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  - Salah Adeen Embirsh, Hifa
AU  - Stajčić, Ivana
AU  - Gržetić, Jelena
AU  - Mladenović, Ivana O.
AU  - Anđelković, Boban
AU  - Marinković, Aleksandar
AU  - Vuksanović, Marija M.
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/6610
AB  - This paper presents sustainable technology for environmentally friendly composite production. Biobased unsaturated polyester resin (b-UPR), synthesized from waste polyethylene terephthalate (PET) glycosylate and renewable origin maleic anhydride (MAnh) and propylene glycol
(PG), was reinforced with unmodified and vinyl-modified biosilica nanoparticles obtained from
rice husk. The structural and morphological properties of the obtained particles, b-UPR, as well as
composites, were characterized by Fourier-transform infrared spectroscopy (FTIR), nuclear magnetic
resonance spectroscopy (NMR), scanning electron microscopy (SEM), and transmission electron
microscopy (TEM) techniques. The study of the influence of biosilica modification on the mechanical
properties of composites was supported by hardness modeling. Improvement of the tensile strength
of the b-UPR-based composite at 2.5 wt.% addition of biosilica modified with vinyl silane, named
“b-UPR/SiO2
-V” composite, has been achieved with 88% increase. The thermal aging process applied
to the b-UPR/SiO2
-V composite, which simulates use over the product’s lifetime, leads to the deterioration of composites that were used as fillers in commercial unsaturated polyester resin (c-UPR).
The grinded artificially aged b-UPR composites were used as filler in c-UPR for the production of a
table top layer with outstanding mechanical properties, i.e., impact resistance and microhardness, as
well as fire resistance rated in the V-0 category according to the UL-94 test. Developing sustainable
composites that are chemically synthesized from renewable sources is important from the aspect of
preserving the environment and existing resources as well as the extending their life cycle.
PB  - MDPI
T2  - Polymers
T1  - Synthesis, Characterization and Application of Biobased Unsaturated Polyester Resin Reinforced with Unmodified/Modified Biosilica Nanoparticles
VL  - 15
IS  - 18
SP  - 3756
DO  - 10.3390/polym15183756
ER  - 

@article{
author = "Salah Adeen Embirsh, Hifa and Stajčić, Ivana and Gržetić, Jelena and Mladenović, Ivana O. and Anđelković, Boban and Marinković, Aleksandar and Vuksanović, Marija M.",
year = "2023",
abstract = "This paper presents sustainable technology for environmentally friendly composite production. Biobased unsaturated polyester resin (b-UPR), synthesized from waste polyethylene terephthalate (PET) glycosylate and renewable origin maleic anhydride (MAnh) and propylene glycol
(PG), was reinforced with unmodified and vinyl-modified biosilica nanoparticles obtained from
rice husk. The structural and morphological properties of the obtained particles, b-UPR, as well as
composites, were characterized by Fourier-transform infrared spectroscopy (FTIR), nuclear magnetic
resonance spectroscopy (NMR), scanning electron microscopy (SEM), and transmission electron
microscopy (TEM) techniques. The study of the influence of biosilica modification on the mechanical
properties of composites was supported by hardness modeling. Improvement of the tensile strength
of the b-UPR-based composite at 2.5 wt.% addition of biosilica modified with vinyl silane, named
“b-UPR/SiO2
-V” composite, has been achieved with 88% increase. The thermal aging process applied
to the b-UPR/SiO2
-V composite, which simulates use over the product’s lifetime, leads to the deterioration of composites that were used as fillers in commercial unsaturated polyester resin (c-UPR).
The grinded artificially aged b-UPR composites were used as filler in c-UPR for the production of a
table top layer with outstanding mechanical properties, i.e., impact resistance and microhardness, as
well as fire resistance rated in the V-0 category according to the UL-94 test. Developing sustainable
composites that are chemically synthesized from renewable sources is important from the aspect of
preserving the environment and existing resources as well as the extending their life cycle.",
publisher = "MDPI",
journal = "Polymers",
title = "Synthesis, Characterization and Application of Biobased Unsaturated Polyester Resin Reinforced with Unmodified/Modified Biosilica Nanoparticles",
volume = "15",
number = "18",
pages = "3756",
doi = "10.3390/polym15183756"
}

Salah Adeen Embirsh, H., Stajčić, I., Gržetić, J., Mladenović, I. O., Anđelković, B., Marinković, A.,& Vuksanović, M. M.. (2023). Synthesis, Characterization and Application of Biobased Unsaturated Polyester Resin Reinforced with Unmodified/Modified Biosilica Nanoparticles. in Polymers
MDPI., 15(18), 3756.
https://doi.org/10.3390/polym15183756

Salah Adeen Embirsh H, Stajčić I, Gržetić J, Mladenović IO, Anđelković B, Marinković A, Vuksanović MM. Synthesis, Characterization and Application of Biobased Unsaturated Polyester Resin Reinforced with Unmodified/Modified Biosilica Nanoparticles. in Polymers. 2023;15(18):3756.
doi:10.3390/polym15183756 .

Salah Adeen Embirsh, Hifa, Stajčić, Ivana, Gržetić, Jelena, Mladenović, Ivana O., Anđelković, Boban, Marinković, Aleksandar, Vuksanović, Marija M., "Synthesis, Characterization and Application of Biobased Unsaturated Polyester Resin Reinforced with Unmodified/Modified Biosilica Nanoparticles" in Polymers, 15, no. 18 (2023):3756,
https://doi.org/10.3390/polym15183756 . .

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  - JOUR
AU  - Popović, Aleksandar R.
AU  - Anđelković, Boban D.
AU  - Đorđević, Dragana
AU  - Sakan, Sanja
AU  - Vujisić, Ljubodrag V.
AU  - Veličković, Sava
AU  - Relić, Dubravka
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5231
AB  - In order to further define the potential use of FTIR-ATR spectroscopy, as a non-destructive and reliable technique, for the analysis of the characteristics of post stamps, certified originals of the Principality of Serbia stamps (“Prince Michael issues”) issued in 1866 and 1868 as well as their forgeries were ana­lyzed. Spectra enabling the comparison of the paper, dye and glue of stamps of so-called “Vienna issues”, having denominations of 10 (orange-yellow), 20 (pink) and 40 para (blue) and “Belgrade issues” (1 para-green and 2 para-reddish brown), as well as 24 expert-certified forgeries, were taken. It was shown that the applied technology was, in most of the cases, a fast and suitable technique for establishing clear differences between the spectral characteristics of the paper and dye used for the original stamps, and forgeries that were most probably made decades after the printing of the genuine stamps. The differences between print­ings of the same issues of the genuine stamps were also elaborated. It is pro­posed, for the first time in philatelic history, the possibility that “Vienna issues” stamps may have been printed on two different papers, and, having in mind the technology of printing in the 19th century, potentially, not even at the same time or in the same printing house.
PB  - Belgrade : Serbian chemical society
T2  - Journal of the Serbian Chemical Society
T1  - To Professor Petar Pfendt, In calidum, et plurium retributivus memoriae: FTIR-ATR analysis of post stamps of the Principality of Serbia issued in 1866 and 1868 and their forgeries
VL  - 87
IS  - 1
SP  - 27
EP  - 40
DO  - 10.2298/JSC210901090P
ER  - 

@article{
author = "Popović, Aleksandar R. and Anđelković, Boban D. and Đorđević, Dragana and Sakan, Sanja and Vujisić, Ljubodrag V. and Veličković, Sava and Relić, Dubravka",
year = "2022",
abstract = "In order to further define the potential use of FTIR-ATR spectroscopy, as a non-destructive and reliable technique, for the analysis of the characteristics of post stamps, certified originals of the Principality of Serbia stamps (“Prince Michael issues”) issued in 1866 and 1868 as well as their forgeries were ana­lyzed. Spectra enabling the comparison of the paper, dye and glue of stamps of so-called “Vienna issues”, having denominations of 10 (orange-yellow), 20 (pink) and 40 para (blue) and “Belgrade issues” (1 para-green and 2 para-reddish brown), as well as 24 expert-certified forgeries, were taken. It was shown that the applied technology was, in most of the cases, a fast and suitable technique for establishing clear differences between the spectral characteristics of the paper and dye used for the original stamps, and forgeries that were most probably made decades after the printing of the genuine stamps. The differences between print­ings of the same issues of the genuine stamps were also elaborated. It is pro­posed, for the first time in philatelic history, the possibility that “Vienna issues” stamps may have been printed on two different papers, and, having in mind the technology of printing in the 19th century, potentially, not even at the same time or in the same printing house.",
publisher = "Belgrade : Serbian chemical society",
journal = "Journal of the Serbian Chemical Society",
title = "To Professor Petar Pfendt, In calidum, et plurium retributivus memoriae: FTIR-ATR analysis of post stamps of the Principality of Serbia issued in 1866 and 1868 and their forgeries",
volume = "87",
number = "1",
pages = "27-40",
doi = "10.2298/JSC210901090P"
}

Popović, A. R., Anđelković, B. D., Đorđević, D., Sakan, S., Vujisić, L. V., Veličković, S.,& Relić, D.. (2022). To Professor Petar Pfendt, In calidum, et plurium retributivus memoriae: FTIR-ATR analysis of post stamps of the Principality of Serbia issued in 1866 and 1868 and their forgeries. in Journal of the Serbian Chemical Society
Belgrade : Serbian chemical society., 87(1), 27-40.
https://doi.org/10.2298/JSC210901090P

Popović AR, Anđelković BD, Đorđević D, Sakan S, Vujisić LV, Veličković S, Relić D. To Professor Petar Pfendt, In calidum, et plurium retributivus memoriae: FTIR-ATR analysis of post stamps of the Principality of Serbia issued in 1866 and 1868 and their forgeries. in Journal of the Serbian Chemical Society. 2022;87(1):27-40.
doi:10.2298/JSC210901090P .

