Novaković, Miroslav M.

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Authority KeyName Variants
orcid::0000-0002-4984-041X
  • Novaković, Miroslav M. (68)
Projects
Natural products of wild, cultivated and edible plants: structure and bioactivity determination Microbial diversity study and characterization of beneficial environmental microorganisms
Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200026 (University of Belgrade, Institute of Chemistry, Technology and Metallurgy - IChTM) Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200168 (University of Belgrade, Faculty of Chemistry)
Micromorphological, phytochemical and molecular investigations of plants - systematic, ecological and applicative aspects Reinforcement of the Faculty of Chemistry, University of Belgrade, towards becoming a Center of Excellence in the region of WB for Molecular Biotechnology and Food research
The synthesis of aminoquinoline-based antimalarials and botulinum neurotoxin A inhibitors Characterization and application of fungal metabolites and assessment of new biofungicides potential
Identification of predictive molecular markers for cancer progression, response to therapy and disease outcome Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200178 (University of Belgrade, Faculty of Biology)
Modulation of intracellular energy balance-controlling signalling pathways in therapy of cancer and neuro-immuno-endocrine disorders Modulation of antioxidative metabolism in plants for improvement of plant abiotic stress tolerance and identification of new biomarkers for application in remediation and monitoring of degraded biotopes
Content of bioactive components in small and stone fruits as affected by cultivar specificities and growing conditions, and obtaining biologically valuable products by improved and newly developed technologies Bioactive natural products as potential sources of new pharmaceuticals and food supplements
Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200007 (University of Belgrade, Institute for Biological Research 'Siniša Stanković') Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200043 (Institute of Oncology and Radiology of Serbia, Belgrade)
Biomarkers in neurodegenerative and malignant processes Sekundarni metaboliti samoniklih, lekovitih biljaka: izolovanje, karakterizacija i biloška aktivnost
Morphological, chemical, pharmacological and agronomic characterization of the Pannonian Thyme (Thymus pannonicus All., Lamiaceae), with the purpose of sustainable production in intensive cropping system “Agricultural Adaptation to Climate Change – Networking, Education, Research and Extension” (Norwegian Programme in Higher Education, Research and Development in Western Balkans)
Bulgarian Academy of Sciences Centre of Excellence in Bioinformatics “BIO-ICT” (Higher Education and Research for Innovation and Competitiveness project, Contract No. 01- 1001)
Department of Agricultural and Food Sciences, University of Bologna, Italy Evaluation of ecophysiological and genetic plant diversity in forest ecosystems
Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200042 (University of Belgrade, Institute of Molecular Genetics and Genetic Engineering) Novel encapsulation and enzyme technologies for designing of new biocatalysts and biologically active compounds targeting enhancement of food quality, safety and competitiveness
Ispitivanje lekovitog potencijala biljaka: morfološka, hemijska i farmakološka karakterizacija Regulacija antioksidativnog metabolizma biljaka u toku rastenja, infekcije patogenima i delovanja abiotičkog stresa: mehanizmi transporta, signalizacije i otpornosti
Biljni proizvodi u preventivi i terapiji nezaraznih hroničnih oboljenja kod ljudi “INGAF” (Ministry of Science of Montenegro)

Author's Bibliography

Bisbibenzyls from Serbian Primula veris subsp. Columnae (Ten.) Lȕdi and P. acaulis (L.) L

Novaković, Miroslav M.; Ilić-Tomić, Tatjana; Đorđević, Iris; Anđelković, Boban D.; Tešević, Vele; Milosavljević, Slobodan M.; Asakawa, Yoshinori

(Elsevier, 2023)

TY  - JOUR
AU  - Novaković, Miroslav M.
AU  - Ilić-Tomić, Tatjana
AU  - Đorđević, Iris
AU  - Anđelković, Boban D.
AU  - Tešević, Vele
AU  - Milosavljević, Slobodan M.
AU  - Asakawa, Yoshinori
PY  - 2023
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6259
AB  - Bisbibenzyls are specialized metabolites found exclusively in liverworts, until recently; they represent chemical markers of liverworts. Their occurrence in vascular plants was noticed in 2007, when they were found in Primula veris subsp. macrocalyx from Russia. This report prompted us to chemically analyze the two most common Serbian Primula species, P. veris subsp. columnae and P. acaulis, in order to determine the presence of bisbibenzyls in them. Our study revealed nine structurally distinct bisbibenzyls (1–9), identified based on 1D and 2D NMR, IR, UV and HRESIMS data. Among them were five previously undescribed compounds (2–6). The remaining com­ pounds found and previously described in the literature were: the bisbibenzyls riccardin C (1), isoperrottetin A (7), isoplagiochin E (8) and 11-O-demethylmarchantin I (9), as well as 4-hydroxyphenylmethylketone (10) and 4-hydroxy-3-methoxyphenylmethylketone (11). Riccardin C was the most dominant bisbibenzyl in both species studied. Previously, it was the first bisbibenzyl found in vascular plants (P. veris subsp. macrocalyx). An assessment of the cytotoxic activity of the isolated compounds against A549 lung cancer and healthy MRC5 cell lines was also the subject of our study. Compounds 6 and 9 exhibited significant cytotoxic activity expressed by IC50 values of 12 μM, but the selectivity was not satisfactory.
PB  - Elsevier
T2  - Phytochemistry
T1  - Bisbibenzyls from Serbian Primula veris subsp. Columnae (Ten.) Lȕdi and P. acaulis (L.) L
VL  - 212
EP  - 113719
DO  - 10.1016/j.phytochem.2023.113719
ER  - 
@article{
author = "Novaković, Miroslav M. and Ilić-Tomić, Tatjana and Đorđević, Iris and Anđelković, Boban D. and Tešević, Vele and Milosavljević, Slobodan M. and Asakawa, Yoshinori",
year = "2023, 2023",
abstract = "Bisbibenzyls are specialized metabolites found exclusively in liverworts, until recently; they represent chemical markers of liverworts. Their occurrence in vascular plants was noticed in 2007, when they were found in Primula veris subsp. macrocalyx from Russia. This report prompted us to chemically analyze the two most common Serbian Primula species, P. veris subsp. columnae and P. acaulis, in order to determine the presence of bisbibenzyls in them. Our study revealed nine structurally distinct bisbibenzyls (1–9), identified based on 1D and 2D NMR, IR, UV and HRESIMS data. Among them were five previously undescribed compounds (2–6). The remaining com­ pounds found and previously described in the literature were: the bisbibenzyls riccardin C (1), isoperrottetin A (7), isoplagiochin E (8) and 11-O-demethylmarchantin I (9), as well as 4-hydroxyphenylmethylketone (10) and 4-hydroxy-3-methoxyphenylmethylketone (11). Riccardin C was the most dominant bisbibenzyl in both species studied. Previously, it was the first bisbibenzyl found in vascular plants (P. veris subsp. macrocalyx). An assessment of the cytotoxic activity of the isolated compounds against A549 lung cancer and healthy MRC5 cell lines was also the subject of our study. Compounds 6 and 9 exhibited significant cytotoxic activity expressed by IC50 values of 12 μM, but the selectivity was not satisfactory.",
publisher = "Elsevier",
journal = "Phytochemistry",
title = "Bisbibenzyls from Serbian Primula veris subsp. Columnae (Ten.) Lȕdi and P. acaulis (L.) L",
volume = "212",
pages = "113719",
doi = "10.1016/j.phytochem.2023.113719"
}
Novaković, M. M., Ilić-Tomić, T., Đorđević, I., Anđelković, B. D., Tešević, V., Milosavljević, S. M.,& Asakawa, Y.. (2023). Bisbibenzyls from Serbian Primula veris subsp. Columnae (Ten.) Lȕdi and P. acaulis (L.) L. in Phytochemistry
Elsevier., 212.
https://doi.org/10.1016/j.phytochem.2023.113719
Novaković MM, Ilić-Tomić T, Đorđević I, Anđelković BD, Tešević V, Milosavljević SM, Asakawa Y. Bisbibenzyls from Serbian Primula veris subsp. Columnae (Ten.) Lȕdi and P. acaulis (L.) L. in Phytochemistry. 2023;212:null-113719.
doi:10.1016/j.phytochem.2023.113719 .
Novaković, Miroslav M., Ilić-Tomić, Tatjana, Đorđević, Iris, Anđelković, Boban D., Tešević, Vele, Milosavljević, Slobodan M., Asakawa, Yoshinori, "Bisbibenzyls from Serbian Primula veris subsp. Columnae (Ten.) Lȕdi and P. acaulis (L.) L" in Phytochemistry, 212 (2023),
https://doi.org/10.1016/j.phytochem.2023.113719 . .

A New Auronolignan from the Cotinus coggygria Heartwood

Novaković, Miroslav M.; Todorović, Nina; Jadranin, Milka; Đorđević, Iris; Milosavljević, Slobodan M.; Mandić, Boris; Tešević, Vele

(Springer, 2023)

TY  - JOUR
AU  - Novaković, Miroslav M.
AU  - Todorović, Nina
AU  - Jadranin, Milka
AU  - Đorđević, Iris
AU  - Milosavljević, Slobodan M.
AU  - Mandić, Boris
AU  - Tešević, Vele
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6264
AB  - A new auronolignan, named cotinignan B, was isolated from Cotinus coggygria Scop. Structure elucidation was performed on the basis of 1H, 13C NMR, COSY, NOESY, HSQC, and HMBC experiments, supported with HR-ESI-MS, IR and UV. Additional J-HMBC NMR experiment was essential to resolve the configuration of the trisubstituted double bond. This compound represents the secondly discovered natural compound belonging to the rare auronolignan type.
PB  - Springer
T2  - Chemistry of Natural Compounds
T1  - A New Auronolignan from the Cotinus coggygria Heartwood
VL  - 59
IS  - 3
SP  - 428
EP  - 430
DO  - 10.1007/s10600-023-04016-5
ER  - 
@article{
author = "Novaković, Miroslav M. and Todorović, Nina and Jadranin, Milka and Đorđević, Iris and Milosavljević, Slobodan M. and Mandić, Boris and Tešević, Vele",
year = "2023",
abstract = "A new auronolignan, named cotinignan B, was isolated from Cotinus coggygria Scop. Structure elucidation was performed on the basis of 1H, 13C NMR, COSY, NOESY, HSQC, and HMBC experiments, supported with HR-ESI-MS, IR and UV. Additional J-HMBC NMR experiment was essential to resolve the configuration of the trisubstituted double bond. This compound represents the secondly discovered natural compound belonging to the rare auronolignan type.",
publisher = "Springer",
journal = "Chemistry of Natural Compounds",
title = "A New Auronolignan from the Cotinus coggygria Heartwood",
volume = "59",
number = "3",
pages = "428-430",
doi = "10.1007/s10600-023-04016-5"
}
Novaković, M. M., Todorović, N., Jadranin, M., Đorđević, I., Milosavljević, S. M., Mandić, B.,& Tešević, V.. (2023). A New Auronolignan from the Cotinus coggygria Heartwood. in Chemistry of Natural Compounds
Springer., 59(3), 428-430.
https://doi.org/10.1007/s10600-023-04016-5
Novaković MM, Todorović N, Jadranin M, Đorđević I, Milosavljević SM, Mandić B, Tešević V. A New Auronolignan from the Cotinus coggygria Heartwood. in Chemistry of Natural Compounds. 2023;59(3):428-430.
doi:10.1007/s10600-023-04016-5 .
Novaković, Miroslav M., Todorović, Nina, Jadranin, Milka, Đorđević, Iris, Milosavljević, Slobodan M., Mandić, Boris, Tešević, Vele, "A New Auronolignan from the Cotinus coggygria Heartwood" in Chemistry of Natural Compounds, 59, no. 3 (2023):428-430,
https://doi.org/10.1007/s10600-023-04016-5 . .

Novel artesunate–pyrimidine-based hybrids with anticancer potential against multidrug-resistant cancer cells

Koračak, Ljiljana; Lupšić, Ema; Terzić-Jovanović, Nataša; Jovanović, Mirna; Novaković, Miroslav M.; Nedialkov, Paraskev; Trendafilova, Antoaneta; Zlatović, Mario; Pešić, Milica; Opsenica, Igor

(Royal Society of Chemistry, 2023)

