TY  - JOUR
AU  - Jadranin, Milka
AU  - Savić, Danica
AU  - Lupšić, Ema
AU  - Podolski-Renić, Ana
AU  - Pešić, Milica
AU  - Tešević, Vele
AU  - Milosavljević, Slobodan M.
AU  - Krstić, Gordana B.
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7540
AB  - Euphorbia seguieriana ssp. seguieriana Necker (ES) and Euphorbia cyparissias (EC) with a habitat in the Deliblato Sands were the subject of this examination. The latexes of these so far insufficiently investigated species of the Euphorbia genus are used in traditional medicine for the treatment of wounds and warts on the skin. To determine their chemical composition, non-targeted screening of the latexes’ chloroform extracts was performed using liquid chromatography coupled with quadrupole time-of-flight mass spectrometry employing an electrospray ionization source (LC-ESI QTOF MS). The analysis of the obtained results showed that the latexes of ES and EC represent rich sources of diterpenes, tentatively identified as jatrophanes, ingenanes, tiglianes, myrsinanes, premyrsinanes, and others. Examination of the anticancer activity of the ES and EC latex extracts showed that both extracts significantly inhibited the growth of the non-small cell lung carcinoma NCI-H460 and glioblastoma U87 cell lines as well as of their corresponding multi-drug resistant (MDR) cell lines, NCI-H460/R and U87-TxR. The obtained results also revealed that the ES and EC extracts inhibited the function of P-glycoprotein (P-gp) in MDR cancer cells, whose overexpression is one of the main mechanisms underlying MDR.
PB  - MDPI
T2  - Plants
T1  - LC-ESI QToF MS Non-Targeted Screening of Latex Extracts of Euphorbia seguieriana ssp. seguieriana Necker and Euphorbia cyparissias and Determination of Their Potential Anticancer Activity
VL  - 12
IS  - 24
SP  - 4181
DO  - 10.3390/plants12244181
ER  - 

@article{
author = "Jadranin, Milka and Savić, Danica and Lupšić, Ema and Podolski-Renić, Ana and Pešić, Milica and Tešević, Vele and Milosavljević, Slobodan M. and Krstić, Gordana B.",
year = "2023",
abstract = "Euphorbia seguieriana ssp. seguieriana Necker (ES) and Euphorbia cyparissias (EC) with a habitat in the Deliblato Sands were the subject of this examination. The latexes of these so far insufficiently investigated species of the Euphorbia genus are used in traditional medicine for the treatment of wounds and warts on the skin. To determine their chemical composition, non-targeted screening of the latexes’ chloroform extracts was performed using liquid chromatography coupled with quadrupole time-of-flight mass spectrometry employing an electrospray ionization source (LC-ESI QTOF MS). The analysis of the obtained results showed that the latexes of ES and EC represent rich sources of diterpenes, tentatively identified as jatrophanes, ingenanes, tiglianes, myrsinanes, premyrsinanes, and others. Examination of the anticancer activity of the ES and EC latex extracts showed that both extracts significantly inhibited the growth of the non-small cell lung carcinoma NCI-H460 and glioblastoma U87 cell lines as well as of their corresponding multi-drug resistant (MDR) cell lines, NCI-H460/R and U87-TxR. The obtained results also revealed that the ES and EC extracts inhibited the function of P-glycoprotein (P-gp) in MDR cancer cells, whose overexpression is one of the main mechanisms underlying MDR.",
publisher = "MDPI",
journal = "Plants",
title = "LC-ESI QToF MS Non-Targeted Screening of Latex Extracts of Euphorbia seguieriana ssp. seguieriana Necker and Euphorbia cyparissias and Determination of Their Potential Anticancer Activity",
volume = "12",
number = "24",
pages = "4181",
doi = "10.3390/plants12244181"
}

Jadranin, M., Savić, D., Lupšić, E., Podolski-Renić, A., Pešić, M., Tešević, V., Milosavljević, S. M.,& Krstić, G. B.. (2023). LC-ESI QToF MS Non-Targeted Screening of Latex Extracts of Euphorbia seguieriana ssp. seguieriana Necker and Euphorbia cyparissias and Determination of Their Potential Anticancer Activity. in Plants
MDPI., 12(24), 4181.
https://doi.org/10.3390/plants12244181

Jadranin M, Savić D, Lupšić E, Podolski-Renić A, Pešić M, Tešević V, Milosavljević SM, Krstić GB. LC-ESI QToF MS Non-Targeted Screening of Latex Extracts of Euphorbia seguieriana ssp. seguieriana Necker and Euphorbia cyparissias and Determination of Their Potential Anticancer Activity. in Plants. 2023;12(24):4181.
doi:10.3390/plants12244181 .

Jadranin, Milka, Savić, Danica, Lupšić, Ema, Podolski-Renić, Ana, Pešić, Milica, Tešević, Vele, Milosavljević, Slobodan M., Krstić, Gordana B., "LC-ESI QToF MS Non-Targeted Screening of Latex Extracts of Euphorbia seguieriana ssp. seguieriana Necker and Euphorbia cyparissias and Determination of Their Potential Anticancer Activity" in Plants, 12, no. 24 (2023):4181,
https://doi.org/10.3390/plants12244181 . .

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 .

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 .

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 .

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 .

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 .

TY  - JOUR
AU  - Sofrenić, Ivana
AU  - Anđelković, Boban
AU  - Gođevac, Dejan
AU  - Ivanović, Stefan
AU  - Simić, Katarina
AU  - Ljujić, Jovana
AU  - Tešević, Vele
AU  - Milosavljević, Slobodan
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5655
AB  - Chemotaxonomy presents various challenges that need to be overcome in order to obtain valid and reliable results. Individual genetic and environmental variations can give a false picture and lead to wrong conclusions. Applying a holistic approach, based on multivariate data analysis, these challenges can be overcome. Thus, a metabolomics approach has to be optimized depending on the subject of research. We used 1H NMR-based metabolomics as a potential chemotaxonomic tool on the selected Euphorbia species growing wild in Serbia. Principal components analysis (PCA), soft independent modeling by class analogy (SIMCA) and Orthogonal Projections to Latent Structures Discriminant Analysis (OPLS-DA) were used to analyze obtained NMR data in order to reveal chemotaxonomic biomarkers. The standard protocol for plant metabolomics was optimized aiming to extract more specific metabolites, which are characteristic for the Euphorbia genus. The obtained models were validated, which revealed that variables unique for each species were associated with certain classes of molecules according to literature data. In E. salicifolia, acacetin-7-O-glycoside (not found before in the species) was detected, and the structure of the aglycone part was solved based on 2D NMR data. In the presented paper, we have shown that metabolomics can be successfully used in Euphorbia chemotaxonomy.
PB  - Switzerland : Multidisciplinary Digital Publishing Institute (MDPI)
T2  - Plants
T1  - Metabolomics as a Potential Chemotaxonomical Tool: Application on the Selected Euphorbia Species Growing Wild in Serbia
VL  - 12
IS  - 2
SP  - 262
DO  - 10.3390/plants12020262
ER  - 

@article{
author = "Sofrenić, Ivana and Anđelković, Boban and Gođevac, Dejan and Ivanović, Stefan and Simić, Katarina and Ljujić, Jovana and Tešević, Vele and Milosavljević, Slobodan",
year = "2023",
abstract = "Chemotaxonomy presents various challenges that need to be overcome in order to obtain valid and reliable results. Individual genetic and environmental variations can give a false picture and lead to wrong conclusions. Applying a holistic approach, based on multivariate data analysis, these challenges can be overcome. Thus, a metabolomics approach has to be optimized depending on the subject of research. We used 1H NMR-based metabolomics as a potential chemotaxonomic tool on the selected Euphorbia species growing wild in Serbia. Principal components analysis (PCA), soft independent modeling by class analogy (SIMCA) and Orthogonal Projections to Latent Structures Discriminant Analysis (OPLS-DA) were used to analyze obtained NMR data in order to reveal chemotaxonomic biomarkers. The standard protocol for plant metabolomics was optimized aiming to extract more specific metabolites, which are characteristic for the Euphorbia genus. The obtained models were validated, which revealed that variables unique for each species were associated with certain classes of molecules according to literature data. In E. salicifolia, acacetin-7-O-glycoside (not found before in the species) was detected, and the structure of the aglycone part was solved based on 2D NMR data. In the presented paper, we have shown that metabolomics can be successfully used in Euphorbia chemotaxonomy.",
publisher = "Switzerland : Multidisciplinary Digital Publishing Institute (MDPI)",
journal = "Plants",
title = "Metabolomics as a Potential Chemotaxonomical Tool: Application on the Selected Euphorbia Species Growing Wild in Serbia",
volume = "12",
number = "2",
pages = "262",
doi = "10.3390/plants12020262"
}

