YU-ISSN 0352-5139
J.Serb.Chem.Soc. Vol 68, No 1 (2003)
CONTENTS
Organic Chemistry and Biochemistry
R. Markovi}, A. Shirazi, Z. D`ambaski, M. Baranac and D. Mini}: Hydrogen bonding in push-pull 5substituted-2-alkylidene-4-oxothiazolidines: 1H-MNR spectroscopic study
1
N. C. Nikoli} and M. Z. Stankovi}: Kinetics of solanidine hydrolytic extraction from potato (Solanum
tuberosum L) haulm solid-liquid systems
9
D. T. Veli~kovi}, N. V. Randjelovi}, M. S. Risti}, A. S. Veli~kovi} and A. [melcerovi}: Chemical
constituents and antimicrobial activity of the ethanol extracts obtained from the flower, leaf and stem of
Salvia officinalis L.
17
N. Toma{evi}, M. Nikoli}, K. Klappe, D. Hoekstra and V. Niketi}: Insulin-induced lipid binding to
hemoglobin
25
Physical Chemistry
M. Lj. Kijev~anin, A. B. Djordjevi}, I. R. Grguri}, B. D. Djordjevi} and S. P. [erbanovi}: Simultaneous
correlation of the excess enthalpy and W-shaped excess heat capacity of 1,4-dioxane-n-alkane systems by
PRSV-HVOS CEOS
35
I. R. Grguri}, M. Lj. Kijev~anin, B. D. Djordjevi}, A. @. Tasi} and S. P. [erbanovi}: Excess molar volume
of acetonitrile + alcohol systems at 298.15 K. Part II: Correlation by cubic equation of state
47
M. M. A~anski, S. Jovanovi}-[anta and L. R. Jevri}: Normal and reversed phase thin-layer chromatography
of new 16,17-secoestrone derivatives
57
Analtytical Chemistry
R. P. Mihajlovi}, N. R. Ignjatovi}, M. R. Todorovi}, I. Holclajtner-Antunovi} and V. M. Kaljevi}:
Spectrophotometric determination of phosphorus in coal and coal ash using bismuth-phosphomobybdate
complex
65
J.Serb.Chem.Soc. 68(1)1–7(2003)
UDC 541.11.027+547.313:543.422.25
JSCS – 3014
Original scientific paper
Hydrogen bonding in push-pull 5-substituted-2-alkylidene-4-oxothiazolidines: 1H-NMR spectroscopic
study
R. MARKOVI]a,b, A. SHIRAZIc, Z. D@AMBASKIb#, M. BARANACa,b and D. MINI]d
aFaculty of Chemistry, University of Belgrade, Studentski trg 16, P. O. Box 158, YU-11001 Belgrade,
bCenter for Chemistry ICTM, P. O. Box 815, YU-11000 Belgrade, cChemistry Department, University of
California, Santa Barbara, Santa Barbara, CA 93106, USA and dFaculty of Physical Chemistry, University
of Belgrade, Studentski trg 12-16, P. O. Box 137, YU-11001 Belgrade, Yugoslavia
(Received 7 March, revised 24 September 2002)
Abstract: Application of dynamic 1H-NMR spectroscopy added to the understanding of the hydrogen
bonds existing in the structurally related 5-substituted-2-alkylidene-4-oxothiazolidines in polar and apolar
solvents. The equilibrated mixtures of these typical push-pull alkenes in CDCl3 consist of the
intramolecularly H-bonded (E)-isomer and intermolecularly H-bonded (Z)-isomer in varying proportions
which depend on the solvent polarity. For the representative of the series, (Z)-2-(5-ethoxycarbonylmethyl4-oxothiazolidin-2-ylidene)-1-phenylethanone, a concentration effect on the degree of intermolecular
hydrogen bonding in apolar CDCl3 has been studied.
Keywords: push-pull alkenes, hydrogen bonding, 1H-NMR spectroscopy.
