Search results for: hydroxy marilone C
Commenced in January 2007
Frequency: Monthly
Edition: International
Paper Count: 124

Search results for: hydroxy marilone C

124 Production of Hydroxy Marilone C as a Bioactive Compound from Streptomyces badius

Authors: Osama H. Elsayed, Mohsen M. S. Asker, Mahmoud A. Swelim, Ibrahim H. Abbas, Aziza I. Attwa, Mohamed E. El Awady

Abstract:

Hydroxy marilone C is a bioactive metabolite was produced from the culture broth of Streptomyces badius isolated from Egyptian soil. hydroxy marilone C was purified and fractionated by silica gel column with a gradient mobile phase dicloromethane (DCM) : Methanol then Sephadex LH-20 column using methanol as a mobile phase. It was subjected to many instruments as Infrared (IR), nuclear magnetic resonance (NMR), Mass spectroscopy (MS) and UV spectroscopy to the elucidation of its structure. It was evaluated for antioxidant, cytotoxicity against human alveolar basal epithelial cell line (A-549) and human breast adenocarcinoma cell line (MCF-7) and antiviral activities; showed that the maximum antioxidant activity was 78.8 % at 3000 µg/ml after 90 min. and the IC50 value against DPPH radical found about 1500 µg/ml after 60 min. By Using MTT assay the effect of the pure compound on the proliferation of A-549 cells and MCF-7 cells were 443 µg/ml and 147.9 µg/ml, respectively. While for detection of antiviral activity using Madin-Darby canine kidney (MDCK) cells the maximum cytotoxicity was at 27.9% and IC50 was 128.1µg/ml. The maximum concentration required for protecting 50% of the virus-infected cells against H1N1 viral cytopathogenicity (EC50) was 33.25% for 80 µg/ml. This results indicated that the hydroxy marilone C has a potential antitumor and antiviral activities.

Keywords: hydroxy marilone C, production, bioactive compound, Streptomyces badius

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123 Copper Related Toxicity of 1-Hydroxy-2-Thiopyridines

Authors: Elena G. Salina, Vadim A. Makarov

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With the emergence of primary resistance to the current drugs and wide distribution of latent tuberculosis infection, a need for new compounds with a novel mode of action is growing steadily. Copper-mediated innate immunity and antibacterial toxicity propose novel strategies in TB drug discovery and development. Transcriptome of M. tuberculosis was obtained by RNA-seq, intracellular copper content was measured by ISP MS and complexes of 1-hydroxy-2-thiopyridines with copper were detected by HPLC.1-hydroxy-2-thiopyridine derivatives were found to be highly active in vitro against both actively growing and dormant non-culturable M. tuberculosis. Transcriptome response to 1-hydroxy-2-thiopyridines revealed signs of copper toxicity in M. tuberculosis bacilli. Indeed, Cu was found to accumulate inside cells treated with 1-hydroxy-2-thiopyridines. These compounds were found to form stable charged lipophylic complexes with Cu²⁺ ions which transport into mycobacterial cell. Subsequent metabolic destruction of the complex led to transformation of 1-hydroxy-2-thiopyridines into 2-methylmercapto-2-ethoxycarbonylpyridines, which did not possess antitubercular activity and releasing of free Cu²⁺ in the cytoplasm. 1-hydroxy-2-thiopyridines are a potent class of Cu-dependent inhibitors of M. tuberculosis which may control M. tuberculosis infection by impairment of copper homeostasis. Acknowledgment: This work was financially supported by the Ministry of Education and Science of the RussianFederation (Agreement No 14.616.21.0065; unique identifier RFMEFI61616X0065).

Keywords: copper toxicity, drug discovery, M. tuberculosis inhibitors, 2-thiopyridines

Procedia PDF Downloads 143
122 Successful Immobilization of Alcohol Dehydrogenase on Natural and Synthetic Support and Its Reaction on Ethanol

Authors: Hiral D. Trivedi, Dinesh S. Patel, Sachin P. Shukla

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We have immobilized alcohol dehydrogenase on k-carrageenan, which is a natural polysaccharide obtained from seaweeds by entrapment and on copolymer of acrylamide and 2-hydroxy ethylmethaacrylate by covalent coupling. We have optimized all the immobilization parameters and also carried the comparison studies of both. In case of copolymer of acrylamide and 2-hydroxy ethylmethaacrylate, we have activated both the amino and hydroxyl group individually and simultaneously using different activating agents and obtained some interesting results. We have found that covalently bound enzyme was found to be better under all tested conditions. The reaction on ethanol was carried out using these immobilized systems.

Keywords: alcohol dehydrogenase, acrylamide-co-2-hydroxy ethylmethaacrylate, ethanol, k-carrageenan

Procedia PDF Downloads 115
121 Ultrasonic Investigation as Tool for Study of Molecular Interaction of 2-Hydroxy Substituted Pyrimidine Derivative at Different Concentrations

Authors: Shradha S. Binani, P. S. Bodke, R. V. Joat

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Recent decades have witnessed an exponential growth in the field of acoustical parameters and ultrasound on solid, liquid and gases. Ultrasonic propagation parameters yield valuable information regarding the behavior of liquid systems because intra and intermolecular association, dipolar interaction, complex formation and related structural changes affecting the compressibility of the system which in turn produces variations in the ultrasonic velocity. The acoustic and thermo dynamical parameters obtained in ultrasonic study show that ion-solvation is accompanied by the destruction or enhancement of the solvent structure. In the present paper the ultrasonic velocity (v), density (ρ), viscosity(η) have been measured for the pharmacological important compound 2-hydroxy substituted phenyl pyrimidine derivative (2-hydroxy-4-(4’-methoxy phenyl)-6-(2’-hydroxy-4’-methyl-5’-chlorophenyl)pyrimidine) in ethanol as a solvent by using different concentration at constant room temperature. These experimental data have been used to estimate physical parameter like adiabatic compressibility, intermolecular free length, relaxation time, free volume, specific acoustic impedance, relative association, Wada’s constant, Rao’s constant etc. The above parameters provide information in understanding the structural and molecular interaction between solute-solvent in the drug solution with respect to change in concentration.

Keywords: acoustical parameters, ultrasonic velocity, density, viscosity, 2-hydroxy substituted phenyl pyrimidine derivative

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120 Morphological Evaluation of Mesenchymal Stem Cells Derived from Adipose Tissue of Dog Treated with Different Concentrations of Nano-Hydroxy Apatite

Authors: K. Barbaro, F. Di Egidio, A. Amaddeo, G. Lupoli, S. Eramo, G. Barraco, D. Amaddeo, C. Gallottini

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In this study, we wanted to evaluate the effects of nano-hydroxy apatite (NHA) on mesenchymal stem cells extracted from subcutaneous adipose tissue of the dog. The stem cells were divided into 6 experimental groups at different concentrations of NHA. The comparison was made with a control group of stem cell grown in standard conditions without NHA. After 1 week, the cells were fixed with 10% buffered formalin for 1 hour at room temperature and stained with Giemsa, measured at the inverted optical microscope. The morphological evaluation of the control samples and those treated showed that stem cells adhere to the substrate and proliferate in the presence of nanohydroxy apatite at different concentrations showing no detectable toxic effects.