Popović, Aleksandar R., Anđelković, Boban D., Đorđević, Dragana, Sakan, Sanja, Vujisić, Ljubodrag V., Veličković, Sava, Relić, Dubravka, "To Professor Petar Pfendt, In calidum, et plurium retributivus memoriae: FTIR-ATR analysis of post stamps of the Principality of Serbia issued in 1866 and 1868 and their forgeries" in Journal of the Serbian Chemical Society, 87, no. 1 (2022):27-40,
https://doi.org/10.2298/JSC210901090P . .

TY  - JOUR
AU  - Gođevac, Dejan
AU  - Ivanović, Stefan
AU  - Simić, Katarina
AU  - Anđelković, Boban
AU  - Jovanović, Živko
AU  - Rakić, Tamara
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5165
AB  - Introduction
Ramonda serbica and R. nathaliae are resurrection plants that have the remarkable ability to survive the complete desiccation of their vegetative organs (i.e. leaves, stem, roots) during periods of drought and rapidly revive when rewatered and rehydrated.

Objective
To investigate metabolic changes in R. serbica and R. nathaliae during their desiccation and recovery process

Methods
Proton nuclear magnetic resonance (1H-NMR) and gas chromatography–mass spectrometry (GC–MS)-based metabolomics approach coupled with multivariate data analysis was utilised to identify the metabolomes of the plants from 90 biological replicates.

Results
Sucrose and the polyphenolic glycoside myconoside were predominant in almost equal amounts in all samples studied, regardless of their water content at sampling. During the dehydration process, a decrease in the relative content of fructose, galactose, and galactinol was observed while the contents of those metabolites were preserved in the partially rehydrated plants. Raffinose and myo-inositol were accumulated in dry samples.

Conclusion
Using 1H-NMR and GC–MS as two complementary analytical platforms provided a more complete picture of the metabolite composition for investigation of the desiccation and recovery process in resurrection plants.
PB  - Willey
T2  - Phytochemical Analysis
T1  - Metabolomics study of the desiccation and recovery process in the resurrection plants Ramonda serbica and R. nathaliae
VL  - 33
IS  - 6
SP  - 961
SP  - 961
EP  - 970
DO  - 10.1002/pca.3151
ER  - 

@article{
author = "Gođevac, Dejan and Ivanović, Stefan and Simić, Katarina and Anđelković, Boban and Jovanović, Živko and Rakić, Tamara",
year = "2022",
abstract = "Introduction
Ramonda serbica and R. nathaliae are resurrection plants that have the remarkable ability to survive the complete desiccation of their vegetative organs (i.e. leaves, stem, roots) during periods of drought and rapidly revive when rewatered and rehydrated.

Objective
To investigate metabolic changes in R. serbica and R. nathaliae during their desiccation and recovery process

Methods
Proton nuclear magnetic resonance (1H-NMR) and gas chromatography–mass spectrometry (GC–MS)-based metabolomics approach coupled with multivariate data analysis was utilised to identify the metabolomes of the plants from 90 biological replicates.

Results
Sucrose and the polyphenolic glycoside myconoside were predominant in almost equal amounts in all samples studied, regardless of their water content at sampling. During the dehydration process, a decrease in the relative content of fructose, galactose, and galactinol was observed while the contents of those metabolites were preserved in the partially rehydrated plants. Raffinose and myo-inositol were accumulated in dry samples.

Conclusion
Using 1H-NMR and GC–MS as two complementary analytical platforms provided a more complete picture of the metabolite composition for investigation of the desiccation and recovery process in resurrection plants.",
publisher = "Willey",
journal = "Phytochemical Analysis",
title = "Metabolomics study of the desiccation and recovery process in the resurrection plants Ramonda serbica and R. nathaliae",
volume = "33",
number = "6",
pages = "961-961-970",
doi = "10.1002/pca.3151"
}

Gođevac, D., Ivanović, S., Simić, K., Anđelković, B., Jovanović, Ž.,& Rakić, T.. (2022). Metabolomics study of the desiccation and recovery process in the resurrection plants Ramonda serbica and R. nathaliae. in Phytochemical Analysis
Willey., 33(6), 961-970.
https://doi.org/10.1002/pca.3151

Gođevac D, Ivanović S, Simić K, Anđelković B, Jovanović Ž, Rakić T. Metabolomics study of the desiccation and recovery process in the resurrection plants Ramonda serbica and R. nathaliae. in Phytochemical Analysis. 2022;33(6):961-970.
doi:10.1002/pca.3151 .

Gođevac, Dejan, Ivanović, Stefan, Simić, Katarina, Anđelković, Boban, Jovanović, Živko, Rakić, Tamara, "Metabolomics study of the desiccation and recovery process in the resurrection plants Ramonda serbica and R. nathaliae" in Phytochemical Analysis, 33, no. 6 (2022):961-970,
https://doi.org/10.1002/pca.3151 . .

TY  - CONF
AU  - Ivanović, Stefan
AU  - Gođevac, Dejan
AU  - Simić, Katarina
AU  - Anđelković, Boban
AU  - Jovanović, Ž. D.
AU  - Rakić, Tamara
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5522
AB  - Ramonda serbica and R. nathaliae are resurrection plants that have the
remarkable ability to survive the complete desiccation during periods of drought and
rapidly revive when rewatered and rehydrated. To investigate metabolic changes
during their desiccation and recovery process NMR-based metabolomics approach
coupled with multivariate data analysis was utilized to identify the metabolomes of
the plants from 90 biological replicates. The NMR metabolomics profiles of R.
serbica and R. nathaliae were subjected to multivariate data analysis. PCA was
performed, which resulted in eight principal components (PCs) in both models,
explaining 77.0% of the total data variance in the model with R. serbica samples,
and 79.5% of the variance in the model with R. nathaliae samples. Using NMR
experiments, the content of the two most dominant polar components found in the
leaves of these two plants was determined. Sucrose and the polyphenolic glycoside
myconoside were predominant in almost equal amounts in all samples studied,
regardless of their water content at sampling. Using of 1D and 2D NMR
experiments the main components have been successfully identified. Also, it was
necessary to isolate and purify the myconoside to confirm the structure.
PB  - Niš : Department of Biology and Ecology, Faculty of Science and  Mathematics
PB  - Belgrade : Institute for Nature Conservation of  Serbia
C3  - Book of Abstracts - 14th Symposium on the Flora of Southeastern  Serbia and Neighboring Regions, 26th to 29th June, 2022, Kladovo
T1  - NMR metabolomics study of the desiccation and recovery process in the resurrection plants Ramonda serbica and Ramonda nathaliae
SP  - 171
EP  - 171
UR  - https://hdl.handle.net/21.15107/rcub_cer_5522
ER  - 

@conference{
author = "Ivanović, Stefan and Gođevac, Dejan and Simić, Katarina and Anđelković, Boban and Jovanović, Ž. D. and Rakić, Tamara",
year = "2022",
abstract = "Ramonda serbica and R. nathaliae are resurrection plants that have the
remarkable ability to survive the complete desiccation during periods of drought and
rapidly revive when rewatered and rehydrated. To investigate metabolic changes
during their desiccation and recovery process NMR-based metabolomics approach
coupled with multivariate data analysis was utilized to identify the metabolomes of
the plants from 90 biological replicates. The NMR metabolomics profiles of R.
serbica and R. nathaliae were subjected to multivariate data analysis. PCA was
performed, which resulted in eight principal components (PCs) in both models,
explaining 77.0% of the total data variance in the model with R. serbica samples,
and 79.5% of the variance in the model with R. nathaliae samples. Using NMR
experiments, the content of the two most dominant polar components found in the
leaves of these two plants was determined. Sucrose and the polyphenolic glycoside
myconoside were predominant in almost equal amounts in all samples studied,
regardless of their water content at sampling. Using of 1D and 2D NMR
experiments the main components have been successfully identified. Also, it was
necessary to isolate and purify the myconoside to confirm the structure.",
publisher = "Niš : Department of Biology and Ecology, Faculty of Science and  Mathematics, Belgrade : Institute for Nature Conservation of  Serbia",
journal = "Book of Abstracts - 14th Symposium on the Flora of Southeastern  Serbia and Neighboring Regions, 26th to 29th June, 2022, Kladovo",
title = "NMR metabolomics study of the desiccation and recovery process in the resurrection plants Ramonda serbica and Ramonda nathaliae",
pages = "171-171",
url = "https://hdl.handle.net/21.15107/rcub_cer_5522"
}

Ivanović, S., Gođevac, D., Simić, K., Anđelković, B., Jovanović, Ž. D.,& Rakić, T.. (2022). NMR metabolomics study of the desiccation and recovery process in the resurrection plants Ramonda serbica and Ramonda nathaliae. in Book of Abstracts - 14th Symposium on the Flora of Southeastern  Serbia and Neighboring Regions, 26th to 29th June, 2022, Kladovo
Niš : Department of Biology and Ecology, Faculty of Science and  Mathematics., 171-171.
https://hdl.handle.net/21.15107/rcub_cer_5522

Ivanović S, Gođevac D, Simić K, Anđelković B, Jovanović ŽD, Rakić T. NMR metabolomics study of the desiccation and recovery process in the resurrection plants Ramonda serbica and Ramonda nathaliae. in Book of Abstracts - 14th Symposium on the Flora of Southeastern  Serbia and Neighboring Regions, 26th to 29th June, 2022, Kladovo. 2022;:171-171.
https://hdl.handle.net/21.15107/rcub_cer_5522 .

