Natural products of wild, cultivated and edible plants: structure and bioactivity determination

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Natural products of wild, cultivated and edible plants: structure and bioactivity determination (en)
Биоактивни природни производи самониклих, гајених и јестивих биљака: одређивање структура и активности (sr)
Bioaktivni prirodni proizvodi samoniklih, gajenih i jestivih biljaka: određivanje struktura i aktivnosti (sr_RS)
Authors

Publications

Phytochemical parameters as indicators of the authenticity of monofloral honey from the territory of the Republic of Serbia

Milosavljević, Saša; Jadranin, Milka; Mladenović, Mića; Tešević, Vele; Menković, Nebojša; Mutavdžić, Dragoslav; Krstić, Gordana

(North Macedonia : Society of Chemists and Technologists of Macedonia, 2021)

TY  - JOUR
AU  - Milosavljević, Saša
AU  - Jadranin, Milka
AU  - Mladenović, Mića
AU  - Tešević, Vele
AU  - Menković, Nebojša
AU  - Mutavdžić, Dragoslav
AU  - Krstić, Gordana
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4681
AB  - The aim of this research was to verify the authenticity of monofloral honeys from the territory of the Republic of Serbia on the basis of physicochemical parameters routinely measured in honey quality control using multivariate analysis. Seventeen samples of monofloral honey (11 samples of acacia honey and 6 samples of sunflower honey) from the territory of the Republic of Serbia were analyzed. Physico-chemical analysis of the samples included the examination of basic quality parameters and qualitative and quantitative analyses of phenolic compounds. In the samples tested, a total of 93 phenolic compounds were tentatively identified, and 19 of them were quantified. The obtained physicochemical analysis of the data served as input for the multivariate analysis. The hеаt map, which is useful for visualizing numerical data, was used for this purpose. The obtained results showed that the applied data can serve to clearly separate acacia and sunflower honeys.
AB  - Целта на ова истражување е да се потврди автентичноста на моноцветен мед од територијата на Република Србија врз основа на физичкохемиските параметри што рутински се мерат при контрола на квалитет на мед со примена на мултиваријантна анализа. Беа анализирани 17 примероци на моноцветен мед (11 примероци мед од акација и 6 примероци мед од сончоглед) од територијата на Република Србија. Физичкохемиските анализа на примероците вклучуваа испитување на основните параметри за квалитет како и квалитативна и квантитативна анализа на фенолните соединенија. Во примероците што беа тестирани, хипотетички беа идентификувани вкупно 93 фенолни соединенија, а 19 од нив беа и квантификувани. Добиените податоци од физичкохемиска анализа на овие податоци беа употребени како влезна податоци за мултиваријантна анализа. Беше применета топлинска мапа која е корисна за визуализација на нумеричките податоци. Добиените резултати покажуваат дека применетите податоци може да послужат за јасно да се раздели медот од акација и од сончоглед.
PB  - North Macedonia : Society of Chemists and Technologists of Macedonia
T2  - Macedonian Journal of Chemistry and Chemical Engineering
T1  - Phytochemical parameters as indicators of the authenticity of monofloral honey from the territory of the Republic of Serbia
T1  - Физичкохемијски параметри како индикатори на автентичноста на монофлорален мед од територијата на Република Србија
VL  - 40
IS  - 1
DO  - 10.20450/mjcce.2021.2186
ER  - 
@article{
author = "Milosavljević, Saša and Jadranin, Milka and Mladenović, Mića and Tešević, Vele and Menković, Nebojša and Mutavdžić, Dragoslav and Krstić, Gordana",
year = "2021",
abstract = "The aim of this research was to verify the authenticity of monofloral honeys from the territory of the Republic of Serbia on the basis of physicochemical parameters routinely measured in honey quality control using multivariate analysis. Seventeen samples of monofloral honey (11 samples of acacia honey and 6 samples of sunflower honey) from the territory of the Republic of Serbia were analyzed. Physico-chemical analysis of the samples included the examination of basic quality parameters and qualitative and quantitative analyses of phenolic compounds. In the samples tested, a total of 93 phenolic compounds were tentatively identified, and 19 of them were quantified. The obtained physicochemical analysis of the data served as input for the multivariate analysis. The hеаt map, which is useful for visualizing numerical data, was used for this purpose. The obtained results showed that the applied data can serve to clearly separate acacia and sunflower honeys., Целта на ова истражување е да се потврди автентичноста на моноцветен мед од територијата на Република Србија врз основа на физичкохемиските параметри што рутински се мерат при контрола на квалитет на мед со примена на мултиваријантна анализа. Беа анализирани 17 примероци на моноцветен мед (11 примероци мед од акација и 6 примероци мед од сончоглед) од територијата на Република Србија. Физичкохемиските анализа на примероците вклучуваа испитување на основните параметри за квалитет како и квалитативна и квантитативна анализа на фенолните соединенија. Во примероците што беа тестирани, хипотетички беа идентификувани вкупно 93 фенолни соединенија, а 19 од нив беа и квантификувани. Добиените податоци од физичкохемиска анализа на овие податоци беа употребени како влезна податоци за мултиваријантна анализа. Беше применета топлинска мапа која е корисна за визуализација на нумеричките податоци. Добиените резултати покажуваат дека применетите податоци може да послужат за јасно да се раздели медот од акација и од сончоглед.",
publisher = "North Macedonia : Society of Chemists and Technologists of Macedonia",
journal = "Macedonian Journal of Chemistry and Chemical Engineering",
title = "Phytochemical parameters as indicators of the authenticity of monofloral honey from the territory of the Republic of Serbia, Физичкохемијски параметри како индикатори на автентичноста на монофлорален мед од територијата на Република Србија",
volume = "40",
number = "1",
doi = "10.20450/mjcce.2021.2186"
}
Milosavljević, S., Jadranin, M., Mladenović, M., Tešević, V., Menković, N., Mutavdžić, D.,& Krstić, G.. (2021). Phytochemical parameters as indicators of the authenticity of monofloral honey from the territory of the Republic of Serbia. in Macedonian Journal of Chemistry and Chemical Engineering
North Macedonia : Society of Chemists and Technologists of Macedonia., 40(1).
https://doi.org/10.20450/mjcce.2021.2186
Milosavljević S, Jadranin M, Mladenović M, Tešević V, Menković N, Mutavdžić D, Krstić G. Phytochemical parameters as indicators of the authenticity of monofloral honey from the territory of the Republic of Serbia. in Macedonian Journal of Chemistry and Chemical Engineering. 2021;40(1).
doi:10.20450/mjcce.2021.2186 .
Milosavljević, Saša, Jadranin, Milka, Mladenović, Mića, Tešević, Vele, Menković, Nebojša, Mutavdžić, Dragoslav, Krstić, Gordana, "Phytochemical parameters as indicators of the authenticity of monofloral honey from the territory of the Republic of Serbia" in Macedonian Journal of Chemistry and Chemical Engineering, 40, no. 1 (2021),
https://doi.org/10.20450/mjcce.2021.2186 . .
3
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Cytotoxic triterpenoids and triterpene sugar esters from the medicinal mushroom Fomitopsis betulina

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

(Elsevier, 2021)