Keywords: nano-hydroxy apatite, adipose mesenchymal stem cells, dog, morphological evaluation

Procedia PDF Downloads 445
119 Sonochemical Zinc Oxide and Layered Hydroxy Zinc Acetate Synthesis in Fenton-Like Reactions

Authors: Durata Haciu, Ozgur Birer

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Zinc acetate solution is sonicated at high power in water and in ethanol in the absence and presence of various peroxides. In the absence of peroxides, the products are zinc oxide and layered hydroxy zinc acetate in water and in ethanol, respectively. Layered basic zinc acetate are prepared for the first time using sonochemical methods. The addition of peroxides alters the reaction mechanisms. In water, insoluble peroxides produce zinc oxides while the water soluble peroxide, i.e.hydrogen peroxide, completely destroyed the structure and casted a doubt on the accepted peroxide initiated mechanism of reactions. In ethanol,peroxide addition caused the reaction mechanism to change and some oxide formation is observed. The reaction mechanism is sensitive to water/ethanol amounts as well as the peroxide to zinc ion mole ratio.Thin zinc oxide wafers (ca. 30 nm) with band gaps of 3.24 eV were obtained.

Keywords: ultrasound, zinc oxide, hydroxy zinc acetate, fenton, peroxide initiation

Procedia PDF Downloads 265
118 Effect of Ethyl Cellulose and Hydroxy Propyl Methyl Cellulose Polymer on the Release Profile of Diltiazem Hydrochloride Sustained Release Pellets

Authors: Shahana Sharmin

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In the present study, the effect of cellulose polymers Ethyl Cellulose and Hydroxy Propyl Methyl Cellulose was evaluated on the release profile of drug from sustained release pellet. Diltiazem Hydrochloride, an antihypertensive, cardio-protective agent and slow channel blocker were used as a model drug to evaluate its release characteristics from different pellets formulations. Diltiazem Hydrochloride sustained release pellets were prepared by drug loading (drug binder suspension) on neutral pellets followed by different percentages of spraying, i.e. 2%,4%, 6%, 8% and 10% coating suspension using ethyl cellulose and hydroxy-propyl methyl cellulose polymer in a fixed 85:15 ratios respectively. The in vitro dissolution studies of Diltiazem Hydrochloride from these sustained release pellets were carried out in pH 7.2 phosphate buffer for 1, 2, 3, 4, 5, 6, 7, and 8 hrs using USP-I method. Statistically, significant differences were found among the drug release profile from different formulations. Polymer content with the highest concentration of Ethyl cellulose on the pellets shows the highest release retarding rate of the drug. The retarding capacity decreases with the decreased concentration of ethyl cellulose. The release mechanism was explored and explained with zero order, first order, Higuchi and Korsmeyer’s equations. Finally, the study showed that the profile and kinetics of drug release were functions of polymer type, polymer concentration & the physico-chemical properties of the drug.

Keywords: diltiazem hydrochloride, ethyl cellulose, hydroxy propyl methyl cellulose, release kinetics, sustained release pellets

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117 Boryl Radical-Promoted Dehydroxylative Alkylation of 3-Hydroxyoxindole Derivatives

Authors: Tesfaye Tebeka Simur, Tian-Yu Peng, Yi-Feng Wang, Xiu-Wei Wu, Feng-Lian Zhang

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A boryl radical-promoted dehydroxylative alkylation of 3-hydroxy-oxindole derivatives is achieved. The reaction starts from addition of 4-dimethylaminopyridine (DMAP)-boryl radical to the amide carbonyl oxygen atom, which induces a spin-center shift process to promote the C−O bond cleavage. The elimination of a hydroxide anion from a free hydroxy group is also accomplished. Capture of the generated carbon radical with alkenes furnishes a variety of C-3 alkylated oxindoles. This method features a simple operation and broad substrate scope.

Keywords: boryl radical, C-O, C-F, C=C, C=N bond activation, spin center shift

Procedia PDF Downloads 61
116 Design and Development of Bioactive a-Hydroxy Carboxylate Group Modified MnFe₂O₄ Nanoparticle: Comparative Fluorescence Study, Magnetism and DNA Nuclease Activity

Authors: Indranil Chakraborty, Kalyan Mandal

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Three new α-hydroxy carboxylate group functionalized MnFe₂O₄ nanoparticles (NPs) have been developed to explore the microscopic origin of ligand modified fluorescence and magnetic properties of nearly monodispersed MnFe₂O₄ NPs. The surface functionalization has been carried out with three small organic ligands (tartrate, malate, and citrate) having different number of α-hydroxy carboxylate functional group along with steric effect. Detailed study unveils that α-hydroxy carboxylate moiety of the ligands plays key role to generate intrinsic fluorescence in functionalized MnFe₂O₄ NPs through the activation of ligand to metal charge transfer transitions, associated with ligand-Mn²⁺/Fe³⁺ interactions along with d-d transition corresponding to d-orbital energy level splitting of Fe³⁺ ions on NP surface. Further, MnFe₂O₄ NPs show a maximum 140.88% increase in coercivity and 97.95% decrease in magnetization compared to its bare one upon functionalization. The ligands that induce smallest crystal field splitting of d-orbital energy level of transition metal ions are found to result in strongest ferromagnetic activation of the NPs. Finally, our developed tartrate functionalized MnFe₂O₄ (T-MnFe₂O₄) NPs have been utilized for studying DNA binding interaction and nuclease activity for stimulating their beneficial activities toward diverse biomedical applications. The spectroscopic measurements indicate that T-MnFe₂O₄ NPs bind calf thymus DNA by intercalative mode. The ability of T-MnFe₂O₄ NPs to induce DNA cleavage was studied by gel electrophoresis technique where the complex is found to promote the cleavage of pBR322 plasmid DNA from the super coiled form I to linear coiled form II and nicked coiled form III with good efficiency. This may be taken into account for designing new biomolecular detection agents and anti-cancer drug which can open up a new door toward diverse non-invasive biomedical applications.

Keywords: MnFe₂O₄ nanoparticle, α-hydroxy carboxylic acid, comparative fluorescence, magnetism study, DNA interaction, nuclease activity

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115 Functionalization of Carboxylated Single-Walled Carbon Nanotubes with 2-En 4-Hydroxy Cyclo 1-Octanon and Toxicity Investigation

Authors: D. ChobfroushKhoei, S. K. Heidari , Sh. Dariadel

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Carbon nanotubes were used in medical sciences especially in drug delivery system and cancer therapy. In this study, we functionalized carboxylated single-wall carbon nanotubes (SWNT-COOH) with 2-en 4-hydroxy cyclo 1-octanon. Synthesized sample was characterized by FT-IR, Raman spectroscopy, SEM, TGA and cellular investigations. The results showed well formation of SWNT-Ester. Cell viability assay results and microscopic observations demonstrated that cancerous cells were killed in the sample. The synthesized sample can be used as a toxic material for cancer therapy.