Ivanović, Stefan, Gođevac, Dejan, Simić, Katarina, Anđelković, Boban, Jovanović, Ž. D., Rakić, Tamara, "NMR metabolomics study of the desiccation and recovery process in the resurrection plants Ramonda serbica and Ramonda nathaliae" in Book of Abstracts - 14th Symposium on the Flora of Southeastern  Serbia and Neighboring Regions, 26th to 29th June, 2022, Kladovo (2022):171-171,
https://hdl.handle.net/21.15107/rcub_cer_5522 .

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  - 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  - DATA
AU  - Nikolić, Andrea
AU  - Stanić, Jelena
AU  - Zlatar, Matija
AU  - Gruden, Maja
AU  - Anđelković, Boban
AU  - Selaković, Života
AU  - Ajdačić, Vladimir
AU  - Opsenica, Igor
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4444
AB  - Copies of 1H and 13C NMR spectra for the synthesized compounds; Extended computational results, and total electronic energies, number of imaginary frequencies;  Cartesian coordinates of all structures.
PB  - American Chemical Society (ACS)
T2  - The Journal of Organic Chemistry
T1  - Supporting information for: "Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines"
DO  - 10.1021/acs.joc.1c00282.s001
ER  - 

@misc{
author = "Nikolić, Andrea and Stanić, Jelena and Zlatar, Matija and Gruden, Maja and Anđelković, Boban and Selaković, Života and Ajdačić, Vladimir and Opsenica, Igor",
year = "2021",
abstract = "Copies of 1H and 13C NMR spectra for the synthesized compounds; Extended computational results, and total electronic energies, number of imaginary frequencies;  Cartesian coordinates of all structures.",
publisher = "American Chemical Society (ACS)",
journal = "The Journal of Organic Chemistry",
title = "Supporting information for: "Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines"",
doi = "10.1021/acs.joc.1c00282.s001"
}

Nikolić, A., Stanić, J., Zlatar, M., Gruden, M., Anđelković, B., Selaković, Ž., Ajdačić, V.,& Opsenica, I.. (2021). Supporting information for: "Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines". in The Journal of Organic Chemistry
American Chemical Society (ACS)..
https://doi.org/10.1021/acs.joc.1c00282.s001

Nikolić A, Stanić J, Zlatar M, Gruden M, Anđelković B, Selaković Ž, Ajdačić V, Opsenica I. Supporting information for: "Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines". in The Journal of Organic Chemistry. 2021;.
doi:10.1021/acs.joc.1c00282.s001 .

Nikolić, Andrea, Stanić, Jelena, Zlatar, Matija, Gruden, Maja, Anđelković, Boban, Selaković, Života, Ajdačić, Vladimir, Opsenica, Igor, "Supporting information for: "Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines"" in The Journal of Organic Chemistry (2021),
https://doi.org/10.1021/acs.joc.1c00282.s001 . .

TY  - JOUR
AU  - Nikolić, Andrea
AU  - Stanić, Jelena
AU  - Zlatar, Matija
AU  - Gruden, Maja
AU  - Anđelković, Boban
AU  - Selaković, Života
AU  - Ajdačić, Vladimir
AU  - Opsenica, Igor
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4443
AB  - The Pd-catalyzed N-arylation method for the synthesis of eighteen N,1-diaryl-1H-tetrazol-5-amine derivatives is reported. By running the reactions at 35 °C, compounds were isolated as single isomers since the undesired Dimroth rearrangement was completely suppressed. Furthermore, the Dimroth rearrangement of N,1-diaryl-1H-tetrazol-5-amines was rationalized by conducting comprehensive experiments and NMR analysis as well as density functional theory (DFT) calculations of thermodynamic stability of the compounds. It was established that the Dimroth rearrangement is thermodynamically controlled, and the equilibrium of the reaction is determined by the stability of the corresponding isomers. The mechanism was investigated by additional DFT calculations, and the opening of the tetrazole ring was shown to be the rate-determining step. By maneuvering Pd-catalyzed N-arylation and the subsequent Dimroth rearrangement, two more N,1-diaryl-1H-tetrazol-5-amine derivatives were acquired, which otherwise cannot be synthesized by employing the C–N cross-coupling reaction.
PB  - American Chemical Society (ACS)
T2  - The Journal of Organic Chemistry
T1  - Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines
VL  - 86
IS  - 6
SP  - 4794
EP  - 4803
DO  - 10.1021/acs.joc.1c00282
ER  - 

@article{
author = "Nikolić, Andrea and Stanić, Jelena and Zlatar, Matija and Gruden, Maja and Anđelković, Boban and Selaković, Života and Ajdačić, Vladimir and Opsenica, Igor",
year = "2021",
abstract = "The Pd-catalyzed N-arylation method for the synthesis of eighteen N,1-diaryl-1H-tetrazol-5-amine derivatives is reported. By running the reactions at 35 °C, compounds were isolated as single isomers since the undesired Dimroth rearrangement was completely suppressed. Furthermore, the Dimroth rearrangement of N,1-diaryl-1H-tetrazol-5-amines was rationalized by conducting comprehensive experiments and NMR analysis as well as density functional theory (DFT) calculations of thermodynamic stability of the compounds. It was established that the Dimroth rearrangement is thermodynamically controlled, and the equilibrium of the reaction is determined by the stability of the corresponding isomers. The mechanism was investigated by additional DFT calculations, and the opening of the tetrazole ring was shown to be the rate-determining step. By maneuvering Pd-catalyzed N-arylation and the subsequent Dimroth rearrangement, two more N,1-diaryl-1H-tetrazol-5-amine derivatives were acquired, which otherwise cannot be synthesized by employing the C–N cross-coupling reaction.",
publisher = "American Chemical Society (ACS)",
journal = "The Journal of Organic Chemistry",
title = "Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines",
volume = "86",
number = "6",
pages = "4794-4803",
doi = "10.1021/acs.joc.1c00282"
}

Nikolić, A., Stanić, J., Zlatar, M., Gruden, M., Anđelković, B., Selaković, Ž., Ajdačić, V.,& Opsenica, I.. (2021). Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines. in The Journal of Organic Chemistry
American Chemical Society (ACS)., 86(6), 4794-4803.
https://doi.org/10.1021/acs.joc.1c00282

Nikolić A, Stanić J, Zlatar M, Gruden M, Anđelković B, Selaković Ž, Ajdačić V, Opsenica I. Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines. in The Journal of Organic Chemistry. 2021;86(6):4794-4803.
doi:10.1021/acs.joc.1c00282 .

Nikolić, Andrea, Stanić, Jelena, Zlatar, Matija, Gruden, Maja, Anđelković, Boban, Selaković, Života, Ajdačić, Vladimir, Opsenica, Igor, "Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines" in The Journal of Organic Chemistry, 86, no. 6 (2021):4794-4803,
https://doi.org/10.1021/acs.joc.1c00282 . .

TY  - JOUR
AU  - Nikolić, Andrea
AU  - Stanić, Jelena
AU  - Zlatar, Matija
AU  - Gruden, Maja
AU  - Anđelković, Boban
AU  - Selaković, Života
AU  - Ajdačić, Vladimir
AU  - Opsenica, Igor
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4431
AB  - The Pd-catalyzed N-arylation method for the synthesis of eighteen N,1-diaryl-1H-tetrazol-5-amine derivatives is reported. By running the reactions at 35 °C, compounds were isolated as single isomers since the undesired Dimroth rearrangement was completely suppressed. Furthermore, the Dimroth rearrangement of N,1-diaryl-1H-tetrazol-5-amines was rationalized by conducting comprehensive experiments and NMR analysis as well as density functional theory (DFT) calculations of thermodynamic stability of the compounds. It was established that the Dimroth rearrangement is thermodynamically controlled, and the equilibrium of the reaction is determined by the stability of the corresponding isomers. The mechanism was investigated by additional DFT calculations, and the opening of the tetrazole ring was shown to be the rate-determining step. By maneuvering Pd-catalyzed N-arylation and the subsequent Dimroth rearrangement, two more N,1-diaryl-1H-tetrazol-5-amine derivatives were acquired, which otherwise cannot be synthesized by employing the C–N cross-coupling reaction.
PB  - American Chemical Society (ACS)
T2  - The Journal of Organic Chemistry
T1  - Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines
VL  - 86
IS  - 6
SP  - 4794
EP  - 4803
DO  - 10.1021/acs.joc.1c00282
ER  - 

@article{
author = "Nikolić, Andrea and Stanić, Jelena and Zlatar, Matija and Gruden, Maja and Anđelković, Boban and Selaković, Života and Ajdačić, Vladimir and Opsenica, Igor",
year = "2021",
abstract = "The Pd-catalyzed N-arylation method for the synthesis of eighteen N,1-diaryl-1H-tetrazol-5-amine derivatives is reported. By running the reactions at 35 °C, compounds were isolated as single isomers since the undesired Dimroth rearrangement was completely suppressed. Furthermore, the Dimroth rearrangement of N,1-diaryl-1H-tetrazol-5-amines was rationalized by conducting comprehensive experiments and NMR analysis as well as density functional theory (DFT) calculations of thermodynamic stability of the compounds. It was established that the Dimroth rearrangement is thermodynamically controlled, and the equilibrium of the reaction is determined by the stability of the corresponding isomers. The mechanism was investigated by additional DFT calculations, and the opening of the tetrazole ring was shown to be the rate-determining step. By maneuvering Pd-catalyzed N-arylation and the subsequent Dimroth rearrangement, two more N,1-diaryl-1H-tetrazol-5-amine derivatives were acquired, which otherwise cannot be synthesized by employing the C–N cross-coupling reaction.",
publisher = "American Chemical Society (ACS)",
journal = "The Journal of Organic Chemistry",
title = "Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines",
volume = "86",
number = "6",
pages = "4794-4803",
doi = "10.1021/acs.joc.1c00282"
}

Nikolić, A., Stanić, J., Zlatar, M., Gruden, M., Anđelković, B., Selaković, Ž., Ajdačić, V.,& Opsenica, I.. (2021). Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines. in The Journal of Organic Chemistry
American Chemical Society (ACS)., 86(6), 4794-4803.
https://doi.org/10.1021/acs.joc.1c00282

Nikolić A, Stanić J, Zlatar M, Gruden M, Anđelković B, Selaković Ž, Ajdačić V, Opsenica I. Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines. in The Journal of Organic Chemistry. 2021;86(6):4794-4803.
doi:10.1021/acs.joc.1c00282 .