TY  - JOUR
AU  - Sofrenić, Ivana
AU  - Anđelković, Boban
AU  - Todorović, Nina
AU  - Stanojković, Tatjana
AU  - Vujisić, Ljubodrag V.
AU  - Novaković, Miroslav
AU  - Milosavljević, Slobodan
AU  - Tešević, Vele
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4038
AB  - Thirteen undescribed 24-methylene lanostane triterpenoids, named polyporenic acids E-M and fomitosides L-O, as well as seventeen known analogues, were isolated from the fruiting bodies of the mushroom Fomitopsis betulina. Their structures were determined using 1D, 2D NMR, IR, and HRESIMS. Fomitoside L and fomitoside N exhibited cytotoxicity against HL60 leukemia cells (IC50 = 15.8 and 23.7 μM, respectively). Among the known compounds, notable cytotoxicities against HL60 leukemia cells and selectivity with respect to MRC-5 healthy cells were noticed for dehydropachymic acid (IC50 = 10.9 μM, SI 8.6), pachymic acid (IC50 = 11.0 μM, SI 9.8), 3-epi-dehydrotumulosic acid (IC50 = 19.9 μM, SI 5.8) and 12α-hydroxy-3α-(3′-hydroxy-4′-methoxycarbonyl-3′-methylbutyryloxy)-24-methyllanosta-8,24 (31)-dien-26-oic acid (IC50 = 19.2 μM, SI 2.2).
PB  - Elsevier
T2  - Phytochemistry
T1  - Cytotoxic triterpenoids and triterpene sugar esters from the medicinal mushroom Fomitopsis betulina
VL  - 181
SP  - 112580
DO  - 10.1016/j.phytochem.2020.112580
ER  - 
@article{
author = "Sofrenić, Ivana and Anđelković, Boban and Todorović, Nina and Stanojković, Tatjana and Vujisić, Ljubodrag V. and Novaković, Miroslav and Milosavljević, Slobodan and Tešević, Vele",
year = "2021",
abstract = "Thirteen undescribed 24-methylene lanostane triterpenoids, named polyporenic acids E-M and fomitosides L-O, as well as seventeen known analogues, were isolated from the fruiting bodies of the mushroom Fomitopsis betulina. Their structures were determined using 1D, 2D NMR, IR, and HRESIMS. Fomitoside L and fomitoside N exhibited cytotoxicity against HL60 leukemia cells (IC50 = 15.8 and 23.7 μM, respectively). Among the known compounds, notable cytotoxicities against HL60 leukemia cells and selectivity with respect to MRC-5 healthy cells were noticed for dehydropachymic acid (IC50 = 10.9 μM, SI 8.6), pachymic acid (IC50 = 11.0 μM, SI 9.8), 3-epi-dehydrotumulosic acid (IC50 = 19.9 μM, SI 5.8) and 12α-hydroxy-3α-(3′-hydroxy-4′-methoxycarbonyl-3′-methylbutyryloxy)-24-methyllanosta-8,24 (31)-dien-26-oic acid (IC50 = 19.2 μM, SI 2.2).",
publisher = "Elsevier",
journal = "Phytochemistry",
title = "Cytotoxic triterpenoids and triterpene sugar esters from the medicinal mushroom Fomitopsis betulina",
volume = "181",
pages = "112580",
doi = "10.1016/j.phytochem.2020.112580"
}
Sofrenić, I., Anđelković, B., Todorović, N., Stanojković, T., Vujisić, L. V., Novaković, M., Milosavljević, S.,& Tešević, V.. (2021). Cytotoxic triterpenoids and triterpene sugar esters from the medicinal mushroom Fomitopsis betulina. in Phytochemistry
Elsevier., 181, 112580.
https://doi.org/10.1016/j.phytochem.2020.112580
Sofrenić I, Anđelković B, Todorović N, Stanojković T, Vujisić LV, Novaković M, Milosavljević S, Tešević V. Cytotoxic triterpenoids and triterpene sugar esters from the medicinal mushroom Fomitopsis betulina. in Phytochemistry. 2021;181:112580.
doi:10.1016/j.phytochem.2020.112580 .
Sofrenić, Ivana, Anđelković, Boban, Todorović, Nina, Stanojković, Tatjana, Vujisić, Ljubodrag V., Novaković, Miroslav, Milosavljević, Slobodan, Tešević, Vele, "Cytotoxic triterpenoids and triterpene sugar esters from the medicinal mushroom Fomitopsis betulina" in Phytochemistry, 181 (2021):112580,
https://doi.org/10.1016/j.phytochem.2020.112580 . .
2
15
4
15

Phytochemical investigation of Pimpinella serbica

Vučković, Ivan; Stiković, Sonja; Stešević, Danijela; Jadranin, Milka; Trifunović, Snežana

(Serbian Chemical Society, 2021)

TY  - JOUR
AU  - Vučković, Ivan
AU  - Stiković, Sonja
AU  - Stešević, Danijela
AU  - Jadranin, Milka
AU  - Trifunović, Snežana
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4919
AB  - The plant species Pimpinella serbica (Vis.) Drude, endemic to West Balkans, belongs to the genus Pimpinella L. (Apiaceae) according to newer botanical classification. Initially, the plant was described as Pancicia serbica Vis. and long considered as a monotypic genus. Previous phytochemical inves­tigations of this plant were limited to the essential oil analysis by the GC–MS method. This is first study that includes LC-DAD–MS screening of the extracts of the roots and aerial parts, followed by isolation of secondary metabolites using chromatographic techniques. Five compounds belonging to phenylpropanoids and polyacetylenes, well known for their bioactivities, were isolated and struc­turally determined by combined spectroscopic methods (UV, NMR, MS). Dil­lapiole (1), nothoapiole (2) and oplopantriol A 18-acetate (4) were found in both extracts, while falcarindiol (3) was isolated from the roots and dendrotrifidol (5) from the aerial parts only. The phytochemical profile of P. serbica L. supports its position in the Pimpinella L. genus.
AB  - Ендемска врста Западног Балкана Pimpinella serbica (Vis.) Drude према последњој ботаничкој класификацији припада роду Pimpinella L. (Apiaceae), мада је најпре била описана као Pancicia serbica Vis. и дуго је сматрана једином припадајућом врстом овог рода. Претходна фитохемијска испитивања ове врсте обухватају само анализу етарског уља GC–MS техником, тако да је ово прво детаљно испитивање биљке које укључује LCDAD– MS анализу праћену изоловањем секундарних метаболита биљке применом хро- матографских техника. Пет једињења која припадају групи фенилпропаноида и поли- ацетилена, добро познатих по својим биолошким активностима, изоловано је из екстра- ката надземног дела и корена биљке. Њихова структура је одређена применом спек- троскопских метода (UV, NMR, MS). Дилапиол (1), нотоапиол (2) и оплопантриол А 18-ацетат (4) нађени су у оба екстракта, док је фалкариндиол (3) изолован само из екс- тракта корена, а дендротрифидол (5) само из екстракта надземног дела биљке. Фито- хемијски профил биљке P. serbica подржава њену припадност роду Pimpinella L.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Phytochemical investigation of Pimpinella serbica
T1  - Фитохемијско испитивање врсте Pimpinella serbica
IS  - 12
SP  - 1241
EP  - 1247
DO  - 10.2298/JSC210816081V
ER  - 
@article{
author = "Vučković, Ivan and Stiković, Sonja and Stešević, Danijela and Jadranin, Milka and Trifunović, Snežana",
year = "2021",
abstract = "The plant species Pimpinella serbica (Vis.) Drude, endemic to West Balkans, belongs to the genus Pimpinella L. (Apiaceae) according to newer botanical classification. Initially, the plant was described as Pancicia serbica Vis. and long considered as a monotypic genus. Previous phytochemical inves­tigations of this plant were limited to the essential oil analysis by the GC–MS method. This is first study that includes LC-DAD–MS screening of the extracts of the roots and aerial parts, followed by isolation of secondary metabolites using chromatographic techniques. Five compounds belonging to phenylpropanoids and polyacetylenes, well known for their bioactivities, were isolated and struc­turally determined by combined spectroscopic methods (UV, NMR, MS). Dil­lapiole (1), nothoapiole (2) and oplopantriol A 18-acetate (4) were found in both extracts, while falcarindiol (3) was isolated from the roots and dendrotrifidol (5) from the aerial parts only. The phytochemical profile of P. serbica L. supports its position in the Pimpinella L. genus., Ендемска врста Западног Балкана Pimpinella serbica (Vis.) Drude према последњој ботаничкој класификацији припада роду Pimpinella L. (Apiaceae), мада је најпре била описана као Pancicia serbica Vis. и дуго је сматрана једином припадајућом врстом овог рода. Претходна фитохемијска испитивања ове врсте обухватају само анализу етарског уља GC–MS техником, тако да је ово прво детаљно испитивање биљке које укључује LCDAD– MS анализу праћену изоловањем секундарних метаболита биљке применом хро- матографских техника. Пет једињења која припадају групи фенилпропаноида и поли- ацетилена, добро познатих по својим биолошким активностима, изоловано је из екстра- ката надземног дела и корена биљке. Њихова структура је одређена применом спек- троскопских метода (UV, NMR, MS). Дилапиол (1), нотоапиол (2) и оплопантриол А 18-ацетат (4) нађени су у оба екстракта, док је фалкариндиол (3) изолован само из екс- тракта корена, а дендротрифидол (5) само из екстракта надземног дела биљке. Фито- хемијски профил биљке P. serbica подржава њену припадност роду Pimpinella L.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Phytochemical investigation of Pimpinella serbica, Фитохемијско испитивање врсте Pimpinella serbica",
number = "12",
pages = "1241-1247",
doi = "10.2298/JSC210816081V"
}
Vučković, I., Stiković, S., Stešević, D., Jadranin, M.,& Trifunović, S.. (2021). Phytochemical investigation of Pimpinella serbica. in Journal of the Serbian Chemical Society
Serbian Chemical Society.(12), 1241-1247.
https://doi.org/10.2298/JSC210816081V
Vučković I, Stiković S, Stešević D, Jadranin M, Trifunović S. Phytochemical investigation of Pimpinella serbica. in Journal of the Serbian Chemical Society. 2021;(12):1241-1247.
doi:10.2298/JSC210816081V .
Vučković, Ivan, Stiković, Sonja, Stešević, Danijela, Jadranin, Milka, Trifunović, Snežana, "Phytochemical investigation of Pimpinella serbica" in Journal of the Serbian Chemical Society, no. 12 (2021):1241-1247,
https://doi.org/10.2298/JSC210816081V . .
2

