Novaković, Miroslav

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Authority KeyName Variants
orcid::0000-0002-4984-041X
  • Novaković, Miroslav (101)
Projects
Natural products of wild, cultivated and edible plants: structure and bioactivity determination 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
Microbial diversity study and characterization of beneficial environmental microorganisms Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200178 (University of Belgrade, Faculty of Biology)
Matsumae International Foundation Identification of predictive molecular markers for cancer progression, response to therapy and disease outcome
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 The synthesis of aminoquinoline-based antimalarials and botulinum neurotoxin A inhibitors
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')
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 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
Characterization and application of fungal metabolites and assessment of new biofungicides potential 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 Regulacija antioksidativnog metabolizma biljaka u toku rastenja, infekcije patogenima i delovanja abiotičkog stresa: mehanizmi transporta, signalizacije i otpornosti
Evaluation of ecophysiological and genetic plant diversity in forest ecosystems Modulation of intracellular energy balance-controlling signalling pathways in therapy of cancer and neuro-immuno-endocrine disorders
Simultaneous Bioremediation and Soilification of Degraded Areas to Preserve Natural Resources of Biologically Active Substances, and Development and Production of Biomaterials and Dietetic Products Traditional and new products of cultivated and wild growing fruits and grape vines, and by-products durring processing, with special emphasis on indigenous varieties: chemical characterization and biological profile
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
Phytobiotechnology Research Foundation of Cameroon “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 Department of Chemistry, University of Houston, 112 Fleming Building, Houston TX 77204- 5003, USA

Author's Bibliography

Analysis of terpenoids from the latex of Euphorbia cyparissias by liquid chromatography-electrospray ionization mass spectrometry

Jadranin, Milka; Krstić, Gordana; Savić, Danica; Novaković, Miroslav; Lekić, Stefan; Tešević, Vele; Pešić, Milica; Podolski-Renić, Ana; Lupšić, Ema; Milosavljević, Slobodan

(International Conference on Natural Products Utilization - ICNPU2023, 2023)

TY  - CONF
AU  - Jadranin, Milka
AU  - Krstić, Gordana
AU  - Savić, Danica
AU  - Novaković, Miroslav
AU  - Lekić, Stefan
AU  - Tešević, Vele
AU  - Pešić, Milica
AU  - Podolski-Renić, Ana
AU  - Lupšić, Ema
AU  - Milosavljević, Slobodan
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7270
AB  - Euphorbia cyparissias L. (cypress spurge) is one of the many species of the genus Euphorbia. Like other plant species of the genus, E. cyparissias is a source of biologically active compounds [1, 2]. The aim of this research was to profile the chloroform-methanol latex extract and detect the type of secondary metabolites of Serbian E. cyparissias, collected in Deliblato Sand 
(Serbia) in May 2022, using liquid chromatography – electrospray ionisation mass spectrometry. Based on the obtained results, terpene derivatives have been found as the most abundant in the latex extract, mainly diterpenes (jatrophanes and ingenanes) and triterpenes. Also, the anticancer activ ity of the latex extract on the cell lines NCI-H460, NCI-H460/R, U87, U87/
TxR and MRC-5, as well as the ability to inhibit P-gp, were examined. Latex extract exhibited anticancer activity against all tested cell lines, and also 
proved to be a strong P-gp inhibitor. The obtained results are in accordance with the literature data because jatrophanes are well-known strong P-gp 
inhibitors [3]. These preliminary results indicate that this plant material is a rich source of biologically active compounds and detailed phytochemical research of E. cyparissias is further planned.
PB  - International Conference on Natural Products Utilization - ICNPU2023
C3  - Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria
T1  - Analysis of terpenoids from the latex of Euphorbia cyparissias by liquid chromatography-electrospray ionization mass spectrometry
SP  - 184
EP  - 185
UR  - https://hdl.handle.net/21.15107/rcub_cer_7270
ER  - 
@conference{
author = "Jadranin, Milka and Krstić, Gordana and Savić, Danica and Novaković, Miroslav and Lekić, Stefan and Tešević, Vele and Pešić, Milica and Podolski-Renić, Ana and Lupšić, Ema and Milosavljević, Slobodan",
year = "2023",
abstract = "Euphorbia cyparissias L. (cypress spurge) is one of the many species of the genus Euphorbia. Like other plant species of the genus, E. cyparissias is a source of biologically active compounds [1, 2]. The aim of this research was to profile the chloroform-methanol latex extract and detect the type of secondary metabolites of Serbian E. cyparissias, collected in Deliblato Sand 
(Serbia) in May 2022, using liquid chromatography – electrospray ionisation mass spectrometry. Based on the obtained results, terpene derivatives have been found as the most abundant in the latex extract, mainly diterpenes (jatrophanes and ingenanes) and triterpenes. Also, the anticancer activ ity of the latex extract on the cell lines NCI-H460, NCI-H460/R, U87, U87/
TxR and MRC-5, as well as the ability to inhibit P-gp, were examined. Latex extract exhibited anticancer activity against all tested cell lines, and also 
proved to be a strong P-gp inhibitor. The obtained results are in accordance with the literature data because jatrophanes are well-known strong P-gp 
inhibitors [3]. These preliminary results indicate that this plant material is a rich source of biologically active compounds and detailed phytochemical research of E. cyparissias is further planned.",
publisher = "International Conference on Natural Products Utilization - ICNPU2023",
journal = "Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria",
title = "Analysis of terpenoids from the latex of Euphorbia cyparissias by liquid chromatography-electrospray ionization mass spectrometry",
pages = "184-185",
url = "https://hdl.handle.net/21.15107/rcub_cer_7270"
}
Jadranin, M., Krstić, G., Savić, D., Novaković, M., Lekić, S., Tešević, V., Pešić, M., Podolski-Renić, A., Lupšić, E.,& Milosavljević, S.. (2023). Analysis of terpenoids from the latex of Euphorbia cyparissias by liquid chromatography-electrospray ionization mass spectrometry. in Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria
International Conference on Natural Products Utilization - ICNPU2023., 184-185.
https://hdl.handle.net/21.15107/rcub_cer_7270
Jadranin M, Krstić G, Savić D, Novaković M, Lekić S, Tešević V, Pešić M, Podolski-Renić A, Lupšić E, Milosavljević S. Analysis of terpenoids from the latex of Euphorbia cyparissias by liquid chromatography-electrospray ionization mass spectrometry. in Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria. 2023;:184-185.
https://hdl.handle.net/21.15107/rcub_cer_7270 .
Jadranin, Milka, Krstić, Gordana, Savić, Danica, Novaković, Miroslav, Lekić, Stefan, Tešević, Vele, Pešić, Milica, Podolski-Renić, Ana, Lupšić, Ema, Milosavljević, Slobodan, "Analysis of terpenoids from the latex of Euphorbia cyparissias by liquid chromatography-electrospray ionization mass spectrometry" in Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria (2023):184-185,
https://hdl.handle.net/21.15107/rcub_cer_7270 .

LC-HRESI-MS Technique as the best choice for rapid screening of secondary metabolites of Euphorbia palustris latex extract

Krstić, Gordana; Jadranin, Milka; Savić, Danica; Novaković, Miroslav; Lekić, Stefan; Tešević, Vele; Milosavljević, Slobodan

(International Conference on Natural Products Utilization - ICNPU2023, 2023)

TY  - CONF
AU  - Krstić, Gordana
AU  - Jadranin, Milka
AU  - Savić, Danica
AU  - Novaković, Miroslav
AU  - Lekić, Stefan
AU  - Tešević, Vele
AU  - Milosavljević, Slobodan
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7268
AB  - The genus Euphorbia represents one of the largest and most diverse plant genera. Plant species of this genera are a rich source of biologically active compounds. Our previous investigation of E. palustris L. revealed an excellent anti-melanoma activity of 3β-benzoyloxy-13α-dodecanoyloxy-ingenol (1), and 3β,13α,17-tribenzoyloxy-ingenol (2), significantly better than ingenol-mebutate (Picato®), a commercial anti-melanoma agent approved by the U.S. Food and Drug Administration (FDA) and by the European Medicines Agency (EMA) for the topical treatment of actinic keratosis [1]. Hence, in this research, using liquid chromatography–electrospray ionization mass spectrometry, chloroform-methanolic extracts of two samples of E. palustris collected at different localities in Serbia were analysed in order to confirm the presence of 1.Based on the tentative analysis of the LC-HRESI-MS and the previous examination of this plant species, ingenanes 1 and 2 were confirmed in both extracts examined. Additionally, both extracts contained several metabolites that structurally corresponds to ingenol, with a decanoyl group in their structure. Based on these preliminary results, our goal in further investigation is to isolate other ingenane molecules and test their anti-melanoma activity.
PB  - International Conference on Natural Products Utilization - ICNPU2023
C3  - Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria
T1  - LC-HRESI-MS Technique as the best choice for rapid screening of secondary metabolites of Euphorbia palustris latex extract
SP  - 43
EP  - 44
UR  - https://hdl.handle.net/21.15107/rcub_cer_7268
ER  - 
@conference{
author = "Krstić, Gordana and Jadranin, Milka and Savić, Danica and Novaković, Miroslav and Lekić, Stefan and Tešević, Vele and Milosavljević, Slobodan",
year = "2023",
abstract = "The genus Euphorbia represents one of the largest and most diverse plant genera. Plant species of this genera are a rich source of biologically active compounds. Our previous investigation of E. palustris L. revealed an excellent anti-melanoma activity of 3β-benzoyloxy-13α-dodecanoyloxy-ingenol (1), and 3β,13α,17-tribenzoyloxy-ingenol (2), significantly better than ingenol-mebutate (Picato®), a commercial anti-melanoma agent approved by the U.S. Food and Drug Administration (FDA) and by the European Medicines Agency (EMA) for the topical treatment of actinic keratosis [1]. Hence, in this research, using liquid chromatography–electrospray ionization mass spectrometry, chloroform-methanolic extracts of two samples of E. palustris collected at different localities in Serbia were analysed in order to confirm the presence of 1.Based on the tentative analysis of the LC-HRESI-MS and the previous examination of this plant species, ingenanes 1 and 2 were confirmed in both extracts examined. Additionally, both extracts contained several metabolites that structurally corresponds to ingenol, with a decanoyl group in their structure. Based on these preliminary results, our goal in further investigation is to isolate other ingenane molecules and test their anti-melanoma activity.",
publisher = "International Conference on Natural Products Utilization - ICNPU2023",
journal = "Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria",
title = "LC-HRESI-MS Technique as the best choice for rapid screening of secondary metabolites of Euphorbia palustris latex extract",
pages = "43-44",
url = "https://hdl.handle.net/21.15107/rcub_cer_7268"
}
Krstić, G., Jadranin, M., Savić, D., Novaković, M., Lekić, S., Tešević, V.,& Milosavljević, S.. (2023). LC-HRESI-MS Technique as the best choice for rapid screening of secondary metabolites of Euphorbia palustris latex extract. in Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria
International Conference on Natural Products Utilization - ICNPU2023., 43-44.
https://hdl.handle.net/21.15107/rcub_cer_7268
Krstić G, Jadranin M, Savić D, Novaković M, Lekić S, Tešević V, Milosavljević S. LC-HRESI-MS Technique as the best choice for rapid screening of secondary metabolites of Euphorbia palustris latex extract. in Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria. 2023;:43-44.
https://hdl.handle.net/21.15107/rcub_cer_7268 .
Krstić, Gordana, Jadranin, Milka, Savić, Danica, Novaković, Miroslav, Lekić, Stefan, Tešević, Vele, Milosavljević, Slobodan, "LC-HRESI-MS Technique as the best choice for rapid screening of secondary metabolites of Euphorbia palustris latex extract" in Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria (2023):43-44,
https://hdl.handle.net/21.15107/rcub_cer_7268 .