Nikolić, Andrea, Stanić, Jelena, Zlatar, Matija, Gruden, Maja, Anđelković, Boban, Selaković, Života, Ajdačić, Vladimir, Opsenica, Igor, "Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines" in The Journal of Organic Chemistry, 86, no. 6 (2021):4794-4803,
https://doi.org/10.1021/acs.joc.1c00282 . .

TY  - CONF
AU  - Anđelković, Boban
AU  - Sofrenić, Ivana
AU  - Ljujić, Jovana
AU  - Simić, Katarina
AU  - Ivanović, Stefan
AU  - Gođevac, Dejan
AU  - Tešević, Vele
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5528
AB  - FTIR spectroscopy is non-destructive and simple analytical technique that requires
small sample amounts for providing information about functional groups in molecules. In
certain cases, it is indispensable for structure elucidation of complex organic molecules such as
triterpene derivatives1. Applying this technique, it is possible to monitor the change in the
secondary structure of the protein.2.
Combined with various statistical methods it is a powerful analytical tool in
metabolomics. Thus, FTIR data based statistical models enabled propolis classification and
floral origin determination3. In combination with biological tests such as cytotoxic activity), it
can be used for biologically guided isolation of active compounds4.
Nowadays FTIR spectroscopy is being routinely used for solving various practical
analytical problems, e. g. quality analysis of bees products (beeswax and honey), quantitative
determination of the major constituents in most types of food and agricultural products,
straightforward identification of kidney and bladder stones etc.
PB  - Societat Catalana de Química (SCQ) (Catalan Chemical Society)
PB  - EuChemS Divison of Organic Chemistry
C3  - XII Young Investigator Workshop, 25th – 26th November 2021, Barcelona, Spain
T1  - Ft-IR spectroscopy as a simple tool for rapid solution of various problems
SP  - 35
EP  - 35
UR  - https://hdl.handle.net/21.15107/rcub_cer_5528
ER  - 

@conference{
author = "Anđelković, Boban and Sofrenić, Ivana and Ljujić, Jovana and Simić, Katarina and Ivanović, Stefan and Gođevac, Dejan and Tešević, Vele",
year = "2021",
abstract = "FTIR spectroscopy is non-destructive and simple analytical technique that requires
small sample amounts for providing information about functional groups in molecules. In
certain cases, it is indispensable for structure elucidation of complex organic molecules such as
triterpene derivatives1. Applying this technique, it is possible to monitor the change in the
secondary structure of the protein.2.
Combined with various statistical methods it is a powerful analytical tool in
metabolomics. Thus, FTIR data based statistical models enabled propolis classification and
floral origin determination3. In combination with biological tests such as cytotoxic activity), it
can be used for biologically guided isolation of active compounds4.
Nowadays FTIR spectroscopy is being routinely used for solving various practical
analytical problems, e. g. quality analysis of bees products (beeswax and honey), quantitative
determination of the major constituents in most types of food and agricultural products,
straightforward identification of kidney and bladder stones etc.",
publisher = "Societat Catalana de Química (SCQ) (Catalan Chemical Society), EuChemS Divison of Organic Chemistry",
journal = "XII Young Investigator Workshop, 25th – 26th November 2021, Barcelona, Spain",
title = "Ft-IR spectroscopy as a simple tool for rapid solution of various problems",
pages = "35-35",
url = "https://hdl.handle.net/21.15107/rcub_cer_5528"
}

Anđelković, B., Sofrenić, I., Ljujić, J., Simić, K., Ivanović, S., Gođevac, D.,& Tešević, V.. (2021). Ft-IR spectroscopy as a simple tool for rapid solution of various problems. in XII Young Investigator Workshop, 25th – 26th November 2021, Barcelona, Spain
Societat Catalana de Química (SCQ) (Catalan Chemical Society)., 35-35.
https://hdl.handle.net/21.15107/rcub_cer_5528

Anđelković B, Sofrenić I, Ljujić J, Simić K, Ivanović S, Gođevac D, Tešević V. Ft-IR spectroscopy as a simple tool for rapid solution of various problems. in XII Young Investigator Workshop, 25th – 26th November 2021, Barcelona, Spain. 2021;:35-35.
https://hdl.handle.net/21.15107/rcub_cer_5528 .

Anđelković, Boban, Sofrenić, Ivana, Ljujić, Jovana, Simić, Katarina, Ivanović, Stefan, Gođevac, Dejan, Tešević, Vele, "Ft-IR spectroscopy as a simple tool for rapid solution of various problems" in XII Young Investigator Workshop, 25th – 26th November 2021, Barcelona, Spain (2021):35-35,
https://hdl.handle.net/21.15107/rcub_cer_5528 .

TY  - CONF
AU  - Lješević, Marija
AU  - Troncozo, M.I.
AU  - Balatti, P.A.
AU  - Saparrat, M.C.N.
AU  - Anđelković, Boban D.
AU  - Beškoski, Vladimir
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5143
AB  - The main goal of this study was to analyze the transformation of grape pomace by six different fungal strains and assess if it can be a successful pretreatment method for the grape pomace waste.
PB  - Opole, Poland : University of Opole
C3  - QUO VADIS Life Sciences Conference, Abstract book, 23-27 June 2021, Opole, Poland
T1  - Fungal transformation of grape pomace- analysis using GCxGC-MS
SP  - 146
UR  - https://hdl.handle.net/21.15107/rcub_cer_5143
ER  - 

@conference{
author = "Lješević, Marija and Troncozo, M.I. and Balatti, P.A. and Saparrat, M.C.N. and Anđelković, Boban D. and Beškoski, Vladimir",
year = "2021",
abstract = "The main goal of this study was to analyze the transformation of grape pomace by six different fungal strains and assess if it can be a successful pretreatment method for the grape pomace waste.",
publisher = "Opole, Poland : University of Opole",
journal = "QUO VADIS Life Sciences Conference, Abstract book, 23-27 June 2021, Opole, Poland",
title = "Fungal transformation of grape pomace- analysis using GCxGC-MS",
pages = "146",
url = "https://hdl.handle.net/21.15107/rcub_cer_5143"
}

Lješević, M., Troncozo, M.I., Balatti, P.A., Saparrat, M.C.N., Anđelković, B. D.,& Beškoski, V.. (2021). Fungal transformation of grape pomace- analysis using GCxGC-MS. in QUO VADIS Life Sciences Conference, Abstract book, 23-27 June 2021, Opole, Poland
Opole, Poland : University of Opole., 146.
https://hdl.handle.net/21.15107/rcub_cer_5143

Lješević M, Troncozo M, Balatti P, Saparrat M, Anđelković BD, Beškoski V. Fungal transformation of grape pomace- analysis using GCxGC-MS. in QUO VADIS Life Sciences Conference, Abstract book, 23-27 June 2021, Opole, Poland. 2021;:146.
https://hdl.handle.net/21.15107/rcub_cer_5143 .

Lješević, Marija, Troncozo, M.I., Balatti, P.A., Saparrat, M.C.N., Anđelković, Boban D., Beškoski, Vladimir, "Fungal transformation of grape pomace- analysis using GCxGC-MS" in QUO VADIS Life Sciences Conference, Abstract book, 23-27 June 2021, Opole, Poland (2021):146,
https://hdl.handle.net/21.15107/rcub_cer_5143 .

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  - CONF
AU  - Gođevac, Dejan
AU  - Simić, Katarina
AU  - Ivanović, Stefan
AU  - Anđelković, Boban
AU  - Jovanović, Živko
AU  - Rakić, Tamara
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5524
AB  - Ramonda serbica represents the remnant of the Tertiary tropical and subtropical flora in Europe and is the rare resurrection plants of Northern Hemisphere temperate zone. The plant remains well-hydrated during spring, late autumn and in winter. In summer and early autumn when plants are subjected to drought, their desiccation tolerance comes into operation and they spend it in anabiosis [1]. In this study, metabolic responses to dehydration and rehydration of R. serbica, were investigated. For this purpose, GC-MS/FID
based metabolomics method was performed. Leaves from the control (well-watered), dehydrated and partially rehydrated plants were sampled. Each leaf was powdered using liquid nitrogen and then freeze-dried. The internal standard (10-undecenoic acid) was added to the dry plant material and then extracted in methanol/water using ultra-sonication. After centrifugation of the mixture, the supernatant was dried and derivatized using two-step procedure involving oximation and silylation. GC-MS/FID analysis of each sample was then performed. The metabolites were identified using El-MS spectra. The areas from FID chromatograms were used for multivariate data analysis. Two OPLS-DA models were applied to investigate dehydration and rehydration process. According to high VIP scores, sugars, such as fructose, glucose, galactinol, sucrose, together with glyceric acid, xylonic acid 8-lactone and aspartic acid were found to be the most influential in the OPLS-DA models.
PB  - ICNPU-2019
C3  - Book of abstracts - 4th international conference on  natural products utilization: from plants to pharmacy shelf, 29/05-01/06 2019, Albena, Bulgaria
T1  - GC-MS based metabolomics study of the resurrection plant Ramonda serbica
SP  - 189
EP  - 190
UR  - https://hdl.handle.net/21.15107/rcub_cer_5524
ER  - 