TY  - JOUR
AU  - Koračak, Ljiljana
AU  - Lupšić, Ema
AU  - Terzić-Jovanović, Nataša
AU  - Jovanović, Mirna
AU  - Novaković, Miroslav M.
AU  - Nedialkov, Paraskev
AU  - Trendafilova, Antoaneta
AU  - Zlatović, Mario
AU  - Pešić, Milica
AU  - Opsenica, Igor
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6245
AB  - The synthesis of 17 hybrid molecules, consisting of artesunate, a derivative of naturally occurring artemisinin, and synthetic 4-aryl-2-aminopyrimidines, is described. New compounds were designed to improve the parent compounds' cytotoxic properties, activity, and selectivity. The synthesized hybrid molecules (15a–f with ethylenediamine linker and 16a–k with piperazine linker), as well as their precursors – pyrimidine derivatives (13a–f and 14a–k), artemisinin, and artesunate, were tested on sensitive and multidrug-resistant (MDR) human non-small cell lung carcinoma (NSCLC) cells. All hybrid compounds with piperazine linker 16a–k were selective toward NSCLC cells and displayed IC50 values below 5 μM. Although they showed similar anticancer potency as artesunate, their selectivity against cancer cells was considerably improved. Importantly, 16h–k hybrid compounds were able to evade MDR phenotype, inhibit P-glycoprotein (P-gp) activity, and increase the sensitivity of MDR NSCLC cells to doxorubicin (DOX). The inhibition of P-gp activity induced by 16h–j was stronger than the one obtained with artesunate. Among these four hybrid compounds, 16k was the most potent anticancer agent with similar IC50 values of around 1.5 μM (for comparison – over 3.1 μM for artesunate) in sensitive and MDR NSCLC cells.
PB  - Royal Society of Chemistry
T2  - New Journal of Chemistry
T1  - Novel artesunate–pyrimidine-based hybrids with anticancer potential against multidrug-resistant cancer cells
VL  - 47
IS  - 14
SP  - 6844
EP  - 6855
DO  - 10.1039/D3NJ00427A
ER  - 
@article{
author = "Koračak, Ljiljana and Lupšić, Ema and Terzić-Jovanović, Nataša and Jovanović, Mirna and Novaković, Miroslav M. and Nedialkov, Paraskev and Trendafilova, Antoaneta and Zlatović, Mario and Pešić, Milica and Opsenica, Igor",
year = "2023",
abstract = "The synthesis of 17 hybrid molecules, consisting of artesunate, a derivative of naturally occurring artemisinin, and synthetic 4-aryl-2-aminopyrimidines, is described. New compounds were designed to improve the parent compounds' cytotoxic properties, activity, and selectivity. The synthesized hybrid molecules (15a–f with ethylenediamine linker and 16a–k with piperazine linker), as well as their precursors – pyrimidine derivatives (13a–f and 14a–k), artemisinin, and artesunate, were tested on sensitive and multidrug-resistant (MDR) human non-small cell lung carcinoma (NSCLC) cells. All hybrid compounds with piperazine linker 16a–k were selective toward NSCLC cells and displayed IC50 values below 5 μM. Although they showed similar anticancer potency as artesunate, their selectivity against cancer cells was considerably improved. Importantly, 16h–k hybrid compounds were able to evade MDR phenotype, inhibit P-glycoprotein (P-gp) activity, and increase the sensitivity of MDR NSCLC cells to doxorubicin (DOX). The inhibition of P-gp activity induced by 16h–j was stronger than the one obtained with artesunate. Among these four hybrid compounds, 16k was the most potent anticancer agent with similar IC50 values of around 1.5 μM (for comparison – over 3.1 μM for artesunate) in sensitive and MDR NSCLC cells.",
publisher = "Royal Society of Chemistry",
journal = "New Journal of Chemistry",
title = "Novel artesunate–pyrimidine-based hybrids with anticancer potential against multidrug-resistant cancer cells",
volume = "47",
number = "14",
pages = "6844-6855",
doi = "10.1039/D3NJ00427A"
}
Koračak, L., Lupšić, E., Terzić-Jovanović, N., Jovanović, M., Novaković, M. M., Nedialkov, P., Trendafilova, A., Zlatović, M., Pešić, M.,& Opsenica, I.. (2023). Novel artesunate–pyrimidine-based hybrids with anticancer potential against multidrug-resistant cancer cells. in New Journal of Chemistry
Royal Society of Chemistry., 47(14), 6844-6855.
https://doi.org/10.1039/D3NJ00427A
Koračak L, Lupšić E, Terzić-Jovanović N, Jovanović M, Novaković MM, Nedialkov P, Trendafilova A, Zlatović M, Pešić M, Opsenica I. Novel artesunate–pyrimidine-based hybrids with anticancer potential against multidrug-resistant cancer cells. in New Journal of Chemistry. 2023;47(14):6844-6855.
doi:10.1039/D3NJ00427A .
Koračak, Ljiljana, Lupšić, Ema, Terzić-Jovanović, Nataša, Jovanović, Mirna, Novaković, Miroslav M., Nedialkov, Paraskev, Trendafilova, Antoaneta, Zlatović, Mario, Pešić, Milica, Opsenica, Igor, "Novel artesunate–pyrimidine-based hybrids with anticancer potential against multidrug-resistant cancer cells" in New Journal of Chemistry, 47, no. 14 (2023):6844-6855,
https://doi.org/10.1039/D3NJ00427A . .
3
1
1

Novel hybrids of sclareol and 1,2,4-triazolo[1,5-a]pyrimidine show collateral sensitivity in multidrug-resistant glioblastoma cells

Stojković, Pavle; Kostić, Ana; Lupšić, Ema; Jovanović, Nataša Terzić; Novaković, Miroslav M.; Nedialkov, Paraskev; Trendafilova, Antoaneta; Pešić, Milica; Opsenica, Igor

(Elsevier, 2023)

TY  - JOUR
AU  - Stojković, Pavle
AU  - Kostić, Ana
AU  - Lupšić, Ema
AU  - Jovanović, Nataša Terzić
AU  - Novaković, Miroslav M.
AU  - Nedialkov, Paraskev
AU  - Trendafilova, Antoaneta
AU  - Pešić, Milica
AU  - Opsenica, Igor 
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6258
AB  - The synthesis of 24 hybrid molecules, consisting of naturally occurring sclareol (SCL) and synthetic 1,2,4-triazolo[1,5-a]pyrimidines (TPs), is described. New compounds were designed with the aim of improving the cytotoxic properties, activity, and selectivity of the parent compounds. Six analogs (12a-f) contained 4-benzylpiperazine linkage, while 4-benzyldiamine linkage was present in eighteen derivatives (12g-r and 13a-f). Hybrids 13a-f consist of two TP units. After purification, all hybrids (12a-r and 13a-f), as well as their precursors (9a-e and 11a-c), were tested on human glioblastoma U87 cells. More than half of the tested synthesized molecules, 16 out of 31, caused a significant reduction of U87 cell viability (more than 75% reduction) at 30 µM. The concentration-dependent cytotoxicity of these 16 compounds was also examined on U87 cells, corresponding multidrug-resistant (MDR) U87-TxR cells with increased P-glycoprotein (P-gp) expression and activity, and normal lung fibroblasts MRC-5. Importantly, 12l and 12r were active in the nanomolar range, while seven compounds (11b, 11c, 12i, 12l, 12n, 12q, and 12r) were more selective towards glioblastoma cells than SCL. All compounds except 12r evaded MDR, showing even better cytotoxicity in U87-TxR cells. In particular, 11c, 12a, 12g, 12j, 12k, 12m, 12n, and SCL showed collateral sensitivity. Hybrid compounds 12l, 12q, and 12r decreased P-gp activity to the same extent as a well-known P-gp inhibitor - tariquidar (TQ). Hybrid compound 12l and its precursor 11c affected different cellular processes including the cell cycle, cell death, and mitochondrial membrane potential, and changed the levels of reactive oxygen and nitrogen species (ROS/RNS) in glioblastoma cells. Collateral sensitivity towards MDR glioblastoma cells was caused by the modulation of oxidative stress accompanied by inhibition of mitochondria.
PB  - Elsevier
T2  - Bioorganic Chemistry
T1  - Novel hybrids of sclareol and 1,2,4-triazolo[1,5-a]pyrimidine show collateral sensitivity in multidrug-resistant glioblastoma cells
VL  - 138
SP  - 106605
DO  - 10.1016/j.bioorg.2023.106605
ER  - 
@article{
author = "Stojković, Pavle and Kostić, Ana and Lupšić, Ema and Jovanović, Nataša Terzić and Novaković, Miroslav M. and Nedialkov, Paraskev and Trendafilova, Antoaneta and Pešić, Milica and Opsenica, Igor ",
year = "2023",
abstract = "The synthesis of 24 hybrid molecules, consisting of naturally occurring sclareol (SCL) and synthetic 1,2,4-triazolo[1,5-a]pyrimidines (TPs), is described. New compounds were designed with the aim of improving the cytotoxic properties, activity, and selectivity of the parent compounds. Six analogs (12a-f) contained 4-benzylpiperazine linkage, while 4-benzyldiamine linkage was present in eighteen derivatives (12g-r and 13a-f). Hybrids 13a-f consist of two TP units. After purification, all hybrids (12a-r and 13a-f), as well as their precursors (9a-e and 11a-c), were tested on human glioblastoma U87 cells. More than half of the tested synthesized molecules, 16 out of 31, caused a significant reduction of U87 cell viability (more than 75% reduction) at 30 µM. The concentration-dependent cytotoxicity of these 16 compounds was also examined on U87 cells, corresponding multidrug-resistant (MDR) U87-TxR cells with increased P-glycoprotein (P-gp) expression and activity, and normal lung fibroblasts MRC-5. Importantly, 12l and 12r were active in the nanomolar range, while seven compounds (11b, 11c, 12i, 12l, 12n, 12q, and 12r) were more selective towards glioblastoma cells than SCL. All compounds except 12r evaded MDR, showing even better cytotoxicity in U87-TxR cells. In particular, 11c, 12a, 12g, 12j, 12k, 12m, 12n, and SCL showed collateral sensitivity. Hybrid compounds 12l, 12q, and 12r decreased P-gp activity to the same extent as a well-known P-gp inhibitor - tariquidar (TQ). Hybrid compound 12l and its precursor 11c affected different cellular processes including the cell cycle, cell death, and mitochondrial membrane potential, and changed the levels of reactive oxygen and nitrogen species (ROS/RNS) in glioblastoma cells. Collateral sensitivity towards MDR glioblastoma cells was caused by the modulation of oxidative stress accompanied by inhibition of mitochondria.",
publisher = "Elsevier",
journal = "Bioorganic Chemistry",
title = "Novel hybrids of sclareol and 1,2,4-triazolo[1,5-a]pyrimidine show collateral sensitivity in multidrug-resistant glioblastoma cells",
volume = "138",
pages = "106605",
doi = "10.1016/j.bioorg.2023.106605"
}
Stojković, P., Kostić, A., Lupšić, E., Jovanović, N. T., Novaković, M. M., Nedialkov, P., Trendafilova, A., Pešić, M.,& Opsenica, I.. (2023). Novel hybrids of sclareol and 1,2,4-triazolo[1,5-a]pyrimidine show collateral sensitivity in multidrug-resistant glioblastoma cells. in Bioorganic Chemistry
Elsevier., 138, 106605.
https://doi.org/10.1016/j.bioorg.2023.106605
Stojković P, Kostić A, Lupšić E, Jovanović NT, Novaković MM, Nedialkov P, Trendafilova A, Pešić M, Opsenica I. Novel hybrids of sclareol and 1,2,4-triazolo[1,5-a]pyrimidine show collateral sensitivity in multidrug-resistant glioblastoma cells. in Bioorganic Chemistry. 2023;138:106605.
doi:10.1016/j.bioorg.2023.106605 .
Stojković, Pavle, Kostić, Ana, Lupšić, Ema, Jovanović, Nataša Terzić, Novaković, Miroslav M., Nedialkov, Paraskev, Trendafilova, Antoaneta, Pešić, Milica, Opsenica, Igor , "Novel hybrids of sclareol and 1,2,4-triazolo[1,5-a]pyrimidine show collateral sensitivity in multidrug-resistant glioblastoma cells" in Bioorganic Chemistry, 138 (2023):106605,
https://doi.org/10.1016/j.bioorg.2023.106605 . .
3
1
1

DNA protective activity of triterpenoids isolated from medicinal mushroom Fomitopsis betulina

Sofrenić, Ivana V.; Anđelković, Boban D.; Vujisić, Ljubodrag V.; Novaković, Miroslav M.; Knežević, Aleksandar; Stanković, Miroslava ; Milosavljević, Slobodan M.; Tešević, Vele

(Serbian Chemical Society, 2021)

TY  - JOUR
AU  - Sofrenić, Ivana V.
AU  - Anđelković, Boban D.
AU  - Vujisić, Ljubodrag V.
AU  - Novaković, Miroslav M.
AU  - Knežević, Aleksandar
AU  - Stanković, Miroslava

AU  - Milosavljević, Slobodan M.
AU  - Tešević, Vele
PY  - 2021
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/4819
AB  - Eleven 31-methylenlanostane triterpenoids, i.e., seven 21- and four 26-oic acids, as well as a lupane triterpenoid betulin, isolated from the fruiting bodies of the mushroom Fomitopsis betulina, were tested for in vitro protective effect on chromosome aberrations in peripheral human lymphocytes using cytochalasin-B blocked micronucleus (CBMN) assay. Most of the tested compounds showed a beneficial effect by reducing DNA damage of human lymphocytes more effectively than amifostine, a radioprotective agent, used as a positive control. All the tested compounds decreased MN frequency in the concentration dependent manner, with the concentration of 2.0 µg mL-1 being the most effective – with increase of the concentration the activity slightly decreases. The structure–activity relationship (SAR) studies indicated that the lanostanes containing a conjugated 7,9 (11)-diene system exhibit lower activity than Δ8-analogues. It was also demonstrated that the DNA protective activities within the Δ8-lanostane-26-oic acid group are affected by the substitution in position 3 pattern. In the Δ8 series the oxygenation at C-12 or 16 as well as 21- or 26-oic acid functionality proved beneficial for in vitro protective effect on chromosomal aberrations. Betulin exhibited the lowest protective activity, but it is still comparable to that of amifostine.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - DNA protective activity of triterpenoids isolated from medicinal mushroom Fomitopsis betulina
VL  - 86
IS  - 9
SP  - 809
EP  - 817
DO  - 10.2298/JSC210401039S
ER  - 
@article{
author = "Sofrenić, Ivana V. and Anđelković, Boban D. and Vujisić, Ljubodrag V. and Novaković, Miroslav M. and Knežević, Aleksandar and Stanković, Miroslava
 and Milosavljević, Slobodan M. and Tešević, Vele",
year = "2021",
abstract = "Eleven 31-methylenlanostane triterpenoids, i.e., seven 21- and four 26-oic acids, as well as a lupane triterpenoid betulin, isolated from the fruiting bodies of the mushroom Fomitopsis betulina, were tested for in vitro protective effect on chromosome aberrations in peripheral human lymphocytes using cytochalasin-B blocked micronucleus (CBMN) assay. Most of the tested compounds showed a beneficial effect by reducing DNA damage of human lymphocytes more effectively than amifostine, a radioprotective agent, used as a positive control. All the tested compounds decreased MN frequency in the concentration dependent manner, with the concentration of 2.0 µg mL-1 being the most effective – with increase of the concentration the activity slightly decreases. The structure–activity relationship (SAR) studies indicated that the lanostanes containing a conjugated 7,9 (11)-diene system exhibit lower activity than Δ8-analogues. It was also demonstrated that the DNA protective activities within the Δ8-lanostane-26-oic acid group are affected by the substitution in position 3 pattern. In the Δ8 series the oxygenation at C-12 or 16 as well as 21- or 26-oic acid functionality proved beneficial for in vitro protective effect on chromosomal aberrations. Betulin exhibited the lowest protective activity, but it is still comparable to that of amifostine.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "DNA protective activity of triterpenoids isolated from medicinal mushroom Fomitopsis betulina",
volume = "86",
number = "9",
pages = "809-817",
doi = "10.2298/JSC210401039S"
}
Sofrenić, I. V., Anđelković, B. D., Vujisić, L. V., Novaković, M. M., Knežević, A., Stanković, M., Milosavljević, S. M.,& Tešević, V.. (2021). DNA protective activity of triterpenoids isolated from medicinal mushroom Fomitopsis betulina. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 86(9), 809-817.
https://doi.org/10.2298/JSC210401039S
Sofrenić IV, Anđelković BD, Vujisić LV, Novaković MM, Knežević A, Stanković M, Milosavljević SM, Tešević V. DNA protective activity of triterpenoids isolated from medicinal mushroom Fomitopsis betulina. in Journal of the Serbian Chemical Society. 2021;86(9):809-817.
doi:10.2298/JSC210401039S .
Sofrenić, Ivana V., Anđelković, Boban D., Vujisić, Ljubodrag V., Novaković, Miroslav M., Knežević, Aleksandar, Stanković, Miroslava
, Milosavljević, Slobodan M., Tešević, Vele, "DNA protective activity of triterpenoids isolated from medicinal mushroom Fomitopsis betulina" in Journal of the Serbian Chemical Society, 86, no. 9 (2021):809-817,
https://doi.org/10.2298/JSC210401039S . .