Lamiaceae in the treatment of cardiovascular diseases

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

(Frontiers in Bioscience - Landmark, 2021)

TY  - JOUR
AU  - Patrignani, Francesca
AU  - Prasad, Sahdeo
AU  - Novaković, Miroslav
AU  - Marin, Petar D.
AU  - Bukvicki, Danka
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4522
AB  - Lamiaceae (Labiatae) are an important group of medicinal plants, which have been used for treating heart disease in traditional medicine for centuries. These mainly aromatic plants are used as essential oils, extracts or isolated components (polyphenols, phenolic compounds, terpenes, iridoids etc.). Some Labiatae species (more than 30, such as cornmint, lavender, patchouli, rosemary etc.) are famous for their use in essential oil production worldwide. In this review, cardioprotective effects of Lamiaceae and their active secondary metabolites, as well as mechanism of action against cardiovascular diseases (hypertension, angina pectoris, hyperlipidemia, thromboembolism, coronary heart disease, heart failure, venous insufficiency, arrhythmia) will be discussed. Use of Labiatae as food or food additives (such as spices) may prevent risk of cardiovascular diseases, diabetes and cancer. This approach is also described as a part of the article. Studies on developing new, effective and safe natural products from Lamiaceae (rich source of flavonoids and other active compounds) are promising and may offer prevention and treatment for patients with coronary disease and other related diseases.
PB  - Frontiers in Bioscience - Landmark
T2  - Frontiers in Bioscience-Landmark
T1  - Lamiaceae in the treatment of cardiovascular diseases
VL  - 26
IS  - 4
SP  - 612
EP  - 643
DO  - 10.2741/4909
ER  - 
@article{
author = "Patrignani, Francesca and Prasad, Sahdeo and Novaković, Miroslav and Marin, Petar D. and Bukvicki, Danka",
year = "2021",
abstract = "Lamiaceae (Labiatae) are an important group of medicinal plants, which have been used for treating heart disease in traditional medicine for centuries. These mainly aromatic plants are used as essential oils, extracts or isolated components (polyphenols, phenolic compounds, terpenes, iridoids etc.). Some Labiatae species (more than 30, such as cornmint, lavender, patchouli, rosemary etc.) are famous for their use in essential oil production worldwide. In this review, cardioprotective effects of Lamiaceae and their active secondary metabolites, as well as mechanism of action against cardiovascular diseases (hypertension, angina pectoris, hyperlipidemia, thromboembolism, coronary heart disease, heart failure, venous insufficiency, arrhythmia) will be discussed. Use of Labiatae as food or food additives (such as spices) may prevent risk of cardiovascular diseases, diabetes and cancer. This approach is also described as a part of the article. Studies on developing new, effective and safe natural products from Lamiaceae (rich source of flavonoids and other active compounds) are promising and may offer prevention and treatment for patients with coronary disease and other related diseases.",
publisher = "Frontiers in Bioscience - Landmark",
journal = "Frontiers in Bioscience-Landmark",
title = "Lamiaceae in the treatment of cardiovascular diseases",
volume = "26",
number = "4",
pages = "612-643",
doi = "10.2741/4909"
}
Patrignani, F., Prasad, S., Novaković, M., Marin, P. D.,& Bukvicki, D.. (2021). Lamiaceae in the treatment of cardiovascular diseases. in Frontiers in Bioscience-Landmark
Frontiers in Bioscience - Landmark., 26(4), 612-643.
https://doi.org/10.2741/4909
Patrignani F, Prasad S, Novaković M, Marin PD, Bukvicki D. Lamiaceae in the treatment of cardiovascular diseases. in Frontiers in Bioscience-Landmark. 2021;26(4):612-643.
doi:10.2741/4909 .
Patrignani, Francesca, Prasad, Sahdeo, Novaković, Miroslav, Marin, Petar D., Bukvicki, Danka, "Lamiaceae in the treatment of cardiovascular diseases" in Frontiers in Bioscience-Landmark, 26, no. 4 (2021):612-643,
https://doi.org/10.2741/4909 . .
19
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17

NMR metabolomics insight into phytochemistry

Anđelković, Boban; Sofrenić, Ivana; Đorđević, Iris; Ivanović, Stefan; Cvetković, Mirjana; Gođevac, Dejan; Milosavljević, Slobodan

(Zagreb, Croatia : Department of Chemistry, Faculty of Science, University of Zagreb, 2020)

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 .

Nonacosan-10-ol and n-Alkanes in Needles of Pinus halepensis

Nikolić, Biljana; Todosijević, Marina; Đorđević, Iris; Stanković, Jovana; Mitić, Zorica S.; Tešević, Vele; Marin, Petar D.

(SAGE Publications Inc., 2020)

TY  - JOUR
AU  - Nikolić, Biljana
AU  - Todosijević, Marina
AU  - Đorđević, Iris
AU  - Stanković, Jovana
AU  - Mitić, Zorica S.
AU  - Tešević, Vele
AU  - Marin, Petar D.
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3620
AB  - In needle cuticular wax of Pinus halepensis, nonacosan-10-ol
is high (77.08% on average). n-Alkanes
ranged from C18 to C35 with the
most dominant C27 and C29 (32.4% and 25.8%, respectively). The carbon preference index ranged from 3.2 to 5.4 (3.4 on average),
while the average chain length ranged from 14.0 to 18.0 (17.2 on average). Long-chain
n-alkanes
strongly dominated (95.1%).
PB  - SAGE Publications Inc.
T2  - Natural Product Communications
T1  - Nonacosan-10-ol and n-Alkanes in Needles of Pinus halepensis
VL  - 15
IS  - 5
SP  - 1
EP  - 4
DO  - 10.1177/1934578X20920970
ER  - 
@article{
author = "Nikolić, Biljana and Todosijević, Marina and Đorđević, Iris and Stanković, Jovana and Mitić, Zorica S. and Tešević, Vele and Marin, Petar D.",
year = "2020",
abstract = "In needle cuticular wax of Pinus halepensis, nonacosan-10-ol
is high (77.08% on average). n-Alkanes
ranged from C18 to C35 with the
most dominant C27 and C29 (32.4% and 25.8%, respectively). The carbon preference index ranged from 3.2 to 5.4 (3.4 on average),
while the average chain length ranged from 14.0 to 18.0 (17.2 on average). Long-chain
n-alkanes
strongly dominated (95.1%).",
publisher = "SAGE Publications Inc.",
journal = "Natural Product Communications",
title = "Nonacosan-10-ol and n-Alkanes in Needles of Pinus halepensis",
volume = "15",
number = "5",
pages = "1-4",
doi = "10.1177/1934578X20920970"
}
Nikolić, B., Todosijević, M., Đorđević, I., Stanković, J., Mitić, Z. S., Tešević, V.,& Marin, P. D.. (2020). Nonacosan-10-ol and n-Alkanes in Needles of Pinus halepensis. in Natural Product Communications
SAGE Publications Inc.., 15(5), 1-4.
https://doi.org/10.1177/1934578X20920970
Nikolić B, Todosijević M, Đorđević I, Stanković J, Mitić ZS, Tešević V, Marin PD. Nonacosan-10-ol and n-Alkanes in Needles of Pinus halepensis. in Natural Product Communications. 2020;15(5):1-4.
doi:10.1177/1934578X20920970 .
Nikolić, Biljana, Todosijević, Marina, Đorđević, Iris, Stanković, Jovana, Mitić, Zorica S., Tešević, Vele, Marin, Petar D., "Nonacosan-10-ol and n-Alkanes in Needles of Pinus halepensis" in Natural Product Communications, 15, no. 5 (2020):1-4,
https://doi.org/10.1177/1934578X20920970 . .
1
2

