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EDITORIAL
This issue of the Journal of the Serbian Chemical Society is dedicated to an
accomplished scientist and excellent mentor Academician Slobodan Milosav-
ljević, Professor Emeritus at the University of Belgrade – Faculty of Chemistry,
on the occasion of his 80th birthday, in honor of his many achievements in
chemistry, his contribution to university education, structural instrumental
analysis and natural products chemistry at the University of Belgrade.
Slobodan was born in Belgrade on 30 Dec-
ember, 1941. He grew up in Belgrade, where his
mother was philologist and the father university
professor, and where he finished the high school.
He received B.S. (in 1965) from Faculty of Tech-
nology and Metallurgy, University of Belgrade,
M.S. (in 1970) as well as PhD (in 1974) at Dep-
artment of Chemistry, Faculty of Science and
Mathematics (later Faculty of Chemistry) Univer-
sity of Belgrade.
The two years of postdoctoral studies (1974–
–1976) included the synthesis of natural products,
at The Polytechnic of North London, with Dr. A.
P. Johnson.
The first job was in INEP Institute for Application of Nuclear Energy 1965,
but Slobodan soon moved to Institute for Chemistry 1966, and finally to Faculty
of Chemistry 1970, where stayed till retirement. He became assistant, associate,
and full professor at the University of Belgrade in 1970, 1986 and 1992, respec-
tively.
Slobodan’s lifelong interest for structural analysis started when he joined
prof Jeremić at the Institute for Chemistry in 1966, and helped develop modern
Laboratory for instrumental analysis.
The Laboratory, later Center for instrumental analysis (CIA), equipped with
IR, UV–Vis, MS and NMR gradually became a core for further teaching and
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1132 EDITORIAL
scientific work in chemistry. Main task and interest was structure determination
of organic compounds.
Slobodan dedicated most of his energy creating better conditions for sci-
entific work in chemistry and similar, related sciences, like biology, that use the
aforementioned analytical tools. He is still involved in work of this Centre
assisting in solving problems concerning structure elucidation of various com-
pounds and commercial products.
As a researcher, Slobodan mostly deals with investigation and interpretation
of NMR and mass spectra of syntetised and natural compounds. It presents a
permanent scientific interest and have started with M.S. thesis.
The main research topic in last two decades was isolation and identification
of natural products, the constituents of wild-growing plant species from Serbia
and Montenegro by means of spectroscopic and chromatographic methods (1D
and 2D NMR, MS, GLC–MS, IR, UV–Vis, HPLC). Lately he is involved in
metabolomics investigations of plants.
Besides intensive scientific work (about 150 original papers and reviews),
Slobodan was dedicated to teaching 1979-1986 “Structural instrumental
methods” at the same faculty. From 1979 teaching in “Organic chemistry of
natural products” for the third-year undergraduate students of Molecular biology
at the Faculty of Biology, Belgrade; from 2000 teaching in “Structural
instrumental methods II” at the Faculty of Chemistry.
In his very good textbook “Structural instrumental methods” (in Serbian), II
edition published at the Faculty of Chemistry (2004) Slobodan treats the subjects
in more than 500 pages.
Slobodan also served as a visiting professor, teaching Structural instrumental
methods at the University of Niš and Kragujevac. He led numerous students in
their diploma (B.S.) works, M.S. theses, and Ph.D. dissertations. As a member of
committees, he selflessly helped students and degree candidates mentored by his
colleagues.
Students, associates and colleagues respect Slobodan as a scholar and admire
him as a man for his modesty and fine humor. He has trained many academics,
collaborated with others in research, and influenced large number of students
over the decades of his academic career. Some of these students contribute to this
Special Issue.
Serbian Academy of Sciences and Arts elected Slobodan as a Corresponding
Member in 2009 and as a Full Member in 2018.
Serbian Chemical Society gave Slobodan a Medal for his lasting and out-
standing contribution to science in 2006. University of Belgrade appointed him
Professor Emeritus 2012.
Besides chemistry, Slobodan enjoys fishing, tennis and skiing.
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EDITORIAL 1133
The papers in this issue deal mostly with natural products chemistry. Space
limits prevented us from inviting contributions by other, equally deserving
authors affiliated with Faculties Chemistry, Biology and Pharmacy. We thank all
contributors for their efforts, as well as for financial support.
On behalf of your colleagues, collaborators and students, we dedicate this
Special Issue to you, Slobodan, and hope that you will enjoy it for years to come.