Cytotoxic triterpenoids and triterpene sugar esters from the medicinal mushroom Fomitopsis betulina

Sofrenić, Ivana V.; Anđelković, Boban D.; Todorović, Nina; Stanojković, Tatjana; Vujisić, Ljubodrag V.; Novaković, Miroslav M.; Milosavljević, Slobodan M.; Tešević, Vele

(2021)

TY  - JOUR
AU  - Sofrenić, Ivana V.
AU  - Anđelković, Boban D.
AU  - Todorović, Nina
AU  - Stanojković, Tatjana
AU  - Vujisić, Ljubodrag V.
AU  - Novaković, Miroslav M.
AU  - Milosavljević, Slobodan M.
AU  - Tešević, Vele
PY  - 2021
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/4945
AB  - 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 (IC50 = 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 (IC50 = 10.9 μM, SI 8.6), pachymic acid (IC50 = 11.0 μM, SI 9.8), 3-epi-dehydrotumulosic acid (IC50 = 19.9 μM, SI 5.8) and 12α-hydroxy-3α-(3′-hydroxy-4′-methoxycarbonyl-3′-methylbutyryloxy)-24-methyllanosta-8,24 (31)-dien-26-oic acid (IC50 = 19.2 μM, SI 2.2).
T2  - Phytochemistry
T1  - Cytotoxic triterpenoids and triterpene sugar esters from the medicinal mushroom Fomitopsis betulina
VL  - 181
SP  - 112580
DO  - 10.1016/j.phytochem.2020.112580
ER  - 
@article{
author = "Sofrenić, Ivana V. and Anđelković, Boban D. and Todorović, Nina and Stanojković, Tatjana and Vujisić, Ljubodrag V. and Novaković, Miroslav M. and Milosavljević, Slobodan M. and Tešević, Vele",
year = "2021",
abstract = "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 (IC50 = 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 (IC50 = 10.9 μM, SI 8.6), pachymic acid (IC50 = 11.0 μM, SI 9.8), 3-epi-dehydrotumulosic acid (IC50 = 19.9 μM, SI 5.8) and 12α-hydroxy-3α-(3′-hydroxy-4′-methoxycarbonyl-3′-methylbutyryloxy)-24-methyllanosta-8,24 (31)-dien-26-oic acid (IC50 = 19.2 μM, SI 2.2).",
journal = "Phytochemistry",
title = "Cytotoxic triterpenoids and triterpene sugar esters from the medicinal mushroom Fomitopsis betulina",
volume = "181",
pages = "112580",
doi = "10.1016/j.phytochem.2020.112580"
}
Sofrenić, I. V., Anđelković, B. D., Todorović, N., Stanojković, T., Vujisić, L. V., Novaković, M. M., Milosavljević, S. M.,& Tešević, V.. (2021). Cytotoxic triterpenoids and triterpene sugar esters from the medicinal mushroom Fomitopsis betulina. in Phytochemistry, 181, 112580.
https://doi.org/10.1016/j.phytochem.2020.112580
Sofrenić IV, Anđelković BD, Todorović N, Stanojković T, Vujisić LV, Novaković MM, Milosavljević SM, Tešević V. Cytotoxic triterpenoids and triterpene sugar esters from the medicinal mushroom Fomitopsis betulina. in Phytochemistry. 2021;181:112580.
doi:10.1016/j.phytochem.2020.112580 .
Sofrenić, Ivana V., Anđelković, Boban D., Todorović, Nina, Stanojković, Tatjana, Vujisić, Ljubodrag V., Novaković, Miroslav M., Milosavljević, Slobodan M., Tešević, Vele, "Cytotoxic triterpenoids and triterpene sugar esters from the medicinal mushroom Fomitopsis betulina" in Phytochemistry, 181 (2021):112580,
https://doi.org/10.1016/j.phytochem.2020.112580 . .
2
15
4
15
11

Supplementary data for the article: Sofrenić, I.; Anđelković, B.; Todorović, N.; Stanojković, T.; Vujisić, L.; Novaković, M.; Milosavljević, S.; Tešević, V. Cytotoxic Triterpenoids and Triterpene Sugar Esters from the Medicinal Mushroom Fomitopsis Betulina. Phytochemistry 2021, 181, 112580. https://doi.org/10.1016/j.phytochem.2020.112580.

Sofrenić, Ivana V.; Anđelković, Boban D.; Todorović, Nina; Stanojković, Tatjana; Vujisić, Ljubodrag V.; Novaković, Miroslav M.; Milosavljević, Slobodan M.; Tešević, Vele

(2021)

TY  - DATA
AU  - Sofrenić, Ivana V.
AU  - Anđelković, Boban D.
AU  - Todorović, Nina
AU  - Stanojković, Tatjana
AU  - Vujisić, Ljubodrag V.
AU  - Novaković, Miroslav M.
AU  - Milosavljević, Slobodan M.
AU  - Tešević, Vele
PY  - 2021
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/4946
T2  - Phytochemistry
T1  - Supplementary data for the article: Sofrenić, I.; Anđelković, B.; Todorović, N.; Stanojković, T.; Vujisić, L.; Novaković, M.; Milosavljević, S.; Tešević, V. Cytotoxic Triterpenoids and Triterpene Sugar Esters from the Medicinal Mushroom Fomitopsis Betulina. Phytochemistry 2021, 181, 112580. https://doi.org/10.1016/j.phytochem.2020.112580.
UR  - https://hdl.handle.net/21.15107/rcub_cherry_4946
ER  - 
@misc{
author = "Sofrenić, Ivana V. and Anđelković, Boban D. and Todorović, Nina and Stanojković, Tatjana and Vujisić, Ljubodrag V. and Novaković, Miroslav M. and Milosavljević, Slobodan M. and Tešević, Vele",
year = "2021",
journal = "Phytochemistry",
title = "Supplementary data for the article: Sofrenić, I.; Anđelković, B.; Todorović, N.; Stanojković, T.; Vujisić, L.; Novaković, M.; Milosavljević, S.; Tešević, V. Cytotoxic Triterpenoids and Triterpene Sugar Esters from the Medicinal Mushroom Fomitopsis Betulina. Phytochemistry 2021, 181, 112580. https://doi.org/10.1016/j.phytochem.2020.112580.",
url = "https://hdl.handle.net/21.15107/rcub_cherry_4946"
}
Sofrenić, I. V., Anđelković, B. D., Todorović, N., Stanojković, T., Vujisić, L. V., Novaković, M. M., Milosavljević, S. M.,& Tešević, V.. (2021). Supplementary data for the article: Sofrenić, I.; Anđelković, B.; Todorović, N.; Stanojković, T.; Vujisić, L.; Novaković, M.; Milosavljević, S.; Tešević, V. Cytotoxic Triterpenoids and Triterpene Sugar Esters from the Medicinal Mushroom Fomitopsis Betulina. Phytochemistry 2021, 181, 112580. https://doi.org/10.1016/j.phytochem.2020.112580.. in Phytochemistry.
https://hdl.handle.net/21.15107/rcub_cherry_4946
Sofrenić IV, Anđelković BD, Todorović N, Stanojković T, Vujisić LV, Novaković MM, Milosavljević SM, Tešević V. Supplementary data for the article: Sofrenić, I.; Anđelković, B.; Todorović, N.; Stanojković, T.; Vujisić, L.; Novaković, M.; Milosavljević, S.; Tešević, V. Cytotoxic Triterpenoids and Triterpene Sugar Esters from the Medicinal Mushroom Fomitopsis Betulina. Phytochemistry 2021, 181, 112580. https://doi.org/10.1016/j.phytochem.2020.112580.. in Phytochemistry. 2021;.
https://hdl.handle.net/21.15107/rcub_cherry_4946 .
Sofrenić, Ivana V., Anđelković, Boban D., Todorović, Nina, Stanojković, Tatjana, Vujisić, Ljubodrag V., Novaković, Miroslav M., Milosavljević, Slobodan M., Tešević, Vele, "Supplementary data for the article: Sofrenić, I.; Anđelković, B.; Todorović, N.; Stanojković, T.; Vujisić, L.; Novaković, M.; Milosavljević, S.; Tešević, V. Cytotoxic Triterpenoids and Triterpene Sugar Esters from the Medicinal Mushroom Fomitopsis Betulina. Phytochemistry 2021, 181, 112580. https://doi.org/10.1016/j.phytochem.2020.112580." in Phytochemistry (2021),
https://hdl.handle.net/21.15107/rcub_cherry_4946 .

Flavonoids of the Heartwood of Cotinus coggygria Scop. Showing Protective Effect on Human Lymphocyte DNA

Milosavljević, Slobodan M.; Đorđević, Iris; Mandić, Boris; Tešević, Vele; Stanković, Miroslava; Todorović, Nina; Novaković, Miroslav M.

(SAGE Publications, 2021)

TY  - JOUR
AU  - Milosavljević, Slobodan M.
AU  - Đorđević, Iris
AU  - Mandić, Boris
AU  - Tešević, Vele
AU  - Stanković, Miroslava
AU  - Todorović, Nina
AU  - Novaković, Miroslav M.
PY  - 2021
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/4838
AB  - 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.
PB  - SAGE Publications
T2  - Natural Product Communications
T1  - Flavonoids of the Heartwood of Cotinus coggygria Scop. Showing Protective Effect on Human Lymphocyte DNA
VL  - 16
IS  - 12
SP  - 1
EP  - 8
DO  - 10.1177/1934578X211067289
ER  - 
@article{
author = "Milosavljević, Slobodan M. and Đorđević, Iris and Mandić, Boris and Tešević, Vele and Stanković, Miroslava and Todorović, Nina and Novaković, Miroslav M.",
year = "2021",
abstract = "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.",
publisher = "SAGE Publications",
journal = "Natural Product Communications",
title = "Flavonoids of the Heartwood of Cotinus coggygria Scop. Showing Protective Effect on Human Lymphocyte DNA",
volume = "16",
number = "12",
pages = "1-8",
doi = "10.1177/1934578X211067289"
}
Milosavljević, S. M., Đorđević, I., Mandić, B., Tešević, V., Stanković, M., Todorović, N.,& Novaković, M. M.. (2021). Flavonoids of the Heartwood of Cotinus coggygria Scop. Showing Protective Effect on Human Lymphocyte DNA. in Natural Product Communications
SAGE Publications., 16(12), 1-8.
https://doi.org/10.1177/1934578X211067289
Milosavljević SM, Đorđević I, Mandić B, Tešević V, Stanković M, Todorović N, Novaković MM. Flavonoids of the Heartwood of Cotinus coggygria Scop. Showing Protective Effect on Human Lymphocyte DNA. in Natural Product Communications. 2021;16(12):1-8.
doi:10.1177/1934578X211067289 .
Milosavljević, Slobodan M., Đorđević, Iris, Mandić, Boris, Tešević, Vele, Stanković, Miroslava, Todorović, Nina, Novaković, Miroslav M., "Flavonoids of the Heartwood of Cotinus coggygria Scop. Showing Protective Effect on Human Lymphocyte DNA" in Natural Product Communications, 16, no. 12 (2021):1-8,
https://doi.org/10.1177/1934578X211067289 . .
2
2

Supplementary data for the article: Novakovic, M.; Simić, S.; Koračak, L.; Zlatović, M.; Ilic-Tomic, T.; Asakawa, Y.; Nikodinovic-Runic, J.; Opsenica, I. Chemo- and Biocatalytic Esterification of Marchantin A and Cytotoxic Activity of Ester Derivatives. Fitoterapia 2020, 142. https://doi.org/10.1016/j.fitote.2020.104520.oxic activity of ester derivatives http://cherry.chem.bg.ac.rs/handle/123456789/3867

Novaković, Miroslav M.; Simić, Stefan; Koračak, Ljiljana; Zlatović, Mario; Ilić-Tomič, Tatjana; Asakawa, Yoshinori; Nikodinović-Runić, Jasmina; Opsenica, Igor

(Elsevier, 2020)

TY  - DATA
AU  - Novaković, Miroslav M.
AU  - Simić, Stefan
AU  - Koračak, Ljiljana
AU  - Zlatović, Mario
AU  - Ilić-Tomič, Tatjana
AU  - Asakawa, Yoshinori
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3889
PB  - Elsevier
T2  - Fitoterapia
T1  - Supplementary data for the article: Novakovic, M.; Simić, S.; Koračak, L.; Zlatović, M.; Ilic-Tomic, T.; Asakawa, Y.; Nikodinovic-Runic, J.; Opsenica, I. Chemo- and Biocatalytic Esterification of Marchantin A and Cytotoxic Activity of Ester Derivatives. Fitoterapia 2020, 142. https://doi.org/10.1016/j.fitote.2020.104520.oxic activity of ester derivatives http://cherry.chem.bg.ac.rs/handle/123456789/3867
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3889
ER  - 
@misc{
author = "Novaković, Miroslav M. and Simić, Stefan and Koračak, Ljiljana and Zlatović, Mario and Ilić-Tomič, Tatjana and Asakawa, Yoshinori and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2020",
publisher = "Elsevier",
journal = "Fitoterapia",
title = "Supplementary data for the article: Novakovic, M.; Simić, S.; Koračak, L.; Zlatović, M.; Ilic-Tomic, T.; Asakawa, Y.; Nikodinovic-Runic, J.; Opsenica, I. Chemo- and Biocatalytic Esterification of Marchantin A and Cytotoxic Activity of Ester Derivatives. Fitoterapia 2020, 142. https://doi.org/10.1016/j.fitote.2020.104520.oxic activity of ester derivatives http://cherry.chem.bg.ac.rs/handle/123456789/3867",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3889"
}
Novaković, M. M., Simić, S., Koračak, L., Zlatović, M., Ilić-Tomič, T., Asakawa, Y., Nikodinović-Runić, J.,& Opsenica, I.. (2020). Supplementary data for the article: Novakovic, M.; Simić, S.; Koračak, L.; Zlatović, M.; Ilic-Tomic, T.; Asakawa, Y.; Nikodinovic-Runic, J.; Opsenica, I. Chemo- and Biocatalytic Esterification of Marchantin A and Cytotoxic Activity of Ester Derivatives. Fitoterapia 2020, 142. https://doi.org/10.1016/j.fitote.2020.104520.oxic activity of ester derivatives http://cherry.chem.bg.ac.rs/handle/123456789/3867. in Fitoterapia
Elsevier..
https://hdl.handle.net/21.15107/rcub_cherry_3889
Novaković MM, Simić S, Koračak L, Zlatović M, Ilić-Tomič T, Asakawa Y, Nikodinović-Runić J, Opsenica I. Supplementary data for the article: Novakovic, M.; Simić, S.; Koračak, L.; Zlatović, M.; Ilic-Tomic, T.; Asakawa, Y.; Nikodinovic-Runic, J.; Opsenica, I. Chemo- and Biocatalytic Esterification of Marchantin A and Cytotoxic Activity of Ester Derivatives. Fitoterapia 2020, 142. https://doi.org/10.1016/j.fitote.2020.104520.oxic activity of ester derivatives http://cherry.chem.bg.ac.rs/handle/123456789/3867. in Fitoterapia. 2020;.
https://hdl.handle.net/21.15107/rcub_cherry_3889 .
Novaković, Miroslav M., Simić, Stefan, Koračak, Ljiljana, Zlatović, Mario, Ilić-Tomič, Tatjana, Asakawa, Yoshinori, Nikodinović-Runić, Jasmina, Opsenica, Igor, "Supplementary data for the article: Novakovic, M.; Simić, S.; Koračak, L.; Zlatović, M.; Ilic-Tomic, T.; Asakawa, Y.; Nikodinovic-Runic, J.; Opsenica, I. Chemo- and Biocatalytic Esterification of Marchantin A and Cytotoxic Activity of Ester Derivatives. Fitoterapia 2020, 142. https://doi.org/10.1016/j.fitote.2020.104520.oxic activity of ester derivatives http://cherry.chem.bg.ac.rs/handle/123456789/3867" in Fitoterapia (2020),
https://hdl.handle.net/21.15107/rcub_cherry_3889 .

Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives

Novaković, Miroslav M.; Simić, Stefan; Koračak, Ljiljana; Zlatović, Mario; Ilić-Tomič, Tatjana; Asakawa, Yoshinori; Nikodinović-Runić, Jasmina; Opsenica, Igor

(Elsevier, 2020)

TY  - JOUR
AU  - Novaković, Miroslav M.
AU  - Simić, Stefan
AU  - Koračak, Ljiljana
AU  - Zlatović, Mario
AU  - Ilić-Tomič, Tatjana
AU  - Asakawa, Yoshinori
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3890
AB  - Chemical and biocatalytic synthesis of seven previously undescribed marchantin A ester derivatives has been presented. Chemical synthesis afforded three peresterified bisbibenzyl products (TE1-TE3), while enzymatic method, using lipase, produced regioselective monoester derivatives (ME1-ME4). The antiproliferative activities of all prepared derivatives of marchantin A were tested on MRC-5 healthy human lung fibroblast, A549 human lung cancer, and MDA-MB-231 human breast cancer cell lines. All tested esters were less cytotoxic in comparison to marchantin A, but they also exhibited lower cytotoxicity against healthy cells. Monoesters displayed higher cytotoxic activities than the corresponding peresterified products, presumably due to the presence of free catechol group. Monohexanoyl ester ME3 displayed the same IC50 like marchantin A against MDA-MB-231 cells, but the selectivity was higher. In this way, regioselective enzymatic monoesterification enhanced selectivity of marchantin A. ME3 was also the most active among all derivatives against lung cancer cells A549 with the slightly lower activity and selectivity in comparison to marchantin A.
PB  - Elsevier
T2  - Fitoterapia
T1  - Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives
VL  - 142
SP  - 104520
DO  - 10.1016/j.fitote.2020.104520
ER  - 
@article{
author = "Novaković, Miroslav M. and Simić, Stefan and Koračak, Ljiljana and Zlatović, Mario and Ilić-Tomič, Tatjana and Asakawa, Yoshinori and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2020",
abstract = "Chemical and biocatalytic synthesis of seven previously undescribed marchantin A ester derivatives has been presented. Chemical synthesis afforded three peresterified bisbibenzyl products (TE1-TE3), while enzymatic method, using lipase, produced regioselective monoester derivatives (ME1-ME4). The antiproliferative activities of all prepared derivatives of marchantin A were tested on MRC-5 healthy human lung fibroblast, A549 human lung cancer, and MDA-MB-231 human breast cancer cell lines. All tested esters were less cytotoxic in comparison to marchantin A, but they also exhibited lower cytotoxicity against healthy cells. Monoesters displayed higher cytotoxic activities than the corresponding peresterified products, presumably due to the presence of free catechol group. Monohexanoyl ester ME3 displayed the same IC50 like marchantin A against MDA-MB-231 cells, but the selectivity was higher. In this way, regioselective enzymatic monoesterification enhanced selectivity of marchantin A. ME3 was also the most active among all derivatives against lung cancer cells A549 with the slightly lower activity and selectivity in comparison to marchantin A.",
publisher = "Elsevier",
journal = "Fitoterapia",
title = "Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives",
volume = "142",
pages = "104520",
doi = "10.1016/j.fitote.2020.104520"
}
Novaković, M. M., Simić, S., Koračak, L., Zlatović, M., Ilić-Tomič, T., Asakawa, Y., Nikodinović-Runić, J.,& Opsenica, I.. (2020). Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives. in Fitoterapia
Elsevier., 142, 104520.
https://doi.org/10.1016/j.fitote.2020.104520
Novaković MM, Simić S, Koračak L, Zlatović M, Ilić-Tomič T, Asakawa Y, Nikodinović-Runić J, Opsenica I. Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives. in Fitoterapia. 2020;142:104520.
doi:10.1016/j.fitote.2020.104520 .
Novaković, Miroslav M., Simić, Stefan, Koračak, Ljiljana, Zlatović, Mario, Ilić-Tomič, Tatjana, Asakawa, Yoshinori, Nikodinović-Runić, Jasmina, Opsenica, Igor, "Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives" in Fitoterapia, 142 (2020):104520,
https://doi.org/10.1016/j.fitote.2020.104520 . .
1
5
1
4
2

Supplementary data for the article: Novakovic, M.; Ilic-Tomic, T.; Tesevic, V.; Simic, K.; Ivanovic, S.; Simic, S.; Opsenica, I.; Nikodinovic-Runic, J. Bisaurones – Enzymatic Production and Biological Evaluation. New J. Chem. 2020, 44 (23), 9647–9655. https://doi.org/10.1039/D0NJ00758G

Novaković, Miroslav M.; Ilić-Tomić, Tatjana; Tešević, Vele; Simić, Katarina; Ivanović, Stefan; Simić, Stefan; Opsenica, Igor; Nikodinović-Runić, Jasmina

(Royal Society of Chemistry, 2020)

TY  - DATA
AU  - Novaković, Miroslav M.
AU  - Ilić-Tomić, Tatjana
AU  - Tešević, Vele
AU  - Simić, Katarina
AU  - Ivanović, Stefan
AU  - Simić, Stefan
AU  - Opsenica, Igor
AU  - Nikodinović-Runić, Jasmina
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4078
PB  - Royal Society of Chemistry
T2  - New Journal of Chemistry
T1  - Supplementary data for the article: Novakovic, M.; Ilic-Tomic, T.; Tesevic, V.; Simic, K.; Ivanovic, S.; Simic, S.; Opsenica, I.; Nikodinovic-Runic, J. Bisaurones – Enzymatic Production and Biological Evaluation. New J. Chem. 2020, 44 (23), 9647–9655. https://doi.org/10.1039/D0NJ00758G
UR  - https://hdl.handle.net/21.15107/rcub_cherry_4078
ER  - 
@misc{
author = "Novaković, Miroslav M. and Ilić-Tomić, Tatjana and Tešević, Vele and Simić, Katarina and Ivanović, Stefan and Simić, Stefan and Opsenica, Igor and Nikodinović-Runić, Jasmina",
year = "2020",
publisher = "Royal Society of Chemistry",
journal = "New Journal of Chemistry",
title = "Supplementary data for the article: Novakovic, M.; Ilic-Tomic, T.; Tesevic, V.; Simic, K.; Ivanovic, S.; Simic, S.; Opsenica, I.; Nikodinovic-Runic, J. Bisaurones – Enzymatic Production and Biological Evaluation. New J. Chem. 2020, 44 (23), 9647–9655. https://doi.org/10.1039/D0NJ00758G",
url = "https://hdl.handle.net/21.15107/rcub_cherry_4078"
}
Novaković, M. M., Ilić-Tomić, T., Tešević, V., Simić, K., Ivanović, S., Simić, S., Opsenica, I.,& Nikodinović-Runić, J.. (2020). Supplementary data for the article: Novakovic, M.; Ilic-Tomic, T.; Tesevic, V.; Simic, K.; Ivanovic, S.; Simic, S.; Opsenica, I.; Nikodinovic-Runic, J. Bisaurones – Enzymatic Production and Biological Evaluation. New J. Chem. 2020, 44 (23), 9647–9655. https://doi.org/10.1039/D0NJ00758G. in New Journal of Chemistry
Royal Society of Chemistry..
https://hdl.handle.net/21.15107/rcub_cherry_4078
Novaković MM, Ilić-Tomić T, Tešević V, Simić K, Ivanović S, Simić S, Opsenica I, Nikodinović-Runić J. Supplementary data for the article: Novakovic, M.; Ilic-Tomic, T.; Tesevic, V.; Simic, K.; Ivanovic, S.; Simic, S.; Opsenica, I.; Nikodinovic-Runic, J. Bisaurones – Enzymatic Production and Biological Evaluation. New J. Chem. 2020, 44 (23), 9647–9655. https://doi.org/10.1039/D0NJ00758G. in New Journal of Chemistry. 2020;.
https://hdl.handle.net/21.15107/rcub_cherry_4078 .
Novaković, Miroslav M., Ilić-Tomić, Tatjana, Tešević, Vele, Simić, Katarina, Ivanović, Stefan, Simić, Stefan, Opsenica, Igor, Nikodinović-Runić, Jasmina, "Supplementary data for the article: Novakovic, M.; Ilic-Tomic, T.; Tesevic, V.; Simic, K.; Ivanovic, S.; Simic, S.; Opsenica, I.; Nikodinovic-Runic, J. Bisaurones – Enzymatic Production and Biological Evaluation. New J. Chem. 2020, 44 (23), 9647–9655. https://doi.org/10.1039/D0NJ00758G" in New Journal of Chemistry (2020),
https://hdl.handle.net/21.15107/rcub_cherry_4078 .

Chemical Composition, Total Phenols and Flavonoids Contents and Antioxidant Activity as Nutritive Potential of Roasted Hazelnut Skins (Corylus avellana L.)

Ivanović, Stefan; Avramović, Nataša; Dojčinović, Biljana P.; Trifunović, Snežana S.; Novaković, Miroslav M.; Tešević, Vele; Mandić, Boris

(Multidisciplinary Digital Publishing Institute(Multidisciplinary Digital Publishing Institute (MDPI), 2020)

TY  - JOUR
AU  - Ivanović, Stefan
AU  - Avramović, Nataša
AU  - Dojčinović, Biljana P.
AU  - Trifunović, Snežana S.
AU  - Novaković, Miroslav M.
AU  - Tešević, Vele
AU  - Mandić, Boris
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3992
AB  - The present study evaluates natural composition of Serbian roasted hazelnut skins (HS) with potential role in application as functional nutrient of various food products. Total phenols (TPC) and flavonoids contents (TFC) in HS extracts obtained with dierent ethanol concentrations (10%—I, 50%—II and 96%—III) and their antioxidant activities were investigated. The highest total phenols content (706.0  9.7 mgGAE/gextract) was observed in 96% ethanol HS extract. Ethanol HS extracts showed very high antioxidant activity with eective concentrations (EC50) ranged between 0.052 and 0.066 mg/mL. The phenol and flavonoid content of roasted HS extracts I–III was determined by HPLC-ESI-MS/MS analyses. Contents of lipids, proteins, carbohydrates, metals, and C, H, N, S elements in roasted HS were also determined. Relatively high C/N, C/P and C/N/P ratios, rich metal contents and fatty acids composition indicated that hazelnut skin might be a good candidate for use as either human or fungal functional nutrient. In addition, possible application of phenolic HS extracts as UV booster was studied by recording UV spectra (220–440 nm) of 10 mg/L of HS extracts I–III combined with 10 mg/L of chemical sunscreen agent benzophenone-3 and in vitro sun protection factor (SPF) was calculated.
PB  - Multidisciplinary Digital Publishing Institute(Multidisciplinary Digital Publishing Institute (MDPI)
T2  - Foods
T1  - Chemical Composition, Total Phenols and Flavonoids Contents and Antioxidant Activity as Nutritive Potential of Roasted Hazelnut Skins (Corylus avellana L.)
VL  - 9
IS  - 4
SP  - 430
DO  - 10.3390/foods9040430
ER  - 
@article{
author = "Ivanović, Stefan and Avramović, Nataša and Dojčinović, Biljana P. and Trifunović, Snežana S. and Novaković, Miroslav M. and Tešević, Vele and Mandić, Boris",
year = "2020",
abstract = "The present study evaluates natural composition of Serbian roasted hazelnut skins (HS) with potential role in application as functional nutrient of various food products. Total phenols (TPC) and flavonoids contents (TFC) in HS extracts obtained with dierent ethanol concentrations (10%—I, 50%—II and 96%—III) and their antioxidant activities were investigated. The highest total phenols content (706.0  9.7 mgGAE/gextract) was observed in 96% ethanol HS extract. Ethanol HS extracts showed very high antioxidant activity with eective concentrations (EC50) ranged between 0.052 and 0.066 mg/mL. The phenol and flavonoid content of roasted HS extracts I–III was determined by HPLC-ESI-MS/MS analyses. Contents of lipids, proteins, carbohydrates, metals, and C, H, N, S elements in roasted HS were also determined. Relatively high C/N, C/P and C/N/P ratios, rich metal contents and fatty acids composition indicated that hazelnut skin might be a good candidate for use as either human or fungal functional nutrient. In addition, possible application of phenolic HS extracts as UV booster was studied by recording UV spectra (220–440 nm) of 10 mg/L of HS extracts I–III combined with 10 mg/L of chemical sunscreen agent benzophenone-3 and in vitro sun protection factor (SPF) was calculated.",
publisher = "Multidisciplinary Digital Publishing Institute(Multidisciplinary Digital Publishing Institute (MDPI)",
journal = "Foods",
title = "Chemical Composition, Total Phenols and Flavonoids Contents and Antioxidant Activity as Nutritive Potential of Roasted Hazelnut Skins (Corylus avellana L.)",
volume = "9",
number = "4",
pages = "430",
doi = "10.3390/foods9040430"
}
Ivanović, S., Avramović, N., Dojčinović, B. P., Trifunović, S. S., Novaković, M. M., Tešević, V.,& Mandić, B.. (2020). Chemical Composition, Total Phenols and Flavonoids Contents and Antioxidant Activity as Nutritive Potential of Roasted Hazelnut Skins (Corylus avellana L.). in Foods
Multidisciplinary Digital Publishing Institute(Multidisciplinary Digital Publishing Institute (MDPI)., 9(4), 430.
https://doi.org/10.3390/foods9040430
Ivanović S, Avramović N, Dojčinović BP, Trifunović SS, Novaković MM, Tešević V, Mandić B. Chemical Composition, Total Phenols and Flavonoids Contents and Antioxidant Activity as Nutritive Potential of Roasted Hazelnut Skins (Corylus avellana L.). in Foods. 2020;9(4):430.
doi:10.3390/foods9040430 .
Ivanović, Stefan, Avramović, Nataša, Dojčinović, Biljana P., Trifunović, Snežana S., Novaković, Miroslav M., Tešević, Vele, Mandić, Boris, "Chemical Composition, Total Phenols and Flavonoids Contents and Antioxidant Activity as Nutritive Potential of Roasted Hazelnut Skins (Corylus avellana L.)" in Foods, 9, no. 4 (2020):430,
https://doi.org/10.3390/foods9040430 . .
22
7
23
17

