Papers by Slobodan Milosavljevi
Phytochemistry Letters, 2018
The genus Amphoricarpos Vis. is endemic of westpart of Balkan peninsula. In order to get more ins... more The genus Amphoricarpos Vis. is endemic of westpart of Balkan peninsula. In order to get more insight into the ambiguous taxonomy of the genus, the metabolomic study of the Amphoricarpos samples, has been undertaken. The 1 H NMR spectroscopy combined with multivariate data analysis has been applied. OPLS-DA has been shown to be the best method for clear discrimination of these samples based on the metabolites present in the extracts. The main difference between A. autariatus and A. neumayeri has been found to be the presence of characteristic sesquiterpene lactones of guaianolide type named amphoricarpolides. While the main sesquiterpene lactone in A. neumayeri was oxidized in position 2, those present in both subspecies of A. autariatus samples were oxidized in position 9.The use of sesquiterpene lactones as taxonomic characters for differentiating species of the Asteraceae family was reviewed elsewhere. For the differentiation of two subspecies, A. autariatus ssp. autariatus, and A. autariatus ssp. bertisceus, chlorogenic and malic acid have been found to be decisive, but these compounds do not have chemotaxonomic significance. Our results were in accordance with above mentioned classification of Blečić and Mayer but they differentiate from those of the recent genomic study of the genus indicating a single, genetically, morphologically and ecologically variable species, without intraspecific taxa.
Journal of Essential Oil Research, 2002
The oil of a wild growing population of Achillea asplenifolia Vent, was studied for yield, compos... more The oil of a wild growing population of Achillea asplenifolia Vent, was studied for yield, composition and antibacterial activity. The major components in the oil were β-caryophyllene (17.6%), germacrene D (15.6%) and chamazulene (13.3%). In an antibacterial diffusion assay, the oil showed activity against all tested Gram-negative bacteria (Escherichia coli, Klebsiella pneumoniae and Pseudomonas aeruginosa) and Gram-positive Staphylococcus aureus.
The Gentianaceae - Volume 2: Biotechnology and Applications, 2015
The results are presented of phytochemical investigations, during the last decade, of some wild-g... more The results are presented of phytochemical investigations, during the last decade, of some wild-growing species of the family Gentianaceae from Serbia and Montenegro. Some of the species investigated, members of the genera Gentiana, Gentianella, and Swertia, are endemic, and the emphasis in this report is on those exhibiting biological activities that could be regarded as a potential source of drugs. This review discusses more than fifty compounds, such as xanthones, secoiridoids, and C-glucoflavonoids.
Journal of Ethnopharmacology, 2011
Aim of the study: The main objectives were to collect information on the use of wild growing medi... more Aim of the study: The main objectives were to collect information on the use of wild growing medicinal plants by local people living in high mountain region of Montenegro and conduct local botanical and ecological surveys. Active ingredients of plant species officinal in European Pharmacopoeia 6.0 (Ph. Eur. 6.0) were studied and we assessed possibilities for commercial exploitation for local economic development. Materials and methods: The 75 people that were interviewed (40-82 years old) identified 94 species for treatment of various human ailments. For each named species, the following elements are provided: botanical name, family, part(s) used, medicinal use and perceived property, listing in published pharmacopoeias, the relative abundance of each species and locality where the plant was collected. Chemical analyses were done according to prescriptions of Ph. Eur. 6.0 in order to estimate potential commercial use of native plants. Results and conclusion: The most common in traditional usage were Rosaceae (11 species) making 11.7%, Asteraceae (10 species) 10.6% and Lamiaceae (7 species) 7.4%. From 94 species reported, 35 (37.2%) are officinal in Ph. Eur. 6.0 and 12 in national pharmacopoeias (12.8%). Aerial parts were mostly used (43.6%). The most frequently reported medicinal uses were for treating gastrointestinal (57.4%) and respiratory diseases (41.5%).
Natural Product Communications, 2021
In continuation of our study on Cotinus coggygria from Serbia, 10 known flavonoids (1-10) were is... more In continuation of our study on Cotinus coggygria from Serbia, 10 known flavonoids (1-10) were isolated from the methylene chloride/methanol extract of the heartwood. They were tested for in vitro protective effect against chromosome aberrations in peripheral human lymphocytes, using the cytokinesis-block micronucleus assay. All tested compounds (in minimal doses of 1 μg/mL) exerted a beneficial effect by decreasing DNA damage of human lymphocytes in the range of 24.2% to 54.5%, better than the radio protectant control, amifostine. Functional groups, such as 3′,4′-dihydroxyphenyl (catechol), 5-OH, 3-OH, and 4-keto in flavonoids (3-keto in aurones), which play a key role in antioxidant activity, are proposed to be responsible for the DNA protective activity of the tested compounds.