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

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

(Elsevier, 2020)

TY  - JOUR
AU  - Novaković, Miroslav
AU  - Simić, Stefan
AU  - Koračak, Ljiljana
AU  - Zlatović, Mario
AU  - Ilić-Tomić, Tatjana
AU  - Asakawa, Yoshinori
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2020
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3867
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3441
AB  - Chemical and biocatalytic synthesis of seven previously undescribed marchantin A ester derivatives has been presented. Chemical synthesis afforded three peresterified bisbibenzyl products (TE1-TE3), while enzymatic method, using lipase, produced regioselective monoester derivatives (ME1-ME4). The antiproliferative activities of all prepared derivatives of marchantin A were tested on MRC-5 healthy human lung fibroblast, A549 human lung cancer, and MDA-MB-231 human breast cancer cell lines. All tested esters were less cytotoxic in comparison to marchantin A, but they also exhibited lower cytotoxicity against healthy cells. Monoesters displayed higher cytotoxic activities than the corresponding peresterified products, presumably due to the presence of free catechol group. Monohexanoyl ester ME3 displayed the same IC50 like marchantin A against MDA-MB-231 cells, but the selectivity was higher. In this way, regioselective enzymatic monoesterification enhanced selectivity of marchantin A. ME3 was also the most active among all derivatives against lung cancer cells A549 with the slightly lower activity and selectivity in comparison to marchantin A.
PB  - Elsevier
T2  - Fitoterapia
T1  - Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives
VL  - 142
SP  - 104520
DO  - 10.1016/j.fitote.2020.104520
ER  - 
@article{
author = "Novaković, Miroslav and Simić, Stefan and Koračak, Ljiljana and Zlatović, Mario and Ilić-Tomić, Tatjana and Asakawa, Yoshinori and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2020",
abstract = "Chemical and biocatalytic synthesis of seven previously undescribed marchantin A ester derivatives has been presented. Chemical synthesis afforded three peresterified bisbibenzyl products (TE1-TE3), while enzymatic method, using lipase, produced regioselective monoester derivatives (ME1-ME4). The antiproliferative activities of all prepared derivatives of marchantin A were tested on MRC-5 healthy human lung fibroblast, A549 human lung cancer, and MDA-MB-231 human breast cancer cell lines. All tested esters were less cytotoxic in comparison to marchantin A, but they also exhibited lower cytotoxicity against healthy cells. Monoesters displayed higher cytotoxic activities than the corresponding peresterified products, presumably due to the presence of free catechol group. Monohexanoyl ester ME3 displayed the same IC50 like marchantin A against MDA-MB-231 cells, but the selectivity was higher. In this way, regioselective enzymatic monoesterification enhanced selectivity of marchantin A. ME3 was also the most active among all derivatives against lung cancer cells A549 with the slightly lower activity and selectivity in comparison to marchantin A.",
publisher = "Elsevier",
journal = "Fitoterapia",
title = "Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives",
volume = "142",
pages = "104520",
doi = "10.1016/j.fitote.2020.104520"
}
Novaković, M., Simić, S., Koračak, L., Zlatović, M., Ilić-Tomić, T., Asakawa, Y., Nikodinović-Runić, J.,& Opsenica, I.. (2020). Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives. in Fitoterapia
Elsevier., 142, 104520.
https://doi.org/10.1016/j.fitote.2020.104520
Novaković M, Simić S, Koračak L, Zlatović M, Ilić-Tomić T, Asakawa Y, Nikodinović-Runić J, Opsenica I. Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives. in Fitoterapia. 2020;142:104520.
doi:10.1016/j.fitote.2020.104520 .
Novaković, Miroslav, Simić, Stefan, Koračak, Ljiljana, Zlatović, Mario, Ilić-Tomić, Tatjana, Asakawa, Yoshinori, Nikodinović-Runić, Jasmina, Opsenica, Igor, "Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives" in Fitoterapia, 142 (2020):104520,
https://doi.org/10.1016/j.fitote.2020.104520 . .
1
5
1
4

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

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

(Elsevier, 2020)

TY  - JOUR
AU  - Novaković, Miroslav
AU  - Simić, Stefan
AU  - Koračak, Ljiljana
AU  - Zlatović, Mario
AU  - Ilić-Tomić, Tatjana
AU  - Asakawa, Yoshinori
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3449
AB  - Chemical and biocatalytic synthesis of seven previously undescribed marchantin A ester derivatives has been presented. Chemical synthesis afforded three peresterified bisbibenzyl products (TE1-TE3), while enzymatic method, using lipase, produced regioselective monoester derivatives (ME1-ME4). The antiproliferative activities of all prepared derivatives of marchantin A were tested on MRC-5 healthy human lung fibroblast, A549 human lung cancer, and MDA-MB-231 human breast cancer cell lines. All tested esters were less cytotoxic in comparison to marchantin A, but they also exhibited lower cytotoxicity against healthy cells. Monoesters displayed higher cytotoxic activities than the corresponding peresterified products, presumably due to the presence of free catechol group. Monohexanoyl ester ME3 displayed the same IC50 like marchantin A against MDA-MB-231 cells, but the selectivity was higher. In this way, regioselective enzymatic monoesterification enhanced selectivity of marchantin A. ME3 was also the most active among all derivatives against lung cancer cells A549 with the slightly lower activity and selectivity in comparison to marchantin A.
PB  - Elsevier
T2  - Fitoterapia
T1  - Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives
VL  - 142
SP  - 104520
DO  - 10.1016/j.fitote.2020.104520
ER  - 
@article{
author = "Novaković, Miroslav and Simić, Stefan and Koračak, Ljiljana and Zlatović, Mario and Ilić-Tomić, Tatjana and Asakawa, Yoshinori and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2020",
abstract = "Chemical and biocatalytic synthesis of seven previously undescribed marchantin A ester derivatives has been presented. Chemical synthesis afforded three peresterified bisbibenzyl products (TE1-TE3), while enzymatic method, using lipase, produced regioselective monoester derivatives (ME1-ME4). The antiproliferative activities of all prepared derivatives of marchantin A were tested on MRC-5 healthy human lung fibroblast, A549 human lung cancer, and MDA-MB-231 human breast cancer cell lines. All tested esters were less cytotoxic in comparison to marchantin A, but they also exhibited lower cytotoxicity against healthy cells. Monoesters displayed higher cytotoxic activities than the corresponding peresterified products, presumably due to the presence of free catechol group. Monohexanoyl ester ME3 displayed the same IC50 like marchantin A against MDA-MB-231 cells, but the selectivity was higher. In this way, regioselective enzymatic monoesterification enhanced selectivity of marchantin A. ME3 was also the most active among all derivatives against lung cancer cells A549 with the slightly lower activity and selectivity in comparison to marchantin A.",
publisher = "Elsevier",
journal = "Fitoterapia",
title = "Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives",
volume = "142",
pages = "104520",
doi = "10.1016/j.fitote.2020.104520"
}
Novaković, M., Simić, S., Koračak, L., Zlatović, M., Ilić-Tomić, T., Asakawa, Y., Nikodinović-Runić, J.,& Opsenica, I.. (2020). Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives. in Fitoterapia
Elsevier., 142, 104520.
https://doi.org/10.1016/j.fitote.2020.104520
Novaković M, Simić S, Koračak L, Zlatović M, Ilić-Tomić T, Asakawa Y, Nikodinović-Runić J, Opsenica I. Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives. in Fitoterapia. 2020;142:104520.
doi:10.1016/j.fitote.2020.104520 .
Novaković, Miroslav, Simić, Stefan, Koračak, Ljiljana, Zlatović, Mario, Ilić-Tomić, Tatjana, Asakawa, Yoshinori, Nikodinović-Runić, Jasmina, Opsenica, Igor, "Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives" in Fitoterapia, 142 (2020):104520,
https://doi.org/10.1016/j.fitote.2020.104520 . .
1
5
1
4