REFERENCES
1. R. Markovi}, M. Baranac, J. Serb. Chem. Soc. 63 (1998) 165
2. R. Markovi}, M. Baranac, Heterocycles 48 (1998) 893
3. R. Markovi}, M. Baranac, Synlett (2000) 607
4. R. Markovi}, Z. D`ambaski, M. Baranac, Tetrahedron 57 (2001) 5833
5. S. Rajappa, Tetrahedron 55 (1999) 7065
6. S. P. Singh, S. S. Parmar, K. Raman, V. I. Stenberg, Chem. Rev. 81 (1981) 175
7. J. Sandström, J. Top. Stereochem. 14 (1983) 83
8. J-M. Lehn, Angew. Chem. Int. Ed. Engl. 29 (1990) 1304 and references therein
9. Manuscript in preparation
10. O. Ceder, U. Stenhede, K.-I. Dahlquist, J. M. Waisvisz, M. G. van der Hoeven, Acta Chem. Scand. 27
(1973) 1914
11. L. Forlani, E. Mezzina, C. Boga, M. Forconi, Eur. J. Org. Chem. (2001) 2779
12. E. Kleinpeter, A. Koch, M. Heydenreich, S. K. Chatterjee, W.-D. Rudorf, J. Mol. Sruct. 356 (1995) 25
13. A. Gómez-Sánchez, R. Paredes-León, J. Cámpora, Magn. Reson. Chem. 36 (1998) 154
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J.Serb.Chem.Soc. 68(1)9–16(2003)
UDC 633.491:531.3+66.01+66.094.941
JSCS – 3015
Original scientific paper
Kinetics of solanidine hydrolytic extraction from potato (Solanum tuberosum L.) haulm in solid-liquid
systems
NADA ^. NIKOLI] and MIHAJLO Z. STANKOVI]
Faculty of Technology, University of Ni{, Bulevar oslobodjenja 124, 16000 Leskovac, Yugoslavia
(Received 11 July, revised 19 September 2002)
Abstract: Dried and milled haulm of potato (Solanum tuberosum L.) was used as the solid phase. An
ethanolic solution of hydrochloric acid mixed with chloroform in different volume ratios was the liquid
phase. The aim of paper was to unite in a single step the processes of glycoalkaloids extraction from haulm,
their hydrolysis to solanidine and the extraction of solanidine. This could make the procedure of obtaining
solanidine faster and simpler. The best degree of solanidine hydrolytic extraction of 84.5 % was achieved
using 10 % w/v hydrochloric acid in 96 % vol. ethanol mixed with chloroform in a volume ratio of 2:3,
after 120 min of hydrolytic extraction.
Keywords: potato, haulm, glycoalkaloids, hydrolysis, solanidine, extraction.
REFERENCES
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14. K. M. Ga{i, Z. O. Saka~, D. M. Rackov, D. S. Rausavljevi}, Review of Research, Faculty of Science University of Novi Sad 14 (1984) 5
15. M. Z. Stankovi}, N. C. Nikoli}, R. Pali}, M. D. Caki}, V. B. Veljkovi}, Potato Res. 37 (1994) 271
16. W. M. Gelder, J. Agric. Food Chem. 35 (1984) 487.
J.Serb.Chem.Soc. 68(1)17–24(2003)
UDC 615.281:635.74+547.262
JSCS – 3016
Original scientific paper
Chemical constituents and antimicrobial activity of the
ethanol extracts obtained from the flower, leaf and stem of Salvia officinalis L.
DRAGAN T. VELI^KOVI]*1, NOVICA V. RANDJELOVI]2, MIHAILO S. RISTI]3, ANA S.
VELI^KOVI]4 and ANDRIJA A. [MELCEROVI]5
*1AD “Zdravlje” Pharmaceutical and Chemical Industry, Vlajkova St. 199, YU-16000 Leskovac, 2Faculty
of Technology, Bulevar Oslobodjenja St. 124, YU-16000 Leskovac, 3Institute for Medicinal Plants
Research “Dr. Josif Pan~i}”, Tadeu{a Ko{}u{ka St. 1, YU-11000 Belgrade, 4Medical Center “Mo{a
Pijade”, Department of General Practice, Rade Kon~ara St. 2, YU-16000 Leskovac and 5Chemical
Industry “Nevena”, Djordja Stamenkovi}a St. bb., YU-16000 Leskovac, Yugoslavia
(Received 19 August 2002)
Abstract: In this paper a comparison of the chemical composition and antimicrobial action of the ethanol
extracts from the flower, leaf and stem of the herbal species Salvia officinalis L. (Lamiaceae), originating
from the southeast region of Serbia was carried out. The chemical composition of the extracts was
determined by GC-FID and GC-MS analyses. Manool has the highest level of all the components (9.0–11.1
%). Antimicrobial activity was determined by the diffusion and dilution method, whereby the latter one was
modified by use of cellulose discs, and it was applied for the determination of the minimal inhibitory (MIC)
and minimal lethal concentrations (MLC). The leaf extract has a stronger antimicrobial activity than those
of the flower and stem.
