JSCS Vol 76, No. 4

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J. Serb. Chem. Soc. 76 (4) 479–490 (2011)

UDC 547.466.23+547.416:616.8+620.266.1:628.513; JSCS–4134; doi: 10.2298/JSC100629047L; Review

 

REVIEW

Excitatory AMino acid b-N-methylAMino-L-alanine is a putative environmental neurotoxin

SRDJAN LOPIČIć, MARIJA bratić-STANOJEVIć, PATHAK DHRUBA, DRAGAN PAVLOVIć*, MILICA PROSTRAN** and VLADIMIR NEDELJKOV

Institute for Pathological Physiology, School of Medicine, University of Belgrade, 11000 Belgrade, Serbia

*Ernst Moritz Arndt University, Greifswald, Germany

**Institute of Pharmacology, Clinical Pharmacology and Toxicology, School of Medicine, University of Belgrade, 11000 Belgrade, Serbia

 

(Received 29 July, revised 4 October 2010)

The AMino acid b-N-methylAMino-L-alanine (L-BMAA) has been associated with the AMyotrophic lateral sclerosis/parkinsonism-dementia complex in three distinct western Pacific populations. The putative neurotoxin is produced by cyanobacteria, which live symbiotically in the roots of cycad trees. L-BMAA was thought to be a threat only to those few populations whose diet and medicines rely heavily on cycad seeds. However, the recent discovery that cyanobacteria from diverse terrestrial, freshwater, and saltwater ecosystems around the world produce the toxin requires a reassessment of whether it poses a larger health threat. Therefore, it is proposed that monitoring L-BMAA levels in cyanobacteria-contAMinated water supplies might be prudent.

 

Keywords: b-N-methylAMino-L-alanine; neurodegenerative diseases; neurotoxicity; environmental toxin.

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J. Serb. Chem. Soc. 76 (4) 491–497 (2011)

UDC 542.913:549.52+547.564.7+547.572; JSCS–4135; doi: 10.2298/JSC100517043T; Original scientific paper

 

Evaluation of the radical scavenging activity of a series of synthetic hydroxychalcones towards the DPPH radical

IVA T. TODOROVA, DANIELA I. BATOVSKA, BISTRA A. STAMBOLIYSKA and STOYAN P. PARUSHEV

Institute of Organic Chemistry, Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Str. Bl. 9, Sofia, 1113, Bulgaria

 

(Received 23 August, revised 15 November 2010)

Sixteen hydroxychalcones were synthesized in sufficient purity by the Claisen–Schmidt condensation between appropriate acetophenones and aromatic aldehydes. All the compounds were evaluated for their ability to scavenge the stable free 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical. Important structure–activity relationships were observed that strongly contribute to the knowledge for the design of DPPH radical scavenging chalcones. Relevant theoretical parAMeters were computed in an attempt to understand and explain the obtained experimental results.

 

Keywords: hydroxychalcones; 4’-chlorohydroxychalcones; synthesis; radical-scavenging activity; DPPH free radical.

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J. Serb. Chem. Soc. 76 (4) 499–504 (2011)

UDC 547.235+547.828+547.491:66.095.3.095.252; JSCS–4136; doi: 10.2298/JSC100618044D; Short communication

 

SHORT COMMUNICATION

Synthesis of 5-(substituted phenylazo)-6-hydroxy-4-methyl-3-cyano-2-pyridones from ethyl 3-oxo-2-(substituted phenylazo)butanoates

JASMINA DOSTANIĆ, NATAŠA VALENTIĆ*, GORDANA UŠĆUMLIĆ* and DUŠAN MIJIN*

Institute of Chemistry, Technology and Metallurgy, University of Belgrade, Department of Catalysis and Chemical Engineering, Njegoševa 12, 11000 Belgrade, Serbia

*Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, 11120 Belgrade, Serbia

 

(Received 11 June, revised 22 November 2010)

A new procedure for the synthesis of known azo pyridone dyes is presented. A series of 5-(substituted arylazo)-6-hydroxy-4-methyl-3-cyano-2-pyridones were prepared from ethyl 3-oxo-2-(substituted phenylazo)butanoates and cyanoacetAMide in acetone using potassium hydroxide as a catalyst by simple refluxing the reaction mixture. The structure of these dyes was confirmed by FT-IR, NMR and UV–Vis spectroscopy.