Bisaurones-enzymatic production and biological evaluation

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

(Royal Society of Chemistry, 2020)

TY  - JOUR
AU  - Novaković, Miroslav
AU  - Ilić-Tomić, Tatjana
AU  - Tešević, Vele
AU  - Simić, Katarina
AU  - Ivanović, Stefan
AU  - Simić, Stefan
AU  - Opsenica, Igor
AU  - Nikodinović-Runić, Jasmina
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3639
AB  - The Trametes versicolor laccase catalyzed oxidation of chalcone butein afforded four dimers of aurone sulfuretin (i.e. two regioisomeric pairs of diasteromers, 1-4) as the major products. The formation of the dimers was explained by a two step process involving the initial cyclization of butein into aurone sulfuretin, followed by the combination of two molecules of sulfuretin. The coupling process occurred between the 2,10-double bond of one molecule of sulfuretin and the (3′,4′) catechol group of the other to yield a dimeric structure. This was confirmed by the experiment involving the laccase catalyzed oxidation of sulfuretin yielding the same dimeric bisaurones. Compounds 1, 3 and 4, were isolated using semipreparative HPLC and characterized by the detailed analysis of the NMR, MS, IR, and UV-vis data. The structure of compound 2, isolated as a mixture containing ca. 25% of compound 1, was proposed by the comparison of 1H NMR data to compound 1 and by using LC-ESIMS analysis. The starting chalcone butein and the products of the biocatalytic transformation, aurone sulfuretin and sulfuretin dimers 1, 3 and 4, were evaluated for their cytotoxic and antioxidative properties in vitro using a healthy human fibroblast (MRC5) cell line. The biotransformation products showed lower cytotoxicity but higher antioxidative properties. The C. coggygria bark methanol extract rich in butein and sulfuretin was also biotransformed by laccase. The transformed extract exhibited significantly improved antioxidative activities.
PB  - Royal Society of Chemistry
T2  - New Journal of Chemistry
T1  - Bisaurones-enzymatic production and biological evaluation
VL  - 44
IS  - 23
SP  - 9647
EP  - 9655
DO  - 10.1039/d0nj00758g
ER  - 
@article{
author = "Novaković, Miroslav and Ilić-Tomić, Tatjana and Tešević, Vele and Simić, Katarina and Ivanović, Stefan and Simić, Stefan and Opsenica, Igor and Nikodinović-Runić, Jasmina",
year = "2020",
abstract = "The Trametes versicolor laccase catalyzed oxidation of chalcone butein afforded four dimers of aurone sulfuretin (i.e. two regioisomeric pairs of diasteromers, 1-4) as the major products. The formation of the dimers was explained by a two step process involving the initial cyclization of butein into aurone sulfuretin, followed by the combination of two molecules of sulfuretin. The coupling process occurred between the 2,10-double bond of one molecule of sulfuretin and the (3′,4′) catechol group of the other to yield a dimeric structure. This was confirmed by the experiment involving the laccase catalyzed oxidation of sulfuretin yielding the same dimeric bisaurones. Compounds 1, 3 and 4, were isolated using semipreparative HPLC and characterized by the detailed analysis of the NMR, MS, IR, and UV-vis data. The structure of compound 2, isolated as a mixture containing ca. 25% of compound 1, was proposed by the comparison of 1H NMR data to compound 1 and by using LC-ESIMS analysis. The starting chalcone butein and the products of the biocatalytic transformation, aurone sulfuretin and sulfuretin dimers 1, 3 and 4, were evaluated for their cytotoxic and antioxidative properties in vitro using a healthy human fibroblast (MRC5) cell line. The biotransformation products showed lower cytotoxicity but higher antioxidative properties. The C. coggygria bark methanol extract rich in butein and sulfuretin was also biotransformed by laccase. The transformed extract exhibited significantly improved antioxidative activities.",
publisher = "Royal Society of Chemistry",
journal = "New Journal of Chemistry",
title = "Bisaurones-enzymatic production and biological evaluation",
volume = "44",
number = "23",
pages = "9647-9655",
doi = "10.1039/d0nj00758g"
}
Novaković, M., Ilić-Tomić, T., Tešević, V., Simić, K., Ivanović, S., Simić, S., Opsenica, I.,& Nikodinović-Runić, J.. (2020). Bisaurones-enzymatic production and biological evaluation. in New Journal of Chemistry
Royal Society of Chemistry., 44(23), 9647-9655.
https://doi.org/10.1039/d0nj00758g
Novaković M, Ilić-Tomić T, Tešević V, Simić K, Ivanović S, Simić S, Opsenica I, Nikodinović-Runić J. Bisaurones-enzymatic production and biological evaluation. in New Journal of Chemistry. 2020;44(23):9647-9655.
doi:10.1039/d0nj00758g .
Novaković, Miroslav, Ilić-Tomić, Tatjana, Tešević, Vele, Simić, Katarina, Ivanović, Stefan, Simić, Stefan, Opsenica, Igor, Nikodinović-Runić, Jasmina, "Bisaurones-enzymatic production and biological evaluation" in New Journal of Chemistry, 44, no. 23 (2020):9647-9655,
https://doi.org/10.1039/d0nj00758g . .
1
1

Bisaurones-enzymatic production and biological evaluation

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

(Royal Society of Chemistry, 2020)