Belgrade, December 2021
Guest Editors
Dr. Vele Tešević, Full Professor
University of Belgrade – Faculty of Chemistry
Dr. Ljubodrag Vujisić, Associate Professor
University of Belgrade – Faculty of Chemistry
SELECTED PUBLICATIONS
S. Milosavljević, D. Jeremić and M. Lj. Mihailović, 1,5-Shift of Hydrogen from Carbon to
Carbon in the Lead Tetraacetate Oxidation of 5,5-Dimethyl-2- heptanol, Tetrahedron 29
(1973) 3547
F. W. Wehrli, D. Jeremić, M. Lj. Mihailović and S. Milosavljević, Long-range Deuterium-
-induced 13C Nuclear Magnetic Resonance Isotope Shifts for Signal Assignment and Deter-
mination of Deuteriation Site in Cyclodecanone Isotopomers, Chem. Commun. (1978) 302
M. Stefanović, I. Aljančić-Šolaja and S. Milosavljević, A 3,4-seco-Ambrosanolide from
Ambrosia artemisiifolia, Phytochemistry 26 (1987) 850
V. Vajs, D. Jeremić, S. Milosavljević and S. Macura, Two-dimensional NMR Spectra of
Sesquiterpenes. I - NOESY Study of Caryophyllenes from Inula spiraeifolia, Magnetic Reson.
Chem. 25 (1987) 889
S. Milosavljević, I. Aljančić, S. Macura, D. Milinković and M. Stefanović, Sesquiterpene
Lactones from Achillea crithmifolia, Phytochemistry 30 (1991) 3464
V. Bulatović, V. Vajs, S. Macura, N. Juranić and S. Milosavljević, Highly Oxygenated
Guaianolides from Anthemis carpatica, J. Nat. Prod. 60 (1997) 1222
S. Trifunović, V. Vajs, S. Macura, N. Juranić, Z. Djarmati, R. Jankov and S. Milosavljević,
Oxidation Products of Hyperforin from Hypericum perforatum, Phytochemistry 49 (1998)
1305-1310
M. Malinar, Dj. Miodragović, S. Milosavljević, M. Ćelap and D. Vučelić, Mixed Cobalt(III)
Complexes with S-Tyrosine and 1,3-Diaminopropane, Enantiomer 3 (1998) 349-356
S. Milosavljević, V. Vajs, V. Bulatović, D. Djoković, I. Aljančić, N. Juranić and S. Macura,
Application of two-dimensional nuclear magnetic resonance methods for structure elucidation
of sesquiterpene lactones (guaianolides) from Anthemis carpatica and diterpenes (kauranes)
from Achillea clypeolata, Recent Res. Dev. Phytochem. 2 (1998) 383
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1134 EDITORIAL
S. Milosavljević, V. Bulatović and M. Stefanović, Sesquiterpene lactones from the Yugo-
slavian wild growing plant families Asteraceae and Apiaceae, J. Serb. Chem. Soc. 64 (1999)
397
I. Aljančić, V. Vajs. N. Menković, I. Karadžić, N. Juranić, S. Milosavljević and S. Macura,
Flavones and Sesquiterpene Lactones from Achillea atrata subsp. multifida: Antimicrobial
Activity, J. Nat. Prod. 62 (1999) 909-911
V. Vajs, N. Todorović, M. Ristić, V. Tešević, B. Todorović, P. Janaćković, P. Marin and S.
Milosavljević, Guaianolides from Centaurea nicolai: antifungal activity, Phytochemistry 52
(1999) 383
N. Menković, K. Šavikin-Fodulović, V. Bulatović, I. Aljančić, N. Juranić, S. Macura, V. Vajs,
S. Milosavljević, Xanthones from Swertia punctata, Phytochemistry 61 (2002) 415
K. Šavikin-Fodulović, I. Aljančić, V. Vajs, N. Menković, S. Macura, G. Gojgić, S. Milosav-
ljević, Hyperatomarin, an Antibacterial Prenylated Phloroglucinol from Hypericum atoma-
rium ssp. degenii, J. Nat. Prod. 66 (2003) 1236
I. Djordjević, V. Vajs, V. Bulatović, N. Menković, V. Tešević, S. Macura, P. Janaćković, S.
Milosavljević, Guaianolides from two subspecies of Amphoricarpos neumayeri from Monte-
negro, Phytochemistry 65 (2004) 2337
S. Trifunović, V. Vajs, Z. Juranić, Ž. Žižak, V. Tešević, S. Macura, S. Milosavljević, Cyto-
toxic constituents of Achillea clavennae from Montenegro, Phytochemistry 67 (2006) 887
I. S. Aljancic, V. E. Vajs, V. V. Tesevic, S. M. Milosavljevic, Some Wild-Growing Plant
Species from Serbia and Montenegro as the Potential Sources of Drugs, Curr. Pharmaceut.