Keywords: Salvia officinalis L., Lamiaceae, extracts composition, manool, antimicrobial activity.
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J.Sereb.Chem.Soc. 68(1)25–33(2003)
UDC 612.349.8:611.018.5+612.111:616.379–008.61
JSCS – 3017
Original scientific paper
Insulin-induced lipid binding to hemoglobin
NENAD TOMA[EVI]1, MILAN NIKOLI]1, KAREN KLAPPE2, DICK HOEKSTRA2 and
VESNA NIKETI]1
1Chemistry Department, University of Belgrade, Studentski trg 16, P. O. Box 158, YU-11001 Belgrade,
Yugoslavia and 2Laboratory of Physiological Chemistry, University of Groningen, Bloemsingel 10, 9712
KZ Groningen, The Netherlands
(Received 22 July 2002)
Abstract: Under hypoglycemic conditions, concomitant hyperinsulinism causes an apparent modification of
hemoglobin (Hb) which is manifested by its aggregation (Niketi} et al., Clin. Chim. Acta 197 (1991) 47).
In the present work the causes and mechanisms underlying this Hb modification were studied. Hemoglobin
isolated from normal erythrocytes incubated with insulin was analyzed by applying 31P-spectrometry and
lipid extraction and analysis. To study the dynamics of the plasma membrane during hyperinsulinism, a
fluorescent lipid-analog was applied. In the presence of insulin, phosphatidylserine (PS),
phosphatidylethanolamine (PE) and cholesterol were found to bind to Hb. Lipid binding resulted in Hb
aggregation, a condition that can be reproduced when phospholipids are incubated with Hb in vitro. Using a
fluorescent lipid-analog, it was also shown that exposing erythrocytes to supraphysiological concentrations
of insulin in vitro resulted in the internalization of lipids. The results presented in this work may have
relevance to cases of diabetes mellitus and hypoglycemia.
Keywords: insulin, erythrocyte, hypoglycemia, hyperinsulinism, membrane lipids, hemoglobin.
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J.Serb.Chem.Soc. 68(1)35–46(2003)
UDC 541.21+547.94:536.722
JSCS – 3018
Original scientific paper
Simultaneous correlation of the excess enthalpy and W-shaped excess heat capacity of 1,4-dioxane+nalkane
systems by PRSV-HVOS CEOS
MIRJANA LJ. KIJEV^ANIN#, ALEKSANDAR B. DJORDJEVI], IVONA R. GRGURI]#, BOJAN D.
DJORDJEVI]# and SLOBODAN P. [ERBANOVI]
Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, P. O. Box 35-03, Belgrade,
Yugoslavia
(Received 9 September 2002)
Abstract: In this work the Peng-Robinson-Stryjek-Vera (PRSV) equation of state coupled with the HuronVidal-Orbey-Sandler (HVOS) rule was tested for the correlation of the excess enthalpy (HE) and the excess
heat capacity (cpE) alone and simultaneously. The HVOS mixing rule incorporates the NRTL equation as
the GE model. All calculations were performed using the linear and reciprocal forms of the temperature
dependent parameters of the models. For all the evaluations the 1,4-dioxane+n-alkane systems were chosen
having in mind the unusually W-shaped concentration dependence of cpE for these systems. The
correlation of the HE and cpE data alone for all the investigated systems using four coefficients and for the
simultaneous correlation of HE+cpE data using six coefficients of the temperature dependent parameters of
the PRSV-HVOS models could be considered as being very satisfactory.
Keywords: thermodynamics, n-alkane, 1,4-dioxane, excess properties, CEOS.
REFERENCES
1. H. Orbey, S. I. Sandler, Fluid Phase Equilibria 121 (1996) 67
2. T. Ohta, Fluid Phase Equilibria 129 (1997) 89
3. B. D. Djordjevi}, M. Lj. Kijev~anin, S. P. [erbanovi}, Fluid Phase Equilibria 155 (1999) 205
4. B. D. Djordjevi}, M. Lj. Kijev~anin, A. @. Tasi}, S. P. [erbanovi}, J. Serb. Chem. Soc. 64 (1999) 801
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J.Serb.Chem.Soc. 68(1)47–56(2003)
UDC 547.261/.262+547.239:541.24/.25
JSCS–3019
Original scientific paper
Excess molar volume of acetonitrile + alcohol systems at 298.15 K. Part II: Correlation by cubic equation
of state
IVONA R. GRGURI]#, MIRJANA LJ. KIJEV^ANIN#, BOJAN D. DJORDJEVI]#, ALEKSANDAR @.
