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Sample records for caffeic acid ascorbyl

  1. Additions of caffeic acid, ascorbyl palmitate or gamma-tocopherol to fish oil-enriched energy bars affect lipid oxidation differently

    DEFF Research Database (Denmark)

    Horn, Anna Frisenfeldt; Nielsen, Nina Skall; Jacobsen, Charlotte

    2009-01-01

    The objectives of the study were to investigate the effects of caffeic acid, ascorbyl palmitate and gamma-tocopherol on protection of fish oil-enriched energy bars against lipid oxidation during storage for 10 weeks at room temperature. The lipophilic gamma-tocopherol reduced lipid oxidation during...... storage when added at a concentration above 440 mu g/g fish oil. However, the best antioxidative effect was observed when it was added at a concentration of 660 mu g/g fish oil. In contrast, prooxidative effects were observed when using either gamma-tocopherol at concentrations below 220 mu g/g fish oil......, or the hydrophilic caffeic acid, or the amphiphilic ascorbyl palmitate at concentrations of 75, 150 and 300 mu g/g fish oil. Prooxidative effects were observed as an increase in the formation of lipid hydroperoxides and volatile secondary oxidation products, as well as the development of rancid off...

  2. Butylated caffeic acid: An efficient novel antioxidant

    Directory of Open Access Journals (Sweden)

    G. Shi

    2017-09-01

    Full Text Available A novel antioxidant, butylated caffeic acid (BCA was rationally designed by adding a tert-butyl group to caffeic acid, which was synthesized at a high yield (36.2% from 2-methoxy-4-methylphenol by a four-step reaction including Friedel-Crafts alkylation, bromine oxidation, ether bond hydrolysis and Knoevenagel condensation. Its antioxidant capacity was much stronger than common commercial antioxidant tert-butyl hydroquinone (TBHQ and its mother compound, caffeic acid, in both rancimat and deep frying tests. When investigated via the DPPH method, the antioxidant capacity of BCA was almost equal to TBHQ, but lower than caffeic acid. BCA could be a potentially strong antioxidant, especially for food processing at high temperatures such as deep frying and baking.

  3. Butylated caffeic acid: An efficient novel antioxidant

    International Nuclear Information System (INIS)

    Shi, G.; Liao, X.; Olajide, T.M.; Liu, J.; Jiang, X.; Weng, X.

    2017-01-01

    A novel antioxidant, butylated caffeic acid (BCA) was rationally designed by adding a tert-butyl group to caffeic acid, which was synthesized at a high yield (36.2%) from 2-methoxy-4-methylphenol (1) by a four-step reaction including Friedel-Crafts alkylation, bromine oxidation, ether bond hydrolysis and Knoevenagel condensation. Its antioxidant capacity was much stronger than common commercial antioxidant tert-butyl hydroquinone (TBHQ) and its mother compound, caffeic acid, in both rancimat and deep frying tests. When investigated via the DPPH method, the antioxidant capacity of BCA was almost equal to TBHQ, but lower than caffeic acid. BCA could be a potentially strong antioxidant, especially for food processing at high temperatures such as deep frying and baking. [es

  4. Chlorogenic acid and caffeic acid are absorbed in humans

    NARCIS (Netherlands)

    Olthof, Margreet R.; Hollman, Peter C H; Katan, Martijn B.

    2001-01-01

    Chlorogenic acid, an ester of caffeic acid and quinic acid, is a major phenolic compound in coffee; daily intake in coffee drinkers is 0.5-1 g. Chlorogenic acid and caffeic acid are antioxidants in vitro and might therefore contribute to the prevention of cardiovascular disease. However, data on the

  5. Pharmacokinetics of Caffeic Acid from Methanol Seed Extract of ...

    African Journals Online (AJOL)

    Methods: A dose of the extract (500 mg, equivalent to 37.135 mg caffeic acid) was administered orally to 6 male .... emission. Validation studies. Linearity. The rat plasma samples were spiked by caffeic acid solutions ..... Atomic structure of.

  6. Application of l-ascorbic acid and its derivatives (sodium ascorbyl phosphate and magnesium ascorbyl phosphate) in topical cosmetic formulations: stability studies

    International Nuclear Information System (INIS)

    Smaoui, S.; Hilima, H.B.

    2013-01-01

    The present study aimed to formulate and subsequently evaluate a topical skin-care cream (o/w emulsion) from l-ascorbic acid and its derivatives (sodium ascorbyl phosphate and magnesium ascorbyl phosphate) at 2% versus its vehicle (Control). Formulations were developed by entrapping it in the oily phase of o/w emulsion and were stored at 8 degree C, 25 degree C and 40 degree C (in incubator) for a period of four weeks to investigate their stability. In the physical analysis, the evaluation parameters consisted of color, smell, phase separation, centrifugation, and liquefaction. Chemical stability of both derivatives was established by HPLC analysis. In the chemical analysis, the formulation with sodium ascorbyl phosphate was more stable than those with magnesium ascorbyl phosphate and l-ascorbic acid. The microbiological stability of the formulations was also evaluated. The findings indicated that the formulations with l-ascorbic acid and its derivatives were efficient against the proliferation of various spoilage microorganisms, including aerobic plate counts as well as Pseudomonas aeruginosa, Staphylococcus aureus, and yeast and mold counts. The results presented in this work showed good stability throughout the experimental period. Newly formulated emulsion proved to exhibit a number of promising properties and attributes that might open new opportunities for the construction of more efficient, safe, and cost-effective skin-care, cosmetic, and pharmaceutical products. (author)

  7. Caffeic acid derivative from Clinopodium umbrosum

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    M. Esfahanizadeh

    2017-11-01

    Full Text Available Background and objectives: Plants of genus Clinopodium have been used in different cultures as traditional medicines.Due to theimportance of medicinal properties of the genus Clinopodium, C. umbrosum was selected for phytochemical analysis along with evaluation of its antioxidant property. Methods: The aerial parts of C. umbrosum were extracted with petroleum ether, chloroform, and methanol. Later, the methanol extract was fractionated via solid phase extraction and reversed phase high performance liquid chromatography. Consequently, structure of the isolated compound was analyzed through spectral analysis of 1D and 2D NMR data. Besides, the essential oil of C. umbrosum achieved through hydrodistillation was analyzed via gas chromatography-mass spectrometry (GC-MS. Additionally, the antioxidant property of C. umbrosum methanol extracttogether with its phenolics and flavonoids content were assessed. Results: Structure elucidation of the purified compound revealed presence of a caffeic acid derivative in C. umbrosum methanol extract. GC-MS analysis of the essential oil showed limonene, acetophenone, palmitic acid and phytol as the most frequent components of the essential oil. Moreover, the RC50 value for free radical scavenging activity of  the methanol extract was determined as 38.52 µg/mL and values for the total phenolics and flavonoids contact were calculated as 5.14 g gallic acid equivalent and 4.25 g quercetin equivalent per 100 g of dried plant material, respectively.  Conclusion: Overall, the present study was the first report on the phytochemical analysis of C. umbrosum whichrevealed presence of rosmarinic acid as the main component of the methanol extract with prominent antioxidant activity.

  8. Pharmacokinetics of Caffeic Acid from Methanol Seed Extract of ...

    African Journals Online (AJOL)

    Purpose: To describe caffeic acid-based pharmacokinetics of methanol extract of seed of Syzygium cumini L. in rats. Methods: A dose of the extract (500 mg, equivalent to 37.135 mg caffeic acid) was administered orally to 6 male Wister rats, weighing 200 ± 10 g. Blood samples (0.5 mL), collected from the tail vein at 0, 15, ...

  9. Novel Caffeic Acid Nanocarrier: Production, Characterization, and Release Modeling

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    Milad Fathi

    2013-01-01

    Full Text Available This paper deals with the development of novel nanocarriers using layer by layer carbohydrate coating of caffeic acid loaded solid lipid nanoparticles (SLNs to improve stability and colon delivery of the poorly water-soluble caffeic acid. Three biopolymers (chitosan, alginate, and pectin in different concentrations (0.1, 0.25, and 0.5% were electrostatically coated over the SLN surface. The size and zeta potential of produced nanocarriers were measured using photon correlation spectroscopy. Mathematical models (i.e., zero-order, first-order, Higuchi, Ritger-Peppas, reciprocal powered time, Weibull, and quadratic models were used to describe the release and kinetic modeling in gastrointestinal solution (GIS. Also, antioxidant activity of caffeic acid during the release in GIS was investigated using DPPH and reducing activity methods. The prepared treatments coated by alginate-chitosan as well as pectin-chitosan coated SLN at the concentration of 0.1% showed nanosized bead; the latter efficiently retarded the release of caffeic acid in gastric media up to 2.5 times higher than that of SLN. Zeta potential values of coated samples were found to significantly increase in comparison to SLN indicating the higher stability of produced nanocarriers. Antioxidant activity of caffeic acid after gastric release did not result in the same trend as observed for caffeic acid release from different treatments; however, in line with less caffeic acid release in the intestine solution by the effect of coating, lower antioxidant activity was determined at the end stage of the experiment.

  10. Final report of the safety assessment of L-Ascorbic Acid, Calcium Ascorbate, Magnesium Ascorbate, Magnesium Ascorbyl Phosphate, Sodium Ascorbate, and Sodium Ascorbyl Phosphate as used in cosmetics.

    Science.gov (United States)

    Elmore, Amy R

    2005-01-01

    L-Ascorbic Acid, Calcium Ascorbate, Magnesium Ascorbate, Magnesium Ascorbyl Phosphate, Sodium Ascorbate, and Sodium Ascorbyl Phosphate function in cosmetic formulations primarily as antioxidants. Ascorbic Acid is commonly called Vitamin C. Ascorbic Acid is used as an antioxidant and pH adjuster in a large variety of cosmetic formulations, over 3/4 of which were hair dyes and colors at concentrations between 0.3% and 0.6%. For other uses, the reported concentrations were either very low (cosmetics, but are not currently used. Sodium Ascorbyl Phosphate functions as an antioxidant in cosmetic products and is used at concentrations ranging from 0.01% to 3%. Magnesium Ascorbyl Phosphate functions as an antioxidant in cosmetics and was reported being used at concentrations from 0.001% to 3%. Sodium Ascorbate also functions as an antioxidant in cosmetics at concentrations from 0.0003% to 0.3%. Related ingredients (Ascorbyl Palmitate, Ascorbyl Dipalmitate, Ascorbyl Stearate, Erythorbic Acid, and Sodium Erythorbate) have been previously reviewed by the Cosmetic Ingredient Review (CIR) Expert Panel and found "to be safe for use as cosmetic ingredients in the present practices of good use." Ascorbic Acid is a generally recognized as safe (GRAS) substance for use as a chemical preservative in foods and as a nutrient and/or dietary supplement. Calcium Ascorbate and Sodium Ascorbate are listed as GRAS substances for use as chemical preservatives. L-Ascorbic Acid is readily and reversibly oxidized to L-dehydroascorbic acid and both forms exist in equilibrium in the body. Permeation rates of Ascorbic Acid through whole and stripped mouse skin were 3.43 +/- 0.74 microg/cm(2)/h and 33.2 +/- 5.2 microg/cm(2)/h. Acute oral and parenteral studies in mice, rats, rabbits, guinea pigs, dogs, and cats demonstrated little toxicity. Ascorbic Acid and Sodium Ascorbate acted as a nitrosation inhibitor in several food and cosmetic product studies. No compound-related clinical signs or gross or

  11. Caffeic Acid Induces Apoptosis in Human Cervical Cancer Cells Through the Mitochondrial Pathway

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    Wei-Chun Chang

    2010-12-01

    Conclusion: Caffeic acid induces apoptosis by inhibiting Bcl-2 activity, leading to release of cytochrome c and subsequent activation of caspase-3, indicating that caffeic acid induces apoptosis via the mitochondrial apoptotic pathway. This also suggests that caffeic acid has a strong anti-tumor effect and may be a promising chemopreventive or chemotherapeutic agent.

  12. Inhibitory mechanism against oxidative stress of caffeic acid

    Directory of Open Access Journals (Sweden)

    Farhan Ahmed Khan

    2016-10-01

    Full Text Available The purpose of this article is to summarize the reported antioxidant activities of a naturally abundant bioactive phenolic acid, caffeic acid (CA, 3,4-dihydroxycinnamic acid, so that new avenues for future research involving CA can be explored. CA is abundantly found in coffee, fruits, vegetables, oils, and tea. CA is among the most potential and abundantly found in nature, hydroxycinnamic acids with the potential of antioxidant behavior. Reactive oxygen species produced as a result of endogenous processes can lead to pathophysiological disturbances in the human body. Foods containing phenolic substances are a potential source for free radical scavenging; these chemicals are known as antioxidants. This review is focused on CA's structure, availability, and potential as an antioxidant along with its mode of action. A brief overview of the literature published about the prooxidant potential of caffeic acid as well as the future perspectives of caffeic acid research is described. CA can be effectively employed as a natural antioxidant in various food products such as oils.

  13. Grape skins (Vitis vinifera L.) catalyze the in vitro enzymatic hydroxylation of p-coumaric acid to caffeic acid

    DEFF Research Database (Denmark)

    Arnous, Anis; Meyer, Anne S.

    2009-01-01

    The ability of grape skins to catalyze in vitro conversion of p-coumaric acid to the more potent antioxidant caffeic acid was studied. Addition of different concentrations of p-coumaric to red grape skins (Cabernet Sauvignon) resulted in formation of caffeic acid. This caffeic acid formation (Y...

  14. Caffeic acid treatment alters the extracellular adenine nucleotide hydrolysis in platelets and lymphocytes of adult rats.

    Science.gov (United States)

    Anwar, Javed; Spanevello, Roselia Maria; Pimentel, Victor Camera; Gutierres, Jessié; Thomé, Gustavo; Cardoso, Andreia; Zanini, Daniela; Martins, Caroline; Palma, Heloisa Einloft; Bagatini, Margarete Dulce; Baldissarelli, Jucimara; Schmatz, Roberta; Leal, Cláudio Alberto Martins; da Costa, Pauline; Morsch, Vera Maria; Schetinger, Maria Rosa Chitolina

    2013-06-01

    This study evaluated the effects of caffeic acid on ectonucleotidase activities such as NTPDase (nucleoside triphosphate diphosphohydrolase), Ecto-NPP (nucleotide pyrophosphatase/phosphodiesterase), 5'-nucleotidase and adenosine deaminase (ADA) in platelets and lymphocytes of rats, as well as in the profile of platelet aggregation. Animals were divided into five groups: I (control); II (oil); III (caffeic acid 10 mg/kg); IV (caffeic acid 50 mg/kg); and V (caffeic acid 100 mg/kg). Animals were treated with caffeic acid diluted in oil for 30 days. In platelets, caffeic acid decreased the ATP hydrolysis and increased ADP hydrolysis in groups III, IV and V when compared to control (P<0.05). The 5'-nucleotidase activity was decreased, while E-NPP and ADA activities were increased in platelets of rats of groups III, IV and V (P<0.05). Caffeic acid reduced significantly the platelet aggregation in the animals of groups III, IV and V in relation to group I (P<0.05). In lymphocytes, the NTPDase and ADA activities were increased in all groups treated with caffeic acid when compared to control (P<0.05). These findings demonstrated that the enzymes were altered in tissues by caffeic acid and this compound decreased the platelet aggregation suggesting that caffeic acid should be considered a potentially therapeutic agent in disorders related to the purinergic system. Copyright © 2013 Elsevier Ltd. All rights reserved.

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

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    Zhiqian Liu

    2014-05-01

    Full Text Available 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.

  16. Antioxidative effect of lipophilized caffeic acid in fish oil enriched mayonnaise and milk

    DEFF Research Database (Denmark)

    Alemán, Mercedes; Bou, Ricard; Guardiola, Francesc

    2015-01-01

    The antioxidative effect of lipophilized caffeic acid was assessed in two different fish oil enriched food products: mayonnaise and milk. In both emulsion systems, caffeic acid esterified with fatty alcohols of different chain lengths (C1–C20) were better antioxidants than the original phenolic c...

  17. Microencapsulation of caffeic acid phenethyl ester and caffeic acid phenethyl amide by inclusion in hydroxypropyl-β-cyclodextrin.

    Science.gov (United States)

    Garrido, E Manuela P J; Cerqueira, Ana S; Chavarria, Daniel; Silva, Tiago; Borges, Fernanda; Garrido, Jorge M P J

    2018-07-15

    Caffeic acid phenethyl ester (CAPE) is a bioactive polyphenolic compound obtained from propolis extract. Although it has a broad therapeutic potential, the bioavailability of CAPE is limited, due to reduced solubility and poor plasmatic stability. Efforts to reduce these pharmacokinetic drawbacks resulted in the synthesis of caffeic acid phenethyl amide (CAPA). Cyclodextrins have been proved as promising excipients for the formulation of active ingredients. Herein, we report the inclusion complexation behavior and binding ability of CAPE and CAPA with hydroxypropyl-β-cyclodextrin (HP-β-CD). The supramolecular interactions were examined through UV and FTIR spectroscopy, DSC, 1 H NMR and 2D ROESY. The CAPE/HP-β-CD and CAPA/HP-β-CD inclusion complexes stability constants were determined to be, respectively, 2911.6 and 584.6 M -1 in water and 2866.2 and 700.1 M -1 at physiological pH. The aqueous solubility increased notably, proving that HP-β-CD can be potentially useful to improve the biological, chemical and physical properties of CAPE and CAPA. Copyright © 2018 Elsevier Ltd. All rights reserved.

  18. System Development from Organic Solvents to Ionic Liquids for Synthesiz-ing Ascorbyl Esters with Conjugated Linoleic Acids

    DEFF Research Database (Denmark)

    Yang, Zhiyong; Schultz, Lise; Guo, Zheng

    2012-01-01

    . Results show that only Novozym® 435 turned out to be a useful enzymatic preparation for the production of ascorbyl-CLA ester. The optimum reaction conditions in the or-ganic solvent system were 4 h at 55°C and at a molar ratio of 5 (CLA/ascorbic acid). The esterification reaction was trans......-ferred to an ionic liquid system for the purpose of improving solubility of the polar substrate and avoiding the application of organic solvents. From screening experiments, it was evident that only methyltrioctylammonium triflouroacetate (tO-MA·TFA) could provide a proper reaction environment for production...... of ascorbyl-CLA ester when using Novozym® 435 as biocatalyst. It was possible to significantly increase the productivity (150 g/l) through the increase of ascorbic acid sol-ubility in ionic liquids by super saturation together with the increase of reaction temperature to 70°C, far beyond than that in organic...

  19. Efficacy Of Trichloro-acetic Acid Peel Alone Versus Combined Topical Magnesium Ascorbyl Phosphate For Epidermal Melasma

    International Nuclear Information System (INIS)

    Murtaza, F.; Noor, S. M.; Bangash, A. R.

    2016-01-01

    Objective: To compare the efficacy in terms of reduction in melasma area and severity index (MASI) score by more than 10 of a combination of 20% trichloro-acetic acid peel plus 5% topical magnesium ascorbyl phosphate versus 20 percent trichloroacetic acid peel alone in the treatment of epidermal melasma. Study Design: Randomized controlled trial. Place and Duration of Study: Department of Dermatology, Lady Reading Hospital (LRH), Peshawar, from May 2012 to May 2013. Methodology: Patients aged 18 - 65 years, with Fitzpatrick skin type III-V were divided into two equal groups having 74 patients each. Detailed history was taken and Wood's lamp examination done to rule out mixed and dermal melasma. Melasma area and severity index (MASI) score was calculated for every patient. Priming was done for all patients with tretinoin cream applied once daily at night for 2 weeks, and to use a broad spectrum sun block cream before sun exposure. Patients in group A were subjected to combined treatment, i.e. trichloro-acetic acid peel 20 percent (weekly) plus magnesium ascorbyl phosphate cream (applied once daily), while patients in group B were subjected to trichloro-acetic acid peel 20 percent (weekly) alone. Treatment was continued for 6 weeks. After completion of treatment, MASI score was recalculated. Proportion of patients with significant MASI score reduction was compared using chi-square test with significance at p < 0.05. Results: Male and female patients were 11 (14.9 percent) and 63 (85.1 percent), respectively in group A, whereas 13 (17.6 percent) and 61 (82.4 percent) in group B. The mean age in group A was 30.28±8.08 years, and 29.36±6.84 years in group B. Significant MASI score reduction in group A was seen in 60 (81.1 percent) patients and in group B 49 (66.2 percent, p= 0.040). Conclusion: Combination of trichloro-acetic acid peel and topical magnesium ascorbyl phosphate cream was significantly more effective than trichloro-acetic acid peel alone in

  20. In vitro antiviral efficacy of caffeic acid against canine distemper virus.

    Science.gov (United States)

    Wu, Zong-Mei; Yu, Zhen-Jiang; Cui, Zhen-Qiang; Peng, Lu-Yuan; Li, Hao-Ran; Zhang, Chun-Lei; Shen, Hai-Qing; Yi, Peng-Fei; Fu, Ben-Dong

    2017-09-01

    Canine distemper (CD) is a highly contagious disease caused by the canine distemper virus (CDV), and mortality can be as high as 100%. However, there is no specific treatment for CD. In this study, the antiviral activity of the caffeic acid against CDV was evaluated in vitro. The results showed that the IC 50 of the caffeic acid against CDV at 1 and 2 h post infection (PI) is 23.3 and 32.3 μg/mL, respectively. Consistently, at 1 and 2 h PI, the caffeic acid exhibited a reduced (23.3-57.0% and 37.2-38.1%) viral inhibitory effect in vero cells. Furthermore, the caffeic acid plus Ribavirin (RBV) has greater antiviral activity against CDV than the caffeic acid or RBV individually. In addition, the caffeic acid reduced the total viral RNA synthesis by 59-86% at 24-72 h. Therefore, our data provided the experimental evidence that the caffeic acid effectively inhibited CDV infection in vero cells, which may potentially be used to treat clinical disease associated with CDV infection. Copyright © 2017. Published by Elsevier Ltd.

  1. Caffeic acid production by simultaneous saccharification and fermentation of kraft pulp using recombinant Escherichia coli.

    Science.gov (United States)

    Kawaguchi, Hideo; Katsuyama, Yohei; Danyao, Du; Kahar, Prihardi; Nakamura-Tsuruta, Sachiko; Teramura, Hiroshi; Wakai, Keiko; Yoshihara, Kumiko; Minami, Hiromichi; Ogino, Chiaki; Ohnishi, Yasuo; Kondo, Ahikiko

    2017-07-01

    Caffeic acid (3,4-dihydroxycinnamic acid) serves as a building block for thermoplastics and a precursor for biologically active compounds and was recently produced from glucose by microbial fermentation. To produce caffeic acid from inedible cellulose, separate hydrolysis and fermentation (SHF) and simultaneous saccharification and fermentation (SSF) reactions were compared using kraft pulp as lignocellulosic feedstock. Here, a tyrosine-overproducing Escherichia coli strain was metabolically engineered to produce caffeic acid from glucose by introducing the genes encoding a 4-hydroxyphenyllactate 3-hydroxylase (hpaBC) from Pseudomonas aeruginosa and tyrosine ammonia lyase (fevV) from Streptomyces sp. WK-5344. Using the resulting recombinant strain, the maximum yield of caffeic acid in SSF (233 mg/L) far exceeded that by SHF (37.9 mg/L). In the SSF with low cellulase loads (≤2.5 filter paper unit/g glucan), caffeic acid production was markedly increased, while almost no glucose accumulation was detected, indicating that the E. coli cells experienced glucose limitation in this culture condition. Caffeic acid yield was also negatively correlated with the glucose concentration in the fermentation medium. In SHF, the formation of by-product acetate and the accumulation of potential fermentation inhibitors increased significantly with kraft pulp hydrolysate than filter paper hydrolysate. The combination of these inhibitors had synergistic effects on caffeic acid fermentation at low concentrations. With lower loads of cellulase in SSF, less potential fermentation inhibitors (furfural, 5-hydroxymethyfurfural, and 4-hydroxylbenzoic acid) accumulated in the medium. These observations suggest that glucose limitation in SSF is crucial for improving caffeic acid yield, owing to reduced by-product formation and fermentation inhibitor accumulation.

  2. Interactive effects of gallic/ferulic/caffeic acids and anthocyanins on pigment thermal stabilities.

    Science.gov (United States)

    Qian, Bing-Jun; Liu, Jian-Hua; Zhao, Shu-Juan; Cai, Jian-Xiong; Jing, Pu

    2017-06-01

    The data presented in this article are related to the research article entitled "The effects of gallic/ferulic/caffeic acids on colour intensification and anthocyanin stability" (Qian et al., 2017) [1]. This paper described preparation and isolation of anthocyanins from purple sweet potatoes (PSP) and the time-course of anthocyanin profiles treated with gallic, ferulic, or caffeic acids at 95 °C. The color appearance of PSPanthocyanins alone, or with gallic, ferulic, or caffeic acids was described after the 15 h of thermal treatment. The high resolution mass spectrographs of PSP anthocyanins were determined using UPLC-ESI-HRMS. The spatial interaction of peonidin 3-O-(2-O-β-D-glucopyranocyl-β-D-glucopyranoide)-5-O-β-D-glucopyranoside and gallic/ferulic/caffeic acids was illustrated by molecular dynamic simulation.

  3. The Sonodegradation of Caffeic Acid under Ultrasound Treatment: Relation to Stability

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    Yujing Sun

    2013-01-01

    Full Text Available 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.

  4. Synthesis of labelled compound of ferulic acid and caffeic acid with tritium

    International Nuclear Information System (INIS)

    Yi Mingguang; Wang Caiyun

    1986-01-01

    Effective components of Chinese traditional herbs consist of many compounds, but some of the compounds usually contain unsaturated carbon-carbon double bonds. The unsaturated organic compounds 3 H-Ferulic acid and 3 H-Caffeic acid are prepared with their tritiated intermediates made by electric-dischange exposure method, which ensures the compounds contaning double bonds not hydrogenated. The 3 H-Ferulic acid is composed of 3 H-vanillin and Malonic acid. The 3 H-Caffeic acid is composed of 3 H-protocatechuyl aldehyde and Malonic acid and the specific activity of the products is 0.2 mCi/mg. The radiochemicaly purity is greater than 90%

  5. Preparation and characterization of SPION functionalized via caffeic acid

    International Nuclear Information System (INIS)

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

    2015-01-01

    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 (D mag ) 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 (σ s ) is 44.11 emu/g and measured magnetic moment is 1.83 µ B . These parameters assign small order of magnetization for NPs with respect to bulk Fe 3 O 4 . Magnetic anisotropy was offered as uniaxial and calculated effective anisotropy constant (K eff ) is 34.82×10 4 Erg/g. The size-dependent saturation magnetization suggests the existence of a magnetically inactive layer as 1.035 nm for SPION-CFA. - Highlights: • The effects of CFA on the microstructure and magnetic properties of SPION have been investigated. • Product was structurally and magnetically characterized. • Product presented superparamagnetic behavior at room temperature

  6. Aspergillus niger whole-cell catalyzed synthesis of caffeic acid phenethyl ester in ionic liquids.

    Science.gov (United States)

    Rajapriya, Govindaraju; Morya, Vivek Kumar; Mai, Ngoc Lan; Koo, Yoon-Mo

    2018-04-01

    Synthesis of caffeic acid ester essentially requires an efficient esterification process to produce various kinds of medicinally important ester derivatives. In the present study, a comprehensive and comparative analysis of whole-cell catalyzed caffeic acid esters production in ionic liquids (ILs) media was performed. Olive oil induced mycelial mass of halotolerant Aspergillus niger (A.niger) EXF 4321 was freeze dried and used as a catalyst. To ensure maximum solubilization of caffeic acid for highest substrate loading several ILs were screened and 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([Emim][Tf 2 N]) was found to have the maximum solubility and favoured for enzymatic activity of freeze dried mycelia. The whole-cell catalyzed synthesis of caffeic acid phenethyl ester (CAPE) conditions were optimized and bioconversion up to 84% was achieved at a substrate molar ratio of 1:20 (caffeic acid:2-phenyl ethanol), 30°C for 12h. Results obtained during this study were encouraging and helpful to design a bioreactor system to produce caffeic acid derived esters. Copyright © 2017 Elsevier Inc. All rights reserved.

  7. Phytochemical profile of Orthosiphon aristatus extracts after storage: Rosmarinic acid and other caffeic acid derivatives.

    Science.gov (United States)

    Chua, Lee Suan; Lau, Cher Haan; Chew, Chee Yung; Ismail, Nurul Izzati Mohd; Soontorngun, Nitnipa

    2018-01-15

    Orthosiphon aristatus (Blume) Miq. is a medicinal herb which is traditionally used for the treatment of diabetes and kidney diseases in South East Asia. Previous studies reported higher concentration of antioxidative phytochemicals, especially rosmarinic acid (ester of caffeic acid) and other caffeic acid derivatives in this plant extract than the other herbs such as rosemary and sage which are usually used as raw materials to produce rosmarinic acid supplement in the market. The phytochemical profile of O. aristatus was investigated at different storage durations for quality comparison. The phytochemicals were extracted from the leaves and stems of O. aristatus using a reflux reactor. The extracts were examined for total phenolic and flavonoid contents, as well as their antioxidant capacities, in terms of radical scavenging, metal chelating and reducing power. The phytochemical profiles were also analyzed by unsupervised principal component analysis and hierarchical cluster analysis, in relation to the factor of storage at 4 °C for 5 weeks. The leaf extract was likely to have more phytochemicals than stem extract, particularly caffeic acid derivatives including glycosylated and alkylated caffeic acids. This explains higher ratio of total phenolic content to total flavonoid content with higher antioxidant capacities for the leaf extracts. Rosmarinic acid dimer and salvianolic acid B appeared to be the major constituents, possibly contributing to the previously reported pharmacological properties. However, the phytochemical profiles were found changing, even though the extracts were stored in the refrigerator (4 °C). The change was significantly observed at the fifth week based on the statistical pattern recognition technique. O. aristatus could be a promising source of rosmarinic acid and its dimer, as well as salvianolic acid B with remarkably antioxidant properties. The phytochemical profile was at least stable for a month stored at 4 °C. It is likely to be

  8. Effects of caffeic and chlorogenic acids on the rat skeletal system.

    Science.gov (United States)

    Folwarczna, J; Pytlik, M; Zych, M; Cegieła, U; Nowinska, B; Kaczmarczyk-Sedlak, I; Sliwinski, L; Trzeciak, H; Trzeciak, H I

    2015-02-01

    Caffeic acid, predominantly as esters linked to quinic acid (chlorogenic acids), is a phenolic acid present at high levels in coffee. The aim of the study was to investigate effects of caffeic and chlorogenic acids on the skeletal system of female rats with normal estrogen levels and estrogen-deficient. Caffeic acid (5 and 50 mg/kg p.o. daily) and chlorogenic acid (100 mg/kg p.o. daily) were administered for 4 weeks to non-ovariectomized and bilaterally ovariectomized mature Wistar rats, and their effects were compared with appropriate controls. Moreover, estradiol (0.2 mg/kg p.o. daily) was administered to ovariectomized rats. Bone turnover markers, mass, mineralization and mechanical properties were examined. Although caffeic acid at a low dose exerted some unfavorable effects on the skeletal system, at high doses, caffeic and chlorogenic acids slightly increased mineralization in the tibia and improved mechanical properties of the femoral diaphysis (compact bone). Unlike estradiol, they did not counteract the worsening of the tibial metaphysis bone strength (cancellous bone) and increases in osteocalcin concentration induced by estrogen deficiency. High doses of the phenolic acids slightly favorably affected the rat skeletal system independently of the estrogen status.

  9. Preparation and characterization of SPION functionalized via caffeic acid

    Energy Technology Data Exchange (ETDEWEB)

    Baykal, A. [Department of Chemistry, Fatih University, B.Çekmece, 34500 Istanbul (Turkey); Amir, Md., E-mail: mda.fatih@gmail.com [Department of Chemistry, Fatih University, B.Çekmece, 34500 Istanbul (Turkey); Günerb, S. [Department of Physics, Fatih University, B.Çekmece, 34500 Istanbul (Turkey); Sözeri, H. [TUBITAK-UME, National Metrology Institute, 41470 Gebze, Kocaeli (Turkey)

    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 (D{sub mag}) 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 (σ{sub s}) is 44.11 emu/g and measured magnetic moment is 1.83 µ{sub B}. These parameters assign small order of magnetization for NPs with respect to bulk Fe{sub 3}O{sub 4}. Magnetic anisotropy was offered as uniaxial and calculated effective anisotropy constant (K{sub eff}) is 34.82×10{sup 4} Erg/g. The size-dependent saturation magnetization suggests the existence of a magnetically inactive layer as 1.035 nm for SPION-CFA. - Highlights: • The effects of CFA on the microstructure and magnetic properties of SPION have been investigated. • Product was structurally and magnetically characterized. • Product presented superparamagnetic behavior at room temperature.

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

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    Lucia Natarelli

    Full Text Available 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.

  11. Biosynthesis of caffeic acid in Escherichia coli using its endogenous hydroxylase complex

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    Lin Yuheng

    2012-04-01

    Full Text Available Abstract Background Caffeic acid (3,4-dihydroxycinnamic acid is a natural phenolic compound derived from the plant phenylpropanoid pathway. Caffeic acid and its phenethyl ester (CAPE have attracted increasing attention for their various pharmaceutical properties and health-promoting effects. Nowadays, large-scale production of drugs or drug precursors via microbial approaches provides a promising alternative to chemical synthesis and extraction from plant sources. Results We first identified that an Escherichia coli native hydroxylase complex previously characterized as the 4-hydroxyphenylacetate 3-hydroxylase (4HPA3H was able to convert p-coumaric acid to caffeic acid efficiently. This critical enzymatic step catalyzed in plants by a membrane-associated cytochrome P450 enzyme, p-coumarate 3-hydroxylase (C3H, is difficult to be functionally expressed in prokaryotic systems. Moreover, the performances of two tyrosine ammonia lyases (TALs from Rhodobacter species were compared after overexpression in E. coli. The results indicated that the TAL from R. capsulatus (Rc possesses higher activity towards both tyrosine and L-dopa. Based on these findings, we further designed a dual pathway leading from tyrosine to caffeic acid consisting of the enzymes 4HPA3H and RcTAL. This heterologous pathway extended E. coli native tyrosine biosynthesis machinery and was able to produce caffeic acid (12.1 mg/L in minimal salt medium. Further improvement in production was accomplished by boosting tyrosine biosynthesis in E. coli, which involved the alleviation of tyrosine-induced feedback inhibition and carbon flux redirection. Finally, the titer of caffeic acid reached 50.2 mg/L in shake flasks after 48-hour cultivation. Conclusion We have successfully established a novel pathway and constructed an E. coli strain for the production of caffeic acid. This work forms a basis for further improvement in production, as well as opens the possibility of microbial synthesis

  12. Quantification of caffeic acid content in 4 species of mullein (Verbascum sp. ecotypes from southwest Iran

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    F. Jamshidi kia

    2017-11-01

    Full Text Available Background and objectives: The Verbascum genus is the largest genus of Scrophulariaceae family which has extensive natural habitat in southwest of Iran. Phenolic acids are one of the most important chemical compounds that have different biological activities including anti-inflammatory, antibacterial, antiviral, anti-tumor and antioxidant. Therefore, this study was conducted with the aim of caffeic acid quantification of 4 species of Verbascum sp. ecotypes from southwest Iran. Methods: Nine ecotypes of the 4 species (V. macrophyllus, V. pseudo- digitalis, V. sinatum, V. songaricum were collected from the southwest of Iran. Quantification of caffeic acid contentusing reversed-phase high-performance liquid chromatography (RP-HPLC with UV PDA 2800 detector, a C18 column with dimensions of 250×4.6 mm was performed. Results: The results showed that Verbascum sp. contained caffeic acid compound and there was a difference among species and ecotypes. The results showed the highest and lowest content of caffeic acid obtained from the V. sinatum species and ecotype Sepidan (7.76 μg/mg extract and V. songaricum species and ecotype Farokhshahr (0.54 μg/mg extract, respectively. Conclusion: The results revealed a high level of variation in caffeic acid among Verbascum sp. which was affected by habitat and climatic. The pattern of habitats of suitable ecotypes superior in terms of composition to should be selected and used for breeding and cropping mullein.

  13. Activity of caffeic acid in different fish lipid matrices: A review

    DEFF Research Database (Denmark)

    Medina, Isabel; Undeland, Ingrid; Larsson, Karin

    2012-01-01

    that the antioxidant activity depends on the physical state of the lipids and the composition of the intrinsic matrix in which they are situated. Caffeic acid significantly prevented rancidity in both unwashed and washed fish mince, the latter which was fortified with haemoglobin. In the unwashed mince, the activity......Caffeic acid, a hydroxycinnamic acid common in different vegetable sources, has been employed as a natural antioxidant for inhibiting oxidation of fish lipids present in different food matrices. The aim of this review is to discuss the mechanisms involved in the antioxidative and prooxidative...... effects of caffeic acid found in different model systems containing fish lipids. These model systems include bulk fish oils, liposomes from cod roe phospholipids, fish oil emulsions, washed cod mince, regular horse mackerel mince and a fish oil fortified fitness bar. The data reported show...

  14. [Determination of chlorogenic acid, caffeic acid and linarin in Flos Chrysanthemi Indici from different places by RP-hPLC].

    Science.gov (United States)

    Guo, Qiaosheng; Fang, Hailing; Shen, Haijin

    2010-05-01

    To evaluate the quality of Flos Chrysanthemi Indici which produced in twenty-two different producing places. Chlorogenic acid and caffeic acid were analyzed on a Shim-pack C8 colunm (4.6 mm x 250 mm, 5 microm) eluted with the mobile phase consisted of acetonitrile-0.5% phosphoric acid( 19:81). The detection wavelength was set at 326 nm. Linarin were eluted with the mobile phase consisted of methanol-water-acetic acid(26: 23: 1). The detection wavelength was set at 334 nm. The column temperature was 25 degrees C. The flow rate was 1.0 mL x min . The linear response ranged within 2.5-50 microg for chlorogenic acid (r = 0.998), 2.5-25 microg for caffeic acid (r = 0.998) and 4.97-41.47 microg for linarin (r = 0.999), respectively. Recoveries were 100.8% with RSD 2.1% for chlorogenic acid, 96.2% with RSD 2.3% for caffeic acid and 103.7% with RSD 1.8% for linarin. There was a significant difference in the content of chlorogenic acid, caffeic acid, linarin among the samples. The content of chlorogenic in the sample from Fengdou Chongqing city was the highest in those from other places. The content of caffeic acid in the all samples is very low. The content of linarin in the samples from Jiangsu province and Anhui province almost reached the national standard in pharmacopoeia.

  15. The timing of caffeic acid treatment with cisplatin determines sensitization or resistance of ovarian carcinoma cell lines

    Directory of Open Access Journals (Sweden)

    R. Sirota

    2017-04-01

    The use of caffeic acid as adjuvant for cisplatin should be carefully examined due to different pharmacokinetic profiles of caffeic acid and cisplatin. Thus, it is questionable if the two agents can reach the tumors at the right time frame in vivo.

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

    Science.gov (United States)

    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.

  17. Antimicrobial and enhancement of the antibiotic activity by phenolic compounds: Gallic acid, caffeic acid and pyrogallol.

    Science.gov (United States)

    Lima, Valéria N; Oliveira-Tintino, Cícera D M; Santos, Enaide S; Morais, Luís P; Tintino, Saulo R; Freitas, Thiago S; Geraldo, Yuri S; Pereira, Raimundo L S; Cruz, Rafael P; Menezes, Irwin R A; Coutinho, Henrique D M

    2016-10-01

    The indiscriminate use of antimicrobial drugs has increased the spectrum of exposure of these organisms. In our studies, these phenolic compounds were evaluated: gallic acid, caffeic acid and pyrogallol. The antibacterial, antifungal and modulatory of antibiotic activities of these compounds were assayed using microdilution method of Minimum Inhibitory Concentration (MIC) to bacteria and Minimum Fungicide Concentration (MFC) to fungi. The modulation was made by comparisons of the MIC and MFC of the compounds alone and combined with drugs against bacteria and fungi respectively, using a sub-inhibitory concentration of 128 μg/mL of substances (MIC/8). All substances not demonstrated clinically relevant antibacterial activity with a MIC above ≥1024 μg/mL. As a result, we observed that the caffeic acid presented a potentiating antibacterial effect over the 3 groups of bacteria studied. Pyrogallol showed a synergistic effect with two of the antibiotics tested, but only against Staphylococcus aureus. In general, caffeic acid was the substance that presented with the greatest number of antibiotics and with the greatest number of bacteria. In relation to the antifungal activity of all the compounds, the verified results were ≥1024 μg/mL, not demonstrating significant activity. Regarding potentiation of the effect of fluconazole, was observed synergistic effect only when assayed against Candida tropicalis, with all substances. Therefore, as can be seen, the compounds presented as substances that can be promising potentiating agents of antimicrobial drugs, even though they do not have direct antibacterial and antifungal action. Copyright © 2016 Elsevier Ltd. All rights reserved.

  18. Determination of caffeic acid in root and rhizome of Black cohosh (Cimicifuga racemosa (L. Nutt.

    Directory of Open Access Journals (Sweden)

    Zapala Karolina

    2014-06-01

    Full Text Available Cimicifuga racemosa, is a plant with a diverse and long history of medicinal use. Caffeic acid, bioactive compound, which often occurs with other polyphenols can influence the biological activity of this plant. The aim of our work was quantitative analysis of caffeic acid in roots and rhizomes of two varieties of C. racemosa. Analysis was performed by HPLC method. The extracts were separated on C18 reversed-phase column using mixture of methanol, water and formic acid (25:75:0.5 v/v/v as a mobile phase. The flow rate of eluent was 1.0 ml·min-1. The obtained validation parameters such as linearity, linear regression equation and precision expressed as a relative standard deviation were adequate for quantitative determination. Caffeic acid was found in all tested extracts. The highest total amount of caffeic acid was determined in C. racemosa var. racemosa (255.3 μg·g-1 while its concentration in C. racemosa var. cordifolia was significantly lower (213.0 μg·g-1.

  19. Mechanism and kinetics in reactions of caffeic acid with radicals by pulse radiolysis and calculation

    International Nuclear Information System (INIS)

    Li, Xifeng; Cai, Zhongli; Katsumura, Yosuke

    2000-01-01

    The interaction of caffeic acid with e aq - , (CH 3 ) 2 (OH) CCH 2 · , CO 2 ·- , H · , ·OH and N 3 · radicals were studied by γ-, pulse radiolysis and molecular orbital calculation. UV-visible spectra of electron/·OH adducts, semi-quinone radicals of caffeic ions, and the stable products from the reactions were derived. The rate constants were determined. The attacked sites and the most favorable structures of the transient radicals were predicted. Reaction mechanisms were proposed. (author)

  20. HIGH PERFORMANCE THIN LAYER CHROMATOGRAPHIC DETERMINATION OF CAFFEIC ACID AND ROSMARINIC ACID FROM THE LEAVES OF Orthosiphon stamineus

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    M. Amzad Hossain

    2010-06-01

    Full Text Available This paper presents the studies performed on extraction of Orthosiphon stamineus, Benth by using different solvent for the identification and quantification of the caffeic acid derivatives such as caffeic acid  and rosmarinic acid which confers to the leaves of this plant with remarkable pharmaceutical properties. High performance thin-layer chromatographic (HPTLC allows the identification and the quantification of more than 20 samples in the same chromatographic run. The analysis of the samples requires 15-30 min compared with more than 2 h using a typical HPLC method. Using the techniques of the HPTLC and the UV-VIS spectra we have found that the extraction of this herb plant contain, the caffeic acid and rosmarinic acid ranging between 0.029% up to 0.506% and up to 0.24% to 2.24% respectively.     Keywords: Caffice acid derivatives, quantification, Malaysian Orthosiphon stamineus, HPTLC

  1. Chitosan-caffeic acid-genipin films presenting enhanced antioxidant activity and stability in acidic media.

    Science.gov (United States)

    Nunes, Cláudia; Maricato, Élia; Cunha, Ângela; Nunes, Alexandra; da Silva, José A Lopes; Coimbra, Manuel A

    2013-01-02

    The use of chitosan films has been limited due to their high degradability in aqueous acidic media. In order to produce chitosan films with high antioxidant activity and insoluble in acid solutions caffeic acid was grafted to chitosan by a radical mechanism using ammonium cerium (IV) nitrate (60 mM). Genipin was used as cross-linker. This methodology originated films with 80% higher antioxidant activity than the pristine film. Also, these films only lost 11% of their mass upon seven days immersion into an aqueous solution at pH 3.5 under stirring. The films surface wettability (contact angle 105°), mechanical properties (68 MPa of tensile strength and 4% of elongation at break), and thermal stability for temperatures lower than 300 °C were not significantly influenced by the covalent linkage of caffeic acid and genipin to chitosan. Due to their characteristics, mainly higher antioxidant activity and lower solubility, these are promising materials to be used as active films. Copyright © 2012 Elsevier Ltd. All rights reserved.

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

    Science.gov (United States)

    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...

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

    Science.gov (United States)

    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.

  4. Biotechnological production of caffeic acid derivatives from cell and organ cultures of Echinacea species.

    Science.gov (United States)

    Murthy, Hosakatte Niranjana; Kim, Yun-Soo; Park, So-Young; Paek, Kee-Yoeup

    2014-09-01

    Caffeic acid derivatives (CADs) are a group of bioactive compounds which are produced in Echinacea species especially Echinacea purpurea, Echinacea angustifolia, and Echinacea pallida. Echinacea is a popular herbal medicine used in the treatment of common cold and it is also a prominent dietary supplement used throughout the world. Caffeic acid, chlorogenic acid (5-O-caffeoylquinic acid), caftaric acid (2-O-caffeoyltartaric acid), cichoric acid (2, 3-O-dicaffeoyltartaric acid), cynarin, and echinacoside are some of the important CADs which have varied pharmacological activities. The concentrations of these bioactive compounds are species specific and also they vary considerably with the cultivated Echinacea species due to geographical location, stage of development, time of harvest, and growth conditions. Due to these reasons, plant cell and organ cultures have become attractive alternative for the production of biomass and caffeic acid derivatives. Adventitious and hairy roots have been induced in E. pupurea and E. angustifolia, and suspension cultures have been established from flask to bioreactor scale for the production of biomass and CADs. Tremendous progress has been made in this area; various bioprocess methods and strategies have been developed for constant high-quality productivity of biomass and secondary products. This review is aimed to discuss biotechnological methods and approaches employed for the sustainable production of CADs.

  5. Design, synthesis, and evaluation of caffeic acid amides as synergists to sensitize fluconazole-resistant Candida albicans to fluconazole.

    Science.gov (United States)

    Dai, Li; Zang, Chengxu; Tian, Shujuan; Liu, Wei; Tan, Shanlun; Cai, Zhan; Ni, Tingjunhong; An, Maomao; Li, Ran; Gao, Yue; Zhang, Dazhi; Jiang, Yuanying

    2015-01-01

    A series of caffeic acid amides were designed, synthesized, and their synergistic activity with fluconazole against fluconazole-resistant Candida albicans was evaluated in vitro. The title caffeic acid amides 3-30 except 26 exhibited potent activity, and the subsequent SAR study was conducted. Compound 3, 5, 21, and 34c, at a concentration of 1.0 μg/ml, decreased the MIC₈₀ of fluconazole from 128.0 μg/ml to 1.0-0.5 μg/ml against the fluconazole-resistant C. albicans. This result suggests that the caffeic acid amides, as synergists, can sensitize drug-resistant fungi to fluconazole. The SAR study indicated that the dihydroxyl groups and the amido groups linking to phenyl or heterocyclic rings are the important pharmacophores of the caffeic acid amides.

  6. Antioxidative effect of lipophilized caffeic acid in fish oil enriched mayonnaise and milk.

    Science.gov (United States)

    Alemán, Mercedes; Bou, Ricard; Guardiola, Francesc; Durand, Erwann; Villeneuve, Pierre; Jacobsen, Charlotte; Sørensen, Ann-Dorit Moltke

    2015-01-15

    The antioxidative effect of lipophilized caffeic acid was assessed in two different fish oil enriched food products: mayonnaise and milk. In both emulsion systems, caffeic acid esterified with fatty alcohols of different chain lengths (C1-C20) were better antioxidants than the original phenolic compound. The optimal chain length with respect to protection against oxidation was, however, different for the two food systems. Fish oil enriched mayonnaise with caffeates of medium alkyl chain length (butyl, octyl and dodecyl) added resulted in a better oxidative stability than caffeates with shorter (methyl) or longer (octadecyl) alkyl chains. Whereas in fish oil enriched milk emulsions the most effective caffeates were those with shorter alkyl chains (methyl and butyl) rather than the ones with medium and long chains (octyl, dodecyl, hexadecyl and eicosyl). These results demonstrate that there might be an optimum alkyl chain length for each phenolipid in each type of emulsion systems. Copyright © 2014 Elsevier Ltd. All rights reserved.

  7. Bioavailability of Echinacea Constituents: Caco-2 Monolayers and Pharmacokinetics of the Alkylamides and Caffeic Acid Conjugates

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    R. Lehmann

    2005-10-01

    Full Text Available Many studies have been done over the years to assess the effectiveness of Echinacea as an immunomodulator. We have assessed the potential bioavailability of alkyl- amides and caffeic acid conjugates using Caco-2 monolayers and compared it to their actual bioavailability in a Phase I clinical trial. The caffeic acid conjugates permeated poorly through the Caco-2 monolayers. Alkylamides were found to diffuse rapidly through Caco-2 monolayers. Differences in diffusion rates for each alkylamide correlated to structural variations, with saturation and N-terminal methylation contributing to decreases in diffusion rates. Alkylamide diffusion is not affected by the presence of other constituents and the results for a synthetic alkylamide were in line with those for alkylamides found in an ethanolic Echinacea preparation. We examined plasma from healthy volunteers for 12 hours after ingestion of Echinacea tablets manufactured from an ethanolic liquid extract. Caffeic acid conjugates could not be identified in any plasma sample at any time after tablet ingestion. Alkylamides were detected in plasma 20 minutes after tablet ingestion and for each alkylamide, pharmacokinetic profiles were devised. The data are consistent with the dosing regimen of one tablet three times daily and supports their usage as the primary markers for quality Echinacea preparations.

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

    Science.gov (United States)

    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.

  9. Mechanism and kinetics in reactions of caffeic acid with radicals by pulse radiolysis and calculation

    Energy Technology Data Exchange (ETDEWEB)

    Li, Xifeng; Cai, Zhongli; Katsumura, Yosuke [Tokyo Univ., Tokai, Ibaraki (Japan). Nuclear Engineering Research Lab

    2000-03-01

    The interaction of caffeic acid with e{sub aq}{sup -}, (CH{sub 3}){sub 2}(OH) CCH{sub 2}{sup {center_dot}}, CO{sub 2}{sup {center_dot}}{sup -}, H{sup {center_dot}}, {center_dot}OH and N{sub 3}{sup {center_dot}} radicals were studied by {gamma}-, pulse radiolysis and molecular orbital calculation. UV-visible spectra of electron/{center_dot}OH adducts, semi-quinone radicals of caffeic ions, and the stable products from the reactions were derived. The rate constants were determined. The attacked sites and the most favorable structures of the transient radicals were predicted. Reaction mechanisms were proposed. (author)

  10. Antistaphylococcal and biofilm inhibitory activities of gallic, caffeic, and chlorogenic acids.

    Science.gov (United States)

    Luís, Ângelo; Silva, Filomena; Sousa, Sónia; Duarte, Ana Paula; Domingues, Fernanda

    2014-01-01

    Staphylococcus aureus is a Gram-positive pathogen which is able to form biofilms, exhibiting a more pronounced resistance to antibiotics and disinfectants. The hurdles posed in eradicating biofilms have driven the search for new compounds able to fight these structures. Phenolic compounds constitute one of the most numerous and ubiquitous group of plant secondary metabolites with many biological activities. The aim of the present work was to study the potential antimicrobial and antibiofilm properties of gallic, caffeic, and chlorogenic acids against S. aureus as well to elucidate its mechanism of action. It was concluded that the phenolic acids studied in this work have antistaphylococcal properties. For instance, gallic acid is able to influence the adhesion properties of S. aureus. The phenolic acids tested were also able to inhibit the production of α-hemolysin by this microorganism, with the exception of chlorogenic acid. Regarding its mechanism of action, caffeic acid interferes with the stability of the cell membrane and with the metabolic activity of the cells of S. aureus.

  11. Effects of roasting temperatures and gamma irradiation on the content of chlorogenic acid, caffeic acid and soluble carbohydrates of coffee

    International Nuclear Information System (INIS)

    Deshpande, S.N.; Aguilar, A.A.

    1975-01-01

    Two varieties of Puerto Rican coffee, Coffea canephora L. var. Robusta, and Coffea arabica L. var. Borbon, were subjected to four different doses of radiation and roasted at two different temperatures. Aqueous extracts of the ground coffee beans were analyzed for chlorogenic acid and caffeic acid at 324 nm and 360 nm wavelength settings, respectively. Samples subjected to the roasting treatments in conjuction with irradiation treatments were treated with basic lead acetate prior to the colorimetric analyses in order to eliminate interfering substances. The total carbohydrate content was also determined by colorimetric techniques with anthrone reagent. The total nitrogen content of the pulverized samples were determined by the micro-Kjeldahl method. While roasting treatments caused a reduction in the concentrations of the chlorogenic acid, caffeic acid, and the carbohydrates, the radiation treatments increased the concentrations of soluble carbohydrates without affecting the concentrations of chlorogenic acid or caffeic acid. It therefore appears that radiation treatments seem to cause degradation of the acid-polysaccharide complexes liberating soluble sugars. There were no noticable changes in the total content of nitrogen caused by roasting or the radiation treatments as indicated by the statistical analysis employing the split plot design. (author)

  12. The effects of gallic/ferulic/caffeic acids on colour intensification and anthocyanin stability.

    Science.gov (United States)

    Qian, Bing-Jun; Liu, Jian-Hua; Zhao, Shu-Juan; Cai, Jian-Xiong; Jing, Pu

    2017-08-01

    The mechanism by which copigments stabilize colour, by protecting anthocyanin chromophores from nucleophilic attack, seems well accepted. This study was to determine effects of gallic/ferulic/caffeic acids on colour intensification and anthocyanin stability. Molecular dynamics simulations were applied to explore molecular interactions. Phenolic acids intensified the colour by 19%∼27%. Colour fading during heating followed first-order reactions with half-lives of 3.66, 9.64, 3.50, and 3.39h, whereas anthocyanin degradation, determined by the pH differential method (or HPLC-PDA), followed second-order reactions with half-lives of 3.29 (3.40), 3.43 (3.39), 2.29 (0.39), and 2.72 (0.32)h alone or with gallic/ferulic/caffeic acids, respectively, suggesting that anthocyanin degradation was faster than the colour fading. The strongest protection of gallic acids might be attributed to the shortest distance (4.37Å) of its aromatic ring to the anthocyanin (AC) panel. Hyperchromic effects induced by phenolic acids were pronounced and they obscured the accelerated anthocyanin degradation due to self-association interruption. Copyright © 2017 Elsevier Ltd. All rights reserved.

  13. Chemical Properties of Caffeic and Ferulic Acids in Biological System: Implications in Cancer Therapy. A Review.

    Science.gov (United States)

    Damasceno, Sarah S; Dantas, Bruna B; Ribeiro-Filho, Jaime; Antônio M Araújo, Demetrius; Galberto M da Costa, José

    2017-01-01

    The antioxidant properties of caffeic and ferulic acids in biological systems have been extensively demonstrated. As antioxidants, these compounds prevent the production of reactive oxygen species (ROS), which cause cell lesions that are associated with the development of several diseases, including cancer. Recent findings suggest that the chemoprotective action of these phenolic acids occurs through the following mechanisms: regulation of gene expression, chelation and / or reduction of transition metals, formation of covalent adducts and direct toxicity. The biological efficacy of these promising chemoprotective agents is strongly related with their chemical structure. Therefore, in this study, we discuss the structural characteristics of ferulic and caffeic acids that are responsible for their biological activities, as well as the mechanisms of action involved with the anti-cancer activity. Several reports indicated that the antioxidant effect of these phenylpropanoids results from reactions with free radicals with formation of stable products in the cells. The chelating effect of these compounds was also reported as an important protective mechanism against oxidative. Finally, the lipophilicity of these agents facilitates their entry into the cells, and thus, contributes to the anticancer activity. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

  14. Synthesis and Antiradical/Antioxidant Activities of Caffeic Acid Phenethyl Ester and Its Related Propionic, Acetic, and Benzoic Acid Analoguesc

    Directory of Open Access Journals (Sweden)

    Mohamed Touaibia

    2012-12-01

    Full Text Available Caffeic acid phenethyl ester (CAPE is a bioactive component isolated from propolis. A series of CAPE analogues was synthesized and their antiradical/antioxidant effects analyzed. The effect of the presence of the double bond and of the conjugated system on the antioxidant effect is evaluated with the analogues obtained from 3-(3,4-dihydroxyphenyl propanoic acid. Those obtained from 2-(3,4-dihydroxyphenyl acetic acid and 3,4-dihydroxybenzoic acid allow the evaluation of the effect of the presence of two carbons between the carbonyl and aromatic system.

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

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    Cheng-Fang Tsai

    2015-03-01

    Full Text Available 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.

  16. Choline chloride-based deep eutectic solvents as additives for optimizing chromatographic behavior of caffeic acid

    International Nuclear Information System (INIS)

    Li, Guizhen; Zhu, Tao; Lei, Yingjie

    2015-01-01

    A series of deep eutectic solvents (DESs) were prepared using glycerol and choline chloride (ChCl), and Fourier transform infrared spectrometer (FT-IR) was used to analyze the spectra of glycerol, choline chloride and DESs based on glycerol and choline chloride. Then DESs were used as the additives of mobile phase to optimize chromatographic behavior of caffeic acid in high performance liquid chromatography (HPLC). A 17-run Box-Behnken design (BBD) was employed to evaluate effect of DESs as additives by analyzing the maximum theoretical plate number. Three factors, reaction temperature (60 .deg. C, 80 .deg. C, 100 .deg. C), molar ratio of glycerol and choline chloride (2 : 1, 3 : 1, 4 : 1, n/n), and volume percent of additives (0.05%, 0.10%, 0.15%, v/v), were investigated in BBD. The optimum experiment condition was that of reaction temperature (80 .deg. C), molar ratio of glycerol and ChCl (3 : 1, n/n), and volume percent of additive (0.10%, v/v). The mean chromatographic theoretical plate number of the caffeic acid this condition was 1567.5, and DESs as additives shorten the retention time and modify the chromatogram shape, proving DESs as additives for effective theoretical plate number and column efficiency in HPLC.

  17. Choline chloride-based deep eutectic solvents as additives for optimizing chromatographic behavior of caffeic acid

    Energy Technology Data Exchange (ETDEWEB)

    Li, Guizhen; Zhu, Tao; Lei, Yingjie [Tianjin University of Technology, Tianjin (China)

    2015-10-15

    A series of deep eutectic solvents (DESs) were prepared using glycerol and choline chloride (ChCl), and Fourier transform infrared spectrometer (FT-IR) was used to analyze the spectra of glycerol, choline chloride and DESs based on glycerol and choline chloride. Then DESs were used as the additives of mobile phase to optimize chromatographic behavior of caffeic acid in high performance liquid chromatography (HPLC). A 17-run Box-Behnken design (BBD) was employed to evaluate effect of DESs as additives by analyzing the maximum theoretical plate number. Three factors, reaction temperature (60 .deg. C, 80 .deg. C, 100 .deg. C), molar ratio of glycerol and choline chloride (2 : 1, 3 : 1, 4 : 1, n/n), and volume percent of additives (0.05%, 0.10%, 0.15%, v/v), were investigated in BBD. The optimum experiment condition was that of reaction temperature (80 .deg. C), molar ratio of glycerol and ChCl (3 : 1, n/n), and volume percent of additive (0.10%, v/v). The mean chromatographic theoretical plate number of the caffeic acid this condition was 1567.5, and DESs as additives shorten the retention time and modify the chromatogram shape, proving DESs as additives for effective theoretical plate number and column efficiency in HPLC.

  18. 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.

    Science.gov (United States)

    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. Copyright © 2016 Elsevier Inc. All rights reserved.

  19. Analysis of Caffeic Acid Extraction From Ocimum gratissimum Linn. by High Performance Liquid Chromatography and its Effects on a Cervical Cancer Cell Line

    Directory of Open Access Journals (Sweden)

    Je-Chiuan Ye

    2010-09-01

    Conclusion: This paper shows that high performance liquid chromatography is a suitable analytical method for determining caffeic acid levels in O. gratissimum, Ju ZenTa, and several vegetable oils. Caffeic acid can suppress the proliferation of HeLa cells.

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

    Science.gov (United States)

    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 ...

  1. Square-wave stripping voltammetric determination of caffeic acid on electrochemically reduced graphene oxide-Nafion composite film.

    Science.gov (United States)

    Filik, Hayati; Çetintaş, Gamze; Avan, Asiye Aslıhan; Aydar, Sevda; Koç, Serkan Naci; Boz, İsmail

    2013-11-15

    An electrochemical sensor composed of Nafion-graphene nanocomposite film for the voltammetric determination of caffeic acid (CA) was studied. A Nafion graphene oxide-modified glassy carbon electrode was fabricated by a simple drop-casting method and then graphene oxide was electrochemically reduced over the glassy carbon electrode. The electrochemical analysis method was based on the adsorption of caffeic acid on Nafion/ER-GO/GCE and then the oxidation of CA during the stripping step. The resulting electrode showed an excellent electrocatalytical response to the oxidation of caffeic acid (CA). The electrochemistry of caffeic acid on Nafion/ER-GO modified glassy carbon electrodes (GCEs) were studied by cyclic voltammetry and square-wave adsorption stripping voltammetry (SW-AdSV). At optimized test conditions, the calibration curve for CA showed two linear segments: the first linear segment increased from 0.1 to 1.5 and second linear segment increased up to 10 µM. The detection limit was determined as 9.1×10(-8) mol L(-1) using SW-AdSV. Finally, the proposed method was successfully used to determine CA in white wine samples. Copyright © 2013 Elsevier B.V. All rights reserved.

  2. Antiviral Properties of Caffeic Acid Phenethyl Ester and Its Potential Application

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    Haci Kemal Erdemli

    2015-12-01

    Full Text Available Caffeic acid phenethyl ester (CAPE is found in variety of plants and well known 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. [J Intercult Ethnopharmacol 2015; 4(4.000: 344-347

  3. Can propolis and caffeic acid phenethyl ester (CAPE be promising agents against cyclophosphamide toxicity?

    Directory of Open Access Journals (Sweden)

    Sumeyya Akyol

    2016-03-01

    Full Text Available 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 has been used to treat a broad of malignancies including Hodgkin’s and non-Hodgking’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 cyclophosphamide-induced injuries. [J Complement Med Res 2016; 5(1.000: 105-107

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

    Directory of Open Access Journals (Sweden)

    Kazancioglu HO

    2015-12-01

    Full Text Available Hakki Oguz Kazancioglu,1 Sertac Aksakalli,2 Seref Ezirganli,1 Muhammet Birlik,2 Mukaddes Esrefoglu,3 Ahmet Hüseyin Acar1 1Department of Oral and Maxillofacial Surgery, 2Department of Orthodontics, Faculty of Dentistry, 3Department of Histology, Faculty of Medicine, Bezmialem Vakif University, Istanbul, Turkey 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 application has 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 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 of new bone formation.Results: New bone formation was significantly greater in 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. Keywords: rapid maxillary expansion, bone formation, caffeic acid phenethyl ester, midpalatal suture, histopathology

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

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    Francesca Selmin

    2015-01-01

    Full Text Available 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.

  6. Sensitive Determination of 6-Thioguanine Using Caffeic Acid-functionalized Fe3O4 Nanoparticles as an Electrochemical Sensor

    Science.gov (United States)

    Amir, Md.; Tunesi, Mawada M.; Soomro, Razium A.; Baykal, Abdülhadi; Kalwar, Nazar H.

    2018-04-01

    The study demonstrates the potential application of caffeic acid-functionalized magnetite nanoparticles (CA-Fe3O4 NPs) as an effective electrode modifying material for the electrochemical oxidation of the 6-thioguanine (6-TG) drug. The functionalized Fe3O4 NPs were prepared using simple wet-chemical methodology where the used caffeic acid acted simultaneously as growth controlling and functionalizing agent. The study discusses the influence of an effective functionalization on the signal sensitivity observed for the electro-oxidation of 6-TG over CA-Fe3O4 NPs in comparison to a glassy carbon electrode modified with bare and nicotinic acid (NA)-functionalized Fe3O4 NPs. The experiment results provided sufficient evidence to support the importance of favorable functionality to achieve higher signal sensitivity for the electro-oxidation of 6-TG. The presence of favorable interactions between the active functional moieties of caffeic acid and 6-TG synergized with the greater surface area of magnetic NPs produces a stable electro-oxidation signal within the working range of 0.01-0.23 μM with sensitive up to 0.001 μM. Additionally, the sensor showed the strong anti-interference potential against the common co-existing drug molecules such as benzoic acid, acetaminophen, epinephrine, norepinephrine, glucose, ascorbic acid and l-cysteine. In addition, the successful quantification of 6-TG from the commercial tablets obtained from local pharmacy further signified the practical capability of the discussed sensor.

  7. Antineurodegenerative effect of phenolic extracts and caffeic acid derivatives in romaine lettuce on neuron-like PC-12 cells.

    Science.gov (United States)

    Im, Sung-Eun; Yoon, Hyungeun; Nam, Tae-Gyu; Heo, Ho Jin; Lee, Chang Yong; Kim, Dae-Ok

    2010-08-01

    In recent decades, romaine lettuce has been one of the fastest growing vegetables with respect to its consumption and production. An understanding is needed of the effect of major phenolic phytochemicals from romaine lettuce on biological protection for neuron-like PC-12 cells. Phenolics in fresh romaine lettuce were extracted, and then its total phenolics and total antioxidant capacity were measured spectrophotometrically. Neuroprotective effects of phenolic extract of romaine lettuce and its pure caffeic acid derivatives (caffeic, chicoric, chlorogenic, and isochlorogenic acids) in PC-12 cells were evaluated using two different in vitro methods: lactate dehydrogenase release and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide reduction assays. Total phenolics and total antioxidant capacity of 100 g of fresh romaine lettuce averaged 22.7 mg of gallic acid equivalents and 31.0 mg of vitamin C equivalents, respectively. The phenolic extract of romaine lettuce protected PC-12 cells against oxidative stress caused by H(2)O(2) in a dose-dependent manner. Isochlorogenic acid, one of the phenolics in romaine lettuce, showed stronger neuroprotection than the other three caffeic acid derivatives also found in the lettuce. Although romaine lettuce had lower levels of phenolics and antioxidant capacity compared to other common vegetables, its contribution to total antioxidant capacity and antineurodegenerative effect in human diets would be higher because of higher amounts of its daily per capita consumption compared to other common vegetables.