TY  - JOUR
AU  - Novaković, Miroslav
AU  - Ilić-Tomić, Tatjana
AU  - Tešević, Vele
AU  - Simić, Katarina
AU  - Ivanović, Stefan
AU  - Simić, Stefan
AU  - Opsenica, Igor
AU  - Nikodinović-Runić, Jasmina
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3717
AB  - The Trametes versicolor laccase catalyzed oxidation of chalcone butein afforded four dimers of aurone sulfuretin (i.e. two regioisomeric pairs of diasteromers, 1-4) as the major products. The formation of the dimers was explained by a two step process involving the initial cyclization of butein into aurone sulfuretin, followed by the combination of two molecules of sulfuretin. The coupling process occurred between the 2,10-double bond of one molecule of sulfuretin and the (3′,4′) catechol group of the other to yield a dimeric structure. This was confirmed by the experiment involving the laccase catalyzed oxidation of sulfuretin yielding the same dimeric bisaurones. Compounds 1, 3 and 4, were isolated using semipreparative HPLC and characterized by the detailed analysis of the NMR, MS, IR, and UV-vis data. The structure of compound 2, isolated as a mixture containing ca. 25% of compound 1, was proposed by the comparison of 1H NMR data to compound 1 and by using LC-ESIMS analysis. The starting chalcone butein and the products of the biocatalytic transformation, aurone sulfuretin and sulfuretin dimers 1, 3 and 4, were evaluated for their cytotoxic and antioxidative properties in vitro using a healthy human fibroblast (MRC5) cell line. The biotransformation products showed lower cytotoxicity but higher antioxidative properties. The C. coggygria bark methanol extract rich in butein and sulfuretin was also biotransformed by laccase. The transformed extract exhibited significantly improved antioxidative activities.
PB  - Royal Society of Chemistry
T2  - New Journal of Chemistry
T1  - Bisaurones-enzymatic production and biological evaluation
VL  - 44
IS  - 23
SP  - 9647
EP  - 9655
DO  - 10.1039/d0nj00758g
ER  - 
@article{
author = "Novaković, Miroslav and Ilić-Tomić, Tatjana and Tešević, Vele and Simić, Katarina and Ivanović, Stefan and Simić, Stefan and Opsenica, Igor and Nikodinović-Runić, Jasmina",
year = "2020",
abstract = "The Trametes versicolor laccase catalyzed oxidation of chalcone butein afforded four dimers of aurone sulfuretin (i.e. two regioisomeric pairs of diasteromers, 1-4) as the major products. The formation of the dimers was explained by a two step process involving the initial cyclization of butein into aurone sulfuretin, followed by the combination of two molecules of sulfuretin. The coupling process occurred between the 2,10-double bond of one molecule of sulfuretin and the (3′,4′) catechol group of the other to yield a dimeric structure. This was confirmed by the experiment involving the laccase catalyzed oxidation of sulfuretin yielding the same dimeric bisaurones. Compounds 1, 3 and 4, were isolated using semipreparative HPLC and characterized by the detailed analysis of the NMR, MS, IR, and UV-vis data. The structure of compound 2, isolated as a mixture containing ca. 25% of compound 1, was proposed by the comparison of 1H NMR data to compound 1 and by using LC-ESIMS analysis. The starting chalcone butein and the products of the biocatalytic transformation, aurone sulfuretin and sulfuretin dimers 1, 3 and 4, were evaluated for their cytotoxic and antioxidative properties in vitro using a healthy human fibroblast (MRC5) cell line. The biotransformation products showed lower cytotoxicity but higher antioxidative properties. The C. coggygria bark methanol extract rich in butein and sulfuretin was also biotransformed by laccase. The transformed extract exhibited significantly improved antioxidative activities.",
publisher = "Royal Society of Chemistry",
journal = "New Journal of Chemistry",
title = "Bisaurones-enzymatic production and biological evaluation",
volume = "44",
number = "23",
pages = "9647-9655",
doi = "10.1039/d0nj00758g"
}
Novaković, M., Ilić-Tomić, T., Tešević, V., Simić, K., Ivanović, S., Simić, S., Opsenica, I.,& Nikodinović-Runić, J.. (2020). Bisaurones-enzymatic production and biological evaluation. in New Journal of Chemistry
Royal Society of Chemistry., 44(23), 9647-9655.
https://doi.org/10.1039/d0nj00758g
Novaković M, Ilić-Tomić T, Tešević V, Simić K, Ivanović S, Simić S, Opsenica I, Nikodinović-Runić J. Bisaurones-enzymatic production and biological evaluation. in New Journal of Chemistry. 2020;44(23):9647-9655.
doi:10.1039/d0nj00758g .
Novaković, Miroslav, Ilić-Tomić, Tatjana, Tešević, Vele, Simić, Katarina, Ivanović, Stefan, Simić, Stefan, Opsenica, Igor, Nikodinović-Runić, Jasmina, "Bisaurones-enzymatic production and biological evaluation" in New Journal of Chemistry, 44, no. 23 (2020):9647-9655,
https://doi.org/10.1039/d0nj00758g . .
1
1

Integration of dry-column flash chromatography with NMR and FTIR metabolomics to reveal cytotoxic metabolites from Amphoricarpos autariatus

Cvetković, Mirjana; Damjanović, Ana; Stanojković, Tatjana; Đorđević, Iris; Tešević, Vele; Milosavljević, Slobodan; Gođevac, Dejan

(Elsevier, 2020)

TY  - JOUR
AU  - Cvetković, Mirjana
AU  - Damjanović, Ana
AU  - Stanojković, Tatjana
AU  - Đorđević, Iris
AU  - Tešević, Vele
AU  - Milosavljević, Slobodan
AU  - Gođevac, Dejan
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3054
AB  - Metabolomics generate a profile of small molecules from plant extracts, which could be directly responsible for bioactivity effects. Using dry-column flash chromatography enabled a rapid and inexpensive method for the very efficient separation of plant extract with a high resolution. This separation method coupled to NMR and FTIR based metabolomics is applied to identify bioactive natural products. OPLS multivariate analysis method, was used for correlation the chemical composition of the plant extracts, Amphoricarpos autariatus, with the results of cytotoxic activity against Human cervical adenocarcinoma cell line (HeLa) and epithelial lung cancer cell line
(A549). In this way, the highest contribution to the cytotoxic activity was recorded for the guaianolide sesquiterpene lactones named amphoricarpolides. The compounds indicated as bioactive after metabolomics analysis were tested, and their cytotoxic activity were confirmed.
PB  - Elsevier
T2  - Talanta
T1  - Integration of dry-column flash chromatography with NMR and FTIR metabolomics to reveal cytotoxic metabolites from Amphoricarpos autariatus
VL  - 206
SP  - 120248
DO  - 10.1016/j.talanta.2019.120248
ER  - 
@article{
author = "Cvetković, Mirjana and Damjanović, Ana and Stanojković, Tatjana and Đorđević, Iris and Tešević, Vele and Milosavljević, Slobodan and Gođevac, Dejan",
year = "2020",
abstract = "Metabolomics generate a profile of small molecules from plant extracts, which could be directly responsible for bioactivity effects. Using dry-column flash chromatography enabled a rapid and inexpensive method for the very efficient separation of plant extract with a high resolution. This separation method coupled to NMR and FTIR based metabolomics is applied to identify bioactive natural products. OPLS multivariate analysis method, was used for correlation the chemical composition of the plant extracts, Amphoricarpos autariatus, with the results of cytotoxic activity against Human cervical adenocarcinoma cell line (HeLa) and epithelial lung cancer cell line
(A549). In this way, the highest contribution to the cytotoxic activity was recorded for the guaianolide sesquiterpene lactones named amphoricarpolides. The compounds indicated as bioactive after metabolomics analysis were tested, and their cytotoxic activity were confirmed.",
publisher = "Elsevier",
journal = "Talanta",
title = "Integration of dry-column flash chromatography with NMR and FTIR metabolomics to reveal cytotoxic metabolites from Amphoricarpos autariatus",
volume = "206",
pages = "120248",
doi = "10.1016/j.talanta.2019.120248"
}
Cvetković, M., Damjanović, A., Stanojković, T., Đorđević, I., Tešević, V., Milosavljević, S.,& Gođevac, D.. (2020). Integration of dry-column flash chromatography with NMR and FTIR metabolomics to reveal cytotoxic metabolites from Amphoricarpos autariatus. in Talanta
Elsevier., 206, 120248.
https://doi.org/10.1016/j.talanta.2019.120248
Cvetković M, Damjanović A, Stanojković T, Đorđević I, Tešević V, Milosavljević S, Gođevac D. Integration of dry-column flash chromatography with NMR and FTIR metabolomics to reveal cytotoxic metabolites from Amphoricarpos autariatus. in Talanta. 2020;206:120248.
doi:10.1016/j.talanta.2019.120248 .
Cvetković, Mirjana, Damjanović, Ana, Stanojković, Tatjana, Đorđević, Iris, Tešević, Vele, Milosavljević, Slobodan, Gođevac, Dejan, "Integration of dry-column flash chromatography with NMR and FTIR metabolomics to reveal cytotoxic metabolites from Amphoricarpos autariatus" in Talanta, 206 (2020):120248,
https://doi.org/10.1016/j.talanta.2019.120248 . .
10
5
7

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

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

(MDPI, 2020)