Plants, Jan 6, 2023
This article is an open access article distributed under the terms and conditions of the Creative... more This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY
Journal of the Serbian Chemical Society, 2022
The application of high performance thin layer chromatography (HPTLC)-based non-targeted metabolo... more The application of high performance thin layer chromatography (HPTLC)-based non-targeted metabolomics as a holistic approach to compare fingerprints of metabolite changes during Artemisia annua development is described. Images of HPTLC chromatograms obtained after derivatization with anisaldehyde-sulphuric acid reagent were used as a dataset for multivariate analysis. Principal component analysis and orthogonal partial least squares discriminant analysis confirmed the differentiation of samples belonging to vegetative phase, flowering stage, and seed formation stage of the plant development. The obtained results showed that the HPTLC-based metabolomics approach can be a very reliable technique for the investigation of metabolic changes during plant development, complementary to gas chromatography?mass spectrometry and nuclear magnetic resonance-based metabolomics.
Phytochemistry, 2021
Thirteen undescribed 24-methylene lanostane triterpenoids, named polyporenic acids E-M and fomito... more Thirteen undescribed 24-methylene lanostane triterpenoids, named polyporenic acids E-M and fomitosides L-O, as well as seventeen known analogues, were isolated from the fruiting bodies of the mushroom Fomitopsis betulina. Their structures were determined using 1D, 2D NMR, IR, and HRESIMS. Fomitoside L and fomitoside N exhibited cytotoxicity against HL60 leukemia cells (IC 50 = 15.8 and 23.7 µM, respectively). Among the known compounds, notable cytotoxicities against HL60 leukemia cells and selectivity with respect to MRC-5 healthy cells were noticed for dehydropachymic acid (IC 50 = 10.9 µM, SI 8.6), pachymic acid (IC 50 = 11.0 µM, SI 9.8), 3-epidehydrotumulosic acid (IC 50 = 19.9 µM, SI 5.8) and 12R-hydroxy-3R-(3-hydroxy-4methoxycarbonyl-3-methylbutyryloxy)-24-methyllanosta-8,24(31)-dien-26-oic acid (IC 50 = 19.2 µM, SI 2.2). a Injection volume, 200 μL (c ca. 10 mg/mL, MeOH); diode array detector (DAD; λ = 210 nm and 254 nm), Column temp., 25°C; mobile phase (4 mL/min), H 2 O (A) + CH 3 CN (B). b Rtretention time (min)
Talanta, 2020
Metabolomics generate a profile of small molecules from plant extracts, which could be directly r... more Metabolomics generate a profile of small molecules from plant extracts, which could be directly responsible for bioactivity effects. Using dry-column flash chromatography enabled a rapid and inexpensive method for the very efficient separation of plant extract with a high resolution. This separation method coupled to NMR and FTIRbased metabolomics is applied to identify bioactive natural products. OPLS multivariate analysis method, was used for correlation the chemical composition of the plant extracts, Amphoricarpos autariatus, with the results of cytotoxic activity against Human cervical adenocarcinoma cell line (HeLa) and epithelial lung cancer cell line (A549). In this way, the highest contribution to the cytotoxic activity was recorded for the guaianolide sesquiterpene lactones named amphoricarpolides. The compounds indicated as bioactive after metabolomics analysis were tested, and their cytotoxic activity were confirmed.
Journal of the Serbian Chemical Society, 1999
1. Introduction 2. Results 3. Asteraceae 3.1. Genus Artemisia L. 3.1.1. Artemisia annua L. 3.1.2.... more 1. Introduction 2. Results 3. Asteraceae 3.1. Genus Artemisia L. 3.1.1. Artemisia annua L. 3.1.2. Artemisia vulgaris L. 3.1.3. Artemisia absinthium L. (warmwood) 3.1.4. Artemisia scoparia W. et K. 3.1.5. Artemisia camprestris L. 3.2. Genus Ambrosia L. 3.2.1. Ambrosia artemisiifolia L. (the common rag weed) 3.3. Genus Tanacetum L. ( syn. Chrysanthemum L.) 3.3.1. Tanacetum parthenium L. (feverfew) 3.3.2. Tanacetum serotinum L. 3.3.3. Tanacetum vulgare L. (tansy) 3.3.4. Tanacetum macrophyllum Willd. 3.3.5. Tanacetum corymbosum L. 3.4. Genus Telekia Baumg. 3.4.1. Telekia speciosa (Schreb.) Baumg. 3.5. Genus Inula L. 3.5.1. Inula helenium L. 3.5.2. Inula spiraeifolia L. 3.6. Genus Eupatorium L. 3.6.1. Eupatorium cannabinum L. 3.7. Genus Achillea L. 3.7.1. Achillea abrotanoides Vis. 3.7.2. Achillea millefolium subsp. pannonica 3.7.3. Achillea crithmifolia W. et K. 3.7.4. Achillea clypeolata Sibth. et Sm. 3.7.5. Achillea serbica Nyman 3.7.6. Achillea depressa Janka 3.8. Genus Anthemis L. 3...