Sofrenić, I., Anđelković, B., Gođevac, D., Ivanović, S., Simić, K., Ljujić, J., Tešević, V.,& Milosavljević, S.. (2023). Metabolomics as a Potential Chemotaxonomical Tool: Application on the Selected Euphorbia Species Growing Wild in Serbia. in Plants
Switzerland : Multidisciplinary Digital Publishing Institute (MDPI)., 12(2), 262.
https://doi.org/10.3390/plants12020262

Sofrenić I, Anđelković B, Gođevac D, Ivanović S, Simić K, Ljujić J, Tešević V, Milosavljević S. Metabolomics as a Potential Chemotaxonomical Tool: Application on the Selected Euphorbia Species Growing Wild in Serbia. in Plants. 2023;12(2):262.
doi:10.3390/plants12020262 .

Sofrenić, Ivana, Anđelković, Boban, Gođevac, Dejan, Ivanović, Stefan, Simić, Katarina, Ljujić, Jovana, Tešević, Vele, Milosavljević, Slobodan, "Metabolomics as a Potential Chemotaxonomical Tool: Application on the Selected Euphorbia Species Growing Wild in Serbia" in Plants, 12, no. 2 (2023):262,
https://doi.org/10.3390/plants12020262 . .

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 . .

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 . .

TY  - CONF
AU  - Krstić, Gordana
AU  - Jadranin, Milka
AU  - Jovanović Stojanov, Sofija
AU  - Pešić, Milica
AU  - Tešević, Vele
AU  - Milosavljević, Slobodan
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5862
AB  - In this research, from two species, E. palustris and E.  lucida, four ingenane derivatives were isolated. Their anticancer effects were evaluated in the human melanoma  – 518A2 cell line and compared with the effects of ingenolmebutate. Selectivity towards human melanoma cells was  determined using normal human keratinocytes – HaCaT.
PB  - Macedonian Pharmaceutical Association
C3  - Macedonian Pharmaceutical Bulletin
T1  - Anti-melanoma effects of ingenanes isolated from Euphorbia species
VL  - 68
IS  - Suppl.2
SP  - 23
EP  - 24
DO  - 10.33320/maced.pharm.bull.2022.68.04.006
ER  - 

@conference{
author = "Krstić, Gordana and Jadranin, Milka and Jovanović Stojanov, Sofija and Pešić, Milica and Tešević, Vele and Milosavljević, Slobodan",
year = "2022",
abstract = "In this research, from two species, E. palustris and E.  lucida, four ingenane derivatives were isolated. Their anticancer effects were evaluated in the human melanoma  – 518A2 cell line and compared with the effects of ingenolmebutate. Selectivity towards human melanoma cells was  determined using normal human keratinocytes – HaCaT.",
publisher = "Macedonian Pharmaceutical Association",
journal = "Macedonian Pharmaceutical Bulletin",
title = "Anti-melanoma effects of ingenanes isolated from Euphorbia species",
volume = "68",
number = "Suppl.2",
pages = "23-24",
doi = "10.33320/maced.pharm.bull.2022.68.04.006"
}

Krstić, G., Jadranin, M., Jovanović Stojanov, S., Pešić, M., Tešević, V.,& Milosavljević, S.. (2022). Anti-melanoma effects of ingenanes isolated from Euphorbia species. in Macedonian Pharmaceutical Bulletin
Macedonian Pharmaceutical Association., 68(Suppl.2), 23-24.
https://doi.org/10.33320/maced.pharm.bull.2022.68.04.006

Krstić G, Jadranin M, Jovanović Stojanov S, Pešić M, Tešević V, Milosavljević S. Anti-melanoma effects of ingenanes isolated from Euphorbia species. in Macedonian Pharmaceutical Bulletin. 2022;68(Suppl.2):23-24.
doi:10.33320/maced.pharm.bull.2022.68.04.006 .

Krstić, Gordana, Jadranin, Milka, Jovanović Stojanov, Sofija, Pešić, Milica, Tešević, Vele, Milosavljević, Slobodan, "Anti-melanoma effects of ingenanes isolated from Euphorbia species" in Macedonian Pharmaceutical Bulletin, 68, no. Suppl.2 (2022):23-24,
https://doi.org/10.33320/maced.pharm.bull.2022.68.04.006 . .

TY  - CONF
AU  - Jadranin, Milka
AU  - Cvetković, Mirjana
AU  - Đorđević, Iris
AU  - Krstić, Gordana
AU  - Tešević, Vele
AU  - Milosavljević, Slobodan
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5863
AB  - This study revealed results from reinvestigation of  sesquiterpene lactones composition in the crude and leaf  surface extracts of Amphoricarpos plants by rapid  resolution liquid chromatography (RRLC) coupled with  quadrupole time-of-flight mass spectrometry (QToF MS)  and the tentative identification of undescribed  sesquiterpene lactones is presented.
PB  - Macedonian Pharmaceutical Association
C3  - Macedonian Pharmaceutical Bulletin
T1  - New insights into sesquiterpene lactones composition of 
Western Balkan’s genus Amphoricarpos revealed by rapid 
resolution liquid chromatography coupled with quadrupole time-of-flight mass spectrometry
VL  - 68
IS  - Suppl.2
SP  - 71
EP  - 72
DO  - 10.33320/maced.pharm.bull.2022.68.04.030
ER  - 

@conference{
author = "Jadranin, Milka and Cvetković, Mirjana and Đorđević, Iris and Krstić, Gordana and Tešević, Vele and Milosavljević, Slobodan",
year = "2022",
abstract = "This study revealed results from reinvestigation of  sesquiterpene lactones composition in the crude and leaf  surface extracts of Amphoricarpos plants by rapid  resolution liquid chromatography (RRLC) coupled with  quadrupole time-of-flight mass spectrometry (QToF MS)  and the tentative identification of undescribed  sesquiterpene lactones is presented.",
publisher = "Macedonian Pharmaceutical Association",
journal = "Macedonian Pharmaceutical Bulletin",
title = "New insights into sesquiterpene lactones composition of 
Western Balkan’s genus Amphoricarpos revealed by rapid 
resolution liquid chromatography coupled with quadrupole time-of-flight mass spectrometry",
volume = "68",
number = "Suppl.2",
pages = "71-72",
doi = "10.33320/maced.pharm.bull.2022.68.04.030"
}

Jadranin, M., Cvetković, M., Đorđević, I., Krstić, G., Tešević, V.,& Milosavljević, S.. (2022). New insights into sesquiterpene lactones composition of 
Western Balkan’s genus Amphoricarpos revealed by rapid 
resolution liquid chromatography coupled with quadrupole time-of-flight mass spectrometry. in Macedonian Pharmaceutical Bulletin
Macedonian Pharmaceutical Association., 68(Suppl.2), 71-72.
https://doi.org/10.33320/maced.pharm.bull.2022.68.04.030

Jadranin M, Cvetković M, Đorđević I, Krstić G, Tešević V, Milosavljević S. New insights into sesquiterpene lactones composition of 
Western Balkan’s genus Amphoricarpos revealed by rapid 
resolution liquid chromatography coupled with quadrupole time-of-flight mass spectrometry. in Macedonian Pharmaceutical Bulletin. 2022;68(Suppl.2):71-72.
doi:10.33320/maced.pharm.bull.2022.68.04.030 .

