lignins were found to mirror nicely those evidenced in stem lignins. The Bd5139 grains displayed similar size and composition to the control. Complementation experiments carried out by introducing the mutated gene into the AtCOMT1-deficient Arabidopsis mutant demonstrated that the mutated BdCOMT6 protein was still functional. Such a moderate down-regulation of lignin-related COMT enzyme reduced the straw recalcitrance to saccharification, without compromising the vegetative or reproductive development of the plant. PMID:26433202

  20. Cloning of Arabidopsis serotonin N-acetyltransferase and its role with caffeic acid O-methyltransferase in the biosynthesis of melatonin in vitro despite their different subcellular localizations.

    PubMed

    Lee, Hyoung Yool; Byeon, Yeong; Lee, Kyungjin; Lee, Hye-Jung; Back, Kyoungwhan

    2014-11-01

    Serotonin N-acetyltransferase (SNAT) is the penultimate enzyme in melatonin biosynthesis. We cloned SNAT from Arabidopsis thaliana (AtSNAT) and functionally characterized this enzyme for the first time from dicotyledonous plants. Similar to rice SNAT, AtSNAT was found to localize to chloroplasts with peak enzyme activity at 45 °C (Km , 309 μm; Vmax , 1400 pmol/min/mg protein). AtSNAT also catalyzed 5-methoxytryptamine (5-MT) into melatonin with high catalytic activity (Km , 51 μm; Vmax , 5300 pmol/min/mg protein). In contrast, Arabidopsis caffeic acid O-methyltransferase (AtCOMT) localized to the cytoplasm. Interestingly, AtCOMT can methylate serotonin into 5-MT with low catalytic activity (Km , 3.396 mm; Vmax , 528 pmol/min/mg protein). These data suggest that serotonin can be converted into either N-acetylserotonin by SNAT or into 5-MT by COMT, after which it is metabolized into melatonin by COMT or SNAT, respectively. To support this hypothesis, serotonin was incubated in the presence of both AtSNAT and AtCOMT enzymes. In addition to melatonin production, the production of major intermediates depended on incubation temperatures; N-acetylserotonin was predominantly produced at high temperatures (45 °C), while low temperatures (37 °C) favored the production of 5-MT. Our results provide biochemical evidence for the presence of a serotonin O-methylation pathway in plant melatonin biosynthesis. PMID:25250906

  1. Nrf2-Mediated HO-1 Induction Coupled with the ERK Signaling Pathway Contributes to Indirect Antioxidant Capacity of Caffeic Acid Phenethyl Ester in HepG2 Cells

    PubMed Central

    Kim, Jin-Kyoung; Jang, Hae-Dong

    2014-01-01

    The objective of this study is to investigate the contributing effect of the nuclear transcription factor-erythroid 2-related factor 2 (Nrf2)-mediated signaling pathway on the indirect antioxidant capacity of caffeic acid phenethyl ester (CAPE) against oxidative stress in HepG2 cells. The result of an antioxidant response element (ARE)-luciferase assay showed that CAPE stimulated ARE promoter activity resulting in increased transcriptional and translational activities of heme oxygenase-1 (HO-1). In addition, CAPE treatment enhanced Nrf2 accumulation in the nucleus and the post-translational phosphorylation level of extracellular signal-regulated kinase (ERK) among several protein kinases tested. Treatment with ERK inhibitor U126 completely suppressed CAPE-induced ERK phosphorylation and HO-1 expression, but it only partly inhibited CAPE-induced Nrf2 accumulation and ARE promoter. Using the 2',7'-dichlorofluorescein-diacetate (DCFH-DA) method, the cellular antioxidant capacity of CAPE against 2,2'-azobis (2-amidinopropane) dihydrochloride (AAPH)- or H2O2-induced oxidative stress also was shown to be partially suppressed by the ERK inhibitor. From the overall results it is proposed that the indirect antioxidant activity of CAPE against oxidative stress in HepG2 cells is partially attributed to induction of HO-1, which is regulated by Kelch-like erythroid-cell-derived protein with CNC homology (ECH)-associated protein 1 (Keap1)-independent Nrf2 activation relying on post-translational phosphorylation of ERK. PMID:25007817

  2. Caffeic acid phenethyl ester inhibits 3-MC-induced CYP1A1 expression through induction of hypoxia-inducible factor-1α

    SciTech Connect

    Kim, Hyung Gyun; Han, Eun Hee; Im, Ji Hye; Lee, Eun Ji; Jin, Sun Woo; Jeong, Hye Gwang

    2015-09-25

    Caffeic acid phenethyl ester (CAPE), a natural component of propolis, is reported to have anticarcinogenic properties, although its precise chemopreventive mechanism remains unclear. In this study, we examined the effects of CAPE on 3-methylcholanthrene (3-MC)-induced CYP1A1 expression and activities. CAPE reduced the formation of the benzo[a]pyrene-DNA adduct. Moreover, CAPE inhibited 3-MC-induced CYP1A1 activity, mRNA expression, protein level, and promoter activity. CAPE treatment also decreased 3-MC-inducible xenobiotic-response element (XRE)-linked luciferase, aryl hydrocarbons receptor (AhR) transactivation and nuclear localization. CAPE induced hypoxia inducible factor-1α (HIF-1α) protein level and HIF-1α responsible element (HRE) transcriptional activity. CAPE-mediated HIF-1α reduced 3-MC-inducible CYP1A1 protein expression. Taken together, CAPE decreases 3-MC-mediated CYP1A1 expression, and this inhibitory response is associated with inhibition of AhR and HIF-1α induction. - Highlights: • CAPE reduced the formation of the benzo[a]pyrene-DNA adduct. • CAPE inhibited 3-MC-induced CYP1A1 expression. • CAPE induced HIF-1α induction. • CAPE-mediated HIF-1α reduced 3-MC-inducible CYP1A1 expression.

  3. Caffeic Acid Phenylethyl Ester and MG-132 Have Apoptotic and Antiproliferative Effects on Leukemic Cells But Not on Normal Mononuclear Cells12

    PubMed Central

    Cavaliere, Victoria; Papademetrio, Daniela L; Lorenzetti, Mario; Valva, Pamela; Preciado, María Victoria; Gargallo, Patricia; Larripa, Irene; Monreal, Mariela B; Pardo, María Laura; Hajos, Silvia E; Blanco, Guillermo AC; Álvarez, Élida MC

    2009-01-01

    Chemotherapy aims to limit proliferation and induce apoptotic cell death in tumor cells. Owing to blockade of signaling pathways involved in cell survival and proliferation, nuclear factor κB (NF-κB) inhibitors can induce apoptosis in a number of hematological malignancies. The efficacy of conventional chemotherapeutic drugs, such as vincristine (VCR) and doxorubicine (DOX), may be enhanced with combined therapy based on NF-κB modulation. In this study, we evaluated the effect of caffeic acid phenylethyl ester (CAPE) and MG-132, two nonspecific NF-κB inhibitors, and conventional chemotherapeutics drugs DOX and VCR on cell proliferation and apoptosis induction on a lymphoblastoid B-cell line, PL104, established and characterized in our laboratory. CAPE and MG-132 treatment showed a strong antiproliferative effect accompanied by clear cell cycle deregulation and apoptosis induction. Doxorubicine and VCR showed antiproliferative effects similar to those of CAPE and MG-132, although the latter drugs showed an apoptotic rate two-fold higher than DOX and VCR. None of the four compounds showed cytotoxic effect on peripheral mononuclear cells from healthy volunteers. CAPE- and MG-132-treated bone marrow cells from patients with myeloid and lymphoid leukemias showed 69% (P < .001) and 25% decrease (P < .01) in cell proliferation and 42% and 34% (P < .01) apoptosis induction, respectively. Overall, our results indicate that CAPE and MG-132 had a strong and selective apoptotic effect on tumor cells that may be useful in future treatment of hematological neoplasias. PMID:19252751

  4. Determination of the Structure and Catalytic Mechanism of Sorghum bicolor Caffeic Acid O-Methyltransferase and the Structural Impact of Three brown midrib12 Mutations.

    PubMed

    Green, Abigail R; Lewis, Kevin M; Barr, John T; Jones, Jeffrey P; Lu, Fachuang; Ralph, John; Vermerris, Wilfred; Sattler, Scott E; Kang, ChulHee

    2014-06-19

    Using S-adenosyl-methionine as the methyl donor, caffeic acid O-methyltransferase from sorghum (Sorghum bicolor; SbCOMT) methylates the 5-hydroxyl group of its preferred substrate, 5-hydroxyconiferaldehyde. In order to determine the mechanism of SbCOMT and understand the observed reduction in the lignin syringyl-to-guaiacyl ratio of three brown midrib12 mutants that carry COMT gene missense mutations, we determined the apo-form and S-adenosyl-methionine binary complex SbCOMT crystal structures and established the ternary complex structure with 5-hydroxyconiferaldehyde by molecular modeling. These structures revealed many features shared with monocot ryegrass (Lolium perenne) and dicot alfalfa (Medicago sativa) COMTs. SbCOMT steady-state kinetic and calorimetric data suggest a random bi-bi mechanism. Based on our structural, kinetic, and thermodynamic results, we propose that the observed reactivity hierarchy among 4,5-dihydroxy-3-methoxycinnamyl (and 3,4-dihydroxycinnamyl) aldehyde, alcohol, and acid substrates arises from the ability of the aldehyde to stabilize the anionic intermediate that results from deprotonation of the 5-hydroxyl group by histidine-267. Additionally, despite the presence of other phenylpropanoid substrates in vivo, sinapaldehyde is the preferential product, as demonstrated by its low Km for 5-hydroxyconiferaldehyde. Unlike its acid and alcohol substrates, the aldehydes exhibit product inhibition, and we propose that this is due to nonproductive binding of the S-cis-form of the aldehydes inhibiting productive binding of the S-trans-form. The S-cis-aldehydes most likely act only as inhibitors, because the high rotational energy barrier around the 2-propenyl bond prevents S-trans-conversion, unlike alcohol substrates, whose low 2-propenyl bond rotational energy barrier enables rapid S-cis/S-trans-interconversion. PMID:24948836

  5. Polyphenol-chitosan conjugates: Synthesis, characterization, and applications.

    PubMed

    Hu, Qiaobin; Luo, Yangchao

    2016-10-20

    Chitosan, the only positively charged polysaccharide in the world, is very attractive for food, medicinal and pharmaceutical applications because of its promising properties, including non-toxicity, superb biodegradability, high biocompatibility, abundant availability and low cost. In order to overcome the poor water solubility and widen the applications of chitosan, various polyphenol-chitosan conjugates have been synthesized in recent years. The present review focuses on the chitosan-based conjugates formed using different polyphenols, including gallic acid, caffeic acid, ferulic acid, salicylic acid, catechin, and EGGE, etc. Three major synthesis techniques, namely, activated ester-mediated modification, enzyme-mediated strategy, and free radical induced grafting approach are introduced in detail. In addition, the new physicochemical and biological properties of polyphenol-chitosan conjugates are introduced, including water solubility, thermo stability, in vitro and in vivo antioxidant activity, antimicrobial and anticancer activity. Furthermore, the novel applications of each conjugate are discussed in detail. Lastly, the challenges and prospective areas of study related to polyphenol-chitosan are summarized. PMID:27474608

  6. Effects of caffeic acid phenethyl ester on matrix molecules and angiogenetic and anti-angiogenetic factors in gastric cancer cells cultured on different substrates.

    PubMed

    Kosova, F; Kurt, F O; Olmez, E; Tuğlu, I; Arı, Z

    2016-01-01

    Migration, invasion, metastasis and angiogenesis associated with cancer depend on the surrounding microenvironment. Angiogenesis, the growth of new capillaries, is a regulator of cancer growth and a useful target for cancer therapy. We examined matrix protein interactions in a gastric cancer cell culture that was treated with different doses of caffeic acid (3,4-dihydroxycinnamic acid) phenethyl ester (CAPE). We also investigated the relations among the levels of vascular endothelial growth factor (VEGF), matrix metalloproteinase-9 (MMP-9), endostatin (ES) and trombospondin-1 (TSP-1). Cytotoxity of CAPE was measured using the 3-(4,5-dmethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) assay. We examined the behavior of cells on laminin and collagen I coated surfaces in response to the angiogenic effect of these matrix molecules. We examined the protein alterations of these matrix molecules immunohistochemically and measured the levels of VEGF, MMP-9, ES and TSP-1 using the ELISA test. We showed that application of CAPE to the gastric cancer cell line on tissue culture plastic, laminin and collagen I significantly decreased the VEGF and MMP-9 protein levels. We found that TSP-1 levels were increased significantly in the gastric cancer cells after application of CAPE. The protein levels of gastric cancer cells also were increased significantly when tissue was cultured on laminin and collagen I. Application of CAPE to cells on laminin or collagen I coated surfaces significantly increased all of the proteins except ES. ES levels were increased on the collagen I covered surfaces, but the laminin surface decreased the levels of ES significantly. We demonstrated the beneficial effect of CAPE on a gastric cancer cell line including inhibition of proliferation and induction of some proteins that might be related to decreased angiogenesis. PMID:26523612

  7. Optimization of polyphenol extraction from red grape pomace using aqueous glycerol/tartaric acid mixtures and response surface methodology.

    PubMed

    Makris, Dimitris P; Passalidi, Vassiliki; Kallithraka, Stamatina; Mourtzinos, Ioannis

    2016-01-01

    Grape pomace is a food industry waste containing a high burden of antioxidant polyphenols and several methodologies have been developed for their efficient extraction. However, a sustainable and environmentally friendly process should involve recovery means composed of benign, non-toxic solvents, such as tartaric acid and glycerol, which are natural food constituents. In this line, this study examined the extraction of polyphenols using aqueous tartaric acid/glycerol solutions. The aim was to assess the role of acid and glycerol concentration in the extraction yield, employing a Box-Behnken experimental design and response surface methodology. The results showed that solutions containing only glycerol (20%, w/v) are more suitable for retrieving polyphenols, flavonoids, and pigments from grape pomace, while tartaric acid exerted a negative effect in this regard, when tested at concentrations up to 2% (w/v). PMID:25806718

  8. Establishment of Hairy Root Cultures of Rhaponticum carthamoides (Willd.) Iljin for the Production of Biomass and Caffeic Acid Derivatives

    PubMed Central

    Skała, Ewa; Kicel, Agnieszka; Olszewska, Monika A.; Kiss, Anna K.

    2015-01-01

    The aim of the study was to obtain transformed roots of Rhaponticum carthamoides and evaluate their phytochemical profile. Hairy roots were induced from leaf explants by the transformation of Agrobacterium rhizogenes strains A4 and ATCC 15834. The best response (43%) was achieved by infection with A4 strain. The effects of different liquid media (WPM, B5, SH) with full and half-strength concentrations of macro- and micronutrients on biomass accumulation of the best grown hairy root line (RC3) at two different lighting conditions (light or dark) were investigated. The highest biomass (93 g L−1 of the fresh weight after 35 days) was obtained in WPM medium under periodic light. UPLC-PDA-ESI-MS3 and HPLC-PDA analyses of 80% aqueous methanol extracts from the obtained hairy roots revealed the presence of eleven caffeoylquinic acids and their derivatives and five flavonoid glycosides. The production of caffeoylquinic acids and their derivatives was elevated in hairy roots grown in the light. Only light-grown hairy roots demonstrated the capability for the biosynthesis of such flavonoid glycosides as quercetagetin, quercetin, luteolin, and patuletin hexosides. Chlorogenic acid, 3,5-di-O-caffeoylquinic acid and a tentatively identified tricaffeoylquinic acid derivative were detected as the major compounds present in the transformed roots. PMID:25811023

  9. Application of Cornelian Cherry Iridoid-Polyphenolic Fraction and Loganic Acid to Reduce Intraocular Pressure

    PubMed Central

    Szumny, Dorota; Sozański, Tomasz; Kucharska, Alicja Z.; Dziewiszek, Wojciech; Piórecki, Narcyz; Magdalan, Jan; Chlebda-Sieragowska, Ewa; Kupczynski, Robert; Szeląg, Adam; Szumny, Antoni

    2015-01-01

    One of the most common diseases of old age in modern societies is glaucoma. It is strongly connected with increased intraocular pressure (IOP) and could permanently damage vision in the affected eye. As there are only a limited number of chemical compounds that can decrease IOP as well as blood flow in eye vessels, the up-to-date investigation of new molecules is important. The chemical composition of the dried Cornelian cherry (Cornus mas L.) polar, iridoid-polyphenol-rich fraction was investigated. Loganic acid (50%) and pelargonidin-3-galactoside (7%) were found as the main components. Among the other constituents, iridoid compound cornuside and the anthocyans cyanidin 3-O-galactoside, cyanidin 3-O-robinobioside, and pelargonidin 3-O-robinobioside were quantified in the fraction. In an animal model (New Zealand rabbits), the influence of loganic acid and the polyphenolic fraction isolated from Cornelian cherry fruit was investigated. We found a strong IOP-hypotensive effect for a 0.7% solution of loganic acid, which could be compared with the widely ophthalmologically used timolol. About a 25% decrease in IOP was observed within the first 3 hours of use. PMID:26124854

  10. Antioxidant-guided isolation and mass spectrometric identification of the major polyphenols in barley (Hordeum vulgare) grain.

    PubMed

    Gangopadhyay, Nirupama; Rai, Dilip K; Brunton, Nigel P; Gallagher, Eimear; Hossain, Mohammad B

    2016-11-01

    In the present study, the relative contribution of individual/classes of polyphenols in barley, to its antioxidant properties, was evaluated. Flash chromatography was used to fractionate the total polyphenol extract of Irish barley cultivar 'Irina', and fractions with highest antioxidant properties were identified using total phenolic content and three in vitro antioxidant assays: DPPH, FRAP, and ORAC. Flavanols (catechin, procyanidin B, prodelphinidin B, procyanidin C) and a novel substituted flavanol (catechin dihexoside, C27H33O16(-), m/z 613.17), were identified as constituents of the fraction with highest antioxidant capacity. Upon identification of phenolics in the other active fractions, the order of most potent contributors to observed antioxidant capacity of barley extract were, flavanols>flavonols (quercetin)>hydroxycinnamic acids (ferulic, caffeic, coumaric acids). The most abundant polyphenol in the overall extract was ferulic acid (277.7μg/gdw barley), followed by procyanidin B (73.7μg/gdw barley). PMID:27211640

  11. Correlations between polyphenolic composition and antioxidant activity of Venetian propolis.

    PubMed

    Gregoris, Elena; Stevanato, Roberto

    2010-01-01

    Four propolis samples have been picked up in the Venetian region, from different orography and habitative density areas with the purpose to: (i) evaluate propolis' antioxidant activity, measured by inhibition of lipid peroxidation; (ii) determine the polyphenolic components--flavonoids and caffeic acid derivatives--which give antioxidant activity to propolis; (iii) verify the potential correlations between antioxidant activity, polyphenolic content, that has been determined by Folin-Ciocalteu, enzymatic, DPPH quenching, TEAC-like assays, and spectroscopic characteristics of propolis and (iv) correlate chemical structure and antioxidant efficacy of each of the major components. The possible localization of the lipophylic components of propolis into the phospholipidic bilayer by thermal analysis (DSC) and spin label EPR techniques has also been investigated. PMID:19766694

  12. The effects of pentoxifylline and caffeic acid phenethyl ester in the treatment of d-galactosamine-induced acute hepatitis in rats.

    PubMed

    Taslidere, E; Vardi, N; Esrefoglu, M; Ates, B; Taskapan, C; Yologlu, S

    2016-04-01

    The aim of this study was to investigate histological changes in hepatic tissue and effects of pentoxifylline (PTX) and caffeic acid phenethyl ester (CAPE) on these changes using histochemical and biochemical methods in rats, in which hepatitis was established by D-galactosamine (D-GAL). Rats were divided into five groups as follows: control group, D-GAL (24 h) group, D-GAL group, d-GAL + PTX group, and D-GAL + CAPE group. In histological evaluations, the control group showed normal appearance of the liver cells. However in the d-GAL groups, focal areas consisting of inflammatory, necrotic, and apoptotic cells were detected in parenchyma. Glycogen loss was observed in the hepatocytes localized at the periphery of lobule. It was found that number of mast cells of portal areas were significantly higher in D-GAL groups compared with other groups (p = 0.0001). In addition, the number of cells with positive staining by Ki-67 and caspase-3 were significantly increased in GAL groups compared with the control group (p = 0.0001). In biochemical analysis, there was an increase in malondialdehyde and myeloperoxidase levels, while a decrease was observed in glutathione level and glutathione peroxidase activity in groups treated with d-GAL compared with the control group. On the other hand, it was seen that, in the groups treated with D-GAL, histological and biochemical injuries in the liver were reduced by administration of PTX and CAPE. In this study, we demonstrated the ameliorative effects of PTX and CAPE on D-GAL-induced liver injury. PMID:25977259

  13. Caffeic acid phenethyl ester enhances TRAIL-mediated apoptosis via CHOP-induced death receptor 5 upregulation in hepatocarcinoma Hep3B cells.

    PubMed

    Dilshara, Matharage Gayani; Jayasooriya, Rajapaksha Gedara Prasad Tharanga; Park, Sang Rul; Choi, Yung-Hyun; Choi, Il-Whan; Kim, Gi-Young

    2016-07-01

    Caffeic acid phenethyl ester (CAPE) exhibits various pharmaceutical properties, including anti-bacterial, anti-inflammatory, anti-viral, anti-cancer, and anti-oxidative activity. Tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) has been a promising anti-cancer agent that preferentially induces cancer cell apoptosis with negligible cytotoxicity toward normal cells. Therefore, the present study investigated whether CAPE promotes TRAIL-mediated cytotoxicity in hepatocarcinoma Hep3B cells. The present study demonstrated that CAPE sensitized TRAIL-mediated cell death in Hep3B carcinoma cells. The percentages of the apoptotic cells and annexin-V(+) cells significantly increased in combined treatment with CAPE and TRAIL (CAPE/TRAIL). Treatment with pancaspase inhibitor, z-VAD-fmk, attenuated CAPE/TRAIL-induced apoptosis, suggesting that the combined treatment triggers caspase-dependent apoptosis. Additionally, we found that CAPE stimulated the expression of death receptor 5 (DR5) and treatment with DR5/Fc chimera protein significantly blocked CAPE/TRAIL-induced apoptosis, which indicates that CAPE/TRAIL stimulated apoptosis through the binding of TRAIL to DR5. Moreover, expression of transcription factor C/EBP homologous protein (CHOP) markedly increased in response to CAPE and transient knockdown of CHOP abolished CAPE/TRAIL-mediated apoptosis. These results suggest that CHOP is a key regulator in CAPE/TRAIL-mediated apoptosis. Taken together, the present study found that CAPE significantly enhanced TRAIL-mediated apoptosis in Hep3B carcinoma cells and suggested that CAPE has promising potential in chemoprevention of hepatocellular carcinomas. PMID:27260301

  14. Effects of Caffeic Acid Phenethyl Ester and 4-Vinylcatechol on the Stabilities of Oil-in-Water Emulsions of Stripped Soybean Oil.

    PubMed

    Jia, Cai-Hua; Shin, Jung-Ah; Lee, Ki-Teak

    2015-12-01

    Caffeic acid phenethyl ester (CAPE) and 4-vinylcatechol (4-VC) were prepared for studying their antioxidative activities in emulsion. Oil-in-water emulsions of stripped soybean oil containing 200 ppm of CAPE, 4-VC, or α-tocopherol were stored at 40 °C in the dark for 50 days, and proton nuclear magnetic resonance ((1)H NMR) was used to identify and quantify the oxidation products. Emulsion droplet sizes, peroxide values, and levels of primary oxidation products (i.e., hydroperoxides) and secondary oxidation products (i.e., aldehydes) were determined. The results showed that CAPE (200 ppm) and 4-VC (200 ppm) had significantly greater antioxidant activities on the oxidation of stripped soybean oil-in-water emulsions than α-tocopherol (200 ppm). The peroxide values of CAPE (8.4 mequiv/L emulsion) and 4-VC (15.0 mequiv/L emulsion) were significantly lower than that of α-tocopherol (33.4 mequiv/L emulsion) (p < 0.05) on 36 days. In addition, the combinations of CAPE + α-tocopherol (100 + 100 ppm) or 4-VC + α-tocopherol (100 + 100 ppm) had better antioxidant activities than α-tocopherol (200 ppm). For CAPE + α-tocopherol, 4-VC + α-tocopherol, and α-tocopherol, the amounts of conjugated diene forms were 16.67, 13.72, and 16.32 mmol/L emulsion, and the concentrations of aldehydes were 2.15, 1.13, and 4.26 mmol/L emulsion, respectively, after 50 days of storage. PMID:26492097

  15. Anti-Neoplastic and Calcium Modulatory Action of Caffeic Acid Phenethyl Ester and Dasatinib in C6 Glial Cells: A Therapeutic Perspective.

    PubMed

    Balkhi, Henah M; Gul, Taseen; Haq, Ehtishamul

    2016-01-01

    Gliomas are often recognized as highly heterogeneous cancerous phenotype. They are perpetually recurrent, obstinately resistant to treatment and hence almost incurable. Drug development studies to date have revealed only modest effect in attenuating growth of these tumors. The present study was aimed at elucidating the potential of targeting glioma through a novel combination of drugs in comparison to single agent. Here, we show that the combined administration of Caffeic acid phenethyl ester [CAPE] and Dasatinib exerts a strong antitumor action on C6 glioma cells. Combinational treatment inhibits proliferation, induces apoptosis, modulates astrocytic phenotype and decreases cell density. Results suggest that combinational therapy inhibits migration and invasiveness, decreases cell survival fraction and hence clonogenic property of C6 cells. The Nitric oxide [NO] levels were significantly reduced by combination treatment at all time points and effect was persistent over the time in comparison to single drug treatment. Atomic Absorption Spectroscopy [AAS] analysis of intracellular and extracellular calcium revealed that the treatment with CAPE and Dasatinib strongly modulates the calcium [Ca(2+)] levels. Herein, we demonstrate that treatment of C6 glioma cells with CAPE and Dasatinib significantly decrease the activity of catalase [CAT]. The results in totality suggest that the combinational therapy remarkably reduces the proliferation of glioma cells possibly through different mechanisms, targeting multiple pathways involved in tumor growth, proliferation and development implicating the relevance of using these drugs in combination therapy for effective treatment of glioma. In vitro results suggest that CAPE and Dasatinib cotreatment could be therapeutically exploited for the management of gliomas. PMID:26553160

  16. Caffeic Acid, a Phenol Found in White Wine, Modulates Endothelial Nitric Oxide Production and Protects from Oxidative Stress-Associated Endothelial Cell Injury

    PubMed Central

    Mannari, Claudio; Bertelli, Alberto A. E.; Medica, Davide; Quercia, Alessandro Domenico; Navarro, Victor; Scatena, Alessia; Giovannini, Luca; Biancone, Luigi; Panichi, Vincenzo

    2015-01-01

    Introduction Several studies demonstrated that endothelium dependent vasodilatation is impaired in cardiovascular and chronic kidney diseases because of oxidant stress-induced nitric oxide availability reduction. The Mediterranean diet, which is characterized by food containing phenols, was correlated with a reduced incidence of cardiovascular diseases and delayed progression toward end stage chronic renal failure. Previous studies demonstrated that both red and white wine exert cardioprotective effects. In particular, wine contains Caffeic acid (CAF), an active component with known antioxidant activities. Aim of the study The aim of the present study was to investigate the protective effect of low doses of CAF on oxidative stress-induced endothelial injury. Results CAF increased basal as well as acetylcholine—induced NO release by a mechanism independent from eNOS expression and phosphorylation. In addition, low doses of CAF (100 nM and 1 μM) increased proliferation and angiogenesis and inhibited leukocyte adhesion and endothelial cell apoptosis induced by hypoxia or by the uremic toxins ADMA, p-cresyl sulfate and indoxyl sulfate. The biological effects exerted by CAF on endothelial cells may be at least in part ascribed to modulation of NO release and by decreased ROS production. In an experimental model of kidney ischemia-reperfusion injury in mice, CAF significantly decreased tubular cell apoptosis, intraluminal cast deposition and leukocyte infiltration. Conclusion The results of the present study suggest that CAF, at very low dosages similar to those observed after moderate white wine consumption, may exert a protective effect on endothelial cell function by modulating NO release independently from eNOS expression and phosphorylation. CAF-induced NO modulation may limit cardiovascular and kidney disease progression associated with oxidative stress-mediated endothelial injury. PMID:25853700

  17. TALEN mediated targeted mutagenesis of the caffeic acid O-methyltransferase in highly polyploid sugarcane improves cell wall composition for production of bioethanol.

    PubMed

    Jung, Je Hyeong; Altpeter, Fredy

    2016-09-01

    Sugarcane (Saccharum spp. hybrids) is a prime crop for commercial biofuel production. Advanced conversion technology utilizes both, sucrose accumulating in sugarcane stems as well as cell wall bound sugars for commercial ethanol production. Reduction of lignin content significantly improves the conversion of lignocellulosic biomass into ethanol. Conventional mutagenesis is not expected to confer reduction in lignin content in sugarcane due to its high polyploidy (x = 10-13) and functional redundancy among homo(eo)logs. Here we deploy transcription activator-like effector nuclease (TALEN) to induce mutations in a highly conserved region of the caffeic acid O-methyltransferase (COMT) of sugarcane. Capillary electrophoresis (CE) was validated by pyrosequencing as reliable and inexpensive high throughput method for identification and quantitative characterization of TALEN mediated mutations. Targeted COMT mutations were identified by CE in up to 74 % of the lines. In different events 8-99 % of the wild type COMT were converted to mutant COMT as revealed by pyrosequencing. Mutation frequencies among mutant lines were positively correlated to lignin reduction. Events with a mutation frequency of 99 % displayed a 29-32 % reduction of the lignin content compared to non-transgenic controls along with significantly reduced S subunit content and elevated hemicellulose content. CE analysis displayed similar peak patterns between primary COMT mutants and their vegetative progenies suggesting that TALEN mediated mutations were faithfully transmitted to vegetative progenies. This is the first report on genome editing in sugarcane. The findings demonstrate that targeted mutagenesis can improve cell wall characteristics for production of lignocellulosic ethanol in crops with highly complex genomes. PMID:27306903

  18. Anti-Apoptotic and Anti-Oxidant Effects of Caffeic Acid Phenethyl Ester on Cadmium-Induced Testicular Toxicity in Rats.

    PubMed

    Erboga, Mustafa; Kanter, Mehmet; Aktas, Cevat; Bozdemir Donmez, Yeliz; Fidanol Erboga, Zeynep; Aktas, Emel; Gurel, Ahmet

    2016-05-01

    Cadmium (Cd) is a serious environmental and occupational contaminant and may represent a serious health hazard to humans and other animals. Cd is reported to induce the generation of reactive oxygen species, and induces testicular damage in many species of animals. The goal of our study was to examine the anti-apoptotic and anti-oxidant effects of caffeic acid phenethyl ester (CAPE) on Cd-induced oxidative stress, apoptosis, and testicular injury in rats. A total of 40 male Wistar albino rats were divided into four groups: control, CAPE alone, Cd-treated, and Cd-treated with CAPE; each group consisted of 10 animals. To induce toxicity, Cd (1 mg/kg body weight) was dissolved in normal saline and subcutaneously injected into rats for 30 days. The rats in CAPE-treated group were given a daily dose of 10 μmol/kg body weight of CAPE by using intraperitoneal injection. This application was continued daily for a total of 30 days. To date, no examinations of the anti-apoptotic and anti-oxidant properties of CAPE on Cd-induced apoptosis, oxidative damage, and testicular injury in rat testes have been reported. CAPE-treated animals showed an improved histological appearance and serum testosterone levels in Cd-treated group. Our data indicate a significant reduction in the number of apoptotic cells in testis tissues of the Cd-treated group with CAPE treatment. Moreover, CAPE significantly suppressed lipid peroxidation, compensated deficits in the anti-oxidant defenses in testes tissue resulted from Cd administration. These findings suggest that the protective potential of CAPE in Cd toxicity might be due to its anti-oxidant and anti-apoptotic properties, which could be useful for achieving optimum effects in Cd-induced testicular injury. PMID:26424218

  19. Fabrication of Novel Bioactive Cellulose-Based Films Derived from Caffeic Acid Phenethyl Ester-Loaded Nanoparticles via a Rapid Expansion Process: RESOLV.

    PubMed

    Saelo, Suparak; Assatarakul, Kitipong; Sane, Amporn; Suppakul, Panuwat

    2016-09-01

    Caffeic acid phenethyl ester (CAPE) nanoparticles (NPs) with an average size of ∼40 nm obtained from TEM and binomial average sizes of ∼90 and ∼400 nm obtained from DLS were successfully produced by rapid expansion of subcritical solutions into liquid solvents (RESOLV). The minimum inhibitory concentrations (MICs) and minimum bactericidal concentrations (MBCs) of CAPE and CAPE-NPs were determined by plate count method against 12 pathogenic and spoilage bacteria and 3 strains of yeast. Total phenolic content (TPC) and antioxidant activities of CAPE-NPs were quantified and subsequently investigated using two assays, including 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging and ferric reducing antioxidant power (FRAP). CAPE-NP-incorporated cellulose-based films were prepared and characterized. MICs and MBCs of CAPE-NPs against most bacteria and Candida albicans were 700 and 1400 μg/mL, respectively. CAPE-NPs yielded a TPC value of 426.74 μgGAE/mg and lower antioxidant activities than those of CAPE in ethanol (CAPE-EtOH), whereas BHT yielded lower FRAP than that of CAPE-NPs. The impregnation of CAPE into cellulose-based films was confirmed by FTIR spectra. Moreover, incorporation of only 0.5 wt % CAPE-NPs into the films resulted in an inhibitory effect against microorganisms. Fortunately, incorporation of higher concentration of CAPE-NPs-MC films led to a significantly higher antioxidant activity and vice versa. This indicated that CAPE-NPs significantly enhanced the antimicrobial and antioxidant activities of CAPE. The results show that the environmentally benign supercritical CO2 technique should be generally applicable to NP fabrication of other important bioactive ingredients, especially in liquid form. In addition, it is suggested that CAPE-NPs can be used to reduce the dosage of CAPE and improve their bioavailability and thus merit further investigation for bioactive packaging film and coating applications. PMID:27548627

  20. Urinary excretions of 34 dietary polyphenols and their associations with lifestyle factors in the EPIC cohort study.

    PubMed

    Zamora-Ros, Raul; Achaintre, David; Rothwell, Joseph A; Rinaldi, Sabina; Assi, Nada; Ferrari, Pietro; Leitzmann, Michael; Boutron-Ruault, Marie-Christine; Fagherazzi, Guy; Auffret, Aurélie; Kühn, Tilman; Katzke, Verena; Boeing, Heiner; Trichopoulou, Antonia; Naska, Androniki; Vasilopoulou, Effie; Palli, Domenico; Grioni, Sara; Mattiello, Amalia; Tumino, Rosario; Ricceri, Fulvio; Slimani, Nadia; Romieu, Isabelle; Scalbert, Augustin

    2016-01-01

    Urinary excretion of 34 dietary polyphenols and their variations according to diet and other lifestyle factors were measured by tandem mass spectrometry in 475 adult participants from the European Prospective Investigation into Cancer and Nutrition (EPIC) cross-sectional study. A single 24-hour urine sample was analysed for each subject from 4 European countries. The highest median levels were observed for phenolic acids such as 4-hydroxyphenylacetic acid (157 μmol/24 h), followed by 3-hydroxyphenylacetic, ferulic, vanillic and homovanillic acids (20-50 μmol/24 h). The lowest concentrations were observed for equol, apigenin and resveratrol (<0.1 μmol/24 h). Urinary polyphenols significantly varied by centre, followed by alcohol intake, sex, educational level, and energy intake. This variability is largely explained by geographical variations in the diet, as suggested by the high correlations (r > 0.5) observed between urinary polyphenols and the intake of their main food sources (e.g., resveratrol and gallic acid ethyl ester with red wine intake; caffeic, protocatechuic and ferulic acids with coffee consumption; and hesperetin and naringenin with citrus fruit intake). The large variations in urinary polyphenols observed are largely determined by food preferences. These polyphenol biomarkers should allow more accurate evaluation of the relationships between polyphenol exposure and the risk of chronic diseases in large epidemiological studies. PMID:27273479

  1. Urinary excretions of 34 dietary polyphenols and their associations with lifestyle factors in the EPIC cohort study

    PubMed Central

    Zamora-Ros, Raul; Achaintre, David; Rothwell, Joseph A.; Rinaldi, Sabina; Assi, Nada; Ferrari, Pietro; Leitzmann, Michael; Boutron-Ruault, Marie-Christine; Fagherazzi, Guy; Auffret, Aurélie; Kühn, Tilman; Katzke, Verena; Boeing, Heiner; Trichopoulou, Antonia; Naska, Androniki; Vasilopoulou, Effie; Palli, Domenico; Grioni, Sara; Mattiello, Amalia; Tumino, Rosario; Ricceri, Fulvio; Slimani, Nadia; Romieu, Isabelle; Scalbert, Augustin

    2016-01-01

    Urinary excretion of 34 dietary polyphenols and their variations according to diet and other lifestyle factors were measured by tandem mass spectrometry in 475 adult participants from the European Prospective Investigation into Cancer and Nutrition (EPIC) cross-sectional study. A single 24-hour urine sample was analysed for each subject from 4 European countries. The highest median levels were observed for phenolic acids such as 4-hydroxyphenylacetic acid (157 μmol/24 h), followed by 3-hydroxyphenylacetic, ferulic, vanillic and homovanillic acids (20–50 μmol/24 h). The lowest concentrations were observed for equol, apigenin and resveratrol (<0.1 μmol/24 h). Urinary polyphenols significantly varied by centre, followed by alcohol intake, sex, educational level, and energy intake. This variability is largely explained by geographical variations in the diet, as suggested by the high correlations (r > 0.5) observed between urinary polyphenols and the intake of their main food sources (e.g., resveratrol and gallic acid ethyl ester with red wine intake; caffeic, protocatechuic and ferulic acids with coffee consumption; and hesperetin and naringenin with citrus fruit intake). The large variations in urinary polyphenols observed are largely determined by food preferences. These polyphenol biomarkers should allow more accurate evaluation of the relationships between polyphenol exposure and the risk of chronic diseases in large epidemiological studies. PMID:27273479

  2. Spectroscopic (FT-IR, FT-Raman, UV absorption, 1H and 13C NMR) and theoretical (in B3LYP/6-311++G** level) studies on alkali metal salts of caffeic acid

    NASA Astrophysics Data System (ADS)

    Świsłocka, Renata

    The effect of some metals on the electronic system of benzoic and nicotinic acids has recently been investigated by IR, Raman and UV spectroscopy [1-3]. Benzoic and nicotinic acids are regarded model systems representing a wide group of aromatic ligands which are incorporated into enzymes. In this work the FT-IR (in solid state and in solution), FT-Raman, UV absorption and 1H and 13C NMR spectra of caffeic acid (3,4-dihydroxycinnamic acid) and its salts with lithium, sodium, potassium, rubidium and caesium were registered, assigned and analyzed. The effect of alkali metals on the electronic system of ligands was discussed. Studies of differences in the number and position of bands from the IR, Raman, UV absorption spectra and chemical shifts from NMR spectra allowed to conclude on the distribution of electronic charge in the molecules, the delocalization energy of π electrons and the reactivity of ligands in metal complexes. Optimized geometrical structures of studied compounds were calculated by B3LYP method using 6-311++G** basis set. Bond lengths, angles and dipole moments for the optimized structures of caffeic acid and lithium, sodium, potassium caffeinates were also calculated. The theoretical wavenumbers and intensities of IR spectra were obtained. The calculated parameters were compared to the experimental characteristics of investigated compounds. Microbial activity of studied compounds was tested against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Proteus vulgaris.

  3. Spectroscopic (FT-IR, FT-Raman, UV absorption, 1H and 13C NMR) and theoretical (in B3LYP/6-311++G** level) studies on alkali metal salts of caffeic acid.

    PubMed

    Świsłocka, Renata

    2013-01-01

    The effect of some metals on the electronic system of benzoic and nicotinic acids has recently been investigated by IR, Raman and UV spectroscopy [1-3]. Benzoic and nicotinic acids are regarded model systems representing a wide group of aromatic ligands which are incorporated into enzymes. In this work the FT-IR (in solid state and in solution), FT-Raman, UV absorption and (1)H and (13)C NMR spectra of caffeic acid (3,4-dihydroxycinnamic acid) and its salts with lithium, sodium, potassium, rubidium and caesium were registered, assigned and analyzed. The effect of alkali metals on the electronic system of ligands was discussed. Studies of differences in the number and position of bands from the IR, Raman, UV absorption spectra and chemical shifts from NMR spectra allowed to conclude on the distribution of electronic charge in the molecules, the delocalization energy of π electrons and the reactivity of ligands in metal complexes. Optimized geometrical structures of studied compounds were calculated by B3LYP method using 6-311++G** basis set. Bond lengths, angles and dipole moments for the optimized structures of caffeic acid and lithium, sodium, potassium caffeinates were also calculated. The theoretical wavenumbers and intensities of IR spectra were obtained. The calculated parameters were compared to the experimental characteristics of investigated compounds. Microbial activity of studied compounds was tested against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Proteus vulgaris. PMID:22369898

  4. Evaluation of antioxidant activity, polyphenolic compounds, amino acids and mineral elements of representative genotypes of Lonicera edulis.

    PubMed

    Sochor, Jiri; Jurikova, Tunde; Pohanka, Miroslav; Skutkova, Helena; Baron, Mojmir; Tomaskova, Lenka; Balla, Stefan; Klejdus, Borivoj; Pokluda, Robert; Mlcek, Jiri; Trojakova, Zuzana; Saloun, Jan

    2014-01-01

    The aim of this study was to evaluate the bioactive substances in 19 berry cultivars of edible honeysuckle (Lonicera edulis). A statistical evaluation was used to determine the relationship between the content of selected bioactive substances and individual cultivars. Regarding mineral elements, the content of sodium was measured using potentiometry and spectrophotometry. The content of selected polyphenolic compounds with high antioxidant activity was determined by a HPLC-UV/ED method. The total amount of polyphenols was determined by the Folin-Ciocalteu method. The antioxidant activity was determined using five methods (DPPH, FRAP, ABTS, FR and DMPD) that differ in their principles. The content of 13 amino acids was determined by ion-exchange chromatography. The experimental results obtained for the different cultivars were evaluated and compared by statistical and bioinformatic methods. A unique feature of this study lies in the exhaustive analysis of the chosen parameters (amino acids, mineral elements, polyphenolic compounds and antioxidant activity) during one growing season. PMID:24853714

  5. HCT2, a Novel Hydroxycinnamoyl-Malate Transferase, is Responsible for Phaselic Acid (2-O-Caffeoyl-L-Malate) Biosynthesis in Red Clover

    Technology Transfer Automated Retrieval System (TEKTRAN)

    In red clover, post-harvest oxidation of o-diphenol caffeic acid derivatives to o-quinones by an endogenous polyphenol oxidase (PPO) prevents breakdown of forage protein during storage (1). Agronomically important forages like alfalfa lack both PPO and o-diphenols. Consequently, breakdown of their p...

  6. Extraction of Honey Polyphenols: Method Development and Evidence of Cis Isomerization

    PubMed Central

    Istasse, Thibaut; Jacquet, Nicolas; Berchem, Thomas; Haubruge, Eric; Nguyen, Bach Kim; Richel, Aurore

    2016-01-01

    Honey polyphenols have been studied with the objective of relating honeys to their floral sources. Initially synthesized by plant, these polyphenols can be found in the plant’s nectar, which are collected by bees, which convert the nectar into honey. Consequently, polyphenols constitute minor components of honey. The development of a solid-phase extraction method for honey polyphenols is presented in this study. The technique employs Amberlite XAD-2 adsorbent and was tested on monofloral honeys from six different plants: acacia, chestnut, eucalyptus, thyme, sunflower, and wild carrot. Analyses were performed using high-performance liquid chromatography coupled with UV detection and mass spectrometry. Several phenolic acids and flavonoids were identified: caffeic and p-coumaric acids, quercetin, kaempferol, naringenin, chrysin, and pinocembrin. Generally, the quantity of a given polyphenol in the honey was around 0.2 mg/100 g of honey, except for chestnut honey, which contained around 3.0 mg of p-coumaric acid/100 g of honey. Analyses highlighted significant formation of cis isomers for phenolic acids during the extraction despite protection from light. PMID:27547032

  7. Extraction of Honey Polyphenols: Method Development and Evidence of Cis Isomerization.

    PubMed

    Istasse, Thibaut; Jacquet, Nicolas; Berchem, Thomas; Haubruge, Eric; Nguyen, Bach Kim; Richel, Aurore

    2016-01-01

    Honey polyphenols have been studied with the objective of relating honeys to their floral sources. Initially synthesized by plant, these polyphenols can be found in the plant's nectar, which are collected by bees, which convert the nectar into honey. Consequently, polyphenols constitute minor components of honey. The development of a solid-phase extraction method for honey polyphenols is presented in this study. The technique employs Amberlite XAD-2 adsorbent and was tested on monofloral honeys from six different plants: acacia, chestnut, eucalyptus, thyme, sunflower, and wild carrot. Analyses were performed using high-performance liquid chromatography coupled with UV detection and mass spectrometry. Several phenolic acids and flavonoids were identified: caffeic and p-coumaric acids, quercetin, kaempferol, naringenin, chrysin, and pinocembrin. Generally, the quantity of a given polyphenol in the honey was around 0.2 mg/100 g of honey, except for chestnut honey, which contained around 3.0 mg of p-coumaric acid/100 g of honey. Analyses highlighted significant formation of cis isomers for phenolic acids during the extraction despite protection from light. PMID:27547032

  8. Polyphenols from artichoke heads (Cynara cardunculus (L.) subsp. scolymus Hayek): in vitro bio-accessibility, intestinal uptake and bioavailability.

    PubMed

    D'Antuono, Isabella; Garbetta, Antonella; Linsalata, Vito; Minervini, Fiorenza; Cardinali, Angela

    2015-04-01

    Artichoke is a rich source of health promoting compounds such as polyphenols, important for their pharmaceutical and nutritional properties. In this study, the potential for bioavailability of the artichoke polyphenols was estimated by using both in vitro digestion and Caco-2 human intestinal cell models. In vitro digestive recoveries (bio-accessibility) were found to be 55.8% for total artichoke phenolics and in particular, 70.0% for chlorogenic acid, 41.3% for 3,5-O-dicaffeoylquinic acid, and 50.3% for 1,5-O-dicaffeoylquinic acid, highlighting potential sensitivity of these compounds to gastric and small intestinal digestive conditions. Uptake of artichoke polyphenols was rapid with peak accumulation occurring after 30 min with an efficiency of 0.16%, according to the poor uptake of dietary polyphenols. Some compounds, such as coumaric acid, caffeic acid and caffeic acid derivatives, were also detected in the basolateral side assuming extra and intracellular esterase activities on chlorogenic acid. Only apigenin-7-O-glucoside was transported through the Caco-2 monolayer demonstrating its bioavailability to the extent of 1.15% at 60 min. In addition, permeability coefficient (Papp = 2.29 × 10(-5) cm s(-1)), involving apical to basolateral transport of apigenin 7-O-glucoside, was calculated to facilitate estimation of transport through the Caco-2 monolayer. Finally, the mono and dicaffeoylquinic acids present in artichoke heads exert an antioxidant activity on the human low density lipoprotein system correlated to their chemical structure. In conclusion, the utilized in vitro models, although not fully responding to the morphological and physiological features of human in vivo conditions, could be a useful tool for investigating mechanistic effects of polyphenols released from the food matrix. PMID:25758164

  9. Chitosan crosslinked microparticles with encapsulated polyphenols: Water sorption and release properties.

    PubMed

    Trifković, Kata; Milašinović, Nikola; Djordjević, Verica; Zdunić, Gordana; Kalagasidis Krušić, Melina; Knežević-Jugović, Zorica; Šavikin, Katarina; Nedović, Viktor; Bugarski, Branko

    2015-11-01

    Chitosan-glutaraldehyde microparticles were produced by emulsion crosslinking method to be used as drug delivery system for polyphenols from Thymus serpyllum L. aqueous extract. The effect of preparation conditions, chitosan concentration (1.5-3% w/v), and glutaraldehyde/chitosan (GA/Ch) mass ratio (0.15-1.20) on water and polyphenols transport properties was investigated. Swelling ratio of dry particles (68-230 µm) in water ranged from 280% to 530%, depending on the formulation. The decrease in swelling was observed with increased GA/Ch mass ratio (i.e. crosslinking degree) at the same chitosan concentration, or with increased chitosan concentration at the same GA/Ch mass ratio. The increase in GA/Ch mass ratio was also manifested by increased particle compactness i.e. decreased size and reduced surface roughness. The sorption capacity for polyphenols seems to be a complex interplay of swelling behaviour and interactions chitosan-glutaraldehyde-polyphenols identified by Fourier transmission infrared analysis. An increase in crystallinity of chitosan was observed upon crosslinking with glutaraldehyde and encapsulation of polyphenols, as observed by X-ray diffraction analysis. The results obtained from release kinetics of selected polyphenolic compounds (caffeic acid, rosmarinic acid, total flavonoids, and total phenol content) showed that polyphenols were released at a lower amount (2-4 times) in water, but more rapidly (45-120 min) in comparison with the release in gastric followed by intestinal simulated fluid (SGF-SIF) (120-240 min). The experimental results of the time-dependent swelling in water and polyphenols release in both, water and SGF-SIF, were analyzed with several mathematical models. The results depicted Fickian diffusion as the water transport mechanism. In the case of polyphenols, only empirical Weibull model could be suggested for describing release kinetics. PMID:26250360

  10. Three-year comparative study of polyphenol contents and antioxidant capacities in fruits of tomato (Lycopersicon esculentum Mill.) cultivars grown under organic and conventional conditions.

    PubMed

    Anton, Dea; Matt, Darja; Pedastsaar, Priit; Bender, Ingrid; Kazimierczak, Renata; Roasto, Mati; Kaart, Tanel; Luik, Anne; Püssa, Tõnu

    2014-06-01

    In the present study, four tomato cultivars were grown under organic and conventional conditions in separate unheated greenhouses in three consecutive years. The objective was to assess the influence of the cultivation system on the content of individual polyphenols, total phenolics, and antioxidant capacity of tomatoes. The fruits were analyzed for total phenolic content by the Folin-Ciocalteau method and antioxidant capacity by the DPPH free radical scavenging assay. Individual phenolic compounds were analyzed using HPLC-DAD-MS/MS. Among 30 identified and quantified polyphenols, significantly higher contents of apigenin acetylhexoside, caffeic acid hexoside I, and phloretin dihexoside were found in all organic samples. The content of polyphenols was more dependent on year and cultivar than on cultivation conditions. Generally, the cultivation system had minor impact on polyphenols content, and only a few compounds were influenced by the mode of cultivation in all tested cultivars during all three years. PMID:24811708

  11. Caffeic acid phenethyl ester stimulates human antioxidant response element-mediated expression of the NAD(P)H:quinone oxidoreductase (NQO1) gene.