Bisbibenzyls in Primula species

Novaković, Miroslav; Jadranin, Milka; Lekić, Stefan; Savić, Danica; Krstić, Gordana; Tešević, Vele; Milosavljević, Slobodan

(International Conference on Natural Products Utilization - ICNPU2023, 2023)

TY  - CONF
AU  - Novaković, Miroslav
AU  - Jadranin, Milka
AU  - Lekić, Stefan
AU  - Savić, Danica
AU  - Krstić, Gordana
AU  - Tešević, Vele
AU  - Milosavljević, Slobodan
PY  - 2023
AB  - Bisbibenzyls represent chemical class of compounds containing two bibenzyl units mutually connected by an oxygen atom and/or directly by the “C-C” bonds. They are chemical markers of liverworts, the ancestors of higher vascular plants. Marchantin A from Marchantia polymorpha was the first discovered bisbibenzyl. More than 120 chemically characterized bisbibenzyls 
were reported up to 2020 with numerous biological activities [1]. The first report on bisbibenzyls in higher (vascular) plants was published in 2007, when 
Kosenkova et al. (2007) isolated riccardin C in Primula veris subsp. macrocalyx from Mt. Altay in Russia as the dominant compound in the extract of the whole plant [2]. In the repeated study of the same species, Kosenkova et al. (2009) confirmed their findings discovering an additional bisbibenzyl constituent, perrottetin E [3].
In this investigation from the CH2Cl2/CH3OH (1:1) extract of the air-dried, powdered roots nine isbibenzyls, five new, have been isolated from P. veris subsp. columnae and P. acaulis using dry column flash chromatography followed by semipreparative HPLC chromatography and identified on the basis of 1D and 2D NMR, IR, UV and HRESIMS data. This investigation widens the knowledge about the presence of bisbibenzyls in vascular plants since only two bisbibenzyls have been previously found in vascular plants, in Primula veris subsp. macrocalyx.
PB  - International Conference on Natural Products Utilization - ICNPU2023
C3  - Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria
T1  - Bisbibenzyls in Primula species
SP  - 47
EP  - 48
UR  - https://hdl.handle.net/21.15107/rcub_cer_7269
ER  - 
@conference{
author = "Novaković, Miroslav and Jadranin, Milka and Lekić, Stefan and Savić, Danica and Krstić, Gordana and Tešević, Vele and Milosavljević, Slobodan",
year = "2023",
abstract = "Bisbibenzyls represent chemical class of compounds containing two bibenzyl units mutually connected by an oxygen atom and/or directly by the “C-C” bonds. They are chemical markers of liverworts, the ancestors of higher vascular plants. Marchantin A from Marchantia polymorpha was the first discovered bisbibenzyl. More than 120 chemically characterized bisbibenzyls 
were reported up to 2020 with numerous biological activities [1]. The first report on bisbibenzyls in higher (vascular) plants was published in 2007, when 
Kosenkova et al. (2007) isolated riccardin C in Primula veris subsp. macrocalyx from Mt. Altay in Russia as the dominant compound in the extract of the whole plant [2]. In the repeated study of the same species, Kosenkova et al. (2009) confirmed their findings discovering an additional bisbibenzyl constituent, perrottetin E [3].
In this investigation from the CH2Cl2/CH3OH (1:1) extract of the air-dried, powdered roots nine isbibenzyls, five new, have been isolated from P. veris subsp. columnae and P. acaulis using dry column flash chromatography followed by semipreparative HPLC chromatography and identified on the basis of 1D and 2D NMR, IR, UV and HRESIMS data. This investigation widens the knowledge about the presence of bisbibenzyls in vascular plants since only two bisbibenzyls have been previously found in vascular plants, in Primula veris subsp. macrocalyx.",
publisher = "International Conference on Natural Products Utilization - ICNPU2023",
journal = "Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria",
title = "Bisbibenzyls in Primula species",
pages = "47-48",
url = "https://hdl.handle.net/21.15107/rcub_cer_7269"
}
Novaković, M., Jadranin, M., Lekić, S., Savić, D., Krstić, G., Tešević, V.,& Milosavljević, S.. (2023). Bisbibenzyls in Primula species. in Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria
International Conference on Natural Products Utilization - ICNPU2023., 47-48.
https://hdl.handle.net/21.15107/rcub_cer_7269
Novaković M, Jadranin M, Lekić S, Savić D, Krstić G, Tešević V, Milosavljević S. Bisbibenzyls in Primula species. in Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria. 2023;:47-48.
https://hdl.handle.net/21.15107/rcub_cer_7269 .
Novaković, Miroslav, Jadranin, Milka, Lekić, Stefan, Savić, Danica, Krstić, Gordana, Tešević, Vele, Milosavljević, Slobodan, "Bisbibenzyls in Primula species" in Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria (2023):47-48,
https://hdl.handle.net/21.15107/rcub_cer_7269 .

Diarylheptanoids from gray alder

Lekić, Stefan; Novaković, Miroslav; Savić, Danica; Тrendafilova, Antoaneta; Ivanova, Viktoria; Krstić, Gordana; Tešević, Vele; Milosavljević, Slobodan

(International Conference on Natural Products Utilization - ICNPU2023, 2023)

TY  - CONF
AU  - Lekić, Stefan
AU  - Novaković, Miroslav
AU  - Savić, Danica
AU  - Тrendafilova, Antoaneta
AU  - Ivanova, Viktoria
AU  - Krstić, Gordana
AU  - Tešević, Vele
AU  - Milosavljević, Slobodan
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7271
AB  - In this investigation nine known diarylheptanoids, namely platyphyllenone, hirsutenone, alnuside A and B, platyphylloside, oregonin, platyphyllonol-5-O-β-D-xylopyranoside, oregonoyl A and oregonoyl B have 
been isolated from the bark of A. incana using dry column flash chromatography followed by semipreparative HPLC chromatography. The structure elucidation has been performed using 1D and 2D NMR, as well as, IR and UV spectroscopy.
PB  - International Conference on Natural Products Utilization - ICNPU2023
C3  - Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria
T1  - Diarylheptanoids from gray alder
SP  - 201
EP  - 200
UR  - https://hdl.handle.net/21.15107/rcub_cer_7271
ER  - 
@conference{
author = "Lekić, Stefan and Novaković, Miroslav and Savić, Danica and Тrendafilova, Antoaneta and Ivanova, Viktoria and Krstić, Gordana and Tešević, Vele and Milosavljević, Slobodan",
year = "2023",
abstract = "In this investigation nine known diarylheptanoids, namely platyphyllenone, hirsutenone, alnuside A and B, platyphylloside, oregonin, platyphyllonol-5-O-β-D-xylopyranoside, oregonoyl A and oregonoyl B have 
been isolated from the bark of A. incana using dry column flash chromatography followed by semipreparative HPLC chromatography. The structure elucidation has been performed using 1D and 2D NMR, as well as, IR and UV spectroscopy.",
publisher = "International Conference on Natural Products Utilization - ICNPU2023",
journal = "Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria",
title = "Diarylheptanoids from gray alder",
pages = "201-200",
url = "https://hdl.handle.net/21.15107/rcub_cer_7271"
}
Lekić, S., Novaković, M., Savić, D., Тrendafilova, A., Ivanova, V., Krstić, G., Tešević, V.,& Milosavljević, S.. (2023). Diarylheptanoids from gray alder. in Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria
International Conference on Natural Products Utilization - ICNPU2023., 201-200.
https://hdl.handle.net/21.15107/rcub_cer_7271
Lekić S, Novaković M, Savić D, Тrendafilova A, Ivanova V, Krstić G, Tešević V, Milosavljević S. Diarylheptanoids from gray alder. in Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria. 2023;:201-200.
https://hdl.handle.net/21.15107/rcub_cer_7271 .
Lekić, Stefan, Novaković, Miroslav, Savić, Danica, Тrendafilova, Antoaneta, Ivanova, Viktoria, Krstić, Gordana, Tešević, Vele, Milosavljević, Slobodan, "Diarylheptanoids from gray alder" in Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria (2023):201-200,
https://hdl.handle.net/21.15107/rcub_cer_7271 .

Tigliane diterpenes isolated from the latex of Euphorbia lucida

Savić, Danica; Krstić, Gordana; Jadranin, Milka; Novaković, Miroslav; Lekić, Stefan; Tešević, Vele; Milosavljević, Slobodan

(International Conference on Natural Products Utilization - ICNPU2023, 2023)

TY  - CONF
AU  - Savić, Danica
AU  - Krstić, Gordana
AU  - Jadranin, Milka
AU  - Novaković, Miroslav
AU  - Lekić, Stefan
AU  - Tešević, Vele
AU  - Milosavljević, Slobodan
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7272
AB  - The diversity of plant species from the genus Euphorbia and wide variety of secondary metabolites they produce contributed to their successful use in the traditional medicine all over the world. Therapeutic applications have been attributed to different compounds such as diterpenes and triterpenes. Previous investigations revealed that Euphorbia diterpenes possess a variety of biological activities such as anti-inflammatory, antitumor and antiviral. Some of them showed that tigliane diterpenes, beside other potential pharmaceutical activities, inhibited wild-type HIV-1 and HIV-2 strains as well as drug resistant strains of HIV 1 and that they exhibited low cytotoxicity. Two tigliane diterpenes were 
isolated from the latex of E. lucida, using classical and instrumental chromatographic techniques. ESI-HRMS spectra showed that both isolated compounds possess the same molecular formula (C31H38O6). 1D NMR spectra revealed benzoate and isobutanoate ester groups in both molecules, Using HMBC spectra their position was determined: C-13 for isobutanoate and C-20 for benzoate. Exact configurations were discovered by NOE correlations. It was concluded that these two molecules differ in the way of the binding the five-membered and seven-membered rings, i.e., that these two molecules are C-4-epimers. Compound 1 (20-benzoyloxy-13α-isobutanoyloxy-4,12-dideoxyphorbol) was already described in the literature as a metabolite of E. pannonica [1], while compound 2 (20-benzoyloxy-13α-isobutanoyloxy-4-epi-4,12-dideoxyphorbol) represents a new tigliane derivative.
PB  - International Conference on Natural Products Utilization - ICNPU2023
C3  - Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria
T1  - Tigliane diterpenes isolated from the latex of Euphorbia lucida
SP  - 239
EP  - 239
UR  - https://hdl.handle.net/21.15107/rcub_cer_7272
ER  - 
@conference{
author = "Savić, Danica and Krstić, Gordana and Jadranin, Milka and Novaković, Miroslav and Lekić, Stefan and Tešević, Vele and Milosavljević, Slobodan",
year = "2023",
abstract = "The diversity of plant species from the genus Euphorbia and wide variety of secondary metabolites they produce contributed to their successful use in the traditional medicine all over the world. Therapeutic applications have been attributed to different compounds such as diterpenes and triterpenes. Previous investigations revealed that Euphorbia diterpenes possess a variety of biological activities such as anti-inflammatory, antitumor and antiviral. Some of them showed that tigliane diterpenes, beside other potential pharmaceutical activities, inhibited wild-type HIV-1 and HIV-2 strains as well as drug resistant strains of HIV 1 and that they exhibited low cytotoxicity. Two tigliane diterpenes were 
isolated from the latex of E. lucida, using classical and instrumental chromatographic techniques. ESI-HRMS spectra showed that both isolated compounds possess the same molecular formula (C31H38O6). 1D NMR spectra revealed benzoate and isobutanoate ester groups in both molecules, Using HMBC spectra their position was determined: C-13 for isobutanoate and C-20 for benzoate. Exact configurations were discovered by NOE correlations. It was concluded that these two molecules differ in the way of the binding the five-membered and seven-membered rings, i.e., that these two molecules are C-4-epimers. Compound 1 (20-benzoyloxy-13α-isobutanoyloxy-4,12-dideoxyphorbol) was already described in the literature as a metabolite of E. pannonica [1], while compound 2 (20-benzoyloxy-13α-isobutanoyloxy-4-epi-4,12-dideoxyphorbol) represents a new tigliane derivative.",
publisher = "International Conference on Natural Products Utilization - ICNPU2023",
journal = "Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria",
title = "Tigliane diterpenes isolated from the latex of Euphorbia lucida",
pages = "239-239",
url = "https://hdl.handle.net/21.15107/rcub_cer_7272"
}
Savić, D., Krstić, G., Jadranin, M., Novaković, M., Lekić, S., Tešević, V.,& Milosavljević, S.. (2023). Tigliane diterpenes isolated from the latex of Euphorbia lucida. in Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria
International Conference on Natural Products Utilization - ICNPU2023., 239-239.
https://hdl.handle.net/21.15107/rcub_cer_7272
Savić D, Krstić G, Jadranin M, Novaković M, Lekić S, Tešević V, Milosavljević S. Tigliane diterpenes isolated from the latex of Euphorbia lucida. in Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria. 2023;:239-239.
https://hdl.handle.net/21.15107/rcub_cer_7272 .
Savić, Danica, Krstić, Gordana, Jadranin, Milka, Novaković, Miroslav, Lekić, Stefan, Tešević, Vele, Milosavljević, Slobodan, "Tigliane diterpenes isolated from the latex of Euphorbia lucida" in Book of Abstracts - The 5th International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU-2023), 30 May–02 June 2023, Sts. Constantine and Helena - Varna, Bulgaria (2023):239-239,
https://hdl.handle.net/21.15107/rcub_cer_7272 .