Bisaurones – enzymatic production and biological evaluation

Novaković, Miroslav M.; Ilić-Tomić, Tatjana; Tešević, Vele; Simić, Katarina; Ivanović, Stefan; Simić, Stefan; Opsenica, Igor; Nikodinović-Runić, Jasmina

(Royal Society of Chemistry, 2020)

TY  - JOUR
AU  - Novaković, Miroslav M.
AU  - Ilić-Tomić, Tatjana
AU  - Tešević, Vele
AU  - Simić, Katarina
AU  - Ivanović, Stefan
AU  - Simić, Stefan
AU  - Opsenica, Igor
AU  - Nikodinović-Runić, Jasmina
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4052
AB  - The Trametes versicolor laccase catalyzed oxidation of chalcone butein afforded four dimers of aurone sulfuretin (i.e. two regioisomeric pairs of diasteromers, 1-4) as the major products. The formation of the dimers was explained by a two step process involving the initial cyclization of butein into aurone sulfuretin, followed by the combination of two molecules of sulfuretin. The coupling process occurred between the 2,10-double bond of one molecule of sulfuretin and the (3′,4′) catechol group of the other to yield a dimeric structure. This was confirmed by the experiment involving the laccase catalyzed oxidation of sulfuretin yielding the same dimeric bisaurones. Compounds 1, 3 and 4, were isolated using semipreparative HPLC and characterized by the detailed analysis of the NMR, MS, IR, and UV-vis data. The structure of compound 2, isolated as a mixture containing ca. 25% of compound 1, was proposed by the comparison of 1H NMR data to compound 1 and by using LC-ESIMS analysis. The starting chalcone butein and the products of the biocatalytic transformation, aurone sulfuretin and sulfuretin dimers 1, 3 and 4, were evaluated for their cytotoxic and antioxidative properties in vitro using a healthy human fibroblast (MRC5) cell line. The biotransformation products showed lower cytotoxicity but higher antioxidative properties. The C. coggygria bark methanol extract rich in butein and sulfuretin was also biotransformed by laccase. The transformed extract exhibited significantly improved antioxidative activities.
PB  - Royal Society of Chemistry
T2  - New Journal of Chemistry
T1  - Bisaurones – enzymatic production and biological evaluation
VL  - 44
IS  - 23
SP  - 9647
EP  - 9655
DO  - 10.1039/d0nj00758g
ER  - 
@article{
author = "Novaković, Miroslav M. and Ilić-Tomić, Tatjana and Tešević, Vele and Simić, Katarina and Ivanović, Stefan and Simić, Stefan and Opsenica, Igor and Nikodinović-Runić, Jasmina",
year = "2020",
abstract = "The Trametes versicolor laccase catalyzed oxidation of chalcone butein afforded four dimers of aurone sulfuretin (i.e. two regioisomeric pairs of diasteromers, 1-4) as the major products. The formation of the dimers was explained by a two step process involving the initial cyclization of butein into aurone sulfuretin, followed by the combination of two molecules of sulfuretin. The coupling process occurred between the 2,10-double bond of one molecule of sulfuretin and the (3′,4′) catechol group of the other to yield a dimeric structure. This was confirmed by the experiment involving the laccase catalyzed oxidation of sulfuretin yielding the same dimeric bisaurones. Compounds 1, 3 and 4, were isolated using semipreparative HPLC and characterized by the detailed analysis of the NMR, MS, IR, and UV-vis data. The structure of compound 2, isolated as a mixture containing ca. 25% of compound 1, was proposed by the comparison of 1H NMR data to compound 1 and by using LC-ESIMS analysis. The starting chalcone butein and the products of the biocatalytic transformation, aurone sulfuretin and sulfuretin dimers 1, 3 and 4, were evaluated for their cytotoxic and antioxidative properties in vitro using a healthy human fibroblast (MRC5) cell line. The biotransformation products showed lower cytotoxicity but higher antioxidative properties. The C. coggygria bark methanol extract rich in butein and sulfuretin was also biotransformed by laccase. The transformed extract exhibited significantly improved antioxidative activities.",
publisher = "Royal Society of Chemistry",
journal = "New Journal of Chemistry",
title = "Bisaurones – enzymatic production and biological evaluation",
volume = "44",
number = "23",
pages = "9647-9655",
doi = "10.1039/d0nj00758g"
}
Novaković, M. M., Ilić-Tomić, T., Tešević, V., Simić, K., Ivanović, S., Simić, S., Opsenica, I.,& Nikodinović-Runić, J.. (2020). Bisaurones – enzymatic production and biological evaluation. in New Journal of Chemistry
Royal Society of Chemistry., 44(23), 9647-9655.
https://doi.org/10.1039/d0nj00758g
Novaković MM, Ilić-Tomić T, Tešević V, Simić K, Ivanović S, Simić S, Opsenica I, Nikodinović-Runić J. Bisaurones – enzymatic production and biological evaluation. in New Journal of Chemistry. 2020;44(23):9647-9655.
doi:10.1039/d0nj00758g .
Novaković, Miroslav M., Ilić-Tomić, Tatjana, Tešević, Vele, Simić, Katarina, Ivanović, Stefan, Simić, Stefan, Opsenica, Igor, Nikodinović-Runić, Jasmina, "Bisaurones – enzymatic production and biological evaluation" in New Journal of Chemistry, 44, no. 23 (2020):9647-9655,
https://doi.org/10.1039/d0nj00758g . .
1
1
1

Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives

Novaković, Miroslav M.; Simić, Stefan; Koračak, Ljiljana; Zlatović, Mario; Ilić-Tomič, Tatjana; Asakawa, Yoshinori; Nikodinović-Runić, Jasmina; Opsenica, Igor

(Elsevier, 2020)

TY  - JOUR
AU  - Novaković, Miroslav M.
AU  - Simić, Stefan
AU  - Koračak, Ljiljana
AU  - Zlatović, Mario
AU  - Ilić-Tomič, Tatjana
AU  - Asakawa, Yoshinori
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3867
AB  - Chemical and biocatalytic synthesis of seven previously undescribed marchantin A ester derivatives has been presented. Chemical synthesis afforded three peresterified bisbibenzyl products (TE1-TE3), while enzymatic method, using lipase, produced regioselective monoester derivatives (ME1-ME4). The antiproliferative activities of all prepared derivatives of marchantin A were tested on MRC-5 healthy human lung fibroblast, A549 human lung cancer, and MDA-MB-231 human breast cancer cell lines. All tested esters were less cytotoxic in comparison to marchantin A, but they also exhibited lower cytotoxicity against healthy cells. Monoesters displayed higher cytotoxic activities than the corresponding peresterified products, presumably due to the presence of free catechol group. Monohexanoyl ester ME3 displayed the same IC50 like marchantin A against MDA-MB-231 cells, but the selectivity was higher. In this way, regioselective enzymatic monoesterification enhanced selectivity of marchantin A. ME3 was also the most active among all derivatives against lung cancer cells A549 with the slightly lower activity and selectivity in comparison to marchantin A.
PB  - Elsevier
T2  - Fitoterapia
T1  - Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives
VL  - 142
SP  - 104520
DO  - 10.1016/j.fitote.2020.104520
ER  - 
@article{
author = "Novaković, Miroslav M. and Simić, Stefan and Koračak, Ljiljana and Zlatović, Mario and Ilić-Tomič, Tatjana and Asakawa, Yoshinori and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2020",
abstract = "Chemical and biocatalytic synthesis of seven previously undescribed marchantin A ester derivatives has been presented. Chemical synthesis afforded three peresterified bisbibenzyl products (TE1-TE3), while enzymatic method, using lipase, produced regioselective monoester derivatives (ME1-ME4). The antiproliferative activities of all prepared derivatives of marchantin A were tested on MRC-5 healthy human lung fibroblast, A549 human lung cancer, and MDA-MB-231 human breast cancer cell lines. All tested esters were less cytotoxic in comparison to marchantin A, but they also exhibited lower cytotoxicity against healthy cells. Monoesters displayed higher cytotoxic activities than the corresponding peresterified products, presumably due to the presence of free catechol group. Monohexanoyl ester ME3 displayed the same IC50 like marchantin A against MDA-MB-231 cells, but the selectivity was higher. In this way, regioselective enzymatic monoesterification enhanced selectivity of marchantin A. ME3 was also the most active among all derivatives against lung cancer cells A549 with the slightly lower activity and selectivity in comparison to marchantin A.",
publisher = "Elsevier",
journal = "Fitoterapia",
title = "Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives",
volume = "142",
pages = "104520",
doi = "10.1016/j.fitote.2020.104520"
}
Novaković, M. M., Simić, S., Koračak, L., Zlatović, M., Ilić-Tomič, T., Asakawa, Y., Nikodinović-Runić, J.,& Opsenica, I.. (2020). Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives. in Fitoterapia
Elsevier., 142, 104520.
https://doi.org/10.1016/j.fitote.2020.104520
Novaković MM, Simić S, Koračak L, Zlatović M, Ilić-Tomič T, Asakawa Y, Nikodinović-Runić J, Opsenica I. Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives. in Fitoterapia. 2020;142:104520.
doi:10.1016/j.fitote.2020.104520 .
Novaković, Miroslav M., Simić, Stefan, Koračak, Ljiljana, Zlatović, Mario, Ilić-Tomič, Tatjana, Asakawa, Yoshinori, Nikodinović-Runić, Jasmina, Opsenica, Igor, "Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives" in Fitoterapia, 142 (2020):104520,
https://doi.org/10.1016/j.fitote.2020.104520 . .
1
5
1
4
2

Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia cruciata

Novaković, Miroslav M.; Bukvicki, Danka; Anđelković, Boban D.; Ilić-Tomić, Tatjana; Veljić, Milan; Tešević, Vele; Asakawa, Yoshinori

(American Chemical Society and American Society of Pharmacognosy, 2019)

TY  - JOUR
AU  - Novaković, Miroslav M.
AU  - Bukvicki, Danka
AU  - Anđelković, Boban D.
AU  - Ilić-Tomić, Tatjana
AU  - Veljić, Milan
AU  - Tešević, Vele
AU  - Asakawa, Yoshinori
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3096
AB  - Seven new bisbibenzyls (1-7) were isolated from the methanol extract of the liverwort Lunularia cruciata along with one previously known bibenzyl and five known bisbibenzyls. The structures of compounds 1-7 were elucidated on the basis of the spectroscopic data. These newly isolated bisbibenzyls may be divided into two groups, the acyclic bisbibenzyls, perrottetins (1-3), and the cyclic analogues, riccardins (4-7). Besides standard perrottetin and riccardin structures (1 and 4, respectively), they contain phenanthrene (3 and 5), dihydrophenanthrene (2), and quinone moieties (6 and 7), rarely found in natural products. The new compounds 3 and 5, as well as the known riccardin G, exhibited cytotoxic activity against the A549 lung cancer cell line with IC 50 values of 5.0, 5.0, and 2.5 μM, respectively.
PB  - American Chemical Society and American Society of Pharmacognosy
T2  - Journal of Natural Products
T1  - Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia cruciata
VL  - 82
IS  - 4
SP  - 694
EP  - 701
DO  - 10.1021/acs.jnatprod.8b00390
ER  - 
@article{
author = "Novaković, Miroslav M. and Bukvicki, Danka and Anđelković, Boban D. and Ilić-Tomić, Tatjana and Veljić, Milan and Tešević, Vele and Asakawa, Yoshinori",
year = "2019",
abstract = "Seven new bisbibenzyls (1-7) were isolated from the methanol extract of the liverwort Lunularia cruciata along with one previously known bibenzyl and five known bisbibenzyls. The structures of compounds 1-7 were elucidated on the basis of the spectroscopic data. These newly isolated bisbibenzyls may be divided into two groups, the acyclic bisbibenzyls, perrottetins (1-3), and the cyclic analogues, riccardins (4-7). Besides standard perrottetin and riccardin structures (1 and 4, respectively), they contain phenanthrene (3 and 5), dihydrophenanthrene (2), and quinone moieties (6 and 7), rarely found in natural products. The new compounds 3 and 5, as well as the known riccardin G, exhibited cytotoxic activity against the A549 lung cancer cell line with IC 50 values of 5.0, 5.0, and 2.5 μM, respectively.",
publisher = "American Chemical Society and American Society of Pharmacognosy",
journal = "Journal of Natural Products",
title = "Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia cruciata",
volume = "82",
number = "4",
pages = "694-701",
doi = "10.1021/acs.jnatprod.8b00390"
}
Novaković, M. M., Bukvicki, D., Anđelković, B. D., Ilić-Tomić, T., Veljić, M., Tešević, V.,& Asakawa, Y.. (2019). Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia cruciata. in Journal of Natural Products
American Chemical Society and American Society of Pharmacognosy., 82(4), 694-701.
https://doi.org/10.1021/acs.jnatprod.8b00390
Novaković MM, Bukvicki D, Anđelković BD, Ilić-Tomić T, Veljić M, Tešević V, Asakawa Y. Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia cruciata. in Journal of Natural Products. 2019;82(4):694-701.
doi:10.1021/acs.jnatprod.8b00390 .
Novaković, Miroslav M., Bukvicki, Danka, Anđelković, Boban D., Ilić-Tomić, Tatjana, Veljić, Milan, Tešević, Vele, Asakawa, Yoshinori, "Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia cruciata" in Journal of Natural Products, 82, no. 4 (2019):694-701,
https://doi.org/10.1021/acs.jnatprod.8b00390 . .
1
23
8
23
19