    PubMed

    Jaiswal, A K; Venugopal, R; Mucha, J; Carothers, A M; Grunberger, D

    1997-02-01

    Caffeic acid phenethyl ester (CAPE) is a phenolic antioxidant derived from the propolis of honeybee hives. CAPE was shown to inhibit the formation of intracellular hydrogen peroxide and oxidized bases in DNA of 12-O-tetradecanoylphorbol-13-acetate (TPA)-treated HeLa cells and was also found to induce a redox change that correlated with differential growth effects in transformed cells but not the nontumorigenic parental ones. Mediated via the electrophile or human antioxidant response element (hARE), induction of the expression of NAD(P)H quinone oxidoreductase (NQO1) and glutathione S-transferase Ya subunit genes by certain phenolic antioxidants has been correlated with the chemopreventive properties of these agents. Here, we determined by Northern analysis that CAPE treatment of hepatoma cells stimulates NQO1 gene expression in cultured human hepatoma cells (HepG2), and we characterized the effects of CAPE treatment on the expression of a reporter gene either containing or lacking the hARE or carrying a mutant version of this element in rodent hepatoma (Hepa-1) transfectants. A dose-dependent transactivation of human hARE-mediated chloramphenicol acetyltransferase (cat) gene expression was observed upon treatments of the Hepa-1 transfectants with TPA, a known inducer, as well as with CAPE. The combined treatments resulted in an apparent additive stimulation of the reporter expression. To learn whether this activation of cat gene expression was effected by protein kinase C in CAPE-treated cells, a comparison was made of cat gene activity after addition of calphostin, a protein kinase C inhibitor. Calphostin reduced the cat gene induction by TPA but not by CAPE, suggesting that stimulation of gene expression in this system by these agents proceeds via distinct mechanisms. Band-shift experiments to examine binding of transactivator proteins from nuclear extracts of treated and untreated cells to a hARE DNA probe showed that TPA exposure increased the binding level

  12. Bioconversion of grape and chokeberry wine polyphenols during simulated gastrointestinal in vitro digestion.

    PubMed

    Gumienna, Małgorzata; Lasik, Małgorzata; Czarnecki, Zbigniew

    2011-05-01

    The primary objective of the present study was to assess the qualitative and quantitative changes of wine polyphenols during in vitro digestion process conducted in a gastrointestinal tract model. Wines selected for these experiments were red grape, white grape and chokeberry wines. Following the stages of in vitro digestion-stomach, small and large intestine-qualitative and quantitative changes particularly in phenolic acids were monitored. Decomposition of resveratrol and chlorogenic acid, secretion of caffeic acid and formation of other derivatives characterized with high antioxidant activity were determined. As a second focus of this work the evaluation of interactions between human fecal microflora (Enterobacteriaceae, Lactobacillus, Enterococcus and Bifidobacterium) and polyphenolic compounds and their derivatives secreted during the digestion were performed. PMID:21138407

  13. Diphenol activation of the monophenolase and diphenolase activities of field bean (Dolichos lablab) polyphenol oxidase.

    PubMed

    Gowda, Lalitha R; Paul, Beena

    2002-03-13

    This paper reports a study on the hydroxylation of ferulic acid and tyrosine by field bean (Dolichos lablab) polyphenol oxidase, a reaction that does not take place without the addition of catechol. A lag period similar to the characteristic lag of tyrosinase activity was observed, the length of which decreased with increasing catechol concentration and increased with increasing ferulic acid concentration. The activation constant K(a) of catechol for ferulic acid hydroxylation reaction was 5 mM. The kinetic parameters of field bean polyphenol oxidase toward ferulic acid and tyrosine were evaluated in the presence of catechol. 4-Methyl catechol, L-dihydroxyphenylalanine, pyrogallol, and 2,3,4-trihydroxybenzoic acid, substrates with high binding affinity to field bean polyphenol oxidase, could stimulate this hydroxylation reaction. In contrast, diphenols such as protocatechuic acid, gallic acid, chlorogenic acid, and caffeic acid, which were not substrates for the oxidation reaction, were unable to bring about this activation. It is most likely that only o-diphenols that are substrates for the diphenolase serve as cosubstrates by donating electrons at the active site for the monophenolase activity. The reaction mechanism for this activation is consistent with that proposed for tyrosinase (Sanchez-Ferrer, A.; Rodriguez-Lopez, J. N.; Garcia-Canovas, F.; Garcia-Carmona, F. Biochim. Biophys. Acta 1995, 1247, 1-11). The presence of o-diphenols, viz. catechol, L-dihydroxyphenylalanine, and 4-methyl catechol, is also necessary for the oxidation of the diphenols, caffeic acid, and catechin to their quinones by the field bean polyphenol oxidase. This oxidation reaction occurs immediately with no lag period and does not occur without the addition of diphenol. The kinetic parameters for caffeic acid (K(m) = 0.08 mM, V(max) = 32440 u/mg) in the presence of catechol and the activation constant K(a) of catechol (4.6 mM) for this reaction were enumerated. The absence of a lag

  14. Induction of nodD Gene in a Betarhizobium Isolate, Cupriavidus sp. of Mimosa pudica, by Root Nodule Phenolic Acids.

    PubMed

    Mandal, Santi M; Chakraborty, Dipjyoti; Dutta, Suhrid R; Ghosh, Ananta K; Pati, Bikas R; Korpole, Suresh; Paul, Debarati

    2016-06-01

    A range of phenolic acids, viz., p-coumaric acid, 4-hydroxybenzaldehyde, 4-hydroxybenzoic acid, protocatechuic acid, caffeic acid, ferulic acid, and cinnamic acid have been isolated and identified by LC-MS analysis in the roots and root nodules of Mimosa pudica. The effects of identified phenolic acids on the regulation of nodulation (nod) genes have been evaluated in a betarhizobium isolate of M. pudica root nodule. Protocatechuic acid and p-hydroxybenzoic acid were most effective in inducing nod gene, whereas caffeic acid had no significant effect. Phenylalanine ammonia lyase, peroxidase, and polyphenol oxidase activities were estimated, indicating regulation and metabolism of phenolic acids in root nodules. These results showed that nodD gene expression of betarhizobium is regulated by simple phenolic acids such as protocatechuic acid and p-hydroxybenzoic acid present in host root nodule and sustains nodule organogenesis. PMID:26897126

  15. Mediterranean diet and cardioprotection: the role of nitrite, polyunsaturated fatty acids and polyphenols

    PubMed Central

    Nadtochiy, Sergiy M.; Redman, Emily K.

    2010-01-01

    The continually increasing rate of myocardial infarction (MI) in the Western world at least partly can be explained by a poor diet lacking in green vegetables, fruits, and fish, and enriched in food that contains saturated fat. In contrast, a number of epidemiological studies provide strong evidence highlighting the cardioprotective benefits of the Mediterranean diet enriched in green vegetables, fruits, fish and grape wine. Regular consumption of these products leads to an accumulation of nitrate/nitrite/NO•, polyunsaturated fatty acids (PUFA), and polyphenolic compounds, such as resveratrol, in the human body. Studies have confirmed that these constituents are bioactive exogenous mediators, which induce strong protection against MI. The aim of this review is to provide a critical, in-depth analysis of the cardioprotective pathways mediated by nitrite/NO•, PUFA, and phenolic compounds of grape wines discovered in the recent years, including cross-talk between different mechanisms and compounds. Overall, these findings may facilitate the design and synthesis of novel therapeutic tools for the treatment of MI. PMID:21454053

  16. Polyphenol oxidase from yacon roots (Smallanthus sonchifolius).

    PubMed

    Neves, Valdir Augusto; da Silva, Maraiza Aparecida

    2007-03-21

    Polyphenol oxidase (E.C. 1.14.18.1) (PPO) extracted from yacon roots (Smallanthus sonchifolius) was partially purified by ammonium sulfate fractionation and separation on Sephadex G-100. The enzyme had a molecular weight of 45 490+/-3500 Da and Km values of 0.23, 1.14, 1.34, and 5.0 mM for the substrates caffeic acid, chlorogenic acid, 4-methylcatechol, and catechol, respectively. When assayed with resorcinol, DL-DOPA, pyrogallol, protocatechuic, p-coumaric, ferulic, and cinnamic acids, catechin, and quercetin, the PPO showed no activity. The optimum pH varied from 5.0 to 6.6, depending on substrate. PPO activity was inhibited by various phenolic and nonphenolic compounds. p-Coumaric and cinnamic acids showed competitive inhibition, with Ki values of 0.017 and 0.011 mM, respectively, using chlorogenic acid as substrate. Heat inactivation from 60 to 90 degrees C showed the enzyme to be relatively stable at 60-70 degrees C, with progressive inactivation when incubated at 80 and 90 degrees C. The Ea (apparent activation energy) for inactivation was 93.69 kJ mol-1. Sucrose, maltose, glucose, fructose, and trehalose at high concentrations appeared to protect yacon PPO against thermal inactivation at 75 and 80 degrees C. PMID:17316020

  17. Development of an optimized hyaluronic acid-based lipidic nanoemulsion co-encapsulating two polyphenols for nose to brain delivery.

    PubMed

    Nasr, Maha

    2016-05-01

    The development of mucoadhesive lipidic nanoemulsion based on hyaluronic acid, co-encapsulating two polyphenols (resveratrol and curcumin) for the transnasal treatment of neurodegenerative diseases was attempted in the current manuscript. Nanoemulsions were prepared by the spontaneous emulsification method, and were characterized for their particle size, zeta potential, mucoadhesive strength and morphology. The selected formula was tested for its antioxidant potential, in vitro and ex vivo release of the two polyphenols, safety on nasal mucosa and in vivo quantification of the two drugs in rat brains. Its stability was tested by monitoring the change in particle size, zeta potential, drugs' content and antioxidant potential upon storage for 3 months. The optimized hyaluronic acid based nanoemulsion formula displayed a particle size of 115.2 ± 0.15 and a zeta potential of -23.9 ± 1.7. The formula displayed a spherical morphology and significantly higher mucoadhesive strength compared to its non mucoadhesive counterpart. In addition, the nanoemulsion was able to preserve the antioxidant ability of the two polyphenols and protect them from degradation. Diffusion controlled release of the two drugs was achievable till 6 hours, with an ex vivo flux across sheep nasal mucosa of 2.86 and 2.09 µg/cm(2)hr for resveratrol and curcumin, respectively. Moreover, the mucoadhesive nanoemulsion was safe on nasal mucosa and managed to increase the amounts of the two polypehnols in the brain (about 7 and 9 folds increase in AUC0-7 h for resveratrol and curcumin, respectively). Hyaluronic acid based lipidic nanoemulsion proved itself as a successful carrier enhancing the solubility, stability and brain targetability of polyphenols. PMID:26401600

  18. Acid production and conversion of konjac glucomannan during in vitro colonic fermentation affected by exogenous microorganisms and tea polyphenols.

    PubMed

    Zhao, Xin-Huai; Geng, Qian

    2016-05-01

    Impacts of exogenous microorganisms and tea polyphenols on acid production and conversion during in vitro colonic fermentation of konjac glucomannan (KGM) were assessed in this study. Colonic fermentation of KGM by the fecal extract of healthy adults resulted in a propionate-rich profile, as acetic, propionic, butyric and lactic acids production were 16.1, 13.0, 3.3 and 20.2 mmol/L, respectively. Inoculation of one of ten exogenous microorganisms in the fermentative systems increased acetic, propionic and butyric acids production by 50-230%, 9-190% and 110-350%, respectively, and also accelerated lactic acid conversion by 14-40%. Tea polyphenols in the fermentative systems showed clear inhibition on both acid production and conversion; however, this inhibition could be partially or mostly antagonised by the inoculated exogenous microorganisms, resulting in improved acid production and conversion. In total, Lactobacillus brevis and Sterptococcus thermophilus were more able to increase acid production, and the propionate-rich profile was not changed in all cases. PMID:26902110

  19. Heterogeneous photodegradation of methylene blue with iron and tea or coffee polyphenols in aqueous solutions.

    PubMed

    Morikawa, Claudio Kendi; Shinohara, Makoto

    2016-01-01

    Recently, we developed two new Fenton catalysts using iron (Fe) and spent tea leaves or coffee grounds as raw material. In this study, Fe-to-tea or Fe-to-coffee polyphenol complexes were successfully tested as heterogeneous photo-Fenton catalysts. The photodegradation efficiency of methylene blue solutions with Fe-to-polyphenol complexes was higher than that of homogeneous iron salts in the photo-Fenton process. Furthermore, the tested Fe-to-polyphenol complexes could be reused by simply adding H2O2 to the solutions. After three sequential additions of H2O2, the conventional catalysts FeCl2·4H2O and FeCl3 removed only 16.6% and 53.6% of the dye, while the catalysts made using spent coffee grounds and tea leaves removed 94.4% and 96.0% of the dye, respectively. These results showed that the complexes formed between Fe and chlorogenic acid, caffeic acid, gallic acid and catechin, which are the main polyphenols in tea and coffee, can be used to improve the photo-Fenton process. PMID:27120642

  20. Spinach thylakoid polyphenol oxidase isolation, activation, and properties of the native chloroplast enzyme

    SciTech Connect

    Golbeck, J.H.; Cammarata, K.V.

    1981-05-01

    Polyphenol oxidase activity (E.C. 1.14,18.1) has been found in two enzyme species isolated from thylakoid membranes of spinach chloroplasts. The proteins were released from the membrane by sonication and purified >900-fold by ammonium sulfate precipitation, gel filtration, and ion-exchange chromatography. The enzymes appear to be the tetramer and monomer of a subunit with a molecular weight of 42,500 as determined by lithium dodecyl sulfate gel electrophoresis. Sonication releases polyphenol oxidase from the membrane largely in the latent state. In the absence of added fatty acids, the isolated enzyme spontaneously, but slowly, activates with time. Purified polyphenol oxidase utilizes o-diphenols as substrates and shows no detectable levels of monophenol or p-diphenol oxidase activities. Suitable substrates include chlorogenic acid, catechol, caffeic acid, pyrogallol, and dopamine; however, the enzyme is substrate-inhibited by the last four at concentrations near their K/sub m/. A large seasonal variation in polyphenol oxidase activity may result from a decrease in enzyme content rather than inhibition of the enzyme present.

  1. From the X-rays to a reliable “low cost” computational structure of caffeic acid: DFT, MP2, HF and integrated molecular dynamics-X-ray diffraction approach to condensed phases

    NASA Astrophysics Data System (ADS)

    Lombardo, Giuseppe M.; Portalone, Gustavo; Colapietro, Marcello; Rescifina, Antonio; Punzo, Francesco

    2011-05-01

    The ability of caffeic acid to act as antioxidant against hyperoxo-radicals as well as its recently found therapeutic properties in the treatment of hepatocarcinoma, still make this compound, more than 20 years later the refinement of its crystal structure, object of study. It belongs to the vast family of humic substances, which play a key role in the biodegradation processes and easily form complexes with ions widely diffused in the environment. This class of compounds is therefore interesting for potential environmental chemistry applications concerning the possible complexation of heavy metals. Our study focused on the characterization of caffeic acid as a starting necessary step, which will be followed in the future by the application of our findings on the study of the properties of caffeate anion interaction with heavy metal ions. To reach this goal, we applied a low cost approach - in terms of computational time and resources - aimed at the achievement of a high resolution, robust and trustable structure using the X-ray single crystal data, recollected with a higher resolution, as touchstone for a detailed check. A comparison between the calculations carried out with density functional theory (DFT), Hartree-Fock (HF) method and post SCF second order Møller-Plesset perturbation method (MP2), at the 6-31G ** level of the theory, molecular mechanics (MM) and molecular dynamics (MD) was performed. As a consequence we explained on one hand the possible reasons for the pitfalls of the DFT approach and on the other the benefits of using a good and robust force field developed for condensed phases, as AMBER, with MM and MD. The reliability of the latter, highlighted by the overall agreement extended up to the anisotropic displacement parameters calculated by means of MD and the ones gathered by X-ray measurements, makes it very promising for the above-mentioned goals.

  2. Ascorbic Acid Offsets the Inhibitory Effect of Bioactive Dietary Polyphenolic Compounds on Transepithelial Iron Transport in Caco-2 Intestinal Cells12

    PubMed Central

    Kim, Eun-Young; Ham, Soo-Kyung; Bradke, Daniel; Ma, Qianyi; Han, Okhee

    2011-01-01

    We previously reported that (-)-epigallocatechin-3-gallate (EGCG) and grape seed extract (GSE) at high concentration nearly blocked intestinal iron transport across the enterocyte. In this study, we aimed to determine whether small amounts of EGCG, GSE, and green tea extract (GT) are capable of inhibiting iron absorption, to examine if ascorbic acid counteracts the inhibitory action of polyphenols on iron absorption, and to explore the mechanisms of polyphenol-mediated apical iron uptake and basolateral iron release. An55Fe absorption study was conducted by adding various concentrations of EGCG, GSE, and GT using Caco-2 intestinal cells. Polyphenols were found to inhibit the transepithelial 55Fe transport in a dose-dependent manner. The addition of ascorbic acid offset the inhibitory effects of polyphenols on iron transport. Ascorbic acid modulated the transepithelial iron transport without changing the apical iron uptake and the expression of ferroportin-1 protein in the presence of EGCG. The polyphenol-mediated apical iron uptake was inhibited by membrane impermeable Fe2+ chelators (P < 0.001), but at a low temperature (4°C), the apical iron uptake was still higher than the control values at 37°C (P < 0.001). These results suggest that polyphenols enhance the apical iron uptake partially by reducing the conversion of ferric to ferrous ions and possibly by increasing the uptake of polyphenol-iron complexes via the energy-independent pathway. The present results indicate that the inhibitory effects of dietary polyphenols on iron absorption can be offset by ascorbic acid. Further studies are needed to confirm the current findings in vivo. PMID:21430251

  3. Polyphenolic compounds progress during olive mill wastewater sludge and poultry manure co-composting, and humic substances building (Southeastern Tunisia).

    PubMed

    Rigane, Hafedh; Chtourou, Mohamed; Ben Mahmoud, Imen; Medhioub, Khaled; Ammar, Emna

    2015-01-01

    In Mediterranean areas, olive mill wastes pose a major environmental problem owing to their important production and their high polyphenolic compounds and organic acids concentrations. In this work, the evolution of polyphenolic compounds was studied during co-composting of olive mill wastewater sludge and poultry manure, based on qualitative (G-50 sephadex) and quantitative (Folin-Ciocalteu), as well as high pressure liquid chromatography analyses. Results showed a significant polyphenolic content decrease of 99% and a noticeable transformation of low to high molecular weight fraction during the compost maturation period. During this step, polyphenols disappearance suggested their assimilation by thermophilic bacteria as a carbon and energy source, and contributed to humic substances synthesis. Polyphenolic compounds, identified initially by high pressure liquid chromatography, disappeared by composting and only traces of caffeic, coumaric and ferulic acids were detected in the compost. In the soil, the produced compost application improved the chemical and physico-chemical soil properties, mainly fertilising elements such as calcium, magnesium, nitrogen, potassium and phosphorus. Consequently, a higher potato production was harvested in comparison with manure amendment. PMID:25502693

  4. Gastrointestinal absorption and metabolism of apple polyphenols ex vivo by the pig intestinal mucosa in the Ussing chamber.

    PubMed

    Deusser, Hannah; Rogoll, Dorothee; Scheppach, Wolfgang; Volk, Antje; Melcher, Ralph; Richling, Elke

    2013-03-01

    Polyphenols contained in food have various positive effects on human health. The absorption and metabolism of polyphenols in the intestinal tract needs to be studied to estimate these effects. The Ussing chamber technique was used to investigate the transport behavior of apple polyphenols through pig small intestinal mucosa, which served as a model for human gastrointestinal mucosa. The identities and concentrations of polyphenols and their metabolites in the half-chambers (luminal and basolateral) within an incubation period of 4 h were determined by HPLC-MS/MS and HPLC-DAD (DAD = diode-array detection). Flux values were also measured. It was found that 5-caffeoylquinic acid and caffeic acid were absorbed and translocated to the basolateral side (1.9 and 3.7%, respectively), but other compounds, including glycosides of phloretin and quercetin, were observed without translocation. A Ussing chamber utilizing pig small intestinal mucosa is a suitable model for assessing the effect of apple polyphenols on mucosal integrity and nutrition absorption across porcine mucosa. PMID:23229958

  5. Chemical fingerprint and quantitative analysis for quality control of polyphenols extracted from pomegranate peel by HPLC.

    PubMed

    Li, Jianke; He, Xiaoye; Li, Mengying; Zhao, Wei; Liu, Liu; Kong, Xianghong

    2015-06-01

    A simple and efficient HPLC fingerprint method was developed and validated for quality control of the polyphenols extracted from pomegranate peel (PPPs). Ten batches of pomegranate collected from different orchards in Shaanxi Lintong of China were used to establish the fingerprint. For the fingerprint analysis, 15 characteristic peaks were selected to evaluate the similarities of 10 batches of the PPPs. The similarities of the PPPs samples were all more than 0.968, indicating that the samples from different areas of Lintong were consistent. Additionally, simultaneous quantification of eight monophenols (including gallic acid, punicalagin, catechin, chlorogenic acid, caffeic acid, epicatechin, rutin, and ellagic acid) in the PPPs was conducted to interpret the consistency of the quality test. The results demonstrated that the HPLC fingerprint as a characteristic distinguishing method combining similarity evaluation and quantitative analysis can be successfully used to assess the quality and to identify the authenticity of the PPPs. PMID:25624199

  6. Visible Light-Induced Lipid Peroxidation of Unsaturated Fatty Acids in the Retina and the Inhibitory Effects of Blueberry Polyphenols.

    PubMed

    Liu, Yixiang; Zhang, Di; Hu, Jimei; Liu, Guangming; Chen, Jun; Sun, Lechang; Jiang, Zedong; Zhang, Xichun; Chen, Qingchou; Ji, Baoping

    2015-10-28

    The lipid peroxidation of unsaturated fatty acids (UFAs) in the retina not only threatens visual cells but also affects the physiological health of the retina. In this work, the potential damages caused by daily visible light exposure on retinal UFAs were evaluated via a simulated in vitro model. At the same time, the benefits of dietary supplementation of blueberries to the eyes were also assessed. After prolonged light exposure, lipid peroxidation occurred for both docosahexaenoic and arachidonic acids (DHA and AA, respectively). The oxidized UFAs presented obvious cytotoxicity and significantly inhibited cell growth in retinal pigment epithelium cells. Among the different blueberry polyphenol fractions, the flavonoid-rich fraction, in which quercetin was discovered as the main component, was considerably better in preventing visible light-induced DHA lipid peroxidation than the anthocyanin- and phenolic acid-rich fractions. Then the retinal protective activity of blueberry polyphenols against light-induced retinal injury was confirmed in vivo. On the basis of the above results, inhibiting lipid peroxidation of UFAs in the retina is proposed to be another important function mechanism for antioxidants to nourish eyes. PMID:26456696

  7. Rosmarinic Acid, a New Polyphenol from Baccaurea ramiflora Lour. Leaf: A Probable Compound for Its Anti-Inflammatory Activity

    PubMed Central

    Usha, Talambedu; Middha, Sushil Kumar; Bhattacharya, Malay; Lokesh, Prakash; Goyal, Arvind Kumar

    2014-01-01

    Despite several pharmacological applications of Baccaurea ramiflora Lour., studies on the influence of its polyphenol content on pharmacological activity such as anti-inflammatory properties have been scarce. Here we evaluated in vitro antioxidant activity, poyphenolics by HPLC and the anti-inflammatory potential of the methanolic leaf extract of Baccaurea ramiflora (BME) and its protective effects in carrageenan-induced paw edema model of inflammation in rats. The BME extract contained 79.06 ± 0.03 mg gallic acid equivalent (GAE)/g total polyphenols, 28.80 ± 0.01 mg quercetin equivalent (QE)/g flavonoid and 29.42 ± 0.01 μg cathechin equivalent/g proanthocyanidin respectively and rosmarinic acid (8 mg/kg) as a main component was identified by HPLC. Results demonstrate that administration of BME at the dose of 200 mg/kg can reduce paw edema by over 63%, and it exhibits a dose-response effect. Depending on concentration, the extract exerted scavenging activity on DPPH radical (IC50 36.4 μg/mL), significantly inhibited IL-1β (4.4 pg/mg protein) and TNF-α (0.21 ng/μg protein). Therefore, we conclude BME causes a substantial reduction of inflammation in in vivo models. We propose that rosmarinic acid and similar phenolic compounds may be useful in the therapy of inflammation-related injuries. PMID:26785243

  8. trans-Caffeic acid stearyl ester from Paeonia suffruticosa inhibits melanin synthesis by cAMP-mediating down-regulation of α-melanocyte-stimulating hormone-stimulated melanogenesis signaling pathway in B16 cells.

    PubMed

    Liang, Chia-Hua; Chou, Tzung-Han; Tseng, Ya-Ping; Ding, Hsiou-Yu

    2012-01-01

    trans-Caffeic acid stearyl ester (TCASE) from the root cortex of Paeonia suffruticosa ANDREWS is a traditional medicinal herb that has several beneficial properties. However, the inhibitory effect of TCASE on melanogenesis has not been explored. In the cell viability assay, TCASE did not show a cytotoxic effect at a dose of 65 µM for 48 h in B16, HaCaT and Hs68 cells. TCASE considerably inhibits melanin synthesis, and reduces intracellular cyclic adenosine monophosphate (cAMP) levels, tyrosinase activity and L-3-(3,4-dihydroxyphenyl)-alanine (DOPA) oxidase activity in a concentration-dependent manner in the presence of α-melanocyte-stimulating hormone (α-MSH) in B16 cells, and the inhibition efficiency of TCASE exceeds that of ascorbic acid and arbutin. TCASE reduces melanocortin-1 receptor (MC1R), microphthalmia transcription factor (MITF), tyrosinase, tyrosinase-related protein-2 (TRP-2) and TRP-1 mRNA and protein levels in B16 cells. Based on the findings, TCASE is posited to inhibit melanogenesis signaling while suppressing cAMP levels and, subsequently, MC1R, MITF, tyrosinase, TRP-2 and TRP-1 down-regulation, resulting in the suppression of tyrosinase activity, DOPA oxidase activity and melanin synthesis. PMID:23207771

  9. Polyphenol fraction of extra virgin olive oil protects against endothelial dysfunction induced by high glucose and free fatty acids through modulation of nitric oxide and endothelin-1

    PubMed Central

    Storniolo, Carolina Emilia; Roselló-Catafau, Joan; Pintó, Xavier; Mitjavila, María Teresa; Moreno, Juan José

    2014-01-01

    Epidemiological and clinical studies have reported that olive oil reduces the incidence of cardiovascular disease. However, the mechanisms involved in this beneficial effect have not been delineated. The endothelium plays an important role in blood pressure regulation through the release of potent vasodilator and vasoconstrictor agents such as nitric oxide (NO) and endothelin-1 (ET-1), respectively, events that are disrupted in type 2 diabetes. Extra virgin olive oil contains polyphenols, compounds that exert a biological action on endothelial function. This study analyzes the effects of olive oil polyphenols on endothelial dysfunction using an in vitro model that simulates the conditions of type 2 diabetes. Our findings show that high glucose and linoleic and oleic acids decrease endothelial NO synthase phosphorylation, and consequently intracellular NO levels, and increase ET-1 synthesis by ECV304 cells. These effects may be related to the stimulation of reactive oxygen species production in these experimental conditions. Hydroxytyrosol and the polyphenol extract from extra virgin olive oil partially reversed the above events. Moreover, we observed that high glucose and free fatty acids reduced NO and increased ET-1 levels induced by acetylcholine through the modulation of intracellular calcium concentrations and endothelial NO synthase phosphorylation, events also reverted by hydroxytyrosol and polyphenol extract. Thus, our results suggest a protective effect of olive oil polyphenols on endothelial dysfunction induced by hyperglycemia and free fatty acids. PMID:25460732

  10. Black tea polyphenols and polysaccharides improve body composition, increase fecal fatty acid, and regulate fat metabolism in high-fat diet-induced obese rats.

    PubMed

    Wu, Tao; Guo, Yu; Liu, Rui; Wang, Kuan; Zhang, Min

    2016-05-18

    With the current changes in diet and living habits, obesity has become a global health problem. Thus, the weight-reducing function of tea has attracted considerable attention. This study investigated the anti-obesity effect and the mechanism of black tea (BT) polyphenols and polysaccharides in male Sprague-Dawley rats. The BT polyphenols and polysaccharides reduced the body weight, Lee's index, visceral fat weight, and fat cell size but improved the biochemical profile and increased the fecal fatty acid content, thereby preventing high-fat diet-induced obesity. A gene expression profile array was used to screen eight upregulated and five downregulated differentially expressed genes that affect fat metabolic pathways, such as glycerolipid and glycerophospholipid metabolism, fatty acid degradation, glycolysis and gluconeogenesis, bile and pancreatic secretion, the insulin signaling pathway, and steroid hormone secretion. The BT polyphenols and polysaccharides suppressed the formation and accumulation of fat and promoted its decomposition to prevent obesity. PMID:27161951

  11. Blockage of TGFβ-SMAD2 by demethylation-activated miR-148a is involved in caffeic acid-induced inhibition of cancer stem cell-like properties in vitro and in vivo

    PubMed Central

    Li, Yuan; Jiang, Fei; Chen, Lijun; Yang, Ye; Cao, Shuyuan; Ye, Yuting; Wang, Xingxing; Mu, Juan; Li, Zhong; Li, Lei

    2015-01-01

    Current standard practices for treatment of cancers are less than satisfactory because of recurrence mediated by cancer stem cells (CSCs). Caffeic acid (CaA) is a novel anti-tumor agent that inhibits proliferation, migration, and invasion in human cancer cells. However, little is known about the functions of CaA in regulating CSCs-like properties and the potential molecular mechanisms. Here, we found that CaA attenuated the CSCs-like properties by the microRNA-148a (miR-148a)-mediated inhibition of transforming growth factor beta (TGFβ)-SMAD2 signaling pathway both in vitro and in vivo. CaA enhanced the expression of miR-148a by inducing DNA methylation. MiR-148a, which targeted the SMAD2-3′UTR, decreased the expression of SMAD2. Knockdown of miR-148a abolished the CaA-induced inhibition of TGFβ-SMAD2 signal pathway and the CSCs-like properties. Our study found a novel mechanism that CaA inhibits the CSCs-like properties via miR-148a-mediated inhibition of TGFβ-SMAD2 signaling pathway, which may help to identify a new approach for the treatment of human cancers. PMID:26106521

  12. A green ultrasonic-assisted liquid-liquid microextraction based on deep eutectic solvent for the HPLC-UV determination of ferulic, caffeic and cinnamic acid from olive, almond, sesame and cinnamon oil.

    PubMed

    Khezeli, Tahere; Daneshfar, Ali; Sahraei, Reza

    2016-04-01

    A simple, inexpensive and sensitive ultrasonic-assisted liquid-liquid microextraction method based on deep eutectic solvent (UALLME-DES) was used for the extraction of three phenolic acids (ferulic, caffeic and cinnamic) from vegetable oils. In a typical experiment, deep eutectic solvent as green extraction solvent was added to n-hexane (as a typical oil medium) containing target analytes. Subsequently, the extraction was accelerated by sonication. After the extraction, phase separation (DES rich phase/n-hexane phase) was performed by centrifugation. DES rich phase (lower phase) was withdrawn by a micro-syringe and submitted to isocratic reverse-phase HPLC with UV detection. Under optimum conditions obtained by response surface methodology (RSM) and desirability function (DF), the method has good linear calibration ranges (between 1.30 and 1000 µg L(-1)), coefficients of determination (r(2)>0.9949) and low limits of detection (between 0.39 and 0.63 µg L(-1)). This procedure was successfully applied to the determination of target analytes in olive, almond, sesame and cinnamon oil samples. The relative mean recoveries ranged from 94.7% to 104.6%. PMID:26838445

  13. Infrared Spectroscopy as a Tool to Study the Antioxidant Activity of Polyphenolic Compounds in Isolated Rat Enterocytes.

    PubMed

    Barraza-Garza, Guillermo; Castillo-Michel, Hiram; de la Rosa, Laura A; Martinez-Martinez, Alejandro; Pérez-León, Jorge A; Cotte, Marine; Alvarez-Parrilla, Emilio

    2016-01-01

    The protective effect of different polyphenols, catechin (Cat), quercetin (Qc) (flavonoids), gallic acid (GA), caffeic acid (CfA), chlorogenic acid (ChA) (phenolic acids), and capsaicin (Cap), against H2O2-induced oxidative stress was evaluated in rat enterocytes using Attenuated Total Reflectance-Fourier Transform Infrared (ATR-FTIR) Spectroscopy and Fourier Transform Infrared Microspectroscopy (FTIRM), and results were compared to standard lipid peroxidation techniques: conjugated dienes (CD) and Thiobarbituric Acid Reactive Substances (TBARS). Analysis of ATR-FTIR and FTIRM spectral data allowed the simultaneous evaluation of the effects of H2O2 and polyphenols on lipid and protein oxidation. All polyphenols showed a protective effect against H2O2-induced oxidative stress in enterocytes, when administered before or after H2O2. Cat and capsaicin showed the highest protective effect, while phenolic acids had weaker effects and Qc presented a mild prooxidative effect (IR spectral profile of biomolecules between control and H2O2-treated cells) according to FTIR analyses. These results demonstrated the viability to use infrared spectroscopy to evaluate the oxidant and antioxidant effect of molecules in cell systems assays. PMID:27213031

  14. Infrared Spectroscopy as a Tool to Study the Antioxidant Activity of Polyphenolic Compounds in Isolated Rat Enterocytes

    PubMed Central

    Barraza-Garza, Guillermo; Castillo-Michel, Hiram; de la Rosa, Laura A.; Martinez-Martinez, Alejandro; Pérez-León, Jorge A.; Cotte, Marine; Alvarez-Parrilla, Emilio

    2016-01-01

    The protective effect of different polyphenols, catechin (Cat), quercetin (Qc) (flavonoids), gallic acid (GA), caffeic acid (CfA), chlorogenic acid (ChA) (phenolic acids), and capsaicin (Cap), against H2O2-induced oxidative stress was evaluated in rat enterocytes using Attenuated Total Reflectance-Fourier Transform Infrared (ATR-FTIR) Spectroscopy and Fourier Transform Infrared Microspectroscopy (FTIRM), and results were compared to standard lipid peroxidation techniques: conjugated dienes (CD) and Thiobarbituric Acid Reactive Substances (TBARS). Analysis of ATR-FTIR and FTIRM spectral data allowed the simultaneous evaluation of the effects of H2O2 and polyphenols on lipid and protein oxidation. All polyphenols showed a protective effect against H2O2-induced oxidative stress in enterocytes, when administered before or after H2O2. Cat and capsaicin showed the highest protective effect, while phenolic acids had weaker effects and Qc presented a mild prooxidative effect (IR spectral profile of biomolecules between control and H2O2-treated cells) according to FTIR analyses. These results demonstrated the viability to use infrared spectroscopy to evaluate the oxidant and antioxidant effect of molecules in cell systems assays. PMID:27213031

  15. Evaluation of biological value and appraisal of polyphenols and glucosinolates from organic baby-leaf salads as antioxidants and antimicrobials against important human pathogenic bacteria.

    PubMed

    Aires, Alfredo; Marques, Esperança; Carvalho, Rosa; Rosa, Eduardo A S; Saavedra, Maria J

    2013-01-01

    The present investigation has been carried out to investigate the biological role of four different types of baby-leaf salads and to study their potential as natural sources of antioxidants and antimicrobials against several isolates from important human pathogenic bacteria. Four single types of salads (green lettuce, red lettuce, rucola and watercress) and two mixtures [(1) red lettuce+green lettuce; (2) green lettuce + red lettuce + watercress + rucola] were assayed. The HPLC analysis revealed interesting levels of polyphenols and glucosinolates. The results showed a significant variation (p < 0.05) of polyphenols and glucosinolates with plant material. Nine different types of polyphenols grouped in three major classes were found: gallic acid, chlorogenic acid, caffeic acid and dicaffeoyltartaric acid (phenolic acids); quercitin-3-O-rutinoside, quercitin-3-O-rhamnoside, luteolin-7-O-glucoside and isorhamnetin (flavonoids); and cyanidin-3-glucoside (anthocyanins). Only three different glucosinolates were found: glucoraphanin; gluconasturtiin and 4-methoxy-glucobrassicin. A positive correlation was detected between polyphenol contents and antioxidant activity. Red lettuce and mixture 1 were the baby-leaf salads with the highest antioxidant potential. As for the antimicrobial activity, the results showed a selective effect of chemicals against Gram-positive and Gram-negative bacteria and Enterococcus faecalis and Staphylococcus aureus were the bacteria most affected by the phytochemicals. Based on the results achieved baby-leaf salads represent an important source of natural antioxidants and antimicrobial substances. PMID:23603948

  16. NMR-based identification of the phenolic profile of fruits of Lycium barbarum (goji berries). Isolation and structural determination of a novel N-feruloyl tyramine dimer as the most abundant antioxidant polyphenol of goji berries.

    PubMed

    Forino, Martino; Tartaglione, Luciana; Dell'Aversano, Carmela; Ciminiello, Patrizia

    2016-03-01

    Biological properties of fruits of Lycium barbarum (goji berries) have been ascribed to their high content of nutrients and phenolics. Comprehensive studies aimed at unambiguously identifying the phenolic components in goji berries are still lacking. In this paper, we report on the isolation and NMR-based identification of the major phenolics in commercially available goji berries. Together with already known phenolics, including caffeic acid, p-coumaric acid, rutin, scopoletin, N-trans-feruloyl tyramine, and N-cis-feruloyl tyramine, an unreported N-feruloyl tyramine dimer was characterized as the most abundant polyphenol isolated from the berries. Usually divalent molecules show enhanced biological activities than their corresponding monomers. PMID:26471679

  17. Evidences for Chlorogenic Acid — A Major Endogenous Polyphenol Involved in Regulation of Ripening and Senescence of Apple Fruit

    PubMed Central

    Xi, Yu; Cheng, Dai; Zeng, Xiangquan; Cao, Jiankang; Jiang, Weibo

    2016-01-01

    To learn how the endogenous polyphenols may play a role in fruit ripening and senescence, apple pulp discs were used as a model to study the influences of chlorogenic acid (CHA, a major polyphenol in apple pulp) on fruit ripening and senescence. Apple (‘Golden Delicious’) pulp discs prepared from pre-climacteric fruit were treated with 50 mg L-1 CHA and incubated in flasks with 10 mM MES buffer (pH 6.0, 11% sorbitol). Compared to the control samples, treatment with CHA significantly reduced ethylene production and respiration rate, and enhanced levels of firmness and soluble solids content of the pulp discs during incubation at 25°C. These results suggested that CHA could retard senescence of the apple pulp discs. Proteomics analysis with sodium dodecyl sulfate-polyacrylamide gel electrophoresis and mass spectrometry (MALDI-TOF/TOF) revealed that the expressions of several key proteins correlated to fruit ripening and senescence were affected by the treatment with CHA. Further study showed that treating the pulp discs with CHA remarkably reduced levels of lipoxygenase, β-galactosidase, NADP-malic enzyme, and enzymatic activities of lipoxygenase and UDP-glucose pyrophosphorylase, all of which are known as promoters of fruit ripening and senescence. These results could provide new insights into the functions of endogenous phenolic compounds in fruit ripening and senescence. PMID:26756813

  18. Evidences for Chlorogenic Acid--A Major Endogenous Polyphenol Involved in Regulation of Ripening and Senescence of Apple Fruit.

    PubMed

    Xi, Yu; Cheng, Dai; Zeng, Xiangquan; Cao, Jiankang; Jiang, Weibo

    2016-01-01

    To learn how the endogenous polyphenols may play a role in fruit ripening and senescence, apple pulp discs were used as a model to study the influences of chlorogenic acid (CHA, a major polyphenol in apple pulp) on fruit ripening and senescence. Apple ('Golden Delicious') pulp discs prepared from pre-climacteric fruit were treated with 50 mg L(-1) CHA and incubated in flasks with 10 mM MES buffer (pH 6.0, 11% sorbitol). Compared to the control samples, treatment with CHA significantly reduced ethylene production and respiration rate, and enhanced levels of firmness and soluble solids content of the pulp discs during incubation at 25°C. These results suggested that CHA could retard senescence of the apple pulp discs. Proteomics analysis with sodium dodecyl sulfate-polyacrylamide gel electrophoresis and mass spectrometry (MALDI-TOF/TOF) revealed that the expressions of several key proteins correlated to fruit ripening and senescence were affected by the treatment with CHA. Further study showed that treating the pulp discs with CHA remarkably reduced levels of lipoxygenase, β-galactosidase, NADP-malic enzyme, and enzymatic activities of lipoxygenase and UDP-glucose pyrophosphorylase, all of which are known as promoters of fruit ripening and senescence. These results could provide new insights into the functions of endogenous phenolic compounds in fruit ripening and senescence. PMID:26756813

  19. Blueberry polyphenols attenuate kainic acid-induced decrements in cognition and alter inflammatory gene expression in rat hippocampus

    PubMed Central

    Shukitt-Hale, Barbara; Lau, Francis C.; Carey, Amanda N.; Galli, Rachel L.; Spangler, Edward L.; Ingram, Donald K.; Joseph, James A.

    2016-01-01

    Cognitive impairment in age-related neurodegenerative diseases such as Alzheimer's disease may be partly due to long-term exposure and increased susceptibility to inflammatory insults. In the current study, we investigated whether polyphenols in blueberries can reduce the deleterious effects of inflammation induced by central administration of kainic acid by altering the expression of genes associated with inflammation. To this end, 4-month-old male Fischer-344 (F344) rats were fed a control, 0.015% piroxicam (an NSAID) or 2% blueberry diet for 8 weeks before either Ringer's buffer or kainic acid was bilaterally micro-infused into the hippocampus. Two weeks later, following behavioral evaluation, the rats were killed and total RNA from the hippocampus was extracted and used in real-time quantitative RT-PCR (qRT-PCR) to analyze the expression of inflammation-related genes. Kainic acid had deleterious effects on cognitive behavior as kainic acid-injected rats on the control diet exhibited increased latencies to find a hidden platform in the Morris water maze compared to Ringer's buffer-injected rats and utilized non-spatial strategies during probe trials. The blueberry diet, and to a lesser degree the piroxicam diet, was able to improve cognitive performance. Immunohistochemical analyses of OX-6 expression revealed that kainic acid produced an inflammatory response by increasing the OX-6 positive areas in the hippocampus of kainic acid-injected rats. Kainic acid up-regulated the expression of the inflammatory cytokines IL-1β and TNF-α, the neurotrophic factor IGF-1, and the transcription factor NF-κB. Blueberry and piroxicam supplementations were found to attenuate the kainic acid-induced increase in the expression of IL-1β, TNF-α, and NF-κB, while only blueberry was able to augment the increased IGF-1 expression. These results indicate that blueberry polyphenols attenuate learning impairments following neurotoxic insult and exert anti-inflammatory actions

  20. Modeling the survival of Salmonella on slice cooked ham as a function of apple skin polyphenols, acetic acid, oregano essential oil and carvacrol

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Response surface methodology was applied to investigate the combined effect of apple skin polyphenols (ASP), acetic acid (AA), oregano essential oil (O) and carvacrol (C) on the inactivation of Salmonella on sliced cooked ham. A full factorial experimental design was employed with control variables ...

  1. Polyphenols rich fraction from Geoffroea decorticans fruits flour affects key enzymes involved in metabolic syndrome, oxidative stress and inflammatory process.

    PubMed

    Costamagna, M S; Zampini, I C; Alberto, M R; Cuello, S; Torres, S; Pérez, J; Quispe, C; Schmeda-Hirschmann, G; Isla, M I

    2016-01-01

    Geoffroea decorticans (chañar), is widely distributed throughout Northwestern Argentina. Its fruit is consumed as flour, arrope or hydroalcoholic beverage. The chañar fruits flour was obtained and 39 phenolic compounds were tentatively identified by HPLC-MS/MS(n). The compounds comprised caffeic acid glycosides, simple phenolics (protocatechuic acid and vanillic acid), a glycoside of vanillic acid, p-coumaric acid and its phenethyl ester as well as free and glycosylated flavonoids. The polyphenols enriched extract with and without gastroduodenal digestion inhibited enzymes associated with metabolic syndrome, including α-amylase, α-glucosidase, lipase and hydroxyl methyl glutaryl CoA reductase. The polyphenolic extract exhibited antioxidant activity by different mechanisms and inhibited the pro-inflammatory enzymes (ciclooxygenase, lipoxygenase and phospholipase A2). The polyphenolic extract did not showed mutagenic effect by Ames test against Salmonella typhimurium TA98 and TA100 strains. These findings add evidence that chañar fruit flour may be considered a functional food with preventive properties against diseases associated with oxidative stress, inflammatory mediators and metabolic syndrome. PMID:26212988

  2. Bioaccessibility of Ca, Mg, Mn and Cu from whole grain tea-biscuits: Impact of proteins, phytic acid and polyphenols.

    PubMed

    Vitali, D; Vedrina Dragojević, I; Šebečić, B

    2008-09-01

    Levels of some essential minerals (Ca, Mg, Cu and Mn) were determined in ten different types of experimentally prepared hard biscuits. In relation to the wheat flour-based reference sample, other investigated samples were enriched with different ratios of integral raw materials of different origin or various dietary fibers in view of improving their functionality and nutritive quality. The goal of the research was to evaluate enriched biscuits as additional sources of calcium, magnesium, copper and manganese in nutrition and to investigate if the modifications of wheat flour based biscuit composition significantly change the amounts of total and bioaccessible minerals in the final product. Since our results indicated significant changes of mineral bioaccessibility among the samples, obtained results were correlated to the content of proteins, phytic acid and polyphenols for the sake of assessing their impact as limiting factors of mineral bioaccessibility in these types of foods. PMID:26050166

  3. Role of intestinal microbiota in the generation of polyphenol derived phenolic acid mediated attenuation of Alzheimer’s disease β-amyloid oligomerization

    PubMed Central

    Wang, Dongjie; Ho, Lap; Faith, Jeremiah; Ono, Kenjiro; Janle, Elsa M.; Lachcik, Pamela J.; Cooper, Bruce R.; Jannasch, Amber H.; D’Arcy, Bruce R.; Williams, Barbara A.; Ferruzzi, Mario G.; Levine, Samara; Zhao, Wei; Dubner, Lauren; Pasinetti, Giulio M.

    2015-01-01

    Scope Grape seed polyphenol extract (GSPE) is receiving increasing attention for its potential preventative and therapeutic roles in Alzheimer’s disease (AD) and other age-related neurodegenerative disorders. The intestinal microbiota is known to actively convert many dietary polyphenols, including GSPE, to phenolic acids. There is limited information on the bioavailability and bioactivity of GSPE-derived phenolic acid in the brain. Methods and Results We orally administered GSPE to rats and investigated the bioavailability of 12 phenolic acids known to be generated by microbiota metabolism of anthocyanidins. GSPE treatment significantly increased the content of 2 of the phenolic acids in the brain: 3-hydroxybenzoic acid (3-HBA) and 3-(3′-hydroxyphenyl) propionic acid (3-HPP), resulting in the brain accumulations of the two phenolic acids at μM concentrations. We also provided evidence that 3-HBA and 3-HPP potently interfere with the assembly of β-amyloid (Aβ) peptides into neurotoxic Aβ aggregates that play key roles in AD pathogenesis. Conclusion Our observation suggests important contribution of the intestinal microbiota to the protective activities of GSPE (as well as other polyphenol preparations) in AD. Outcomes from our studies support future preclinical and clinical investigations exploring the potential contributions of the intestinal microbiota in protecting against the onset/progression of AD and other neurodegenerative conditions. PMID:25689033

  4. Both caffeoyl Coenzyme A 3-O-methyltransferase 1 and caffeic acid O-methyltransferase 1 are involved in redundant functions for lignin, flavonoids and sinapoyl malate biosynthesis in Arabidopsis.

    PubMed

    Do, Cao-Trung; Pollet, Brigitte; Thévenin, Johanne; Sibout, Richard; Denoue, Dominique; Barrière, Yves; Lapierre, Catherine; Jouanin, Lise

    2007-10-01

    Two methylation steps are necessary for the biosynthesis of monolignols, the lignin precursors. Caffeic acid O-methyltransferase (COMT) O-methylates at the C5 position of the phenolic ring. COMT is responsible for the biosynthesis of sinapyl alcohol, the precursor of syringyl lignin units. The O-methylation at the C3 position of the phenolic ring involves the Caffeoyl CoA 3-O-methyltransferase (CCoAOMT). The CCoAOMT 1 gene (At4g34050) is believed to encode the enzyme responsible for the first O-methylation in Arabidopsis thaliana. A CCoAOMT1 promoter-GUS fusion and immunolocalization experiments revealed that this gene is strongly and exclusively expressed in the vascular tissues of stems and roots. An Arabidopsis T-DNA null mutant named ccomt 1 was identified and characterised. The mutant stems are slightly smaller than wild-type stems in short-day growth conditions and has collapsed xylem elements. The lignin content of the stem is low and the S/G ratio is high mainly due to fewer G units. These results suggest that this O-methyltransferase is involved in G-unit biosynthesis but does not act alone to perform this step in monolignol biosynthesis. To determine which O-methyltransferase assists CCoAOMT 1, a comt 1 ccomt1 double mutant was generated and studied. The development of comt 1 ccomt1 is arrested at the plantlet stage in our growth conditions. Lignins of these plantlets are mainly composed of p-hydroxyphenyl units. Moreover, the double mutant does not synthesize sinapoyl malate, a soluble phenolic. These results suggest that CCoAOMT 1 and COMT 1 act together to methylate the C3 position of the phenolic ring of monolignols in Arabidopsis. In addition, they are both involved in the formation of sinapoyl malate and isorhamnetin. PMID:17594112

  5. CD133⁺ melanoma subpopulation acquired resistance to caffeic acid phenethyl ester-induced apoptosis is attributed to the elevated expression of ABCB5: significance for melanoma treatment.

