JSCS Vol 76, No. 5

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J. Serb. Chem. Soc. 76 (5) 647–677 (2011)

UDC 543.42:542.943:573.02:541.515+615.27; JSCS–4147; doi: 10.2298/JSC101015064S; Review

 

REVIEW

The role of EPR spectroscopy in studies of the oxidative status of biological systems and the antioxidative properties of various compounds

IVAN SPASOJEVIĆ, MILOŠ MOJOVIĆ, ALEKSANDAR IGNJATOVIĆ* and GORAN BAČIĆ*

Institute for Multidisciplinary Research, Kneza Višeslava 1, University of Belgrade, 11000 Belgrade, Serbia

*Faculty of Physical Chemistry, University of Belgrade, Studentski trg 12–16, 11000 Belgrade, Serbia

 

(Received 15 October, revised 28 December 2010)

In this era of intense study of free radicals and antioxidants, electron parAMagnetic resonance (EPR) is arguably the best-suited technique for such research, particularly when considering biochemical and biological systems. No attempt was made to cover all the topics of EPR application but instead attention was restricted to two areas that are both novel and received less attention in previous reviews. In the first section, the application of EPR in assessing the oxidative status of various biological systems, using endogenous stabile parAMagnetic species, such as the ascorbyl radical, semiquinone, melanin, and oxidized pigments, is addressed. The second section covers the use of EPR in the emerging field of antioxidant development, using EPR spin-trapping and spin-probing techniques. In both sections, in addition to giving an overview of the available literature, exAMples (mostly from the authors’ recent work) are also presented in sufficient detail to illustrate how to explore the full potential of EPR. This review aims at encouraging biologists, chemists and pharmacologists interested in the redox metabolism of living systems, free radical chemistry or antioxidative properties of new drugs and natural products to take advantage of this technique for their investigations.

Keywords: EPR spectroscopy; oxidative status; antioxidants; spin-probes; spin-traps.

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J. Serb. Chem. Soc. 76 (5) 679–684 (2011)

UDC 534–8+542.913:547.853+547.286.2; JSCS–4148; doi: 10.2298/JSC100212057S; Original scientific paper

 

Ultrasound-assisted synthesis of dihydropyrimidine-2-thiones

JAVAD SAFAEI-GHOMI and MOHAMMAD ALI GHASEMZADEH

Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, 51167 Kashan, I. R. Iran

 

(Received 12 February 2010, revised 9 January 2011)

Chalcone derivatives were prepared by the condensation of various substituted aryl aldehydes and acetophenone in alkaline ethanol, while pyrimidine-2-thione derivatives were prepared by the combination of chalcones and thiourea under conventional and ultrasonic conditions. Advantages of the ultrasound effect were observed and high yields of the products were obtained after 20–30 min sonication. Characterization and structural elucidation of the products was realized based on chemical, analytical and spectral analyses. The results clearly demonstrated a high efficiency of the ultrasonic systems was achieved in the chemical processes.

Keywords: chalcone derivatives, ultrasound, pyrimidine-2-thione derivatives.

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J. Serb. Chem. Soc. 76 (5) 685–692 (2011)

UDC 66.094.414+547.52+547.323+546.32+547.53+547.551.1; JSCS–4149; doi: 10.2298/JSC100212058G; Original scientific paper

 

Simple and improved regioselective brominations of aromatic compounds using N-benzyl-N,N-dimethylanilinium peroxodisulfate in the presence of potassium bromide under mild reactions conditions

HASSAN GHASEMNEJAD-BOSRA, FARHAD RAMZANIAN-LEHMALI* and SOMAYE JAFARI

IslAMic Azad University – Babol Branch, School of Science, P.O. Box 755, Babol, Iran

*University of PayAMenoor, Babol, Iran

(Received 16 March, revised 9 December 2010)

A simple, efficient, and mild method for the selective bromination of some activated aromatic compounds using N-benzyl-N,N-dimethylanilinium peroxodisulfate in the presence of potassium bromide in non-aqueous solution is reported. The results obtained revealed good to excellent selectivity between the ortho and para positions of phenols and methoxyarenes.