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

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

(Elsevier, 2023)

TY  - JOUR
AU  - Novaković, Miroslav
AU  - Ilić-Tomić, Tatjana
AU  - Đorđević, Iris
AU  - Anđelković, Boban D.
AU  - Tešević, Vele
AU  - Milosavljević, Slobodan
AU  - Asakawa, Yoshinori
PY  - 2023
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7188
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
SP  - 113719
DO  - 10.1016/j.phytochem.2023.113719
ER  - 
@article{
author = "Novaković, Miroslav and Ilić-Tomić, Tatjana and Đorđević, Iris and Anđelković, Boban D. and Tešević, Vele and Milosavljević, Slobodan 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., Ilić-Tomić, T., Đorđević, I., Anđelković, B. D., Tešević, V., Milosavljević, S.,& Asakawa, Y.. (2023). Bisbibenzyls from Serbian Primula veris subsp. Columnae (Ten.) Lȕdi and P. acaulis (L.) L. in Phytochemistry
Elsevier., 212, 113719.
https://doi.org/10.1016/j.phytochem.2023.113719
Novaković M, Ilić-Tomić T, Đorđević I, Anđelković BD, Tešević V, Milosavljević S, Asakawa Y. Bisbibenzyls from Serbian Primula veris subsp. Columnae (Ten.) Lȕdi and P. acaulis (L.) L. in Phytochemistry. 2023;212:113719.
doi:10.1016/j.phytochem.2023.113719 .
Novaković, Miroslav, Ilić-Tomić, Tatjana, Đorđević, Iris, Anđelković, Boban D., Tešević, Vele, Milosavljević, Slobodan, Asakawa, Yoshinori, "Bisbibenzyls from Serbian Primula veris subsp. Columnae (Ten.) Lȕdi and P. acaulis (L.) L" in Phytochemistry, 212 (2023):113719,
https://doi.org/10.1016/j.phytochem.2023.113719 . .

A New Auronolignan from the Cotinus coggygria Heartwood

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

(Springer, 2023)

TY  - JOUR
AU  - Novaković, Miroslav
AU  - Todorović, Nina
AU  - Jadranin, Milka
AU  - Đorđević, Iris
AU  - Milosavljević, Slobodan M.
AU  - Mandić, Boris
AU  - Tešević, Vele
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7191
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 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., 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 M, 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, 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 . .

Antiproliferative Activity of Natural Flavonoid Fustin Isolated from the Heartwood of Cotinus Coggygria Scop. Against Breast and Colon Cancer Cell Lines

Gospodinova, Z.; Antov, G.; Novaković, Miroslav; Tešević, Vele; Krasteva, N.; Pavlov, D.; Valcheva-Kuzmanova, S.

(Walter de Gruyter GmbH, 2023)

TY  - JOUR
AU  - Gospodinova, Z.
AU  - Antov, G.
AU  - Novaković, Miroslav
AU  - Tešević, Vele
AU  - Krasteva, N.
AU  - Pavlov, D.
AU  - Valcheva-Kuzmanova, S.
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7225
AB  - Background and objective: Cotinus coggygria Scop. is a valuable medicinal  plant species with pronounced pharmacological potential due to its numerous biological  activities. The herb is characterized by a high content of polyphenols among which is fustin.  The anticancer activities of fustin, however, are extremely weakly studied. The aim of the  present study was to investigate the in vitro antiproliferative potential of fustin isolated from  the heartwood of C. coggygria against cell lines originating from two of the most common  cancer types – breast (MDA-MB-231 and MCF7), and colon cancer (Colon 26). Materials  and methods: Cell growth inhibitory properties of fustin were examined by MTT assay.  Subsequently, phase-contrast and fl uorescence microscopy analysis as well as colonyforming assay were carried out on the most sensitive to the cytostatic action of the fustin  cell line. Results: The obtained results showed that fustin reduced the proliferation of  all studied cell lines. The highest cytostatic eff ect was registered towards breast cancer  MDA-MB-231 cells with a half maximal inhibitory concentration (IC50) value of 56.02 μg/ ml followed by colon cancer cells with an IC50 of 78.07 μg/ml. MCF7 cell proliferation was  least aff ected with a calculated IC50 of 187.8 μg/ml. Further investigations on breast cancer  MDA-MB-231 cells indicated decreased density of cell monolayer and some morphological  alterations, signifi cant attenuation in the number of viable cells, and diminished clonogenic  ability of cells after fustin exposure. Conclusion: It could be concluded that fustin isolated  from the heartwood of medicinal plant C. coggygria possesses marked antiproliferative  properties against breast cancer cell line MDA-MB-231 which will be a subject of our more  detailed future investigations.
PB  - Walter de Gruyter GmbH
T2  - Acta Medica Bulgarica
T1  - Antiproliferative Activity of Natural Flavonoid Fustin Isolated from the Heartwood of                    Cotinus Coggygria                    Scop. Against Breast and Colon Cancer Cell Lines
VL  - 50
IS  - 1
SP  - 27
EP  - 33
DO  - 10.2478/amb-2023-0004
ER  - 
@article{
author = "Gospodinova, Z. and Antov, G. and Novaković, Miroslav and Tešević, Vele and Krasteva, N. and Pavlov, D. and Valcheva-Kuzmanova, S.",
year = "2023",
abstract = "Background and objective: Cotinus coggygria Scop. is a valuable medicinal  plant species with pronounced pharmacological potential due to its numerous biological  activities. The herb is characterized by a high content of polyphenols among which is fustin.  The anticancer activities of fustin, however, are extremely weakly studied. The aim of the  present study was to investigate the in vitro antiproliferative potential of fustin isolated from  the heartwood of C. coggygria against cell lines originating from two of the most common  cancer types – breast (MDA-MB-231 and MCF7), and colon cancer (Colon 26). Materials  and methods: Cell growth inhibitory properties of fustin were examined by MTT assay.  Subsequently, phase-contrast and fl uorescence microscopy analysis as well as colonyforming assay were carried out on the most sensitive to the cytostatic action of the fustin  cell line. Results: The obtained results showed that fustin reduced the proliferation of  all studied cell lines. The highest cytostatic eff ect was registered towards breast cancer  MDA-MB-231 cells with a half maximal inhibitory concentration (IC50) value of 56.02 μg/ ml followed by colon cancer cells with an IC50 of 78.07 μg/ml. MCF7 cell proliferation was  least aff ected with a calculated IC50 of 187.8 μg/ml. Further investigations on breast cancer  MDA-MB-231 cells indicated decreased density of cell monolayer and some morphological  alterations, signifi cant attenuation in the number of viable cells, and diminished clonogenic  ability of cells after fustin exposure. Conclusion: It could be concluded that fustin isolated  from the heartwood of medicinal plant C. coggygria possesses marked antiproliferative  properties against breast cancer cell line MDA-MB-231 which will be a subject of our more  detailed future investigations.",
publisher = "Walter de Gruyter GmbH",
journal = "Acta Medica Bulgarica",
title = "Antiproliferative Activity of Natural Flavonoid Fustin Isolated from the Heartwood of                    Cotinus Coggygria                    Scop. Against Breast and Colon Cancer Cell Lines",
volume = "50",
number = "1",
pages = "27-33",
doi = "10.2478/amb-2023-0004"
}
Gospodinova, Z., Antov, G., Novaković, M., Tešević, V., Krasteva, N., Pavlov, D.,& Valcheva-Kuzmanova, S.. (2023). Antiproliferative Activity of Natural Flavonoid Fustin Isolated from the Heartwood of                    Cotinus Coggygria                    Scop. Against Breast and Colon Cancer Cell Lines. in Acta Medica Bulgarica
Walter de Gruyter GmbH., 50(1), 27-33.
https://doi.org/10.2478/amb-2023-0004
Gospodinova Z, Antov G, Novaković M, Tešević V, Krasteva N, Pavlov D, Valcheva-Kuzmanova S. Antiproliferative Activity of Natural Flavonoid Fustin Isolated from the Heartwood of                    Cotinus Coggygria                    Scop. Against Breast and Colon Cancer Cell Lines. in Acta Medica Bulgarica. 2023;50(1):27-33.
doi:10.2478/amb-2023-0004 .
Gospodinova, Z., Antov, G., Novaković, Miroslav, Tešević, Vele, Krasteva, N., Pavlov, D., Valcheva-Kuzmanova, S., "Antiproliferative Activity of Natural Flavonoid Fustin Isolated from the Heartwood of                    Cotinus Coggygria                    Scop. Against Breast and Colon Cancer Cell Lines" in Acta Medica Bulgarica, 50, no. 1 (2023):27-33,
https://doi.org/10.2478/amb-2023-0004 . .

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; Terzić-Jovanović, Nataša; Novaković, Miroslav; Nedialkov, Paraskev; Trendafilova, Antoaneta; Pešić, Milica; Opsenica, Igor

(Elsevier, 2023)

TY  - JOUR
AU  - Stojković, Pavle
AU  - Kostić, Ana
AU  - Lupšić, Ema
AU  - Terzić-Jovanović, Nataša
AU  - Novaković, Miroslav
AU  - Nedialkov, Paraskev
AU  - Trendafilova, Antoaneta
AU  - Pešić, Milica
AU  - Opsenica, Igor
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7183
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 Terzić-Jovanović, Nataša and Novaković, Miroslav 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., Terzić-Jovanović, N., Novaković, 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, Terzić-Jovanović N, Novaković M, 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, Terzić-Jovanović, Nataša, Novaković, Miroslav, 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

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

Koračak, Ljiljana; Lupšić, Ema; Terzić-Jovanović, Nataša; Jovanović, Mirna; Novaković, Miroslav; 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
AU  - Nedialkov, Paraskev
AU  - Trendafilova, Antoaneta
AU  - Zlatović, Mario
AU  - Pešić, Milica
AU  - Opsenica, Igor
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7172
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 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., 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 M, 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, 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

Analysis of diterpenoids from the latex of E. seguieriana Neck. subsp. seguieriana by liquid chromatography–electrospray ionisation mass spectrometry

Jadranin, Milka; Krstić, Gordana; Novaković, Miroslav; Anđelković, Boban; Tešević, Vele; Milosavljević, Slobodan

(Belgrade : University of Belgrade - Faculty of Agriculture, 2022)