    PubMed

    El-Khattouti, Abdelouahid; Sheehan, Natale T; Monico, Jesus; Drummond, Heather A; Haikel, Youssef; Brodell, Robert T; Megahed, Mosaad; Hassan, Mohamed

    2015-02-01

    According to the cancer stem-like cell (CSC) hypothesis, neoplastic clones are maintained by a small fraction of cells with stem cell properties. Also, melanoma resistance to chemo- and radiotherapy is thought to be attributed to melanoma stem-like cells (MSCs). Caffeic acid phenethyl ester (CAPE) is a bioactive molecule, whose antitumor activity is approved in different tumor types. CAPE induced both apoptosis and E2F1 expression in CD133(-), but not in CD133(+) melanoma subpopulations. The resistance of CD133(+) melanoma subpopulation is attributed to the enhanced drug efflux mediated by ATP-binding cassette sub-family B member 5 (ABCB5), since the knockdown of ABCB5 was found to sensitize CD133(+) cells to CAPE. CAPE-induced apoptosis is mediated by E2F1 as evidenced by the abrogation of apoptosis induced in response to the knockdown of E2F1. The functional analysis of E2F1 in CD133(+) melanoma subpopulation demonstrated the ability of E2F1 gene transfer to trigger apoptosis of CD133(+) cells and to enhance the activation of apoptosis signal-regulating kinase (ASK1), c-Jun N-terminal kinase and p38, and the DNA-binding activities of the transcription factors AP-1 and p53. Also, the induction of E2F1 expression was found to enhance the expression of the pro-apoptotic proteins Bax, Noxa and Puma, and to suppress the anti-apoptotic protein Mcl-1. Using specific pharmacological inhibitors we could demonstrate that E2F1 overcomes the chemo-resistance of MSCs/CD133(+) cells by a mechanism mediated by both mitochondrial dysregulation and ER-stress-dependent pathways. In conclusion, our data addresses the mechanisms of CAPE/E2F1-induced apoptosis of chemo-resistant CD133(+) melanoma subpopulation. PMID:25449786

  6. Caffeic acid phenethyl ester reduces the secretion of vascular endothelial growth factor through the inhibition of the ROS, PI3K and HIF-1α signaling pathways in human retinal pigment epithelial cells under hypoxic conditions.

    PubMed

    Paeng, Sung Hwa; Jung, Won-Kyo; Park, Won Sun; Lee, Dae-Sung; Kim, Gi-Young; Choi, Yung Hyun; Seo, Su-Kil; Jang, Won Hee; Choi, Jung Sik; Lee, Young-Min; Park, Saegwang; Choi, Il-Whan

    2015-05-01

    Choroidal neovascularization (CNV) can lead to progressive and severe visual loss. Vascular endothelial growth factor (VEGF) promotes the development of CNV. Caffeic acid phenethyl ester (CAPE), a biologically active component of the honeybee (Apis mellifera) propolis, has been demonstrated to have several interesting biological regulatory properties. The objective of this study was to determine whether treatment with CAPE results in the inhibition of the production of vascular endothelial growth factor (VEGF) in retinal pigment epithelial cells (RPE cells) under hypoxic conditions and to explore the possible underlying mechanisms. An in vitro experimental model of hypoxia was used to mimic an ischemic microenvironment for the RPE cells. Human RPE cells (ARPE-19) were exposed to hypoxia with or without CAPE pre-treatment. ARPE-19 cells were used to investigate the pathway involved in the regulation of VEGF production under hypoxic conditions, based on western blot analysis, enzyme-linked immunosorbent assay (ELISA) and electrophoretic mobility shift assay (EMSA). The amount of VEGF released from the hypoxia-exposed cells was significantly higher than that of the normoxic controls. Pre-treatment with CAPE suppressed the hypoxia-induced production of VEGF in the ARPE-19 cells, and this effect was inhibited through the attenuation of reactive oxygen species (ROS) production, and the inhibition of phosphoinositide 3-kinase (PI3K)/AKT and hypoxia-inducible factor-1α (HIF-1α) expression. These in vitro findings suggest that CAPE may prove to be a novel anti-angiogenic agent for the treatment of diseases associated with CNV. PMID:25738890

  7. Caffeic acid phenethyl ester induced cell cycle arrest and growth inhibition in androgen-independent prostate cancer cells via regulation of Skp2, p53, p21Cip1 and p27Kip1

    PubMed Central

    Su, Liang-Cheng; Jiang, Shih Sheng; Chan, Tzu-Min; Chang, Chung-Ho; Chen, Li-Tzong; Kung, Hsing-Jien; Wang, Horng-Dar; Chuu, Chih-Pin

    2015-01-01

    Prostate cancer (PCa) patients receiving the androgen ablation therapy ultimately develop recurrent castration-resistant prostate cancer (CRPC) within 1–3 years. Treatment with caffeic acid phenethyl ester (CAPE) suppressed cell survival and proliferation via induction of G1 or G2/M cell cycle arrest in LNCaP 104-R1, DU-145, 22Rv1, and C4–2 CRPC cells. CAPE treatment also inhibited soft agar colony formation and retarded nude mice xenograft growth of LNCaP 104-R1 cells. We identified that CAPE treatment significantly reduced protein abundance of Skp2, Cdk2, Cdk4, Cdk7, Rb, phospho-Rb S807/811, cyclin A, cyclin D1, cyclin H, E2F1, c-Myc, SGK, phospho-p70S6kinase T421/S424, phospho-mTOR Ser2481, phospho-GSK3α Ser21, but induced p21Cip1, p27Kip1, ATF4, cyclin E, p53, TRIB3, phospho-p53 (Ser6, Ser33, Ser46, Ser392), phospho-p38 MAPK Thr180/Tyr182, Chk1, Chk2, phospho-ATM S1981, phospho-ATR S428, and phospho-p90RSK Ser380. CAPE treatment decreased Skp2 and Akt1 protein expression in LNCaP 104-R1 tumors as compared to control group. Overexpression of Skp2, or siRNA knockdown of p21Cip1, p27Kip1, or p53 blocked suppressive effect of CAPE treatment. Co-treatment of CAPE with PI3K inhibitor LY294002 or Bcl-2 inhibitor ABT737 showed synergistic suppressive effects. Our finding suggested that CAPE treatment induced cell cycle arrest and growth inhibition in CRPC cells via regulation of Skp2, p53, p21Cip1, and p27Kip1. PMID:25788262

  8. Bioavailability of lemon verbena (Aloysia triphylla) polyphenols in rats: impact of colonic inflammation.

    PubMed

    Felgines, Catherine; Fraisse, Didier; Besson, Catherine; Vasson, Marie-Paule; Texier, Odile

    2014-05-28

    Lemon verbena (Aloysia triphylla) infusion, a widely consumed herbal tea, contains significant amounts of polyphenols such as flavone diglucuronides and phenylpropanoid glycosides (mainly verbascoside). We have recently shown that lemon verbena infusion offers beneficial effects against dextran sodium sulphate (DSS)-induced colonic inflammation in rats. The present study aimed to evaluate the bioavailability and intestinal absorption of polyphenols derived from lemon verbena infusion in both healthy and colitic rats. For this purpose, lemon verbena infusion was given to rats ad libitum for 14 d, and then 4 % DSS was added to the infusion for 7 d. Before and after DSS administration, 24 h urinary excretion of polyphenols was determined. Flavones were excreted in the urine as conjugated aglycones, and their excretion was not significantly altered by colonic inflammation. Only trace amounts of verbascoside were excreted in the urine, but various metabolites (hydroxycinnamic acids) were detected. The urinary excretion of hydroxycinnamic acids, particularly that of caffeic acid, increased after DSS administration (P< 0·05). Only flavone aglycones (luteolin and diosmetin) were excreted in the faeces in small proportions (3·2 % of ingested flavones). Intestinal absorption of lemon verbena polyphenols was examined using an in situ intestinal perfusion model. Intestinal absorption of verbascoside and flavone diglucuronides did not significantly differ between the healthy and colitic rats. Collectively, these results show that intestinal absorption and urinary excretion of lemon verbena flavone diglucuronides were not altered by colonic inflammation, but that urinary excretion of hydroxycinnamic acids derived from verbascoside was affected in a colitic situation. PMID:24513110

  9. Effects of certain polyphenols and extracts on furans and acrylamide formation in model system, and total furans during storage.

    PubMed

    Oral, Rasim Alper; Dogan, Mahmut; Sarioglu, Kemal

    2014-01-01

    Using a glucose-glycine and asparagine-fructose system as a Maillard reaction model, the effects of seven polyphenols and solid phase extracts of three plants on the formation of furans and acrylamide were investigated. The polyphenols and extracts were used in biscuit formulation and acrylamide formation was observed. They were used for the storage of the glycine-glucose model system at three different temperatures. The addition of some of the extracts and polyphenols significantly decreased furan formation to different extents. All phenolic compounds and plant extracts decreased in the range of 30.8-85% in the model system except for oleuropein, and all of them decreased in the range of 10.3-19.2% in biscuit. Total furan formation was inhibited by caffeic acid, punicalagin, epicatechin, ECE and PPE during storage. This study evaluated and found the inhibitory effect on the formation of furans and acrylamide in Maillard reactions by the use of some plant extracts and polyphenols. PMID:24001861

  10. Development of a rapid method based on solid-phase extraction and liquid chromatography with ultraviolet absorbance detection for the determination of polyphenols in alcohol-free beers.

    PubMed

    García, A Alonso; Grande, B Cancho; Gándara, J Simal

    2004-10-29

    An analytical method based on solid-phase extraction (SPE) and followed by liquid chromatographic separation and ultraviolet detection (HPLC-UV) is proposed for the determination of 10 phenolic compounds which participate on beer stability and sensory properties in alcohol-free beers. Acetonitrile was found to be the most appropriate solvent for the elution of polyphenolic compounds adsorbed on C18 cartridges. The performance of the method was assessed by the evaluation of parameters such as absolute recovery (generally higher than 60%), repeatability (lower than 10%), linearity (r2 higher than 0.993) and limits of quantitation (ranging from 1 to 37 microg/L); no matrix effects were observed. The polyphenol content of different Spanish alcohol-free beers is presented. Five phenolic compounds such as protocatechuic, p-coumaric, ferulic, caffeic acids, and (+)-catechin were identified at levels lower than 10 mg/L. PMID:15553142

  11. Vascular effects of the Mediterranean diet-part II: role of omega-3 fatty acids and olive oil polyphenols.

    PubMed

    Scoditti, Egeria; Capurso, Cristiano; Capurso, Antonio; Massaro, Marika

    2014-12-01

    The lower occurrence of cardiovascular disease and cancer in populations around the Mediterranean basin as detected in the 1950s was correctly attributed to the peculiar dietary habits of those populations. Essentially, until the mid-20th century, typical Mediterranean diets were rich in fruits, vegetables, legumes, whole-wheat bread, nuts, fish, and, as a common culinary trait, the routine use of extra-virgin olive oil. Nowadays, the regular adoption of such dietary patterns is still thought to result in healthful benefits. Such patterns ensure the assumption of molecules with antioxidant and anti-inflammatory actions, among which ω-3 polyunsaturated fatty acids (PUFAs), ω-9 monounsaturated fatty acids (oleic acid), and phenolic compounds. The aim of this review is to provide an update of the vasculo-protective pathways mediated by ω-3 PUFAs and polyphenols in the context of the modern Mediterranean dietary habits, including the possible cross-talk and synergy between these typical components. This review complements a parallel one focusing on the role of dietary nitrates and alimentary fats. PMID:25446163

  12. Protective effects of Ocimum gratissimum polyphenol extract on carbon tetrachloride-induced liver fibrosis in rats.

    PubMed

    Chen, Yieng-How; Chiu, Yung-Wei; Shyu, Jyh-Cherng; Tsai, Chin-Chiu; Lee, Hsueh-Hui; Hung, Chuan-Chen; Hwang, Jin-Ming; Liu, Jer-Yuh; Wang, Wen-Hong

    2015-02-28

    Ocimum gratissimum found in tropical regions is a traditional herb commonly which prevents free radical damage and protects liver from oxidative stress and fibrosis. Ocimum gratissimum polyphenol extract (OGPE) was purified by resin tube to 33.24% polyphenol and 8.2% flavonoid, which were three-fold higher compared with the pre-purification concentrations. The abstract was used to determine if the antioxidant components in the O. gratissimum extract (OGE) were responsible for protective effects on liver fibrosis. High-performance liquid chromatography analysis revealed that the content levels of catechin, caffeic acid and epicatechin in OGPE also increased three-fold. Male Wistar rats were administered with carbon tetrachloride (CCl₄) and varying amounts of OGPE doses [0-12 mg/kg body weight (BW)] or OGE dose (40 mg/kg BW) for 8 weeks. Results showed that OGPE at 12 mg/kg BW, similar to OGE at 40 mg/kg BW, maintained the liver weight, significantly ameliorated CCl₄-induced steatosis, and mitigated other pathological changes. OGPE (12 mg/kg BW) also maintained the levels of serum alanine aminotransferase and aspartate aminotransferase, as well as the levels of malondialdehyde, catalase and α-smooth muscle actin in liver tissues from CCl₄-induced changes. These findings suggest that antioxidant components in OGPE were the major factors that prevented liver fibrosis. Moreover, higher polyphenol concentrations were necessary for higher effectiveness. PMID:25687492

  13. A comprehensive characterisation of beer polyphenols by high resolution mass spectrometry (LC-ESI-LTQ-Orbitrap-MS).

    PubMed

    Quifer-Rada, Paola; Vallverdú-Queralt, Anna; Martínez-Huélamo, Miriam; Chiva-Blanch, Gemma; Jáuregui, Olga; Estruch, Ramon; Lamuela-Raventós, Rosa

    2015-02-15

    Beer is the second most consumed alcoholic beverage in Europe and shown by the European Prospective Investigation into Cancer and Nutrition cohort study to be the main food contributor to hydroxybenzoic acid intake. About 70-80% of the total polyphenol content in beer comes from malt, and the remaining 30-20% from hops. In this work, liquid chromatography coupled with an electrospray ionization hybrid linear ion trap quadrupole Orbitrap mass spectrometry technique has been used for an accurate identification of beer polyphenols. 47 phenolic compounds were identified using high mass accuracy and confirmed by MS(2) experiments, including simple phenolic acids, hydroxycinnamoylquinics, flavanols, flavonols, flavones, alkylmethoxyphenols, alpha- and iso-alpha-acids, hydroxyphenylacetic acids and prenylflavonoids. As far as we know, 7 of these compounds have been recognised in beer for the first time: feruloylquinic acid, caffeic acid-O-hexoside, coumaric acid-O-hexoside, sinapic acid-O-hexoside, catechin-O-dihexoside, kaempferol-O-hexoside, and apigenin-C-hexoside-pentoside. PMID:25236235

  14. CHARACTERISTICS OF POLYPHENOL OXIDASES

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Polyphenol oxidase (PPO, EC 1.14.18.1 or EC 1.10.3.1) catalyzes the oxidation of o-diphenols to o-quinones. Highly reactive o-quinones couple with phenolics and specific amino acids on proteins to form the characteristic browning products in many wounded fruits, vegetables, and leaf tissues of plant...

  15. The conformational state of polyphenol oxidase from field bean (Dolichos lablab) upon SDS and acid-pH activation.

    PubMed

    Kanade, Santosh R; Paul, Beena; Rao, A G Appu; Gowda, Lalitha R

    2006-05-01

    Field bean (Dolichos lablab) contains a single isoform of PPO (polyphenol oxidase)--a type III copper protein that catalyses the o-hydroxylation of monophenols and oxidation of o-diphenols using molecular oxygen--and is a homotetramer with a molecular mass of 120 kDa. The enzyme is activated manyfold either in the presence of the anionic detergent SDS below its critical micellar concentration or on exposure to acid-pH. The enhancement of kcat upon activation is accompanied by a marked shift in the pH optimum for the oxidation of t-butyl catechol from 4.5 to 6.0, an increased sensitivity to tropolone, altered susceptibility to proteolytic degradation and decreased thermostability. The Stokes radius of the native enzyme is found to increase from 49.1+/-2 to 75.9+/-0.6 A (1 A=0.1 nm). The activation by SDS and acid-pH results in a localized conformational change that is anchored around the catalytic site of PPO that alters the microenvironment of an essential glutamic residue. Chemical modification of field bean and sweet potato PPO with 1-ethyl-3-(3-dimethylaminopropyl)carbodi-imide followed by kinetic analysis leads to the conclusion that both the enzymes possess a core carboxylate essential to activity. This enhanced catalytic efficiency of PPO, considered as an inducible defence oxidative enzyme, is vital to the physiological defence strategy adapted by plants to insect herbivory and pathogen attack. PMID:16393141

  16. Polyphenol oxidases in Physcomitrella: functional PPO1 knockout modulates cytokinin-dependent developmentin the moss Physcomitrella patens

    PubMed Central

    von Schwartzenberg, Klaus

    2012-01-01

    Polyphenol oxidases (PPOs) are copper-binding enzymes of the plant secondary metabolism that oxidize polyphenols to quinones. Although PPOs are nearly ubiquitous in seed plants, knowledge on their evolution and function in other plant groups is missing. This study reports on the PPO gene family in the moss Physcomitrella patens (Hedw.) B.S.G. asan example for an early divergent plant. The P. patens PPO multigene family comprises 13 paralogues. Phylogenetic analyses suggest that plant PPOs evolved with the colonization of land and that PPO duplications within the monophyletic P. patens paralogue clade occurred after the separation of the moss and seed plant lineages. PPO functionality was demonstrated for recombinant PPO6. P. patens was analysed for phenolic compounds and six substances were detected intracellularly by LC-MS analysis: 4-hydroxybenzoic acid, p-cumaric acid, protocatechuic acid, salicylic acid, caffeic acid, and an ester of caffeic acid. Targeted PPO1 knockout (d|ppo1) plants were generated and plants lacking PPO1 exhibited only ~30% of the wild-type PPO activity in the culture medium, thus suggesting extracellular localization of PPO1, which is in contrast to the mostly plastidic PPO localization in seed plants. Further, d|ppo1 lines formed significantly more gametophores with a reduced areal plant size, which could be related to an increase of endogenously produced cytokinins and indicates an impact of PPO1 on plant development. d|ppo1 plants were less tolerant towards applied 4-methylcatechol compared to the wild type, which suggests a role of extracellular PPO1 in establishing appropriate conditions by the removal of inhibitory extracellular phenolic compounds. PMID:22865913

  17. No difference in fecal levels of bacteria or short chain fatty acids in humans, when consuming fruit juice beverages containing fruit fiber, fruit polyphenols, and their combination.

    PubMed

    Wallace, Alison J; Eady, Sarah L; Hunter, Denise C; Skinner, Margot A; Huffman, Lee; Ansell, Juliet; Blatchford, Paul; Wohlers, Mark; Herath, Thanuja D; Hedderley, Duncan; Rosendale, Douglas; Stoklosinski, Halina; McGhie, Tony; Sun-Waterhouse, Dongxiao; Redman, Claire

    2015-01-01

    This study examined the effect of a Boysenberry beverage (750 mg polyphenols), an apple fiber beverage (7.5 g dietary fiber), and a Boysenberry plus apple fiber beverage (750 mg polyphenols plus 7.5 g dietary fiber) on gut health. Twenty-five individuals completed the study. The study was a placebo-controlled crossover study, where every individual consumed 1 of the 4 treatments in turn. Each treatment phase was 4-week long and was followed by a 2-week washout period. The trial beverages were 350 g taken in 2 doses every day (ie, 175 mL taken twice daily). The hypothesis for the study was that the combination of polyphenols and fiber would have a greater benefit on gut health than the placebo product or the fiber or polyphenols on their own. There were no differences in fecal levels of total bacteria, Bacteroides-Prevotella-Porphyromonas group, Bifidobacteriumspecies, Clostridium perfringens, or Lactobacillus species among any of the treatment groups. Fecal short chain fatty acid concentrations did not vary among treatment groups, although prostaglandin E2 concentrations were higher after consumption of the Boysenberry juice beverage. No significant differences were found in quantitative measures of gut health between the Boysenberry juice beverage, the apple fiber beverage, the Boysenberry juice plus apple fiber beverage, and the placebo beverage. PMID:25530011

  18. Mid-infrared spectral characteristics of lipid molecular structures in Brassica carinata seeds: relationship to oil content, fatty acid and glucosinolate profiles, polyphenols, and condensed tannins.

    PubMed

    Xin, Hangshu; Khan, Nazir A; Falk, Kevin C; Yu, Peiqiang

    2014-08-13

    The objectives of this study were to quantify lipid-related inherent molecular structures using a Fourier transform infrared spectroscopy (FT-IR) technique and determine their relationship to oil content, fatty acid and glucosinolate profile, total polyphenols, and condensed tannins in seeds from newly developed yellow-seeded and brown-seeded Brassica carinata lines. Canola seeds were used as a reference. The lipid-related molecular spectral band intensities were strongly correlated to the contents of oil, fatty acids, glucosinolates, and polyphenols. The regression equations gave relatively high predictive power for the estimation of oil (R² = 0.99); all measured fatty acids (R² > 0.80), except C14:0, C20:3n-3, C22:2n-9, and C22:2n-6; 3-butenyl, 2-OH-3-butenyl, 4-OH-3-CH3-indolyl, and total glucosinolates (R² > 0.686); and total polyphenols (R² = 0.935). However, further study is required to obtain predictive equations based on large numbers of samples from diverse sources to illustrate the general applicability of these regression equations. PMID:25046077

  19. Expression of cell wall related genes in basal and ear internodes of silking brown-midrib-3, caffeic acid O-methyltransferase (COMT) down-regulated, and normal maize plants

    PubMed Central

    Guillaumie, Sabine; Goffner, Deborah; Barbier, Odile; Martinant, Jean-Pierre; Pichon, Magalie; Barrière, Yves

    2008-01-01

    Background Silage maize is a major forage and energy resource for cattle feeding, and several studies have shown that lignin content and structure are the determining factors in forage maize feeding value. In maize, four natural brown-midrib mutants have modified lignin content, lignin structure and cell wall digestibility. The greatest lignin reduction and the highest cell wall digestibility were observed in the brown-midrib-3 (bm3) mutant, which is disrupted in the caffeic acid O-methyltransferase (COMT) gene. Results Expression of cell wall related genes was investigated in basal and ear internodes of normal, COMT antisens (AS225), and bm3 maize plants of the INRA F2 line. A cell wall macro-array was developed with 651 gene specific tags of genes specifically involved in cell wall biogenesis. When comparing basal (older lignifying) and ear (younger lignifying) internodes of the normal line, all genes known to be involved in constitutive monolignol biosynthesis had a higher expression in younger ear internodes. The expression of the COMT gene was heavily reduced, especially in the younger lignifying tissues of the ear internode. Despite the fact that AS225 transgene expression was driven only in sclerenchyma tissues, COMT expression was also heavily reduced in AS225 ear and basal internodes. COMT disruption or down-regulation led to differential expressions of a few lignin pathway genes, which were all over-expressed, except for a phenylalanine ammonia-lyase gene. More unexpectedly, several transcription factor genes, cell signaling genes, transport and detoxification genes, genes involved in cell wall carbohydrate metabolism and genes encoding cell wall proteins, were differentially expressed, and mostly over-expressed, in COMT-deficient plants. Conclusion Differential gene expressions in COMT-deficient plants highlighted a probable disturbance in cell wall assembly. In addition, the gene expressions suggested modified chronology of the different events leading

  20. Dual laccase-tyrosinase based Sonogel-Carbon biosensor for monitoring polyphenols in beers.

    PubMed

    ElKaoutit, Mohammed; Naranjo-Rodriguez, Ignacio; Temsamani, Khalid Riffi; de la Vega, Manuel Domínguez; de Cisneros, Jose Luis Hidalgo-Hidalgo

    2007-10-01

    A biosensor based on the bi-immobilization of laccase and tyrosinase phenoloxidase enzymes has been successfully developed. This biosensor employs as the electrochemical transducer the Sonogel-Carbon, a novel type of electrode developed by our group. The immobilization step was accomplished by doping the electrode surface with a mixture of the enzymes, glutaricdialdehyde, and Nafion-ion exchanger, as protective additive. The response of this biosensor, denoted the dual Trametes versicolor laccase (La) and Mushroom tyrosinase (Ty) based Sonogel-Carbon, was optimized directly in beer real samples and its analytical performance with respect to five individual polyphenols was evaluated. The Lac-Ty/Sonogel-Carbon electrode responds to nanomolar concentrations of flavan-3-ols, hydroxycinnamic acids, and hydroxybenzoic acids. The limit of detection, sensitivity, and linear range for caffeic acid, taken as an example, were 26 nM, 167.53 nA M (-1), and 0.01-2 microM, respectively. In addition, the stability and reproducibility of the biosensor were also evaluated in beer samples. The Lac-Ty/sonogel-carbon electrode was verified as very stable in this matrix, maintaining 80% of its stable response for at least three weeks, with a RSD of 3.6% ( n = 10). The biosensor was applied to estimate the total polyphenol index in ten beer samples, and a correlation of 0.99 was obtained when the results were compared with those obtained using the Folin-Ciocalteau reagent. PMID:17848081

  1. Green tea polyphenol epigallocatechin-O-gallate induces cell death by acid sphingomyelinase activation in chronic myeloid leukemia cells.

    PubMed

    Huang, Yuhui; Kumazoe, Motofumi; Bae, Jaehoon; Yamada, Shuhei; Takai, Mika; Hidaka, Shiori; Yamashita, Shuya; Kim, Yoonhee; Won, Yeongseon; Murata, Motoki; Tsukamoto, Shuntaro; Tachibana, Hirofumi

    2015-09-01

    An epidemiological study showed that green tea consumption is associated with a reduced risk of hematopoietic malignancy. The major green tea polyphenol epigallocatechin‑3-O-gallate (EGCG) is reported to have anticancer effects. Chronic myeloid leukemia (CML) is a major hematopoietic malignancy characterized by expansion of myeloid cells. In the present study, we showed EGCG-induced acid sphingomyelinase (ASM) activation and lipid raft clustering in CML cells. The ASM inhibitor desipramine significantly reduced EGCG-induced cell death. Protein kinase Cδ is a well‑known kinase that plays an important role in ASM activation. We observed EGCG-induced phosphorylation of protein kinase Cδ at Ser664. Importantly, EGCG-induced ASM activation was significantly reduced by pretreatment of CML cells with the soluble guanylate cyclase inhibitor NS2028, suggesting that EGCG induced ASM activation through the cyclic guanosine monophosphate (cGMP)-dependent pathway. Indeed, pharmacological inhibition of a cGMP-negative regulator enhanced the anti-CML effect of EGCG. These results indicate that EGCG-induced cell death via the cGMP/ASM pathway in CML cells. PMID:26135316

  2. Green tea polyphenol epigallocatechin-O-gallate induces cell death by acid sphingomyelinase activation in chronic myeloid leukemia cells

    PubMed Central

    HUANG, YUHUI; KUMAZOE, MOTOFUMI; BAE, JAEHOON; YAMADA, SHUHEI; TAKAI, MIKA; HIDAKA, SHIORI; YAMASHITA, SHUYA; KIM, YOONHEE; WON, YEONGSEON; MURATA, MOTOKI; TSUKAMOTO, SHUNTARO; TACHIBANA, HIROFUMI

    2015-01-01

    An epidemiological study showed that green tea consumption is associated with a reduced risk of hematopoietic malignancy. The major green tea polyphenol epigallocatechin-3-O-gallate (EGCG) is reported to have anticancer effects. Chronic myeloid leukemia (CML) is a major hematopoietic malignancy characterized by expansion of myeloid cells. In the present study, we showed EGCG-induced acid sphingomyelinase (ASM) activation and lipid raft clustering in CML cells. The ASM inhibitor desipramine significantly reduced EGCG-induced cell death. Protein kinase Cδ is a well-known kinase that plays an important role in ASM activation. We observed EGCG-induced phos-phorylation of protein kinase Cδ at Ser664. Importantly, EGCG-induced ASM activation was significantly reduced by pretreatment of CML cells with the soluble guanylate cyclase inhibitor NS2028, suggesting that EGCG induced ASM activation through the cyclic guanosine monophosphate (cGMP)-dependent pathway. Indeed, pharmacological inhibition of a cGMP-negative regulator enhanced the anti-CML effect of EGCG. These results indicate that EGCG-induced cell death via the cGMP/ASM pathway in CML cells. PMID:26135316

  3. The Polyphenol Chlorogenic Acid Attenuates UVB-mediated Oxidative Stress in Human HaCaT Keratinocytes

    PubMed Central

    Cha, Ji Won; Piao, Mei Jing; Kim, Ki Cheon; Yao, Cheng Wen; Zheng, Jian; Kim, Seong Min; Hyun, Chang Lim; Ahn, Yong Seok; Hyun, Jin Won

    2014-01-01

    We investigated the protective effects of chlorogenic acid (CGA), a polyphenol compound, on oxidative damage induced by UVB exposure on human HaCaT cells. In a cell-free system, CGA scavenged 1,1-diphenyl-2-picrylhydrazyl radicals, superoxide anions, hydroxyl radicals, and intracellular reactive oxygen species (ROS) generated by hydrogen peroxide and ultraviolet B (UVB). Furthermore, CGA absorbed electromagnetic radiation in the UVB range (280–320 nm). UVB exposure resulted in damage to cellular DNA, as demonstrated in a comet assay; pre-treatment of cells with CGA prior to UVB irradiation prevented DNA damage and increased cell viability. Furthermore, CGA pre-treatment prevented or ameliorated apoptosis-related changes in UVB-exposed cells, including the formation of apoptotic bodies, disruption of mitochondrial membrane potential, and alterations in the levels of the apoptosis-related proteins Bcl-2, Bax, and caspase-3. Our findings suggest that CGA protects cells from oxidative stress induced by UVB radiation. PMID:24753819

  4. Catecholaminergic and cholinergic systems of mouse brain are modulated by LMN diet, rich in theobromine, polyphenols and polyunsaturated fatty acids.

    PubMed

    Fernández-Fernández, Laura; Esteban, Gerard; Giralt, Mercedes; Valente, Tony; Bolea, Irene; Solé, Montse; Sun, Ping; Benítez, Susana; Morelló, José Ramón; Reguant, Jordi; Ramírez, Bartolomé; Hidalgo, Juan; Unzeta, Mercedes

    2015-04-01

    The possible modulatory effect of the functional LMN diet, rich in theobromine, polyphenols and polyunsaturated fatty acids, on the catecholaminergic and cholinergic neurotransmission, affecting cognition decline during aging has been studied. 129S1/SvlmJ mice were fed for 10, 20, 30 and 40 days with either LMN or control diets. The enzymes involved in catecholaminergic and cholinergic metabolism were determined by both immunohistological and western blot analyses. Noradrenalin, dopamine and other metabolites were quantified by HPLC analysis. Theobromine, present in cocoa, the main LMN diet component, was analysed in parallel using SH-SY5Y and PC12 cell lines. An enhanced modulatory effect on both cholinergic and catecholaminergic transmissions was observed on 20 day fed mice. Similar effect was observed with theobromine, besides its antioxidant capacity inducing SOD-1 and GPx expression. The enhancing effect of the LMN diet and theobromine on the levels of acetylcholine-related enzymes, dopamine and specially noradrenalin confirms the beneficial role of this diet on the "cognitive reserve" and hence a possible reducing effect on cognitive decline underlying aging and Alzheimer's disease. PMID:25756794

  5. Polyphenolic Secondary Metabolites Synergize the Activity of Commercial Antibiotics against Clinical Isolates of β-Lactamase-producing Klebsiella pneumoniae.

    PubMed

    Dey, Diganta; Ghosh, Subhalakshmi; Ray, Ratnamala; Hazra, Banasri

    2016-02-01

    Emergence of worldwide antimicrobial resistance prompted us to study the resistance modifying potential of plant-derived dietary polyphenols, mainly caffeic acid, ellagic acid, epigallocatechin-3-gallate (EGCG) and quercetin. These compounds were studied in logical combination with clinically significant antibiotics (ciprofloxacin/gentamicin/tetracycline) against Klebsiella pneumoniae, after conducting phenotypic screening of a large number of clinical isolates and selecting the relevant strains possessing extended-spectrum β-lactamase (ESBL) and K. pneumoniae carbapenemase (KPC)-type carbapenemase enzymes only. The study demonstrated that EGCG and caffeic acid could synergize the activity of tested antibiotics within a major population of β-lactamase-producing K. pneumoniae. In spectrofluorimetric assay, ~17-fold greater ciprofloxacin accumulation was observed within K. pneumoniae cells pre-treated with EGCG in comparison with the untreated control, indicating its ability to synergize ciprofloxacin to restrain active drug-efflux. Further, electron micrograph of ESBL-producing K. pneumoniae clearly demonstrated the prospective efficacy of EGCG towards biofilm degradation. PMID:26668123

  6. The conformational state of polyphenol oxidase from field bean (Dolichos lablab) upon SDS and acid-pH activation

    PubMed Central

    Kanade, Santosh R.; Paul, Beena; Rao, A. G. Appu; Gowda, Lalitha R.

    2006-01-01

    Field bean (Dolichos lablab) contains a single isoform of PPO (polyphenol oxidase) – a type III copper protein that catalyses the o-hydroxylation of monophenols and oxidation of o-diphenols using molecular oxygen – and is a homotetramer with a molecular mass of 120 kDa. The enzyme is activated manyfold either in the presence of the anionic detergent SDS below its critical micellar concentration or on exposure to acid-pH. The enhancement of kcat upon activation is accompanied by a marked shift in the pH optimum for the oxidation of t-butyl catechol from 4.5 to 6.0, an increased sensitivity to tropolone, altered susceptibility to proteolytic degradation and decreased thermostability. The Stokes radius of the native enzyme is found to increase from 49.1±2 to 75.9±0.6 Å (1 Å=0.1 nm). The activation by SDS and acid-pH results in a localized conformational change that is anchored around the catalytic site of PPO that alters the microenvironment of an essential glutamic residue. Chemical modification of field bean and sweet potato PPO with 1-ethyl-3-(3-dimethylaminopropyl)carbodi-imide followed by kinetic analysis leads to the conclusion that both the enzymes possess a core carboxylate essential to activity. This enhanced catalytic efficiency of PPO, considered as an inducible defence oxidative enzyme, is vital to the physiological defence strategy adapted by plants to insect herbivory and pathogen attack. PMID:16393141

  7. Ferulic acid, a natural polyphenol, alleviates insulin resistance and hypertension in fructose fed rats: Effect on endothelial-dependent relaxation.

    PubMed

    El-Bassossy, Hany; Badawy, Dina; Neamatallah, Thikryat; Fahmy, Ahmed

    2016-07-25

    Ferulic acid (FER) is a polyphenolic compound contained in various types of fruits. It has a substantial therapeutic effect inhibitory activity against aldose reductase (AR) inhibition. In this study, we examined the effect of FER on fructose-fed rats in comparison to a standard AR inhibitor, zopolrestat (ZOP). We determined the protective role of FER against metabolic syndrome by examining serum insulin/Glucose levels, triglycerides (TGs), cholesterol and advanced glycation end product (AGE) in rats supplied with 10% fructose drinking water. In addition, blood pressure, vascular reactivity of isolated thoracic aortas and acetylcholine-induced NO were all evaluated to estimate the cardiovascular complications of metabolic syndrome (MetS) associated with fructose feeding. Animals were randomly divided into four groups: control, (+10% fructose, Fru), zopolrestat-treated fructose fed (Fru-zop) and ferulic acid-treated fructose fed rats (Fru-Fer). After 12 weeks of FER treatment, we found significant reduction in both hyperinsulinemia and elevated diastolic blood pressure associated with fructose-fed to levels comparable to those achieved with ZOP. Both FER and ZOP significantly augmented the impaired relaxation associated with fructose-fed, whereas neither showed any significant effect on the developed vasoconstriction. Isolated aortas from fructose-fed rats incubated with either FER or ZOP, reinstated normal relaxation response to acetylcholine (ACh). Furthermore, isolated aortas showed attenuated nitric oxide (NO) production following the addition of (ACh), while both FER and ZOP restored normal induction of NO. Taken together, the current study shows that, FER alleviated insulin resistance and hypertension associated with metabolic syndrome compared to the standard AR inhibitor (ZOP). This potential protective effect is at least mediated by restoring endothelial relaxation. PMID:27287418

  8. Pro-autophagic polyphenols reduce the acetylation of cytoplasmic proteins

    PubMed Central

    Pietrocola, Federico; Mariño, Guillermo; Lissa, Delphine; Vacchelli, Erika; Malik, Shoaib Ahmad; Niso-Santano, Mireia; Zamzami, Naoufal; Galluzzi, Lorenzo; Maiuri, Maria Chiara; Kroemer, Guido

    2012-01-01

    Resveratrol is a polyphenol contained in red wine that has been amply investigated for its beneficial effects on organismal metabolism, in particular in the context of the so-called “French paradox,” i.e., the relatively low incidence of coronary heart disease exhibited by a population with a high dietary intake of cholesterol and saturated fats. At least part of the beneficial effect of resveratrol on human health stems from its capacity to promote autophagy by activating the NAD-dependent deacetylase sirtuin 1. However, the concentration of resveratrol found in red wine is excessively low to account alone for the French paradox. Here, we investigated the possibility that other mono- and polyphenols contained in red wine might induce autophagy while affecting the acetylation levels of cellular proteins. Phenolic compounds found in red wine, including anthocyanins (oenin), stilbenoids (piceatannol), monophenols (caffeic acid, gallic acid) glucosides (delphinidin, kuronamin, peonidin) and flavonoids (catechin, epicatechin, quercetin, myricetin), were all capable of stimulating autophagy, although with dissimilar potencies. Importantly, a robust negative correlation could be established between autophagy induction and the acetylation levels of cytoplasmic proteins, as determined by a novel immunofluorescence staining protocol that allows for the exclusion of nuclear components from the analysis. Inhibition of sirtuin 1 by both pharmacological and genetic means abolished protein deacetylation and autophagy as stimulated by resveratrol, but not by piceatannol, indicating that these compounds act through distinct molecular pathways. In support of this notion, resveratrol and piceatannol synergized in inducing autophagy as well as in promoting cytoplasmic protein deacetylation. Our results highlight a cause-effect relationship between the deacetylation of cytoplasmic proteins and autophagy induction by red wine components. PMID:23070521

  9. The effects of different night-time temperatures and cultivation durations on the polyphenolic contents of lettuce: Application of principal component analysis

    PubMed Central

    Jeong, Sung Woo; Kim, Gon-Sup; Lee, Won Sup; Kim, Yun-Hi; Kang, Nam Jun; Jin, Jong Sung; Lee, Gye Min; Kim, Soo Taek; Abd El-Aty, A.M.; Shim, Jae-Han; Shin, Sung Chul

    2015-01-01

    The present study was conducted to characterize the polyphenolic contents of lettuce leaves grown under different night-time temperatures (4, 12, and 20 °C) and cultivation durations (5, 15, and 20 days) using high performance liquid chromatography-tandem mass spectrometry (LC/MS/MS). The assay method was validated based on specificity, linearity, accuracy, precision, and the performance limit. The total polyphenolic contents were highest (2462.6 mg/kg) after transplantation at a night temperature of 20 °C on day 20 and lowest (1132.7 mg/kg) at the same temperature on day 5. Quantification and principal component analysis showed that the relative contents of quercetin and kaempferol were markedly higher during the early stage of cultivation (day 5) than those of day 15 and 20, and that night-time temperatures of 12 and 20 °C on day 20 were favorable for producing polyphenol-rich lettuce containing caffeic acid. In conclusion, a synergistic effect between high night-time temperatures (12 and 20 °C) and cultivation duration (20 days) produced lettuce rich in polyphenols compared to that at low temperature (4 °C). PMID:26257947

  10. Sonication enhances polyphenolic compounds, sugars, carotenoids and mineral elements of apple juice.

    PubMed

    Abid, Muhammad; Jabbar, Saqib; Wu, Tao; Hashim, Malik Muhammad; Hu, Bing; Lei, Shicheng; Zeng, Xiaoxiong

    2014-01-01

    A study was initiated with the objective of evaluating the effects of sonication treatment on quality characteristics of apple juice such as polyphenolic compounds (chlorogenic acid, caffeic acid, catechin, epicatechin and phloridzin), sugars (fructose, glucose and sucrose), mineral elements (Na, K, Ca, P, Mg, Cu and Zn), total carotenoids, total anthocyanins, viscosity and electrical conductivity. The fresh apple juice samples were sonicated for 0, 30 and 60 min at 20 °C (frequency 25 kHz and amplitude 70%), respectively. As results, the contents of polyphenolic compounds and sugars significantly increased (P<0.05) but the increases were more pronounced in juice samples sonicated for 30 min whereas, total carotenoids, mineral elements (Na, K and Ca) and viscosity significantly increased (P<0.05) in samples treated for 60 min sonication. Losses of some mineral elements (P, Mg and Cu) also occurred. Total anthocyanins, Zn and electrical conductivity did not undergo any change in the sonicated samples. Findings of the present study suggest that sonication technique may be applied to improve phytonutrients present naturally in apple juice. PMID:23835397

  11. Urinary Excretion of Select Dietary Polyphenol Metabolites Is Associated with a Lower Risk of Type 2 Diabetes in Proximate but Not Remote Follow-Up in a Prospective Investigation in 2 Cohorts of US Women123

    PubMed Central

    Sun, Qi; Wedick, Nicole M; Tworoger, Shelley S; Pan, An; Townsend, Mary K; Cassidy, Aedin; Franke, Adrian A; Rimm, Eric B; Hu, Frank B; van Dam, Rob M

    2015-01-01

    Background: Polyphenols are phytochemicals that possess antioxidant and anti-inflammatory properties and improve glucose metabolism in animal experiments, although data from prospective epidemiologic studies examining polyphenol intakes in relation to type 2 diabetes (T2D) risk are inconsistent. Objectives: We examined urinary excretion of select flavonoid and phenolic acid metabolites, as biomarkers of intake, in relation to T2D risk. Methods: Eight polyphenol metabolites (naringenin, hesperetin, quercetin, isorhamnetin, catechin, epicatechin, caffeic acid, and ferulic acid) were quantified in spot urine samples by liquid chromatography/mass spectrometry among 1111 T2D case-control pairs selected from the Nurses’ Health Study (NHS) and NHSII. Results: Higher urinary excretion of hesperetin was associated with a lower T2D risk after multivariate adjustment: the OR comparing top vs. bottom quartiles was 0.68 (95% CI: 0.49, 0.96), although a linear trend was lacking (P = 0.30). The other measured polyphenols were not significantly associated with T2D risk after multivariate adjustment. However, during the early follow-up period [≤4.6 y (median) since urine sample collection], markers of flavanone intakes (naringenin and hesperetin) and flavonol intakes (quercetin and isorhamnetin) were significantly associated with a lower T2D risk. The ORs (95% CIs) comparing extreme quartiles were 0.61 (0.39, 0.98; P-trend: 0.03) for total flavanones and 0.55 (0.33, 0.92; P-trend: 0.04) for total flavonols (P-interaction with follow-up length: ≤0.04). An inverse association was also observed for caffeic acid during early follow-up only: the OR was 0.52 (95% CI: 0.32, 0.84; P-trend: 0.03). None of these markers was associated with T2D risk during later follow-up. Metabolites of flavan-3-ols and ferulic acid were not associated with T2D risk in either period. Conclusions: These results suggest that specific flavonoid subclasses, including flavanones and flavonols, as well as

  12. Polyphenolic responses of grapevine berries to light, temperature, oxidative stress, abscisic acid and jasmonic acid show specific developmental-dependent degrees of metabolic resilience to perturbation.

    PubMed

    Degu, Asfaw; Ayenew, Biruk; Cramer, Grant R; Fait, Aaron

    2016-12-01

    Grape-berries are exposed to a plethora of abiotic and biotic stimuli during their development. The developmental and temporal regulation of grape berry polyphenol metabolism in response to various cues was investigated using LC-QTOF-MS based metabolite profiling. High light (2500μmolm(-2)s(-1)), high temperature (40°C), jasmonic acid (200μM), menadione (120μM) and abscisic acid (3.026mM) treatments were applied to detached berries. Greater magnitudes of metabolite fluctuations characterize the pre-veraison berries than the veraison stage in response to the treatments. Furthermore, a tighter co-response of metabolic processes was shown at veraison, likely supporting the resilience to change in response to stress. High temperature and ABA treatments led to greater magnitudes of change during the course of the experiment. The present study demonstrates the occurrence of differential patterns of metabolic responses specific to individual cues and berry developmental stage, which in the field are commonly associated and thus hardly discernable. PMID:27374601

  13. A comparison of three amperometric phenoloxidase-Sonogel-Carbon based biosensors for determination of polyphenols in beers.

    PubMed

    ElKaoutit, Mohammed; Naranjo-Rodriguez, Ignacio; Temsamani, Khalid Riffi; Hernández-Artiga, Maria P; Bellido-Milla, Dolores; Cisneros, Jose Luis Hidalgo-Hidalgo de

    2008-10-15

    Three phenoloxidases based biosensors were successfully developed using as electrochemical transducer a new type of electrode recently developed by our group: the "Sonogel-Carbon electrode". The employed enzymes were Trametes versicolor laccase (Lac), Mushroom tyrosinase (Tyr), and Horseradish peroxidase (HRP). Immobilization step was accomplished by doping the electrode surface with a mixture of the individual enzyme and Nafion ion exchanger as additive-protective. The biosensor responses, optimized in beer real samples, were evaluated for five individual polyphenols. It was found that the developed biosensors were sensitive to nanomolar concentrations of the tested polyphenols. As example, the limit of detection, sensitivity, and response linear range for caffeic acid for Nafion-Lac/Sonogel-Carbon biosensor were 0.06μmolL(-1), 99.6nAμmol(-1)L, and 0.04-2μmolL(-1), respectively. The stability and reproducibility of the biosensors were evaluated by applying them directly to beer real samples. It has been demonstrated that the Nafion-Lac/Sonogel-Carbon system is the more stable with a relative standard deviation of 3.3% (n=10), maintaining 84% of its stable response for at least three weeks. Estimation of polyphenol index in eight lager beers and a comparison of the results with those obtained by a classical method was carried out. PMID:26047296

  14. Ellagic acid and polyphenolics present in walnut kernels inhibit in vitro human peripheral blood mononuclear cell proliferation and alter cytokine production.

    PubMed

    Anderson, Koren C; Teuber, Suzanne S

    2010-03-01

    Tree nuts, including walnuts, are important elicitors of food allergy. We examined the ability of walnut kernel polyphenolics and purified ellagic acid (EA) to modulate cytokine production and cellular proliferation from stimulated human peripheral blood mononuclear cells (PBMC). IL-13 and TNF-alpha production decreased while no change was observed in IL-4 production. Paradoxically, EA and the walnut polyphenolics all significantly and dose-dependently inhibited stimulated [phytohemagglutin (PHA), alpha-CD3, and phorbol myristate acetate (PMA)/ionomycin] PBMC proliferation while simultaneously increasing IL-2 production. When added at time 0 min and 2 h, EA dose-dependently inhibited PHA-induced proliferation. However, at 30 min and 1 h, low doses of EA (10 and 1 muM) significantly increased proliferation above that of PHA alone, although higher doses led to inhibition. Our data do not support the hypothesis that walnut polyphenolics skew a cytokine response toward Th2 in an in vitro environment. However, immunomodulatory effects are present, including an inhibition of cellular proliferation despite no decrease in IL-4 or IL-2. PMID:20388139

  15. Effect of sample preparation on the measurement of sugars, organic acids, and polyphenols in apple fruit by mid-infrared spectroscopy.

    PubMed

    Bureau, Sylvie; Scibisz, Iwona; Le Bourvellec, Carine; Renard, Catherine M G C

    2012-04-11

    The objectives of this study were (i) to test different conditions of freezing, thawing, and grinding during sample preparation and (ii) to evaluate the possibility of using mid-infrared spectroscopy for analyzing the composition of sugars, organic acids, and polyphenols in apples. Seven commercial apple cultivars were chosen for their large variability in composition (total polyphenols from 406 to 1033 mg kg(-1) fresh weight). The different conditions of sample preparation affected only the phenolic compounds and not sugars or organic acids. The regression models of the mid-infrared spectra showed a good ability to estimate sugar and organic acid contents (R(2) ≥ 0.96), except for citric acid. Good predictions were obtained for total phenolic, flavan-3-ols, and procyanidins (R(2) ≥ 0.94) provided oxidation was avoided during sample preparation. A rapid and simple procedure was then proposed for phenolic compounds using sodium fluoride during sample homogenization at ambient temperature and freeze-drying before spectra acquisition. PMID:22409403

  16. Glutathione and cinnamic acid: natural dietary components used in preventing the process of browning by inhibition of Polyphenol Oxidase in apple juice.

    PubMed

    Gacche, R N; Warangkar, S C; Ghole, V S

    2004-04-01

    Consumer demands for 'freshness' in processed foods has been given increasing attention by food processing industries by searching for minimally processed products. Polyphenol Oxidase (PPO) mediated browning is a major cause of undesirable flavors and nutritional losses in fruit juices. Here the anti-browning efficiency of glutathione (GSH, reduced form) and cinnamic acid (CA) in apple juice is evaluated. It was observed that the rate of the browning reaction could be efficiently delayed using GSH and CA, which act as inhibitors of PPO. Kinetic studies confirm that GSH and CA are non-competitive and competitive inhibitors of PPO respectively. PMID:15449733

  17. Reducing peanut allergens by high pressure combined with polyphenol oxidase

    NASA Astrophysics Data System (ADS)

    Chung, Si-Yin; Houska, Milan; Reed, Shawndrika

    2013-12-01

    Polyphenol oxidase (PPO) has been shown to reduce major peanut allergens. Since high pressure (HP) can increase enzyme activity, we postulated that further reduction of peanut allergens can be achieved through HP combined with PPO. Peanut extracts containing caffeic acid were treated with each of the following: (1) HP; (2) HP+PPO; (3) PPO; and (4) none. HP was conducted at 300 and 500 MPa, each for 3 and 10 min, 37 °C. After treatment, SDS-PAGE was performed and allergenic capacity (IgE binding) was determined colorimetrically in inhibition enzyme-linked immunosorbent assay and Western blots, using a pooled plasma from peanut-allergic patients. Data showed that HP alone had no effect on major peanut allergens. However, HP at 500 MPa combined with PPO (HP500/PPO) induced a higher (approximately twofold) reduction of major peanut allergens and IgE binding than PPO alone or HP300/PPO. There was no difference between treatment times. We concluded that HP500/PPO at 3-min enhanced a twofold reduction of the allergenic capacity of peanut extracts, as compared to PPO itself.