Natural Product Research, 2018
From the methylene chloride/methanol extract of Cotinus coggygria Scop. heartwood one new aurone ... more From the methylene chloride/methanol extract of Cotinus coggygria Scop. heartwood one new aurone epoxide, 2,10-oxy-10-methoxysulfuretin (14), and one auronolignan (15), named cotinignan A, were isolated by silica gel column and semipreparative HPLC chromatography. In addition, thirteen known secondary metabolites
Medicinal and Aromatic Plants of the World, 2015
Through the selected examples of different classes of secondary metabolites two general approache... more Through the selected examples of different classes of secondary metabolites two general approaches in the analysis of complex mixtures of natural products are presented. The first one involves isolation of the constituents using optimized semi-prep LC in combination with classical column chromatography (CC) and the second one represents direct (on-line) analysis of complex plant extracts prior to isolation of the constituents. Thus the isolation of mg-quantities of jatrophanes the bioactive constituents of Euphorbia dendroides, with their structure determination on the basis of spectroscopic data interpretation (IR, NMR, MS), is described. The direct analysis of the plant extracts is demonstrated by the characterization of antioxidative polyphenols, i.e. oligomeric proanthocynidins from the MeOH extracts of grape Vitis vinifera seeds by the application of hyphenated methods (LC/UV/MS) in combination with 13C NMR spectroscopy, as well as tandem mass spectrometry (MS/MS) and MSn in combination with and without LC for identification of oligomeric proanthocynidins from other sources. The potential of another hyphenated instrumentation, LC/UV/SPE-NMR is shown by on-line identification of the various constituents of the crude extract of Hypericum perforatum. The possibilities and limitations of the NMR technique named diffusion ordered spectroscopy (DOSY) for direct analysis of the complex mixture, such as e.g. methanolic extract of Gentiana lutea, is discussed.
Journal of the Chemical Society D: Chemical Communications, 1971
Natural Product Research, 2019
Analysis of composition of CH2Cl2 surface extract of leaves of Amphoricarpos neumayeri Vis. revea... more Analysis of composition of CH2Cl2 surface extract of leaves of Amphoricarpos neumayeri Vis. revealed 16 sesquiterpene lactones with guaianolide skeleton, so called amphoricarpolides, typical for this genus. Four of them, 13-16, were new derivatives and their structures were elucidated by detailed analyses of IR, NMR and MS data. Amphoricarpolide (9), its 15-O-acetyl derivative (5), and two 9β-hydroxyamphoricarpolides, 3,15-di-O-acetyl-and 3-O-acetyl-15-O-isovaleroyl derivatives (3 and 6, respectively) were tested for in vitro protective effect on chromosome aberrations in peripheral human lymphocytes using cytochalasin-B blocked micronucleus (CBMN) assay. The tested compound exerted a beneficial effect by decreasing DNA damage of human lymphocytes.
Collection of Sideritis raeseri subsp. raeseri has a long tradition in local communities in the O... more Collection of Sideritis raeseri subsp. raeseri has a long tradition in local communities in the O hridPrespa region. The aim of the present study was the analysis of bioactive compounds especially those w ith antiinflammatory activity. Combination of the UV and MS data allowed the characterization of 17 compounds, which could be classified into flavonoid glycosides or hydroxycynnamic acid derivatives. Six of them w ere isolated using preparative HPLC: isoscutellarein 7O-[6′′′-O-acetyl-β-D-allopyranosyl-(1→2)]-β-Dglucopyranoside, 4 ′-O-methylhypolaetin 7O-[6′′′-O-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside, hypolaetin 7O-[6′′′-O-acetyl-β-D-allopyranosyl-(1→2)]-6′′-O-acetyl-β-D-glucopyranoside, 4 ′-Omethylisoscutellarein 7O-[6′′′-O-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside, isoscutellarein 7O[6′′′-O-acetyl-β-D-allopyranosyl-(1→2)]-6′′-O-acetyl-β-D-glucopyranoside and 4 ′-O-methylhypolaetin 7O-[6′′′O-acetyl-β-D-allopyranosyl-(1→2)]-6′′-O-acetyl-β-D-glucopyranoside. Th...
The hydrocarbon fraction of Achillea asplenifolia Vent. has been analyzed by capillary gas chroma... more The hydrocarbon fraction of Achillea asplenifolia Vent. has been analyzed by capillary gas chromatography (GC) and GCmass spectrometry (GC-MS). It was found to consist of the usual odd-carbon number dominant distribution of n-alkane homologues (C21-C33). The main compound was nonacosane (C29, 25.5%) and the carbon preference index (CPI) was low (6.87).
Journal of Coordination Chemistry, 2002
Two diastereomers of bis(1,3-diaminopropane)(S-phenylalaninato)cobalt(III) were prepared by react... more Two diastereomers of bis(1,3-diaminopropane)(S-phenylalaninato)cobalt(III) were prepared by reaction of S-phenylalanine with carbonatobis(1,3-diaminopropane)cobalt(III). The diastereomers were separated on an optically active Sephadex QAE column and their absolute configurations assigned by means of circular dichroism. In addition, HNMR spectra of the diastereomers were analyzed in terms of the population of the three predominant rotamers of the coordinated S-phenylalaninato ligand. One out of
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Papers by Slobodan Milosavljevi