@conference{
author = "Gođevac, Dejan and Simić, Katarina and Ivanović, Stefan and Anđelković, Boban and Jovanović, Živko and Rakić, Tamara",
year = "2019",
abstract = "Ramonda serbica represents the remnant of the Tertiary tropical and subtropical flora in Europe and is the rare resurrection plants of Northern Hemisphere temperate zone. The plant remains well-hydrated during spring, late autumn and in winter. In summer and early autumn when plants are subjected to drought, their desiccation tolerance comes into operation and they spend it in anabiosis [1]. In this study, metabolic responses to dehydration and rehydration of R. serbica, were investigated. For this purpose, GC-MS/FID
based metabolomics method was performed. Leaves from the control (well-watered), dehydrated and partially rehydrated plants were sampled. Each leaf was powdered using liquid nitrogen and then freeze-dried. The internal standard (10-undecenoic acid) was added to the dry plant material and then extracted in methanol/water using ultra-sonication. After centrifugation of the mixture, the supernatant was dried and derivatized using two-step procedure involving oximation and silylation. GC-MS/FID analysis of each sample was then performed. The metabolites were identified using El-MS spectra. The areas from FID chromatograms were used for multivariate data analysis. Two OPLS-DA models were applied to investigate dehydration and rehydration process. According to high VIP scores, sugars, such as fructose, glucose, galactinol, sucrose, together with glyceric acid, xylonic acid 8-lactone and aspartic acid were found to be the most influential in the OPLS-DA models.",
publisher = "ICNPU-2019",
journal = "Book of abstracts - 4th international conference on  natural products utilization: from plants to pharmacy shelf, 29/05-01/06 2019, Albena, Bulgaria",
title = "GC-MS based metabolomics study of the resurrection plant Ramonda serbica",
pages = "189-190",
url = "https://hdl.handle.net/21.15107/rcub_cer_5524"
}

Gođevac, D., Simić, K., Ivanović, S., Anđelković, B., Jovanović, Ž.,& Rakić, T.. (2019). GC-MS based metabolomics study of the resurrection plant Ramonda serbica. in Book of abstracts - 4th international conference on  natural products utilization: from plants to pharmacy shelf, 29/05-01/06 2019, Albena, Bulgaria
ICNPU-2019., 189-190.
https://hdl.handle.net/21.15107/rcub_cer_5524

Gođevac D, Simić K, Ivanović S, Anđelković B, Jovanović Ž, Rakić T. GC-MS based metabolomics study of the resurrection plant Ramonda serbica. in Book of abstracts - 4th international conference on  natural products utilization: from plants to pharmacy shelf, 29/05-01/06 2019, Albena, Bulgaria. 2019;:189-190.
https://hdl.handle.net/21.15107/rcub_cer_5524 .

Gođevac, Dejan, Simić, Katarina, Ivanović, Stefan, Anđelković, Boban, Jovanović, Živko, Rakić, Tamara, "GC-MS based metabolomics study of the resurrection plant Ramonda serbica" in Book of abstracts - 4th international conference on  natural products utilization: from plants to pharmacy shelf, 29/05-01/06 2019, Albena, Bulgaria (2019):189-190,
https://hdl.handle.net/21.15107/rcub_cer_5524 .

TY  - JOUR
AU  - Novaković, Miroslav
AU  - Bukvicki, Danka
AU  - Anđelković, Boban D.
AU  - Ilić-Tomić, Tatjana
AU  - Veljić, Milan
AU  - Tešević, Vele
AU  - Asakawa, Yoshinori
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2838
AB  - Seven new bisbibenzyls (1−7) were isolated from the methanol extract of the liverwort Lunularia cruciata along with one previously known bibenzyl and five known bisbibenzyls. The structures of compounds 1−7 were elucidated on the basis of the spectroscopic data. These newly isolated bisbibenzyls may be divided into two groups, the acyclic bisbibenzyls, perrottetins (1− 3), and the cyclic analogues, riccardins (4−7). Besides standard perrottetin and riccardin structures (1 and 4, respectively), they contain phenanthrene (3 and 5), dihydrophenanthrene (2), and quinone moieties (6 and 7), rarely found in natural products. The new compounds 3 and 5, as well as the known riccardin G, exhibited cytotoxic activity against the A549 lung cancer cell line with IC50 values of 5.0, 5.0, and 2.5 μM, respectively.
PB  - American Chemical Society (ACS)
T2  - Journal of Natural Products
T1  - Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia cruciata
VL  - 82
IS  - 4
SP  - 694
EP  - 701
DO  - 10.1021/acs.jnatprod.8b00390
ER  - 

@article{
author = "Novaković, Miroslav and Bukvicki, Danka and Anđelković, Boban D. and Ilić-Tomić, Tatjana and Veljić, Milan and Tešević, Vele and Asakawa, Yoshinori",
year = "2019",
abstract = "Seven new bisbibenzyls (1−7) were isolated from the methanol extract of the liverwort Lunularia cruciata along with one previously known bibenzyl and five known bisbibenzyls. The structures of compounds 1−7 were elucidated on the basis of the spectroscopic data. These newly isolated bisbibenzyls may be divided into two groups, the acyclic bisbibenzyls, perrottetins (1− 3), and the cyclic analogues, riccardins (4−7). Besides standard perrottetin and riccardin structures (1 and 4, respectively), they contain phenanthrene (3 and 5), dihydrophenanthrene (2), and quinone moieties (6 and 7), rarely found in natural products. The new compounds 3 and 5, as well as the known riccardin G, exhibited cytotoxic activity against the A549 lung cancer cell line with IC50 values of 5.0, 5.0, and 2.5 μM, respectively.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Natural Products",
title = "Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia cruciata",
volume = "82",
number = "4",
pages = "694-701",
doi = "10.1021/acs.jnatprod.8b00390"
}

Novaković, M., Bukvicki, D., Anđelković, B. D., Ilić-Tomić, T., Veljić, M., Tešević, V.,& Asakawa, Y.. (2019). Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia cruciata. in Journal of Natural Products
American Chemical Society (ACS)., 82(4), 694-701.
https://doi.org/10.1021/acs.jnatprod.8b00390

Novaković M, Bukvicki D, Anđelković BD, Ilić-Tomić T, Veljić M, Tešević V, Asakawa Y. Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia cruciata. in Journal of Natural Products. 2019;82(4):694-701.
doi:10.1021/acs.jnatprod.8b00390 .

Novaković, Miroslav, Bukvicki, Danka, Anđelković, Boban D., Ilić-Tomić, Tatjana, Veljić, Milan, Tešević, Vele, Asakawa, Yoshinori, "Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia cruciata" in Journal of Natural Products, 82, no. 4 (2019):694-701,
https://doi.org/10.1021/acs.jnatprod.8b00390 . .

TY  - JOUR
AU  - Ozek, Gulmira
AU  - Yur, Suleyman
AU  - Goger, Fatih
AU  - Ozek, Temel
AU  - Anđelković, Boban D.
AU  - Gođevac, Dejan
AU  - Sofrenić, Ivana
AU  - Aneva, Ina
AU  - Todorova, Milka
AU  - Trendafilova, Antoaneta
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2869
AB  - Hexane extracts of Heracleum verticillatum, H. sibiricum, H. angustisectum, and H. ternatum were studied for their furanocoumarin content antioxidant potential and acetylcholinesterase and α-amylase inhibitory activities. Quantification of the furanocoumarins was performed by 1H-NMR. Pimpinellin was found to be the main component in the roots of all studied species. Bergapten and imperatorin were the major compounds in the fruits of H. sibiricum and H. verticillatum, respectively, while byakangelicol dominated in H. angustisectum and H. ternatum fruits. The leaf and fruit extracts of H. angustisectum demonstrated the highest DPPH radical scavenging activity and TEAC (IC50 0.58 mg/mL and 1.83 mM, respectively). The root extracts of H. verticillatum and H.angustisectum were found to be the most effective against acetylcholinesterase (IC50 0.30 and 0.34 mg/mL, respectively). The studied extracts were not active or demonstrated a weak inhibitory effect (%Inh. up to 29.7) towards α-amylase.
PB  - Willey
T2  - Chemistry and Biodiversity
T1  - Furanocoumarin Content, Antioxidant Activity, and Inhibitory Potential of Heracleum verticillatum, Heracleum sibiricum, Heracleum angustisectum, and Heracleum ternatum Extracts against Enzymes Involved in Alzheimer’s Disease and Type II Diabetes
VL  - 16
IS  - 4
SP  - e1800672
DO  - 10.1002/cbdv.201800672
ER  - 

@article{
author = "Ozek, Gulmira and Yur, Suleyman and Goger, Fatih and Ozek, Temel and Anđelković, Boban D. and Gođevac, Dejan and Sofrenić, Ivana and Aneva, Ina and Todorova, Milka and Trendafilova, Antoaneta",
year = "2019",
abstract = "Hexane extracts of Heracleum verticillatum, H. sibiricum, H. angustisectum, and H. ternatum were studied for their furanocoumarin content antioxidant potential and acetylcholinesterase and α-amylase inhibitory activities. Quantification of the furanocoumarins was performed by 1H-NMR. Pimpinellin was found to be the main component in the roots of all studied species. Bergapten and imperatorin were the major compounds in the fruits of H. sibiricum and H. verticillatum, respectively, while byakangelicol dominated in H. angustisectum and H. ternatum fruits. The leaf and fruit extracts of H. angustisectum demonstrated the highest DPPH radical scavenging activity and TEAC (IC50 0.58 mg/mL and 1.83 mM, respectively). The root extracts of H. verticillatum and H.angustisectum were found to be the most effective against acetylcholinesterase (IC50 0.30 and 0.34 mg/mL, respectively). The studied extracts were not active or demonstrated a weak inhibitory effect (%Inh. up to 29.7) towards α-amylase.",
publisher = "Willey",
journal = "Chemistry and Biodiversity",
title = "Furanocoumarin Content, Antioxidant Activity, and Inhibitory Potential of Heracleum verticillatum, Heracleum sibiricum, Heracleum angustisectum, and Heracleum ternatum Extracts against Enzymes Involved in Alzheimer’s Disease and Type II Diabetes",
volume = "16",
number = "4",
pages = "e1800672",
doi = "10.1002/cbdv.201800672"
}

