JSCS Vol 72, No. 4

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J. Serb. Chem. Soc. 72 (4) 311–320 (2007)

UDC 582.475/.477:665.5:615.28+615.33, JSCS–3560, doi: 10.2298/JSC0704320G; Original scientific paper

Antimicrobial activity of the essential oil and different fractions of Juniperus communis L. and a comparison with some commercial antibiotics

SANDRA B. GLIIC, SVETOMIR Ž. MILOJEVIC*, SUZANA I. DIMITRIJEVIC, ALEKSANDAR M. ORLOVIC and DEJAN U. SKALA

Faculty of Technology and Metallurgy, Karnegijeva 4, P.O Box 494, YU-11001 Belgrade, Serbia

*Faculty of Tehnical Sciences, 38220 Kosovska Mitrovica, Serbia

(Received 30 December 2005, revised 9 October 2006)

The essential oil of common juniper (Juniperus communis L., from the southern part of Serbia) and its fractions of different composition, as well as commercial antibiotics were used for testing their antimicrobial activity against bacteria, yeast and fungi. The essential oil was produced by hydro-distillation in a pilot plant (130 dm³) and then fractionated by distillation over a column, with 36 theoretical stages, under vacuum (26–66 mbar). The essential oil was also fractionated using pure CO₂ or CO₂ and methanol as co-solvent under supercritical conditions. The native oil showed weak antimicrobial activity, while the fractions with a high content of a-pinene, and mixture of a-pinene and sabinene showed the highest antimicrobial activity, especially against fungi. In comparison to the commercial antibiotics, the oil fractions showed more extensive spectra of antimicrobial activity, as well as wider inhibition zones.

Keywords: Juniperus communis L., essential oil, distillation, supercritical fractionation, antimicrobial activity, antibiotics.

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J. Serb. Chem. Soc. 72 (4) 321–329

UDC 582.916.51:547.972.2:615.28+615.277, JSCS–3561 doi: 10.2298/JSC0704321M; Original scientific paper

Cytotoxic and antimicrobial activities of two new synthetic 2'-oxygenated flavones reported from Andrographis viscosula

SOHEL MOSTAHAR, SAYED ALAM*^,** and AZIZUL ISLAM*

Department of Chemistry, University of Rajshahi, Rajshahi-6205, Bangladesh,

*Department of Chemistry, Rajshahi University of Engineering &AMp; Technology, Rajshahi-6204, Bangladesh

**Department of Life Science and Biotechnology, Shimane University, Matsue, Shimane 690-8504, Japan

(Received 16 March 2006)

Two new 2'-oxygenated flavones have been synthesized via chalcone precursors and the biocidal activity of these two flavones, along with the corresponding chalcones against microbes (bacteria and fungi) and brine shrimp nauplii were investigated. Both the flavones (compounds 6 and 7) and their corresponding chalcones (compounds 4 and 5) showed good activity against all the tested bacterial and fungal strains. The LC₅₀ values of compounds 4– 7 were found to be 2.31, 0.94, 1.39 and 0.58 mgmL^-1, respectively. The synthesized compoundswere characterized using UV–VIS, IR, ¹H-NMR and ¹³C-NMR spectral data, together with elemental analysis.

Keywords: 2'-oxygenated flavone, Andrographis viscosula, cytotoxicity, antibacterial and antifungal activity, inhibition zone.

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J. Serb. Chem. Soc. 72 (4) 331–337 (2007)

UDC 547.926.3+546.47:66.022.393+536.6, JSCS–3562, 10.2298/JSC0704331O; Original scientific paper

A DSC study of zinc binding to bovine serum albumin (BSA)

SANJA OSTOJIC, VIDA DRAGUTINOVIC, MIODRAG KICANOVIC and BRANISLAV R. SIMONOVIC

Holding Institute of General and Physical Chemistry, Studentski trg 12/V, P. O. Box 551, 11000 Belgrade, Serbia

(Received 20 March, revised 10 April 2006)