TASI] and SLOBODAN P. [ERBANOVI]
Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, P. O. Box 35-03, Belgrade,
Yugoslavia
(Received 18 September 2002)
Abstract: The excess molar volume VE of the binary liquid systems acetonitrile + methanol and acetonitrile
+ ethanol, experimentally determined in the previous part, were correlated by the PRSV CEOS coupled
with the vdW and TCBT mixing rules. The results obtained show that the number and position of the
interaction parameters of these models are of great importance for a satisfactory fitting of VE data.
Keywords: excess molar volume, CEOS, correlation, alcohol, acetonitrile.
REFERENCES
1. H. Orbey, S. I. Sandler, Fluid Phase Equilibria 121 (1996) 67
2. B. D. Djordjevi}, M. Lj. Kijev~anin, S. P. [erbanovi}, Fluid Phase Equilibria 155 (1999) 215
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67 (2002) 581
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15. S. Malinowski, A. Anderko, Modeling Phase Equilibria, Wiley, New York, 1992, p. 153
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J.Serb.Chem.Soc. 68(1)57–63(2003)
UDC 661.183.7/.8:543.544.7
JSCS – 3020
Original scientific paper
Normal and reversed phase thin-layer chromatography of new 16,17-secoestrone derivatives
MARIJANA M. A^ANSKI1, SUZANA JOVANOVI]-[ANTA2# and LIDIJA R. JEVRI]1
1Department of General and Inorganic Chemistry, Faculty of Technology, University of Novi Sad, Bulevar
cara Lazara 1, YU-21000 Novi Sad and 2Institute of Chemistry, Faculty of Science, University of Novi
Sad, Trg Dositeja Obradovi}a 3, YU-21000 Novi Sad, Yugoslavia
(Received 31 August, revised 18 September 2002)
Abstract: The retention behaviour and separation ability of a series of new 16,17-secoestrone derivatives
has been studied on silica gel, alumina and C-18 silica gel layers with non-aqueous and aqueous-organic
mobile phases. The retention behavour and separation ability are discussed in terms of the nature of the
solute, eluent and stationary phase.
Keywords: thin-layer chromatography, silica gel, alumina, C-18 silica gel, 16,17-secoestrone derivatives.
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J.Serb.Chem.Soc. 68(1)65–73(2003)
UDC 543.482/485:546.18+552.574+561.877
JSCS–3021
Original scientific paper
Spectrophotometric determination of phosphorus in coal and coal ash using bismuth-phosphomolybdate
complex
RANDJEL P. MIHAJLOVI],1 NATA[A R. IGNJATOVI]1, MARIJA R. TODOROVI],2# IVANKA
HOCLAJTNER-ANTUNOVI]3# and VESNA M. KALJEVI]1
1Faculty of Science, University of Kragujevac, P. O. Box 60, YU-34000 Kragujevac, 2Faculty of
Chemistry, University of Belgrade, P. O. Box 158, YU-1001 Belgrade and 3Faculty of Physical Chemistry,
University of Belgrade, YU-11001 Belgrade, Yugoslavia
(Received 5 March, revised 7 October 2002)
Abstract: A modified spectrophotometric method using the bismuth phosphomolybdate complex for the
determination of phosphorus in coal and coal ash is suggested. Bismuth together with phosphate and
molybdate forms a very stable complex in acid medium which turns blue (“molibdenum blue”) by
reduction with ascorbic acid. The apparent molar absorptivity of PBiMo is 1.66´104 dm3 mol-1cm-1 at 720
nm and 2.10´104 dm3 mol-1cm-1 at 670 nm isobutyl methyl ketone (MIBK). Interference caused by the
ions present are within the tolerance limits (±2 %). Beer’s law is obeyed in the for concentration range to
0.6 mg/mL (aqueous solution) and to 1.2 mg/mL P (MIBK). The sesitivity of the proposed method is
0.0078 mg/mL (aqueous solution) and 0.0066 mg/mL (MIBK).
Keywords: spectrophotomery, phosphorus determination, coal, coal ash, bismuth phosphomolybdate
complex.
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