Ozek, G., Yur, S., Goger, F., Ozek, T., Anđelković, B. D., Gođevac, D., Sofrenić, I., Aneva, I., Todorova, M.,& Trendafilova, A.. (2019). Furanocoumarin Content, Antioxidant Activity, and Inhibitory Potential of Heracleum verticillatum, Heracleum sibiricum, Heracleum angustisectum, and Heracleum ternatum Extracts against Enzymes Involved in Alzheimer’s Disease and Type II Diabetes. in Chemistry and Biodiversity
Willey., 16(4), e1800672.
https://doi.org/10.1002/cbdv.201800672

Ozek G, Yur S, Goger F, Ozek T, Anđelković BD, Gođevac D, Sofrenić I, Aneva I, Todorova M, Trendafilova A. Furanocoumarin Content, Antioxidant Activity, and Inhibitory Potential of Heracleum verticillatum, Heracleum sibiricum, Heracleum angustisectum, and Heracleum ternatum Extracts against Enzymes Involved in Alzheimer’s Disease and Type II Diabetes. in Chemistry and Biodiversity. 2019;16(4):e1800672.
doi:10.1002/cbdv.201800672 .

Ozek, Gulmira, Yur, Suleyman, Goger, Fatih, Ozek, Temel, Anđelković, Boban D., Gođevac, Dejan, Sofrenić, Ivana, Aneva, Ina, Todorova, Milka, Trendafilova, Antoaneta, "Furanocoumarin Content, Antioxidant Activity, and Inhibitory Potential of Heracleum verticillatum, Heracleum sibiricum, Heracleum angustisectum, and Heracleum ternatum Extracts against Enzymes Involved in Alzheimer’s Disease and Type II Diabetes" in Chemistry and Biodiversity, 16, no. 4 (2019):e1800672,
https://doi.org/10.1002/cbdv.201800672 . .

TY  - JOUR
AU  - Ozek, Gulmira
AU  - Yur, Suleyman
AU  - Goger, Fatih
AU  - Ozek, Temel
AU  - Anđelković, Boban D.
AU  - Gođevac, Dejan
AU  - Sofrenić, Ivana
AU  - Aneva, Ina
AU  - Todorova, Milka
AU  - Trendafilova, Antoaneta
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2869
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2899
AB  - Hexane extracts of Heracleum verticillatum, H. sibiricum, H. angustisectum, and H. ternatum were studied fortheir furanocoumarin content antioxidant potential and acetylcholinesterase and α-amylase inhibitory activities.Quantification of the furanocoumarins was performed by 1H-NMR. Pimpinellin was found to be the maincomponent in the roots of all studied species. Bergapten and imperatorin were the major compounds in thefruits of H. sibiricum and H. verticillatum, respectively, while byakangelicol dominated in H. angustisectum and H.ternatum fruits. The leaf and fruit extracts of H. angustisectum demonstrated the highest DPPH radical scavengingactivity and TEAC (IC50 0.58 mg/mL and 1.83 mM, respectively). The root extracts of H. verticillatum and H.angustisectum were found to be the most effective against acetylcholinesterase (IC50 0.30 and 0.34 mg/mL,respectively). The studied extracts were not active or demonstrated a weak inhibitory effect (%Inh. up to 29.7)towards α-amylase.
PB  - Willey
T2  - Chemistry and Biodiversity
T1  - Furanocoumarin Content, Antioxidant Activity, and Inhibitory Potential of Heracleum verticillatum, Heracleum sibiricum, Heracleum angustisectum, and Heracleum ternatum Extracts against Enzymes Involved in Alzheimer’s Disease and Type II Diabetes
VL  - 16
IS  - 4
SP  - e1800672
DO  - 10.1002/cbdv.201800672
ER  - 

@article{
author = "Ozek, Gulmira and Yur, Suleyman and Goger, Fatih and Ozek, Temel and Anđelković, Boban D. and Gođevac, Dejan and Sofrenić, Ivana and Aneva, Ina and Todorova, Milka and Trendafilova, Antoaneta",
year = "2019",
abstract = "Hexane extracts of Heracleum verticillatum, H. sibiricum, H. angustisectum, and H. ternatum were studied fortheir furanocoumarin content antioxidant potential and acetylcholinesterase and α-amylase inhibitory activities.Quantification of the furanocoumarins was performed by 1H-NMR. Pimpinellin was found to be the maincomponent in the roots of all studied species. Bergapten and imperatorin were the major compounds in thefruits of H. sibiricum and H. verticillatum, respectively, while byakangelicol dominated in H. angustisectum and H.ternatum fruits. The leaf and fruit extracts of H. angustisectum demonstrated the highest DPPH radical scavengingactivity and TEAC (IC50 0.58 mg/mL and 1.83 mM, respectively). The root extracts of H. verticillatum and H.angustisectum were found to be the most effective against acetylcholinesterase (IC50 0.30 and 0.34 mg/mL,respectively). The studied extracts were not active or demonstrated a weak inhibitory effect (%Inh. up to 29.7)towards α-amylase.",
publisher = "Willey",
journal = "Chemistry and Biodiversity",
title = "Furanocoumarin Content, Antioxidant Activity, and Inhibitory Potential of Heracleum verticillatum, Heracleum sibiricum, Heracleum angustisectum, and Heracleum ternatum Extracts against Enzymes Involved in Alzheimer’s Disease and Type II Diabetes",
volume = "16",
number = "4",
pages = "e1800672",
doi = "10.1002/cbdv.201800672"
}

Ozek, G., Yur, S., Goger, F., Ozek, T., Anđelković, B. D., Gođevac, D., Sofrenić, I., Aneva, I., Todorova, M.,& Trendafilova, A.. (2019). Furanocoumarin Content, Antioxidant Activity, and Inhibitory Potential of Heracleum verticillatum, Heracleum sibiricum, Heracleum angustisectum, and Heracleum ternatum Extracts against Enzymes Involved in Alzheimer’s Disease and Type II Diabetes. in Chemistry and Biodiversity
Willey., 16(4), e1800672.
https://doi.org/10.1002/cbdv.201800672

Ozek G, Yur S, Goger F, Ozek T, Anđelković BD, Gođevac D, Sofrenić I, Aneva I, Todorova M, Trendafilova A. Furanocoumarin Content, Antioxidant Activity, and Inhibitory Potential of Heracleum verticillatum, Heracleum sibiricum, Heracleum angustisectum, and Heracleum ternatum Extracts against Enzymes Involved in Alzheimer’s Disease and Type II Diabetes. in Chemistry and Biodiversity. 2019;16(4):e1800672.
doi:10.1002/cbdv.201800672 .

Ozek, Gulmira, Yur, Suleyman, Goger, Fatih, Ozek, Temel, Anđelković, Boban D., Gođevac, Dejan, Sofrenić, Ivana, Aneva, Ina, Todorova, Milka, Trendafilova, Antoaneta, "Furanocoumarin Content, Antioxidant Activity, and Inhibitory Potential of Heracleum verticillatum, Heracleum sibiricum, Heracleum angustisectum, and Heracleum ternatum Extracts against Enzymes Involved in Alzheimer’s Disease and Type II Diabetes" in Chemistry and Biodiversity, 16, no. 4 (2019):e1800672,
https://doi.org/10.1002/cbdv.201800672 . .

TY  - JOUR
AU  - Troncozo, María I.
AU  - Lješević, Marija
AU  - Beškoski, Vladimir
AU  - Anđelković, Boban D.
AU  - Ballati, Pedro A.
AU  - Saparrat, Mario C. N.
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3055
AB  - Grape pomace (GP) from Vitis labrusca, the main byproduct from “American table wine” production, is recalcitrant to degradation, and its accumulation is a serious problem with negative environmental impacts. In this work, transformation of grape pomace using a steam pretreatment followed by incubation of GP during a 90-day period with six different fungi were evaluated. Several fungi tested reduced the phytotoxicity of water-soluble fraction (WSFd) from steam-pretreated GP after 90 days’ incubation to lettuce and tomato seeds. U. botrytis caused the largest effective phytotoxicity reduction ofWSFd (used in the concentration range of 10e1.25% p/v) and was the only fungus causing the removal of monoaromatic compounds. Therefore, this procedure with U. botrytis effectively reduces the availability of phytotoxic monoaromatic compounds in GP, which opens a way for the development of guidelines for the management of these wastes and their potential use as organic amendments in agricultural soil.
PB  - Elsevier
T2  - Chemosphere
T1  - Fungal transformation and reduction of phytotoxicity of grape pomace waste
VL  - 237
SP  - 124458
DO  - 10.1016/j.chemosphere.2019.124458
ER  - 

@article{
author = "Troncozo, María I. and Lješević, Marija and Beškoski, Vladimir and Anđelković, Boban D. and Ballati, Pedro A. and Saparrat, Mario C. N.",
year = "2019",
abstract = "Grape pomace (GP) from Vitis labrusca, the main byproduct from “American table wine” production, is recalcitrant to degradation, and its accumulation is a serious problem with negative environmental impacts. In this work, transformation of grape pomace using a steam pretreatment followed by incubation of GP during a 90-day period with six different fungi were evaluated. Several fungi tested reduced the phytotoxicity of water-soluble fraction (WSFd) from steam-pretreated GP after 90 days’ incubation to lettuce and tomato seeds. U. botrytis caused the largest effective phytotoxicity reduction ofWSFd (used in the concentration range of 10e1.25% p/v) and was the only fungus causing the removal of monoaromatic compounds. Therefore, this procedure with U. botrytis effectively reduces the availability of phytotoxic monoaromatic compounds in GP, which opens a way for the development of guidelines for the management of these wastes and their potential use as organic amendments in agricultural soil.",
publisher = "Elsevier",
journal = "Chemosphere",
title = "Fungal transformation and reduction of phytotoxicity of grape pomace waste",
volume = "237",
pages = "124458",
doi = "10.1016/j.chemosphere.2019.124458"
}

Troncozo, M. I., Lješević, M., Beškoski, V., Anđelković, B. D., Ballati, P. A.,& Saparrat, M. C. N.. (2019). Fungal transformation and reduction of phytotoxicity of grape pomace waste. in Chemosphere
Elsevier., 237, 124458.
https://doi.org/10.1016/j.chemosphere.2019.124458

Troncozo MI, Lješević M, Beškoski V, Anđelković BD, Ballati PA, Saparrat MCN. Fungal transformation and reduction of phytotoxicity of grape pomace waste. in Chemosphere. 2019;237:124458.
doi:10.1016/j.chemosphere.2019.124458 .