  8. Effects of caffeic acid phenethyl ester on palatal mucosal defects and tooth extraction sockets

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    Günay A

    2014-10-01

    Full Text Available Ahmet Günay,1 Osman Fatih Arpağ,2 Serhat Atilgan,3 Ferhan Yaman,3 Yusuf Atalay,4 İzzet Acikan3 1Department of Periodontology, Faculty of Dentistry, Dicle University, Diyarbakir, Turkey; 2Department of Periodontology, Faculty of Dentistry, Mustafa Kemal University, Hatay, Turkey; 3Department of Maxillofacial Surgery, Faculty of Dentistry, Dicle University, Diyarbakir, Turkey; 4Department of Maxillofacial Surgery, Faculty of Dentistry, Kocatepe University, Afyon, Turkey Aim: The purpose of this study was to evaluate the effects of caffeic acid phenethyl ester (CAPE on palatal mucosal defects and tooth extraction sockets in an experimental model.Materials and methods: Forty-two male Sprague-Dawley rats with a mean age of 7 weeks and weighing 280–490 g were used in this study. The rats were randomly divided into two groups: group A (the control group, n=21 and group B (the experimental group, n=21. Under anesthesia with ketamine (8 mg/100 g, intraperitoneally, palatal mucosal defects were created and tooth extraction was performed in the rats in groups A and B. Group A received no treatment, whereas group B received CAPE. CAPE was injected daily (10 µmol/kg, intraperitoneally. The rats were killed on days 7, 14, and 30 after the procedures. Palatal mucosa healing and changes in bone tissue and fibrous tissue were evaluated histopathologically.Result: Pairwise comparisons showed no statistically significant difference between days 7 and 14 in either group (P>0.05. At day 30, bone healing was significantly better in group B (CAPE than in group A (control (P<0.05. Fibrinogen levels at day 30 were significantly higher in group A (control than in group B (CAPE (P<0.05. Pairwise comparisons showed no statistically significant difference in palatal mucosa healing levels between days 7 and 14 in both groups (P>0.05.Conclusion: In conclusion, the findings of this study suggest that CAPE can significantly improve tooth socket healing. Keywords: caffeic

  9. Caffeic acid and quercetin exert caspases-independent apoptotic effects on Leishmania major promastigotes, and reactivate the death of infected phagocytes derived from BALB/c mice

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    Radia Belkhelfa-Slimani

    2017-04-01

    Conclusions: The leishmanicidal effect of caffeic acid and quercetin on promastigotes and amastigotes, as well as reactivation of infected phagocytes apoptosis, suggested a potential therapeutic role against cutaneous leishmaniasis.

  10. Butylated caffeic acid: An efficient novel antioxidant; Ácido cafeico butilado: un nuevo y eficaz antioxidante.

    Energy Technology Data Exchange (ETDEWEB)

    Shi, G.; Liao, X.; Olajide, T.M.; Liu, J.; Jiang, X.; Weng, X.

    2017-07-01

    A novel antioxidant, butylated caffeic acid (BCA) was rationally designed by adding a tert-butyl group to caffeic acid, which was synthesized at a high yield (36.2%) from 2-methoxy-4-methylphenol (1) by a four-step reaction including Friedel-Crafts alkylation, bromine oxidation, ether bond hydrolysis and Knoevenagel condensation. Its antioxidant capacity was much stronger than common commercial antioxidant tert-butyl hydroquinone (TBHQ) and its mother compound, caffeic acid, in both rancimat and deep frying tests. When investigated via the DPPH method, the antioxidant capacity of BCA was almost equal to TBHQ, but lower than caffeic acid. BCA could be a potentially strong antioxidant, especially for food processing at high temperatures such as deep frying and baking. [Spanish] Se diseñó razonadamente un nuevo antioxidante, el ácido cafeico butilado (BCA) mediante la adición de un grupo terc-butilo al ácido cafeico, que se sintetizó con un alto rendimiento (36,2%) a partir de 2-metoxi-4-metilfenol, reacción de Friedel-Crafts, oxidación de bromo, hidrólisis del enlace éter y condensación de Knoevenagel. Su capacidad antioxidante fué mucho más fuerte que la del antioxidante comercial mas común el terc-butil hidroquinona (TBHQ) y la de su compuesto madre el ácido cafeico, tanto en rancimat como en pruebas de fritura. Cuando se investigó mediante el método DPPH, la capacidad antioxidante de BCA fue casi igual a TBHQ, pero menor que la del ácido cafeico. BCA podría ser un fuerte antioxidante potencial, especialmente para el procesamiento de alimentos a alta temperatura, tales como freír y hornear.

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

    OpenAIRE

    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 wh...

  12. Cell killing and radiosensitization by caffeic acid phenethyl ester (CAPE) in lung cancer cells

    International Nuclear Information System (INIS)

    Chen, Miao-Fen; Chen, Wen-Cheng; Wu, Chun-Te; King, P.C.

    2004-01-01

    Caffeic acid phenethyl ester (CAPE) is a biologically active ingredient of honeybee propoplis. The cytotoxicity and radiation sensitization effects of CAPE were evaluated in human lung cancer A549 cells and normal lung fibroblast WI-38 cells. A549 cells treated with 6 μg/ml CAPE showed marked growth inhibition (60%) at 48 hr after treatments. During the same time, the number of viable cells decreased to 46% of the control value. In contrast, WI-38 cells showed 20% growth inhibition with no change in the number of viable cells under the same treatment conditions. At 72 hr after CAPE treatment (6 μg/ml), the percentage of apoptotic cells in A549 cultures increased significantly to 67% and an S/G2 arrest was also detected in the culture. Furthermore, there was a significant decrease in the level of intracellular glutathione and hydrogen peroxide contents within one hr after CAPE treatment, and the expression of cyclin B 1 was reduced 6 hr after treatment. The radiation sensitization effect of CAPE on A549 cells was determined from the clonogenic survival curves, and the results showed a small but significant difference in radiation survival between cells treated with or without CAPE. Taken together, our results suggest that the effects of CAPE on differential cytotoxicity, apoptosis, and radiosensitization are associated with glutathione depletion that occurred shortly after treatments. (author)

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

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    Muhammet Murat Celik

    2015-01-01

    Full Text Available 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.

  14. Effects of caffeic acid phenethyl ester on palatal mucosal defects and tooth extraction sockets

    Science.gov (United States)

    Günay, Ahmet; Arpağ, Osman Fatih; Atilgan, Serhat; Yaman, Ferhan; Atalay, Yusuf; Acikan, İzzet

    2014-01-01

    Aim The purpose of this study was to evaluate the effects of caffeic acid phenethyl ester (CAPE) on palatal mucosal defects and tooth extraction sockets in an experimental model. Materials and methods Forty-two male Sprague-Dawley rats with a mean age of 7 weeks and weighing 280–490 g were used in this study. The rats were randomly divided into two groups: group A (the control group, n=21) and group B (the experimental group, n=21). Under anesthesia with ketamine (8 mg/100 g, intraperitoneally), palatal mucosal defects were created and tooth extraction was performed in the rats in groups A and B. Group A received no treatment, whereas group B received CAPE. CAPE was injected daily (10 μmol/kg, intraperitoneally). The rats were killed on days 7, 14, and 30 after the procedures. Palatal mucosa healing and changes in bone tissue and fibrous tissue were evaluated histopathologically. Result Pairwise comparisons showed no statistically significant difference between days 7 and 14 in either group (P>0.05). At day 30, bone healing was significantly better in group B (CAPE) than in group A (control) (P0.05). Conclusion In conclusion, the findings of this study suggest that CAPE can significantly improve tooth socket healing. PMID:25364232

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

    Directory of Open Access Journals (Sweden)

    Tarek K. Motawi

    2016-01-01

    Full Text Available 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.

  16. Early Treatment of radiation-Induced Heart Damage in Rats by Caffeic acid phenethyl Ester

    International Nuclear Information System (INIS)

    Tawfik, S.S.; Mansour, H. H.

    2012-12-01

    The study designed to determine the therapeutic effect of caffeic acid phenethyl ester (CAPE) in minimising radiation-induced injuries in rats. Rats were exposed to 7 Gy γ-rays, 30 minutes later; rats were injected with CAPE (10μmol/ kg body, i.p.) for 7 consecutive days. Rats were sacrificed at 8 and 15 days after starting the experiment. Gamma-irradiation induced significant increase in malonaldehyde (MDA) level and xanthine oxidase (XO) and adenosine deaminase (ADA) activities, and significant decrease in total nitrate/nitrate (NO (x)) level and glutathione peroxidise (Gpx), superoxide dismutase (SOD)and catalase (CAT) activities in heart tissue and augmented activities of lactate dehydrogenase (LDH), creatine phosphokinase (CPK) and aspartate transaminase (AST) in serum. Irradiated rats early treated with CAPE showed significant decrease in MDA, XO and ADA and significant increase in group. Cardiac enzymes were restored. Conclusion, CAPE could exhibits curable effect on gamma irradiation-induced cardiac-oxidative impairment in rats. (Author)

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

    Science.gov (United States)

    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

  18. Phenolic profiling of caffeic acid O-methyltransferase-deficient poplar reveals novel benzodioxane oligolignols.

    Science.gov (United States)

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

    2004-12-01

    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.

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

    Directory of Open Access Journals (Sweden)

    Ying-Yu Kuo

    2015-05-01

    Full Text Available 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.

  20. EFFECTS OF EXERCISE AND CAFFEIC ACID PHENETHYL ESTER AFTER CHRONIC EXERCISE RAT MODEL

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    Ayse Alp

    2011-01-01

    Full Text Available In order to understand whether exercise and caffeic acid phenethyl ester (CAPE has an effect on obesity and weight control, we investigated the effects of CAPE, and exercise on lipid parameters (triglyceride, total cholesterol, HDL-C, LDL-C, and adipokine substances such as leptin and resistin in rats. 40 male rat were randomly assigned into 4 groups. It was determined that CAPE does not have any significant effect on these parameters but that lipid parameters and leptin values in exercise groups decreased considerably, while no significant change occurred in resistin levels. In order to understand whether diet has an effect on exercise, body weights of all animal groups in pre and post-exercise were compared. A significant weight gain was observed (p = 0.005 in all groups. This study concluded that exercise has a considerable effect on leptin and lipid parameters; however, exercise alone was not sufficient for weight control and could be effective in weight control only when accompanied by a restricted diet.

  1. Ascorbyl radical disproportionation in reverse micellar systems

    Science.gov (United States)

    Gębicki, J. L.; Szymańska-Owczarek, M.; Pacholczyk-Sienicka, B.; Jankowski, S.

    2018-04-01

    Ascorbyl radical was generated by the pulse radiolysis method and observed with the fast kinetic spectrophotometry within reverse micelles stabilized by AOT in n-heptane or by Igepal CO-520 in cyclohexane at different water to surfactant molar ratio, w0. Rate constants for the disproportionation of the ascorbyl radicals were smaller than those for intermicellar exchange for both type of reverse micelles and slower than those in homogeneous aqueous solutions. However, they increased with increasing w0 for AOT/n-heptane system, while they decreased for Igepal CO-520 system. The absorption spectra of ascorbic acid AOT/n-heptane reverse micellar system showed that the "pH" sensed by this molecule is lower than that in respective homogeneous aqueous solutions. The obtained results were rationalized taking into account three main factors (i) preferential location of ascorbic acid molecules in the interfacial region of the both types of reverse micelles; (ii) postulate that the pH of the interface is lower than that of the water pool of reverse micelles and (iii) different structure of the interface of the reverse micelles made by AOT in n-heptane and those formed by Igepal CO-520 I cyclohexane. Some possible consequences of these findings are discussed.

  2. Caffeic acid, tyrosol and p-coumaric acid are potent inhibitors of 5-S-cysteinyl-dopamine induced neurotoxicity.

    Science.gov (United States)

    Vauzour, David; Corona, Giulia; Spencer, Jeremy P E

    2010-09-01

    Parkinson's disease is characterized by a progressive and selective loss of dopaminergic neurons in the substantia nigra. Recent investigations have shown that conjugates such as the 5-S-cysteinyl-dopamine, possess strong neurotoxicity and may contribute to the underlying progression of the disease pathology. Although the neuroprotective actions of flavonoids are well reported, that of hydroxycinnamates and other phenolic acids is less established. We show that the hydroxycinnamates caffeic acid and p-coumaric acid, the hydroxyphenethyl alcohol, tyrosol, and a Champagne wine extract rich in these components protect neurons against injury induced by 5-S-cysteinyl-dopamine in vitro. The protection induced by these polyphenols was equal to or greater than that observed for the flavonoids, (+)-catechin, (-)-epicatechin and quercetin. For example, p-coumaric acid evoked significantly more protection at 1muM (64.0+/-3.1%) than both (-)-epicatechin (46.0+/-4.1%, p<0.05) and (+)-catechin (13.1+/-3.0%, p<0.001) at the same concentration. These data indicate that hydroxycinnamates, phenolic acids and phenolic alcohol are also capable of inducing neuroprotective effects to a similar extent to that seen with flavonoids. Copyright © 2010. Published by Elsevier Inc.

  3. Restorative Effects of Caffeic Acid Phenethyl Ester in Radiation-Induced Oxidative Hepatic Disorders

    International Nuclear Information System (INIS)

    El-Fatih, N.M.; EI-Tawil, G.A.

    2009-01-01

    The potential role of antioxidant natural phenolic compounds in the prevention of oxidative tissue-damage associated with ionizing-radiation has accumulated over the past decades. The possible restorative effect of caffeic acid phenethyl ester (CAPE) in minimizing radiation-induced hepatic injury in male albino rats was investigated. CAPE was given to rats via intraperitoneal (ip.) injection at a dose of (10μmol/ kg b.wt.) for 21 successive days throughout exposure to gamma radiation and continued for 15 successive days post gamma-radiation exposure. Whole body gamma-irradiation was delivered as fractionated doses (3 weeks) 2 Gy increment every week up to total cumulative dose of G Gy. Rats were sacrificed at either I, or 15 days after last dose of radiation. Malondialdehyde (MDA) content was determined in plasma and hepatic tissues. In addition, the activities of xanthine oxidase (XO), superoxide dismutase (SOD), catalase (CAT), glutathione peroxidase (GSH-Px) as well as the level of reduced glutathione (GSH) were determined to evaluate the changes of antioxidant-status in blood systems and hepatic tissues. Meantime, alanine aminotransferase (ALT), aspartate aminotransferase (AST), alkaline phosphatase (ALP) activities were estimated in rat serum. Results showed that exposure to gamma-radiation significantly increased the MDA levels and the activities of XO, ALT, AST and ALP. Moreover, SOD, CAT and GSH-Px activities as well GSH contents showed significant consumption in irradiated rats. Treatment with CAPE showed a significant decrease in MDA level and caused significant increases in all enzymes measured in hepatic tissues and blood systems when compared with irradiated group. Conclusion: radiation-exposure leads to a reduction in antioxidant enzymatic activities and causes lipid peroxidation in hepatic tissues and blood. Under experimental condition, CAPE exhibits restorative effects on gamma-rays-induced hepatic-oxidative impairment in rats

  4. Restorative Effects of Caffeic Acid Phenethyl Ester in Radiation-Induced Oxidative Hepatic Disorders

    International Nuclear Information System (INIS)

    El-Fatih, N.M.; EI-Tawil, G.A.

    2008-01-01

    The potential role of antioxidant natural phenolic compounds in the prevention of oxidative tissue-damage associated with ionizing-radiation has accumulated over the past decades. The possible restorative effect of caffeic acid phenethyl ester (CAPE) in minimizing radiation-induced hepatic injury in male albino rats was investigated. CAPE was given to rats via intraperitoneal (ip.) injection at a dose of (10μmol/ kg b.wt.) for 21 successive days throughout exposure to gamma radiation and continued for 15 successive days post gamma-radiation exposure. Whole body gamma-irradiation was delivered as fractionated doses (3 weeks) 2 Gy increment every week up to total cumulative dose of G Gy. Rats were sacrificed at either I, or 15 days after last dose of radiation. Malondialdehyde (MDA) content was determined in plasma and hepatic tissues. In addition, the activities of xanthine oxidase (XO), superoxide dismutase (SOD), catalase (CAT), glutathione peroxidase (GSH-Px) as well as the level of reduced glutathione (GSH) were determined to evaluate the changes of antioxidant-status in blood systems and hepatic tissues. Meantime, alanine aminotransferase (ALT), aspartate aminotransferase (AST), alkaline phosphatase (ALP) activities were estimated in rat serum. Results showed that exposure to gamma-radiation significantly increased the MDA levels and the activities of XO, ALT, AST and ALP. Moreover, SOD, CAT and GSH-Px activities as well GSH contents showed significant consumption in irradiated rats. Treatment with CAPE showed a significant decrease in MDA level and caused significant increases in all enzymes measured in hepatic tissues and blood systems when compared with irradiated group. Conclusion: radiation-exposure leads to a reduction in antioxidant enzymatic activities and causes lipid peroxidation in hepatic tissues and blood. Under experimental condition, CAPE exhibits restorative effects on gamma-rays-induced hepatic-oxidative impairment in rats

  5. Potential Effects of Caffeic Acid in Suppression of Matrix Metalloproteinases Activities in Irradiated Rats

    International Nuclear Information System (INIS)

    Zahran, A.M.

    2008-01-01

    Great Number of researches on the potential role of antioxidant nutrients and phenolic compounds in the prevention of chronic diseases has been accumulated over the past several decades. Despite this effort, there is much that remains uncertain. Bio markers research in this field has the potential to help fill the gaps in current knowledge. The present study was designed to evaluate, in one aspect, the probable direction expression of proteolytic enzymes as indices for gamma-irradiation-induced oxidative stress and their relationship, in other aspect with one antioxidant micro nutrient phenolic compound: caffeic acid (CA). Sprague Dawley male albino rats were administrated CA intraperitoneally (i.p.) 10 μmol/ kg body wt/ day for 8 consecutive days pre irradiation exposure (fractionated doses, instalment as 1 Gy every day up to total dose of 8 Gy). The treatment was continued for 15 successive days following irradiation processing. Quantitative assay of gelatinolytic zymo graphic analysis of serum and hepatic tissues showed that exposure to gamma-rays yields a marked significant increase in the activities of both latent and active MMP-9 (92 and 86 kDa), respectively, and both latent and active MMP-2 (72 and 66 kDa), respectively. Administration of CA significantly decreased the activities of MMP-2 and MMP-9 in gamma-irradiated rats. Conclusion: the present findings demonstrated that irradiation-exposure leads to enhancement of enzymatic activities of MMP-2 and MMP-9 in their inactive and active forms in the serum and liver. Meanwhile, administration of CA exhibits protective effects in gamma-irradiated rats through down-regulation of MMP-2 and MMP-9 activities

  6. Effect of antioxidant activity of caffeic acid with cyclodextrins using ground mixture method

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    Ryota Shiozawa

    2018-01-01

    Full Text Available In the current study, we prepared a ground mixture (GM of caffeic acid (CA with α-cyclodextrin (αCD and with β-cyclodextrin (βCD, and then comparatively assessed the physicochemical properties and antioxidant capacities of these GMs. Phase solubility diagrams indicated that both CA/αCD and CA/βCD formed a complex at a molar ratio of 1/1. In addition, stability constants suggested that CA was more stable inside the cavity of αCD than inside the cavity of βCD. Results of powder X-ray diffraction (PXRD indicated that the characteristic diffraction peaks of CA and CD disappeared and a halo pattern was produced by the GMs of CA/αCD and CA/βCD (molar ratios = 1/1. Dissolution testing revealed that both GMs had a higher rate of dissolution than CA alone did. Based on the 1H-1H NOESY NMR spectra for the GM of CA/αCD, the vinylene group of the CA molecule appeared to be included from the wider to the narrower rim of the αCD ring. Based on spectra for the GM of CA/βCD, the aromatic ring of the CA molecule appeared to be included from the wider to the narrower rim of the βCD ring. This suggests that the structures of the CA inclusion complexes differed between those involving αCD rings and those involving βCD rings. Results of a DPPH radical-scavenging activity test indicated that the GM of CA/αCD had a higher antioxidant capacity than that of the GM of CA/βCD. The differences in the antioxidant capacities of the GMs of CA/αCD and CA/βCD are presumably due to differences in stability constants and structures of the inclusion complexes.

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

    Science.gov (United States)

    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. © 2015 Institute of Food Technologists®

  8. Anti-inflammatory and anti-coagulatory activities of caffeic acid and ellagic acid in cardiac tissue of diabetic mice

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    Hsu Cheng-chin

    2009-08-01

    Full Text Available Abstract Background Caffeic acid (CA and ellagic acid (EA are phenolic acids naturally occurring in many plant foods. Cardiac protective effects of these compounds against dyslipidemia, hypercoagulability, oxidative stress and inflammation in diabetic mice were examined. Methods Diabetic mice were divided into three groups (15 mice per group: diabetic mice with normal diet, 2% CA treatment, or 2% EA treatment. One group of non-diabetic mice with normal diet was used for comparison. After 12 weeks supplement, mice were sacrificed, and the variation of biomarkers for hypercoagulability, oxidative stress and inflammation in cardiac tissue of diabetic mice were measured. Results The intake of CA or EA significantly increased cardiac content of these compounds, alleviated body weight loss, elevated plasma insulin and decreased plasma glucose levels in diabetic mice (p p p p p p p Conclusion These results support that CA and EA could provide triglyceride-lowering, anti-coagulatory, anti-oxidative, and anti-inflammatory protection in cardiac tissue of diabetic mice. Thus, the supplement of these agents might be helpful for the prevention or attenuation of diabetic cardiomyopathy.

  9. Development of an Electrochemical Sensor for NADH Determination Based on a Caffeic Acid Redox Mediator Supported on Carbon Black

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    Chiara Zanardi

    2015-04-01

    Full Text Available Screen-printed electrode (SPE modified with carbon black nanoparticles (CB has been tested as a new platform for the stable deposition of caffeic acid (CFA on the electrode surface. The electrochemical performance from varying the amount of CFA/CB composite has been tested with respect to NADH determination. The electrocatalytic activity of CFA/CB has also been compared with that of SPEs modified by a single component of the coating, i.e., either CFA or CB. Finally, glycerol dehydrogenase, a typical NADH-dependent enzyme, was deposited on the CFA/CB coating in order to test the applicability of the sensor in glycerol determination.

  10. Improved Stability of Tuberculosis Drug Fixed-Dose Combination Using Isoniazid-Caffeic Acid and Vanillic Acid Cocrystal.

    Science.gov (United States)

    Battini, Swapna; Mannava, M K Chaitanya; Nangia, Ashwini

    2018-06-01

    The classic fixed-dose combination (FDC) of 4 tuberculosis drugs, namely rifampicin (RIF), isoniazid (INH), pyrazinamide (PZA), and ethambutol dihydrochloride (EDH) has the twin issues of physical stability and RIF cross-reaction in the 4-FDC. The major reason for these quality issues is the interaction between RIF and INH to yield isonicotinyl hydrazone in drug tablets. Pharmaceutical cocrystals of INH with caffeic acid (CFA) (PZA + EDH + RIF + INH-CFA cocrystal) and vanillic acid (VLA) (PZA + EDH + RIF + INH-VLA cocrystal) are able to stabilize the FDC formulation compared with the reference batch (PZA + EDH + RIF + INH). Stability studies under accelerated humidity and temperature stress conditions of 40°C and 75% relative humidity showed that the physical stability of the cocrystal formulation was superior by powder X-ray diffraction and scanning electron microscopy analysis, and chemical purity was analyzed by high-performance liquid chromatography. Changes in the composition and structure were monitored on samples drawn at 7, 15, 22, and 30 days of storage. FDC-INH-CFA cocrystal batch exhibited greater stability compared with FDC-INH-VLA cocrystal and FDC reference drug batches. The superior stability of INH-CFA cocrystal is attributed to the presence of stronger hydrogen bonds and cyclic O-H⋯O synthon in the crystal structure. Copyright © 2018 American Pharmacists Association®. Published by Elsevier Inc. All rights reserved.

  11. Caffeic acid phenethyl ester prevents cadmium-induced cardiac impairment in rat

    International Nuclear Information System (INIS)

    Mollaoglu, Hakan; Gokcimen, Alpaslan; Ozguner, Fehmi; Oktem, Faruk; Koyu, Ahmet; Kocak, Ahmet; Demirin, Hilmi; Gokalp, Osman; Cicek, Ekrem

    2006-01-01

    Caffeic acid phenethyl ester (CAPE), a flavonoid like compound, is one of the major components of honeybee propolis. It was found to be a potent free radical scavenger and antioxidant recently. The aim of this study was to examine the effect of CAPE on cadmium (Cd)-induced hypertension and cardiomyopathy in rats. In particular, nitric oxide (NO) may contribute to the pathophysiology of Cd induced cardiac impairment. Malondialdehyde (MDA, an index of lipid peroxidation) levels and nitric oxide (NO, a vasodilator) levels were used as markers Cd-induced cardiac impairment and the success of CAPE treatment. Also, the findings have been supported by the histopathologic evidences. The rats were randomly divided into three experimental groups each (12), as follows: the control group, Cd-treated group (Cd) and Cd plus CAPE-treated group (Cd + CAPE). CdCl 2 in 0.9% NaCl was administrated intraperitoneally (i.p.) with a dose of 1 mg/kg/day. CAPE was co-administered i.p. a dose of 10 μM/kg for 15 days. Hypertension was found to be induced by intraperitoneal administration of Cd in a dose of 1 mg/kg/day on the measurements taken 15 days later. MDA levels were increased (p < 0.001) in cardiac tissue and NO levels were decreased (p < 0.05) in serum in the Cd group than those of the control group had. On the other hand, there was a slight difference (increase) in MDA levels in the Cd + CAPE group than the ones in the control group (p < 0.003). In addition, MDA levels were decreased and NO levels were increased in the Cd + CAPE group compared with the Cd group (p < 0.001, p < 0.0001, respectively). As a result, treatment with CAPE significantly reversed the increased lipid peroxidation (LPO) product, MDA, and decreased NO levels in Cd treated animals. In the histopathologic examination, a significant hypertrophy in atrial and ventricular myofibrils was observed in only Cd administered group, in comparison with the control group. There was no statistically significant difference

  12. Is caffeic acid phenethyl ester more protective than doxycycline in experimental periodontitis?

    Science.gov (United States)

    Yiğit, Umut; Kırzıoğlu, Fatma Yeşim; Uğuz, Abdülhadi Cihangir; Nazıroğlu, Mustafa; Özmen, Özlem

    2017-09-01

    Host modulation therapies (anti-inflammatory drugs, bone-stimulating agents, anti-proteinase etc.) target the inhibition or stabilization of tissue breakdown. The aim of the present study was to evaluate the effects of caffeic acid phenethyl ester (CAPE) and/or low dose doxycycline (LDD) administrations on alveolar bone loss (ABL), serum cytokines and gingival apoptosis, as well as the levels of oxidants and anti-oxidants in rats with ligature-induced periodontitis. The animals were randomly divided into five groups: Group C (periodontally healthy), Group PC (Periodontitis+CAPE), Group PD (Periodontitis+LDD), Group PCD (Periodontitis+CAPE+LDD), Group P (Periodontitis). Experimental periodontitis was induced for 14days. Levels of ABL, and the serum cytokines, interleukin (IL)-1 β, IL-6, tumor necrosis factor-α (TNF-α) and IL-10 were assessed as were the levels of the oxidants and anti-oxidants, malondialdehyde (MDA), glutathione (GSH) and glutathione peroxidase (GSH-Px), and levels of gingival apoptosis. The lowest ABL levels was evident in the PC group, among the experimental groups. There was also less inflammatory infiltration in the PC group than the PD group. IL-1β, IL-6, and IL-10 were lower in the PC group and higher in the P group in comparison to the levels in the other experiment groups. TNF-α levels in the PD group were higher than levels in the PC and PCD groups. The PC and PCD groups did not differ from the C group in regard to MDA levels. The highest GSH-Px level was found in the PC group. Gingival apoptosis in the PC group was not only lower than the PD and PCD groups, but also lower than in the C group. The present study suggests that CAPE has more anti-inflammatory, anti-oxidant and anti-apoptotic effects than LDD, with no additive benefits of a CAPE+LDD combination being evident in rats with periodontitis. Copyright © 2017 Elsevier Ltd. All rights reserved.

  13. A Comparative Study of the Radical-scavenging Activity of the Phenolcarboxylic Acids Caffeic Acid, p-Coumaric Acid, Chlorogenic Acid and Ferulic Acid, With or Without 2-Mercaptoethanol, a Thiol, Using the Induction Period Method

    Directory of Open Access Journals (Sweden)

    Seiichiro Fujisawa

    2008-10-01

    Full Text Available Phenolcarboxylic acid antioxidants do not act in vivo as radical-scavengers in isolation, but rather together with GSH (glutathione, a coantioxidant, they constitute an intricate antioxidant network. Caffeic acid, p-coumaric acid, ferulic acid and chlorogenic acid with or without 2-mercaptoethanol (ME, as a substitute for GSH, was investigated by the induction period (IP method for polymerization of methyl methacrylate (MMA initiated by thermal decomposition of 2,2'-azobisisobutyronitrile (AIBN, a source of alkyl radicals, R. and benzoyl peroxide (BPO, a source of peroxy radicals, PhCOO. using differential scanning calorimetry (DSC. Upon PhCOO. radical scavenging, the stoichiometric factors (n, number of free radical trapped by one mole of antioxidant for caffeic acid, ferulic acid, p-coumaric acid and chlorogenic acid were 2.4, 1.8, 1.7 and 0.9, whereas upon R. radical scavenging, the corresponding values were 1.3, 1.2, 1.0 and 0.8, respectively. Antioxidants with n values close to 2 suggest the stepwise formation of semiquinone radicals and quinones. By contrast, those with n values close to 1 suggest the formation of dimers after single-electron oxidation, possibly due to recombination of corresponding aryloxy radicals. The ratio of the rate constant of inhibition to that of propagation (kinh/kp declined in the order chlorogenic acid > p-coumaric acid > ferulic acid > caffeic acid. The ratio of the observed IP for the phenolcarboxylic acid/2-mercapto-ethanol (ME mixture (1:1 molar ratio (A to the calculated IP (the simple sum of phenol acid antioxidant and ME (B was investigated. Upon R. scavenging, the caffeic acid or p-coumaric acid/ME mixture was A/B > 1, particularly the former was 1.2, suggesting a synergic effect. By contrast, upon PhCOO. scavenging, the corresponding mixture was A/B < 1, particularly the latter was 0.7, suggesting an antagonistic effect. Upon both radicals scavenging, the A/B for the ferulic acid or chlorogenic acid

  14. 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

    International Nuclear Information System (INIS)

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

    1989-01-01

    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)

  15. Suppression of skin inflammation in keratinocytes and acute/chronic disease models by caffeic acid phenethyl ester.

    Science.gov (United States)

    Lim, Kyung-Min; Bae, SeungJin; Koo, Jung Eun; Kim, Eun-Sun; Bae, Ok-Nam; Lee, Joo Young

    2015-04-01

    Skin inflammation plays a central role in the pathophysiology and symptoms of diverse chronic skin diseases including atopic dermatitis (AD). In this study, we examined if caffeic acid phenethyl ester (CAPE), a skin-permeable bioactive compound from propolis, was protective against skin inflammation using in vitro cell system and in vivo animal disease models. CAPE suppressed TNF-α-induced NF-κB activation and expression of inflammatory cytokines in human keratinocytes (HaCaT). The potency and efficacy of CAPE were superior to those of a non-phenethyl derivative, caffeic acid. Consistently, topical treatment of CAPE (0.5 %) attenuated 12-O-tetradecanoylphorbol-13-acetate(TPA)-induced skin inflammation on mouse ear as CAPE reduced ear swelling and histologic inflammation scores. CAPE suppressed increased expression of pro-inflammatory molecules such as TNF-α, cyclooxygenase-2 and inducible NO synthase in TPA-stimulated skin. TPA-induced phosphorylation of IκB and ERK was blocked by CAPE suggesting that protective effects of CAPE on skin inflammation is attributed to inhibition of NF-κB activation. Most importantly, in an oxazolone-induced chronic dermatitis model, topical application of CAPE (0.5 and 1 %) was effective in alleviating AD-like symptoms such as increases of trans-epidermal water loss, skin thickening and serum IgE as well as histologic inflammation assessment. Collectively, our results propose CAPE as a promising candidate for a novel topical drug for skin inflammatory diseases.

  16. Reduction of the DNA damages, Hepatoprotective Effect and Antioxidant Potential of the Coconut Water, ascorbic and Caffeic Acids in Oxidative Stress Mediated by Ethanol

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    VANDERSON S. BISPO

    Full Text Available ABSTRACT Hepatic disorders such as steatosis and alcoholic steatohepatitis are common diseases that affect thousands of people around the globe. This study aims to identify the main phenol compounds using a new HPLC-ESI+-MS/MS method, to evaluate some oxidative stress parameters and the hepatoprotective action of green dwarf coconut water, caffeic and ascorbic acids on the liver and serum of rats treated with ethanol. The results showed five polyphenols in the lyophilized coconut water spiked with standards: chlorogenic acid (0.18 µM, caffeic acid (1.1 µM, methyl caffeate (0.03 µM, quercetin (0.08 µM and ferulic acid (0.02 µM isomers. In the animals, the activity of the serum γ-glutamyltranspeptidase (γ-GT was reduced to 1.8 I.U/L in the coconut water group, 3.6 I.U/L in the ascorbic acid group and 2.9 I.U/L in the caffeic acid groups, when compared with the ethanol group (5.1 I.U/L, p<0.05. Still in liver, the DNA analysis demonstrated a decrease of oxidized bases compared to ethanol group of 36.2% and 48.0% for pretreated and post treated coconut water group respectively, 42.5% for the caffeic acid group, and 34.5% for the ascorbic acid group. The ascorbic acid was efficient in inhibiting the thiobarbituric acid reactive substances (TBARS in the liver by 16.5% in comparison with the ethanol group. These data indicate that the green dwarf coconut water, caffeic and ascorbic acids have antioxidant, hepatoprotective and reduced DNA damage properties, thus decreasing the oxidative stress induced by ethanol metabolism.

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

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    Sumeyya Akyol

    2014-01-01

    Full Text Available 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.

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

    Science.gov (United States)

    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).

  19. Evaluation of Chemical Constituents and Antioxidant Activity of Coconut Water (Cocus nucifera L. and Caffeic Acid in Cell Culture

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    JOAO L.A. SANTOS

    2013-09-01

    Full Text Available 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.

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

    Energy Technology Data Exchange (ETDEWEB)

    Park, Mi Hee; Kang, Dong Woo [Department of Molecular Biology, Pusan National University, Busan 609-735 (Korea, Republic of); Jung, Yunjin [College of Pharmacy, Pusan National University, Busan 609-735 (Korea, Republic of); Choi, Kang-Yell [Translational Research Center for Protein Function Control, Department of Biotechnology, College of Life Science and Biotechnology, Yonsei University, Seoul (Korea, Republic of); Min, Do Sik, E-mail: minds@pusan.ac.kr [Department of Molecular Biology, Pusan National University, Busan 609-735 (Korea, Republic of)

    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.

  1. Constituents of Propolis: Chrysin, Caffeic Acid, p-Coumaric Acid, and Ferulic Acid Induce PRODH/POX-Dependent Apoptosis in Human Tongue Squamous Cell Carcinoma Cell (CAL-27).

    Science.gov (United States)

    Celińska-Janowicz, Katarzyna; Zaręba, Ilona; Lazarek, Urszula; Teul, Joanna; Tomczyk, Michał; Pałka, Jerzy; Miltyk, Wojciech

    2018-01-01

    Propolis evokes several therapeutic properties, including anticancer activity. These activities are attributed to the action of polyphenols. Previously it has been demonstrated, that one of the most abundant polyphenolic compounds in ethanolic extracts of propolis are chrysin, caffeic acid, p -coumaric acid, and ferulic acid. Although their pro-apoptotic activity on human tongue squamous cell carcinoma cells (CAL-27) was established previously, the detailed mechanism of this process remains unclear. Considering the crucial role of proline metabolism and proline dehydrogenase/proline oxidase (PRODH/POX) in the regulation of cancer cell survival/apoptosis, we studied these processes in polyphenol-treated CAL-27 cells. All studied polyphenols evoked anti-proliferative activity, accompanied by increased PRODH/POX, P53, active caspases-3 and -9 expressions and decreased collagen biosynthesis, prolidase activity and proline concentration in CAL-27 cells. These data suggest that polyphenols of propolis induce PRODH/POX-dependent apoptosis through up-regulation of mitochondrial proline degradation and down-regulation of proline utilization for collagen biosynthesis.

  2. Caffeic acid, morin hydrate and quercetin partially attenuate sulfur mustard-induced cell death by inhibiting the lipoxygenase pathway.

    Science.gov (United States)

    Kim, Shin; Jeong, Kwang-Joon; Cho, Sung Kweon; Park, Joo-Won; Park, Woo-Jae

    2016-11-01

    Sulfur mustard (SM) is an alkylating agent, which has been used as in chemical warfare in a number of conflicts. As the generation of reactive oxygen species (ROS), and adducts in DNA and proteins have been suggested as the mechanism underlying SM‑induced cytotoxicity, the present study screened several antioxidant candidates, including tannic acid, deferoxamine mesylate, trolox, vitamin C, ellagic acid and caffeic acid (CA) to assess their potential as therapeutic agents for SM‑induced cell death. Among several antioxidants, CA partially alleviated SM‑induced cell death in a dose‑dependent manner. Although CA treatment decreased the phosphorylation of p38 mitogen‑activated protein (MAP) kinase and p53, p38 MAP kinase inhibition by SB203580 did not affect SM‑induced cell death. As CA has also been reported as a 15‑lipoxygenase (15‑LOX) inhibitor, the role of 15‑LOX in SM‑induced cytotoxicity was also examined. Similar to the results observed with CA, treatment with PD146176, a specific 15‑LOX inhibitor, decreased SM‑induced cytotoxicity, accompanied by decreases in the production of tumor necrosis factor‑α and 15‑hydroxyeicosatetraenoic acid. Furthermore, the present study investigated the protective effects of two natural 15‑LOX inhibitors, morin hydrate and quercetin, in SM‑induced cytotoxicity. As expected, these inhibitors had similar protective effects against SM‑induced cytotoxicity. These antioxidants also reduced the generation of ROS and nitrate/nitrite. Therefore, the results of the present study indicated that the natural products, CA, quercetin and morin hydrate, offer potential as adjuvant therapeutic agents for SM‑induced toxicity, not only by reducing inflammation mediated by the p38 and LOX signaling pathways, but also by decreasing the generation of ROS and nitrate/nitrite.

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

    Science.gov (United States)

    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...

  4. Poly(3-hydroxybutyrate)/caffeic acid electrospun fibrous materials coated with polyelectrolyte complex and their antibacterial activity and in vitro antitumor effect against HeLa cells

    Energy Technology Data Exchange (ETDEWEB)

    Ignatova, Milena G. [Laboratory of Bioactive Polymers, Institute of Polymers, Bulgarian Academy of Sciences, Acad. G. Bonchev St, Bl. 103A, BG-1113 Sofia (Bulgaria); Manolova, Nevena E., E-mail: manolova@polymer.bas.bg [Laboratory of Bioactive Polymers, Institute of Polymers, Bulgarian Academy of Sciences, Acad. G. Bonchev St, Bl. 103A, BG-1113 Sofia (Bulgaria); Rashkov, Iliya B. [Laboratory of Bioactive Polymers, Institute of Polymers, Bulgarian Academy of Sciences, Acad. G. Bonchev St, Bl. 103A, BG-1113 Sofia (Bulgaria); Markova, Nadya D. [Institute of Microbiology, Bulgarian Academy of Sciences, Acad. G. Bonchev Bl. 26, BG-1113 Sofia (Bulgaria); Toshkova, Reneta A.; Georgieva, Ani K.; Nikolova, Elena B. [Institute of Experimental Morphology, Pathology and Anthropology with Museum, Bulgarian Academy of Sciences, Acad. G. Bonchev St, bl. 25, BG-1113 Sofia (Bulgaria)

    2016-08-01

    The purpose of this work was to investigate the possibility for the preparation of new poly(3-hydroxybutyrate) (PHB)/poly(ethylene glycol) (PEG)-based fibrous materials containing natural phenolic compound caffeic acid (CA) of diverse architectures, as well as to study the impact of the fiber composition on the in vitro CA release profile and on the biological properties of the fibrous materials. The application of the one-pot electrospinning enabled the fabrication of nanofibrous materials from PHB and PEG loaded with the CA. Materials with targeted design were obtained by coating with polyelectrolyte complex of alginate (Alg) and N,N,N-trimethylchitosan (TMCh). Three different processing paths were used to obtain coated mats: (i) with CA incorporated in the PHB/PEG core; (ii) with CA embedded in the Alg layer; and (iii) with CA included in the TMCh layer. The in vitro release of CA was modulated by controlling the composition and the architecture of the nanofibrous mats. The performed microbiological screening and MTT cell viability studies revealed that in contrast to the bare mats, the CA-containing nanofibrous materials were effective in suppressing the growth of the Gram-positive bacteria Staphylococcus aureus and the Gram-negative bacteria Escherichia coli and displayed good cytotoxicity against human cervical HeLa tumor cells. In addition, the proliferation of murine spleen lymphocytes and peritoneal macrophages was increased by the prepared CA-containing nanofibrous materials. The obtained materials are promising for antibacterial wound dressing applications as well as for application in local treatment of cervical tumors. - Highlights: • New caffeic acid-loaded materials from PHB and PEG were prepared by electrospinning. • Different design is achieved by coating and formation of polyelectrolyte complexes. • The control on the architecture of the mats enables modulating caffeic acid release. • The caffeic acid-loaded mats suppress the growth of

  5. Poly(3-hydroxybutyrate)/caffeic acid electrospun fibrous materials coated with polyelectrolyte complex and their antibacterial activity and in vitro antitumor effect against HeLa cells

    International Nuclear Information System (INIS)

    Ignatova, Milena G.; Manolova, Nevena E.; Rashkov, Iliya B.; Markova, Nadya D.; Toshkova, Reneta A.; Georgieva, Ani K.; Nikolova, Elena B.

    2016-01-01

    The purpose of this work was to investigate the possibility for the preparation of new poly(3-hydroxybutyrate) (PHB)/poly(ethylene glycol) (PEG)-based fibrous materials containing natural phenolic compound caffeic acid (CA) of diverse architectures, as well as to study the impact of the fiber composition on the in vitro CA release profile and on the biological properties of the fibrous materials. The application of the one-pot electrospinning enabled the fabrication of nanofibrous materials from PHB and PEG loaded with the CA. Materials with targeted design were obtained by coating with polyelectrolyte complex of alginate (Alg) and N,N,N-trimethylchitosan (TMCh). Three different processing paths were used to obtain coated mats: (i) with CA incorporated in the PHB/PEG core; (ii) with CA embedded in the Alg layer; and (iii) with CA included in the TMCh layer. The in vitro release of CA was modulated by controlling the composition and the architecture of the nanofibrous mats. The performed microbiological screening and MTT cell viability studies revealed that in contrast to the bare mats, the CA-containing nanofibrous materials were effective in suppressing the growth of the Gram-positive bacteria Staphylococcus aureus and the Gram-negative bacteria Escherichia coli and displayed good cytotoxicity against human cervical HeLa tumor cells. In addition, the proliferation of murine spleen lymphocytes and peritoneal macrophages was increased by the prepared CA-containing nanofibrous materials. The obtained materials are promising for antibacterial wound dressing applications as well as for application in local treatment of cervical tumors. - Highlights: • New caffeic acid-loaded materials from PHB and PEG were prepared by electrospinning. • Different design is achieved by coating and formation of polyelectrolyte complexes. • The control on the architecture of the mats enables modulating caffeic acid release. • The caffeic acid-loaded mats suppress the growth of

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

    Science.gov (United States)

    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.

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

    Directory of Open Access Journals (Sweden)

    Aburrahman Gun

    2016-01-01

    Full Text Available 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.

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

    Science.gov (United States)

    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. Copyright © 2015 The Authors. Published by Elsevier Ltd.. All rights reserved.

  9. Nanomolar electrochemical detection of caffeic acid in fortified wine samples based on gold/palladium nanoparticles decorated graphene flakes.

    Science.gov (United States)

    Thangavelu, Kokulnathan; Raja, Nehru; Chen, Shen-Ming; Liao, Wei-Cheng

    2017-09-01

    Amalgamation of noble metal nanomaterials on graphene flakes potentially paves one way to improve their physicochemical properties. This paper deals with the simultaneous electrochemical deposition of gold and palladium nanoparticles on graphene flakes (Au/PdNPs-GRF) for the sensitive determination of caffeic acid (CA). The physiochemical properties of the prepared Au/PdNPs-GRF was characterized by using numerous analytical techniques such as scanning electron microscopy, electron dispersive X-ray spectroscopy, Fourier transform infrared spectroscopy, X-ray powder diffraction, Raman spectroscopy and electrochemical impedance spectroscopy. The enhanced electrochemical determination of CA at Au/PdNPs deposition on GRF were studied by using cyclic voltammetry and differential pulse voltammetry. In results, Au/PdNPs-GRF electrode exhibited an excellent electrocatalytic activity towards CA with wide linear range and low limit of detection of 0.03-938.97µM and 6nM, respectively. Eventually, the Au/PdNPs-GRF was found as a selective and stable active material for the sensing of CA. In addition, the proposed sensor showed the adequate results in real sample analysis. Copyright © 2017 Elsevier Inc. All rights reserved.

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

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    Abuzar Elnager

    2015-01-01

    Full Text Available 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.

  11. Protective role of caffeic acid on lambda cyhalothrin-induced changes in sperm characteristics and testicular oxidative damage in rats.

    Science.gov (United States)

    Abdallah, Fatma Ben; Fetoui, Hamadi; Zribi, Nassira; Fakhfakh, Feiza; Keskes, Leila

    2012-08-01

    The synthetic pyrethroids are expected to cause deleterious effects on most of the organs and especially on the male reproductive system. The current study was performed to assess the adverse effect of lambda cyhalothrin (LC) on reproductive organs and fertility in male rats and to evaluate the protective role of caffeic acid phenethyl ester (CAPE) in alleviating the detrimental effect of LC on male fertility. A total of 48 male rats were divided into 4 groups (12 rats each): control group received distilled water ad libitum and 1 ml of vehicle solution given intraperitoneally (i.p.); CAPE-treated group received a single i.p. dose of CAPE (10 μmol kg⁻¹ day⁻¹); LC-treated group received 668 ppm of LC through drinking water; and CAPE + LC-treated group received an i.p. injection of CAPE (10 μmol kg⁻¹ day⁻¹) 12 h before the LC administration. The experiment was conducted for 10 consecutive weeks. LC caused a significant increase in testicular malondialdehyde, catalase, superoxide dismutase, glutathione-S-transferase activities, and sperm abnormalities and a significant reduction in testicular glutathione concentration, sperm count, sperm motility, and a live sperm percentage. Conversely, treatment with CAPE improved the reduction in the sperm characteristics, LC-induced oxidative damage of testes and the testicular histopathological alterations. Results indicate that LC exerts significant harmful effects on the male reproductive system and that CAPE reduced the deleterious effects of LC on male fertility.

  12. Novel Antidepressant-Like Activity of Caffeic Acid Phenethyl Ester Is Mediated by Enhanced Glucocorticoid Receptor Function in the Hippocampus

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    Mi-Sook Lee

    2014-01-01

    Full Text Available Caffeic acid phenethyl ester (CAPE is an active component of propolis that has a variety of potential pharmacological effects. Although we previously demonstrated that propolis has antidepressant-like activity, the effect of CAPE on this activity remains unknown. The present study assessed whether treatment with CAPE (5, 10, and 20 µmol/kg for 21 days has an antidepressant-like effect in mice subjected to chronic unpredictable stress via tail suspension (TST and forced swim (FST tests. CAPE administration induced behaviors consistent with an antidepressant effect, evidenced by decreased immobility in the TST and FST independent of any effect on serum corticosterone secretion. Western blots, conducted subsequent to behavioral assessment, revealed that CAPE significantly decreased glucocorticoid receptor phosphorylation at S234 (pGR(S234, resulting in an increased pGR(S220/S234 ratio. We also observed negative correlations between pGR(S220/(S234 and p38 mitogen-activated protein kinase (p38MAPK phosphorylation, which was decreased by CAPE treatment. These findings suggest that CAPE treatment exerts an antidepressant-like effect via downregulation of p38MAPK phosphorylation, thereby contributing to enhanced GR function.

  13. Synergistic Antibacterial Effects of Chitosan-Caffeic Acid Conjugate against Antibiotic-Resistant Acne-Related Bacteria.

    Science.gov (United States)

    Kim, Ji-Hoon; Yu, Daeung; Eom, Sung-Hwan; Kim, Song-Hee; Oh, Junghwan; Jung, Won-Kyo; Kim, Young-Mog

    2017-06-08

    The object of this study was to discover an alternative therapeutic agent with fewer side effects against acne vulgaris, one of the most common skin diseases. Acne vulgaris is often associated with acne-related bacteria such as Propionibacterium acnes , Staphylococcus epidermidis , Staphylococcus aureus , and Pseudomonas aeruginosa . Some of these bacteria exhibit a resistance against commercial antibiotics that have been used in the treatment of acne vulgaris (tetracycline, erythromycin, and lincomycin). In the current study, we tested in vitro antibacterial effect of chitosan-phytochemical conjugates on acne-related bacteria. Three chitosan-phytochemical conjugates used in this study exhibited stronger antibacterial activity than that of chitosan (unmodified control). Chitosan-caffeic acid conjugate (CCA) showed the highest antibacterial effect on acne-related bacteria along with minimum inhibitory concentration (MIC; 8 to 256 μg/mL). Additionally, the MIC values of antibiotics against antibiotic-resistant P. acnes and P. aeruginosa strains were dramatically reduced in combination with CCA, suggesting that CCA would restore the antibacterial activity of the antibiotics. The analysis of fractional inhibitory concentration (FIC) indices clearly revealed a synergistic antibacterial effect of CCA with antibiotics. Thus, the median sum of FIC (∑FIC) values against the antibiotic-resistant bacterial strains ranged from 0.375 to 0.533 in the combination mode of CCA and antibiotics. The results of the present study suggested a potential possibility of chitosan-phytochemical conjugates in the control of infections related to acne vulgaris.

  14. Crystallization and preliminary X-ray diffraction analysis of a Lys49-phospholipase A2 complexed with caffeic acid, a molecule with inhibitory properties against snake venoms

    International Nuclear Information System (INIS)

    Shimabuku, Patrícia S.; Fernandes, Carlos A. H.; Magro, Angelo J.; Costa, Tássia R.; Soares, Andreimar M.; Fontes, Marcos R. M.

    2011-01-01

    Piratoxin I, a noncatalytic and myotoxic Lys49-phospholipase A 2 from B. pirajai venom, was cocrystallized with the inhibitor caffeic acid and a data set was collected to a resolution of 1.65 Å. The electron-density map unambiguously indicated that three inhibitor molecules interact with the C-terminus of the protein. Phospholipases A 2 (PLA 2 s) are one of the main components of bothropic venoms; in addition to their phospholipid hydrolysis action, they are involved in a wide spectrum of pharmacological activities, including neurotoxicity, myotoxicity and cardiotoxicity. Caffeic acid is an inhibitor that is present in several plants and is employed for the treatment of ophidian envenomations in the folk medicine of many developing countries; as bothropic snake bites are not efficiently neutralized by conventional serum therapy, it may be useful as an antivenom. In this work, the cocrystallization and preliminary X-ray diffraction analysis of the Lys49-PLA 2 piratoxin I from Bothrops pirajai venom in the presence of the inhibitor caffeic acid (CA) are reported. The crystals diffracted X-rays to 1.65 Å resolution and the structure was solved by molecular-replacement techniques. The electron-density map unambiguously indicated the presence of three CA molecules that interact with the C-terminus of the protein. This is the first time a ligand has been observed bound to this region and is in agreement with various experiments previously reported in the literature

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

    International Nuclear Information System (INIS)

    Chen, Y.-J.; Liao, H.-F.; Tsai, T.-H.; Wang, S.-Y.; Shiao, M.-S.

    2005-01-01

    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-κB 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 γ-glutamyl transpeptidase activity. Radiation activated NF-κB 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-κB activity, without toxicity to bone marrow, liver, and kidney

  16. Direct interaction between caffeic acid phenethyl ester and human neutrophil elastase inhibits the growth and migration of PANC-1 cells.

    Science.gov (United States)

    Duan, Jianhui; Xiaokaiti, Yilixiati; Fan, Shengjun; Pan, Yan; Li, Xin; Li, Xuejun

    2017-05-01

    Pancreatic ductal adenocarcinoma (PDAC) is one of the most lethal malignant tumors of the digestive system, but the mechanisms of its development and progression are unclear. Inflammation is thought to be fundamental to pancreatic cancer development and caffeic acid phenethyl ester (CAPE) is an active component of honey bee resin or propolis with anti-inflammatory and anticancer activities. We investigated the inhibitory effects of CAPE on cell growth and migration induced by human neutrophil elastase (HNE) and report that HNE induced cancer cell migration at low doses and growth at higher doses. In contrast, lower CAPE doses inhibited migration and higher doses of CAPE inhibited the growth induced by HNE. HNE activity was significantly inhibited by CAPE (7.5-120 µM). Using quantitative real-time PCR and western blotting, we observed that CAPE (18-60 µM) did not affect transcription and translation of α1-antitrypsin (α1-AT), an endogenous HNE inhibitor. However, in an in silico drug target docking model, we found that CAPE directly bound to the binding pocket of HNE (25.66 kcal/mol) according to CDOCKER, and the residue of the catalytic site stabilized the interaction between CAPE and HNE as evidenced by molecular dynamic simulation. Response unit (RU) values of surface plasmon resonance (SPR) significantly increased with incremental CAPE doses (7.5-120 µM), indicating that CAPE could directly bind to HNE in a concentration-dependent manner. Thus, CAPE is an effective inhibitor of HNE via direct interaction whereby it inhibits the migration and growth of PANC-1 cells in a dose-dependent manner.

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

    Science.gov (United States)

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

    2015-09-01

    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 bmr-12 mutants (0.29) was significantly (P 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.

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

    Science.gov (United States)

    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

  19. Caffeic acid phenethyl ester suppresses melanoma tumor growth by inhibiting PI3K/AKT/XIAP pathway.

    Science.gov (United States)

    Pramanik, Kartick C; Kudugunti, Shashi K; Fofaria, Neel M; Moridani, Majid Y; Srivastava, Sanjay K

    2013-09-01

    Melanoma is highly metastatic and resistant to chemotherapeutic drugs. Our previous studies have demonstrated that caffeic acid phenethyl ester (CAPE) suppresses the growth of melanoma cells and induces reactive oxygen species generation. However, the exact mechanism of the growth suppressive effects of CAPE was not clear. Here, we determined the potential mechanism of CAPE against melanoma in vivo and in vitro. Administration of 10 mg/kg/day CAPE substantially suppressed the growth of B16F0 tumor xenografts in C57BL/6 mice. Tumors from CAPE-treated mice showed reduced phosphorylation of phosphoinositide 3-kinase, AKT, mammalian target of rapamycin and protein level of X-linked inhibitor of apoptosis protein (XIAP) and enhanced the cleavage of caspase-3 and poly (ADP ribose) polymerase. In order to confirm the in vivo observations, melanoma cells were treated with CAPE. CAPE treatment suppressed the activating phosphorylation of phosphoinositide 3-kinase at Tyr 458, phosphoinositide-dependent kinase-1 at Ser 241, mammalian target of rapamycin at Ser 2448 and AKT at Ser 473 in B16F0 and SK-MEL-28 cells in a concentration and time-dependent study. Furthermore, the expression of XIAP, survivin and BCL-2 was downregulated by CAPE treatment in both cell lines. Significant apoptosis was observed by CAPE treatment as indicated by cleavage of caspase-3 and poly (ADP ribose) polymerase. AKT kinase activity was inhibited by CAPE in a concentration-dependent manner. CAPE treatment increased the nuclear translocation of XIAP, indicating increased apoptosis in melanoma cells. To confirm the involvement of reactive oxygen species in the inhibition of AKT/XIAP pathway, cells were treated with antioxidant N-acetyl-cysteine (NAC) prior to CAPE treatment. Our results indicate that NAC blocked CAPE-mediated AKT/XIAP inhibition and protected the cells from apoptosis. Because AKT regulates XIAP, their interaction was examined by immunoprecipitation studies. Our results show that CAPE

  20. Effect of caffeic acid phenethyl ester on Prevotella intermedia lipopolysaccharide-induced production of proinflammatory mediators in murine macrophages.

    Science.gov (United States)

    Choi, E-Y; Choe, S-H; Hyeon, J-Y; Choi, J-I; Choi, I S; Kim, S-J

    2015-12-01

    Caffeic acid phenethyl ester (CAPE) has numerous potentially beneficial properties, including antioxidant, immunomodulatory and anti-inflammatory activities. However, the effect of CAPE on periodontal disease has not been studied before. This study was designed to investigate the efficacy of CAPE in ameliorating the production of proinflammatory mediators in macrophages activated by lipopolysaccharide (LPS) from Prevotella intermedia, a pathogen implicated in periodontal disease. LPS from P. intermedia ATCC 25611 was isolated by using the standard hot phenol-water method. Culture supernatants were assayed for nitric oxide (NO), interleukin (IL)-1β and IL-6. We used real-time polymerase chain reaction to quantify inducible NO synthase, IL-1β, IL-6, heme oxygenase (HO)-1 and suppressors of cytokine signaling (SOCS) 1 mRNA expression. HO-1 protein expression and levels of signaling proteins were assessed by immunoblot analysis. DNA-binding activities of NF-κB subunits were analyzed by using the enzyme-linked immunosorbent assay-based kits. CAPE exerted significant inhibitory effects on P. intermedia LPS-induced production of NO, IL-1β and IL-6 as well as their mRNA expression in RAW264.7 cells. CAPE-induced HO-1 expression in cells activated with P. intermedia LPS, and selective inhibition of HO-1 activity by tin protoporphyrin IX attenuated the inhibitory effect of CAPE on LPS-induced NO production. CAPE did not interfere with IκB-α degradation induced by P. intermedia LPS. Instead, CAPE decreased nuclear translocation of NF-κB p65 and p50 subunits induced with LPS, and lessened LPS-induced p50 binding activity. Further, CAPE showed strong inhibitory effects on LPS-induced signal transducer and activator of transcription 1 and 3 phosphorylation. Besides, CAPE significantly elevated SOCS1 mRNA expression in P. intermedia LPS-stimulated cells. Modulation of host response by CAPE may represent an attractive strategy towards the treatment of periodontal disease

  1. Experimental and theoretical investigation of interaction between bovine serum albumin and the mixture of caffeic acid and salicylic acid as the antioxidants

    International Nuclear Information System (INIS)

    Benvidi, Ali; Rezaeinasab, Masoud; Gharaghani, Sajjad; Abbasi, Saleheh; Zare, Hamid R.

    2017-01-01

    In the present work, interaction between bovine serum albumin (BSA) with caffeic acid (CA), salicylic acid (SA) and the mixture of these components were studied by experimental and computational methods In the experimental measurements, differential pulse voltammetry (DPV) and UV–vis spectrophotometry (UV–Vis) were separately used to investigate the nature of interactions. Also, some of the thermodynamics parameters were obtained from these measurements. At the second step, the chemometric methods including multivariate curve resolution–alternating least squares (MCR–ALS) and parallel factor analysis (PARAFAC) were used since the results of the experimental measurements have a strongly overlapping signals. For this purpose, a three-way array was resolved by PARAFAC and a row- and column-wise augmented matrix, which built with DPV and UV–vis sub-matrices, were analyzed using MCR-ALS. The interesting results for stoichiometry and electrochemical behaviors of these components were obtained by using the proposed algorithms. Finally, molecular docking were applied to compare experimentally determined binding parameters with molecular modelling. According to the obtained results an excellent agreement was found between experimental and computational results.

  2. Reaction Mechanisms and Structural and Physicochemical Properties of Caffeic Acid Grafted Chitosan Synthesized in Ascorbic Acid and Hydroxyl Peroxide Redox System.

    Science.gov (United States)

    Liu, Jun; Pu, Huimin; Chen, Chong; Liu, Yunpeng; Bai, Ruyu; Kan, Juan; Jin, Changhai

    2018-01-10

    The ascorbic acid (AA) and hydroxyl peroxide (H 2 O 2 ) redox pair induced free radical grafting reaction is a promising approach to conjugate phenolic groups with chitosan (CS). In order to reveal the exact mechanisms of the AA/H 2 O 2 redox pair induced grafting reaction, free radicals generated in the AA/H 2 O 2 redox system were compared with hydroxyl radical ( • OH) produced in the Fe 2+ /H 2 O 2 redox system. Moreover, the structural and physicochemical properties of caffeic acid grafted CS (CA-g-CS) synthesized in these two redox systems were compared. Results showed that only ascorbate radical (Asc •- ) was produced in the AA/H 2 O 2 system. The reaction between Asc •- and CS produced novel carbon-centered radicals, whereas no new free radicals were detected when • OH reacted with CS. Thin layer chromatography, UV-vis, Fourier transform infrared, and nuclear magnetic resonance spectroscopic analyses all confirmed that CA was successfully grafted onto CS through Asc •- . However, CA could be hardly grafted onto CS via • OH. CA-g-CS synthesized through Asc •- exhibited lower thermal stability and crystallinity than the reaction product obtained through • OH. For the first time, our results demonstrated that the synthesis of CA-g-CS in the AA/H 2 O 2 redox system was mediated by Asc •- rather than • OH.

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

    Science.gov (United States)

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

    2016-07-08

    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.

  4. Caffeic acid, a coffee-related organic acid, inhibits infection by severe fever with thrombocytopenia syndrome virus in vitro.

    Science.gov (United States)

    Ogawa, Motohiko; Shirasago, Yoshitaka; Ando, Shuji; Shimojima, Masayuki; Saijo, Masayuki; Fukasawa, Masayoshi

    2018-04-05

    Severe fever with thrombocytopenia syndrome (SFTS) virus (SFTSV) causes tick-borne hemorrhagic fever in East Asia. The disease is characterized by high morbidity and mortality. Here, we evaluated the effects of caffeic acid (CA), a coffee-related organic acid with antiviral effects, against SFTSV infection. CA dose-dependently inhibited SFTSV infection in permissive human hepatoma Huh7.5.1-8 cells when SFTSV was added into the culture medium with CA. However, quinic acid (QA), another coffee-related organic acid, did not inhibit SFTSV infection. The 50% inhibitory concentration (IC 50 ) of CA against SFTSV was 0.048 mM, whereas its 50% cytotoxic concentration was 7.6 mM. The selectivity index (SI) was 158. Pre-incubation of SFTSV with CA for 4 h resulted in a greater inhibition of SFTSV infection (IC 50  = 0.019 mM; SI = 400). The pre-incubation substantially decreased viral attachment to the cells. CA treatment of the SFTSV-infected cells also inhibited the infection, albeit less effectively. CA activity after cell infection with SFTSV was more pronounced at a low multiplicity of infection (MOI) of 0.01 per cell (IC 50  = 0.18 mM) than at a high MOI of 1 per cell (IC 50  > 1 mM). Thus, CA inhibited virus spread by acting directly on the virus rather than on the infected cells. In conclusion, CA acted on SFTSV and inhibited viral infection and spread, mainly by inhibiting the binding of SFTSV to the cells. We therefore demonstrated CA to be a potential anti-SFTSV drug for preventing and treating SFTS. Copyright © 2018 Japanese Society of Chemotherapy and The Japanese Association for Infectious Diseases. Published by Elsevier Ltd. All rights reserved.

  5. Caffeic acid phenethyl ester protects against glucocorticoid-induced osteoporosis in vivo: Impact on oxidative stress and RANKL/OPG signals

    International Nuclear Information System (INIS)

    Tolba, Mai F.; El-Serafi, Ahmed T.; Omar, Hany A.

    2017-01-01

    Glucocorticoid-induced osteoporosis (GIO) is one of the most common causes of secondary osteoporosis. Given that glucocorticoids are considered as a main component of the treatment protocols for a variety of inflammation and immune-mediated diseases besides its use as adjuvant to several chemotherapeutic agents, it is crucial to find ways to overcome this critical adverse effect. Caffeic acid phenethyl ester (CAPE), which is a natural compound derived from honeybee propolis displayed promising antiosteoporotic effects against mechanical bone injury in various studies. The current work aimed at investigating the potential protective effect of CAPE against GIO in vivo with emphasis on the modulation of oxidative status and receptor activator of NF-kB ligand (RANKL)/osteoprotegrin (OPG) signaling. The results showed that CAPE opposed dexamethasone (DEX)-mediated alterations in bone histology and tartarate-resistant acid phosphatase (TRAP) activity. In addition, CAPE restored oxidative balance, Runt-related transcription factor 2 (RunX2) expression and reduced caspase-3 activity in femur tissues. Co-administration of CAPE with DEX normalized RANKL/OPG ratio and Akt activation indicating a reduction in DEX-osteoclastogenesis. In conclusion, concurrent treatment of CAPE with DEX exhibited promising effects in the protection against DEX-induced osteoporosis through opposing osteoclastogenesis and protecting osteoblasts. The potent antioxidant activity of CAPE is, at least in part, involved in its anti-apoptotic effects and modulation of RunX2 and RANKL/OPG signals. The use of CAPE-enriched propolis formulas is strongly recommended for patients on chronic glucocorticoid therapy to help in the attenuation of GIO. - Highlights: • Caffeic acid phenethyl ester (CAPE) counteracts DEX-induced osteoporosis. • CAPE hinders DEX-induced alterations in oxidation parameters as GSH, SOD and MDA. • CAPE opposes osteoclastogenesis via suppressing RANL/OPG ratio and Akt signals.

  6. Caffeic acid phenethyl ester protects against glucocorticoid-induced osteoporosis in vivo: Impact on oxidative stress and RANKL/OPG signals

    Energy Technology Data Exchange (ETDEWEB)

    Tolba, Mai F. [Department of Pharmacology and Toxicology, Faculty of Pharmacy, Ain Shams University, Cairo 11566 (Egypt); Chapman University, Irvine 92618, CA (United States); El-Serafi, Ahmed T. [Sharjah Institute for Medical Research, University of Sharjah, Sharjah 27272 (United Arab Emirates); Department of Medical Biochemistry, Faculty of Medicine, Suez Canal University, Ismailia (Egypt); Omar, Hany A., E-mail: hanyomar@sharjah.ac.ae [Sharjah Institute for Medical Research, University of Sharjah, Sharjah 27272 (United Arab Emirates); Department of Pharmacology, Faculty of Pharmacy, Beni-Suef University, Beni-Suef 62514 (Egypt)

    2017-06-01

    Glucocorticoid-induced osteoporosis (GIO) is one of the most common causes of secondary osteoporosis. Given that glucocorticoids are considered as a main component of the treatment protocols for a variety of inflammation and immune-mediated diseases besides its use as adjuvant to several chemotherapeutic agents, it is crucial to find ways to overcome this critical adverse effect. Caffeic acid phenethyl ester (CAPE), which is a natural compound derived from honeybee propolis displayed promising antiosteoporotic effects against mechanical bone injury in various studies. The current work aimed at investigating the potential protective effect of CAPE against GIO in vivo with emphasis on the modulation of oxidative status and receptor activator of NF-kB ligand (RANKL)/osteoprotegrin (OPG) signaling. The results showed that CAPE opposed dexamethasone (DEX)-mediated alterations in bone histology and tartarate-resistant acid phosphatase (TRAP) activity. In addition, CAPE restored oxidative balance, Runt-related transcription factor 2 (RunX2) expression and reduced caspase-3 activity in femur tissues. Co-administration of CAPE with DEX normalized RANKL/OPG ratio and Akt activation indicating a reduction in DEX-osteoclastogenesis. In conclusion, concurrent treatment of CAPE with DEX exhibited promising effects in the protection against DEX-induced osteoporosis through opposing osteoclastogenesis and protecting osteoblasts. The potent antioxidant activity of CAPE is, at least in part, involved in its anti-apoptotic effects and modulation of RunX2 and RANKL/OPG signals. The use of CAPE-enriched propolis formulas is strongly recommended for patients on chronic glucocorticoid therapy to help in the attenuation of GIO. - Highlights: • Caffeic acid phenethyl ester (CAPE) counteracts DEX-induced osteoporosis. • CAPE hinders DEX-induced alterations in oxidation parameters as GSH, SOD and MDA. • CAPE opposes osteoclastogenesis via suppressing RANL/OPG ratio and Akt signals.

  7. Inhibition of Procarcinogen Activating Enzyme CYP1A2 Activity and Free Radical Formation by Caffeic Acid and its Amide Analogues.