Keywords: MWNT-COOH, functionalization, phenylisocyanate, phenylisothiocyanate, 1, 4-phenylendiamine, toxicity investigation

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114 Acanthopanax koreanum and Major Ingredient, Impressic Acid, Possess Matrix Metalloproteinase-13 Down-Regulating Capacity and Protect Cartilage Destruction

Authors: Hyun Lim, Dong Sook Min, Han Eul Yun, Kil Tae Kim, Ya Nan Sun, Young Ho Kim, Hyun Pyo Kim

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Matrix metalloproteinase (MMP)-13 has an important role for degrading cartilage materials under inflammatory conditions such as arthritis. Since the 70% ethanol extract of Acanthopanax koreanum inhibited MMP-13 expression in IL-1β-treated human chondrocyte cell line, SW1353, two major constituents including acanthoic acid and impressic acid were initially isolated from the same plant materials and their MMP-13 down-regulating capacity was examined. In IL-1β-treated SW1353 cells, acanthoic acid and impressic acid significantly and concentration-dependently inhibited MMP-13 expression at 10 – 100 μM and 0.5 – 10 μM, respectively. The potent one, impressic acid, was found to inhibit MMP-13 expression by blocking the phosphorylation of signal transducer and activator of transcription-1/-2 (STAT-1/-2) and activation of c-Jun and c-Fos among cellular signaling pathway involved, but did not affect the activation of mitogen-activated protein kinases (MAPKs) and nuclear transcription factor-κB (NF-κB). Further, impressic acid was also found to inhibit the expression of MMP-13 mRNA (47.7% inhibition at 10 μM), the glycosaminoglycan release (42.2% reduction at 10 μM) and proteoglycan loss in IL-1-treated rabbit cartilage explants culture. For a further study, 21 impressic acid derivatives were isolated from the same plant materials and their suppressive activities against MMP-13 expression were examined. Among the derivatives, 3α-hydroxy-lup-20(29)-en-23-oxo,28-oic acid, (20R)-3α-hydroxy-29-dimethoxylupan-23,28-dioic acid, acankoreoside F and acantrifoside A clearly down-regulated MMP-13 expression, but impressic acid being most potent. All these results suggest that impressic acid, 3α-hydroxy-lup-20(29)-en-23-oxo,28-oic acid, (20R)-3α-hydroxy-29-dimethoxylupan-23,28-dioic acid, acankoreoside F, acantrifoside A and A. koreanum may have a potential for therapeutic agents to prevent cartilage degradation possibly by inhibiting matrix protein degradation.

Keywords: acanthoic acid, Acanthopanax koreanum, cartilage, impressic acid, matrix metalloproteinase

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113 Research and Innovation Centre

Authors: Krasimir Ivanov, Tonyo Tonev, Nguyen Nguyen, Alexander Peltekov, Anyo Mitkov

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Maize is among the most economically important crops and at the same time one of the most sensitive to soil deficiency in zinc. In this paper, the impact of the foliar zinc application in the form of zinc hydroxy nitrate suspension on the micro and macro elements partitioning in maize leaves and grain was studied during spring maize season, 2017. The impact of the foliar zinc fertilization on the grain yield and quality was estimated too. The experiment was performed by the randomized block design with 8 variants in 3 replications. Seven suspension solutions whit different Zn concentration were used, including ZnO suspension and zinc hydroxyl nitrate alone or nixed with other nutrients. Fertilization and irrigation were the same for all variants. The Zn content and the content of selected micro (Cu, Fe) and macro (Ca, Mg, P and K) elements in maize leaves were determined two weeks after the first spraying (5-6 sheets), two weeks after the second spraying (9-10 sheets) and after harvesting. It was concluded that the synthesized zinc hydroxy nitrate demonstrates potential as the long-term foliar fertilizer. A significant (p < 0.05) effect of zinc accumulation in maize leaves by foliar zinc application during the first growth stage was found, followed by its reutilization to other plants organs during the second growth stage. Significant export of Cu, P, and K from lower and middle leaves was observed. The content of Ca and Mg remains constant in the whole longevity period, while the content of Fe decreases sharply.

Keywords: foliar fertilization, zinc hydroxy nitrate, maize, zinc

Procedia PDF Downloads 131
112 Anti-Bacterial Activity Studies of Derivatives of 6β-Hydroxy Betunolic Acid against Selected Stains of Gram (+) and Gram (-) Bacteria

Authors: S. Jayasinghe, W. G. D. Wickramasingha, V. Karunaratne, D. N. Karunaratne, A. Ekanayake

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Multi-drug resistant microbial pathogens are a serious global health problem, and hence, there is an urgent necessity for discovering new drug therapeutics. However, finding alternatives is a one of the biggest challenges faced by the global drug industry due to the spiraling high cost and serious side effects associated with modern medicine. On the other hand, plants and their secondary metabolites can be considered as good sources of scaffolds to provide structurally diverse bioactive compounds as potential therapeutic agents. 6β-hydroxy betunolic acid is a triterpenoid isolated from bark of Schumacheria castaneifolia which is an endemic plant to Sri Lanka which has shown antibacterial activity against both Staphylococcus aureus (ATCC 29213) and methicillin-resistant S. aureus with Minimum Inhibition Concentration (MIC) of 16 µg/ml. The objective of this study was to determine the anti-bacterial activity for the derivatives of 6β- hydroxy betunolic acid against standard strains of Staphylococcus aureus (ATCC 29213 and ATCC 25923), Enterococcus faecalis (ATCC 29212), Escherichia coli (ATCC 35218 and ATCC 25922), Pseudomonas aeruginosa (ATCC 27853), carbepenemas produce Kebsiella pneumonia (ATCC BAA 1705) and carbepenemas non produce Kebsiella pneumonia (ATCC BAA 1706) and four stains of clinically isolated methicillin resistance S. aureus and Acinetobacter. Structural analogues of 6β-hydroxy betunolic acid were synthesized by modifying the carbonyl group at C-3 to obtain olefin and oxime, the hydroxyl group at C-6 position to a ketone, the carboxylic acid at C-17 to obtain amide and halo ester and the olefin group at C-20 position to obtain epoxide. Chemical structures of the synthesized analogues were confirmed with spectroscopic data and antibacterial activity was determined through broth micro dilution assay. Results revealed that 6β- hydroxy betunolic acid shows significant antibacterial activity only against the Gram positive strains and it was inactive against all the tested Gram negative strains for the tested concentration range. However, structural modifications into oxime and olefin at C-3, ketone at C-6 and epoxide at C-20 decreased its antibacterial activity against the gram positive organisms and it was totally lost with the both modifications at C-17 into amide and ester. These results concluded that the antibacterial activity of 6β- hydroxy betunolic acid and derivatives is predominantly depending on the cell wall difference of the bacteria and the presence of carboxylic acid at C-17 is highly important for the antibacterial activity against Gram positive organisms.