TY  - CONF
AU  - Jadranin, Milka
AU  - Krstić, Gordana
AU  - Novaković, Miroslav
AU  - Anđelković, Boban
AU  - Tešević, Vele
AU  - Milosavljević, Slobodan
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5864
AB  - In this study, we analysed the chloroform extract of the latex of E. seguieriana Neck. subsp. 
seguieriana collected on Deliblato sand in flowering season by reversed-phase liquid chromatography–electrospray ionisation mass spectrometry (LC-ESI MS). From the data obtained from LC-ESI MS analysis, premyrsinane, myrsinane and lathyrane nicotinoyl esters are the dominant diterpene metabolites of the latex. In the continuation of the research, compounds will be isolated, their structures elucidated, and their biological activities examined.
PB  - Belgrade : University of Belgrade - Faculty of Agriculture
C3  - Book of Abstracts - 1st European Symposium on Phytochemicals in Medicine and Food (1-EuSPMF), 7–9 September 2022, Belgrade, Serbia
T1  - Analysis of diterpenoids from the latex of E. seguieriana Neck. subsp. seguieriana by liquid chromatography–electrospray ionisation mass spectrometry
SP  - 86
EP  - 86
UR  - https://hdl.handle.net/21.15107/rcub_cer_5864
ER  - 
@conference{
author = "Jadranin, Milka and Krstić, Gordana and Novaković, Miroslav and Anđelković, Boban and Tešević, Vele and Milosavljević, Slobodan",
year = "2022",
abstract = "In this study, we analysed the chloroform extract of the latex of E. seguieriana Neck. subsp. 
seguieriana collected on Deliblato sand in flowering season by reversed-phase liquid chromatography–electrospray ionisation mass spectrometry (LC-ESI MS). From the data obtained from LC-ESI MS analysis, premyrsinane, myrsinane and lathyrane nicotinoyl esters are the dominant diterpene metabolites of the latex. In the continuation of the research, compounds will be isolated, their structures elucidated, and their biological activities examined.",
publisher = "Belgrade : University of Belgrade - Faculty of Agriculture",
journal = "Book of Abstracts - 1st European Symposium on Phytochemicals in Medicine and Food (1-EuSPMF), 7–9 September 2022, Belgrade, Serbia",
title = "Analysis of diterpenoids from the latex of E. seguieriana Neck. subsp. seguieriana by liquid chromatography–electrospray ionisation mass spectrometry",
pages = "86-86",
url = "https://hdl.handle.net/21.15107/rcub_cer_5864"
}
Jadranin, M., Krstić, G., Novaković, M., Anđelković, B., Tešević, V.,& Milosavljević, S.. (2022). Analysis of diterpenoids from the latex of E. seguieriana Neck. subsp. seguieriana by liquid chromatography–electrospray ionisation mass spectrometry. in Book of Abstracts - 1st European Symposium on Phytochemicals in Medicine and Food (1-EuSPMF), 7–9 September 2022, Belgrade, Serbia
Belgrade : University of Belgrade - Faculty of Agriculture., 86-86.
https://hdl.handle.net/21.15107/rcub_cer_5864
Jadranin M, Krstić G, Novaković M, Anđelković B, Tešević V, Milosavljević S. Analysis of diterpenoids from the latex of E. seguieriana Neck. subsp. seguieriana by liquid chromatography–electrospray ionisation mass spectrometry. in Book of Abstracts - 1st European Symposium on Phytochemicals in Medicine and Food (1-EuSPMF), 7–9 September 2022, Belgrade, Serbia. 2022;:86-86.
https://hdl.handle.net/21.15107/rcub_cer_5864 .
Jadranin, Milka, Krstić, Gordana, Novaković, Miroslav, Anđelković, Boban, Tešević, Vele, Milosavljević, Slobodan, "Analysis of diterpenoids from the latex of E. seguieriana Neck. subsp. seguieriana by liquid chromatography–electrospray ionisation mass spectrometry" in Book of Abstracts - 1st European Symposium on Phytochemicals in Medicine and Food (1-EuSPMF), 7–9 September 2022, Belgrade, Serbia (2022):86-86,
https://hdl.handle.net/21.15107/rcub_cer_5864 .

Bis-bibenzyls, Bibenzyls, and Terpenoids in 33 Genera of the Marchantiophyta (Liverworts): Structures, Synthesis, and Bioactivity

Asakawa, Yoshinori; Ludwiczuk, Agnieszka; Novaković, Miroslav; Bukvicki, Danka; Anchang, Kenneth Yongabi

(USA : American Chemical Society, 2022)

TY  - JOUR
AU  - Asakawa, Yoshinori
AU  - Ludwiczuk, Agnieszka
AU  - Novaković, Miroslav
AU  - Bukvicki, Danka
AU  - Anchang, Kenneth Yongabi
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5404
AB  - The Marchantiophyta (liverworts) are rich sources of phenolic substances, especially cyclic and acyclic bis-bibenzyls, which are rare natural products in the plant kingdom, together with bibenzyls and characteristic terpenoids. At present, more than 125 bis-bibenzyls have been found in liverworts. They are biosynthesized from the dimerization of lunularic acid via dihydrocoumaric acid and prelunularin. The structurally unusual cyclic and acyclic bis-bibenzyls show various biological activities such as antimicrobial, antifungal, cytotoxic, muscle relaxation, antioxidant, tubulin polymerization inhibitory, and antitrypanosomal activities, among others. The present review article deals with the distribution and structure of bis-bibenzyls, bibenzyls, and several characteristic ent-sesqui- and diterpenoids in liverworts. Furthermore, the biosynthesis and total syntheses and biological activities of bis-bibenzyls are also surveyed.
PB  - USA : American Chemical Society
T2  - Journal of Natural Products
T1  - Bis-bibenzyls, Bibenzyls, and Terpenoids in 33 Genera of the Marchantiophyta (Liverworts): Structures, Synthesis, and Bioactivity
VL  - 85
IS  - 3
SP  - 729
EP  - 762
DO  - 10.1021/acs.jnatprod.1c00302
ER  - 
@article{
author = "Asakawa, Yoshinori and Ludwiczuk, Agnieszka and Novaković, Miroslav and Bukvicki, Danka and Anchang, Kenneth Yongabi",
year = "2022",
abstract = "The Marchantiophyta (liverworts) are rich sources of phenolic substances, especially cyclic and acyclic bis-bibenzyls, which are rare natural products in the plant kingdom, together with bibenzyls and characteristic terpenoids. At present, more than 125 bis-bibenzyls have been found in liverworts. They are biosynthesized from the dimerization of lunularic acid via dihydrocoumaric acid and prelunularin. The structurally unusual cyclic and acyclic bis-bibenzyls show various biological activities such as antimicrobial, antifungal, cytotoxic, muscle relaxation, antioxidant, tubulin polymerization inhibitory, and antitrypanosomal activities, among others. The present review article deals with the distribution and structure of bis-bibenzyls, bibenzyls, and several characteristic ent-sesqui- and diterpenoids in liverworts. Furthermore, the biosynthesis and total syntheses and biological activities of bis-bibenzyls are also surveyed.",
publisher = "USA : American Chemical Society",
journal = "Journal of Natural Products",
title = "Bis-bibenzyls, Bibenzyls, and Terpenoids in 33 Genera of the Marchantiophyta (Liverworts): Structures, Synthesis, and Bioactivity",
volume = "85",
number = "3",
pages = "729-762",
doi = "10.1021/acs.jnatprod.1c00302"
}
Asakawa, Y., Ludwiczuk, A., Novaković, M., Bukvicki, D.,& Anchang, K. Y.. (2022). Bis-bibenzyls, Bibenzyls, and Terpenoids in 33 Genera of the Marchantiophyta (Liverworts): Structures, Synthesis, and Bioactivity. in Journal of Natural Products
USA : American Chemical Society., 85(3), 729-762.
https://doi.org/10.1021/acs.jnatprod.1c00302
Asakawa Y, Ludwiczuk A, Novaković M, Bukvicki D, Anchang KY. Bis-bibenzyls, Bibenzyls, and Terpenoids in 33 Genera of the Marchantiophyta (Liverworts): Structures, Synthesis, and Bioactivity. in Journal of Natural Products. 2022;85(3):729-762.
doi:10.1021/acs.jnatprod.1c00302 .
Asakawa, Yoshinori, Ludwiczuk, Agnieszka, Novaković, Miroslav, Bukvicki, Danka, Anchang, Kenneth Yongabi, "Bis-bibenzyls, Bibenzyls, and Terpenoids in 33 Genera of the Marchantiophyta (Liverworts): Structures, Synthesis, and Bioactivity" in Journal of Natural Products, 85, no. 3 (2022):729-762,
https://doi.org/10.1021/acs.jnatprod.1c00302 . .
23
19

Two new jatrophane diterpenes from the roots of Euphorbia nicaeensis

Krstić, Gordana; Kostić, Ana; Jadranin, Milka; Pešić, Milica; Novaković, Miroslav; Aljančić, Ivana; Vajs, Vlatka

(Serbian Chemical Society, 2021)

TY  - JOUR
AU  - Krstić, Gordana
AU  - Kostić, Ana
AU  - Jadranin, Milka
AU  - Pešić, Milica
AU  - Novaković, Miroslav
AU  - Aljančić, Ivana
AU  - Vajs, Vlatka
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4910
AB  - In the previous study fifteen jatrophane diterpenes were isolated from the Euphorbia nicaeensis latex. Fourteen of them have been shown to be potent P-glycoprotein (P-gp) inhibitor in two MDR cancer cells (NCI-H460/R and DLD1-TxR). The aim of this study was to determine whether and which jatro­phane diterpenes can be isolated from the root of the plant, and then to examine their inhibition power on P-glycoprotein of selected cancer cell lines (NCI-H460, DLD1, U87, NCI-H460/R, DLD1-TxR and U87-TxR). Two previously undes­cribed jatrophane diterpenes were isolated from the root of E. nicaeensis col­lected in Deliblato Sand (Serbia). The structures of the isolated compounds were determined using 1D and 2D NMR, as well as HRESIMS data. The results obtained by MTT assay showed different antitumor potential of these two jatrophanes. Compound 1 inhibited cell growth of non-small cell lung car­cinoma cell lines NCI-H460 and NCI-H460/R, as well as glioblastoma cell lines U87 and U87-TxR, while jatrophane 2 was almost completely inactive in the suppression of cancer cell growth in a given range of concentrations. The obtained results also showed that the isolated compounds have an inhibitory effect on P-glycoprotein, as well as that their inhibitory potential is similar.
AB  - У претходном истраживању, петнаест дитерпена јатрофанског типа изоловано је из латекса Euphorbia nicaeensis. Њих четрнаест показала су се као снажни инхибитори P-гликопротеина (P-gp) у две MDR ћелијске линије рака (NCI-H460/R и DLD1-TxR). Циљ ове студије био је да се утврди да ли је и које јатрофанске дитерпене могуће изо- ловати из корена биљке, а затим испитивање њихове инхибиторне моћи на P-гликопро- теину одабраних ћелијских линија рака (NCI-H460, DLD1, U87, NCI-H460/R, DLD1-TxR и U87-TxR). Два претходно непозната јатрофана изолованa су из корена E. nicaeensis прикупљеног у Делиблатској пешчари. Структуре изолованих једињења одређене су применом 1D и 2D NMR метода, као и HRESIMS експеримента. Резултати добијени МТТ тестом показали су различит антиканцерогени потенцијал ова два јатрофана. Једињење 1 је инхибирало раст ћелија ћелијских линија неситноћелијског карцинома плућа NCI-H460 и NCI-H460/R, као и ћелијских линија глиобластома U87 и U87-TxR, док је јатрофан 2 био готово потпуно неефикасан у сузбијању растa ћелија карцинома у датом концентрационом опсегу. Добијени резултати су такође показали да 1 и 2 имају инхибиторно дејство на P-гликопротеин, као и да је њихов инхибиторни потенцијал сличан.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Two new jatrophane diterpenes from the roots of Euphorbia nicaeensis
T1  - Два нова јатрофанска дитерпена из корена Euphorbia nicaeensis
IS  - 12
SP  - 1219
EP  - 1228
DO  - 10.2298/JSC210806085K
ER  - 
@article{
author = "Krstić, Gordana and Kostić, Ana and Jadranin, Milka and Pešić, Milica and Novaković, Miroslav and Aljančić, Ivana and Vajs, Vlatka",
year = "2021",
abstract = "In the previous study fifteen jatrophane diterpenes were isolated from the Euphorbia nicaeensis latex. Fourteen of them have been shown to be potent P-glycoprotein (P-gp) inhibitor in two MDR cancer cells (NCI-H460/R and DLD1-TxR). The aim of this study was to determine whether and which jatro­phane diterpenes can be isolated from the root of the plant, and then to examine their inhibition power on P-glycoprotein of selected cancer cell lines (NCI-H460, DLD1, U87, NCI-H460/R, DLD1-TxR and U87-TxR). Two previously undes­cribed jatrophane diterpenes were isolated from the root of E. nicaeensis col­lected in Deliblato Sand (Serbia). The structures of the isolated compounds were determined using 1D and 2D NMR, as well as HRESIMS data. The results obtained by MTT assay showed different antitumor potential of these two jatrophanes. Compound 1 inhibited cell growth of non-small cell lung car­cinoma cell lines NCI-H460 and NCI-H460/R, as well as glioblastoma cell lines U87 and U87-TxR, while jatrophane 2 was almost completely inactive in the suppression of cancer cell growth in a given range of concentrations. The obtained results also showed that the isolated compounds have an inhibitory effect on P-glycoprotein, as well as that their inhibitory potential is similar., У претходном истраживању, петнаест дитерпена јатрофанског типа изоловано је из латекса Euphorbia nicaeensis. Њих четрнаест показала су се као снажни инхибитори P-гликопротеина (P-gp) у две MDR ћелијске линије рака (NCI-H460/R и DLD1-TxR). Циљ ове студије био је да се утврди да ли је и које јатрофанске дитерпене могуће изо- ловати из корена биљке, а затим испитивање њихове инхибиторне моћи на P-гликопро- теину одабраних ћелијских линија рака (NCI-H460, DLD1, U87, NCI-H460/R, DLD1-TxR и U87-TxR). Два претходно непозната јатрофана изолованa су из корена E. nicaeensis прикупљеног у Делиблатској пешчари. Структуре изолованих једињења одређене су применом 1D и 2D NMR метода, као и HRESIMS експеримента. Резултати добијени МТТ тестом показали су различит антиканцерогени потенцијал ова два јатрофана. Једињење 1 је инхибирало раст ћелија ћелијских линија неситноћелијског карцинома плућа NCI-H460 и NCI-H460/R, као и ћелијских линија глиобластома U87 и U87-TxR, док је јатрофан 2 био готово потпуно неефикасан у сузбијању растa ћелија карцинома у датом концентрационом опсегу. Добијени резултати су такође показали да 1 и 2 имају инхибиторно дејство на P-гликопротеин, као и да је њихов инхибиторни потенцијал сличан.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Two new jatrophane diterpenes from the roots of Euphorbia nicaeensis, Два нова јатрофанска дитерпена из корена Euphorbia nicaeensis",
number = "12",
pages = "1219-1228",
doi = "10.2298/JSC210806085K"
}
Krstić, G., Kostić, A., Jadranin, M., Pešić, M., Novaković, M., Aljančić, I.,& Vajs, V.. (2021). Two new jatrophane diterpenes from the roots of Euphorbia nicaeensis. in Journal of the Serbian Chemical Society
Serbian Chemical Society.(12), 1219-1228.
https://doi.org/10.2298/JSC210806085K
Krstić G, Kostić A, Jadranin M, Pešić M, Novaković M, Aljančić I, Vajs V. Two new jatrophane diterpenes from the roots of Euphorbia nicaeensis. in Journal of the Serbian Chemical Society. 2021;(12):1219-1228.
doi:10.2298/JSC210806085K .
Krstić, Gordana, Kostić, Ana, Jadranin, Milka, Pešić, Milica, Novaković, Miroslav, Aljančić, Ivana, Vajs, Vlatka, "Two new jatrophane diterpenes from the roots of Euphorbia nicaeensis" in Journal of the Serbian Chemical Society, no. 12 (2021):1219-1228,
https://doi.org/10.2298/JSC210806085K . .
2