  18. Blueberry polyphenols attenuate kainic acid-induced decrements in cognition and alter inflammatory gene expression in rat hippocampus

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Cognitive impairment in age-related neurodegenerative diseases such as Alzheimer's disease may be partly due to long-term exposure and increased susceptibility to inflammatory insults. In the current study we investigated whether polyphenols in blueberries (BBs) can reduce the deleterious effects o...

  19. Polyphenol composition and antioxidant capacity from different extracts of Aster scaber.

    PubMed

    Thiruvengadam, M; Praveen, N; Yu, B R; Kim, S H; Chung, I M

    2014-06-01

    Phenolic contents and antioxidant capacities from different solvent extracts (petroleum ether, ethyl acetate, methanol, butanol and water) of Aster scaber leaf were investigated. Antioxidant activity was evaluated by three different methods, namely DPPH radical scavenging activity, reducing power assay and phosphomolybdenum activity. A total of twenty-three polyphenolic compounds were identified and quantified from A. scaber leaf extracts, including hydroxybenzoic acids, hydroxycinnamic acids, flavonols and other groups of phenolic compounds. Ultra high performance liquid chromatography (UHPLC) analysis of the leaf extract revealed that myricetin (4850.45 μg/g) was the most dominant flavonols, compared to quercetin and kaempferol. Caffeic acid was the dominant phenolic compound in A. scaber leaf extracts, it constituted about 104.20 μg/g, followed by gentisic acid (84.50 μg/g), gallic acid (61.05 μg/g) and homogentisic acid (55.65 μg/g). The total phenolic and flavonoid content was the highest in ethyl acetate extract (322.43 and 6.51 mg/g). The decreasing order of antioxidant activity among the A. scaber leaf extracts assayed through all the three methods was found to be ethyl acetate > butanol > methanol > petroleum ether > water extract. PMID:24873908

  20. Evaluation of physicochemical properties and intestinal permeability of six dietary polyphenols in human intestinal colon adenocarcinoma Caco-2 cells.

    PubMed

    Rastogi, Himanshu; Jana, Snehasis

    2016-02-01

    Phenolic compounds are common ingredients in many dietary supplements and functional foods. However, data concerning physicochemical properties and permeability of polyphenols on the intestinal epithelial cells are scarce. The aims of this study were to determine the experimental partition coefficient (Log P), and parallel artificial membrane permeability assay (PAMPA), to characterize the bi-directional transport of six phenolic compounds viz. caffeic acid, chrysin, gallic acid, quercetin, resveratrol and rutin in Caco-2 cells. The experimental Log P values of six polyphenols were correlated (R (2) = 0.92) well with the calculated Log P values. The apparent permeability (P app) range of all polyphenols in PAMPA for the apical (AP) to basolateral (BL) was 1.18 ± 0.05 × 10(-6) to 5.90 ± 0.16 × 10(-6) cm/s. The apparent Caco-2 permeability (P app) range for the AP-BL was 0.96 ± 0.03 × 10(-6) to 3.80 ± 0.45 × 10(-6) cm/s. The efflux ratio of P app (BL → AP) to P app (AP → BL) for all phenolics was <2, suggesting greater permeability in the absorptive direction. Six compounds exhibited strong correlations between Log P and PAMPA/Caco-2 cell monolayer permeation data. Dietary six polyphenols were poorly absorbed through PAMPA and Caco-2 cells, and their transepithelial transports were mainly by passive diffusion. PMID:25351179

  1. Brassinosteroids Improve Quality of Summer Tea (Camellia sinensis L.) by Balancing Biosynthesis of Polyphenols and Amino Acids

    PubMed Central

    Li, Xin; Ahammed, Golam J.; Li, Zhi-Xin; Zhang, Lan; Wei, Ji-Peng; Shen, Chen; Yan, Peng; Zhang, Li-Ping; Han, Wen-Yan

    2016-01-01

    Summer grown green tea is less popular due to bitterness and high astringency, which are attributed to high levels of tea polyphenols (TP) and low levels of amino acids (AA) in tea leaves (Camellia sinensis L.). Brassinosteroids (BRs), a group of steroidal plant hormones can regulate primary and secondary metabolism in a range of plant species under both normal and stress conditions. However, specific effects of BRs on the photosynthesis of tea plants and the quality of summer green tea are largely unknown. Here we show that 24-epibrassinolide (EBR), a bioactive BR, promoted photosynthesis in tea plants in a concentration-dependent manner. Stimulation in photosynthesis by EBR resulted in an increased summer tea yield. Although all tested concentrations (0.01, 0.05, 0.1, 0.5, and 1.0 ppm) of EBR increased concentrations of TP and AA, a moderate concentration (0.5 ppm) caused the highest decrease in TP to AA ratio, an important feature of quality tea. Time-course analysis using 0.5 ppm EBR as foliar spray revealed that TP or AA concentration increased as early as 3 h after EBR application, reaching the highest peak at 24 h and that remained more or less stable. Importantly, such changes in TP and AA concentration by EBR resulted in a remarkably decreased but stable TP to AA ratio at 24 h and onward. Furthermore, concentrations of catechins and theanine increased, while that of caffeine remained unaltered following treatment with EBR. EBR improved activity of phenylalanine ammonia-lyase (PAL) and glutamine: 2-oxoglutarate aminotransferase (GOGAT) enzymes involved in catechins and theanine biosynthesis, respectively. Transcript analysis revealed that transcript levels of CsPAL and CsGS peaked as early as 6 h, while that of CsGOGAT peaked at 12 h following application of EBR, implying that EBR increased the concentration of TP and AA by inducing their biosynthesis. These results suggest a positive role of BR in enhancing green tea quality, which might have potential

  2. Brassinosteroids Improve Quality of Summer Tea (Camellia sinensis L.) by Balancing Biosynthesis of Polyphenols and Amino Acids.

    PubMed

    Li, Xin; Ahammed, Golam J; Li, Zhi-Xin; Zhang, Lan; Wei, Ji-Peng; Shen, Chen; Yan, Peng; Zhang, Li-Ping; Han, Wen-Yan

    2016-01-01

    Summer grown green tea is less popular due to bitterness and high astringency, which are attributed to high levels of tea polyphenols (TP) and low levels of amino acids (AA) in tea leaves (Camellia sinensis L.). Brassinosteroids (BRs), a group of steroidal plant hormones can regulate primary and secondary metabolism in a range of plant species under both normal and stress conditions. However, specific effects of BRs on the photosynthesis of tea plants and the quality of summer green tea are largely unknown. Here we show that 24-epibrassinolide (EBR), a bioactive BR, promoted photosynthesis in tea plants in a concentration-dependent manner. Stimulation in photosynthesis by EBR resulted in an increased summer tea yield. Although all tested concentrations (0.01, 0.05, 0.1, 0.5, and 1.0 ppm) of EBR increased concentrations of TP and AA, a moderate concentration (0.5 ppm) caused the highest decrease in TP to AA ratio, an important feature of quality tea. Time-course analysis using 0.5 ppm EBR as foliar spray revealed that TP or AA concentration increased as early as 3 h after EBR application, reaching the highest peak at 24 h and that remained more or less stable. Importantly, such changes in TP and AA concentration by EBR resulted in a remarkably decreased but stable TP to AA ratio at 24 h and onward. Furthermore, concentrations of catechins and theanine increased, while that of caffeine remained unaltered following treatment with EBR. EBR improved activity of phenylalanine ammonia-lyase (PAL) and glutamine: 2-oxoglutarate aminotransferase (GOGAT) enzymes involved in catechins and theanine biosynthesis, respectively. Transcript analysis revealed that transcript levels of CsPAL and CsGS peaked as early as 6 h, while that of CsGOGAT peaked at 12 h following application of EBR, implying that EBR increased the concentration of TP and AA by inducing their biosynthesis. These results suggest a positive role of BR in enhancing green tea quality, which might have potential

  3. Effect of lipolytic activity of Candida adriatica, Candida diddensiae and Yamadazyma terventina on the acidity of extra-virgin olive oil with a different polyphenol and water content.

    PubMed

    Ciafardini, G; Zullo, B A

    2015-05-01

    Previous microbiological research demonstrated the presence of a rich micro-flora composed mainly of yeasts in the suspended fraction of freshly produced olive oil. Some of the yeasts are considered harmful as they can damage the quality of the olive oil through the hydrolysis of the triacylglycerols. Present research has demonstrated that the lipolytic activity of some lipase-producer strains belonging to a yeast species called Candida adriatica, Candida diddensiae and Yamadazyma terventina can be modulated by the water and the polyphenol content of olive oil. Laboratory tests highlighted a substantial increase in free fatty acid in the inoculated olive oil characterized by high water content and low polyphenol concentration. The acidity of the olive oil samples containing 0.06% and 0.31% of water increased significantly by 33% in the lipase-producer yeast strains tested during a period of 2 weeks of incubation at 30 °C. All other yeasts showed strong lipolytic activity in the presence of 1.31% of water - the only exception to this was the C. adriatica 1985 strain. The phenolic compounds typical of olive oil represent another important factor able to condition the viability and the lipolytic activity of the lipase-producer yeasts. From the tests performed on the olive oil characterized by an increasing content of total polyphenols equal to 84, 150 and 510 mg per kg of oil, the percentage of the lipase-producer yeasts able to hydrolyse the triacylglycerols was respectively 100%, 67% and 11%. PMID:25583333

  4. Polyphenols from wolfberry and their bioactivities.

    PubMed

    Zhou, Zheng-Qun; Xiao, Jia; Fan, Hong-Xia; Yu, Yang; He, Rong-Rong; Feng, Xiao-Lin; Kurihara, Hiroshi; So, Kwok-Fai; Yao, Xin-Sheng; Gao, Hao

    2017-01-01

    Nine new phenylpropanoids, one new coumarin, and 43 known polyphenols were isolated from wolfberry. Their structures were determined by spectroscopic analyses, chemical methods, and comparison of NMR data. Polyphenols, an important type of natural products, are notable constituents in wolfberry. 53 polyphenols, including 28 phenylpropanoids, four coumarins, eight lignans, five flavonoids, three isoflavonoids, two chlorogenic acid derivatives, and three other constituents, were identified from wolfberry. Lignans and isoflavonoids were firstly reported from wolfberry. 22 known polyphenols were the first isolates from the genus Lycium. This research presents a systematic study on wolfberry polyphenols, including their bioactivities. All these compounds exhibited oxygen radical absorbance capacity (ORAC), and some compounds displayed DPPH radical scavenging activity. One compound had acetylcholinesterase inhibitory activity. The discovery of new polyphenols and their bioactivities is beneficial for understanding the scientific basis of the effects of wolfberry. PMID:27507521

  5. Characterization of polyphenolic metabolites in grape hybrids

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The composition and content of polyphenolic compounds in the berries of 48 hybrid grapes (Vitis) were characterized for two consecutive years. A total of 48 polyphenolic compounds including 28 anthocyanins, 2 hydroxybenzoic acids, 6 hydroxycinnamic derivatives, 6 flavonols and 6 flavanols were ident...

  6. Guava leaves polyphenolics-rich extract inhibits vital enzymes implicated in gout and hypertension in vitro

    PubMed Central

    Irondi, Emmanuel Anyachukwu; Agboola, Samson Olalekan; Oboh, Ganiyu; Boligon, Aline Augusti; Athayde, Margareth Linde; Shode, Francis O.

    2016-01-01

    Background/Aim: Elevated uric acid level, an index of gout resulting from the over-activity of xanthine oxidase (XO), increases the risk of developing hypertension. However, research has shown that plant-derived inhibitors of XO and angiotensin 1-converting enzyme (ACE), two enzymes implicated in gout and hypertension, respectively, can prevent or ameliorate both diseases, without noticeable side effects. Hence, this study characterized the polyphenolics composition of guava leaves extract and evaluated its inhibitory effect on XO and ACE in vitro. Materials and Methods: The polyphenolics (flavonoids and phenolic acids) were characterized using high-performance liquid chromatography (HPLC) coupled with diode array detection (DAD). The XO, ACE, and Fe2+-induced lipid peroxidation inhibitory activities, and free radicals (2,2-diphenylpicrylhydrazyl [DPPH]* and 2,2´-azino-bis-3-ethylbenzthiazoline-6-sulphonic [ABTS]*+) scavenging activities of the extract were determined using spectrophotometric methods. Results: Flavonoids were present in the extract in the order of quercetin > kaempferol > catechin > quercitrin > rutin > luteolin > epicatechin; while phenolic acids were in the order of caffeic acid > chlorogenic acid > gallic acids. The extract effectively inhibited XO, ACE and Fe2+-induced lipid peroxidation in a dose-dependent manner; having half-maximal inhibitory concentrations (IC50) of 38.24 ± 2.32 μg/mL, 21.06 ± 2.04 μg/mL and 27.52 ± 1.72 μg/mL against XO, ACE and Fe2+-induced lipid peroxidation, respectively. The extract also strongly scavenged DPPH* and ABTS*+. Conclusion: Guava leaves extract could serve as functional food for managing gout and hypertension and attenuating the oxidative stress associated with both diseases. PMID:27104032

  7. Highly sensitive analysis of polyphenols and their metabolites in human blood cells using dispersive SPE extraction and LC-MS/MS.

    PubMed

    Mülek, Melanie; Högger, Petra

    2015-03-01

    Blood cells, particularly erythrocytes, present a significant compartment for distribution of drugs and endogenous compounds and have been suggested to be factored in pharmacokinetic and pharmacodynamic evaluations. We previously detected the binding of polyphenols to red blood cells and found indications for a facilitated uptake of the bioactive procyanidin metabolite δ-(3,4-dihydroxy-phenyl)-γ-valerolactone (M1) into human erythrocytes. The purpose of the present investigation was to develop an effective, sensitive and robust liquid chromatography tandem mass spectrometry (LC-MS/MS) method to quantify low concentrations of polyphenols in human blood cells. Various sample preparation methods including classic sample clean-up techniques and variations of the QuEChERS (quick, easy, cheap, effective, rugged and safe) approach were compared regarding compound recovery, matrix effects and overall process efficiency. The QuEChERS technique which involves a liquid-liquid extraction and clean-up by dispersive solid-phase extraction yielded best results. The method was fully validated for the six analytes: (+)-catechin, ferulic acid, M1, taxifolin, caffeic acid and δ-3-methoxy-4-hydroxy-phenyl- γ-valerolactone (M2) in human blood cells with an optimised QuEChERS sample preparation and prior enzymatic hydrolysis of analyte conjugates. The lower limits of quantification for the analytes ranged from 0.12 ng/mL for M1, M2 and taxifolin to 48.40 ng/mL for caffeic acid. The application of the method to a blood cell sample of a volunteer ingesting 100 mg/day of the standardised pine bark extract Pycnogenol(®) over the course of 3 weeks revealed measurable steady-state concentrations of catechin, M1, taxifolin, ferulic acid and M2. To our knowledge, this is the first report of using the QuEChERS approach for detection and quantification of plant-derived compounds in human blood cells. The method can be applied in pharmacokinetic studies to determine the distribution of

  8. Antioxidant activities and liquid chromatography with electrospray ionization tandem mass spectrometry characterization and quantification of the polyphenolic contents of Rumex nervosus Vahl leaves and stems.

    PubMed

    Desta, Kebede Taye; Lee, Won Sup; Lee, Sung Joong; Kim, Yun-Hi; Kim, Gon-Sup; Lee, Soo Jung; Kim, Soo Taek; Abd El-Aty, A M; Warda, Mohamad; Shin, Ho-Chul; Shim, Jae Han; Shin, Sung Chul

    2016-04-01

    In the present study, four compounds, viz. chlorogenic acid, catechin, orientin, and apigenin-O-acetylglycoside among 18 polyphenol compounds (17 flavonoids and one hydroxycinnamic acid derivative) were characterized for the first time in Rumex nervosus leaves and stems by using liquid chromatography with electrospray ionization tandem mass spectrometry. Method validation in terms of determination coefficient, limits of detection, and quantification were ≥ 0.9979, 0.68-1.61, and 2.27-5.38 mg/L, respectively. Accuracy, expressed as percent recovery for two spiking levels (10 and 50 mg/L), were in the range 78.9-110.6% with the exception of caffeic acid. The relative standard deviations were 1-17%. The total polyphenol content was higher by approximately two times in the leaf (1073 mg/kg fresh sample) than in the stem (519.86 mg/kg fresh sample). The antioxidant effects increased in a dose-dependent manner, and the scavenging activities, investigated by measuring 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) scavenging activity, ferrous ions chelating activity, superoxide anion radical scavenging activity, and ferric reducing antioxidant power activity, were significant (p < 0.05) using low concentrations of the leaf extract. Overall, the present study suggests that different parts of R. nervosus have great potential for producing a range of extracts with potential applications in medicine. PMID:26899192

  9. Evaluation of ozonation technique for pesticide residue removal and its effect on ascorbic acid, cyanidin-3-glucoside, and polyphenols in apple (Malus domesticus) fruits.

    PubMed

    Swami, Saurabh; Muzammil, Raunaq; Saha, Supradip; Shabeer, Ahammed; Oulkar, Dasharath; Banerjee, Kaushik; Singh, Shashi Bala

    2016-05-01

    Ozonated water dip technique was evaluated for the detoxification of six pesticides, i.e., chlorpyrifos, cypermethrin, azoxystrobin, hexaconazole, methyl parathion, and chlorothalonil from apple fruits. Results revealed that ozonation was better than washing alone. Ozonation for 15 min decreased residues of the test pesticides in the range of from 26.91 to 73.58%, while ozonation for 30 min could remove the pesticide residues by 39.39-95.14 % compared to 19.05-72.80 % by washing. Cypermethrin was the least removed pesticide by washing as well as by ozonation. Chlorothalonil, chlorpyrifos, and azoxystrobin were removed up to 71.45-95.14 % in a 30-min ozonation period. In case of methyl parathion removal, no extra advantage could be obtained by ozonation. The HPLC analysis indicated that ozonation also affected adversely the ascorbic acid and cyanidin-3-glucoside content of apples. However, 11 polyphenols studied showed a mixed trend. Gallic acid, 3,4-dihydroxybenzoic acid, catechin, epicatechin, p-coumaric acid, quercetin-3-O-glucoside, quercetin, and kaempferol were found to decrease while syringic acid, rutin, and resveratrol were found to increase in 30-min ozonation. PMID:27098519

  10. Antioxidant activity of polyphenolic extracts of Ichnocarpus frutescens.

    PubMed

    Kumarappan, C T; Thilagam, E; Mandal, Subhash C

    2012-07-01

    In the present study antioxidant activities by (1,1-diphenyl-2-picrylhydrazyl radical (DPPH), hydrogen peroxide, hydroxyl radical inhibition, hemolysis by hydrogen peroxide assay, reducing power and total antioxidant activities of polyphenolic extract of Ichnocarpus frutescens leaves were investigated. The flavonoids and total polyphenolic contents of the extract were also determined using standard methods. Phytochemical analyses revealed the presence of flavonoids, polyphenols, anthocyanins and simple phenolic acids. The results of antioxidant activities of polyphenol extract obtained by different in vitro methods were varied depending on the method used. Nevertheless, polyphenol extract showed significant inhibitory activities in all in vitro reactive oxygen species scavenging, might be attributed due to the high level of polyphenolic compound. Also, these various antioxidant activities were compared to α-tocopherol and l-ascorbic acid as reference antioxidant compounds. These findings provide evidence that the polyphenolic extract of I. frutescens is a natural source of antioxidant against oxidative damage. PMID:23961196

  11. Phylogenetic, molecular, and biochemical characterization of caffeic aicd O-methyltransferase (COMT) gene family in Brachypodium distachyon

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Caffeic acid O-methyltransferase (COMT) is one of the important enzymes controlling lignin monomer production in plant cell wall synthesis. Analysis of the genome sequence of new grass model Brachypodium distachyon identified four COMT gene homologues, designated as BdCOMT1, BdCOMT2, BdCOMT3, and ...

  12. Impact of packaging material and storage conditions on polyphenol stability, colour and sensory characteristics of freeze-dried sour cherry (prunus cerasus var. Marasca).

    PubMed

    Zorić, Zoran; Pedisić, Sandra; Kovačević, Danijela Bursać; Ježek, Damir; Dragović-Uzelac, Verica

    2016-02-01

    The aim of this study was to evaluate the influence of packaging materials and storage conditions on polyphenols stability, colour and sensory characteristics of freeze-dried sour cherry (Prunus cerasus var. Marasca). Freeze-dried sour cherries were packed in high barrier metalized polypropylene and aluminium packaging (PET/PPmet/PE and PET/Al/PE) for up to 12 months at 4, 20 and 37 °C. Characterisation of polyphenol compounds was done by HPLC UV/Vis PDA and in all samples individual anthocyanins (ANTs), flavonol-glycosides (FGs) and hydroxycinnamic acids (HCAs) were determined. Polyphenol content was not markedly affected by freeze-drying and decreases were amounted 1.5-5 %. Furthermore, obtained results indicated that minimal loss of polyphenol content in freeze dried sour cherries were achieved at 4 °C and 3 months of storage. Regardless of the type of packaging materials, samples stored at lower temperature during 12 months, retained the higher content of FGs (quercetin-3-glucoside, kaempferol-3-glucoside, kaempferol-3-rutinoside) and HCAs (neochlorogenic, chlorogenic, p-coumaric, caffeic and ferulic acid) than ANTs (cyanidin-3-glucosylrutinoside, cyanidin-3-rutinoside, cyanidin-3-glucoside, cyanidin-3-sophoroside). The same trend was confirmed with kinetic parameters, also. Sour cherry products packed in both type of laminate and stored at lower temperature retained characteristic dark red colour and sensory properties. This study showed that freeze-dried cherry products have pleasant sensory and very good nutritional properties, and storage in both type of laminates at 4 and 20 °C up to 6 months ensured good product quality. PMID:27162405

  13. Polyphenolic composition, antioxidant and antibacterial activities for two Romanian subspecies of Achillea distans Waldst. et Kit. ex Willd.

    PubMed

    Benedec, Daniela; Vlase, Laurian; Oniga, Ilioara; Mot, Augustin C; Damian, Grigore; Hanganu, Daniela; Duma, Mihaela; Silaghi-Dumitrescu, Radu

    2013-01-01

    The aim of this work was to study the chemical composition, antioxidant and antibacterial properties of Achillea distans Waldst. et Kit. subsp. distans and Achillea distans Waldst. et Kit. subsp. alpina Rochel, from the Rodna Mountains (Romania). The identification and quantification of major phenolic compounds was performed by a HPLC-MS method. The total polyphenolic and flavonoid content was determined spectrophotometrically. The antioxidant activity was evaluated using the DPPH bleaching method, trolox equivalent antioxidant capacity assay (TEAC), hemoglobin ascorbate peroxidase activity inhibition (HAPX) assay, and an Electron Paramagnetic Resonance (EPR) spectroscopy method. A data indicated that A. distans subsp. alpina extract has more antioxidant activity than A. distans subsp. distans extract. Luteolin, apigenin, quercetin, caffeic and chlorogenic acids were present in the two extracts of A. distans, but in different amounts. Three flavonoids were detected only in A. distans subsp. alpina. The polyphenol-richer A. distans subsp. alpina extract showed a higher antioxidant activity than A. distans subsp. distans extract. A. distans subsp. distans extract showed inhibitory activity for Gram-positive bacteria, as evaluated with four species. The quantitative and qualitative differences between the two subspecies of Achillea distans could be used as a potential taxonomic marker in order to distinguish the species. PMID:23887715

  14. Antioxidant status of blood and liver of turkeys fed diets enriched with polyunsaturated fatty acids and fruit pomaces as a source of polyphenols.

    PubMed

    Jankowski, J; Juśkiewicz, J; Zduńczyk, P; Kosmala, M; Zieliński, H; Antoszkiewicz, Z; Zduńczyk, Z

    2016-01-01

    It was hypothesized that dietary polyphenol-rich fruit pomaces can improve the antioxidant status of both diets and the tissues of turkeys fed such diets. Turkeys were fed diets containing a cellulose preparation (C) or 5% dried apple pomace (AP), blackcurrant pomace (BCP), strawberry pomace (SP) and seedless strawberry pomace (SSP). Blood and liver biochemical parameters were determined in 7 birds from each experimental group slaughtered at 15 weeks of age, after 5 weeks of feeding diets containing soybean oil and linseed oil (approx. 1:1 ratio). Dietary linseed oil added to diets at 2.5% lowered the n-6/n-3 PUFA ratio from approx. 7:1 to below 2:1, thus reducing the antioxidant properties of diets measured using DPPH, ABTS and photo-chemiluminescence assays, compared with diets containing only soybean oil and administered to birds in the first phase of feeding. Fruit pomaces, in particular SSP with the highest polyphenol content (32.81 g/kg) and the highest antioxidant activity (256.4 μM Trolox/g), increased the antioxidant capacity of turkey diets. In comparison with the control group, the dietary treatments with fruit pomaces improved blood antioxidant parameters, including catalase activity (groups AP and BCP), the total antioxidant capacity of hydrophilic (group AP) and lipophilic (groups AP, SP, and SSP) compounds, peroxide levels (groups AP and SSP) and antioxidant capacity measured by the FRAP (ferric reducing antioxidant power of plasma) assay (groups AP, BCP and SSP). Significantly lower concentrations of both vitamin E and thiobarbituric acid reactive substances (TBARS) were noted in the livers of turkeys fed all diets with dried fruit pomaces. PMID:27096792

  15. Impacts of selected dietary polyphenols on caramelization in model systems.

    PubMed

    Zhang, Xinchen; Chen, Feng; Wang, Mingfu

    2013-12-15

    This study investigated the impacts of six dietary polyphenols (phloretin, naringenin, quercetin, epicatechin, chlorogenic acid and rosmarinic acid) on fructose caramelization in thermal model systems at either neutral or alkaline pH. These polyphenols were found to increase the browning intensity and antioxidant capacity of caramel. The chemical reactions in the system of sugar and polyphenol, which include formation of polyphenol-sugar adducts, were found to be partially responsible for the formation of brown pigments and heat-induced antioxidants based on instrumental analysis. In addition, rosmarinic acid was demonstrated to significantly inhibit the formation of 5-hydroxymethylfurfural (HMF). Thus this research added to the efforts of controlling caramelization by dietary polyphenols under thermal condition, and provided some evidence to propose dietary polyphenols as functional ingredients to modify the caramel colour and bioactivity as well as to lower the amount of heat-induced contaminants such as 5-hydroxymethylfurfural (HMF). PMID:23993506

  16. Polyphenolic composition of grape stem extracts affects antioxidant activity in endothelial and muscle cells.

    PubMed

    Goutzourelas, Nikolaos; Stagos, Dimitrios; Spanidis, Ypatios; Liosi, Maria; Apostolou, Anna; Priftis, Alexandros; Haroutounian, Serko; Spandidos, Demetrios A; Tsatsakis, Aristidis M; Kouretas, Demetrios

    2015-10-01

    The aim of the present study was the assessment of the antioxidant effects of polyphenolic extracts derived from the stems of three Greek grape varieties (Moshomayro, Mavrotragano and Mandilaria) in endothelial (EA.hy926) and muscle (C2C12) cells. We also investigated the effects of the polyphenolic composition on the antioxidant effects of the grape stem extracts. For this purpose, the endothelial and muscle cells were treated with low non-cytotoxic concentrations of the extracts for 24 h in order to assess the effects of the extracts on cellular redox status using oxidative stress biomarkers. The oxidative stress markers were thiobarbituric acid reactive substances (TBARS), protein carbonyl (CARB) levels, reactive oxygen species (ROS) levels and glutathione (GSH) levels. The results revealed that treatment of the EA.hy926 cells with Mandilaria extract significantly decreased the TBARS levels by 14.8% and the CARB levels by 25.9 %, while it increased the GSH levels by 15.8% compared to the controls. Moreover, treatment of the EA.hy926 cells with Mavrotragano extract significantly increased the GSH levels by 20.2%, while it significantly decreased the TBARS and CARB levels by 12.5% and 16.6%, respectively. Treatment of the C2C12 cells with Mandilaria extract significantly decreased the TBARS levels by 47.3 %, the CARB levels by 39.0 % and the ROS levels by 21.8%, while it increased the GSH levels by 22.6% compared to the controls. Moreover, treatment of the C2C12 cells with Mavrotragano significantly decreased the TBARS, CARB and ROS levels by 36.2%, 35.9% and 16.5%, respectively. In conclusion, to the best of our knowledgel, our results demonstrate for the first time that treatment with grape stem extracts at low concentrations improves the redox status of endothelial and muscle cells. Thus, grape stem extracts may be used for developing antioxidant food supplements or biofunctional foods. However, it was also found that the polyphenolic composition of grape stem

  17. Polyphenolic composition of grape stem extracts affects antioxidant activity in endothelial and muscle cells

    PubMed Central

    GOUTZOURELAS, NIKOLAOS; STAGOS, DIMITRIOS; SPANIDIS, YPATIOS; LIOSI, MARIA; APOSTOLOU, ANNA; PRIFTIS, ALEXANDROS; HAROUTOUNIAN, SERKO; SPANDIDOS, DEMETRIOS A.; TSATSAKIS, ARISTIDIS M.; KOURETAS, DEMETRIOS

    2015-01-01

    The aim of the present study was the assessment of the antioxidant effects of polyphenolic extracts derived from the stems of three Greek grape varieties (Moshomayro, Mavrotragano and Mandilaria) in endothelial (EA.hy926) and muscle (C2C12) cells. We also investigated the effects of the polyphenolic composition on the antioxidant effects of the grape stem extracts. For this purpose, the endothelial and muscle cells were treated with low non-cytotoxic concentrations of the extracts for 24 h in order to assess the effects of the extracts on cellular redox status using oxidative stress biomarkers. The oxidative stress markers were thiobarbituric acid reactive substances (TBARS), protein carbonyl (CARB) levels, reactive oxygen species (ROS) levels and glutathione (GSH) levels. The results revealed that treatment of the EA.hy926 cells with Mandilaria extract significantly decreased the TBARS levels by 14.8% and the CARB levels by 25.9 %, while it increased the GSH levels by 15.8% compared to the controls. Moreover, treatment of the EA.hy926 cells with Mavrotragano extract significantly increased the GSH levels by 20.2%, while it significantly decreased the TBARS and CARB levels by 12.5% and 16.6%, respectively. Treatment of the C2C12 cells with Mandilaria extract significantly decreased the TBARS levels by 47.3 %, the CARB levels by 39.0 % and the ROS levels by 21.8%, while it increased the GSH levels by 22.6% compared to the controls. Moreover, treatment of the C2C12 cells with Mavrotragano significantly decreased the TBARS, CARB and ROS levels by 36.2%, 35.9% and 16.5%, respectively. In conclusion, to the best of our knowledgel, our results demonstrate for the first time that treatment with grape stem extracts at low concentrations improves the redox status of endothelial and muscle cells. Thus, grape stem extracts may be used for developing antioxidant food supplements or biofunctional foods. However, it was also found that the polyphenolic composition of grape stem

  18. Polyphenols as possible bioprotectors against cytotoxicity and DNA damage induced by ochratoxin A.

    PubMed

    Cariddi, L N; Sabini, M C; Escobar, F M; Montironi, I; Mañas, F; Iglesias, D; Comini, L R; Sabini, L I; Dalcero, A M

    2015-05-01

    The present study aimed to investigate the protective effects of luteolin (L), chlorogenic acid (ChlA) and caffeic acid (CafA) against cyto-genotoxic effects caused by OTA. Vero cells and rat lymphocytes were used and viability was measured by neutral red uptake, MTT and trypan blue dye exclusion method. L (50 and 100μg/mL), ChlA (100 and 200μg/mL) and CafA (10-50μg/mL) reduced the damage induced by OTA (10μg/mL) on both cells type shown a good protective effect. The comet and micronucleus tests in Balb/c mice were performed. ChlA (10mg/kg bw) reduced OTA (0.85mg/kg bw)-induced DNA damage on blood and bone marrow cells, CafA (10mg/kg bw) showed protective effect only in blood cells and luteolin (2.5mg/kg bw) failed to protect DNA integrity on cells. In conclusion, polyphenols tested reduced the toxicity caused by OTA on different target cells with good protective effect, being ChlA the compound that showed the best effects. PMID:25867686

  19. Inhibitory effects of low molecular weight polyphenolics from Inonotus obliquus on human DNA topoisomerase activity and cancer cell proliferation.

    PubMed

    Kuriyama, Isoko; Nakajima, Yuki; Nishida, Hiroshi; Konishi, Tetsuya; Takeuchi, Toshifumi; Sugawara, Fumio; Yoshida, Hiromi; Mizushina, Yoshiyuki

    2013-08-01

    Low molecular weight (LMW) polyphenolics containing a polyhydroxylated benzyl moiety are abundant in medicinal plants. In the present study, we report on the activities of seven LMW polyphenolics isolated from Inonotus obliquus, a medicinal mushroom. The isolated compounds included caffeic acid (CA), 3,4-dihydroxybenzalacetone (DBL), gallic acid, syringic acid, protocatechuic acid, 3,4-dihydroxybenzaldehyde and 2,5-dihydroxyterephthalic acid. We analyzed their inhibitory effects on DNA polymerase (pol) and DNA topoisomerase (topo), and their effects on human cancer cell growth. All isolated compounds inhibited human topo II activity; the most potent were DBL and CA, which contain a catechol propanoid moiety. CA and DBL inhibited the activity of human topo I, whereas other compounds had no effect. No compound modulated the activities of 11 mammalian pol species or other DNA metabolic enzymes, including T7 RNA polymerase, mouse IMP dehydrogenase (type II), T4 polynucleotide kinase and bovine deoxyribonuclease I. CA and DBL markedly suppressed the proliferation of human colon HCT116 carcinoma cells with an LD50 of 70.0 and 49.4 µM, respectively, and halted the cell cycle in the G2/M phase. The suppressive effect of these compounds on cancer cell growth correlated with their ability to inhibit topo II. These results suggest that CA- and DBL-dependent decreases in cell proliferation are due to the inhibition of cellular topo II. The mechanism of action of these catechol propanoid compounds and the implication for their use as anticancer agents are discussed. PMID:23799608

  20. Impact of Dietary Polyphenols on Carbohydrate Metabolism

    PubMed Central

    Hanhineva, Kati; Törrönen, Riitta; Bondia-Pons, Isabel; Pekkinen, Jenna; Kolehmainen, Marjukka; Mykkänen, Hannu; Poutanen, Kaisa

    2010-01-01

    Polyphenols, including flavonoids, phenolic acids, proanthocyanidins and resveratrol, are a large and heterogeneous group of phytochemicals in plant-based foods, such as tea, coffee, wine, cocoa, cereal grains, soy, fruits and berries. Growing evidence indicates that various dietary polyphenols may influence carbohydrate metabolism at many levels. In animal models and a limited number of human studies carried out so far, polyphenols and foods or beverages rich in polyphenols have attenuated postprandial glycemic responses and fasting hyperglycemia, and improved acute insulin secretion and insulin sensitivity. The possible mechanisms include inhibition of carbohydrate digestion and glucose absorption in the intestine, stimulation of insulin secretion from the pancreatic β–cells, modulation of glucose release from the liver, activation of insulin receptors and glucose uptake in the insulin-sensitive tissues, and modulation of intracellular signalling pathways and gene expression. The positive effects of polyphenols on glucose homeostasis observed in a large number of in vitro and animal models are supported by epidemiological evidence on polyphenol-rich diets. To confirm the implications of polyphenol consumption for prevention of insulin resistance, metabolic syndrome and eventually type 2 diabetes, human trials with well-defined diets, controlled study designs and clinically relevant end-points together with holistic approaches e.g., systems biology profiling technologies are needed. PMID:20480025

  1. Polyphenols: well beyond the antioxidant capacity: gallic acid and related compounds as neuroprotective agents: you are what you eat!

    PubMed

    Daglia, Maria; Di Lorenzo, Arianna; Nabavi, Seyed F; Talas, Zeliha S; Nabavi, Seyed M

    2014-01-01

    Gallic acid (3,4,5-trihydroxybenzoic acid) is a phenolic acid widely distributed in many different families of higher plants, both in free state, and as a part of more complex molecules, such as ester derivatives or polymers. In nature, gallic acid and its derivatives are present in nearly every part of the plant, such as bark, wood, leaf, fruit, root and seed. They are present in different concentrations in common foodstuffs such as blueberry, blackberry, strawberry, plums, grapes, mango, cashew nut, hazelnut, walnut, tea, wine and so on. After consumption, about 70% of gallic acid is adsorbed and then excreted in the urine as 4-O-methylgallic acid. Differently, the ester derivatives of gallic acid, such as catechin gallate ester or gallotannins, are hydrolyzed to gallic acid before being metabolized to methylated derivatives. Gallic acid is a well known antioxidant compounds which has neuroprotective actions in different models of neurodegeneration, neurotoxicity and oxidative stress. In this review, we discuss about the neuroprotective actions of gallic acid and derivatives and their potential mechanisms of action. PMID:24938889

  2. Abscisic Acid and LATERAL ROOT ORGAN DEFECTIVE/NUMEROUS INFECTIONS AND POLYPHENOLICS Modulate Root Elongation via Reactive Oxygen Species in Medicago truncatula1[W][OPEN

    PubMed Central

    Zhang, Chang; Bousquet, Amanda; Harris, Jeanne M.

    2014-01-01

    Abscisic acid (ABA) modulates root growth in plants grown under normal and stress conditions and can rescue the root growth defects of the Medicago truncatula lateral root-organ defective (latd) mutant. Here, we demonstrate that reactive oxygen species (ROS) function downstream of ABA in the regulation of root growth by controlling cell elongation. We also show that the MtLATD/NUMEROUS INFECTIONS AND POLYPHENOLICS (NIP) nitrate transporter is required for ROS homeostasis and cell elongation in roots and that this balance is perturbed in latd mutants, leading to an excess of superoxide and hydrogen peroxide and a corresponding decrease in cell elongation. We found that expression of the superoxide-generating NADPH oxidase genes, MtRbohA and MtRbohC (for respiratory burst oxidase homologs), is increased in latd roots and that inhibition of NADPH oxidase activity pharmacologically can both reduce latd root ROS levels and increase cell length, implicating NADPH oxidase function in latd root growth defects. Finally, we demonstrate that ABA treatment alleviates ectopic ROS accumulation in latd roots, restores MtRbohC expression to wild-type levels, and promotes an increase in cell length. Reducing the expression of MtRbohC using RNA interference leads to increased root elongation in both wild-type and latd roots. These results reveal a mechanism by which the MtLATD/NIP nitrate transporter and ABA modulate root elongation via superoxide generation by the MtRbohC NADPH oxidase. PMID:25192698

  3. Voltammetric determination of polyphenolic content in pomegranate juice using a poly(gallic acid)/multiwalled carbon nanotube modified electrode.

    PubMed

    Abdel-Hamid, Refat; Newair, Emad F

    2016-01-01

    A simple and sensitive poly(gallic acid)/multiwalled carbon nanotube modified glassy carbon electrode (PGA/MWCNT/GCE) electrochemical sensor was prepared for direct determination of the total phenolic content (TPC) as gallic acid equivalent. The GCE working electrode was electrochemically modified and characterized using scanning electron microscope (SEM), cyclic voltammetry (CV), chronoamperometry and chronocoulometry. It was found that gallic acid (GA) exhibits a superior electrochemical response on the PGA/MWCNT/GCE sensor in comparison with bare GCE. The results reveal that a PGA/MWCNT/GCE sensor can remarkably enhance the electro-oxidation signal of GA as well as shift the peak potentials towards less positive potential values. The dependence of peak current on accumulation potential, accumulation time and pH were investigated by square-wave voltammetry (SWV) to optimize the experimental conditions for the determination of GA. Using the optimized conditions, the sensor responded linearly to a GA concentration throughout the range of 4.97 × 10(-6) to 3.38 × 10(-5) M with a detection limit of 3.22 × 10(-6) M (S/N = 3). The fabricated sensor shows good selectivity, stability, repeatability and (101%) recovery. The sensor was successfully utilized for the determination of total phenolic content in fresh pomegranate juice without interference of ascorbic acid, fructose, potassium nitrate and barbituric acid. The obtained data were compared with the standard Folin-Ciocalteu spectrophotometric results. PMID:27547628

  4. Voltammetric determination of polyphenolic content in pomegranate juice using a poly(gallic acid)/multiwalled carbon nanotube modified electrode

    PubMed Central

    Newair, Emad F

    2016-01-01

    Summary A simple and sensitive poly(gallic acid)/multiwalled carbon nanotube modified glassy carbon electrode (PGA/MWCNT/GCE) electrochemical sensor was prepared for direct determination of the total phenolic content (TPC) as gallic acid equivalent. The GCE working electrode was electrochemically modified and characterized using scanning electron microscope (SEM), cyclic voltammetry (CV), chronoamperometry and chronocoulometry. It was found that gallic acid (GA) exhibits a superior electrochemical response on the PGA/MWCNT/GCE sensor in comparison with bare GCE. The results reveal that a PGA/MWCNT/GCE sensor can remarkably enhance the electro-oxidation signal of GA as well as shift the peak potentials towards less positive potential values. The dependence of peak current on accumulation potential, accumulation time and pH were investigated by square-wave voltammetry (SWV) to optimize the experimental conditions for the determination of GA. Using the optimized conditions, the sensor responded linearly to a GA concentration throughout the range of 4.97 × 10−6 to 3.38 × 10−5 M with a detection limit of 3.22 × 10−6 M (S/N = 3). The fabricated sensor shows good selectivity, stability, repeatability and (101%) recovery. The sensor was successfully utilized for the determination of total phenolic content in fresh pomegranate juice without interference of ascorbic acid, fructose, potassium nitrate and barbituric acid. The obtained data were compared with the standard Folin–Ciocalteu spectrophotometric results. PMID:27547628

  5. Characterisation of Polyphenols in Terminalia arjuna Bark Extract.

    PubMed

    Saha, Anumita; Pawar, V M; Jayaraman, Sujatha

    2012-07-01

    The bark of Terminalia arjuna is known for its heart-health benefits in ayurvedic literature. This has been further supported by in vivo studies on animal and human volunteers. But there is no detailed study on identification of the active ingredients such as polyphenols. Polyphenols possesses antioxidant properties and are well-known health actives, it is important to characterise polyphenols in Terminalia arjuna. Aqueous extract of Terminalia arjuna bark was analysed for its composition and molecular weight distribution by dialysis. Compositional analysis revealed that it has 44% polyphenols and dialysis study showed that 70% of the polyphenols have molecular weight greater than 3.5 kDa. High performance liquid chromatography and liquid chromatography-mass spectrometry analysis of Terminalia arjuna, confirmed that it contains flavon-3-ols such as (+)-catechin, (+)-gallocatechin and (-)-epigallocatechin. Phenolic acids such as gallic acid, ellagic acid and its derivatives were also found in Terminalia arjuna extract. Ellagic acid derivatives were isolated and their spectral studies indicated that isolated compounds were 3-O-methyl-ellagic acid 4-O-β-D-xylopyranoside, ellagic acid and 3-O-methyl ellagic acid 3-O-rhamnoside. Hydrolysis and thiolysis studies of high molecular weight polyphenols indicated that they are proanthocyanidins. Given these results, it may be possible to attribute the heart-health effects of Terminalia arjuna to these polyphenols which may be responsible for the endothelial benefit functions like tea. PMID:23626389

  6. Characterisation of Polyphenols in Terminalia arjuna Bark Extract

    PubMed Central

    Saha, Anumita; Pawar, V. M.; Jayaraman, Sujatha

    2012-01-01

    The bark of Terminalia arjuna is known for its heart-health benefits in ayurvedic literature. This has been further supported by in vivo studies on animal and human volunteers. But there is no detailed study on identification of the active ingredients such as polyphenols. Polyphenols possesses antioxidant properties and are well-known health actives, it is important to characterise polyphenols in Terminalia arjuna. Aqueous extract of Terminalia arjuna bark was analysed for its composition and molecular weight distribution by dialysis. Compositional analysis revealed that it has 44% polyphenols and dialysis study showed that 70% of the polyphenols have molecular weight greater than 3.5 kDa. High performance liquid chromatography and liquid chromatography–mass spectrometry analysis of Terminalia arjuna, confirmed that it contains flavon-3-ols such as (+)-catechin, (+)-gallocatechin and (−)-epigallocatechin. Phenolic acids such as gallic acid, ellagic acid and its derivatives were also found in Terminalia arjuna extract. Ellagic acid derivatives were isolated and their spectral studies indicated that isolated compounds were 3-O-methyl-ellagic acid 4-O-β-D-xylopyranoside, ellagic acid and 3-O-methyl ellagic acid 3-O-rhamnoside. Hydrolysis and thiolysis studies of high molecular weight polyphenols indicated that they are proanthocyanidins. Given these results, it may be possible to attribute the heart-health effects of Terminalia arjuna to these polyphenols which may be responsible for the endothelial benefit functions like tea. PMID:23626389

  7. Use of Polyphenolic Compounds in Dermatologic Oncology.

    PubMed

    Costa, Adilson; Bonner, Michael Yi; Arbiser, Jack L

    2016-08-01

    Polyphenols are a widely used class of compounds in dermatology. While phenol itself, the most basic member of the phenol family, is chemically synthesized, most polyphenolic compounds are found in plants and form part of their defense mechanism against decomposition. Polyphenolic compounds, which include phenolic acids, flavonoids, stilbenes, and lignans, play an integral role in preventing the attack on plants by bacteria and fungi, as well as serving as cross-links in plant polymers. There is also mounting evidence that polyphenolic compounds play an important role in human health as well. One of the most important benefits, which puts them in the spotlight of current studies, is their antitumor profile. Some of these polyphenolic compounds have already presented promising results in either in vitro or in vivo studies for non-melanoma skin cancer and melanoma. These compounds act on several biomolecular pathways including cell division cycle arrest, autophagy, and apoptosis. Indeed, such natural compounds may be of potential for both preventive and therapeutic fields of cancer. This review evaluates the existing scientific literature in order to provide support for new research opportunities using polyphenolic compounds in oncodermatology. PMID:27164914

  8. A review on protocatechuic Acid and its pharmacological potential.

    PubMed

    Kakkar, Sahil; Bais, Souravh

    2014-01-01

    Flavonoids and polyphenols are heterocyclic molecules that have been associated with beneficial effects on human health, such as reducing the risk of various diseases like cancer, diabetes, and cardiovascular and brain diseases. Protocatechuic acid (PCA) is a type of widely distributed naturally occurring phenolic acid. PCA has structural similarity with gallic acid, caffeic acid, vanillic acid, and syringic acid which are well-known antioxidant compounds. More than 500 plants contain PCA as active constituents imparting various pharmacological activity and these effects are due to their antioxidant activities, along with other possible mechanisms, such as anti-inflammatory properties and interaction with several enzymes. Over the past two decades, there have been an increasing number of publications on polyphenols and flavonoids, which demonstrate the importance of understanding the chemistry behind the antioxidant activities of both natural and synthesized compounds, considering the benefits from their dietary ingestion as well as pharmacological use. This work aims to review the pharmacological effects of PCA molecules in humans and the structural aspects that contribute to these effects. PMID:25006494

  9. A Review on Protocatechuic Acid and Its Pharmacological Potential

    PubMed Central

    Kakkar, Sahil; Bais, Souravh

    2014-01-01

    Flavonoids and polyphenols are heterocyclic molecules that have been associated with beneficial effects on human health, such as reducing the risk of various diseases like cancer, diabetes, and cardiovascular and brain diseases. Protocatechuic acid (PCA) is a type of widely distributed naturally occurring phenolic acid. PCA has structural similarity with gallic acid, caffeic acid, vanillic acid, and syringic acid which are well-known antioxidant compounds. More than 500 plants contain PCA as active constituents imparting various pharmacological activity and these effects are due to their antioxidant activities, along with other possible mechanisms, such as anti-inflammatory properties and interaction with several enzymes. Over the past two decades, there have been an increasing number of publications on polyphenols and flavonoids, which demonstrate the importance of understanding the chemistry behind the antioxidant activities of both natural and synthesized compounds, considering the benefits from their dietary ingestion as well as pharmacological use. This work aims to review the pharmacological effects of PCA molecules in humans and the structural aspects that contribute to these effects. PMID:25006494

  10. Polyphenols and Glycemic Control

    PubMed Central

    Kim, Yoona; Keogh, Jennifer B.; Clifton, Peter M.

    2016-01-01

    Growing evidence from animal studies supports the anti-diabetic properties of some dietary polyphenols, suggesting that dietary polyphenols could be one dietary therapy for the prevention and management of Type 2 diabetes. This review aims to address the potential mechanisms of action of dietary polyphenols in the regulation of glucose homeostasis and insulin sensitivity based on in vitro and in vivo studies, and to provide a comprehensive overview of the anti-diabetic effects of commonly consumed dietary polyphenols including polyphenol-rich mixed diets, tea and coffee, chocolate and cocoa, cinnamon, grape, pomegranate, red wine, berries and olive oil, with a focus on human clinical trials. Dietary polyphenols may inhibit α-amylase and α-glucosidase, inhibit glucose absorption in the intestine by sodium-dependent glucose transporter 1 (SGLT1), stimulate insulin secretion and reduce hepatic glucose output. Polyphenols may also enhance insulin-dependent glucose uptake, activate 5′ adenosine monophosphate-activated protein kinase (AMPK), modify the microbiome and have anti-inflammatory effects. However, human epidemiological and intervention studies have shown inconsistent results. Further intervention studies are essential to clarify the conflicting findings and confirm or refute the anti-diabetic effects of dietary polyphenols. PMID:26742071

  11. Polyphenols and Glycemic Control.

    PubMed

    Kim, Yoona; Keogh, Jennifer B; Clifton, Peter M

    2016-01-01

    Growing evidence from animal studies supports the anti-diabetic properties of some dietary polyphenols, suggesting that dietary polyphenols could be one dietary therapy for the prevention and management of Type 2 diabetes. This review aims to address the potential mechanisms of action of dietary polyphenols in the regulation of glucose homeostasis and insulin sensitivity based on in vitro and in vivo studies, and to provide a comprehensive overview of the anti-diabetic effects of commonly consumed dietary polyphenols including polyphenol-rich mixed diets, tea and coffee, chocolate and cocoa, cinnamon, grape, pomegranate, red wine, berries and olive oil, with a focus on human clinical trials. Dietary polyphenols may inhibit α-amylase and α-glucosidase, inhibit glucose absorption in the intestine by sodium-dependent glucose transporter 1 (SGLT1), stimulate insulin secretion and reduce hepatic glucose output. Polyphenols may also enhance insulin-dependent glucose uptake, activate 5' adenosine monophosphate-activated protein kinase (AMPK), modify the microbiome and have anti-inflammatory effects. However, human epidemiological and intervention studies have shown inconsistent results. Further intervention studies are essential to clarify the conflicting findings and confirm or refute the anti-diabetic effects of dietary polyphenols. PMID:26742071

  12. Binding geometry, stoichiometry, and thermodynamics of cyclomalto-oligosaccharide (cyclodextrin) inclusion complex formation with chlorogenic acid, the major substrate of apple polyphenol oxidase.