The thermal denaturation of bovine serum albumin (BSA) is a kinetically and thermodynAMically controlled process. The effects of zinc binding to bovine serum albumin (BSA), followed by differential scanning calorimetry (DSC), were investigated in this work, with the purpose of obtaining a better understanding of the albumin/zinc interaction. From the DSC curves, the thermodynAMic parAMeters of protein denaturation were obtained, i.e., the temperature of thermal transition maximum (T_m), calorimetric enthalpy (DH^cal), van't Hoff enthalpy (DH^vH), the number of binding sites (I, II), the binding constants for each binding site (K_bI, K_bII) and the average number of ligands bound per mole of native protein X_N. The thermodynAMic data of protein unfolding showed that zinc binding to bovine serum albumin increases the stability of the protein (higher values of DH^cal) and the different ratio DH^cal/DH^vH indicates the perturbation of the protein during thermal denaturation.

Keywords: bovine serum albumin, thermal denaturation, DSC, zinc, binding.

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J. Serb. Chem. Soc. 72 (4) 339–345 (2007)

UDC 547.922:612.11:611.018.5:577.15, JSCS–3563, 10.2298/JSC0704339N; Short communication

Short communication

Does cholesterol bound to hemoglobin affect the anti-oxidant enzyme defense system in human erythrocytes?

MILAN NIKOLIC*, ALEKSANDRA NIKOLIC KOKIC**, DRAGANA STANIC***, DUSKO P. BLAGOJEVIC**, DANIJELA VRANIC****, DAVID R. JONES*, VESNA NIKETIC* and MIHAJLO B. SPASIC*^,**

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

**Department of Physiology, Institute of Biological Research "Sinisa Stankovic", Bulevar Despota Stefana 142, 11060 Belgrade, Serbia

***Center for Chemistry - ICTM, Njegoseva 12, 11000 Belgrade, Serbia

****Institute of Meat Hygiene and Technology, Kacanskog 13, Belgrade, Serbia

(Received 29 November 2005)

In a previous study, it was shown that the lipid fraction, which is occasionally observed in red blood cell hemolysates, represents cholesterol (Ch) associated with phospholipid firmly bound to haemoglobin (termed Hb-Ch). The current study was conducted to investigate whether Hb-Ch could affect the primary anti-oxidant enzyme defense system in human erythrocytes. Sixty healthy volunteers were used for the current study. Group 1 consisted of 28 subjects without or with a low level of Hb-Ch. Group 2 comprised 32 subjects with a considerably higher level of Hb-Ch. The activities of erythrocyte superoxide dismutase, catalase, glutathione peroxidase and glutathione reductase, as well as the content of methaemoglobin (metHb) were measured in both groups. The results indicated that the AMount ofHb-Ch neither influenced the activities of the erythrocyte anti-oxidant enzymes nor altered the level of metHb. However, a higher AMount ofHb-Ch changed the correlations in the part of the anti-oxidant defence system relating to glutathione, suggesting increased peroxidative pressure from plasma lipids. Group 2 also had significantly increased concentrations of total plasma Ch and triglycerides. Together, these facts are strong indications that the anti-oxidant defence system in human erythrocytes finely retunes its composition according to plasma oxidative demands.

Keywords: erythrocytes, haemoglobin, cholesterol, anti-oxidant defense enzymes.

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J. Serb. Chem. Soc. 72 (4) 347–356 (2007)

UDC 543.62+546.175:620.266.1:591.481.1, JSCS–3564, doi: 10.2298/JSC0704347C; Original scientific paper

Determination of nitrate by the IE-HPLC-UV method in the brain tissues of Wistar rats poisoned with paraquat

MARIJANA CURCIC JOVANOVIC, MIRJANA DJUKIC, IVANA VASILJEVIC*, MILICA NINKOVIC* and MARINA JOVANOVIC*

Institute of Toxicological Chemistry, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, 11221 Belgrade, Serbia

*Institute for Medical Research, Military Medical Academy, Crnotravska 17, 11000 Belgrade, Serbia

(Received 17 February, revised 5 July 2006)