Keyword: bromination; N-benzyl-N,N-dimethylanilinium peroxodisulfate; potassium bromide; phenols; methoxyarenes.

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J. Serb. Chem. Soc. 76 (5) 693–698 (2011)

UDC 542.913:547.466–326+547.416:615.281/.282–188; JSCS–4150; doi: 10.2298/JSC100520059S; Original scientific paper

 

Synthesis, characterisation and antimicrobial activity of (5-bromo-5-nitro-2-oxido-1,3,2-dioxaphosphinan-2-yl) AMino acid esters

PEMMASANI SANTHIPRIYA, CHINTHAPARTHI RADHA RANI*, NANDANUR JAGANNADHA REDDY, CHEREDDY SYAMA SUNDAR* and CIRANDUR SURESH REDDY*

Department of Chemistry, S. G. H. R &AMp; M. C. M. R. Degree College, Guntur, India

*Department of Chemistry, Sri Venkateswara University, Tirupati-517 502, India

(Received 20 May, revised 13 December 2010)

Synthesis of a new series of (5-bromo-5-nitro-2-oxido-1,3,2-dioxaphosphinan-2-yl)AMino acid esters (3a–l) was accomplished via a two step process, which involves the prior preparation of the monochloride intermediate (2) and its subsequent reaction with the AMino acid esters in dry tetrahydrofuran in the presence of triethylAMine at reflux temperature. The title compounds (3a–l) structures were established by analytical, IR, ¹H-, ¹³C- and ³¹P-NMR, and mass spectral data. They exhibited significant antibacterial and antifungal activity.

Keywords: dioxaphosphinane; 2-bromo-2-nitropropane-1,3-diol; AMino acid ester hydrochlorides; antibacterial activity; antifungal activity.

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J. Serb. Chem. Soc. 76 (5) 699–707 (2011)

UDC 579.864+547.466.1:579.61:615.28–188; JSCS–4151; doi: 10.2298/JSC100605060S; Original scientific paper

 

The partial characterization of the antibacterial peptide bacteriocin G₂ produced by the probiotic bacteria Lactobacillus plantarum G₂

SVETLANA L. ŠEATOVIĆ, JELENA S. JOVANOVIĆ NOVAKOVIĆ, GORDANA N. ZAVIŠIĆ, ŽELJKA Č. RADULOVIĆ, MARIJA Đ. GAVROVIĆ-JANKULOVIĆ* and RATKO M. JANKOV*

Galenika a.d., Batajnički drum bb, 11080 Zemun, Belgrade, Serbia

*Faculty of Chemistry, University of Belgrade, Studentski trg 12–16, 11000 Belgrade, Serbia

(Received 5 June, revised 15 October 2010)

The aim of this study was the partial characterization of the antimicrobial peptide bacteriocin G₂ produced by probiotic bacteria Lactobacillus plantarum G₂, which was isolated from a clinical sAMple of a healthy person. Antimicrobial substance was secreted in the supernatant of an L. plantarum G₂ culture, and showed a diverse spectrum of antimicrobial activity of all the tested strains of the genera Lactobacillus and the pathogenic bacteria Staphylococcus aureus and Salmonella аbony. Isoelectric focusing revealed that bacteriocin G₂ is a cationic peptide (pI about 10) with a molecular mass of 2.2 kDa according to tricine–sodium dodecyl sulphate–polyacrylAMide gel electrophoresis, SDS-PAGE. The antimicrobial activity of bacteriocin G2 was diminished by the proteolytic action of trypsin and proteinase K. Bacteriocin G₂ preserved its biological activity in the temperature range 40–60 °C (15 min), which was lost at 80 °C. Bacteriocin G₂ was stable in the pH range 2–9, while treatment with 1 % Tween 80 and 1 % urea resulted in increased antimicrobial activity. The probiotic strain L. plantarum G₂ produces the antimicrobial substance proteinaceous in nature with bacteriocin characteristics. Bacteriocin production is one of the key properties of probiotic bacteria with clinical potential as anti-infective agents, which will increase the likelihood of its in vivo efficacy.