 

Keywords: azo compounds; cyclocondensation reaction; cyanoacetAMide; pyridone.

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J. Serb. Chem. Soc. 76 (4) 505–512 (2011)

UDC Oxytropis pilosa:577.151.6:547.972.2:535.379:615.27; JSCS–4137; doi: 10.2298/JSC100701045M; Original scientific paper

 

A study of the antioxidants in Oxytropis pilosa (L.) DC.

DRAGOLJUB MILADINOVIĆ, LJILJANA MILADINOVIĆ* and STEVO NAJMAN**

Department of Pharmacy, School of Medicine, University of Niš, Bulevar dr Zorana Đinđića 81, 18000 Niš, Serbia

*High school B. Stanković, Voždova 27, 18000 Niš, Serbia

**Department of Biology, School of Medicine, University of Niš, Bulevar dr Zorana Đinđića 81, 18000 Niš, Serbia

 

(Received 1 July, revised 27 August 2010)

The objective of this study was to estimate the antioxidative potential of Oxytropis pilosa (L.) DC. during the active vegetative period. The activities of the antioxidant enzymes (superoxide dismutase, catalase, peroxidase), the quantities of malonyldialdehyde, superoxide and hydroxyl radicals and reduced glutathione and the content of total flavonoids, chlorophylls a and b, carotenoids and soluble proteins were determined. The results showed that extracts from all plant organs exhibited antioxidant activity. The highest antioxidant ability was observed in the leaves where all the investigated antioxidant enzymes were active in a specific way: During the spring season, peroxidase showed the maximum activity 18.54 U mg^-1 protein, catalase peaked in summer 9.04 U mg^-1 protein, whereas, during the autumn season, superoxide dis-mutase showed maximum activity, 54.28 U mg^-1 protein. Reduced glutathione, pigments and carotenoids present in the leaves contribute to the high antioxidant activity. Furthermore, inhibition of chemiluminescence activity of Balb/c mice blood phagocytes by crude leaf extracts at concentrations of 3.5 and 7.0 mg cm^-3 were 30.2 and 36.5 %, respectively.

 

Keywords: Oxytropis pilosa; superoxide dismutase; catalase; peroxidase; antioxidant activity; total flavonoids, chemiluminescence.

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J. Serb. Chem. Soc. 76 (4) 513–522 (2011)

UDC 66.091.8+547.56+620.266.1; JSCS–4138; doi: 10.2298/JSC100619046L; Original scientific paper

 

Removal of aqueous phenol and phenol derivatives by immobilized potato polyphenol oxidase

NIKOLA LONČAR, NATAŠA BOŽIĆ*, IVAN ANĐELKOVIĆ, ALEKSANDRA MILOVANOVIĆ*, BILJANA DOJNOV*, MIROSLAVA VUJČIĆ*, GORAN ROGLIĆ and ZORAN VUJČIĆ

Faculty of Chemistry, University of Belgrade, Studentski trg 12–16, Belgrade, Serbia

*Institute of Chemistry, Technology and Metallurgy – Center of Chemistry, University of Belgrade, Studentski trg 12–16, Belgrade, Serbia

 

(Received 19 July, revised 6 September 2010)

Phenols containing halogens, which tend to deactivate the aromatic nuclei, constitute a significant category of highly toxic and difficult-to-degrade pollutants, which arise from a wide variety of industries. The main purpose of this study was to obtain an inexpensive immobilized enzyme for the removal of phenols. Partially purified potato polyphenol oxidase (PPO) was immobilized onto different commercial and laboratory produced carriers. Three of the obtained biocatalysts, with the highest PPO activities, nAMely Eupergit C250L–PPO; Celite–PPO and CelluloseM–PPO, were tested in a batch reactor for the removal of phenol, 4-chlorophenol and 4-bromophenol. In the case of 2.5 mM substrates with Eupergit C250L–PPO, an around 45 % removal of 4-bromophenol was achieved, while the removals 4-chlorophenol and phenol were 35 and 20 %, respectively. The reusability of Eupergit C250L–PPO for the removal of 4-chlorophenol was tested. After eight repeated tests, the efficiency of 4-chlorophenol removal by Eupergit C250L–PPO immobilisate had decreased to 55 %.