Jadranin, Milka, Cvetković, Mirjana, Đorđević, Iris, Krstić, Gordana, Tešević, Vele, Milosavljević, Slobodan, "New insights into sesquiterpene lactones composition of 
Western Balkan’s genus Amphoricarpos revealed by rapid 
resolution liquid chromatography coupled with quadrupole time-of-flight mass spectrometry" in Macedonian Pharmaceutical Bulletin, 68, no. Suppl.2 (2022):71-72,
https://doi.org/10.33320/maced.pharm.bull.2022.68.04.030 . .

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 .

TY  - CONF
AU  - Savić, Danica
AU  - Krstić, Gordana
AU  - Jadranin, Milka
AU  - Tešević, Vele
AU  - Milosavljević, Slobodan
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5875
AB  - Plant species of the genus Euphorbia have an important place in the traditional medicine due to the secondary metabolites which they produce. The most important metabolites  come from the classes of diterpenes and triterpenes. The studies have shown that these  compounds can have antitumour, antiviral, antibacterial, anti-inflammatory and other  properties. The aim of the research was to investigatethe triterpene composition of  Euphorbia palustris. Using chromatographic techniques, four triterpene derivatives were  isolated from the plant material, as follows: (+)-tirucallol (1), lanosterol (2), 27-nor-3βhydroxycycloart-23-en-25-one (3) and (+)-obtusifoliol (4). In the continuation of the  research, their biological activities will be examined.
AB  - Biljne vrste roda Euphorbia imaju važno mesto u tradicionalnoj medicini zahvaljujući  sekundarnim metabolitima koje proizvode. Najznačajniji metaboliti pripadaju klasama  diterpena i triterpena. Istraživanja su pokazala da ova jedinjenja imaju antitumorska,  antivirusna, antibakterijska, antiinflamatorna i druga svojstva. Cilj ovog istraživanja bio je  ispitivanje triterpenskog sastava biljne vrste Euphorbia palustris. Primenom  hromatografskih tehnika iz biljnog materijala izolovana su četiri triterpenska derivata i  to:(+)-tirukalol (1), lanosterol (2), 27-nor-3β-hidroksicikloart-23-en-25-on (3) i (+)- obtusifoliol (4). U nastavku istraživanja biće ispitane njihove biološke aktivnosti.
PB  - Serbian Chemical Society
C3  - Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, June 9-10, 2022 / Kratki izvodi radova, kjniga radova - 58. Savetovanje Srpskog hemijskog društva, Beograd 9. i 10. jun 2022. godine
T1  - Triterpene composition of the plant species Euphorbia palustris
T1  - Triterpeni biljne vrste Euphorbia palustris
SP  - 143
UR  - https://hdl.handle.net/21.15107/rcub_cer_5875
ER  - 

@conference{
author = "Savić, Danica and Krstić, Gordana and Jadranin, Milka and Tešević, Vele and Milosavljević, Slobodan",
year = "2022",
abstract = "Plant species of the genus Euphorbia have an important place in the traditional medicine due to the secondary metabolites which they produce. The most important metabolites  come from the classes of diterpenes and triterpenes. The studies have shown that these  compounds can have antitumour, antiviral, antibacterial, anti-inflammatory and other  properties. The aim of the research was to investigatethe triterpene composition of  Euphorbia palustris. Using chromatographic techniques, four triterpene derivatives were  isolated from the plant material, as follows: (+)-tirucallol (1), lanosterol (2), 27-nor-3βhydroxycycloart-23-en-25-one (3) and (+)-obtusifoliol (4). In the continuation of the  research, their biological activities will be examined., Biljne vrste roda Euphorbia imaju važno mesto u tradicionalnoj medicini zahvaljujući  sekundarnim metabolitima koje proizvode. Najznačajniji metaboliti pripadaju klasama  diterpena i triterpena. Istraživanja su pokazala da ova jedinjenja imaju antitumorska,  antivirusna, antibakterijska, antiinflamatorna i druga svojstva. Cilj ovog istraživanja bio je  ispitivanje triterpenskog sastava biljne vrste Euphorbia palustris. Primenom  hromatografskih tehnika iz biljnog materijala izolovana su četiri triterpenska derivata i  to:(+)-tirukalol (1), lanosterol (2), 27-nor-3β-hidroksicikloart-23-en-25-on (3) i (+)- obtusifoliol (4). U nastavku istraživanja biće ispitane njihove biološke aktivnosti.",
publisher = "Serbian Chemical Society",
journal = "Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, June 9-10, 2022 / Kratki izvodi radova, kjniga radova - 58. Savetovanje Srpskog hemijskog društva, Beograd 9. i 10. jun 2022. godine",
title = "Triterpene composition of the plant species Euphorbia palustris, Triterpeni biljne vrste Euphorbia palustris",
pages = "143",
url = "https://hdl.handle.net/21.15107/rcub_cer_5875"
}

Savić, D., Krstić, G., Jadranin, M., Tešević, V.,& Milosavljević, S.. (2022). Triterpene composition of the plant species Euphorbia palustris. in Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, June 9-10, 2022 / Kratki izvodi radova, kjniga radova - 58. Savetovanje Srpskog hemijskog društva, Beograd 9. i 10. jun 2022. godine
Serbian Chemical Society., 143.
https://hdl.handle.net/21.15107/rcub_cer_5875

Savić D, Krstić G, Jadranin M, Tešević V, Milosavljević S. Triterpene composition of the plant species Euphorbia palustris. in Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, June 9-10, 2022 / Kratki izvodi radova, kjniga radova - 58. Savetovanje Srpskog hemijskog društva, Beograd 9. i 10. jun 2022. godine. 2022;:143.
https://hdl.handle.net/21.15107/rcub_cer_5875 .

Savić, Danica, Krstić, Gordana, Jadranin, Milka, Tešević, Vele, Milosavljević, Slobodan, "Triterpene composition of the plant species Euphorbia palustris" in Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, June 9-10, 2022 / Kratki izvodi radova, kjniga radova - 58. Savetovanje Srpskog hemijskog društva, Beograd 9. i 10. jun 2022. godine (2022):143,
https://hdl.handle.net/21.15107/rcub_cer_5875 .

TY  - JOUR
AU  - Stanković Jeremić, Jovana
AU  - Gođevac, Dejan
AU  - Ivanović, Stefan
AU  - Simić, Katarina
AU  - Trendafilova, Antoaneta
AU  - Aćimović, Milica
AU  - Milosavljević, Slobodan
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5166
AB  - The application of High Performance Thin Layer Chromatography
(HPTLC)-based non-targeted metabolomics as a holistic approach to compare
fingerprints of metabolite changes during Artemisia annua development is
described. Images of HPTLC chromatograms obtained after derivatization with
anisaldehyde-sulphuric acid reagent were used as a dataset for multivariate
analysis. Principal component analysis and Orthogonal Partial Least Squares
Discriminant Analysis confirmed the discrimination of samples belonging to
vegetative phase, flowering stage, and seed formation stage of the plant
development. The obtained results showed that the HPTLC-based metabolomics
approach can be a very reliable technique for the investigation of metabolic
changes during plant development, complementary to GC-MS and NMR-based
metabolomics.
AB  - Описана је холистичка примена нетаргетне метаболомике базиране на високоефикасној танкослојној хроматографији (HPTLC) која омогућава поређење метаболичких профила Artemisia annua и праћење њихових промена током развоја биљке. HPTLC хроматограми након развијања анизалдехидом и сумпорном киселином су коришћени за генерисање података за мултиваријантну анализу. Анализа главних компоненти (PCA) и ортогонална дискриминанта анализа најмањих квадрата (OPLS-DA) су потврдиле разлике између узорака који припадају различитим фенофазама - вегетативној фази, фази цветања и фази формирања семена. Добијени резултати указују да метаболомички приступ заснован на HPTLC методи која је комплементарна са GC-MS и NMR анализом, може бити веома поуздана техника за анализу промене током развоја биљке.
PB  - Belgrade : Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - HPTLC-based metabolomics for the investigation of metabolic changes during plant development: The case study of Artemisia annua
T1  - Mетаболомикa базиранa на HPTLC за испитивање метаболичких промена током развоја биљке:  Artemisia annua студија случаја
VL  - 87
IS  - 11
SP  - 1237
EP  - 1244
DO  - 10.2298/JSC210507007S
ER  - 