TY  - JOUR
AU  - Ivanović, Stefan
AU  - Avramović, Nataša
AU  - Dojčinović, Biljana
AU  - Trifunović, Snežana
AU  - Novaković, Miroslav
AU  - Tešević, Vele
AU  - Mandić, Boris
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3492
AB  - The present study evaluates natural composition of Serbian roasted hazelnut skins (HS) with potential role in application as functional nutrient of various food products. Total phenols (TPC) and flavonoids contents (TFC) in HS extracts obtained with different ethanol concentrations (10%—I, 50%—II and 96%—III) and their antioxidant activities were investigated. The highest total phenols content (706.0 ± 9.7 mgGAE/gextract) was observed in 96% ethanol HS extract. Ethanol HS extracts showed very high antioxidant activity with effective concentrations (EC50) ranged between 0.052 and 0.066 mg/mL. The phenol and flavonoid content of roasted HS extracts I–III was determined by HPLC-ESI-MS/MS analyses. Contents of lipids, proteins, carbohydrates, metals, and C, H, N, S elements in roasted HS were also determined. Relatively high C/N, C/P and C/N/P ratios, rich metal contents and fatty acids composition indicated that hazelnut skin might be a good candidate for use as either human or fungal functional nutrient. In addition, possible application of phenolic HS extracts as UV booster was studied by recording UV spectra (220–440 nm) of 10 mg/L of HS extracts I–III combined with 10 mg/L of chemical sunscreen agent benzophenone-3 and in vitro sun protection factor (SPF) was calculated.
PB  - MDPI
T2  - Foods
T1  - Chemical Composition, Total Phenols and Flavonoids Contents and Antioxidant Activity as Nutritive Potential of Roasted Hazelnut Skins (Corylus avellana L.)
VL  - 9
IS  - 4
SP  - 430
DO  - 10.3390/foods9040430
ER  - 
@article{
author = "Ivanović, Stefan and Avramović, Nataša and Dojčinović, Biljana and Trifunović, Snežana and Novaković, Miroslav and Tešević, Vele and Mandić, Boris",
year = "2020",
abstract = "The present study evaluates natural composition of Serbian roasted hazelnut skins (HS) with potential role in application as functional nutrient of various food products. Total phenols (TPC) and flavonoids contents (TFC) in HS extracts obtained with different ethanol concentrations (10%—I, 50%—II and 96%—III) and their antioxidant activities were investigated. The highest total phenols content (706.0 ± 9.7 mgGAE/gextract) was observed in 96% ethanol HS extract. Ethanol HS extracts showed very high antioxidant activity with effective concentrations (EC50) ranged between 0.052 and 0.066 mg/mL. The phenol and flavonoid content of roasted HS extracts I–III was determined by HPLC-ESI-MS/MS analyses. Contents of lipids, proteins, carbohydrates, metals, and C, H, N, S elements in roasted HS were also determined. Relatively high C/N, C/P and C/N/P ratios, rich metal contents and fatty acids composition indicated that hazelnut skin might be a good candidate for use as either human or fungal functional nutrient. In addition, possible application of phenolic HS extracts as UV booster was studied by recording UV spectra (220–440 nm) of 10 mg/L of HS extracts I–III combined with 10 mg/L of chemical sunscreen agent benzophenone-3 and in vitro sun protection factor (SPF) was calculated.",
publisher = "MDPI",
journal = "Foods",
title = "Chemical Composition, Total Phenols and Flavonoids Contents and Antioxidant Activity as Nutritive Potential of Roasted Hazelnut Skins (Corylus avellana L.)",
volume = "9",
number = "4",
pages = "430",
doi = "10.3390/foods9040430"
}
Ivanović, S., Avramović, N., Dojčinović, B., Trifunović, S., Novaković, M., Tešević, V.,& Mandić, B.. (2020). Chemical Composition, Total Phenols and Flavonoids Contents and Antioxidant Activity as Nutritive Potential of Roasted Hazelnut Skins (Corylus avellana L.). in Foods
MDPI., 9(4), 430.
https://doi.org/10.3390/foods9040430
Ivanović S, Avramović N, Dojčinović B, Trifunović S, Novaković M, Tešević V, Mandić B. Chemical Composition, Total Phenols and Flavonoids Contents and Antioxidant Activity as Nutritive Potential of Roasted Hazelnut Skins (Corylus avellana L.). in Foods. 2020;9(4):430.
doi:10.3390/foods9040430 .
Ivanović, Stefan, Avramović, Nataša, Dojčinović, Biljana, Trifunović, Snežana, Novaković, Miroslav, Tešević, Vele, Mandić, Boris, "Chemical Composition, Total Phenols and Flavonoids Contents and Antioxidant Activity as Nutritive Potential of Roasted Hazelnut Skins (Corylus avellana L.)" in Foods, 9, no. 4 (2020):430,
https://doi.org/10.3390/foods9040430 . .
22
7
23

Composition, Antioxidant Potential, and Antimicrobial Activity of Helichrysum plicatum DC. Various Extracts

Vujić, Bojan; Vidaković, Vera; Jadranin, Milka; Novaković, Irena; Trifunović, Snežana; Tešević, Vele; Mandić, Boris

(MDPI, 2020)

TY  - JOUR
AU  - Vujić, Bojan
AU  - Vidaković, Vera
AU  - Jadranin, Milka
AU  - Novaković, Irena
AU  - Trifunović, Snežana
AU  - Tešević, Vele
AU  - Mandić, Boris
PY  - 2020
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3962
UR  - http://ibiss-r.rcub.bg.ac.rs/handle/123456789/3620
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3581
AB  - Helichrysum plicatum DC. is widely used in folk medicine in treating a variety of health disorders. The aim of this study was to examine the influence of different extraction solvents on the chemical composition, antioxidant potential, and antimicrobial activities of H. plicatum. Aerial parts were separately extracted with ethanol, dichloromethane, and sunflower oil. The oil extract (OE) was re-extracted with acetonitrile. A total of 142 compounds were tentatively identified in ethanolic (EE), dichloromethane (DCME), and acetonitrile (ACNE) extracts using HPLC-DAD/ESI-ToF-MS. The dominant compound class in all extracts were α-pyrones, alongside flavonoids in EE, terpenoids in DCME and ACNE, and phloroglucinols in DCME. The antioxidant potential of the extracts was assessed by the 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) assay. EE and DCME possessed the most potent radical scavenging capacity. Antimicrobial activity was investigated on eight bacterial, two yeast, and one fungal species. All extracts exhibited high antifungal and notable antibacterial activities compared to control substances, with DCME being the most potent. DCME exhibited stronger antimicrobial activity against P. aeruginosa than the standard chloramphenicol.
PB  - MDPI
T2  - Plants
T1  - Composition, Antioxidant Potential, and Antimicrobial Activity of Helichrysum plicatum DC. Various Extracts
VL  - 9
IS  - 3
SP  - 337
DO  - 10.3390/plants9030337
ER  - 
@article{
author = "Vujić, Bojan and Vidaković, Vera and Jadranin, Milka and Novaković, Irena and Trifunović, Snežana and Tešević, Vele and Mandić, Boris",
year = "2020",
abstract = "Helichrysum plicatum DC. is widely used in folk medicine in treating a variety of health disorders. The aim of this study was to examine the influence of different extraction solvents on the chemical composition, antioxidant potential, and antimicrobial activities of H. plicatum. Aerial parts were separately extracted with ethanol, dichloromethane, and sunflower oil. The oil extract (OE) was re-extracted with acetonitrile. A total of 142 compounds were tentatively identified in ethanolic (EE), dichloromethane (DCME), and acetonitrile (ACNE) extracts using HPLC-DAD/ESI-ToF-MS. The dominant compound class in all extracts were α-pyrones, alongside flavonoids in EE, terpenoids in DCME and ACNE, and phloroglucinols in DCME. The antioxidant potential of the extracts was assessed by the 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) assay. EE and DCME possessed the most potent radical scavenging capacity. Antimicrobial activity was investigated on eight bacterial, two yeast, and one fungal species. All extracts exhibited high antifungal and notable antibacterial activities compared to control substances, with DCME being the most potent. DCME exhibited stronger antimicrobial activity against P. aeruginosa than the standard chloramphenicol.",
publisher = "MDPI",
journal = "Plants",
title = "Composition, Antioxidant Potential, and Antimicrobial Activity of Helichrysum plicatum DC. Various Extracts",
volume = "9",
number = "3",
pages = "337",
doi = "10.3390/plants9030337"
}
Vujić, B., Vidaković, V., Jadranin, M., Novaković, I., Trifunović, S., Tešević, V.,& Mandić, B.. (2020). Composition, Antioxidant Potential, and Antimicrobial Activity of Helichrysum plicatum DC. Various Extracts. in Plants
MDPI., 9(3), 337.
https://doi.org/10.3390/plants9030337
Vujić B, Vidaković V, Jadranin M, Novaković I, Trifunović S, Tešević V, Mandić B. Composition, Antioxidant Potential, and Antimicrobial Activity of Helichrysum plicatum DC. Various Extracts. in Plants. 2020;9(3):337.
doi:10.3390/plants9030337 .
Vujić, Bojan, Vidaković, Vera, Jadranin, Milka, Novaković, Irena, Trifunović, Snežana, Tešević, Vele, Mandić, Boris, "Composition, Antioxidant Potential, and Antimicrobial Activity of Helichrysum plicatum DC. Various Extracts" in Plants, 9, no. 3 (2020):337,
https://doi.org/10.3390/plants9030337 . .
15
2
10