 

Keywords: polyphenol oxidase; potato; phenol; immobilization; Eupergit.

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J. Serb. Chem. Soc. 76 (4) 523–528 (2011)

UDC *Laggera crispata+582.998.1:665.52/.54+543.51+543.544.3(540); JSCS–4139; doi: 10.2298/JSC100801048V; Short communication

 

SHORT COMMUNICATION

Chemical investigation of the essential oil of Laggera crispata (Vahl) Hepper &AMp; Wood from India

RAM S. VERMA, RAJENDRA C. PADALIA, CHANDAN S. CHANOTIYA*, AMIT CHAUHAN and ANJU YADAV*

Central Institute of Medicinal and Aromatic Plants (CIMAP, CSIR), Research Centre, Pantnagar, P. O. – Dairy farm Nagla, UdhAM Singh Nagar, Uttarakhand-263149, India

*Central Institute of Medicinal and Aromatic Plants (CIMAP, CSIR), P. O. CIMAP, Lucknow-226015, India

 

(Received 1 August, revised 22 September 2010)

Hydrodistilled essential oil of the aerial parts of Laggera crispata (Vahl) Hepper &AMp; Wood, collected from the Kumaon region of the western Himalayas was analysed by gas chromatography and gas chromatography–mass spectrometry. Eighty constituents, accounting for 83.9 % of the total oil composition, were identified. The oil was mainly dominated by sesquiterpenoids (45.3 %) and benzenoid compounds (33.9 %). Among them, 2,5-dimethoxy-p-cymene (32.2 %), 10-epi-γ-eudesmol (14.7 %), β-caryophyllene (6.9 %) and caryophyllene oxide (5.4 %) were major components of the oil.

 

Keywords: Laggera crispata; Asteraceae; essential oil; GC–MS; 2,5-dimethoxy-p-cymene; 10-epi-γ-eudesmol.

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J. Serb. Chem. Soc. 76 (4) 529–537 (2011)

UDC 547.461.2+547.831+546.472:548.7; JSCS–4140; doi: 10.2298/JSC100822049W; Original scientific paper

 

Crystal structure of an oxalate-bridged tetranuclear 8-hydroxyquinoline Zn(II) cluster: [Zn₄Q₆(O_x)]_0.5n

JIAJUN WANG, QIANG WANG*, YANJUN SUN**, YUEMEI WANG***, GUOSHENG ZHAO and YUNCHENG CUI

Chemistry College of Jilin Normal University, Key Laboratory of Preparation and Application of Environmentally Friendly Materials (Jilin Normal University), Ministry of Education, Siping, 136000, China

*Department of Biological Medicine and Chemical Engineering, Liaoning Institute of Science and Technology, Benxi, 117004, China

**Boda College of Jilin Normal University, Siping, 136000, China

***Xi’an Modern Chemistry Research Institute, Xi’an, 710065, China

 

(Received 22 August, revised 22 October 2010)

The chain structure of a tetranuclear zinc(II) cluster [Zn₄Q₆(Ox)]_0.5n ([Zn₄ (C₉H₆NO) ₆(C₂O₄)]_0.5n) (1) (Q = 8-hydroxyquinoline anion, Ox = oxalate dianion) was determined by X-ray crystallography and characterized by elemental analysis, IR spectroscopy and thermal analysis. It crystallizes in the monoclinic system, space group P2₁/n (No. 14), with the lattice parAMeters a = 13.2222(15) Å, b = 11.0566(12) Å, c = 16.2224(18) Å, β = 92.1770(10)°, V = 2369.9(5) Å³, Z = 4, M_r = 607.23 g mol^-1, Dc = 1.702 g cm^-3. The tetranuclear zinc(II) clusters form 1D polymeric chains parallel to the b-axis. The π–π stacking interactions involving aryl rings support the formation of the 1D polymeric structure. The neighboring polymeric chains are connected by C–H···π interactions.