Keywords: antibacterial activity, 6β- hydroxy betunolic acid, broth micro dilution assay, structure activity relationship

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111 Role of NaOH in the Synthesis of Waste-derived Solid Hydroxy Sodalite Catalyst for the Transesterification of Waste Animal Fat to Biodiesel

Authors: Thomas Chinedu Aniokete, Gordian Onyebuchukwu Mbah, Michael Daramola

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A sustainable NaOH integrated hydrothermal protocol was developed for the synthesis of waste-derived hydroxy sodalite catalysts for transesterification of waste animal fat (WAF) with a high per cent free fatty acid (FFA) to biodiesel. In this work, hydroxy sodalite catalyst was synthesized from two complex waste materials namely coal fly ash (CFA) and waste industrial brine (WIB). Measured amounts of South African CFA and WIB obtained from a coal mine field were mixed with NaOH solution at different concentrations contained in secured glass vessels equipped with magnetic stirrers and formed consistent slurries after aging condition at 47 oC for 48 h. The slurries were then subjected to hydrothermal treatments at 140 oC for 48 h, washed thoroughly and separated by the action of a centrifuge on the mixture. The resulting catalysts were calcined in a muffle furnace for 2 h at 200 oC and subsequently characterized for different effects using X-ray diffraction (XRD), scanning electron microscopy (SEM), Fourier transform infrared (FT-IR), and Bennett Emmet Teller (BET) adsorption-desorption techniques. The produced animal fat methyl ester (AFME) was analyzed using the gas chromatography-mass spectrometry (GC-MS) method. Results of the investigation indicate profoundly an enhanced catalyst purity, textural property and desired morphology due to the action of NaOH. Similarly, the performance evaluation with respect to catalyst activity reveals a high catalytic conversion efficiency of 98 % of the high FFA WAF to biodiesel under the following reaction conditions; a methanol-to-WAF ratio of 15:1, amount of SOD catalyst of 3 wt % with a stirring speed of 300-500 rpm, a reaction temperature of 60 oC and a reaction time of 8 h. There was a recovered 96 % stable catalyst after reactions and potentially recyclable, thus contributing to the economic savings to the process that had been a major bottleneck to the production of biodiesel. This NaOH route for synthesizing waste-derived hydroxy sodalite (SOD) catalyst is a sustainable and eco-friendly technology that speaks directly to the global quest for renewable-fossil fuel controversy enforcing sustainable development goal 7.

Keywords: coal fly ash, waste industrial brine, waste-derived hydroxy sodalite catalyst, sodium hydroxide, biodiesel, transesterification, biomass conversion

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110 25-Hydroxy Vit D, Adiponectin Levels and Cardiometabolic Risk Factors in a Sample of Obese Children

Authors: Nayera E. Hassan, Sahar A. El-Masry, Rokia A. El Banna, Mones M. Abu Shady, Muhammad Al-Tohamy, Manal Mouhamed Ali, Mehrevan M. Abd El-Moniem, Mona Anwar

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Association between vitamin D, adiponectin and obesity is a matter of debate, as they play important role in linking obesity with different cardiometabolic risk factors. Objectives: Evaluation of the association between metabolic risk factors with both adiponectin and vitamin D levels and that between adiponectin and vitamin D among obese Egyptian children. Subjects and Methods: This case-control cross-sectional study consisted of 65 obese and 30 healthy children, aged 8-11 years. 25-hydroxy vitamin D (25(OH) D) level, serum adiponectin, total cholesterol (TC), triglycerides (TG), high-density lipoprotein-cholesterol (HDL-C) and low-density lipoprotein-cholesterol (LDL-C) were measured. Results: The mean 25(OH) D levels in the obese and control groups were 29.9± 10.3 and 39.7 ± 12.7 ng/mL respectively (P < 0.001). The mean 25(OH) D and adiponectin levels in the obese were lower than that in the control group (P < 0.0001). 25(OH) D were inversely correlated with body mass index (BMI), triglyceride, total cholesterol and LDL-cholesterol (LDL-C), while adiponectin level were inversely correlated with systolic blood pressure (SBP), and diastolic blood pressure (DBP), and positively correlated with HDL-C. However, there is no relation between 25(OH) D and adiponectin levels among obese children and total sample. Conclusion: In spite of strong association between vitamin D and adiponectin levels with metabolic risk factors and obesity, there is no relation between 25(OH) D and adiponectin levels. In obese children, there are significant negative correlations between 25(OH) D with lipid profile, and between adiponectin levels with blood pressure. At certain adiponectin level, the relation between it and BMI disappears.

Keywords: 25-hydroxy vitamin D, adiponectin, lipid profile, blood pressure, children

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109 Flavonoids and Phenolic Acids from the Aerial Parts of Alyssum alyssoides

Authors: Olga St. Tsiftsoglou, Diamanto M. Lazari, Eugene L. Kokkalou

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Most of Alyssum species of Brassicaceae family have been mainly studied for their contribution in ecology. In this study, A. alyssoides was examined for its chemical substitutes. The methanol extract of its aerial parts was fractionated with liquid-liquid extraction (distribution) with four different solvents of increasing polarity: diethyl ether, ethyl acetate, 1-butanol and water. The diethyl ether and ethyl acetate extracts were further studied for their chemical composition. So far, secondary metabolites which belong to phenolics were isolated by using several chromatographic methods (C.C. and HPLC) and were identified by using spectroscopic methods (UV/Vis, NMR and MS): two phenolic acids (p-hydroxy-benzoic acid and 3-methoxy-4-hydroxy-benzoic acid (vanillic acid)), and five flavonoids, which are derivatives of flavonol: kaempferol 3-O-β-D-glucopyranoside (astragalin), kaempferol 3-O-(6′′-α-L-rhamnopyranosyl)-β-D-glucopyranoside (nicotiflorin), quercetin 3-O-β-D-glucopyranoside (isoquercetin), isorhamnetin-3-O-β-D-glucopyranoside, and isoramnetin 3-O-(6′′-α-L-rhamnopyranosyl)-β-D-glucopyranoside (narcissin).

Keywords: Alyssum, chemical substitutes, flavonoids, phenolic acids

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108 Anti-Aging Effects of Retinol and Alpha Hydroxy Acid on Elastin Fibers of Artificially Photo-Aged Human Dermal Fibroblast Cell Lines

Authors: Mohammed Jarrar, Shalini Behl, Nadia Shaheen, Abeer Fatima, Reem Nasab

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Skin aging is a slow multifactorial process influenced by both internal as well as external factors. Ultra-violet radiations (UV), diet, smoking and personal habits are the most common environmental factors that affect skin aging. Fat contents and fibrous proteins as collagen and elastin are core internal structural components. The direct influence of UV on elastin integrity and health is crucial on aging of skin by time. The deposition of abnormal elastic material is a major marker in a photo-aged skin. Searching for compounds that may protect against cutaneous photo-damage is highly valued. Retinoids and Alpha Hydroxy Acids protective and or repairing effects of UV have been endorsed by some researchers. For consolidating a better understanding of anti and protective effects of such anti-aging agents, we evaluated the combinatory effects of various dosages of lactic acid and retinol on the dermal fibroblasts elastin levels exposed to UV. The UV exposed cells showed significant reduction in the elastin levels. A combination of drugs with a higher concentration of lactic acid (30-35 mM) and a lower concentration of retinol (10-15mg/mL) showed to work better in enhancing elastin concentration in UV exposed cells. We assume this enhancement could be the result of increased tropo-elastin gene expression stimulated by retinol and lactic acid probably repaired the UV irradiated damage by enhancing the amount and integrity of the elastin fibers.