@article{
author = "Stanković Jeremić, Jovana and Gođevac, Dejan and Ivanović, Stefan and Simić, Katarina and Trendafilova, Antoaneta and Aćimović, Milica and Milosavljević, Slobodan",
year = "2022",
abstract = "The application of High Performance Thin Layer Chromatography
(HPTLC)-based non-targeted metabolomics as a holistic approach to compare
fingerprints of metabolite changes during Artemisia annua development is
described. Images of HPTLC chromatograms obtained after derivatization with
anisaldehyde-sulphuric acid reagent were used as a dataset for multivariate
analysis. Principal component analysis and Orthogonal Partial Least Squares
Discriminant Analysis confirmed the discrimination of samples belonging to
vegetative phase, flowering stage, and seed formation stage of the plant
development. The obtained results showed that the HPTLC-based metabolomics
approach can be a very reliable technique for the investigation of metabolic
changes during plant development, complementary to GC-MS and NMR-based
metabolomics., Описана је холистичка примена нетаргетне метаболомике базиране на високоефикасној танкослојној хроматографији (HPTLC) која омогућава поређење метаболичких профила Artemisia annua и праћење њихових промена током развоја биљке. HPTLC хроматограми након развијања анизалдехидом и сумпорном киселином су коришћени за генерисање података за мултиваријантну анализу. Анализа главних компоненти (PCA) и ортогонална дискриминанта анализа најмањих квадрата (OPLS-DA) су потврдиле разлике између узорака који припадају различитим фенофазама - вегетативној фази, фази цветања и фази формирања семена. Добијени резултати указују да метаболомички приступ заснован на HPTLC методи која је комплементарна са GC-MS и NMR анализом, може бити веома поуздана техника за анализу промене током развоја биљке.",
publisher = "Belgrade : Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "HPTLC-based metabolomics for the investigation of metabolic changes during plant development: The case study of Artemisia annua, Mетаболомикa базиранa на HPTLC за испитивање метаболичких промена током развоја биљке:  Artemisia annua студија случаја",
volume = "87",
number = "11",
pages = "1237-1244",
doi = "10.2298/JSC210507007S"
}

Stanković Jeremić, J., Gođevac, D., Ivanović, S., Simić, K., Trendafilova, A., Aćimović, M.,& Milosavljević, S.. (2022). HPTLC-based metabolomics for the investigation of metabolic changes during plant development: The case study of Artemisia annua. in Journal of the Serbian Chemical Society
Belgrade : Serbian Chemical Society., 87(11), 1237-1244.
https://doi.org/10.2298/JSC210507007S

Stanković Jeremić J, Gođevac D, Ivanović S, Simić K, Trendafilova A, Aćimović M, Milosavljević S. HPTLC-based metabolomics for the investigation of metabolic changes during plant development: The case study of Artemisia annua. in Journal of the Serbian Chemical Society. 2022;87(11):1237-1244.
doi:10.2298/JSC210507007S .

Stanković Jeremić, Jovana, Gođevac, Dejan, Ivanović, Stefan, Simić, Katarina, Trendafilova, Antoaneta, Aćimović, Milica, Milosavljević, Slobodan, "HPTLC-based metabolomics for the investigation of metabolic changes during plant development: The case study of Artemisia annua" in Journal of the Serbian Chemical Society, 87, no. 11 (2022):1237-1244,
https://doi.org/10.2298/JSC210507007S . .

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 . .

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 . .

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 . .

TY  - CONF
AU  - Anđelković, Boban
AU  - Gođevac, Dejan
AU  - Stanković, Jovana
AU  - Cvetković, Mirjana
AU  - Tešević, Vele
AU  - Milosavljević, Slobodan
AU  - Simić, Katarina
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5526
AB  - A large number of plant metabolites has provided an incomparable chemical source of the pharmaceutical
products. The two major fields of chemical research on biological active small molecules, metabolomics and
natural product discovery, have the similar goals of identifying and characterizing small molecules, either in
their isolated active state (natural product chemistry). Metabolomics generate a profile of small molecules
from plant extracts, which could be directly responsible for bioactivity effects. Using dry-column flash
chromatography enable a rapid and inexpensive method for the very efficient separation of plant extract with
a high resolution. This separation method coupled to NMR and FTIR-based metabolomics is applied to identify
bioactive natural products. OPLS multivariate analysis method, was used for correlation the chemical
composition of the plant extracts, Amphoricarpos autariatus, with the results of cytotoxic activity against
Human cervical adenocarcinoma cell line (HeLa) and epithelial lung cancer cell line (A549). In this way, the
highest contribution to the cytotoxic activity was recorded for the guaianolide sesquiterpene lactone were
tested, and their cytotoxic activity were conformed.
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  - Integration	of	dry-column	flash	chromatography	with	NMR	 and	 FTIR	 metabolomics	 to	 reveal	 cytotoxic	 metabolites	 from	 Amphoricarpos	autariatus
SP  - 148
EP  - 148
UR  - https://hdl.handle.net/21.15107/rcub_cer_5526
ER  - 

@conference{
author = "Anđelković, Boban and Gođevac, Dejan and Stanković, Jovana and Cvetković, Mirjana and Tešević, Vele and Milosavljević, Slobodan and Simić, Katarina",
year = "2021",
abstract = "A large number of plant metabolites has provided an incomparable chemical source of the pharmaceutical
products. The two major fields of chemical research on biological active small molecules, metabolomics and
natural product discovery, have the similar goals of identifying and characterizing small molecules, either in
their isolated active state (natural product chemistry). Metabolomics generate a profile of small molecules
from plant extracts, which could be directly responsible for bioactivity effects. Using dry-column flash
chromatography enable a rapid and inexpensive method for the very efficient separation of plant extract with
a high resolution. This separation method coupled to NMR and FTIR-based metabolomics is applied to identify
bioactive natural products. OPLS multivariate analysis method, was used for correlation the chemical
composition of the plant extracts, Amphoricarpos autariatus, with the results of cytotoxic activity against
Human cervical adenocarcinoma cell line (HeLa) and epithelial lung cancer cell line (A549). In this way, the
highest contribution to the cytotoxic activity was recorded for the guaianolide sesquiterpene lactone were
tested, and their cytotoxic activity were conformed.",
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 = "Integration	of	dry-column	flash	chromatography	with	NMR	 and	 FTIR	 metabolomics	 to	 reveal	 cytotoxic	 metabolites	 from	 Amphoricarpos	autariatus",
pages = "148-148",
url = "https://hdl.handle.net/21.15107/rcub_cer_5526"
}

Anđelković, B., Gođevac, D., Stanković, J., Cvetković, M., Tešević, V., Milosavljević, S.,& Simić, K.. (2021). Integration	of	dry-column	flash	chromatography	with	NMR	 and	 FTIR	 metabolomics	 to	 reveal	 cytotoxic	 metabolites	 from	 Amphoricarpos	autariatus. in Book of abstracts - 5th International Caparica Christmas Conference  on Sample Treatment (ST 2021), 15th – 18th November 2021, Caparica, Portugal
Portugal : PROTEOMASS Scientific Society., 148-148.
https://hdl.handle.net/21.15107/rcub_cer_5526

Anđelković B, Gođevac D, Stanković J, Cvetković M, Tešević V, Milosavljević S, Simić K. Integration	of	dry-column	flash	chromatography	with	NMR	 and	 FTIR	 metabolomics	 to	 reveal	 cytotoxic	 metabolites	 from	 Amphoricarpos	autariatus. in Book of abstracts - 5th International Caparica Christmas Conference  on Sample Treatment (ST 2021), 15th – 18th November 2021, Caparica, Portugal. 2021;:148-148.
https://hdl.handle.net/21.15107/rcub_cer_5526 .

Anđelković, Boban, Gođevac, Dejan, Stanković, Jovana, Cvetković, Mirjana, Tešević, Vele, Milosavljević, Slobodan, Simić, Katarina, "Integration	of	dry-column	flash	chromatography	with	NMR	 and	 FTIR	 metabolomics	 to	 reveal	 cytotoxic	 metabolites	 from	 Amphoricarpos	autariatus" in Book of abstracts - 5th International Caparica Christmas Conference  on Sample Treatment (ST 2021), 15th – 18th November 2021, Caparica, Portugal (2021):148-148,
https://hdl.handle.net/21.15107/rcub_cer_5526 .