 

Keywords: 8-hydroxyquinoline; zinc(II) cluster; single crystal structure.

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J. Serb. Chem. Soc. 76 (4) 539–555 (2011)

UDC 544.112:517.544.4:621.376.2; JSCS–4141; doi: 10.2298/JSC101126052S; Original scientific paper

 

On the relationship between molecular spectroscopy and statistical mechanics: calculation of partition functionsfor triatomic molecules undergoing large-AMplitude bending vibrations

MILAN V. SENĆANSKI, JELENA RADIĆ-PERIĆ* and MILJENKO PERIĆ*

Innovation Centre of the Faculty of Chemistry, University of Belgrade, Studentski Trg 12–16, 11158 Belgrade, Serbia

*Faculty of Physical Chemistry, University of Belgrade, Studentski Trg 12–16, P.O. Box 47, 11158 Belgrade, Serbia

 

(Received 26 November 2010)

The evaluation of partition functions for triatomic molecules undergoing large-AMplitude bending vibrations is discussed. It was supposed that the needed molecular structure data were obtained by means of ab initio calculations. Special attention is paid to the coupling between the bending and stretching modes and the interplay between bending motions and rotations. An appropriate scheme for variational computation of the energy levels is developed.

 

Keywords: partition functions; triatomic molecules; large-AMplitude bending.

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J. Serb. Chem. Soc. 76 (4) 557–573 (2011)

UDC 536.722:517.544.4:533.912; JSCS–4142; doi: 10.2298/JSC101126053S; Original scientific paper

 

On the relationship between molecular spectroscopy and statistical mechanics: calculation of vibrational–rotational energy levels and partition functions in the ground electronic state of BC₂

MILAN V. SENĆANSKI, LJILJANA STOJANOVIĆ*, STANKA JEROSIMIĆ*, JELENA RADIĆ-PERIĆ* and MILJENKO PERIĆ*

Innovation Centre of the Faculty of Chemistry, University of Belgrade, Studentski Trg 12–16, 11158 Belgrade, Serbia

*Faculty of Physical Chemistry, University of Belgrade, Studentski Trg 12–16, P.O. Box 47, 11158 Belgrade, Serbia

 

(Received 26 November 2010)

The results of extensive ab initio calculations of the vibrational–rotational energy spectrum in the ground electronic state of the BC₂ molecule are presented. These data were employed to discuss the evaluation of the corresponding partition functions. Special attention was paid to the problems connected with the calculation of the partition functions for the bending vibrations and rotations about the axis corresponding to the smallest moment of inertia.

 

Keywords: vibrational–rotational energy; partition functions; BC₂.

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J. Serb. Chem. Soc. 76 (4) 575–589 (2011)

UDC 546.776+546.824–31:539.12+541.135.5–039.26:544.4; JSCS–4143; doi: 10.2298/JSC100504042M; Original scientific paper

 

Fabrication and characterization of molybdenum(VI) complex–TiO₂ nanoparticles modified electrode for the electrocatalytic determination of L-cysteine

MOHAMMAD MAZLOUM-ARDAKANI, HADI BEITOLLAHI, ZAHRA TALEAT and MASOUD SALAVATI-NIASARI*

Department of Chemistry, Faculty of Science, Yazd University, Yazd, 89195-741, I.R. Iran

*Department of Inorganic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, I.R. Iran

 

(Received 4 May, revised 15 October 2010)

A novel voltAMmetric sensor for the determination of L-cysteine (L-Cys) was fabricated based on a TiO₂ nanoparticles/bis[bis(salicylidene-1,4-phenylenediAMine) molybdenum(VI)] carbon paste electrode. The electroche­mical behavior of the sensor was investigated in detail by cyclic voltAMmetry. The apparent electron transfer rate constant (k_s) and charge transfer coefficient (α) of the TiO₂ nanoparticles/molybdenum(VI) complex/carbon paste electrode (CPE) were also deter­mined by cyclic voltAMmetry and found to be about 4.53 s^-1 and 0.54, respec­tively. The sensor displayed good electrocatalytic activity towards the oxi­dation of L-Cys. The peak potential for the oxidation of L-Cys was low­ered by at least 130 mV compared with that obtained at an unmodified CPE. Under optimal conditions, the linear range spans L-Cys concentrations from 1.5×10^-6 to 1.2×10^-3 M and the detection limit was 0.70±0.01 µM at a signal-to-noise ratio of 2. In addition, the sensor showed good stability and reproducibility.