Supplementary data for article: Novakovic, M.; Bukvicki, D.; Andjelkovic, B.; Ilic-Tomic, T.; Veljic, M.; Tesevic, V.; Asakawa, Y. Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia Cruciata. Journal of Natural Products 2019, 82 (4), 694–701. https://doi.org/10.1021/acs.jnatprod.8b00390

Novaković, Miroslav M.; Bukvicki, Danka; Anđelković, Boban D.; Ilić-Tomić, Tatjana; Veljić, Milan; Tešević, Vele; Asakawa, Yoshinori

(American Chemical Society and American Society of Pharmacognosy, 2019)

TY  - DATA
AU  - Novaković, Miroslav M.
AU  - Bukvicki, Danka
AU  - Anđelković, Boban D.
AU  - Ilić-Tomić, Tatjana
AU  - Veljić, Milan
AU  - Tešević, Vele
AU  - Asakawa, Yoshinori
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3097
PB  - American Chemical Society and American Society of Pharmacognosy
T2  - Journal of Natural Products
T1  - Supplementary data for article:   	Novakovic, M.; Bukvicki, D.; Andjelkovic, B.; Ilic-Tomic, T.; Veljic, M.; Tesevic, V.; Asakawa, Y. Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia Cruciata. Journal of Natural Products 2019, 82 (4), 694–701. https://doi.org/10.1021/acs.jnatprod.8b00390
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3097
ER  - 
@misc{
author = "Novaković, Miroslav M. and Bukvicki, Danka and Anđelković, Boban D. and Ilić-Tomić, Tatjana and Veljić, Milan and Tešević, Vele and Asakawa, Yoshinori",
year = "2019",
publisher = "American Chemical Society and American Society of Pharmacognosy",
journal = "Journal of Natural Products",
title = "Supplementary data for article:   	Novakovic, M.; Bukvicki, D.; Andjelkovic, B.; Ilic-Tomic, T.; Veljic, M.; Tesevic, V.; Asakawa, Y. Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia Cruciata. Journal of Natural Products 2019, 82 (4), 694–701. https://doi.org/10.1021/acs.jnatprod.8b00390",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3097"
}
Novaković, M. M., Bukvicki, D., Anđelković, B. D., Ilić-Tomić, T., Veljić, M., Tešević, V.,& Asakawa, Y.. (2019). Supplementary data for article:   	Novakovic, M.; Bukvicki, D.; Andjelkovic, B.; Ilic-Tomic, T.; Veljic, M.; Tesevic, V.; Asakawa, Y. Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia Cruciata. Journal of Natural Products 2019, 82 (4), 694–701. https://doi.org/10.1021/acs.jnatprod.8b00390. in Journal of Natural Products
American Chemical Society and American Society of Pharmacognosy..
https://hdl.handle.net/21.15107/rcub_cherry_3097
Novaković MM, Bukvicki D, Anđelković BD, Ilić-Tomić T, Veljić M, Tešević V, Asakawa Y. Supplementary data for article:   	Novakovic, M.; Bukvicki, D.; Andjelkovic, B.; Ilic-Tomic, T.; Veljic, M.; Tesevic, V.; Asakawa, Y. Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia Cruciata. Journal of Natural Products 2019, 82 (4), 694–701. https://doi.org/10.1021/acs.jnatprod.8b00390. in Journal of Natural Products. 2019;.
https://hdl.handle.net/21.15107/rcub_cherry_3097 .
Novaković, Miroslav M., Bukvicki, Danka, Anđelković, Boban D., Ilić-Tomić, Tatjana, Veljić, Milan, Tešević, Vele, Asakawa, Yoshinori, "Supplementary data for article:   	Novakovic, M.; Bukvicki, D.; Andjelkovic, B.; Ilic-Tomic, T.; Veljic, M.; Tesevic, V.; Asakawa, Y. Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia Cruciata. Journal of Natural Products 2019, 82 (4), 694–701. https://doi.org/10.1021/acs.jnatprod.8b00390" in Journal of Natural Products (2019),
https://hdl.handle.net/21.15107/rcub_cherry_3097 .

Tetracyclic triterpenoids from Euphorbia nicaeensis All

Krstić, Gordana B.; Novaković, Miroslav M.; Jadranin, Milka; Tešević, Vele

(2019)

TY  - JOUR
AU  - Krstić, Gordana B.
AU  - Novaković, Miroslav M.
AU  - Jadranin, Milka
AU  - Tešević, Vele
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3931
AB  - In this study, three tetracyclic triterpenes: (3S,24S)-tirucall-7-ene-3,24,25-triol (1), (3S,24R)-tirucall-7-ene-3,24,25-triol (2) and inoterpene C (3), were isolated from the milkweed Euphorbia nicaeensis All. using dry-column flash silica gel chromatography and semipreparative normal-phase HPLC. Their structures were determined on the basis of 1D and 2D NMR spectra and literature review. Although these three compounds have previously been isolated from other plant species, this is the first time that they have been isolated from E. nicaeensis.
T2  - Advanced Technologies
T1  - Tetracyclic triterpenoids from Euphorbia nicaeensis All
VL  - 8
IS  - 2
SP  - 37
EP  - 45
DO  - 10.5937/savteh1902037K
ER  - 
@article{
author = "Krstić, Gordana B. and Novaković, Miroslav M. and Jadranin, Milka and Tešević, Vele",
year = "2019",
abstract = "In this study, three tetracyclic triterpenes: (3S,24S)-tirucall-7-ene-3,24,25-triol (1), (3S,24R)-tirucall-7-ene-3,24,25-triol (2) and inoterpene C (3), were isolated from the milkweed Euphorbia nicaeensis All. using dry-column flash silica gel chromatography and semipreparative normal-phase HPLC. Their structures were determined on the basis of 1D and 2D NMR spectra and literature review. Although these three compounds have previously been isolated from other plant species, this is the first time that they have been isolated from E. nicaeensis.",
journal = "Advanced Technologies",
title = "Tetracyclic triterpenoids from Euphorbia nicaeensis All",
volume = "8",
number = "2",
pages = "37-45",
doi = "10.5937/savteh1902037K"
}
Krstić, G. B., Novaković, M. M., Jadranin, M.,& Tešević, V.. (2019). Tetracyclic triterpenoids from Euphorbia nicaeensis All. in Advanced Technologies, 8(2), 37-45.
https://doi.org/10.5937/savteh1902037K
Krstić GB, Novaković MM, Jadranin M, Tešević V. Tetracyclic triterpenoids from Euphorbia nicaeensis All. in Advanced Technologies. 2019;8(2):37-45.
doi:10.5937/savteh1902037K .
Krstić, Gordana B., Novaković, Miroslav M., Jadranin, Milka, Tešević, Vele, "Tetracyclic triterpenoids from Euphorbia nicaeensis All" in Advanced Technologies, 8, no. 2 (2019):37-45,
https://doi.org/10.5937/savteh1902037K . .
2
2

Antibacterial and Antibiofilm Activity of Flavonoid and Saponin Derivatives from Atriplex tatarica against Pseudomonas aeruginosa

Stanković, Jovana; Gođevac, Dejan; Tešević, Vele; Dajić-Stevanović, Zora; Ćirić, Ana D.; Soković, Marina; Novaković, Miroslav M.

(American Chemical Society, 2019)

TY  - JOUR
AU  - Stanković, Jovana
AU  - Gođevac, Dejan
AU  - Tešević, Vele
AU  - Dajić-Stevanović, Zora
AU  - Ćirić, Ana D.
AU  - Soković, Marina
AU  - Novaković, Miroslav M.
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3725
AB  - A new flavonoid glucoside derivative, patuletin 3-O-(2-O-feruloyl)-β-d-glucuronopyranosyl-(1→2)-β-d-glucopyranoside, named atriplexin IV (1), and three new triterpenoid saponin derivatives, two sulfonylated, β-d-glucopyranosyl-3-O-(2-O-sulfo-β-d-galactopyranosyl)-(1→2)-α-l-arabinopyranoside-30-alolean-12-en-28-oate (2), named atriplexogenin I, β-d-glucopyranosyl-3-O-(2-O-sulfo-β-d-galactopyranosyl)-(1→2)-α-l-arabinopyranoside)-30-hydroxyolean-12-en-28-oate (3), named atriplexogenin II, and β-d-glucopyranosyl-3-O-(β-d-glucopyranosyl-(1→2)-β-d-galactopyranosyl-(1→2)-α-l-arabinopyranoside)-30-alolean-12-en-28-oate (4), named atriplexogenin III, were isolated by silica gel column and semipreparative HPLC chromatography from the n-butanol extract of the salt marsh plant Atriplex tatarica. In addition, two known secondary metabolites, patuletin3-O-β-d-apiofuranosyl-(1'→2″)-β-d-glucopyranoside (5) and patuletin 3-O-5'-O-feruloyl-β-d-apiofuranosyl-(1'→2″)-β-d-glucopyranoside (6), were isolated for the first time from A. tatarica. The structures of the isolated compounds were elucidated by 1D and 2D NMR, HRESIMS, IR, and UV data. Antibacterial activity by the microdilution method and antibiofilm activity against P. aeruginosa were assessed. Compound 5 possesses significant antibacterial activity, while the most potent antibiofilm agent is compound 2.
PB  - American Chemical Society
T2  - Journal of Natural Products
T1  - Antibacterial and Antibiofilm Activity of Flavonoid and Saponin Derivatives from Atriplex tatarica against Pseudomonas aeruginosa
VL  - 82
IS  - 6
SP  - 1487
EP  - 1495
DO  - 10.1021/acs.jnatprod.8b00970
ER  - 
@article{
author = "Stanković, Jovana and Gođevac, Dejan and Tešević, Vele and Dajić-Stevanović, Zora and Ćirić, Ana D. and Soković, Marina and Novaković, Miroslav M.",
year = "2019",
abstract = "A new flavonoid glucoside derivative, patuletin 3-O-(2-O-feruloyl)-β-d-glucuronopyranosyl-(1→2)-β-d-glucopyranoside, named atriplexin IV (1), and three new triterpenoid saponin derivatives, two sulfonylated, β-d-glucopyranosyl-3-O-(2-O-sulfo-β-d-galactopyranosyl)-(1→2)-α-l-arabinopyranoside-30-alolean-12-en-28-oate (2), named atriplexogenin I, β-d-glucopyranosyl-3-O-(2-O-sulfo-β-d-galactopyranosyl)-(1→2)-α-l-arabinopyranoside)-30-hydroxyolean-12-en-28-oate (3), named atriplexogenin II, and β-d-glucopyranosyl-3-O-(β-d-glucopyranosyl-(1→2)-β-d-galactopyranosyl-(1→2)-α-l-arabinopyranoside)-30-alolean-12-en-28-oate (4), named atriplexogenin III, were isolated by silica gel column and semipreparative HPLC chromatography from the n-butanol extract of the salt marsh plant Atriplex tatarica. In addition, two known secondary metabolites, patuletin3-O-β-d-apiofuranosyl-(1'→2″)-β-d-glucopyranoside (5) and patuletin 3-O-5'-O-feruloyl-β-d-apiofuranosyl-(1'→2″)-β-d-glucopyranoside (6), were isolated for the first time from A. tatarica. The structures of the isolated compounds were elucidated by 1D and 2D NMR, HRESIMS, IR, and UV data. Antibacterial activity by the microdilution method and antibiofilm activity against P. aeruginosa were assessed. Compound 5 possesses significant antibacterial activity, while the most potent antibiofilm agent is compound 2.",
publisher = "American Chemical Society",
journal = "Journal of Natural Products",
title = "Antibacterial and Antibiofilm Activity of Flavonoid and Saponin Derivatives from Atriplex tatarica against Pseudomonas aeruginosa",
volume = "82",
number = "6",
pages = "1487-1495",
doi = "10.1021/acs.jnatprod.8b00970"
}
Stanković, J., Gođevac, D., Tešević, V., Dajić-Stevanović, Z., Ćirić, A. D., Soković, M.,& Novaković, M. M.. (2019). Antibacterial and Antibiofilm Activity of Flavonoid and Saponin Derivatives from Atriplex tatarica against Pseudomonas aeruginosa. in Journal of Natural Products
American Chemical Society., 82(6), 1487-1495.
https://doi.org/10.1021/acs.jnatprod.8b00970
Stanković J, Gođevac D, Tešević V, Dajić-Stevanović Z, Ćirić AD, Soković M, Novaković MM. Antibacterial and Antibiofilm Activity of Flavonoid and Saponin Derivatives from Atriplex tatarica against Pseudomonas aeruginosa. in Journal of Natural Products. 2019;82(6):1487-1495.
doi:10.1021/acs.jnatprod.8b00970 .
Stanković, Jovana, Gođevac, Dejan, Tešević, Vele, Dajić-Stevanović, Zora, Ćirić, Ana D., Soković, Marina, Novaković, Miroslav M., "Antibacterial and Antibiofilm Activity of Flavonoid and Saponin Derivatives from Atriplex tatarica against Pseudomonas aeruginosa" in Journal of Natural Products, 82, no. 6 (2019):1487-1495,
https://doi.org/10.1021/acs.jnatprod.8b00970 . .
4
16
7
17
14

Supplementary data for the article: Stanković, J.; Godevac, D.; Tešević, V.; Dajić-Stevanović, Z.; Ćirić, A.; Soković, M.; Novaković, M. Antibacterial and Antibiofilm Activity of Flavonoid and Saponin Derivatives from Atriplex Tatarica against Pseudomonas Aeruginosa. Journal of Natural Products 2019, 82 (6), 1487–1495. https://doi.org/10.1021/acs.jnatprod.8b00970

Stanković, Jovana; Gođevac, Dejan; Tešević, Vele; Dajić-Stevanović, Zora; Ćirić, Ana D.; Soković, Marina; Novaković, Miroslav M.