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

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

(Elsevier, 2021)

TY  - JOUR
AU  - Sofrenić, Ivana
AU  - Anđelković, Boban
AU  - Todorović, Nina
AU  - Stanojković, Tatjana
AU  - Vujisić, Ljubodrag V.
AU  - Novaković, Miroslav
AU  - Milosavljević, Slobodan
AU  - Tešević, Vele
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4038
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).
PB  - Elsevier
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 and Anđelković, Boban and Todorović, Nina and Stanojković, Tatjana and Vujisić, Ljubodrag V. and Novaković, Miroslav and Milosavljević, Slobodan 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).",
publisher = "Elsevier",
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., Anđelković, B., Todorović, N., Stanojković, T., Vujisić, L. V., Novaković, M., Milosavljević, S.,& Tešević, V.. (2021). Cytotoxic triterpenoids and triterpene sugar esters from the medicinal mushroom Fomitopsis betulina. in Phytochemistry
Elsevier., 181, 112580.
https://doi.org/10.1016/j.phytochem.2020.112580
Sofrenić I, Anđelković B, Todorović N, Stanojković T, Vujisić LV, Novaković M, Milosavljević S, 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, Anđelković, Boban, Todorović, Nina, Stanojković, Tatjana, Vujisić, Ljubodrag V., Novaković, Miroslav, Milosavljević, Slobodan, 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
13

DNA protective activity of triterpenoids isolated from medicinal mushroom Fomitopsis betulina

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

(Belgrade : Serbian Chemical Society, 2021)

TY  - JOUR
AU  - Sofrenić, Ivana
AU  - Anđelković, Boban D.
AU  - Vujisić, Ljubodrag V.
AU  - Novaković, Miroslav
AU  - Knežević, Aleksandar
AU  - Stanković, Miroslava
AU  - Milosavljević, Slobodan
AU  - Tešević, Vele
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4801
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.
AB  - Једанаест 31-метиленланостанских тритерпеноида, то јест седам 21- и четири 26-
ланостанских киселина, као и лупански тритерпеноид бетулин изолованих из плодонос-
них тела гљиве Fomitopsis betulina тестирани су in vitro на заштитни ефекат на аберације
хромозома у периферним хуманим лимфоцитима. Примењен је тест мерења учес-
талости микронуклеуса индукованих применом инхибитора цитокинезе, цитохалазина
Б. Испитивања су показала да већина тестираних једињења показује значајан протек-
тивни ефекат на ДНК хуманих лимфоцита, већи него комерцијални радиопротективни
агенс аминофостин. У опсегу концентрација 1, 2 и 4 μg mL-1 сва испитивана једињења су
смањивала учесталост микронуклеуса (MN), при чему је најефиканија била концентра-
ција од 2,0 μg mL-1. Са повећањем концентрације (4 μg mL-1) активност се благо смањује.
Студије односа структуре и активности (SAR) показале су да ланостани који садрже кон-
југовани 7,9-(11)-диенски систем имају нижу активност од _8-аналога. Такође је пока-
зано да на заштитне активности ДНК унутар групе _8-ланостан-26-киселина утиче суп-
ституција у положају 3. У _8-серији присуство кисеоничних функција на C-12 или C-16,
као и C-21 или C-26 карбоксилних група повећава in vitro протективни ефекат на на
ДНК хуманих лимфоцита. Међу испитиваним једињењима тритерпен бетулин (лупанска
серија) је показао најмањи протективни ефекат сличан са протективним ефектом ами-
фостина.
PB  - Belgrade : Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - DNA protective activity of triterpenoids isolated from medicinal mushroom Fomitopsis betulina
T1  - DNK protektivna aktivnost triterpena izolovanih iz medicinske gljive Fomitopsis betulina
VL  - 86
IS  - 9
SP  - 809
EP  - 817
DO  - 10.2298/JSC210401039S
ER  - 
@article{
author = "Sofrenić, Ivana and Anđelković, Boban D. and Vujisić, Ljubodrag V. and Novaković, Miroslav and Knežević, Aleksandar and Stanković, Miroslava and Milosavljević, Slobodan 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., Једанаест 31-метиленланостанских тритерпеноида, то јест седам 21- и четири 26-
ланостанских киселина, као и лупански тритерпеноид бетулин изолованих из плодонос-
них тела гљиве Fomitopsis betulina тестирани су in vitro на заштитни ефекат на аберације
хромозома у периферним хуманим лимфоцитима. Примењен је тест мерења учес-
талости микронуклеуса индукованих применом инхибитора цитокинезе, цитохалазина
Б. Испитивања су показала да већина тестираних једињења показује значајан протек-
тивни ефекат на ДНК хуманих лимфоцита, већи него комерцијални радиопротективни
агенс аминофостин. У опсегу концентрација 1, 2 и 4 μg mL-1 сва испитивана једињења су
смањивала учесталост микронуклеуса (MN), при чему је најефиканија била концентра-
ција од 2,0 μg mL-1. Са повећањем концентрације (4 μg mL-1) активност се благо смањује.
Студије односа структуре и активности (SAR) показале су да ланостани који садрже кон-
југовани 7,9-(11)-диенски систем имају нижу активност од _8-аналога. Такође је пока-
зано да на заштитне активности ДНК унутар групе _8-ланостан-26-киселина утиче суп-
ституција у положају 3. У _8-серији присуство кисеоничних функција на C-12 или C-16,
као и C-21 или C-26 карбоксилних група повећава in vitro протективни ефекат на на
ДНК хуманих лимфоцита. Међу испитиваним једињењима тритерпен бетулин (лупанска
серија) је показао најмањи протективни ефекат сличан са протективним ефектом ами-
фостина.",
publisher = "Belgrade : Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "DNA protective activity of triterpenoids isolated from medicinal mushroom Fomitopsis betulina, DNK protektivna aktivnost triterpena izolovanih iz medicinske gljive Fomitopsis betulina",
volume = "86",
number = "9",
pages = "809-817",
doi = "10.2298/JSC210401039S"
}
Sofrenić, I., Anđelković, B. D., Vujisić, L. V., Novaković, M., Knežević, A., Stanković, M., Milosavljević, S.,& Tešević, V.. (2021). DNA protective activity of triterpenoids isolated from medicinal mushroom Fomitopsis betulina. in Journal of the Serbian Chemical Society
Belgrade : Serbian Chemical Society., 86(9), 809-817.
https://doi.org/10.2298/JSC210401039S
Sofrenić I, Anđelković BD, Vujisić LV, Novaković M, Knežević A, Stanković M, Milosavljević S, 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, Anđelković, Boban D., Vujisić, Ljubodrag V., Novaković, Miroslav, Knežević, Aleksandar, Stanković, Miroslava, Milosavljević, Slobodan, 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 . .

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

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

(SAGE Publications, 2021)

TY  - JOUR
AU  - Milosavljević, Slobodan
AU  - Đorđević, Iris
AU  - Mandić, Boris
AU  - Tešević, Vele
AU  - Stanković, Miroslava
AU  - Todorović, Nina
AU  - Novaković, Miroslav
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4913
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 and Đorđević, Iris and Mandić, Boris and Tešević, Vele and Stanković, Miroslava and Todorović, Nina and Novaković, Miroslav",
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., Đorđević, I., Mandić, B., Tešević, V., Stanković, M., Todorović, N.,& Novaković, 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 S, Đorđević I, Mandić B, Tešević V, Stanković M, Todorović N, Novaković M. 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, Đorđević, Iris, Mandić, Boris, Tešević, Vele, Stanković, Miroslava, Todorović, Nina, Novaković, Miroslav, "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 . .
3

Inhibition potency of disulphides and trisulphides on various tumor cell lines growth

Mandić, Boris; Simić, Katarina; Trifunović, Snežana; Vujisić, Ljubodrag; Novaković, Miroslav; Tešević, Vele; Miljanić, Ognjen Š.

(S.C. Virtual Company of Phisics S.R.L, 2021)