    PubMed

    Irwin, P L; Pfeffer, P E; Doner, L W; Sapers, G M; Brewster, J D; Nagahashi, G; Hicks, K B

    1994-03-18

    The inclusion complexes of cyclomaltohexaose (alpha-CD), cyclomaltoheptaose (beta-CD), cyclomaltooctaose (gamma-CD), and polymerized beta-CD (beta-CDn) with chlorogenic acid (CA), the major substrate of apple fruit polyphenol oxidase (PPO), were studied with regard to pH, ionic strength, and temperature in model buffer systems and apple juice. The thermodynamics of CD.CA inclusion complex formation, which were studied in solution using UV spectrophotometry, displayed enthalpy-entropy compensation typical of processes driven by solvation phenomena. We also found that the apparent association constants (K) of the CD.CA equilibrium were relatively insensitive to pH for beta-CD, compared to alpha- and gamma-CDs, but were subject to substantial enhancement at low ionic strengths. The beta-CD.CA inclusion complex was also characterized for binding geometry and stoichiometry at 9.4 T and 25 degrees C in 0.05 M Na phosphate buffer by 1H NMR spectroscopy. A 1:1 stoichiometric ratio for the complex was found using the method of continuous variations. 1H Spin-lattice relaxation and chemical-shift data indicate that the phenolic ring of CA docks within the cavity of beta-CD. The Ks for beta-, alpha-, and gamma-CD determined in apple juice, which contains a mixture of PPO substrates, were found to correlate with PPO activity-related data. Apple juice, treated with beta-CDn, did not brown until CA was added back. These latter findings strongly argue that the mechanism for inhibition of juice browning with cyclodextrins was mainly due to the binding of PPO substrates and not some other means such as enzyme inactivation via sequestration of Cu2+ by CDs. PMID:8194069

  13. The effect of high polyphenol oxidase grass silage on metabolism of polyunsaturated fatty acids and nitrogen across the rumen of beef steers.

    PubMed

    Lee, M R F; Theobald, V J; Gordon, N; Leyland, M; Tweed, J K S; Fychan, R; Scollan, N D

    2014-11-01

    Polyphenol oxidase (PPO) activity in red clover (Trifolium pratense) has been reported to reduce both proteolysis and lipolysis, resulting in greater N use efficiency and protection of PUFA across the rumen. Although high levels of PPO have been reported in grasses such as cocksfoot (orchard grass; Dactylis glomerata), no in vivo research has determined whether grass PPO elicits the same response as red clover PPO. To test the hypothesis that silage ensiled from grass with high levels of PPO protects N and PUFA across the rumen, 6 steers with ruminal and duodenal cannulas were offered cocksfoot silage (CO; high-PPO grass), perennial ryegrass silage (PR; Lolium perenne; low-PPO grass), or red clover silage (RC; high-PPO control) at 16 g DM/kg BW daily with the experiment consisting of two 3 × 3 Latin squares with 21-d periods, consisting of 12 d of diet adaptation, 6 d of duodenal marker infusion, 2 d of duodenal sampling, and 1 d of ruminal sampling. All silages were well preserved, with DM of 34.4, 55.3, and 45.4% for CO, PR, and RC. Activity of PPO in silages was low due to deactivation but was greater in CO than either PR or RC (0.15 vs. 0.05 and 0.08 μkatal/g DM). Protein-bound phenol (mg/g DM) as a measure of the degree of oxidation and an indication of PPO protection was greatest for RC (15.9) but comparable for PR (10.1) and CO (12.2). Biohydrogenation of C18 PUFA was significantly lower on RC compared to the 2 grass silages with CO greater than PR. Despite lower levels of total fatty acid intake and subsequent duodenal flow, CO resulted in greater levels of phytanic acid and total branched and odd chain fatty acids in duodenal digesta than RC or PR. Ruminal ammonia concentration was greatest for RC, with no difference between the grasses. Duodenal flow of microbial N and efficiency of microbial protein synthesis were lowest for CO and comparable for RC and PR. The CO (high-grass PPO) did not result in elevated levels of C18 PUFA escaping the rumen or

  14. Ferulic Acid, an Angelica sinensis-Derived Polyphenol, Slows the Progression of Membranous Nephropathy in a Mouse Model

    PubMed Central

    Cheng, Chao-Wen; Chang, Wen-Liang; Chang, Li-Cheng; Wu, Chia-Chao; Lin, Yuh-Feng; Chen, Jin-Shuen

    2012-01-01

    Membranous nephropathy (MN) is a leading cause of adult nephrotic syndrome but lacks adequate treatment. Different extracts of Angelica sinensis (AS) and one of its active compounds, ferulic acid (FA), were used to evaluate the therapeutic effects in a MN mouse model. The MN model was grouped into three subgroups: no treatment (N-T), treatment at induction of MN (Pre-T), and treatment after full-blown MN (Post-T). The results showed that the methanol (ME) layer of AS extract exhibited a therapeutic effect on MN-induced proteinuria. The ME layer-enriched compound, FA, improved the hypoalbuminemia, hyperlipidemia, and proteinuria in both Pre-T and Post-T groups. Ferulic acid also reduced the formation of oxidative protein products and increased the synthesis of antioxidant enzymes in groups Pre-T and Post-T. Regarding angiogenesis factors, the antiangiogenic factors in renal glomeruli were increased in group N-T, but, after FA treatment, only one of the antiangiogenic factors, thrombospondin-1, showed a significant decrease. Furthermore, the expression of Th2 predominant showed significant decrease in both Pre-T and Post-T groups when compared to that of N-T group. In summary, FA retarded the progression of MN, and the mechanisms involved the regulation of oxidative stresses, angiogenic and antiangiogenic factors, and attenuation of Th2 response. PMID:22844329

  15. Polyphenolic Composition and Evaluation of Antioxidant Activity, Osmotic Fragility and Cytotoxic Effects of Raphiodon echinus (Nees & Mart.) Schauer.

    PubMed

    Duarte, Antonia Eliene; Waczuk, Emily Pansera; Roversi, Katiane; da Silva, Maria Arlene Pessoa; Barros, Luiz Marivando; da Cunha, Francisco Assis Bezerra; de Menezes, Irwin Rose Alencar; da Costa, José Galberto Martins; Boligon, Aline Augusti; Ademiluyi, Adedayo Oluwaseun; Kamdem, Jean Paul; Rocha, João Batista Teixeira; Burger, Marilise Escobar

    2015-01-01

    Raphiodon echinus (R. echinus) is used in Brazilian folk medicine for the treatment of inflammation, coughs, and infectious diseases. However, no information is available on the potential antioxidant, cytotoxicity and genotoxicity of this plant. In this study, the polyphenolic constituents, antioxidant capacity and potential toxic effects of aqueous and ethanolic extracts of R. echinus on human erythrocytes and leukocytes were investigated for the first time. R. echinus extracts showed the presence of Gallic, chlorogenic, caffeic and ellagic acids, rutin, quercitrin and quercetin. Aqueous and ethanolic extracts of R. echinus exhibited antioxidant activity in DPPH radical scavenging with IC50 = 111.9 μg/mL (EtOH extract) and IC50 = 227.9 μg/mL (aqueous extract). The extracts inhibited Fe(2+) (10 μM) induced thiobarbituric acid reactive substances (TBARS) formation in rat brain and liver homogenates. The extracts (30-480 μg/mL) did not induce genotoxicity, cytotoxicity or osmotic fragility in human blood cells. The findings of this present study therefore suggest that the therapeutic effect of R. echinus may be, in part, related to its antioxidant potential. Nevertheless, further in vitro and in vivo studies are required to ascertain the safety margin of its use in folk medicine. PMID:26729080

  16. Dietary Phenolic Acids Act as Effective Antioxidants in Membrane Models and in Cultured Cells, Exhibiting Proapoptotic Effects in Leukaemia Cells

    PubMed Central

    Zambonin, Laura; Caliceti, Cristiana; Vieceli Dalla Sega, Francesco; Fiorentini, Diana; Hrelia, Silvana; Landi, Laura; Prata, Cecilia

    2012-01-01

    Caffeic, syringic, and protocatechuic acids are phenolic acids derived directly from food intake or come from the gut metabolism of polyphenols. In this study, the antioxidant activity of these compounds was at first evaluated in membrane models, where caffeic acid behaved as a very effective chain-breaking antioxidant, whereas syringic and protocatechuic acids were only retardants of lipid peroxidation. However, all three compounds acted as good scavengers of reactive species in cultured cells subjected to exogenous oxidative stress produced by low level of H2O2. Many tumour cells are characterised by increased ROS levels compared with their noncancerous counterparts. Therefore, we investigated whether phenolic acids, at low concentrations, comparable to those present in human plasma, were able to decrease basal reactive species. Results show that phenolic acids reduced ROS in a leukaemia cell line (HEL), whereas no effect was observed in normal cells, such as HUVEC. The compounds exhibited no toxicity to normal cells while they decreased proliferation in leukaemia cells, inducing apoptosis. In the debate on optimal ROS-manipulating strategies in cancer therapy, our work in leukaemia cells supports the antioxidant ROS-depleting approach. PMID:22792417

  17. Ellagic acid, a natural polyphenol protects rat peripheral blood lymphocytes against nicotine-induced cellular and DNA damage in vitro: with the comparison of N-acetylcysteine.

    PubMed

    Sudheer, Adluri Ram; Muthukumaran, Shanmugavelu; Devipriya, Nagarajan; Menon, Venugopal Padmanabhan

    2007-01-25

    The present work is aimed at evaluating the protective effect of ellagic acid (EA), a natural polyphenolic compound that is widely distributed in fruits and nuts against nicotine-induced toxicity in rat peripheral blood lymphocytes. The effect of EA against nicotine toxicity was compared with N-acetylcysteine (NAC), a well-known antioxidant. Lymphocytes were exposed to nicotine at the doses of 0.125, 0.25, 0.5, 1, 2, 3 and 4 mM for 1h in culture media. Thiobarbituric acid reactive substances (TBARS), a lipid peroxidative marker and reduced glutathione (GSH), as indicative of endogenous antioxidant status were analyzed to fix the optimum dose. The lowest concentration eliciting significant damage was 1 mM nicotine and maximum damage was observed with 3 mM concentration, as evidenced by increased levels of TBARS and decreased levels of GSH. Hence, the test concentration was fixed at 3 mM nicotine. To establish most effective protective support we used five different concentrations of EA (10, 50, 100, 150 and 300 microM) against 3 mM nicotine. A dose-dependent inhibitory effect was observed with all doses of EA. Maximum protection was observed at the dose of 100 microM EA. So, 100 microM dose was used for further studies. We have tested five different concentrations of NAC-0.25, 0.5, 1, 2 and 4 mM to elucidate the optimum protective dose against nicotine toxicity. One millimolar NAC showed a significant protection against nicotine toxicity. Protective effect of EA against nicotine toxicity was elucidated by analyzing the lipid peroxidative index, viz., TBARS, hydroperoxides (HP) and endogenous antioxidant status, viz., superoxide dismutase (SOD), catalase (CAT), glutathione peroxidase (GPx), reduced glutathione (GSH), Vitamins A, E and C. DNA damage and repair were assessed by using alkaline single-cell microgel electrophoresis (Comet assay) and micronucleus assay. There was a significant increase in the levels of lipid peroxidative index, severity in DNA damage and

  18. Total polyphenolic contents and in vitro antioxidant properties of eight Sida species from Western Ghats, India

    PubMed Central

    Subramanya, M. D.; Pai, Sandeep R.; Upadhya, Vinayak; Ankad, Gireesh M.; Bhagwat, Shalini S.; Hegde, Harsha V.

    2015-01-01

    Background: Sida L., is a medicinally important genus, the species of which are widely used in traditional systems of medicine in India. Pharmacologically, roots are known for anti-tumor, anti-HIV, hepatoprotective, and many other properties. Phenolic antioxidants help in reducing oxidative stress occurring during treatment of such diseases. Objective: The study aimed to evaluate and compare polyphenol contents and antioxidant properties of eight selected species of Sida from Western Ghats, India. Materials and Methods: Methanolic root extracts (10% w/v) of Sida species, viz., S. acuta, S. cordata, S. cordifolia, S. indica, S. mysorensis, S. retusa, S. rhombifolia, and S. spinosa were analyzed. Results: Sida cordifolia possessed highest total phenolic content (TPC: 1.92 ± 0.10 mg Caffeic Acid Equivalent/g and 2.13 ± 0.11 mg Tannic Acid Equivalant/g), total flavonoid content (TF: 2.60 ± 0.13 mg Quercetin Equivalent/g) and also possessed highest antioxidant activities in 2,2-diphenylpicrylhydrazyl (DPPH) radical scavenging (51.31 ± 2.57% Radical Scavenging Activity, (RSA); Trolox Equivalent Antioxidant Capacity: 566.25 ± 28.31μM; Ascorbic acid Equivalent Antioxidant Capacity: 477.80 ± 23.89 μM) and Ferric Reducing Antioxidant Power assays (TEAC: 590.67 ± 29.53 μM; AEAC: 600.67 ± 30.03 μM). Unlike DPPH and Ferric Reducing Antioxidant Power (FRAP) activity, 2, 2′-Azinobis (3-ethyl Benzo Thiazoline-6-Sulfonic acid) ABTS+ antioxidant activity was highest in S. indica (TEAC: 878.44 ± 43.92 μM; AEAC 968.44 ± 48.42 μM). It was significant to note that values of AEAC (μM) for all the antioxidant activities analyzed were higher than that of TEAC. Conclusion: The high contents of phenolic compounds in the root extracts of selected Sida species have direct correlation with their antioxidant properties. Conclusively, roots of S. cordifolia can be considered as the potential source of polyphenols and antioxidants. PMID:25878460

  19. Polyphenols and gastrointestinal diseases

    PubMed Central

    Dryden, Gerald W.; Song, Ming; McClain, Craig

    2014-01-01

    Purpose of review This article will review the role of polyphenols in gastrointestinal diseases. Ingested polyphenols are concentrated in the gastrointestinal tract and are not well absorbed into the rest of the body. Thus, the high luminal concentrations achieved support a potential for therapeutic uses in the gastrointestinal tract. Additionally, there is great interest from the general public in complementary and alternative medicine. Recent findings Dietary polyphenols are a major source of antioxidants consumed by humans. Polyphenols possess not only antioxidant properties but also antiviral, antibacterial, antiinflammatory and anticarcinogenic effects, as well as the ability to modulate certain signaling pathways such as nuclear factor-κB activation. Green tea polyphenols have been shown to have efficacy in various models of inflammatory bowel disease. Silymarin, or milk thistle, is hepatoprotective against many forms of experimental liver injury and is widely used in human liver diseases, such as hepatitis C and alcoholic cirrhosis, with an excellent safety profile (but with unclear efficacy). Summary Substantial in-vitro and animal studies support the beneficial effects of polyphenols in many gastrointestinal diseases. Well designed multicenter trials in humans, such as those called for in the 2005 National Institutes of Health Requests for Applications for Silymarin Centers, will be critical for defining the safety, appropriate dosing and therapeutic efficacy of such agents. PMID:16462174

  20. Accumulation of Phenolic Compounds and Expression Profiles of Phenolic Acid Biosynthesis-Related Genes in Developing Grains of White, Purple, and Red Wheat

    PubMed Central

    Ma, Dongyun; Li, Yaoguang; Zhang, Jian; Wang, Chenyang; Qin, Haixia; Ding, Huina; Xie, Yingxin; Guo, Tiancai

    2016-01-01

    Polyphenols in whole grain wheat have potential health benefits, but little is known about the expression patterns of phenolic acid biosynthesis genes and the accumulation of phenolic acid compounds in different-colored wheat grains. We found that purple wheat varieties had the highest total phenolic content (TPC) and antioxidant activity. Among phenolic acid compounds, bound ferulic acid, vanillic, and caffeic acid levels were significantly higher in purple wheat than in white and red wheat, while total soluble phenolic acid, soluble ferulic acid, and vanillic acid levels were significantly higher in purple and red wheat than in white wheat. Ferulic acid and syringic acid levels peaked at 14 days after anthesis (DAA), whereas p-coumaric acid and caffeic acid levels peaked at 7 DAA, and vanillic acid levels gradually increased during grain filling and peaked near ripeness (35 DAA). Nine phenolic acid biosynthesis pathway genes (TaPAL1, TaPAL2, TaC3H1, TaC3H2, TaC4H, Ta4CL1, Ta4CL2, TaCOMT1, and TaCOMT2) exhibited three distinct expression patterns during grain filling, which may be related to the different phenolic acids levels. White wheat had higher phenolic acid contents and relatively high gene expression at the early stage, while purple wheat had the highest phenolic acid contents and gene expression levels at later stages. These results suggest that the expression of phenolic acid biosynthesis genes may be closely related to phenolic acids accumulation. PMID:27148345

  1. Accumulation of Phenolic Compounds and Expression Profiles of Phenolic Acid Biosynthesis-Related Genes in Developing Grains of White, Purple, and Red Wheat.

    PubMed

    Ma, Dongyun; Li, Yaoguang; Zhang, Jian; Wang, Chenyang; Qin, Haixia; Ding, Huina; Xie, Yingxin; Guo, Tiancai

    2016-01-01

    Polyphenols in whole grain wheat have potential health benefits, but little is known about the expression patterns of phenolic acid biosynthesis genes and the accumulation of phenolic acid compounds in different-colored wheat grains. We found that purple wheat varieties had the highest total phenolic content (TPC) and antioxidant activity. Among phenolic acid compounds, bound ferulic acid, vanillic, and caffeic acid levels were significantly higher in purple wheat than in white and red wheat, while total soluble phenolic acid, soluble ferulic acid, and vanillic acid levels were significantly higher in purple and red wheat than in white wheat. Ferulic acid and syringic acid levels peaked at 14 days after anthesis (DAA), whereas p-coumaric acid and caffeic acid levels peaked at 7 DAA, and vanillic acid levels gradually increased during grain filling and peaked near ripeness (35 DAA). Nine phenolic acid biosynthesis pathway genes (TaPAL1, TaPAL2, TaC3H1, TaC3H2, TaC4H, Ta4CL1, Ta4CL2, TaCOMT1, and TaCOMT2) exhibited three distinct expression patterns during grain filling, which may be related to the different phenolic acids levels. White wheat had higher phenolic acid contents and relatively high gene expression at the early stage, while purple wheat had the highest phenolic acid contents and gene expression levels at later stages. These results suggest that the expression of phenolic acid biosynthesis genes may be closely related to phenolic acids accumulation. PMID:27148345

  2. Antioxidant, Antinociceptive and CNS Activities of Viscum orientale and High Sensitive Quantification of Bioactive Polyphenols by UPLC

    PubMed Central

    Khatun, Amina; Rahman, Mahmudur; Rahman, Md. Mahfizur; Hossain, Hemayet; Jahan, Ismet A.; Nesa, Mst. Luthfun

    2016-01-01

    Viscum orientale Willd. (Loranthaceae) has long been used in traditional medicine to treat pain, neuropharmacological disorders and various forms of tumor but not yet been reported. The aim of this study is to rationalize the traditional medicinal use of this plant by evaluating the methanol extract of V. orientale leaves (MEVOL) for anti-nociceptive, CNS depressant and antioxidant activities and to quantify the bioactive polyphenols present in this plant. Five polyphenolic compounds namely gallic acid, vanillic acid, caffeic acid, ellagic acid, and quercetin (17.54, 8.99, 99.61, 4523.31, and 100.15 mg/100 g of dry weight, respectively) have been identified in MEVOL using Ultra Performance Liquid Chromatography. Qualitative antioxidant activity determined by Thin Layer Chromatography indicated the presence of antioxidants. In quantitative antioxidant test using 2,2-diphenyl 1-picrylhydrazyl, MEVOL exhibited strong free antioxidant activity in a dose dependant manner (IC50 = 6.63 μg/ml) compared with ascorbic acid (IC50 = 1.91 μg/ml) and butylatedhydroxyanisole (IC50 = 2.27 μg/ml) controls. Total phenolic content determined using Folin Ciocaltu reagent was found to be 73.4 mg gallic acid equivalent/g of extract, while flavonoid content estimated using aluminum chloride colorimetric method was 170.7 mg quercetin equivalent/g of extract. Anti-nociceptive activity of MEVOL measured using acetic acid and formalin induced pain models in mice was significant (p < 0.001). MEVOL showed 65.6 and 88.8% writhing inhibition at 300 and 500 mg/kg body weight, respectively, comparing with standard diclofenac-Na (75.2% inhibition) at 25 mg/kg body weight in acetic acid induced pain model. In formalin induced pain model, paw licking was inhibited 45.93 and 56.4% in early phase and 55.66 and 72.64% in late phase at 300 and 500 mg/kg body weight, respectively, while diclofenac-Na inhibited 60.47 and 61.32% in early and late phase at 10 mg/kg body weight, respectively. In

  3. Antioxidant, Antinociceptive and CNS Activities of Viscum orientale and High Sensitive Quantification of Bioactive Polyphenols by UPLC.

    PubMed

    Khatun, Amina; Rahman, Mahmudur; Rahman, Md Mahfizur; Hossain, Hemayet; Jahan, Ismet A; Nesa, Mst Luthfun

    2016-01-01

    Viscum orientale Willd. (Loranthaceae) has long been used in traditional medicine to treat pain, neuropharmacological disorders and various forms of tumor but not yet been reported. The aim of this study is to rationalize the traditional medicinal use of this plant by evaluating the methanol extract of V. orientale leaves (MEVOL) for anti-nociceptive, CNS depressant and antioxidant activities and to quantify the bioactive polyphenols present in this plant. Five polyphenolic compounds namely gallic acid, vanillic acid, caffeic acid, ellagic acid, and quercetin (17.54, 8.99, 99.61, 4523.31, and 100.15 mg/100 g of dry weight, respectively) have been identified in MEVOL using Ultra Performance Liquid Chromatography. Qualitative antioxidant activity determined by Thin Layer Chromatography indicated the presence of antioxidants. In quantitative antioxidant test using 2,2-diphenyl 1-picrylhydrazyl, MEVOL exhibited strong free antioxidant activity in a dose dependant manner (IC50 = 6.63 μg/ml) compared with ascorbic acid (IC50 = 1.91 μg/ml) and butylatedhydroxyanisole (IC50 = 2.27 μg/ml) controls. Total phenolic content determined using Folin Ciocaltu reagent was found to be 73.4 mg gallic acid equivalent/g of extract, while flavonoid content estimated using aluminum chloride colorimetric method was 170.7 mg quercetin equivalent/g of extract. Anti-nociceptive activity of MEVOL measured using acetic acid and formalin induced pain models in mice was significant (p < 0.001). MEVOL showed 65.6 and 88.8% writhing inhibition at 300 and 500 mg/kg body weight, respectively, comparing with standard diclofenac-Na (75.2% inhibition) at 25 mg/kg body weight in acetic acid induced pain model. In formalin induced pain model, paw licking was inhibited 45.93 and 56.4% in early phase and 55.66 and 72.64% in late phase at 300 and 500 mg/kg body weight, respectively, while diclofenac-Na inhibited 60.47 and 61.32% in early and late phase at 10 mg/kg body weight, respectively. In

  4. Polyphenolic composition, antioxidant activity, and polyphenol oxidase (PPO) activity of quince (Cydonia oblonga Miller) varieties.

    PubMed

    Wojdyło, Aneta; Oszmiański, Jan; Bielicki, Paweł

    2013-03-20

    Phytochemical profiles (phenolic compounds, L-ascorbic acid, antioxidant and PPO activities) of 13 different quince varieties and 5 genotypes were studied. Polyphenols were identified by LC-PDA-QTof/MS and quantified by UPLC-PDA and UPLC-FL. A total of 26 polyphenolic compounds found in quince tissues were identified and presented: 9 flavan-3-ols ((-)-epicatechin, procyanidin B2, 3 procyanidin dimers and trimers, and 1 tetramer); 8 hydroxycinnamates, derivatives of caffeoylquinic and coumaroylquinic acid; and 9 kaempferol and quercetin derivatives. The content of total polyphenols was between 1709.43 (genotype 'S1') and 3436.56 mg/100 g dry weight ('Leskovač'). Flavan-3-ols, which are the major class of quince polyphenols, represented between 78 and 94% of the total polyphenolic compounds. The activity of PPO enzyme ranged from 709.85 to 1284.59 ΔU/min, and that of L-ascorbic acid ranged from 5.86 to 26.42 mg/100 g. Some quince varieties and their products characterized by a higher content of phenolic compounds may be selected to promote their positive effect on health. PMID:23461298

  5. Caffeic acid 3,4-dihydroxy-phenethyl ester suppresses receptor activator of NF-κB ligand–induced osteoclastogenesis and prevents ovariectomy-induced bone loss through inhibition of mitogen-activated protein kinase/activator protein 1 and Ca2+–nuclear factor of activated T-cells cytoplasmic 1 signaling pathways.

    PubMed

    Wu, Xian; Li, Zhenxi; Yang, Zhengfang; Zheng, Chunbing; Jing, Ji; Chen, Yihua; Ye, Xiyun; Lian, Xiaoyuan; Qiu, Wenwei; Yang, Fan; Tang, Jie; Xiao, Jianru; Liu, Mingyao; Luo, Jian

    2012-06-01

    Receptor activator of NF-κB ligand (RANKL) stimulation leads to the activation of mitogen-activated protein kinase (MAPK)/AP-1 and Ca2+–nuclear factor of activated T-cells cytoplasmic 1 (NFATc1) signaling pathways in osteoclastogenesis. Targeting these pathways has been an encouraging strategy for bone-related diseases, such as postmenopausal osteoporosis. In this study, we examined the effects of caffeic acid 3,4-dihydroxy-phenethyl ester (CADPE) on osteoclastogenesis. In mouse bone marrow monocytes (BMMs) and RAW264.7 cells, CADPE suppressed RANKL-induced osteoclast differentiation and actin-ring formation in a dose-dependent manner within non–growth inhibitory concentrations at the early stage, while CADPE had no effect on macrophage colony-stimulating factor (M-CSF)-induced proliferation and differentiation. At the molecular level, CADPE inhibited RANKL-induced phosphorylation of MAPKs, including extracellular signal-regulated kinases 1/2 (ERK1/2), p38, and c-Jun N-terminal kinase (JNK), without significantly affecting the NF-κB signaling pathway. CADPE abrogated RANKL-induced activator protein 1 (AP-1)/FBJ murine osteosarcoma viral oncogene homolog (c-Fos) nuclear translocation and activation. Overexpression of c-Fos prevented the inhibition by CADPE of osteoclast differentiation. Furthermore, CADPE suppressed RANKL-induced the tumor necrosis factor receptor associated factor 6 (TRAF6) interaction with c-src tyrosine kinase (c-Src), blocked RANKL-induced the phosphorylation of protein kinase B (AKT), and inhibited RANKL-induced Ca2+ oscillation. As a result, CADPE decreased osteoclastogenesis-related marker gene expression, including NFATc1, TRAP, cathepsin K, and c-Src. To test the effects of CADPE on osteoclast activity in vivo, we showed that CADPE prevented ovariectomy-induced bone loss by inhibiting osteoclast activity. Together, our data demonstrate that CADPE suppresses osteoclastogenesis and bone loss through inhibiting RANKL-induced MAPKs and Ca

  6. Coffee Polyphenols Change the Expression of STAT5B and ATF-2 Modifying Cyclin D1 Levels in Cancer Cells

    PubMed Central

    Oleaga, Carlota; Ciudad, Carlos J.; Noé, Véronique; Izquierdo-Pulido, Maria

    2012-01-01

    Background. Epidemiological studies suggest that coffee consumption reduces the risk of cancer, but the molecular mechanisms of its chemopreventive effects remain unknown. Objective. To identify differentially expressed genes upon incubation of HT29 colon cancer cells with instant caffeinated coffee (ICC) or caffeic acid (CA) using whole-genome microarrays. Results. ICC incubation of HT29 cells caused the overexpression of 57 genes and the underexpression of 161, while CA incubation induced the overexpression of 12 genes and the underexpression of 32. Using Venn-Diagrams, we built a list of five overexpressed genes and twelve underexpressed genes in common between the two experimental conditions. This list was used to generate a biological association network in which STAT5B and ATF-2 appeared as highly interconnected nodes. STAT5B overexpression was confirmed at the mRNA and protein levels. For ATF-2, the changes in mRNA levels were confirmed for both ICC and CA, whereas the decrease in protein levels was only observed in CA-treated cells. The levels of cyclin D1, a target gene for both STAT5B and ATF-2, were downregulated by CA in colon cancer cells and by ICC and CA in breast cancer cells. Conclusions. Coffee polyphenols are able to affect cyclin D1 expression in cancer cells through the modulation of STAT5B and ATF-2. PMID:22919439

  7. African eggplant (Solanum anguivi Lam.) fruit with bioactive polyphenolic compounds exerts in vitro antioxidant properties and inhibits Ca2+-induced mitochondrial swelling

    PubMed Central

    Elekofehinti, Olusola Olalekan; Kamdem, Jean Paul; Bolingon, Aline Augusti; Athayde, Margareth Linde; Lopes, Seeger Rodrigo; Waczuk, Emily Pansera; Kade, Ige Joseph; Adanlawo, Isaac Gbadura; Rocha, Joao Batista Teixeira

    2013-01-01

    Objective To evaluate the antioxidant and radical scavenging activities of Solanum anguivi fruit (SAG) and its possible effect on mitochondrial permeability transition pore as well as mitochondrial membrane potential (ΔΨm) isolated from rat liver. Methods Antioxidant activity of SAG was assayed by using 2,2-diphenyl-1-picrylhydrazyl (DPPH), reducing power, iron chelation and ability to inhibit lipid peroxidation in both liver and brain homogenate of rats. Also, the effect of SAG on mitochondrial membrane potential and mitochondrial swelling were determined. Identification and quantification of bioactive polyphenolics was done by HPLC-DAD. Results SAG exhibited potent and concentration dependent free radical-scavenging activity (IC50/DPPH=275.03±7.8 µg/mL). Reductive and iron chelation abilities also increase with increase in SAG concentration. SAG also inhibited peroxidation of cerebral and hepatic lipids subjected to iron oxidative assault. SAG protected against Ca2+ (110 µmol/L)-induced mitochondrial swelling and maintained the ΔΨm. HPLC analysis revealed the presence of gallic acid [(17.54±0.04) mg/g], chlorogenic acid (21.90±0.02 mg/g), caffeic acid (16.64±0.01 mg/g), rutin [(14.71±0.03) mg/g] and quercetin [(7.39±0.05) mg/g]. Conclusions These effects could be attributed to the bioactive polyphenolic compounds present in the extract. Our results suggest that SAG extract is a potential source of natural antioxidants that may be used not only in pharmaceutical and food industry but also in the treatment of diseases associated with oxidative stress. PMID:24075339

  8. A Fluorescent Assay for Plant Caffeic Acid O-methyltransferases

    Technology Transfer Automated Retrieval System (TEKTRAN)

    We have developed a facile, sensitive and continuous assay to measure the activities of plant COMTs using s-adenosyl homocysteine hydrolase as a coupling enzyme and and adeonsine a thiol-specific fluor, Thioglo1, as the detecting reagent. This assay was validated using recombinant sorghum COMT (BMR-...

  9. Plant Polyphenols as Chemopreventive Agents for Lung Cancer

    PubMed Central

    Amararathna, Madumani; Johnston, Michael R.; Rupasinghe, H. P. Vasantha

    2016-01-01

    Lung cancer may be prevented by a diet rich in fruits and vegetables as they are enriched with dietary antioxidant polyphenols, such as flavonoids, proanthocyanidins, lignans, stilbenes, and phenolic acids. Dietary polyphenols exert a wide range of beneficial biological functions beyond their antioxidative properties and are involved in regulation of cell survival pathways leading to anticarcinogenic and antimutagenic functions. There are sufficient evidence from in vitro, in vivo, and epidemiological studies to suggest that the dietary intervention of polyphenols in cancer prevention, including the chemopreventive ability of dietary polyphenols, act against lung carcinogens. Cohort and epidemiological studies in selected risk populations have evaluated clinical effects of polyphenols. Polyphenols have demonstrated three major actions: antioxidative activity, regulation of phase I and II enzymes, and regulation of cell survival pathways against lung carcinogenesis. They have also shown an inverse association of lung cancer occurrences among high risk populations who consumed considerable amounts of fruits and vegetables in their daily diet. In in vitro cell culture experimental models, polyphenols bind with electrophilic metabolites from carcinogens, inactivate cellular oxygen radicals, prevent membrane lipid peroxidation and DNA oxidative damage, and adduct formation. Further, polyphenols enhance the detoxifying enzymes such as the phase II enzymes, glutathione transferases and glucuronosyl transferases. PMID:27548149

  10. Soil microbial communities respond differently to three chemically defined polyphenols.

    PubMed

    Schmidt, Michael A; Kreinberg, Allison J; Gonzalez, Javier M; Halvorson, Jonathan J; French, Elizabeth; Bollmann, Annette; Hagerman, Ann E

    2013-11-01

    High molecular weight polyphenols (e.g. tannins) that enter the soil may affect microbial populations, by serving as substrates for microbial respiration or by selecting for certain microbes. In this study we examined how three phenolic compounds that represent some environmentally widespread tannins or their constituent functional groups were respired by soil microorganisms and how the compounds affected the abundance and diversity of soil bacteria and archaea, including ammonia oxidizers. An acidic, silt loam soil from a pine forest was incubated for two weeks with the monomeric phenol methyl gallate, the small polyphenol epigallocatechin gallate, or the large polyphenol oenothein B. Respiration of the polyphenols during the incubation was measured using the Microresp™ system. After incubation, metabolic diversity was determined by community level physiological profiling (CLPP), and genetic diversity was determined using denaturing gradient gel electrophoresis (DGGE) analysis on DNA extracted from the soil samples. Total microbial populations and ammonia-oxidizing populations were measured using real time quantitative polymerase chain reaction (qPCR). Methyl gallate was respired more efficiently than the higher molecular weight tannins but not as efficiently as glucose. Methyl gallate and epigallocatechin gallate selected for genetically or physiologically unique populations compared to glucose. None of the polyphenols supported microbial growth, and none of the polyphenols affected ammonia-oxidizing bacterial populations or ammonia-oxidizing archaea. Additional studies using both a wider range of polyphenols and a wider range of soils and environments are needed to elucidate the role of polyphenols in determining soil microbiological diversity. PMID:23545181

  11. Antisense downregulation of polyphenol oxidase results in enhanced disease susceptibility.

    PubMed

    Thipyapong, Piyada; Hunt, Michelle D; Steffens, John C

    2004-11-01

    Polyphenol oxidases (PPOs; EC 1.14.18.1 or EC 1.10.3.2) catalyze the oxidation of phenolics to quinones, highly reactive intermediates whose secondary reactions are responsible for much of the oxidative browning that accompanies plant senescence, wounding, and responses to pathogens. To assess the impact of PPO expression on resistance to Pseudomonas syringae pv. tomato we introduced a chimeric antisense potato PPO cDNA into tomato (Lycopersicon esculentum L.). Oxidation of caffeic acid, the dominant o-diphenolic aglycone of tomato foliage, was decreased ca. 40-fold by antisense expression of PPO. All members of the PPO gene family were downregulated: neither immunoreactive PPO nor PPO-specific mRNA were detectable in the transgenic plants. In addition, the antisense PPO construct suppressed inducible increases in PPO activity. Downregulation of PPO in antisense plants did not affect growth, development, or reproduction of greenhouse-grown plants. However, antisense PPO expression dramatically increased susceptibility to P. syringae expressing the avirulence gene avrPto in both Pto and pto backgrounds. In a compatible (pto) interaction, plants constitutively expressing an antisense PPO construct exhibited a 55-fold increase in bacterial growth, three times larger lesion area, and ten times more lesions cm(-2) than nontransformed plants. In an incompatible (Pto) interaction, antisense PPO plants exhibited 100-fold increases in bacterial growth and ten times more lesions cm(-2) than nontransformed plants. Although it is not clear whether hypersusceptibility of antisense plants is due to low constitutive PPO levels or failure to induce PPO upon infection, these findings suggest a critical role for PPO-catalyzed phenolic oxidation in limiting disease development. As a preliminary effort to understand the role of induced PPO in limiting disease development, we also examined the response of PPO promoter::beta-glucuronidase constructs when plants are challenged with P

  12. Managing hypertension by polyphenols.

    PubMed

    Fernández-Arroyo, Salvador; Camps, Jordi; Menendez, Javier A; Joven, Jorge

    2015-06-01

    Some polyphenols, obtained from plants of broad use, induce a favorable endothelial response in hypertension and beneficial effects in the management of other metabolic cardiovascular risks. Previous studies in our laboratories using the calyces of Hibiscus sabdariffa as a source of polyphenols show that significant effects on hypertension are noticeable in humans only when provided in high amounts. Available data are suggestive in animal models and ex vivo experiments, but data in humans are difficult to acquire. Additionally, and despite the low bioavailability of polyphenols, intervention studies provide evidence for the protective effects of secondary plant metabolites. Assumptions on public health benefits are limited by the lack of scientific knowledge, robust data derived from large randomized clinical trials, and an accurate assessment of the bioactive components provided by common foodstuff. Because it is likely that clinical effects are the result of multiple interactions among different polyphenols rather than the isolated action of unique compounds, to provide polyphenol-rich botanical extracts as dietary supplements is a suggestive option. Unfortunately, the lack of patent perspectives for the pharmaceutical industries and the high cost of production and release for alimentary industries will hamper the performance of the necessary clinical trials. Here we briefly discuss whether and how such limitations may complicate the extensive use of plant-derived products in the management of hypertension and which steps are the necessary to deal with the predictable complexity in a possible clinical practice. PMID:25714729

  13. Activation of Polyphenol Oxidase of Chloroplasts 1

    PubMed Central

    Tolbert, N. E.

    1973-01-01

    Polyphenol oxidase of leaves is located mainly in chloroplasts isolated by differential or sucrose density gradient centrifugation. This activity is part of the lamellar structure that is not lost on repeated washing of the plastids. The oxidase activity was stable during prolonged storage of the particles at 4 C or —18 C. The Km (dihydroxyphenylalanine) for spinach leaf polyphenol oxidase was 7 mm by a spectrophotometric assay and 2 mm by the manometric assay. Polyphenol oxidase activity in the leaf peroxisomal fraction, after isopycnic centrifugation on a linear sucrose gradient, did not coincide with the peroxisomal enzymes but was attributed to proplastids at nearly the same specific density. Plants were grouped by the latency properties for polyphenol oxidase in their isolated chloroplasts. In a group including spinach, Swiss chard, and beet leaves the plastids immediately after preparation from fresh leaves required a small amount of light for maximal rates of oxidation of dihydroxyphenylalanine. Polyphenol oxidase activity in the dark or light increased many fold during aging of these chloroplasts for 1 to 5 days. Soluble polyphenol oxidase of the cytoplasm was not so stimulated. Chloroplasts prepared from stored leaves were also much more active than from fresh leaves. Maximum rates of dihydroxyphenylalanine oxidation were 2 to 6 mmoles × mg−1 chlorophyll × hr−1. Equal stimulation of latent polyphenol oxidase in fresh or aged chloroplasts in this group was obtained by either light, an aged trypsin digest, 3-(4-chlorophenyl)-1, 1-dimethylurea, or antimycin A. A variety of other treatments did not activate or had little effect on the oxidase, including various peptides, salts, detergents, and other proteolytic enzymes. Activation of latent polyphenol oxidase in spinach chloroplasts by trypsin amounted to as much as 30-fold. The trypsin activation occurred even after the trypsin had been treated with 10% trichloroacetic acid, 1.0 n HCl or boiled for 30

  14. Anti-necrosis potential of polyphenols against snake venoms.

    PubMed

    Leanpolchareanchai, Jiraporn; Pithayanukul, Pimolpan; Bavovada, Rapepol

    2009-01-01

    Polyphenols from the extracts of Areca catechu L. and Quercus infectoria Oliv. inhibited phospholipase A(2), proteases, hyaluronidase and L-amino acid oxidase of Naja naja kaouthia Lesson (NK) and Calloselasma rhodostoma Kuhl (CR) venoms by in vitro tests. Both extracts inhibited the hemorrhagic activity of CR venom and the dermonecrotic activity of NK venom by in vivo tests. The inhibitory activity of plant polyphenols against local tissue necrosis induced by snake venoms may be caused by inhibition of inflammatory reactions, hemorrhage, and necrosis. The result implies the therapeutic potential of plant polyphenols against necrosis in snakebite victims. PMID:19874222

  15. Natural Polyphenols for Prevention and Treatment of Cancer

    PubMed Central

    Zhou, Yue; Zheng, Jie; Li, Ya; Xu, Dong-Ping; Li, Sha; Chen, Yu-Ming; Li, Hua-Bin

    2016-01-01

    There is much epidemiological evidence that a diet rich in fruits and vegetables could lower the risk of certain cancers. The effect has been attributed, in part, to natural polyphenols. Besides, numerous studies have demonstrated that natural polyphenols could be used for the prevention and treatment of cancer. Potential mechanisms included antioxidant, anti-inflammation as well as the modulation of multiple molecular events involved in carcinogenesis. The current review summarized the anticancer efficacy of major polyphenol classes (flavonoids, phenolic acids, lignans and stilbenes) and discussed the potential mechanisms of action, which were based on epidemiological, in vitro, in vivo and clinical studies within the past five years. PMID:27556486

  16. Natural Polyphenols for Prevention and Treatment of Cancer.

    PubMed

    Zhou, Yue; Zheng, Jie; Li, Ya; Xu, Dong-Ping; Li, Sha; Chen, Yu-Ming; Li, Hua-Bin

    2016-01-01

    There is much epidemiological evidence that a diet rich in fruits and vegetables could lower the risk of certain cancers. The effect has been attributed, in part, to natural polyphenols. Besides, numerous studies have demonstrated that natural polyphenols could be used for the prevention and treatment of cancer. Potential mechanisms included antioxidant, anti-inflammation as well as the modulation of multiple molecular events involved in carcinogenesis. The current review summarized the anticancer efficacy of major polyphenol classes (flavonoids, phenolic acids, lignans and stilbenes) and discussed the potential mechanisms of action, which were based on epidemiological, in vitro, in vivo and clinical studies within the past five years. PMID:27556486

  17. Anticancer Efficacy of Polyphenols and Their Combinations.

    PubMed

    Niedzwiecki, Aleksandra; Roomi, Mohd Waheed; Kalinovsky, Tatiana; Rath, Matthias

    2016-01-01

    Polyphenols, found abundantly in plants, display many anticarcinogenic properties including their inhibitory effects on cancer cell proliferation, tumor growth, angiogenesis, metastasis, and inflammation as well as inducing apoptosis. In addition, they can modulate immune system response and protect normal cells against free radicals damage. Most investigations on anticancer mechanisms of polyphenols were conducted with individual compounds. However, several studies, including ours, have indicated that anti-cancer efficacy and scope of action can be further enhanced by combining them synergistically with chemically similar or different compounds. While most studies investigated the anti-cancer effects of combinations of two or three compounds, we used more comprehensive mixtures of specific polyphenols and mixtures of polyphenols with vitamins, amino acids and other micronutrients. The mixture containing quercetin, curcumin, green tea, cruciferex, and resveratrol (PB) demonstrated significant inhibition of the growth of Fanconi anemia head and neck squamous cell carcinoma and dose-dependent inhibition of cell proliferation, matrix metalloproteinase (MMP)-2 and -9 secretion, cell migration and invasion through Matrigel. PB was found effective in inhibition of fibrosarcoma HT-1080 and melanoma A2058 cell proliferation, MMP-2 and -9 expression, invasion through Matrigel and inducing apoptosis, important parameters for cancer prevention. A combination of polyphenols (quercetin and green tea extract) with vitamin C, amino acids and other micronutrients (EPQ) demonstrated significant suppression of ovarian cancer ES-2 xenograft tumor growth and suppression of ovarian tumor growth and lung metastasis from IP injection of ovarian cancer A-2780 cells. The EPQ mixture without quercetin (NM) also has shown potent anticancer activity in vivo and in vitro in a few dozen cancer cell lines by inhibiting tumor growth and metastasis, MMP-2 and -9 secretion, invasion, angiogenesis

  18. Polyphenols in whole rice grain: genetic diversity and health benefits.

    PubMed

    Shao, Yafang; Bao, Jinsong

    2015-08-01

    Polyphenols, such as phenolic acid, anthocyanin and proanthocyanidins, have both nutraceutical properties and functional significance for human health. Identification of polyphenolic compounds and investigation of their genetic basis among diverse rice genotypes provides the basis for the improvement of the nutraceutical properties of whole rice grain. This review focuses on current information on the identification, genetic diversity, formation and distribution patterns of the phenolic acid, anthocyanin, and proanthocyanidins in whole rice grain. The genetic analysis of polyphenol content and antioxidant capacity allows the identification of several candidate genes or quantitative trait loci (QTL) responsible for polyphenol variation, which may be useful in improvement of these phytochemicals by breeding. Future challenges such as how to mitigate the effects of climate change while improving nutraceutical properties in whole grain, and how to use new technology to develop new rice high in nutraceutical properties are also presented. PMID:25766805

  19. Polyphenols, Inflammation, and Cardiovascular Disease

    PubMed Central

    Tangney, Christy; Rasmussen, Heather E.

    2013-01-01

    Polyphenols are compounds found in foods such as tea, coffee, cocoa, olive oil, and red wine and have been studied to determine if their intake may modify cardiovascular disease (CVD) risk. Historically, biologic actions of polyphenols have been attributed to antioxidant activities, but recent evidence suggests that immunomodulatory and vasodilatory properties of polyphenols may also contribute to CVD risk reduction. These properties will be discussed, and recent epidemiological evidence and intervention trials will be reviewed. Further identification of polyphenols in foods and accurate assessment of exposures through measurement of biomarkers (i.e., polyphenol metabolites) could provide the needed impetus to examine the impact of polyphenol-rich foods on CVD intermediate outcomes (especially those signifying chronic inflammation) and hard endpoints among high risk patients. Although we have mechanistic insight into how polyphenols may function in CVD risk reduction, further research is needed before definitive recommendations for consumption can be made. PMID:23512608

  20. Acidic Potassium Permanganate Chemiluminescence for the Determination of Antioxidant Potential in Three Cultivars of Ocimum basilicum.