This work was a part of an initial study regarding the involvement of reactive nitrogen species (RNS) in paraquat (PQ) neurotoxicity. The nitrate concentration

in the vulnerable regions of the brain (cortex, striatum and hippocAMpus) of Wistar rats was used as a measure of nitric oxide (NO) production or catabolism of the formed RNS. The tissue homogenates were deproteinized with acetonitrile and then centrifuged. Nitrate was measured in filtrated supernatants by simple and rapid isocratic ion-exchange high performance liquid chromatography with UV detection (IE-HPLC-UV) at 214 nm. The mobile phase (pH 8.5) consisted of borate buffer/gluconate concentrate, methanol, acetonitrile and deionized water (2:12:12:74, v/v/v/v), and the flow rate was 1.3 mL/min. Physiological nitrate levels (18.8 ± 6.1 nmol/mg of proteins), as well as a diverse range of nitrate concentrations could be determined with good precision (CV = 2.2 %) and accuracy (recovery of spiked sAMples was 99 ± 4%) in the brain tissue homogenates. Linearity was achieved in the range of nitrate from 0‑80 mM. The retention time of nitrate anion was 5.3 ± 0.3 min.

Keywords: nitrate, IE-HPLC-UV, brain, paraquat.

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J. Serb. Chem. Soc. 72 (4) 357–366 (2007)

UDC 547.78+546.712'732'742'542'472:54–74:57–188, JSCS–3565, doi: 10.2298/JSC0704357G; Original scientific paper

Transition metal complexes with a new tridentate ligand, 5-[6-(5-mercapto-1,3,4-oxadiazol-2-yl)pyridin-2-yl]-1,3,4-oxadiazole-2-thiol

KALAGOUDA GUDASI, MANJULA PATIL, RAMESH VADAVI, RASHMI SHENOY and SIDDAPPA PATIL

Department of Chemistry, Karnatak University, Dharwad-580 003, India

(Received 13 January, revised 20 July 2006)

A new ligand 5-[6-(5-mercapto-1,3,4-oxadiazol-2-yl)pyridin-2-yl]-1,3,4-oxadiazole-2-thiol (L) and its Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) complexes were synthesized. The authenticity of the ligand and its transition metal complexes were established by elemental analyses, conductance and magnetic susceptibility measurements, as well as spectroscopic (IR, ¹H- and ¹³C-NMR, electronic, mass, ESR) and thermal studies. The IR and ¹H-NMR spectral studies revealed the existence of the ligand in the thiol form in the solid state, whereas in the thione form in the dissolved state. The magnetic and electronic spectral studies suggest an octahedral geometry for all the complexes. The ligand acts as a tridentate ligand coordinating through the pyridine nitrogen and the nitrogen atoms (N-3' and N-3'') of the two oxadiazole rings. Antimicrobial screening of the ligand and its metal complexes were determined against the bacteria Escherichia coli and Bacillus cirroflagellosus, as well as against the fungi, Aspergillus niger and Candida albicans.

Keywords: oxadiazole, transition metal complexes, magnetic moments, IR spectra, electronic spectra, biological activity.

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J. Serb. Chem. Soc. 72 (4) 367–374 (2007)

UDC 542.913+661.65+547.85:547.516:54–74:615.282, JSCS–3566, doi: 10.2298/JSC0704367G; Original scientific paper

Synthesis and characterizaton of some new coordination compounds of boron with mixed azines

MANISH GODARA, R. MAHESHWARI, S. VARSHNEY and A. K. VARSHNEY

Department of Chemistry, University of Rajasthan, Jaipur-302004, India

(Received 8 February, revised 4 September 2006)

Some new boron complexes have been synthesized by the reaction of triisopropohxyborane with the mixed azines, prepared by the condensation of salicylaldehyde and hydrazine with aldehydes/ketones in a 1:1:1 mole ratio to give a new series of (OPrⁱ)2B(NO) type of complexes. Their structures were confirmed on the basis of elemental analyses, ultraviolet, infrared, ¹H-NMR and ¹¹B-NMR spectral studies. The ligands and their boron complexes were also screened for their antifungal activity. Several of these complexes were found to be quite active in this respect.