TY  - JOUR
AU  - Mandić, Boris
AU  - Simić, Katarina
AU  - Trifunović, Snežana
AU  - Vujisić, Ljubodrag
AU  - Novaković, Miroslav
AU  - Tešević, Vele
AU  - Miljanić, Ognjen Š.
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7389
AB  - Tumor is one of the leading diseases of today. Chemotherapy and radiation therapy healing chances are limited, so some alternative methods are resorted to. Many papers indicated that garlic and organosulphur compounds diallyldisulphide (DADS) and diallyltrisulphide, which are main components of garlic decrease the cancer risk and inhibit the cell proliferation. In this paper inhibition potency of disulphides (DADS and its synthetic analogues) and trisulphides with different alkyl and phenyl substituents on growth of various tumor (Non-Small cell Lung Cancer, Colon cancer, CNS Cancer, Melanoma, Ovarian Cancer, Renal Cancer, Prostate Cancer, Breast Cancer, Leukemia) cell lines was investigated. Concentration of each compound (DADS, diethyl disulphide, dipropyl disulphide, diphenyl disulphide, tetraethylthiuram disulphide (TETUDS), dimetil trisulphide, dipropyl trisulphide and metilpropyl trisulphide (MPTS) was 10 µmol/L. It was found that DADS has an inhibitory effect on the growth of several cancer cell lines, but synthetic analogues TETUDS and MPTS exhibit stronger effect on certain cells lines. MPTS inhibits the growth of even 12 cell lines for more than 10%, especially leukemia cell line SR and NCI-H522 cell line of Non-Small cell Lung Cancer (reduction of growth for 24% and 47%, resp.). Trisulphide analogues exhibit little higher inhibitory effects in comparison to disulphide ones.
PB  - S.C. Virtual Company of Phisics S.R.L
T2  - Digest Journal of Nanomaterials and Biostructures
T1  - Inhibition potency of disulphides and trisulphides on various tumor cell lines growth
VL  - 16
IS  - 2
SP  - 585
EP  - 592
DO  - 10.15251/DJNB.2021.162.585
ER  - 
@article{
author = "Mandić, Boris and Simić, Katarina and Trifunović, Snežana and Vujisić, Ljubodrag and Novaković, Miroslav and Tešević, Vele and Miljanić, Ognjen Š.",
year = "2021",
abstract = "Tumor is one of the leading diseases of today. Chemotherapy and radiation therapy healing chances are limited, so some alternative methods are resorted to. Many papers indicated that garlic and organosulphur compounds diallyldisulphide (DADS) and diallyltrisulphide, which are main components of garlic decrease the cancer risk and inhibit the cell proliferation. In this paper inhibition potency of disulphides (DADS and its synthetic analogues) and trisulphides with different alkyl and phenyl substituents on growth of various tumor (Non-Small cell Lung Cancer, Colon cancer, CNS Cancer, Melanoma, Ovarian Cancer, Renal Cancer, Prostate Cancer, Breast Cancer, Leukemia) cell lines was investigated. Concentration of each compound (DADS, diethyl disulphide, dipropyl disulphide, diphenyl disulphide, tetraethylthiuram disulphide (TETUDS), dimetil trisulphide, dipropyl trisulphide and metilpropyl trisulphide (MPTS) was 10 µmol/L. It was found that DADS has an inhibitory effect on the growth of several cancer cell lines, but synthetic analogues TETUDS and MPTS exhibit stronger effect on certain cells lines. MPTS inhibits the growth of even 12 cell lines for more than 10%, especially leukemia cell line SR and NCI-H522 cell line of Non-Small cell Lung Cancer (reduction of growth for 24% and 47%, resp.). Trisulphide analogues exhibit little higher inhibitory effects in comparison to disulphide ones.",
publisher = "S.C. Virtual Company of Phisics S.R.L",
journal = "Digest Journal of Nanomaterials and Biostructures",
title = "Inhibition potency of disulphides and trisulphides on various tumor cell lines growth",
volume = "16",
number = "2",
pages = "585-592",
doi = "10.15251/DJNB.2021.162.585"
}
Mandić, B., Simić, K., Trifunović, S., Vujisić, L., Novaković, M., Tešević, V.,& Miljanić, O. Š.. (2021). Inhibition potency of disulphides and trisulphides on various tumor cell lines growth. in Digest Journal of Nanomaterials and Biostructures
S.C. Virtual Company of Phisics S.R.L., 16(2), 585-592.
https://doi.org/10.15251/DJNB.2021.162.585
Mandić B, Simić K, Trifunović S, Vujisić L, Novaković M, Tešević V, Miljanić OŠ. Inhibition potency of disulphides and trisulphides on various tumor cell lines growth. in Digest Journal of Nanomaterials and Biostructures. 2021;16(2):585-592.
doi:10.15251/DJNB.2021.162.585 .
Mandić, Boris, Simić, Katarina, Trifunović, Snežana, Vujisić, Ljubodrag, Novaković, Miroslav, Tešević, Vele, Miljanić, Ognjen Š., "Inhibition potency of disulphides and trisulphides on various tumor cell lines growth" in Digest Journal of Nanomaterials and Biostructures, 16, no. 2 (2021):585-592,
https://doi.org/10.15251/DJNB.2021.162.585 . .

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

Stanković, Jovana; Gođevac, Dejan; Cvetković, Mirjana; Tešević, Vele; Sofrenić, Ivana; Ivanović, Stefan; Novaković, Miroslav

(Portugal : PROTEOMASS Scientific Society, 2021)

TY  - CONF
AU  - Stanković, Jovana
AU  - Gođevac, Dejan
AU  - Cvetković, Mirjana
AU  - Tešević, Vele
AU  - Sofrenić, Ivana
AU  - Ivanović, Stefan
AU  - Novaković, Miroslav
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5527
AB  - A new flavonoid glucoside derivative, patuletin 3-O-(2-O-feruloyl)-β-D-glucuronopyranosyl-(1→2)-β-Dglucopyranoside, 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-Larabinopyranoside)-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, patuletin 3-O-β-D-apiofuranosyl-(1‴→2″)-β-D-glucopyranoside (5) and patuletin 3-O-5‴-Oferuloyl-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.
The best activity against Micrococcus flavus and Pseudomonas aeruginosa showed compound 1, while against
Listeria monocytogenes and Escherichia coli the strongest activity was shown by compound 5. Isolated
saponins (2-4) exhibited a more pronounced biofilm inhibition activity than flavonoid glycosides (1, 5-6). The
best anti-biofilm activity showed compound 2.
PB  - Portugal : PROTEOMASS Scientific Society
C3  - Book of abstracts - 5th International Caparica Christmas Conference on Sample Treatment (ST 2021), 15th – 18th November 2021, Caparica, Portugal
T1  - Antibacterial	 and	 Antibiofilm	 Activity	 of	 Flavonoid	 and	 Saponin	 Derivatives	 from	 Atriplex	 tatarica against	 Pseudomonas	 aeruginosa
SP  - 150
EP  - 150
UR  - https://hdl.handle.net/21.15107/rcub_cer_5527
ER  - 
@conference{
author = "Stanković, Jovana and Gođevac, Dejan and Cvetković, Mirjana and Tešević, Vele and Sofrenić, Ivana and Ivanović, Stefan and Novaković, Miroslav",
year = "2021",
abstract = "A new flavonoid glucoside derivative, patuletin 3-O-(2-O-feruloyl)-β-D-glucuronopyranosyl-(1→2)-β-Dglucopyranoside, 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-Larabinopyranoside)-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, patuletin 3-O-β-D-apiofuranosyl-(1‴→2″)-β-D-glucopyranoside (5) and patuletin 3-O-5‴-Oferuloyl-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.
The best activity against Micrococcus flavus and Pseudomonas aeruginosa showed compound 1, while against
Listeria monocytogenes and Escherichia coli the strongest activity was shown by compound 5. Isolated
saponins (2-4) exhibited a more pronounced biofilm inhibition activity than flavonoid glycosides (1, 5-6). The
best anti-biofilm activity showed compound 2.",
publisher = "Portugal : PROTEOMASS Scientific Society",
journal = "Book of abstracts - 5th International Caparica Christmas Conference on Sample Treatment (ST 2021), 15th – 18th November 2021, Caparica, Portugal",
title = "Antibacterial	 and	 Antibiofilm	 Activity	 of	 Flavonoid	 and	 Saponin	 Derivatives	 from	 Atriplex	 tatarica against	 Pseudomonas	 aeruginosa",
pages = "150-150",
url = "https://hdl.handle.net/21.15107/rcub_cer_5527"
}
Stanković, J., Gođevac, D., Cvetković, M., Tešević, V., Sofrenić, I., Ivanović, S.,& Novaković, M.. (2021). Antibacterial	 and	 Antibiofilm	 Activity	 of	 Flavonoid	 and	 Saponin	 Derivatives	 from	 Atriplex	 tatarica against	 Pseudomonas	 aeruginosa. in Book of abstracts - 5th International Caparica Christmas Conference on Sample Treatment (ST 2021), 15th – 18th November 2021, Caparica, Portugal
Portugal : PROTEOMASS Scientific Society., 150-150.
https://hdl.handle.net/21.15107/rcub_cer_5527
Stanković J, Gođevac D, Cvetković M, Tešević V, Sofrenić I, Ivanović S, Novaković M. Antibacterial	 and	 Antibiofilm	 Activity	 of	 Flavonoid	 and	 Saponin	 Derivatives	 from	 Atriplex	 tatarica against	 Pseudomonas	 aeruginosa. in Book of abstracts - 5th International Caparica Christmas Conference on Sample Treatment (ST 2021), 15th – 18th November 2021, Caparica, Portugal. 2021;:150-150.
https://hdl.handle.net/21.15107/rcub_cer_5527 .
Stanković, Jovana, Gođevac, Dejan, Cvetković, Mirjana, Tešević, Vele, Sofrenić, Ivana, Ivanović, Stefan, Novaković, Miroslav, "Antibacterial	 and	 Antibiofilm	 Activity	 of	 Flavonoid	 and	 Saponin	 Derivatives	 from	 Atriplex	 tatarica against	 Pseudomonas	 aeruginosa" in Book of abstracts - 5th International Caparica Christmas Conference on Sample Treatment (ST 2021), 15th – 18th November 2021, Caparica, Portugal (2021):150-150,
https://hdl.handle.net/21.15107/rcub_cer_5527 .

Bis-Bibenzyls from the Liverwort Pellia endiviifolia and Their Biological Activity

Ivković, Ivana; Novaković, Miroslav; Veljić, Milan; Mojsin, Marija; Stevanović, Milena J.; Marin, Petar D.; Bukvički, Danka

(MDPI, 2021)

TY  - JOUR
AU  - Ivković, Ivana
AU  - Novaković, Miroslav
AU  - Veljić, Milan
AU  - Mojsin, Marija
AU  - Stevanović, Milena J.
AU  - Marin, Petar D.
AU  - Bukvički, Danka
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4696
AB  - Based on previous investigations where bis-bibenzyls isolated from liverworts showed various biological activities (cytotoxic, antimicrobial, and antiviral), we investigated their cytotoxic activity in several human cancer cell lines. From the methylene-chloride/methanol extract of the liverwort Pellia endiviifolia, three bis-bibenzyls of the perrottetin type were isolated, namely perrottetin E, 10′-hydroxyperrottetin E, and 10,10′-dihydroxyperrottetin E. The last two were found for the first time in this species. Their structures were resolved using 1D and 2D NMR, as well as by comparison with data in the literature. Cytotoxic activity of the isolated compounds was tested on three human leukemia cell lines, HL-60 (acute promyelocytic leukemia cells), U-937 (acute monocytic leukemia cells), and K-562 (human chronic myelogenous leukemia cells), as well as on human embryonal teratocarcinoma cell line (NT2/D1) and human glioblastoma cell lines A-172 and U-251, and compared to the previously isolated bis-bibenzyls (perrottetins) of similar structure. The isolated compounds exhibited modest activity against leukemia cells and significant activity against NT2/D1 and A-172. Overall, the most active cytotoxic compounds in this investigation were perrottetin E (1), isolated in this work from Pellia endiviifolia, and perrottetin F phenanthrene derivative (7), previously isolated from Lunularia cruciata and added for a comparison of their cytotoxic activity.
PB  - MDPI
T2  - Plants
T1  - Bis-Bibenzyls from the Liverwort Pellia endiviifolia and Their Biological Activity
VL  - 10
IS  - 6
SP  - 1063
DO  - 10.3390/plants10061063
ER  - 
@article{
author = "Ivković, Ivana and Novaković, Miroslav and Veljić, Milan and Mojsin, Marija and Stevanović, Milena J. and Marin, Petar D. and Bukvički, Danka",
year = "2021",
abstract = "Based on previous investigations where bis-bibenzyls isolated from liverworts showed various biological activities (cytotoxic, antimicrobial, and antiviral), we investigated their cytotoxic activity in several human cancer cell lines. From the methylene-chloride/methanol extract of the liverwort Pellia endiviifolia, three bis-bibenzyls of the perrottetin type were isolated, namely perrottetin E, 10′-hydroxyperrottetin E, and 10,10′-dihydroxyperrottetin E. The last two were found for the first time in this species. Their structures were resolved using 1D and 2D NMR, as well as by comparison with data in the literature. Cytotoxic activity of the isolated compounds was tested on three human leukemia cell lines, HL-60 (acute promyelocytic leukemia cells), U-937 (acute monocytic leukemia cells), and K-562 (human chronic myelogenous leukemia cells), as well as on human embryonal teratocarcinoma cell line (NT2/D1) and human glioblastoma cell lines A-172 and U-251, and compared to the previously isolated bis-bibenzyls (perrottetins) of similar structure. The isolated compounds exhibited modest activity against leukemia cells and significant activity against NT2/D1 and A-172. Overall, the most active cytotoxic compounds in this investigation were perrottetin E (1), isolated in this work from Pellia endiviifolia, and perrottetin F phenanthrene derivative (7), previously isolated from Lunularia cruciata and added for a comparison of their cytotoxic activity.",
publisher = "MDPI",
journal = "Plants",
title = "Bis-Bibenzyls from the Liverwort Pellia endiviifolia and Their Biological Activity",
volume = "10",
number = "6",
pages = "1063",
doi = "10.3390/plants10061063"
}
Ivković, I., Novaković, M., Veljić, M., Mojsin, M., Stevanović, M. J., Marin, P. D.,& Bukvički, D.. (2021). Bis-Bibenzyls from the Liverwort Pellia endiviifolia and Their Biological Activity. in Plants
MDPI., 10(6), 1063.
https://doi.org/10.3390/plants10061063
Ivković I, Novaković M, Veljić M, Mojsin M, Stevanović MJ, Marin PD, Bukvički D. Bis-Bibenzyls from the Liverwort Pellia endiviifolia and Their Biological Activity. in Plants. 2021;10(6):1063.
doi:10.3390/plants10061063 .
Ivković, Ivana, Novaković, Miroslav, Veljić, Milan, Mojsin, Marija, Stevanović, Milena J., Marin, Petar D., Bukvički, Danka, "Bis-Bibenzyls from the Liverwort Pellia endiviifolia and Their Biological Activity" in Plants, 10, no. 6 (2021):1063,
https://doi.org/10.3390/plants10061063 . .
13
2
9