TY  - CONF
AU  - Anđelković, Boban
AU  - Sofrenić, Ivana
AU  - Đorđević, Iris
AU  - Ivanović, Stefan
AU  - Cvetković, Mirjana
AU  - Gođevac, Dejan
AU  - Milosavljević, Slobodan
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5525
AB  - Metabolomics has emerged in recent years as an indispensable tool for the analysis of thousands
of metabolites from crude natural extracts, leading to a paradigm shift in natural products drug
research. Many of the technologies used in metabolomics have method-specific advantages and
drawbacks in terms of diversity of metabolites detected, sensitivity, or resolution.
We will describe the use of metabolomic methods for:
• Correlation of propolis composition to altitude of collection and revealing its major botanical
origin.
• revealing cytotoxic metabolites from Mahonia aquifolium stem-bark
• application for differentiation of the ambiguous taxonomy of the genus Amphoricarpos Vis.
In order to correlate variability in Populus type propolis composition with the altitude of its
collection, NMR spectroscopy followed by OPLS was conducted. The botanical origin of propolis
was established by comparing propolis spectral data to those of buds of various Populus species.
An O2PLS method was utilized to integrate two blocks of data. The utilization of various NMR
experiments, in combination with sophisticated multivariate analysis methods, was demonstrated
to be a powerful tool to correlate propolis composition to altitude of collection and reveal its major
botanical origin. OPLS methods were used to identify changes in the chemical composition of
propolis, while O2PLS methods enabled the identification of the botanical origin of propolis.[1]
A 1H NMR-based metabolomics method was used to reveal cytotoxic metabolites from Mahonia
aquifolium stem-bark. Primary and secondary metabolites in the Mahonia aquifolium extracts
were identified by thorough analysis of 1H and 2D NMR spectra, without prior isolation. An OPLS
multivariate analysis method was used to correlate the chemical composition of the plant extracts
with the results of cytotoxic activity against Human cervical adenocarcinoma cell line.[2]
Metabolomic methods were used to get more insight into the ambiguous taxonomy of the genus
Amphoricarpos Vis. The 1H NMR spectroscopy combined with multivariate data analysis has been
applied. OPLS-DA has been shown to be the best method for clear discrimination of these samples
based on the metabolites present in the extracts. 1H NMR fingerprinting in combination with PCA
and OPLS-DA showed a clear separation between the species resulting in two groups according to
metabolomic similarities.
PB  - Zagreb, Croatia : Department of Chemistry, Faculty of Science, University of Zagreb
C3  - Book of abstracts - The Adriatic NMR Conference, 22–24 September 2020, Peroj, Croatia
T1  - NMR metabolomics insight into phytochemistry
SP  - 30
EP  - 30
UR  - https://hdl.handle.net/21.15107/rcub_cer_5525
ER  - 

@conference{
author = "Anđelković, Boban and Sofrenić, Ivana and Đorđević, Iris and Ivanović, Stefan and Cvetković, Mirjana and Gođevac, Dejan and Milosavljević, Slobodan",
year = "2020",
abstract = "Metabolomics has emerged in recent years as an indispensable tool for the analysis of thousands
of metabolites from crude natural extracts, leading to a paradigm shift in natural products drug
research. Many of the technologies used in metabolomics have method-specific advantages and
drawbacks in terms of diversity of metabolites detected, sensitivity, or resolution.
We will describe the use of metabolomic methods for:
• Correlation of propolis composition to altitude of collection and revealing its major botanical
origin.
• revealing cytotoxic metabolites from Mahonia aquifolium stem-bark
• application for differentiation of the ambiguous taxonomy of the genus Amphoricarpos Vis.
In order to correlate variability in Populus type propolis composition with the altitude of its
collection, NMR spectroscopy followed by OPLS was conducted. The botanical origin of propolis
was established by comparing propolis spectral data to those of buds of various Populus species.
An O2PLS method was utilized to integrate two blocks of data. The utilization of various NMR
experiments, in combination with sophisticated multivariate analysis methods, was demonstrated
to be a powerful tool to correlate propolis composition to altitude of collection and reveal its major
botanical origin. OPLS methods were used to identify changes in the chemical composition of
propolis, while O2PLS methods enabled the identification of the botanical origin of propolis.[1]
A 1H NMR-based metabolomics method was used to reveal cytotoxic metabolites from Mahonia
aquifolium stem-bark. Primary and secondary metabolites in the Mahonia aquifolium extracts
were identified by thorough analysis of 1H and 2D NMR spectra, without prior isolation. An OPLS
multivariate analysis method was used to correlate the chemical composition of the plant extracts
with the results of cytotoxic activity against Human cervical adenocarcinoma cell line.[2]
Metabolomic methods were used to get more insight into the ambiguous taxonomy of the genus
Amphoricarpos Vis. The 1H NMR spectroscopy combined with multivariate data analysis has been
applied. OPLS-DA has been shown to be the best method for clear discrimination of these samples
based on the metabolites present in the extracts. 1H NMR fingerprinting in combination with PCA
and OPLS-DA showed a clear separation between the species resulting in two groups according to
metabolomic similarities.",
publisher = "Zagreb, Croatia : Department of Chemistry, Faculty of Science, University of Zagreb",
journal = "Book of abstracts - The Adriatic NMR Conference, 22–24 September 2020, Peroj, Croatia",
title = "NMR metabolomics insight into phytochemistry",
pages = "30-30",
url = "https://hdl.handle.net/21.15107/rcub_cer_5525"
}

Anđelković, B., Sofrenić, I., Đorđević, I., Ivanović, S., Cvetković, M., Gođevac, D.,& Milosavljević, S.. (2020). NMR metabolomics insight into phytochemistry. in Book of abstracts - The Adriatic NMR Conference, 22–24 September 2020, Peroj, Croatia
Zagreb, Croatia : Department of Chemistry, Faculty of Science, University of Zagreb., 30-30.
https://hdl.handle.net/21.15107/rcub_cer_5525

Anđelković B, Sofrenić I, Đorđević I, Ivanović S, Cvetković M, Gođevac D, Milosavljević S. NMR metabolomics insight into phytochemistry. in Book of abstracts - The Adriatic NMR Conference, 22–24 September 2020, Peroj, Croatia. 2020;:30-30.
https://hdl.handle.net/21.15107/rcub_cer_5525 .

Anđelković, Boban, Sofrenić, Ivana, Đorđević, Iris, Ivanović, Stefan, Cvetković, Mirjana, Gođevac, Dejan, Milosavljević, Slobodan, "NMR metabolomics insight into phytochemistry" in Book of abstracts - The Adriatic NMR Conference, 22–24 September 2020, Peroj, Croatia (2020):30-30,
https://hdl.handle.net/21.15107/rcub_cer_5525 .

TY  - JOUR
AU  - Cvetković, Mirjana
AU  - Damjanović, Ana
AU  - Stanojković, Tatjana
AU  - Đorđević, Iris
AU  - Tešević, Vele
AU  - Milosavljević, Slobodan
AU  - Gođevac, Dejan
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3054
AB  - Metabolomics generate a profile of small molecules from plant extracts, which could be directly responsible for bioactivity effects. Using dry-column flash chromatography enabled a rapid and inexpensive method for the very efficient separation of plant extract with a high resolution. This separation method coupled to NMR and FTIR based metabolomics is applied to identify bioactive natural products. OPLS multivariate analysis method, was used for correlation the chemical composition of the plant extracts, Amphoricarpos autariatus, with the results of cytotoxic activity against Human cervical adenocarcinoma cell line (HeLa) and epithelial lung cancer cell line
(A549). In this way, the highest contribution to the cytotoxic activity was recorded for the guaianolide sesquiterpene lactones named amphoricarpolides. The compounds indicated as bioactive after metabolomics analysis were tested, and their cytotoxic activity were confirmed.
PB  - Elsevier
T2  - Talanta
T1  - Integration of dry-column flash chromatography with NMR and FTIR metabolomics to reveal cytotoxic metabolites from Amphoricarpos autariatus
VL  - 206
SP  - 120248
DO  - 10.1016/j.talanta.2019.120248
ER  - 