    Science.gov (United States)

    Narongchai, Paitoon; Niwatananun, Kanokporn; Narongchai, Siripun; Kusirisin, Winthana; Jaikang, Churdsak

    2016-01-01

    Caffeic acid (CAF) and its amide analogues, ethyl 1-(3',4'-dihydroxyphenyl) propen amide (EDPA), phenethyl 1-(3',4'-dihydroxyphenyl) propen amide (PEDPA), phenmethyl 1- (3',4'-dihydroxyphenyl) propen amide (PMDPA) and octyl 1-(3',4'-dihydroxyphenyl) propen amide (ODPA) were investigated for the inhibition of procarcinogen activating enzyme. CYP1A2 and scavenging activity on formation of nitric oxide, superoxide anion, DPPH radical and hydroxyl radical. It was found that they inhibited CYP1A2 enzyme by uncompetitive inhibition. Apparent Ki values of CAF, EDPA, PEDPA, PMDPA and ODPA were 0.59, 0.39, 0.45, 0.75 and 0.80 µM, respectively suggesting potent inhibitors of CYP1A2. Moreover, they potentially scavenged nitric oxide radical with IC 50 values of 0.12, 0.22, 0.28, 0.22 and 0.51 mM, respectively. The IC50 values of superoxide anion scavenging were 0.20, 0.22, 0.44, 2.18 and 2.50 mM, respectively. 1, 1- diphenyl-2- picrylhydrazyl (DPPH) radical-scavenging ability, shown as IC50 values, were 0.41, 0.29, 0.30, 0.89 and 0.84 mM, respectively. Moreover, the hydroxyl radical scavenging in vitro model was shown as IC50 values of 23.22, 21.06, 17.10, 17.21 and 15.81 µM, respectively. From our results, caffeic acid and its amide analogues are in vitro inhibitors of human CYP1A2 catalytic activity and free radical formation. They may be useful to be developed as potential chemopreventive agents that block CYP1A2-mediated chemical carcinogenesis.

  8. Catechol Groups Enable Reactive Oxygen Species Scavenging-Mediated Suppression of PKD-NFkappaB-IL-8 Signaling Pathway by Chlorogenic and Caffeic Acids in Human Intestinal Cells

    Directory of Open Access Journals (Sweden)

    Hee Soon Shin

    2017-02-01

    Full Text Available Chlorogenic acid (CHA and caffeic acid (CA are phenolic compounds found in coffee, which inhibit oxidative stress-induced interleukin (IL-8 production in intestinal epithelial cells, thereby suppressing serious cellular injury and inflammatory intestinal diseases. Therefore, we investigated the anti-inflammatory mechanism of CHA and CA, both of which inhibited hydrogen peroxide (H2O2-induced IL-8 transcriptional activity. They also significantly suppressed nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB transcriptional activity, nuclear translocation of the p65 subunit, and phosphorylation of IκB kinase (IKK. Additionally, upstream of IKK, protein kinase D (PKD was also suppressed. Finally, we found that they scavenged H2O2-induced reactive oxygen species (ROS and the functional moiety responsible for the anti-inflammatory effects of CHA and CA was the catechol group. Therefore, we conclude that the presence of catechol groups in CHA and CA allows scavenging of intracellular ROS, thereby inhibiting H2O2-induced IL-8 production via suppression of PKD-NF-κB signaling in human intestinal epithelial cells.

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

    Science.gov (United States)

    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

  10. Structure-function analyses of a caffeic acid O-methyltransferase from perennial ryegrass reveal the molecular basis for substrate preference.

    Science.gov (United States)

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

    2010-12-01

    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.

  11. Drug Nanoparticle Formulation Using Ascorbic Acid Derivatives

    Directory of Open Access Journals (Sweden)

    Kunikazu Moribe

    2011-01-01

    Full Text Available Drug nanoparticle formulation using ascorbic acid derivatives and its therapeutic uses have recently been introduced. Hydrophilic ascorbic acid derivatives such as ascorbyl glycoside have been used not only as antioxidants but also as food and pharmaceutical excipients. In addition to drug solubilization, drug nanoparticle formation was observed using ascorbyl glycoside. Hydrophobic ascorbic acid derivatives such as ascorbyl mono- and di-n-alkyl fatty acid derivatives are used either as drugs or carrier components. Ascorbyl n-alkyl fatty acid derivatives have been formulated as antioxidants or anticancer drugs for nanoparticle formulations such as micelles, microemulsions, and liposomes. ASC-P vesicles called aspasomes are submicron-sized particles that can encapsulate hydrophilic drugs. Several transdermal and injectable formulations of ascorbyl n-alkyl fatty acid derivatives were used, including ascorbyl palmitate.

  12. Caffeic Acid Phenethyl Ester Inhibits Oral Cancer Cell Metastasis by Regulating Matrix Metalloproteinase-2 and the Mitogen-Activated Protein Kinase Pathway

    Directory of Open Access Journals (Sweden)

    Chih-Yu Peng

    2012-01-01

    Full Text Available Caffeic acid phenethyl ester (CAPE, an active component extracted from honeybee hives, exhibits anti-inflammatory and anticancer activities. However, the molecular mechanism by which CAPE affects oral cancer cell metastasis has yet to be elucidated. In this study, we investigated the potential mechanisms underlying the effects of CAPE on the invasive ability of SCC-9 oral cancer cells. Results showed that CAPE attenuated SCC-9 cell migration and invasion at noncytotoxic concentrations (0 μM to 40 μM. Western blot and gelatin zymography analysis findings further indicated that CAPE downregulated matrix metalloproteinase-2 (MMP-2 protein expression and inhibited its enzymatic activity. CAPE exerted its inhibitory effects on MMP-2 expression and activity by upregulating tissue inhibitor of metalloproteinase-2 (TIMP-2 and potently decreased migration by reducing focal adhesion kinase (FAK phosphorylation and the activation of its downstream signaling molecules p38/MAPK and JNK. These data indicate that CAPE could potentially be used as a chemoagent to prevent oral cancer metastasis.

  13. Caffeic Acid Phenethyl Ester and Ethanol Extract of Propolis Induce the Complementary Cytotoxic Effect on Triple-Negative Breast Cancer Cell Lines

    Directory of Open Access Journals (Sweden)

    Anna Rzepecka-Stojko

    2015-05-01

    Full Text Available 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.

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

    Energy Technology Data Exchange (ETDEWEB)

    Kim, Hyung Gyun [Department of Toxicology, College of Pharmacy, Chungnam National University, Daejeon (Korea, Republic of); Han, Eun Hee [Division of Life Science, Korea Basic Science Institute, Daejeon (Korea, Republic of); Im, Ji Hye; Lee, Eun Ji; Jin, Sun Woo [Department of Toxicology, College of Pharmacy, Chungnam National University, Daejeon (Korea, Republic of); Jeong, Hye Gwang, E-mail: hgjeong@cnu.ac.kr [Department of Toxicology, College of Pharmacy, Chungnam National University, Daejeon (Korea, Republic of)

    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.

  15. Development of novel antibacterial active, HaCaT biocompatible and biodegradable CA-g-P(3HB-EC biocomposites with caffeic acid as a functional entity

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    H. M. N. Iqbal

    2015-09-01

    Full Text Available We have developed novel composites by grafting caffeic acid (CA onto the P(3HB-EC based material and laccase from Trametes versicolor was used for grafting purposes. The resulting composites were designated as CA-g-P(3HB-EC i.e., P(3HB-EC (control, 5CA-g-P(3HB-EC, 10CA-g-P(3HB-EC, 15CA-g-P(3HB-EC and 20CA-g-P(3HB-EC. FT-IR (Fourier-transform infrared spectroscopy was used to examine the functional and elemental groups of the control and laccase-assisted graft composites. Evidently, 15CA-g-P(3HB-EC composite exhibited resilient antibacterial activity against Gram-positive and Gram-negative bacterial strains. Moreover, a significant level of biocompatibility and biodegradability of the CA-g-P(3HB-EC composites was also achieved with the human keratinocytes-like HaCaT cells and soil burial evaluation, respectively. In conclusion, the newly developed novel composites with multi characteristics could well represent the new wave of biomaterials for medical applications, and more specifically have promising future in the infection free would dressings, burn and/or skin regeneration field due to their sophisticated characteristics.

  16. Protective Effect of Caffeic Acid on Paclitaxel Induced Anti-Proliferation and Apoptosis of Lung Cancer Cells Involves NF-κB Pathway

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    Yao Fong

    2012-05-01

    Full Text Available Caffeic acid (CA, a natural phenolic compound, is abundant in medicinal plants. CA possesses multiple biological effects such as anti-bacterial and anti-cancer growth. CA was also reported to induce fore stomach and kidney tumors in a mouse model. Here we used two human lung cancer cell lines, A549 and H1299, to clarify the role of CA in cancer cell proliferation. The growth assay showed that CA moderately promoted the proliferation of the lung cancer cells. Furthermore, pre-treatment of CA rescues the proliferation inhibition induced by a sub-IC50 dose of paclitaxel (PTX, an anticancer drug. Western blot showed that CA up-regulated the pro-survival proteins survivin and Bcl-2, the down-stream targets of NF-κB. This is consistent with the observation that CA induced nuclear translocation of NF-κB p65. Our study suggested that the pro-survival effect of CA on PTX-treated lung cancer cells is mediated through a NF-κB signaling pathway. This may provide mechanistic insights into the chemoresistance of cancer calls.

  17. Evaluation of the effect of Chrysin and Caffeic acid phenethyl ester on eIF4E expression in AGS cell line

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    Abolhasani Marziyeh

    2014-04-01

    Full Text Available Introduction: The Ras/Akt/mTORC1 signal transduction pathways play a critical role in regulating translation and converge on initiation factor eukaryotic translation initiation factor 4E (eIF4E which is overexpressed in various malignancies. In the current study we aimed to assess the effect of chrysin and caffeic acid phenethyl ester (CAPE on eIF4E expression level in human stomach cancer AGS cell line. Methods: AGS cells were treated with 15, 20, 30 and 40 μM concentration of chrysin and CAPE separately, then eIF4E expression was evaluated in treated cells using real time-PCR method. Results: A significant decrease in eIF4E expression in the cells following 40 μM chrysin treatment was observed (p<0.05. There was a significant decrease in CAPE-treated cells in a dose dependent manner. Indeed the cells treated with 30 and 40 μM concentrations of CAPE, showed a significant decline in eIF4E expression (p<0.05. Conclusion: Our results suggest that CAPE and chrysin may be useful as a potential therapeutic agent for treatment of gastric cancers with an elevated eIF4E expression level.

  18. Determination of the Structure and Catalytic Mechanism of Sorghum bicolor Caffeic Acid O-Methyltransferase and the Structural Impact of Three brown midrib12 Mutations1[W

    Science.gov (United States)

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

    2014-01-01

    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

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

    Science.gov (United States)

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

    2014-08-01

    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 K m 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. © 2014 American Society of Plant Biologists. All Rights Reserved.

  20. Caffeic acid attenuates the inflammatory stress induced by glycated LDL in human endothelial cells by mechanisms involving inhibition of AGE-receptor, oxidative, and endoplasmic reticulum stress.

    Science.gov (United States)

    Toma, Laura; Sanda, Gabriela M; Niculescu, Loredan S; Deleanu, Mariana; Stancu, Camelia S; Sima, Anca V

    2017-09-10

    Type 2 diabetes mellitus is a worldwide epidemic and its atherosclerotic complications determine the high morbidity and mortality of diabetic patients. Caffeic acid (CAF), a phenolic acid present in normal diets, is known for its antioxidant properties. The aim of this study was to investigate CAF's anti-inflammatory properties and its mechanism of action, using cultured human endothelial cells (HEC) incubated with glycated low-density lipoproteins (gLDL). Levels of the receptor for advanced glycation end-products (RAGE), inflammatory stress markers (C reactive protein, CRP; vascular cell adhesion molecule-1, VCAM-1; monocyte chemoattractant protein-1, MCP-1), and oxidative stress and endoplasmic reticulum stress (ERS) markers were evaluated in gLDL-exposed HEC, in the presence/absence of CAF. RAGE silencing or blocking, specific inhibitors for oxidative stress (apocynin, N-acetyl-cysteine), and ERS (salubrinal) were used. The results showed that: (i) gLDL induced CRP synthesis and secretion through mechanisms involving NADPH oxidase-dependent oxidative stress and ERS in HEC; (ii) gLDL-RAGE interaction, oxidative stress, and ERS stimulated the secretion of VCAM-1 and MCP-1 in HEC; and (iii) CAF reduced the secretion of CRP, VCAM-1, and MCP-1 in gLDL-exposed HEC by inhibiting RAGE expression, oxidative stress, and ERS. In conclusion, CAF might be a promising alternative to ameliorate a wide spectrum of disorders due to its complex mechanisms of action resulting in anti-inflammatory and antioxidative properties. © 2017 BioFactors, 43(5):685-697, 2017. © 2017 International Union of Biochemistry and Molecular Biology.

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

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    Ewa Skała

    2015-01-01

    Full Text Available 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.

  2. PHYSICAL AND CHEMICAL STABILITY ANALYSIS OF COSMETIC MULTI- PLE EMULSIONS LOADED WITH ASCORBYL PALMITATE AND SODIUM ASCORBYL PHOSPHATE SALTS.

    Science.gov (United States)

    Khan, Hira; Akhtar, Naveed; Ali, Atif; Khan, Haji M Shoaib; Sohail, Muhammad; Naeem, Muhammad; Nawaz, Zarqa

    2016-09-01

    Stability of hydrophilic and lipophilic vitamin C derivatives for quenching synergistic antioxidant activities and to treat oxidative related diseases is a major issue. This study was aimed to encapsulate hydrophilic and lipophilic vitamin C derivatives (ascorbyl palmitate and sodium ascorbyl phosphate) as functional ingredients in a newly formulated multiple emulsion of the W//W type to attain the synergistic antioxidant effects and the resultant system's long term physical and chemical stability. Several multiple emulsions using the same concentration of emulsifiers but different concentrations of ascorbyl palmitate and sodium ascorbyl phosphate were developed. Three finally selected multiple emulsions (ME₁, ME₂ and ME₃) were evaluated for physical stability in terms of rheology, microscopy, conductivity, pH, and organoleptic characteristics under different storage conditions for 3 months. Chemical stability was determined by HPLC on Sykam GmbH HPLC system (Germany), equipped with a variable UV detector. Results showed that at accelerated storage conditions all the three multiple emulsions had shear thinning behavior of varying shear stress with no influence of location of functional ingredients in a carrier system. Conductivity values increased and pH values remained within the skin pH range for 3 months. Microscopic analysis showed an increase in globule size with the passage of time, especially at higher temperatures while decreased at low temperatures. Centrifugation test did not cause phase separation till the 45th day, but little effects after 2 months. Chemical stability analysis by HPLC at the end of 3 months showed that ascorbyl palmitate and sodium ascorbyl phosphate were almost stable in all multiple emulsions with no influence of their location in a carrier system. Multiple emulsions were found a stable carrier for hydrophilic and lipophilic vitamin C derivatives to enhance their desired effects. Considering that many topical formulations

  3. An unusual caffeic acid derived bicyclic [2.2.2] octane lignan and other constituents from Cordia rufescens.

    Science.gov (United States)

    do Vale, Ademir E; David, Jorge M; dos Santos, Edlene O; David, Juceni P; e Silva, Lidercia C R C; Bahia, Marcus V; Brandão, Hugo N

    2012-04-01

    This work reports isolation of an unusual lignan with a bicyclic [2.2.2] octene skeleton, named rufescenolide (1), from stems of Cordia rufescens, along with β-sitosterol, stigmasterol, syringaldehyde, 3-β-O-D-glucopyranosyl-sitosterol, methyl caffeate, 4-methoxy-protocatechuic acid and methyl rosmarinate. Structural characterizations employed IR spectroscopic, ESIHRMS and mono and dimensional NMR spectroscopy. Copyright © 2011 Elsevier Ltd. All rights reserved.

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

    Science.gov (United States)

    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.

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

    Science.gov (United States)

    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

  6. Caffeic acid, a phenol found in white wine, modulates endothelial nitric oxide production and protects from oxidative stress-associated endothelial cell injury.

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    Massimiliano Migliori

    Full Text Available 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.The aim of the present study was to investigate the protective effect of low doses of CAF on oxidative stress-induced endothelial injury.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.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.

  7. Chloroplast overexpression of rice caffeic acid O-methyltransferase increases melatonin production in chloroplasts via the 5-methoxytryptamine pathway in transgenic rice plants.

    Science.gov (United States)

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

    2017-08-01

    Recent analyses of the enzymatic features of various melatonin biosynthetic genes from bacteria, animals, and plants have led to the hypothesis that melatonin could be synthesized via the 5-methoxytryptamine (5-MT) pathway. 5-MT is known to be synthesized in vitro from serotonin by the enzymatic action of O-methyltransferases, including N-acetylserotonin methyltransferase (ASMT) and caffeic acid O-methyltransferase (COMT), leading to melatonin synthesis by the subsequent enzymatic reaction with serotonin N-acetyltransferase (SNAT). Here, we show that 5-MT was produced and served as a precursor for melatonin synthesis in plants. When rice seedlings were challenged with senescence treatment, 5-MT levels and melatonin production were increased in transgenic rice seedlings overexpressing the rice COMT in chloroplasts, while no such increases were observed in wild-type or transgenic seedlings overexpressing the rice COMT in the cytosol, suggesting a 5-MT transport limitation from the cytosol to chloroplasts. In contrast, cadmium treatment led to results different from those in senescence. The enhanced melatonin production was not observed in the chloroplast COMT lines relative over the cytosol COMT lines although 5-MT levels were equally induced in all genotypes upon cadmium treatment. The transgenic seedlings with enhanced melatonin in their chloroplasts exhibited improved seedling growth vs the wild type under continuous light conditions. This is the first report describing enhanced melatonin production in chloroplasts via the 5-MT pathway with the ectopic overexpression of COMT in chloroplasts in plants. © 2017 John Wiley & Sons A/S. Published by John Wiley & Sons Ltd.

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

    Directory of Open Access Journals (Sweden)

    Christine Becker

    Full Text Available 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.

  9. 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

    OpenAIRE

    Lin, Hui-Ping; Lin, Ching-Yu; Huo, Chieh; Hsiao, Ping-Hsuan; 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 CAP...

  10. Sulfated caffeic acid dehydropolymer attenuates elastase and cigarette smoke extract-induced emphysema in rats: sustained activity and a need of pulmonary delivery.

    Science.gov (United States)

    Saluja, Bhawana; Li, Hua; Desai, Umesh R; Voelkel, Norbert F; Sakagami, Masahiro

    2014-08-01

    Although emphysema destroys alveolar structures progressively and causes death eventually, no drug has been discovered to prevent, intervene, and/or resolve this life-threatening disease. We recently reported that sulfated caffeic acid dehydropolymer CDSO3 is a novel potent triple-action inhibitor of elastolysis, oxidation, and inflammation in vitro, and therefore, a potential anti-emphysema agent. However, the in vivo therapeutic potency, duration and mode of actions, and effective route remain to be demonstrated. Emphysema was induced in rats with human sputum elastase (HSE) combined with cigarette smoke extract (CSE). CDSO3 at 5, 30, or 100 μg/kg was dosed to the lung or injected subcutaneously at 2, 6, or 24 h before or 1 or 24 h or 1 week after the HSE/CSE instillation. At 1 h or 48 h or on day 21-22 or day 28, lungs were examined for airway-to-blood injurious barrier damage; their elastolytic, oxidative, and inflammatory activities; lung luminal leukocytes infiltration; functional treadmill exercise endurance; and/or morphological airspace enlargement. CDSO3, when dosed to the lung at 30 or 100 μg/kg, but not via systemic subcutaneous injection, significantly (43-93 %) attenuated HSE/CSE-induced (1) barrier damage measured by luminal hemorrhage and protein leak; (2) elastolytic, oxidative, and inflammatory activities measured with elastase, reduced glutathione, and TNFα levels, respectively; (3) luminal neutrophil infiltration and tissue myeloperoxidase activity; (4) functional impairment of exercise endurance; and (5) airspace enlargement, in both preventive and interventional dosing protocols. Notably, the effects were shown to last for 24 h at the greater 100-μg/kg dose, and the 1-week-delayed administration was also capable of attenuating the development of emphysema. CDSO3 is a novel, potent, long-acting, nonpeptidic macromolecule that inhibits HSE/CSE-induced elastolysis, oxidation, and inflammation in the lung and thereby attenuates the development

  11. Ameliorating Role of Caffeic Acid Phenethyl Ester (CAPE Against Methotrexate-Induced Oxidative Stress in the Sciatic Nerve, Spinal Cord and Brain Stem Tissues of Rats

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    Ertuğrul Uzar

    2010-03-01

    Full Text Available OBJECTIVE: Methotrexate (MTX-associated neurotoxicity is an important clinical problem in cancer patients, but the mechanisms of MTX-induced neurotoxicity are not yet known exactly. The aims of this study were (1 to investigate the possible role of malondialdehyde (MDA, superoxide dismutase (SOD enzyme, glutathione peroxidase (GSH-Px and catalase (CAT in the pathogenesis of MTX-induced neurotoxicity and (2 to determine whether there is a putative protective effect of caffeic acid phenethyl ester (CAPE on MTX-induced neurotoxicity in the spinal cord, brainstem and sciatic nerve of rats. METHODS: A total of 19 adult Wistar male rats were divided into three experimental groups. Group I, control group; Group II, MTX-treated group; and Group III, MTX + CAPE-treated group. MTX was administered to the MTX and MTX + CAPE groups intraperitoneally (IP with a single dose of 20 mg/kg on the second day of the experiment. CAPE was administered to the MTX + CAPE group IP with a dose of 10 μmol/kg for 7 days. RESULTS: In the sciatic nerve and spinal cord tissue, CAT and GSH-Px activities were increased in the MTX group in comparison with the control group. CAPE treatment with MTX significantly decreased CAT and GSH-Px activities in the neuronal tissues of rats in comparison with the MTX group. In the spinal cord and brainstem tissues, SOD activity in the MTX group was decreased in comparison with the control group, but in the sciatic nerve, there was no significant difference. In the spinal cord and brainstem of rats, SOD activity was increased in the CAPE + MTX group when compared with the MTX group. The level of MDA was higher in the MTX group than in the control group. CAPE administration with MTX injection caused a significant decrease in MDA level when compared with the MTX group. CONCLUSION: These results reveal that MTX increases oxidative stress in the sciatic nerve, spinal cord and brainstem of rats and that CAPE has a preventive effect on the

  12. Protective Effect of Combined Caffeic Acid Phenethyl Ester and Bevacizumab Against Hydrogen Peroxide-Induced Oxidative Stress in Human RPE Cells.

    Science.gov (United States)

    Dinc, Erdem; Ayaz, Lokman; Kurt, Akif Hakan

    2017-12-01

    This study aimed to evaluate the protective effects of caffeic acid phenethyl ester (CAPE) and combined CAPE-bevacizumab against oxidative stress induced by hydrogen peroxide (H 2 O 2 ) in human retinal pigment epithelium. ARPE-19 cells were pretreated with 5, 10, and 30 μM CAPE alone and in combination with bevacizumab for 3 h, then exposed to H 2 O 2 for 16 h. Cell viability was evaluated with the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Vascular endothelial growth factor (VEGF) protein levels in the medium were measured using a human VEGF ELISA kit. Total antioxidant status (TAS) and total oxidant status (TOS) were measured in ARPE-19 cells using the test kit from Rel Assay. Expression levels of VEGF, Bax, Bcl-2, cytochrome c, apoptotic protease activating factor-1 (apaf-1), and caspase-3 were determined using reverse transcription polymerase chain reaction. Pretreatment of ARPE-19 cells with 30 μM CAPE and combined CAPE-bevacizumab reduced H 2 O 2 mediated cell death. H 2 O 2 -induced oxidative stress increased TOS and VEGF production, which was significantly inhibited by CAPE and the CAPE-bevacizumab combination. VEGF, Bax, cytochrome c, apaf-1, and caspase-3 gene expressions were significantly decreased in cells pretreated with 5, 10, and 30 μM CAPE and combined CAPE-bevacizumab compared to the H 2 O 2 group. In addition, Bcl-2 expression was significantly increased in both the CAPE and CAPE-bevacizumab combination groups compared to the H 2 O 2 group. CAPE has a protective effect on ARPE-19 cells against oxidative stress, and VEGF protein level and expression can be decreased by incubation with different concentrations of CAPE. These results demonstrate that CAPE suppresses the mitochondria-mediated apoptosis in ARPE-19 cells under oxidative stress. In addition, the use of CAPE in combination with bevacizumab has an additive effect.

  13. Reuse of Organomineral Substrate Waste from Hydroponic Systems as Fertilizer in Open-Field Production Increases Yields, Flavonoid Glycosides, and Caffeic Acid Derivatives of Red Oak Leaf Lettuce (Lactuca sativa L.) Much More than Synthetic Fertilizer.

    Science.gov (United States)

    Dannehl, Dennis; Becker, Christine; Suhl, Johanna; Josuttis, Melanie; Schmidt, Uwe

    2016-09-28

    Effects of organic waste from a hydroponic system added with minerals (organomineral fertilizer) and synthetic fertilizer on major polyphenols of red oak leaf lettuce using HPLC-DAD-ESI-MS(3) were investigated. Interestingly, contents of the main flavonoid glycosides and caffeic acid derivatives of lettuce treated with organomineral fertilizer were equal to those synthesized without soil additives. This was found although soil nutrient concentrations, including that of nitrogen, were much lower without additives. However, lettuce treated with synthetic fertilizer showed a significant decrease in contents of caffeic acid derivatives and flavonoid glycosides up to 78.3 and 54.2%, respectively. It is assumed that a negative effect of a high yield on polyphenols as described in the growth-differentiation balance hypothesis can be counteracted by (i) a higher concentration of Mg or (ii) optimal physical properties of the soil structure. Finally, the organomineral substrate waste reused as fertilizer and soil improver resulted in the highest yield (+78.7%), a total fertilizer saving of 322 kg ha(-1) and waste reduction in greenhouses.

  14. Optimization of α-tocopherol and ascorbyl palmitate addition for the stabilization of sardine oil

    Directory of Open Access Journals (Sweden)

    Morales-Medina, R.

    2015-06-01

    Full Text Available The purpose of the present work was to optimize the addition of natural antioxidants (α- tocopherol and ascorbyl palmitate for the stabilization of sardine oil rich in omega-3 PUFA. The optimal values for peroxide value (PV, which minimizes primary oxidation products, were obtained at low concentrations of α-tocopherol (50–207 ppm, high content of ascorbyl palmitate (450 ppm and 50 ppm citric acid. On the other hand, optimal values for p-anisidine value (AV, which minimizes secondary oxidation products, were found at medium concentrations of α-tocopherol (478–493 ppm, high contents of ascorbyl palmitate (390–450 ppm and 50 ppm citric acid. The conflicting effect of α-tocopherol on the individual optimization of PV and AV motivated the generation of a Pareto front (set of non inferior solutions employing the weighted-sum multi-objective optimization technique.El objetivo de este trabajo fue optimizar la adición de antioxidantes naturales (α-tocoferol y palmitato de ascorbilo para la estabilización de aceite de sardina rico en omega-3 PUFA. Bajas concentraciones de α-tocoferol (50–207 ppm combinadas con la adicción de antioxidantes secundarios como palmitato de ascorbilo (450 ppm y ácido cítrico (50 ppm, minimizaron la formación de hidroperóxidos en el aceite de sardina estudiado. Sin embargo, los productos secundarios de oxidación se redujeron para concentraciones medias de α-tocoferol (478–493 ppm, altas de palmitato de ascorbilo (390–450 ppm y 50 ppm de ácido cítrico. El efecto contradictorio de la concentración de α-tocoferol en la optimización individual del índice de peróxidos e índice de p-anisidina motivó la realización de una optimización simultánea que permite satisfacer la optimización de cada una de las variables individuales en el grado deseado.

  15. 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

    Science.gov (United States)

    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.

  16. Synthesis of L-Ascorbyl Flurbiprofenate by Lipase-Catalyzed Esterification and Transesterification Reactions

    Directory of Open Access Journals (Sweden)

    Jia-ying Xin

    2017-01-01

    Full Text Available The synthesis of L-ascorbyl flurbiprofenate was achieved by esterification and transesterification in nonaqueous organic medium with Novozym 435 lipase as biocatalyst. The conversion was greatly influenced by the kinds of organic solvents, speed of agitation, catalyst loading amount, reaction time, and molar ratio of acyl donor to L-ascorbic acid. A series of solvents were investigated, and tert-butanol was found to be the most suitable from the standpoint of the substrate solubility and the conversion for both the esterification and transesterification. When flurbiprofen was used as acyl donor, 61.0% of L-ascorbic acid was converted against 46.4% in the presence of flurbiprofen methyl ester. The optimal conversion of L-ascorbic acid was obtained when the initial molar ratio of acyl donor to ascorbic acid was 5 : 1. kinetics parameters were solved by Lineweaver-Burk equation under nonsubstrate inhibition condition. Since transesterification has lower conversion, from the standpoint of productivity and the amount of steps required, esterification is a better method compared to transesterification.

  17. Structural Alterations of Lignins in Transgenic Poplars with Depressed Cinnamyl Alcohol Dehydrogenase or Caffeic Acid O-Methyltransferase Activity Have an Opposite Impact on the Efficiency of Industrial Kraft Pulping1

    Science.gov (United States)

    Lapierre, Catherine; Pollet, Brigitte; Petit-Conil, Michel; Toval, Gabriel; Romero, Javier; Pilate, Gilles; Leplé, Jean-Charles; Boerjan, Wout; Ferret, Valérie; De Nadai, Véronique; Jouanin, Lise

    1999-01-01

    We evaluated lignin profiles and pulping performances of 2-year-old transgenic poplar (Populus tremula × Populus alba) lines severely altered in the expression of caffeic acid/5-hydroxyferulic acid O-methyltransferase (COMT) or cinnamyl alcohol dehydrogenase (CAD). Transgenic poplars with CAD or COMT antisense constructs showed growth similar to control trees. CAD down-regulated poplars displayed a red coloration mainly in the outer xylem. A 90% lower COMT activity did not change lignin content but dramatically increased the frequency of guaiacyl units and resistant biphenyl linkages in lignin. This alteration severely lowered the efficiency of kraft pulping. The Klason lignin level of CAD-transformed poplars was slightly lower than that of the control. Whereas CAD down-regulation did not change the frequency of labile ether bonds or guaiacyl units in lignin, it increased the proportion of syringaldehyde and diarylpropane structures and, more importantly with regard to kraft pulping, of free phenolic groups in lignin. In the most depressed line, ASCAD21, a substantially higher content in free phenolic units facilitated lignin solubilization and fragmentation during kraft pulping. These results point the way to genetic modification of lignin structure to improve wood quality for the pulp industry. PMID:9880356

  18. Caffeic Acid Phenethyl Ester (Propolis Extract) Ameliorates Insulin Resistance by Inhibiting JNK and NF-κB Inflammatory Pathways in Diabetic Mice and HepG2 Cell Models.

    Science.gov (United States)

    Nie, Jiarui; Chang, Yaning; Li, Yujia; Zhou, Yingjun; Qin, Jiawen; Sun, Zhen; Li, Haibin

    2017-10-18

    Caffeic acid phenethyl ester (CAPE), extracted from propolis, was evaluated for the ameliorative effects on insulin resistance and the mechanisms were identified, using non-insulin-dependent diabetes mellitus (NIDDM) model mice and insulin resistance (IR) model cells. After 5 weeks of CAPE supplementation, insulin sensitivity, hyperlipidemia, and peroxisome proliferator-activated receptor-α (PPAR-α) levels were improved in mice. Proinflammatory cytokines in serum and the expressions of tumor necrosis factor-alpha (TNF-α) mRNA in tissues were markedly downregulated from CAPE-treated mice. In vitro, CAPE supplement significantly improved glucose consumption, glucose uptake, glycogen content, and oxidative stress and decreased expression of glucose-6-phosphatase (G6Pase) mRNA in cells. Both in vivo and in vitro, CAPE enhanced p-Akt (Ser473) and p-insulin receptor substrate (IRS)-1 (Tyr612), but inhibited p-JNK (Thr183/Tyr185), p-NF-κB p65 (Ser536), and nuclear translocation of p-NF-κB p65 (Ser536). In summary, CAPE can ameliorate insulin resistance through modulation of JNK and NF-κB signaling pathway in mice and HepG2 cells.

  19. Ascorbyl Stearate Promotes Apoptosis Through Intrinsic Mitochondrial Pathway in HeLa Cancer Cells.

    Science.gov (United States)

    Mane, Shirish D; Thoh, Maikho; Sharma, Deepak; Sandur, Santosh K; Naidu, K Akhilender

    2016-12-01

    Ascorbic acid is proposed to have antitumor potential against certain cancer types but has the limitation of requiring high doses for treating cancer. Ascorbyl stearate (ASC-S) is a fatty acid ester derivative of ascorbic acid with comparable potent apoptotic activity. The present study was aimed at understanding the pathway involved in apoptotic activity of ASC-S in cervical cancer cells. The effect of ASC-S on reactive oxygen species (ROS), and mitochondrial membrane potential (MMP) was studied in HeLa cells. Furthermore, the dose-dependent effect of ASC-S on release of cytochrome c, pro-caspase-9, caspase-3, BH3 interacting-domain death agonist (BID), truncated BH3 interacting-domain death agonist (t-BID), FAS ligand (FASL) and transcription factors nuclear factor-kappa B (NF-ĸB), nuclear factor of activated T-cells (NFAT) and activator protein-1 (AP1) were studied in HeLa cells. Treatment of HeLa cells with ASC-S significantly increased the MMP. The modulation of MMP resulted in cleavage of BID, expression of FAS, cleavage of pro-caspase-9 and release of cytochrome c into cytosol. In addition, ASC-S treatment resulted in deregulation of transcription factors NF-ĸB, NFAT and AP1, which play an important role in the development of inflammation and cancer. Our data, for the first time, suggest that ASC-S has an apoptotic effect against HeLa cells by inducing change in mitochondrial membrane permeability, cytochrome c release and subsequent activation of caspase-3 and NF-ĸB. Copyright© 2016 International Institute of Anticancer Research (Dr. John G. Delinassios), All rights reserved.

  20. Caffeic acid phenethylester increases stress resistance and enhances lifespan in Caenorhabditis elegans by modulation of the insulin-like DAF-16 signalling pathway.

    Science.gov (United States)

    Havermann, Susannah; Chovolou, Yvonni; Humpf, Hans-Ulrich; Wätjen, Wim

    2014-01-01

    CAPE is an active constituent of propolis which is widely used in traditional medicine. This hydroxycinnamic acid derivate is a known activator of the redox-active Nrf2 signalling pathway in mammalian cells. We used C. elegans to investigate the effects of this compound on accumulation of reactive oxygen species and the modulation of the pivotal redox-active pathways SKN-1 and DAF-16 (homologues of Nrf2 and FoxO, respectively) in this model organism; these results were compared to the effects in Hct116 human colon carcinoma cells. CAPE exerts a strong antioxidative effect in C. elegans: The increase of reactive oxygen species induced by thermal stress was diminished by about 50%. CAPE caused a nuclear translocation of DAF-16, but not SKN-1. CAPE increased stress resistance of the nematode against thermal stress and finally a prolongation of the median and maximum lifespan by 9 and 17%, respectively. This increase in stress resistance and lifespan was dependent on DAF-16 as shown in experiments using a DAF-16 loss of function mutant strain. Life prolongation was retained under SKN-1 RNAi conditions showing that the effect is SKN-1 independent. The results of CAPE obtained in C. elegans differed from the results obtained in Hct116 colon carcinoma cells: CAPE also caused strong antioxidative effects in the mammalian cells, but no activation of the FoxO4 signalling pathway was detectable. Instead, an activation of the Nrf2 signalling pathway was shown by luciferase assay and western blots. CAPE activates the insulin-like DAF-16, but not the SKN-1 signalling pathway in C. elegans and therefore enhances the stress resistance and lifespan of this organism. Since modulation of the DAF-16 pathway was found to be a pivotal effect of CAPE in C. elegans, this has to be taken into account for the investigation of the molecular mechanisms of the traditional use of propolis.

  1. Determination of tocopheryl acetate and ascorbyl tetraisopalmitate in cosmetic formulations by HPLC.

    Science.gov (United States)

    Almeida, M M; Alves, J M P; Patto, D C S; Lima, C R R C; Quenca-Guillen, J S; Santoro, M I R M; Kedor-Hackmann, E R M

    2009-12-01

    A rapid HPLC method was developed for the assay of tocopheryl acetate and ascorbyl tetraisopalmitate in cosmetic formulations. The validated method was applied for quantitative determination of these vitamins in simulated emulsion formulation. Samples were analysed directly on a RP-18 reverse phase column with UV detection at 222 nm. A mixture of methanol and isopropanol (25 : 75 v/v) was used as mobile phase. The retention time of tocopheryl acetate and ascorbyl tetraisopalmitate were 3.0 min and 5.9 min, respectively. Recovery was between 95% and 104%. In addition, the excipients did not interfere in the analysis. The method is simple, reproducible, selective and is suitable for routine analyses of commercial products.

  2. Multivariate optimization of a synergistic blend of oleoresin sage (Salvia officinalis L.) and ascorbyl palmitate to stabilize sunflower oil.

    Science.gov (United States)

    Upadhyay, Rohit; Mishra, Hari Niwas

    2016-04-01

    The simultaneous optimization of a synergistic blend of oleoresin sage (SAG) and ascorbyl palmitate (AP) in sunflower oil (SO) was performed using central composite and rotatable design coupled with principal component analysis (PCA) and response surface methodology (RSM). The physicochemical parameters viz., peroxide value, anisidine value, free fatty acids, induction period, total polar matter, antioxidant capacity and conjugated diene value were considered as response variables. PCA reduced the original set of correlated responses to few uncorrelated principal components (PC). The PC1 (eigen value, 5.78; data variance explained, 82.53 %) was selected for optimization using RSM. The quadratic model adequately described the data (R (2) = 0. 91, p  0.05). The contour plot of PC 1 score indicated the optimal synergistic combination of 1289.19 and 218.06 ppm for SAG and AP, respectively. This combination of SAG and AP resulted in shelf life of 320 days at 25 °C estimated using linear shelf life prediction model. In conclusion, the versatility of PCA-RSM approach has resulted in an easy interpretation in multiple response optimizations. This approach can be considered as a useful guide to develop new oil blends stabilized with food additives from natural sources.

  3. Ascorbyl palmitate, gamma-tocopherol, and EDTA affect lipid oxidation in fish oil enriched salad dressing differently

    DEFF Research Database (Denmark)

    Let, M.B.; Jacobsen, Charlotte; Meyer, Anne S.

    2007-01-01

    The aim of the study was to investigate the ability of γ-tocopherol, ethylenediaminetetraacetate (EDTA), and ascorbyl palmitate to protect fish oil enriched salad dressing against oxidation during a 6 week storage period at room temperature. The lipid-soluble γ-tocopherol (220 and 880 µg g-1...

  4. Clicked Cinnamic/Caffeic Esters and Amides as Radical Scavengers and 5-Lipoxygenase Inhibitors

    Directory of Open Access Journals (Sweden)

    Jérémie A. Doiron

    2014-01-01

    Full Text Available 5-Lipoxygenase (5-LO is the key enzyme responsible for the conversion of arachidonic acid to leukotrienes, a class of lipid mediators implicated in inflammatory disorders. In this paper, we describe the design, synthesis, and preliminary activity studies of novel clicked caffeic esters and amides as radical scavengers and 5-LO inhibitors. From known 5-LO inhibitor 3 as a lead, cinnamic esters 8a–h and amides 9a–h as well as caffeic esters 15a–h and amides 16a–h were synthesized by Cu(I-catalyzed [1,3]-dipolar cycloaddition with the appropriate azide precursors and terminal alkynes. All caffeic analogs are proved to be good radical scavengers (IC50: 10–20 μM. Esters 15g and 15f possessed excellent 5-LO inhibition activity in HEK293 cells and were equipotent with the known 5-LO inhibitor CAPE and more potent than Zileuton. Several synthesized esters possess activities rivaling Zileuton in stimulated human polymorphonuclear leukocytes.

  5. Ascorbyl stearate and ionizing radiation potentiate apoptosis through intracellular thiols and oxidative stress in murine T lymphoma cells.

    Science.gov (United States)

    Mane, Shirish D; Kamatham, Akhilender Naidu

    2018-02-01

    Ascorbyl stearate (Asc-s) is a derivative of ascorbic acid with better anti-tumour efficacy compared to its parent compound ascorbic acid. In this study, we have examined radio-sensitizing effect of Asc-s in murine T cell lymphoma (EL4) cells at 4 Gy. Asc-s and radiation treatment reduced cell proliferation, induced apoptosis in a dose dependent manner by arresting the cells at S/G2-M phase of cell cycle. It also decreased the frequency of cancer stem cells per se, with significantly higher decrease in combination with radiation treatment./Further, Asc-s and radiation treatment increased the level of reactive oxygen species (ROS), drop in mitochondrial membrane potential (MMP) and increased caspase-3 activity resulting in apoptosis of EL4 cells. Further it also significantly decreased GSH/GSSG ratio due to binding of Asc-s with thiols. The increase in oxidative stress induced by Asc-s and radiation treatment was abrogated by thiol antioxidants in EL4 cells. Interestingly, this redox modulation triggered significant increase in protein glutathionylation in a time dependent manner. Asc-s treatment resulted in glutathionylation of IKK, p50-NF-kB and mutated p53, thereby inhibiting cancer progression during oxidative stress. Asc-s quenches GSH ensuing Asc-s + GSH adduct thereby further modulating GSH/GSSG ratio as evident from HPLC and docking studies. The anti-tumour effect of Asc-s along with radiation was studied by injecting EL4 cells in synegenicC57/BL6 male mice. Intraperitoneal injection of Asc-s followed by radiation exposure at 4 Gy to the tumour bearing mice resulted in radio-sensitization which is evident from significant regression of tumour as evident from tumour burden index. The survival study supports the data that Asc-s pre-treatment enhances radio-sensitization in murine lymphoma. Our data, suggest that Asc-s and ionizing radiation induced cell cycle arrest and apoptosis by perturbing redox balance through irreversible complexes of thiols with Asc

  6. The Effect of 3% Phosphate Ascorbyl Gel on Bond Strength of Composite Resin to Enamel treated with 35% Hydrogen Peroxide.

    Science.gov (United States)

    de Castro, Milena de Fátima Schalcher; Silva, Alice Carvalho; Franco, Marcela Mayana Pereira; Silva, Ana Paula Brito; Bramante, Fausto da Silva; da Silva, Monica Barros; Lima, Darlon Martins; Pereira, Adriana de Fátima Vasconcelos

    2015-05-01

    To evaluate the effect of 3% phosphate ascorbyl gel (PA) in different times onto the microshear bond strength of composite resin (CR) to bovine enamel treated with 35% hydrogen peroxide (HP). Thirty enamel blocks of bovine incisors were made and divided into 5 groups (n = 6) with three specimens per group (n = 18), according to treatment: G1= No bleaching + CR; G2 = HP + CR after 15d; G3 = HP + CR after 24 hours; G4 = HP + PA (15 min) + CR after 24 hours; G5 = HP + PA (2 hours) + CR after 24 hours. The resin cylinders were made by Tygon matrices. Microshear bond strength test was performed using universal testing machine with a 50N load at a speed of 0.5 mm/min. Fracture modes were assessed by a stereomicroscope 40 ×. Microshear bond strength values were submitted to the analysis of variance (ANOVA) one-way and Tukey test (p 0.05). Failure modes were categorized into adhesive (90%) and mixed (10%). The use of 3% phosphate ascorbyl gel for 15 minutes was able to improve bond strength of composite resin to bleached bovine enamel, but when 3% phosphate ascorbyl gel was applied during 40 minutes it negatively interfered in the adhesion of the resin to bleached bovine enamel.

  7. Topical Application of Trisodium Ascorbyl 6-Palmitate 2-Phosphate Actively Supplies Ascorbate to Skin Cells in an Ascorbate Transporter-Independent Manner

    Directory of Open Access Journals (Sweden)

    Shuichi Shibuya

    2017-06-01

    Full Text Available Ascorbic acid (AA possesses multiple beneficial functions, such as regulating collagen biosynthesis and redox balance in the skin. AA derivatives have been developed to overcome this compound’s high fragility and to assist with AA supplementation to the skin. However, how AA derivatives are transferred into cells and converted to AA in the skin remains unclear. In the present study, we showed that AA treatment failed to increase the cellular AA level in the presence of AA transporter inhibitors, indicating an AA transporter-dependent action. In contrast, torisodium ascorbyl 6-palmitate 2-phosphate (APPS treatment significantly enhanced the cellular AA level in skin cells despite the presence of inhibitors. In ex vivo experiments, APPS treatment also increased the AA content in a human epidermis model. Interestingly, APPS was readily metabolized and converted to AA in keratinocyte lysates via an intrinsic mechanism. Furthermore, APPS markedly repressed the intracellular superoxide generation and promoted viability associated with an enhanced AA level in Sod1-deficient skin cells. These findings indicate that APPS effectively restores the AA level and normalizes the redox balance in skin cells in an AA transporter-independent manner. Topical treatment of APPS is a beneficial strategy for supplying AA and improving the physiology of damaged skin.

  8. Nanocarrier with self-antioxidative property for stabilizing and delivering ascorbyl palmitate into skin.

    Science.gov (United States)

    Janesirisakule, Sirinapa; Sinthusake, Tarit; Wanichwecharungruang, Supason

    2013-08-01

    The concept of a nanocarrier with a self-antioxidative property to deliver and stabilize a labile drug while at the same time providing a free radical scavenging activity is demonstrated. Curcumin was grafted onto a poly(vinyl alcohol) [PV(OH)] chain, and the nanocarriers fabricated from the obtained curcumin-grafted PV(OH) polymer [CUR-PV(OH)] showed a good free radical scavenging activity. Ascorbyl palmitate (AP) could be effectively loaded into the CUR-PV(OH) at 29% by weight. The CUR-PV(OH)-encapsulated AP was 77% more stable than the free (unencapsulated) AP, and 47% more stable than AP encapsulated in the control nanocarrier with no antioxidative property [cinnamoyl-grafted PV(OH); CIN-PV(OH)]. Although coencapsulation of curcumin and AP into CIN-PV(OH) showed some improvement on the AP stability, AP was more stable when encapsulated in CUR-PV(OH). Compared with the free AP, encapsulated AP within the CUR-PV(OH) nanocarriers showed not only a better penetration into pig skin dermis via hair follicle pathway followed by the release and diffusion of the AP, but also a greater AP stability after skin application. Although a proof of principle is shown for CUR-PV(OH) and AP, it is likely that other carriers of the same principal could be designed and applied to different oxidation-sensitive drugs. Copyright © 2013 Wiley Periodicals, Inc.

  9. Simultaneous determination of chlorogenic acid, caffeic acid and caffeine in hydroalcoholic and aqueous extracts of Ilex paraguariensis by HPLC and correlation with antioxidant capacity of the extracts by DPPH· reduction Determinação simultânea de ácido clorogênico, ácido caféico e cafeína, no extrato aquoso e hidroalcoólico de Ilex paraguariensis por CLAE e correlação com a capacidade antioxidante dos extratos por redução do DPPH·

    Directory of Open Access Journals (Sweden)

    Diogo Pineda Rivelli

    2007-06-01

    Full Text Available A new high performance liquid chromatographic method has been established for simultaneous determination of chlorogenic acid, caffeic acid and caffeine in hydroalcoholic and aqueous extracts of Ilex paraguariensis. Analytical curves showed good linear regression in the concentration ranges 0.49-7.8 µg/mL for chlorogenic acid, 0.25-3.9 µg/mL for caffeic acid and 0.244-7.8 µg/mL for caffeine. Reduction of the DPPH· radical was used to determine the antioxidant capacity of the extracts. Our method for the simultaneous determination of chlorogenic acid, caffeic acid and caffeine was highly sensitive, having lower detection and quantitation limits than other papers that used similar methodology.Um novo método de cromatografia líquida de alta eficiência foi desenvolvido para a determinação simultânea de ácido clorogênico, ácido caféico e cafeína no extrato hidroalcoólico e aquoso de Ilex paraguariensis. As curvas de calibração mostraram boa regressão linear nas faixas de concentração 0,49-7,8 µg/mL para o ácido clorogênico, 0,25-3,9 µg/mL para ácido caféico e 0,244-7,8 µg/mL para cafeína. A redução do radical DPPH· foi usada para determinar a capacidade antioxidante dos extratos. Nosso método para a determinação simultânea de ácido caféico, ácido clorogênico e cafeína foi altamente sensível, possuindo limites de detecção e de quantificação menores do que em outros trabalhos que empregaram metodologias semelhantes.

  10. A Fluorescent Assay for Plant Caffeic Acid O-methyltransferases

    Science.gov (United States)

    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-...

  11. Caffeic Acid Phenethyl Ester (CAPE) mediated decrease in ...

    African Journals Online (AJOL)

    ... is a phytochemically active component obtained from honeybee hive propolis. ... We hypothesize the effect of CAPE on the metastasis of colon cancer cells in ... evaluated also expression of protein and matrix metalloproteinases (MMPs) ...

  12. Effect of L-Ascorbyl-2-Phosphate Magnesium as a Vitamin C Source in Different Doses on Growth of Patin Pangasius Hypophthalmus Fingerlings

    Directory of Open Access Journals (Sweden)

    D. Jusadi

    2007-01-01

    Full Text Available This study was aimed to determine optimum dose of L-Ascorbyl-2-Phosphate Magnesium in the diet of patin, Pangasius hypophthalmus fingerlings.  Five isoprotein and isocaloric diets containing different dose of L-Ascorbyl-2-Phosphate Magnesium, i.e. 0, 25, 75 and 100 mg/kg diet were used in this experiment.  Fish with an average size of 5.00±0.11 g were maintained at a density of 15 fish per aquarium.  Fish were fed three times a day at satiation, for 40 days.  The results of study shows that vitamin C content in fish body increased as the vitamin C level of the diet increased.  Similar pattern to vitamin C content was also found in protein retention, lipid retention, daily growth rate, and feed efficiency (p Keywords: vitamin C, patin, Pangasius hypophthalmus.   ABSTRAK Penelitian ini bertujuan untuk menentukan kadar optimum L-Ascorbyl-2-Phosphate Magnesium dalam pakan ikan patin, Pangasius hypophthalmus ukuran sejari. Lima macam pakan isoprotein dan isokalori mempunyai kandungan L-Ascorbyl-2-Phosphate Magnesium berbeda, berturut-turut 0, 25, 50, 75 dan 100 mg/kg pakan telah digunakan dalam penelitian ini. Benih berukuran rata-rata 5,00±0,11 g dipelihara dalam akuarium dengan kepadatan 15 ekor per akuarium. Ikan diberi pakan tiga kali sehari, secara at satiation, selama 40 hari. Hasil penelitian menunjukkan bahwa kadar vitamin C tubuh meningkat sejalan dengan kadar vitamin C pakan. Demikian pula retensi protein, retensi lemak laju pertumbuhan harian, efisiensi pakan mengikuti pola yang sama seperti kandungan vitamin C tubuh (p Kata kunci: vitamin C, ikan patin, Pangasius hypophthalmus.

  13. Oxidative stability of a heme iron-fortified bakery product: Effectiveness of ascorbyl palmitate and co-spray-drying of heme iron with calcium caseinate.

    Science.gov (United States)

    Alemán, Mercedes; Bou, Ricard; Tres, Alba; Polo, Javier; Codony, Rafael; Guardiola, Francesc

    2016-04-01

    Fortification of food products with iron is a common strategy to prevent or overcome iron deficiency. However, any form of iron is a pro-oxidant and its addition will cause off-flavours and reduce a product's shelf life. A highly bioavailable heme iron ingredient was selected to fortify a chocolate cream used to fill sandwich-type cookies. Two different strategies were assessed for avoiding the heme iron catalytic effect on lipid oxidation: ascorbyl palmitate addition and co-spray-drying of heme iron with calcium caseinate. Oxidation development and sensory acceptability were monitored in the cookies over one-year of storage at room temperature in the dark. The addition of ascorbyl palmitate provided protection against oxidation and loss of tocopherols and tocotrienols during the preparation of cookies. In general, ascorbyl palmitate, either alone or in combination with the co-spray-dried heme iron, prevented primary oxidation and hexanal formation during storage. The combination of both strategies resulted in cookies that were acceptable from a sensory point of view after 1year of storage. Copyright © 2015 Elsevier Ltd. All rights reserved.

  14. Electrochemical behavior of antioxidants: Part 3. Electrochemical studies of caffeic Acid–DNA interaction and DNA/carbon nanotube biosensor for DNA damage and protection

    Directory of Open Access Journals (Sweden)

    Refat Abdel-Hamid

    2016-05-01

    Full Text Available Multi-walled carbon nanotubes-modified glassy carbon electrode biosensor was used for electrochemical studies of caffeic acid–dsDNA interaction in phosphate buffer solution at pH 2.12. Caffeic acid, CAF, shows a well-defined cyclic voltammetric wave. Its anodic peak current decreases and the peak potential shifts positively on the addition of dsDNA. This behavior was ascribed to an interaction of CAF with dsDNA giving CAF–dsDNA complex by intercalative binding mode. The apparent binding constant of CAF–dsDNA complex was determined using amperometric titrations. The oxidative damage caused to DNA was detected using the biosensor. The damage caused by the reactive oxygen species, hydroxyl radical (·−OH generated by the Fenton system on the DNA-biosensor was detected. It was found that CAF has the capability of scavenging the hydroxide radical and protecting the DNA immobilized on the GCE surface.

  15. Differential effects of the ascorbyl and tocopheryl derivative on the methamphetamine-induced toxic behavior and toxicity

    International Nuclear Information System (INIS)

    Ito, Shinobu; Mori, Tomohisa; Kanazawa, Hideko; Sawaguchi, Toshiko

    2007-01-01

    A previous study showed that high doses of methamphetamine induce self-injurious behavior (SIB) in rodents. Furthermore, the combination of methamphetamine and morphine increased lethality in mice. We recently surmised that the rise in SIB and mortality induced by methamphetamine and/or morphine may be related to oxidative stress. The present study was designed to determine whether an antioxidant could inhibit SIB or mortality directly induced by methamphetamine and/or morphine. The SIB induced by 20 mg/kg of methamphetamine was abolished by the administration of Na L-ascorbyl-2-phosphate (APS: 300 mg/kg), but not Na DL-α-tocopheryl phosphate (TPNa: 200 mg/kg). In contrast, APS (300 mg/kg) and TPNa (200 mg/kg) each significantly attenuated the lethality induced by methamphetamine and morphine. The present study showed that the signal intensity of superoxide adduct was increased by 20 mg/kg of methamphetamine in the heart and lungs, and methamphetamine plus morphine tended to increase superoxide adduct in all of the tissues measured by ESR spin trap methods. Adduct signal induced in brain by methamphetamine administration increased in significance, but in mouse administrated methamphetamine plus morphine. There are differential effects of administration of methamphetamine and coadministration of methamphetamine plus morphine on adduct signal. These results suggest that APS and TPNa are effective for reducing methamphetamine-induced toxicity and/or toxicological behavior. While APS and TPNa each affected methamphetamine- and/or morphine-induced toxicology and/or toxicological behavior, indicating that both drugs have antioxidative effects, their effects differed

  16. Stability evaluation of tocopheryl acetate and ascorbyl tetraisopalmitate in isolation and incorporated in cosmetic formulations using thermal analysis

    Directory of Open Access Journals (Sweden)

    Mariana Mandelli de Almeida

    2010-03-01

    Full Text Available In view of the increase in the number of cosmetic preparations containing antioxidant vitamins, chiefly, due to their action in preventing the process of skin aging, there is a need to develop pre-formulation studies and to validate analytical methods in order to obtain high quality products. Thus, the objective of this research was to evaluate and compare the thermal behavior of tocopheryl acetate and ascorbyl tetraisopalmitate as raw materials, and incorporated into a base cream. Thermogravimetry (TG / DTG and differential scanning calorimetry (DSC were used for this purpose. Both vitamins were found to be stable up to 250ºC. The base cream (placebo and the sample (base cream containing the vitamins presented different weight loss. Thermal analysis has shown itself to be an excellent tool for the characterization of these vitamins and can be used in routine analysis for quality control of this type of cosmetic formulation.Considerando o potencial antioxidante das vitaminas utilizadas em produtos cosméticos, seu uso na prevenção do processo de envelhecimento da pele e a necessidade de estudos de pré-formulação que garantam o desenvolvimento de cosméticos de qualidade, foi objetivo deste trabalho avaliar e comparar o comportamento térmico dos ativos acetato de tocoferila e tetraisopalmitato de ascorbila, matérias-primas, isoladamente e incorporados em creme base. As técnicas termogravimetria/termogravimetria derivada (TG/DTG e calorimetria exploratória diferencial (DSC foram utilizadas para tal finalidade. Verificou-se que as vitaminas mantiveram-se estáveis até a temperatura de, aproximadamente, 250 ºC, observando-se diferença na perda de massa entre o creme base e o creme base associado às vitaminas. Assim sendo, a análise térmica mostrou-se como excelente ferramenta para caracterização das vitaminas e do creme base, podendo ser empregada em análises de rotina no controle de qualidade deste tipo de formulação cosmética.

  17. Encapsulating fatty acid esters of bioactive compounds in starch

    Science.gov (United States)

    Lay Ma, Ursula Vanesa

    Interest in the use of many bioactive compounds in foods is growing in large part because of the apparent health benefits of these molecules. However, many of these compounds can be easily degraded during processing, storage, or their passage through the gastrointestinal tract before reaching the target site. In addition, they can be bitter, acrid, or astringent, which may negatively affect the sensory properties of the product. Encapsulation of these molecules may increase their stability during processing, storage, and in the gastrointestinal tract, while providing controlled release properties. The ability of amylose to form inclusion complexes and spherulites while entrapping certain compounds has been suggested as a potential method for encapsulation of certain molecules. However, complex formation and spherulitic crystallization are greatly affected by the type of inclusion molecules, type of starch, and processing conditions. The objectives of the present investigation were to: (a) study the effect of amylose, amylopectin, and intermediate material on spherulite formation and its microstructure; (b) investigate the formation of amylose and high amylose starch inclusion complexes with ascorbyl palmitate, retinyl palmitate, and phytosterol esters; (c) evaluate the ability of spherulites to form in the presence of fatty acid esters and to entrap ascorbyl palmitate, retinyl palmitate, and phytosterol esters; and (d) evaluate the effect of processing conditions on spherulite formation and fatty acid ester entrapment. Higher ratios of linear to branched molecules resulted in the formation of more and rounder spherulites with higher heat stability. In addition to the presence of branches, it appears that spherulitic crystallization is also affected by other factors, such as degree of branching, chain length, and chain length distribution. Amylose and Hylon VII starch formed inclusion complexes with fatty acid esters of ascorbic acid, retinol, or phytosterols

  18. Oxidative stability of structured lipids produced from sunflower oil and caprylic acid

    DEFF Research Database (Denmark)

    Timm Heinrich, Maike; Xu, Xuebing; Nielsen, Nina Skall

    2003-01-01

    Traditional sunflower oil (SO), randomized lipid (RL) and specific structured lipid (SL), both produced from SO and tricaprylin/caprylic acid, respectively, were stored for up to 12 wk to compare their oxidative stabilities by chemical and sensory analyses. Furthermore, the effect of adding...... a commercial antioxidant blend Grindox 117 (propyl gallate/citric acid/ascorbyl palmitate) or gallic acid to the SL was investigated. The lipid type affected the oxidative stability: SL was less stable than SO and RL. The reduced stability was most likely caused by both the structure of the lipid...

  19. Synthesis, Anti-HCV, Antioxidant and Reduction of Intracellular Reactive Oxygen Species Generation of a Chlorogenic Acid Analogue with an Amide Bond Replacing the Ester Bond.

    Science.gov (United States)

    Wang, Ling-Na; Wang, Wei; Hattori, Masao; Daneshtalab, Mohsen; Ma, Chao-Mei

    2016-06-08

    Chlorogenic acid is a well known natural product with important bioactivities. It contains an ester bond formed between the COOH of caffeic acid and the 3-OH of quinic acid. We synthesized a chlorogenic acid analogue, 3α-caffeoylquinic acid amide, using caffeic and quinic acids as starting materials. The caffeoylquinc acid amide was found to be much more stable than chlorogenic acid and showed anti-Hepatitis C virus (anti-HCV) activity with a potency similar to chlorogenic acid. The caffeoylquinc acid amide potently protected HepG2 cells against oxidative stress induced by tert-butyl hydroperoxide.

  20. Antioxidant Activities and Caffeic Acid Content in New Zealand Asparagus (Asparagus officinalis Roots Extracts

    Directory of Open Access Journals (Sweden)

    Abbey Symes

    2018-04-01

    Full Text Available Asparagus officinalis are perennial plants that require re-planting every 10–20 years. The roots are traditionally mulched in the soil or treated as waste. The A. officinalis roots (AR contain valuable bioactive compounds that may have some health benefiting properties. The aim of this study was to investigate the total polyphenol and flavonoid contents (TPC and TFC, respectively and antioxidant (2,2-diphenyl-1-picrylhydrazyl (DPPH, Oxygen Radical Absorbance Capacity (ORAC and Ferric Reducing/Antioxidant Power (FRAP assays activities of New Zealand AR extract. The antioxidant activity decreased with a longer extraction time.

  1. OH-radical induced degradation of hydroxybenzoic- and hydroxycinnamic acids and formation of aromatic products-A gamma radiolysis study

    Energy Technology Data Exchange (ETDEWEB)

    Krimmel, Birgit; Swoboda, Friederike [University of Vienna, Department of Nutritional Sciences, Section Radiation Biology (Austria); Solar, Sonja, E-mail: sonja.solar@univie.ac.a [University of Vienna, Department of Nutritional Sciences, Section Radiation Biology (Austria); Reznicek, Gottfried [Department of Pharmacognosy, Althanstrasse 14, A-1090 Vienna (Austria)

    2010-12-15

    The OH-radical induced degradation of hydroxybenzoic acids (HBA), hydroxycinnamic acids (HCiA) and methoxylated derivatives, as well as of chlorogenic acid and rosmarinic acid was studied by gamma radiolysis in aerated aqueous solutions. Primary aromatic products resulting from an OH-radical attachment to the ring (hydroxylation), to the position occupied by the methoxyl group (replacement -OCH{sub 3} by -OH) as well as to the propenoic acid side chain of the cinnamic acids (benzaldehyde formations) were analysed by HPLC-UV and LC-ESI-MS. A comparison of the extent of these processes is given for 3,4-dihydroxybenzoic acid, vanillic acid, isovanillic acid, syringic acid, cinnamic acid, 4-hydroxycinnamic acid, caffeic acid, ferulic acid, isoferulic acid, chlorogenic acid, and rosmarinic acid. For all cinnamic acids and derivatives benzaldehydes were significant oxidation products. With the release of caffeic acid from chlorogenic acid the cleavage of a phenolic glycoside could be demonstrated. Reaction mechanisms are discussed.

  2. Neuroprotection comparison of chlorogenic acid and its metabolites against mechanistically distinct cell death-inducing agents in cultured cerebellar granule neurons.

    Science.gov (United States)

    Taram, Faten; Winter, Aimee N; Linseman, Daniel A

    2016-10-01

    While the number of patients diagnosed with neurodegenerative disorders like Alzheimer's disease, amyotrophic lateral sclerosis, and Parkinson's disease is increasing, there are currently no effective treatments that significantly limit the neuronal cell death underlying these diseases. Chlorogenic acid (CGA), a polyphenolic compound found in high concentration in coffee, is known to possess antioxidant and free radical scavenging activity. In this study, we investigated the neuroprotective effects of CGA and its major metabolites in primary cultures of rat cerebellar granule neurons. We show that CGA and caffeic acid displayed a dramatic protective effect against the nitric oxide donor, sodium nitroprusside. In marked contrast, ferulic acid and quinic acid had no protective effect against this nitrosative stress. While CGA and quinic acid had no protective effect against glutamate-induced cell death, caffeic acid and ferulic acid significantly protected neurons from excitotoxicity. Finally, caffeic acid was the only compound to display significant protective activity against hydrogen peroxide, proteasome inhibition, caspase-dependent intrinsic apoptosis, and endoplasmic reticulum stress. These results indicate that caffeic acid displays a much broader profile of neuroprotection against a diverse range of stressors than its parent polyphenol, CGA, or the other major metabolites, ferulic acid and quinic acid. We conclude that caffeic acid is a promising candidate for testing in pre-clinical models of neurodegeneration. Copyright © 2016 Elsevier B.V. All rights reserved.

  3. Ascorbyl Tetraisopalmitate Inclusion into Υ-Cyclodextrin and Mesoporous SBA-15: Preparation, Characterization and In Vitro Release Study

    Directory of Open Access Journals (Sweden)

    Maria Bastianini

    2017-07-01

    Full Text Available Ascorbic acid or vitamin C is a strong antioxidant widely used in cosmetic and food fields. This vitamin is very unstable and rapidly undergoes degradation. In order to solve this problem and to obtain a stable ascorbic acid, Nikkol Group has developed ascorbyltetraisopalmitate (VC-IP. This raw material is an oil phase, already well-known and employed in the cosmetic market. The objective of this study is to obtain VC-IP in micro-powder form, in order to produce a new raw material that is easily dispersible in oil and water phases and useful for make-up and color cosmetic applications. Various types of drug carriers were studied and considered in order to support VC-IP and obtain the conversion in powder. Υ-cyclodextrin and mesoporous silica SBA-15 were chosen as the best candidates. A white powder of supported VC-IP was obtained with each carrier (VC-IP@cyclodextrin, VC-IP@SBA-15. The systems underwent physicochemical characterization and in vitro release tests were carried out. Based on the conducted study, it can be concluded that by supporting VC-IP on Υ-cyclodextrin and SBA-15, it is feasible to obtain a new raw material in powder form. The two carriers possess different release profiles, adding the possibility to finely tune the release of the active component in smart formulations.

  4. Enzymatic Extraction of Hydroxycinnamic Acids from Coffee Pulp

    Directory of Open Access Journals (Sweden)

    Ernesto Favela-Torres

    2011-01-01

    Full Text Available Ferulic, caffeic, p-coumaric and chlorogenic acids are classified as hydroxycinnamic acids, presenting anticarcinogenic, anti-inflammatory and antioxidant properties. In this work, enzymatic extraction has been studied in order to extract high value-added products like hydroxycinnamic acids from coffee pulp. A commercial pectinase and enzyme extract produced by Rhizomucor pusillus strain 23aIV in solid-state fermentation using olive oil or coffee pulp (CP as an inducer of the feruloyl esterase activity were evaluated separately and mixed. The total content (covalently linked and free of ferulic, caffeic, p-coumaric and chlorogenic acids was 5276 mg per kg of coffee pulp. Distribution was as follows (in %: chlorogenic acid 58.7, caffeic acid 37.6, ferulic acid 2.1 and p-coumaric acid 1.5. Most of the hydroxycinnamic acids were covalently bound to the cell wall (in %: p-coumaric acid 97.2, caffeic acid 94.4, chlorogenic acid 76.9 and ferulic acid 73.4. The content of covalently linked hydroxycinnamic acid was used to calculate the enzyme extraction yield. The maximum carbon dioxide rate for the solid-state fermentation using olive oil as an inducer was higher and it was reached in a short cultivation time. Nevertheless, the feruloyl esterase (FAE activity (units per mg of protein obtained in the fermentation using CP as an inducer was 31.8 % higher in comparison with that obtained in the fermentation using olive oil as the inducer. To our knowledge, this is the first report indicating the composition of both esterified and free ferulic, caffeic, p-coumaric and chlorogenic acids in coffee pulp. The highest yield of extraction of hydroxycinnamic acids was obtained by mixing the produced enzyme extract using coffee pulp as an inducer and a commercial pectinase. Extraction yields were as follows (in %: chlorogenic acid 54.4, ferulic acid 19.8, p-coumaric acid 7.2 and caffeic acid 2.3. An important increase in the added value of coffee pulp was mainly

  5. Production of caffeoylmalic acid from glucose in engineered Escherichia coli.

    Science.gov (United States)

    Li, Tianzhen; Zhou, Wei; Bi, Huiping; Zhuang, Yibin; Zhang, Tongcun; Liu, Tao

    2018-07-01

    To achieve biosynthesis of caffeoylmalic acid from glucose in engineered Escherichia coli. We constructed the biosynthetic pathway of caffeoylmalic acid in E. coli by co-expression of heterologous genes RgTAL, HpaBC, At4CL2 and HCT2. To enhance the production of caffeoylmalic acid, we optimized the tyrosine metabolic pathway of E. coli to increase the supply of the substrate caffeic acid. Consequently, an E. coli-E. coli co-culture system was used for the efficient production of caffeoylmalic acid. The final titer of caffeoylmalic acid reached 570.1 mg/L. Microbial production of caffeoylmalic acid using glucose has application potential. In addition, microbial co-culture is an efficient tool for producing caffeic acid esters.