Antibacterial properties of thalloid liverworts Marchantia polymorpha L., Conocephalum conicum (L.) Dum. and Pellia endiviifolia (Dicks.) Dumort

Ivković, Ivana; Bukvički, Danka; Novaković, Miroslav; Ivanović, Stefan; Stanojević, Olja; Nikolić, Ivan; Veljić, Milan

(Serbian Chemical Society, 2021)

TY  - JOUR
AU  - Ivković, Ivana
AU  - Bukvički, Danka
AU  - Novaković, Miroslav
AU  - Ivanović, Stefan
AU  - Stanojević, Olja
AU  - Nikolić, Ivan
AU  - Veljić, Milan
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4920
AB  - The antimicrobial activity of methanol extracts of three thalloid liver­worts, Marchantia polymorpha, Conocephalum conicum and Pellia endiviifolia and bis-bibenzyl marchantin A, the most dominant compound in the methanol extract of M. polymorpha, have been investigated in this research. 1H-NMR spec­troscopy revealed that the M. polymorpha and P. endiviifolia extracts of liverwort contain terpenes, oils, sugars and bis-bibenzyls, while these specific macrocyclic compounds were absent in the C. conicum extract. The anti­mic­robial potential was tested on eight bacterial strains. Antimicrobial effects of extracts and mar­chantin A were observed against Gram-positive bacteria, while they showed no effect against Gram-negative bacteria in both methods used – well diffusion and broth microdilution.
AB  - У овом раду испитиван је хемијски састав и антибактеријска активност метанолних екстраката три јетрењачe, Marchantia polymorpha, Conocephalum conicum и Pellia endiveifolia и бис-бибензила маршанцина A, доминантне компоненте у метанолном екстракту M. polymorpha. 1H-NMR спектроскопија је показала присуство терпена, уља, шећера и бис-бибензила у екстрактима M. polymorpha и P. endiviifolia, док екстракт C. conicum не садржи специфична макроциклична једињења – бис-бибензиле. Антимикробни потен- цијал је тестиран на осам бактеријских сојева. Антимикробни ефекат маршанцина А уочен је на све грам позитивне сојеве, док је ефекат изостао код грам негативних сојева у обе тестиране методе – дифузионе методе у бунарима и микродилуционе методе у хранљивом бујону.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Antibacterial properties of thalloid liverworts Marchantia polymorpha L., Conocephalum conicum (L.) Dum. and Pellia endiviifolia (Dicks.) Dumort
T1  - Антибактеријска својства талусних јетрењача marchantia polymorpha l., conocephalum conicum (l.) dum. И pellia endiviifolia (dicks.) dumort.
IS  - 12
SP  - 1249
EP  - 1258
DO  - 10.2298/JSC210728084I
ER  - 
@article{
author = "Ivković, Ivana and Bukvički, Danka and Novaković, Miroslav and Ivanović, Stefan and Stanojević, Olja and Nikolić, Ivan and Veljić, Milan",
year = "2021",
abstract = "The antimicrobial activity of methanol extracts of three thalloid liver­worts, Marchantia polymorpha, Conocephalum conicum and Pellia endiviifolia and bis-bibenzyl marchantin A, the most dominant compound in the methanol extract of M. polymorpha, have been investigated in this research. 1H-NMR spec­troscopy revealed that the M. polymorpha and P. endiviifolia extracts of liverwort contain terpenes, oils, sugars and bis-bibenzyls, while these specific macrocyclic compounds were absent in the C. conicum extract. The anti­mic­robial potential was tested on eight bacterial strains. Antimicrobial effects of extracts and mar­chantin A were observed against Gram-positive bacteria, while they showed no effect against Gram-negative bacteria in both methods used – well diffusion and broth microdilution., У овом раду испитиван је хемијски састав и антибактеријска активност метанолних екстраката три јетрењачe, Marchantia polymorpha, Conocephalum conicum и Pellia endiveifolia и бис-бибензила маршанцина A, доминантне компоненте у метанолном екстракту M. polymorpha. 1H-NMR спектроскопија је показала присуство терпена, уља, шећера и бис-бибензила у екстрактима M. polymorpha и P. endiviifolia, док екстракт C. conicum не садржи специфична макроциклична једињења – бис-бибензиле. Антимикробни потен- цијал је тестиран на осам бактеријских сојева. Антимикробни ефекат маршанцина А уочен је на све грам позитивне сојеве, док је ефекат изостао код грам негативних сојева у обе тестиране методе – дифузионе методе у бунарима и микродилуционе методе у хранљивом бујону.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Antibacterial properties of thalloid liverworts Marchantia polymorpha L., Conocephalum conicum (L.) Dum. and Pellia endiviifolia (Dicks.) Dumort, Антибактеријска својства талусних јетрењача marchantia polymorpha l., conocephalum conicum (l.) dum. И pellia endiviifolia (dicks.) dumort.",
number = "12",
pages = "1249-1258",
doi = "10.2298/JSC210728084I"
}
Ivković, I., Bukvički, D., Novaković, M., Ivanović, S., Stanojević, O., Nikolić, I.,& Veljić, M.. (2021). Antibacterial properties of thalloid liverworts Marchantia polymorpha L., Conocephalum conicum (L.) Dum. and Pellia endiviifolia (Dicks.) Dumort. in Journal of the Serbian Chemical Society
Serbian Chemical Society.(12), 1249-1258.
https://doi.org/10.2298/JSC210728084I
Ivković I, Bukvički D, Novaković M, Ivanović S, Stanojević O, Nikolić I, Veljić M. Antibacterial properties of thalloid liverworts Marchantia polymorpha L., Conocephalum conicum (L.) Dum. and Pellia endiviifolia (Dicks.) Dumort. in Journal of the Serbian Chemical Society. 2021;(12):1249-1258.
doi:10.2298/JSC210728084I .
Ivković, Ivana, Bukvički, Danka, Novaković, Miroslav, Ivanović, Stefan, Stanojević, Olja, Nikolić, Ivan, Veljić, Milan, "Antibacterial properties of thalloid liverworts Marchantia polymorpha L., Conocephalum conicum (L.) Dum. and Pellia endiviifolia (Dicks.) Dumort" in Journal of the Serbian Chemical Society, no. 12 (2021):1249-1258,
https://doi.org/10.2298/JSC210728084I . .
7
1

Assessment of the Biological Effects of Pellia endiviifolia and its Constituents in Vitro

Ivković, Ivana; Bukvicki, Danka; Novaković, Miroslav; Majstorović, Ivana; Leskovac, Andreja; Petrović, Sandra; Veljić, Milan

(SAGE Publications Inc., 2021)

TY  - JOUR
AU  - Ivković, Ivana
AU  - Bukvicki, Danka
AU  - Novaković, Miroslav
AU  - Majstorović, Ivana
AU  - Leskovac, Andreja
AU  - Petrović, Sandra
AU  - Veljić, Milan
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4894
AB  - Liverworts are characterized by a high content of bioactive compounds reported to show antimicrobial, anticancer, and antioxidant properties. In this study, the biological effects of the methanol extract of the liverwort Pellia endiviifolia and its constituents, bis-bibenzyls perrottetin E, 10′-hydroxyperrottetin E, and 10,10′-dihydroxyperrottetin E, were investigated using human peripheral blood cells as a model system. The assessment of the investigated compounds comprised testing their genotoxicity, apoptotic potential, and redox modulating activities. The genotoxicity testing indicated that medium (25 µM) and high concentrations (100 µM) of the investigated compounds displayed genotoxic and antiproliferative effects in human lymphocytes as revealed by significant, concentration-dependent enhancement of the micronuclei incidence and decrease in the cytokinesis-block proliferation index compared to the control (P <.001). Analysis of leukocyte apoptosis showed a substantial potential of all investigated compounds to induce apoptosis, which was not concentration-dependent. The P endiviifolia extract and perrottetin E demonstrated considerable pro-apoptotic potential, even at the lowest concentration (1 µM) applied. Evaluation of the redox modulating effects, which comprised measuring erythrocyte catalase activity and the lymphocyte malondialdehyde level, showed that the investigated compounds did not induce oxidative stress in human peripheral blood cells (P >.05). The observed genotoxic, antiproliferative, and proapoptotic effects of the investigated compounds make them suitable for further comprehensive studies related to their possible applications as anticancer agents.
PB  - SAGE Publications Inc.
T2  - Natural Product Communications
T1  - Assessment of the Biological Effects of Pellia endiviifolia and its Constituents in Vitro
VL  - 16
IS  - 11
SP  - 1
EP  - 9
DO  - 10.1177/1934578X211056422
ER  - 
@article{
author = "Ivković, Ivana and Bukvicki, Danka and Novaković, Miroslav and Majstorović, Ivana and Leskovac, Andreja and Petrović, Sandra and Veljić, Milan",
year = "2021",
abstract = "Liverworts are characterized by a high content of bioactive compounds reported to show antimicrobial, anticancer, and antioxidant properties. In this study, the biological effects of the methanol extract of the liverwort Pellia endiviifolia and its constituents, bis-bibenzyls perrottetin E, 10′-hydroxyperrottetin E, and 10,10′-dihydroxyperrottetin E, were investigated using human peripheral blood cells as a model system. The assessment of the investigated compounds comprised testing their genotoxicity, apoptotic potential, and redox modulating activities. The genotoxicity testing indicated that medium (25 µM) and high concentrations (100 µM) of the investigated compounds displayed genotoxic and antiproliferative effects in human lymphocytes as revealed by significant, concentration-dependent enhancement of the micronuclei incidence and decrease in the cytokinesis-block proliferation index compared to the control (P <.001). Analysis of leukocyte apoptosis showed a substantial potential of all investigated compounds to induce apoptosis, which was not concentration-dependent. The P endiviifolia extract and perrottetin E demonstrated considerable pro-apoptotic potential, even at the lowest concentration (1 µM) applied. Evaluation of the redox modulating effects, which comprised measuring erythrocyte catalase activity and the lymphocyte malondialdehyde level, showed that the investigated compounds did not induce oxidative stress in human peripheral blood cells (P >.05). The observed genotoxic, antiproliferative, and proapoptotic effects of the investigated compounds make them suitable for further comprehensive studies related to their possible applications as anticancer agents.",
publisher = "SAGE Publications Inc.",
journal = "Natural Product Communications",
title = "Assessment of the Biological Effects of Pellia endiviifolia and its Constituents in Vitro",
volume = "16",
number = "11",
pages = "1-9",
doi = "10.1177/1934578X211056422"
}
Ivković, I., Bukvicki, D., Novaković, M., Majstorović, I., Leskovac, A., Petrović, S.,& Veljić, M.. (2021). Assessment of the Biological Effects of Pellia endiviifolia and its Constituents in Vitro. in Natural Product Communications
SAGE Publications Inc.., 16(11), 1-9.
https://doi.org/10.1177/1934578X211056422
Ivković I, Bukvicki D, Novaković M, Majstorović I, Leskovac A, Petrović S, Veljić M. Assessment of the Biological Effects of Pellia endiviifolia and its Constituents in Vitro. in Natural Product Communications. 2021;16(11):1-9.
doi:10.1177/1934578X211056422 .
Ivković, Ivana, Bukvicki, Danka, Novaković, Miroslav, Majstorović, Ivana, Leskovac, Andreja, Petrović, Sandra, Veljić, Milan, "Assessment of the Biological Effects of Pellia endiviifolia and its Constituents in Vitro" in Natural Product Communications, 16, no. 11 (2021):1-9,
https://doi.org/10.1177/1934578X211056422 . .
2
1

Biotransformation of Perrottetin F by Aspergillus niger: New Bioactive Secondary Metabolites

Bukvicki, Danka; Novaković, Miroslav; Ilić - Tomić, Tatjana; Nikodinović-Runić, Jasmina; Todorović, Nina; Veljić, Milan; Asakawa, Yoshinori

(Türkiye : ACG Publications, 2021)