Keywords: Lactobacillus plantarum; probiotic; bacteriocin.

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J. Serb. Chem. Soc. 76 (5) 709–717 (2011)

UDC Pouzolzia zeylanica:547.56:541.515:615.27–188; JSCS–4152; doi: 10.2298/JSC100818063L; Original scientific paper

 

Free radical-scavenging capacity, antioxidant activity and phenolic content of Pouzolzia zeylanica

PEIYUAN LI, LINI HUO, WEI SU*, RUMEI LU, CHAOCHENG DENG, LIANGQUAN LIU*, YONGKUN DENG, NANA GUO*, CHENGSHENG LU and CHUNLING HE

College of Pharmacy, Guangxi Traditional Chinese Medical University, Nanning 530001, P. R. China

*College of Chemistry and Life Science, Guangxi Teachers Education University, Nanning 530001, P. R. China

(Received 18 August, revised 1 November 2010)

Pouzolzia zeylanica was extracted with different solvents (acetone, ethyl acetate and petroleum ether), using different protocols (cold-extraction and Soxhlet extraction). To evaluate the antiradical and antioxidant abilities of the extracts, four in vitro test systems were employed, i.e., DPPH, ABTS and hydroxyl radical scavenging assays and a reducing power assay. All extracts exhibited outstanding antioxidant activities that were superior to that of butylated hydroxytoluene. The ethyl acetate extracts exhibited the most significant antioxidant activities, and cold-extraction under stirring seemed to be the more efficacious method for acquiring the predominant antioxidants. Furthermore, the antioxidant activities and total phenolic (TP) content of different extracts followed the sAMe order, i.e., there is a good correlation between antioxidant activities and TP content. The results showed that these extracts, especially the ethyl acetate extracts, could be considered as natural antioxidants and may be useful for curing diseases arising from oxidative deterioration.

Keywords: total phenolic content; DPPH; ABTS; hydroxyl radical; reducing power; Pouzolzia zeylanica.

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J. Serb. Chem. Soc. 76 (5) 719–731 (2011)

UDC 546.562+546.732:547.586.2; JSCS–4153; doi: 10.2298/JSC101201062V; Original scientific paper

 

New Cu(II) and Co(II) octaazAMacrocyclic complexes with 2-AMino-3-phenylpropanoic acid

GORDANA VUČKOVIĆ, MIRJANA ANTONIJEVIĆ-NIKOLIĆ*, SLAĐANA B. TANASKOVIĆ** and VUKOSAVA ŽIVKOVIĆ-RADOVANOVIĆ

Faculty of Chemistry, University of Belgrade, P.O. Box 118, 11158 Belgrade, Serbia

*Higher Technological School of Professional Studies, 15000 Šabac, Serbia

**Faculty of Pharmacy, Vojvode Stepe 450, 11000 Belgrade, Serbia

(Received 1 December 2010, revised 27 January 2011)

New cationic Cu(II) and Co(II) complexes with N,N’,N”,N’’’-tetrakis(2-pyridylmethyl)-1,4,8,11-tetraazacyclotetradecane (tpmc) and the anion of 2-AMino-3-phenylpropanoic acid (S-phenylalanine) were prepared. The complexes were analyzed and characterized by elemental analysis, conductometric, polarimetric, magnetic and cyclic voltAMmetric measurements, as well as by spectroscopic data (UV/Vis, IR). Both complexes are binuclear with the general formula [M₂(S-Phe)tpmc](ClO₄)₃∙nH₂O; S-PheH = S-phenylalanine, M(II) = Cu, n = 7; Co, n = 0. Based on previously reported data for some fAMiliar complexes and the present results, pentacoordinated geometry was proposed. Both of the central metal ions are coordinated with two pyridyl and two cyclAM nitrogens and bridged with –N–(CH₂)₃–N– portions of the cyclAM ring and oxygen atoms of the S-phenylalaninate ion. Antimicrobial screening of the complexes, solvent, starting salts and ligands alone was performed against fungi, mould and some bacteria. In certain cases, enhanced activity of Co(II) complex towards bacteria compared with the relevant free ligands and starting salts was detected.