Keywords: alpha hydroxy acid, elastin, retinol, ultraviolet radiations

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107 New Quinazoline Derivative Induce Cytotoxic Effect against Mcf-7 Human Breast Cancer Cell

Authors: Maryam Zahedi Fard, Nazia Abdul Majid, Hapipah Mohd Ali, Mahmood Ameen Abdulla

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New quinazoline schiff base 3-(5-bromo-2-hydroxy-3-methoxybenzylideneamino)-2-(5-bromo-2-hydroxy-3-methoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one was investigated for anticancer activity against MCF-7 human breast cancer cell line with involved mechanism of apoptosis. The compound demonstrated a remarkable antiproliferative effect, with an IC50 value of 3.41 ± 0.34, after 72 hours of treatment. Morphological apoptotic features in treated MCF-7 cells were observed by AO/PI staining. Furthermore, treated MCF-7 cells subjected to apoptosis death, as exhibited by perturbation of mitochondrial membrane potential and cytochrome c release as well as increase in ROS generation. We also found activation of caspases 3/7 and -9. Moreover, acute toxicity test demonstrated the nontoxic nature of the compound in mice. Our results showed the selected compound significantly induce apoptosis in MCF-7 cells via intrinsic pathway, which might be considered as a potent candidate for further in vivo and clinical breast cancer studies.

Keywords: antiproliferative effect, MCF-7 human breast cancer cell line, apoptosis, caspases

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106 Production of Antimicrobial Agents against Multidrug-Resistant Staphylococcus aureus through the Biocatalysis of Vegetable Oils

Authors: Hak-Ryul Kim, Hyung-Geun Lee, Qi Long, Ching Hou

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Structural modification of natural lipids via chemical reaction or microbial bioconversion can change their properties or even create novel functionalities. Enzymatic oxidation of lipids leading to formation of oxylipin is one of those modifications. Hydroxy fatty acids, one of those oxylipins have gained important attentions because of their structural and functional properties compared with other non-hydroxy fatty acids. Recently 7,10-dihydroxy-8(E)-octadecenoic acid (DOD) was produced with high yield from lipid-containing oleic acid by microbial conversion, and the further study confirmed that DOD contained strong antimicrobial activities against a broad range of microorganisms. In this study, we tried to modify DOD molecules by the enzymatic or physical reaction to create new functionality or to enhance the antimicrobial activity of DOD. After modification of DOD molecules by different ways, we confirmed that the antimicrobial activity of DOD was highly enhanced and presented strong antimicrobial activities against multidrug-resistant Staphylococcus aureus, suggesting that DOD and its derivatives can be used as efficient antimicrobial agents for medical and industrial applications.

Keywords: biocatalysis, antimicrobial agent, multidrug-resistant bacteria, vegetable oil

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105 Synthesis, Inhibitory Activity, and Molecular Modelling of 2-Hydroxy-3-Oxo-3-Phenylpropionate Derivatives as HIV-1-Integrase Inhibitors

Authors: O. J. Jesumoroti, Faridoon, R. Klein, K. A. Iobb, D. Mnkadhla, H. C. Hoppe, P. T. Kaye

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The 1, 3-aryl diketo acids (DKA) based agents represent an important class of HIV integrase (IN) strand transfer inhibitors. In other to study the chelating role of the divalent metal ion in the inhibition of IN strand transfer, we designed and synthesized a series of 2-hydroxy-3-oxo-3-phenyl propionate derivatives with the notion that such compounds could interact with the divalent ion in the active site of IN. The synthetic sequence to the desired compounds involves the concept of Doebner knoevenagel condensation, Fischer esterification and ketohydroxylation using neuclophilic re-oxidant; compounds were characterized by their IR, IHNMR, 13CNMR, HRMS spectroscopic data and melting point determination. Also, molecular docking was employed in this study and it was revealed that there is interaction with the active site of the enzyme. However, there is disparity in the corresponding anti-HIV activity determined by the experimental bioassay. These compounds lack potency at low micromolar concentration when compared to the results of the docking studies. Nevertheless, the results of the study suggest modification of the aryl ring with one or two hydroxyl groups to improve the inhibitory activity.

Keywords: anti-HIV-1 integrase, ketohydroxylation, molecular docking, propionate derivatives

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104 Cardioprotective Effect of Oleanolic Acid and Urosolic Acid against Doxorubicin-Induced Cardiotoxicity in Rats

Authors: Sameer N. Goyal, Chandragauda R. Patil

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Oleanolic acid (3/3-hydroxy-olea-12-en-28-oic acid) and its isomer, Ursolic acid (38-hydroxy-urs-12-en-28-oic acid) are triterpenoids compounds which exist widely in plant kingdom in the free acid form or as glycosidic triterpenoids saponins. The aim of the study is to evaluate intravenously administered oleanolic acid and ursolic acid in doxorubicin induced cardiotoxicity. Cardiotoxicity was induced in albino wistar rat with single intravenous injection of doxorubicin at dose of 67.75mg/kg i.v for 48 hrs at 12 hrs interval following doxorubicin administration in the same model cardioprotective effect of amifostine (90 mg/kg i.v, single dose prior 30 min before doxorubicin administration) was evaluated as standard treatment. Induction of cardiotoxicity was confirmed by rise in cardiac markers in serum such as CK–MB, LDH and also by electrocardiographically. The doxorubicin treated group significantly increased in QT interval, serum CK-MB, serum LDH, SGOT, SGPT and antioxidant parameter. Both the treatment group showed significant protective effect on Hemodynamic, electrocardiographic, biochemical, and antioxidant parameters. The oleanolic acid showed slight protective effect in histological lesions in doxorubicin induced cardiotoxicity. Hence, the results indicate that Oleanolic acid has more cardioprotective potential than ursolic acid against doxorubicin induced cardiotoxicity in rats.

Keywords: cardioprotection, doxorubicin, oleanolic acid, ursolic acid

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103 Keto-Enol Tautomerism of Salicylideneaniline Substituted

Authors: Rihana Hadjeb, Djamel Barkat

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Schiff bases derived from o-hydroxybenzaldehyde has attracted a great interest not only for its promising applications towards linear and non-linear optical properties, biological activity and technological applications but also used as model compounds for the theory of hydrogen bonding. Due to its intramolecular hydrogen bonding, depending on the position of proton in the hydrogen bond o-hydroxy salicylidene Schiff bases exhibit two tautomeric forms, enol-imine (E-form) and keto-enamine (K-form) both in solution and in crystalline state. A zwitterionic structure also appears due to a proton transfer in enol – imine and keto – amine tautomer. These classes of compounds also exhibit thermochromic and photochromic behavior. We undertook in this study the synthesis of ten compounds of hydroxy Schiff bases from the condensation of salicylic aldehyde and aniline substituted in the ortho, meta and para by the methyl, chloro and nitro groups. To study the keto-enol equilibrium of the compounds; UV-VIS spectra were studied in different polarity solvents. The compounds were in tautomeric equilibrium (enol imine O–H•••N, keto-amine O•••H–N forms). For some derivatives of salicylideneanilines the keto-amine form was observed in both ethanol and dioxane. IR results showed that all Schiff bases studied favor the enol-imine form over the keto form.