TY  - JOUR
AU  - Bukvicki, Danka
AU  - Novaković, Miroslav
AU  - Ilić - Tomić, Tatjana
AU  - Nikodinović-Runić, Jasmina
AU  - Todorović, Nina
AU  - Veljić, Milan
AU  - Asakawa, Yoshinori
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4630
AB  - Biotransformation of bis-bibenzyl perrottetin F (1), isolated from the liverwort Lunularia cruciata by Aspergillus niger, has been investigated. New metabolites (2-4) have been isolated using reversed phase semipreparative HPLC and their structures were established to be 8-hydroxyperrottetin F, C-7-C-8 cleaved product, and perrottetin F 6’-sulfate using 1D and 2D NMR, HR-ESI-MS, IR and UV spectroscopy. The antimicrobial and cytotoxic properties of these compounds were also evaluated. Given the suggested cytotoxic properties of the parent compound, antiproliferative activity against healthy human lung fibroblasts (MRC5) and human lung carcinoma (A549) of three metabolites were evaluated revealing their lower cytotoxic properties in comparison to the starting compound-perrottetin F. The antimicrobial properties of these compounds were also evaluated, with the inhibitory activity against the Pseudomonas aeruginosa PAO1 and Staphylococcus aureus determined between 100 µM and 450 µM. The metabolites showed remarkable ability to inhibit synthesis of bacterial quorum-sensing signal molecules such as short chain acyl homoserine lactones (AHLs). Therefore, biotransformation method represents fast and effective tool for obtaining new bioactive structures.
PB  - Türkiye : ACG Publications
T2  - Records of Natural Products
T1  - Biotransformation of Perrottetin F by Aspergillus niger: New Bioactive Secondary Metabolites
VL  - 15
IS  - 4
SP  - 281
EP  - 292
DO  - 10.25135/rnp.215.20.09.1812
ER  - 
@article{
author = "Bukvicki, Danka and Novaković, Miroslav and Ilić - Tomić, Tatjana and Nikodinović-Runić, Jasmina and Todorović, Nina and Veljić, Milan and Asakawa, Yoshinori",
year = "2021",
abstract = "Biotransformation of bis-bibenzyl perrottetin F (1), isolated from the liverwort Lunularia cruciata by Aspergillus niger, has been investigated. New metabolites (2-4) have been isolated using reversed phase semipreparative HPLC and their structures were established to be 8-hydroxyperrottetin F, C-7-C-8 cleaved product, and perrottetin F 6’-sulfate using 1D and 2D NMR, HR-ESI-MS, IR and UV spectroscopy. The antimicrobial and cytotoxic properties of these compounds were also evaluated. Given the suggested cytotoxic properties of the parent compound, antiproliferative activity against healthy human lung fibroblasts (MRC5) and human lung carcinoma (A549) of three metabolites were evaluated revealing their lower cytotoxic properties in comparison to the starting compound-perrottetin F. The antimicrobial properties of these compounds were also evaluated, with the inhibitory activity against the Pseudomonas aeruginosa PAO1 and Staphylococcus aureus determined between 100 µM and 450 µM. The metabolites showed remarkable ability to inhibit synthesis of bacterial quorum-sensing signal molecules such as short chain acyl homoserine lactones (AHLs). Therefore, biotransformation method represents fast and effective tool for obtaining new bioactive structures.",
publisher = "Türkiye : ACG Publications",
journal = "Records of Natural Products",
title = "Biotransformation of Perrottetin F by Aspergillus niger: New Bioactive Secondary Metabolites",
volume = "15",
number = "4",
pages = "281-292",
doi = "10.25135/rnp.215.20.09.1812"
}
Bukvicki, D., Novaković, M., Ilić - Tomić, T., Nikodinović-Runić, J., Todorović, N., Veljić, M.,& Asakawa, Y.. (2021). Biotransformation of Perrottetin F by Aspergillus niger: New Bioactive Secondary Metabolites. in Records of Natural Products
Türkiye : ACG Publications., 15(4), 281-292.
https://doi.org/10.25135/rnp.215.20.09.1812
Bukvicki D, Novaković M, Ilić - Tomić T, Nikodinović-Runić J, Todorović N, Veljić M, Asakawa Y. Biotransformation of Perrottetin F by Aspergillus niger: New Bioactive Secondary Metabolites. in Records of Natural Products. 2021;15(4):281-292.
doi:10.25135/rnp.215.20.09.1812 .
Bukvicki, Danka, Novaković, Miroslav, Ilić - Tomić, Tatjana, Nikodinović-Runić, Jasmina, Todorović, Nina, Veljić, Milan, Asakawa, Yoshinori, "Biotransformation of Perrottetin F by Aspergillus niger: New Bioactive Secondary Metabolites" in Records of Natural Products, 15, no. 4 (2021):281-292,
https://doi.org/10.25135/rnp.215.20.09.1812 . .
6
4
5

Lamiaceae in the treatment of cardiovascular diseases

Patrignani, Francesca; Prasad, Sahdeo; Novaković, Miroslav; Marin, Petar D.; Bukvicki, Danka

(Frontiers in Bioscience - Landmark, 2021)

TY  - JOUR
AU  - Patrignani, Francesca
AU  - Prasad, Sahdeo
AU  - Novaković, Miroslav
AU  - Marin, Petar D.
AU  - Bukvicki, Danka
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4522
AB  - Lamiaceae (Labiatae) are an important group of medicinal plants, which have been used for treating heart disease in traditional medicine for centuries. These mainly aromatic plants are used as essential oils, extracts or isolated components (polyphenols, phenolic compounds, terpenes, iridoids etc.). Some Labiatae species (more than 30, such as cornmint, lavender, patchouli, rosemary etc.) are famous for their use in essential oil production worldwide. In this review, cardioprotective effects of Lamiaceae and their active secondary metabolites, as well as mechanism of action against cardiovascular diseases (hypertension, angina pectoris, hyperlipidemia, thromboembolism, coronary heart disease, heart failure, venous insufficiency, arrhythmia) will be discussed. Use of Labiatae as food or food additives (such as spices) may prevent risk of cardiovascular diseases, diabetes and cancer. This approach is also described as a part of the article. Studies on developing new, effective and safe natural products from Lamiaceae (rich source of flavonoids and other active compounds) are promising and may offer prevention and treatment for patients with coronary disease and other related diseases.
PB  - Frontiers in Bioscience - Landmark
T2  - Frontiers in Bioscience-Landmark
T1  - Lamiaceae in the treatment of cardiovascular diseases
VL  - 26
IS  - 4
SP  - 612
EP  - 643
DO  - 10.2741/4909
ER  - 
@article{
author = "Patrignani, Francesca and Prasad, Sahdeo and Novaković, Miroslav and Marin, Petar D. and Bukvicki, Danka",
year = "2021",
abstract = "Lamiaceae (Labiatae) are an important group of medicinal plants, which have been used for treating heart disease in traditional medicine for centuries. These mainly aromatic plants are used as essential oils, extracts or isolated components (polyphenols, phenolic compounds, terpenes, iridoids etc.). Some Labiatae species (more than 30, such as cornmint, lavender, patchouli, rosemary etc.) are famous for their use in essential oil production worldwide. In this review, cardioprotective effects of Lamiaceae and their active secondary metabolites, as well as mechanism of action against cardiovascular diseases (hypertension, angina pectoris, hyperlipidemia, thromboembolism, coronary heart disease, heart failure, venous insufficiency, arrhythmia) will be discussed. Use of Labiatae as food or food additives (such as spices) may prevent risk of cardiovascular diseases, diabetes and cancer. This approach is also described as a part of the article. Studies on developing new, effective and safe natural products from Lamiaceae (rich source of flavonoids and other active compounds) are promising and may offer prevention and treatment for patients with coronary disease and other related diseases.",
publisher = "Frontiers in Bioscience - Landmark",
journal = "Frontiers in Bioscience-Landmark",
title = "Lamiaceae in the treatment of cardiovascular diseases",
volume = "26",
number = "4",
pages = "612-643",
doi = "10.2741/4909"
}
Patrignani, F., Prasad, S., Novaković, M., Marin, P. D.,& Bukvicki, D.. (2021). Lamiaceae in the treatment of cardiovascular diseases. in Frontiers in Bioscience-Landmark
Frontiers in Bioscience - Landmark., 26(4), 612-643.
https://doi.org/10.2741/4909
Patrignani F, Prasad S, Novaković M, Marin PD, Bukvicki D. Lamiaceae in the treatment of cardiovascular diseases. in Frontiers in Bioscience-Landmark. 2021;26(4):612-643.
doi:10.2741/4909 .
Patrignani, Francesca, Prasad, Sahdeo, Novaković, Miroslav, Marin, Petar D., Bukvicki, Danka, "Lamiaceae in the treatment of cardiovascular diseases" in Frontiers in Bioscience-Landmark, 26, no. 4 (2021):612-643,
https://doi.org/10.2741/4909 . .
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Potential for cancer treatment: natural products from the Balkans

Dinić, Jelena; Novaković, Miroslav; Pešić, Milica

(Elsevier, 2020)

TY  - CHAP
AU  - Dinić, Jelena
AU  - Novaković, Miroslav
AU  - Pešić, Milica
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4396
AB  - Natural products represent a key source of novel drug leads and their essential value in anticancer research is being increasingly recognized. The presence, quantity, and structural characteristics of natural compounds within the same species could differ between regions as a result of environmental variations contributing to intraspecific chemodiversity. The Balkan Peninsula is a vital part of Europe’s biodiversity, with a considerable number of endemic species and with a broad ecosystem distribution. This region provides an unlimited supply of unique, structurally diverse compounds and offers vast potential for discovering and developing therapeutics for human benefit. This chapter gives an overview of anticancer compounds derived from natural sources of the Balkans and underlines the importance for the long-term conservation of biodiversity in this part of Europe.
PB  - Elsevier
T2  - Biodiversity and Biomedicine: our future
T1  - Potential for cancer treatment: natural products from the Balkans
SP  - 137
EP  - 159
DO  - 10.1016/B978-0-12-819541-3.00009-8
ER  - 
@inbook{
author = "Dinić, Jelena and Novaković, Miroslav and Pešić, Milica",
year = "2020",
abstract = "Natural products represent a key source of novel drug leads and their essential value in anticancer research is being increasingly recognized. The presence, quantity, and structural characteristics of natural compounds within the same species could differ between regions as a result of environmental variations contributing to intraspecific chemodiversity. The Balkan Peninsula is a vital part of Europe’s biodiversity, with a considerable number of endemic species and with a broad ecosystem distribution. This region provides an unlimited supply of unique, structurally diverse compounds and offers vast potential for discovering and developing therapeutics for human benefit. This chapter gives an overview of anticancer compounds derived from natural sources of the Balkans and underlines the importance for the long-term conservation of biodiversity in this part of Europe.",
publisher = "Elsevier",
journal = "Biodiversity and Biomedicine: our future",
booktitle = "Potential for cancer treatment: natural products from the Balkans",
pages = "137-159",
doi = "10.1016/B978-0-12-819541-3.00009-8"
}
Dinić, J., Novaković, M.,& Pešić, M.. (2020). Potential for cancer treatment: natural products from the Balkans. in Biodiversity and Biomedicine: our future
Elsevier., 137-159.
https://doi.org/10.1016/B978-0-12-819541-3.00009-8
Dinić J, Novaković M, Pešić M. Potential for cancer treatment: natural products from the Balkans. in Biodiversity and Biomedicine: our future. 2020;:137-159.
doi:10.1016/B978-0-12-819541-3.00009-8 .
Dinić, Jelena, Novaković, Miroslav, Pešić, Milica, "Potential for cancer treatment: natural products from the Balkans" in Biodiversity and Biomedicine: our future (2020):137-159,
https://doi.org/10.1016/B978-0-12-819541-3.00009-8 . .
1

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

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

(Elsevier, 2020)

TY  - JOUR
AU  - Novaković, Miroslav
AU  - Simić, Stefan
AU  - Koračak, Ljiljana
AU  - Zlatović, Mario
AU  - Ilić-Tomić, Tatjana
AU  - Asakawa, Yoshinori
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2020
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3867
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3441
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 and Simić, Stefan and Koračak, Ljiljana and Zlatović, Mario and Ilić-Tomić, 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., Simić, S., Koračak, L., Zlatović, M., Ilić-Tomić, 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 M, Simić S, Koračak L, Zlatović M, Ilić-Tomić 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, Simić, Stefan, Koračak, Ljiljana, Zlatović, Mario, Ilić-Tomić, 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 . .
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