@article{
author = "Cvetković, Mirjana and Damjanović, Ana and Stanojković, Tatjana and Đorđević, Iris and Tešević, Vele and Milosavljević, Slobodan and Gođevac, Dejan",
year = "2020",
abstract = "Metabolomics generate a profile of small molecules from plant extracts, which could be directly responsible for bioactivity effects. Using dry-column flash chromatography enabled a rapid and inexpensive method for the very efficient separation of plant extract with a high resolution. This separation method coupled to NMR and FTIR based metabolomics is applied to identify bioactive natural products. OPLS multivariate analysis method, was used for correlation the chemical composition of the plant extracts, Amphoricarpos autariatus, with the results of cytotoxic activity against Human cervical adenocarcinoma cell line (HeLa) and epithelial lung cancer cell line
(A549). In this way, the highest contribution to the cytotoxic activity was recorded for the guaianolide sesquiterpene lactones named amphoricarpolides. The compounds indicated as bioactive after metabolomics analysis were tested, and their cytotoxic activity were confirmed.",
publisher = "Elsevier",
journal = "Talanta",
title = "Integration of dry-column flash chromatography with NMR and FTIR metabolomics to reveal cytotoxic metabolites from Amphoricarpos autariatus",
volume = "206",
pages = "120248",
doi = "10.1016/j.talanta.2019.120248"
}

Cvetković, M., Damjanović, A., Stanojković, T., Đorđević, I., Tešević, V., Milosavljević, S.,& Gođevac, D.. (2020). Integration of dry-column flash chromatography with NMR and FTIR metabolomics to reveal cytotoxic metabolites from Amphoricarpos autariatus. in Talanta
Elsevier., 206, 120248.
https://doi.org/10.1016/j.talanta.2019.120248

Cvetković M, Damjanović A, Stanojković T, Đorđević I, Tešević V, Milosavljević S, Gođevac D. Integration of dry-column flash chromatography with NMR and FTIR metabolomics to reveal cytotoxic metabolites from Amphoricarpos autariatus. in Talanta. 2020;206:120248.
doi:10.1016/j.talanta.2019.120248 .

Cvetković, Mirjana, Damjanović, Ana, Stanojković, Tatjana, Đorđević, Iris, Tešević, Vele, Milosavljević, Slobodan, Gođevac, Dejan, "Integration of dry-column flash chromatography with NMR and FTIR metabolomics to reveal cytotoxic metabolites from Amphoricarpos autariatus" in Talanta, 206 (2020):120248,
https://doi.org/10.1016/j.talanta.2019.120248 . .

TY  - JOUR
AU  - Cvetković, Mirjana
AU  - Đorđević, Iris
AU  - Jadranin, Milka
AU  - Stanković, Miroslava
AU  - Mandić, Boris
AU  - Milosavljević, Slobodan
AU  - Vujisić, Ljubodrag V.
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3266
AB  - Analysis of composition of CH2Cl2 surface extract of leaves of Amphoricarpos neumayeri Vis. revealed 16 sesquiterpene lactones with guaianolide skeleton, so called amphoricarpolides, typical for this genus. Four of them, 13–16, were new derivatives and their structures were elucidated by detailed analyses of IR, NMR and MS data. Amphoricarpolide (9), its 15-O-acetyl derivative (5), and two 9β-hydroxyamphoricarpolides, 3,15-di-O-acetyl- and 3-O-acetyl-15-O-isovaleroyl derivatives (3 and 6, respectively) were tested for in vitro protective effect on chromosome aberrations in peripheral human lymphocytes using cytochalasin-B blocked micronucleus (CBMN) assay. The tested compound exerted a beneficial effect by decreasing DNA damage of human lymphocytes.
PB  - Informa UK Limited
T2  - Natural Product Research
T1  - Leaf-surface guaianolides from Amphoricarpos neumaeyri                    showing protective effect on human lymphocytes DNA
SP  - 1
EP  - 9
DO  - 10.1080/14786419.2019.1687470
ER  - 

@article{
author = "Cvetković, Mirjana and Đorđević, Iris and Jadranin, Milka and Stanković, Miroslava and Mandić, Boris and Milosavljević, Slobodan and Vujisić, Ljubodrag V.",
year = "2019",
abstract = "Analysis of composition of CH2Cl2 surface extract of leaves of Amphoricarpos neumayeri Vis. revealed 16 sesquiterpene lactones with guaianolide skeleton, so called amphoricarpolides, typical for this genus. Four of them, 13–16, were new derivatives and their structures were elucidated by detailed analyses of IR, NMR and MS data. Amphoricarpolide (9), its 15-O-acetyl derivative (5), and two 9β-hydroxyamphoricarpolides, 3,15-di-O-acetyl- and 3-O-acetyl-15-O-isovaleroyl derivatives (3 and 6, respectively) were tested for in vitro protective effect on chromosome aberrations in peripheral human lymphocytes using cytochalasin-B blocked micronucleus (CBMN) assay. The tested compound exerted a beneficial effect by decreasing DNA damage of human lymphocytes.",
publisher = "Informa UK Limited",
journal = "Natural Product Research",
title = "Leaf-surface guaianolides from Amphoricarpos neumaeyri                    showing protective effect on human lymphocytes DNA",
pages = "1-9",
doi = "10.1080/14786419.2019.1687470"
}

Cvetković, M., Đorđević, I., Jadranin, M., Stanković, M., Mandić, B., Milosavljević, S.,& Vujisić, L. V.. (2019). Leaf-surface guaianolides from Amphoricarpos neumaeyri                    showing protective effect on human lymphocytes DNA. in Natural Product Research
Informa UK Limited., 1-9.
https://doi.org/10.1080/14786419.2019.1687470

Cvetković M, Đorđević I, Jadranin M, Stanković M, Mandić B, Milosavljević S, Vujisić LV. Leaf-surface guaianolides from Amphoricarpos neumaeyri                    showing protective effect on human lymphocytes DNA. in Natural Product Research. 2019;:1-9.
doi:10.1080/14786419.2019.1687470 .

Cvetković, Mirjana, Đorđević, Iris, Jadranin, Milka, Stanković, Miroslava, Mandić, Boris, Milosavljević, Slobodan, Vujisić, Ljubodrag V., "Leaf-surface guaianolides from Amphoricarpos neumaeyri                    showing protective effect on human lymphocytes DNA" in Natural Product Research (2019):1-9,
https://doi.org/10.1080/14786419.2019.1687470 . .

TY  - DATA
AU  - Novaković, Miroslav
AU  - Đorđević, Iris
AU  - Todorović, Nina
AU  - Trifunovic, Snežana
AU  - Anđelković, Boban D.
AU  - Mandić, Boris
AU  - Jadranin, Milka
AU  - Vučković, Ivan
AU  - Vajs, Vlatka
AU  - Milosavljević, Slobodan
AU  - Tešević, Vele
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4447
AB  - Table S1. HPLC program for the quantification of the main compounds from the C. coggygria CH2Cl2/MeOH extract Figure S1. UV spectra of 14 in MeOH, with addition of AlCl3, and HCl Figure S2. UV spectra of compound 14 in MeOH, with NaOAc, NaOAc+H3BO3 and with NaOMe Figure S3. 1H NMR spectrum of compound 14 Figure S4. 13C NMR spectrum of compound 14 Figure S5. Aromatic part of the COSY spectrum of 14 Figure S6. Aromatic part of the NOESY spectrum of 14 Figure S7. Aromatic part of the HSQC spectrum of 14 Figure S8. Aromatic part of the HMBC spectrum of 14 Figure S9. Key HMBC correlations of 14 Table S2. 1H, 13C NMR and HMBC data of 14 (CD3OD, δ ppm, J in Hz) Figure S10. Aromatic part of the 1H NMR spectrum of 15 Figure S11. Aliphatic part of the 1H NMR spectrum of 15 Figure S12. 13C NMR spectrum of 15 Figure S13. HSQC spectrum of 15 Figure S14. The first part of the HMBC spectrum of 15 Figure S15. The second part of the HMBC spectrum of 15 Figure S16. HMBC (4 Hz) correlation H-7''/C-4' (15) Figure S17. The first part of the NOESY spectrum of 15 Figure S18. The second part of the NOESY spectrum of 15 Table S3. 1H and 13C NMR data of 15 (CD3OD, δ ppm, J in Hz) Figure S19. 3-Aryl-propanol moiety in 15 Figure S20. Key HMBC correlations in 15 Figure S21. UV spectrum of 15 Figure S22. UV spectrum of 10
PB  - Taylor and Francis Ltd.
T2  - Natural Product Research
T1  - Supplementary material for: "New aurone epoxide and auronolignan from the heartwood of Cotinus coggygria Scop."
DO  - 10.6084/m9.figshare.7418396.v1
ER  - 