 

Keywords: L-cysteine; TiO₂ nanoparticles; carbon paste electrode; electrocatalysis.

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J. Serb. Chem. Soc. 76 (4) 591–606 (2011)

UDC 665.32/.33:547.56:66.095.253:66.095.26–128.4; JSCS–4144; doi: 10.2298/JSC100820050I; Original scientific paper

 

Phenolation of vegetable oils

MIHAIL IONESCU and ZORAN S. PETROVIĆ

Pittsburg State University, Kansas Polymer Research Center, 1701 South Broadway, Pittsburg, Kansas, 66762, USA

 

(Received 20 August, revised 8 December 2010)

Novel bio-based compounds containing phenols suitable for the syn­thesis of polyurethanes were prepared. The direct alkylation of phenols with different vegetable oils in the presence of superacids (HBF₄, triflic acid) as ca­talysts was studied. The reaction kinetics was followed by monitoring the de­crease of the double bond content (iodine value) with time. In order to under­stand the mechanism of the reaction, phenol was alkylated with model com­pounds. The model compounds containing one internal double bond were 9-oc­tadecene and methyl oleate and those with three double bonds were triolein and high oleic safflower oil (82 % oleic acid). It was shown that the best structures for phenol alkylation are fatty acids with only one double bond (oleic acid). Fatty acids with two double bonds (linoleic acid) and three double bonds (lino­lenic acid) lead to polymerized oils by a Diels–Alder reaction, and to a lesser extent to phenol alkylated products. The reaction product of direct alkylation of phenol with vegetable oils is a complex mixture of phenol alkylated with poly­merized oil (30–60 %), phenyl esters formed by transesterification of phenol with triglyceride ester bonds (<10 %) and unreacted oil (30 %). The phenolated vegetable oils are new aromatic–aliphatic bio-based raw materials suitable for the preparation of polyols (by propoxylation, ethoxylation, Mannich reactions) for the preparation of polyurethanes, as intermediates for phenolic resins or as bio-based antioxidants.

 

Keywords: vegetable oils; phenol; alkylation; aromatic electrophilic substi­tution; cationic polymerization.

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J. Serb. Chem. Soc. 76 (4) 607–624 (2011)

UDC 667.2+541.42:66.081+582.998.2+54–145.2; JSCS–4145; doi: 10.2298/JSC100721051S; Original scientific paper

 

Removal of Orange 16 reactive dye from aqueous solutions by waste sunflower seed shells

DANIELA SUTEU, CARMEN ZAHARIA* and TEODOR MALUTAN**

Technical University “Gh. Asachi”, Faculty of Chemical Engineering and Environmental Protection, Department of Organic and Biochemical Engineering, 71A Blv. Prof. D. Mangeron, 700050, Iasi, Romania

*Technical University “Gh. Asachi”, Faculty of Chemical Engineering and Environmental Protection, Department of Environmental Engineering and Management, 71A Blv. Prof. D. Mangeron, 700050, Iasi, Romania

**Technical University “Gh. Asachi”, Faculty of Chemical Engineering and Environmental Protection, Department of Natural and Synthetic Polymers, 71A Blv. Prof. D. Mangeron, 700050, Iasi, Romania

 

(Received 21 July, revised 1 October 2010)