Keywords: mixed azines, aldehydes/ketones, triisopropoxyborane, spectral studies, antifungal activity.

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J. Serb. Chem. Soc. 72 (4) 375–382 (2007)

UDC 678.652+547.6:54–74, JSCS– 3567, doi: 10.2298/JSC0704375Z; Original scientific paper

Ab initio studies on complexes formed by melAMine and cyclotrione

LIANGIANG ZHU, QIWEN TENG and SHI WU

Department of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China

(Received 8 March, revised 15 June 2006)

Ab initio methods were used to study the binding energies of non-bonded complexes formed by melAMine and cyclotrione, with the STO-3G, 3-21G and 6-31G (d) basis sets. The electronic spectra were computed using the INDO/CIS method, and the IR spectra, RAMan and NMR spectra with the RHF/6-31G (d)method. It was demonstrated that the complexes could be formed because of the negative binding energies, which were changed with the change in the electronic properties of the monomers. A red-shift of the first absorptions in the electronic spectra and the vibrational frequencies of the N–H bonds in the IR and RAMan spectra of the complexes, compared with those of the monomers, occurred; simultaneously, the ¹Hand ¹³C chemical shifts were altered, due to the non-bonded interaction.

Keywords: melAMine, cyclotrione, non-bonded interaction, RHF/6-31G (d)

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J. Serb. Chem. Soc. 72 (4) 383–392 (2007)

UDC 577.112+547.466:535.337:54.03, JSCS– 3568, doi: 10.2298/JSC0704383I; Original scientific paper

Analysis of long-range correlation in sequences data of proteins

ADRIANA ISVORAN, LAURA UNIPAN*, DANA CRACIUN** and VASILE MORARIU***

West University of Timisoara, Department of Chemistry, Str. Pestalozzi 16, 300115 Timisoara, Romania

*University of Agricultural Sciences of Banat, Department of Agriculture, Cl. Aradului 119, 300645 Timisoara, Romania

**West University of Timisoara, Teacher Training Department, Blvd. V. Parvan 4, 300223 Timisoara, Romania

***National R&AMp;D Institute for Isotopic and Molecular Technology, Department of Molecular and Biomolecular Physics, P. O. Box 700, 400293 Cluj Napoca, Romania

(Received 9 November 2005, revised 19 July 2006)

The results presented here suggest the existence of correlations in the sequence data of proteins. 32 proteins, both globular and fibrous, both monomeric and polymeric, were analyzed. The primary structures of these proteins were treated as time series. Three spatial series of data for each sequence of a protein were generated from numerical correspondences between each AMino acid and a physical property associated with it, i.e., its electric charge, its polar character and its dipole moment. For each series, the spectral coefficient, the scaling exponent and the Hurst coefficient were determined. The values obtained for these coefficients revealed non-randomness in the series of data.

Keywords: sequences of proteins, long-range correlation, spectral coefficient, scaling exponent, Hurst coefficient.

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J. Serb. Chem. Soc. 72 (4) 393–402 (2007)

UDC 549.514.6+669–034.89:544.526.5, JSCS–3569, doi: 10.2298/JSC0704393L; Original scientific paper

Effect of doping TiO₂ with alkaline-earth metal ions on its photocatalytic activity

YUEXIANG LI, SHAOQIN PENG, FENGYI JIANG*, GONGXUAN LU** and SHUBEN LI**

Department of Chemistry, Nanchang University, Nanchang 330047, PR China

*Institute of Materials Science, Nahchang University, Nahchang 330047, PR China

**State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, PR China

(Received 29 March, revised 10 August 2006)

TiO₂ photocatalysts doped with alkaline-earth metal ions were prepared by the impregnation and coprecipitation methods. The sAMple were characterized by XRD, XPS and IR spectroscopy. Their activities were evaluated by the photocatalytic production of hydrogen. The activities of the doped photocatalysts dopended on the size of the dopant ions and the dopingmethod. The optimum molar contents of dopant ions Be²⁺, Mg²⁺, Ca²⁺, Sr²⁺, Ba²⁺ were 1.25, 1.25, 2.25, 2.25 and 2.25 at. %, respectively. The optimum calcination temperature and time were 400 °C and 1 h.