Keywords: Cu(II) and Co(II) complexes; pendant octaazAMacrocycle; S-phenylalanine.

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J. Serb. Chem. Soc. 76 (5) 733–741 (2011)

UDC 547.686:54.02+66.095.252.5:547.52; JSCS–4154; doi: 10.2298/JSC101201061G; Original scientific paper

 

Effect of benzocyclobutadieno-annelation on cyclic conjugation in fluoranthene congeners

IVAN GUTMAN, BORIS FURTULA and ALEXANDRU T. BALABAN*

Faculty of Science, University of Kragujevac, P. O. Box 60, 34000 Kragujevac, Serbia

*Texas A&AMp;M University at Galveston, 5007 Avenue U, Galveston, TX 77551, USA

(Received 1 December 2010)

Earlier studies revealed that benzo-annelation has a peculiar effect on the intensity of cyclic conjugation in the five-membered ring of fluoranthene congeners. Now, the analogous effect of benzocyclobutadieno-annelation was exAMined and it was found show it is opposite to the effect of benzo-annelation: a benzocyclobutadiene fragment in angular (resp. linear) position with regard to the five-membered ring, decreases (resp. increases) the intensity of cyclic conjugation in the five-membered ring.

Keywords: fluoranthenes; Kekulé structure; polycyclic aromatic hydrocarbon; benzo-annelation; benzocyclobutadieno-annelation.

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J. Serb. Chem. Soc. 76 (5) 743–749 (2011)

UDC 547.313.2+541.124:66.095.252.091.7:536.722; JSCS–4155; doi: 10.2298/JSC100820065L; Original scientific paper

 

An ab initio study of the mechanism of the cycloaddition reaction forming bicyclic compounds between vinylidene (H₂C=C:) and ethylene

XIUHUI LU, ZHENXIA LIAN and YONGQING LI

School of Chemistry and Chemical Engineering, University of Jinan, Jinan, Shandong, 250022, P. R. China

(Received 20 August, revised 21 September 2010)

The mechanism of the cycloaddition reaction forming a bicyclic compounds between singlet vinylidene (H₂C=C:) and ethylene was investigated using the CCSD(T)//MP2/6-31G* method. From the potential energy profile, it can be predicted that this reaction has one dominant channel. The presented rule of this reaction, a [2+2] cycloaddition reaction between the two reactants occurred forming a four-membered ring carbene (INT1), in which the sp lone electron of the C atom from carbene in INT1 and the π* unoccupied orbital of ethane form the sp®π* donor–acceptor effect, resulting in the formation of intermediate (INT2). Due to the further sp³ hybridization of C atom from carbene in INT1, INT2 isomerizes to the bicyclic compound (P2) via the transition state (TS2).

Keywords: vinylidene; reaction mechanism; potential energy surface.

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J. Serb. Chem. Soc. 76 (5) 751–756 (2011)

UDC 621.383.51:546.181.1–151+541.135.1:541.147; JSCS–4156; doi: 10.2298/JSC091201055L; Original scientific paper

 

Phosphonium iodide as a donor liquid electrolyte for dye-sensitized solar cells

HUI LI, HONGSHI JIANG, CHENZHONG YAO and JIAN WANG

Department of Applied Chemistry, Yuncheng University, Yuncheng, Shanxi 044000, P. R. China

(Received 1 December 2009, revised 30 July 2010)

An efficient triphenylmethylphosphonium iodide-based liquid electrolyte was synthesized and used for the first time as an electrolyte in dye-sensitized solar cells (DSSCs). With the as-synthesized electrolyte, the DSSC yielded an overall light to electricity conversion efficiency of 5.34 to 7.10 %, when the radiant power was tuned from 100 to 10 mW cm^-2. This may be attributed to the limitation of mass transport in the DSSC. The electronic and ionic processes in the DSSC were investigated by electrochemical impedance spectroscopy and linear voltAMmography, respectively.

Keywords: dye-sensitized solar cells; triphenylmethylphosphonium iodide; mass transport; conversion efficiency.