    PubMed

    Srivastava, Shivani; Adholeya, Alok; Conlan, Xavier A; Cahill, David M

    2016-03-01

    Ocimum basilicum, a member of the family Lamiaceae, is a rich source of polyphenolics that have antioxidant properties. The present study describes the development and application of an online HPLC-coupled acidic potassium permanganate chemiluminescence assay for the qualitative and quantitative assessment of antioxidants in three cultivars of O. basilicum grown under greenhouse conditions. The chemiluminescence based assay was found to be a sensitive and efficient method for assessment of total and individual compound antioxidant potential. Leaves, flowers and roots were found to be rich reserves of the antioxidant compounds which showed intense chemiluminescence signals. The polyphenolics such as rosmarinic, chicoric, caffeic, p-coumaric, m-coumaric and ferulic acids showed antioxidant activity. Further, rosmarinic acid was found to be the major antioxidant component in water-ethanol extracts. The highest levels of rosmarinic acid was found in the leaves and roots of cultivars "holy green" (14.37; 11.52 mM/100 g DW respectively) followed by "red rubin" (10.02; 10.75 mM/100 g DW respectively) and "subja" (6.59; 4.97 mM/100 g DW respectively). The sensitivity, efficiency and ease of use of the chemiluminescence based assay should now be considered for its use as a primary method for the identification and quantification of antioxidants in plant extracts. PMID:26803763

  1. Reducing Breast Cancer Recurrence: The Role of Dietary Polyphenolics.

    PubMed

    Braakhuis, Andrea J; Campion, Peta; Bishop, Karen S

    2016-01-01

    Evidence from numerous observational and clinical studies suggest that polyphenolic phytochemicals such as phenolic acids in olive oil, flavonols in tea, chocolate and grapes, and isoflavones in soy products reduce the risk of breast cancer. A dietary food pattern naturally rich in polyphenols is the Mediterranean diet and evidence suggests those of Mediterranean descent have a lower breast cancer incidence. Whilst dietary polyphenols have been the subject of breast cancer risk-reduction, this review will focus on the clinical effects of polyphenols on reducing recurrence. Overall, we recommend breast cancer patients consume a diet naturally high in flavonol polyphenols including tea, vegetables (onion, broccoli), and fruit (apples, citrus). At least five servings of vegetables and fruit daily appear protective. Moderate soy protein consumption (5-10 g daily) and the Mediterranean dietary pattern show the most promise for breast cancer patients. In this review, we present an overview of clinical trials on supplementary polyphenols of dietary patterns rich in polyphenols on breast cancer recurrence, mechanistic data, and novel delivery systems currently being researched. PMID:27608040

  2. Targeting Tumor Ubiquitin-Proteasome Pathway with Polyphenols for Chemosensitization

    PubMed Central

    Shen, Min; Chan, Tak Hang; Dou, Q. Ping

    2012-01-01

    The development of tumor drug resistance is one of the biggest obstacles on the way to achieve a favorable outcome of chemotherapy. Among various strategies that have been explored to overcome drug resistance, the combination of current chemotherapy with plant polyphenols as a chemosensitizer has emerged as a promising one. Plant polyphenols are a group of phytochemicals characterized by the presence of more than one phenolic group. Mechanistic studies suggest that polyphenols have multiple intracellular targets, one of which is the proteasome complex. The proteasome is a proteolytic enzyme complex responsible for intracellular protein degradation and has been shown to play an important role in tumor growth and the development of drug resistance. Therefore, proteasome inhibition by plant polyphenols could be one of the mechanisms contributing to their chemosensitizing effect. Plant polyphenols that have been identified to possess proteasome-inhibitory activity include (−)-epigallocatechins-3-gallate (EGCG), genistein, luteolin, apigenin, chrysin, quercetin, curcumin and tannic acid. These polyphenols have exhibited an appreciable effect on overcoming resistance to various chemotherapeutic drugs as well as multidrug resistance in a broad spectrum of tumors ranging from carcinoma and sarcoma to hematological malignances. The in vitro and in vivo studies on polyphenols with proteasome-inhibitory activity have built a solid foundation to support the idea that they could serve as a chemosensitizer for the treatment of cancer. In-depth mechanistic studies and identification of optimal regimen are needed in order to eventually translate this laboratory concept into clinical trials to actually benefit current chemotherapy. PMID:22292765

  3. Antioxidant and antiglycation activity of selected dietary polyphenols in a cookie model.

    PubMed

    Zhang, Xinchen; Chen, Feng; Wang, Mingfu

    2014-02-19

    Dietary polyphenols have been proposed to be promising functional food additives for their potent antioxidant capacity and other health-beneficial bioactivities. The current study prepared cookies fortified with five selected dietary polyphenols (naringenin, quercetin, epicatechin, chlorogenic acid, and rosmarinic acid). Results indicated that the enhancement of the antioxidant capacity was not as obvious as expected because the phenolics' antioxidant activity was seriously lowered by the baking process due to thermal degradation and transformation. Meanwhile, the tested polyphenols, especially quercetin, showed inhibition against formation of both reactive carbonyl species and total fluorescent advanced glycation endproducts (AGEs). Polyphenol fortification could also induce colorimetric changes and alterations in selected quality attributes. Overall, the findings support dietary polyphenols as functional food ingredients in the purpose of health benefits associated with a higher intake of antioxidants and a lower load of reactive carbonyls and AGEs. The polyphenols' stability and reactivity during thermal processing should be an important consideration. PMID:24471469

  4. Cranberry polyphenols: potential benefits for dental caries and periodontal disease.

    PubMed

    Bonifait, Laetitia; Grenier, Daniel

    2010-01-01

    Over the past decade, cranberries and their molecular components have received increasing attention from researchers in human health. In particular, the properties of the high-molecular-weight polyphenols isolated from cranberries have shown promise with regard to dental caries and periodontal disease. These potential anticaries agents inhibit the production of organic acids and the formation of biofilms by cariogenic bacteria. In addition, cranberry polyphenols may reduce the inflammatory response, as well as the production and activity of proteolytic enzymes contributing to the destruction of the extracellular matrix in periodontal disease. The polyphenols of cranberries also interfere with various activities (including formation of biofilm and adhesion) of Porphyromonas gingivalis, the main etiologic agent in chronic periodontitis. This article summarizes the scientific evidence supporting the potential of cranberry polyphenols to prevent and/or treat diseases of the mouth. PMID:20943032

  5. Polyphenols from Eriosema tuberosum.

    PubMed

    Ma, W G; Fuzzati, N; Li, Q S; Yang, C R; Stoeckli-Evans, H; Hostettmann, K

    1995-07-01

    A dichloromethane extract of the roots of Eriosema tuberosum exhibited antifungal activity against Cladosporium cucumerinum and Candida albicans using TLC bioautography. Bioassay-directed fractionation led to the isolation of four new compounds, eriosemaones A-D, together with a known compound, flemichin-D, as the active constituents. Three inactive polyphenols were also isolated after methylation, together with one new chromone, eriosematin. Structures were determined by spectroscopic analysis and from chemical evidence. PMID:7662271

  6. Identification and quantification of novel cranberry-derived plasma and urinary (poly)phenols.

    PubMed

    Feliciano, Rodrigo P; Boeres, Albert; Massacessi, Luca; Istas, Geoffrey; Ventura, M Rita; Nunes Dos Santos, Cláudia; Heiss, Christian; Rodriguez-Mateos, Ana

    2016-06-01

    Cranberries are a rich source of (poly)phenols, in particular proanthocyanidins, anthocyanins, flavonols, and phenolic acids. However, little is known about their bioavailability in humans. We investigated the absorption, metabolism, and excretion of cranberry (poly)phenols in plasma and urine of healthy young men after consumption of a cranberry juice (787 mg (poly)phenols). A total of 60 cranberry-derived phenolic metabolites were identified using UPLC-Q-TOF-MS analysis with authentic standards. These included sulfates of pyrogallol, valerolactone, benzoic acids, phenylacetic acids, glucuronides of flavonols, as well as sulfates and glucuronides of cinnamic acids. The most abundant plasma metabolites were small phenolic compounds, in particular hippuric acid, catechol-O-sulfate, 2,3-dihydroxybenzoic acid, phenylacetic acid, isoferulic acid, 4-methylcatechol-O-sulfate, α-hydroxyhippuric acid, ferulic acid 4-O-sulfate, benzoic acid, 4-hydroxyphenyl acetic acid, dihydrocaffeic acid 3-O-sulfate, and vanillic acid-4-O-sulfate. Some benzoic acids, cinnamic acids, and flavonol metabolites appeared in plasma early, at 1-2 h post-consumption. Others such as phenylacetic acids, benzaldehydes, pyrogallols, catechols, hippuric and dihydrocinnamic acid derivatives appear in plasma later (Tmax 4-22 h). The 24 h urinary recovery with respect to the amount of (poly)phenols consumed was 6.2%. Our extensive description of the bioavailability of cranberry (poly)phenols lays important groundwork necessary to start understanding the fate of these compounds in humans. PMID:26836705

  7. Dentin Biomodification Potential Depends on Polyphenol Source

    PubMed Central

    Aguiar, T.R.; Vidal, C.M.P.; Phansalkar, R.S.; Todorova, I.; Napolitano, J.G.; McAlpine, J.B.; Chen, S.N.; Pauli, G.F.; Bedran-Russo, A.K.

    2014-01-01

    Although proanthocyanidins (PACs) modify dentin, the effectiveness of different PAC sources and the correlation with their specific chemical composition are still unknown. This study describes the chemical profiling of natural PAC-rich extracts from 7 plants using ultra high pressure/performance liquid chromatography (UHPLC) to determine the overall composition of these extracts and, in parallel, comprehensively evaluate their effect on dentin properties. The total polyphenol content of the extracts was determined (as gallic acid equivalents) using Folin-Ciocalteau assays. Dentin biomodification was assessed by the modulus of elasticity, mass change, and resistance to enzymatic biodegradation. Extracts with a high polyphenol and PAC content from Vitis vinifera, Theobroma cacao, Camellia sinensis, and Pinus massoniana induced a significant increase in modulus of elasticity and mass. The UHPLC analysis showed the presence of multiple types of polyphenols, ranging from simple phenolic acids to oligomeric PACs and highly condensed tannins. Protective effect against enzymatic degradation was observed for all experimental groups; however, statistically significant differences were observed between plant extracts. The findings provide clear evidence that the dentin bioactivities of PACs are source dependent, resulting from a combination of concentration and specific chemical constitution of the complex PAC mixtures. PMID:24574140

  8. Dentin biomodification potential depends on polyphenol source.

    PubMed

    Aguiar, T R; Vidal, C M P; Phansalkar, R S; Todorova, I; Napolitano, J G; McAlpine, J B; Chen, S N; Pauli, G F; Bedran-Russo, A K

    2014-04-01

    Although proanthocyanidins (PACs) modify dentin, the effectiveness of different PAC sources and the correlation with their specific chemical composition are still unknown. This study describes the chemical profiling of natural PAC-rich extracts from 7 plants using ultra high pressure/performance liquid chromatography (UHPLC) to determine the overall composition of these extracts and, in parallel, comprehensively evaluate their effect on dentin properties. The total polyphenol content of the extracts was determined (as gallic acid equivalents) using Folin-Ciocalteau assays. Dentin biomodification was assessed by the modulus of elasticity, mass change, and resistance to enzymatic biodegradation. Extracts with a high polyphenol and PAC content from Vitis vinifera, Theobroma cacao, Camellia sinensis, and Pinus massoniana induced a significant increase in modulus of elasticity and mass. The UHPLC analysis showed the presence of multiple types of polyphenols, ranging from simple phenolic acids to oligomeric PACs and highly condensed tannins. Protective effect against enzymatic degradation was observed for all experimental groups; however, statistically significant differences were observed between plant extracts. The findings provide clear evidence that the dentin bioactivities of PACs are source dependent, resulting from a combination of concentration and specific chemical constitution of the complex PAC mixtures. PMID:24574140

  9. Nigerian foodstuffs with prostate cancer chemopreventive polyphenols.

    PubMed

    Atawodi, Sunday Eneojo

    2011-09-23

    Dietary polyphenols are antioxidants that can scavenge biological free radicals, and chemoprevent diseases with biological oxidation as their main etiological factor. In this paper, we review our laboratory data vis-ὰ-vis available literature on prostate cancer chemopreventive substances in Nigerian foodstuffs. Dacryodes edulis fruit, Moringa oleifera and Syzygium aromaticum contained prostate active polyphenols like ellagic acid, gallate, methylgallate, catechol, kaempferol quercetin and their derivatives. Also Canarium schweinfurthii Engl oil contained ten phenolic compounds and lignans, namely; catechol, p-hydroxybenzaldehyde, dihydroxyphenylacetic acid, tyrosol, p-hydroxybenzoic acid, dihydroxybenzoic acid, vanillic acid, phloretic acid, pinoresinol, secoisolariciresinol. In addition, tomatoes (Lycopersicon esculentum Mill) which contains the powerful antioxidant and anti-prostate cancer agent, lycopene; cabbage (Brassica oleracea) containing indole-3-carbinol; citrus fruits containing pectin; Soursop (Annona muricata) containing annonaceous acetogenins; soya beans (Glycine max) containing isoflavones; chilli pepper (Capsicum annuum) containing capsaicin, and green tea (Camellia sinensis) containing (-) epigallocatechin gallate (EGCG), (-) epicatechin, (-) epicatechin-3-gallate and (-) epigallocatechin -3-gallate which are widely reported to posses prostate cancer chemopreventive compounds are also grown in Nigeria and other African countries. Thus, the high incidence of prostate cancer among males of African extraction can be dramatically reduced, and the age of onset drastically increased, if the population at risk consumes the right kinds of foods in the right proportion, beginning early in life, especially as prostate cancer has a latency period of about 50 years. PMID:21992488

  10. Nigerian foodstuffs with prostate cancer chemopreventive polyphenols

    PubMed Central

    2011-01-01

    Dietary polyphenols are antioxidants that can scavenge biological free radicals, and chemoprevent diseases with biological oxidation as their main etiological factor. In this paper, we review our laboratory data vis-ὰ-vis available literature on prostate cancer chemopreventive substances in Nigerian foodstuffs. Dacryodes edulis fruit, Moringa oleifera and Syzygium aromaticum contained prostate active polyphenols like ellagic acid, gallate, methylgallate, catechol, kaempferol quercetin and their derivatives. Also Canarium schweinfurthii Engl oil contained ten phenolic compounds and lignans, namely; catechol, p-hydroxybenzaldehyde, dihydroxyphenylacetic acid, tyrosol, p-hydroxybenzoic acid, dihydroxybenzoic acid, vanillic acid, phloretic acid, pinoresinol, secoisolariciresinol. In addition, tomatoes (Lycopersicon esculentum Mill) which contains the powerful antioxidant and anti-prostate cancer agent, lycopene; cabbage (Brassica oleracea) containing indole-3-carbinol; citrus fruits containing pectin; Soursop (Annona muricata) containing annonaceous acetogenins; soya beans (Glycine max) containing isoflavones; chilli pepper (Capsicum annuum) containing capsaicin, and green tea (Camellia sinensis) containing (-) epigallocatechin gallate (EGCG), (-) epicatechin, (-) epicatechin-3-gallate and (-) epigallocatechin -3-gallate which are widely reported to posses prostate cancer chemopreventive compounds are also grown in Nigeria and other African countries. Thus, the high incidence of prostate cancer among males of African extraction can be dramatically reduced, and the age of onset drastically increased, if the population at risk consumes the right kinds of foods in the right proportion, beginning early in life, especially as prostate cancer has a latency period of about 50 years. PMID:21992488

  11. Use of Moessbauer spectroscopy to study reaction products of polyphenols and iron compounds

    SciTech Connect

    Gust, J. ); Suwalski, J. )

    1994-05-01

    Moessbauer spectroscopy was used to study parameters of the reaction products of iron compounds (Fe[sup III]) and polyphenols with hydroxyl (OH) groups in ortho positions. Polyphenols used in the reaction were catechol, pyrogallol, gallic acid, and oak tannin. The Fe-containing compounds were hydrated ferric sulfate (Fe[sub 2][SO[sub 4

  12. Polyphenol and glycoalkaloid contents in potato cultivars grown in Luxembourg.

    PubMed

    Deusser, Hannah; Guignard, Cédric; Hoffmann, Lucien; Evers, Danièle

    2012-12-15

    The polyphenol (phenolic acids, flavanols and flavonols) and glycoalkaloid (α-chaconine and α-solanine) contents of potato tubers grown in Luxembourg were analyzed by UPLC-DAD and HPLC-MS/MS separately in peel (approx. 2mm), outer (approx. 1cm) and inner flesh. Polyphenol contents decreased from the peel via the outer to the inner flesh and differed among the cultivars. The cultivars Vitelotte and Luminella had the highest polyphenol contents (5202 and 572 μg/g dry weight (DW) in the outer flesh), whereas Charlotte and Bintje had the lowest contents (19.5 and 48.0 μg/g DW). Chlorogenic acid and its isomers (neo- and cryptochlorogenic acid) were the major polyphenols. Glycoalkaloid contents were highest in the peel and lowest in the inner flesh, values in the flesh were below guideline limits in all cultivars. In conclusion, potatoes contribute to the daily intake of polyphenols and their consumption, thereby, may have positive effects on health. PMID:22980877

  13. Prevention of benzene-induced genotoxicity in bone marrow and lung cells: superiority of polyphenolic acetates to polyphenols.

    PubMed

    Kumar, Ajit; Sushama, Anupam; Rohil, Vishwajeet; Manral, Sushma; Gangopadhyay, Sukanya; Prasad, Ashok K; Raj, Hanumantharao G; Parmar, Virender S

    2011-09-01

    Previous investigations carried out in our laboratory have highlighted that 7,8-diacetoxy-4-methylcoumarin demonstrates a mechanism-based inhibition of cytochrome P450 (Cyt-P450) activities such as microsome-mediated aflatoxin B1 (AFB1) epoxidation, dealkylation of alkylated resorufin, and toxicokinetics of benzene. 7,8-Diacetoxy-4-methylcoumarin, quercetin pentaacetate, and ellagic acid peracetate were also found to be effective in giving the protection of AFB1-induced genotoxicity in rat's bone marrow and lung cells possibly due to acetylation of Cyt-P450 apoprotein mediated by acetoxy drug: protein transacetylase. Later, this transacetylase was identified as calreticulin, and the acetyltransferase function of calreticulin was appropriately termed calreticulin transacetylase. In this communication, we have focused on the superiority of several classes of polyphenolic acetates to polyphenols in the modification of Cyt-P450-linked mixed function oxidases (MFOs) such as 7-ethoxyresorufin O-deethylase (EROD) and pentoxyresorufin O-dealkylase (PROD). Special attention has also been focused on benzene-induced genotoxicity in bone marrow and lung cells. Results clearly indicated that polyphenolic acetates demonstrated time-dependent inhibition of Cyt-P450-linked MFOs, while parent polyphenols failed to demonstrate the same. Polyphenolic acetates were found to be more superior to polyphenols in preventing benzene-induced micronuclei formation. The pattern of inhibition of Cyt-P450-dependent MFOs and benzene-induced micronuclei formation by polyphenolic acetates was found in tune with their specificities to calreticulin transacetylase. These results further substantiated that inhibition of Cyt-P450-linked MFOs and benzene-induced genotoxicity in bone marrow and lung cells by polyphenolic acetates are mediated by the action of calreticulin transacetylase that catalyzes the acetylation of concerned proteins. PMID:21267547

  14. Colour Evaluation, Bioactive Compound Content, Phenolic Acid Profiles and in Vitro Biological Activity of Passerina del Frusinate White Wines: Influence of Pre-Fermentative Skin Contact Times.

    PubMed

    Carbone, Katya; Fiordiponti, Luciano

    2016-01-01

    Passerina del Frusinate is an autochthonous wine grape variety, which grows in the Lazio region that is currently being evaluated by local wine producers. In this study, colour properties (CIELab coordinates), bioactive compounds (total polyphenols and flavan-3-ols), HPLC-DAD phenolic acid profiles and in vitro biological activity of monovarietal Passerina del Frusinate white wines and the effect of different maceration times (0, 18 and 24 h) were evaluated based on these parameters. Results highlighted statistically significant differences for almost all analysed parameters due to a strong influence of the pre-fermentative skin contact time. The flavan content of macerated wines was six times higher than that of the control, while total polyphenols were 1.5 times higher. According to their phytochemical content, macerated wines showed the highest antiradical capacity tested by means of DPPH(•) and ABTS(+•) assays. Besides, prolonged maceration resulted in a reduction of CIELab coordinates as well as of the content of phenolic substances and antiradical capacity. Among the phenolic acids analysed, the most abundant were vanillic acid and caffeic acid; the latter proved to be the most susceptible to degradation as a result of prolonged maceration. Passerina del Frusinate appears as a phenol-rich white wine with a strong antioxidant potential similar to that of red wines. PMID:27455227

  15. Antioxidant activity and nutrient release from polyphenol-enriched cheese in a simulated gastrointestinal environment.

    PubMed

    Lamothe, Sophie; Langlois, Ariane; Bazinet, Laurent; Couillard, Charles; Britten, Michel

    2016-03-01

    Green tea polyphenols are recognized for their antioxidant properties and their effects on lipid digestion kinetics. Polyphenols are sensitive to degradation in the intestinal environment. Interactions with dairy proteins could modulate the stability and biological activity of polyphenols during digestion. The objective of this study was to evaluate the release of nutrients (polyphenols, fatty acids and peptides) and the antioxidant activity in polyphenol-enriched cheese containing different levels of calcium in a simulated gastrointestinal environment. The relationship between cheese matrix texture, matrix degradation and nutrient release during digestion was also studied. Green tea extract was added to milk at 0% or 0.1%, and cheeses were produced on a laboratory scale. The level of available calcium was adjusted to low (Ca(low)), regular (Ca(reg)) or high (Ca(high)) during the salting step of the cheese-making process. Cheeses were subjected to simulated digestion. The rate and extent of fatty acid release were 21% lower for Ca(low) cheese than for Ca(reg) and Ca(high) cheeses. The greater adhesiveness of Ca(low) cheese, which resulted in lower rates of matrix degradation and proteolysis, contributed to the reduced rate of lipolysis. The presence of green tea extract in cheese reduced the release of free fatty acids at the end of digestion by 7%. The addition of green tea extract increased cheese hardness but did not influence matrix degradation or proteolysis profiles. The formation of complexes between tea polyphenols and proteins within the cheese matrix resulted in a more than twofold increase in polyphenol recovery in the intestinal phase compared with the control (tea polyphenol extract incubated with polyphenol-free cheese). Antioxidant activity was 14% higher in the digest from polyphenol-enriched cheese than in the control. These results suggest that cheese is an effective matrix for the controlled release of nutrients and for the protection of green

  16. Versatile surface engineering of porous nanomaterials with bioinspired polyphenol coatings for targeted and controlled drug delivery

    NASA Astrophysics Data System (ADS)

    Li, Juan; Wu, Shuxian; Wu, Cuichen; Qiu, Liping; Zhu, Guizhi; Cui, Cheng; Liu, Yuan; Hou, Weijia; Wang, Yanyue; Zhang, Liqin; Teng, I.-Ting; Yang, Huang-Hao; Tan, Weihong

    2016-04-01

    The development of biocompatible drug delivery systems with targeted recognition and controlled release has experienced a number of design challenges, including, for example, complicated preparation steps and premature drug release. Herein, we address these problems through an in situ self-polymerization method that synthesizes biodegradable polyphenol-coated porous nanomaterials for targeted and controlled drug delivery. As a proof of concept, we synthesized polyphenol-coated mesoporous silica nanoparticles, termed MSN@polyphenol. The polyphenol coatings not only improved colloidal stability and prevented premature drug leakage, but also provided a scaffold for immobilization of targeting moieties, such as aptamers. Both immobilization of targeting aptamers and synthesis of polyphenol coating are easily accomplished without the aid of any other organic reagents. Importantly, the polyphenol coating (EGCg) used in this study could be biodegraded by acidic pH and intracellular glutathione, resulting in the release of trapped anticancer drugs. Based on confocal fluorescence microscopy and cytotoxicity experiments, drug-loaded and polyphenol-coated MSNs were shown to possess highly efficient internalization and an apparent cytotoxic effect on target cancer, but not control, cells. Our results suggest that these highly biocompatible and biodegradable polyphenol-coated MSNs are promising vectors for controlled-release biomedical applications and cancer therapy.The development of biocompatible drug delivery systems with targeted recognition and controlled release has experienced a number of design challenges, including, for example, complicated preparation steps and premature drug release. Herein, we address these problems through an in situ self-polymerization method that synthesizes biodegradable polyphenol-coated porous nanomaterials for targeted and controlled drug delivery. As a proof of concept, we synthesized polyphenol-coated mesoporous silica nanoparticles

  17. Cytochrome c catalyses the formation of pentyl radical and octanoic acid radical from linoleic acid hydroperoxide.

    PubMed Central

    Iwahashi, Hideo; Nishizaki, Koji; Takagi, Ichiro

    2002-01-01

    A reaction of 13-hydroperoxide octadecadienoic acid (13-HPODE) with cytochrome c was analysed using ESR, HPLC-ESR and HPLC-ESR-MS by the combined use of the spin-trapping technique. The ESR, HPLC-ESR and HPLC-ESR-MS analyses showed that cytochrome c catalyses formation of pentyl and octanoic acid radicals from 13-HPODE. On the other hand, only the alpha-(4-pyridyl-1-oxide)-N-t-butylnitrone/octanoic acid radical adduct was detected in the elution profile of HPLC-ESR for a mixture of 13-HPODE with haematin, indicating that haematin catalyses the formation of octanoic acid radical. In addition, the reaction of 13-HPODE with cytochrome c was inhibited by chlorogenic acid, caffeic acid and ferulic acid via two possible mechanisms, i.e. reducing cytochrome c (chlorogenic acid and caffeic acid) and scavenging the radical intermediates (chlorogenic acid, caffeic acid and ferulic acid). PMID:11742529

  18. Polyphenol content of plasma and litter after the oral administration of green tea and tea polyphenols in chickens.

    PubMed

    Zhou, Yi-Bin; Wan, Xiao-Chun; Shang, Yan-Yan; Hu, Jing-Wei; Shao, Lei; Chen, Wei; Li, Da-Xiang

    2012-02-22

    Metabolic profiles of broiler chickens were examined after the ingestion of green tea, tea polyphenols, and (-)-epigallocatechin-3-gallate (EGCG). Solid-phase extraction of serum and litters yielded free catechins and their metabolites, which were then identified and quantified by liquid chromatography-tandem mass spectrometry. In plasma samples, (-)-gallocatechin, (+)-catechin, and EGCG were detected in the green tea group; pyrogallol acid, (epi)catechin-O-sulfate, 4'-O-methyl-(epi)gallocatechin-O-glucuronide, and (epi)catechin-3'-O-glucuronide were detected in the tea polyphenols group; and EGCG, (-)-gallocatechin gallate (GCG), and 4'-O-methyl-(epi)gallocatechin-O-glucuronides were detected in the EGCG group. In litters, gallic acid, EGCG, GCG, and ECG were detected in the green tea and tea polyphenols groups; EGCG and ECG were detected in the EGCG group. The conjugated metabolites, 4'-O-methyl-(epi)gallocatechin-O-glucuronide, (epi)catechin-3'-glucuronide, and 4'-O-methyl-(epi)catechin-O-sulfate, were identified in the green tea group; 4'-O-methyl-(epi)catechin-O-sulfate and 4'-O-methyl-(epi)gallocatechin-O-sulfate were identified in the tea polyphenols group; only 4'-O-methyl-(epi)gallocatechin-O-sulfate was detected in the EGCG group. The excretion of tea catechins was 95.8, 87.7, and 97.7% for the green tea, tea polyphenols, and EGCG groups, respectively. PMID:22224899

  19. Purification and characterization of polyphenols from chestnut astringent skin.

    PubMed

    Tsujita, Takahiro; Yamada, Misato; Takaku, Takeshi; Shintani, Tomoyoshi; Teramoto, Kanae; Sato, Takafumi

    2011-08-24

    Polyphenolic compounds from chestnut astringent skin (CAS) were purified by dialysis, using Diaion HP-20 and Sephadex LH-20 columns. During purification, specific α-amylase inhibitory activities were increased about 3.4-fold, and the 50% inhibition value was 5.71 μg/mL in the Sephadex LH-20 fraction (SE-fraction). The SE-fraction contained about 67% of the total polyphenols, 57.3% of the flavanol-type tannins, and 51.3% of the procyanidins. Strong antioxidant activity was observed in the SE-fraction. Oral administration of the SE-fraction in rats fed corn starch significantly suppressed an increase in blood glucose levels. The SE-fraction contained gallic acid and ellagic acid. The MALDI-TOF spectrum showed a peak series exhibiting a mass increment of 288 Da, reflecting the variation in the number of catechin/epicatechin units. Our results suggest CAS contains polyphenols with strong α-amylase inhibitory activity. The data also suggest CAS polyphenols might be oligomeric proanthocyanidins with gallic acid and ellagic acid. PMID:21777007

  20. Analytical condition setting a crucial step in the quantification of unstable polyphenols in acidic conditions: analyzing prenylflavanoids in biological samples by liquid chromatography-electrospray ionization triple quadruple mass spectrometry.

    PubMed

    Quifer-Rada, Paola; Martínez-Huélamo, Miriam; Jáuregui, Olga; Chiva-Blanch, Gemma; Estruch, Ramón; Lamuela-Raventós, Rosa M

    2013-06-01

    The interest in studying hops and beer prenylflavanoids, isoxanthohumol, xanthohumol, and 8-prenylnaringenin, has increased in recent years due to their biological activity as strong phytoestrogens and potent cancer chemopreventive agents. However, prenylflavanoids behave differently from most polyphenols, since they are unstable at acidic pH. To our knowledge, no published studies to date have considered the degradation of these compounds during analytical processes. In the present work, a new sensitive and specific method based on solid phase extraction and liquid chromatography coupled to electrospray ionization triple quadruple mass spectrometry (LC-ESI-MS/MS) was developed and validated. The new method was optimized to avoid degradation of the selected analytes, isoxanthohumol, xanthohumol, and 8-prenylnaringenin, throughout the analytical process and to reduce the urine matrix effect in LC-ESI-MS/MS assays. It was concluded that a neutral pH (pH 7.0) is necessary for the analysis of prenylflavanoids, in order to maintain the stability of compounds for at least 24 h. The addition of ascorbic acid to the media improved stability, calibration curves, coefficients of correlation, accuracy, and precision parameters. Mix-mode cation exchange sorbent yielded the best matrix effect factors and recoveries. Method validation results showed appropriate intraday and interday accuracy and precision (<15%). Recovery of isoxanthohumol, xanthohumol, and 8-prenylnaringenin was 97.1% ± 0.03, 105.8% ± 0.05, and 105.4% ± 0.04, respectively, and matrix effect factors were nearly 100%. The stability assay showed that analytes were stable for at least 24 h. The method was applied to quantify 10 human samples of urine and was able to quantify prenylflavanoids in urine after the consumption of a single dose of beer (330 mL). PMID:23642016

  1. Polyphenols-rich natural products for treatment of diabetes.

    PubMed

    Dragan, S; Andrica, F; Serban, Maria-Corina; Timar, R

    2015-01-01

    Currently, experimental and clinical evidences showed that polyphenols-rich natural products, like nutraceuticals and food supplements, may offer unique treatment modalities in type 2 diabetes mellitus (DM), due to their biological properties. Natural products modulate the carbohydrate metabolism by various mechanisms, such as restoring beta-cells integrity and physiology, enhancing insulin releasing activity, and the glucose using. Sea buckthorn berries, red grapes, bilberries, chokeberries and popular drinks like cocoa, coffee and green tea are all rich in polyphenols and may decrease the insulin response, offer in g a natural alternative of treatment in diabetes. Therefore, researches are now focused on potential efficacies of different types of polyphenols, including flavonoids, phenolic acids, lignans, anthocyans and stilbenes. Animal and human studies showed that polyphenols modulate carbohydrate and lipid metabolism, decrease glycemia and insulin resistance, increase lipid metabolism and optimize oxidative stress and inflammatory processes. It is important to understand the proper dose and duration of supplementation with polyphenols-rich extracts in order to guide effective therapeutic interventions in diabetic patients. PMID:25174925

  2. Inhibition of cyclic diadenylate cyclase, DisA, by polyphenols

    PubMed Central

    Opoku-Temeng, Clement; Sintim, Herman O.

    2016-01-01

    Cyclic di-AMP has emerged as an important signaling molecule that controls a myriad of functions, including cell wall homeostasis in different bacteria. Polyphenols display various biological activities and tea polyphenols in particular have been shown to possess among other properties antioxidant and antibacterial activities. Certain tea polyphenols, such as catechin and epigallocatechin gallate, have been used to augment the action of traditional antibiotics that target the cell wall. Considering the expanding role played by cyclic dinucleotides in bacteria, we investigated whether the action of polyphenols on bacteria could be due in part to modulation of c-di-AMP signaling. Out of 14 tested polyphenols, tannic acid (TA), theaflavin-3′-gallate (TF2B) and theaflavin-3,3′-digallate (TF3) exhibited inhibitory effects on B. subtilis c-di-AMP synthase, DisA. TF2B and TF3 specifically inhibited DisA but not YybT (a PDE) whilst TA was more promiscuous and inhibited both DisA and YybT. PMID:27150552

  3. Chitosan microbeads for encapsulation of thyme (Thymus serpyllum L.) polyphenols.

    PubMed

    Trifković, Kata T; Milašinović, Nikola Z; Djordjević, Verica B; Krušić, Melina T Kalagasidis; Knežević-Jugović, Zorica D; Nedović, Viktor A; Bugarski, Branko M

    2014-10-13

    In this work chitosan microbeads were prepared by emulsion technique and loaded with thyme polyphenols by diffusion from an external aqueous solution of Thymus serpyllum L. The effects of concentrations of chitosan (1.5-3% (w/v)) and GA (glutaraldehyde) (0.1-0.4% (v/v)), as a crosslinking agent on the main properties of microbeads were assessed. The obtained microgel beads from ∼ 220 to ∼ 790 μm in diameter were exposed to controlled drying process at air (at 37 °C) after which they contracted to irregular shapes (∼ 70-230 μm). The loading of dried microbeads with polyphenols was achieved by swelling in the acidic medium. The swelling rate of microbeads decreased with the increase in GA concentration. Upon this rehydration, thyme polyphenols were effectively encapsulated (active load of 66-114 mg GAE g(beads)(-1)) and the microbeads recovered a spherical shape. Both, the increase in the amount of the crosslinking agent and the presence of polyphenols, contributed to a more pronounced surface roughness of microbeads. The release of encapsulated polyphenols in simulated gastrointestinal fluids was prolonged to 3h. PMID:25037430

  4. [Extraction and quantification of polyphenols from coffee pulp].

    PubMed

    García, L A; Vélez, A J; de Rozo, M P

    1985-09-01

    The polyphenol content of coffee pulp extracts was determined using the Folin-Ciocalteau method. The use of polyvynilpirrolidone (PVP) was introduced in order to eliminate interferences. Condensed polyphenols in the extracts were determined by the method of acidified vanillin. Chlorogenic acid and catechin were used as standards for Folin-Ciocalteau and Vanillin methods, respectively, and a calibration curve was constructed for each solvent. The solvents used were methanol, methanol-water (50:50), ammonium hydroxide (3%) and calcium hydroxide (1%), using times of extraction of 10 minutes and 1 hour. No differences were found in the amount of polyphenols extracted by the different solvents at the two extraction times. After 10 minutes, the alkaline solvents NH4OH (3%) and Ca(OH)2 (1%), extracted more polyphenols than the other two solvents. Nevertheless, ammonium hydroxide (3%) was more efficient in extracting condensed polyphenols. The results herein presented suggest that treating coffee pulp with mild alkaline solvents may improve its nutritive value. PMID:3842054

  5. Differential effectiveness of berry polyphenols as anti-giardial agents

    PubMed Central

    ANTHONY, J.-P.; FYFE, L.; STEWART, D.; McDOUGALL, G. J.

    2011-01-01

    SUMMARY Following previous work on the anti-giardial effect of blueberry polyphenols, a range of polyphenol-rich extracts from berries and other fruits was screened for their ability to kill Giardia duodenalis, an intestinal parasite of humans. Polyphenol-rich extracts were prepared from berries using solid-phase extraction and applied to trophozoites of Giardia duodenalis grown in vitro. All berry extracts caused inhibition at 166 μg gallic acid equivalents (GAE)/ml phenol content but extracts from strawberry, arctic bramble, blackberry and cloudberry were as effective as the currently used drug, metronidazole, causing complete trophozoite mortality in vitro. Cloudberry extracts were found to be the most effective causing effectively complete trophozoite mortality at 66 μg GAE/ml. The polyphenol composition of the more effective berry extracts suggested that the presence of ellagitannins could be an important factor. However, the potency of cloudberry could be related to high ellagitannin content but also to the presence of substantial amounts of unconjugated p-coumaric acid and benzoic acid. These in vitro effects occur at concentrations easily achievable in the gut after berry ingestion and we discuss the likelihood that berry extracts could be effective anti-giardial agents in vivo. PMID:21813029

  6. New Polyphenols Identified in Artemisiae abrotani herba Extract.

    PubMed

    Baiceanu, Elisabeta; Vlase, Laurian; Baiceanu, Andrei; Nanes, Madalina; Rusu, Dan; Crisan, Gianina

    2015-01-01

    Artemisia abrotanum L. ("southernwood") belongs to the Artemisia genus and it is used in traditional medicine for the treatment of a variety of illnesses. Scarce data is available on the chemical composition of this medicinal plant, most research being focused on the quantitative and qualitative analyses of its essential oil. Our aim was to investigate the content and profile of polyphenols, flavonoids and hydroxycinnamic derivatives present in the Artemisiae abrotani herba extract. We conducted LC/MS analysis and we screened for 19 polyphenols, flavonoids and hydroxycinnamic derivatives. We determined the total content of these compounds and we screened for antioxidant activity. Most polyphenol acids, hydroxycinnamic derivatives and flavonoids were identified and quantified for the first time in this study. We found an original polyphenol distribution profile with high concentration of sinapic acid, rutin, quercetol, ferulic acid and patuletin. We measured the antioxidant activity, the ethanolic extract presenting a modest radical scavenging activity. The value of this study consists in its novelty as it adds new data on the chemical composition of A. abrotanum L. and it opens novel perspectives for medical and nutritional applications of this plant. PMID:26083039

  7. Differential effectiveness of berry polyphenols as anti-giardial agents.

    PubMed

    Anthony, J-P; Fyfe, L; Stewart, D; McDougall, G J

    2011-08-01

    Following previous work on the anti-giardial effect of blueberry polyphenols, a range of polyphenol-rich extracts from berries and other fruits was screened for their ability to kill Giardia duodenalis, an intestinal parasite of humans. Polyphenol-rich extracts were prepared from berries using solid-phase extraction and applied to trophozoites of Giardia duodenalis grown in vitro. All berry extracts caused inhibition at 166 μg gallic acid equivalents (GAE)/ml phenol content but extracts from strawberry, arctic bramble, blackberry and cloudberry were as effective as the currently used drug, metronidazole, causing complete trophozoite mortality in vitro. Cloudberry extracts were found to be the most effective causing effectively complete trophozoite mortality at 66 μg GAE/ml. The polyphenol composition of the more effective berry extracts suggested that the presence of ellagitannins could be an important factor. However, the potency of cloudberry could be related to high ellagitannin content but also to the presence of substantial amounts of unconjugated p-coumaric acid and benzoic acid. These in vitro effects occur at concentrations easily achievable in the gut after berry ingestion and we discuss the likelihood that berry extracts could be effective anti-giardial agents in vivo. PMID:21813029

  8. Estimated dietary intake and major food sources of polyphenols in the Polish arm of the HAPIEE study☆

    PubMed Central

    Grosso, Giuseppe; Stepaniak, Urszula; Topor-Mądry, Roman; Szafraniec, Krystyna; Pająk, Andrzej

    2014-01-01

    Objective The aim of this study was to estimate the intake of known individual polyphenols and their major dietary sources in the Polish arm of the HAPIEE (Health, Alcohol and Psychosocial factors In Eastern Europe) study. Methods A total of 10,477 random sample (45–69 y) of urban population of Krakow, Poland, completed a validated 148-item food frequency questionnaire. Polyphenol intake was calculated by matching food consumption data with the recently developed Phenol-Explorer database. Results The mean intake of polyphenols was 1756.5 ± 695.8 mg/d (median = 1662.5 mg/d). The main polyphenol groups were flavonoids (897 mg/d) and phenolic acids (800 mg/d). A total of 347 polyphenols from 19 polyphenol subclasses were found. The individual compounds with the highest intakes were isomers of chlorogenic acid (i.e., 5-caffeoylquinic acid and 4-caffeoylquinic acid) among hydroxycinnamic acids (average intake 150 mg/d), that largely originated from coffee, and compounds belonging to the catechin chemical family (i.e., [+]-gallocatechin, [-]-epigallocatechin 3-O-gallate, and [-]-epicatechin) among flavanols (average intake 50 mg/d), that mostly originated from tea and cocoa products. Conclusions The current study provides the most updated data for individual polyphenols intake in the diet of a well-established nutritional cohort. These findings will be useful to assess potential beneficial role on health of specific foods with high polyphenol content and characterize the effects of individual phenolic compounds. PMID:25280419

  9. Polyphenolic Compounds as Pancreatic Lipase Inhibitors.

    PubMed

    Buchholz, Tina; Melzig, Matthias F

    2015-07-01

    Obesity and its associated diseases such as diabetes mellitus and coronary heart diseases are a major challenge for our society. An important target for the treatment of obesity includes the development of inhibitors of nutrient digestion and absorption. Inhibition of pancreatic lipase and the associated reduction of lipid absorption is an attractive approach for the discovery of potent agents. Currently, the only clinically approved pharmacologic agent as pancreatic lipase inhibitor is Orlistat. However, its usage is compromised by unpleasant gastrointestinal adverse reactions (oily stools, oily spotting, flatulence). The use of botanical materials as a potential source of new drugs is of increasing importance and application. Natural products that are interesting for obesity treatment are generally considered to have less toxic and side effects than totally synthetic drugs. One of the most important sources of potential pancreatic lipase inhibitors represents the class of polyphenols. This article summarizes most studied subclasses of polyphenols including flavonoids, hydroxycinnamic acids, hydroxybenzoic acids and lignans with pancreatic lipase inhibitory effects. A structural comparison of potent inhibitors shows an increased inhibitory effect depending on number and position of phenolic hydroxyl groups, degree of polymerization and elimination of glycosylation during digestion. PMID:26132857

  10. Chicoric Acid Found in Basil (Ocimum basilicum L.) Leaves

    Technology Transfer Automated Retrieval System (TEKTRAN)

    This is the first report to identify the presence of chicoric acid (cichoric acid; also known as dicaffeoyltartaric acid) in basil leaves. Rosmarinic acid, chicoric acid, and caftaric acid (in the order of most abundant to least; all derivatives of caffeic acid) were identified in fresh basil leaves...

  11. Versatile surface engineering of porous nanomaterials with bioinspired polyphenol coatings for targeted and controlled drug delivery.

    PubMed

    Li, Juan; Wu, Shuxian; Wu, Cuichen; Qiu, Liping; Zhu, Guizhi; Cui, Cheng; Liu, Yuan; Hou, Weijia; Wang, Yanyue; Zhang, Liqin; Teng, I-Ting; Yang, Huang-Hao; Tan, Weihong

    2016-04-21

    The development of biocompatible drug delivery systems with targeted recognition and controlled release has experienced a number of design challenges, including, for example, complicated preparation steps and premature drug release. Herein, we address these problems through an in situ self-polymerization method that synthesizes biodegradable polyphenol-coated porous nanomaterials for targeted and controlled drug delivery. As a proof of concept, we synthesized polyphenol-coated mesoporous silica nanoparticles, termed MSN@polyphenol. The polyphenol coatings not only improved colloidal stability and prevented premature drug leakage, but also provided a scaffold for immobilization of targeting moieties, such as aptamers. Both immobilization of targeting aptamers and synthesis of polyphenol coating are easily accomplished without the aid of any other organic reagents. Importantly, the polyphenol coating (EGCg) used in this study could be biodegraded by acidic pH and intracellular glutathione, resulting in the release of trapped anticancer drugs. Based on confocal fluorescence microscopy and cytotoxicity experiments, drug-loaded and polyphenol-coated MSNs were shown to possess highly efficient internalization and an apparent cytotoxic effect on target cancer, but not control, cells. Our results suggest that these highly biocompatible and biodegradable polyphenol-coated MSNs are promising vectors for controlled-release biomedical applications and cancer therapy. PMID:27050780

  12. Natural Polyphenols in Cancer Chemoresistance.

    PubMed

    Hussain, Saad A; Sulaiman, Amal A; Balch, Curt; Chauhan, Harsh; Alhadidi, Qasim M; Tiwari, Amit K

    2016-01-01

    Resistance to chemotherapy remains a major impediment to the management of most types of cancer. Both intrinsic and acquired drug resistance are mediated by several cellular and molecular mechanisms, including alternative growth-signaling pathways unaffected by specific therapies, alterations in the tumor microenvironment (e.g., hypoxia and angiogenesis), and active transport of drugs out of the cell. Epidemiological studies have validated an inverse correlation between the consumption of dietary polyphenols and the risk of cancer, which has been attributed to polyphenol antioxidant capacity and their potential to inhibit activation of procarcinogens, cancer cell proliferation, metastasis, and angiogenesis, and inhibition or downregulation of active drug efflux transporters. Moreover, polyphenols can induce apoptosis in cancer cells and modulate immune responses and inflammatory cascades. Augmentation of the efficacy of chemotherapy and prevention of multidrug resistance are other important effects of dietary polyphenols that deserve further research, especially after the discovery of tight "crosstalk" between aberrant growth signaling and metabolic dysfunction in cancer cells. In this review, we cover what is currently known about the role of natural polyphenolic compounds in overcoming cancer drug resistance mediated by diverse primary and secondary resistance mechanisms. PMID:27366999

  13. Black tea polyphenols: a mechanistic treatise.

    PubMed

    Butt, M S; Imran, A; Sharif, M K; Ahmad, Rabia Shabir; Xiao, Hang; Imran, M; Rsool, H A

    2014-01-01

    Dietary interventions are among the emerging trends to curtail physiological malfunctioning like cancer, diabetes, cardiac complications, etc. The essence of phytonutrients has developed the concept of nutraceuticals at the junction of diet health linkages. In this context, theaflavin & thearubigins are the oxidized derivatives of black tea catechins during fermentation having nutraceutical potential owing to esterification of hydroxyl ring with digallate esters. Theaflavin may influence activation of transcription factors such as NFnB or AP-1 that ultimately hinder the formation of nitric oxide expression gene. Likewise, black tea contains a unique amino acid theanine acts as neurotransmitter owing to its ability to cross the blood-brain barrier. Moreover, it boasts immunity by enhancing the disease-fighting ability of gamma delta T cells. Theaflavin & thearubigins act as safeguard against oxidative stress thereby effective in the cardiac functioning. The mechanistic approach of these antioxidants is likely to be associated with inhibition of redox sensitive transcription factors & pro-oxidant enzymes such as xanthine oxidase or nitric oxide synthase. However, their involvement in antioxidative enzyme induction as in glutathione-S-transferases is also well documented. They act as curative agent against numerous pathological disorders by disrupting the electron chain thus inhibiting the progression of certain ailments. Black tea polyphenols established themselves as strong antioxidants due to their standard one-electron potential, and their vitality is dependent on the concentration of polyphenols and pH for their inclusive execution. Present review is an attempt to enrich the readers regarding the health promoting aspects of black tea polyphenols. Concomitantly, it needs core attention of researchers for the exploitations of black tea flavanols as an important dietary constituent for the vulnerable segment. PMID:24499118

  14. Proximate and polyphenolic characterization of cranberry pomace

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The proximate composition and identification and quantification of polyphenolic compounds in dried cranberry pomace were determined. Proximate analysis was conducted based on AOAC methods for moisture, protein, fat, and ash. Total carbohydrates were determined by the difference method. Polyphenolic ...

  15. Biotransformation of caffeoyl quinic acids from green coffee extracts by Lactobacillus johnsonii NCC 533

    PubMed Central

    2013-01-01

    The potential of Lactobacillus johnsonii NCC 533 to metabolize chlorogenic acids from green coffee extract was investigated. Two enzymes, an esterase and a hydroxycinnamate decarboxylase (HCD), were involved in this biotransformation. The complete hydrolysis of 5-caffeoylquinic acid (5-CQA) into caffeic acid (CA) by L. johnsonii esterase occurred during the first 16 h of reaction time. No dihydrocaffeic acid was identified in the reaction mixture. The decarboxylation of CA into 4-vinylcatechol (4-VC) started only when the maximum concentration of CA was reached (10 μmol/ml). CA was completely transformed into 4-VC after 48 h of incubation. No 4-vinylphenol or other derivatives could be identified in the reaction media. In this study we demonstrate the capability of L. johnsonii to transform chlorogenic acids from green coffee extract into 4-VC in two steps one pot reaction. Thus, the enzymatic potential of certain lactobacilli might be explored to generate flavor compounds from plant polyphenols. PMID:23692950

  16. Biotransformation of caffeoyl quinic acids from green coffee extracts by Lactobacillus johnsonii NCC 533.

    PubMed

    Bel-Rhlid, Rachid; Thapa, Dinesh; Kraehenbuehl, Karin; Hansen, Carl Erik; Fischer, Lutz

    2013-01-01

    The potential of Lactobacillus johnsonii NCC 533 to metabolize chlorogenic acids from green coffee extract was investigated. Two enzymes, an esterase and a hydroxycinnamate decarboxylase (HCD), were involved in this biotransformation. The complete hydrolysis of 5-caffeoylquinic acid (5-CQA) into caffeic acid (CA) by L. johnsonii esterase occurred during the first 16 h of reaction time. No dihydrocaffeic acid was identified in the reaction mixture. The decarboxylation of CA into 4-vinylcatechol (4-VC) started only when the maximum concentration of CA was reached (10 μmol/ml). CA was completely transformed into 4-VC after 48 h of incubation. No 4-vinylphenol or other derivatives could be identified in the reaction media. In this study we demonstrate the capability of L. johnsonii to transform chlorogenic acids from green coffee extract into 4-VC in two steps one pot reaction. Thus, the enzymatic potential of certain lactobacilli might be explored to generate flavor compounds from plant polyphenols. PMID:23692950

  17. Cluster analysis of polyphenol intake in a French middle-aged population (aged 35-64 years).

    PubMed

    Julia, Chantal; Touvier, Mathilde; Lassale, Camille; Fezeu, Léopold; Galan, Pilar; Hercberg, Serge; Kesse-Guyot, Emmanuelle

    2016-01-01

    Polyphenols have been suggested as protective factors for a range of chronic diseases. However, studying the impact of individual polyphenols on health is hindered by the intrinsic inter-correlations among polyphenols. Alternatively, studying foods rich in specific polyphenols fails to grasp the ubiquity of these components. Studying overall dietary patterns would allow for a more comprehensive description of polyphenol intakes in the population. Our objective was to identify clusters of dietary polyphenol intakes in a French middle-aged population (35-64 years old). Participants from the primary prevention trial SUpplementation en VItamines et Minéraux AntioXydants (SU.VI.MAX) study were included in the present cross-sectional study (n 6092; 57·8 % females; mean age 48·7 (sd 6·4) years). The fifty most consumed individual dietary polyphenols were divided into energy-adjusted tertiles and introduced in a multiple correspondence analysis (MCA), leading to comprehensive factors of dietary polyphenol intakes. The identified factors discriminating polyphenol intakes were used in a hierarchical clustering procedure. Four clusters were identified, corresponding broadly to clustered preferences for their respective food sources. Cluster 1 was characterised by high intakes of tea polyphenols. Cluster 2 was characterised by high intakes of wine polyphenols. Cluster 3 was characterised by high intakes of flavanones and flavones, corresponding to high consumption of fruit and vegetables, and more broadly to a healthier diet. Cluster 4 was characterised by high intakes of hydroxycinnamic acids, but was also associated with alcohol consumption and smoking. Profiles of polyphenol intakes allowed for the identification of meaningful combinations of polyphenol intakes in the diet. PMID:27547391

  18. Effect of milk on the urinary excretion of microbial phenolic acids after cocoa powder consumption in humans.

    PubMed

    Urpi-Sarda, Mireia; Llorach, Rafael; Khan, Nasiruddin; Monagas, Maria; Rotches-Ribalta, Maria; Lamuela-Raventos, Rosa; Estruch, Ramon; Tinahones, Francisco J; Andres-Lacueva, Cristina

    2010-04-28

    Health effects of cocoa flavonols depend on their bioavailability, which is strongly influenced by the food matrix and the degree of flavanol polymerization. The effect of milk on the bioavailability of cocoa flavanoids considering phase II metabolites of epicatechin has been the subject of considerable debate. This work studies the effect of milk at the colonic microbial metabolism level of the nonabsorbed flavanol fraction that reaches the colon and is metabolized by the colonic microbiota into various phenolic acids. Twenty-one human volunteers followed a diet low in polyphenols for at least 48 h before taking, in a random order, 40 g of cocoa powder dissolved either in 250 mL of whole milk or in 250 mL of water. Urine samples were collected before the intake and during three different periods (0-6, 6-12, and 12-24 h). Phenolic acids were analyzed by LC-MS/MS after solid-phase extraction. Of the 15 metabolites assessed, the excretion of 9 phenolic acids was affected by the intake of milk. The urinary concentration of 3,4-dihydroxyphenylacetic, protocatechuic, 4-hydroxybenzoic, 4-hydroxyhippuric, hippuric, caffeic, and ferulic acids diminished after the intake of cocoa with milk, whereas urinary concentrations of vanillic and phenylacetic acids increased. In conclusion, milk partially affects the formation of microbial phenolic acids derived from the colonic degradation of procyanidins and other compounds present in cocoa powder. PMID:20222713

  19. Dietary intake of polyphenols, nitrate and nitrite and gastric cancer risk in Mexico City

    PubMed Central

    Hernández-Ramírez, Raúl U.; Galván-Portillo, Marcia V.; Ward, Mary H.; Agudo, Antonio; González, Carlos A.; Oñate-Ocaña, Luis F.; Herrera-Goepfert, Roberto; Palma-Coca, Oswaldo; López-Carrillo, Lizbeth

    2009-01-01

    N-Nitroso compounds (NOC) are potent animal carcinogens and potential human carcinogens. The primary source of exposure for most individuals may be endogenous formation, a process that can be inhibited by dietary polyphenols. To estimate the risk of gastric cancer (GC) in relation to the individual and combined consumption of polyphenols and NOC precursors (nitrate and nitrite), a population-based case–control study was carried out in Mexico City from 2004 to 2005 including 257 histologically confirmed GC cases and 478 controls. Intake of polyphenols, nitrate and nitrite were estimated using a food frequency questionnaire. High intakes of cinnamic acids, secoisolariciresinol and coumestrol were associated with an ~50% reduction in GC risk. A high intake of total nitrite as well as nitrate and nitrite from animal sources doubled the GC risk. Odds ratios around 2-fold were observed among individuals with both low intake of cinnamic acids, secoisolariciresinol or coumestrol and high intake of animal-derived nitrate or nitrite, compared to high intake of the polyphenols and low animal nitrate or nitrite intake, respectively. Results were similar for both the intestinal and diffuse types of GC. Our results show, for the first time, a protective effect for GC because of higher intake of cinnamic acids, secoisolariciresinol and coumestrol, and suggest that these polyphenols reduce GC risk through inhibition of endogenous nitrosation. The main sources of these polyphenols were pears, mangos and beans for cinnamic acids; beans, carrots and squash for secoisolariciresinol and legumes for coumestrol. PMID:19449378

  20. Monolignol Pathway 4-Coumaric Acid:Coenzyme A Ligases in Populus. trichocarpa: Novel Specificity, Metabolic Regulation, and Simulation of Coenzyme A Ligation Fluxes1[W

    PubMed Central

    Chen, Hsi-Chuan; Song, Jina; Williams, Cranos M.; Shuford, Christopher M.; Liu, Jie; Wang, Jack P.; Li, Quanzi; Shi, Rui; Gokce, Emine; Ducoste, Joel; Muddiman, David C.; Sederoff, Ronald R.; Chiang, Vincent L.