Keywords: salicylideneaniline, tautomerism, keto-enol equilibrium, UV-VIS spectroscopy, solvent effect

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102 The Impact of Efflux Pump Inhibitor on the Activity of Benzosiloxaboroles and Benzoxadiboroles against Gram-Negative Rods

Authors: Agnieszka E. Laudy, Karolina Stępien, Sergiusz Lulinski, Krzysztof Durka, Stefan Tyski

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1,3-dihydro-1-hydroxy-2,1-benzoxaborole and its derivatives are a particularly interesting group of synthetic agents and were successfully employed in supramolecular chemistry medicine. The first important compounds, 5-fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole and 5-chloro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole were identified as potent antifungal agents. In contrast, (S)-3-(aminomethyl)-7-(3-hydroxypropoxy)-1-hydroxy-1,3-dihydro-2,1-benzoxaborole hydrochloride is in the second phase of clinical trials as a drug for the treatment of Gram-negative bacterial infections of the Enterobacteriaceae family and Pseudomonas aeruginosa. Equally important and difficult task is to search for compounds active against Gram-negative bacilli, which have multi-drug-resistance efflux pumps actively removing many of the antibiotics from bacterial cells. We have examined whether halogen-substituted benzoxaborole-based derivatives and their analogues possess antibacterial activity and are substrates for multi-drug-resistance efflux pumps. The antibacterial activity of 1,3-dihydro-3-hydroxy-1,1-dimethyl-1,2,3-benzosiloxaborole and 10 halogen-substituted its derivatives, as well as 1,2-phenylenediboronic acid and 3 synthesised fluoro-substituted its analogs, were evaluated. The activity against the reference strains of Gram-positive (n=5) and Gram-negative bacteria (n=10) was screened by the disc-diffusion test (0.4 mg of tested compounds was applied onto paper disc). The minimal inhibitory concentration values and the minimal bactericidal concentration values were estimated according to The Clinical and Laboratory Standards Institute and The European Committee on Antimicrobial Susceptibility Testing recommendations. During the minimal inhibitory concentration values determination with or without phenylalanine-arginine beta-naphthylamide (50 mg/L) efflux pump inhibitor, the concentrations of tested compounds ranged 0.39-400 mg/L in the broth medium supplemented with 1 mM magnesium sulfate. Generally, the studied benzosiloxaboroles and benzoxadiboroles showed a higher activity against Gram-positive cocci than against Gram-negative rods. Moreover, benzosiloxaboroles have the higher activity than benzoxadiboroles compounds. In this study, we demonstrated that substitution (mono-, di- or tetra-) of 1,3-dihydro-3-hydroxy-1,1-dimethyl-1,2,3-benzosiloxaborole with halogen groups resulted in an increase in antimicrobial activity as compared to the parent substance. Interestingly, the 6,7-dichloro-substituted parent substance was found to be the most potent against Gram-positive cocci: Staphylococcus sp. (minimal inhibitory concentration 6.25 mg/L) and Enterococcus sp. (minimal inhibitory concentration 25 mg/L). On the other hand, mono- and dichloro-substituted compounds were the most actively removed by efflux pumps present in Gram-negative bacteria mainly from Enterobacteriaceae family. In the presence of efflux pump inhibitor the minimal inhibitory concentration values of chloro-substituted benzosiloxaboroles decreased from 400 mg/L to 3.12 mg/L. Of note, the highest increase in bacterial susceptibility to tested compounds in the presence of phenylalanine-arginine beta-naphthylamide was observed for 6-chloro-, 6,7-dichloro- and 6,7-difluoro-substituted benzosiloxaboroles. In the case of Escherichia coli, Enterobacter cloacae and P. aeruginosa strains at least a 32-fold decrease in the minimal inhibitory concentration values of these agents were observed. These data demonstrate structure-activity relationships of the tested derivatives and highlight the need for further search for benzoxaboroles and related compounds with significant antimicrobial properties. Moreover, the influence of phenylalanine-arginine beta-naphthylamide on the susceptibility of Gram-negative rods to studied benzosiloxaboroles indicate that some tested agents are substrates for efflux pumps in Gram-negative rods.

Keywords: antibacterial activity, benzosiloxaboroles, efflux pumps, phenylalanine-arginine beta-naphthylamide

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101 Algal/Bacterial Membrane Bioreactor for Bioremediation of Chemical Industrial Wastewater Containing 1,4 Dioxane

Authors: Ahmed Tawfik

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Oxidation of 1,4 dioxane produces metabolites by-products involving glycolaldehyde and acids that have geno- and cytotoxicity impact on microbial degradation. Thereby, the incorporation of algae with bacteria in the treatment system would eliminate and overcome the accumulation of metabolites that are utilized as a carbon source for the build-up of biomass. Therefore, the aim of the present study is to assess the potential of algae/bacteria-based membrane bioreactor (AB-MBR) for biodegradation of 1,4 dioxane-rich wastewater at a high imposed loading rate. Three identical reactors, i.e., AB-MBR1, AB-MBR2, and AB-MBR3, were operated in parallel at 1,4 dioxane loading rates of 641.7, 320.9, and 160.4 mg/L. d., and HRTs of 6.0, 12 and 24 h. respectively. The AB-MBR1 achieved 1,4 dioxane removal rate of 263.7 mg/L.d., where the residual value in the treated effluent amounted to 94.4±22.9 mg/L. Reducing the 1,4 dioxane loading rate (LR) to 320.9 mg/L.d in the AB-MBR2 maximized the removal rate efficiency of 265.9 mg/L.d., with a removal efficiency of 82.8±3.2%. The minimum value of 1,4 dioxane of 17.3±1.8 mg/L in the treated effluent of AB-MBR3 was obtained at an HRT of 24.0 h and loading rate of 160.4 mg/L.d. The mechanism of 1,4 dioxane degradation in AB-MBR was a combination of volatilization (8.03±0.6%), UV oxidation (14.1±0.9%), microbial biodegradation (49.1±3.9%) and absorption/uptake and assimilation by algae (28.8±2.%). Further, the Thioclava, Afipia, and Mycobacterium genera oxidized and produced the required enzymes for hydrolysis and cleavage of the dioxane ring into 2-hydroxy-1,4 dioxane. Moreover, the fungi, i.e., Basidiomycota and Cryptomycota, played a big role in the degradation of the 1,4 dioxane into 2-hydroxy-1,4 dioxane. Xanthobacter and Mesorhizobium were involved in the metabolism process by secreting alcohol dehydrogenase (ADH), aldehyde dehydrogenase (ALDH), and glycolate oxidase. Bacteria and fungi produced dehydrogenase (DH) for the transformation of 2-hydroxy-1,4 dioxane into 2-hydroxy-ethoxyacetaldehyde. The latter is converted into Ethylene glycol by Aldehyde hydrogenase (ALDH). Ethylene glycol is oxidized into acids using Alcohol hydrogenase (ADH). The Diatomea, Chlorophyta, and Streptophyta utilize the metabolites for biomass assimilation and produce the required oxygen for further oxidation of the dioxane and its metabolites by-products of bacteria and fungi. The major portion of metabolites (ethylene glycol, glycolic acid, and oxalic acid were removed due to uptake and absorption by algae (43±4.3%), followed by adsorption (18.4±0.9%). The volatilization and UV oxidation contribution for the degradation of metabolites were 8.7±0.7% and 12.3±0.8%, respectively. The capabilities of genera Defluviimonas, Thioclava, Luteolibacter, and Afipia. The genera of Defluviimonas, Thioclava, Luteolibacter, and Mycobacterium were grown under a high 1,4 dioxane LR of 641.7 mg/L.d. The Chlorophyta (4.1-43.6%), Streptophyta (2.5-21.7%), and Diatomea (0.8-1.4%) phyla were dominant for degradation of 1,4 dioxane. The results of this study strongly demonstrated that the bioremediation and bioaugmentation process can safely remove 1,4 dioxane from industrial wastewater while minimizing environmental concerns and reducing economic costs.