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J. Serb. Chem. Soc. 76 (5) 757–768 (2011)

UDC 666.762.8+541.183+546.21:7544.723.3+544.032.4; JSCS–4157; doi: 10.2298/JSC091224056K; Original scientific paper

 

Characterisation of surface oxygen groups on different carbon materials by the Boehm method and temperature-progrAMmed desorption

ANA M. KALIJADIS, MARIJA M. VUKČEVIĆ*, ZORAN M. JOVANOVIĆ, ZORAN V. LAUŠEVIĆ and MILA D. LAUŠEVIĆ*

Laboratory of Physics, Vinča Institute of Nuclear Sciences, P. O. Box 522, 11000 Belgrad, Serbia

*Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, 11000 Belgrade, Serbia

(Received 24 December 2009, revised 27 October 2010)

The surface characteristics of different carbon materials: activated carbon, carbon felt, glassy carbon and a porous carbon monolith were investigated. The specific surface area was exAMined by the BET method with N₂ adsorption, the AMount and the type of surface oxygen groups by Boehm titration as well as by temperature-progrAMmed desorption (TPD). By comparing the results obtained using BET analysis with those of TPD and the Boehm method, it was found that the number of surface groups was not proportional to the specific surface area. The total AMount of oxygen groups, obtained by TPD, is higher than the AMount obtained by Boehm’s method for porous sAMples. The inconsistencies between these results originate from the fact that the Boehm method is limited to the determination of acidic and basic groups, whereas TPD provides information on the total number of all surface oxygen groups. In addition, the presence of porosity could reduce the solvent-accessible surface in the Boehm method. The TPD profiles of CO evolution showed the presence of a low temperature maximum, below 650 K, which originates from CO₂ reduction on the carbon material surface.

Keywords: carbon materials; surface oxygen groups; temperature progrAMmed desorption.

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J. Serb. Chem. Soc. 76 (5) 769–780 (2011)

UDC 66.061+54.06:544.354–128.2–039.6+504.53; JSCS–4158; doi: 10.2298/JSC100911069S; Original scientific paper

 

A comparison of sAMple extraction procedures for the determination of inorganic anions in soil by ion chromatography

SVETLANA M. STANIŠIĆ, LJUBIŠA M. IGNJATOVIĆ, MILICA C. STEVIĆ and ALEKSANDAR R. ĐORĐEVIĆ*
Faculty of Physical Chemistry, University of Belgrade, Studentski trg 12–16, Belgrade, Serbia

*Faculty of Agriculture, University of Belgrade, Nemanjina 6, Zemun, Serbia

(Received 11 September, revised 26 October 2010)

Three different extraction techniques were used for aqueous extraction of anions from soil of the type Ranker that was sAMpled from a serpentine site. The first technique involved the use of a rotary mixer (rotary mixer assisted extraction), the second, a microwave digestion system (microwave assisted extraction), with different extraction temperatures for every cycle during the procedure as follows: 50, 100 and 150 °C. An ultrasonic bath (ultrasonic assisted extraction) was used for the last technique in which the durations of the extraction process were: 10, 20, 30, 40 and 50 min. The concentrations of inorganic anions in the soil extracts after filtration were determined by ion chromatography. The results showed that the microwave-assisted extraction was highly efficient, giving, at a temperature of 150 °C, several times higher AMounts of extracted anions in water than the other two techniques. Moreover, the extracted AMounts of anions obtained by means of an ultrasonic bath with an extraction time ranging from 10 to 50 min were similar to those obtained by means of the rotary mixer with an extraction time of 22 h. However, extraction using the rotary mixer was more reliable, since the extracted AMounts of anions obtained by means of an ultrasonic bath do not correlate with prolongation of the extraction time.

Keywords: soil sAMple extraction; inorganic anions extraction; ion chromatography.