@misc{
author = "Novaković, Miroslav and Đorđević, Iris and Todorović, Nina and Trifunovic, Snežana and Anđelković, Boban D. and Mandić, Boris and Jadranin, Milka and Vučković, Ivan and Vajs, Vlatka and Milosavljević, Slobodan and Tešević, Vele",
year = "2018",
abstract = "Table S1. HPLC program for the quantification of the main compounds from the C. coggygria CH2Cl2/MeOH extract Figure S1. UV spectra of 14 in MeOH, with addition of AlCl3, and HCl Figure S2. UV spectra of compound 14 in MeOH, with NaOAc, NaOAc+H3BO3 and with NaOMe Figure S3. 1H NMR spectrum of compound 14 Figure S4. 13C NMR spectrum of compound 14 Figure S5. Aromatic part of the COSY spectrum of 14 Figure S6. Aromatic part of the NOESY spectrum of 14 Figure S7. Aromatic part of the HSQC spectrum of 14 Figure S8. Aromatic part of the HMBC spectrum of 14 Figure S9. Key HMBC correlations of 14 Table S2. 1H, 13C NMR and HMBC data of 14 (CD3OD, δ ppm, J in Hz) Figure S10. Aromatic part of the 1H NMR spectrum of 15 Figure S11. Aliphatic part of the 1H NMR spectrum of 15 Figure S12. 13C NMR spectrum of 15 Figure S13. HSQC spectrum of 15 Figure S14. The first part of the HMBC spectrum of 15 Figure S15. The second part of the HMBC spectrum of 15 Figure S16. HMBC (4 Hz) correlation H-7''/C-4' (15) Figure S17. The first part of the NOESY spectrum of 15 Figure S18. The second part of the NOESY spectrum of 15 Table S3. 1H and 13C NMR data of 15 (CD3OD, δ ppm, J in Hz) Figure S19. 3-Aryl-propanol moiety in 15 Figure S20. Key HMBC correlations in 15 Figure S21. UV spectrum of 15 Figure S22. UV spectrum of 10",
publisher = "Taylor and Francis Ltd.",
journal = "Natural Product Research",
title = "Supplementary material for: "New aurone epoxide and auronolignan from the heartwood of Cotinus coggygria Scop."",
doi = "10.6084/m9.figshare.7418396.v1"
}

Novaković, M., Đorđević, I., Todorović, N., Trifunovic, S., Anđelković, B. D., Mandić, B., Jadranin, M., Vučković, I., Vajs, V., Milosavljević, S.,& Tešević, V.. (2018). Supplementary material for: "New aurone epoxide and auronolignan from the heartwood of Cotinus coggygria Scop.". in Natural Product Research
Taylor and Francis Ltd...
https://doi.org/10.6084/m9.figshare.7418396.v1

Novaković M, Đorđević I, Todorović N, Trifunovic S, Anđelković BD, Mandić B, Jadranin M, Vučković I, Vajs V, Milosavljević S, Tešević V. Supplementary material for: "New aurone epoxide and auronolignan from the heartwood of Cotinus coggygria Scop.". in Natural Product Research. 2018;.
doi:10.6084/m9.figshare.7418396.v1 .

Novaković, Miroslav, Đorđević, Iris, Todorović, Nina, Trifunovic, Snežana, Anđelković, Boban D., Mandić, Boris, Jadranin, Milka, Vučković, Ivan, Vajs, Vlatka, Milosavljević, Slobodan, Tešević, Vele, "Supplementary material for: "New aurone epoxide and auronolignan from the heartwood of Cotinus coggygria Scop."" in Natural Product Research (2018),
https://doi.org/10.6084/m9.figshare.7418396.v1 . .

TY  - DATA
AU  - Novaković, Miroslav
AU  - Bukvicki, Danka
AU  - Vajs, Vlatka
AU  - Tešević, Vele
AU  - Milosavljević, Slobodan
AU  - Marin, Petar D.
AU  - Asakawa, Yoshinori
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4448
AB  - Text S1. General experimental procedures Table S1. Elution system for the silica gel column chromatography separation of biotransformed products Figure 1S. 1 H NMR spectrum of compound 5 Figure 2S. 13C NMR spectrum of compound 5 Figure 3S. 1 H NMR spectrum of compound 6 Figure 4S. 13C NMR spectrum of compound 6 Figure 5S. 1 H NMR spectrum of compound 7 Figure 6S. Aromatic part of the 1 H NMR spectrum of compound 7 Figure 7S. 13C NMR spectrum of compound 7
PB  - SAGE Publications
T2  - Natural Product Communications
T1  - Supplementary material for: "Microbial Transformation of Calamintha glandulosa Essential Oil by Aspergillus niger"
UR  - https://hdl.handle.net/21.15107/rcub_cer_4448
ER  - 

@misc{
author = "Novaković, Miroslav and Bukvicki, Danka and Vajs, Vlatka and Tešević, Vele and Milosavljević, Slobodan and Marin, Petar D. and Asakawa, Yoshinori",
year = "2018",
abstract = "Text S1. General experimental procedures Table S1. Elution system for the silica gel column chromatography separation of biotransformed products Figure 1S. 1 H NMR spectrum of compound 5 Figure 2S. 13C NMR spectrum of compound 5 Figure 3S. 1 H NMR spectrum of compound 6 Figure 4S. 13C NMR spectrum of compound 6 Figure 5S. 1 H NMR spectrum of compound 7 Figure 6S. Aromatic part of the 1 H NMR spectrum of compound 7 Figure 7S. 13C NMR spectrum of compound 7",
publisher = "SAGE Publications",
journal = "Natural Product Communications",
title = "Supplementary material for: "Microbial Transformation of Calamintha glandulosa Essential Oil by Aspergillus niger"",
url = "https://hdl.handle.net/21.15107/rcub_cer_4448"
}

Novaković, M., Bukvicki, D., Vajs, V., Tešević, V., Milosavljević, S., Marin, P. D.,& Asakawa, Y.. (2018). Supplementary material for: "Microbial Transformation of Calamintha glandulosa Essential Oil by Aspergillus niger". in Natural Product Communications
SAGE Publications..
https://hdl.handle.net/21.15107/rcub_cer_4448

Novaković M, Bukvicki D, Vajs V, Tešević V, Milosavljević S, Marin PD, Asakawa Y. Supplementary material for: "Microbial Transformation of Calamintha glandulosa Essential Oil by Aspergillus niger". in Natural Product Communications. 2018;.
https://hdl.handle.net/21.15107/rcub_cer_4448 .

Novaković, Miroslav, Bukvicki, Danka, Vajs, Vlatka, Tešević, Vele, Milosavljević, Slobodan, Marin, Petar D., Asakawa, Yoshinori, "Supplementary material for: "Microbial Transformation of Calamintha glandulosa Essential Oil by Aspergillus niger"" in Natural Product Communications (2018),
https://hdl.handle.net/21.15107/rcub_cer_4448 .