  6. Ascorbyl palmitate/d-α-tocopheryl polyethylene glycol 1000 succinate monoester mixed micelles for prolonged circulation and targeted delivery of compound K for antilung cancer therapy in vitro and in vivo

    Directory of Open Access Journals (Sweden)

    Zhang Y

    2017-01-01

    Full Text Available Youwen Zhang, Deyin Tong, Daobiao Che, Bing Pei, Xiaodong Xia, Gaofeng Yuan, Xin Jin Department of Hospital Pharmacy, The First Hospital of Suqian, Suqian, People’s Republic of China Abstract: The roles of ginsenoside compound K (CK in inhibiting tumor have been widely recognized in recent years. However, low water solubility and significant P-gp efflux have restricted its application. In this study, CK ascorbyl palmitate (AP/d-α-tocopheryl polyethylene glycol 1000 succinate monoester (TPGS mixed micelles were prepared as a delivery system to increase the absorption and targeted antitumor effect of CK. Consequently, the solubility of CK increased from 35.2±4.3 to 1,463.2±153.3 µg/mL. Furthermore, in an in vitro A549 cell model, CK AP/TPGS mixed micelles significantly inhibited cell growth, induced G0/G1 phase cell cycle arrest, induced cell apoptosis, and inhibited cell migration compared to free CK, all indicating that the developed micellar delivery system could increase the antitumor effect of CK in vitro. Both in vitro cellular fluorescence uptake and in vivo near-infrared imaging studies indicated that AP/TPGS mixed micelles can promote cellular uptake and enhance tumor targeting. Moreover, studies in the A549 lung cancer xenograft mouse model showed that CK AP/TPGS mixed micelles are an efficient tumor-targeted drug delivery system with an effective antitumor effect. Western blot analysis further confirmed that the marked antitumor effect in vivo could likely be due to apoptosis promotion and P-gp efflux inhibition. Therefore, these findings suggest that the AP/TPGS mixed micellar delivery system could be an efficient delivery strategy for enhanced tumor targeting and antitumor effects. Keywords: ginsenoside CK, ascorbyl palmitate, TPGS, mixed micelles, anti-tumor therapy

  7. Enhanced lignin monomer production caused by cinnamic Acid and its hydroxylated derivatives inhibits soybean root growth.

    Directory of Open Access Journals (Sweden)

    Rogério Barbosa Lima

    Full Text Available Cinnamic acid and its hydroxylated derivatives (p-coumaric, caffeic, ferulic and sinapic acids are known allelochemicals that affect the seed germination and root growth of many plant species. Recent studies have indicated that the reduction of root growth by these allelochemicals is associated with premature cell wall lignification. We hypothesized that an influx of these compounds into the phenylpropanoid pathway increases the lignin monomer content and reduces the root growth. To confirm this hypothesis, we evaluated the effects of cinnamic, p-coumaric, caffeic, ferulic and sinapic acids on soybean root growth, lignin and the composition of p-hydroxyphenyl (H, guaiacyl (G and syringyl (S monomers. To this end, three-day-old seedlings were cultivated in nutrient solution with or without allelochemical (or selective enzymatic inhibitors of the phenylpropanoid pathway in a growth chamber for 24 h. In general, the results showed that 1 cinnamic, p-coumaric, caffeic and ferulic acids reduced root growth and increased lignin content; 2 cinnamic and p-coumaric acids increased p-hydroxyphenyl (H monomer content, whereas p-coumaric, caffeic and ferulic acids increased guaiacyl (G content, and sinapic acid increased sinapyl (S content; 3 when applied in conjunction with piperonylic acid (PIP, an inhibitor of the cinnamate 4-hydroxylase, C4H, cinnamic acid reduced H, G and S contents; and 4 when applied in conjunction with 3,4-(methylenedioxycinnamic acid (MDCA, an inhibitor of the 4-coumarate:CoA ligase, 4CL, p-coumaric acid reduced H, G and S contents, whereas caffeic, ferulic and sinapic acids reduced G and S contents. These results confirm our hypothesis that exogenously applied allelochemicals are channeled into the phenylpropanoid pathway causing excessive production of lignin and its main monomers. By consequence, an enhanced stiffening of the cell wall restricts soybean root growth.

  8. Antiproliferative and apoptotic effects of selective phenolic acids on T47D human breast cancer cells: potential mechanisms of action

    International Nuclear Information System (INIS)

    Kampa, Marilena; Boskou, Dimitrios; Gravanis, Achille; Castanas, Elias; Alexaki, Vassilia-Ismini; Notas, George; Nifli, Artemissia-Phoebe; Nistikaki, Anastassia; Hatzoglou, Anastassia; Bakogeorgou, Efstathia; Kouimtzoglou, Elena; Blekas, George

    2004-01-01

    The oncoprotective role of food-derived polyphenol antioxidants has been described but the implicated mechanisms are not yet clear. In addition to polyphenols, phenolic acids, found at high concentrations in a number of plants, possess antioxidant action. The main phenolic acids found in foods are derivatives of 4-hydroxybenzoic acid and 4-hydroxycinnamic acid. This work concentrates on the antiproliferative action of caffeic acid, syringic acid, sinapic acid, protocatechuic acid, ferulic acid and 3,4-dihydroxy-phenylacetic acid (PAA) on T47D human breast cancer cells, testing their antioxidant activity and a number of possible mechanisms involved (interaction with membrane and intracellular receptors, nitric oxide production). The tested compounds showed a time-dependent and dose-dependent inhibitory effect on cell growth with the following potency: caffeic acid > ferulic acid = protocatechuic acid = PAA > sinapic acid = syringic acid. Caffeic acid and PAA were chosen for further analysis. The antioxidative activity of these phenolic acids in T47D cells does not coincide with their inhibitory effect on tumoral proliferation. No interaction was found with steroid and adrenergic receptors. PAA induced an inhibition of nitric oxide synthase, while caffeic acid competes for binding and results in an inhibition of aryl hydrocarbon receptor-induced CYP1A1 enzyme. Both agents induce apoptosis via the Fas/FasL system. Phenolic acids exert a direct antiproliferative action, evident at low concentrations, comparable with those found in biological fluids after ingestion of foods rich in phenolic acids. Furthermore, the direct interaction with the aryl hydrocarbon receptor, the nitric oxide synthase inhibition and their pro-apoptotic effect provide some insights into their biological mode of action

  9. Identification and characterization of 4 missense mutations in brown midrib 12 (Bmr12); the caffeic O-methyltranferase (COMT) of sorghum

    Science.gov (United States)

    Modifying lignin content and composition are targets to improve bioenergy crops for cellulosic conversion to biofuels. In sorghum and other C4 grasses, the brown midrib mutants have been shown to reduce lignin content and alter its composition. Bmr12 encodes the sorghum caffeic O-methyltransferase...

  10. Cytoprotection of Human Endothelial Cells From Menadione Cytotoxicity by Caffeic Acid Phenethyl Ester: The Role of Heme Oxygenase-1

    Science.gov (United States)

    2008-06-08

    cells (HUVEC) to evaluate potential gene expression involvement. CAPE exhibited dose- dependent cytoprotection of HUVEC. A gene screen with...highly induced (8.25-fold) by CAPE compared to DMSO control. To validate this particular microarray screening result, quantitative real-time RT-PCR was...the Nrf2 transcription factor in response to the antioxidant phytochemical carnosol. The Journal of Biological Chemistry 279, 8919–8929. Minami, T

  11. Comparative evaluation of antibacterial activity of caffeic acid phenethyl ester and PLGA nanoparticle formulation by different methods

    International Nuclear Information System (INIS)

    Arasoglu, Tülin; Mansuroglu, Banu; Derman, Serap

    2016-01-01

    The aim of the present study was to evaluate the antimicrobial activity of nanoparticle and free formulations of the CAPE compound using different methods and comparing the results in the literature for the first time. In parallel with this purpose, encapsulation of CAPE with the PLGA nanoparticle system (CAPE-PLGA-NPs) and characterization of nanoparticles were carried out. Afterwards, antimicrobial activity of free CAPE and CAPE-PLGA-NPs was determined using agar well diffusion, disk diffusion, broth microdilution and reduction percentage methods. P. aeroginosa, E. coli, S. aureus and methicillin-resistant S. aureus (MRSA) were chosen as model bacteria since they have different cell wall structures. CAPE-PLGA-NPs within the range of 214.0 ± 8.80 nm particle size and with an encapsulation efficiency of 91.59 ± 4.97% were prepared using the oil-in-water (o–w) single-emulsion solvent evaporation method. The microbiological results indicated that free CAPE did not have any antimicrobial activity in any of the applied methods whereas CAPE-PLGA-NPs had significant antimicrobial activity in both broth dilution and reduction percentage methods. CAPE-PLGA-NPs showed moderate antimicrobial activity against S. aureus and MRSA strains particularly in hourly measurements at 30.63 and 61.25 μg ml −1 concentrations (both p < 0.05), whereas they failed to show antimicrobial activity against Gram-negative bacteria (P. aeroginosa and E. coli, p > 0.05). In the reduction percentage method, in which the highest results of antimicrobial activity were obtained, it was observed that the antimicrobial effect on S. aureus was more long-standing (3 days) and higher in reduction percentage (over 90%). The appearance of antibacterial activity of CAPE-PLGA-NPs may be related to higher penetration into cells due to low solubility of free CAPE in the aqueous medium. Additionally, the biocompatible and biodegradable PLGA nanoparticles could be an alternative to solvents such as ethanol, methanol or DMSO. Consequently, obtained results show that the method of selection is extremely important and will influence the results. Thus, broth microdilution and reduction percentage methods can be recommended as reliable and useful screening methods for determination of antimicrobial activity of PLGA nanoparticle formulations used particularly in drug delivery systems compared to both agar well and disk diffusion methods. (paper)

  12. Comparative evaluation of antibacterial activity of caffeic acid phenethyl ester and PLGA nanoparticle formulation by different methods

    Science.gov (United States)

    Arasoglu, Tülin; Derman, Serap; Mansuroglu, Banu

    2016-01-01

    The aim of the present study was to evaluate the antimicrobial activity of nanoparticle and free formulations of the CAPE compound using different methods and comparing the results in the literature for the first time. In parallel with this purpose, encapsulation of CAPE with the PLGA nanoparticle system (CAPE-PLGA-NPs) and characterization of nanoparticles were carried out. Afterwards, antimicrobial activity of free CAPE and CAPE-PLGA-NPs was determined using agar well diffusion, disk diffusion, broth microdilution and reduction percentage methods. P. aeroginosa, E. coli, S. aureus and methicillin-resistant S. aureus (MRSA) were chosen as model bacteria since they have different cell wall structures. CAPE-PLGA-NPs within the range of 214.0 ± 8.80 nm particle size and with an encapsulation efficiency of 91.59 ± 4.97% were prepared using the oil-in-water (o-w) single-emulsion solvent evaporation method. The microbiological results indicated that free CAPE did not have any antimicrobial activity in any of the applied methods whereas CAPE-PLGA-NPs had significant antimicrobial activity in both broth dilution and reduction percentage methods. CAPE-PLGA-NPs showed moderate antimicrobial activity against S. aureus and MRSA strains particularly in hourly measurements at 30.63 and 61.25 μg ml-1 concentrations (both p 0.05). In the reduction percentage method, in which the highest results of antimicrobial activity were obtained, it was observed that the antimicrobial effect on S. aureus was more long-standing (3 days) and higher in reduction percentage (over 90%). The appearance of antibacterial activity of CAPE-PLGA-NPs may be related to higher penetration into cells due to low solubility of free CAPE in the aqueous medium. Additionally, the biocompatible and biodegradable PLGA nanoparticles could be an alternative to solvents such as ethanol, methanol or DMSO. Consequently, obtained results show that the method of selection is extremely important and will influence the results. Thus, broth microdilution and reduction percentage methods can be recommended as reliable and useful screening methods for determination of antimicrobial activity of PLGA nanoparticle formulations used particularly in drug delivery systems compared to both agar well and disk diffusion methods.

  13. Chlorogenic acid in a Nicotiana plumbaginifolia cell suspension.

    Science.gov (United States)

    Gillet; Mesnard; Fliniaux; Monti; Fliniaux

    1999-11-01

    A phenylpropanoid compound has been characterized in a Nicotiana plumbaginifolia cell suspension. This compound has been isolated and purified by semi-preparative reverse phase-high performance liquid chromatography. Its structure has been identified by NMR spectroscopy as 5-O-caffeoylquinic acid, which is chlorogenic acid (CA). The influence of culture conditions on the accumulation of this metabolite by N. plumbaginifolia cell suspensions has been studied. Darkness strongly inhibits the CA accumulation. Moreover, it has been shown that feeding experiments with caffeic acid had a deleterious effect upon the CA content. This one was not influenced by a supplementation with quinic acid.

  14. Dietary Consumption of Phenolic Acids and Prostate Cancer: A Case-Control Study in Sicily, Southern Italy

    Directory of Open Access Journals (Sweden)

    Giorgio Ivan Russo

    2017-12-01

    Full Text Available Dietary polyphenols gained the interest of the scientific community due to their wide content in a variety of plant-derived foods and beverages commonly consumed, such as fruits, vegetables, coffee, tea, and cocoa. We aimed to investigate whether there was an association between dietary phenolic acid consumption and prostate cancer (PCa in South Italy. We conducted a population-based case-control study from January 2015 to December 2016 in a single institution of the municipality of Catania, southern Italy (Registration number: 41/2015. Patients with elevated PSA and/or suspicious PCa underwent transperineal prostate biopsy. A total of 118 histopathological-verified PCa cases were collected and a total of 222 controls were selected from a sample of 2044 individuals. Dietary data were collected by using two food frequency questionnaires and data on the phenolic acids content in foods was obtained from the Phenol-Explorer database (www.phenol-explorer.eu. Association between dietary intake of phenolic acids and PCa was calculated through logistic regression analysis. We found lower levels of caffeic acid (2.28 mg/day vs. 2.76 mg/day; p < 0.05 and ferulic acid (2.80 mg/day vs. 4.04 mg/day; p < 0.01 in PCa when compared to controls. The multivariate logistic regression showed that both caffeic acid (OR = 0.32; p < 0.05 and ferulic acid (OR = 0.30; p < 0.05 were associated with reduced risk of PCa. Higher intake of hydroxybenzoic acids and caffeic acids were associated with lower risk of advanced PCa. High intake of caffeic acid and ferulic acid may be associated with reduced risk of PCa.

  15. Dietary Consumption of Phenolic Acids and Prostate Cancer: A Case-Control Study in Sicily, Southern Italy.

    Science.gov (United States)

    Russo, Giorgio Ivan; Campisi, Daniele; Di Mauro, Marina; Regis, Federica; Reale, Giulio; Marranzano, Marina; Ragusa, Rosalia; Solinas, Tatiana; Madonia, Massimo; Cimino, Sebastiano; Morgia, Giuseppe

    2017-12-05

    Dietary polyphenols gained the interest of the scientific community due to their wide content in a variety of plant-derived foods and beverages commonly consumed, such as fruits, vegetables, coffee, tea, and cocoa . We aimed to investigate whether there was an association between dietary phenolic acid consumption and prostate cancer (PCa) in South Italy. We conducted a population-based case-control study from January 2015 to December 2016 in a single institution of the municipality of Catania, southern Italy (Registration number: 41/2015). Patients with elevated PSA and/or suspicious PCa underwent transperineal prostate biopsy. A total of 118 histopathological-verified PCa cases were collected and a total of 222 controls were selected from a sample of 2044 individuals. Dietary data were collected by using two food frequency questionnaires and data on the phenolic acids content in foods was obtained from the Phenol-Explorer database (www.phenol-explorer.eu). Association between dietary intake of phenolic acids and PCa was calculated through logistic regression analysis. We found lower levels of caffeic acid (2.28 mg/day vs. 2.76 mg/day; p < 0.05) and ferulic acid (2.80 mg/day vs. 4.04 mg/day; p < 0.01) in PCa when compared to controls. The multivariate logistic regression showed that both caffeic acid (OR = 0.32; p < 0.05) and ferulic acid (OR = 0.30; p < 0.05) were associated with reduced risk of PCa. Higher intake of hydroxybenzoic acids and caffeic acids were associated with lower risk of advanced PCa. High intake of caffeic acid and ferulic acid may be associated with reduced risk of PCa.

  16. Effects of the Aqueous Extract from Tabebuia roseoalba and Phenolic Acids on Hyperuricemia and Inflammation

    Directory of Open Access Journals (Sweden)

    Zilma Schimith Ferraz-Filha

    2017-01-01

    Full Text Available Tabebuia species (Bignoniaceae have long been used in folk medicine as anti-inflammatory, antirheumatic, antimicrobial, and antitumor. The aim of this study was to investigate if aqueous extract from the leaves (AEL of Tabebuia roseoalba (Ridl. Sandwith, Bignoniaceae, and its constituents could be useful to decrease serum uric acid levels and restrain the gout inflammatory process. HPLC analysis identified caffeic acid and chlorogenic acid in AEL. Antihyperuricemic effects and inhibition of liver XOD (xanthine oxidoreductase by AEL and identified compounds were evaluated in hyperuricemic mice. Anti-inflammatory activity was evaluated on MSU (monosodium urate crystal-induced paw edema. In addition, AEL antioxidant activity in vitro was evaluated. AEL, caffeic, and chlorogenic acids were able to reduce serum uric acid levels in hyperuricemic mice probably through inhibition of liver xanthine oxidase activity and significantly decreased the paw edema induced by MSU crystals. AEL showed significant antioxidant activity in all evaluated assays. The results show that the AEL of Tabebuia roseoalba can be a promising agent for treatment for gout and inflammatory diseases. We suggest that caffeic and chlorogenic acids may be responsible for the activities demonstrated by the species.

  17. Identification of Phenolic Acids and Changes in their Content during Fermentation and Ageing of White Wines Pošip and Rukatac

    Directory of Open Access Journals (Sweden)

    Tomislav Lovrić

    2002-01-01

    Full Text Available Identification of phenolic acids was performed and changes in their content during the production of autochthonous Croatian white wines Pošip and Rukatac (Vitis vinifera, L. were registered. In both varieties (Pošip, Rukatac the following phenolic acids were identified: gallic, protocatechuic and vanillic acids as hydroxybenzoic acids; and caffeic, p-coumaric and ferulic acids as hydroxycinnamic acids. It was found that there is a difference between hydroxybenzoic acid group and hydroxycinnamic acid group content and between their influences on the wine colour (colour intensity and hue.

  18. Multifunctional Cinnamic Acid Derivatives

    Directory of Open Access Journals (Sweden)

    Aikaterini Peperidou

    2017-07-01

    Full Text Available Our research to discover potential new multitarget agents led to the synthesis of 10 novel derivatives of cinnamic acids and propranolol, atenolol, 1-adamantanol, naphth-1-ol, and (benzylamino ethan-1-ol. The synthesized molecules were evaluated as trypsin, lipoxygenase and lipid peroxidation inhibitors and for their cytotoxicity. Compound 2b derived from phenoxyphenyl cinnamic acid and propranolol showed the highest lipoxygenase (LOX inhibition (IC50 = 6 μΜ and antiproteolytic activity (IC50 = 0.425 μΜ. The conjugate 1a of simple cinnamic acid with propranolol showed the higher antiproteolytic activity (IC50 = 0.315 μΜ and good LOX inhibitory activity (IC50 = 66 μΜ. Compounds 3a and 3b, derived from methoxylated caffeic acid present a promising combination of in vitro inhibitory and antioxidative activities. The S isomer of 2b also presented an interesting multitarget biological profile in vitro. Molecular docking studies point to the fact that the theoretical results for LOX-inhibitor binding are identical to those from preliminary in vitro study.

  19. Gibbs energies of protonation and complexation of platinum and vanadate metal ions with naringenin and phenolic acids: Theoretical calculations associated with experimental values

    International Nuclear Information System (INIS)

    Fazary, Ahmed E.; Alshihri, Ayed S.; Alfaifi, Mohammad Y.; Saleh, Kamel A.; Elbehairi, Serag Eldin I.; Fawy, Khaled F.; Abd-Rabboh, Hisham S.M.

    2016-01-01

    Highlights: • The experimental thermodynamic equilibrium and stability constants of vanadium and platinum complexes involving naringin, ferulic acid, p-coumaric acid, caffeic acid, vanillic acid, sinapic acid, and gallic acid were determined. • The theoretical calculations of the free energy changes associated with the ligand protonation, and metal ion–ligand complex formation equilibria using density function theory calculations, providing a complete picture of the microscopic equilibria of the studied complex systems. - Abstract: The Experimental thermodynamic equilibrium (pK_a values) and stability (log β) constants of vanadium and platinum binary and mixed ligand complexes involving naringenin, ferulic acid, p-coumaric acid, caffeic acid, vanillic acid, sinapic acid, and gallic acid were determined at 310.15 K in 0.16 mol·dm"−"3 KCl aqueous solutions using pH-potentiometric technique and by means of two estimation models (HYPERQUAD 2008 and Bjerrum–Calvin). The theoretical calculations of overall protonation and stability constants of the metal complex species in solution were predicted as the free energy change associated with the ligand protonation, and metal ion–ligand complex formation equilibria (species solvation/de-solvation) using ab initio and density function theory (DFT) calculations. The usage of the experimental potentiometry technique and theoretical predictions provides a complete picture of the microscopic equilibria of the studied systems (vanadium/platinum–naringenin–phenolic acid). Specifically, this theoretically DFT predications would be useful to determine the most real protonation constants of the studied bioligands in which the binding sites changes due to the ligand protonation/deprotonation equilibria. Also, the complexing capacities of vanadium and platinum towards naringenin, ferulic acid, p-coumaric acid, caffeic acid, vanillic acid, sinapic acid, and gallic acid in solutions were evaluated and discussed. From the

  20. Interaction of milk whey protein with common phenolic acids

    Science.gov (United States)

    Zhang, Hao; Yu, Dandan; Sun, Jing; Guo, Huiyuan; Ding, Qingbo; Liu, Ruihai; Ren, Fazheng

    2014-01-01

    Phenolics-rich foods such as fruit juices and coffee are often consumed with milk. In this study, the interactions of α-lactalbumin and β-lactoglobulin with the phenolic acids (chlorogenic acid, caffeic acid, ferulic acid, and coumalic acid) were examined. Fluorescence, CD, and FTIR spectroscopies were used to analyze the binding modes, binding constants, and the effects of complexation on the conformation of whey protein. The results showed that binding constants of each whey protein-phenolic acid interaction ranged from 4 × 105 to 7 × 106 M-n and the number of binding sites n ranged from 1.28 ± 0.13 to 1.54 ± 0.34. Because of these interactions, the conformation of whey protein was altered, with a significant reduction in the amount of α-helix and an increase in the amounts of β-sheet and turn structures.

  1. Identification/quantification of free and bound phenolic acids in peel and pulp of apples (Malus domestica) using high resolution mass spectrometry (HRMS).

    Science.gov (United States)

    Lee, Jihyun; Chan, Bronte Lee Shan; Mitchell, Alyson E

    2017-01-15

    Free and bound phenolic acids were measured in the pulp and peel of four varieties of apples using high resolution mass spectrometry. Twenty-five phenolic acids were identified and included: 8 hydroxybenzoic acids, 11 hydroxycinnamic acids, 5 hydroxyphenylacetic acids, and 1 hydoxyphenylpropanoic acid. Several phenolics are tentatively identified for the first time in apples and include: methyl gallate, ethyl gallate, hydroxy phenyl acetic acid, three phenylacetic acid isomers, 3-(4-hydroxyphenyl)propionic acid, and homoveratric acid. With exception of chlorogenic and caffeic acid, most phenolic acids were quantified for the first time in apples. Significant varietal differences (pacids were higher in the pulp as compared to apple peel (dry weight) in all varieties. Coumaroylquinic, protocatechuic, 4-hydroxybenzoic, vanillic and t-ferulic acids were present in free forms. With exception of chlorogenic acid, all other phenolic acids were present only as bound forms. Copyright © 2016 Elsevier Ltd. All rights reserved.

  2. The phenolic acids of some species of the Oenothera L. genus

    Directory of Open Access Journals (Sweden)

    Tadeusz Krzaczek

    2014-01-01

    Full Text Available The occurence and approximative quantitative proportions of the phenolic acids in four species of the Oenothera L. genus was determined by the method of TLC and HPLC. In all species of Oenothera L. genus the permanent occurrence of acids: 2-hydroxy-4-metoxybenzoic, salicylic, ferulic, syringic, vanillic, p-coumaric, p-hydroxybenzoic, p-hydroxyphenylacetic, γ-rezorcil, gentysic, protocatechuic, caffeic and gallic has been confirmed. Whereas the other phenolic acids: o-coumaric, o-hydroxyphenylacetic and pirocatechuic were found in some species of the Oenothera L. genus only.

  3. HPLC-ESI-MS/MS analysis of oxidized di-caffeoylquinic acids generated by metalloporphyrin-catalyzed reactions

    Directory of Open Access Journals (Sweden)

    Michel D. Santos

    2008-01-01

    Full Text Available This paper reports an HPLC-ESI-MS/MS investigation on the oxidation of 3,5- and 4,5- dicaffeoylquinic acid using iron(III tetraphenylporphyrin chloride as catalyst. Two major mono-oxidised products of the quinic acid moiety have been identified for both compounds. However, only the 4,5-derivative afforded two different tri-oxo products. Thus, it seems that the oxidation pattern depends on the number and positions of the caffeic acid moieties present in caffeoylquinic acid molecules.

  4. HPLC-ESI-MS/MS analysis of oxidized di-caffeoylquinic acids generated by metalloporphyrin-catalyzed reactions

    International Nuclear Information System (INIS)

    Santos, Michel D.; Lopes, Norberto P.; Iamamoto, Yassuko

    2008-01-01

    This paper reports an HPLC-ESI-MS/MS investigation on the oxidation of 3,5- and 4,5- dicaffeoylquinic acid using iron(III) tetraphenylporphyrin chloride as catalyst. Two major mono-oxidised products of the quinic acid moiety have been identified for both compounds. However, only the 4,5-derivative afforded two different tri-oxo products. Thus, it seems that the oxidation pattern depends on the number and positions of the caffeic acid moieties present in caffeoylquinic acid molecules. (author)

  5. HPLC-ESI-MS/MS analysis of oxidized di-caffeoylquinic acids generated by metalloporphyrin-catalyzed reactions

    Energy Technology Data Exchange (ETDEWEB)

    Santos, Michel D.; Lopes, Norberto P. [Universidade de Sao Paulo (USP), Ribeirao Preto, SP (Brazil). Faculdade de Ciencias Farmaceuticas. Dept. de Fisica e Quimica]. E-mail: npelopes@fcfrp.usp.br; Iamamoto, Yassuko [Universidade de Sao Paulo (USP), Ribeirao Preto, SP (Brazil). Faculdade de Ciencias Farmaceuticas. Dept. de Quimica

    2008-07-01

    This paper reports an HPLC-ESI-MS/MS investigation on the oxidation of 3,5- and 4,5- dicaffeoylquinic acid using iron(III) tetraphenylporphyrin chloride as catalyst. Two major mono-oxidised products of the quinic acid moiety have been identified for both compounds. However, only the 4,5-derivative afforded two different tri-oxo products. Thus, it seems that the oxidation pattern depends on the number and positions of the caffeic acid moieties present in caffeoylquinic acid molecules. (author)

  6. Phenolic acids potentiate colistin-mediated killing of Acinetobacter baumannii by inducing redox imbalance.

    Science.gov (United States)

    Ajiboye, Taofeek O; Skiebe, Evelyn; Wilharm, Gottfried

    2018-05-01

    Phenolic acids with catechol groups are good prooxidants because of their low redox potential. In this study, we provided data showing that phenolic acids, caffeic acid, gallic acid and protocatechuic acid, enhanced colistin-mediated bacterial death by inducing redox imbalance. The minimum inhibitory concentrations of these phenolic acids against Acinetobacter baumannii AB5075 were considerably lowered for ΔsodB and ΔkatG mutants. Checkerboard assay shows synergistic interactions between colistin and phenolic acids. The phenolic acids exacerbated colistin-induced oxidative stress in A. baumannii AB5075 through increased superoxide anion generation, NAD + /NADH and ADP/ATP ratio. In parallel, the level of reduced glutathione was significantly lowered. We conclude that phenolic acids potentiate colistin-induced oxidative stress in A. baumannii AB5075 by increasing ROS generation, energy metabolism and electron transport chain activity with a concomitant decrease in glutathione. Copyright © 2018 Elsevier Masson SAS. All rights reserved.

  7. Antifungal activity of secondary plant metabolites from potatoes (Solanum tuberosum L.): Glycoalkaloids and phenolic acids show synergistic effects.

    Science.gov (United States)

    Sánchez-Maldonado, A F; Schieber, A; Gänzle, M G

    2016-04-01

    To study the antifungal effects of the potato secondary metabolites α-solanine, α-chaconine, solanidine and caffeic acid, alone or combined. Resistance to glycoalkaloids varied among the fungal species tested, as derived from minimum inhibitory concentrations assays. Synergistic antifungal activity between glycoalkaloids and phenolic compounds was found. Changes in the fluidity of fungal membranes caused by potato secondary plant metabolites were determined by calculation of the generalized polarization values. The results partially explained the synergistic effect between caffeic acid and α-chaconine and supported findings on membrane disruption mechanisms from previous studies on artificial membranes. LC/MS analysis was used to determine variability and relative amounts of sterols in the different fungal species. Results suggested that the sterol pattern of fungi is related to their resistance to potato glycoalkaloids and to their taxonomy. Fungal resistance to α-chaconine and possibly other glycoalkaloids is species dependent. α-Chaconine and caffeic acid show synergistic antifungal activity. The taxonomic classification and the sterol pattern play a role in fungal resistance to glycoalkaloids. Results improve the understanding of the antifungal mode of action of potato secondary metabolites, which is essential for their potential utilization as antifungal agents in nonfood systems. © 2016 The Society for Applied Microbiology.

  8. Acidic-alkaline ferulic acid esterase from Chaetomium thermophilum var. dissitum: Molecular cloning and characterization of recombinant enzyme expressed in Pichia pastoris

    DEFF Research Database (Denmark)

    Dotsenko, Gleb; Tong, Xiaoxue; Pilgaard, Bo

    2016-01-01

    A novel ferulic acid esterase encoding gene CtFae, was successfully cloned from a highly esterase active strain of the thermophile ascomycetous fungus Chaetomium thermophilum var. dissitum; the gene was heterologously expressed in Pichia pastoris KM71H. The recombinant enzyme (CtFae) was purified...... to homogeneity and subsequently characterized. CtFae was active towards synthetic esters of ferulic, p-coumaric, and caffeic acids, as well as towards wide range of p-nitrophenyl substrates. Its temperature and pH optima were 55 °C and pH 6.0, respectively. Enzyme rare features were broad pH optimum, high...

  9. Structure-Activity Relationships in the Cytoprotective Effect of Caffeic Acid Phenethyl Ester (CAPE) and Fluorinated Derivatives: Effects on Heme Oxygenase-1 Induction and Antioxidant Activities

    Science.gov (United States)

    2010-03-09

    Hishikawa, K., Nakaki, T., Fujita, T., 2005. Oral flavonoid supplementation attenuates atherosclerosis development in apolipoprotein E-deficient mice... flavonoids . Free Radical Biology & Medicine 20, 331–342. Wakabayashi, N., Dinkova-Kostova, A.T., Holtzclaw, W.D., Kang, M.I., Kobayashi, A., Yamamoto, M

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

    NARCIS (Netherlands)

    Mia, Masum M.; Bank, Ruud A.

    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 (TGF beta 1) plays a major role in the formation of myofibroblasts, e.g. by activating

  11. Natural Product Total Synthesis in the Organic Laboratory: Total Synthesis of Caffeic Acid Phenethyl Ester (CAPE), a Potent 5-Lipoxygenase Inhibitor from Honeybee Hives

    Science.gov (United States)

    Touaibia, Mohamed; Guay, Michel

    2011-01-01

    Natural products play a critical role in modern organic synthesis and learning synthetic techniques is an important component of the organic laboratory experience. In addition to traditional one-step organic synthesis laboratories, a multistep natural product synthesis is an interesting experiment to challenge students. The proposed three-step…

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

    OpenAIRE

    Becker, Christine; Urli?, Branimir; Juki? ?pika, Maja; Kl?ring, 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 nitr...

  13. A spectroelectrochemical and chemical study on oxidation of hydroxycinnamic acids in aprotic medium

    Energy Technology Data Exchange (ETDEWEB)

    Petrucci, Rita [Dipartimento di Ingegneria Chimica M.M.P.M., Universita di Roma ' La Sapienza' , via del Castro Laurenziano 7, I-00161 Rome (Italy)]. E-mail: rita.petrucci@uniroma1.it; Astolfi, Paola [Dipartimento di Scienze dei Materiali e della Terra, Universita Politecnica delle Marche, via Brecce Bianche, I-60131 Ancona (Italy); Greci, Lucedio [Dipartimento di Scienze dei Materiali e della Terra, Universita Politecnica delle Marche, via Brecce Bianche, I-60131 Ancona (Italy); Firuzi, Omidreza [Dipartimento di Farmacologia delle Sostanze Naturali e Fisiologia Generale, Universita di Roma ' La Sapienza' , p.le Aldo Moro 5, I-00185 Rome (Italy); Saso, Luciano [Dipartimento di Farmacologia delle Sostanze Naturali e Fisiologia Generale, Universita di Roma ' La Sapienza' , p.le Aldo Moro 5, I-00185 Rome (Italy); Marrosu, Giancarlo [Dipartimento di Ingegneria Chimica M.M.P.M., Universita di Roma ' La Sapienza' , via del Castro Laurenziano 7, I-00161 Rome (Italy)

    2007-02-01

    Electrochemical and chemical oxidation of hydroxycinnamic acids (HCAs) was studied to investigate the mechanisms occurring in their antioxidant activities in a protons poor medium. Electrolyses and chemical reactions were followed on-line by monitoring the UV-spectral changes with time; final solutions were analysed by HPLC-MS. Anodic oxidation of mono- and di-HCAs, studied by cyclic voltammetry and controlled potential electrolyses, occurs via a reversible one-step two-electrons process, yielding the corresponding stable phenoxonium cation. A cyclization product was also proposed, as supported by ESR studies. Chemical oxidation with lead dioxide leads to different oxidation products according to the starting substrate. Di-HCAs like chlorogenic and rosmarinic acids and the ethyl ester of caffeic acid gave the corresponding neutral o-quinones, while mono-HCAs like cumaric, ferulic and sinapinic acids yielded the corresponding unstable neutral phenoxyl radical, as supported by the formation of dimerization products evidenced by HPLC-MS. In the case of caffeic acid, traces of the dimerization product suggest that the neutral phenoxyl radical may competitively undergo dimerization or decomposition of the neutral quinone. Chemical oxidation of HCAs was also followed by ESR spectroscopy: the di-HCAs radical anions were generated and detected, whereas among the mono-HCAs only the phenoxyl radical of the sinapinic acid was recorded.

  14. Ruminal Methane Production on Simple Phenolic Acids Addition in in Vitro Gas Production Method

    Directory of Open Access Journals (Sweden)

    A. Jayanegara

    2009-04-01

    Full Text Available Methane production from ruminants contributes to total global methane production, which is an important contributor to global warming. In this experiment, six sources of simple phenolic acids (benzoic, cinnamic, phenylacetic, caffeic, p-coumaric and ferulic acids at two different levels (2 and 5 mM added to hay diet were evaluated for their potential to reduce enteric methane production using in vitro Hohenheim gas production method. The measured variables were gas production, methane, organic matter digestibility (OMD, and short chain fatty acids (SCFA. The results showed that addition of cinnamic, caffeic, p-coumaric and ferulic acids at 5 mM significantly (P p-coumaric > ferulic > cinnamic. The addition of simple phenols did not significantly decrease OMD. Addition of simple phenols tends to decrease total SCFA production. It was concluded that methane decrease by addition of phenolic acids was relatively small, and the effect of phenolic acids on methane decrease depended on the source and concentration applied.

  15. Interaction of humic acids and humic-acid-like polymers with herpes simplex virus type 1

    Science.gov (United States)

    Klöcking, Renate; Helbig, Björn

    The study was performed in order to compare the antiviral activity against herpes simplex virus type 1 (HSV-1) of synthetic humic-acid-like polymers to that of their low-molecular-weight basic compounds and naturally occurring humic acids (HA) in vitro. HA from peat water showed a moderate antiviral activity at a minimum effective concentration (MEC) of 20 µg/ml. HA-like polymers, i.e. the oxidation products of caffeic acid (KOP), hydrocaffeic acid (HYKOP), chlorogenic acid (CHOP), 3,4-dihydroxyphenylacetic acid (3,4-DHPOP), nordihydroguaretic acid (NOROP), gentisinic acid (GENOP), pyrogallol (PYROP) and gallic acid (GALOP), generally inhibit virus multiplication, although with different potency and selectivity. Of the substances tested, GENOP, KOP, 3,4-DHPOP and HYKOP with MEC values in the range of 2 to 10 µg/ml, proved to be the most potent HSV-1 inhibitors. Despite its lower antiviral potency (MEC 40 µg/ml), CHOP has a remarkable selectivity due to the high concentration of this polymer that is tolerated by the host cells (>640 µg/ml). As a rule, the antiviral activity of the synthetic compounds was restricted to the polymers and was not preformed in the low-molecular-weight basic compounds. This finding speaks in favour of the formation of antivirally active structures during the oxidative polymerization of phenolic compounds and, indirectly, of corresponding structural parts in different HA-type substances.

  16. Metabolism of Fructophilic Lactic Acid Bacteria Isolated from the Apis mellifera L. Bee Gut: Phenolic Acids as External Electron Acceptors

    Science.gov (United States)

    Filannino, Pasquale; Addante, Rocco; Pontonio, Erica; Gobbetti, Marco

    2016-01-01

    ABSTRACT Fructophilic lactic acid bacteria (FLAB) are strongly associated with the gastrointestinal tracts (GITs) of Apis mellifera L. worker bees due to the consumption of fructose as a major carbohydrate. Seventy-seven presumptive lactic acid bacteria (LAB) were isolated from GITs of healthy A. mellifera L. adults, which were collected from 5 different geographical locations of the Apulia region of Italy. Almost all of the isolates showed fructophilic tendencies: these isolates were identified as Lactobacillus kunkeei (69%) or Fructobacillus fructosus (31%). A high-throughput phenotypic microarray targeting 190 carbon sources was used to determine that 83 compounds were differentially consumed. Phenotyping grouped the strains into two clusters, reflecting growth performance. The utilization of phenolic acids, such as p-coumaric, caffeic, syringic, or gallic acids, as electron acceptors was investigated in fructose-based medium. Almost all FLAB strains showed tolerance to high phenolic acid concentrations. p-Coumaric acid and caffeic acid were consumed by all FLAB strains through reductases or decarboxylases. Syringic and gallic acids were partially metabolized. The data collected suggest that FLAB require external electron acceptors to regenerate NADH. The use of phenolic acids as external electron acceptors by the 4 FLAB showing the highest phenolic acid reductase activity was investigated in glucose-based medium supplemented with p-coumaric acid. Metabolic responses observed through a phenotypic microarray suggested that FLAB may use p-coumaric acid as an external electron acceptor, enhancing glucose dissimilation but less efficiently than other external acceptors such as fructose or pyruvic acid. IMPORTANCE Fructophilic lactic acid bacteria (FLAB) remain to be fully explored. This study intends to link unique biochemical features of FLAB with their habitat. The quite unique FLAB phenome within the group lactic acid bacteria (LAB) may have practical relevance

  17. Heterogeneous kinetics, products, and mechanisms of ferulic acid particles in the reaction with NO3 radicals

    Science.gov (United States)

    Liu, Changgeng; Zhang, Peng; Wen, Xiaoying; Wu, Bin

    2017-03-01

    Methoxyphenols, as an important component of wood burning, are produced by lignin pyrolysis and considered to be the potential tracers for wood smoke emissions. In this work, the heterogeneous reaction between ferulic acid particles and NO3 radicals was investigated. Six products including oxalic acid, 4-vinylguaiacol, vanillin, 5-nitrovanillin, 5-nitroferulic acid, and caffeic acid were confirmed by gas chromatography-mass spectrometry (GC-MS). In addition, the reaction mechanisms were proposed and the main pathways were NO3 electrophilic addition to olefin and the meta-position to the hydroxyl group. The uptake coefficient of NO3 radicals on ferulic acid particles was 0.17 ± 0.02 and the effective rate constant under experimental conditions was (1.71 ± 0.08) × 10-12 cm3 molecule-1 s-1. The results indicate that ferulic acid degradation by NO3 can be an important sink at night.

  18. Polyphenols and phenolic acids in sweet potato (Ipomoea batatas L. roots

    Directory of Open Access Journals (Sweden)

    Janette Musilová

    2017-01-01

    Full Text Available Sweet potato (Ipomoea batatas L. is one of the most important food crops in the world. They are rich in polyphenols, proteins, vitamins, minerals and some functional microcomponents. Polyphenols are bioactive compounds, which can protect the human body from the oxidative stress which may cause many diseases including cancer, aging and cardiovascular problems.The polyphenol content is two to three times higher than in some common vegetables. Total polyphenols (determined spectrophotometrically and phenolic acids (i.e. caffeic acid, chlorogenic acid and isomers - using high performance liquid chromatography contents were determined in three varieties of sweet potatoes (O´Henry - white, Beauregard-orange and 414-purple. Phenolic compounds contents were determined in raw peeled roots, jackets of raw roots and water steamed sweet potato roots. For all analysis lyophilised samples were used. Total polyphenol content ranged from 1161 (O´Henry, flesh-raw to 13998 (414, peel-raw mg.kg-1 dry matter, caffeic acid content from the non-detected values (414, flesh-raw to 320.7 (Beauregard, peel-raw mg.kg-1 dry matter and 3-caffeoylquinic acid content from 57.57 (O´Henry, flesh-raw to 2392 (414, peel-raw mg.kg-1 dry matter. Statistically significant differences (p ≤0.05 existed between varieties, morphological parts of the root, or raw and heat-treated sweet potato in phenolic compounds contents.

  19. Conversion of hydroxycinnamic acids into volatile phenols in a synthetic medium and in red wine by Dekkera bruxellensis

    Directory of Open Access Journals (Sweden)

    Maria João Cabrita

    2012-03-01

    Full Text Available The conversion of p-coumaric acid, ferulic acid, and caffeic acid into 4-ethylphenol, 4-ethylguaiacol and 4-ethylcatechol was studied in Dekkera bruxellensis ISA 1791 under defined conditions in a synthetic medium and in a red wine. Liquid chromatography (HPLC-DAD was used to quantify the phenolic acids, and gas chromatography (GC coupled to a FID detector was used to quantify volatile phenols using a novel analytical methodology that does not require sample derivatization. Identification was achieved by gas chromatography-mass detection (GC-MS. The results show that phenolic acids concentration decreases while volatile phenols concentration increases. The proportion of caffeic acid taken up by Dekkera bruxellensis is lower than that for p-coumaric or ferulic acid; therefore less 4-ethylcatechol is formed. More important, 4-ethylcathecol synthesis by Dekkera bruxellensis in wine has never been demonstrated so far. These results contribute decisively to a better understanding of the origin of the volatile phenols in wines. The accumulation of these compounds in wine is nowadays regarded as one of the key factors of quality control.

  20. Wine phenolic compounds influence the production of volatile phenols by wine-related lactic acid bacteria.

    Science.gov (United States)

    Silva, I; Campos, F M; Hogg, T; Couto, J A

    2011-08-01

    To evaluate the effect of wine phenolic compounds on the production of volatile phenols (4-vinylphenol [4VP] and 4-ethylphenol [4EP]) from the metabolism of p-coumaric acid by lactic acid bacteria (LAB). Lactobacillus plantarum, Lactobacillus collinoides and Pediococcus pentosaceus were grown in MRS medium supplemented with p-coumaric acid, in the presence of different phenolic compounds: nonflavonoids (hydroxycinnamic and benzoic acids) and flavonoids (flavonols and flavanols). The inducibility of the enzymes involved in the p-coumaric acid metabolism was studied in resting cells. The hydroxycinnamic acids tested stimulated the capacity of LAB to synthesize volatile phenols. Growth in the presence of hydroxycinnamic acids, especially caffeic acid, induced the production of 4VP by resting cells. The hydroxybenzoic acids did not significantly affect the behaviour of the studied strains. Some of the flavonoids showed an effect on the production of volatile phenols, although strongly dependent on the bacterial species. Relatively high concentrations (1 g l(-1) ) of tannins inhibited the synthesis of 4VP by Lact. plantarum. Hydroxycinnamic acids were the main compounds stimulating the production of volatile phenols by LAB. The results suggest that caffeic and ferulic acids induce the synthesis of the cinnamate decarboxylase involved in the metabolism of p-coumaric acid. On the other hand, tannins exert an inhibitory effect. This study highlights the capacity of LAB to produce volatile phenols and that this activity is markedly influenced by the phenolic composition of the medium. © 2011 The Authors. Journal of Applied Microbiology © 2011 The Society for Applied Microbiology.

  1. Chromatographical analysis of phenolic acids in some species of Polygonum L. genus. Part 1 Qualitative analysis by two-dimensional thin layer chromatography (TLC

    Directory of Open Access Journals (Sweden)

    Helena D. Smolarz

    2014-01-01

    Full Text Available The Two-Dimensional Thin Layer Chromatography method has been used for the separation and identification of phenolic acids from six taxons of Pohygonum L. genus. The following acids were found: caffeic, p-coumaric, ferulic, p-hydroxybenzoic, m-hydroxybenzoic, vanillic, syringic, p-hydroxyphenylacetic, o-hydroxyphenylacetic, synapic, melillotic, salicylic, gentisic, elagic, gallic, chlorogenic, protocatechuic and homoprotocatechuic. Gallic, ferulic, vanillic, p-coumaric and p-hydroxybenzoic acids were isolated from herb Polygonum convolvulus L. using column chromatography.

  2. Dietary phenolic acids reverse insulin resistance, hyperglycaemia, dyslipidaemia, inflammation and oxidative stress in high-fructose diet-induced metabolic syndrome rats.

    Science.gov (United States)

    Ibitoye, Oluwayemisi B; Ajiboye, Taofeek O

    2017-12-20

    This study investigated the influence of caffeic, ferulic, gallic and protocatechuic acids on high-fructose diet-induced metabolic syndrome in rats. Oral administration of the phenolic acids significantly reversed high-fructose diet-mediated increase in body mass index and blood glucose. Furthermore, phenolic acids restored high-fructose diet-mediated alterations in metabolic hormones (insulin, leptin and adiponectin). Similarly, elevated tumour necrosis factor-α, interleukin-6 and -8 were significantly lowered. Administration of phenolic acids restored High-fructose diet-mediated increase in the levels of lipid parameters and indices of atherosclerosis, cardiac and cardiovascular diseases. High-fructose diet-mediated decrease in activities of antioxidant enzymes (superoxide dismutase, catalase, glutathione peroxidase, glutathione reductase and glucose 6-phosphate dehydrogenase) and increase in oxidative stress biomarkers (reduced glutathione, lipid peroxidation products, protein oxidation and fragmented DNA) were significantly restored by the phenolic acids. The result of this study shows protective influence of caffeic acid, ferulic acid, gallic acid and protocatechuic acid in high-fructose diet-induced metabolic syndrome.

  3. Accumulation of Phenolic Compounds and Expression Profiles of Phenolic Acid Biosynthesis-Related Genes in Developing Grains of White, Purple, and Red Wheat.

    Science.gov (United States)

    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.

  4. Graphene oxide for solid-phase extraction of bioactive phenolic acids.

    Science.gov (United States)

    Hou, Xiudan; Wang, Xusheng; Sun, Yingxin; Wang, Licheng; Guo, Yong

    2017-05-01

    A solid-phase extraction (SPE) method for the efficient analysis of trace phenolic acids (PAs, caffeic acid, ferulic acid, protocatechuic acid, cinnamic acid) in urine was established. In this work, a graphene oxide (GO) coating was grafted onto pure silica to be investigated as SPE material. The prepared GO surface had a layered and wrinkled structure that was rough and well organized, which could provide more open adsorption sites. Owing to its hydrophilicity and polarity, GO showed higher extraction efficiency toward PAs than reduced GO did, in agreement with the theoretical calculation results performed by Gaussian 09 software. The adsorption mechanism of PAs on GO@Sil was also investigated through static state and kinetic state adsorption experiments, which showed a monolayer surface adsorption. Extraction capacity of the as-prepared material was optimized using the response surface methodology. Under the optimized conditions, the as-established method provided wide linearity range (2-50 μg L -1 for protocatechuic acid and 1-50 μg L -1 for caffeic acid, ferulic acid, and cinnamic acid) and low limits of detection (0.25-1 μg L -1 ). Finally, the established method was applied for the analysis of urine from two healthy volunteers. The results indicate that the prepared material is a practical, cost-effective medium for the extraction and determination of phenolic acids in complex matrices. Graphical Abstract A graphene oxide coating was grafted onto pure silica as the SPE material for the extraction of phenolic acids in urines and the extraction mechanism was also mainly investigated.

  5. Influence of phenolic compounds on the growth and arginine deiminase system in a wine lactic acid bacterium

    Directory of Open Access Journals (Sweden)

    María R. Alberto

    2012-03-01

    Full Text Available The influence of seven phenolic compounds, normally present in wine, on the growth and arginine deiminase system (ADI of Lactobacillus hilgardii X1B, a wine lactic acid bacterium, was established. This system provides energy for bacterial growth and produces citrulline that reacts with ethanol forming the carcinogen ethyl carbamate (EC, found in some wines. The influence of phenolic compounds on bacterial growth was compound dependent. Growth and final pH values increased in presence of arginine. Arginine consumption decreased in presence of protocatechuic and gallic acids (31 and 17%, respectively and increased in presence of quercetin, rutin, catechin and the caffeic and vanillic phenolic acids (between 10 and 13%, respectively. ADI enzyme activities varied in presence of phenolic compounds. Rutin, quercetin and caffeic and vanillic acids stimulated the enzyme arginine deiminase about 37-40%. Amounts of 200 mg/L gallic and protocatechuic acids inhibited the arginine deiminase enzyme between 53 and 100%, respectively. Ornithine transcarbamylase activity was not modified at all concentrations of phenolic compounds. As gallic and protocatechuic acids inhibited the arginine deiminase enzyme that produces citrulline, precursor of EC, these results are important considering the formation of toxic compounds.

  6. HPLC determination of phenolic acids, flavonoids and juglone in walnut leaves.

    Science.gov (United States)

    Nour, Violeta; Trandafir, Ion; Cosmulescu, Sina

    2013-10-01

    A high-performance liquid chromatographic method with gradient elution and diode-array detection was developed to quantify free phenolic acids (gallic, vanillic, chlorogenic, caffeic, syringic, p-coumaric, ferulic, sinapic, salycilic, elagic and trans-cinnamic), flavonoids (catechin, epicatechin, rutin, myricetin and quercetin) and juglone in walnut leaves. Chromatographic separation was performed on a Hypersil Gold C18 column (5 µm particle size, 250 × 4.6 mm) and detection was conducted at three different wavelengths (254, 278 and 300 nm) according to the absorption maxima of the analyzed compounds. Validation procedures were conducted and the method was proven to be precise, accurate and sensitive. The developed method has been applied to analyze walnut leaves samples from nine different cultivars, with the same agricultural, geographical and climatic conditions. The experimental results revealed high concentrations of myricetin, catechin hydrate and rutin, and low concentrations of quercetin and epicatechin aglycones. Ellagic acid was established as the dominating phenolic acid of walnut leaves, followed by trans-cinnamic, chlorogenic and caffeic acids. Juglone content varied between 44.55 and 205.12 mg/100 g fresh weight. Significant differences were detected among cultivars for the concentration levels of phenolics.

  7. Radical quenching by rosmarinic acid from Lavandula vera MM cell culture.

    Science.gov (United States)

    Kovacheva, Elena; Georgiev, Milen; Pashova, Svetlana; Angelova, Maria; Ilieva, Mladenka

    2006-01-01

    This study was conducted to evaluate the radical scavenging capacities of extracts and preparations from a Lavandula vera MM plant cell culture with different rosmarinic acid content and to compare them with pure rosmarinic and caffeic acids as well. The methods, which were used are superoxide anion and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt radicals scavenging assays. Results showed that extracts and preparations from Lavandula vera MM possess strong radical scavengers, as the best both radical scavengers appeared to be the fractions with enriched rosmarinic acid content, obtained after ethylacetate fractioning (47.7% inhibition of superoxide radicals and 14.2 microM 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid equivalents, respectively). These data reveal the possibilities for application of these preparations as antioxidants.

  8. Enzymatic Lipophilization of Phenolic Acids through Esterification with Fatty Alcohols in Organic Solvents

    DEFF Research Database (Denmark)

    Yang, Zhiyong; Guo, Zheng; Xu, Xuebing

    2012-01-01

    and octadecenol respectively. However, the conversions of ferulic and caffeic acids under the same conditions were much lower than DHCA. The optimal mixture ratio of hexane to butanone was found to be 65:35. Using octanol and DHCA as model, the reaction parameters, such as temperature, enzyme load, reaction time...... and substrate molar ratio, were optimized with response surface modelling (RSM). The optimum conditions are finalized as: temperature 60 oC, reaction time 7 days, enzyme load 100 mg, and substrate molar ratio 4.34 (octanol/DHCA)....

  9. Antioxidant effects of phenolic rye (Secale cereale L.) extracts, monomeric hydroxycinnamates, and ferulic acid dehydrodimers on human low-density lipoproteins

    DEFF Research Database (Denmark)

    Andreasen, Mette Findal; Landbo, A K; Christensen, L P

    2001-01-01

    Dietary antioxidants that protect low-density lipoprotein (LDL) from oxidation may help to prevent atherosclerosis and coronary heart disease. The antioxidant activities of purified monomeric and dimeric hydroxycinnamates and of phenolic extracts from rye (whole grain, bran, and flour) were...... investigated using an in vitro copper-catalyzed human LDL oxidation assay. The most abundant ferulic acid dehydrodimer (diFA) found in rye, 8-O-4-diFA, was a slightly better antioxidant than ferulic acid and p-coumaric acid. The antioxidant activity of the 8-5-diFA was comparable to that of ferulic acid......, but neither 5-5-diFA nor 8-5-benzofuran-diFA inhibited LDL oxidation when added at 10-40 microM. The antioxidant activity of the monomeric hydroxycinnamates decreased in the following order: caffeic acid > sinapic acid > ferulic acid > p-coumaric acid. The antioxidant activity of rye extracts...

  10. Effects of Phenolic Acids on the Growth and Production of T-2 and HT-2 Toxins by Fusarium langsethiae and F. sporotrichioides.

    Science.gov (United States)

    Ferruz, Elena; Atanasova-Pénichon, Vessela; Bonnin-Verdal, Marie-Noëlle; Marchegay, Gisèle; Pinson-Gadais, Laëtitia; Ducos, Christine; Lorán, Susana; Ariño, Agustín; Barreau, Christian; Richard-Forget, Florence

    2016-04-04

    The effect of natural phenolic acids was tested on the growth and production of T-2 and HT-2 toxins by Fusarium langsethiae and F. sporotrichioides, on Mycotoxin Synthetic medium. Plates treated with 0.5 mM of each phenolic acid (caffeic, chlorogenic, ferulic and p-coumaric) and controls without phenolic acid were incubated for 14 days at 25 °C. Fungal biomass of F. langsethiae and F. sporotrichioides was not reduced by the phenolic acids. However, biosynthesis of T-2 toxin by F. langsethiae was significantly reduced by chlorogenic (23.1%) and ferulic (26.5%) acids. Production of T-2 by F. sporotrichioides also decreased with ferulic acid by 23% (p phenolic acids had a variable effect on fungal growth and mycotoxin production, depending on the strain and the concentration and type of phenolic acid assayed.

  11. Phenolic Acid Content and Antioxidant Properties of Extruded Corn Snacks Enriched with Kale

    Science.gov (United States)

    Kasprzak, Kamila; Oniszczuk, Tomasz; Waksmundzka-Hajnos, Monika; Nowak, Renata; Polak, Renata

    2018-01-01

    Prohealth food contains specific components which have positive influence on the health and well-being of the consumer. An important position among bioactive compounds occurs for polyphenols. Many results have indicated that an increased intake of phenolic compounds may reduce the risk of cardiovascular diseases and type 2 diabetes. The objective of the study was production of extruded corn snacks with addition (0, 2, 4, 6, and 8%) of kale (Brassica oleracea L. var. sabellica)—a polyphenol-rich plant. Afterwards, high-performance liquid chromatography-mass spectrometry (LC-ESI-MS/MS) and antioxidant activity analyses of snack extracts were performed. In the corn snacks enriched with kale, fifteen phenolic acids were indicated. These were protocatechuic, 4-OH-benzoic, vanillic, trans-caffeic, cis-caffeic, trans-p-coumaric, cis-p-coumaric, trans-ferulic, cis-ferulic, salicylic, gentisic, syringic, 3-OH-cinnamic, trans-sinapic, and cis-sinapic acids. Both the qualitative and quantitative content of polyphenols increased with the addition of B. oleracea. Data from spectrophotometric analyses of the samples showed high DPPH radical scavenging potential of snacks enriched with 4, 6, and 8% of kale. Snacks enriched with kale contain high level of phenolic acids and, therefore, have great potential to make a valuable source of natural antioxidants. High-temperature short-time extrusion-cooking process had no negative impact on polyphenol's activity. PMID:29507816

  12. Phenolic Acid Content and Antioxidant Properties of Extruded Corn Snacks Enriched with Kale

    Directory of Open Access Journals (Sweden)

    Kamila Kasprzak

    2018-01-01

    Full Text Available Prohealth food contains specific components which have positive influence on the health and well-being of the consumer. An important position among bioactive compounds occurs for polyphenols. Many results have indicated that an increased intake of phenolic compounds may reduce the risk of cardiovascular diseases and type 2 diabetes. The objective of the study was production of extruded corn snacks with addition (0, 2, 4, 6, and 8% of kale (Brassica oleracea L. var. sabellica—a polyphenol-rich plant. Afterwards, high-performance liquid chromatography-mass spectrometry (LC-ESI-MS/MS and antioxidant activity analyses of snack extracts were performed. In the corn snacks enriched with kale, fifteen phenolic acids were indicated. These were protocatechuic, 4-OH-benzoic, vanillic, trans-caffeic, cis-caffeic, trans-p-coumaric, cis-p-coumaric, trans-ferulic, cis-ferulic, salicylic, gentisic, syringic, 3-OH-cinnamic, trans-sinapic, and cis-sinapic acids. Both the qualitative and quantitative content of polyphenols increased with the addition of B. oleracea. Data from spectrophotometric analyses of the samples showed high DPPH radical scavenging potential of snacks enriched with 4, 6, and 8% of kale. Snacks enriched with kale contain high level of phenolic acids and, therefore, have great potential to make a valuable source of natural antioxidants. High-temperature short-time extrusion-cooking process had no negative impact on polyphenol’s activity.

  13. Phenolic Acid Content and Antioxidant Properties of Extruded Corn Snacks Enriched with Kale.

    Science.gov (United States)

    Kasprzak, Kamila; Oniszczuk, Tomasz; Wójtowicz, Agnieszka; Waksmundzka-Hajnos, Monika; Olech, Marta; Nowak, Renata; Polak, Renata; Oniszczuk, Anna

    2018-01-01

    Prohealth food contains specific components which have positive influence on the health and well-being of the consumer. An important position among bioactive compounds occurs for polyphenols. Many results have indicated that an increased intake of phenolic compounds may reduce the risk of cardiovascular diseases and type 2 diabetes. The objective of the study was production of extruded corn snacks with addition (0, 2, 4, 6, and 8%) of kale ( Brassica oleracea L. var. sabellica )-a polyphenol-rich plant. Afterwards, high-performance liquid chromatography-mass spectrometry (LC-ESI-MS/MS) and antioxidant activity analyses of snack extracts were performed. In the corn snacks enriched with kale, fifteen phenolic acids were indicated. These were protocatechuic, 4-OH-benzoic, vanillic, trans -caffeic, cis -caffeic, trans -p-coumaric, cis -p-coumaric, trans -ferulic, cis -ferulic, salicylic, gentisic, syringic, 3-OH-cinnamic, trans -sinapic, and cis -sinapic acids. Both the qualitative and quantitative content of polyphenols increased with the addition of B. oleracea . Data from spectrophotometric analyses of the samples showed high DPPH radical scavenging potential of snacks enriched with 4, 6, and 8% of kale. Snacks enriched with kale contain high level of phenolic acids and, therefore, have great potential to make a valuable source of natural antioxidants. High-temperature short-time extrusion-cooking process had no negative impact on polyphenol's activity.

  14. Structure Properties and Mechanisms of Action of Naturally Originated Phenolic Acids and Their Derivatives against Human Viral Infections.

    Science.gov (United States)

    Wu, Yi-Hang; Zhang, Bing-Yi; Qiu, Li-Peng; Guan, Rong-Fa; Ye, Zi-Hong; Yu, Xiao-Ping

    2017-01-01

    A great effort has been made to develop efficacious antiviral drugs, but many viral infections are still lack of efficient antiviral therapies so far. The related exploration of natural products to fight viruses has been raised in recent years. Natural compounds with structural diversity and complexity offer a great chance to find new antiviral agents. Particularly, phenolic acids have attracted considerable attention owing to their potent antiviral abilities and unique mechanisms. The aim of this review is to report new discoveries and updates pertaining to antiviral phenolic acids. The relevant references on natural phenolic acids were searched. The antiviral phenolic acids were classified according to their structural properties and antiviral types. Meanwhile, the antiviral characteristics and structure-activity relationships of phenolic acids and their derivatives were summarized. The review finds that natural phenolic acids and their derivatives possessed potent inhibitory effects on multiple virus in humans such as human immunodeficiency virus, hepatitis C virus, hepatitis B virus, herpes simplex virus, influenza virus and respiratory syncytial virus. In particular, caffeic acid/gallic acid and their derivatives exhibited outstanding antiviral properties by a variety of modes of action. Naturally derived phenolic acids especially caffeic acid/gallic acid and their derivatives may be regarded as novel promising antiviral leads or candidates. Additionally, scarcely any of these compounds has been used as antiviral treatment in clinical practice. Therefore, these phenolic acids with diverse skeletons and mechanisms provide us an excellent resource for finding novel antiviral drugs. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

  15. Antioxidant capacity, phenolic acids and caffeine contents of some commercial coffees available on the Romanian market.

    Science.gov (United States)

    Trandafir, Ion; Nour, Violeta; Ionica, Mira Elena

    2013-03-01

    In the present study a simple and highly sensitive RP-HPLC method has been established for simultaneous determination of chlorogenic acid, caffeic acid, vanillic acid and caffeine in coffee samples. The method has been applied to eight different coffees available on the Romanian market which were previously analysed concerning the total polyphenols content and antioxidant capacity. Reduction of the DPPH radical was used to determine the antioxidant capacity of the coffee extracts while the total polyphenols content was determined by spectrophotometry (Folin Ciocalteu's method). The total polyphenols content ranged from 1.98 g GAE/100 g to 4.19 g GAE/100 g while the caffeine content ranged from 1.89 g/100 g to 3.05 g/100 g. A large variability was observed in chlorogenic acid content of the investigated coffee samples which ranged between 0.6 and 2.32 g/100 g.

  16. Characterization of Free, Conjugated, and Bound Phenolic Acids in Seven Commonly Consumed Vegetables

    Directory of Open Access Journals (Sweden)

    Yuan Gao

    2017-11-01

    Full Text Available Phenolic acids are thought to be beneficial for human health and responsible for vegetables’ health-promoting properties. Free, conjugated, and bound phenolic acids of seven commonly consumed vegetables, including kidney bean, cow pea, snow pea, hyacinth bean, green soy bean, soybean sprouts and daylily, from the regions of Beijing, Hangzhou, and Guangzhou, were identified and quantified by ultra-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS. Three vegetables, namely green soy bean, soybean sprouts, and daylily (Hemerocallis fulva L., from the Beijing region contained higher concentrations of total phenolic acids than those from the Hangzhou and Guangzhou regions. The results indicated that the phenolic acid content in the seven vegetables appeared to be species-dependent. The highest content of phenolic acids was found in daylily, followed by green soy bean, while the least amounts were identified in kidney bean and hyacinth bean. Typically, phenolic acids are predominantly found in conjugated forms. Principle component analysis (PCA revealed some key compounds that differentiated the seven vegetables. Green soy bean, compared to the other six vegetables, was characterized by higher levels of syringic acid, ferulic acid, vanillic acid, and sinapic acid. Other compounds, particularly p-coumaric acid, neochlorogenic acid, and caffeic acid, exhibited significantly higher concentrations in daylily. In addition, p-coumaric acid was the characteristic substance in cow pea. Results from this study can contribute to the development of vegetables with specific phytochemicals and health benefits.

  17. Characterization of Free, Conjugated, and Bound Phenolic Acids in Seven Commonly Consumed Vegetables.

    Science.gov (United States)

    Gao, Yuan; Ma, Shuai; Wang, Meng; Feng, Xiao-Yuan

    2017-11-01

    Phenolic acids are thought to be beneficial for human health and responsible for vegetables' health-promoting properties. Free, conjugated, and bound phenolic acids of seven commonly consumed vegetables, including kidney bean, cow pea, snow pea, hyacinth bean, green soy bean, soybean sprouts and daylily, from the regions of Beijing, Hangzhou, and Guangzhou, were identified and quantified by ultra-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS). Three vegetables, namely green soy bean, soybean sprouts, and daylily ( Hemerocallis fulva L.), from the Beijing region contained higher concentrations of total phenolic acids than those from the Hangzhou and Guangzhou regions. The results indicated that the phenolic acid content in the seven vegetables appeared to be species-dependent. The highest content of phenolic acids was found in daylily, followed by green soy bean, while the least amounts were identified in kidney bean and hyacinth bean. Typically, phenolic acids are predominantly found in conjugated forms. Principle component analysis (PCA) revealed some key compounds that differentiated the seven vegetables. Green soy bean, compared to the other six vegetables, was characterized by higher levels of syringic acid, ferulic acid, vanillic acid, and sinapic acid. Other compounds, particularly p -coumaric acid, neochlorogenic acid, and caffeic acid, exhibited significantly higher concentrations in daylily. In addition, p -coumaric acid was the characteristic substance in cow pea. Results from this study can contribute to the development of vegetables with specific phytochemicals and health benefits.

  18. Effect of postharvest methyl jasmonate treatment on fatty acid composition and phenolic acid content in olive fruits during storage.