    2013-01-01

    4-Coumaric acid:coenzyme A ligase (4CL) is involved in monolignol biosynthesis for lignification in plant cell walls. It ligates coenzyme A (CoA) with hydroxycinnamic acids, such as 4-coumaric and caffeic acids, into hydroxycinnamoyl-CoA thioesters. The ligation ensures the activated state of the acid for reduction into monolignols. In Populus spp., it has long been thought that one monolignol-specific 4CL is involved. Here, we present evidence of two monolignol 4CLs, Ptr4CL3 and Ptr4CL5, in Populus trichocarpa. Ptr4CL3 is the ortholog of the monolignol 4CL reported for many other species. Ptr4CL5 is novel. The two Ptr4CLs exhibited distinct Michaelis-Menten kinetic properties. Inhibition kinetics demonstrated that hydroxycinnamic acid substrates are also inhibitors of 4CL and suggested that Ptr4CL5 is an allosteric enzyme. Experimentally validated flux simulation, incorporating reaction/inhibition kinetics, suggested two CoA ligation paths in vivo: one through 4-coumaric acid and the other through caffeic acid. We previously showed that a membrane protein complex mediated the 3-hydroxylation of 4-coumaric acid to caffeic acid. The demonstration here of two ligation paths requiring these acids supports this 3-hydroxylation function. Ptr4CL3 regulates both CoA ligation paths with similar efficiencies, whereas Ptr4CL5 regulates primarily the caffeic acid path. Both paths can be inhibited by caffeic acid. The Ptr4CL5-catalyzed caffeic acid metabolism, therefore, may also act to mitigate the inhibition by caffeic acid to maintain a proper ligation flux. A high level of caffeic acid was detected in stem-differentiating xylem of P. trichocarpa. Our results suggest that Ptr4CL5 and caffeic acid coordinately modulate the CoA ligation flux for monolignol biosynthesis. PMID:23344904

  1. Dietary Polyphenols and Their Biological Significance

    PubMed Central

    Han, Xiuzhen; Shen, Tao; Lou, Hongxiang

    2007-01-01

    Dietary polyphenols represent a wide variety of compounds that occur in fruits, vegetables, wine, tea, extra virgin olive oil, chocolate and other cocoa products. They are mostly derivatives and/or isomers of flavones, isoflavones, flavonols, catechins and phenolic acids, and possess diverse biological properties such as antioxidant, antiapoptosis, anti-aging, anticarcinogen, anti-inflammation, anti-atherosclerosis, cardiovascular protection, improvement of the endothelial function, as well as inhibition of angiogenesis and cell proliferation activity. Most of these biological actions have been attributed to their intrinsic reducing capabilities. They may also offer indirect protection by activating endogenous defense systems and by modulating cellular signaling processes such as nuclear factor-kappa B (NF-κB) activation, activator protein-1(AP-1) DNA binding, glutathione biosynthesis, phosphoinositide 3 (PI3)-kinase/protein kinase B (Akt) pathway, mitogen-activated protein kinase (MAPK) proteins [extracellular signal-regulated protein kinase (ERK), c-jun N-terminal kinase (JNK) and P38 ] activation, and the translocation into the nucleus of nuclear factor erythroid 2 related factor 2 (Nrf2). This paper covers the most recent literature on the subject, and describes the biological mechanisms of action and protective effects of dietary polyphenols.

  2. Physical and antibacterial properties of edible films formulated with apple skin polyphenols.

    PubMed

    Du, W-X; Olsen, C W; Avena-Bustillos, R J; Friedman, M; McHugh, T H

    2011-03-01

    Fruit and vegetable skins have polyphenolic compounds, terpenes, and phenols with antimicrobial and antioxidant activity. These flavoring plant essential oil components are generally regarded as safe. Edible films made from fruits or vegetables containing apple skin polyphenols have the potential to be used commercially to protect food against contamination by pathogenic bacteria. The main objective of this study was to evaluate physical properties as well as antimicrobial activities against Listeria monocytogenes, Escherichia coli O157:H7, and Salmonella enterica of apple skin polyphenols at 0% to 10% (w/w) concentrations in apple puree film-forming solutions formulated into edible films. Commercial apple skin polyphenol powder had a water activity of 0.44 and high total soluble phenolic compounds and antioxidant capacity (995.3 mg chlorogenic acid/100 g and 14.4 mg Trolox/g, respectively). Antimicrobial activities of edible film containing apple skin polyphenols were determined by the overlay method. Apple edible film with apple skin polyphenols was highly effective against L. monocytogenes. The minimum concentration need to inactive L. monocytogenes was 1.5%. However, apple skin polyphenols did not show any antimicrobial effect against E. coli O157:H7 and S. enterica even at 10% level. The presence of apple skin polyphenols reduced water vapor permeability of films. Apple skin polyphenols increased elongation of films and darkened the color of films. The results of the present study show that apple skin polyphenols can be used to prepare apple-based antimicrobial edible films with good physical properties for food applications by direct contact. PMID:21535779

  3. Ellagic acid, a polyphenolic compound, selectively induces ROS-mediated apoptosis in cancerous B-lymphocytes of CLL patients by directly targeting mitochondria

    PubMed Central

    Salimi, Ahmad; Roudkenar, Mehryar Habibi; Sadeghi, Leila; Mohseni, Alireza; Seydi, Enayatollah; Pirahmadi, Nahal; Pourahmad, Jalal

    2015-01-01

    To investigate the effects ofellagic acid (EA) on the cytotoxicity, B-lymphocytes isolated from CLL patients and healthy individuals. Flow cytometric assay was used to measure the percentage of apoptosis versus necrosis, intracellular active oxygen radicals (ROS), mitochondrial membrane potential (MMP) and the caspase-3 activity and then mitochondria were isolated from both groups B-lymphocytes and parameters of mitochondrial toxicity was investigated. Based on our results EA decreased the percentage of viable cells and induced apoptosis. EA increased ROS formation, mitochondria swelling, MMP decrease and cytochrome c release in mitochondria isolated from CLL BUT NOT healthy B-lymphocytes while pre-treatment with cyclosporine A and Butylated hydroxyl toluene (BHT) prevented these effects. Our results suggest that EA can act as an anti cancer candidate by directly and selectively targeting mitochondria could induce apoptosis through mitochondria pathway with increasing ROS production which finally ends in cytochrome c release, caspase 3 activation and apoptosis in cancerous B-lymphocytes isolated from CLL patients. PMID:26418626

  4. Dmp53, basket and drICE gene knockdown and polyphenol gallic acid increase life span and locomotor activity in a Drosophila Parkinson’s disease model

    PubMed Central

    Ortega-Arellano, Hector Flavio; Jimenez-Del-Rio, Marlene; Velez-Pardo, Carlos

    2013-01-01

    Understanding the mechanism(s) by which dopaminergic (DAergic) neurons are eroded in Parkinson’s disease (PD) is critical for effective therapeutic strategies. By using the binary tyrosine hydroxylase (TH)-Gal4/UAS-X RNAi Drosophila melanogaster system, we report that Dmp53, basket and drICE gene knockdown in dopaminergic neurons prolong life span (p < 0.05; log-rank test) and locomotor activity (p < 0.05; χ2 test) in D. melanogaster lines chronically exposed to (1 mM) paraquat (PQ, oxidative stress (OS) generator) compared to untreated transgenic fly lines. Likewise, knockdown flies displayed higher climbing performance than control flies. Amazingly, gallic acid (GA) significantly protected DAergic neurons, ameliorated life span, and climbing abilities in knockdown fly lines treated with PQ compared to flies treated with PQ only. Therefore, silencing specific gene(s) involved in neuronal death might constitute an excellent tool to study the response of DAergic neurons to OS stimuli. We propose that a therapy with antioxidants and selectively “switching off” death genes in DAergic neurons could provide a means for pre-clinical PD individuals to significantly ameliorate their disease condition. PMID:24385865

  5. Profiling Polyphenols in Five Brassica species Microgreens by UHPLC-PDA-ESI/HRMSn

    PubMed Central

    Sun, Jianghao; Xiao, Zhenlei; Lin, Long-ze; Lester, Gene E.; Wang, Qin; Harnly, James M.; Chen, Pei

    2014-01-01

    Brassica vegetables are known to contain relatively high concentrations of bioactive compounds associated with human health. A comprehensive profiling of polyphenols from five Brassica species microgreens was conducted using ultra high-performance liquid chromatography photo diode array high-resolution multi-stage mass spectrometry (UHPLC-PDA-ESI/HRMSn). A total of 164 polyphenols including 30 anthocyanins, 105 flavonol glycosides, and 29 hydroxycinnamic acid and hydroxybenzoic acid derivatives were putatively identified.The putative identifications were based on UHPLC-HRMSn analysis using retention times, elution orders, UV/Vis spectra and high resolution mass spectra, in-house polyphenol database, and as well as literature comparisons. This study showed that these five Brassica species microgreens could be considered as good sources of food polyphenols. PMID:24144328

  6. Polyphenols: a nutraceutical approach against diseases.

    PubMed

    Gollucke, Andréa P B; Peres, Rogério C; Odair A; Ribeiro, Daniel A

    2013-12-01

    Polyphenols are abundant in red grapes and in their derived products, amongst other natural food sources. These compounds are associated with the prevention of diseases caused by oxidative stress. The present review discusses the action of grape polyphenols against diseases and the new polyphenol-rich products developed to be used as nutraceuticals. Grape polyphenols demonstrated effects such as maintenance of endothelial function, increase in antioxidant capacity and protection against LDL oxidation. Recent patents regarding polyphenols show a tendency to use a right-on-target approach and the new patented products are aiming at preventing and treating specific diseases. PMID:24294942

  7. Chlorogenic acid ameliorates intestinal mitochondrial injury by increasing antioxidant effects and activity of respiratory complexes.

    PubMed

    Zhou, Yan; Zhou, Lili; Ruan, Zheng; Mi, Shumei; Jiang, Min; Li, Xiaolan; Wu, Xin; Deng, Zeyuan; Yin, Yulong

    2016-05-01

    Dietary polyphenols are thought to be beneficial for human health by acting as antioxidants. Chlorogenic acid (CGA) is abundant in plant-based foods as an ester of caffeic acid and quinic acid. In this study, we investigated the effects of CGA on mitochondrial protection. Our results demonstrated that pretreatment with CGA ameliorated the intestinal mitochondrial injury induced by H2O2; membrane potential was increased, mitochondrial swelling, levels of reactive oxygen species, contents of 8-hydroxy-2-deoxyguanosine, and cytochrome c released were decreased. The beneficial effects of CGA were accompanied by an increase in antioxidant and respiratory-chain complex I, IV, and V activities. In trinitrobenzene-sulfonic acid-induced colitic rats indicated that CGA supplementation improved mitochondria ultrastructure and decreased mitochondrial injury. Our results suggest a promising role for CGA as a mitochondria-targeted antioxidant in combating intestinal oxidative injury. Daily intake of diets containing CGA, such as coffee and honeysuckle, may be useful for prevention of intestinal diseases. PMID:26824685

  8. Unique metabolites protect earthworms against plant polyphenols

    PubMed Central

    Liebeke, Manuel; Strittmatter, Nicole; Fearn, Sarah; Morgan, A. John; Kille, Peter; Fuchser, Jens; Wallis, David; Palchykov, Vitalii; Robertson, Jeremy; Lahive, Elma; Spurgeon, David J.; McPhail, David; Takáts, Zoltán; Bundy, Jacob G.

    2015-01-01

    All higher plants produce polyphenols, for defence against above-ground herbivory. These polyphenols also influence the soil micro- and macro-fauna that break down plant leaf litter. Polyphenols therefore indirectly affect the fluxes of soil nutrients and, ultimately, carbon turnover and ecosystem functioning in soils. It is unknown how earthworms, the major component of animal biomass in many soils, cope with high-polyphenol diets. Here, we show that earthworms possess a class of unique surface-active metabolites in their gut, which we term ‘drilodefensins'. These compounds counteract the inhibitory effects of polyphenols on earthworm gut enzymes, and high-polyphenol diets increase drilodefensin concentrations in both laboratory and field populations. This shows that drilodefensins protect earthworms from the harmful effects of ingested polyphenols. We have identified the key mechanism for adaptation to a dietary challenge in an animal group that has a major role in organic matter recycling in soils worldwide. PMID:26241769

  9. Unique metabolites protect earthworms against plant polyphenols.

    PubMed

    Liebeke, Manuel; Strittmatter, Nicole; Fearn, Sarah; Morgan, A John; Kille, Peter; Fuchser, Jens; Wallis, David; Palchykov, Vitalii; Robertson, Jeremy; Lahive, Elma; Spurgeon, David J; McPhail, David; Takáts, Zoltán; Bundy, Jacob G

    2015-01-01

    All higher plants produce polyphenols, for defence against above-ground herbivory. These polyphenols also influence the soil micro- and macro-fauna that break down plant leaf litter. Polyphenols therefore indirectly affect the fluxes of soil nutrients and, ultimately, carbon turnover and ecosystem functioning in soils. It is unknown how earthworms, the major component of animal biomass in many soils, cope with high-polyphenol diets. Here, we show that earthworms possess a class of unique surface-active metabolites in their gut, which we term 'drilodefensins'. These compounds counteract the inhibitory effects of polyphenols on earthworm gut enzymes, and high-polyphenol diets increase drilodefensin concentrations in both laboratory and field populations. This shows that drilodefensins protect earthworms from the harmful effects of ingested polyphenols. We have identified the key mechanism for adaptation to a dietary challenge in an animal group that has a major role in organic matter recycling in soils worldwide. PMID:26241769

  10. Matching in Vitro Bioaccessibility of Polyphenols and Antioxidant Capacity of Soluble Coffee by Boosted Regression Trees.

    PubMed

    Podio, Natalia S; López-Froilán, Rebeca; Ramirez-Moreno, Esther; Bertrand, Lidwina; Baroni, María V; Pérez-Rodríguez, María L; Sánchez-Mata, María-Cortes; Wunderlin, Daniel A

    2015-11-01

    The aim of this study was to evaluate changes in polyphenol profile and antioxidant capacity of five soluble coffees throughout a simulated gastro-intestinal digestion, including absorption through a dialysis membrane. Our results demonstrate that both polyphenol content and antioxidant capacity were characteristic for each type of studied coffee, showing a drop after dialysis. Twenty-seven compounds were identified in coffee by HPLC-MS, while only 14 of them were found after dialysis. Green+roasted coffee blend and chicory+coffee blend showed the highest and lowest content of polyphenols and antioxidant capacity before in vitro digestion and after dialysis, respectively. Canonical correlation analysis showed significant correlation between the antioxidant capacity and the polyphenol profile before digestion and after dialysis. Furthermore, boosted regression trees analysis (BRT) showed that only four polyphenol compounds (5-p-coumaroylquinic acid, quinic acid, coumaroyl tryptophan conjugated, and 5-O-caffeoylquinic acid) appear to be the most relevant to explain the antioxidant capacity after dialysis, these compounds being the most bioaccessible after dialysis. To our knowledge, this is the first report matching the antioxidant capacity of foods with the polyphenol profile by BRT, which opens an interesting method of analysis for future reports on the antioxidant capacity of foods. PMID:26457815

  11. Antioxidative Polyphenols from Defatted Oilseed Cakes: Effect of Solvents

    PubMed Central

    Teh, Sue-Siang; Bekhit, Alaa El-Din; Birch, John

    2014-01-01

    Defatted hemp, flax and canola seed cakes were extracted with different solvent systems namely methanol, ethanol, acetone, methanol 80%, acetone 80% and mixed solvent of methanol:acetone:water (MAW, 7:7:6, v/v/v). Each extract was analyzed for antioxidant capacity using ferric reducing/antioxidant power (FRAP) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assays. MAW exhibited the highest extraction of phenolic and flavonoid contents in the seed cakes, followed by acetone 80% and methanol 80%. The antioxidant capacity was proportional to the polyphenols recovery in the extracts. Canola seed cakes possessed the highest recovery of polyphenols and antioxidant capacity, followed by hemp and flax seed cakes. MAW extract of canola contained total phenolic content, 2104.67 ± 2.52 mg GAE/100 g fresh weight; total flavonoids, 37.79 ± 0.04 mg LUE/100 g fresh weight; percentage inhibition of DPPH•, 33.03 ± 0.38%; FRAP assay, 8.78 ± 0.07 μmol Fe (II)/g fresh weight. Identification of individual polyphenol compounds were performed HPLC. MAW extract of canola had the highest (P < 0.05) concentration of all individual polyphenols except gallic acid and catechin. Highest concentration of quercetin and luteolin in MAW extract of hemp was obtained among all solvent systems. PMID:26784664

  12. Glutathione conjugation of chlorambucil: measurement and modulation by plant polyphenols.

    PubMed

    Zhang, K; Wong, K P

    1997-07-15

    Chlorambucil (CMB), an anticancer drug, was cytotoxic at concentrations of 5-20 microM to human colon adenocarcinoma cells. It inhibited [14C]thymidine uptake in a dose-dependent manner. Both effects were potentiated by simultaneous exposure of the cells to 10 microM plant polyphenols. In an attempt to explain the possible mechanism of action of the polyphenols in relation to these observations, an HPLC-radiometric method was developed to measure the conjugation of CMB with glutathione in these cells and to monitor the export of monochloromonoglutathionyl CMB (MG-CMB), its main glutathione conjugate. At micromolar concentrations, five polyphenols, namely quercetin, butein, tannic acid, 2'-hydroxychalcone and morin, inhibited the efflux of CMB significantly; an inhibition of 40% was observed with 10 microM quercetin. The glutathione S-transferase (GST) activity of the cancer cells, measured with 1-chloro-2,4-dinitrobenzene, was also inhibited by the polyphenols. Their combined action on GST and on the efflux of MG-CMB conjugate could provide an enhanced positive modulation of sensitivity of the tumour cells to CMB. PMID:9230122

  13. Bioavailability of dietary polyphenols and gut microbiota metabolism: antimicrobial properties.

    PubMed

    Marín, Laura; Miguélez, Elisa M; Villar, Claudio J; Lombó, Felipe

    2015-01-01

    Polyphenolic compounds are plant nutraceuticals showing a huge structural diversity, including chlorogenic acids, hydrolyzable tannins, and flavonoids (flavonols, flavanones, flavan-3-ols, anthocyanidins, isoflavones, and flavones). Most of them occur as glycosylated derivatives in plants and foods. In order to become bioactive at human body, these polyphenols must undergo diverse intestinal transformations, due to the action of digestive enzymes, but also by the action of microbiota metabolism. After elimination of sugar tailoring (generating the corresponding aglycons) and diverse hydroxyl moieties, as well as further backbone reorganizations, the final absorbed compounds enter the portal vein circulation towards liver (where other enzymatic transformations take place) and from there to other organs, including behind the digestive tract or via blood towards urine excretion. During this transit along diverse tissues and organs, they are able to carry out strong antiviral, antibacterial, and antiparasitic activities. This paper revises and discusses these antimicrobial activities of dietary polyphenols and their relevance for human health, shedding light on the importance of polyphenols structure recognition by specific enzymes produced by intestinal microbial taxa. PMID:25802870

  14. Antioxidative and Antidiabetic Effects of Natural Polyphenols and Isoflavones.

    PubMed

    Umeno, Aya; Horie, Masanori; Murotomi, Kazutoshi; Nakajima, Yoshihiro; Yoshida, Yasukazu

    2016-01-01

    Many polyphenols that contain more than two phenolic hydroxyl groups are natural antioxidants and can provide health benefits to humans. These polyphenols include, for example, oleuropein, hydroxytyrosol, catechin, chlorogenic acids, hesperidin, nobiletin, and isoflavones. These have been studied widely because of their strong radical-scavenging and antioxidative effects. These effects may contribute to the prevention of diseases, such as diabetes. Insulin secretion, insulin resistance, and homeostasis are important factors in the onset of diabetes, a disease that is associated with dysfunction of pancreatic β-cells. Oxidative stress is thought to contribute to this dysfunction and the effects of antioxidants on the pathogenesis of diabetes have, therefore, been investigated. Here, we summarize the antioxidative effects of polyphenols from the perspective of their radical-scavenging activities as well as their effects on signal transduction pathways. We also describe the preventative effects of polyphenols on diabetes by referring to recent studies including those reported by us. Appropriate analytical approaches for evaluating antioxidants in studies on the prevention of diabetes are comprehensively reviewed. PMID:27248987

  15. Bioavailability of Dietary Polyphenols and Gut Microbiota Metabolism: Antimicrobial Properties

    PubMed Central

    Miguélez, Elisa M.; Villar, Claudio J.

    2015-01-01

    Polyphenolic compounds are plant nutraceuticals showing a huge structural diversity, including chlorogenic acids, hydrolyzable tannins, and flavonoids (flavonols, flavanones, flavan-3-ols, anthocyanidins, isoflavones, and flavones). Most of them occur as glycosylated derivatives in plants and foods. In order to become bioactive at human body, these polyphenols must undergo diverse intestinal transformations, due to the action of digestive enzymes, but also by the action of microbiota metabolism. After elimination of sugar tailoring (generating the corresponding aglycons) and diverse hydroxyl moieties, as well as further backbone reorganizations, the final absorbed compounds enter the portal vein circulation towards liver (where other enzymatic transformations take place) and from there to other organs, including behind the digestive tract or via blood towards urine excretion. During this transit along diverse tissues and organs, they are able to carry out strong antiviral, antibacterial, and antiparasitic activities. This paper revises and discusses these antimicrobial activities of dietary polyphenols and their relevance for human health, shedding light on the importance of polyphenols structure recognition by specific enzymes produced by intestinal microbial taxa. PMID:25802870

  16. Molecular structure‐function relationship of dietary polyphenols for inhibiting VEGF‐induced VEGFR‐2 activity

    PubMed Central

    Cerezo, Ana B.; Winterbone, Mark S.; Moyle, Christina W. A.; Needs, Paul W.

    2015-01-01

    1 Scope We recently reported potent inhibition of VEGF signalling by two flavanols at sub‐micromolar concentrations, mediated by direct binding of the flavanols to VEGF. The aim of this study was to quantify the inhibitory potency and binding affinity of a wide range of dietary polyphenols and determine the structural requirements for VEGF inhibition. 2 Methods and results The concentration of polyphenol required to cause 50% inhibition (IC50) of VEGF‐dependent VEGFR‐2 activation in HUVECS was determined after pretreating VEGF with polyphenols at various concentations. Binding affinities and binding sites on VEGF were predicted using in‐silico modelling. Ellagic acid and 15 flavonoids had IC50 values ≤10 μM while 28 other polyhenols were weak/non‐inhibitors. Structural features associated with potent inhibition included 3‐galloylation, C‐ring C2=C3, total OH, B‐ring catechol, C‐ring 3‐OH of flavonoids. Potency was not associated with polyphenol hydrophobicity. There was a strong correlation between potency of inhibition and binding affinities, and all polyphenols were predicted to bind to a region on VEGF involved in VEGFR‐2 binding. 3 Conclusion Specific polyphenols bind directly to a discrete region of VEGF and inhibit VEGF signalling, and this potentially explains the associations between consumption of these polyphenols and CVD risk. PMID:26250940

  17. Effect of polyphenols on glucose and lactate transport by breast cancer cells.

    PubMed

    Martel, F; Guedes, M; Keating, E

    2016-05-01

    One of the cancer molecular hallmarks is a deviant energetic metabolism, known as the Warburg effect, whereby the rate of glucose uptake is significantly increased and a high rate of glycolysis and lactic acid production occurs even when oxygen is present-"aerobic lactatogenesis". Accordingly, GLUT1 and MCT1, which are the main glucose and lactate transporters in cancer cells, respectively, have been proposed as oncogenes and are currently seen as potential therapeutic targets in cancer treatment. Polyphenols, commonly contained in fruits and vegetables, have long been associated with a protective role against cancer. Generally considered as nontoxic, dietary polyphenols are considered ideal chemopreventive and possibly chemotherapeutic agents. Several mechanisms of action of polyphenols in breast cancer cells have been proposed including modulation of intracellular signaling, induction of apoptosis through redox regulation or modulation of epigenetic alterations. Additionally, in vitro studies have shown that several polyphenols act as specific inhibitors of glucose transport in breast cancer cell lines and an association between their anticarcinogenic effect and inhibition of glucose cellular uptake has been described. Also, some polyphenols were found to inhibit lactate transport. Importantly, some polyphenols behave as inhibitors of both glucose and lactate cellular uptake by breast cancer cells and these compounds are thus very interesting in the context of a chemopreventive effect, because they deplete breast cancer cells of their two most important energy suppliers. So, the antimetabolic effect of polyphenols should be regarded as a mechanism of action contributing to their chemopreventive/chemotherapeutic potential in relation to breast cancer. PMID:27097608

  18. [Correlation analysis of nutrients and microorganisms in soils with polyphenols and total flavonoids of Houttuynia cordata].

    PubMed

    Wu, Dan; Luo, Shi-qiong; Yang, Zhan-nan; Ma, Jing; Hong, Liang

    2015-04-01

    The relationship of nutrients and microorganisms in soils with polyphenols and total flavonoids of Houttuynia cordata were investigated by measuring nutrients, enzyme activity, pH, concentrations of microbe phospholipid fatty acids (PLFAs) in soils, and determining concentrations of polyphenols and total flavonoids of H. cordata. The research is aimed to understand characteristics of the planting soils and improve the quality of cultivated H. cordata. The soils at different sample sites varied greatly in nutrients, enzyme activity, pH, microbic PLFAs and polyphenols and all flavonoids. The content of total PLFAs in sample sites was following: bacteria > fungi > actinomyces > nematode. The content of bacteria PLFAs was 37.5%-65.0% at different sample sites. Activities of polyphenol oxidease, concentrations of available P and content of PLFAs of bacteria, actinomyces and total microorganisms in soils were significantly and positively related to the concentrations of polyphenols and total flavonoids of H. cordata, respectively (P < 0.05) . The Content of fungi PLFAs in soils was significantly and negatively related to concentrations of polyphenols and total flavonoids of H. cordata, respectively (P < 0.05). This study provides evidence that effectiveness of the soil nutrient, which may be improved due to transformation of soil microorganisms and enzymes to N and P in the soils, was beneficial to adaptation of H. cordata adapted to different soil conditions, and significantly affects metabolic accumulation of polyphenols and flavonoids of H. cordata. PMID:26281577

  19. In vitro extraction and fermentation of polyphenols from grape seeds (Vitis vinifera) by human intestinal microbiota.

    PubMed

    Zhou, Li; Wang, Wei; Huang, Jun; Ding, Yu; Pan, Zhouqiang; Zhao, Ya; Zhang, Renkang; Hu, Bing; Zeng, Xiaoxiong

    2016-04-20

    The effects of several parameters on the extraction yield of total polyphenols from grape seeds by pressurized liquid extraction were investigated. The highest recovery of total polyphenols occurred at 80 °C within 5 min, and a single extraction allowed a recovery of more than 97% of total polyphenols. Following the purification with macroporous resin, the effects of grape polyphenols (>94.8%) on human intestinal microbiota were monitored over 36 h incubation by fluorescence in situ hybridization, and short-chain fatty acids (SCFAs) were measured by HPLC. The result showed that the grape polyphenols promoted the changes in the relevant microbial populations and shifted the profiles of SCFAs. Fermentation of grape polyphenols resulted in a significant increase in the numbers of Bifidobacterium spp. and Lactobacillus-Enterococcus group and inhibition in the growth of the Clostridium histolyticum group and the Bacteroides-Prevotella group, with no significant effect on the population of total bacteria. The findings suggest that grape polyphenols have potential prebiotic effects on modulating the gut microbiota composition and generating SCFAs that contribute to the improvements of host health. PMID:26980065

  20. Dietary Polyphenol Supplementation Prevents Alterations of Spatial Navigation in Middle-Aged Mice

    PubMed Central

    Bensalem, Julien; Servant, Laure; Alfos, Serge; Gaudout, David; Layé, Sophie; Pallet, Véronique; Lafenetre, Pauline

    2016-01-01

    Spatial learning and memory deficits associated with hippocampal synaptic plasticity impairments are commonly observed during aging. Besides, the beneficial role of dietary polyphenols has been suggested as potential functional food candidates to prevent this memory decline. Indeed, polyphenols could potentiate the signaling pathways of synaptic plasticity underlying learning and memory. In this study, spatial learning deficits of middle-aged mice were first highlighted and characterized according to their navigation patterns in the Morris water maze task. An eight-week polyphenol-enriched diet, containing a polyphenol-rich extract from grape and blueberry (PEGB; from the Neurophenols Consortium) with high contents of flavonoids, stilbenes and phenolic acids, was then successful in reversing these age-induced effects. The use of spatial strategies was indeed delayed with aging whereas a polyphenol supplementation could promote the occurrence of spatial strategies. These behavioral results were associated with neurobiological changes: while the expression of hippocampal calmodulin kinase II (CaMKII) mRNA levels was reduced in middle-aged animals, the polyphenol-enriched diet could rescue them. Besides, an increased expression of nerve growth neurotrophic factor (NGF) mRNA levels was also observed in supplemented adult and middle-aged mice. Thus these data suggest that supplementation with polyphenols could be an efficient nutritional way to prevent age-induced cognitive decline. PMID:26903826

  1. Dietary intake and food contributors of polyphenols in adults and elderly adults of Sao Paulo: a population-based study.

    PubMed

    Miranda, A M; Steluti, J; Fisberg, R M; Marchioni, D M

    2016-03-28

    A comprehensive estimation of polyphenol intake is needed to gain a better understanding of the association between polyphenol-rich food intake and the potential effects of this intake on chronic diseases. The aim of this study was to estimate the intake of polyphenols and the major dietary contributors in the population of Sao Paulo. Data were obtained from the Health Survey-São Paulo (ISA-Capital 2008) and were reported for 1103 adults and elderly adults. Food intake was estimated by one 24-h dietary recall (24HR). Polyphenol intake was calculated by matching food consumption data from the 24HR with the polyphenol content in foods listed in the Phenol-Explorer database. The mean total intake of polyphenols was 377·5 (se 15·3) mg/d. The main polyphenol classes were phenolic acids (284·8 (se 15·9) mg/d) and flavonoids (54·6 (se 3·5) mg/d). Intakes were higher in the elderly adults than in other adults (P<0·001) and higher in individuals with lower educational level (P=0·01) and current smokers (P=0·02). The main dietary contributors for total polyphenols were coffee (70·5 %), citrus fruits (4·6 %) and tropical fruits (3·4 %). Coffee was the major source of polyphenols, providing 266·2 (se 16·5) mg/d, and contributed 92·3 % of the phenolic acids and 93·1 % of the alkylmethoxyphenols. These findings will be useful for assessing the potential role on health of polyphenols and specific polyphenol-rich foods, such as coffee, and enable a comparison with people from other countries. PMID:26810764

  2. Degradation of pentachlorophenol by potato polyphenol oxidase.

    PubMed

    Hou, Mei-Fang; Tang, Xiao-Yan; Zhang, Wei-De; Liao, Lin; Wan, Hong-Fu

    2011-11-01

    In this study, polyphenol oxidase (PPO) was extracted from commercial potatoes. Degradation of pentachlorophenol by potato PPO was investigated. The experimental results show that potato PPO is more active in weak acid than in basic condition and that the optimum pH for the reaction is 5.0. The degradation of pentachlorophenol by potato PPO reaches a maximum at 298 K. After reaction for 1 h, the removal of both pentachlorophenol and total organic carbon is >70% with 6.0 units/mL potato PPO at pH 5.0 and 298 K. Pentachlorophenol can be degraded through dechlorination and ring-opening by potato PPO. The work demonstrates that pentachlorophenol can be effectively eliminated by crude potato PPO. PMID:21967325

  3. Analysis and functionality of major polyphenolic components of Polygonum cuspidatum (itadori).

    PubMed

    Kirino, Akiko; Takasuka, Yuka; Nishi, Asami; Kawabe, Satoko; Yamashita, Hiromi; Kimoto, Masumi; Ito, Hideyuki; Tsuji, Hideaki

    2012-01-01

    Polygonum cuspidatum has been broadly utilized as a herbal medicine in Asia, but the outline of the polyphenol compounds in the plant has not been characterized well. In the present study, the major polyphenolic components were isolated from the roots of P. cuspidatum, and identified as resveratrol and its glucosides, resveratroloside and polydatin. On the other hand, chlorogenic acid was found to be one of the polyphenolic components in the leaves and stems of the plant. Next, we elucidated that resveratrol derivatives and chlorogenic acid exhibit α-glucosidase inhibitory activities, and resveratroloside exhibits the same inhibitory activity as quercetin does. Furthermore, DPPH radical scavenging activities of antioxidants including resveratrol derivatives and chlorogenic acid derivatives were examined by initial rate analyses of their reactions. Subsequently, it was revealed that resveratrol derivatives have slow-acting effects on the radical scavenging activity and that chlorogenic acid derivatives exhibit very fast-acting effects. PMID:23132312

  4. Effect of mash maceration on the polyphenolic content and visual quality attributes of cloudy apple juice.

    PubMed

    Mihalev, Kiril; Schieber, Andreas; Mollov, Plamen; Carle, Reinhold

    2004-12-01

    The effects of enzymatic mash treatments on yield, turbidity, color, and polyphenolic content of cloudy apple juice were studied. Using HPLC-ESI-MS, cryptochlorogenic acid was identified in cv. Brettacher cloudy apple juice for the first time. Commercial pectolytic enzyme preparations with different levels of secondary protease activity were tested under both oxidative and nonoxidative conditions. Without the addition of ascorbic acid, oxidation substantially decreased chlorogenic acid, epicatechin, and procyanidin B2 contents due to enzymatic browning. The content of chlorogenic acid as the major polyphenolic compound was also influenced by the composition of pectolytic enzyme preparations because the presence of secondary protease activity resulted in a rise of chlorogenic acid. The latter effect was probably due to the inhibited protein-polyphenol interactions, which prevented binding of polyphenolic compounds to the matrix, thus increasing their antioxidative potential. The results obtained clearly demonstrate the advantage of the nonoxidative mash maceration for the production of cloud-stable apple juice with a high polyphenolic content, particularly in a premature processing campaign. PMID:15563212

  5. Protective Effects of Chlorogenic Acid against Experimental Reflux Esophagitis in Rats

    PubMed Central

    Kang, Jung-Woo; Lee, Sun-Mee

    2014-01-01

    Esophageal reflux of gastric contents causes esophageal mucosal damage and inflammation. Recent studies show that oxygen-derived free radicals mediate mucosal damage in reflux esophagitis (RE). Chlorogenic acid (CGA), an ester of caffeic acid and quinic acid, is one of the most abundant polyphenols in the human diet and possesses anti-inflammatory, antibacterial and anti-oxidant activities. In this context, we investigated the effects of CGA against experimental RE in rats. RE was produced by ligating the transitional region between the forestomach and the glandular portion and covering the duodenum near the pylorus ring with a small piece of catheter. CGA (10, 30 and 100 mg/kg) and omeprazole (positive control, 10 mg/kg) were administered orally 48 h after the RE operation for 12 days. CGA reduced the severity of esophageal lesions, and this beneficial effect was confirmed by histopathological observations. CGA reduced esophageal lipid peroxidation and increased the reduced glutathione/oxidized glutathione ratio. CGA attenuated increases in the serum level of tumor necrosis factor-α, and expressions of inducible nitric oxide synthase and cyclooxygenase-2 protein. CGA alleviates RE-induced mucosal injury, and this protection is associated with reduced oxidative stress and the anti-inflammatory properties of CGA. PMID:25414772

  6. Role of Chlorogenic Acids in Controlling Oxidative and Inflammatory Stress Conditions

    PubMed Central

    Liang, Ningjian; Kitts, David D.

    2015-01-01

    Chlorogenic acids (CGAs) are esters formed between caffeic and quinic acids, and represent an abundant group of plant polyphenols present in the human diet. CGAs have different subgroups that include caffeoylquinic, p-coumaroylquinic, and feruloyquinic acids. Results of epidemiological studies suggest that the consumption of beverages such as coffee, tea, wine, different herbal infusions, and also some fruit juices are linked to reduced risks of developing different chronic diseases. These beverages contain CGAs present in different concentrations and isomeric mixtures. The underlying mechanism(s) for specific health benefits attributed to CGAs involves mitigating oxidative stress, and hence the related adverse effects associated with an unbalanced intracellular redox state. There is also evidence to show that CGAs exhibit anti-inflammatory activities by modulating a number of important metabolic pathways. This review will focus on three specific aspects of the relevance of CGAs in coffee beverages; namely: (1) the relative composition of different CGA isomers present in coffee beverages; (2) analysis of in vitro and in vivo evidence that CGAs and individual isomers can mitigate oxidative and inflammatory stresses; and (3) description of the molecular mechanisms that have a key role in the cell signaling activity that underlines important functions. PMID:26712785

  7. Bioavailability of polyphenols from peanut skin extract associated with plasma lipid lowering function.

    PubMed

    Bansode, Rishipal R; Randolph, Priscilla; Ahmedna, Mohamed; Hurley, Steven; Hanner, Tracy; Baxter, Sarah A Schwatrz; Johnston, Thomas A; Su, Mingming; Holmes, Bryce M; Yu, Jianmei; Williams, Leonard L

    2014-04-01

    Peanut skin is a rich source of polyphenols including procyanidins and is shown to have hypolipidemic properties. This study investigated the bioavailability of peanut skin polyphenols using a rat model. First, the bioavailability of peanut skin polyphenols in rat plasma was evaluated. Our results showed procyanidin A2 levels in plasma peaked within 30 min of ingestion. The results of a second study show that peanut skin extract supplemented in addition to oil gavage resulted in significant decrease in plasma triglyceride and VLDL within 5h. In the third study, rats were given a Western type diet for 5 weeks with peanut skin extract at a dose of 150 and 300 mg/kg body weight. The main effects observed were lowering of total blood lipid and reduction of the plasma fatty acids profile. Our results suggest that procyanidin A may impart a key role of hypolipidemic effect seen in peanut skin polyphenols. PMID:24262521

  8. The Mechanisms of Inhibition of Advanced Glycation End Products Formation through Polyphenols in Hyperglycemic Condition.

    PubMed

    Khangholi, Shahpour; Majid, Fadzilah Adibah Abdul; Berwary, Najat Jabbar Ahmed; Ahmad, Farediah; Aziz, Ramlan Bin Abd

    2016-01-01

    Glycation, the non-enzymatic binding of glucose to free amino groups of an amino acid, yields irreversible heterogeneous compounds known as advanced glycation end products. Those products play a significant role in diabetic complications. In the present article we briefly discuss the contribution of advanced glycation end products to the pathogenesis of diabetic complications, such as atherosclerosis, diabetic retinopathy, nephropathy, neuropathy, and wound healing. Then we mention the various mechanisms by which polyphenols inhibit the formation of advanced glycation end products. Finally, recent supporting documents are presented to clarify the inhibitory effects of polyphenols on the formation of advanced glycation end products. Phytochemicals apply several antiglycation mechanisms, including glucose metabolism, amelioration of oxidative stress, scavenging of dicarbonyl species, and up/down-regulation of gene expression. To utilize polyphenols in order to remedy diabetic complications, we must explore, examine and clarify the action mechanisms of the components of polyphenols. PMID:26550791

  9. Targeted deuteration of polyphenolics for their qualitative and quantitative metabolomic analysis in plant-derived extracts.

    PubMed

    Roe, Mikel R; Cohen, Jerry D; Hegeman, Adrian D

    2014-01-01

    Polyphenolics are a chemically diverse class of plant specialized metabolites with strong antioxidant properties, and their consumption has been associated with improved human health. Metabolomic analysis of these compounds in both plant and mammalian samples has relied predominantly on liquid chromatography coupled to electrospray ionization mass spectrometry (LC-ESI-MS). Due to variable matrix effects across samples during ionization, the accuracy of this approach for quantifying compounds is greatly improved by incorporating stable isotope-labeled standards into the sample prior to analysis. However, commercially available, stable isotope-labeled, polyphenolic standards are both limited and costly. Here we present a protocol for generating stable isotope-labeled polyphenolics based on their deuteration by mild acid-catalyzed, electrophilic aromatic substitution. Importantly, this protocol is effective for generating stable isotope-labeled standards of many biologically relevant polyphenolics, both aglycones and the various conjugated forms alike. PMID:24218207

  10. Lipophilic modification enhances anti-colitic properties of rosmarinic acid by potentiating its HIF-prolyl hydroxylases inhibitory activity.

    PubMed

    Jeong, Seongkeun; Park, Huijeong; Hong, Sungchae; Yum, Soohwan; Kim, Wooseong; Jung, Yunjin

    2015-01-15

    Inhibition of hypoxia inducible factor-prolyl hydroxylase-2 (HPH), leading to activation of hypoxia inducible factor (HIF)-1 is a potential therapeutic strategy for the treatment of colitis. Rosmarinic acid (RA), an ester of caffeic acid and 3,4-dihydroxyphenyllactic acid is a naturally occurring polyphenolic compound with two catechols, a or inhibition of HPH. To improve accessibility of highly hydrophilic RA to HPH, an intracellular target, RA was chemically modified to decrease hydrophilicity. Of the less-hydrophilic derivatives, rosmarinic acid methyl ester (RAME) most potently inhibited HPH. Accordingly, RAME prevented hydroxylation of HIF-1α and consequently stabilized HIF-1α protein in cells. RAME inhibition of HPH and induction of HIF-1α were diminished by elevated doses of the required factors of HPH, 2-ketoglutarate and ascorbate. RAME induction of HIF-1α led to activation of an ulcer healing pathway, HIF-1-vascular endothelial growth factor (VEGF), in human colon carcinoma cells. RAME administered rectally ameliorated TNBS-induced rat colitis and substantially decreased the levels of pro-inflammatory mediators in the inflamed colonic tissue. In parallel with the cellular effects of RAME, RAME up-regulated HIF-1α and VEGF in the inflamed colonic tissue. Thus, lipophilic modification of RA improves its ability to inhibit HPH, leading to activation of the HIF-1-VEGF pathway. RAME, a lipophilic RA derivative, may exert anti-colitic effects via activation of the ulcer healing pathway. PMID:25483211

  11. Experimental colitis in mice is attenuated by topical administration of chlorogenic acid.

    PubMed

    Zatorski, Hubert; Sałaga, Maciej; Zielińska, Marta; Piechota-Polańczyk, Aleksandra; Owczarek, Katarzyna; Kordek, Radzisław; Lewandowska, Urszula; Chen, Chunqiu; Fichna, Jakub

    2015-06-01

    Epidemiological data suggest that the consumption of polyphenol-rich foods reduces the incidence of cancer, coronary heart disease, and inflammation. Chlorogenic acid (CGA), an ester of caffeic and quinic acids, is one of the most abundant polyphenol compounds in human diet with proven biological effectiveness both in vitro and in vivo. The aim of the study is to investigate the possible anti-inflammatory effect of CGA in the gastrointestinal (GI) tract and its mechanism of action. We used a well-established model of colitis, induced by intracolonic (i.c.) administration of trinitrobenzenesulfonic acid (TNBS) in mice. The anti-inflammatory effect of CGA in the colon was evaluated based on the clinical and macroscopic and microscopic parameters. To investigate the mechanism of protective action of CGA, myeloperoxidase (MPO), H2O2, and NF-κB levels were assessed in the colon tissue. CGA administered i.c. at the dose of 20 mg/kg (two times daily) protected against TNBS-induced colitis more effectively than the same dose administered orally (p.o.), as evidenced by significantly lower macroscopic and ulcer scores. Furthermore, CGA (20 mg/kg, i.c.) reduced neutrophil infiltration, as demonstrated by decreased MPO activity. Moreover, CGA suppressed activation of NF-κB, as evidenced by lower levels of phospho-NF-κB/NF-κB ratio in the tissue. CGA did not affect the oxidative stress pathways. CGA exhibits anti-inflammatory properties through reduction of neutrophil infiltration and inhibition of NF-κB-dependent pathways. Our results suggest that CGA may have the potential to become a valuable supplement in the treatment of GI diseases. PMID:25743575

  12. Chlorogenic Acid Protects against Atherosclerosis in ApoE−/− Mice and Promotes Cholesterol Efflux from RAW264.7 Macrophages

    PubMed Central

    Wu, Chongming; Luan, Hong; Zhang, Xue; Wang, Shuai; Zhang, Xiaopo; Sun, Xiaobo; Guo, Peng

    2014-01-01

    Chlorogenic acid (CGA) is one of the most abundant polyphenols in the human diet and is suggested to be a potential antiatherosclerotic agent due to its proposed hypolipidemic, anti-inflammatory and antioxidative properties. The aim of this study was to evaluate the effect of CGA on atherosclerosis development in ApoE−/− mice and its potential mechanism. ApoE−/− mice were fed a cholesterol-rich diet without (control) or with CGA (200 and 400 mg/kg) or atorvastatin (4 mg/kg) for 12 weeks. During the study plasma lipid and inflammatory parameters were determined. Treatment with CGA (400 mg/kg) reduced atherosclerotic lesion area and vascular dilatation in the aortic root, comparable to atorvastatin. CGA (400 mg/kg) also significantly decreased plasma levels of total cholesterol, triglycerides and low-density lipoprotein-cholesterol as well as inflammatory markers. Supplementation with CGA or CGA metabolites-containing serum suppressed oxidized low-density lipoprotein (oxLDL)-induced lipid accumulation and stimulated cholesterol efflux from RAW264.7 cells. CGA significantly increased the mRNA levels of PPARγ, LXRα, ABCA1 and ABCG1 as well as the transcriptional activity of PPARγ. Cholesterol efflux assay showed that three major metabolites, caffeic, ferulic and gallic acids, significantly stimulated cholesterol efflux from RAW264.7 cells. These results suggest that CGA potently reduces atherosclerosis development in ApoE−/− mice and promotes cholesterol efflux from RAW264.7 macrophages. Caffeic, ferulic and gallic acids may be the potential active compounds accounting for the in vivo effect of CGA. PMID:25187964

  13. Determination of chokeberry (Aronia melanocarpa) polyphenol components using liquid chromatography-tandem mass spectrometry: Overall contribution to antioxidant activity.