Des. 14 (2008) 3089
K. Šavikin, T. Janković, D. Krstić-Milošević, N. Menković, S. Milosavljević, Secondary
Metabolites and Biological Activities of some Gentianaceae Species from Serbia and Monte-
negro, in Comprehensive Bioactive Natural Products Extraction, Isolation & Character-
ization, Studium Press LLC, USA, 2010, pp. 323–340
I. S. Aljančić, M. Pešić, S. M. Milosavljević, N. M. Todorović, M. Jadranin, G. Milo-
savljević, D. Povrenović, J. Banković, N. Tanić, I. D. Marković, S. Ruždijić, V. E. Vajs and
Vele V. Tešević, Isolation and Biological Evaluation of Jatrophane Diterpenoids from
Euphorbia dendroides, J. Nat. Prod. 74 (2011) 1613
D. Gođevac, V. Tešević, V. Vajs, S. Milosavljević, G. Zdunić, B. Ordević and M. Stanković,
Chemical Composition of Currant Seed Extracts and Their Protective Effect on Human Lym-
phocytes DNA, J. Food. Sci. 77 (2012) 779
D. Godevac, V. Tesevic, V. Vajs, S. Milosavljevic and M. Stankovic, Antioxidant Evaluation
of Heterocyclic Compounds by Cytokinesis-Block Micronucleus Assay, In Mini-Reviews in
Medicinal Chemistry, Bentham Sci. 13 (2013) 431
I. S. Aljančić, I. Vučković, M. Jadranin, M. Pešić, I. Đorđević, A. Podolski-Renić, S. Stoj-
ković, N. Menković, V. E. Vajs, S. M. Milosavljević, Two structurally distinct chalcone
dimers from Helichrysum zivojinii and their activities in cancer cell lines, Phytochemistry 98
(2014) 190
M. Novaković, M. Pešić, S. Trifunović, I. Vučković, N. Todorović, A. Podolski-Renić, J.
Dinić, S. Stojković, V. Tešević, V. Vajs, S. Milosavljević, Diarylheptanoids from the bark of
black alder inhibit the growth of sensitive and multi-drug resistant non-small cell lung
carcinoma cells, Phytochemistry 97 (2014) 46
N. Menković, K. Šavikin, G. Zdunić, S. Milosavljević and J. Živković, Medicinal Plants in
Northern Montenegro: Traditional Knowledge, Quality, and Resources, in Ethnobotany and
Biocultural Diversities in the Balkans - Perspectives on Sustainable Rural Development and
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EDITORIAL 1135
Reconciliation, Pieroni, Andrea, Quave, Cassandra L. (Eds.), Springer New York, 2014, pp.
197–228
K. Šavikin, I. S. Aljančić, V. E. Vajs, S. M. Milosavljević, M. Jadranin, I. Đorđević and N. R.
Menković, Bioactive Secondary Metabolites in Several Genera of Gentianaceae Species from
the Central Regions of the Balkan Peninsula, in The Gentianaceae - Vol. 2: Biotechnology and
Applications, J. J Rybczyński, M. R. Davey, M. Anna (Eds.), , Springer-Verlag, Heidelberg,
2015, pp. 319–348
D. Gođevac, M. Jadranin, I. Aljančić, V. Vajs, V. Tešević, and S. Milosavljević, Application
of Spectroscopic Methods and Hyphenated Techniques to the Analysis of Complex Plant
Extracts, in Medicinal and Aromatic Plants of the World, Scientific, Production, Commercial
and Utilization Aspects, A. Máthé (Ed.), Springer-Verlag, Heidelberg, 2015, pp. 61–85
V. Vajs, A. Jokić, S. Milosavljević, Artemisinin Story from the Balkans, Nat. Prod. Commun.
12 (2017) 1157
M. Cvetković, B. Anđelković, V. Stevanović, M. Jadranin, I. Đorđević, V. Tešević, S. Milo-
savljević., D. Gođevac NMR-based metabolomics study of Amphoricarpos species from
Montenegro, Phytochemistry Lett. 25 (2018) 1
M. Novakovic, J. Nikodinovic-Runic, J. Veselinovic, T. Ilic Tomic, V. Vidakovic, V. Tesevic,
S. Milosavljevic, Bioactive Pentacyclic Triterpene Ester Derivatives from Alnus viridis ssp.
viridis Bark, J. Nat. Prod. 80 (2017) 1255
M. Novakovic, D. Bukvicki, V. Vajs, V. Tesevic, S. Milosavljevic, P. Marin, Y. Asakawa,
Microbial Transformation of Calamintha glandulosa Essential Oil by Aspergillus niger, Nat.