(American Chemical Society, 2019)

TY  - DATA
AU  - Stanković, Jovana
AU  - Gođevac, Dejan
AU  - Tešević, Vele
AU  - Dajić-Stevanović, Zora
AU  - Ćirić, Ana D.
AU  - Soković, Marina
AU  - Novaković, Miroslav M.
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3726
PB  - American Chemical Society
T2  - Journal of Natural Products
T1  - Supplementary data for the article: Stanković, J.; Godevac, D.; Tešević, V.; Dajić-Stevanović, Z.; Ćirić, A.; Soković, M.; Novaković, M. Antibacterial and Antibiofilm Activity of Flavonoid and Saponin Derivatives from Atriplex Tatarica against Pseudomonas Aeruginosa. Journal of Natural Products 2019, 82 (6), 1487–1495. https://doi.org/10.1021/acs.jnatprod.8b00970
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3726
ER  - 
@misc{
author = "Stanković, Jovana and Gođevac, Dejan and Tešević, Vele and Dajić-Stevanović, Zora and Ćirić, Ana D. and Soković, Marina and Novaković, Miroslav M.",
year = "2019",
publisher = "American Chemical Society",
journal = "Journal of Natural Products",
title = "Supplementary data for the article: Stanković, J.; Godevac, D.; Tešević, V.; Dajić-Stevanović, Z.; Ćirić, A.; Soković, M.; Novaković, M. Antibacterial and Antibiofilm Activity of Flavonoid and Saponin Derivatives from Atriplex Tatarica against Pseudomonas Aeruginosa. Journal of Natural Products 2019, 82 (6), 1487–1495. https://doi.org/10.1021/acs.jnatprod.8b00970",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3726"
}
Stanković, J., Gođevac, D., Tešević, V., Dajić-Stevanović, Z., Ćirić, A. D., Soković, M.,& Novaković, M. M.. (2019). Supplementary data for the article: Stanković, J.; Godevac, D.; Tešević, V.; Dajić-Stevanović, Z.; Ćirić, A.; Soković, M.; Novaković, M. Antibacterial and Antibiofilm Activity of Flavonoid and Saponin Derivatives from Atriplex Tatarica against Pseudomonas Aeruginosa. Journal of Natural Products 2019, 82 (6), 1487–1495. https://doi.org/10.1021/acs.jnatprod.8b00970. in Journal of Natural Products
American Chemical Society..
https://hdl.handle.net/21.15107/rcub_cherry_3726
Stanković J, Gođevac D, Tešević V, Dajić-Stevanović Z, Ćirić AD, Soković M, Novaković MM. Supplementary data for the article: Stanković, J.; Godevac, D.; Tešević, V.; Dajić-Stevanović, Z.; Ćirić, A.; Soković, M.; Novaković, M. Antibacterial and Antibiofilm Activity of Flavonoid and Saponin Derivatives from Atriplex Tatarica against Pseudomonas Aeruginosa. Journal of Natural Products 2019, 82 (6), 1487–1495. https://doi.org/10.1021/acs.jnatprod.8b00970. in Journal of Natural Products. 2019;.
https://hdl.handle.net/21.15107/rcub_cherry_3726 .
Stanković, Jovana, Gođevac, Dejan, Tešević, Vele, Dajić-Stevanović, Zora, Ćirić, Ana D., Soković, Marina, Novaković, Miroslav M., "Supplementary data for the article: Stanković, J.; Godevac, D.; Tešević, V.; Dajić-Stevanović, Z.; Ćirić, A.; Soković, M.; Novaković, M. Antibacterial and Antibiofilm Activity of Flavonoid and Saponin Derivatives from Atriplex Tatarica against Pseudomonas Aeruginosa. Journal of Natural Products 2019, 82 (6), 1487–1495. https://doi.org/10.1021/acs.jnatprod.8b00970" in Journal of Natural Products (2019),
https://hdl.handle.net/21.15107/rcub_cherry_3726 .

Lipid composition and DPPH activities of the seed oil of five Turkish hazelnut genotypes (Corylus colurna L.)

Ninić-Todorović, Jelena; Novaković, Miroslav M.; Čukanović, Jelena; Sofrenić, Ivana V.; Todorović, Ivan; Todorović, Dragan; Tešević, Vele

(2019)

TY  - JOUR
AU  - Ninić-Todorović, Jelena
AU  - Novaković, Miroslav M.
AU  - Čukanović, Jelena
AU  - Sofrenić, Ivana V.
AU  - Todorović, Ivan
AU  - Todorović, Dragan
AU  - Tešević, Vele
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3929
AB  - Five genotypes of Turkish hazelnuts (Corylus colurna L.) were analyzed for chemical composition, including total oil content, fatty acid and sterol composition. The oil yields from these kernels varied from 36.5% to 60.8% and the main fatty acids were oleic acid (79.34-83.0%) and linoleic acid (7.52-10.81%). The polyunsaturated/saturated fatty acid ratio was low, ranging from 0.87 to 1.25. To-tal phytosterol content ranged from 4.52 to 6.50 mg g -1 of oil. Among the eleven sterols identified and quantified, b-sitosterol was the major one with a mean percentage of 65.09% while fucosterol and campesterol were the second and the third components of the group with mean values of 10.91% and 4.36%, respectively. The radical scavenging activity was evaluated using 2.2-diphenyl-1 picrylhy-drazyl (DPPH) assay.
T2  - Lekovite sirovine
T1  - Lipid composition and DPPH activities of the seed oil of five Turkish hazelnut genotypes (Corylus colurna L.)
IS  - 39
SP  - 18
EP  - 22
DO  - 10.5937/leksir1939018N
ER  - 
@article{
author = "Ninić-Todorović, Jelena and Novaković, Miroslav M. and Čukanović, Jelena and Sofrenić, Ivana V. and Todorović, Ivan and Todorović, Dragan and Tešević, Vele",
year = "2019",
abstract = "Five genotypes of Turkish hazelnuts (Corylus colurna L.) were analyzed for chemical composition, including total oil content, fatty acid and sterol composition. The oil yields from these kernels varied from 36.5% to 60.8% and the main fatty acids were oleic acid (79.34-83.0%) and linoleic acid (7.52-10.81%). The polyunsaturated/saturated fatty acid ratio was low, ranging from 0.87 to 1.25. To-tal phytosterol content ranged from 4.52 to 6.50 mg g -1 of oil. Among the eleven sterols identified and quantified, b-sitosterol was the major one with a mean percentage of 65.09% while fucosterol and campesterol were the second and the third components of the group with mean values of 10.91% and 4.36%, respectively. The radical scavenging activity was evaluated using 2.2-diphenyl-1 picrylhy-drazyl (DPPH) assay.",
journal = "Lekovite sirovine",
title = "Lipid composition and DPPH activities of the seed oil of five Turkish hazelnut genotypes (Corylus colurna L.)",
number = "39",
pages = "18-22",
doi = "10.5937/leksir1939018N"
}
Ninić-Todorović, J., Novaković, M. M., Čukanović, J., Sofrenić, I. V., Todorović, I., Todorović, D.,& Tešević, V.. (2019). Lipid composition and DPPH activities of the seed oil of five Turkish hazelnut genotypes (Corylus colurna L.). in Lekovite sirovine(39), 18-22.
https://doi.org/10.5937/leksir1939018N
Ninić-Todorović J, Novaković MM, Čukanović J, Sofrenić IV, Todorović I, Todorović D, Tešević V. Lipid composition and DPPH activities of the seed oil of five Turkish hazelnut genotypes (Corylus colurna L.). in Lekovite sirovine. 2019;(39):18-22.
doi:10.5937/leksir1939018N .
Ninić-Todorović, Jelena, Novaković, Miroslav M., Čukanović, Jelena, Sofrenić, Ivana V., Todorović, Ivan, Todorović, Dragan, Tešević, Vele, "Lipid composition and DPPH activities of the seed oil of five Turkish hazelnut genotypes (Corylus colurna L.)" in Lekovite sirovine, no. 39 (2019):18-22,
https://doi.org/10.5937/leksir1939018N . .

Microbial Transformation of Calamintha glandulosa Essential Oil by Aspergillus niger

Novaković, Miroslav M.; Bukvicki, Danka; Vajs, Vlatka; Tešević, Vele; Milosavljević, Slobodan M.; Marin, Petar D.; Asakawa, Yoshinori

(Natural Products Inc, Westerville, 2018)

TY  - JOUR
AU  - Novaković, Miroslav M.
AU  - Bukvicki, Danka
AU  - Vajs, Vlatka
AU  - Tešević, Vele
AU  - Milosavljević, Slobodan M.
AU  - Marin, Petar D.
AU  - Asakawa, Yoshinori
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2150
AB  - A number of potentially useful compounds with various biological activities can be obtained from plant metabolites by microorganisms. In present research, essential oil of Calamintha glandulosa was subjected to the biotransformation process by mycromicete Aspergillus niger. GC/MS analyses of the original and biotransformed essential oil have revealed six(1-6) biotransformed compounds from one of the main component-limonene and one biotransformed product (7) originating from the less abundant component-thymol. Piperitone epoxide and piperitenone epoxide, the most abundant components of the original oil, were not biotransformed but gave three artefacts (A1, A2, B1) due to the acidic conditions formed in A. niger medium. Compounds 5, 6 as well as 7 have not been previously found as a biotransformation products of limonene (5 and 6) and thymol (7), respectively. New products (5, 6, and 7) together with the artefacts, were isolated by silica gel column chromatography followed by preparative silica gel thin layer chromatography, and their structures were established by a combination of 1D and 2D NMR spectra and GC/MS data. Biotransformation has one more confirmed as useful method, complementary to synthesis, for obtaining different type of molecules.
PB  - Natural Products Inc, Westerville
T2  - Natural Product Communications
T1  - Microbial Transformation of Calamintha glandulosa Essential Oil by Aspergillus niger
VL  - 13
IS  - 4
SP  - 479
EP  - 482
UR  - https://hdl.handle.net/21.15107/rcub_cherry_2150
ER  - 
@article{
author = "Novaković, Miroslav M. and Bukvicki, Danka and Vajs, Vlatka and Tešević, Vele and Milosavljević, Slobodan M. and Marin, Petar D. and Asakawa, Yoshinori",
year = "2018",
abstract = "A number of potentially useful compounds with various biological activities can be obtained from plant metabolites by microorganisms. In present research, essential oil of Calamintha glandulosa was subjected to the biotransformation process by mycromicete Aspergillus niger. GC/MS analyses of the original and biotransformed essential oil have revealed six(1-6) biotransformed compounds from one of the main component-limonene and one biotransformed product (7) originating from the less abundant component-thymol. Piperitone epoxide and piperitenone epoxide, the most abundant components of the original oil, were not biotransformed but gave three artefacts (A1, A2, B1) due to the acidic conditions formed in A. niger medium. Compounds 5, 6 as well as 7 have not been previously found as a biotransformation products of limonene (5 and 6) and thymol (7), respectively. New products (5, 6, and 7) together with the artefacts, were isolated by silica gel column chromatography followed by preparative silica gel thin layer chromatography, and their structures were established by a combination of 1D and 2D NMR spectra and GC/MS data. Biotransformation has one more confirmed as useful method, complementary to synthesis, for obtaining different type of molecules.",
publisher = "Natural Products Inc, Westerville",
journal = "Natural Product Communications",
title = "Microbial Transformation of Calamintha glandulosa Essential Oil by Aspergillus niger",
volume = "13",
number = "4",
pages = "479-482",
url = "https://hdl.handle.net/21.15107/rcub_cherry_2150"
}
Novaković, M. M., Bukvicki, D., Vajs, V., Tešević, V., Milosavljević, S. M., Marin, P. D.,& Asakawa, Y.. (2018). Microbial Transformation of Calamintha glandulosa Essential Oil by Aspergillus niger. in Natural Product Communications
Natural Products Inc, Westerville., 13(4), 479-482.
https://hdl.handle.net/21.15107/rcub_cherry_2150
Novaković MM, Bukvicki D, Vajs V, Tešević V, Milosavljević SM, Marin PD, Asakawa Y. Microbial Transformation of Calamintha glandulosa Essential Oil by Aspergillus niger. in Natural Product Communications. 2018;13(4):479-482.
https://hdl.handle.net/21.15107/rcub_cherry_2150 .
Novaković, Miroslav M., Bukvicki, Danka, Vajs, Vlatka, Tešević, Vele, Milosavljević, Slobodan M., Marin, Petar D., Asakawa, Yoshinori, "Microbial Transformation of Calamintha glandulosa Essential Oil by Aspergillus niger" in Natural Product Communications, 13, no. 4 (2018):479-482,
https://hdl.handle.net/21.15107/rcub_cherry_2150 .
2
2

Wild Thymus capitatus Hoff. Et Link. Chemical Composition, Antioxidant and Antimicrobial Activities of the Essential Oil

Marin, Marija; Novaković, Miroslav M.; Vučković, Ivan M.; Tešević, Vele; Kolarević, Stoimir; Vuković-Gačić, Branka

(Taylor & Francis Ltd, Abingdon, 2018)

TY  - JOUR
AU  - Marin, Marija
AU  - Novaković, Miroslav M.
AU  - Vučković, Ivan M.
AU  - Tešević, Vele
AU  - Kolarević, Stoimir
AU  - Vuković-Gačić, Branka
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2143
AB  - The composition of the essential oil (EO) obtained by hydrodistillation from the leaves of Thymus capitatus Hoff. et Link. growing wild in Sythonia (Greece) was analysed by GC-FID, GC-MS and quantitative H-1 NMR spectroscopy. Thirty nine compounds were identified, representing approximately 99.0 % of the oil. Major component determined by GC-FID was carvacrol (81.8 %), followed by linalool (3.5 %) and (E)-caryophyllenc (3.5 %). Abundance of carvacrol determined by quantitative H-1 NMR spectroscopy was 74.9 % and was in reasonable agreement with GC-FID result. The oil was tested for the antioxidant activity in DPPH assay and showed a dose dependent free radical scavenging activity with EC50 value of 1.03 mu g/ml. Antimicrobial effect of the EO was tested against Gram negative, Gram positive bacteria, and fungi. The tested EO showed significant activity against fungi, especially S. cerevisiae. The most sensitive bacteria were E. coil ATCC 25922, E. fecalis and S. epidermidis. Human pathogen Burkholderia cepacia, ATCC 25416 was used in the investigation of T capitatus for the fast time.
PB  - Taylor & Francis Ltd, Abingdon
T2  - Journal of Essential Oil Bearing Plants
T1  - Wild Thymus capitatus Hoff. Et Link. Chemical Composition, Antioxidant and Antimicrobial Activities of the Essential Oil
VL  - 21
IS  - 2
SP  - 388
EP  - 399
DO  - 10.1080/0972060X.2018.1449668
ER  - 
@article{
author = "Marin, Marija and Novaković, Miroslav M. and Vučković, Ivan M. and Tešević, Vele and Kolarević, Stoimir and Vuković-Gačić, Branka",
year = "2018",
abstract = "The composition of the essential oil (EO) obtained by hydrodistillation from the leaves of Thymus capitatus Hoff. et Link. growing wild in Sythonia (Greece) was analysed by GC-FID, GC-MS and quantitative H-1 NMR spectroscopy. Thirty nine compounds were identified, representing approximately 99.0 % of the oil. Major component determined by GC-FID was carvacrol (81.8 %), followed by linalool (3.5 %) and (E)-caryophyllenc (3.5 %). Abundance of carvacrol determined by quantitative H-1 NMR spectroscopy was 74.9 % and was in reasonable agreement with GC-FID result. The oil was tested for the antioxidant activity in DPPH assay and showed a dose dependent free radical scavenging activity with EC50 value of 1.03 mu g/ml. Antimicrobial effect of the EO was tested against Gram negative, Gram positive bacteria, and fungi. The tested EO showed significant activity against fungi, especially S. cerevisiae. The most sensitive bacteria were E. coil ATCC 25922, E. fecalis and S. epidermidis. Human pathogen Burkholderia cepacia, ATCC 25416 was used in the investigation of T capitatus for the fast time.",
publisher = "Taylor & Francis Ltd, Abingdon",
journal = "Journal of Essential Oil Bearing Plants",
title = "Wild Thymus capitatus Hoff. Et Link. Chemical Composition, Antioxidant and Antimicrobial Activities of the Essential Oil",
volume = "21",
number = "2",
pages = "388-399",
doi = "10.1080/0972060X.2018.1449668"
}
Marin, M., Novaković, M. M., Vučković, I. M., Tešević, V., Kolarević, S.,& Vuković-Gačić, B.. (2018). Wild Thymus capitatus Hoff. Et Link. Chemical Composition, Antioxidant and Antimicrobial Activities of the Essential Oil. in Journal of Essential Oil Bearing Plants
Taylor & Francis Ltd, Abingdon., 21(2), 388-399.
https://doi.org/10.1080/0972060X.2018.1449668
Marin M, Novaković MM, Vučković IM, Tešević V, Kolarević S, Vuković-Gačić B. Wild Thymus capitatus Hoff. Et Link. Chemical Composition, Antioxidant and Antimicrobial Activities of the Essential Oil. in Journal of Essential Oil Bearing Plants. 2018;21(2):388-399.
doi:10.1080/0972060X.2018.1449668 .
Marin, Marija, Novaković, Miroslav M., Vučković, Ivan M., Tešević, Vele, Kolarević, Stoimir, Vuković-Gačić, Branka, "Wild Thymus capitatus Hoff. Et Link. Chemical Composition, Antioxidant and Antimicrobial Activities of the Essential Oil" in Journal of Essential Oil Bearing Plants, 21, no. 2 (2018):388-399,
https://doi.org/10.1080/0972060X.2018.1449668 . .
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Multielement analysis and antioxidant capacity of Merlot wine clones developed in Montenegro