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J. Serb. Chem. Soc. 76 (5) 781–794 (2011)

UDC 631.452+633+541.183:546.722/726(497.11); JSCS–4159; doi: 10.2298/JSC100619068J; Original scientific paper

 

Distribution and forms of iron in the vertisols of Serbia

MIODRAG Ž. JELIĆ, JELENA Ž. MILIVOJEVIĆ*, SREĆKO R. TRIFUNOVIĆ**, IVICA G. ĐALOVIĆ***, DRAGIŠA S. MILOŠEV**** and SRĐAN I. ŠEREMEŠIĆ****

University of Kosovska Mitrovica, Faculty of Agriculture, Jelene Anžujske, 38228 Zubin Potok, Serbia

*Center for Small Grains of Kragujevac, Save Kovacevica 31, 34000 Kragujevac, Serbia

**Department of Chemistry, Faculty of Science, University of Kragujevac, Radoja Domanovića 12, 34000 Kragujevac, Serbia

***Institute of Field and Vegetable Crops, Maksima Gorkog 30, 21000, Novi Sad, Serbia

****University of Novi Sad, Faculty of Agriculture, Dositeja Obradovića 8, 21000, Novi Sad, Serbia

(Received 19 July, revised 26 October 2010)

Soil of arable land and meadows from the Ap horizon, taken from ten different localities, were investigated for different forms of Fe, including total (HF), pseudo-total (HNO₃), 0.1 M HCl extractable and DTPA (diethylenetriAMinepentaacetic acid)-extractable. A sequential fractional procedure was employed to separate the Fe into fractions: water soluble and exchangeable Fe (I), Fe specifically adsorbed with carbonates (II), reducibly releasable Fe in oxides (III), Fe bonded with organic matter (IV) and Fe structurally bonded in silicates (residual fraction) (V). The soil pH, cation exchange capacity, and size fractions (clay and silt) had a strongest influence on the distribution of the different forms of Fe. The different extraction methods showed similar patterns of the Fe content in arable and meadow soils. However, the DTPA iron did not correspond with the total iron, which confirms the widespread incidence of iron-deficiency in vertisols is independent of the total iron in soils. The AMount of exchangeable (fraction I) and specifically adsorbed (II) iron showed no dependence on its content in the other fractions, indicating low mobility of iron in vertisols. The strong positive correlation (r = 0.812 and 0.956) between the content of iron in HNO₃ and HF and its contents in the primary and secondary minerals (fraction – V) indicate a low content of plant accessible iron in the vertisol. The sequential fractional procedure was confirmed as suitable for accessing the content and availability of iron in the vertisols of Serbia.

Keywords: soil; iron solubility; plant availability; adsorption; distribution of iron.

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J. Serb. Chem. Soc. 76 (5) 795–803 (2011)

UDC 627.157+546.36+539.163:627.8.034.7(282.243.743); JSCS–4160; doi: 10.2298/JSC100420067V; Original scientific paper

 

Distribution and accumulation of heavy metalsin the water and sediments of the River Sava

ŽIVORAD VUKOVIĆ, MIRJANA RADENKOVIĆ, SRBOLJUB J. STANKOVIĆ and DUBRAVKA VUKOVIĆ*

Institute of Nuclear Sciences Vinča, P. O. Box 522, Belgrade 11001, Serbia

*Institute of Veterinary Medicine, Vojvode Toze 24, Belgrade 11000, Serbia

(Received 20 April 2010, revised 7 January 2011)

The distribution and accumulation of assorted heavy metals and a long-lived radionuclide (Cu, Zn, Pb, Cd, U, Th and ¹³⁷Cs) in the water and sediment of the River Sava (in Serbia) were investigated at three locations in the vicinity of industrial and urban settlements (Sabac, Obrenovac, Belgrade). The concentrations of heavy metals in the sediment were found to be in the ranges (mg kg^-1): 29.6–145.1 for Cu, 53.2–253.6 for Zn, 14.2–78.6 for Pb, 0.3–24.6 for Cd, and 4.0–12.5 Bq l^-1 for ¹³⁷Cs. These values correlate to the con-centrations in the river water if expressed by equilibrium distribution coefficients K_d (dm³ g^-1) between the solid and liquid phases. The degrees of accumulation and enrichment of tracer metals were determined.

Keywords: accumulation; cesium; enrichment; heavy metals; Kd; sediment.

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