Prod. Commun. 13 (2018) 479
M. Cvetković, B. Anđelković, V. Stevanović, M. Jadranin. I. Đorđević, V. Tešević, S. Milo-
savljević, D. Gođevac, NMR-bsed metabolomics study of Amphoricarpos species from Mon-
tenegro, Phytochemistry Lett. 25 (2018) 1
V. Vajs, I. Đorđević, Lj. Vujisić, and S. M. Milosavljević, NMR Spectroscopy in the Ana-
lysis of Illegal Drugs, in Chromatographic Techniques in the Forensic Analysis of Designer
Drugs, T. Kowalska, M. Sajewicz and J. Sherma (Eds.), Ch. 10, CRC Press, Taylor and
Francis Group, Boca Raton, FL, 2018, pp. 177–198
M. Novakovic, I. Djordjevic, N. Todorovic, S. Trifunovic, B. Andjelkovic, B. Mandic, M.
Jadranin, I. Vuckovic, V. Vajs, S. Milosavljevic, V. Tesevic, New aurone epoxide and auro-
nolignan from the heartwood of Cotinus coggygria Scop., J. Nat. Prod. Res. 33 (2019) 2837
M. Cvetković, I. Djordjević, M. Jadranin, M. Stanković, B. Mandić, S. Milosavljević, Lj.
Vujisić, Leaf-surface guaianolides from Amphoricarpos neumaeyri showing protective effect
on human lymphocytes DNA, Nat. Prod. Res. 35 (2019) 3040
M. Cvetković, A. Damjanović, T. P. Stanojković, I. Đorđević, V. Tešević, S. Milosavljević,
D. Gođevac, Integration of dry-column flash chromatography with NMR and FTIR metabo-
lomics to reveal cytotoxic metabolites from Amphoricarpos autariatus, Talanta 206 (2020)
120248.
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1136
My collaboration with Prof. Slobodan Milosavljevic
It is hard for me to say when exactly I met Prof. Milosavljevic (Sloba) for
the first time, it was so long ago, further than my memory could reach. But I
remember how Prof. Jeremic (then the chair of the Center for Instrumental
Analysis) brought us together.
After I returned from two years postdoc at ETH in September of 1981, Prof.
Jeremic shown a keen interest in my postdoc experience. I was telling him what I
did and about new development in the field: 2D NMR, COSY, NOESY, double-
-quantum spectroscopy, etc. He was really impressed as he understood immedi-
ately that this was the future. Then Prof. Jeremic asked Sloba, then his young
collaborator to come over and join us in the conversation, and in no time, we
realized that we have complementary interests and expertise that could be aligned
and that we can collaborate fruitfully. At that time, we did not have proper
equipment as the only NMR instrument in the Center was outdated A-60. (A year
earlier I saw the same model in London’s Science Museum as an exhibit of the
lab of 1960s.) Since I was travelling around the globe for my own research, I was
taking along Sloba’s samples and kept recording the spectra wherever I went.
First few papers went through smoothly but on one sent to Magnetic Reso-
nance in Chemistry we got a mixed review with major complaint that “2D NMR
spectrum could be recorded by any average lab”. We were flattered by this rejec-
tion as we interpreted this that in previous papers we were above the average.
Then we wrote back that there is nothing wrong being an average. (In USA there
was very famous show about fictitious place called Lake Wobegon where “… all
the children are above average.”) This paper was eventually published but the
lesson learned was that we must raise the papers on higher level. And Sloba
indeed did just that. There was nothing more I could contribute, I was just rec-
ording and occasionally interpreting the spectra. And we went on and on. Later
when I moved to the USA we included other colleagues from the Chemistry
department who had interest in NMR.
Many years ago, our collaboration naturally winded down as 2D NMR
became quite common and generating useful spectra no longer needed special-
ized expertise. But our friendship has continued till today. We rarely met in
Belgrade outside his lab. But I am grateful for the time we got to spent together
in Rochester (Minnesota), Minneapolis, Chicago, Rio de Janeiro…). Even more
interesting is that both of us had passion for skiing, tennis, and fishing but never
went together to enjoy these activities. I gave up sports long time ago, but I hope
there’s time to go fishing. Happy anniversary, my friend.