Keywords: photocatalysis, titanium dioxide, doping, alkaline-earth metal, activity.

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J. Serb. Chem. Soc. 72(4) 403–406 (2007)

UDC 678.7.004.12:543.544.3.054.1, JSCS–3570, doi: 10.2298/JSC0704403N; Extended Abstract

Extended Abstract

Surface characterization of polymers by inverse gas chromatography

ALEKSANDRA B. NASTASOVIC and ANTONIJE E. ONJIA*

ICTM-Center for Chemistry, Studentski trg 12–16, 11001 Belgrade, Serbia

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

(Received 30 November 2005, revised 30 January 2007)

An inverse gas chromatographic (IGC) study of the sorption properties of macroporous crosslinked poly(glycidyl methacrylate-co-ethylene glycol dimethacrylate), PGME, and PGME modified with ethylene diAMine, PGME-en, was presented. At infinite dilution, the thermodynAMic parAMeters of adsorption, the dispersive components of the surface free energies, the acid/base constants and the interaction parAMeters for the initial and modified copolymer sAMples were investigated. The adsorption isotherms determined by IGC under conditions of finite surface coverage were used to estimate the surface area, the isosteric heat of adsorption and the adsorption energy distribution on the surface of the initial and modified copolymer sAMples.

Keywords: IGC, glycidyl metacrylate based copolymers, acid/base properties, interaction parAMeters.

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J. Serb. Chem. Soc. 72 (4) 407–413 (2007)

UDC *Calendula officinalis L.: 546.264–31:66.061, JSCS–3571, doi: 10.2298/JSC0704407P; Original scientific paper

An investigation of CO₂ extraction of marigold (Calendula officinalis L.)

LIDIJA PETROVIC, ZIKA LEPOJEVIC, VERICA SOVILJ, DUSAN ADAMOVIC* and VELE TESEVIC**

University of Novi Sad, Faculty of Technology, Department of Applied and Engineering Chemistry, Bul. Cara Lazara, 1, 21000 Novi Sad, Serbia

*Institute of Field and Vegetable Corps, 21000 Novi Sad, Serbia

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

(Received 6 April, revised 5 September 2006)

Essential oil content (0.05 %) of marigold (Calendula officinalis L.) was determined using the official steAM distillation procedure. High-pressure CO₂ extraction of plant material under supercritial (100, 200 and 300 bar and 40 °C) and subcritical (60, 90 and 120 bar and 15 °C) conditions for 3 h was investigated. It was found that the increase in the pressure promoted an increase in the yield. The essential oil contents obtained from the investigated CO₂ extracts by steAM distillation were significantly higher (1.52–2.70 times) and increased with pressure.Major constituents of the oil, identified using GC-MS and GC-FID, were a-cadinol (26.54 %), T-cadinol and T-muurolol (9.80 %), g-cadinene (2.99 %), hexadecanoic acid (2.95 %), and ledane (2.45 %). In addition, the essential oils of the CO₂ extracts contained d-cadinene (6.50–19.87 % under supercritical and 16.09–19.41 % under subcritical conditions), which was not found in the essential oil obtained from the plant by steAM distillation. The extraction kinetics was investigated at 200 bar and 40 °C. The total extract obtained after 10 h of extraction was 6.54 % and essential oil content in it, refering to plant material, was 0.209 %, which is 4.16 times more than the one determined by the standard steAM distillation procedure.

Keywords: marigold, Calendula officinalis L., CO₂ extraction, essential oil, GC-MS analysis.

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J. Serb. Chem. Soc. 72 (4) 415–419 (2007)

DIVISION OF ANALYTICAL CHEMISTRY EUROPEAN ASSOCIATION FOR CHEMICAL AND MOLECULAR SCIENCES

EUROPEAN ANALYTICAL COLUMN No. 35

(January 2007)

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May 15, 2007.
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