Đorđević, Neda O.; Pejin, Boris; Novaković, Miroslav M.; Stanković, Dalibor; Mutić, Jelena; Pajović, Snezana B.; Tešević, Vele

(Taylor & Francis Ltd, Abingdon, 2018)

TY  - JOUR
AU  - Đorđević, Neda O.
AU  - Pejin, Boris
AU  - Novaković, Miroslav M.
AU  - Stanković, Dalibor
AU  - Mutić, Jelena
AU  - Pajović, Snezana B.
AU  - Tešević, Vele
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2563
AB  - The overall aim of this paper was to compare the multielement composition and antioxidant capacity of two Montenegrin Merlot wines obtained from specific vine clones (VCR1 and VCR 101) along with commercial Merlot wine throughout the consecutive vintages in 2010 and 2011. Elemental composition was analysed using inductively coupled plasma optical emission spectrometry (ICP-OES) and inductively coupled plasma mass spectrometry (ICP-MS). Additionally, antioxidant capacity was assessed by cyclic voltammetry. VCR 1 wine from 2011 stood out for its elemental composition. On the other hand, antioxidant capacity of VCR 101 wines was the highest one for the both vintages. According to the experimental data obtained, all three wines are good source of essential elements and products with a significant antioxidant activity and specific geographical origin.
PB  - Taylor & Francis Ltd, Abingdon
T2  - Natural Product Research
T1  - Multielement analysis and antioxidant capacity of Merlot wine clones developed in Montenegro
VL  - 32
IS  - 3
SP  - 247
EP  - 251
DO  - 10.1080/14786419.2017.1347171
ER  - 
@article{
author = "Đorđević, Neda O. and Pejin, Boris and Novaković, Miroslav M. and Stanković, Dalibor and Mutić, Jelena and Pajović, Snezana B. and Tešević, Vele",
year = "2018",
abstract = "The overall aim of this paper was to compare the multielement composition and antioxidant capacity of two Montenegrin Merlot wines obtained from specific vine clones (VCR1 and VCR 101) along with commercial Merlot wine throughout the consecutive vintages in 2010 and 2011. Elemental composition was analysed using inductively coupled plasma optical emission spectrometry (ICP-OES) and inductively coupled plasma mass spectrometry (ICP-MS). Additionally, antioxidant capacity was assessed by cyclic voltammetry. VCR 1 wine from 2011 stood out for its elemental composition. On the other hand, antioxidant capacity of VCR 101 wines was the highest one for the both vintages. According to the experimental data obtained, all three wines are good source of essential elements and products with a significant antioxidant activity and specific geographical origin.",
publisher = "Taylor & Francis Ltd, Abingdon",
journal = "Natural Product Research",
title = "Multielement analysis and antioxidant capacity of Merlot wine clones developed in Montenegro",
volume = "32",
number = "3",
pages = "247-251",
doi = "10.1080/14786419.2017.1347171"
}
Đorđević, N. O., Pejin, B., Novaković, M. M., Stanković, D., Mutić, J., Pajović, S. B.,& Tešević, V.. (2018). Multielement analysis and antioxidant capacity of Merlot wine clones developed in Montenegro. in Natural Product Research
Taylor & Francis Ltd, Abingdon., 32(3), 247-251.
https://doi.org/10.1080/14786419.2017.1347171
Đorđević NO, Pejin B, Novaković MM, Stanković D, Mutić J, Pajović SB, Tešević V. Multielement analysis and antioxidant capacity of Merlot wine clones developed in Montenegro. in Natural Product Research. 2018;32(3):247-251.
doi:10.1080/14786419.2017.1347171 .
Đorđević, Neda O., Pejin, Boris, Novaković, Miroslav M., Stanković, Dalibor, Mutić, Jelena, Pajović, Snezana B., Tešević, Vele, "Multielement analysis and antioxidant capacity of Merlot wine clones developed in Montenegro" in Natural Product Research, 32, no. 3 (2018):247-251,
https://doi.org/10.1080/14786419.2017.1347171 . .
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Significance of diarylheptanoids for chemotaxonomical distinguishing between Alnus glutinosa and Alnus incana

Vidaković, Vera; Novaković, Miroslav M.; Popović, Zorica; Janković, Milan; Matić, Rada; Tešević, Vele; Bojović, Srđan R.

(Walter De Gruyter Gmbh, Berlin, 2018)

TY  - JOUR
AU  - Vidaković, Vera
AU  - Novaković, Miroslav M.
AU  - Popović, Zorica
AU  - Janković, Milan
AU  - Matić, Rada
AU  - Tešević, Vele
AU  - Bojović, Srđan R.
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2574
AB  - Diarylheptanoids are a group of secondary metabolites widely distributed in the Betulaceae family and characteristic for Alnus species. In this study, the chemotaxonomic power of diarylheptanoids, such as hirsutanonol-5-O-beta-d-glucopyranoside, rubranoside A, oregonin, platyphylloside, alnuside A and hirsutanonol, has been investigated in combination with principal component analysis (PCA) for differentiation of Alnus species. Concentrations of six diarylheptanoids in the bark extracts of two natural populations of Alnus glutinosa (black alder) and Alnus incana (gray alder) were determined by -ultraperformance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS). PCA clearly shows the separation of three groups. Populations I (A. glutinosa) and II (A. incana) both consisted of individuals of the corresponding species. Four individuals from both sampled populations formed a separate group (population III), which possibly represents a hybrid group. Accordingly, diarylheptanoids may serve in combination with PCA as chemotaxonomic markers at the species level, which may also reveal hybrid species.
PB  - Walter De Gruyter Gmbh, Berlin
T2  - Holzforschung
T1  - Significance of diarylheptanoids for chemotaxonomical distinguishing between Alnus glutinosa and Alnus incana
VL  - 72
IS  - 1
SP  - 9
EP  - 16
DO  - 10.1515/hf-2017-0074
ER  - 
@article{
author = "Vidaković, Vera and Novaković, Miroslav M. and Popović, Zorica and Janković, Milan and Matić, Rada and Tešević, Vele and Bojović, Srđan R.",
year = "2018",
abstract = "Diarylheptanoids are a group of secondary metabolites widely distributed in the Betulaceae family and characteristic for Alnus species. In this study, the chemotaxonomic power of diarylheptanoids, such as hirsutanonol-5-O-beta-d-glucopyranoside, rubranoside A, oregonin, platyphylloside, alnuside A and hirsutanonol, has been investigated in combination with principal component analysis (PCA) for differentiation of Alnus species. Concentrations of six diarylheptanoids in the bark extracts of two natural populations of Alnus glutinosa (black alder) and Alnus incana (gray alder) were determined by -ultraperformance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS). PCA clearly shows the separation of three groups. Populations I (A. glutinosa) and II (A. incana) both consisted of individuals of the corresponding species. Four individuals from both sampled populations formed a separate group (population III), which possibly represents a hybrid group. Accordingly, diarylheptanoids may serve in combination with PCA as chemotaxonomic markers at the species level, which may also reveal hybrid species.",
publisher = "Walter De Gruyter Gmbh, Berlin",
journal = "Holzforschung",
title = "Significance of diarylheptanoids for chemotaxonomical distinguishing between Alnus glutinosa and Alnus incana",
volume = "72",
number = "1",
pages = "9-16",
doi = "10.1515/hf-2017-0074"
}
Vidaković, V., Novaković, M. M., Popović, Z., Janković, M., Matić, R., Tešević, V.,& Bojović, S. R.. (2018). Significance of diarylheptanoids for chemotaxonomical distinguishing between Alnus glutinosa and Alnus incana. in Holzforschung
Walter De Gruyter Gmbh, Berlin., 72(1), 9-16.
https://doi.org/10.1515/hf-2017-0074
Vidaković V, Novaković MM, Popović Z, Janković M, Matić R, Tešević V, Bojović SR. Significance of diarylheptanoids for chemotaxonomical distinguishing between Alnus glutinosa and Alnus incana. in Holzforschung. 2018;72(1):9-16.
doi:10.1515/hf-2017-0074 .
Vidaković, Vera, Novaković, Miroslav M., Popović, Zorica, Janković, Milan, Matić, Rada, Tešević, Vele, Bojović, Srđan R., "Significance of diarylheptanoids for chemotaxonomical distinguishing between Alnus glutinosa and Alnus incana" in Holzforschung, 72, no. 1 (2018):9-16,
https://doi.org/10.1515/hf-2017-0074 . .
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Effects of soil properties and fertilization on quality and biological activity of Swiss chard

Topalović, Ana; Knežević, Mirko; Trifunović, Snežana S.; Novaković, Miroslav M.; Pešić, Milica; Ðurović, Dijana

(International Society for Horticultural Science, 2018)

TY  - JOUR
AU  - Topalović, Ana
AU  - Knežević, Mirko
AU  - Trifunović, Snežana S.
AU  - Novaković, Miroslav M.
AU  - Pešić, Milica
AU  - Ðurović, Dijana
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2886
AB  - Swiss chard (Beta vulgaris L. var. cicla) is a leafy vegetable highly consumed in many parts of the world as a very popular ingredient of different diets. The purpose of this study was to evaluate effects of soil properties and fertilization on yield, mineral composition, total phenolics, antioxidant and biological activity of Swiss chard. The mineral composition of Swiss chard was generally affected by soil properties. The fertilization at 50% of recommended level (110 kg ha -1 N, 90 kg ha -1 P 2 O 5 and 100 kg ha -1 K 2 O per season) affected negatively yield and on the other hand affected positively antioxidant activity, while fertilization at 150% of recommended level had a contrary effect. The available K in soil affected the yield positively. Total phenolics were in negative correlation with the yield. The positive relationship of total phenolics and content of Mn in chard was noticed. The greatest efficacy in human colorectal carcinoma cell lines was obtained by Swiss chard extract from plants fertilized at 150% of recommended level.
PB  - International Society for Horticultural Science
T2  - European Journal of Horticultural Science
T1  - Effects of soil properties and fertilization on quality and biological activity of Swiss chard
VL  - 83
IS  - 6
SP  - 374
EP  - 381
DO  - 10.17660/eJHS.2018/83.6.5
ER  - 
@article{
author = "Topalović, Ana and Knežević, Mirko and Trifunović, Snežana S. and Novaković, Miroslav M. and Pešić, Milica and Ðurović, Dijana",
year = "2018",
abstract = "Swiss chard (Beta vulgaris L. var. cicla) is a leafy vegetable highly consumed in many parts of the world as a very popular ingredient of different diets. The purpose of this study was to evaluate effects of soil properties and fertilization on yield, mineral composition, total phenolics, antioxidant and biological activity of Swiss chard. The mineral composition of Swiss chard was generally affected by soil properties. The fertilization at 50% of recommended level (110 kg ha -1 N, 90 kg ha -1 P 2 O 5 and 100 kg ha -1 K 2 O per season) affected negatively yield and on the other hand affected positively antioxidant activity, while fertilization at 150% of recommended level had a contrary effect. The available K in soil affected the yield positively. Total phenolics were in negative correlation with the yield. The positive relationship of total phenolics and content of Mn in chard was noticed. The greatest efficacy in human colorectal carcinoma cell lines was obtained by Swiss chard extract from plants fertilized at 150% of recommended level.",
publisher = "International Society for Horticultural Science",
journal = "European Journal of Horticultural Science",
title = "Effects of soil properties and fertilization on quality and biological activity of Swiss chard",
volume = "83",
number = "6",
pages = "374-381",
doi = "10.17660/eJHS.2018/83.6.5"
}
Topalović, A., Knežević, M., Trifunović, S. S., Novaković, M. M., Pešić, M.,& Ðurović, D.. (2018). Effects of soil properties and fertilization on quality and biological activity of Swiss chard. in European Journal of Horticultural Science
International Society for Horticultural Science., 83(6), 374-381.
https://doi.org/10.17660/eJHS.2018/83.6.5
Topalović A, Knežević M, Trifunović SS, Novaković MM, Pešić M, Ðurović D. Effects of soil properties and fertilization on quality and biological activity of Swiss chard. in European Journal of Horticultural Science. 2018;83(6):374-381.
doi:10.17660/eJHS.2018/83.6.5 .
Topalović, Ana, Knežević, Mirko, Trifunović, Snežana S., Novaković, Miroslav M., Pešić, Milica, Ðurović, Dijana, "Effects of soil properties and fertilization on quality and biological activity of Swiss chard" in European Journal of Horticultural Science, 83, no. 6 (2018):374-381,
https://doi.org/10.17660/eJHS.2018/83.6.5 . .
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