Troncozo, María I., Lješević, Marija, Beškoski, Vladimir, Anđelković, Boban D., Ballati, Pedro A., Saparrat, Mario C. N., "Fungal transformation and reduction of phytotoxicity of grape pomace waste" in Chemosphere, 237 (2019):124458,
https://doi.org/10.1016/j.chemosphere.2019.124458 . .

TY  - CONF
AU  - Kokalj, Doris
AU  - Gođevac, Dejan
AU  - Anđelković, Boban D.
AU  - Cigić, Blaž
AU  - Zlatić, Emil
AU  - Hribar, Janez
AU  - Vidrih, Rajko
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3068
AB  - A metabolomics approach based on nuclear magnetic resonance (NMR) spectroscopy, a rapid and simple technique, was used for the assessment of chemical changes of ‘Van’ sweet cherries during their storage. This approach affords a holistic analysis since NMR spectroscopy allows the simultaneous detection of diverse groups of secondary and primary metabolites, and reflects the real molar levels of the metabolites. Additionally, color parameters L*, a* and b*, total phenolic content (TPC), total flavonoid content (TFC), anthocyanidins and total antioxidant potential (AOP) were measured. After harvest, cherries were stored at 1°C and sampling was done after 0, 2, 4, 7 and 10 days. Cherry skin was removed, freeze dried and stored at -80°C till analyses. For NMR analyses, freeze dried cherry skins have been extracted with methanol-d4/trifluoroacetic acid-d solvent mixture. For other analyses, samples were extracted in 70% ethanol with 1% of formic acid. The 1D and 2D NMR spectral analysis confirmed that sugars (glucose, fructose, sucrose), organic acids (malic and citric acid), and phenolic compounds (neochlorogenic acid, cyanidin 3-O-rutinoside, and cyanidin 3-O-glucoside) are the main compounds in the cherry skin extracts. The 1H NMR spectral data have been subjected to multivariate analysis. Orthogonal projections to latent structures (OPLS) were applied to correlate the NMR data with the storage time. The changes in chemical composition among the samples with different storage time were clearly visible on the score plot. According to the goodness of fit of the model (R2=0.954), and its predictive ability (Q2=0.634), cherry skin extracts were well-correlated with the storage time. A positive correlation of the signals corresponding to glucose, neochlorogenic acid, cyanidin 3-O-rutinoside, and cyanidin 3-O-glucoside with the storage time of cherries has been observed on the loading plot. According to the loading plot, the increase in the content of glucose, neochlorogenic acid, cyanidin 3-O-rutinoside, and cyanidin 3-O-glucoside has been correlated with the storage time of cherries. Since polyphenolic compounds were found to correlate well with the storage time, the content of redox active compounds was further assessed with AOP, TPC and TFC. All these parameters were increasing for 7 days after harvest then started to decline slightly. The content of all three anthocyanidins increased 2 days after harvest then remained stable till the end of sampling period.
PB  - International Society for Horticultural Science (ISHS)
C3  - Acta Horticulturae
T1  - Nuclear magnetic resonance as a tool for the assessment of postharvest changes in the metabolome of the skin of sweet cherry (                    Prunus avium                    L.)
IS  - 1235
SP  - 483
EP  - 488
DO  - 10.17660/ActaHortic.2019.1235.67
ER  - 

@conference{
author = "Kokalj, Doris and Gođevac, Dejan and Anđelković, Boban D. and Cigić, Blaž and Zlatić, Emil and Hribar, Janez and Vidrih, Rajko",
year = "2019",
abstract = "A metabolomics approach based on nuclear magnetic resonance (NMR) spectroscopy, a rapid and simple technique, was used for the assessment of chemical changes of ‘Van’ sweet cherries during their storage. This approach affords a holistic analysis since NMR spectroscopy allows the simultaneous detection of diverse groups of secondary and primary metabolites, and reflects the real molar levels of the metabolites. Additionally, color parameters L*, a* and b*, total phenolic content (TPC), total flavonoid content (TFC), anthocyanidins and total antioxidant potential (AOP) were measured. After harvest, cherries were stored at 1°C and sampling was done after 0, 2, 4, 7 and 10 days. Cherry skin was removed, freeze dried and stored at -80°C till analyses. For NMR analyses, freeze dried cherry skins have been extracted with methanol-d4/trifluoroacetic acid-d solvent mixture. For other analyses, samples were extracted in 70% ethanol with 1% of formic acid. The 1D and 2D NMR spectral analysis confirmed that sugars (glucose, fructose, sucrose), organic acids (malic and citric acid), and phenolic compounds (neochlorogenic acid, cyanidin 3-O-rutinoside, and cyanidin 3-O-glucoside) are the main compounds in the cherry skin extracts. The 1H NMR spectral data have been subjected to multivariate analysis. Orthogonal projections to latent structures (OPLS) were applied to correlate the NMR data with the storage time. The changes in chemical composition among the samples with different storage time were clearly visible on the score plot. According to the goodness of fit of the model (R2=0.954), and its predictive ability (Q2=0.634), cherry skin extracts were well-correlated with the storage time. A positive correlation of the signals corresponding to glucose, neochlorogenic acid, cyanidin 3-O-rutinoside, and cyanidin 3-O-glucoside with the storage time of cherries has been observed on the loading plot. According to the loading plot, the increase in the content of glucose, neochlorogenic acid, cyanidin 3-O-rutinoside, and cyanidin 3-O-glucoside has been correlated with the storage time of cherries. Since polyphenolic compounds were found to correlate well with the storage time, the content of redox active compounds was further assessed with AOP, TPC and TFC. All these parameters were increasing for 7 days after harvest then started to decline slightly. The content of all three anthocyanidins increased 2 days after harvest then remained stable till the end of sampling period.",
publisher = "International Society for Horticultural Science (ISHS)",
journal = "Acta Horticulturae",
title = "Nuclear magnetic resonance as a tool for the assessment of postharvest changes in the metabolome of the skin of sweet cherry (                    Prunus avium                    L.)",
number = "1235",
pages = "483-488",
doi = "10.17660/ActaHortic.2019.1235.67"
}

Kokalj, D., Gođevac, D., Anđelković, B. D., Cigić, B., Zlatić, E., Hribar, J.,& Vidrih, R.. (2019). Nuclear magnetic resonance as a tool for the assessment of postharvest changes in the metabolome of the skin of sweet cherry (                    Prunus avium                    L.). in Acta Horticulturae
International Society for Horticultural Science (ISHS).(1235), 483-488.
https://doi.org/10.17660/ActaHortic.2019.1235.67

Kokalj D, Gođevac D, Anđelković BD, Cigić B, Zlatić E, Hribar J, Vidrih R. Nuclear magnetic resonance as a tool for the assessment of postharvest changes in the metabolome of the skin of sweet cherry (                    Prunus avium                    L.). in Acta Horticulturae. 2019;(1235):483-488.
doi:10.17660/ActaHortic.2019.1235.67 .

Kokalj, Doris, Gođevac, Dejan, Anđelković, Boban D., Cigić, Blaž, Zlatić, Emil, Hribar, Janez, Vidrih, Rajko, "Nuclear magnetic resonance as a tool for the assessment of postharvest changes in the metabolome of the skin of sweet cherry (                    Prunus avium                    L.)" in Acta Horticulturae, no. 1235 (2019):483-488,
https://doi.org/10.17660/ActaHortic.2019.1235.67 . .

TY  - DATA
AU  - Novaković, Miroslav
AU  - Bukvicki, Danka
AU  - Anđelković, Boban D.
AU  - Ilić-Tomić, Tatjana
AU  - Veljić, Milan
AU  - Tešević, Vele
AU  - Asakawa, Yoshinori
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4449
AB  - NMR spectra of the isolated compounds and additional figures and tables. Table S1. Elution Program for the Silica Gel Column Separation;  Figure S1. Aromatic part of the 1H NMR spectrum of compound 1;
PB  - American Chemical Society (ACS)
T2  - Journal of Natural Products
T1  - Supporting information for: "Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia cruciata"
DO  - 10.1021/acs.jnatprod.8b00390.s001
ER  - 

@misc{
author = "Novaković, Miroslav and Bukvicki, Danka and Anđelković, Boban D. and Ilić-Tomić, Tatjana and Veljić, Milan and Tešević, Vele and Asakawa, Yoshinori",
year = "2019",
abstract = "NMR spectra of the isolated compounds and additional figures and tables. Table S1. Elution Program for the Silica Gel Column Separation;  Figure S1. Aromatic part of the 1H NMR spectrum of compound 1;",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Natural Products",
title = "Supporting information for: "Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia cruciata"",
doi = "10.1021/acs.jnatprod.8b00390.s001"
}

Novaković, M., Bukvicki, D., Anđelković, B. D., Ilić-Tomić, T., Veljić, M., Tešević, V.,& Asakawa, Y.. (2019). Supporting information for: "Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia cruciata". in Journal of Natural Products
American Chemical Society (ACS)..
https://doi.org/10.1021/acs.jnatprod.8b00390.s001

Novaković M, Bukvicki D, Anđelković BD, Ilić-Tomić T, Veljić M, Tešević V, Asakawa Y. Supporting information for: "Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia cruciata". in Journal of Natural Products. 2019;.
doi:10.1021/acs.jnatprod.8b00390.s001 .