In this work, the use of an agro-industrial waste, i.e., sunflower seed shells, was investigated as a sorbent for the removal of Orange 16 reactive dye from aqueous environments. Batch experiments were performed as a function of pH, sorbent dose, dye concentration, temperature and contact time. The per­cent dye removal increased with increasing sorbent dose and temperature of the aqueous solution, and decreased with increasing dye concentration; the re­quired contact time was five hours. The Freundlich, Langmuir, Dubinin–Ra­du­shkevich and Tempkin adsorption isotherms were used to describe the equi­librium sorption data and to determine the corresponding isotherm constants. The thermodynAMic parAMeters, ΔG, ΔH and ΔS, were also determined. These parAMeters indicated that the sorption of reactive dye onto sunflower seed shells was a spontaneous, endothermic and entropy-driven process. The kinetic data were evaluated by pseudo-first order, pseudo-second order and intra-par­ticle diffusion kinetic models. The results of the kinetic study indicated that the sorption of Orange 16 reactive dye onto sunflower seed shells is a complex process and both chemical surface sorption and intra-particle diffusion contri­bute to the rate-limiting step. Therefore, the sunflower seed shell showed itself to be a promising cheap sorbent for the decolourization of aqueous coloured solutions or effluents.

 

Keywords: sorption; sunflower seed shell; reactive dye; Orange 16; equilibrium study.

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J. Serb. Chem. Soc. 76 (4) 625–641 (2011)

UDC 669.04+669.3:504.53.054+669.4/.5(497.11); JSCS–4146; doi: 10.2298/JSC100823054N; Original scientific paper

 

Multi-criteria analysis of soil pollution by heavy metals in the vicinity of the Copper Smelting Plant in Bor (Serbia)

DJORDJE NIKOLIĆ, NOVICA MILOŠEVIĆ*, ŽIVAN ŽIVKOVIĆ, IVAN MIHAJLOVIĆ, RENATA KOVAČEVIĆ* and NEVENKA PETROVIĆ*

University of Belgrade, Technical Faculty in Bor, Vojske Jugoslavije 12, 19210 Bor, Serbia

*Institute for Mining and Metallurgy Bor, Zeleni bulevar 35, 19210 Bor, Serbia

 

(Received 28 March, revised 23 September 2010)

This study highlights the consequences on soil pollution of one hund­red years of manufacturing in the Copper Mining and Smelting Complex RTB-Bor (Serbia). Soil sediments were taken via a probe from the surface layer of the soil at twelve different measuring points. The measuring points were all within 20 km of the smelting plant, which included both urban and rural zones. Soil sAMpling was performed using a soil core sAMpler in such way that a core of a soil of radius 5 cm and depth of 30 cm was removed. Subsequently, the sAMples were analyzed for pH and heavy metal concentrations (Cu, Pb, As, Cd, Mn, Ni and Hg) using different spectrometric methods. The obtained results for the heavy metal contents in the sAMples show high values: 2,540 mg kg^-1 Cu; 230 mg kg^-1 Pb; 6 mg kg^-1 Cd; 530 mg kg^-1 Ni; 1,300 mg kg^-1 Mn; 260 mg kg^-1 As and 0.3 mg kg^-1 Hg. In this study, critical zones of polluted soil were iden­tified and ranked according to their metal contents by the multi-criteria deci­sion method Preference Organization Method for Enrichment Evaluation/Geo­metrical Analysis for Interactive Assistance – PROMETHEE/GAIA, which is the preferred multivariate method commonly used in chemometric studies. The ranking results clearly showed that the most polluted zones are at locations holding the vital functions of the town. Therefore, due to the high bioavail­abi­lity of heavy metals through com­plex reactions with organic species in the sediments, consequences for human health could drastically emerge if these metals enter the food chain.

 

Keywords: heavy metals; soil; pollution; multi-criteria; PROMETHEE /GAIA.

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J. Serb. Chem. Soc. 76 (4) 643–646 (2011)

UDC 543+061.3(4); EuCheMS news

 

EUCHEMS NEWS

European Analytical Column No. 39: Analytical chemistry and bioanalytical chemistry – an unshaped social relationship

(January 2011)

GEORGE HORVAI, PAUL WORSFOLD*, BO KARLBERG** and JENS E. T. ANDERSEN***

Department of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, Gellert ter 4, H-1111 Budapest, Hungary

*School of Geography, Earth and Environmental Sciences, University of Plymouth, Plymouth PL4 8AA, UK

**Department of Analytical Chemistry, Stockholm University, 10691 Stockholm, Sweden

***Department of Chemistry, Technical University of Denmark, Building 207, 2800 Lyngby, Denmark

 

Keywords: analytical chemistry; bioanalysis; EuCheMS-DAC.

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April 16, 2011.
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