    Science.gov (United States)

    Flores, Gema; Blanch, Gracia Patricia; Del Castillo, María Luisa Ruiz

    2017-07-01

    The nutritional effects of both table olives and olive oil are attributed not only to their fatty acids but also to antioxidant phenolics such as phenolic acids. Delays in oil processing usually result in undesirable oxidation and hydrolysis processes leading to formation of free fatty acids. These alterations create the need to process oil immediately after olive harvest. However, phenolic content decreases drastically during olive storage resulting in lower quality oil. In the present study we propose postharvest methyl jasmonate treatment as a mean to avoid changes in fatty acid composition and losses of phenolic acids during olive storage. Contents of fatty acids and phenolic acids were estimated in methyl jasmonate treated olives throughout 30-day storage, as compared with those of untreated olives. Significant decreases of saturated fatty acids were observed in treated samples whereas increases of oleic, linoleic and linolenic acids were respectively measured (i.e. from 50.8% to 64.5%, from 7.2% to 9.1% and from 1.5% to 9.3%). Also, phenolic acid contents increased significantly in treated olives. Particularly, increases of gallic acid from 1.35 to 6.29 mg kg -1 , chlorogenic acid from 9.18 to 16.21 mg kg -1 , vanillic acid from 9.61 to 16.99 mg kg -1 , caffeic acid from 5.12 to 12.55 mg kg -1 , p-coumaric acid from 0.96 to 5.31 mg kg -1 and ferulic acid from 4.05 to 10.43 mg kg -1 were obtained. Methyl jasmonate treatment is proposed as an alternative postharvest technique to traditional methods to guarantee olive oil quality when oil processing is delayed and olive fruits have to necessarily to be stored. © 2016 Society of Chemical Industry. © 2016 Society of Chemical Industry.

  19. Effects of abscisic acid, gibberellin, ethylene and their interactions on production of phenolic acids in salvia miltiorrhiza bunge hairy roots.

    Science.gov (United States)

    Liang, Zongsuo; Ma, Yini; Xu, Tao; Cui, Beimi; Liu, Yan; Guo, Zhixin; Yang, Dongfeng

    2013-01-01

    Salvia miltiorrhiza is one of the most important traditional Chinese medicinal plants because of its excellent performance in treating coronary heart disease. Phenolic acids mainly including caffeic acid, rosmarinic acid and salvianolic acid B are a group of active ingredients in S. miltiorrhiza. Abscisic acid (ABA), gibberellin (GA) and ethylene are three important phytohormones. In this study, effects of the three phytohormones and their interactions on phenolic production in S. miltiorrhiza hairy roots were investigated. The results showed that ABA, GA and ethylene were all effective to induce production of phenolic acids and increase activities of PAL and TAT in S. miltiorrhiza hairy roots. Effects of phytohormones were reversed by their biosynthetic inhibitors. Antagonistic actions between the three phytohormones played important roles in the biosynthesis of phenolic acids. GA signaling is necessary for ABA and ethylene-induced phenolic production. Yet, ABA and ethylene signaling is probably not necessary for GA3-induced phenolic production. The complex interactions of phytohormones help us reveal regulation mechanism of secondary metabolism and scale-up production of active ingredients in plants.

  20. The role of topically applied L-ascorbic acid in ex-vivo examination of burn-injured human skin

    Science.gov (United States)

    Pielesz, Anna; Biniaś, Dorota; Bobiński, Rafał; Sarna, Ewa; Paluch, Jadwiga; Waksmańska, Wioletta

    2017-10-01

    Wound treatment and healing is complex and is comprised of an elaborate set of processes including cellular, spectroscopic and biochemical ones as well as the ;reaction; of local tissue to thermal injury. Vitamin C as L-ascorbic acid (LA) prevents injurious effects of oxidants because it reduces reactive oxygen species to stable molecules, it becomes oxidized to the short-lived ascorbyl radical. As a result, antioxidant treatment may contribute to minimizing injury in burn patients. The aim of this study is to assess changes in molecular structure of collagen extracted from human epidermis burn wound scab during incubation of the epidermis in L-ascorbic acid solution. The study will be performed using FTIR and FT Raman spectroscopies. During this research it was observed that the intensity of Raman peaks increased where healing was being modified by LA. The intensity of the amide III band at 1247 cm- 1 relative to the intensity at 1326 cm- 1 was used to test tissue repair degree at the incision site. FTIR spectra were recorded from frozen specimens of serum modified by LA; an analysis of shifts in the amide I band position was conducted. The appearance of a new band for frozen samples modified by LA was observed around 1149-1220 cm- 1. The above conclusions confirmed the creation of hydrogen bonds between Nsbnd H stretch and Cdbnd O. Samples being incubated in solutions of L-ascorbic acid demonstrated the absence of electrophoretic bands of albumin. Alterations in the surface of the skin incubated in L-ascorbic acid were investigated with the use of Scanning Electron Microscopy (SEM). A decrease in external symptoms of burn injury was noted in the damaged epidermis incubated in L-ascorbic acid.

  1. Transformation of 5-O-caffeoylquinic acid in blueberries during high-temperature processing.

    Science.gov (United States)

    Dawidowicz, Andrzej L; Typek, Rafal

    2014-11-12

    Chlorogenic acid (CQA), an ester of caffeic with quinic acid, is a natural compound found in a wide array of plants. Although coffee beans are most frequently mentioned as plant products remarkably rich in CQAs, their significant amounts can also be found in many berries, for example, blueberries. This paper shows and discusses the thermal stability of the main CQA representative, that is, 5-O-caffeoylquinic acid (5-CQA), during high-temperature processing of blueberries (as in the production of blueberry foods) in systems containing sucrose in low and high concentration. It has been found that up to 11 components (5-CQA derivatives and its reaction product with water) can be formed from 5-CQA during the processing of blueberries. Their formation speed depends on the sucrose concentration in the processed system, which has been confirmed in the artificial system composed of 5-CQA water solution containing different amounts of the sugar.

  2. Hydroxycinnamic acids used as external acceptors of electrons: an energetic advantage for strictly heterofermentative lactic acid bacteria.

    Science.gov (United States)

    Filannino, Pasquale; Gobbetti, Marco; De Angelis, Maria; Di Cagno, Raffaella

    2014-12-01

    The metabolism of hydroxycinnamic acids by strictly heterofermentative lactic acid bacteria (19 strains) was investigated as a potential alternative energy route. Lactobacillus curvatus PE5 was the most tolerant to hydroxycinnamic acids, followed by strains of Weissella spp., Lactobacillus brevis, Lactobacillus fermentum, and Leuconostoc mesenteroides, for which the MIC values were the same. The highest sensitivity was found for Lactobacillus rossiae strains. During growth in MRS broth, lactic acid bacteria reduced caffeic, p-coumaric, and ferulic acids into dihydrocaffeic, phloretic, and dihydroferulic acids, respectively, or decarboxylated hydroxycinnamic acids into the corresponding vinyl derivatives and then reduced the latter compounds to ethyl compounds. Reductase activities mainly emerged, and the activities of selected strains were further investigated in chemically defined basal medium (CDM) under anaerobic conditions. The end products of carbon metabolism were quantified, as were the levels of intracellular ATP and the NAD(+)/NADH ratio. Electron and carbon balances and theoretical ATP/glucose yields were also estimated. When CDM was supplemented with hydroxycinnamic acids, the synthesis of ethanol decreased and the concentration of acetic acid increased. The levels of these metabolites reflected on the alcohol dehydrogenase and acetate kinase activities. Overall, some biochemical traits distinguished the common metabolism of strictly heterofermentative strains: main reductase activity toward hydroxycinnamic acids, a shift from alcohol dehydrogenase to acetate kinase activities, an increase in the NAD(+)/NADH ratio, and the accumulation of supplementary intracellular ATP. Taken together, the above-described metabolic responses suggest that strictly heterofermentative lactic acid bacteria mainly use hydroxycinnamic acids as external acceptors of electrons. Copyright © 2014, American Society for Microbiology. All Rights Reserved.

  3. Effects of low nitrogen supply on tomato (Solanum lycopersicum) fruit yield and quality with special emphasis on sugars, acids, ascorbate, carotenoids, and phenolic compounds.

    Science.gov (United States)

    Bénard, Camille; Gautier, Hélène; Bourgaud, Frédéric; Grasselly, Dominique; Navez, Brigitte; Caris-Veyrat, Catherine; Weiss, Marie; Génard, Michel

    2009-05-27

    The objective of this study was to determine the impact of lowering nitrogen supply from 12 to 6 or 4 mM NO(3)(-) on tomato fruit yield and quality during the growing season. Lowering nitrogen supply had a low impact on fruit commercial yield (-7.5%), but it reduced plant vegetative growth and increased fruit dry matter content, improving consequently fruit quality. Fruit quality was improved due to lower acid (10-16%) and increased soluble sugar content (5-17%). The content of some phenolic compounds (rutin, a caffeic acid glycoside, and a caffeic acid derivate) and total ascorbic acid tended to be higher in fruit with the lowest nitrogen supply, but differences were significant in only a few cases (trusses). With regard to carotenoids, data did not show significant and univocal differences related to different levels of nitrogen supply. Thus, reducing nitrogen fertilization limited environmental pollution, on the one hand, and may improve, on the other hand, both growers' profits, by limiting nitrogen inputs, and fruit quality for consumers, by increasing tomato sugars content. It was concluded that primary and secondary metabolites could be affected as a result of a specific response to low nitrogen, combined with a lower degree of vegetative development, increasing fruit irradiance, and therefore modifying fruit composition.

  4. Investigations on some metabolites of Tecoma stans Juss. callus tissue. Part III. Chromatographical search for iridoids, phenolic acids, terpenoids and sugars

    Directory of Open Access Journals (Sweden)

    Barbara Dohnal

    2015-01-01

    Full Text Available Tissus cultures of Tecoma stans Juss. cultivated on modified Murashige-Skoog medium (RT-k were phytochemically analysed by means of chromatographical methods (PC, TLC. The following products were found as metabolites: phenolic acids - chlorogenics, caffeic, ferulic, vanillic, o-coumaric and sinapic; steroids - β-sitosterol; triterpenes - ursolic and oleanolic acids, α-amyrine; sugars - glucose, fructose, sucrose, xylose. Meso-inositol was isolated in 0.8% yield. In intact plant leaves, some differences concerning the content and/or number of individual compounds were observed, namely: lack of sinapic acid and occurrence of p-coumaric acid, lower content of β-sitosterol, lack of oleanolic acid, occurrence of β-amyrine and of one unidentified triterpenoid, lack of xylose, occurrence of maltose, raffinose, and stachiose. The level of mesoinositol inn leaves was distincly lower than in the callus tissues. Neither in callus tissues nor in leaves iridoid glycosides were found.

  5. Chlorogenic Acid Biosynthesis Appears Linked with Suberin Production in Potato Tuber (Solanum tuberosum).

    Science.gov (United States)

    Valiñas, Matías Ariel; Lanteri, María Luciana; ten Have, Arjen; Andreu, Adriana Balbina

    2015-05-20

    Potato (Solanum tuberosum L.) is a good source of dietary antioxidants. Chlorogenic acid (CGA) and caffeic acid (CA) are the most abundant phenolic acid antioxidants in potato and are formed by the phenylpropanoid pathway. A number of CGA biosynthetic routes that involve hydroxycinnamoyl-CoA quinate hydroxycinnamoyl transferase (HQT) and/or hydroxycinnamoyl-CoA shikimate/quinate hydroxycinnamoyl transferase (HCT) have been proposed, but little is known about their path in potato. CA production requires a caffeoyl shikimate esterase (CSE), and CA serves as a substrate of lignin precursor ferulic acid via the action of caffeic/5-hydroxyferulic acid O-methyltransferase (COMT I). CGA is precursor of caffeoyl-CoA and, via caffeoyl-CoA O-methyltransferase (CCoAOMT), of feruloyl-CoA. Feruloyl-CoA is required for lignin and suberin biosynthesis, crucial for tuber development. Here, metabolite and transcript levels of the mentioned and related enzymes, such as cinnamate 4-hydroxylase (C4H), were determined in the flesh and skin of fresh and stored tubers. Metabolite and transcript levels were higher in skin than in flesh, irrespective of storage. CGA and CA production appear to occur via p-coumaroyl-CoA, using HQT and CSE, respectively. HCT is likely involved in CGA remobilization toward suberin. The strong correlation between CGA and CA, the correspondence with C4H, HQT, CCoAOMT2, and CSE, and the negative correlation of HCT and COMT I in potato tubers suggest a major flux toward suberin.

  6. Effect of processing on phenolic acids composition and radical scavenging capacity of barley pasta.

    Science.gov (United States)

    De Paula, Rosanna; Rabalski, Iwona; Messia, Maria Cristina; Abdel-Aal, El-Sayed M; Marconi, Emanuele

    2017-12-01

    Phenolic acids, total phenolics content and DPPH radical scavenging capacity in raw ingredients, fresh and dried spaghetti, and in uncooked and cooked spaghetti were evaluated and compared with semolina spaghetti as a reference. Ferulic acid was the major phenolic acid found in the free and bound phenolic extracts in all the investigated pasta samples. The addition of barley flour into pasta at incorporation levels of 30, 50 and 100% increased phenolic acids and total phenolics content. Pasta processing did not significantly affect the total phenolics content and free radical scavenging capacity, but a significant reduction in total phenolic acids measured by HPLC was found. Drying process differently affected individual phenolic compounds in the free and bound fractions, and thus, the total phenolic acids content. Free vanillic, caffeic and p-coumaric acids did not significantly change, while p-hydroxybenzoic and ferulic acids of the free extracts showed higher values compared to the corresponding fresh pasta. Cooking did not greatly affect total phenolic acids, more leading to conserving free and bound phenolic compounds. Copyright © 2017 Elsevier Ltd. All rights reserved.

  7. Phenolic acid composition and antioxidant properties of Malaysian honeys.

    Science.gov (United States)

    Khalil, M I; Alam, N; Moniruzzaman, M; Sulaiman, S A; Gan, S H

    2011-08-01

    The phenolic acid and flavonoid contents of Malaysian Tualang, Gelam, and Borneo tropical honeys were compared to those of Manuka honey. Ferric reducing/antioxidant power assay (FRAP) and the 1,1-diphenyl-2-picryl-hydrazyl (DPPH) radical-scavenging activities were also quantified. All honey extracts exhibited high phenolic contents (15.21 ± 0.51- 42.23 ± 0.64 mg/kg), flavonoid contents (11.52 ± 0.27- 25.31 ± 0.37 mg/kg), FRAP values (892.15 ± 4.97- 363.38 ± 10.57 μM Fe[II]/kg), and high IC₅₀ of DPPH radical-scavenging activities (5.24 ± 0.40- 17.51 ± 0.51 mg/mL). Total of 6 phenolic acids (gallic, syringic, benzoic, trans-cinnamic, p-coumaric, and caffeic acids) and 5 flavonoids (catechin, kaempferol, naringenin, luteolin, and apigenin) were identified. Among the Malaysian honey samples, Tualang honey had the highest contents of phenolics, and flavonoids, and DPPH radical-scavenging activities. We conclude that among Malaysian honey samples, Tualang honey is the richest in phenolic acids, and flavonoid compounds, which have strong free radical-scavenging activities. © 2011 Institute of Food Technologists®

  8. Absorption of N-phenylpropenoyl-L-amino acids in healthy humans by oral administration of cocoa (Theobroma cacao).

    Science.gov (United States)

    Stark, Timo; Lang, Roman; Keller, Daniela; Hensel, Andreas; Hofmann, Thomas

    2008-10-01

    Besides flavan-3-ols, a family of N-phenylpropenoyl-L-amino acids (NPAs) has been recently identified as polyphenol/amino acid conjugates in the seeds of Theobroma cacao as well as in a variety of herbal drugs. Stimulated by reports on their biological activity, the purpose of this study was to investigate if these amides are absorbed by healthy volunteers after administration of a cocoa drink. For the first time, 12 NPAs were quantified in human urine by means of a stable isotope dilution analysis with LC-MS/MS (MRM) detection. A maximum amount was found in the urine taken 2 h after the cocoa consumption. The highest absolute amount of NPAs excreted with the urine was found for N-[4'-hydroxy-(E)-cinnamoyl]-L-aspartic acid (5), but the highest recovery rate (57.3 and 22.8%), that means the percentage amount of ingested amides excreted with the urine, were determined for N-[4'-hydroxy-(E)-cinnamoyl]-L-glutamic acid (6) and N-[4'-hydroxy-3'-methoxy-(E)-cinnamoyl]-L-tyrosine (13). In order to gain first insights into the NPA metabolism in vivo, urine samples were analyzed by LC-MS/MS before and after beta-glucuronidase/sulfatase treatment. As independent of the enzyme treatment the same NPA amounts were found in urine, there is strong evidence that these amides are metabolized neither via their O-glucuronides nor their O-sulfates. In order to screen for caffeic acid O-glucuronides as potential NPA metabolites, urine samples were screened by means of LC-MS/MS for caffeic acid 3-O-beta-D-glucuronide and 4-O-beta-D-glucuronide. But not even trace amounts of one of these glucuronides were detectable, thus excluding them as major NPA metabolites and underlining the importance of future investigations on a potential O-methylation or reduction of the N-phenylpropenoyl moiety in NPAs.

  9. Characterization and purification of a bacterial chlorogenic acid esterase detected during the extraction of chlorogenic acid from arbuscular mycorrhizal tomato roots.

    Science.gov (United States)

    Negrel, Jonathan; Javelle, Francine; Morandi, Dominique; Lucchi, Géraldine

    2016-12-01

    A Gram-negative bacterium able to grow using chlorogenic acid (5-caffeoylquinic acid) as sole carbon source has been isolated from the roots of tomato plants inoculated with the arbuscular mycorrhizal fungus Rhizophagus irregularis. An intracellular esterase exhibiting very high affinity (K m  = 2 μM) for chlorogenic acid has been extracted and purified by FPLC from the chlorogenate-grown cultures of this bacterium. The molecular mass of the purified esterase determined by SDS-PAGE was 61 kDa and its isoelectric point determined by chromatofocusing was 7.75. The esterase hydrolysed chlorogenic acid analogues (caffeoylshikimate, and the 4- and 3-caffeoylquinic acid isomers), feruloyl esterases substrates (methyl caffeate and methyl ferulate), and even caffeoyl-CoA in vitro but all of them were less active than chlorogenic acid, demonstrating that the esterase is a genuine chlorogenic acid esterase. It was also induced when the bacterial strain was cultured in the presence of hydroxycinnamic acids (caffeic, p-coumaric or ferulic acid) as sole carbon source, but not in the presence of simple phenolics such as catechol or protocatechuic acid, nor in the presence of organic acids such as succinic or quinic acids. The purified esterase was remarkably stable in the presence of methanol, rapid formation of methyl caffeate occurring when its activity was measured in aqueous solutions containing 10-60% methanol. Our results therefore show that this bacterial chlorogenase can catalyse the transesterification reaction previously detected during the methanolic extraction of chlorogenic acid from arbuscular mycorrhizal tomato roots. Data are presented suggesting that colonisation by Rhizophagus irregularis could increase chlorogenic acid exudation from tomato roots, especially in nutrient-deprived plants, and thus favour the growth of chlorogenate-metabolizing bacteria on the root surface or in the mycorhizosphere. Copyright © 2016 Elsevier Masson SAS. All rights

  10. Aspartic acid

    Science.gov (United States)

    ... we eat. Aspartic acid is also called asparaginic acid. Aspartic acid helps every cell in the body work. It ... release Normal nervous system function Plant sources of aspartic acid include: avocado, asparagus, and molasses. Animal sources of ...

  11. Identification of phenolic acids and flavonoids in monofloral honey from Bangladesh by high performance liquid chromatography: determination of antioxidant capacity.

    Science.gov (United States)

    Moniruzzaman, Mohammed; Yung An, Chua; Rao, Pasupuleti Visweswara; Hawlader, Mohammad Nurul Islam; Azlan, Siti Amirah Binti Mohd; Sulaiman, Siti Amrah; Gan, Siew Hua

    2014-01-01

    The aim of the present study was to characterize the phenolic acids, flavonoids, and antioxidant properties of monofloral honey collected from five different districts in Bangladesh. A new high performance liquid chromatography (HPLC) equipped with a UV detector method was developed for the identification of the phenolic acids and flavonoids. A total of five different phenolic acids were identified, with the most abundant being caffeic acid, benzoic acid, gallic acid, followed by chlorogenic acid and trans-cinnamic acid. The flavonoids, kaempferol, and catechin were most abundant, followed by myricetin and naringenin. The mean moisture content, total sugar content, and color characteristics of the honey samples were 18.36 ± 0.95%, 67.40 ± 5.63 g/100 g, and 129.27 ± 34.66 mm Pfund, respectively. The mean total phenolic acids, total flavonoid content, and proline content were 199.20 ± 135.23, 46.73 ± 34.16, and 556.40 ± 376.86 mg/kg, respectively, while the mean FRAP values and DPPH radical scavenging activity were 327.30 ± 231.87 μM Fe (II)/100 g and 36.95 ± 20.53%, respectively. Among the different types of honey, kalijira exhibited the highest phenolics and antioxidant properties. Overall, our study confirms that all the investigated honey samples are good sources of phenolic acids and flavonoids with good antioxidant properties.

  12. Enhanced production of phenolic acids in cell suspension culture of Salvia leriifolia Benth. using growth regulators and sucrose.

    Science.gov (United States)

    Modarres, Masoomeh; Esmaeilzadeh Bahabadi, Sedigheh; Taghavizadeh Yazdi, Mohammad Ehsan

    2018-04-01

    Salvia leriifolia Benth. (Lamiaceae) is an endangered medicinal plant with hypoglycemic, anti-inflammatory and analgesic properties. Many of the beneficial effects of Salvia spp. are attributed to the phenolic compounds. In the present study, an efficient procedure has been developed for establishment of cell suspension culture of S. leriifolia as a strategy to obtain an in vitro phenolic acids producing cell line for the first time. The effect of growth regulators and various concentrations of sucrose have been analyzed, to optimize biomass growth and phenolic acids production. The callus used for this purpose was obtained from leaves of 15-day-old in vitro seedlings, on Murashige and Skoog (MS) basal medium supplemented with different hormone balances including benzylaminopurine (BAP) and indole butyric acid (IBA); 2,4-dichlorophenoxyacetic acid (2,4-D) and kinetin (KIN); naphthaleneacetic acid (NAA) and BAP. Modified MS medium supplemented with 5 mg/L BAP and 5 mg/L NAA was the optimal condition for callus formation with the highest induction rate (100%), the best callus growth and the highest phenolic acids content. No callus induction was observed in combinations of IBA and BAP. Cell suspension cultures were established by transferring 0.5 g of callus to 30 mL liquid MS medium supplemented with 5 mg/L BAP and 5 mg/L NAA. Dynamics of phenolic acids production has been investigated during the growth cycle of the suspension cultures. The maximum content of caffeic acid and salvianolic acid B were observed on the 15th day of the cultivation cycle while the highest amount of rosmarinic acid was observed on the first day. In response to various sucrose concentrations, cell cultures with 40 g/L sucrose not only produced the highest dry biomass but also the highest induction of caffeic acid and salvianolic acid B. The highest amount of rosmarinic acid was observed in media containing 50 g/L sucrose. These prepared cell suspension cultures provided a useful

  13. Radical Scavenging Capacity of Methanolic Phillyrea latifolia L. Extract: Anthocyanin and Phenolic Acids Composition of Fruits

    Directory of Open Access Journals (Sweden)

    Naciye Erkan

    2013-01-01

    Full Text Available Radical scavenging capacity of a crude methanolic extract from the fruits of Phillyrea latifolia L., commonly known as green olive tree or mock privet, was investigated with reference to anthocyanin standards, as flavonoids, and phenolic acid standards, as phenylpropanoids. Characterization with high performance liquid chromatography-diode array detection (HPLC-DAD indicated the presence of keracyanin, kuromanin, cyanidin, ferulic acid, caffeic acid and rosmarinic acid at amounts of 289.1, 90.4, 191.4, 225.2, 221.2 and 190.1 mg/100 g fresh weight (FW of fruits, respectively. Chlorogenic and p-coumaric acids were found to exist in lower amounts. Trolox equivalent antioxidant capacity (TEAC and IC50 values of the plant extract were found to be 1.8 mM Trolox equivalents (TE/g FW of fruits and 69.4 µg/mL, respectively, indicating the close radical scavenging activity of the extract to those of keracyanin and p-coumaric acid. The crude methanolic P. latifolia L. fruit extract was seen to be fairly potent in radical scavenging. Total phenolic content (TPC of the plant extract was found to be 1652.9 mg gallic acid equivalent (GAE/100 g FW of fruits.

  14. Effects of antioxidants on the lipase-catalyzed acidolysis during production of structured lipids

    DEFF Research Database (Denmark)

    Xu, Xuebing; Timm Heinrich, Maike; Nielsen, Nina Skall

    2005-01-01

    In the production process of structured lipids, the influence of the addition of antioxidants before enzymatic acidolysis was investigated. Eight different antioxidants were screened: butylated hydroxyanisole, butylated hydroxytoluene, propyl gallate, ascorbyl palmitate, citric acid, EDTA...... of the structured lipid produced....

  15. Quantitative determination of chlorogenic acid in γ-ray-irradiated potato tubers by high performance liquid chromatography

    International Nuclear Information System (INIS)

    Nishizawa, Makoto; Chonan, Takao; Yamagishi, Takashi; Ando, Yoshiaki

    1984-01-01

    Chlorogenic acid (CGA) and caffeic acid (CA) in lyophilized potato tubers were quantitatively determined by high performance liquid chromatography (HPLC), and the changes in CGA contents of γ-ray-irradiated potato tubers (100 Gy) during storage at 25 0 C were studied. The CGA contents of the irradiated potato tubers slightly increased immediately after irradiation, but decreased gradually after 29th day and reached the same level as that in the beginning of storage on the 73rd day after irradiation. However, the CGA contents of the unirradiated potato tubers increased steadily with increasing days of storage period, and reached twice that in the beginning of storage on the 73rd day after irradiation. The CGA contents in potato tubers determined by Diazo and Folin-Denis methods were shown to be two - eight times higher than those by HPLC method, and there appeared to be no significant relation between the CGA contents determined by HPLC method and by colorimetrical methods. (author)

  16. Dietary supplementation with phytosterol and ascorbic acid reduces body mass accumulation and alters food transit time in a diet-induced obesity mouse model

    Directory of Open Access Journals (Sweden)

    Kozlowski Petri

    2011-06-01

    Full Text Available Abstract Previous research indicates that animals fed a high fat (HF diet supplemented with disodium ascorbyl phytostanyl phosphate (DAPP exhibit reduced mass accumulation when compared to HF control. This compound is a water-soluble phytostanol ester and consists of a hydrophobic plant stanol covalently bonded to ascorbic acid (Vitamin C. To provide insight into the mechanism of this response, we examined the in vivo effects of a high fat diet supplemented with ascorbic acid (AA in the presence and absence of unesterified phytosterols (PS, and set out to establish whether the supplements have a synergistic effect in a diet-induced obesity mouse model. Our data indicate that HF diet supplementation with a combination of 1% w/w phytosterol and 1% w/w ascorbic acid results in reduced mass accumulation, with mean differences in absolute mass between PSAA and HF control of 10.05%; and differences in mass accumulation of 21.6% (i.e. the PSAA group gained on average 21% less mass each week from weeks 7-12 than the HF control group. In our previous study, the absolute mass difference between the 2% DAPP and HF control was 41%, while the mean difference in mass accumulation between the two groups for weeks 7-12 was 67.9%. Mass loss was not observed in animals supplemented with PS or AA alone. These data suggest that the supplements are synergistic with respect to mass accumulation, and the esterification of the compounds further potentiates the response. Our data also indicate that chronic administration of PS, both in the presence and absence of AA, results in changes to fecal output and food transit time, providing insight into the possibility of long-term changes in intestinal function related to PS supplementation.

  17. Dietary supplementation with phytosterol and ascorbic acid reduces body mass accumulation and alters food transit time in a diet-induced obesity mouse model

    Science.gov (United States)

    2011-01-01

    Previous research indicates that animals fed a high fat (HF) diet supplemented with disodium ascorbyl phytostanyl phosphate (DAPP) exhibit reduced mass accumulation when compared to HF control. This compound is a water-soluble phytostanol ester and consists of a hydrophobic plant stanol covalently bonded to ascorbic acid (Vitamin C). To provide insight into the mechanism of this response, we examined the in vivo effects of a high fat diet supplemented with ascorbic acid (AA) in the presence and absence of unesterified phytosterols (PS), and set out to establish whether the supplements have a synergistic effect in a diet-induced obesity mouse model. Our data indicate that HF diet supplementation with a combination of 1% w/w phytosterol and 1% w/w ascorbic acid results in reduced mass accumulation, with mean differences in absolute mass between PSAA and HF control of 10.05%; and differences in mass accumulation of 21.6% (i.e. the PSAA group gained on average 21% less mass each week from weeks 7-12 than the HF control group). In our previous study, the absolute mass difference between the 2% DAPP and HF control was 41%, while the mean difference in mass accumulation between the two groups for weeks 7-12 was 67.9%. Mass loss was not observed in animals supplemented with PS or AA alone. These data suggest that the supplements are synergistic with respect to mass accumulation, and the esterification of the compounds further potentiates the response. Our data also indicate that chronic administration of PS, both in the presence and absence of AA, results in changes to fecal output and food transit time, providing insight into the possibility of long-term changes in intestinal function related to PS supplementation. PMID:21711516

  18. Ferulic Acid, But Not All Hydroxycinnamic Acids, Is a Novel T3SS Inducer of Ralstonia solanacearum and Promotes Its Infection Process in Host Plants under Hydroponic Condition

    Directory of Open Access Journals (Sweden)

    Yong Zhang

    2017-09-01

    Full Text Available Hydroxycinnamic acids (HCAs are typical monocyclic phenylpropanoids, including cinnamic acid (Cin, coumaric acid (Cou, caffeic acid (Caf, ferulic acid (FA and their isomers, and involved in the interactions between pathogens and host plants. Here, we focused on the impact of HCAs on expression of type III secretion system (T3SS in Ralstonia solanacearum. FA significantly induced the expression of the T3SS and some type III effectors (T3Es genes in hrp-inducing medium, while did not the other HCAs. However, exogenously supplemented FA did not affect the T3SS expression in planta and the elicitation of the hypersensitive response (HR in tobacco leaves. Consistent with its central roles in pathogenicity, the FA-induced expression of the T3SS led to significant promotion on infection process of R. solanacearum in tomato plants under hydroponics cultivation. Moreover, the FA-induced expression of the T3SS was specifically mediated by the well-characterized signaling cascade PrhA-prhI/R-PrhJ-HrpG-HrpB, independent of the other known regulatory pathways. In summary, our results demonstrated that FA, a novel inducer of the T3SS in R. solanacearum, was able to promote its infection process in host plants under hydroponics condition.

  19. Integrated electrochemical gluconic acid biosensor based on self-assembled monolayer-modified gold electrodes. Application to the analysis of gluconic acid in musts and wines.

    Science.gov (United States)

    Campuzano, S; Gamella, M; Serra, B; Reviejo, A J; Pingarrón, J M

    2007-03-21

    An integrated amperometric gluconic acid biosensor constructed using a gold electrode (AuE) modified with a self-assembled monolayer (SAM) of 3-mercaptopropionic acid (MPA) on which gluconate dehydrogenase (GADH, 0.84 U) and the mediator tetrathiafulvalene (TTF, 1.5 micromol) were coimmobilized by covering the electrode surface with a dialysis membrane is reported. The working conditions selected were Eapp=+0.15 V and 25+/-1 degrees C. The useful lifetime of one single TTF-GADH-MPA-AuE was surprisingly long. After 53 days of continuous use, the biosensor exhibited 86% of the original sensitivity. A linear calibration plot was obtained for gluconic acid over the 6.0x10(-7) to 2.0x10(-5) M concentration range, with a limit of detection of 1.9x10(-7) M. The effect of potential interferents (glucose, fructose, galactose, arabinose, and tartaric, citric, malic, ascorbic, gallic, and caffeic acids) on the biosensor response was evaluated. The behavior of the biosensor in a flow-injection system in connection with amperometric detection was tested. The analytical usefulness of the biosensor was evaluated by determining gluconic acid in wine and must samples, and the results obtained were validated by comparison with those provided by using a commercial enzyme test kit.

  20. Ilex paraguariensis and its main component chlorogenic acid inhibit fructose formation of advanced glycation endproducts with amino acids at conditions compatible with those in the digestive system.

    Science.gov (United States)

    Bains, Yasmin; Gugliucci, Alejandro

    2017-03-01

    We have previously shown that Ilex paraguariensis extracts have potent antiglycation actions. Associations of excess free fructose consumption with inflammatory diseases have been proposed to be mediated through in situ enteral formation of fructose AGEs, which, after being absorbed may contribute to inflammatory diseases via engagement of RAGE. In this proof of principle investigation we show fluorescent AGE formation between amino acids (Arg, Lys, Gly at 10-50mM) and fructose (10-50mM) under time, temperature, pH and concentrations compatible with the digestive system lumen and its inhibition by Ilex paraguariensis extracts. Incubation of amino acids with fructose (but not glucose) leads to a time dependent formation of AGE fluorescence, already apparent after just 1h incubation, a time frame well compatible with the digestive process. Ilex paraguariensis (mate tea) inhibited AGE formation by 83% at 50μl/ml (pfructose and amino acids at times and concentrations plausibly found in the intestines. The reaction is inhibited by mate tea and its individual phenolics (caffeic acid and chlorogenic acids). The study provides the first evidence for the proposed mechanism to explain epidemiological correlations between excess fructose consumption and inflammatory diseases. Enteral fructose-AGE formation would be inhibited by co-intake of Ilex paraguariensis, and potentially other beverages, fruits and vegetables that contain comparable concentrations of phenolics as in IP (mate tea). Copyright © 2016 Elsevier B.V. All rights reserved.

  1. Substrate promiscuity of a rosmarinic acid synthase from lavender (Lavandula angustifolia L.).

    Science.gov (United States)

    Landmann, Christian; Hücherig, Stefanie; Fink, Barbara; Hoffmann, Thomas; Dittlein, Daniela; Coiner, Heather A; Schwab, Wilfried

    2011-08-01

    One of the most common types of modification of secondary metabolites is the acylation of oxygen- and nitrogen-containing substrates to produce esters and amides, respectively. Among the known acyltransferases, the members of the plant BAHD family are capable of acylating a wide variety of substrates. Two full-length acyltransferase cDNAs (LaAT1 and 2) were isolated from lavender flowers (Lavandula angustifolia L.) by reverse transcriptase-PCR using degenerate primers based on BAHD sequences. Recombinant LaAT1 exhibited a broad substrate tolerance accepting (hydroxy)cinnamoyl-CoAs as acyl donors and not only tyramine, tryptamine, phenylethylamine and anthranilic acid but also shikimic acid and 4-hydroxyphenyllactic acid as acceptors. Thus, LaLT1 forms esters and amides like its phylogenetic neighbors. In planta LaAT1 might be involved in the biosynthesis of rosmarinic acid, the ester of caffeic acid and 3,4-dihydroxyphenyllactic acid, a major constituent of lavender flowers. LaAT2 is one of three members of clade VI with unknown function.

  2. Antioxidant Activities of Selected Berries and Their Free, Esterified, and Insoluble-Bound Phenolic Acid Contents

    Science.gov (United States)

    2018-01-01

    To explore the potential of berries as natural sources of bioactive compounds, the quantities of free, esterified, and insoluble-bound phenolic acids in a number of berries were determined. In addition, the antioxidant activities of the berries were determined using 2,2-diphenyl-1-picrylhydrazyl radical scavenging activity, ferric reducing antioxidant power, and Trolox equivalent antioxidant capacity assays, in addition to determination of their metal ion chelating activities. Furthermore, several phenolic compounds were detected using high-performance liquid chromatography. Of the 6 tested berries, black chokeberry and blackberry exhibited the strongest antioxidant activities, and the various berry samples were found to contain catechin, caffeic acid, p-coumaric acid, epicatechin, vanillic acid, quercitrin, resveratrol, morin, naringenin, and apigenin. Moreover, the antioxidant activities and total phenolic contents of the fractions containing insoluble-bound phenolic acids were higher than those containing the free and esterified phenolic acids. The results imply that the insoluble-bound fractions of these berries are important natural sources of antioxidants for the preparation of functional food ingredients and preventing diseases associated with oxidative stress. PMID:29662846

  3. Bifunctional Alkylating Agent-Induced p53 and Nonclassical Nuclear Factor kB Responses and Cell Death are Altered by Caffeic Acid Phenethyl Ester: A Potential Role for Antioxidant/Electrophilic Response-Element Signaling

    National Research Council Canada - National Science Library

    Minsavage, Gary D; Dillman III, James F

    2007-01-01

    ...) occurred within 5 min after exposure to tumor necrosis factor-alpha. However, exposure to BFA induced nonclassical NF-kB signaling as loss of IkBa was not observed until 2 or 6 h in NHEK or HaCaT cells, respectively...

  4. Acid Rain

    Science.gov (United States)

    Bricker, Owen P.; Rice, Karen C.

    1995-01-01

    Although acid rain is fading as a political issue in the United States and funds for research in this area have largely disappeared, the acidity of rain in the Eastern United States has not changed significantly over the last decade, and it continues to be a serious environmental problem. Acid deposition (commonly called acid rain) is a term applied to all forms of atmospheric deposition of acidic substances - rain, snow, fog, acidic dry particulates, aerosols, and acid-forming gases. Water in the atmosphere reacts with certain atmospheric gases to become acidic. For example, water reacts with carbon dioxide in the atmosphere to produce a solution with a pH of about 5.6. Gases that produce acids in the presence of water in the atmosphere include carbon dioxide (which converts to carbonic acid), oxides of sulfur and nitrogen (which convert to sulfuric and nitric acids}, and hydrogen chloride (which converts to hydrochloric acid). These acid-producing gases are released to the atmosphere through natural processes, such as volcanic emissions, lightning, forest fires, and decay of organic matter. Accordingly, precipitation is slightly acidic, with a pH of 5.0 to 5.7 even in undeveloped areas. In industrialized areas, most of the acid-producing gases are released to the atmosphere from burning fossil fuels. Major emitters of acid-producing gases include power plants, industrial operations, and motor vehicles. Acid-producing gases can be transported through the atmosphere for hundreds of miles before being converted to acids and deposited as acid rain. Because acids tend to build up in the atmosphere between storms, the most acidic rain falls at the beginning of a storm, and as the rain continues, the acids "wash out" of the atmosphere.

  5. Mathematical Evaluation of the Amino Acid and Polyphenol Content and Antioxidant Activities of Fruits from Different Apricot Cultivars

    Directory of Open Access Journals (Sweden)

    Rene Kizek

    2011-09-01

    Full Text Available Functional foods are of interest because of their significant effects on human health, which can be connected with the presence of some biologically important compounds. In this study, we carried out complex analysis of 239 apricot cultivars (Prunus armeniaca L. cultivated in Lednice (climatic area T4, South Moravia, Czech Republic. Almost all previously published studies have focused only on analysis of certain parameters. However, we focused on detection both primary and secondary metabolites in a selection of apricot cultivars with respect to their biological activity. The contents of thirteen biogenic alpha-L-amino acids (arginine, asparagine, isoleucine, lysine, serine, threonine, valine, leucine, phenylalanine, tryptophan, tyrosine, proline and alanine were determined using ion exchange chromatography with UV-Vis spectrometry detection. Profile of polyphenols, measured as content of ten polyphenols with significant antioxidant properties (gallic acid, procatechinic acid, p-aminobenzoic acid, chlorogenic acid, caffeic acid, vanillin, p-coumaric acid, rutin, ferrulic acid and quercetrin, was determined by high performance liquid chromatography with spectrometric/electrochemical detection. Moreover, content of total phenolics was determined spectrophotometrically using the Folin-Ciocalteu method. Antioxidant activity was determined using five independent spectrophotometric methods: DPPH assay, DMPD method, ABTS method, FRAP and Free Radicals methods. Considering the complexity of the obtained data, they were processed and correlated using bioinformatics techniques (cluster analysis, principal component analysis. The studied apricot cultivars were clustered according to their common biochemical properties, which has not been done before. The observed similarities and differences were discussed.

  6. Chlorogenic acid protects against atherosclerosis in ApoE-/- mice and promotes cholesterol efflux from RAW264.7 macrophages.

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    Chongming Wu

    Full Text Available 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.

  7. Hydroxycinnamic acid bound arabinoxylans from millet brans-structural features and antioxidant activity.

    Science.gov (United States)

    Bijalwan, Vandana; Ali, Usman; Kesarwani, Atul Kumar; Yadav, Kamalendra; Mazumder, Koushik

    2016-07-01

    Hydroxycinnamic acid bound arabinoxylans (HCA-AXs) were extracted from brans of five Indian millet varieties and response surface methodology was used to optimize the extraction conditions. The optimal condition to obtain highest yield of millet HCA-AXs was determined as follows: time 61min, temperature 66°C, ratio of solvent to sample 12ml/g. Linkage analysis indicated that hydroxycinnamic acid bound arabinoxylan from kodo millet (KM-HCA-AX) contained comparatively low branched arabinoxylan consisting of 14.6% mono-substituted, 1.2% di-substituted and 41.2% un-substituted Xylp residues. The HPLC analysis of millet HCA-AXs showed significant variation in the content of three major bound hydroxycinnamic acids (caffeic, p-coumaric and ferulic acid). The antioxidant activity of millet HCA-AXs were evaluated using three in vitro assay methods (DPPH, FRAP and β-carotene linoleate emulsion assays) which suggested both phenolic acid composition and structural characteristics of arabinoxylans could be correlated to their antioxidant potential, the detailed structural analysis revealed that low substituted KM-HCA-AX exhibited relatively higher antioxidant activity compared to other medium and highly substituted HCA-AXs from finger (FM), proso (PM), barnyard (BM) and foxtail (FOXM) millet. Copyright © 2016. Published by Elsevier B.V.

  8. The effect of prefermentative addition of gallic acid and ellagic acid on the red wine color, copigmentation and phenolic profiles during wine aging.

    Science.gov (United States)

    Zhang, Xin-Ke; He, Fei; Zhang, Bo; Reeves, Malcolm J; Liu, Yue; Zhao, Xu; Duan, Chang-Qing

    2018-04-01

    Though non-anthocyanin phenolics normally do not have red color, they affect the red color expression in the copigmentation of red wines. In this study, the influence of prefermentative addition of 300mg/L gallic acid and ellagic acid, as cofactors, on aging dry red wines had been systematically evaluated at the industrial scales from the perspectives of color, phenolic profiles and copigmentation effects of anthocyanins. Red wines made with these two compounds exhibited better color properties than the control, having better CIELAB chromatic parameters. Additionally, significantly higher levels of detectable anthocyanins and copigmented anthocyanin ratio had been observed. Wines with ellagic acid showed better chromatic properties and phenolic profiles than wines with gallic acid, as shown in previous theoretical results. Anti-copigmentation phenomenon was noticed and elucidated. These practical results confirmed that ellagic acid was the better cofactor, and would give more additional guidance for the production of high quality wine. Malvidin-3-O-glucoside (PubChem CID: 443,652); Petunidin-3-O-glucoside (PubChem CID: 443,651); Delphinidin-3-O-glucoside (PubChem CID: 443,650); Peonidin-3-O-glucoside (PubChem CID: 443,654); Ellagic acid (PubChem CID: 5,281,855); Gallic acid (PubChem CID: 370); Quercetin (PubChem CID: 443,654); Caffeic acid (PubChem CID: 689,043); (+)-catechin (PubChem CID: 9064); Vanillic acid (PubChem CID: 8468). Copyright © 2017. Published by Elsevier Ltd.

  9. Simultaneous quantification of eight organic acid components in Artemisia capillaris Thunb (Yinchen extract using high-performance liquid chromatography coupled with diode array detection and high-resolution mass spectrometry

    Directory of Open Access Journals (Sweden)

    Fangjun Yu

    2018-04-01

    Full Text Available We aim to determine the chemical constituents of Yinchen extract and Yinchen herbs using high-performance liquid chromatography coupled with diode array detection and high-resolution mass spectrometry. The method was developed to analyze of eight organic acid components of Yinchen extract (including neochlorogenic acid, chlorogenic acid, cryptochlorogenic acid, caffeic acid, 1,3-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid and 4,5-dicaffeoylquinic acid. The separation was conducted using an Agilent TC-C18 column with acetonitrile – 0.2% formic acid solution as the mobile phases under gradient elution. The analytical method was fully validated in terms of linearity, sensitivity, precision, repeatability as well as recovery, and subsequently the method was performed for the quantitative assessment of Yinchen extracts and Yinchen herbs. In addition, the changes of selected markers were studied when Yinchen herbs decocting in water and isomerization occurred between the chlorogenic acids. The proposed method enables both qualitative and quantitative analyses and could be developed as a new tool for the quality evaluation of Yinchen extract and Yinchen herbs. The changes of selected markers in water decoction process could give us some novel idea when studying the link between substances and drug efficacy. Keywords: Artemisia capillaris Thunb (Yinchen extract, Quality control, Organic acid, Transformation pathways, High-performance liquid chromatography

  10. Simultaneous Determination of Seven Phenolic Acids in Rat Plasma Using UHPLC-ESI-MS/MS after Oral Administration of Echinacea purpurea Extract

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    Yan Du

    2017-09-01

    Full Text Available A rapid and sensitive Ultra High Performance Liquid Chromatography Electrospray Ionization Tandem Mass Spectrometry (UHPLC-ESI-MS/MS method was developed and validated to simultaneously determine the concentration of seven phenolic acids (syringic acid, ferulic acid, caffeic acid, vanillic acid, p-coumaric acid, 3,4-dihydroxybenzoic acid and 4-hydroxybenzoic acid in rat plasma after oral administration of Echinacea purpurea extract. After mixing with the internal standard (IS, butylparaben, plasma samples were prepared by liquid–liquid extraction with ethyl acetate. The separation was performed using the Agilent Eclipse Plus C18 column (1.8 μm, 2.1 mm × 50 mm with a gradient system consisting of solution A (0.1% acetic acid in water and solution B (methanol at a flow rate of 0.3 mL/min. The detection was accomplished by a multiple reaction monitoring (MRM mode with electrospray ionization (ESI. The method was validated in terms of linearity, precision, accuracy, extraction recovery, matrix effect and stability. This method was successfully applied to study the pharmacokinetic properties of the seven compounds after oral administration of Echinacea purpurea extract in rats.

  11. Amino acids

    Science.gov (United States)

    ... this page: //medlineplus.gov/ency/article/002222.htm Amino acids To use the sharing features on this page, please enable JavaScript. Amino acids are organic compounds that combine to form proteins . ...

  12. Valproic Acid

    Science.gov (United States)

    ... acid is in a class of medications called anticonvulsants. It works by increasing the amount of a ... older (about 1 in 500 people) who took anticonvulsants such as valproic acid to treat various conditions ...

  13. Ascorbic Acid

    Science.gov (United States)

    Ascorbic acid is used to prevent and treat scurvy, a disease caused by a lack of vitamin C in ... Ascorbic acid comes in extended-release (long-acting) capsules and tablets, lozenges, syrup, chewable tablets, and liquid drops to ...

  14. Aminocaproic Acid

    Science.gov (United States)

    Aminocaproic acid is used to control bleeding that occurs when blood clots are broken down too quickly. This type ... the baby is ready to be born). Aminocaproic acid is also used to control bleeding in the ...

  15. Ethacrynic Acid

    Science.gov (United States)

    Ethacrynic acid, a 'water pill,' is used to treat swelling and fluid retention caused by various medical problems. It ... Ethacrynic acid comes as a tablet to take by mouth. It is usually taken once or twice a day ...

  16. Analysis of hydroxycinnamic acid degradation in Agrobacterium fabrum reveals a coenzyme A-dependent, beta-oxidative deacetylation pathway.

    Science.gov (United States)

    Campillo, Tony; Renoud, Sébastien; Kerzaon, Isabelle; Vial, Ludovic; Baude, Jessica; Gaillard, Vincent; Bellvert, Floriant; Chamignon, Cécile; Comte, Gilles; Nesme, Xavier; Lavire, Céline; Hommais, Florence

    2014-06-01

    The soil- and rhizosphere-inhabiting bacterium Agrobacterium fabrum (genomospecies G8 of the Agrobacterium tumefaciens species complex) is known to have species-specific genes involved in ferulic acid degradation. Here, we characterized, by genetic and analytical means, intermediates of degradation as feruloyl coenzyme A (feruloyl-CoA), 4-hydroxy-3-methoxyphenyl-β-hydroxypropionyl-CoA, 4-hydroxy-3-methoxyphenyl-β-ketopropionyl-CoA, vanillic acid, and protocatechuic acid. The genes atu1416, atu1417, and atu1420 have been experimentally shown to be necessary for the degradation of ferulic acid. Moreover, the genes atu1415 and atu1421 have been experimentally demonstrated to be essential for this degradation and are proposed to encode a phenylhydroxypropionyl-CoA dehydrogenase and a 4-hydroxy-3-methoxyphenyl-β-ketopropionic acid (HMPKP)-CoA β-keto-thiolase, respectively. We thus demonstrated that the A. fabrum hydroxycinnamic degradation pathway is an original coenzyme A-dependent β-oxidative deacetylation that could also transform p-coumaric and caffeic acids. Finally, we showed that this pathway enables the metabolism of toxic compounds from plants and their use for growth, likely providing the species an ecological advantage in hydroxycinnamic-rich environments, such as plant roots or decaying plant materials.

  17. Increases in Phenolic, Fatty Acid, and Phytosterol Contents and Anticancer Activities of Sweet Potato after Fermentation by Lactobacillus acidophilus.

    Science.gov (United States)

    Shen, Yixiao; Sun, Haiyan; Zeng, Haiying; Prinyawiwatukul, Witoon; Xu, Wenqing; Xu, Zhimin

    2018-03-21

    Phenolic, fatty acid, and phytosterol contents in sweet potato (SP) fermented by Lactobacillus acidophilus were evaluated and compared with those of raw and boiled SPs. The differences in the profiles and levels of phenolics between the raw and boiled SPs were not as significant as the differences between those and the fermented SP. The levels of caffeic acid and 3,5-dicaffeoylquinic acid in fermented SP were more than 4 times higher than those in raw and boiled SPs. Two phenolics, p-coumaric acid and ferulic acid, which were not detected in either raw or boiled SP, were found in fermented SP. The level of each fatty acid or phytosterol increased in fermented SP and decreased in boiled SP. Among the hydrophilic and lipophilic extracts obtained from raw and fermented SPs, the hydrophilic extract of fermented SP exhibited the highest capability of inhibiting cancer-cell PC-12 proliferation. However, each of the extracts had very low cytotoxicities to normal-monkey-kidney-cell growth. The results indicated that SP fermented by L. acidophilus significantly increased free antioxidant-rich phenolics and inhibited cancer-cell-proliferation activity without cytotoxicity to normal cells.

  18. Methyl Jasmonate and Salicylic Acid Induced Oxidative Stress and Accumulation of Phenolics in Panax ginseng Bioreactor Root Suspension Cultures

    Directory of Open Access Journals (Sweden)

    Kee-Yoeup Paek

    2007-03-01

    Full Text Available To investigate the enzyme variations responsible for the synthesis of phenolics, 40 day-old adventitious roots of Panax ginseng were treated with 200 μM methyl jasmonate (MJ or salicylic acid (SA in a 5 L bioreactor suspension culture (working volume 4 L. Both treatments caused an increase in the carbonyl and hydrogen peroxide (H2O2 contents, although the levels were lower in SA treated roots. Total phenolic, flavonoid, ascorbic acid, non-protein thiol (NPSH and cysteine contents and 1,1-diphenyl-2-picrylhydrazyl (DPPH radical reducing activity were increased by MJ and SA. Fresh weight (FW and dry weight (DW decreased significantly after 9 days of exposure to SA and MJ. The highest total phenolics (62%, DPPH activity (40%, flavonoids (88%, ascorbic acid (55%, NPSH (33%, and cysteine (62% contents compared to control were obtained after 9 days in SA treated roots. The activities of glucose 6-phosphate dehydrogenase, phenylalanine ammonia lyase, substrate specific peroxidases (caffeic acid peroxidase, quercetin peroxidase and ferulic acid peroxidase were higher in MJ treated roots than the SA treated ones. Increased shikimate dehydrogenase, chlorogenic acid peroxidase and β-glucosidase activities and proline content were observed in SA treated roots than in MJ ones. Cinnamyl alcohol dehydrogenase activity remained unaffected by both MJ and SA. These results strongly indicate that MJ and SA induce the accumulation of phenolic compounds in ginseng root by altering the phenolic synthesis enzymes.

  19. Protective effect of Heliotropium foertherianum (Boraginaceae) folk remedy and its active compound, rosmarinic acid, against a Pacific ciguatoxin.

    Science.gov (United States)

    Rossi, Fanny; Jullian, Valérie; Pawlowiez, Ralph; Kumar-Roiné, Shilpa; Haddad, Mohamed; Darius, H Taiana; Gaertner-Mazouni, Nabila; Chinain, Mireille; Laurent, Dominique

    2012-08-30

    Senescent leaves of Heliotropium foertherianum Diane & Hilger (Boraginaceae) are traditionally used in the Pacific region to treat Ciguatera Fish Poisoning. This plant contains rosmarinic acid that is known for its multiple biological activities. In the present study, H. foertherianum aqueous extract, rosmarinic acid and its derivatives were evaluated for their capacity to reduce the effect of ciguatoxins. Aqueous extract of H. foertherianum leaves was prepared and studied for its effects against a Pacific ciguatoxin (P-CTX-1B) in the neuroblastoma cell assay and the receptor binding assay. Rosmarinic acid and six derivatives were also evaluated by means of these bioassays. For this purpose, we have developed an improved synthetic route for caffeic acid 3,4-dihydroxy-phenethyl ester (CADPE). Both the aqueous extract of H. foertherianum leaves and rosmarinic acid showed inhibitory activities against a Pacific ciguatoxin in the above bioassays. Among all the molecules that were evaluated, rosmarinic acid was the most active compound. These results confirm further the potential of H. foertherianum in the treatment of Ciguatera Fish Poisoning. Copyright © 2012 Elsevier Ireland Ltd. All rights reserved.

  20. Molecular Pharmacology of Rosmarinic and Salvianolic Acids: Potential Seeds for Alzheimer’s and Vascular Dementia Drugs

    Directory of Open Access Journals (Sweden)

    Solomon Habtemariam

    2018-02-01

    Full Text Available Both caffeic acid and 3,4-dihydroxyphenyllactic acid (danshensu are synthesized through two distinct routs of the shikimic acid biosynthesis pathway. In many plants, especially the rosemary and sage family of Lamiaceae, these two compounds are joined through an ester linkage to form rosmarinic acid (RA. A further structural diversity of RA derivatives in some plants such as Salvia miltiorrhiza Bunge is a form of RA dimer, salvianolic acid-B (SA-B, that further give rise to diverse salvianolic acid derivatives. This review provides a comprehensive perspective on the chemistry and pharmacology of these compounds related to their potential therapeutic applications to dementia. The two common causes of dementia, Alzheimer’s disease (AD and stroke, are employed to scrutinize the effects of these compounds in vitro and in animal models of dementia. Key pharmacological mechanisms beyond the common antioxidant and anti-inflammatory effects of polyphenols are highlighted with emphasis given to amyloid beta (Aβ pathologies among others and neuronal regeneration from stem cells.

  1. Vanillin formation from ferulic acid in Vanilla planifolia is catalysed by a single enzyme

    Science.gov (United States)

    Gallage, Nethaji J.; Hansen, Esben H.; Kannangara, Rubini; Olsen, Carl Erik; Motawia, Mohammed Saddik; Jørgensen, Kirsten; Holme, Inger; Hebelstrup, Kim; Grisoni, Michel; Møller, Birger Lindberg

    2014-01-01

    Vanillin is a popular and valuable flavour compound. It is the key constituent of the natural vanilla flavour obtained from cured vanilla pods. Here we show that a single hydratase/lyase type enzyme designated vanillin synthase (VpVAN) catalyses direct conversion of ferulic acid and its glucoside into vanillin and its glucoside, respectively. The enzyme shows high sequence similarity to cysteine proteinases and is specific to the substitution pattern at the aromatic ring and does not metabolize caffeic acid and p-coumaric acid as demonstrated by coupled transcription/translation assays. VpVAN localizes to the inner part of the vanilla pod and high transcript levels are found in single cells located a few cell layers from the inner epidermis. Transient expression of VpVAN in tobacco and stable expression in barley in combination with the action of endogenous alcohol dehydrogenases and UDP-glucosyltransferases result in vanillyl alcohol glucoside formation from endogenous ferulic acid. A gene encoding an enzyme showing 71% sequence identity to VpVAN was identified in another vanillin-producing plant species Glechoma hederacea and was also shown to be a vanillin synthase as demonstrated by transient expression in tobacco. PMID:24941968

  2. Synthesis and Antiradical Activity of Isoquercitrin Esters with Aromatic Acids and Their Homologues

    Directory of Open Access Journals (Sweden)

    Eva Heřmánková-Vavříková

    2017-05-01

    Full Text Available Isoquercitrin, (IQ, quercetin-3-O-β-d-glucopyranoside is known for strong chemoprotectant activities. Acylation of flavonoid glucosides with carboxylic acids containing an aromatic ring brings entirely new properties to these compounds. Here, we describe the chemical and enzymatic synthesis of a series of IQ derivatives at the C-6″. IQ benzoate, phenylacetate, phenylpropanoate and cinnamate were prepared from respective vinyl esters using Novozym 435 (Lipase B from Candida antarctica immobilized on acrylic resin. The enzymatic procedure gave no products with “hydroxyaromatic” acids, their vinyl esters nor with their benzyl-protected forms. A chemical protection/deprotection method using Steglich reaction yielded IQ 4-hydroxybenzoate, vanillate and gallate. In case of p-coumaric, caffeic, and ferulic acid, the deprotection lead to the saturation of the double bonds at the phenylpropanoic moiety and yielded 4-hydroxy-, 3,4-dihydroxy- and 3-methoxy-4-hydroxy-phenylpropanoates. Reducing capacity of the cinnamate, gallate and 4-hydroxyphenylpropanoate towards Folin-Ciocalteau reagent was significantly lower than that of IQ, while other derivatives displayed slightly better or comparable capacity. Compared to isoquercitrin, most derivatives were less active in 1,1-diphenyl-2-picrylhydrazyl (DPPH radical scavenging, but they showed significantly better 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid, ABTS scavenging activity and were substantially more active in the inhibition of tert-butylhydroperoxide induced lipid peroxidation of rat liver microsomes. The most active compounds were the hydroxyphenylpropanoates.

  3. The shikimic acid: an important metabolite for the Aglianico del Vulture wines

    Directory of Open Access Journals (Sweden)

    Pasquale Tamborra

    2014-12-01

    Full Text Available Shikimic acid is a precursor for the biosynthesis of aromatic amino acids and flavonoids (anthocyanins, tannins and flavonols. In the pharmaceutical industry, it is obtained by extraction of star anise from China, and at a yield of 3-7% it is used for the production of antiviral drug, e.g. oseltamivir. Unlike flavonoids which are only present in the grape skins, shikimic acid is present in the juice together with hydroxycinnamil tartaric acids (caffeic, ferulic and p-coumaric acid. Therefore, their content in white wines may not be negligible and their presence may explain the epidemiological studies that showed a reduced incidence of cardiovascular diseases also in people with moderate white wine consumption. The content of shikimic acid has been used to characterize wines. In southern Italy it has been used to distinguish Aglianico grape, which holds medium-high content, from Negroamaro, Primitivo and Uva di Troia grapes who have rather lower levels. It could be useful also to distinguish Fiano di Avellino (high value from Fiano Minutolo (low value. However, results of a recent work showed that the shikimic acid content decreases significantly during the ripening of the grapes and therefore its content in wine is strongly influenced by the harvest period. Finally, in a recent paper it was highlighted the increase in shikimic acid content at the end of fermentation in an Aglianico del Vulture wine, produced in the area of Rapolla (PZ, Italy municipality during the 2013 harvest. These last experimental results explain why the values of shikimic acid were lower in grapes and surprisingly higher in wines produced in the 2011 and 2012 harvest.

  4. Simultaneous qualitative and quantitative analysis of phenolic acids and flavonoids for the quality control of Apocynum venetum L. leaves by HPLC-DAD-ESI-IT-TOF-MS and HPLC-DAD.

    Science.gov (United States)

    An, Haijuan; Wang, Hong; Lan, Yuexiang; Hashi, Yuki; Chen, Shizhong

    2013-11-01

    A reliable method based on high performance liquid chromatography-diode array detector-electrospray ionization-ion trap-time of flight-mass spectrometry (HPLC-DAD-ESI-IT-TOF-MS) was developed for the identification of phenolic acids and flavonoids in Apocynum venetum L. leaves and its adulterant, Pocynum hendersonii (Hook. f.) Woodson leaves. A total of 21 compounds were identified or tentatively identified, including 4 phenolic acids and 17 flavonoids. 3-O-caffeoylquinic acid (3-CQA) and caffeic acid were detected for the first time in A. venetum leaves; 4-O-caffeoylquinic acid (4-CQA), 3-CQA, caffeic acid, quercetin-3-O-(6"-O-malonyl)-galactoside, quercetin-3-O-(6"-O-malonyl)-glucoside, kaempferol-3-O-(6"-O-malonyl)-glucoside, kaempferol-3-O-(6"-O-acetyl)-glucoside, and kaempferol-3-O-dihexoside were detected for the first time in P. hendersonii leaves. Cluster analysis was employed to analyze 24 batches of A. venetum leaves and 5 batches of P. hendersonii leaves collected from various regions in China. The analysis, which was based on the 21 compounds, indicated that profiles of these compounds were distinct between the two species, and among A. venetum leaf samples from different origins. 18 of these 21 compounds were selected as the markers and simultaneously analyzed by HPLC-DAD for the first time. The quantitative analytical method was validated and subsequently applied to the comprehensive quality evaluation of 24 batches of A. venetum leaves. © 2013 Elsevier B.V. All rights reserved.

  5. Identification and Quantification of Flavonoids and Phenolic Acids in Burr Parsley (Caucalis platycarpos L., Using High-Performance Liquid Chromatography with Diode Array Detection and Electrospray Ionization Mass Spectrometry

    Directory of Open Access Journals (Sweden)

    Ana Mornar

    2009-07-01

    Full Text Available A sensitive method coupling high-performance liquid chromatography (HPLC with diode-array detector (DAD and electrospray ionization mass spectrometry (MS was optimized for the separation and identification of phenolic acids, flavonoid glycosides and flavonoid aglycones in the extract of burr parsley (Caucalis platycarpos L.. Fragmentation behavior of flavonoid glycosides and phenolic acids were investigated using ion trap mass spectrometry in negative electrospray ionization. The MS, MSn and UV data together with HPLC retention time (TR of phenolic acids and flavonoids allowed structural characterization of these compounds. Caffeoylquinic acid (CQA isomers, p-coumaroyl-quinic acids (p-CoQA, feruloylquinic acids (FQA, dicaffeoylquinic acids (diCQA, luteolin-7-O-rutinoside, apigenin-7-O-rutinoside as well as isolated chrysoeriol-7-O-rutinoside have been identified as constituents of C. platycarpos for the first time. An accurate, precise and sensitive LC-DAD method for quantification of four phenolic acids (3-O-caffeoylquinic, caffeic, p-coumaric, o-coumaric acid, four flavonoid glycosides (luteolin-7-O-glucoside, apigenin-7-O-glucoside, quercetin-3-O-galactoside, quercetin-3-O-rhamnoside, and three flavonoid aglycones (luteolin, apigenin, chrysoeriol in C. platycarpos extract was validated in terms of linearity, limit of detection, limit of quantification, precision and accuracy. 3-O-caffeoylquinic acid was the predominant phenolic acid and luteolin-7-O-glucoside was the predominant flavonoid glycoside.

  6. Well acidizing

    Energy Technology Data Exchange (ETDEWEB)

    Street, E H

    1980-01-23

    The apparatus relates in particular to a well-treating process in which an aqueous acid solution having a pH of < 2 is injected into a subterranean reservoir in a manner such that materials that contain ferric ions are present in the acid and, as the acid reacts within the reservoir and attains a pH exceeding 3, tend to be precipitated as ferric ion-containing solid materials that may plug the pores of the reservoir. Such a precipitation is prevented by dissolving in the acid solution an amount of 5-sulfosalicylic acid which is at least sufficient to sequester significant proportions of ferric ions when the pH of the acid is from 0.5 to 3 but is less than enough to cause a significant salting-out of solid materials, and an amount of citric acid which is at least sufficient to sequester significant proportions of ferric ions when the pH of the acid is from 3 to 6 but is less than enough to precipitate a significant amount of calcium citrate. The amount of the 5-sulfosalicylic acid may be from 0.01 to 0.05 moles/l and the amount of citric acid is from 0.001 to 0.009 moles/l. 11 claims.

  7. Ibotenic acid and thioibotenic acid

    DEFF Research Database (Denmark)

    Hermit, Mette B; Greenwood, Jeremy R; Nielsen, Birgitte

    2004-01-01

    In this study, we have determined and compared the pharmacological profiles of ibotenic acid and its isothiazole analogue thioibotenic acid at native rat ionotropic glutamate (iGlu) receptors and at recombinant rat metabotropic glutamate (mGlu) receptors expressed in mammalian cell lines....... Thioibotenic acid has a distinct pharmacological profile at group III mGlu receptors compared with the closely structurally related ibotenic acid; the former is a potent (low microm) agonist, whereas the latter is inactive. By comparing the conformational energy profiles of ibotenic and thioibotenic acid...... with the conformations preferred by the ligands upon docking to mGlu1 and models of the other mGlu subtypes, we propose that unlike other subtypes, group III mGlu receptor binding sites require a ligand conformation at an energy level which is prohibitively expensive for ibotenic acid, but not for thioibotenic acid...

  8. Analysis of Phenolic Acids of Jerusalem Artichoke (Helianthus tuberosus L. Responding to Salt-Stress by Liquid Chromatography/Tandem Mass Spectrometry

    Directory of Open Access Journals (Sweden)

    Fujia Chen

    2014-01-01

    Full Text Available Plant phenolics can have applications in pharmaceutical and other industries. To identify and quantify the phenolic compounds in Helianthus tuberosus leaves, qualitative analysis was performed by a reversed phase high-performance liquid chromatography coupled with tandem mass spectrometry (HPLC-MS/MS and quantitative analysis by HPLC. Ten chlorogenic acids (CGAs were identified (3-o-caffeoylquinic acid, two isomers of caffeoylquinic acid, caffeic acid, p-coumaroyl-quinic acid, feruloylquinic acid, 3,4-dicaffeoyquinic acid, 3,5-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, and 4,5-dicaffeoylquinic acid by comparing their retention times, UV-Vis absorption spectra, and MS/MS spectra with standards. In addition, four other phenolic compounds, including caffeoyl glucopyranose, isorhamnetin glucoside, kaempferol glucuronide, and kaempferol-3-o-glucoside, were tentatively identified in Helianthus tuberosus leaves for the first time. The 3-o-caffeoylquinic acid (7.752 mg/g DW, 4,5-dicaffeoylquinic acid (5.633 mg/g DW, and 3,5-dicaffeoylquinic acid (4.900 mg/g DW were the major phenolic compounds in leaves of Helianthus tuberosus cultivar NanYu in maturity. The variations in phenolic concentrations and proportions in Helianthus tuberosus leaves were influenced by genotype and plant growth stage. Cultivar NanYu had the highest concentration of phenolic compounds, in particular 3-o-caffeoylquinic acid and 4,5-dicaffeoylquinic acid compared with the other genotypes (wild accession and QingYu. Considering various growth stages, the concentration of total phenolics in cultivar NanYu was higher at flowering stage (5.270 mg/g DW than at budding and tuber swelling stages. Cultivar NanYu of Helianthus tuberosus is a potential source of natural phenolics that may play an important role in the development of pharmaceuticals.