    PubMed

    Lee, Ji Eun; Kim, Gon-Sup; Park, Semin; Kim, Yun-Hi; Kim, Man-Bae; Lee, Won Sup; Jeong, Sung Woo; Lee, Soo Jung; Jin, Jong Sung; Shin, Sung Chul

    2014-03-01

    The type and content of plant polyphenols can be influenced by maturity. Korean chokeberry (Aronia melanocarpa) leaves of three different maturities (young, mature, and aged) were extracted with 70% aqueous methanol. The polyphenols in the leaves were analysed for the first time using high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) and comparison with reported data. Among the 12 characterised components, five flavonoids, 3, 4, and 10-12, and a dicaffeoylquinic acid derivative, 6, were characterised for the first time in chokeberry leaves. Each polyphenol component was validated and quantified using a representative polyphenol standard of the same group. The antioxidant activity of the three different mature leaf extracts was determined. The antioxidant activity was highest for young leaves, followed by mature and aged leaves. The results suggest that younger chokeberry leaves may be more favourable for processing a higher quality functional tea due to their higher polyphenol content. PMID:24176305

  14. Bioavailability of the polyphenols: status and controversies.

    PubMed

    D'Archivio, Massimo; Filesi, Carmelina; Varì, Rosaria; Scazzocchio, Beatrice; Masella, Roberta

    2010-01-01

    The current interest in polyphenols has been driven primarily by epidemiological studies. However, to establish conclusive evidence for the effectiveness of dietary polyphenols in disease prevention, it is useful to better define the bioavailability of the polyphenols, so that their biological activity can be evaluated. The bioavailability appears to differ greatly among the various phenolic compounds, and the most abundant ones in our diet are not necessarily those that have the best bioavailability profile. In the present review, we focus on the factors influencing the bioavailability of the polyphenols. Moreover, a critical overview on the difficulties and the controversies of the studies on the bioavailability is discussed. PMID:20480022

  15. Bioavailability of the Polyphenols: Status and Controversies

    PubMed Central

    D’Archivio, Massimo; Filesi, Carmelina; Varì, Rosaria; Scazzocchio, Beatrice; Masella, Roberta

    2010-01-01

    The current interest in polyphenols has been driven primarily by epidemiological studies. However, to establish conclusive evidence for the effectiveness of dietary polyphenols in disease prevention, it is useful to better define the bioavailability of the polyphenols, so that their biological activity can be evaluated. The bioavailability appears to differ greatly among the various phenolic compounds, and the most abundant ones in our diet are not necessarily those that have the best bioavailability profile. In the present review, we focus on the factors influencing the bioavailability of the polyphenols. Moreover, a critical overview on the difficulties and the controversies of the studies on the bioavailability is discussed. PMID:20480022

  16. Polyphenol intake and mortality risk: a re-analysis of the PREDIMED trial

    PubMed Central

    2014-01-01

    Background Polyphenols may lower the risk of cardiovascular disease (CVD) and other chronic diseases due to their antioxidant and anti-inflammatory properties, as well as their beneficial effects on blood pressure, lipids and insulin resistance. However, no previous epidemiological studies have evaluated the relationship between the intake of total polyphenols intake and polyphenol subclasses with overall mortality. Our aim was to evaluate whether polyphenol intake is associated with all-cause mortality in subjects at high cardiovascular risk. Methods We used data from the PREDIMED study, a 7,447-participant, parallel-group, randomized, multicenter, controlled five-year feeding trial aimed at assessing the effects of the Mediterranean Diet in primary prevention of cardiovascular disease. Polyphenol intake was calculated by matching food consumption data from repeated food frequency questionnaires (FFQ) with the Phenol-Explorer database on the polyphenol content of each reported food. Hazard ratios (HR) and 95% confidence intervals (CI) between polyphenol intake and mortality were estimated using time-dependent Cox proportional hazard models. Results Over an average of 4.8 years of follow-up, we observed 327 deaths. After multivariate adjustment, we found a 37% relative reduction in all-cause mortality comparing the highest versus the lowest quintiles of total polyphenol intake (hazard ratio (HR) = 0.63; 95% CI 0.41 to 0.97; P for trend = 0.12). Among the polyphenol subclasses, stilbenes and lignans were significantly associated with reduced all-cause mortality (HR =0.48; 95% CI 0.25 to 0.91; P for trend = 0.04 and HR = 0.60; 95% CI 0.37 to 0.97; P for trend = 0.03, respectively), with no significant associations apparent in the rest (flavonoids or phenolic acids). Conclusions Among high-risk subjects, those who reported a high polyphenol intake, especially of stilbenes and lignans, showed a reduced risk of overall mortality compared to those

  17. Bioactive Dietary Polyphenols Inhibit Heme Iron Absorption in A Dose-Dependent Manner in Human Intestinal Caco-2 cells

    PubMed Central

    Ma, Qianyi; Kim, Eun-Young; Lindsay, Elizabeth Ann; Han, Okhee

    2011-01-01

    Although heme iron is an important form of dietary iron, its intestinal absorption mechanism remains elusive. Our previous work revealed that (−)-epigallocatechin-3-gallate (EGCG) and grape seed extract (GSE) markedly inhibited intestinal heme iron absorption by reducing the basolateral iron export in Caco-2 cells. The aims of this study were to examine whether small amounts of EGCG, GSE and green tea extract (GT) could inhibit heme iron absorption, and to test whether the inhibitory action of polyphenols could be offset by ascorbic acid. A heme-55Fe absorption study was conducted by adding various concentrations of EGCG, GSE and GT to Caco-2 cells in the absence and presence of ascorbic acid. Polyphenolic compounds significantly inhibited heme-55Fe absorption in a dose-dependent manner. The addition of ascorbic acid did not modulate the inhibitory effect of dietary polyphenols on heme iron absorption when the cells were treated with polyphenols at a concentration of 46 mg/L. However, ascorbic acid was able to offset or reverse the inhibitory effects of polyphenolic compounds when lower concentrations of polyphenols were added (≤ 4.6 mg/L). Ascorbic acid modulated the heme iron absorption without changing the apical heme uptake, the expression of the proteins involved in heme metabolism and basolateral iron transport, and heme oxygenase activity, indicating that ascorbic acid may enhance heme iron absorption by modulating the intracellular distribution of 55Fe. These results imply that the regular consumption of dietary ascorbic acid can easily counteract the inhibitory effects of low concentrations of dietary polyphenols on heme iron absorption but cannot counteract the inhibitory actions of high concentrations of polyphenols. PMID:22417433

  18. Gallic Acid, Ellagic Acid and Pyrogallol Reaction with Metallic Iron

    NASA Astrophysics Data System (ADS)

    Jaén, J. A.; González, L.; Vargas, A.; Olave, G.

    2003-06-01

    The reaction between gallic acid, ellagic acid and pyrogallol with metallic iron was studied using infrared and Mössbauer spectroscopy. Most hydrolysable tannins with interesting anticorrosive or inhibition properties are structurally related to these compounds, thus they may be used as models for the study of hydrolysable tannins and related polyphenols. The interaction was followed up to 3 months. Results indicated two different behaviors. At polyphenol concentrations higher than 1% iron converts to sparingly soluble and amorphous ferric (and ferrous) polyphenolate complexes. At lower concentrations (0.1%), the hydrolysis reactions are dominant, resulting in the formation of oxyhydroxides, which can be further reduced to compounds like magnetite by the polyphenols.

  19. Studies on Polyphenol Content, Activities and Isozymes of Polyphenol Oxidase and Peroxidase During Air-Curing in Three Tobacco Types 1

    PubMed Central

    Sheen, S. J.; Calvert, J.

    1969-01-01

    The change in polyphenol content in the primed leaves of burley, flue-cured, and Turkish tobaccos during air-curing was related to the activities and isozymes of polyphenol oxidase and peroxidase. The quantity of chlorogenic acid was rapidly reduced during the first week of curing. The decrease in rutin content during curing was less significant, especially when the concentration of chlorogenic acid was high in leaf tissues. This result was further confirmed by in vitro assays with partially purified tobacco polyphenol oxidase. The polyphenol oxidase activity did not differ at any stage of curing in the 3 tobaccos. When the activity was measured by the oxidation of 3,4-dihydroxyphenylalanine it rose rapidly during the first day of curing and then decreased sharply so that in the fully cured leaf only 15% activity remained. The increase in activity was not observed when chlorogenic acid was used as the substrate. A similar level of peroxidase activity was found in the 3 tobaccos before curing. Peroxidase activities increased rapidly during the first 24 hr of curing, declined thereafter, and remained highest in the flue-cured tobacco, less in the Turkish line, and least in the burley at the end of curing process. By polyacrylamide gel block electrophoresis, 10 peroxidase isozyme bands, 2 cationic and 8 anionic, appeared identical in all 3 tobaccos. When catechol replaced benzidine-2 HCl as the electron donor, 1 cationic and 2 anionic peroxidase isozymes did not form. Of interest is that the same 10 peroxidase isozyme bands also exhibited polyphenol oxidase activities when treated with 3,4-dihydroxyphenylalanine or chlorogenic acid. Results suggest that in the crude tobacco leaf extract the peroxidase and polyphenol oxidase may associate as protein complexes, and peroxidase isozymes may differ in electron-donor requirements. Isozyme patterns for both oxidases at various curing intervals differed only quantitatively. Images PMID:16657046

  20. Harvest date affects aronia juice polyphenols, sugars, and antioxidant activity, but not anthocyanin stability.

    PubMed

    Bolling, Bradley W; Taheri, Rod; Pei, Ruisong; Kranz, Sarah; Yu, Mo; Durocher, Shelley N; Brand, Mark H

    2015-11-15

    The goal of this work was to characterize how the date of harvest of 'Viking' aronia berry impacts juice pigmentation, sugars, and antioxidant activity. Aronia juice anthocyanins doubled at the fifth week of the harvest, and then decreased. Juice hydroxycinnamic acids decreased 33% from the first week, while proanthocyanidins increased 64%. Juice fructose and glucose plateaued at the fourth week, but sorbitol increased 40% to the seventh harvest week. Aronia juice pigment density increased due to anthocyanin concentration, and polyphenol copigmentation did not significantly affect juice pigmentation. Anthocyanin stability at pH 4.5 was similar between weeks. However, addition of quercetin, sorbitol, and chlorogenic acid to aronia anthocyanins inhibited pH-induced loss of color. Sorbitol and citric acid may be partially responsible for weekly variation in antioxidant activity, as addition of these agents inhibited DPPH scavenging 13-30%. Thus, aronia polyphenol and non-polyphenol components contribute to its colorant and antioxidant functionality. PMID:25977015

  1. Polyphenols and Volatile Compounds in Commercial Chokeberry (Aronia melanocarpa) Products.

    PubMed

    Romani, Annalisa; Vignolini, Pamela; Ieri, Francesca; Heimler, Daniela

    2016-01-01

    Aronia melanocarpa (Michx.) Elliott commercial products (dried fruit, juice and compote) were analyzed for their polyphenol content by chromatographic and spectrophotometric analyses in order to ascertain the fate of this group of compounds when fresh fruit is processed and sold in different forms on the market. Different classes of polyphenols were investigated: hydroxycinnamic derivatives ranged from 0.65 mg/g to 4.30 mg/g, flavonoids from 0.36 mg/g to 1.12 mg/g, and anthocyanins from 0.65 to 7.08 mg/g sample. 4-O-Caffeoyl-quinic acid was tentatively identified for the first time in Aronia. In order to characterize better chokeberry juice, a GC profile of aroma compounds was obtained. The aroma juice compounds belong mainly to the chemical classes of alcohols (48.9%) and ketones (30.28%). The most abundant compound is 3-penthen-2-one (23.6%). PMID:26996031

  2. Metabolism of hydroxycinnamic acids and their tartaric acid esters by Brettanomyces and Pediococcus in red wines.

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Caffeic, p-coumaric, and ferulic acids and their corresponding tartaric acid esters (caftaric, coutaric, and fertaric, respectively) are found in wines in varying concentrations. While Brettanomyces and Pediococcus can utilize the free acids, it is not known whether they can metabolize the correspon...

  3. Polyphenolics profile, antioxidant and radical scavenging activity of leaves and stem of Raphanus sativus L.

    PubMed

    Beevi, Syed Sultan; Narasu, Mangamoori Lakshmi; Gowda, Bandi Boje

    2010-03-01

    Aerial parts (leaves and stem) of Raphanus sativus, which are usually discarded were found to possess potent antioxidant and radical scavenging activity, as measured by standard antioxidant assays. Methanolic and acetone extracts of R. sativus leaves had total polyphenolic content of 86.16 and 78.77 mg/g dry extract, which were comparable to the traditional rich sources such as green tea and black tea. HPLC identification of polyphenolics indicated the presence of catechin, protocatechuic acid, syringic acid, vanillic acid, ferulic acid, sinapic acid, o-coumaric acid, myricetin, and quercetin in leaves and stem. Among the different extraction solvents, methanolic extract of leaves and stem showed potent reductive capacity, significantly inhibited linoleic acid peroxidation and displayed metal chelating activity. Further, they scavenged free radicals effectively with IC50 (half maximal inhibitory concentration) of 31 and 42 microg/ml for DPPH radical, 23 and 52 microg/ml for superoxide radical, 67 and 197 microg/ml for hydrogen peroxide,and 56 and 62 microg/ml for nitric oxide, respectively. Leaves showed most potent antioxidant and radical scavenging activity as compared to stem, which may be accounted for the high polyphenolic content. Leaves and stem of R. sativus,often under-utilized part of this vegetable, thus possessed considerable amount of polyphenolics. Hence, it should be egarded as a potential source of natural antioxidants and could be effectively employed as an ingredient in health or in functional food. PMID:20072818

  4. Permeability of rosmarinic acid in Prunella vulgaris and ursolic acid in Salvia officinalis extracts across Caco-2 cell monolayers

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Rosmarinic acid (RA), a caffeic acid derivative found in high concentrations in Prunella vulgaris (self-heal), and ursolic acid (UA), a pentacyclic triterpene acid concentrated in Salvia officinalis (sage), have been traditionally used to treat inflammation in the mouth, and may also be of benefit t...

  5. Effect of polyphenols on the intestinal and placental transport of some bioactive compounds.

    PubMed

    Martel, Fátima; Monteiro, Rosário; Calhau, Conceição

    2010-06-01

    Polyphenols are a group of widely distributed phytochemicals present in most foods of vegetable origin. A growing number of biological effects have been attributed to these molecules in the past few years and only recently has their interference with the transport capacity of epithelial barriers received attention. This review will present data obtained concerning the effect of polyphenols upon the transport of some compounds (organic cations, glucose and the vitamins thiamin and folic acid) at the intestinal and placental barriers. Important conclusions can be drawn: (i) different classes of polyphenols affect transport of these bioactive compounds at the intestinal epithelia and the placenta; (ii) different compounds belonging to the same phenolic family often possess opposite effects upon transport of a given molecule; (iii) the acute and chronic/short-term and long-term exposures to polyphenols do not produce parallel results and, therefore, care should be taken when extrapolating results; (iv) the effect of polyphenolics in combination may be very different from the expected ones taking into account the effect of each of these compounds alone, and so care should be taken when speculating on the effect of a drink based on the effect of one component only; (v) care should be taken in drawing conclusions for alcoholic beverages from results obtained with ethanol alone. Although most of the data reviewed in the present paper refer to in vitro experiments with cell-culture systems, these studies raise a concern about possible changes in the bioavailability of substrates upon concomitant ingestion of polyphenols. PMID:20392307

  6. Effects of the polyphenol content on the anti-diabetic activity of Cinnamomum zeylanicum extracts.

    PubMed

    IM, Krishnakumar; Issac, Abin; NM, Johannah; Ninan, Eapen; Maliakel, Balu; Kuttan, Ramadassan

    2014-09-01

    Cinnamomum zeylanicum is a popular kitchen spice widely investigated for insulin potentiating effects. Though a group of water soluble polyphenols belonging to the oligomeric procyanidins has been identified as the bioactive principle, the lack of systematic information on the effect of the polyphenol content on safety and anti-diabetic efficacy remains as a major limitation for the development of optimized and standardized cinnamon extracts for functional use. In the present paper, water soluble extracts of Cinnamomum zeylanicum containing 45 and 75% gallic acid equivalents (GAE) of polyphenol content were prepared by a novel process and characterized by tandem mass spectrometry. The polyphenol enhanced extracts were shown to be safe and offered better antioxidant potential, hypoglycemic effect, hypolipidimic effect, and significant decrease in other biochemical parameters as compared to the standard aqueous extract containing 15% GAE, when administered to streptozotocin-induced diabetic rats at 200 mg per kg b.w. for 30 days. The efficacy of polyphenol extracts in lowering blood glucose levels and ameliorating oxidative stress was further demonstrated in humans by administrating 'procynZ-45' containing 45% GAE polyphenols at a relatively low dosage of (125 mg × 2) per day for 30 days to 15 volunteers who had elevated fasting blood glucose levels; but not involved in any medication. PMID:25051315

  7. Interaction of green tea polyphenols with dairy matrices in a simulated gastrointestinal environment.

    PubMed

    Lamothe, Sophie; Azimy, Naheed; Bazinet, Laurent; Couillard, Charles; Britten, Michel

    2014-10-01

    The consumption of polyphenols in green tea has been associated with beneficial health effects. Although polyphenols are unstable in the intestinal environment, they may be protected by interactions with dairy proteins during digestion. The objectives of this study were to evaluate the effect of a green tea extract on the digestibility of different dairy matrices and to monitor the antioxidant activity of these matrices with or without the green tea extract during digestion in a simulated gastrointestinal environment. Milk, yogurt and cheese with similar fat-to-protein ratios were subjected to simulated digestion. Matrix degradation, protein and fat hydrolysis, polyphenol concentration and radical scavenging activity were analyzed during gastric and intestinal digestion phases. Cheese was the matrix most resistant to protein and fat digestion. The addition of the green tea extract significantly decreased proteolysis in the gastric phase but had no effect in the intestinal phase. The kinetics of fatty acid release was reduced by the presence of the green tea extract. Transition from the gastric phase to the intestinal phase induced a 50% decrease in the antioxidant activity of the control (tea extract dispersed in water) due to the degradation of polyphenols. The presence of dairy matrices significantly improved polyphenol stability in the intestinal phase and increased the antioxidant activity by 29% (cheese) to 42% (milk) compared to the control. These results suggest that simultaneous consumption of green tea and dairy products helps to maintain the integrity and antioxidant activity of polyphenols during digestion. PMID:25154916

  8. Comparison of Various Databases for Estimation of Dietary Polyphenol Intake in the Population of Polish Adults

    PubMed Central

    Witkowska, Anna M.; Zujko, Małgorzata E.; Waśkiewicz, Anna; Terlikowska, Katarzyna M.; Piotrowski, Walerian

    2015-01-01

    The primary aim of the study was to estimate the consumption of polyphenols in a population of 6661 subjects aged between 20 and 74 years representing a cross-section of the Polish society, and the second objective was to compare the intakes of flavonoids calculated on the basis of the two commonly used databases. Daily food consumption data were collected in 2003–2005 using a single 24-hour dietary recall. Intake of total polyphenols was estimated using an online Phenol-Explorer database, and flavonoid intake was determined using following data sources: the United States Department of Agriculture (USDA) database combined of flavonoid and isoflavone databases, and the Phenol-Explorer database. Total polyphenol intake, which was calculated with the Phenol-Explorer database, was 989 mg/day with the major contributions of phenolic acids 556 mg/day and flavonoids 403.5 mg/day. The flavonoid intake calculated on the basis of the USDA databases was 525 mg/day. This study found that tea is the primary source of polyphenols and flavonoids for the studied population, including mainly flavanols, while coffee is the most important contributor of phenolic acids, mostly hydroxycinnamic acids. Our study also demonstrated that flavonoid intakes estimated according to various databases may substantially differ. Further work should be undertaken to expand polyphenol databases to better reflect their food contents. PMID:26569297

  9. The interaction of polyphenols with bilayers: conditions for increasing bilayer adhesion.

    PubMed

    Huh, N W; Porter, N A; McIntosh, T J; Simon, S A

    1996-12-01

    Because proteins and other molecules with a high polyphenol content are commonly involved in adhesion processes, we are investigating the interactions between polyphenols and biological materials. A naturally occurring polyphenol that binds a variety of proteins and lipids is tannic acid (TA), which contains five digallic acid residues covalently linked to a central D-glucose. A previous study has shown that TA increases the adhesion between apposing phosphatidylcholine (PC) bilayers and over a very narrow concentration range collapses the interbilayer fluid space from about 15 A to 5 A. To determine the chemical requirements a polyphenolic molecule must possess to increase bilayer adhesion, we have synthesized several simpler TA analogs that vary in their size, shape, and number of gallic acid and hydroxyl groups. X-ray diffraction, absorbance, binding, and differential scanning calorimetry measurements were used to investigate the interaction of these polyphenolic molecules with egg PC (EPC) and dipalmitoyl PC (DPPC) bilayers. Of these synthetic polyphenols, only penta-O-galloyl-alpha-D-glucose (PGG) was able to completely mimic the effects of TA by collapsing the interbilayer fluid space from 15 A to 5 A, decreasing the dipole potential by about 300 mV, increasing the transition enthalpy of DPPC liposomes, and inducing an interdigitated phase in DPPC. Binding studies indicated that the fluid space was reduced to 5 A at an EPC:PGG mole ratio of 5:1. We conclude that these polyphenols collapse the fluid space of PC bilayers because they 1) are amphipathic and partition into the bilayers interfacial region, 2) are long enough to span the interbilayer space, 3) contain several gallic acids distributed so that they can partition simultaneously into apposing bilayers, and 4) have sufficient gallic acid residues to interact with all lipid headgroups and cover the bilayer surface. Under these conditions we conclude that the polyphenols from interbilayer bridges. We

  10. The interaction of polyphenols with bilayers: conditions for increasing bilayer adhesion.

    PubMed Central

    Huh, N W; Porter, N A; McIntosh, T J; Simon, S A

    1996-01-01

    Because proteins and other molecules with a high polyphenol content are commonly involved in adhesion processes, we are investigating the interactions between polyphenols and biological materials. A naturally occurring polyphenol that binds a variety of proteins and lipids is tannic acid (TA), which contains five digallic acid residues covalently linked to a central D-glucose. A previous study has shown that TA increases the adhesion between apposing phosphatidylcholine (PC) bilayers and over a very narrow concentration range collapses the interbilayer fluid space from about 15 A to 5 A. To determine the chemical requirements a polyphenolic molecule must possess to increase bilayer adhesion, we have synthesized several simpler TA analogs that vary in their size, shape, and number of gallic acid and hydroxyl groups. X-ray diffraction, absorbance, binding, and differential scanning calorimetry measurements were used to investigate the interaction of these polyphenolic molecules with egg PC (EPC) and dipalmitoyl PC (DPPC) bilayers. Of these synthetic polyphenols, only penta-O-galloyl-alpha-D-glucose (PGG) was able to completely mimic the effects of TA by collapsing the interbilayer fluid space from 15 A to 5 A, decreasing the dipole potential by about 300 mV, increasing the transition enthalpy of DPPC liposomes, and inducing an interdigitated phase in DPPC. Binding studies indicated that the fluid space was reduced to 5 A at an EPC:PGG mole ratio of 5:1. We conclude that these polyphenols collapse the fluid space of PC bilayers because they 1) are amphipathic and partition into the bilayers interfacial region, 2) are long enough to span the interbilayer space, 3) contain several gallic acids distributed so that they can partition simultaneously into apposing bilayers, and 4) have sufficient gallic acid residues to interact with all lipid headgroups and cover the bilayer surface. Under these conditions we conclude that the polyphenols from interbilayer bridges. We

  11. Food Polyphenols Fail to Cause a Biologically Relevant Reduction of COX-2 Activity

    PubMed Central

    Willenberg, Ina; Meschede, Anna K.; Gueler, Faikah; Jang, Mi-Sun; Shushakova, Nelli; Schebb, Nils Helge

    2015-01-01

    Epidemiologic studies show a correlation between the dietary intake of food polyphenols and beneficial health effects. Several in vitro studies indicate that the anti-inflammatory potential of polyphenols is, at least in part, mediated by a modulation of the enzymes of the arachidonic acid cascade, such as the prostaglandin forming cyclooxygenases (COXs). Evidence that this mode of action can be transferred to the situation in vivo is scarce. This study characterized effects of a subset of polyphenols on COX–2 expression and activity in vitro and compared the potency with known drugs. Next, the in vivo relevance of the observed in vitro effects was tested. Enzyme assays and incubations of polyphenols with the cancer cell line HCA–7 and lipopolysaccharide (LPS) stimulated primary monocytes support the hypothesis that polyphenols can effect COX–2 expression and activity in vitro. The effects were most pronounced in the monocyte assay for wogonin, apigenin, resveratrol and genistein with IC50 values of 1.5 μM, 2.6 μM, 2.8 μM and 7.4 μM. However, these values are 100- to 1000-fold higher in comparison to those of the known pharmaceuticals celecoxib, indomethacin and dexamethasone. In an animal model of LPS induced sepsis, pretreatment with polyphenols (i. p. 100 mg/kg bw) did not result in decreased plasma or tissue prostaglandin levels, whereas the positive control celecoxib effectively attenuated LPS induced prostaglandin formation. These data suggest that despite the moderate potency in vitro, an effect of polyphenols on COX–2 during acute inflammation is unlikely, even if a high dose of polyphenols is ingested. PMID:26440517

  12. Use of grape seed and its natural polyphenol extracts as a natural organic coagulant for removal of cationic dyes.

    PubMed

    Jeon, Jong-Rok; Kim, Eun-Ju; Kim, Young-Mo; Murugesan, Kumarasamy; Kim, Jae-Hwan; Chang, Yoon-Seok

    2009-11-01

    Natural organic coagulants (NOCs) such as chitosan and Moringa oleifera seeds have been extensively characterized for potential application in water treatment as an alternative to metal-based coagulants. However, the action of both chitosan and M. oleifera seeds is mainly restricted to anionic organic pollutants because of their cationic functional groups affording poor cationic pollutant coagulation by electrostatic repulsion. In this study, we employed ethanolic grape seed extract (GSE) and grape seed-derived polyphenols such as tannic acid and catechin in an effort to find novel NOCs showing stable anionic forms for removal of cationic organic pollutants. The target substances tested were malachite green (MG) and crystal violet (CV), both mutagenic cationic dyes. Polyphenol treatment induced fast decolorization followed by gradual floc formation concomitant with red or blue shifts in maximum absorbance wavelengths of the cationic dyes. Liquid chromatography analysis of flocs formed by polyphenols directly showed that initial supramolecular complexes attributed mainly to electrostatic attraction between polyphenol hydroxyphenyl groups and cationic dyes further progressed into stronger aggregates, leading to precipitation of dye-polyphenol complexes. Consistent with the results obtained using catechin and tannic acid, use of GSE also resulted in effective decolorization and coagulation of soluble MG and CV in aqueous solutions. Screening of several organic GSE components for NOC activity strongly suggested that natural polyphenols are the main organic ingredients causing MG and CV removal via gradual floc formation. The treatment by natural polyphenols and GSE decreased toxicity of MG- or CV-contaminated water. PMID:19786292

  13. Bioavailability of Polyphenol Liposomes: A Challenge Ahead

    PubMed Central

    Mignet, Nathalie; Seguin, Johanne; Chabot, Guy G.

    2013-01-01

    Dietary polyphenols, including flavonoids, have long been recognized as a source of important molecules involved in the prevention of several diseases, including cancer. However, because of their poor bioavailability, polyphenols remain difficult to be employed clinically. Over the past few years, a renewed interest has been devoted to the use of liposomes as carriers aimed at increasing the bioavailability and, hence, the therapeutic benefits of polyphenols. In this paper, we review the causes of the poor bioavailability of polyphenols and concentrate on their liposomal formulations, which offer a means of improving their pharmacokinetics and pharmacodynamics. The problems linked to their development and their potential therapeutic advantages are reviewed. Future directions for liposomal polyphenol development are suggested. PMID:24300518

  14. A Review of Polyphenolics in Oak Woods

    PubMed Central

    Zhang, Bo; Cai, Jian; Duan, Chang-Qing; Reeves, Malcolm J.; He, Fei

    2015-01-01

    Polyphenolics, which are ubiquitous in plants, currently are among the most studied phytochemicals because of their perceptible chemical properties and antioxidant activity. Oak barrels and their alternatives, which are widely used in winemaking nowadays, contribute polyphenolics to wines and are thought to play crucial roles in the development of wines during aging. This study summarizes the detailed information of polyphenolics in oak woods and their products by examining their structures and discussing their chemical reactions during wine aging. This paper evaluates the most recent developments in polyphenolic chemistry by summarizing their extraction, separation, and their identification by the use of chromatographic and spectral techniques. In addition, this paper also introduces polyphenol bioactive ingredients in other plant foods. PMID:25826529

  15. Polyphenols as active ingredients for cosmetic products.

    PubMed

    Zillich, O V; Schweiggert-Weisz, U; Eisner, P; Kerscher, M

    2015-10-01

    Polyphenols are secondary plant metabolites with antioxidant, anti-inflammatory and anti-microbial activity. They are ubiquitously distributed in the plant kingdom; high amounts contain, for example, green tea and grape seeds. Polyphenolic extracts are attractive ingredients for cosmetics and pharmacy due to their beneficial biological properties. This review summarizes the effects of polyphenols in the context of anti-ageing activity. We have explored in vitro studies, which investigate antioxidant activity, inhibition of dermal proteases and photoprotective activity, mostly studied using dermal fibroblasts or epidermal keratinocytes cell lines. Possible negative effects of polyphenols were also discussed. Further, some physicochemical aspects, namely the possible interactions with emulsifiers and the influence of the cosmetic formulation on the skin delivery, were reported. Finally, few clinical studies, which cover the anti-ageing action of polyphenols on the skin after topical application, were reviewed. PMID:25712493

  16. Anti-metastasis effects of gallic acid on gastric cancer cells involves inhibition of NF-kappaB activity and downregulation of PI3K/AKT/small GTPase signals.

    PubMed

    Ho, Hsieh-Hsun; Chang, Chi-Sen; Ho, Wei-Chi; Liao, Sheng-You; Wu, Cheng-Hsun; Wang, Chau-Jong

    2010-01-01

    Polyphenols are natural antioxidants that are thought to contribute to prevention of cardiovascular disease and malignancy. Although many studies have been carried out to investigate the chemopreventive role of flavonoids, less attention has been focused on phenolic acids. In this study, the aim was to investigate the effect of phenolic acids found abundantly in vegetables, i.e. gallic acid (GA), caffeic acid (CA) and protocatechuic acid (PCA), on the inhibition of gastric adenocarcinoma (AGS) cell metastasis. The results showed 0.01 mM GA induced the same level of cell toxicity as 4.0mM PCA. Using wound-healing assay and Boyden chamber assay, GA had potent inhibitory effects on AGS cell migration. The expression of MMP-2/9 of AGS cells was inhibited by 2.0 microM of GA. It is possible that the suppressive effect of GA on MMP-2/9 might involve the inhibition of NF-kappaB activity. Multiple proteins involved in metastasis and the cytoskeletal reorganization signal pathway, including Ras, Cdc42, Rac1, RhoA, RhoB, PI3K and p38MAPK, were also inhibited by GA. Furthermore, immunoreactivity assay of cytoskeletal F-actin demonstrated a significant inhibitory effect of GA treatment. In conclusion, GA may have the potential to be an effective agent for prevention and treatment of gastric cancer metastasis. PMID:20600540

  17. Usefulness of palladium impregnated magnetite nanoparticles for polyphenol determination.

    PubMed

    Godoy-Navajas, Juan; Aguilar-Caballos, María Paz; Gómez-Hens, Agustina

    2016-07-01

    Palladium impregnated magnetite nanoparticles (Pd-Fe3O4NPs) have been synthesized and used as reusable catalyst for the fluorometric determination of polyphenols in wines. The method is based on the decrease of the indocyanine green fluorescence, which is ascribed to its oxidation by dissolved oxygen in the presence of the nanoparticles, and the inhibition of the fluorescence decrease by polyphenols, which is proportional to the polyphenol concentration. The dynamic range of the calibration graph is 0.1-10.0µM gallic acid, which was chosen as model analyte, and the detection limit is 0.02µM. Precision data, expressed as relative standard deviation, ranged between 3.3% and 5.4%. The method was applied to the analysis of several wine samples, obtaining recovery values in the range of 79.7-102.0%. The results obtained were compared with those obtained using the Folin-Ciocalteu and laccase methods, finding that Pd-Fe3O4NPs provide a better selectivity than the first method and show a catalytic behavior similar to that of laccase. PMID:27154689

  18. Inhibition of non-haem iron absorption in man by polyphenolic-containing beverages.

    PubMed

    Hurrell, R F; Reddy, M; Cook, J D

    1999-04-01

    The effects of different polyphenol-containing beverages on Fe absorption from a bread meal were estimated in adult human subjects from the erythrocyte incorporation of radio-Fe. The test beverages contained different polyphenol structures and were rich in either phenolic acids (chlorogenic acid in coffee), monomeric flavonoids (herb teas, camomile (Matricaria recutita L.), vervain (Verbena officinalis L.), lime flower (Tilia cordata Mill.), pennyroyal (Mentha pulegium L.) and peppermint (Mentha piperita L.), or complex polyphenol polymerization products (black tea and cocoa). All beverages were potent inhibitors of Fe absorption and reduced absorption in a dose-dependent fashion depending on the content of total polyphenols. Compared with a water control meal, beverages containing 20-50 mg total polyphenols/serving reduced Fe absorption from the bread meal by 50-70%, whereas beverages containing 100-400 mg total polyphenols/serving reduced Fe absorption by 60-90%. Inhibition by black tea was 79-94%, peppermint tea 84%, pennyroyal 73%, cocoa 71%, vervain 59%, lime flower 52% and camomile 47%. At an identical concentration of total polyphenols, black tea was more inhibitory than cocoa, and more inhibitory than herb teas camomile, vervain, lime flower and pennyroyal, but was of equal inhibition to peppermint tea. Adding milk to coffee and tea had little or no influence on their inhibitory nature. Our findings demonstrate that herb teas, as well as black tea, coffee and coca can be potent inhibitors of Fe absorption. This property should be considered when giving dietary advice in relation to Fe nutrition. PMID:10999016

  19. Comparison of polyphenol intakes according to distinct dietary patterns and food sources in the Adventist Health Study-2 cohort.

    PubMed

    Burkholder-Cooley, Nasira; Rajaram, Sujatha; Haddad, Ella; Fraser, Gary E; Jaceldo-Siegl, Karen

    2016-06-01

    Evidence suggests a relationship between polyphenol intake and health benefits. Polyphenol intake among a large US cohort with diverse dietary practices ranging from meatless to omnivorous diets has not been previously evaluated. The primary aim of this study was to compare polyphenol intakes of several vegetarian and non-vegetarian dietary patterns and to assess phenolic intake by food source. To characterise dietary intake, a FFQ was administered to 77 441 participants of the Adventist Health Study-2. Dietary patterns were defined based on the absence of animal food consumption as vegan, lacto-ovo-vegetarian, pesco-vegetarian, semi-vegetarian and non-vegetarian. Polyphenol intakes were calculated based on chromatography-derived polyphenol content data of foods from Phenol-Explorer, US Department of Agriculture databases and relevant literature. Results revealed a mean unadjusted total polyphenol intake of 801 (sd 356) mg/d, and the main foods contributing to polyphenol intakes were coffee, fruits and fruit juices. Total polyphenol intake differed significantly between dietary patterns, with phenolic acids from coffee contributing the greatest variation. The dominant classes and sources of dietary polyphenols differed between vegetarian and non-vegetarian diets. Flavonoid intake was the highest among pesco-vegetarians, and phenolic acid intake was the highest among non-vegetarians. In addition, coffee consumers appeared to have a different dietary profile than non-coffee consumers, including greatly reduced contribution of fruits, vegetables and legumes to total phenolic intake. Coffee drinkers were more likely to be non-vegetarians, which explained several of these observations. Further evaluating these differences may be important in identifying relationships between plant-based diets and health outcomes. PMID:27080936

  20. Interaction of chlorogenic acids and quinides from coffee with human serum albumin.

    PubMed

    Sinisi, Valentina; Forzato, Cristina; Cefarin, Nicola; Navarini, Luciano; Berti, Federico

    2015-02-01

    Chlorogenic acids and their derivatives are abundant in coffee and their composition changes between coffee species. Human serum albumin (HSA) interacts with this family of compounds with high affinity. We have studied by fluorescence spectroscopy the specific binding of HSA with eight compounds that belong to the coffee polyphenols family, four acids (caffeic acid, ferulic acid, 5-O-caffeoyl quinic acid, and 3,4-dimethoxycinnamic acid) and four lactones (3,4-O-dicaffeoyl-1,5-γ-quinide, 3-O-[3,4-(dimethoxy)cinnamoyl]-1,5-γ-quinide, 3,4-O-bis[3,4-(dimethoxy)cinnamoyl]-1,5-γ-quinide, and 1,3,4-O-tris[3,4-(dimethoxy)cinnamoyl]-1,5-γ-quinide), finding dissociation constants of the albumin-chlorogenic acids and albumin-quinides complexes in the micromolar range, between 2 and 30μM. Such values are comparable with those of the most powerful binders of albumin, and more favourable than the values obtained for the majority of drugs. Interestingly in the case of 3,4-O-dicaffeoyl-1,5-γ-quinide, we have observed the entrance of two ligand molecules in the same binding site, leading up to a first dissociation constant even in the hundred nanomolar range, which is to our knowledge the highest affinity ever observed for HSA and its ligands. The displacement of warfarin, a reference drug binding to HSA, by the quinide has also been demonstrated. PMID:25172718

  1. Antioxidant capacities and polyphenolics of Chinese cabbage (Brassica rapa L. ssp. Pekinensis) leaves.

    PubMed

    Seong, Gi-Un; Hwang, In-Wook; Chung, Shin-Kyo

    2016-05-15

    Chinese cabbage (Brassica rapa L. ssp. Pekinensis) is a green leafy vegetable used mainly in kimchi, salted and fermented dishes. Consumer preference for the leaf portion differs according to the type of dishes. In this study, Chinese cabbage was divided into three parts, and their antioxidant activities were investigated through in vitro assays. The total phenolic contents (TPC), total flavonoid contents (TFC), and vitamin C contents were also determined as indicators of antioxidant contents. The phenolic acids and flavonoids were separated and identified using high performance liquid chromatography (HPLC) and liquid chromatography/mass spectrometry (LC/MS). The outer leaf had the strongest antioxidant activity with the maximum antioxidant contents, followed by the mid- and inner leaves. Principal component analysis (PCA) revealed that outer leaf is positively related to caffeic acid, p-coumaric acid, ferulic acid, and myricetin contents, whereas the mid- and inner leaves are negatively related to sinapic acid contents. PMID:26776015

  2. Water stress induces changes in polyphenol profile and antioxidant capacity in poplar plants (Populus spp.).

    PubMed

    Popović, B M; Štajner, D; Ždero-Pavlović, R; Tumbas-Šaponjac, V; Čanadanović-Brunet, J; Orlović, S

    2016-08-01

    This paper is aimed to characterize young poplar plants under the influence of water stress provoked by polyethileneglycol 6000 (PEG 6000). Three polar genotypes (M1, B229, and PE19/66) were grown in hydroponics and subjected to 100 and 200 mOsm PEG 6000 during six days. Polyphenol characterization, two enzymatic markers and antioxidant capacity in leaves and roots were investigated in stressed plants. Total phenol content, ferric reducing antioxidant capacity (FRAP) and DPPH antiradical power (DPPH ARP) were determined for estimating total antioxidant capacity. Polyphenol oxidase (PPO) and phenylalanine ammonia lyase (PAL) were determined as enzymatic markers. Polyphenol characterization of poplar samples was performed by HPLC-PDA analysis. All results were subjected to correlation analysis and principal component analysis (PCA). Inspite of the decrease of total phenol content in investigated genotypes, as well as total antioxidant capacity, some of polyphenols were affected by stress like flavonoids chrysin, myricetine, kaempferol and isoferulic acid in roots of B229 genotype (Populus deltoides). Genotype B229 also showed the increase of antioxidant capacity and PAL activity in root and leaves under stress what could be the indicator of the adaptability of poplar plants to water stress. Significant positive correlations were obtained between PAL, antioxidant capacity as well as phenolic acids among themselves. Chemometric evaluation showed close interdependence between flavonoids, FRAP, DPPH antiradical power and both investigated enzymes of polyphenol metabolism, PAL and PPO. PMID:27116372

  3. Metabolism of hydroxycinnamic acids and esters by Brettanomyces in different red wines

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Depending on the cultivars and other factors, differing concentrations of hydroxycinnamic acids (caffeic, p-coumaric, and ferulic acids) and their corresponding tartaric acid esters (caftaric, coutaric, and fertaric acid, respectively) are found in red wines. Hydroxycinnamic acids are metabolized by...

  4. Encapsulation of Natural Polyphenolic Compounds; a Review

    PubMed Central

    Munin, Aude; Edwards-Lévy, Florence

    2011-01-01

    Natural polyphenols are valuable compounds possessing scavenging properties towards radical oxygen species, and complexing properties towards proteins. These abilities make polyphenols interesting for the treatment of various diseases like inflammation or cancer, but also for anti-ageing purposes in cosmetic formulations, or for nutraceutical applications. Unfortunately, these properties are also responsible for a lack in long-term stability, making these natural compounds very sensitive to light and heat. Moreover, polyphenols often present a poor biodisponibility mainly due to low water solubility. Lastly, many of these molecules possess a very astringent and bitter taste, which limits their use in food or in oral medications. To circumvent these drawbacks, delivery systems have been developed, and among them, encapsulation would appear to be a promising approach. Many encapsulation methods are described in the literature, among which some have been successfully applied to plant polyphenols. In this review, after a general presentation of the large chemical family of plant polyphenols and of their main chemical and biological properties, encapsulation processes applied to polyphenols are classified into physical, physico-chemical, chemical methods, and other connected stabilization methods. After a brief description of each encapsulation process, their applications to polyphenol encapsulation for pharmaceutical, food or cosmetological purposes are presented. PMID:24309309

  5. Colonic metabolites of berry polyphenols: the missing link to biological activity?

    PubMed

    Williamson, Gary; Clifford, Michael N

    2010-10-01

    The absorption of dietary phenols, polyphenols and tannins (PPT) is an essential step for biological activity and effects on health. Although a proportion of these dietary bioactive compounds are absorbed intact, depending on their chemical structure and the nature of any attached moiety (e.g. sugar, organic acid), substantial amounts of lower molecular weight catabolites are absorbed after biotransformation by the colon microflora. The main products in the colon are (a) benzoic acids (C6-C1), especially benzoic acid and protocatechuic acid; (b) phenylacetic acids (C6-C2), especially phenylacetic acid per se; (c) phenylpropionic acids (C6-C3), where the latter are almost entirely in the dihydro form, notably dihydrocaffeic acid, dihydroferulic acid, phenylpropionic acid and 3-(3'-hydroxyphenyl)-propionic acid. As a result of this biotransformation, some of these compounds can each reach mm concentrations in faecal water. Many of these catabolites are efficiently absorbed in the colon, appear in the blood and are ultimately excreted in the urine. In the case of certain polyphenols, such as anthocyanins, these catabolites are major products in vivo; protocatechuic acid is reported to represent a substantial amount of the ingested dose of cyanidin-3-O-glucoside. The major catabolites of berries, and especially blackcurrants, are predicted based on compositional data for polyphenols from berries and other sources. Since microbial catabolites may be present at many sites of the body in higher concentration than the parent compound, it is proposed that at least a part of the biological activities ascribed to berry polyphenols and other PPT are due to their colonic catabolites. PMID:20955650

  6. Antioxidant activity, lipophilicity and extractability of polyphenols from pig skin - development of analytical methods for skin permeation studies.

    PubMed

    Zillich, Olesya V; Schweiggert-Weisz, Ute; Hasenkopf, Katrin; Eisner, Peter; Kerscher, Martina

    2013-11-01

    Permeation of polyphenols through the stratum corneum barrier is a precondition for the protective action of polyphenols against oxidative skin damage. Prior to in vitro skin permeation experiments, we developed a method for the quantification of polyphenols in pig skin, including organic solvent extraction and HPLC analysis. Catechine hydrate, epigallocatechin gallate, trans-resveratrol, quercetin, rutin and protocatechuic acid were chosen for this study as representatives of phenolics with different lipophilicity and molecular weight. The antioxidative activities of polyphenols as well as their octanol-water partition coefficients at different pH values were determined. Extraction of polyphenols from pig skin was optimized by variation of solvent composition, homogenization intensity and time, as well as partial exclusion of oxygen during extraction. The highest recovery rates could be reached by extraction with the methanol-water mixture (90:10, v/v), containing 0.2 g/L l-ascorbic acid, after the cryo-milling for 4 min. Recoveries of 72% for total phenolics, 96% for quercetin and protocatechuic acid, 90% for rutin and 74% for trans-resveratrol, were achieved. These extraction parameters will be selected for the polyphenol extraction from pig skin for further in vitro drug permeation studies. PMID:23703300

  7. Wine Polyphenols: Potential Agents in Neuroprotection

    PubMed Central

    Basli, Abdelkader; Soulet, Stéphanie; Chaher, Nassima; Mérillon, Jean-Michel; Chibane, Mohamed; Monti, Jean-Pierre; Richard, Tristan

    2012-01-01

    There are numerous studies indicating that a moderate consumption of red wine provides certain health benefits, such as the protection against neurodegenerative diseases. This protective effect is most likely due to the presence of phenolic compounds in wine. Wine polyphenolic compounds are well known for the antioxidant properties. Oxidative stress is involved in many forms of cellular and molecular deterioration. This damage can lead to cell death and various neurodegenerative disorders, such as Parkinson's or Alzheimer's diseases. Extensive investigations have been undertaken to determine the neuroprotective effects of wine-related polyphenols. In this review we present the neuroprotective abilities of the major classes of wine-related polyphenols. PMID:22829964

  8. Polyphenols as mitochondria-targeted anticancer drugs.

    PubMed

    Gorlach, Sylwia; Fichna, Jakub; Lewandowska, Urszula

    2015-10-01

    Mitochondria are the respiratory and energetic centers of the cell where multiple intra- and extracellular signal transduction pathways converge leading to dysfunction of those organelles and, consequently, apoptotic or/and necrotic cell death. Mitochondria-targeted anticancer drugs are referred to as mitocans; they have recently been classified by Neuzil et al. (2013) according to their molecular mode of action into: hexokinase inhibitors; mimickers of the Bcl-2 homology-3 (BH3) domains; thiol redox inhibitors; deregulators of voltage-dependent anionic channel (VDAC)/adenine nucleotide translocase (ANT) complex; electron redox chain-targeting agents; lipophilic cations targeting the mitochondrial inner membrane; tricarboxylic acid cycle-targeting agents; and mitochondrial DNA-targeting agents. Polyphenols of plant origin and their synthetic or semisynthetic derivatives exhibit pleiotropic biological activities, including the above-mentioned modes of action characteristic of mitocans. Some of them have already been tested in clinical trials. Gossypol has served as a lead compound for developing more efficient BH3 mimetics such as ABT-737 and its orally available structural analog ABT-263 (Navitoclax). Furthermore, mitochondriotropic derivatives of phenolic compounds such as quercetin and resveratrol have been synthesized and reported to efficiently induce cancer cell death in vitro. PMID:26185003

  9. Polyphenolic extracts of cherry (Prunus cerasus L.) and blackcurrant (Ribes nigrum L.) leaves as natural preservatives in meat products.

    PubMed

    Nowak, Agnieszka; Czyzowska, Agata; Efenberger, Magdalena; Krala, Lucjan

    2016-10-01

    The objective of this study was to evaluate the possibility of using polyphenolic extracts from cherry and blackcurrant leaves as natural antimicrobial agents in meat products. The polyphenolic composition of the extracts was analyzed and their impact on the microbial quality, lipid oxidation, color, and sensory evaluation of pork sausages was studied. Polyphenolic extracts were obtained from leaves collected in September. The total polyphenolic content in sour cherry leaf extract was 1.5 times higher than that found in blackcurrant leaf extract. Analysis of the polyphenol profile of each extract revealed two major groups: phenolic acids and flavonoids, including epigallocatechin and glycosides of quercetin and kaempferol. After chilling the sausages for 14 and 28 days, the extracts caused significantly lower MDA generation, indicating an antioxidant effect. Color changes after 28 days of storage were perceptible in the case of all treatments, with and without polyphenols. The application of sour cherry and black currant leaf extracts increased the shelf life of vacuum-packed sausages. Both extracts enhanced the microbial quality of the pork sausages over 14 days of refrigerated storage. Sour cherry leaf polyphenols were more effective against almost all studied groups of microorganisms. PMID:27375255

  10. Polyphenolic Antioxidants and Neuronal Regeneration.

    PubMed

    Ataie, Amin; Shadifar, Mohammad; Ataee, Ramin

    2016-04-01

    Many studies indicate that oxidative stress is involved in the pathophysiology of neurodegenerative diseases. Oxidative stress can induce neuronal damages, modulate intracellular signaling and ultimately leads to neuronal death by apoptosis or necrosis. To review antioxidants preventive effects on oxidative stress and neurodegenerative diseases we accumulated data from international medical journals and academic informations' sites. According to many studies, antioxidants could reduce toxic neuronal damages and many studies confirmed the efficacy of polyphenol antioxidants in fruits and vegetables to reduce neuronal death and to diminish oxidative stress. This systematic review showed the antioxidant activities of phytochemicals which play as natural neuroprotectives with low adverse effects against some neurodegenerative diseases as Parkinson or Alzheimer diseases. PMID:27303602

  11. Polyphenolic Antioxidants and Neuronal Regeneration

    PubMed Central

    Ataie, Amin; Shadifar, Mohammad; Ataee, Ramin

    2016-01-01

    Many studies indicate that oxidative stress is involved in the pathophysiology of neurodegenerative diseases. Oxidative stress can induce neuronal damages, modulate intracellular signaling and ultimately leads to neuronal death by apoptosis or necrosis. To review antioxidants preventive effects on oxidative stress and neurodegenerative diseases we accumulated data from international medical journals and academic informations’ sites. According to many studies, antioxidants could reduce toxic neuronal damages and many studies confirmed the efficacy of polyphenol antioxidants in fruits and vegetables to reduce neuronal death and to diminish oxidative stress. This systematic review showed the antioxidant activities of phytochemicals which play as natural neuroprotectives with low adverse effects against some neurodegenerative diseases as Parkinson or Alzheimer diseases. PMID:27303602

  12. Polyphenol content and antioxidant activity of California almonds depend on cultivar and harvest year

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The polyphenol content and antioxidant activity of Nonpareil, Carmel, Butte, Sonora, Fritz, Mission, and Monterey almond cultivars harvested over 3 seasons in California were examined. LC-MS was employed to quantify 16 flavonoids and 2 phenolic acids in acidified methanol extracts of almond skins. T...

  13. Murta leaves (Ugni molinae Turcz) as a source of antioxidant polyphenols.

    PubMed

    Rubilar, Mónica; Pinelo, Manuel; Ihl, Mónica; Scheuermann, Erik; Sineiro, Jorge; Nuñez, María José

    2006-01-11

    Extracts from Murta leaves are used by Chilean natives for their benefits on health and cosmetic properties, which are mainly due to the presence of polyphenolic compounds. Extraction of such compounds is strongly influenced by several variables, the effects of which are studied in this work; the antioxidant power of the resulting extracts was measured by two different methods [2,2-diphenyl-1-picrylhydrazyl (DPPH) and thiobarbituric acid reactive substances (TBARS)]. On the whole, maximum values of polyphenolic yields and antiradical power (DPPH method) were attained at 50 degrees C (from 25 to 50 degrees C) and a solvent-to-solid ratio (v/w) of 15:1 (15:1-25:1). The solvents assayed were ethanol, methanol, and water. The highest polyphenolic yield values (2.6% expressed as gallic acid) were reached with methanol, whereas maximum EC50 was attained by the ethanol extract (0.121 mol gallic acid/mol DPPH). Contact time was shown to have only a slight influence in alcoholic extraction, while in water a remarkable effect of increasing contact times (30-90 min) was observed. Just water was the solvent that offered the best result when the antioxidant power was measured by the TBARS method. High-performance liquid chromatography-mass spectrometry analysis revealed the presence of polyphenols, basically flavonols and flavanols, sometimes glycosilated; myricetin and quercetin glycosides were detected in all extracts, whereas epicatechin was present in alcoholic extracts and gallic acid was only present in water. PMID:16390178

  14. Polyphenols in Barringtonia racemosa and their protection against oxidation of LDL, serum and haemoglobin.