Keywords: wastewater, membrane bioreactor, bacterial community, algal community

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100 The Levels of Neurosteroid 7β-Hydroxy-Epiandrosterone in Men and Pregnant Women

Authors: J. Vitku, L. Kolatorova, T. Chlupacova, J. Heracek, M. Hill, M. Duskova, L. Starka

Abstract:

Background: 7β-hydroxy-epiandrosterone (7β–OH-EpiA) is an endogenous steroid, that has been shown to exert neuroprotective and anti-inflammatory effects in vitro as well as in animal models. However, to the best of our knowledge no information is available about concentration of this androgen metabolite in human population. The aim of the study was to measure and compare levels of 7β–OH-EpiA in men and pregnant women in different biological fluids and evaluate the relationship between 7β–OH-EpiA in men and their sperm quality. Methods: First, a sensitive isotope dilution high performance liquid chromatography-mass spectrometry method for measurement of 7β–OH-EpiA in different biological fluids was developed. Validation of the method met the requirements of FDA guidelines. Afterwards 7β–OH-EpiA in plasma and seminal plasma of 191 men with different degree of infertility (healthy men, lightly infertile men, moderately infertile men, severely infertile men) was analysed. Furthermore, the levels of 7β–OH-EpiA in plasma of 34 pregnant women in 37th week of gestation and corresponding cord plasma that reflects steroid levels in the fetus were measured. Results: Concentrations of 7β–OH-EpiA in seminal plasma were significantly higher in severely infertile men in comparison with healthy men and lightly infertile men. The same trend was observed when blood plasma was evaluated. Furthermore, plasmatic 7β –OH-EpiA negatively correlated with concentration (-0.215; p < 0.01) and total count (-0.15; p < 0.05). Seminal 7β–OH-EpiA was negatively associated with motility (-0.26; p < 0.01), progressively motile sperms (-0.233; p < 0.01) and nonprogressively motile sperms (-0.188; p < 0.05). Plasmatic 7β –OH-EpiA levels in men were generally higher in comparison with pregnant women. Levels 7β–OH-EpiA were under the lower limit of quantification (LLOQ) in majority of samples of pregnant women and cord plasma. Only 4 plasma samples of pregnant women and 7 cord blood plasma samples were above LLOQ and where in range of units of pg/ml. Conclusion: Based on available information, this is the first study measuring 7β–OH-EpiA in human samples. 7β–OH-EpiA is associated with lower sperm quality and certainly it is worth to explore its role in this field thoroughly. Interestingly, levels of 7β–OH-EpiA in pregnant women were extremely low despite the fact that steroid levels including androgens are generally higher during pregnancy. Acknowledgements: This work was supported by the project MH CR 17-30528 A from the Czech Health Research Council, MH CZ - DRO (Institute of Endocrinology - EU, 00023761) and by the MEYS CR (OP RDE, Excellent research - ENDO.CZ).

Keywords: 7β-hydroxy-epiandrosterone, steroid, sperm quality, pregnancy

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99 Effect of Hydroxy Propyl Methyl Cellulose (HPMC) Coating in Combination with MGSO4 on Some Guava Cultivars

Authors: Muhammad Randhawa, Muhammad Nadeem

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Guava (Psidium guajava L.) is a vital source of minerals, vitamins, dietary fiber and antioxidants. Owing to highly perishable nature and proning towards chilling injury, diseases, insect-pests and physical damage the main drawbacks of guava after harvesting, present study was designed. Due to its delicacy in physiology, economic importance, effects of pre and postharvest factors and maturity indices, guava fruits should be given prime importance for good quality attributes. In this study guava fruits were stored at 10°C with 80% relative humidity after treating with different levels of sulphate salt of magnesium followed by dipping in cellulose based edible coating hydroxy propyl methyl cellulose (HPMC). The main objective of this coating was to enhance the shelf life of guava by inhibiting the respiration and also by binding the dissolved solids with salt application. Characterization for quality attributes including physical, physiological and bio chemical analysis was performed after every 7 days interval till the fruit remains edible during the storage period of 4 weeks. Finally, data obtained was subjected to statistical analysis. It was concluded on statistical basis that Surahi variety (treated with 5% MgSO4) showed best storage stability and kept its original quality up to almost 23 days during storage.

Keywords: edible coating, guava cultivars, physicochemical attributes, storage

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98 Development of Method for Recovery of Nickel from Aqueous Solution Using 2-Hydroxy-5-Nonyl- Acetophenone Oxime Impregnated on Activated Charcoal

Authors: A. O. Adebayo, G. A. Idowu, F. Odegbemi

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Investigations on the recovery of nickel from aqueous solution using 2-hydroxy-5-nonyl- acetophenone oxime (LIX-84I) impregnated on activated charcoal was carried out. The LIX-84I was impregnated onto the pores of dried activated charcoal by dry method and optimum conditions for different equilibrium parameters (pH, adsorbent dosage, extractant concentration, agitation time and temperature) were determined using a simulated solution of nickel. The kinetics and adsorption isotherm studies were also evaluated. It was observed that the efficiency of recovery with LIX-84I impregnated on charcoal was dependent on the pH of the aqueous solution as there was little or no recovery at pH below 4. However, as the pH was raised, percentage recovery increases and peaked at pH 5.0. The recovery was found to increase with temperature up to 60ºC. Also it was observed that nickel adsorbed onto the loaded charcoal best at a lower concentration (0.1M) of the extractant when compared with higher concentrations. Similarly, a moderately low dosage (1 g) of the adsorbent showed better recovery than larger dosages. These optimum conditions were used to recover nickel from the leachate of Ni-MH batteries dissolved with sulphuric acid, and a 99.6% recovery was attained. Adsorption isotherm studies showed that the equilibrium data fitted best to Temkin model, with a negative value of constant, b (-1.017 J/mol) and a high correlation coefficient, R² of 0.9913. Kinetic studies showed that the adsorption process followed a pseudo-second order model. Thermodynamic parameter values (∆G⁰, ∆H⁰, and ∆S⁰) showed that the adsorption was endothermic and spontaneous. The impregnated charcoal appreciably recovered nickel using a relatively smaller volume of extractant than what is required in solvent extraction. Desorption studies showed that the loaded charcoal is reusable for three times, and so might be economical for nickel recovery from waste battery.