  9. Schizosaccharomyces pombe and Saccharomyces cerevisiae yeasts in sequential fermentations: Effect on phenolic acids of fermented Kei-apple (Dovyalis caffra L.) juice.

    Science.gov (United States)

    Minnaar, P P; Jolly, N P; Paulsen, V; Du Plessis, H W; Van Der Rijst, M

    2017-09-18

    Kei-apple (Dovyalis caffra) is an evergreen tree indigenous to Southern Africa. The fruit contains high concentrations of l-malic acid, ascorbic acid, and phenolic acids. Kei-apple juice was sequentially inoculated with Schizosaccharomyces pombe and Saccharomyces cerevisiae yeasts. A reference fermentation using only S. cerevisiae was included. The fermentation was monitored by recording mass loss. At the end of fermentation, twelve untrained judges conducted free choice aroma profiling on the fruit wines. The Kei-apple juice and wines were analysed for total titratable acidity, total soluble solids, pH, alcohol, l-malic acid, and phenolic acids. Total titratable acidity was ca. 70% lower in Kei-apple wines produced with S. pombe+S. cerevisiae than in Kei-apple juice. Kei-apple wines produced with S. pombe+S. cerevisiae showed substantially lower concentrations of l-malic acid than Kei-apple wines produced with S. cerevisiae only. Wines produced with S. cerevisiae only proved higher in phenolic acid concentrations than wines produced with S. pombe+S. cerevisiae. Chlorogenic acid was the most abundant phenolic acid measured in the Kei-apple wines, followed by protocatechuic acid. Judges described the Kei-apple wines produced with S. pombe+S. cerevisiae as having noticeable off-odours, while wines produced with S. cerevisiae were described as fresh and fruity. Kei-apple wines (S. pombe+S. cerevisiae and S. cerevisiae) were of comparable vegetative and organic character. Saccharomyces cerevisiae produced Kei-apple wine with increased caffeic, chlorogenic, protocatechuic, and sinapic acids, whereas S. pombe+S. cerevisiae produced Kei-apple wines with increased ferulic, and p-coumaric acids and low l-malic acid. Copyright © 2017 Elsevier B.V. All rights reserved.

  10. Combining bar adsorptive microextraction with capillary electrophoresis--application for the determination of phenolic acids in food matrices.

    Science.gov (United States)

    da Rosa Neng, Nuno; Sequeiros, Rute C P; Florêncio Nogueira, José Manuel

    2014-09-01

    In this contribution, bar adsorptive microextraction coated with a mixed-mode anion exchange/RP followed by liquid desorption was combined for the first time with a capillary electrophoresis-diode array detection system (BAμE(MAX)-LD/CE-DAD), for the determination of phenolic acids in food matrices, using chlorogenic, ferulic, cumaric, and caffeic acids as model compounds. Assays performed in aqueous media spiked at the 0.8 mg/L level yielded average recoveries up to 40% for all four phenolic acids, under optimized experimental conditions. The analytical performance showed also good precision (RSD 0.9900). By using the standard addition method, the application to food matrices such as green tea, red fruit juice, and honey allowed very good performances for the determination of minor amounts of phenolic acids. The proposed methodology proved to be a suitable alternative for the analysis of polar to ionic compounds, showing to be easy to implement, reliable, sensitive, and requiring a low sample volume to determine phenolic acids in food samples. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  11. Correlated accumulation of anthocyanins and rosmarinic acid in mechanically stressed red cell suspensions of basil (Ocimum basilicum).

    Science.gov (United States)

    Strazzer, Pamela; Guzzo, Flavia; Levi, Marisa

    2011-02-15

    A red basil cell line (T2b) rich in rosmarinic acid (RA) was selected for the stable production of anthocyanins (ACs) in the dark. Cell suspension cultures were subjected to mechanical stress through increased agitation (switch from 90 to 150 rpm) to determine the relationship between AC and RA accumulation. Cell extracts were analyzed by HPLC and LC-MS, and the resulting data were processed with multivariate statistical analysis. MS and MS/MS spectra facilitated the putative annotation of several complex cyanidin-based ACs, which were esterified with coumaric acid and, in some cases, also with malonic acid. It was also possible to identify various RA-related molecules, some caffeic and coumaric acid derivatives and some flavanones. Mechanical stress increased the total AC and RA contents, but reduced biomass accumulation. Many metabolites were induced by mechanical stress, including RA and some of its derivatives, most ACs, hydroxycinnamic acids and flavonoids, whereas the abundance of some RA dimers was reduced. Although AC and RA share a common early biosynthetic pathway (from phenylalanine to 4-coumaroyl-CoA) and could have similar or overlapping functions providing antioxidant activity against stress-generated reactive oxygen species, there appeared to be no competition between their individual pathways. Copyright © 2010 Elsevier GmbH. All rights reserved.

  12. First identification of dimethoxycinnamic acids in human plasma after coffee intake by liquid chromatography-mass spectrometry.

    Science.gov (United States)

    Nagy, Kornél; Redeuil, Karine; Williamson, Gary; Rezzi, Serge; Dionisi, Fabiola; Longet, Karin; Destaillats, Frédéric; Renouf, Mathieu

    2011-01-21

    There is a substantial amount of published literature on the bioavailability of various coffee components including the most abundant metabolites, caffeic and ferulic acids. Surprisingly, to date, the appearance of dimethoxycinnamic acid derivatives in humans has not been reported despite the fact that methylated form of catechol-type polyphenols could help maintain, modify or even improve their biological activities. This study reports an LC-MS method for the detection of dimethoxycinnamic acid in human plasma after treatment with an esterase. Liquid chromatography, including the combination of methanol and acetonitrile as organic eluent, was optimized to resolve all interferences and enable reliable detection and identification of 3,4-dimethoxycinnamic and 3,4-dimethoxy-dihydrocinnamic acids. In addition to the good mass accuracy achieved (better than 5 ppm), tandem mass spectrometric and co-chromatography experiments further confirmed the identity of the compounds. The optimized method was applied to analyze samples obtained immediately, 1 and 10 h after coffee ingestion. The results show that in particular 3,4-dimethoxycinnamic acid appears in high abundance (∼380 nM at 60 min) in plasma upon coffee intake, indicating that it is important to consider these derivatives in future bioavailability and bioefficacy studies. Copyright © 2010 Elsevier B.V. All rights reserved.

  13. Dynamics in the concentrations of health-promoting compounds: lupeol, mangiferin and different phenolic acids during postharvest ripening of mango fruit.

    Science.gov (United States)

    Vithana, Mekhala Dk; Singh, Zora; Johnson, Stuart K

    2018-03-01

    Mango fruit (Mangifera indica L.) is renowned for its pleasant taste and as a rich source of health beneficial compounds. The aim of this study was to investigate the changes in concentrations of health-promoting compounds, namely ascorbic acid, carotenoids, antioxidants, lupeol, mangiferin, total phenols and individual phenolic acids, as well as ethylene production and respiration rates during climacteric ripening in 'Kensington Pride' and 'R2E2' mango fruit. The climacteric ethylene and respiration peaks were noted on the third day of the fruit ripening period. The concentrations of total carotenoids in the pulp, total antioxidants in both pulp and peel, and total phenols of the peel, lupeol and mangiferin were significantly elevated, whereas the concentration of ascorbic acid declined during post-climacteric ripening. Gallic, chlorogenic and vanillic acids were identified as the major phenolic acids in both pulp and peel of 'Kensington Pride' and 'R2E2' mangoes. The concentrations of phenolic acids (gallic, chlorogenic, vanillic, ferulic and caffeic acids) also increased during the post-climacteric phase. The concentrations of all phenolic compounds were several-fold higher in the peel than pulp. Mangoes at post-climacteric ripening phase offer the highest concentrations of health-promoting compounds. Peel, at this stage of fruit ripening, could be exploited as a good source for extraction of these compounds. © 2017 Society of Chemical Industry. © 2017 Society of Chemical Industry.

  14. Formic acid

    Energy Technology Data Exchange (ETDEWEB)

    Nielsen, H; Laing, B

    1921-12-03

    The production of formic acid by the oxidation of methane with a metallic oxide or by the interaction of carbon monoxide and water vapor in the presence of a catalyst, preferably a metallic oxide, is described along with the destructive distillation of carbonaceous material in the preesnce of formic acid vapor for the purpose of increasing the yield of condensible hydrocarbons.

  15. A p-coumaroyl esterase from Rhizoctonia solani with a pronounced chlorogenic acid esterase activity.

    Science.gov (United States)

    Nieter, Annabel; Kelle, Sebastian; Linke, Diana; Berger, Ralf G

    2017-07-25

    Extracellular esterase activity was detected in submerged cultures of Rhizoctonia solani grown in the presence of sugar beet pectin or Tween 80. Putative type B feruloyl esterase (FAE) coding sequences found in the genome data of the basidiomycete were heterologously expressed in Pichia pastoris. Recombinant enzyme production on the 5-L bioreactor scale (Rs pCAE: 3245UL -1 ) exceeded the productivity of the wild type strain by a factor of 800. Based on substrate specificity profiling, the purified recombinant Rs pCAE was classified as a p-coumaroyl esterase (pCAE) with a pronounced chlorogenic acid esterase side activity. The Rs pCAE was also active on methyl cinnamate, caffeate and ferulate and on feruloylated saccharides. The unprecedented substrate profile of Rs pCAE together with the lack of sequence similarity to known FAEs or pCAEs suggested that the Rs pCAE represents a new type of enzyme. Hydroxycinnamic acids were released from agro-industrial side-streams, such as destarched wheat bran (DSWB), sugar beet pectin (SBP) and coffee pulp (CP). Overnight incubation of coffee pulp with the Rs pCAE resulted in the efficient release of p-coumaric (100%), caffeic (100%) and ferulic acid (85%) indicating possible applications for the valorization of food processing wastes and for the enhanced degradation of lignified biomass. Copyright © 2017 Elsevier B.V. All rights reserved.

  16. Role of Chlorogenic Acids in Controlling Oxidative and Inflammatory Stress Conditions

    Directory of Open Access Journals (Sweden)

    Ningjian Liang

    2015-12-01

    Full Text Available 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 is 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.

  17. Simultaneous determination of phenolic acids and flavonoids in Chenopodium formosanum Koidz. (djulis) by HPLC-DAD-ESI-MS/MS.

    Science.gov (United States)

    Hsu, B Y; Lin, S W; Inbaraj, B Stephen; Chen, B H

    2017-01-05

    A high performance liquid chromatography-diode array detection-tandem mass spectrometry method (HPLC-DAD-MS/MS) was developed for simultaneous determination of phenolic acids and flavonoids in djulis (Chenopodium formosanum Koidz.), a traditional Chinese herb reported to possess vital biological activities. A high yield of phenolic acids and flavonoids was attained by employing 50% ethanol in water as the extraction solvent and shaking in a 60°C water bath for 3h. A total of 8 phenolic acids and 14 flavonoids were separated and identified within 55min by using a Poroshell 120 EC-C18 column with detection at 280nm, flow rate at 0.8mL/min, column temperature at 35°C, and a gradient solvent system of 0.1% formic acid in water and acetonitrile. Two internal standards caffeic acid and kaempferol-3-O-rutinoside were used for quantitation of phenolic acids and flavonoids in djulis respectively. The amounts of phenolic acids ranged from 11.5±0.8μg/g (caffeoyl-putrescine-derivative (2)) to 1855.3±16.9μg/g (hydroxylphenylacetic acid pentoside), while the flavonoids ranged from 19.93±2.29μg/g (quercetin-3-O-(coumaryl)-rutinoside-pentoside (1)) to 257.3±2.05μg/g (rutin-O-pentoside (2)). A high recovery (89.68-97.20%) and high reproducibility was obtained for both phenolic acids and flavonoids with the relative standard deviation (RSD) for the latter ranging from 0.09-8.22% (intra-day variability) and 0.80-8.48% (inter-day variability). This method may be applied to determination of both phenolic acids and flavonoids in food products and Chinese herbs. Copyright © 2016 Elsevier B.V. All rights reserved.

  18. Enhancement of the catalytic activity of ferulic acid decarboxylase from Enterobacter sp. Px6-4 through random and site-directed mutagenesis.

    Science.gov (United States)

    Lee, Hyunji; Park, Jiyoung; Jung, Chaewon; Han, Dongfei; Seo, Jiyoung; Ahn, Joong-Hoon; Chong, Youhoon; Hur, Hor-Gil

    2015-11-01

    The enzyme ferulic acid decarboxylase (FADase) from Enterobacter sp. Px6-4 catalyzes the decarboxylation reaction of lignin monomers and phenolic compounds such as p-coumaric acid, caffeic acid, and ferulic acid into their corresponding 4-vinyl derivatives, that is, 4-vinylphenol, 4-vinylcatechol, and 4-vinylguaiacol, respectively. Among various ferulic acid decarboxylase enzymes, we chose the FADase from Enterobacter sp. Px6-4, whose crystal structure is known, and produced mutants to enhance its catalytic activity by random and site-directed mutagenesis. After three rounds of sequential mutations, FADase(F95L/D112N/V151I) showed approximately 34-fold higher catalytic activity than wild-type for the production of 4-vinylguaiacol from ferulic acid. Docking analyses suggested that the increased activity of FADase(F95L/D112N/V151I) could be due to formation of compact active site compared with that of the wild-type FADase. Considering the amount of phenolic compounds such as lignin monomers in the biomass components, successfully bioengineered FADase(F95L/D112N/V151I) from Enterobacter sp. Px6-4 could provide an ecofriendly biocatalytic tool for producing diverse styrene derivatives from biomass.

  19. In Vitro Antioxidant Activities of Phenols and Oleanolic Acid from Mango Peel and Their Cytotoxic Effect on A549 Cell Line

    Directory of Open Access Journals (Sweden)

    Xuelian Bai

    2018-06-01

    Full Text Available Mango peel, the main by-product of juice processing, possesses appreciable quantities of bioactive phenolic compounds and is worthy of further utilization. The present work reports for the first time the HPLC analysis and in vitro antioxidant evaluation of mango peel phenols (MPPs and their cytotoxic effect on the A549 lung cancer cell line. These results indicated that mango peel has the total phenolic content of 723.2 ± 0.93 mg·kg−1 dry mango peel (DMP, which consisted mainly of vanillic aldehyde, caffeic acid, chlorogenic acid, gallic acid, procyanidin B2 and oleanolic acid. Antioxidant assays showed that MPPs had strong antioxidant activities, with 92 ± 4.2% of DPPH radical scavenging rate, 79 ± 2.5% of ABTS radical inhibition rate and 4.7 ± 0.5 μM Trolox equivalents per kg−1 DMP of ferric reducing power. Gallic acid possess a stronger antioxidant capacity than other phenols. In vitro cytotoxic tests suggested that mango peel extract (MPE had an IC50 value of 15 mg·mL−1 and MPPs had a stronger inhibitory effect on the A549 cell line. Oleanolic acid exhibited the strongest cytotoxicity, with an IC50 value of 4.7 μM, which was similar with that of the positive control 5-fluorouracil.

  20. Identification of new derivatives of 2-S-glutathionylcaftaric acid in aged white wines by HPLC-DAD-ESI-MS(n).

    Science.gov (United States)

    Cejudo-Bastante, María Jesús; Pérez-Coello, María Soledad; Hermosín-Gutiérrez, Isidro

    2010-11-10

    Glutathione, a natural occurring antioxidant, is a thiol-containing peptide present in grape must and wine. It is able to regenerate the o-diphenol group of enzymatically oxidized trans-caftaric acid, giving rise to 2-S-glutathionyl-trans-caftaric acid (also known as grape reaction product, GRP) and thus inhibiting the browning of wine. The amount of GRP present in a wine provides information on the oxidation history of the wine over its elaboration and aging. GRP has been proved to suffer hydrolysis in model solutions and wines. To know the actual content of glutathione involved in white wine browning inhibition as GRP, the GRP-derived products have been studied in 1-year-aged white wines by HPLC-DAD-ESI-MS(n). Online UV-vis spectra and pseudomolecular ions [(M + H)(+)] obtained by LC-MS supported the formation of some of the expected GRP hydrolysis products, mainly 2-S-glutathionyl-trans-caffeic acid (trans-GSCf), together with minor 2-S-(cysteinylglycyl)-trans-caftaric acid, 2-S-(γ-glutamylcysteinyl)-trans-caftaric acid, and 2-S-cysteinyl-trans-caftaric acid. On the basis of UV-vis and LC-MS(2) spectra, new GRP derivatives in aged white wines have been tentatively characterized for the first time as three monoethyl esters of GRP (GRP-Et) and also the cis isomers of GRP, GSCf, and some of the GRP-Et.

  1. Comparison of phenolic acids and flavonoids contents in various cultivars and parts of common lavender (Lavandula angustifolia) derived from Poland.

    Science.gov (United States)

    Adaszyńska-Skwirzyńska, M; Dzięcioł, M

    2017-11-01

    The aim of study was to compare the content of phenolic acids and flavonoids in two cultivars of Lavandula angustifolia: 'Blue River' and 'Ellagance Purple', including flowers and leafy stalks. Total phenolics and total flavonoids contents were determined by UV-Vis spectroscopy. The contents of total phenolics in leafy stalks (3.71-4.06 mg g -1 d.m.) were higher than in flowers (1.13-1.14 mg g -1 d.m.). Similarly, higher total contents of flavonoids were determined in leafy stalks (3.41-3.51 mg g -1 d.m.), as compared with flowers (0.86-0.91 mg g -1 d.m.). Phenolic acids and flavonoids were identified and quantified using HPLC and UPLC methods. Three phenolic acids were determined: rosmarinic, ferulic and caffeic acid. Lavender extracts contained also flavonoids from group of apigenin, luteolin and quercetin. Higher amounts of luteolin diglucuronide and luteolin glucuronide were found in leafy stalks in comparison to flowers. Obtained results indicate that leafy stalks of lavender can be also valuable source of antioxidant compounds.

  2. Inhibition of Fusarium Growth and Mycotoxin Production in Culture Medium and in Maize Kernels by Natural Phenolic Acids.

    Science.gov (United States)

    Ferruz, Elena; Loran, Susana; Herrera, Marta; Gimenez, Isabel; Bervis, Noemi; Barcena, Carmen; Carramiñana, Juan Jose; Juan, Teresa; Herrera, Antonio; Ariño, Agustin

    2016-10-01

    The possible role of natural phenolic compounds in inhibiting fungal growth and toxin production has been of recent interest as an alternative strategy to the use of chemical fungicides for the maintenance of food safety. Fusarium is a worldwide fungal genus mainly associated with cereal crops. The most important Fusarium mycotoxins are trichothecenes, zearalenone, and fumonisins. This study was conducted to evaluate the potential of four natural phenolic acids (caffeic, ferulic, p-coumaric, and chlorogenic) for the control of mycelial growth and mycotoxin production by six toxigenic species of Fusarium . The addition of phenolic acids to corn meal agar had a marked inhibitory effect on the radial growth of all Fusarium species at levels of 2.5 to 10 mM in a dose-response pattern, causing total inhibition (100%) in all species except F. sporotrichioides and F. langsethiae . However, the effects of phenolic acids on mycotoxin production in maize kernels were less evident than the effects on growth. The fungal species differed in their responses to the phenolic acid treatments, and significant reductions in toxin concentrations were observed only for T-2 and HT-2 (90% reduction) and zearalenone (48 to 77% reduction). These results provide data that could be used for developing pre- and postharvest strategies for controlling Fusarium infection and subsequent toxin production in cereal grains.

  3. Determination of Flavonoids, Phenolic Acids, and Xanthines in Mate Tea (Ilex paraguariensis St.-Hil.

    Directory of Open Access Journals (Sweden)

    Mirza Bojić

    2013-01-01

    Full Text Available Raw material, different formulations of foods, and dietary supplements of mate demands control of the content of bioactive substances for which high performance thin layer chromatography (TLC, described here, presents simple and rapid approach for detections as well as quantification. Using TLC densitometry, the following bioactive compounds were identified and quantified: chlorogenic acid (2.1 mg/g, caffeic acid (1.5 mg/g, rutin (5.2 mg/g, quercetin (2.2 mg/g, and kaempferol (4.5 mg/g. The results obtained with TLC densitometry for caffeine (5.4 mg/g and theobromine (2.7 mg/g show no statistical difference to the content of total xanthines (7.6 mg/g obtained by UV-Vis spectrophotometry. Thus, TLC remains a technique of choice for simple and rapid analysis of great number of samples as well as a primary screening technique in plant analysis.

  4. Lipoic Acid

    Directory of Open Access Journals (Sweden)

    Ramazan Tetikcok

    2015-09-01

    Full Text Available Lipoic acid, which is defined as a miralce antioxidan, is used by many departments. Eventhough clinical using data are very limited , it is used in treatment of diabetic neuropathy, physical therapy and rehabilitation clinic, dermatology clinic, geriatric clinics. It has usage area for cosmetic purposes. Although there are reports there are the direction of the effectiveness in these areas, the works done are not enough. Today lipoic acid , used in many areas ,is evaluated as universal antioxidant [J Contemp Med 2015; 5(3.000: 206-209

  5. Effect of maceration duration on physicochemical characteristics, organic acid, phenolic compounds and antioxidant activity of red wine from Vitis vinifera L. Karaoglan.

    Science.gov (United States)

    Kocabey, N; Yilmaztekin, M; Hayaloglu, A A

    2016-09-01

    Effects of different maceration times (5, 10 and 15 days) on composition, phenolic compounds and antioxidant activities of red wines made from the Vitis vinifera L. Karaoglan grown in Malatya were investigated. Maceration duration changed some chemical constituents and color of Karaoglan red wines. A linear relationship was observed between antioxidant activity of wine and maceration duration. Major organic acid was tartaric acid which was at the highest concentration in wine macerated for 10 days. A total of 25 phenolic compounds was determined in wine samples. Within these phenolics; procyanidin B2, trans -caftaric acid, gallic acid, trans -caffeic acid, (+) catechin, (-) epicatechin and quercetin-3- O -glucoside were the most abundant phenolics regardless of maceration duration. In general, extended maceration duration resulted in increase in the concentration of phenolic compounds, reflecting the antioxidant activities of wine. In conclusion, the highest concentrations of total and individual phenolic compounds as well as antioxidant activities were found in wines macerated for 15 days.

  6. Characterization of flavonoids and phenolic acids in Myrcia bella Cambess. using FIA-ESI-IT-MS(n) and HPLC-PAD-ESI-IT-MS combined with NMR.

    Science.gov (United States)

    Saldanha, Luiz L; Vilegas, Wagner; Dokkedal, Anne L

    2013-07-16

    The leaves of Myrcia DC. ex Guill species are used in traditional medicine and are also exploited commercially as herbal drugs for the treatment of diabetes mellitus. The present work aimed to assess the qualitative and quantitative profiles of M. bella hydroalcoholic extract, due to these uses, since the existing legislation in Brazil determines that a standard method must be developed in order to be used for quality control of raw plant materials. The current study identified eleven known flavonoid-O-glycosides and six acylated flavonoid derivatives of myricetin and quercetin, together with two kaempferol glycosides and phenolic acids such as caffeic acid, ethil galate, gallic acid and quinic acid. In total, 24 constituents were characterized, by means of extensive preparative chromatographic analyses, along with MS and NMR techniques. An HPLC-PAD-ESI-IT-MS and FIA-ESI-IT-MS(n) method were developed for rapid identification of acylated flavonoids, flavonoid-O-glycosides derivatives of myricetin and quercetin and phenolic acids in the hydroalcoholic M. bella leaves extract. The FIA-ESI-IT-MS techinique is a powerful tool for direct and rapid identification of the constituents after isolation and NMR characterization. Thus, it could be used as an initial method for identification of authentic samples concerning quality control of Myrcia spp extracts.

  7. Characterization of Flavonoids and Phenolic Acids in Myrcia bella Cambess. Using FIA-ESI-IT-MSn and HPLC-PAD-ESI-IT-MS Combined with NMR

    Directory of Open Access Journals (Sweden)

    Anne L. Dokkedal

    2013-07-01

    Full Text Available The leaves of Myrcia DC. ex Guill species are used in traditional medicine and are also exploited commercially as herbal drugs for the treatment of diabetes mellitus. The present work aimed to assess the qualitative and quantitative profiles of M. bella hydroalcoholic extract, due to these uses, since the existing legislation in Brazil determines that a standard method must be developed in order to be used for quality control of raw plant materials. The current study identified eleven known flavonoid-O-glycosides and six acylated flavonoid derivatives of myricetin and quercetin, together with two kaempferol glycosides and phenolic acids such as caffeic acid, ethil galate, gallic acid and quinic acid. In total, 24 constituents were characterized, by means of extensive preparative chromatographic analyses, along with MS and NMR techniques. An HPLC-PAD-ESI-IT-MS and FIA-ESI-IT-MSn method were developed for rapid identification of acylated flavonoids, flavonoid-O-glycosides derivatives of myricetin and quercetin and phenolic acids in the hydroalcoholic M. bella leaves extract. The FIA-ESI-IT-MS techinique is a powerful tool for direct and rapid identification of the constituents after isolation and NMR characterization. Thus, it could be used as an initial method for identification of authentic samples concerning quality control of Myrcia spp extracts.

  8. Characterization and quantification of flavonoids and hydroxycinnamic acids in curly kale (Brassica oleracea L. Convar. acephala Var. sabellica) by HPLC-DAD-ESI-MSn.

    Science.gov (United States)

    Olsen, Helle; Aaby, Kjersti; Borge, Grethe Iren A

    2009-04-08

    Kale is a leafy green vegetable belonging to the Brassicaceae family, a group of vegetables including cabbage, broccoli, cauliflower, and Brussels sprouts, with a high content of health-promoting phytochemicals. The flavonoids and hydroxycinammic acids of curly kale ( Brassica oleracea L. ssp. oleracea convar. acephala (DC.) Alef. var. sabellica L.), a variety of kale, were characterized and identified primarily through HPLC-DAD-ESI-MS(n) analysis. Thirty-two phenolic compounds including glycosides of quercetin and kaempferol and derivatives of p-coumaric, ferulic, sinapic, and caffeic acid were tentatively identified, providing a more complete identification of phenolic compounds in curly kale than previously reported. Moreover, three hydroxycinnamic acids and one flavonoid with an unusual high grade of glycosylation, quercetin-3-disinapoyl-triglucoside-7-diglucoside, have been tentatively identified for the first time. The influence of different extraction conditions (extraction method, solvent type, solvent/solid ratio, and duration of extraction) was investigated. The total flavonol and hydroxycinnamic acid contents in curly kale determined as rutin equivalents (RE) were 646 and 204 mg of RE/100 g of fresh weight (fw), respectively. The contents of individual flavonoids ranged from 2 to 159 mg of RE/100 g of fw, with main compounds kaempferol-3-sinapoyl-diglucoside-7-diglucoside (18.7%) and quercetin-3-sinapoyl-diglucoside-7-diglucoside (16.5%). After acidic hydrolysis, two flavonol aglycones were identified in curly kale, quercetin and kaempferol, with total contents of 44 and 58 mg/100 g of fw, respectively.

  9. [Exploration on feasibility of introducing bioassay method into quality evaluation of Chinese herbal medicines by studying on the correlation between antioxidant activity of Prunella vulgaris and its total phenolic acids content for example].

    Science.gov (United States)

    Feng, Wei-Hong; Li, Chun; Xin, Wei-Mei; Lin, Li-Mei; Xia, Bo-Hou; Rong, Li-Xin; Yang, Li-Xin; Yi, Hong; Zhang, Yong-Xin; Chen, Liang-Mian; Wang, Zhi-Min

    2016-07-01

    This paper aims to investigate the correlation between the antioxidant activity of Prunella vulgaris and its total phenolic acids content by measuring the antioxidant activity of different sources and different organs of P. vulgaris and the total contents of protocatechuic acid, protocatechuic aldehyde, caffeic acid, salviaflaside and rosmarinic acid in these samples. Using the 50% methanol extract of P. vulgaris samples as the research object, DPPH method and HPLC method were used respectively to determine the antioxidant activities and the total contents of the above-mentioned five analytes in P. vulgaris samples. 0.5 mL of 50% methanol extract of P. vulgaris reacts with 0.1 mmol•L⁻¹ DPPH ethanol solution for 60 min, then the absorbance of the reaction solution was measured at 517 nm, scavenging rate and IC₅₀ values were calculated by the absorbance and the sample concentration for evaluating the antioxidant activity. HPLC analysis was made on a C₁₈ Epic column, with acetonitrile-0.1% formic acid aqueous solution as mobile phase (gradient elution), and the detection wavelength was set at 280 nm. The correlation between the antioxidant capacity of different habitats and different organs of P. vulgaris and the total contents of five kinds of phenolic acids was analyzed by partial least squares method. The reaction dose-response range of 50% methanol extract of P. vulgaris with 0.1 mmol•L⁻¹ DPPH ethanol solution was 0.300-1.65 g•L⁻¹. When the quantities of potocatechuic acid, protocatechuic aldehyde, caffeic acid, salviaflaside and rosmarinic acid were respectively in 0.007 84-0.980, 0.011 5-1.44, 0.008 64-1.08, 0.080 0-1.00 and 0.079 8-0.998 μg range, their quantities were in good linear relationship with the corresponding peak areas. The average recovery of 5 components were 97.76%, 96.88%, 100.3%, 102.1%, 104.5%, with RSD of 1.8%, 1.6%, 1.7%, 1.6% and 1.7%, respectively. In a certain range of crude drug quantity, the antioxidant activity

  10. Mefenamic Acid

    Science.gov (United States)

    Mefenamic acid comes as a capsule to take by mouth. It is usually taken with food every 6 hours as needed for up to 1 week. Follow ... pain vomit that is bloody or looks like coffee grounds black, tarry, or bloody stools slowed breathing ...

  11. Acid rain. Les pluies acides

    Energy Technology Data Exchange (ETDEWEB)

    Curren, T

    1979-11-28

    This report was produced for the use of Members of Parliament and House of Commons committees. The document describes the formation of acid rain, emissions of acidifying pollutants in North America, the growth of the problem and its environmental effects on aquatic and terrestrial ecosystems, human health and man-made structures. Areas of Canada which are most susceptible are identified. Actions taken by Parliament are given, including the formation of a sub-committee on acid rain and the passing of Bill C-51 in 1980 to amend the Clean Air Act, bringing it closer to a similar law in the U.S. A chronology of government responses to acid rain at the international, national and provincial level, is given. The most recent government actions included the passing of the US Clean Air Act by the Senate, the amending of the act into law, and commencement of negotiations to develop a Canada-US Air Quality Accord. 10 refs.

  12. Suitability of antioxidant capacity, flavonoids and phenolic acids for floral authentication of honey. Impact of industrial thermal treatment.

    Science.gov (United States)

    Escriche, Isabel; Kadar, Melinda; Juan-Borrás, Marisol; Domenech, Eva

    2014-01-01

    Total antioxidant activity, physicochemical parameters, and the profile of flavonoids and phenolic acid compounds were evaluated for: their ability to distinguish between the botanical origins of four types of Spanish honey, the impact of industrial thermal treatment, and the effect of the year of collection. Citrus honey had the lowest levels of all the analysed variables, then rosemary and polyfloral, and honeydew the highest ones. Botanical origin affects the profile of flavonoids and phenolic compounds sufficiently to permit discrimination thanks to the predominance of particular compounds such as: hesperetin (in citrus honey); kaempferol, chrysin, pinocembrin, caffeic acid and naringenin (in rosemary honey) and myricetin, quercetin, galangin and particularly p-coumaric acid (in honeydew honey). The impact of industrial thermal treatments is lower than the expected variability as a consequence of the year of collection, though neither factor has enough influence to alter these constituent compounds to the point of affecting the discrimination of honey by botanical origin. Copyright © 2013 Elsevier Ltd. All rights reserved.

  13. Is comfrey root more than toxic pyrrolizidine alkaloids? Salvianolic acids among antioxidant polyphenols in comfrey (Symphytum officinale L.) roots.

    Science.gov (United States)

    Trifan, Adriana; Opitz, Sebastian E W; Josuran, Roland; Grubelnik, Andreas; Esslinger, Nils; Peter, Samuel; Bräm, Sarah; Meier, Nadja; Wolfram, Evelyn

    2018-02-01

    Comfrey root preparations are used for the external treatment of joint distortions and myalgia, due to its analgesic and anti-inflammatory properties. Up to date, key activity-determining constituents of comfrey root extracts have not been completely elucidated. Therefore, we applied different approaches to further characterize a comfrey root extract (65% ethanol). The phenolic profile of comfrey root sample was characterized by HPLC-DAD-QTOF-MS/MS. Rosmarinic acid was identified as main phenolic constituent (7.55 mg/g extract). Moreover, trimers and tetramers of caffeic acid (isomers of salvianolic acid A, B and C) were identified and quantified for the first time in comfrey root. In addition, pyrrolizidine alkaloids were evaluated by HPLC-QQQ-MS/MS and acetylintermedine, acetyllycopsamine and their N-oxides were determined as major pyrrolizidine alkaloids in the comfrey root sample. Lastly, the antioxidant activity was determined using four assays: DPPH and ABTS radicals scavenging assays, reducing power assay and 15-lipoxygenase inhibition assay. Comfrey root extract exhibited significant antioxidant activities when compared to known antioxidants. Thus, comfrey root is an important source of phenolic compounds endowed with antioxidant activity which may contribute to the overall bioactivity of Symphytum preparations. Copyright © 2017 Elsevier Ltd. All rights reserved.

  14. Graphene/dodecanol floating solidification microextraction for the preconcentration of trace levels of cinnamic acid derivatives in traditional Chinese medicines.

    Science.gov (United States)

    Hu, Shuang; Yang, Xiao; Xue, Jiao; Chen, Xuan; Bai, Xiao-Hong; Yu, Zhi-Hui

    2017-07-01

    A novel graphene/dodecanol floating solidification microextraction followed by HPLC with diode-array detection has been developed to extract trace levels of four cinnamic acid derivatives in traditional Chinese medicines. Several parameters affecting the performance were investigated and optimized. Also, possible microextraction mechanism was analyzed and discussed. Under the optimum conditions (amount of graphene in dodecanol: 0.25 mg/mL; volume of extraction phase: 70 μL; pH of sample phase: 3; extraction time: 30   min; stirring rate: 1000 rpm; salt amount: 26.5% NaCl; volume of sample phase: 10 mL, and without dispersant addition), the enrichment factors of four cinnamic acid derivatives ranged from 26 to 112, the linear ranges were 1.0 × 10 -2 -10.0 μg/mL for caffeic acid, 1.3 × 10 -3 -1.9 μg/mL for p-hydroxycinnamic acid, 2.8 × 10 -3 -4.1 μg/mL for ferulic acid, and 2.7 × 10 -3 -4.1 μg/mL for cinnamic acid, with r 2 ≥ 0.9993. The detection limits were found to be in the range of 0.1-1.0 ng/mL, and satisfactory recoveries (92.5-111.2%) and precisions (RSDs 1.1-9.5%) were also achieved. The results showed that the approach is simple, effective and sensitive for the preconcentration and determination of trace levels of cinnamic acid derivatives in Chinese medicines. The proposed method was compared with conventional dodecanol floating solidification microextraction and other extraction methods. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  15. Rosmarinic acid, a new snake venom phospholipase A2 inhibitor from Cordia verbenacea (Boraginaceae): antiserum action potentiation and molecular interaction.

    Science.gov (United States)

    Ticli, Fábio K; Hage, Lorane I S; Cambraia, Rafael S; Pereira, Paulo S; Magro, Angelo J; Fontes, Marcos R M; Stábeli, Rodrigo G; Giglio, José R; França, Suzelei C; Soares, Andreimar M; Sampaio, Suely V

    2005-09-01

    Many plants are used in traditional medicine as active agents against various effects induced by snakebite. The methanolic extract from Cordia verbenacea (Cv) significantly inhibited paw edema induced by Bothrops jararacussu snake venom and by its main basic phospholipase A2 homologs, namely bothropstoxins I and II (BthTXs). The active component was isolated by chromatography on Sephadex LH-20 and by RP-HPLC on a C18 column and identified as rosmarinic acid (Cv-RA). Rosmarinic acid is an ester of caffeic acid and 3,4-dihydroxyphenyllactic acid [2-O-cafeoil-3-(3,4-di-hydroxy-phenyl)-R-lactic acid]. This is the first report of RA in the species C. verbenacea ('baleeira', 'whaler') and of its anti-inflammatory and antimyotoxic properties against snake venoms and isolated toxins. RA inhibited the edema and myotoxic activity induced by the basic PLA2s BthTX-I and BthTX-II. It was, however, less efficient to inhibit the PLA2 activity of BthTX-II and, still less, the PLA2 and edema-inducing activities of the acidic isoform BthA-I-PLA2 from the same venom, showing therefore a higher inhibitory activity upon basic PLA2s. RA also inhibited most of the myotoxic and partially the edema-inducing effects of both basic PLA2s, thus reinforcing the idea of dissociation between the catalytic and pharmacological domains. The pure compound potentiated the ability of the commercial equine polyvalent antivenom in neutralizing lethal and myotoxic effects of the crude venom and of isolated PLA2s in experimental models. CD data presented here suggest that, after binding, no significant conformation changes occur either in the Cv-RA or in the target PLA2. A possible model for the interaction of rosmarinic acid with Lys49-PLA2 BthTX-I is proposed.

  16. Levulinic acid

    Directory of Open Access Journals (Sweden)

    Barbara Hachuła

    2013-09-01

    Full Text Available The title compound (systematic name: 4-oxopentanoic acid, C5H8O3, is close to planar (r.m.s. deviation = 0.0762 Å. In the crystal, the molecules interact via O—H...O hydrogen bonds in which the hydroxy O atoms act as donors and the ketone O atoms in adjacent molecules as acceptors, forming C(7 chains along [20-1].

  17. 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.

    Science.gov (United States)

    Carbone, Katya; Fiordiponti, Luciano

    2016-07-22

    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.

  18. 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

    Directory of Open Access Journals (Sweden)

    Katya Carbone

    2016-07-01

    Full Text Available 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.

  19. Understanding Acid Rain

    Science.gov (United States)

    Damonte, Kathleen

    2004-01-01

    The term acid rain describes rain, snow, or fog that is more acidic than normal precipitation. To understand what acid rain is, it is first necessary to know what an acid is. Acids can be defined as substances that produce hydrogen ions (H+), when dissolved in water. Scientists indicate how acidic a substance is by a set of numbers called the pH…

  20. The effects of oxidative stress on phenolic composition and ...

    African Journals Online (AJOL)

    Twenty phenolic compounds (apigenin, caffeic acid, p-coumaric acid, gallic acid, ... quercetin, rutin hydrate, vanillic acid, ferulic acid, salicylic acid, sinapic acid, ... phenolic molecules biosynthesis and activation of antioxidant metabolism on ...

  1. Structure of Selected Derivates of p-Hydroxy Cynamonic Acid According to 13C CP MAS NMR and DFT Calculation

    International Nuclear Information System (INIS)

    Pisklak, D.M.; Wawer, I.; Tkaczyk, M.

    2005-01-01

    Derivatives of p-hydroxy cynamonic acid are widely occurring in fruits, vegetables, tea and coffee. They exhibit strong antioxidant activity due to the presence of phenolic group. Epidemiological, biological and biochemical data support health beneficial role of this group of compounds and anticarcinogenic, antimutagenic and antiinflamatory effects have been reported. The most common caffeic acid contributes significantly to the total polyphenol intake and has been suggested to play a role in the apparent association between the regular consumption of polyphenol-rich food and beverages, and the prevetion of inflammatory and proliferative diseases. 13 C MAS NMR spectra were recorded on a BRUKER DSX 400 spectrometer at 400,13. Powder samples were spun in a 4 mm rotor at 10 kHz ( 13 C). Signals were assigned:- By comparison with solution spectra; - Using dipolar dephasing and variable contact time experiments; - Confirmed by DFT calculations of shielding constants. The differences in chemical shifts between solution and solid state spectra are due to the formation of intramolecular and intermolecular hydrogen bonds, including C-OH...OC within cyclic dimers. (author)

  2. Simultaneous determination of ascorbic acid and caffeine in commercial soft drinks using reversed-phase ultraperformance liquid chromatography.

    Science.gov (United States)

    Turak, Fatma; Güzel, Remziye; Dinç, Erdal

    2017-04-01

    A new reversed-phase ultraperformance liquid chromatography method with a photodiode array detector was developed for the quantification of ascorbic acid (AA) and caffeine (CAF) in 11 different commercial drinks consisting of one energy drink and 10 ice tea drinks. Separation of the analyzed AA and CAF with an internal standard, caffeic acid, was performed on a Waters BEH C 18 column (100 mm × 2.1 mm, 1.7 μm i.d.), using a mobile phase consisting of acetonitrile and 0.2M H 3 PO 4 (11:89, v/v) with a flow rate of 0.25 mL/min and an injection volume of 1.0 μL. Calibration graphs for AA and CAF were computed from the peak area ratio of AA/internal standard and CAF/internal standard detected at 244.0 nm and 273.6 nm, respectively. The developed reversed-phase ultraperformance liquid chromatography method was validated by analyzing standard addition samples. The proposed reversed-phase ultraperformance liquid chromatography method gave us successful results for the quantitative analysis of commercial drinks containing AA and CAF substances. Copyright © 2016. Published by Elsevier B.V.

  3. Simultaneous determination of ascorbic acid and caffeine in commercial soft drinks using reversed-phase ultraperformance liquid chromatography

    Directory of Open Access Journals (Sweden)

    Fatma Turak

    2017-04-01

    Full Text Available A new reversed-phase ultraperformance liquid chromatography method with a photodiode array detector was developed for the quantification of ascorbic acid (AA and caffeine (CAF in 11 different commercial drinks consisting of one energy drink and 10 ice tea drinks. Separation of the analyzed AA and CAF with an internal standard, caffeic acid, was performed on a Waters BEH C18 column (100 mm × 2.1 mm, 1.7 μm i.d., using a mobile phase consisting of acetonitrile and 0.2M H3PO4 (11:89, v/v with a flow rate of 0.25 mL/min and an injection volume of 1.0 μL. Calibration graphs for AA and CAF were computed from the peak area ratio of AA/internal standard and CAF/internal standard detected at 244.0 nm and 273.6 nm, respectively. The developed reversed-phase ultraperformance liquid chromatography method was validated by analyzing standard addition samples. The proposed reversed-phase ultraperformance liquid chromatography method gave us successful results for the quantitative analysis of commercial drinks containing AA and CAF substances.

  4. The acidic functional groups of humic acid

    Energy Technology Data Exchange (ETDEWEB)

    Shanxiang, Li; Shuhe, Sun; Zhai Zongxi, Wu Qihu

    1983-09-01

    The acidic functional groups content, pK value, DELTAH and DELTAS of humic acid (HA) and nitro-humic acid (NHA) were determined by potentiometry, conductometry and calorimetric titration. The thermodynamic parameters of carboxylic groups and phenolic hydroxyl groups of humic acid are similar to that of simple hydroxy-benzoic acid. The configuration sites of acidic functional groups in humic acid from different coals are different. The carbonyl groups on aromatic rings are probably ortho to phenolic -OH for HA and NHA extracted from Huangxian's brown coal and Japanese lignite, while those from Lingshi's weathered coal are not. The weak -COOH groups of the latter possess higher chemical activity. The -COOH content in HA increases, phenolic -OH group decreases and the chemical acidity of acidic functional groups increases when HA is oxidized by nitric acid. (14 refs.)

  5. Application of response surface methodology optimization for the ...

    African Journals Online (AJOL)

    STORAGESEVER

    2009-04-20

    Apr 20, 2009 ... of CQAs in tobacco waste were identified as three isomers containing chlorogenic acid (5-caffecylquinic acid ... Key words: Caffeic acid, caffeoylquinic acids (CQAs), hydrolysis reaction parameter optimization, response surface ..... Rosmarinic acid and caffeic acid produce antidepressive-like effect in.

  6. Okadaic acid

    DEFF Research Database (Denmark)

    Danielsen, E Michael; Hansen, Gert H; Severinsen, Mai C K

    2014-01-01

    are the hallmark of phospholipidosis, a pathological condition characterized by lysosomal phospholipid accumulation. Phospholipidosis is observed in acquired lysosomal storage diseases and is induced by a large number of cationic amphiphilic drugs. Unlike the latter, however, OA does not act by accumulating...... in acidic organelles, implying a different toxic mechanism of action. We propose that rapid induction of LBs, an indicator of phospholipidosis, should be included in the future toxicity profile of OA....... hyper protein phosphorylation, but no detectable loss of cell polarity or cytoskeletal integrity of the enterocytes. Using a fluorescent membrane marker, FM dye, endocytosis from the brush border was affected by the toxin. Although constitutive uptake into subapical terminal web-localized early...

  7. Analysis of organic acids and phenols of interest in the wine industry using Langmuir-Blodgett films based on functionalized nanoparticles.

    Science.gov (United States)

    Medina-Plaza, C; García-Cabezón, C; García-Hernández, C; Bramorski, C; Blanco-Val, Y; Martín-Pedrosa, F; Kawai, T; de Saja, J A; Rodríguez-Méndez, M L

    2015-01-01

    A chemically modified electrode consisting of Langmuir-Blodgett (LB) films of n-dodecanethiol functionalized gold nanoparticles (SDODAuNP-LB), was investigated as a voltammetric sensor of organic and phenolic acids of interest in the wine industry. The nanostructured films demonstrated interfacial properties being able to detect the main organic acids present in grapes and wines (tartaric, malic, lactic and citric). Compared to a bare ITO electrode, the modified electrodes exhibited a shift of the reduction potential in the less positive direction and a marked enhancement in the current response. Moreover, the increased electrocatalytic properties made it possible to distinguish between the different dissociable protons of polyprotic acids. The SDODAuNP-LB sensor was also able to provide enhanced responses toward aqueous solutions of phenolic acids commonly found in wines (caffeic and gallic acids). The presence of nanoparticles increased drastically the sensitivity toward organic acids and phenolic compounds. Limits of detection as low as 10(-6) mol L(-1) were achieved. Efficient catalytic activity was also observed in mixtures of phenolic acid/tartaric in the range of pHs typically found in wines. In such mixtures, the electrode was able to provide simultaneous information about the acid and the phenol concentrations with a complete absence of interferences. The excellent sensing properties shown by these sensors could be attributed to the electrocatalytic properties of the nanoparticles combined with the high surface to volume ratio and homogeneity provided by the LB technique used for the immobilization. Moreover, the LB technique also provided an accurate method to immobilize the gold nanoparticles giving rise to stable and reproducible sensors showing repeatability lower than 2% and reproducibility lower than 4% for all the compounds analyzed. Copyright © 2014. Published by Elsevier B.V.

  8. Effect of Chlorogenic Acid on Melanogenesis of B16 Melanoma Cells

    Directory of Open Access Journals (Sweden)

    Hao-Rong Li

    2014-08-01

    Full Text Available Chlorogenic acid (CGA, the ester formed between caffeic acid and l-quinic acid, is a widespread phenolic compound. It is part of the human diet, found in foods such as coffee, apples, pears, etc. CGA is also was widely used in cosmetics, but the effects of CGA on melanogenesis are unknown. In this study, we analyzed the effects of CGA on cell proliferation, melanin content and tyrosinase of B16 murine melanoma cells. Additionally, the enzymatic reactions of CGA in B16 melanoma cells lytic solution were detected by UV spectrophotometry. Results showed CGA at 30 and 60 μM significantly suppresses cell proliferation. 8-MOP at 100 μM significantly promotes cell proliferation, but CGA can counter this. Incubated for 24 h, CGA (500 μM improves melanogenesis while suppressing tyrosinase activity in B16 melanoma cells or 8-methoxypsoralen (8-MOP co-incubated B16 melanoma cells. After 12 h, B16 melanoma cell treatment with CGA leads to an increase in melanin accumulation, however, after 48 h there is a decrease in melanin production which correlates broadly with a decrease in tyrosinase activity. CGA incubated with lytic solution 24 h turned brown at 37 °C. The formation of new products (with a maximum absorption at 295 nm is associated with reduction of CGA (maximum absorption at 326 nm. Therefore, CGA has its two sidesroles in melanogenesis of B16 melanoma cells. CGA is a likely a substrate of melanin, but the metabolic product(s of CGA may suppress melanogenesis in B16 melanoma cells by inhibiting tyrosinase activity.

  9. Temporary reduction of radiation does not permanently reduce flavonoid glycosides and phenolic acids in red lettuce.

    Science.gov (United States)

    Becker, Christine; Kläring, Hans-Peter; Kroh, Lothar W; Krumbein, Angelika

    2013-11-01

    Applying transparent daytime screens in greenhouses in cool seasons reduces the amount of energy needed for heating, but also the solar radiation available for crops. This can reduce yield and product quality of leafy vegetables because of constrained photosynthesis and altered biosynthesis. To study this, we cultivated five-week old red leaf lettuce (Lactuca sativa L.) for four weeks in growth chambers under a photosynthetic photon flux density (PPFD) of 225 and 410 μmol m(-2) s(-1), respectively. Some plants were exchanged between radiation intensities after two weeks. We investigated the concentration of five flavonoid glycosides, three caffeic acid derivatives, reducing sugars as well as plant growth. Remarkably, no significant influence of radiation intensity on the concentration of phenolic acids or anthocyanin glycosides was observed. In contrast, quercetin and luteolin glycoside concentration was between 14 and 34% lower in plants growing under lower compared to higher PPFD. Already after two weeks of cultivation, plants grown under lower PPFD contained less quercetin and luteolin glycosides but they completely compensated if subsequently transferred to higher PPFD until harvest. Hence, marketable lettuce heads which experienced temporary shading followed by an unshaded phase did not contain lower concentrations of flavonoid glycosides or phenolic acids. Also, there was no reduction of head mass in this variant. Our results suggest that saving energy in early growth stages is feasible without losses in yield or health promoting phenolic substances. In addition, there was a close correlation between the concentration of reducing sugars and some flavonoid glycosides, indicating a close metabolic connection between their biosynthesis and the availability of carbohydrates. Copyright © 2013 The Authors. Published by Elsevier Masson SAS.. All rights reserved.

  10. In-vial liquid-liquid microextraction-capillary electrophoresis method for the determination of phenolic acids in vegetable oils.

    Science.gov (United States)

    Abu Bakar, Nur Bahiyah; Makahleh, Ahmad; Saad, Bahruddin

    2012-09-12

    An in-vial liquid-liquid microextraction method was developed for the selective extraction of the phenolic acids (caffeic, gallic, cinnamic, ferulic, chlorogenic, syringic, vanillic, benzoic, p-hydroxybenzoic, 2,4-dihydroxybenzoic, o-coumaric, m-coumaric and p-coumaric) in vegetable oil samples. The optimised extraction conditions for 20 g sample were: volume of diluent (n-hexane), 2 mL; extractant, methanol: 5 mM sodium hydroxide (60:40; v/v); volume of extractant, 300 μL (twice); vortex, 1 min; centrifugation, 5 min. Recoveries for the studied phenolic acids were 80.1-119.5%. The simultaneous determination of the phenolic acid extracts was investigated by capillary electrophoresis (CE). Separations were carried out on a bare fused-silica capillary (50 μm i.d.× 40 cm length) involving 25 mM sodium tetraborate (pH 9.15) and 5% methanol as CE background electrolyte in the normal polarity mode, voltage of 30 kV, temperature of 25°C, injection time of 4s (50 mbar) and electropherograms were recorded at 200 nm. The phenolic acids were successfully separated in less than 10 min. The validated in-vial LLME-CE method was applied to the determination of phenolic acids in vegetable oil samples (extra virgin olive oil, virgin olive oil, pure olive oil, walnut oil and grapeseed oil). The developed method shows significant advantages over the current methods as lengthy evaporation step is not required. Copyright © 2012 Elsevier B.V. All rights reserved.

  11. Dietary ascorbic acid modulates the expression profile of stress protein genes in hepatopancreas of adult Pacific abalone Haliotis discus hannai Ino.

    Science.gov (United States)

    Wu, Chenglong; Wang, Jia; Xu, Wei; Zhang, Wenbing; Mai, Kangsen

    2014-12-01

    This study was conducted to investigate the effects of dietary ascorbic acid (AA) on transcriptional expression patterns of antioxidant proteins, heat shock proteins (HSP) and nuclear factor kappa B (NF-κB) in the hepatopancreas of Pacific abalone Haliotis discus hannai Ino (initial average length: 84.36 ± 0.24 mm) using real-time quantitative PCR assays. L-ascorbyl-2-molyphosphate (LAMP) was added to the basal diet to formulate four experimental diets containing 0.0, 70.3, 829.8 and 4967.5 mg AA equivalent kg(-1) diets, respectively. Each diet was fed to triplicate groups of adult abalone in acrylic tanks (200 L) in a flow-through seawater system. Each tank was stocked with 15 abalone. Animals were fed once daily (17:00) to apparent satiation for 24 weeks. The results showed that the dietary AA (70.3 mg kg(-1)) could significantly up-regulate the expression levels of Cu/Zn superoxide dismutase (SOD), catalase (CAT), glutathione-S-transferase (GST), feritin (FT) and heat shock protein 26 (HSP26) in the hepatopancreas of abalone in this treatment compared to the controls. However, the expression levels of Mn-SOD, glutathione peroxidase (GPX), thioredoxin peroxidase (TPx), selenium-binding protein (SEBP), HSP70 and HSP90 were significantly down-regulated. Compared with those in the group with 70.3 mg kg(-1) dietary AA, the expression levels of CAT, GST and HSP26 were decreased in abalone fed with very high dietary AA (4967.5 mg kg(-1)). In addition, significant up-regulations of expression levels of Mn-SOD, GPX, TPx, SEBP, FT, HSP70, HSP90 and NF-κB were observed in abalone fed with apparently excessive dietary AA (829.8 and 4967.5 mg kg(-1)) as compared to those fed 70.3 mg kg(-1) dietary AA. These findings showed that dietary AA influenced the expression levels of antioxidant proteins, heat shock proteins and NF-κB in the hepatopancreas of abalone at transcriptional level. Levels of dietary AA that appeared adequate (70.3 mg kg(-1)) reduced the oxidative stress

  12. Diagnostic fragment-ion-based and extension strategy coupled to DFIs intensity analysis for identification of chlorogenic acids isomers in Flos Lonicerae Japonicae by HPLC-ESI-MS(n).

    Science.gov (United States)

    Zhang, Jia-Yu; Zhang, Qian; Li, Ning; Wang, Zi-Jian; Lu, Jian-Qiu; Qiao, Yan-Jiang

    2013-01-30

    A method of modified diagnostic fragment-ion-based extension strategy (DFIBES) coupled to DFIs (diagnostic fragmentation ions) intensity analysis was successfully established to simultaneously screen and identify the chlorogenic acids (CGAs) in Flos Lonicerae Japonicae (FLJ) by HPLC-ESI-MS(n). DFIs, such as m/z 191 [quinic acid-H](-), m/z 179 [caffeic acid-H](-) and m/z 173 [quinic acid-H-H2O](-) were determined or proposed from the fragmentation patterns analysis of corresponding reference substances for every chemical family of CGAs. A "structure extension" method was then proposed based on the well-demonstrated fragmentation patterns and was successively applied into the rapid screening of CGAs in FLJ. Considering that substitution isomerism is a common phenomenon, a full ESI-MS(n) fragmentation analysis according to the intensity of DFIs has been performed to identify the CGA isomers. Based on the DFIs and intensity analysis, 41 peaks attributed to CGAs including 4 caffeoylquinic acids (CQA), 7 CQA glycosides, 6 dicaffeoylquinic acids (DiCQA), 10 DiCQA glycosides, 1 tricaffeoylquinic acids (TriCQA), 4p-coumaroylquinic acids (pCoQA), 3 feruloylquinic acids (FQA) and 6 caffeoylferuloylquinic acids (CFQA) were identified preliminarily in a 65-min chromatographic run. It was the first time to systematically report the presence of CGAs in FLJ, especially for CQA glycosides, DiCQA glycosides, TriCQA, pCoQA and CFQA. All the results indicated that the method of developed DFIBES coupled to DFIs analysis was feasible, reliable and universal for screening and identifying the constituents with the same carbon skeletons especially the isomeric compounds from the complex extract of TCMs. Copyright © 2012 Elsevier B.V. All rights reserved.

  13. Application of antioxidants during short-path distillation of structured lipids

    DEFF Research Database (Denmark)

    Timm-Heinrich, Maike; Xu, Xuebing; Nielsen, Nina Skall

    2007-01-01

    A specific structured lipid was produced from sunflower oil and caprylic acid. The antioxidative effect of adding alpha-tocopherol, ascorbyl palmitate or citric acid (each in three different concentrations) was investigated before and after the purification process (short-path distillation...

  14. Effect of Storage Temperature on Vitamin C, Total Phenolics, UPLC Phenolic Acid Profile and Antioxidant Capacity of Eleven Potato (Solanum tuberosum Varieties

    Directory of Open Access Journals (Sweden)

    Joseph Hubert Yamdeu Galani

    2017-03-01

    Full Text Available Storage of potato tubers at low temperature affects their metabolism and may alter their phytochemical properties. There is a need to elucidate the changes in antioxidant compounds, activity and enzymes during storage of tubers. Eleven Indian potato varieties were evaluated for antioxidant parameters, after 0, 30, 60 and 90 days of storage at room temperature, 15 °C and 4 °C. Total phenolics (0.0786–0.1546 mg gallic acid equivalents⋅g−1 FW and vitamin C content (0.0828–0.2416 mg⋅g−1 FW varied among the varieties and were different with storage temperature; their levels fluctuated during storage but remained above the initial level until the last day of observation. Phenolic acid profiling by UPLC identified 12 compounds among which the most abundant was chlorogenic acid followed by gallic acid, sinapic acid and ellagic acid. Except para-coumaric acid which decreased at 4 °C, all the phenolic acids increased with storage. Caffeic acid, chlorogenic acid, protocatechuic acid and gallic acid mostly correlated with total phenolic content (r = 0.456, 0.482, 0.588 and 0.620, respectively. Antioxidant activity against both DPPH and ABTS radicals increased during the initial days of storage and then dropped to a level comparable or lower than the original value, irrespective of the storage temperature. Correlation study revealed that chlorogenic acid, gallic acid and ferulic acid mostly contributed to antioxidant activity. Activity of both antioxidant enzymes, superoxide dismutase and ascorbate peroxidase, increased initially but then decreased to values lower than the initial level and were not influenced by storage temperature. Correlation with antioxidant activity indicated that the enhancement of reactive oxygen scavenging species in cold stored tubers could result mainly from ascorbate peroxidase activity. Our results demonstrate that storage temperature adversely influences the metabolism and the content of

  15. [Teichoic acids from lactic acid bacteria].

    Science.gov (United States)

    Livins'ka, O P; Harmasheva, I L; Kovalenko, N K

    2012-01-01

    The current view of the structural diversity of teichoic acids and their involvement in the biological activity of lactobacilli has been reviewed. The mechanisms of effects of probiotic lactic acid bacteria, in particular adhesive and immunostimulating functions have been described. The prospects of the use of structure data of teichoic acid in the assessment of intraspecific diversity of lactic acid bacteria have been also reflected.

  16. Plasma amino acids

    Science.gov (United States)

    Amino acids blood test ... types of methods used to determine the individual amino acid levels in the blood. ... test is done to measure the level of amino acids in the blood. An increased level of a ...

  17. Uric acid - urine

    Science.gov (United States)

    ... this page: //medlineplus.gov/ency/article/003616.htm Uric acid urine test To use the sharing features on ... are no risks with this test. Images Uric acid test Uric acid crystals References Burns CM, Wortmann RL. Clinical ...

  18. Uric acid test (image)

    Science.gov (United States)

    Uric acid urine test is performed to check for the amount of uric acid in urine. Urine is collected over a 24 ... for testing. The most common reason for measuring uric acid levels is in the diagnosis or treatment of ...

  19. Methylmalonic acid blood test

    Science.gov (United States)

    ... medlineplus.gov/ency/article/003565.htm Methylmalonic acid blood test To use the sharing features on this page, please enable JavaScript. The methylmalonic acid blood test measures the amount of methylmalonic acid in the ...

  20. Facts about Folic Acid

    Science.gov (United States)

    ... Information For… Media Policy Makers Facts About Folic Acid Language: English (US) Español (Spanish) Recommend on Facebook ... of the baby’s brain and spine. About folic acid Folic acid is a B vitamin. Our bodies ...

  1. Protective effect of gallic acid and Syzygium cumini extract against oxidative stress-induced cellular injury in human lymphocytes.

    Science.gov (United States)

    De Bona, Karine Santos; Bonfanti, Gabriela; Bitencourt, Paula Eliete Rodrigues; da Silva, Thainan Paz; Borges, Raphaela Maleski; Boligon, Aline; Pigatto, Aline; Athayde, Margareth Lynde; Moretto, Maria Beatriz

    2016-01-01

    Syzygium cumini (Myrtaceae) presents antioxidant, anti-inflammatory, hypoglycemic and antibacterial effects; however, the cellular and molecular mechanisms of action in the immune system are not yet completely elucidated. This study evaluates the in vitro effect of gallic acid and aqueous S. cumini leaf extract (ASc) on adenosine deaminase (ADA) and dipeptidyl peptidase IV (DPP-IV) activities, cell viability and oxidative stress parameters in lymphocytes exposed to 2, 2'-azobis-2-amidinopropane dihydrochloride (AAPH). Lymphocytes were incubated with ASc (100 and 500 µg/ml) and gallic acid (50 and 200 µM) at 37 °C for 30 min followed by incubation with AAPH (1 mM) at 37 °C for 2 h. After the incubation time, the lymphocytes were used for determinations of ADA, DPP-IV and lactate dehydrogenase (LDH) activities, lipid peroxidation, protein thiol (P-SH) group levels and cellular viability by colorimetric methods. (i) HPLC fingerprinting of ASc revealed the presence of catechin, epicatechin, rutin, quercitrin, isoquercitrin, quercetin, kaempferol and chlorogenic, caffeic, gallic and ellagic acids; (ii) for the first time, ASc reduced the AAPH-induced increase in ADA activity, but no effect was observed on DPP-IV activity; (iii) ASc increased P-SH groups and cellular viability and decreased LDH activity, but was not able to reduce the AAPH-induced lipid peroxidation; (iv) gallic acid showed less protective effects than ASc. ASc affects the purinergic system and may modulate adenosine levels, indicating that the extract of this plant exhibits immunomodulatory properties. ASc also may potentially prevent the cellular injury induced by oxidative stress, highlighting its cytoprotective effects.

  2. Retrobiosynthetic NMR studies with 13C-labeled glucose. Formation of gallic acid in plants and fungi

    International Nuclear Information System (INIS)

    Werner, I.; Bacher, A.; Eisenreich, W.

    1997-01-01

    The biosynthesis of gallic acid was studied in cultures of the fungus Phycomyces blakesleeanus and in leaves of the tree Rhus typhina. Fungal cultures were grown with [1-13C]glucose or with a mixture of unlabeled glucose and [U-13C6]glucose. Young leaves of R. typhina were kept in an incubation chamber and were supplied with a solution containing a mixture of unlabeled glucose and [U-13C6]glucose via the leaf stem. Isotope distributions in isolated gallic acid and aromatic amino acids were analyzed by one-dimensional 1H and 13C NMR spectroscopy. A quantitative analysis of the complex isotopomer composition of metabolites was obtained by deconvolution of the 13C13C coupling multiplets using numerical simulation methods. This approach required the accurate analysis of heavy isotope chemical shift effects in a variety of different isotopomers and the analysis of long range 13C13C coupling constants. The resulting isotopomer patterns were interpreted using a retrobiosynthetic approach based on a comparison between the isotopomer patterns of gallic acid and tyrosine. The data show that both in the fungus and in the plant all carbon atoms of gallic acid are biosynthetically equivalent to carbon atoms of shikimate. Notably, the carboxylic group of gallic acid is derived from the carboxylic group of an early intermediate of the shikimate pathway and not from the side chain of phenylalanine or tyrosine. It follows that the committed precursor of gallic acid is an intermediate of the shikimate pathway prior to prephenate or arogenate, most probably 5-dehydroshikimate. A formation of gallic acid via phenylalanine, the lignin precursor, caffeic acid, or 3,4, 5-trihydroxycinnamic acid can be ruled out as major pathways in the fungus and in young leaves of R. typhina. The incorporation of uniformly 13C-labeled glucose followed by quantitative NMR analysis of isotopomer patterns is suggested as a general method for biosynthetic studies. As shown by the plant experiment, this

  3. Acid distribution in phosphoric acid fuel cells

    Energy Technology Data Exchange (ETDEWEB)

    Okae, I.; Seya, A.; Umemoto, M. [Fuji Electric Co., Ltd., Chiba (Japan)

    1996-12-31

    Electrolyte acid distribution among each component of a cell is determined by capillary force when the cell is not in operation, but the distribution under the current load conditions had not been clear so far. Since the loss of electrolyte acid during operation is inevitable, it is necessary to store enough amount of acid in every cell. But it must be under the level of which the acid disturbs the diffusion of reactive gases. Accordingly to know the actual acid distribution during operation in a cell is very important. In this report, we carried out experiments to clarify the distribution using small single cells.

  4. Alkyl caffeates as antioxidants in O/W emulsions: Impact of emulsifier type and endogenous tocopherols

    DEFF Research Database (Denmark)

    Sørensen, Ann-Dorit Moltke; Villeneuve, Pierre; Jacobsen, Charlotte

    2017-01-01

    , the aim was to evaluate the impact of emulsifiers (Citrem and Tween80) and presence of endogenous tocopherols on the efficacies of caffeic acid and caffeates (C1–C20) as antioxidants in emulsions. Lipid oxidation was evaluated during storage and partitioning of caffeic acid and caffeates was estimated...... by measuring their concentrations in the aqueous phase. Partitioning of caffeic acid and caffeates was influenced by emulsifier type and the presence of endogenous tocopherols. Caffeic acid was the most efficient antioxidant in Citrem and Tween stabilized emulsions in the presence of endogenous tocopherol....... In contrast, for Tween stabilized emulsions, caffeic acid acted as a prooxidant and the evaluated caffeates acted as strong antioxidants in the absence of endogenous tocopherol. Thus, when endogenous tocopherol was present lipophilization of caffeic acid did not increase its efficacy as an antioxidant...