Novaković, Miroslav, Bukvicki, Danka, Anđelković, Boban D., Ilić-Tomić, Tatjana, Veljić, Milan, Tešević, Vele, Asakawa, Yoshinori, "Supporting information for: "Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia cruciata"" in Journal of Natural Products (2019),
https://doi.org/10.1021/acs.jnatprod.8b00390.s001 . .

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  - JOUR
AU  - Konstantinović, Jelena M.
AU  - Kiris, Erkan
AU  - Kota, Krishna P.
AU  - Kugelman-Tonos, Johanny
AU  - Videnović, Milica
AU  - Cazares, Lisa H.
AU  - Terzić-Jovanović, Nataša
AU  - Verbić, Tatjana
AU  - Anđelković, Boban D.
AU  - Duplantier, Allen J.
AU  - Bavari, Sina
AU  - Šolaja, Bogdan
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2325
AB  - The synthesis and inhibitory potencies against botulinum neurotoxin serotype A light chain (BoNT/A LC) using in vitro HPLC based enzymatic assay for various steroidal, benzothiophene, thiophene, and adamantane 4-aminoquinoline derivatives are described. In addition, the compounds were evaluated for the activity against BoNT/A holotoxin in mouse embryonic stem cell derived motor neurons. Steroidal derivative 16 showed remarkable protection (up to 89% of uncleaved SNAP-25) even when administered 30 min postintoxication. This appears to be the first example of LC inhibitors antagonizing BoNT intoxication in mouse embryonic stem cell derived motor neurons (mES-MNs) in a postexposure model. Oral administration of 16 was well tolerated in the mouse up to 600 mg/kg, q.d. Although adequate unbound drug levels were not achieved at this dose, the favorable in vitro ADMET results strongly support further work in this series.
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model
VL  - 61
IS  - 4
SP  - 1595
EP  - 1608
DO  - 10.1021/acs.jmedchem.7b01710
ER  - 

@article{
author = "Konstantinović, Jelena M. and Kiris, Erkan and Kota, Krishna P. and Kugelman-Tonos, Johanny and Videnović, Milica and Cazares, Lisa H. and Terzić-Jovanović, Nataša and Verbić, Tatjana and Anđelković, Boban D. and Duplantier, Allen J. and Bavari, Sina and Šolaja, Bogdan",
year = "2018",
abstract = "The synthesis and inhibitory potencies against botulinum neurotoxin serotype A light chain (BoNT/A LC) using in vitro HPLC based enzymatic assay for various steroidal, benzothiophene, thiophene, and adamantane 4-aminoquinoline derivatives are described. In addition, the compounds were evaluated for the activity against BoNT/A holotoxin in mouse embryonic stem cell derived motor neurons. Steroidal derivative 16 showed remarkable protection (up to 89% of uncleaved SNAP-25) even when administered 30 min postintoxication. This appears to be the first example of LC inhibitors antagonizing BoNT intoxication in mouse embryonic stem cell derived motor neurons (mES-MNs) in a postexposure model. Oral administration of 16 was well tolerated in the mouse up to 600 mg/kg, q.d. Although adequate unbound drug levels were not achieved at this dose, the favorable in vitro ADMET results strongly support further work in this series.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model",
volume = "61",
number = "4",
pages = "1595-1608",
doi = "10.1021/acs.jmedchem.7b01710"
}

Konstantinović, J. M., Kiris, E., Kota, K. P., Kugelman-Tonos, J., Videnović, M., Cazares, L. H., Terzić-Jovanović, N., Verbić, T., Anđelković, B. D., Duplantier, A. J., Bavari, S.,& Šolaja, B.. (2018). New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model. in Journal of Medicinal Chemistry
American Chemical Society (ACS)., 61(4), 1595-1608.
https://doi.org/10.1021/acs.jmedchem.7b01710

Konstantinović JM, Kiris E, Kota KP, Kugelman-Tonos J, Videnović M, Cazares LH, Terzić-Jovanović N, Verbić T, Anđelković BD, Duplantier AJ, Bavari S, Šolaja B. New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model. in Journal of Medicinal Chemistry. 2018;61(4):1595-1608.
doi:10.1021/acs.jmedchem.7b01710 .

Konstantinović, Jelena M., Kiris, Erkan, Kota, Krishna P., Kugelman-Tonos, Johanny, Videnović, Milica, Cazares, Lisa H., Terzić-Jovanović, Nataša, Verbić, Tatjana, Anđelković, Boban D., Duplantier, Allen J., Bavari, Sina, Šolaja, Bogdan, "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model" in Journal of Medicinal Chemistry, 61, no. 4 (2018):1595-1608,
https://doi.org/10.1021/acs.jmedchem.7b01710 . .

TY  - JOUR
AU  - Konstantinović, Jelena M.
AU  - Kiris, Erkan
AU  - Kota, Krishna P.
AU  - Kugelman-Tonos, Johanny
AU  - Videnović, Milica
AU  - Cazares, Lisa H.
AU  - Terzić-Jovanović, Nataša
AU  - Verbić, Tatjana
AU  - Anđelković, Boban D.
AU  - Duplantier, Allen J.
AU  - Bavari, Sina
AU  - Šolaja, Bogdan
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2935
AB  - The synthesis and inhibitory potencies against botulinum neurotoxin serotype A light chain (BoNT/A LC) using in vitro HPLC based enzymatic assay for various steroidal, benzothiophene, thiophene, and adamantane 4-aminoquinoline derivatives are described. In addition, the compounds were evaluated for the activity against BoNT/A holotoxin in mouse embryonic stem cell derived motor neurons. Steroidal derivative 16 showed remarkable protection (up to 89% of uncleaved SNAP-25) even when administered 30 min postintoxication. This appears to be the first example of LC inhibitors antagonizing BoNT intoxication in mouse embryonic stem cell derived motor neurons (mES-MNs) in a postexposure model. Oral administration of 16 was well tolerated in the mouse up to 600 mg/kg, q.d. Although adequate unbound drug levels were not achieved at this dose, the favorable in vitro ADMET results strongly support further work in this series.
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model
VL  - 61
IS  - 4
SP  - 1595
EP  - 1608
DO  - 10.1021/acs.jmedchem.7b01710
ER  - 

@article{
author = "Konstantinović, Jelena M. and Kiris, Erkan and Kota, Krishna P. and Kugelman-Tonos, Johanny and Videnović, Milica and Cazares, Lisa H. and Terzić-Jovanović, Nataša and Verbić, Tatjana and Anđelković, Boban D. and Duplantier, Allen J. and Bavari, Sina and Šolaja, Bogdan",
year = "2018",
abstract = "The synthesis and inhibitory potencies against botulinum neurotoxin serotype A light chain (BoNT/A LC) using in vitro HPLC based enzymatic assay for various steroidal, benzothiophene, thiophene, and adamantane 4-aminoquinoline derivatives are described. In addition, the compounds were evaluated for the activity against BoNT/A holotoxin in mouse embryonic stem cell derived motor neurons. Steroidal derivative 16 showed remarkable protection (up to 89% of uncleaved SNAP-25) even when administered 30 min postintoxication. This appears to be the first example of LC inhibitors antagonizing BoNT intoxication in mouse embryonic stem cell derived motor neurons (mES-MNs) in a postexposure model. Oral administration of 16 was well tolerated in the mouse up to 600 mg/kg, q.d. Although adequate unbound drug levels were not achieved at this dose, the favorable in vitro ADMET results strongly support further work in this series.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model",
volume = "61",
number = "4",
pages = "1595-1608",
doi = "10.1021/acs.jmedchem.7b01710"
}

Konstantinović, J. M., Kiris, E., Kota, K. P., Kugelman-Tonos, J., Videnović, M., Cazares, L. H., Terzić-Jovanović, N., Verbić, T., Anđelković, B. D., Duplantier, A. J., Bavari, S.,& Šolaja, B.. (2018). New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model. in Journal of Medicinal Chemistry
American Chemical Society (ACS)., 61(4), 1595-1608.
https://doi.org/10.1021/acs.jmedchem.7b01710

Konstantinović JM, Kiris E, Kota KP, Kugelman-Tonos J, Videnović M, Cazares LH, Terzić-Jovanović N, Verbić T, Anđelković BD, Duplantier AJ, Bavari S, Šolaja B. New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model. in Journal of Medicinal Chemistry. 2018;61(4):1595-1608.
doi:10.1021/acs.jmedchem.7b01710 .

Konstantinović, Jelena M., Kiris, Erkan, Kota, Krishna P., Kugelman-Tonos, Johanny, Videnović, Milica, Cazares, Lisa H., Terzić-Jovanović, Nataša, Verbić, Tatjana, Anđelković, Boban D., Duplantier, Allen J., Bavari, Sina, Šolaja, Bogdan, "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model" in Journal of Medicinal Chemistry, 61, no. 4 (2018):1595-1608,
https://doi.org/10.1021/acs.jmedchem.7b01710 . .