Keywords: charcoal, impregnated, LIX-84I, nickel, recovery

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97 Chemical and Electrochemical Syntheses of Two Organic Components of Ginger

Authors: Adrienn Kiss, Karoly Zauer, Gyorgy Keglevich, Rita Molnarne Bernath

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Ginger (Zingiber officinale) is a perennial plant from Southeast Asia, widely used as a spice, herb, and medicine for many illnesses since its beneficial health effects were observed thousands of years ago. Among the compounds found in ginger, zingerone [4-hydroxy-3- methoxyphenyl-2-butanone] deserves special attention: it has an anti-inflammatory and antispasmodic effect, it can be used in case of diarrheal disease, helps to prevent the formation of blood clots, has antimicrobial properties, and can also play a role in preventing the Alzheimer's disease. Ferulic acid [(E)-3-(4-hydroxy-3-methoxyphenyl)-prop-2-enoic acid] is another cinnamic acid derivative in ginger, which has promising properties. Like many phenolic compounds, ferulic acid is also an antioxidant. Based on the results of animal experiments, it is assumed to have a direct antitumoral effect in lung and liver cancer. It also deactivates free radicals that can damage the cell membrane and the DNA and helps to protect the skin against UV radiation. The aim of this work was to synthesize these two compounds by new methods. A few of the reactions were based on the hydrogenation of dehydrozingerone [4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one] to zingerone. Dehydrozingerone can be synthesized by a relatively simple method from acetone and vanillin with good yield (80%, melting point: 41 °C). Hydrogenation can be carried out chemically, for example by the reaction of zinc and acetic acid, or Grignard magnesium and ethyl alcohol. Another way to complete the reduction is the electrochemical pathway. The electrolysis of dehydrozingerone without diaphragm in aqueous media was attempted to produce ferulic acid in the presence of sodium carbonate and potassium iodide using platinum electrodes. The electrolysis of dehydrozingerone in the presence of potassium carbonate and acetic acid to prepare zingerone was carried out similarly. Ferulic acid was expected to be converted to dihydroferulic acid [3-(4-Hydroxy-3-methoxyphenyl)propanoic acid] in potassium hydroxide solution using iron electrodes, separating the anode and cathode space with a Soxhlet paper sheath impregnated with saturated magnesium chloride solution. For this reaction, ferulic acid was synthesized from vanillin and malonic acid in the presence of pyridine and piperidine (yield: 88.7%, melting point: 173°C). Unfortunately, in many cases, the expected transformations did not happen or took place in low conversions, although gas evolution occurred. Thus, a deeper understanding of these experiments and optimization are needed. Since both compounds are found in different plants, they can also be obtained by alkaline extraction or steam distillation from distinct plant parts (ferulic acid from ground bamboo shoots, zingerone from grated ginger root). The products of these reactions are rich in several other organic compounds as well; therefore, their separation must be solved to get the desired pure material. The products of the reactions described above were characterized by infrared spectral data and melting points. The use of these two simple methods may be informative for the formation of the products. In the future, we would like to study the ferulic acid and zingerone content of other plants and extract them efficiently. The optimization of electrochemical reactions and the use of other test methods are also among our plans.

Keywords: ferulic acid, ginger, synthesis, zingerone

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96 Solid Phase Micro-Extraction/Gas Chromatography-Mass Spectrometry Study of Volatile Compounds from Strawberry Tree and Autumn Heather Honeys

Authors: Marinos Xagoraris, Elisavet Lazarou, Eleftherios Alissandrakis, Christos S. Pappas, Petros A. Tarantilis

Abstract:

Strawberry tree (Arbutus unedo L.) and autumn heather (Erica manipuliflora Salisb.) are important beekeeping plants of Greece. Six monofloral honeys (four strawberry tree, two autumn heather) were analyzed by means of Solid Phase Micro-Extraction (SPME, 60 min, 60 oC) followed by Gas Chromatography coupled to Mass Spectrometry (GC-MS) for the purpose of assessing the botanical origin. A Divinylbenzene/Carboxen/Polydimethylsiloxane (DVB/CAR/PDMS) fiber was employed, and benzophenone was used as internal standard. The volatile compounds with higher concentration (μg/ g of honey expressed as benzophenone) from strawberry tree honey samples, were α-isophorone (2.50-8.12); 3,4,5-trimethyl-phenol (0.20-4.62); 2-hydroxy-isophorone (0.06-0.53); 4-oxoisophorone (0.38-0.46); and β-isophorone (0.02-0.43). Regarding heather honey samples, the most abundant compounds were 1-methoxy-4-propyl-benzene (1.22-1.40); p-anisaldehyde (0.97-1.28); p-anisic acid (0.35-0.58); 2-furaldehyde (0.52-0.57); and benzaldehyde (0.41-0.56). Norisoprenoids are potent floral markers for strawberry-tree honey. β-isophorone is found exclusively in the volatile fraction of this type of honey, while also α-isophorone, 4-oxoisophorone and 2-hydroxy-isophorone could be considered as additional marker compounds. The analysis of autumn heather honey revealed that phenolic compounds are the most abundant and p-anisaldehyde; 1-methoxy-4-propyl-benzene; and p-anisic acid could serve as potent marker compounds. In conclusion, marker compounds for the determination of the botanical origin for these honeys could be identified as several norisoprenoids and phenolic components were found exclusively or in higher concentrations compared to common Greek honey varieties.

Keywords: SPME/GC-MS, volatile compounds, heather honey, strawberry tree honey

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95 Kinetics and Thermodynamics Adsorption of Phenolic Compounds on Organic-Inorganic Hybrid Mesoporous Material

Authors: Makhlouf Mourad, Messabih Sidi Mohamed, Bouchher Omar, Houali Farida, Benrachedi Khaled

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Mesoporous materials are very commonly used as adsorbent materials for removing phenolic compounds. However, the adsorption mechanism of these compounds is still poorly controlled. However, understanding the interactions mesoporous materials/adsorbed molecules is very important in order to optimize the processes of liquid phase adsorption. The difficulty of synthesis is to keep an orderly and cubic pore structure and achieve a homogeneous surface modification. The grafting of Si(CH3)3 was chosen, to transform hydrophilic surfaces hydrophobic surfaces. The aim of this work is to study the kinetics and thermodynamics of two volatile organic compounds VOC phenol (PhOH) and P hydroxy benzoic acid (4AHB) on a mesoporous material of type MCM-48 grafted with an organosilane of the Trimethylchlorosilane (TMCS) type, the material thus grafted or functionalized (hereinafter referred to as MCM-48-G). In a first step, the kinetic and thermodynamic study of the adsorption isotherms of each of the VOCs in mono-solution was carried out. In a second step, a similar study was carried out on a mixture of these two compounds. Kinetic models (pseudo-first order, pseudo-second order) were used to determine kinetic adsorption parameters. The thermodynamic parameters of the adsorption isotherms were determined by the adsorption models (Langmuir, Freundlich). The comparative study of adsorption of PhOH and 4AHB proved that MCM-48-G had a high adsorption capacity for PhOH and 4AHB; this may be related to the hydrophobicity created by the organic function of TMCS in MCM-48-G. The adsorption results for the two compounds using the Freundlich and Langmuir models show that the adsorption of 4AHB was higher than PhOH. The values ​​obtained by the adsorption thermodynamics show that the adsorption interactions for our sample with the phenol and 4AHB are of a physical nature. The adsorption of our VOCs on the MCM-48 (G) is a spontaneous and exothermic process.

Keywords: adsorption, kinetics, isotherm, mesoporous materials, Phenol, P-hydroxy benzoique acid

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