  5. Omega-3 fatty acids, phenolic compounds and antioxidant characteristics of chia oil supplemented margarine.

    Science.gov (United States)

    Nadeem, Muhammad; Imran, Muhammad; Taj, Imran; Ajmal, Muhammad; Junaid, Muhammad

    2017-05-31

    Chia (Salvia hispanica L.) is known as power house of omega fatty acids which has great health benefits. It contains up to 78% linolenic acid (ω-3) and 18% linoleic acid (ω-6), which could be a great source of omega-3 fatty acids for functional foods. Therefore, in this study, margarines were prepared with supplementation of different concentrations of chia oil to enhance omega-3 fatty acids, antioxidant characteristics and oxidative stability of the product. Margarines were formulated from non-hydrogenated palm oil, palm kernel and butter. Margarines were supplemented with 5, 10, 15 and 20% chia oil (T 1 , T 2 , T 3 and T 4 ), respectively. Margarine without any addition of chia oil was kept as control. Margarine samples were stored at 5 °C for a period of 90 days. Physico-chemical (fat, moisture, refractive index, melting point, solid fat index, fatty acids profile, total phenolic contents, DPPH free radical scavenging activity, free fatty acids and peroxide value) and sensory characteristics were studied at the interval of 45 days. The melting point of T 1 , T 2 , T 3 and T 4 developed in current investigation were 34.2, 33.8, 33.1 and 32.5 °C, respectively. The solid fat index of control, T 1 , T 2 , T 3 and T 4 were 47.21, 22.71, 20.33, 18.12 and 16.58%, respectively. The α-linolenic acid contents in T 1 , T 2 , T 3 and T 4 were found 2.92, 5.85, 9.22, 12.29%, respectively. The concentration of eicosanoic acid in T 2 , T 3 and T 4 was 1.82, 3.52, 6.43 and 9.81%, respectively. The content of docosahexanoic acid in T 2 , T 3 and T 4 was present 1.26, 2.64, 3.49 and 5.19%, respectively. The omega-3 fatty acids were not detected in the control sample. Total phenolic contents of control, T 1 , T 2 , T 3 and T 4 samples were 0.27, 2.22, 4.15, 7.23 and 11.42 mg GAE/mL, respectively. DPPH free radical scavenging activity for control, T 1 , T 2 , T 3 and T 4 was noted 65.8, 5.37, 17.82, 24.95, 45.42 and 62.8%, respectively. Chlorogenic acid, caffeic acid

  6. Cinnamic Acid Derivatives Enhance the Efficacy of Transarterial Embolization in a Rat Model of Hepatocellular Carcinoma

    International Nuclear Information System (INIS)

    Wilkins, Luke R.; Brautigan, David L.; Wu, Hanping; Yarmohammadi, Hooman; Kubicka, Ewa; Serbulea, Vlad; Leitinger, Norbert; Liu, Wendy; Haaga, John R.

    2017-01-01

    IntroductionWe hypothesize that the combination of transarterial embolization (TAE) plus inhibition of lactate export will limit anaerobic metabolism and reduce tumor survival compared to TAE alone. The purpose of this study was to test this hypothesis in a rat model of hepatocellular carcinoma (HCC).MethodsRat N1-S1 hepatoma cells were assayed in vitro using the Seahorse XF analyzer to measure extracellular acidification (lactate excretion) comparing effects of the addition of caffeic acid (CA) or ferulic acid (FA) or UK-5099 with control. Monocarboxylate transporter Slc16a3 was knocked down by RNAi. N1S1 tumors were orthotopically implanted in rats and 4 groups evaluated: (1) Control, (2) TAE-only, (3) TAE plus CA, and (4) TAE plus FA. Tumor size was determined by ultrasound and analyzed by repeated measures statistics. Tumors harvested at 4 weeks were examined by microscopy.ResultsSeahorse assays showed that CA and FA caused a significant reduction by >90% in lactate efflux by N1S1 tumor cells (p < 0.01). Knockdown of Slc16a3 prevented inhibition by CA. In vivo tumors grew 30-fold in volume over 4 weeks in untreated controls. By comparison, TAE resulted in near cessation of growth (10% in 4-week time period). However, both TAE + CA and TAE + FA caused a significant reduction of tumor volumes (87 and 72%, respectively) compared to control and TAE (p < 0.05). Pathologic evaluation revealed residual tumor in the TAE group but no residual viable tumor cells in the TAE + CA and TAE + FA groups.ConclusionAddition of CA or FA enhances the effectiveness of TAE therapy for HCC in part by blocking lactate efflux.

  7. Cinnamic Acid Derivatives Enhance the Efficacy of Transarterial Embolization in a Rat Model of Hepatocellular Carcinoma

    Energy Technology Data Exchange (ETDEWEB)

    Wilkins, Luke R., E-mail: lrw6n@virginia.edu [University of Virginia Health Systems, Department of Radiology and Medical Imaging (United States); Brautigan, David L., E-mail: db8g@virginia.edu [University of Virginia, Department of Microbiology, Immunology, and Cancer Biology (United States); Wu, Hanping, E-mail: hanpingwumd@gmail.com [University Hospitals of Cleveland, Case Western Reserve University, Department of Radiology (United States); Yarmohammadi, Hooman, E-mail: yar.hooman@gmail.com [Memorial Sloan-Kettering Cancer Center, Department of Radiology (United States); Kubicka, Ewa, E-mail: emk6d@virginia.edu [University of Virginia, Department of Microbiology, Immunology, and Cancer Biology (United States); Serbulea, Vlad, E-mail: vs9ck@virginia.edu; Leitinger, Norbert, E-mail: nl2q@virginia.edu [University of Virginia, Department of Pharmacology (United States); Liu, Wendy, E-mail: wendy.liu@uhhospitals.org [University Hospitals of Cleveland, Case Western Reserve University, Department of Pathology (United States); Haaga, John R., E-mail: john.haaga@uhhospitals.org [University Hospitals of Cleveland, Case Western Reserve University, Department of Radiology (United States)

    2017-03-15

    IntroductionWe hypothesize that the combination of transarterial embolization (TAE) plus inhibition of lactate export will limit anaerobic metabolism and reduce tumor survival compared to TAE alone. The purpose of this study was to test this hypothesis in a rat model of hepatocellular carcinoma (HCC).MethodsRat N1-S1 hepatoma cells were assayed in vitro using the Seahorse XF analyzer to measure extracellular acidification (lactate excretion) comparing effects of the addition of caffeic acid (CA) or ferulic acid (FA) or UK-5099 with control. Monocarboxylate transporter Slc16a3 was knocked down by RNAi. N1S1 tumors were orthotopically implanted in rats and 4 groups evaluated: (1) Control, (2) TAE-only, (3) TAE plus CA, and (4) TAE plus FA. Tumor size was determined by ultrasound and analyzed by repeated measures statistics. Tumors harvested at 4 weeks were examined by microscopy.ResultsSeahorse assays showed that CA and FA caused a significant reduction by >90% in lactate efflux by N1S1 tumor cells (p < 0.01). Knockdown of Slc16a3 prevented inhibition by CA. In vivo tumors grew 30-fold in volume over 4 weeks in untreated controls. By comparison, TAE resulted in near cessation of growth (10% in 4-week time period). However, both TAE + CA and TAE + FA caused a significant reduction of tumor volumes (87 and 72%, respectively) compared to control and TAE (p < 0.05). Pathologic evaluation revealed residual tumor in the TAE group but no residual viable tumor cells in the TAE + CA and TAE + FA groups.ConclusionAddition of CA or FA enhances the effectiveness of TAE therapy for HCC in part by blocking lactate efflux.

  8. Topical Vitamin C and the Skin: Mechanisms of Action and Clinical Applications

    OpenAIRE

    Al-Niaimi, Firas; Chiang, Nicole Yi Zhen

    2017-01-01

    OBJECTIVE: This review article details the main mechanisms of action and clinical applications of topical vitamin C on the skin, including its antioxidative, photoprotective, antiaging, and antipigmentary effects. DESIGN: A PubMed search for the relevant articles on vitamin C and the skin was conducted using the following key words: “vitamin C,” “ascorbic acid,” “ascorbyl-6-palmitate,”and “magnesium ascorbyl phosphate.” RESULTS: As one of the most powerful antioxidants in the skin, vitamin C ...

  9. Photochemical reduction of water-soluble C60 derivatives (EPR study)

    International Nuclear Information System (INIS)

    Brezova, V.; Stasko, A.; Dvoranova, D.; Asmus, K.D.; Guldi, D.M.

    1999-01-01

    The photochemical reduction of three bis-functionalized C 60 derivatives resulted in the formation of a single radical product, characterized by relatively narrow EPR line (g M = 2.0007, pp < 0.02 mT). In the irradiated aqueous solutions containing L-ascorbic acid, in the addition to the EPR line related to bis-adduct mono-anion, also 6-line EPR spectrum of ascorbyl radical was observed. Consequently, the photoinduced formation of ascorbyl radical was attributed to the intermolecular quenching of fullerenes excited states. (authors)

  10. Citric acid urine test

    Science.gov (United States)

    Urine - citric acid test; Renal tubular acidosis - citric acid test; Kidney stones - citric acid test; Urolithiasis - citric acid test ... No special preparation is necessary for this test. But the results ... test is usually done while you are on a normal diet. Ask your ...

  11. Synthesis of Selective Butyrylcholinesterase Inhibitors Coupled between α-Lipoic Acid and Polyphenols by Using 2-(Piperazin-1-yl)ethanol Linker

    Energy Technology Data Exchange (ETDEWEB)

    Yeun, Go Heun; Lee, Seung Hwan; LIm, Yong Bae; Lee, Hye Sook; Lee, Bong Ho; Park, Jeong Ho [Hanbat National Univ., Daejeon (Korea, Republic of); Won, Mooho [Kangwon National Univ., Chuncheon (Korea, Republic of)

    2013-04-15

    In the previous paper (Bull. Korean Chem. Soc., 2011, 32, 2997), the hybrid molecules between α-lipoic acid (ALA) and polyphenols (PPs) connected with neutral 2-(2-aminoethoxy)ethanol linker (linker-1) showed new biological activity such as butyrylcholinesterase (BuChE) inhibition. In order to increase the binding affinity of the hybrid compounds to cholinesterase (ChE), the neutral 2-(2-aminoethoxy)ethanol (linker 1) was switched to the cationic 2-(piperazin-1-yl)ethanol linker (linker 2). The IC{sub 50} values of the linker-2 hybrid molecules for BuChE inhibition were lower than those of linker-1 hybrid molecules (except 9-2) and they also had the same great selectivity for BuChE over AChE (> 800 fold) as linker-1 hybrid molecules. ALA-acetyl caffeic acid (10-2, ALA-AcCA) was shown as an effective inhibitor of BuChE (IC{sub 50} = 0.44 ± 0.24 μM). A kinetic study using 7-2 showed that it is the same mixed type inhibition as 7-1. Its inhibition constant (Ki) to BuChE is 4.3 ± 0.09 μM.

  12. Synthesis of Selective Butyrylcholinesterase Inhibitors Coupled between α-Lipoic Acid and Polyphenols by Using 2-(Piperazin-1-yl)ethanol Linker

    International Nuclear Information System (INIS)

    Yeun, Go Heun; Lee, Seung Hwan; LIm, Yong Bae; Lee, Hye Sook; Lee, Bong Ho; Park, Jeong Ho; Won, Mooho

    2013-01-01

    In the previous paper (Bull. Korean Chem. Soc., 2011, 32, 2997), the hybrid molecules between α-lipoic acid (ALA) and polyphenols (PPs) connected with neutral 2-(2-aminoethoxy)ethanol linker (linker-1) showed new biological activity such as butyrylcholinesterase (BuChE) inhibition. In order to increase the binding affinity of the hybrid compounds to cholinesterase (ChE), the neutral 2-(2-aminoethoxy)ethanol (linker 1) was switched to the cationic 2-(piperazin-1-yl)ethanol linker (linker 2). The IC 50 values of the linker-2 hybrid molecules for BuChE inhibition were lower than those of linker-1 hybrid molecules (except 9-2) and they also had the same great selectivity for BuChE over AChE (> 800 fold) as linker-1 hybrid molecules. ALA-acetyl caffeic acid (10-2, ALA-AcCA) was shown as an effective inhibitor of BuChE (IC 50 = 0.44 ± 0.24 μM). A kinetic study using 7-2 showed that it is the same mixed type inhibition as 7-1. Its inhibition constant (Ki) to BuChE is 4.3 ± 0.09 μM

  13. Antioxidant, anti-inflammatory and anti-septic potential of phenolic acids and flavonoid fractions isolated from Lolium multiflorum.

    Science.gov (United States)

    Choi, Ki-Choon; Son, Young-Ok; Hwang, Jung-Min; Kim, Beom-Tae; Chae, Minseon; Lee, Jeong-Chae

    2017-12-01

    Interest has recently renewed in using Lolium multiflorum Lam. (Poaceae) (called Italian ryegrass; IRG) silage as an antioxidant and anti-inflammatory diet. This study investigated the antioxidant, anti-inflammatory and anti-septic potential of IRG silage and identified the primary components in IRG active fractions. Total 16 fractions were separated from the chloroform-soluble extract of IRG aerial part using Sephadex LH-20 column before HPLC analysis. Antioxidant and anti-inflammatory activities of the fractions at doses of 0-100 μg/mL were investigated using various cell-free and cell-mediated assay systems. To explore anti-septic effect of IRG fractions, female ICR and BALB/c mice orally received 40 mg/kg of phenolic acid and flavonoid-rich active fractions F 7 and F 8 every other day for 10 days, respectively, followed by LPS challenge. The active fractions showed greater antioxidant and anti-inflammatory potential compared with other fractions. IC 50 values of F 7 and F 8 to reduce LPS-stimulated NO and TNF-α production were around 15 and 30 μg/mL, respectively. Comparison of retention times with authentic compounds through HPLC analysis revealed the presence of caffeic acid, ferulic acid, myricetin and kaempferol in the fractions as primary components. These fractions inhibited LPS-stimulated MAPK and NF-κB activation. Supplementation with F 7 or F 8 improved the survival rates of mice to 70 and 60%, respectively, in LPS-injected mice and reduced near completely serum TNF-α and IL-6 levels. This study highlights antioxidant, anti-inflammatory and anti-septic activities of IRG active fractions, eventually suggesting their usefulness in preventing oxidative damage and inflammatory disorders.

  14. Phenolic acid intake, delivered via moderate champagne wine consumption, improves spatial working memory via the modulation of hippocampal and cortical protein expression/activation.

    Science.gov (United States)

    Corona, Giulia; Vauzour, David; Hercelin, Justine; Williams, Claire M; Spencer, Jeremy P E

    2013-11-10

    While much data exist for the effects of flavonoid-rich foods on spatial memory in rodents, there are no such data for foods/beverages predominantly containing hydroxycinnamates and phenolic acids. To address this, we investigated the effects of moderate Champagne wine intake, which is rich in these components, on spatial memory and related mechanisms relative to the alcohol- and energy-matched controls. In contrast to the isocaloric and alcohol-matched controls, supplementation with Champagne wine (1.78 ml/kg BW, alcohol 12.5% vol.) for 6 weeks led to an improvement in spatial working memory in aged rodents. Targeted protein arrays indicated that these behavioral effects were paralleled by the differential expression of a number of hippocampal and cortical proteins (relative to the isocaloric control group), including those involved in signal transduction, neuroplasticity, apoptosis, and cell cycle regulation. Western immunoblotting confirmed the differential modulation of brain-derived neurotrophic factor, cAMP response-element-binding protein (CREB), p38, dystrophin, 2',3'-cyclic-nucleotide 3'-phosphodiesterase, mammalian target of rapamycin (mTOR), and Bcl-xL in response to Champagne supplementation compared to the control drink, and the modulation of mTOR, Bcl-xL, and CREB in response to alcohol supplementation. Our data suggest that smaller phenolics such as gallic acid, protocatechuic acid, tyrosol, caftaric acid, and caffeic acid, in addition to flavonoids, are capable of exerting improvements in spatial memory via the modulation in hippocampal signaling and protein expression. Changes in spatial working memory induced by the Champagne supplementation are linked to the effects of absorbed phenolics on cytoskeletal proteins, neurotrophin expression, and the effects of alcohol on the regulation of apoptotic events in the hippocampus and cortex.

  15. Acid Deposition Phenomena

    International Nuclear Information System (INIS)

    Ramadan, A.E.K.

    2004-01-01

    Acid deposition, commonly known as acid rain, occurs when emissions from the combustion of fossil fuels and other industrial processes undergo complex chemical reactions in the atmosphere and fall to the earth as wet deposition (rain, snow, cloud, fog) or dry deposition (dry particles, gas). Rain and snow are already naturally acidic, but are only considered problematic when less than a ph of 5.0 The main chemical precursors leading to acidic conditions are atmospheric concentrations of sulfur dioxide (SO 2 ) and nitrogen oxides (NO x ). When these two compounds react with water, oxygen, and sunlight in the atmosphere, the result is sulfuric (H 2 SO 4 ) and nitric acids (HNO 3 ), the primary agents of acid deposition which mainly produced from the combustion of fossil fuel and from petroleum refinery. Airborne chemicals can travel long distances from their sources and can therefore affect ecosystems over broad regional scales and in locations far from the sources of emissions. According to the concern of petroleum ministry with the environment and occupational health, in this paper we will discussed the acid deposition phenomena through the following: Types of acidic deposition and its components in the atmosphere Natural and man-made sources of compounds causing the acidic deposition. Chemical reactions causing the acidic deposition phenomenon in the atmosphere. Factors affecting level of acidic deposition in the atmosphere. Impact of acid deposition. Procedures for acidic deposition control in petroleum industry

  16. Acid Lipase Disease

    Science.gov (United States)

    ... of Neurological Disorders and Stroke conducts and supports research to understand lipid storage diseases such as acid lipase deficiency and ... of Neurological Disorders and Stroke conducts and supports research to understand lipid storage diseases such as acid lipase deficiency and ...

  17. Lactic acid test

    Science.gov (United States)

    ... this page: //medlineplus.gov/ency/article/003507.htm Lactic acid test To use the sharing features on this page, please enable JavaScript. Lactic acid is mainly produced in muscle cells and red ...

  18. Amino Acid Metabolism Disorders

    Science.gov (United States)

    ... this process. One group of these disorders is amino acid metabolism disorders. They include phenylketonuria (PKU) and maple syrup urine disease. Amino acids are "building blocks" that join together to form ...

  19. Folic Acid and Pregnancy

    Science.gov (United States)

    ... Fitness Diseases & Conditions Infections Drugs & Alcohol School & Jobs Sports Expert Answers (Q&A) Staying Safe Videos for Educators Search English Español Folic Acid and Pregnancy KidsHealth / For Parents / Folic Acid and Pregnancy Print ...

  20. Omega-6 Fatty Acids

    Science.gov (United States)

    Omega-6 fatty acids are types of fats. Some types are found in vegetable oils, including corn, evening primrose seed, safflower, and soybean oils. Other types of omega-6 fatty acids are found in black currant seed, borage seed, ...

  1. Hydrochloric acid poisoning

    Science.gov (United States)

    Hydrochloric acid is a clear, poisonous liquid. It is highly corrosive, which means it immediately causes severe damage, such ... poisoning due to swallowing or breathing in hydrochloric acid. This article is for information only. Do NOT ...

  2. Aminolevulinic Acid Topical

    Science.gov (United States)

    Aminolevulinic acid is used in combination with photodynamic therapy (PDT; special blue light) to treat actinic keratoses (small crusty ... skin cancer) of the face or scalp. Aminolevulinic acid is in a class of medications called photosensitizing ...

  3. Zoledronic Acid Injection

    Science.gov (United States)

    Zoledronic acid (Reclast) is used to prevent or treat osteoporosis (condition in which the bones become thin and weak ... of life,' end of regular menstrual periods). Zoledronic acid (Reclast) is also used to treat osteoporosis in ...

  4. Azelaic Acid Topical

    Science.gov (United States)

    Azelaic acid gel and foam is used to clear the bumps, lesions, and swelling caused by rosacea (a skin ... redness, flushing, and pimples on the face). Azelaic acid cream is used to treat the pimples and ...

  5. Aminocaproic Acid Injection

    Science.gov (United States)

    Aminocaproic acid injection is used to control bleeding that occurs when blood clots are broken down too quickly. This ... the baby is ready to be born). Aminocaproic acid injection is also used to control bleeding in ...

  6. Deoxycholic Acid Injection

    Science.gov (United States)

    Deoxycholic acid injection is used to improve the appearance and profile of moderate to severe submental fat ('double chin'; fatty tissue located under the chin). Deoxycholic acid injection is in a class of medications called ...

  7. Amino acids and proteins

    NARCIS (Netherlands)

    van Goudoever, Johannes B.; Vlaardingerbroek, Hester; van den Akker, Chris H.; de Groof, Femke; van der Schoor, Sophie R. D.

    2014-01-01

    Amino acids and protein are key factors for growth. The neonatal period requires the highest intake in life to meet the demands. Those demands include amino acids for growth, but proteins and amino acids also function as signalling molecules and function as neurotransmitters. Often the nutritional

  8. Acid Rain Study Guide.

    Science.gov (United States)

    Hunger, Carolyn; And Others

    Acid rain is a complex, worldwide environmental problem. This study guide is intended to aid teachers of grades 4-12 to help their students understand what acid rain is, why it is a problem, and what possible solutions exist. The document contains specific sections on: (1) the various terms used in conjunction with acid rain (such as acid…

  9. Immunoglobulin and fatty acids

    DEFF Research Database (Denmark)

    2009-01-01

    The present invention relates to a composition comprising 0.1-10 w/w % immunoglobulin (Ig), 4-14 w/w % saturated fatty acids, 4-14 w/w % mono-unsaturated fatty acids and 0-5 w/w % poly-unsaturated fatty acids, wherein the weight percentages are based on the content of dry matter in the composition...

  10. The Acid Rain Reader.

    Science.gov (United States)

    Stubbs, Harriett S.; And Others

    A topic which is often not sufficiently dealt with in elementary school textbooks is acid rain. This student text is designed to supplement classroom materials on the topic. Discussed are: (1) "Rain"; (2) "Water Cycle"; (3) "Fossil Fuels"; (4) "Air Pollution"; (5) "Superstacks"; (6) "Acid/Neutral/Bases"; (7) "pH Scale"; (8) "Acid Rain"; (9)…

  11. Stomach acid test

    Science.gov (United States)

    Gastric acid secretion test ... of the cells in the stomach to release acid. The stomach contents are then removed and analyzed. ... 3.5). These numbers are converted to actual acid production in units of milliequivalents per hour (mEq/ ...

  12. Effect of pH on the copigmentation of anthocyanins from Cabernet Sauvignon grape extracts with organic acids Efeito do pH na copigmentação de antocianinas do extrato de uvas Cabernet Sauvignon com ácidos orgânicos

    Directory of Open Access Journals (Sweden)

    Cony Gauche

    2010-02-01

    Full Text Available Anthocyanins show low-stability when exposed to different food processing conditions. Copigmentation is one of the main reactions contributing to the in vivo color responsible to the stability of anthocyanins. In the aim of holding the red color, copigmentation effect of organic acids (caffeic, ferulic, gallic and tannic acids combined with anthocyanins in crude Cabernet Sauvignon (Vitis vinifera L. grape skin extract at pH values (1.0, 2.0, 3.0, 3.3, 3.5, 3.7, 4.0, 4.5 was evaluated in this research. The maximum copigmentation effect, revealed by the hyperchromic and bathochromic shifts in anthocyanin maximum absorbance wavelength, was obtained at pH 3.3 with every acid used. Anthocyanin stability was followed by measuring the loss of color, thus it was possible to determine the protecting effects of these copigments. Tannic acid was the best copigment in our model system, giving half-life time of 2,585 h. We are suggesting the formation of pyranoanthocyanins by the reactions of anthocyanins with caffeic and ferulic acid, these substances could be avoiding the observation of the copigmentation effect. Addition of organic acids could improve the anthocyanin stability; though, more studies are needed to justify the lack of copigmenting effect observed with the caffeic and ferulic acids.Antocianinas apresentam baixa estabilidade frente aos fatores que afetam o processamento de alimentos. A copigmentação é uma das principais reações responsáveis pela estabilidade da coloração de antocianinas in vivo. Com objetivo de manter a coloração vermelha, a copigmentação das antocianinas do extrato bruto de uvas Cabernet Sauvignon (Vitis vinifera L. com ácidos orgânicos (ácidos caféico, ferrúlico, gálico e tânico em diferentes valores de pH (1,0; 2,0; 3,0; 3,3; 3,5; 3,7; 4,0; 4,5 foi avaliada neste estudo. O efeito máximo de copigmentação, revelado pelos deslocamentos hipercrômico e batocrômico, foi obtido em pH 3,3 para todos os

  13. Selection of optimum ionic liquid solvents for flavonoid and phenolic acids extraction

    Science.gov (United States)

    Rahman, N. R. A.; Yunus, N. A.; Mustaffa, A. A.

    2017-06-01

    Phytochemicals are important in improving human health with their functions as antioxidants, antimicrobials and anticancer agents. However, the quality of phytochemicals extract relies on the efficiency of extraction process. Ionic liquids (ILs) have become a research phenomenal as extraction solvent due to their unique properties such as unlimited range of ILs, non-volatile, strongly solvating and may become either polarity. In phytochemical extraction, the determination of the best solvent that can extract highest yield of solute (phytochemical) is very important. Therefore, this study is conducted to determine the best IL solvent to extract flavonoids and phenolic acids through a property prediction modeling approach. ILs were selected from the imidazolium-based anion for alkyl chains ranging from ethyl > octyl and cations consisting of Br, Cl, [PF6], BF4], [H2PO4], [SO4], [CF3SO3], [TF2N] and [HSO4]. This work are divided into several stages. In Stage 1, a Microsoft Excel-based database containing available solubility parameter values of phytochemicals and ILs including its prediction models and their parameters has been established. The database also includes available solubility data of phytochemicals in IL, and activity coefficient models, for solid-liquid phase equilibrium (SLE) calculations. In Stage 2, the solubility parameter values of the flavonoids (e.g. kaempferol, quercetin and myricetin) and phenolic acids (e.g. gallic acid and caffeic acid) are determined either directly from database or predicted using Stefanis and Marrero-Gani group contribution model for the phytochemicals. A cation-anion contribution model is used for IL. In Stage 3, the amount of phytochemicals extracted can be determined by using SLE relationship involving UNIFAC-IL model. For missing parameters (UNIFAC-IL), they are regressed using available solubility data. Finally, in Stage 4, the solvent candidates are ranked and five ILs, ([OMIM] [TF2N], [HeMIM] [TF2N], [HMIM] [TF2N

  14. Changes in the flavonoid and phenolic acid contents and antioxidant activity of red leaf lettuce (Lollo Rosso) due to cultivation under plastic films varying in ultraviolet transparency.

    Science.gov (United States)

    García-Macías, Paulina; Ordidge, Matthew; Vysini, Eleni; Waroonphan, Saran; Battey, Nicholas H; Gordon, Michael H; Hadley, Paul; John, Philip; Lovegrove, Julie A; Wagstaffe, Alexandra

    2007-12-12

    Red leaf lettuce (Lollo Rosso) was grown under three types of plastic films that varied in transparency to UV radiation (designated as UV block, UV low, and UV window). Flavonoid composition was determined by high-performance liquid chromatography (HPLC), total phenolics by the Folin-Ciocalteu assay, and antioxidant capacity by the oxygen radical absorbance capacity (ORAC) assay. Exposure to increased levels of UV radiation during cultivation caused the leaves to redden and increased concentrations of total phenols and the main flavonoids, quercetin and cyanidin glycosides, as well as luteolin conjugates and phenolic acids. The total phenol content increased from 1.6 mg of gallic acid equivalents (GAE)/g of fresh weight (FW) for lettuce grown under UV block film to 2.9 and 3.5 mg of GAE/g of FW for lettuce grown under the UV low and UV window films. The antioxidant activity was also higher in lettuce exposed to higher levels of UV radiation with ORAC values of 25.4 and 55.1 micromol of Trolox equivalents/g of FW for lettuce grown under the UV block and UV window films, respectively. The content of phenolic acids, quantified as caffeic acid, was also different, ranging from 6.2 to 11.1 micromol/g of FW for lettuce cultivated under the lowest and highest UV exposure plastic films, respectively. Higher concentrations of the flavonoid glycosides were observed with increased exposure to UV radiation, as demonstrated by the concentrations of aglycones after hydrolysis, which were cyanidin (ranging from 165 to 793 microg/g), quercetin (ranging from 196 to 880 microg/g), and luteolin (ranging from 19 to 152 microg/g). The results demonstrate the potential of the use of UV-transparent plastic as a means of increasing beneficial flavonoid content of red leaf lettuce when the crop is grown in polytunnels.

  15. Acidic Ionic Liquids.

    Science.gov (United States)

    Amarasekara, Ananda S

    2016-05-25

    Ionic liquid with acidic properties is an important branch in the wide ionic liquid field and the aim of this article is to cover all aspects of these acidic ionic liquids, especially focusing on the developments in the last four years. The structural diversity and synthesis of acidic ionic liquids are discussed in the introduction sections of this review. In addition, an unambiguous classification system for various types of acidic ionic liquids is presented in the introduction. The physical properties including acidity, thermo-physical properties, ionic conductivity, spectroscopy, and computational studies on acidic ionic liquids are covered in the next sections. The final section provides a comprehensive review on applications of acidic ionic liquids in a wide array of fields including catalysis, CO2 fixation, ionogel, electrolyte, fuel-cell, membrane, biomass processing, biodiesel synthesis, desulfurization of gasoline/diesel, metal processing, and metal electrodeposition.

  16. Process for the preparation of lactic acid and glyceric acid

    Science.gov (United States)

    Jackson, James E [Haslett, MI; Miller, Dennis J [Okemos, MI; Marincean, Simona [Dewitt, MI

    2008-12-02

    Hexose and pentose monosaccharides are degraded to lactic acid and glyceric acid in an aqueous solution in the presence of an excess of a strongly anionic exchange resin, such as AMBERLITE IRN78 and AMBERLITE IRA400. The glyceric acid and lactic acid can be separated from the aqueous solution. Lactic acid and glyceric acid are staple articles of commerce.

  17. Amino acids in the sedimentary humic and fulvic acids

    Digital Repository Service at National Institute of Oceanography (India)

    Sardessai, S.

    acids in the coastal Arabian Sea sediments: whereas amino acids content of fulvic acids was lower than that of humic acids in the coastal sediments of Bay of Bengal. Slope sedimentary humic acids were relatively enriched in amino acids as compared...

  18. 78 FR 20029 - Castor Oil, Polymer With Adipic Acid, Linoleic Acid, Oleic Acid and Ricinoleic Acid; Tolerance...

    Science.gov (United States)

    2013-04-03

    ..., Polymer With Adipic Acid, Linoleic Acid, Oleic Acid and Ricinoleic Acid; Tolerance Exemption AGENCY... from the requirement of a tolerance for residues of castor oil, polymer with adipic acid, linoleic acid... pesticide formulation. Advance Polymer Technology submitted a petition to EPA under the Federal Food, Drug...

  19. Analysis of organic acids and phenols of interest in the wine industry using Langmuir–Blodgett films based on functionalized nanoparticles

    International Nuclear Information System (INIS)

    Medina-Plaza, C.; García-Cabezón, C.; García-Hernández, C.; Bramorski, C.; Blanco-Val, Y.; Martín-Pedrosa, F.; Kawai, T.; Saja, J.A. de; Rodríguez-Méndez, M.L.

    2015-01-01

    Highlights: • For the first time functionalized NPs immobilized in LB films have been used as voltammetric sensors. • Films showed excellent electrocatalytic properties toward phenols and acids found in wines. • Improved performance is due to combination of electrocatalytic NPs with the high surface/volume of LB films. • The potential applications in the wine industry have been evidenced. - Abstract: A chemically modified electrode consisting of Langmuir–Blodgett (LB) films of n-dodecanethiol functionalized gold nanoparticles (S DOD AuNP-LB), was investigated as a voltammetric sensor of organic and phenolic acids of interest in the wine industry. The nanostructured films demonstrated interfacial properties being able to detect the main organic acids present in grapes and wines (tartaric, malic, lactic and citric). Compared to a bare ITO electrode, the modified electrodes exhibited a shift of the reduction potential in the less positive direction and a marked enhancement in the current response. Moreover, the increased electrocatalytic properties made it possible to distinguish between the different dissociable protons of polyprotic acids. The S DOD AuNP-LB sensor was also able to provide enhanced responses toward aqueous solutions of phenolic acids commonly found in wines (caffeic and gallic acids). The presence of nanoparticles increased drastically the sensitivity toward organic acids and phenolic compounds. Limits of detection as low as 10 −6 mol L −1 were achieved. Efficient catalytic activity was also observed in mixtures of phenolic acid/tartaric in the range of pHs typically found in wines. In such mixtures, the electrode was able to provide simultaneous information about the acid and the phenol concentrations with a complete absence of interferences. The excellent sensing properties shown by these sensors could be attributed to the electrocatalytic properties of the nanoparticles combined with the high surface to volume ratio and homogeneity

  20. Analysis of organic acids and phenols of interest in the wine industry using Langmuir–Blodgett films based on functionalized nanoparticles

    Energy Technology Data Exchange (ETDEWEB)

    Medina-Plaza, C. [Department of Inorganic Chemistry, Engineers School, Universidad de Valladolid (Spain); García-Cabezón, C. [Department of Materials Science, Engineers School, Universidad de Valladolid (Spain); García-Hernández, C.; Bramorski, C. [Department of Inorganic Chemistry, Engineers School, Universidad de Valladolid (Spain); Blanco-Val, Y.; Martín-Pedrosa, F. [Department of Materials Science, Engineers School, Universidad de Valladolid (Spain); Kawai, T. [Department of Industrial Chemistry, Tokyo University of Science (Japan); Saja, J.A. de [Department of Condensed Matter Physics, Universidad de Valladolid (Spain); Rodríguez-Méndez, M.L., E-mail: mluz@eii.uva.es [Department of Inorganic Chemistry, Engineers School, Universidad de Valladolid (Spain)

    2015-01-01

    Highlights: • For the first time functionalized NPs immobilized in LB films have been used as voltammetric sensors. • Films showed excellent electrocatalytic properties toward phenols and acids found in wines. • Improved performance is due to combination of electrocatalytic NPs with the high surface/volume of LB films. • The potential applications in the wine industry have been evidenced. - Abstract: A chemically modified electrode consisting of Langmuir–Blodgett (LB) films of n-dodecanethiol functionalized gold nanoparticles (S{sub DOD}AuNP-LB), was investigated as a voltammetric sensor of organic and phenolic acids of interest in the wine industry. The nanostructured films demonstrated interfacial properties being able to detect the main organic acids present in grapes and wines (tartaric, malic, lactic and citric). Compared to a bare ITO electrode, the modified electrodes exhibited a shift of the reduction potential in the less positive direction and a marked enhancement in the current response. Moreover, the increased electrocatalytic properties made it possible to distinguish between the different dissociable protons of polyprotic acids. The S{sub DOD}AuNP-LB sensor was also able to provide enhanced responses toward aqueous solutions of phenolic acids commonly found in wines (caffeic and gallic acids). The presence of nanoparticles increased drastically the sensitivity toward organic acids and phenolic compounds. Limits of detection as low as 10{sup −6} mol L{sup −1} were achieved. Efficient catalytic activity was also observed in mixtures of phenolic acid/tartaric in the range of pHs typically found in wines. In such mixtures, the electrode was able to provide simultaneous information about the acid and the phenol concentrations with a complete absence of interferences. The excellent sensing properties shown by these sensors could be attributed to the electrocatalytic properties of the nanoparticles combined with the high surface to volume ratio

  1. Bile acid sequestrants

    DEFF Research Database (Denmark)

    Hansen, Morten; Sonne, David P; Knop, Filip K

    2014-01-01

    Bile acids are synthesized in the liver from cholesterol and have traditionally been recognized for their role in absorption of lipids and in cholesterol homeostasis. In recent years, however, bile acids have emerged as metabolic signaling molecules that are involved in the regulation of lipid...... and glucose metabolism, and possibly energy homeostasis, through activation of the bile acid receptors farnesoid X receptor (FXR) and TGR5. Bile acid sequestrants (BASs) constitute a class of drugs that bind bile acids in the intestine to form a nonabsorbable complex resulting in interruption...... of the enterohepatic circulation. This increases bile acid synthesis and consequently reduces serum low-density lipoprotein cholesterol. Also, BASs improve glycemic control in patients with type 2 diabetes. Despite a growing understanding of the impact of BASs on glucose metabolism, the mechanisms behind their glucose...

  2. Online identification of chlorogenic acids, sesquiterpene lactones, and flavonoids in the Brazilian arnica Lychnophora ericoides Mart. (Asteraceae) leaves by HPLC-DAD-MS and HPLC-DAD-MS/MS and a validated HPLC-DAD method for their simultaneous analysis.

    Science.gov (United States)

    Gobbo-Neto, Leonardo; Lopes, Norberto P

    2008-02-27

    Lychnophora ericoides Mart. (Asteraceae, Vernonieae) is a plant, endemic to Brazil, with occurrence restricted to the "cerrado" biome. Traditional medicine employs alcoholic and aqueous-alcoholic preparations of leaves from this species for the treatment of wounds, inflammation, and pain. Furthermore, leaves of L. ericoides are also widely used as flavorings for the Brazilian traditional spirit "cachaça". A method has been developed for the extraction and HPLC-DAD analysis of the secondary metabolites of L. ericoides leaves. This analytical method was validated with 11 secondary metabolites chosen to represent the different classes and polarities of secondary metabolites occurring in L. ericoides leaves, and good responses were obtained for each validation parameter analyzed. The same HPLC analytical method was also employed for online secondary metabolite identification by HPLC-DAD-MS and HPLC-DAD-MS/MS, leading to the identification of di- C-glucosylflavones, coumaroylglucosylflavonols, flavone, flavanones, flavonols, chalcones, goyazensolide, and eremantholide-type sesquiterpene lactones and positional isomeric series of chlorogenic acids possessing caffeic and/or ferulic moieties. Among the 52 chromatographic peaks observed, 36 were fully identified and 8 were attributed to compounds belonging to series of caffeoylferuloylquinic and diferuloylquinic acids that could not be individualized from each other.

  3. Citric Acid Alternative to Nitric Acid Passivation

    Science.gov (United States)

    Lewis, Pattie L. (Compiler)

    2013-01-01

    The Ground Systems Development and Operations GSDO) Program at NASA John F. Kennedy Space Center (KSC) has the primary objective of modernizing and transforming the launch and range complex at KSC to benefit current and future NASA programs along with other emerging users. Described as the launch support and infrastructure modernization program in the NASA Authorization Act of 2010, the GSDO Program will develop and implement shared infrastructure and process improvements to provide more flexible, affordable, and responsive capabilities to a multi-user community. In support of the GSDO Program, the purpose of this project is to demonstratevalidate citric acid as a passivation agent for stainless steel. Successful completion of this project will result in citric acid being qualified for use as an environmentally preferable alternative to nitric acid for passivation of stainless steel alloys in NASA and DoD applications.

  4. USGS Tracks Acid Rain

    Science.gov (United States)

    Gordon, John D.; Nilles, Mark A.; Schroder, LeRoy J.

    1995-01-01

    The U.S. Geological Survey (USGS) has been actively studying acid rain for the past 15 years. When scientists learned that acid rain could harm fish, fear of damage to our natural environment from acid rain concerned the American public. Research by USGS scientists and other groups began to show that the processes resulting in acid rain are very complex. Scientists were puzzled by the fact that in some cases it was difficult to demonstrate that the pollution from automobiles and factories was causing streams or lakes to become more acidic. Further experiments showed how the natural ability of many soils to neutralize acids would reduce the effects of acid rain in some locations--at least as long as the neutralizing ability lasted (Young, 1991). The USGS has played a key role in establishing and maintaining the only nationwide network of acid rain monitoring stations. This program is called the National Atmospheric Deposition Program/National Trends Network (NADP/NTN). Each week, at approximately 220 NADP/NTN sites across the country, rain and snow samples are collected for analysis. NADP/NTN site in Montana. The USGS supports about 72 of these sites. The information gained from monitoring the chemistry of our nation's rain and snow is important for testing the results of pollution control laws on acid rain.

  5. Multiple anti-inflammatory and anti-atherosclerotic properties of red wine polyphenolic extracts: differential role of hydroxycinnamic acids, flavonols and stilbenes on endothelial inflammatory gene expression.

    Science.gov (United States)

    Calabriso, Nadia; Scoditti, Egeria; Massaro, Marika; Pellegrino, Mariangela; Storelli, Carlo; Ingrosso, Ilaria; Giovinazzo, Giovanna; Carluccio, Maria Annunziata

    2016-03-01

    The aim of the study was to evaluate the vascular anti-inflammatory effects of polyphenolic extracts from two typical South Italy red wines, the specific contribution of individual polyphenols and the underlying mechanisms of action. Human endothelial cells were incubated with increasing concentrations (1-50 μg/mL) of Primitivo and Negroamaro polyphenolic extracts (PWPE and NWPE, respectively) or pure polyphenols (1-25 μmol/L), including hydroxycinnamic acids (p-coumaric, caffeic and caftaric acids), flavonols (kaempferol, quercetin, myricetin) or stilbenes (trans-resveratrol, trans-piceid) before stimulation with lipopolysaccharide. Through multiple assays, we analyzed the endothelial-monocyte adhesion, the endothelial expression of adhesion molecules (ICAM-1, VCAM-1 and E-Selectin), monocyte chemoattractant protein-1 (MCP-1) and macrophage colony-stimulating factor (M-CSF), as well as ROS intracellular levels and the activation of NF-κB and AP-1. Both PWPE and NWPE, already at 1 μg/mL, inhibited monocyte adhesion to stimulated endothelial cells, a key event in triggering vascular inflammation. They down-regulated the expression of adhesion molecules, ICAM-1, VCAM-1, E-Selectin, as well as MCP-1 and M-CSF, at mRNA and protein levels. All polyphenols reduced intracellular ROS, and everything, except caftaric acid, inhibited the endothelial expression of adhesion molecules and MCP-1, although with different potency. Flavonols and resveratrol significantly reduced also the endothelial expression and release of M-CSF. The decrease in endothelial inflammatory gene expression was related to the inhibition of NF-κB and AP-1 activation but not to intracellular oxidative stress. This study showed multiple anti-inflammatory and anti-atherosclerotic properties of red wine polyphenolic extracts and indentified specific bioactive polyphenols which could counteract inflammatory diseases including atherosclerosis.

  6. Acidity of hydroxamic acids and amides

    Czech Academy of Sciences Publication Activity Database

    Böhm, S.; Exner, Otto

    2003-01-01

    Roč. 1, č. 7 (2003), s. 1176-1180 ISSN 1477-0520 R&D Projects: GA AV ČR IAA4072005 Institutional research plan: CEZ:AV0Z4055905 Keywords : hydroxamic acids * DFT calculations * isodesmic reactions Subject RIV: CC - Organic Chemistry

  7. Fusidic acid in dermatology

    DEFF Research Database (Denmark)

    Schöfer, Helmut; Simonsen, Lene

    1995-01-01

    Studies on the clinical efficacy of fusidic acid in skin and soft-tissue infections (SSTIs), notably those due to Staphylococcus aureus, are reviewed. Oral fusidic acid (tablets dosed at 250 mg twice daily, or a suspension for paediatric use at 20 mg/kg/day given as two daily doses) has shown goo...

  8. Characterization of acid tars

    International Nuclear Information System (INIS)

    Leonard, Sunday A.; Stegemann, Julia A.; Roy, Amitava

    2010-01-01

    Acid tars from the processing of petroleum and petrochemicals using sulfuric acid were characterized by gas chromatography/mass spectrometry (GC/MS), inductively coupled plasma/optical emission spectrometry (ICP/OES), differential scanning calorimetry (DSC), Fourier transform infrared (FTIR) spectrometry, and scanning electron microscopy/energy dispersive X-ray (SEM/EDX) micro-analysis. Leaching of contaminants from the acid tars in 48 h batch tests with distilled water at a liquid-to-solid ratio 10:1 was also studied. GC/MS results show that the samples contained aliphatic hydrocarbons, cyclic hydrocarbons, up to 12 of the 16 USEPA priority polycyclic aromatic hydrocarbons (PAHs), and numerous other organic groups, including organic acids (sulfonic acids, carboxylic acids and aromatic acids), phenyl, nitrile, amide, furans, thiophenes, pyrroles, and phthalates, many of which are toxic. Metals analysis shows that Pb was present in significant concentration. DSC results show different transition peaks in the studied samples, demonstrating their complexity and variability. FTIR analysis further confirmed the presence of the organic groups detected by GC/MS. The SEM/EDX micro-analysis results provided insight on the surface characteristics of the samples and show that contaminants distribution was heterogeneous. The results provide useful data on the composition, complexity, and variability of acid tars; information which hitherto have been scarce in public domain.

  9. Characterization of acid tars

    Energy Technology Data Exchange (ETDEWEB)

    Leonard, Sunday A., E-mail: sunday.leonard@ucl.ac.uk [Department of Civil Environmental and Geomatic Engineering, University College London, Chadwick Building, Gower Street, London, WC1E 6BT (United Kingdom); Stegemann, Julia A. [Department of Civil Environmental and Geomatic Engineering, University College London, Chadwick Building, Gower Street, London, WC1E 6BT (United Kingdom); Roy, Amitava [J. Bennett Johnston, Sr., Centre for Advance Microstructures and Devices (CAMD), 6980 Jefferson Highway, Louisiana State University, Baton Rouge, LA, 70806 (United States)

    2010-03-15

    Acid tars from the processing of petroleum and petrochemicals using sulfuric acid were characterized by gas chromatography/mass spectrometry (GC/MS), inductively coupled plasma/optical emission spectrometry (ICP/OES), differential scanning calorimetry (DSC), Fourier transform infrared (FTIR) spectrometry, and scanning electron microscopy/energy dispersive X-ray (SEM/EDX) micro-analysis. Leaching of contaminants from the acid tars in 48 h batch tests with distilled water at a liquid-to-solid ratio 10:1 was also studied. GC/MS results show that the samples contained aliphatic hydrocarbons, cyclic hydrocarbons, up to 12 of the 16 USEPA priority polycyclic aromatic hydrocarbons (PAHs), and numerous other organic groups, including organic acids (sulfonic acids, carboxylic acids and aromatic acids), phenyl, nitrile, amide, furans, thiophenes, pyrroles, and phthalates, many of which are toxic. Metals analysis shows that Pb was present in significant concentration. DSC results show different transition peaks in the studied samples, demonstrating their complexity and variability. FTIR analysis further confirmed the presence of the organic groups detected by GC/MS. The SEM/EDX micro-analysis results provided insight on the surface characteristics of the samples and show that contaminants distribution was heterogeneous. The results provide useful data on the composition, complexity, and variability of acid tars; information which hitherto have been scarce in public domain.

  10. Peptide Nucleic Acids

    DEFF Research Database (Denmark)

    2003-01-01

    A novel class of compounds, known as peptide nucleic acids, bind complementary ssDNA and RNA strands more strongly than a corresponding DNA. The peptide nucleic acids generally comprise ligands such as naturally occurring DNA bases attached to a peptide backbone through a suitable linker....

  11. Peptide Nucleic Acids

    DEFF Research Database (Denmark)

    1998-01-01

    A novel class of compounds, known as peptide nucleic acids, bind complementary ssDNA and RNA strands more strongly than a corresponding DNA. The peptide nucleic acids generally comprise ligands such as naturally occurring DNA bases attached to a peptide backbone through a suitable linker....

  12. Peptide Nucleic Acids (PNA)

    DEFF Research Database (Denmark)

    2002-01-01

    A novel class of compounds, known as peptide nucleic acids, bind complementary ssDNA and RNA strands more strongly than a corresponding DNA. The peptide nucleic acids generally comprise ligands such as naturally occurring DNA bases attached to a peptide backbone through a suitable linker....

  13. Peptide Nucleic Acids

    DEFF Research Database (Denmark)

    2004-01-01

    A novel class of compounds known as peptide nucleic acids, bind complementary DNA and RNA strands, and generally do so more strongly than the corresponding DNA or RNA strands while exhibiting increased sequence specificity and solubility. The peptide nucleic acids comprise ligands selected from...

  14. Folic acid in diet

    Science.gov (United States)

    ... regularly removed from the body through urine, so excess amounts do not build up in the body. You should not get more than 1000 mcg per day of folic acid. Using higher levels of folic acid can mask vitamin B12 deficiency.

  15. Peptide Nucleic Acid Synthons

    DEFF Research Database (Denmark)

    2004-01-01

    A novel class of compounds, known as peptide nucleic acids, bind complementary ssDNA and RNA strands more strongly than a corresponding DNA. The peptide nucleic acids generally comprise ligands such as naturally occurring DNA bases attached to a peptide backbone through a suitable linker....

  16. Locked nucleic acid

    DEFF Research Database (Denmark)

    Jepsen, Jan Stenvang; Sørensen, Mads D; Wengel, Jesper

    2004-01-01

    Locked nucleic acid (LNA) is a class of nucleic acid analogs possessing very high affinity and excellent specificity toward complementary DNA and RNA, and LNA oligonucleotides have been applied as antisense molecules both in vitro and in vivo. In this review, we briefly describe the basic...

  17. Halogenated fatty acids

    DEFF Research Database (Denmark)

    Mu, Huiling; Wesén, Clas; Sundin, Peter

    1997-01-01

    Chlorinated fatty acids have been found to be major contributors to organohalogen compounds in fish, bivalves, jellyfish, and lobster, and they have been indicated to contribute considerably to organohalogens in marine mammals. Brominated fatty acids have been found in marine sponges. Also...

  18. Amino Acid Crossword Puzzle

    Science.gov (United States)

    Sims, Paul A.

    2011-01-01

    Learning the 20 standard amino acids is an essential component of an introductory course in biochemistry. Later in the course, the students study metabolism and learn about various catabolic and anabolic pathways involving amino acids. Learning new material or concepts often is easier if one can connect the new material to what one already knows;…

  19. Phosphates and phosphoric acid

    Energy Technology Data Exchange (ETDEWEB)

    Becker, P [Compagnie Francaise de l' Azote, Paris (France)

    1983-01-01

    In chapter 8.5 the following aspects of uranium recovery are treated: basis of extraction process, extraction principle, solvents, strength of the acid to be treated, technology, main processes in use, impact of uranium recovery on phosphoric acid plants, and economics of uranium recovery plants.

  20. Omega-3 Fatty Acids

    Science.gov (United States)

    Omega-3 fatty acids are used together with lifestyle changes (diet, weight-loss, exercise) to reduce the amount of triglycerides (a fat- ... in people with very high triglycerides. Omega-3 fatty acids are in a class of medications called antilipemic ...

  1. Enzymatic formation of hexadecenoic acid from palmitic acid

    International Nuclear Information System (INIS)

    Nakano, Masao; Fujino, Yasuhiko

    1975-01-01

    Desaturation of palmitic acid was investigated in an enzyme system prepared from rat liver. 2-trans-Hexadecenoic acid as well as 9-cis-gexadecenoic acid (palmitoleic acid) were found to be formed as monoenoic acid in this system. (author)

  2. Lewis Acidic Ionic Liquids.

    Science.gov (United States)

    Brown, Lucy C; Hogg, James M; Swadźba-Kwaśny, Małgorzata

    2017-08-21

    Until very recently, the term Lewis acidic ionic liquids (ILs) was nearly synonymous with halometallate ILs, with a strong focus on chloroaluminate(III) systems. The first part of this review covers the historical context in which these were developed, speciation of a range of halometallate ionic liquids, attempts to quantify their Lewis acidity, and selected recent applications: in industrial alkylation processes, in supported systems (SILPs/SCILLs) and in inorganic synthesis. In the last decade, interesting alternatives to halometallate ILs have emerged, which can be divided into two sub-sections: (1) liquid coordination complexes (LCCs), still based on halometallate species, but less expensive and more diverse than halometallate ionic liquids, and (2) ILs with main-group Lewis acidic cations. The two following sections cover these new liquid Lewis acids, also highlighting speciation studies, Lewis acidity measurements, and applications.

  3. Acidity in rainfall

    International Nuclear Information System (INIS)

    Tisue, G.T.; Kacoyannakis, J.

    1975-01-01

    The reported increasing acidity of rainfall raises many interesting ecological and chemical questions. In spite of extensive studies in Europe and North America there are, for example, great uncertainties in the relative contributions of strong and weak acids to the acid-base properties of rainwater. Unravelling this and similar problems may require even more rigorous sample collection and analytical procedures than previously employed. Careful analysis of titration curves permits inferences to be made regarding chemical composition, the possible response of rainwater to further inputs of acidic components to the atmosphere, and the behavior to be expected when rainwater interacts with the buffers present in biological materials and natural waters. Rainwater samples collected during several precipitation events at Argonne National Laboratory during October and November 1975 have been analyzed for pH, acid and base neutralizing properties, and the ions of ammonium, nitrate, chloride, sulfate, and calcium. The results are tabulated

  4. Conjugated Fatty Acid Synthesis

    Science.gov (United States)

    Rawat, Richa; Yu, Xiao-Hong; Sweet, Marie; Shanklin, John

    2012-01-01

    Conjugated linolenic acids (CLNs), 18:3 Δ9,11,13, lack the methylene groups found between the double bonds of linolenic acid (18:3 Δ9,12,15). CLNs are produced by conjugase enzymes that are homologs of the oleate desaturases FAD2. The goal of this study was to map the domain(s) within the Momordica charantia conjugase (FADX) responsible for CLN formation. To achieve this, a series of Momordica FADX-Arabidopsis FAD2 chimeras were expressed in the Arabidopsis fad3fae1 mutant, and the transformed seeds were analyzed for the accumulation of CLN. These experiments identified helix 2 and the first histidine box as a determinant of conjugase product partitioning into punicic acid (18:3 Δ9cis,11trans,13cis) or α-eleostearic acid (18:3 Δ9cis,11trans,13trans). This was confirmed by analysis of a FADX mutant containing six substitutions in which the sequence of helix 2 and first histidine box was converted to that of FAD2. Each of the six FAD2 substitutions was individually converted back to the FADX equivalent identifying residues 111 and 115, adjacent to the first histidine box, as key determinants of conjugase product partitioning. Additionally, expression of FADX G111V and FADX G111V/D115E resulted in an approximate doubling of eleostearic acid accumulation to 20.4% and 21.2%, respectively, compared with 9.9% upon expression of the native Momordica FADX. Like the Momordica conjugase, FADX G111V and FADX D115E produced predominantly α-eleostearic acid and little punicic acid, but the FADX G111V/D115E double mutant produced approximately equal amounts of α-eleostearic acid and its isomer, punicic acid, implicating an interactive effect of residues 111 and 115 in punicic acid formation. PMID:22451660

  5. Glycosyltransferase glycosylating flavokermesic acid and/or kermesic acid

    DEFF Research Database (Denmark)

    2016-01-01

    An isolated glycosyltransferase (GT) polypeptide capable of: (I) : conjugating glucose to flavokermesic acid (FK); and/or (II) : conjugating glucose to kermesic acid (KA) and use of this GT to e.g. make Carminic acid.......An isolated glycosyltransferase (GT) polypeptide capable of: (I) : conjugating glucose to flavokermesic acid (FK); and/or (II) : conjugating glucose to kermesic acid (KA) and use of this GT to e.g. make Carminic acid....

  6. GLYCOSYLTRANSFERASE GLYCOSYLATING FLAVOKERMESIC ACID AND/OR KERMESIC ACID

    DEFF Research Database (Denmark)

    2015-01-01

    An isolated glycosyltransferase (GT) polypeptide capable of: (I): conjugating glucose to flavokermesic acid (FK); and/or (II): conjugating glucose to kermesic acid (KA) and use of this GT to e.g. make Carminic acid.......An isolated glycosyltransferase (GT) polypeptide capable of: (I): conjugating glucose to flavokermesic acid (FK); and/or (II): conjugating glucose to kermesic acid (KA) and use of this GT to e.g. make Carminic acid....

  7. Mechanism of protection of adenosine from sulphate radical anion ...

    Indian Academy of Sciences (India)

    Unknown

    Keywords. Repair by caffeic acid; repair of adenosine radicals; oxidation by sulphate radical anions. ... known that hydroxycinnamic acids are natural anti- oxidants ... acid. 2. Experimental ..... ously and independently under kinetic conditions at.

  8. Antioxidative activity and emulsifying properties of cuttlefish skin gelatin modified by oxidised phenolic compounds

    NARCIS (Netherlands)

    Aewsiri, T.; Benjakul, S.; Visessanguan, W.; Eun, J.B.; Wierenga, P.A.; Gruppen, H.

    2009-01-01

    Antioxidative activity and emulsifying properties of cuttlefish skin gelatin modified by different oxidised phenolic compounds including caffeic acid, ferulic acid and tannic acid at different concentrations were investigated. Oxidised phenolic compounds were covalently attached to gelatin as

  9. Waht is 'molybdic acid' or 'polymolybdic acid'?

    International Nuclear Information System (INIS)

    Tytko, K.H.; Baethe, G.; Mehmke, K.

    1987-01-01

    According to a comparative study of the literature, supplemented by well-aimed experimental investigations and equilibrium calculations, the terms 'molybdic acid' or 'polymolybdic acid', used for many substances, species, or solutions in the literature, are applicable to a species, a solution, and two solids: a) The monomeric molybdic acid, most probably having the formula MoO 2 (OH) 2 (H 2 O) 2 (= H 2 MoO 4 , aq), exists in (aqueous) solution only and never exceeds a concentration of ∼ 10 -3 M since at higher concentrations it reacts with other monomeric molybdenum(VI) species to give anionic or cationic polymers. b) A concentrated (> 0.1 M Mo VI ) aqueous molybdate solution of degree of acidification P = 2 (realized, e.g., by a solution of one of the Mo VI oxides; by any molybdate solutions whose cations have been exchanged by H 2 O + on a cation exchanger; by suitable acidification of a molybdate solution) contains 8 H 3 O + and the well-known polyanion Mo 36 O 112 (H 2 O) 16 8- exactly in the stoichiometric proportions. c) A glassy substance, obtained from an alkali metal salt-free solution prepared acording to (b), refers to the compound (H 3 O) 8 [Mo 36 O 112 (H 2 O) 16 ] · xH 2 O, x = 25 - 29. d) A solid having the ideal composition [(H 3 O)Mo 5 O 15 (OH)H 2 O · H 2 O] ∞ consists of a polymolybdate skeleton (the well-known 'decamolybdate' structure), in the tunnels of which H 3 O + and H 2 O are intercalated. The structure is very unstable if only H 3 O + cations are present, but it is enormously stabilized by a partial exchange of H 3 O + by certain alkali or alkaline earth metal cations. For the compounds MoO 3 , MoO 3 ·H 2 O, and MoO 3 · 2 H 2 O the term 'molybdic acid' is unjustified. The commercial product 'molybdic acid, ∼ 85% MoO 3 ' is the well-known polymolybdate (NH 4 ) 2 O · 4 MoO 3 with a layer structure of the polyanion. 84 refs. (author)

  10. Amino acid racemisation dating

    International Nuclear Information System (INIS)

    Murray-Wallace, C.V.

    1999-01-01

    The potential of the time-dependent amino acid racemisation reaction as a method of age assessment was first reported by Hare and Abelson (1968). They noted that in specimens of the bivalve mollusc Mercenaria sp., greater concentrations of amino acids in the D-configuration with increasing fossil age. Hare and Abelson (1968) also reported negligible racemisation in a modern specimen of Mecanaria sp. On this basis they suggested that the extent of amino acid racemisation (epimerisation in the case of isoleucine) may be used to assess the age of materials within and beyond the range of radiocarbon dating. For the past thirty years amino acid racemisation has been extensively applied in Quaternary research as a method of relative and numeric dating, and a particularly large literature has emerged on the subject

  11. Amino Acids and Chirality

    Science.gov (United States)

    Cook, Jamie E.

    2012-01-01

    Amino acids are among the most heavily studied organic compound class in carbonaceous chondrites. The abundance, distributions, enantiomeric compositions, and stable isotopic ratios of amino acids have been determined in carbonaceous chondrites fi'om a range of classes and petrographic types, with interesting correlations observed between these properties and the class and typc of the chondritcs. In particular, isomeric distributions appear to correlate with parent bodies (chondrite class). In addition, certain chiral amino acids are found in enantiomeric excess in some chondrites. The delivery of these enantiomeric excesses to the early Earth may have contributed to the origin of the homochirality that is central to life on Earth today. This talk will explore the amino acids in carbonaceous chondritcs and their relevance to the origin of life.

  12. Acid Mine Drainage Treatment

    National Research Council Canada - National Science Library

    Fripp, Jon

    2000-01-01

    .... Acid mine drainage (AMD) can have severe impacts to aquatic resources, can stunt terrestrial plant growth and harm wetlands, contaminate groundwater, raise water treatment costs, and damage concrete and metal structures...

  13. Amoxicillin and Clavulanic Acid

    Science.gov (United States)

    ... in a class of medications called penicillin-like antibiotics. It works by stopping the growth of bacteria. Clavulanic acid ... It works by preventing bacteria from destroying amoxicillin. Antibiotics will not work for colds, flu, or other viral infections.

  14. Alpha Hydroxy Acids

    Science.gov (United States)

    ... or tenderness (8), chemical burns (6), and increased sunburn (3). The frequency of such reports for skin ... bear a statement that conveys the following information: Sunburn Alert: This product contains an alpha hydroxy acid ( ...

  15. Azetidinic amino acids

    DEFF Research Database (Denmark)

    Bräuner-Osborne, Hans; Bunch, Lennart; Chopin, Nathalie

    2005-01-01

    A set of ten azetidinic amino acids, that can be envisioned as C-4 alkyl substituted analogues of trans-2-carboxyazetidine-3-acetic acid (t-CAA) and/or conformationally constrained analogues of (R)- or (S)-glutamic acid (Glu) have been synthesized in a diastereo- and enantiomerically pure form from...... of two diastereoisomers that were easily separated and converted in two steps into azetidinic amino acids. Azetidines 35-44 were characterized in binding studies on native ionotropic Glu receptors and in functional assays at cloned metabotropic receptors mGluR1, 2 and 4, representing group I, II and III...... beta-amino alcohols through a straightforward five step sequence. The key step of this synthesis is an original anionic 4-exo-tet ring closure that forms the azetidine ring upon an intramolecular Michael addition. This reaction was proven to be reversible and to lead to a thermodynamic distribution...

  16. Valproic Acid and Pregnancy

    Science.gov (United States)

    ... is possible. Studies have found that women with seizure disorders and women with bipolar disorder might have menstrual ... valproic acid to leave your body. Women with epilepsy or bipolar disorder who are planning a pregnancy ...

  17. Determination of phenolic acids and flavonoids in raw propolis by silica-supported ionic liquid-based matrix solid phase dispersion extraction high performance liquid chromatography-diode array detection.

    Science.gov (United States)

    Wang, Zhibing; Sun, Rui; Wang, Yuanpeng; Li, Na; Lei, Lei; Yang, Xiao; Yu, Aimin; Qiu, Fangping; Zhang, Hanqi

    2014-10-15

    The silica-supported ionic liquid (S-SIL) was prepared by impregnation and used as the dispersion adsorbent of matrix solid phase dispersion (MSPD) for the simultaneous extraction of eight phenolic acids and flavonoids, including caffeic acid, ferulic acid, morin, luteolin, quercetin, apigenin, chrysin, and kaempferide in raw propolis. High performance liquid chromatography with a Zorbax SB-C18 column (150mm×4.6mm, 3.5μm) was used for separation of the analytes. The mobile phase consisted of 0.2% phosphoric acid aqueous solution and acetonitrile and the flow rate of the mobile phase was 0.5mL/min. The experimental conditions for silica-supported ionic liquid-based matrix solid phase dispersion (S-SIL-based MSPD) were optimized. S-SIL containing 10% [C6MIM]Cl was used as dispersant, 20mL of n-hexane as washing solvent and 15mL of methanol as elution solvent. The ratio of S-SIL to sample was selected to be 4:1. The standard curves showed good linear relationship (r>0.9995). The limits of detection and quantification were in the range of 5.8-22.2ngmL(-1) and 19.2-74.0ngmL(-1), respectively. The relative standard deviations (RSDs) of intra-day and inter-day determination were lower than 8.80% and 11.19%, respectively. The recoveries were between 65.51% and 92.32% with RSDs lower than 8.95%. Compared with ultrasound-assisted extraction (UAE) and soxhlet extraction, the present method consumed less sample, organic solvent, and extraction time, although the extraction yields obtained by S-SIL-based MSPD are slightly lower than those obtained by UAE. Copyright © 2014 Elsevier B.V. All rights reserved.

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

    Science.gov (United States)

    Engelhardt, U H; Maier, H G

    1985-07-01

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

  19. Portable nucleic acid thermocyclers.

    Science.gov (United States)

    Almassian, David R; Cockrell, Lisa M; Nelson, William M

    2013-11-21

    A nucleic acid thermal cycler is considered to be portable if it is under ten pounds, easily carried by one individual, and battery powered. Nucleic acid amplification includes both polymerase chain reaction (e.g. PCR, RT-PCR) and isothermal amplification (e.g. RPA, HDA, LAMP, NASBA, RCA, ICAN, SMART, SDA). There are valuable applications for portable nucleic acid thermocyclers in fields that include clinical diagnostics, biothreat detection, and veterinary testing. A system that is portable allows for the distributed detection of targets at the point of care and a reduction of the time from sample to answer. The designer of a portable nucleic acid thermocycler must carefully consider both thermal control and the detection of amplification. In addition to thermal control and detection, the designer may consider the integration of a sample preparation subsystem with the nucleic acid thermocycler. There are a variety of technologies that can achieve accurate thermal control and the detection of nucleic acid amplification. Important evaluation criteria for each technology include maturity, power requirements, cost, sensitivity, speed, and manufacturability. Ultimately the needs of a particular market will lead to user requirements that drive the decision between available technologies.

  20. Fatty Acid Biosynthesis IX

    DEFF Research Database (Denmark)

    Carey, E. M.; Hansen, Heinz Johs. Max; Dils, R.

    1972-01-01

    # 1. I. [I-14C]Acetate was covalently bound to rabbit mammary gland fatty acid synthetase by enzymic transacylation from [I-14C]acetyl-CoA. Per mole of enzyme 2 moles of acetate were bound to thiol groups and up to I mole of acetate was bound to non-thiol groups. # 2. 2. The acetyl-fatty acid...... synthetase complex was isolated free from acetyl-CoA. It was rapidly hydrolysed at 30°C, but hydrolysis was greatly diminished at o°C and triacetic lactone synthesis occurred. In the presence of malonyl-CoA and NADPH, all the acetate bound to fatty acid synthetase was incorporated into long-chain fatty acids....... Hydrolysis of bound acetate and incorporation of bound acetate into fatty acids were inhibited to the same extent by guanidine hydrochloride. # 3. 3. Acetate was also covalently bound to fatty acid synthetase by chemical acetylation with [I-14C]acetic anhydride in the absence of CoASH. A total of 60 moles...

  1. Acidification and Acid Rain

    Science.gov (United States)

    Norton, S. A.; Veselã½, J.

    2003-12-01

    Air pollution by acids has been known as a problem for centuries (Ducros, 1845; Smith, 1872; Camuffo, 1992; Brimblecombe, 1992). Only in the mid-1900s did it become clear that it was a problem for more than just industrially developed areas, and that precipitation quality can affect aquatic resources ( Gorham, 1955). The last three decades of the twentieth century saw tremendous progress in the documentation of the chemistry of the atmosphere, precipitation, and the systems impacted by acid atmospheric deposition. Chronic acidification of ecosystems results in chemical changes to soil and to surface waters and groundwater as a result of reduction of base cation supply or an increase in acid (H+) supply, or both. The most fundamental changes during chronic acidification are an increase in exchangeable H+ or Al3+ (aluminum) in soils, an increase in H+ activity (˜concentration) in water in contact with soil, and a decrease in alkalinity in waters draining watersheds. Water draining from the soil is acidified and has a lower pH (=-log [H+]). As systems acidify, their biotic community changes.Acidic surface waters occur in many parts of the world as a consequence of natural processes and also due to atmospheric deposition of strong acid (e.g., Canada, Jeffries et al. (1986); the United Kingdom, Evans and Monteith (2001); Sweden, Swedish Environmental Protection Board (1986); Finland, Forsius et al. (1990); Norway, Henriksen et al. (1988a); and the United States (USA), Brakke et al. (1988)). Concern over acidification in the temperate regions of the northern hemisphere has been driven by the potential for accelerating natural acidification by pollution of the atmosphere with acidic or acidifying compounds. Atmospheric pollution ( Figure 1) has resulted in an increased flux of acid to and through ecosystems. Depending on the ability of an ecosystem to neutralize the increased flux of acidity, acidification may increase only imperceptibly or be accelerated at a rate that

  2. Why is hydrofluoric acid a weak acid?

    Science.gov (United States)

    Ayotte, Patrick; Hébert, Martin; Marchand, Patrick

    2005-11-08

    The infrared vibrational spectra of amorphous solid water thin films doped with HF at 40 K reveal a strong continuous absorbance in the 1000-3275 cm(-1) range. This so-called Zundel continuum is the spectroscopic hallmark for aqueous protons. The extensive ionic dissociation of HF at such low temperature suggests that the reaction enthalpy remains negative down to 40 K. These observations support the interpretation that dilute HF aqueous solutions behave as weak acids largely due to the large positive reaction entropy resulting from the structure making character of the hydrated fluoride ion.