Slobodan Macura, Ph.D., Professor of Biochemistry
Department of Biochemistry and Molecular Biology
Mayo Clinic Graduate School of Biomedical Sciences
Mayo Clinic
Rochester, MN, USA
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EDITORIAL 1137
Slobodan Milosavljević, dear friend, distinguished scientist
It is difficult to describe dedication and devotion of Prof. Slobodan Milosav-
ljević, member of Academy of Sciences and Arts, tireless scientist, postdoc at
London University, researcher and promoter, who selflessly transferred know-
ledge to students and associates of faculty for chemistry as well as biology.
My dear friend Slobodan is specially excelling in the field of education and
formation of young people through mutual work and numerous tasks performed
on the Faculty of Chemistry in Belgrade. He led students from basic level to the
highest degrees, with great knowledge and enthusiasm, so later they felt at home
in world of chemistry and biology. Slobodan is still in this noble mission.
I shall remark on his work as much as I can see it from our longstanding
collaboration and friendship. We have spent time mostly on the Montenegro
mountains and in the botanic garden Dulovina in Kolašin. Academician Slobodan
took part, with group of botanist led by dr Nebojsa Menković, in long-term quest
to discover medicinal and endemic plants of east Balkans, namely Montenegro
and Serbia. The stress was on the complex mountain system Prokletije, and the
mountain massif Orjen. Going through unexplored landscape, through rocky
paths and inaccessible remote stones they have collected many precious medi-
cinal as well as endemic plants. All mentioned activities were well documented,
with photographs and botanical specimens for herbarium. Those investigations
were important for botanical garden in Kolašin and later for garden Velemun in
Plav. Furthermore, the research was significant and useful for many institutions
in Serbia and Montenegro such as: Faculty for Chemistry, Faculty for Biology,
Institute Josif Pančić in Belgrade and Biotechnical institute, in Podgorica.
One of the results of the explorations is the book on medicinal plants by
Nebojsa Menković et al. entitled:”A guide to medicinal plants”.
Slobodan made a great contribution to development and growth of the bot-
anic garden Dulovina, however it was not only scientifically significant, but the
garden has become more visible. In other words, papers published in domestic
and international magazines made mountains of Montenegro and their botanical
gardens more popular and more frequently visited by general public.
Daniel Vincek (1926–2021),
Founder and director of the botanic garden Dulovine
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/HRV (Za stvaranje Adobe PDF dokumenata najpogodnijih za visokokvalitetni ispis prije tiskanja koristite ove postavke. Stvoreni PDF dokumenti mogu se otvoriti Acrobat i Adobe Reader 5.0 i kasnijim verzijama.)
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/NLD (Gebruik deze instellingen om Adobe PDF-documenten te maken die zijn geoptimaliseerd voor prepress-afdrukken van hoge kwaliteit. De gemaakte PDF-documenten kunnen worden geopend met Acrobat en Adobe Reader 5.0 en hoger.)
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/ENU (Use these settings to create Adobe PDF documents best suited for high-quality prepress printing. Created PDF documents can be opened with Acrobat and Adobe Reader 5.0 and later.)
>>
/Namespace [
(Adobe)
(Common)
(1.0)
]
/OtherNamespaces [
<<
/AsReaderSpreads false
/CropImagesToFrames true
/ErrorControl /WarnAndContinue
/FlattenerIgnoreSpreadOverrides false
/IncludeGuidesGrids false
/IncludeNonPrinting false
/IncludeSlug false
/Namespace [
(Adobe)
(InDesign)
(4.0)
]
/OmitPlacedBitmaps false
/OmitPlacedEPS false
/OmitPlacedPDF false
/SimulateOverprint /Legacy
>>
<<
/AddBleedMarks false
/AddColorBars false
/AddCropMarks false
/AddPageInfo false
/AddRegMarks false
/ConvertColors /ConvertToCMYK
/DestinationProfileName ()
/DestinationProfileSelector /DocumentCMYK
/Downsample16BitImages true
/FlattenerPreset <<
/PresetSelector /MediumResolution
>>
/FormElements false
/GenerateStructure false
/IncludeBookmarks false
/IncludeHyperlinks false
/IncludeInteractive false
/IncludeLayers false
/IncludeProfiles false
/MultimediaHandling /UseObjectSettings
/Namespace [
(Adobe)
(CreativeSuite)
(2.0)
]
/PDFXOutputIntentProfileSelector /DocumentCMYK
/PreserveEditing true
/UntaggedCMYKHandling /LeaveUntagged
/UntaggedRGBHandling /UseDocumentProfile
/UseDocumentBleed false
>>
]
>> setdistillerparams
<<
/HWResolution [2400 2400]
/PageSize [612.000 792.000]
>> setpagedevice