TY  - CHAP
AU  - Vajs, Vlatka
AU  - Đorđević, Iris
AU  - Vujisić, Ljubodrag V.
AU  - Milosavljević, Slobodan
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3106
AB  - The detection of illegal drugs in various samples has been among the most fascinating objects for the practicing analytical chemist involved in forensic analysis. For centuries (until the end of the nineteenth century), drugs were almost entirely of natural origin, mostly herbal, and in some cases slightly chemically modified (e.g., through acetylation of morphine to heroin). By the development of synthetic organic chemistry (commencing at the beginning of the twentieth century), quite a few synthetic drugs designed to mimic the pharmacological effects of drugs originating from natural sources have been designed (e.g., cannabimimetic indazole derivatives or amphetamines, etc.). Detection of such synthetic drugs, named “designer drugs,” due to a large number of new substances continuously emerging on the market, is crucial. The efficacy of this analysis has become a tremendous challenge in the analytical forensic field. A development of fast identification and structural characterization is greatly facilitated by the advent of modern spectroscopic techniques, namely nuclear magnetic resonance spectroscopy (NMR) and modern mass spectrometry (MS) as well as separation techniques, such as gas and liquid chromatography (GC and LC). Nowadays, rapid strategies for chemical characterizations of illicit drugs are available.
PB  - Taylor & Francis
T2  - Chromatographic Techniques in the Forensic Analysis of Designer Drugs
T1  - NMR Spectroscopy in the Analysis of Illegal Drugs
SP  - 177
EP  - 197
DO  - 10.1201/9781315313177
ER  - 

@inbook{
author = "Vajs, Vlatka and Đorđević, Iris and Vujisić, Ljubodrag V. and Milosavljević, Slobodan",
year = "2018",
abstract = "The detection of illegal drugs in various samples has been among the most fascinating objects for the practicing analytical chemist involved in forensic analysis. For centuries (until the end of the nineteenth century), drugs were almost entirely of natural origin, mostly herbal, and in some cases slightly chemically modified (e.g., through acetylation of morphine to heroin). By the development of synthetic organic chemistry (commencing at the beginning of the twentieth century), quite a few synthetic drugs designed to mimic the pharmacological effects of drugs originating from natural sources have been designed (e.g., cannabimimetic indazole derivatives or amphetamines, etc.). Detection of such synthetic drugs, named “designer drugs,” due to a large number of new substances continuously emerging on the market, is crucial. The efficacy of this analysis has become a tremendous challenge in the analytical forensic field. A development of fast identification and structural characterization is greatly facilitated by the advent of modern spectroscopic techniques, namely nuclear magnetic resonance spectroscopy (NMR) and modern mass spectrometry (MS) as well as separation techniques, such as gas and liquid chromatography (GC and LC). Nowadays, rapid strategies for chemical characterizations of illicit drugs are available.",
publisher = "Taylor & Francis",
journal = "Chromatographic Techniques in the Forensic Analysis of Designer Drugs",
booktitle = "NMR Spectroscopy in the Analysis of Illegal Drugs",
pages = "177-197",
doi = "10.1201/9781315313177"
}

Vajs, V., Đorđević, I., Vujisić, L. V.,& Milosavljević, S.. (2018). NMR Spectroscopy in the Analysis of Illegal Drugs. in Chromatographic Techniques in the Forensic Analysis of Designer Drugs
Taylor & Francis., 177-197.
https://doi.org/10.1201/9781315313177

Vajs V, Đorđević I, Vujisić LV, Milosavljević S. NMR Spectroscopy in the Analysis of Illegal Drugs. in Chromatographic Techniques in the Forensic Analysis of Designer Drugs. 2018;:177-197.
doi:10.1201/9781315313177 .

Vajs, Vlatka, Đorđević, Iris, Vujisić, Ljubodrag V., Milosavljević, Slobodan, "NMR Spectroscopy in the Analysis of Illegal Drugs" in Chromatographic Techniques in the Forensic Analysis of Designer Drugs (2018):177-197,
https://doi.org/10.1201/9781315313177 . .

TY  - JOUR
AU  - Cvetković, Mirjana
AU  - Anđelković, Boban D.
AU  - Stevanovic, Vladimir
AU  - Jadranin, Milka
AU  - Đorđević, Iris
AU  - Tešević, Vele
AU  - Milosavljević, Slobodan
AU  - Gođevac, Dejan
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2316
AB  - The genus Amphoricarpos Vis. is endemic of westpart of Balkan peninsula. In order to get more insight into the ambiguous taxonomy of the genus, the metabolomic study of the Amphoricarpos samples, has been undertaken. The(1)H NMR spectroscopy combined with multivariate data analysis has been applied. OPLS-DA has been shown to be the best method for clear discrimination of these samples based on the metabolites present in the extracts. The main difference between A. autariatus and A. neumayeri has been found to be the presence of characteristic sesquiterpene lactones of guaianolide type named amphoricarpolides. While the main sesquiterpene lactone in A. neumayeri was oxidized in position 2, those present in both subspecies of A. autariatus samples were oxidized in position 9. The use of sesquiterpene lactones as taxonomic characters for differentiating species of the Asteraceae family was reviewed elsewhere. For the differentiation of two subspecies, A. autariatus ssp. autariatus, and A. autariatus ssp. bertisceus, chlorogenic and malic acid have been found to be decisive, but these compounds do not have chemotaxonomic significance. Our results were in accordance with above mentioned classification of Blecic and Mayer but they differentiate from those of the recent genomic study of the genus indicating a single, genetically, morphologically and ecologically variable species, without intraspecific taxa.
PB  - Elsevier
T2  - Phytochemistry Letters
T1  - NMR-based metabolomics study of Amphoricarpos species from Montenegro
VL  - 25
SP  - 1
EP  - 5
DO  - 10.1016/j.phytol.2018.03.013
ER  - 

@article{
author = "Cvetković, Mirjana and Anđelković, Boban D. and Stevanovic, Vladimir and Jadranin, Milka and Đorđević, Iris and Tešević, Vele and Milosavljević, Slobodan and Gođevac, Dejan",
year = "2018",
abstract = "The genus Amphoricarpos Vis. is endemic of westpart of Balkan peninsula. In order to get more insight into the ambiguous taxonomy of the genus, the metabolomic study of the Amphoricarpos samples, has been undertaken. The(1)H NMR spectroscopy combined with multivariate data analysis has been applied. OPLS-DA has been shown to be the best method for clear discrimination of these samples based on the metabolites present in the extracts. The main difference between A. autariatus and A. neumayeri has been found to be the presence of characteristic sesquiterpene lactones of guaianolide type named amphoricarpolides. While the main sesquiterpene lactone in A. neumayeri was oxidized in position 2, those present in both subspecies of A. autariatus samples were oxidized in position 9. The use of sesquiterpene lactones as taxonomic characters for differentiating species of the Asteraceae family was reviewed elsewhere. For the differentiation of two subspecies, A. autariatus ssp. autariatus, and A. autariatus ssp. bertisceus, chlorogenic and malic acid have been found to be decisive, but these compounds do not have chemotaxonomic significance. Our results were in accordance with above mentioned classification of Blecic and Mayer but they differentiate from those of the recent genomic study of the genus indicating a single, genetically, morphologically and ecologically variable species, without intraspecific taxa.",
publisher = "Elsevier",
journal = "Phytochemistry Letters",
title = "NMR-based metabolomics study of Amphoricarpos species from Montenegro",
volume = "25",
pages = "1-5",
doi = "10.1016/j.phytol.2018.03.013"
}

Cvetković, M., Anđelković, B. D., Stevanovic, V., Jadranin, M., Đorđević, I., Tešević, V., Milosavljević, S.,& Gođevac, D.. (2018). NMR-based metabolomics study of Amphoricarpos species from Montenegro. in Phytochemistry Letters
Elsevier., 25, 1-5.
https://doi.org/10.1016/j.phytol.2018.03.013

Cvetković M, Anđelković BD, Stevanovic V, Jadranin M, Đorđević I, Tešević V, Milosavljević S, Gođevac D. NMR-based metabolomics study of Amphoricarpos species from Montenegro. in Phytochemistry Letters. 2018;25:1-5.
doi:10.1016/j.phytol.2018.03.013 .

Cvetković, Mirjana, Anđelković, Boban D., Stevanovic, Vladimir, Jadranin, Milka, Đorđević, Iris, Tešević, Vele, Milosavljević, Slobodan, Gođevac, Dejan, "NMR-based metabolomics study of Amphoricarpos species from Montenegro" in Phytochemistry Letters, 25 (2018):1-5,
https://doi.org/10.1016/j.phytol.2018.03.013 . .