  3. Acid Rain, pH & Acidity: A Common Misinterpretation.

    Science.gov (United States)

    Clark, David B.; Thompson, Ronald E.

    1989-01-01

    Illustrates the basis for misleading statements about the relationship between pH and acid content in acid rain. Explains why pH cannot be used as a measure of acidity for rain or any other solution. Suggests that teachers present acidity and pH as two separate and distinct concepts. (RT)

  4. [Lipid synthesis by an acidic acid tolerant Rhodotorula glutinis].

    Science.gov (United States)

    Lin, Zhangnan; Liu, Hongjuan; Zhang, Jian'an; Wang, Gehua

    2016-03-01

    Acetic acid, as a main by-product generated in the pretreatment process of lignocellulose hydrolysis, significantly affects cell growth and lipid synthesis of oleaginous microorganisms. Therefore, we studied the tolerance of Rhodotorula glutinis to acetic acid and its lipid synthesis from substrate containing acetic acid. In the mixed sugar medium containing 6 g/L glucose and 44 g/L xylose, and supplemented with acetic acid, the cell growth was not:inhibited when the acetic acid concentration was below 10 g/L. Compared with the control, the biomass, lipid concentration and lipid content of R. glutinis increased 21.5%, 171% and 122% respectively when acetic acid concentration was 10 g/L. Furthermore, R. glutinis could accumulate lipid with acetate as the sole carbon source. Lipid concentration and lipid yield reached 3.20 g/L and 13% respectively with the initial acetic acid concentration of 25 g/L. The lipid composition was analyzed by gas chromatograph. The main composition of lipid produced with acetic acid was palmitic acid, stearic acid, oleic acid, linoleic acid and linolenic acid, including 40.9% saturated fatty acids and 59.1% unsaturated fatty acids. The lipid composition was similar to that of plant oil, indicating that lipid from oleaginous yeast R. glutinis had potential as the feedstock of biodiesel production. These results demonstrated that a certain concentration of acetic acid need not to be removed in the detoxification process when using lignocelluloses hydrolysate to produce microbial lipid by R. glutinis.

  5. Synthesis and anticonvulsant activity of novel bicyclic acidic amino acids

    DEFF Research Database (Denmark)

    Conti, Paola; De Amici, Marco; Joppolo Di Ventimiglia, Samuele

    2003-01-01

    Bicyclic acidic amino acids (+/-)-6 and (+/-)-7, which are conformationally constrained homologues of glutamic acid, were prepared via a strategy based on a 1,3-dipolar cycloaddition. The new amino acids were tested toward ionotropic and metabotropic glutamate receptor subtypes; both of them...

  6. Salvianolic acid A alleviates ischemic brain injury through the inhibition of inflammation and apoptosis and the promotion of neurogenesis in mice.

    Science.gov (United States)

    Chien, Mei-Yin; Chuang, Cheng-Hung; Chern, Chang-Ming; Liou, Kou-Tong; Liu, Der-Zen; Hou, Yu-Chang; Shen, Yuh-Chiang

    2016-10-01

    Salvianolic acid A (SalA), a chemical type of caffeic acid trimer, has drawn great attention for its potent bioactivities against ischemia-induced injury both in vitro and in vivo. In this study, we evaluated SalA's protective effects against acute ischemic stroke by inducing middle cerebral artery occlusion/reperfusion (MCAO) injuries in mice. Treatment of the mice with SalA (50 and 100μg/kg, i.v.) at 2h after MCAO enhanced their survival rate, improved their moving activity, and ameliorated the severity of brain infarction and apoptosis seen in the mice by diminishing pathological changes such as the extensive breakdown of the blood-brain barrier (BBB), nitrosative stress, and the activation of an inflammatory transcriptional factor p65 nuclear factor-kappa B (NF-κB) and a pro-apoptotic kinase p25/Cdk5. SalA also intensively limited cortical infarction and promoted the expression of neurogenesis protein near the peri-infarct cortex and subgranular zone of the hippocampal dentate gyrus by compromising the activation of GSK3β and p25/Cdk5, which in turn upregulated β-catenin, doublecortin (DCX), and Bcl-2, most possibly through the activation of PI3K/Akt signaling via the upregulation of brain-derived neurotrophic factor. We conclude that SalA blocks inflammatory responses by impairing NF-κB signaling, thereby limiting inflammation/nitrosative stress and preserving the integrity of the BBB; SalA also concomitantly promotes neurogenesis-related protein expression by compromising GSK3β/Cdk5 activity to enhance the expression levels of β-catenin/DCX and Bcl-2 for neuroprotection. Copyright © 2016 Elsevier Inc. All rights reserved.

  7. Chemistry and electrochemistry in trifluoroacetic acid. Comparison with acetic acid

    International Nuclear Information System (INIS)

    Petit, Gerard

    1972-01-01

    As the trifluoroacetic acid is, with the acetic acid, one of most often used carboxylic acids as solvent, notably in organic chemistry, this research thesis addresses some relatively simple complexing and redox reactions to highlight the peculiar feature of this acid, and to explain its very much different behaviour with respect to acetic acid. The author develops the notion of acidity level in solvents of low dielectric constant. The second part addresses a specific solvent: BF 3 (CH 3 COOH) 2 . The boron trifluoride strengthens the acidity of acetic acid and modifies its chemical and physical-chemical properties. In the third part, the author compares solvent properties of CF 3 COOH and CH 3 COOH. Noticed differences explain why the trifluoroacetic acid is a more interesting reaction environment than acetic acid for reactions such as electrophilic substitutions or protein solubilisation [fr

  8. Domoic Acid Epileptic Disease

    Directory of Open Access Journals (Sweden)

    John S. Ramsdell

    2014-03-01

    Full Text Available Domoic acid epileptic disease is characterized by spontaneous recurrent seizures weeks to months after domoic acid exposure. The potential for this disease was first recognized in a human case study of temporal lobe epilepsy after the 1987 amnesic shellfish-poisoning event in Quebec, and was characterized as a chronic epileptic syndrome in California sea lions through investigation of a series of domoic acid poisoning cases between 1998 and 2006. The sea lion study provided a breadth of insight into clinical presentations, unusual behaviors, brain pathology, and epidemiology. A rat model that replicates key observations of the chronic epileptic syndrome in sea lions has been applied to identify the progression of the epileptic disease state, its relationship to behavioral manifestations, and to define the neural systems involved in these behavioral disorders. Here, we present the concept of domoic acid epileptic disease as a delayed manifestation of domoic acid poisoning and review the state of knowledge for this disease state in affected humans and sea lions. We discuss causative mechanisms and neural underpinnings of disease maturation revealed by the rat model to present the concept for olfactory origin of an epileptic disease; triggered in dendodendritic synapases of the olfactory bulb and maturing in the olfactory cortex. We conclude with updated information on populations at risk, medical diagnosis, treatment, and prognosis.

  9. Citric acid by fermentation

    Energy Technology Data Exchange (ETDEWEB)

    El-Sayed, R M

    1978-11-30

    Citric acid is produced in 2 stages, in the first of which Escherichia coli KG93 F-is cultured on a substrate consisting of whey permeate to which phosphate and nitrate or urea is added. In the second stage, Hansenula wickerhamii CBS 4308 is cultured on the culture solution from the first stage and the citric acid isolated in the usual manner. Thus, a whey permeate comprising fat 0.20, protein 0.05, lactose 5.0, lactic acid 0.1, and salts 0.6% (Ca 0.06, P 0.06, K 0.16, N 0.03, and NaCl 0.3%) was amended with 1.2 g phosphate/L and 1.0 g NO/sub 3/sup -///L. After introducing the whey permeate into a continuous fermentor, it was inoculated with E. coli K693 F- and allowed to incubate at 37/sup 0/ and pH 7 (Maintained with NH/sub 3/ gas) for 12 h with aeration, thereby producing concentration pyruvic acid. After an additional 6 h cultivation without aeration, the broth was transferred to another fermentor and there inoculated with H. wickerhamii CBS 4308. The second cultivation step was carried out at 30/sup 0/ and a pH of 5 for 24 h with the pH stabilized by NH/sub 3/ gas. To the second stage culture, 0.3 g Fe(CN)/sup 4 -//L was added. The yield of pyruvic acid in the first stage was 32 g/L and the final yield of citric acid was 43 g/L.

  10. 2-arylureidobenzoic acids

    DEFF Research Database (Denmark)

    Valgeirsson, Jon; Nielsen, Elsebet Ø; Peters, Dan

    2003-01-01

    A series of 2-arylureidobenzoic acids (AUBAs) was prepared by a short and effective synthesis, and the pharmacological activity at glutamate receptors was evaluated in vitro and in vivo. The compounds showed noncompetitive antagonistic activity at the kainate receptor subtype GluR5. The most potent...... on the benzoic acid moiety (ring A), whereas ring B tolerated a variety of substituents, but with a preference for lipophilic substituents. The most potent compounds had a 4-chloro substituent on ring A and 3-chlorobenzene (6b), 2-naphthalene (8h), or 2-indole (8k) as ring B and had IC(50) values of 1.3, 1...

  11. Whither Acid Rain?

    Directory of Open Access Journals (Sweden)

    Peter Brimblecombe

    2000-01-01

    Full Text Available Acid rain, the environmental cause célèbre of the 1980s seems to have vanished from popular conscience. By contrast, scientific research, despite funding difficulties, has continued to produce hundreds of research papers each year. Studies of acid rain taught much about precipitation chemistry, the behaviour of snow packs, long-range transport of pollutants and new issues in the biology of fish and forested ecosystems. There is now evidence of a shift away from research in precipitation and sulfur chemistry, but an impressive theoretical base remains as a legacy.

  12. The Acid-Base Titration of a Very Weak Acid: Boric Acid

    Science.gov (United States)

    Celeste, M.; Azevedo, C.; Cavaleiro, Ana M. V.

    2012-01-01

    A laboratory experiment based on the titration of boric acid with strong base in the presence of d-mannitol is described. Boric acid is a very weak acid and direct titration with NaOH is not possible. An auxiliary reagent that contributes to the release of protons in a known stoichiometry facilitates the acid-base titration. Students obtain the…

  13. Catalytic acetoxylation of lactic acid to 2-acetoxypropionic acid, en route to acrylic acid

    NARCIS (Netherlands)

    Beerthuis, R.; Granollers, M.; Brown, D.R.; Salavagione, H.J.; Rothenberg, G.; Shiju, N.R.

    2015-01-01

    We present an alternative synthetic route to acrylic acid, starting from the platform chemical lactic acid and using heterogeneous catalysis. To improve selectivity, we designed an indirect dehydration reaction that proceeds via acetoxylation of lactic acid to 2-acetoxypropionic acid. This

  14. Comparison of Buffer Effect of Different Acids During Sandstone Acidizing

    International Nuclear Information System (INIS)

    Shafiq, Mian Umer; Mahmud, Hisham Khaled Ben; Hamid, Mohamed Ali

    2015-01-01

    The most important concern of sandstone matrix acidizing is to increase the formation permeability by removing the silica particles. To accomplish this, the mud acid (HF: HCl) has been utilized successfully for many years to stimulate the sandstone formations, but still it has many complexities. This paper presents the results of laboratory investigations of different acid combinations (HF: HCl, HF: H 3 PO 4 and HF: HCOOH). Hydrofluoric acid and fluoboric acid are used to dissolve clays and feldspar. Phosphoric and formic acids are added as a buffer to maintain the pH of the solution; also it allows the maximum penetration of acid into the core sample. Different tests have been performed on the core samples before and after the acidizing to do the comparative study on the buffer effect of these acids. The analysis consists of permeability, porosity, color change and pH value tests. There is more increase in permeability and porosity while less change in pH when phosphoric and formic acids were used compared to mud acid. From these results it has been found that the buffer effect of phosphoric acid and formic acid is better than hydrochloric acid. (paper)

  15. Usnic acid controls the acidity tolerance of lichens

    International Nuclear Information System (INIS)

    Hauck, Markus; Juergens, Sascha-Rene

    2008-01-01

    The hypotheses were tested that, firstly, lichens producing the dibenzofuran usnic acid colonize substrates characterized by specific pH ranges, secondly, this preferred pH is in a range where soluble usnic acid and its corresponding anion occur in similar concentrations, and thirdly, usnic acid makes lichens vulnerable to acidity. Lichens with usnic acid prefer an ambient pH range between 3.5 and 5.5 with an optimum between 4.0 and 4.5. This optimum is close to the pK a1 value of usnic acid of 4.4. Below this optimum pH, dissolved SO 2 reduces the chlorophyll fluorescence yield more in lichens with than without their natural content of usnic acid. This suggests that usnic acid influences the acidity tolerance of lichens. The putative mechanism of the limited acidity tolerance of usnic acid-containing lichens is the acidification of the cytosol by molecules of protonated usnic acid shuttling protons through the plasma membrane at an apoplastic pH a1 . - Combined field and experimental data suggest that usnic acid makes lichens sensitive to acidity at pH <3.5

  16. [Studies on interaction of acid-treated nanotube titanic acid and amino acids].

    Science.gov (United States)

    Zhang, Huqin; Chen, Xuemei; Jin, Zhensheng; Liao, Guangxi; Wu, Xiaoming; Du, Jianqiang; Cao, Xiang

    2010-06-01

    Nanotube titanic acid (NTA) has distinct optical and electrical character, and has photocatalysis character. In accordance with these qualities, NTA was treated with acid so as to enhance its surface activity. Surface structures and surface groups of acid-treated NTA were characterized and analyzed by Transmission Electron Microscope (TEM) and Fourier Transform Infrared Spectrometry (FT-IR). The interaction between acid-treated NTA and amino acids was investigated. Analysis results showed that the lengths of acid-treated NTA became obviously shorter. The diameters of nanotube bundles did not change obviously with acid-treating. Meanwhile, the surface of acid-treated NTA was cross-linked with carboxyl or esterfunction. In addition, acid-treated NTA can catch amino acid residues easily, and then form close combination.

  17. A Direct, Biomass-Based Synthesis of Benzoic Acid: Formic Acid-Mediated Deoxygenation of the Glucose-Derived Materials Quinic Acid and Shikimic Acid

    Energy Technology Data Exchange (ETDEWEB)

    Arceo, Elena; Ellman, Jonathan; Bergman, Robert

    2010-05-03

    An alternative biomass-based route to benzoic acid from the renewable starting materials quinic acid and shikimic acid is described. Benzoic acid is obtained selectively using a highly efficient, one-step formic acid-mediated deoxygenation method.

  18. Molecular interaction of pinic acid with sulfuric acid

    DEFF Research Database (Denmark)

    Elm, Jonas; Kurtén, Theo; Bilde, Merete

    2014-01-01

    We investigate the molecular interactions between the semivolatile α-pinene oxidation product pinic acid and sulfuric acid using computational methods. The stepwise Gibbs free energies of formation have been calculated utilizing the M06-2X functional, and the stability of the clusters is evaluated...... cluster. The involvement of more than one pinic acid molecule in a single cluster is observed to lead to the formation of favorable (pinic acid)2(H2SO4) and (pinic acid)2(H2SO4)2 clusters. The identified most favorable growth paths starting from a single pinic acid molecule lead to closed structures...

  19. Alkyl phosphonic acids and sulfonic acids in the Murchison meteorite

    Science.gov (United States)

    Cooper, George W.; Onwo, Wilfred M.; Cronin, John R.

    1992-01-01

    Homologous series of alkyl phosphonic acids and alkyl sulfonic acids, along with inorganic orthophosphate and sulfate, are identified in water extracts of the Murchison meteorite after conversion to their t-butyl dimethylsilyl derivatives. The methyl, ethyl, propyl, and butyl compounds are observed in both series. Five of the eight possible alkyl phosphonic acids and seven of the eight possible alkyl sulfonic acids through C4 are identified. Abundances decrease with increasing carbon number as observed of other homologous series indigenous to Murchison. Concentrations range downward from approximately 380 nmol/gram in the alkyl sulfonic acid series, and from 9 nmol/gram in the alkyl phosphonic acid series.

  20. Koetjapic acid chloroform hemisolvate

    Directory of Open Access Journals (Sweden)

    Z. D. Nassar

    2010-06-01

    Full Text Available The asymmetric unit of the title compound, C30H46O4·0.5CHCl3, consists of one koetjapic acid [systematic name: (3R,4aR,4bS,7S,8S,10bS,12aS-7-(2-carboxyethyl-3,4b,7,10b,12a-pentamethyl-8-(prop-1-en-2-yl-1,2,3,4,4a,4b,5,6,7,8,9,10,10b,11,12,12a-hexadecahydrochrysene-3-carboxylic acid] molecule and one half-molecule of chloroform solvent, which is disordered about a twofold rotation axis. The symmetry-independent component is further disordered over two sites, with occupancies of 0.30 and 0.20. The koetjapic acid contains a fused four-ring system, A/B/C/D. The A/B, B/C and C/D junctions adopt E/trans/cis configurations, respectively. The conformation of ring A is intermediate between envelope and half-chair and ring B adopts an envelope conformation whereas rings C and D adopt chair conformations. A weak intramolecular C—H...O hydrogen bond is observed. The koetjapic acid molecules are linked into dimers by two pairs of intermolecular O—H...O hydrogen bonds. The dimers are stacked along the c axis.

  1. Microbial Propionic Acid Production

    Directory of Open Access Journals (Sweden)

    R. Axayacatl Gonzalez-Garcia

    2017-05-01

    Full Text Available Propionic acid (propionate is a commercially valuable carboxylic acid produced through microbial fermentation. Propionic acid is mainly used in the food industry but has recently found applications in the cosmetic, plastics and pharmaceutical industries. Propionate can be produced via various metabolic pathways, which can be classified into three major groups: fermentative pathways, biosynthetic pathways, and amino acid catabolic pathways. The current review provides an in-depth description of the major metabolic routes for propionate production from an energy optimization perspective. Biological propionate production is limited by high downstream purification costs which can be addressed if the target yield, productivity and titre can be achieved. Genome shuffling combined with high throughput omics and metabolic engineering is providing new opportunities, and biological propionate production is likely to enter the market in the not so distant future. In order to realise the full potential of metabolic engineering and heterologous expression, however, a greater understanding of metabolic capabilities of the native producers, the fittest producers, is required.

  2. Acid dip for dosemeter

    International Nuclear Information System (INIS)

    Stewart, J.C.; McWhan, A.F.

    1982-01-01

    Background signal in a PTFE based dosemeter caused by impurities in the PTFE and in the active component such as lithium fluoride is substantially reduced by treating the dosemeter with acid. The optimum treatment involves use of hydrofluoric acid at room temperature for approximately one minute, followed by thorough washing with methanol, and finally drying. This treatment is best applied after the original manufacture of the dosemeters. It may also be applied to existing dosemeters after they have been in use for some time. The treatment produces a permanent effect in reducing both the light induced signal and the non-light induced signal. The process may be applied to all types of dosemeter manufactured from PTFE or other plastics or resins which are able to resist brief exposure to acid. The treatment works particularly well with dosemeters based on PTFE and lithium fluoride. It is also applicable to dosemeters based on calcium sulphate, lithium borate and magnesium borate. Acids which may be used include hydrofluoric, hydrochloric, nitric, phosphoric and sulphuric. (author)

  3. Acid Ceramidase in Melanoma

    DEFF Research Database (Denmark)

    Realini, Natalia; Palese, Francesca; Pizzirani, Daniela

    2016-01-01

    Acid ceramidase (AC) is a lysosomal cysteine amidase that controls sphingolipid signaling by lowering the levels of ceramides and concomitantly increasing those of sphingosine and its bioactive metabolite, sphingosine 1-phosphate. In the present study, we evaluated the role of AC-regulated sphing...

  4. Nucleic acids in circulation

    Indian Academy of Sciences (India)

    Elevated blood levels of extracellular nucleic acids have been reported in various disease conditions; such as ageing and age-related degenerative disorders, cancer; acute and chronic inflammatory conditions, severe trauma and autoimmune disorders. In addition to genomic DNA and nucleosomes, mitochondrial DNA is ...

  5. Salicylic Acid Topical

    Science.gov (United States)

    ... the package label for more information.Apply a small amount of the salicylic acid product to one or two small areas you want to treat for 3 days ... know that children and teenagers who have chicken pox or the flu should not use topical salicylic ...

  6. Acid Rain: Science Projects.

    Science.gov (United States)

    Stubbs, Harriett S.

    1989-01-01

    Presented is a science activity designed to help students monitor the pH of rainfall. Materials, procedures and follow-up activities are listed. A list of domestic and foreign sources of information is provided. Topics which relate to acid precipitation are outlined. (CW)

  7. Hyaluronic Acid Assays

    DEFF Research Database (Denmark)

    Itenov, Theis S; Kirkby, Nikolai S; Bestle, Morten H

    2015-01-01

    BACKGROUD: Hyaluronic acid (HA) is proposed as a marker of functional liver capacity. The aim of the present study was to compare a new turbidimetric assay for measuring HA with the current standard method. METHODS: HA was measured by a particle-enhanced turbidimetric immunoassay (PETIA) and enzyme...

  8. Accidents with sulfuric acid

    Directory of Open Access Journals (Sweden)

    Rajković Miloš B.

    2006-01-01

    Full Text Available Sulfuric acid is an important industrial and strategic raw material, the production of which is developing on all continents, in many factories in the world and with an annual production of over 160 million tons. On the other hand, the production, transport and usage are very dangerous and demand measures of precaution because the consequences could be catastrophic, and not only at the local level where the accident would happen. Accidents that have been publicly recorded during the last eighteen years (from 1988 till the beginning of 2006 are analyzed in this paper. It is very alarming data that, according to all the recorded accidents, over 1.6 million tons of sulfuric acid were exuded. Although water transport is the safest (only 16.38% of the total amount of accidents in that way 98.88% of the total amount of sulfuric acid was exuded into the environment. Human factor was the common factor in all the accidents, whether there was enough control of the production process, of reservoirs or transportation tanks or the transport was done by inadequate (old tanks, or the accidents arose from human factor (inadequate speed, lock of caution etc. The fact is that huge energy, sacrifice and courage were involved in the recovery from accidents where rescue teams and fire brigades showed great courage to prevent real environmental catastrophes and very often they lost their lives during the events. So, the phrase that sulfuric acid is a real "environmental bomb" has become clearer.

  9. Pantothenic acid and biotin

    Science.gov (United States)

    Pantothenic acid and biotin are types of B vitamins. They are water-soluble, which means that the body can't store them. If the body can't use all of the vitamin, the extra vitamins leave the body through the ...

  10. and amino acids

    Indian Academy of Sciences (India)

    Unknown

    P RABINDRA REDDY* and A MOHAN REDDY. Department of ... The mixed ligand complexes of Cu(II), Ni(II) and Co(II) with uridine and amino acids ..... Sabat M, Satyashur K A and Sundaralingam M 1983 J. Am. Chem. Soc. ... Uemura T, Shimura T, Nakamishi H, Tomahiro T, Nagawa Y and Okuno (Yohmei) H 1991. Inorg.

  11. Lactic acid and lactates

    NARCIS (Netherlands)

    Schreurs, V.V.A.M.

    2010-01-01

    This review aims to integrate the present state of knowledge on lactate metabolism in human and mammalian physiology as far as it could be subject to nutritional interventions. An integrated view on the nutritional, metabolic and physiological aspects of lactic acid and lactates might open a

  12. Influence of Light and Temperature on Gene Expression Leading to Accumulation of Specific Flavonol Glycosides and Hydroxycinnamic Acid Derivatives in Kale (Brassica oleracea var. sabellica).

    Science.gov (United States)

    Neugart, Susanne; Krumbein, Angelika; Zrenner, Rita

    2016-01-01

    Light intensity and temperature are very important signals for the regulation of plant growth and development. Plants subjected to less favorable light or temperature conditions often respond with accumulation of secondary metabolites. Some of these metabolites have been identified as bioactive compounds, considered to exert positive effects on human health when consumed regularly. In order to test a typical range of growth parameters for the winter crop Brassica oleracea var. sabellica, plants were grown either at 400 μmol m(-2) s(-1) or 100 μmol m(-2) s(-1) at 10°C, or at 400 μmol m(-2) s(-1) with 5 or 15°C. The higher light intensity overall increased flavonol content of leaves, favoring the main quercetin glycosides, a caffeic acid monoacylated kaempferol triglycoside, and disinapoyl-gentiobiose. The higher temperature mainly increased the hydroxycinnamic acid derivative disinapoyl-gentiobiose, while at lower temperature synthesis is in favor of very complex sinapic acid acylated flavonol tetraglycosides such as kaempferol-3-O-sinapoyl-sophoroside-7-O-diglucoside. A global analysis of light and temperature dependent alterations of gene expression in B. oleracea var. sabellica leaves was performed with the most comprehensive Brassica microarray. When compared to the light experiment much less genes were differentially expressed in kale leaves grown at 5 or 15°C. A structured evaluation of differentially expressed genes revealed the expected enrichment in the functional categories of e.g. protein degradation at different light intensities or phytohormone metabolism at different temperature. Genes of the secondary metabolism namely phenylpropanoids are significantly enriched with both treatments. Thus, the genome of B. oleracea was screened for predicted genes putatively involved in the biosynthesis of flavonoids and hydroxycinnamic acid derivatives. All identified B. oleracea genes were analyzed for their most specific 60-mer oligonucleotides present on the

  13. Origin of fatty acids

    International Nuclear Information System (INIS)

    Prieur, B.E.

    1995-01-01

    The appearance of fatty acids and membranes is one of the most important events of the prebiotic world because genesis of life required the compartmentalization of molecules. Membranes allowed cells to become enriched with molecules relevant for their evolution and gave rise to gradients convertible into energy. By virtue of their hydrophobic/hydrophilic interface, membranes developed certain enzymatic activities impossible in the aqueous phase. A prebiotic cell is an energy unit but it is also an information unit. It has a past, a present and a future. The biochemistry of fatty acids involves acetylCoA, malonylCoA and an enzyme, acyl synthetase, which joins both molecules. After substitution of the acetyl group in place of the carboxyl group of malonyl derivatives, the chain is reduced and dehydrated to crotonyl derivatives. These molecules can again react with malonylCoA to form unsaturated chain; they can also undergo a new reduction step to form butyryl derivatives which can react with malonylCoA to form a longer aliphatic chain. The formation of malonylCoA consumes ATP. The reduction step needs NADPH and proton. Dehydration requires structural information because the reduction product is chiral (D configuration). It is unlikely that these steps were possible in a prebiotic environment. Thus we have to understand how fatty acids could appear in the prebiotic era. This hypothesis about the origin of fatty acids is based on the chemistry of sulfonium ylides and sulfonium salts. The most well-known among these molecules are S-melthyl-methionine and S-adenosyl methionine. The simplest sulfonium cation is the trimethylsulfonium cation. Chemists have evidence that these products can produce olefin when they are heated or flashed with UV light in some conditions. I suggest that these volatile products can allow the formation of fatty acids chains in atmospheric phase with UV and temperature using methanol as starting material. Different synthetic pathways will be

  14. Fatty acid-producing hosts

    Science.gov (United States)

    Pfleger, Brian F; Lennen, Rebecca M

    2013-12-31

    Described are hosts for overproducing a fatty acid product such as a fatty acid. The hosts include an exogenous nucleic acid encoding a thioesterase and, optionally, an exogenous nucleic acid encoding an acetyl-CoA carboxylase, wherein an acyl-CoA synthetase in the hosts are functionally delected. The hosts prefereably include the nucleic acid encoding the thioesterase at an intermediate copy number. The hosts are preferably recominantly stable and growth-competent at 37.degree. C. Methods of producing a fatty acid product comprising culturing such hosts at 37.degree. C. are also described.

  15. Acetic acid extraction from aqueous solutions using fatty acids

    NARCIS (Netherlands)

    IJmker, H.M.; Gramblicka, M.; Kersten, Sascha R.A.; van der Ham, Aloysius G.J.; Schuur, Boelo

    2014-01-01

    A major challenge for production of acetic acid via bio-based routes is cost-effective concentration and purification of the acetic acid from the aqueous solutions, for which liquid–liquid extraction is a possible method. A main challenge in extraction of acetic acid from dilute aqueous solutions is

  16. College Chemistry Students' Mental Models of Acids and Acid Strength

    Science.gov (United States)

    McClary, LaKeisha; Talanquer, Vicente

    2011-01-01

    The central goal of this study was to characterize the mental models of acids and acid strength expressed by advanced college chemistry students when engaged in prediction, explanation, and justification tasks that asked them to rank chemical compounds based on their relative acid strength. For that purpose we completed a qualitative research…

  17. Cytotoxic effect of betulinic acid and betulinic acid acetate isolated ...

    African Journals Online (AJOL)

    Cytotoxic effect of betulinic acid and betulinic acid acetate isolated from Melaleuca cajuput on human myeloid leukemia (HL-60) cell line. ... The cytotoxic effect of betulinic acid (BA), isolated from Melaleuca cajuput a Malaysian plant and its four synthetic derivatives were tested for their cytotoxicity in various cell line or ...

  18. Chemical composition of Clinopodium menthifolium aqueous extract

    African Journals Online (AJOL)

    Analysis by HPLC confirmed the presence of gallic acid, caffeic acid and .... The total flavonoids were estimated according to the method described by Markham .... centrifugation, supernatants were used for protein quantification and enzyme ...

  19. Physicochemical properties, phenolic acids and volatile compounds of oil extracted from dry alhydwan (Boerhavia elegana Choisy seeds

    Directory of Open Access Journals (Sweden)

    Al-Farga, A.

    2015-09-01

    Full Text Available In this study, the chemical composition, physicochemical properties, phenolic acids and volatile compounds of alhydwan (Boerhavia elegana Choisy seed oil were evaluated. The crude oil content was 11.49%, ash 6.88%, moisture 6.12%, protein content 14.60%, total carbohydrate 24.77% and fiber 36.13%. The oil contain a high quantity of unsaturated fatty acids (74.63 mg·100 g−1 with oleic (C18:1 (57.77%, palmitic (C16:0 (18.65% and linoleic (C18:2 (12.88% acids as the most abundant. The relative density was 0.88 and the iodine value 105.59. The color analysis showed a value of 28.33 Y+1.43 R. The oil also had a high relative oxidative stability. The tocol composition showed that α-tocotrienol, γ-tocopherol and γ-tocotrienol were in a higher concentration than the rest. Seven phenolic acids (caffeic, vanillic, galic, p-coumaric, ascorbic, cinnamic and ferulic were detected, with ascorbic acid as the predominant one (5.44 mg·100 g−1. In relation to the volatile composition, 48 compounds were found with Z-10-Pentadecen-1-ol (56.73%; Hexadecenoic acid, Z-11- (18.52%; 9,12-Octadecadienoic acid (Z,Z- (3.93% and 9,12-Octadecadienoic acid (Z,Z-, 2-hydroxy-1-(hydroxymethyl ethyl ester (3.04% as the most abundant. These findings demonstrated the potential of alhydwan seeds to be used as a good source of quality edible oil.En este estudio se ha determinado la composición química, las propiedades físico-químicas, ácidos fenólicos y compuestos volátiles de aceites de semillas de alhydwan (Boerhavia elegana Choisy. Las semillas contenían un 11.49% de aceite, 6.88% de cenizas, 6,12% de humedad, 14.60% de proteínas, 24.77% de carbohidratos totales y 36.13% de fibra. El aceite contiene 74,63 mg·100 g−1 de ácidos grasos insaturados, con oleico (C18: 1 (57,77%, palmítico (C16: 0 (18,65% y linoleico (C18: 2 (12,88% como los más abundantes. La densidad relativa fue de 0,88 y el índice de yodo de 105,59. El análisis del color mostró un valor de

  20. Industrial ecotoxicology "acid rain".

    Science.gov (United States)

    Astolfi, E; Gotelli, C; Higa, J

    1986-01-01

    The acid rain phenomenon was studied in the province of Cordoba, Argentina. This study, based on a previously outlined framework, determined the anthropogenic origin of the low pH due to the presence of industrial hydrochloric acid wastage. This industrial ecotoxicological phenomenon seriously affected the forest wealth, causing a great defoliation of trees and shrubs, with a lower effect on crops. A survey on its effects on human beings has not been carried out, but considering the corrosion caused to different metals and its denouncing biocide effect on plants and animals, we should expect to find some kind of harm to the health of the workers involved or others engaged in farming, and even to those who are far away from the polluting agent.

  1. Radioimmunoassay for jasmonic acid

    Energy Technology Data Exchange (ETDEWEB)

    Knoefel, H.D.; Brueckner, C.; Kramell, R.; Sembdner, G.; Schreiber, K. (Akademie der Wissenschaften der DDR, Halle/Saale. Inst. fuer Biochemie der Pflanzen)

    1984-01-01

    A radioimmunoassay (RIA) for the natural plant growth regulator jasmonic acid (JA) was developed. The antiserum was raised in rabbits against (+-)-JA linked to bovine serum albumin. As tracer tritium labelled (+-)-JA (spec. act. 7.4 x 10/sup 9/ Bq x mmol/sup -1/) was used. Cross-reactivity studies with compounds structurally related to JA demonstrated the antiserum to be specific for JA, abscisic acid normally present in the same extract does not interfer. The RIA has a detection limit of 2 ng (-)-JA methylester, a measuring range 2-200 ng, and no extensive purification is required prior to estimation. Therefore, in JA analysis the RIA described is superior to GC, HPLC, and bioassay. This new method has been employed for studies on the distribution of JA in different plant organs of the broad bean, Vicia faba L.

  2. Acid corrosion inhibitor

    Energy Technology Data Exchange (ETDEWEB)

    Chen, N G

    1964-04-28

    An acid corrosion inhibitor is prepared by a 2-stage vacuum evaporation of effluents obtained from the ammonia columns of the coking oven plant. The effluent, leaving a scrubber in which the phenols are removed at a temperature of 98$C, passes through a quartz filter and flows into a heated chamber in which it is used for preheating a solution circulating through a vacuum unit, maintaining the temperature of the solution at 55$ to 60$C. The effluent enters a large tank in which it is boiled at 55$ to 60$C under 635 to 640 mm Hg pressure. Double evaporation of this solution yields a very effective acid corrosion inhibitor. Its corrosion-preventing effect is 97.9% compared with 90.1% for thiourea and 88.5% for urotropin under identical conditions.

  3. N-(3-Methylphenylsuccinamic acid

    Directory of Open Access Journals (Sweden)

    B. Thimme Gowda

    2010-02-01

    Full Text Available In the crystal structure of the title compound, C11H13NO3, the conformations of the N—H and C=O bonds in the amide segment are anti to each other, and that of the amide H atom is anti to the meta-methyl group in the benzene ring. Furthermore, the conformations of the amide oxygen and the carbonyl O atom of the acid segment are also anti to the adjacent –CH2 groups. The C=O and O—H bonds of the acid group are syn to each other. In the crystal, the molecules are packed into infinite chains through intermolecular N—H...O and O—H...O hydrogen bonds.

  4. N-(3-Chlorophenylmaleamic acid

    Directory of Open Access Journals (Sweden)

    B. Thimme Gowda

    2010-07-01

    Full Text Available In the title compound, C10H8ClNO3, the molecular conformation is stabilized by two intramolecular hydrogen bonds. The first is a short O—H...O hydrogen bond within the maleamic acid unit and the second is a C—H...O hydrogen bond which connects the amide group with the phenyl ring. The maleamic acid unit is essentially planar, with an r.m.s. deviation of 0.044 Å, and makes a dihedral angle of 15.2 (1° with the phenyl ring. In the crystal, intermolecular N—H...O hydrogen bonds link the molecules into C(7 chains running [010].

  5. Mortar fights acid corrosion

    Energy Technology Data Exchange (ETDEWEB)

    1982-05-14

    The burning of coal or oil to produce heat required to operate a power boiler also generates a severe corrosion problem within the interior of the duct and stacks used to emit the flue gas into the atmosphere. How can concrete and steel be protected from the effects of acid attack, when the acids are carried in a gas form, or come into direct contact with the steel or concrete from spillage or immersion conditions. Industry in North America has found that the solution to this problem is to build an outside concrete column, in this case of Portland cement, and inside that column, build a totally independent brick liner bonded with Sauereisen mortar.

  6. (Radioiodinated free fatty acids)

    Energy Technology Data Exchange (ETDEWEB)

    Knapp, Jr., F. F.

    1987-12-11

    The traveler participated in the Second International Workshop on Radioiodinated Free Fatty Acids in Amsterdam, The Netherlands where he presented an invited paper describing the pioneering work at the Oak Ridge National Laboratory (ORNL) involving the design, development and testing of new radioiodinated methyl-branched fatty acids for evaluation of heart disease. He also chaired a technical session on the testing of new agents in various in vitro and in vivo systems. He also visited the Institute for Clinical and Experimental Nuclear Medicine in Bonn, West Germany, to review, discuss, plan and coordinate collaborative investigations with that institution. In addition, he visited the Cyclotron Research Center in Liege, Belgium, to discuss continuing collaborative studies with the Osmium-191/Iridium-191m radionuclide generator system, and to complete manuscripts and plan future studies.

  7. Acidity of Scandinavian precipitation

    Energy Technology Data Exchange (ETDEWEB)

    Barrett, E; Bordin, G

    1955-01-01

    Data on the pH of the total monthly precipitation at stations of a Swedish network for sampling and chemical analysis of precipitation and atmospheric aerosols during the year July 1953 to June 1954 are presented and discussed, together with the pH data from the first two months of operation of a large pan-Scandinavian net. It is found that well-defined regions of acidity and alkalinity relative to the pH of water in equilibrium with atmospheric carbon dioxide exist, and that these regions persist to such an extent that the monthly deviations from the pattern of the annual mean pH at stations unaffected by local pollution show persistently high acidity, while inland northern stations show equally persistent alkalinity. Some possible reasons for the observed distributions are considered.

  8. Omega-3 fatty acids (image)

    Science.gov (United States)

    Omega-3 fatty acids are a form of polyunsaturated fat that the body derives from food. Omega-3s (and omega-6s) are known as essential fatty acids (EFAs) because they are important for good health. ...

  9. Bile acids for viral hepatitis

    DEFF Research Database (Denmark)

    Chen, Weikeng; Liu, J; Gluud, C

    2007-01-01

    Trials have assessed bile acids for patients with viral hepatitis, but no consensus has been reached regarding their usefulness.......Trials have assessed bile acids for patients with viral hepatitis, but no consensus has been reached regarding their usefulness....

  10. Halogenated fatty acids

    DEFF Research Database (Denmark)

    Mu, Huiling; Sundin, Peter; Wesén, Clas

    1997-01-01

    Halogenated fatty acids are the major contributors to organohalogen compounds in lipids of marine mammals, fish, and bivalves. For the initial characterization of these recently noticed compounds, a determination of the halogen concentration has usually been combined with some lipid isolation......), atomic emission spectrometry, and mass spectrometry. For most environmental samples, chlorinated FAMEs must be enriched prior to GC. ELCD is a useful detection method for indicating halogenated FAMEs in the chromatograms, and tentative identification of the halogenated species can be obtained...

  11. Accidents with sulfuric acid

    OpenAIRE

    Rajković Miloš B.

    2006-01-01

    Sulfuric acid is an important industrial and strategic raw material, the production of which is developing on all continents, in many factories in the world and with an annual production of over 160 million tons. On the other hand, the production, transport and usage are very dangerous and demand measures of precaution because the consequences could be catastrophic, and not only at the local level where the accident would happen. Accidents that have been publicly recorded during the last eigh...

  12. Sources of atmospheric acidity

    International Nuclear Information System (INIS)

    Clarke, A.G.

    1992-01-01

    The emissions of acid gases from anthropogenic sources and their impact on the environment are the main concern of this book. However, that impact can only be assessed if all the naturally occurring sources of these gases are also known and can be quantified. Given the widely dispersed nature of the natural sources and the problems of measurement of trace species at low concentrations, often in remote regions, the quantification is a very difficult task. Nevertheless, considerable progress has been made over the last decade. In this chapter both man-made and natural sources of atmospheric acidity will be reviewed, but the emphasis will be placed not so much on the global balances as on the scale of the natural sources in relation to the man-made sources. This requires that the very uneven geographical distribution of emissions and the lifetime of individual chemical species be taken into account. The emissions considered are sulphur compounds, nitrogen compounds, chlorine compounds and organic acids. The anthropogenic sources discussed are the combustion of fossil fuels and certain industrial processes. Emissions data for anthropogenic sources are given for the United Kingdom, Europe, USA and globally. A list of 95 references is given. (Author)

  13. Whence the acid raindrop

    International Nuclear Information System (INIS)

    Heaton, T.H.E.

    1987-01-01

    Absorption of NO 2 can cause damage in animals and plants and, if present trends for NO x emissions continue, their by-product nitric acid may soon overtake sulphuric acid as the main acidifying agent of 'acid' rain. In response to this problem the feasibility of reducing NO x emissions from power stations is being studied. Although there can be no doubt that these expensive controls are desirable, their benefits are difficult to predict for two reasons: NO x is not only emitted by fuel combustion and the degree to which an industrialised country benefits from the implementation of NO x emission controls depends on how much its pollutant 'fall out' is immediately returned from the atmosphere, and how much is exported to neighbouring countries. The above factors involve questions regarding the source and reaction mechanisms for nitrogen compounds in the atmosphere. Because stable isotope ratio analysis has proved to be of value in providing answers to such questions in other environments, an investigation of the 15 N/ 14 N ratios of atmospheric gases (NO x , NH 3 ) and their solution products in rain (NO 3 , NH + 4 ) seemed to be justified

  14. Hepatic Toxicity of Perfluorocarboxylic Acids.

    Science.gov (United States)

    1996-07-01

    1995). 3. N. V. Reo, C. M. Goecke, L. Narayanan, and B. M. Jarnot. "Effects of Perfluoro-n-octanoic Acid , Perfluoro-n-decanoic Acid , and Clofibrate ...Artz, and B. M. Jarnot: "ILiver Phosphorous Metabolic Response to Perfluorocarboxylic Acids and Clofibrate in Rats and Guinea Pigs: A 31 P NMR Study...Peroxisome Induction by Perfluoro-n-decanoic Acid and Clofibrate in the Rat: Proliferation Versus Activity." International Society for the Study of

  15. Acids and bases solvent effects on acid-base strenght

    CERN Document Server

    Cox, Brian G

    2013-01-01

    Acids and bases are ubiquitous in chemistry. Our understanding of them, however, is dominated by their behaviour in water. Transfer to non-aqueous solvents leads to profound changes in acid-base strengths and to the rates and equilibria of many processes: for example, synthetic reactions involving acids, bases and nucleophiles; isolation of pharmaceutical actives through salt formation; formation of zwitter- ions in amino acids; and chromatographic separation of substrates. This book seeks to enhance our understanding of acids and bases by reviewing and analysing their behaviour in non-aqueous solvents. The behaviour is related where possible to that in water, but correlations and contrasts between solvents are also presented.

  16. Sequential injection redox or acid-base titration for determination of ascorbic acid or acetic acid.

    Science.gov (United States)

    Lenghor, Narong; Jakmunee, Jaroon; Vilen, Michael; Sara, Rolf; Christian, Gary D; Grudpan, Kate

    2002-12-06

    Two sequential injection titration systems with spectrophotometric detection have been developed. The first system for determination of ascorbic acid was based on redox reaction between ascorbic acid and permanganate in an acidic medium and lead to a decrease in color intensity of permanganate, monitored at 525 nm. A linear dependence of peak area obtained with ascorbic acid concentration up to 1200 mg l(-1) was achieved. The relative standard deviation for 11 replicate determinations of 400 mg l(-1) ascorbic acid was 2.9%. The second system, for acetic acid determination, was based on acid-base titration of acetic acid with sodium hydroxide using phenolphthalein as an indicator. The decrease in color intensity of the indicator was proportional to the acid content. A linear calibration graph in the range of 2-8% w v(-1) of acetic acid with a relative standard deviation of 4.8% (5.0% w v(-1) acetic acid, n=11) was obtained. Sample throughputs of 60 h(-1) were achieved for both systems. The systems were successfully applied for the assays of ascorbic acid in vitamin C tablets and acetic acid content in vinegars, respectively.

  17. Molecular Structure of Nucleic Acids

    Indian Academy of Sciences (India)

    Molecular Structure of Nucleic Acids. A Structure for Deoxyribose Nucleic Acid. J. D. Watson and F. H. C. Crick. Medical Research Council Unit for the Study of the Molecular Structure of Biological. Systems, Cavendish Laboratory, Cambridge. April 2. We wish to suggest a structure for the salt of deoxyribose nucleic acid ...

  18. Fumaric acid production by fermentation

    NARCIS (Netherlands)

    Roa Engel, C.A.; Straathof, A.J.J.; Zijlmans, T.W.; Van Gulik, W.M.; Van der Wielen, L.A.M.

    2008-01-01

    Abstract The potential of fumaric acid as a raw material in the polymer industry and the increment of cost of petroleum-based fumaric acid raises interest in fermentation processes for production of this compound from renewable resources. Although the chemical process yields 112% w/w fumaric acid

  19. Pantothenic acid biosynthesis in zymomonas

    Energy Technology Data Exchange (ETDEWEB)

    Tao, Luan; Tomb, Jean-Francois; Viitanen, Paul V.

    2014-07-01

    Zymomonas is unable to synthesize pantothenic acid and requires this essential vitamin in growth medium. Zymomonas strains transformed with an operon for expression of 2-dehydropantoate reductase and aspartate 1-decarboxylase were able to grow in medium lacking pantothenic acid. These strains may be used for ethanol production without pantothenic acid supplementation in seed culture and fermentation media.

  20. Attenuation of dermal wounds via downregulating oxidative stress and inflammatory markers by protocatechuic acid rich n-butanol fraction of Trianthema portulacastrum Linn. in wistar albino rats.

    Science.gov (United States)

    Yadav, Ekta; Singh, Deepika; Yadav, Pankajkumar; Verma, Amita

    2017-12-01

    Oxidative stress and inflammation contribute as a key factor for retarding the process of dermal wound healing. Trianthema portulcastrum Linn. (TP) leaves reported to possess antioxidant, antifungal, anti-inflammatory and antibacterial properties, which could make TP a promising wound healing agent. The current study was aimed to estimate the antioxidant potential of the fractionated hydroethanolic extract of TP leaves and evaluate wound healing activity by excision and incision wound models along with the assessment of possible underlying mechanism. Ethyl acetate, chloroform and n-butanol fractions of the hydroethanolic extract of TP leaves were examined for in vitro antioxidant ability by DPPH method. Strongest antioxidant activity bearing n-butanol fraction (nBuTP) was further analyzed quantitatively by High Performance Liquid Chromatography coupled with Diode Array Detector (HPLC-DAD). Wound healing potential of nBUTP using excision and incision wound model was studied. Wistar albino rats were randomly divided into four groups, containing six animals in each group; group I served as control treated with simple ointment base, group II was standard group, treated with povidone-iodine ointment USP (5%), group III treated with nBuTP 5% w/w ointment, and group IV treated with nBuTP 10%w/w ointment. All the groups were topically applied their respective ointments, once daily, till the complete healing achieved. Wound healing was assessed by analyzing % wound closure, hydroxyproline content, epithelialization period, tensile strength, enzymatic antioxidative status and inflammatory markers. Total phenolic and flavonoid content of the extract was estimated to be 112.32±1.12 and 84.42±0.47mg/g, respectively. HPLC-DAD of nBuTP confirmed the presence of chlorogenic acid (20.74±0.03), protocatechuic acid (34.45±0.02mg/g), caffeic acid (4.31±0.03mg/g) and ferulic acid (1.43±0.01mg/g). 5% and 10%w/w nBuTP ointment significantly accelerated the wound healing process

  1. Danburite decomposition by hydrochloric acid

    International Nuclear Information System (INIS)

    Mamatov, E.D.; Ashurov, N.A.; Mirsaidov, U.

    2011-01-01

    Present article is devoted to decomposition of danburite of Ak-Arkhar Deposit of Tajikistan by hydrochloric acid. The interaction of boron containing ores of Ak-Arkhar Deposit of Tajikistan with mineral acids, including hydrochloric acid was studied. The optimal conditions of extraction of valuable components from danburite composition were determined. The chemical composition of danburite of Ak-Arkhar Deposit was determined as well. The kinetics of decomposition of calcined danburite by hydrochloric acid was studied. The apparent activation energy of the process of danburite decomposition by hydrochloric acid was calculated.

  2. Waste acid detoxification and reclamation

    International Nuclear Information System (INIS)

    Brouns, T.M.; Stewart, T.L.

    1988-01-01

    Economically feasible processes that reduce the volume, quantity, and toxicity of metal-bearing waste acids by reclaiming, reusing, and recycling spent acids and metal salts are being developed and demonstrated. The acids used in the demonstrations are generated during metal-finishing operations used in nuclear fuel fabrication; HF-HNO 3 , HNO 3 , and HNO 3 -H 2 SO 4 wastes result from Zr etching, Cu stripping, and chemical milling of U. At discharge, wastes contain high concentrations of acid and one major metal impurity. The waste minimization process used to reclaim acid from these three streams incorporates three processes for acid regeneration and reclamation. Normally, HNO 3 remains in the bottoms when an aqueous acid solution is distilled; however, in the presence of H 2 SO 4 , HNO 3 will distill to the overhead stream. In this process, nitrates and fluorides present as free acid and metal salts can be reclaimed as acid for recycle to the metal-finishing processes. Uranium present in the chemical milling solution can be economically recovered from distillation bottoms and refined. Using acid distillation, the volume of chemical milling solution discharged as waste can be reduced by as much as 60% depending on the H 2 SO 4 concentration. A payback period of 2.2 years has been estimated for this process. The development and demonstration of precipitation and distillation processes for detoxification and reclamation of waste acid is supported by the US Department of Energy's Hazardous Waste Remedial Actions Program (HAZWRAP)

  3. New Acid Combination for a Successful Sandstone Acidizing

    Science.gov (United States)

    Shafiq, M. U.; Mahmud, H. K. B.; Rezaee, R.

    2017-05-01

    With the development of new enhanced oil recovery techniques, sandstone acidizing has been introduced and played a pivotal role in the petroleum industry. Different acid combinations have been applied, which react with the formation, dissolve the soluble particles; thus increase the production of hydrocarbons. To solve the problems which occurred using current preflush sandstone acidizing technology (hydrochloric acid); a new acid combination has been developed. Core flooding experiments on sandstone core samples with dimensions 1.5 in. × 3 in. were conducted at a flow rate of 2 cm3/min. A series of hydrochloric-acetic acid mixtures with different ratios were tested under 150°F temperature. The core flooding experiments performed are aimed to dissolve carbonate, sodium, potassium and calcium particles from the core samples. These experiments are followed by few important tests which include, porosity-permeability, pH value, Inductively Coupled Plasma (ICP) analysis and Nuclear Magnetic Resonance (NMR measurements). All the results are compared with the results of conventional hydrochloric acid technology. NMR and porosity analysis concluded that the new acid combination is more effective in creating fresh pore spaces and thus increasing the reservoir permeability. It can be seen from the pore distribution before and after the acidizing. Prior applying acid; the large size of pores appears most frequently in the pore distribution while with the applied acid, it was found that the small pore size is most the predominant of the pore distribution. These results are validated using ICP analysis which shows the effective removal of calcium and other positive ions from the core sample. This study concludes that the combination of acetic-hydrochloric acid can be a potential candidate for the preflush stage of sandstone acidizing at high temperature reservoirs.

  4. Urban acid deposition

    Energy Technology Data Exchange (ETDEWEB)

    Conlan, D.E.; Longhurst, J.W.S.; Gee, D.R.; Hare, S.E.

    1991-07-01

    In this document results from the Greater Manchester Acid Deposition Survey (GMADS), an urban precipitation chemistry network, for 1990 are presented. Full analytical methods are described along with the precision and accuracy of the methods used. The spatial variability of precipitation chemistry and deposition over this urban region was investigated using a network of twenty collectors. Concentrations of non marine sulphate, ammonium, calcium and hydrogen, and nitrogen dioxide gas concentrations all show significant spatial variability. The spatial variability of the deposition rates of non marine sulphate, nitrate, ammonium, hydrogen and calcium were significant. (Author).

  5. Synthesis of aminoaldonic acids

    DEFF Research Database (Denmark)

    Jørgensen, Christel Thea

    With the aim of synthesising aminoaldonic acids, two 2-acetamido-2-deoxyaldonolactones with D-galacto (6) and D-arabino (11) configuration were prepared from acetylated sugar formazans in analogy with a known procedure. Empolying the same procedure to acetylated sugar phenylhydrazones gave mixtures...... and 82, respectively. The aminolactone 84 was converted into the corresponding amino sugar 89.With the aim of synthesising substrates for the Pictet-Spengler reaction three 4-aldehydo acetamidodideoxytetronolactones 92, 97 and 103 were prepared by periodate cleavage of the corresponding hexonolactones...

  6. Conversion of hydroxycinnamic acids into volatile phenols in a synthetic medium and in red wine by Dekkera bruxellensis Transformação de ácidos hidroxicinâmicos em fenóis voláteis em meio sintético e em vinho tinto por Dekkera bruxellensis

    Directory of Open Access Journals (Sweden)

    Maria João Cabrita

    2012-03-01

    Full Text Available The conversion of p-coumaric acid, ferulic acid, and caffeic acid into 4-ethylphenol, 4-ethylguaiacol and 4-ethylcatechol was studied in Dekkera bruxellensis ISA 1791 under defined conditions in a synthetic medium and in a red wine. Liquid chromatography (HPLC-DAD was used to quantify the phenolic acids, and gas chromatography (GC coupled to a FID detector was used to quantify volatile phenols using a novel analytical methodology that does not require sample derivatization. Identification was achieved by gas chromatography-mass detection (GC-MS. The results show that phenolic acids concentration decreases while volatile phenols concentration increases. The proportion of caffeic acid taken up by Dekkera bruxellensis is lower than that for p-coumaric or ferulic acid; therefore less 4-ethylcatechol is formed. More important, 4-ethylcathecol synthesis by Dekkera bruxellensis in wine has never been demonstrated so far. These results contribute decisively to a better understanding of the origin of the volatile phenols in wines. The accumulation of these compounds in wine is nowadays regarded as one of the key factors of quality control.A transformação do ácido p-cumárico, ácido ferúlico e ácido cafeico em 4-etilfenol, 4-etilguaiacol e 4-etilcatecol foi estudada na presença de Dekkera bruxelensis ISA 1791, sob condições controladas, em meio sintético e em vinho tinto. Os compostos fenólicos foram doseados por cromatografia em fase líquida (HPLC-DAD e os fenóis voláteis foram doseados por cromatografia em fase gasosa (GC com detector de ionização de chama (FID, recorrendo a uma metodologia que não requer prévia derivatização da amostra. A identificação dos compostos foi comprovada por espectrometria de massa (GC-MS. Os resultados demonstram que os teores em ácidos fenólicos diminuem enquanto se observa um aumento dos teores em fenóis voláteis. O ácido cafeico é dos três ácidos em estudo, o menos utilizado pela levedura, da

  7. Investigating the synergistic antioxidant effects of some flavonoid and phenolic compounds

    Directory of Open Access Journals (Sweden)

    H. Hajimehdipoor

    2014-04-01

    Full Text Available Phenolic and flavonoid compounds are secondary metabolites of plants which possess various activities such as anti-inflammatory, analgesic, anti-diabetes and anticancer effects. It has been established that these compounds can scavenge free radicals produced in the body. Because of this ability, not only the plants containing phenolic and flavonoid compounds but also, the pure compounds are used in medicinal products for prevention and treatment of many disorders. Considering that the golden aim of the pharmaceutical industries is using the most effective compounds with lower concentrations, determination of the best combination of the compounds with synergistic effects is important. In the present study, synergistic antioxidant effects of four phenolic compounds including caffeic acid, gallic acid, rosmarinic acid, chlorogenic acid and two flavonoids,  rutin and quercetin, have been investigated by FRAP (Ferric Reducing Antioxidant Power method. The synergistic effect was assessed by comparing the experimental antioxidant activity of the mixtures with calculated theoretical values and the interactions of the compounds were determined. The results showed that combination of gallic acid and caffeic acid demonstrated considerable synergistic effects (137.8% while other combinations were less potent. Among examined substances, rutin was the only one which had no effect on the other compounds. The results of ternary combinations of compounds demonstrated antagonistic effects in some cases. This was more considerable in mixture of rutin, caffeic acid, rosmarinic acid (-21.8%, chlorogenic acid, caffeic acid, rosmarinic acid (-20%, rutin, rosmarinic acid, gallic acid (-18.5% and rutin, chlorogenic acid, caffeic acid (-15.8%, while, combination of quercetin, gallic acid, caffeic acid (59.4% and quercetin, gallic acid, rutin (55.2% showed the most synergistic effects. It was concluded that binary and ternary combination of quercetin, rutin, caffeic acid

  8. Folic Acid: MedlinePlus Health Topic

    Science.gov (United States)

    ... acid in diet (Medical Encyclopedia) Also in Spanish Topic Image MedlinePlus Email Updates Get Folic Acid updates ... acid - test Folic acid in diet Related Health Topics Vitamins National Institutes of Health The primary NIH ...

  9. Solid acid catalysis from fundamentals to applications

    CERN Document Server

    Hattori, Hideshi

    2014-01-01

    IntroductionTypes of solid acid catalystsAdvantages of solid acid catalysts Historical overviews of solid acid catalystsFuture outlookSolid Acids CatalysisDefinition of acid and base -Brnsted acid and Lewis acid-Acid sites on surfacesAcid strengthRole of acid sites in catalysisBifunctional catalysisPore size effect on catalysis -shape selectivity-Characterization of Solid Acid Catalysts Indicator methodTemperature programmed desorption (TPD) of ammoniaCalorimetry of adsorption of basic moleculesInfrare

  10. Uracil in formic acid hydrolysates of deoxyribonucleic acid

    Science.gov (United States)

    Schein, Arnold H.

    1966-01-01

    1. When DNA is hydrolysed with formic acid for 30min. at 175° and the hydrolysate is chromatographed on paper with propan-2-ol–2n-hydrochloric acid, in addition to expected ultraviolet-absorbing spots corresponding to guanine, adenine, cytosine and thymine, an ultraviolet-absorbing region with RF similar to that of uracil can be detected. Uracil was separated from this region and identified by its spectra in acid and alkali, and by its RF in several solvent systems. 2. Cytosine, deoxyribocytidine and deoxyribocytidylic acid similarly treated with formic acid all yielded uracil, as did a mixture of deoxyribonucleotides. 3. Approx. 4% of deoxyribonucleotide cytosine was converted into uracil by the formic acid treatment. ImagesFig. 1. PMID:5949371

  11. Uric acid nephrolithiasis: An update.

    Science.gov (United States)

    Cicerello, Elisa

    2018-04-01

    Uric acid nephrolithiasis appears to increase in prevalence. While a relationship between uric acid stones and low urinary pH has been for long known, additional association with various metabolic conditions and pathophysiological basis has recently been elucidated. Some conditions such as diabetes and metabolic syndrome disease, excessive dietary intake, and increased endogenous uric acid production and/or defect in ammoniagenesis are associated with low urinary pH. In addition, the phenomenon of global warming could result in an increase in areas with greater climate risk for uric acid stone formation. There are three therapeutic steps to be taken for management of uric acid stones: identification of urinary pH profiles, assessment of urinary volume status, and identification of disorders leading to excessive uric acid production. However, the most important factor for uric acid stone formation is acid urinary pH, which is a prerequisite for uric acid precipitation. This article reviews recent insights into the pathophysiology of uric acid stones and their management.

  12. Bile Acid Metabolism and Signaling

    Science.gov (United States)

    Chiang, John Y. L.

    2015-01-01

    Bile acids are important physiological agents for intestinal nutrient absorption and biliary secretion of lipids, toxic metabolites, and xenobiotics. Bile acids also are signaling molecules and metabolic regulators that activate nuclear receptors and G protein-coupled receptor (GPCR) signaling to regulate hepatic lipid, glucose, and energy homeostasis and maintain metabolic homeostasis. Conversion of cholesterol to bile acids is critical for maintaining cholesterol homeostasis and preventing accumulation of cholesterol, triglycerides, and toxic metabolites, and injury in the liver and other organs. Enterohepatic circulation of bile acids from the liver to intestine and back to the liver plays a central role in nutrient absorption and distribution, and metabolic regulation and homeostasis. This physiological process is regulated by a complex membrane transport system in the liver and intestine regulated by nuclear receptors. Toxic bile acids may cause inflammation, apoptosis, and cell death. On the other hand, bile acid-activated nuclear and GPCR signaling protects against inflammation in liver, intestine, and macrophages. Disorders in bile acid metabolism cause cholestatic liver diseases, dyslipidemia, fatty liver diseases, cardiovascular diseases, and diabetes. Bile acids, bile acid derivatives, and bile acid sequestrants are therapeutic agents for treating chronic liver diseases, obesity, and diabetes in humans. PMID:23897684

  13. Electrolytic nature of aqueous sulfuric acid. 2. Acidity.

    Science.gov (United States)

    Fraenkel, Dan

    2012-09-27

    In part 1 of this study, I reported that the Debye-Hückel limiting law and the smaller-ion shell (SiS) model of strong electrolyte solutions fit nicely with the experimental mean ionic activity coefficient (γ(±)) of aqueous sulfuric acid as a function of concentration and of temperature when the acid is assumed to be a strong 1-3 electrolyte. Here, I report that the SiS-derived activity coefficient of H(+), γ(H(+)), of the 1-3 acid is comparable to that of aqueous HCl. This agrees with titration curves showing, as well-known, that sulfuric acid in water is parallel in strength to aqueous HCl. The calculated pH is in good accord with the Hammett acidity function, H(0), of aqueous sulfuric acid at low concentration, and differences between the two functions at high concentration are discussed and explained. This pH-H(0) relation is consistent with the literature showing that the H(0) of sulfuric acid (in the 1-9 M range) is similar to those of HCl and the other strong mineral monoprotic acids. The titration of aqueous sulfuric acid with NaOH does not agree with the known second dissociation constant of 0.010 23; rather, the constant is found to be ~0.32 and the acid behaves upon neutralization as a strong diprotic acid practically dissociating in one step. A plausible reaction pathway is offered to explain how the acid may transform, upon base neutralization, from a dissociated H(4)SO(5) (as 3H(+) and HSO(5)(3-)) to a dissociated H(2)SO(4) even though the equilibrium constant of the reaction H(+) + HSO(5)(3-) ↔ SO(4)(2-) + H(2)O, at 25 °C, is 10(-37) (part 1).

  14. Counter current extraction of phosphoric acid: Food grade acid production

    International Nuclear Information System (INIS)

    Shlewit, H.; AlIbrahim, M.

    2009-01-01

    Extraction, scrubbing and stripping of phosphoric acid from the Syrian wet-phosphoric acid was carried out using Micro-pilot plant of mixer settler type of 8 l/h capacity. Tributyl phosphate (TBP)/di-isopropyl ether (DIPE) in kerosene was used as extractant. Extraction and stripping equilibrium curves were evaluated. The number of extraction and stripping stages to achieve the convenient and feasible yield was determined. Detailed flow sheet was suggested for the proposed continuous process. Data obtained include useful information for the design of phosphoric acid extraction plant. The produced phosphoric acid was characterized using different analytical techniques. (author)

  15. Acidizing reservoirs while chelating iron with sulfosalicylic acid

    Energy Technology Data Exchange (ETDEWEB)

    McLaughlin, W A; Berkshire, D C

    1980-09-30

    A well treating process is described in which an aqueous solution of a strong acid capable of dissolving solids in a manner increasing the permeability of a subterranean earth formation is injected into a subterranean reservoir that contains an asphaltenic oil. At least the first injected portion of the aqueous acid and a solution or homogeneous dispersion of at least enough 5-sulfosalicylic acid to chelate with and prevent the formation of iron-asphaltene solids are included with substantially all of the ferric ions that become dissolved within the strong acid solution that enters the earth formation. 10 claims.

  16. Danburite decomposition by sulfuric acid

    International Nuclear Information System (INIS)

    Mirsaidov, U.; Mamatov, E.D.; Ashurov, N.A.

    2011-01-01

    Present article is devoted to decomposition of danburite of Ak-Arkhar Deposit of Tajikistan by sulfuric acid. The process of decomposition of danburite concentrate by sulfuric acid was studied. The chemical nature of decomposition process of boron containing ore was determined. The influence of temperature on the rate of extraction of boron and iron oxides was defined. The dependence of decomposition of boron and iron oxides on process duration, dosage of H 2 SO 4 , acid concentration and size of danburite particles was determined. The kinetics of danburite decomposition by sulfuric acid was studied as well. The apparent activation energy of the process of danburite decomposition by sulfuric acid was calculated. The flowsheet of danburite processing by sulfuric acid was elaborated.

  17. Recovering uranium from phosphoric acid

    International Nuclear Information System (INIS)

    Anon.

    1979-01-01

    Wet-process phosphoric acid contains a significant amount of uranium. This uranium totals more than 1,500 tons/yr in current U.S. acid output--and projections put the uranium level at 8,000 tons/yr in the year 2000. Since the phosphoric acid is a major raw material for fertilizers, uranium finds its way into those products and is effectively lost as a resource, while adding to the amount of radioactive material that can contaminate the food chain. So, resource-conservation and environmental considerations both make recovery of the uranium from phosphoric acid desirable. This paper describes the newly developed process for recovering uranium from phosphoric acid by using solvent-extraction technique. After many extractants had been tested, the researchers eventually selected the combination of di (2-ethylhexyl) phosphoric acid (DEPA) and trioctylphosphine oxide (TOPO) as the most suitable. The flowscheme of the process is included

  18. Acid mine drainage

    Science.gov (United States)

    Bigham, Jerry M.; Cravotta, Charles A.

    2016-01-01

    Acid mine drainage (AMD) consists of metal-laden solutions produced by the oxidative dissolution of iron sulfide minerals exposed to air, moisture, and acidophilic microbes during the mining of coal and metal deposits. The pH of AMD is usually in the range of 2–6, but mine-impacted waters at circumneutral pH (5–8) are also common. Mine drainage usually contains elevated concentrations of sulfate, iron, aluminum, and other potentially toxic metals leached from rock that hydrolyze and coprecipitate to form rust-colored encrustations or sediments. When AMD is discharged into surface waters or groundwaters, degradation of water quality, injury to aquatic life, and corrosion or encrustation of engineered structures can occur for substantial distances. Prevention and remediation strategies should consider the biogeochemical complexity of the system, the longevity of AMD pollution, the predictive power of geochemical modeling, and the full range of available field technologies for problem mitigation.

  19. Dicarboxylic acids from electric discharge

    Science.gov (United States)

    Zeitman, B.; Chang, S.; Lawless, J. G.

    1974-01-01

    An investigation was conducted concerning the possible synthesis of a suite of dicarboxylic acids similar to that found in the Murchison meteorite. The investigation included the conduction of a chemical evolution experiment which simulated electric discharge through the primitive atmosphere of the earth. The suite of dicarboxylic acids obtained in the electric discharge experiment is similar to that of the Murchison meteorite, except for the fact that 2-chlorosuccinic acid is present in the spark discharge.

  20. Uranium extraction from phosphoric acid

    International Nuclear Information System (INIS)

    Araujo Figueiredo, C. de

    1984-01-01

    The recovery of uranium from phosphoric liquor by two extraction process is studied. First, uranium is reduced to tetravalent condition and is extracted by dioctypyrophosphoric acid. The re-extraction is made by concentrated phosphoric acid with an oxidizing agent. The re-extract is submitted to the second process and uranium is extracted by di-ethylhexilphosphoric acid and trioctylphosphine oxide. (M.A.C.) [pt