Leaf epicuticular waxes of eleven Euphorbia species (Euphorbiaceae) from the central Balkans: Impact on chemotaxonomy

Krstić, Gordana; Aljančić, Ivana; Stanković, Jovana; Cvetković, Mirjana; Marin, Petar D.; Janaćković, Peđa T.; Tešević, Vele

(2019)

TY  - JOUR
AU  - Krstić, Gordana
AU  - Aljančić, Ivana
AU  - Stanković, Jovana
AU  - Cvetković, Mirjana
AU  - Marin, Petar D.
AU  - Janaćković, Peđa T.
AU  - Tešević, Vele
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2923
AB  - The presence of n-alkanes, free alcohols and free acids in leaf epicuticular wax extracts of 22 samples of 11 Euphorbia L. species belonging to the sections Paralias, Esula, Myrsiniteae and Helioscopia, 10 of which were never examined before, were analyzed by gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS), and n-alkane C27 was detected as the principal component of leaf epicuticular waxes in the majority of the examined species, while the most abundant free alcohol was C26. Three Euphorbia species belonging to section Helioscopia were characterized by a predominance of alcohol C28. Free acid (C16) was the major component in 21 investigated samples. The usefulness of n-alkanes and free alcohols and free acids as potential chemotaxonomic markers is briefly discussed.
T2  - Archives of Biological Sciences
T1  - Leaf epicuticular waxes of eleven Euphorbia species (Euphorbiaceae) from the central Balkans: Impact on chemotaxonomy
VL  - 71
IS  - 1
SP  - 21
EP  - 26
DO  - 10.2298/ABS180608041K
ER  - 
@article{
author = "Krstić, Gordana and Aljančić, Ivana and Stanković, Jovana and Cvetković, Mirjana and Marin, Petar D. and Janaćković, Peđa T. and Tešević, Vele",
year = "2019",
abstract = "The presence of n-alkanes, free alcohols and free acids in leaf epicuticular wax extracts of 22 samples of 11 Euphorbia L. species belonging to the sections Paralias, Esula, Myrsiniteae and Helioscopia, 10 of which were never examined before, were analyzed by gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS), and n-alkane C27 was detected as the principal component of leaf epicuticular waxes in the majority of the examined species, while the most abundant free alcohol was C26. Three Euphorbia species belonging to section Helioscopia were characterized by a predominance of alcohol C28. Free acid (C16) was the major component in 21 investigated samples. The usefulness of n-alkanes and free alcohols and free acids as potential chemotaxonomic markers is briefly discussed.",
journal = "Archives of Biological Sciences",
title = "Leaf epicuticular waxes of eleven Euphorbia species (Euphorbiaceae) from the central Balkans: Impact on chemotaxonomy",
volume = "71",
number = "1",
pages = "21-26",
doi = "10.2298/ABS180608041K"
}
Krstić, G., Aljančić, I., Stanković, J., Cvetković, M., Marin, P. D., Janaćković, P. T.,& Tešević, V.. (2019). Leaf epicuticular waxes of eleven Euphorbia species (Euphorbiaceae) from the central Balkans: Impact on chemotaxonomy. in Archives of Biological Sciences, 71(1), 21-26.
https://doi.org/10.2298/ABS180608041K
Krstić G, Aljančić I, Stanković J, Cvetković M, Marin PD, Janaćković PT, Tešević V. Leaf epicuticular waxes of eleven Euphorbia species (Euphorbiaceae) from the central Balkans: Impact on chemotaxonomy. in Archives of Biological Sciences. 2019;71(1):21-26.
doi:10.2298/ABS180608041K .
Krstić, Gordana, Aljančić, Ivana, Stanković, Jovana, Cvetković, Mirjana, Marin, Petar D., Janaćković, Peđa T., Tešević, Vele, "Leaf epicuticular waxes of eleven Euphorbia species (Euphorbiaceae) from the central Balkans: Impact on chemotaxonomy" in Archives of Biological Sciences, 71, no. 1 (2019):21-26,
https://doi.org/10.2298/ABS180608041K . .
2
1
2

Tetracyclic triterpenoids from Euphorbia nicaeensis All

Krstić, Gordana; Novaković, Miroslav; Jadranin, Milka; Tešević, Vele

(Leskovac: University of Niš - Faculty of Technology, Leskovac, 2019)

TY  - JOUR
AU  - Krstić, Gordana
AU  - Novaković, Miroslav
AU  - Jadranin, Milka
AU  - Tešević, Vele
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3471
AB  - In this study, three tetracyclic triterpenes: (3S,24S)-tirucall-7-ene-3,24,25-triol (1), (3S,24R)-tirucall-7-ene-3,24,25-triol (2) and inoterpene C (3), were isolated from the milkweed Euphorbia nicaeensis All. using dry-column flash silica gel chromatography and semipreparative normal-phase HPLC. Their structures were determined on the basis of 1D and 2D NMR spectra and literature review. Although these three compounds have previously been isolated from other plant species, this is the first time that they have been isolated from E. nicaeensis.
AB  - U ovom radu, tri tetraciklična triterpena: (3S,24S)-tirukal-7-en-3,24,25-triol (1), (3S,24R)-tirukal-7-en-3,24,25-triol (2) i inoterpen C (3) su izolovana iz mlečike Euphorbia nicaeensis All. koristeći brzu hromatografiju na suvom stubu silika gela i semipreparativnu normalno-faznu HPLC. Strukture su određene na osnovu 1D i 2D NMR spektara i poređenjem sa literaturom. Iako su ova tri jedinjenja ranije izolovana iz drugih biljnih vrsta, ovo je prvi put da su izolovana iz E. nicaeensis.
PB  - Leskovac: University of Niš - Faculty of Technology, Leskovac
T2  - Advanced Technologies
T1  - Tetracyclic triterpenoids from Euphorbia nicaeensis All
T1  - Tetraciklični triterpenoidi iz vrste Euphorbia nicaeensis All
VL  - 8
IS  - 2
SP  - 37
EP  - 45
DO  - 10.5937/savteh1902037K
ER  - 
@article{
author = "Krstić, Gordana and Novaković, Miroslav and Jadranin, Milka and Tešević, Vele",
year = "2019",
abstract = "In this study, three tetracyclic triterpenes: (3S,24S)-tirucall-7-ene-3,24,25-triol (1), (3S,24R)-tirucall-7-ene-3,24,25-triol (2) and inoterpene C (3), were isolated from the milkweed Euphorbia nicaeensis All. using dry-column flash silica gel chromatography and semipreparative normal-phase HPLC. Their structures were determined on the basis of 1D and 2D NMR spectra and literature review. Although these three compounds have previously been isolated from other plant species, this is the first time that they have been isolated from E. nicaeensis., U ovom radu, tri tetraciklična triterpena: (3S,24S)-tirukal-7-en-3,24,25-triol (1), (3S,24R)-tirukal-7-en-3,24,25-triol (2) i inoterpen C (3) su izolovana iz mlečike Euphorbia nicaeensis All. koristeći brzu hromatografiju na suvom stubu silika gela i semipreparativnu normalno-faznu HPLC. Strukture su određene na osnovu 1D i 2D NMR spektara i poređenjem sa literaturom. Iako su ova tri jedinjenja ranije izolovana iz drugih biljnih vrsta, ovo je prvi put da su izolovana iz E. nicaeensis.",
publisher = "Leskovac: University of Niš - Faculty of Technology, Leskovac",
journal = "Advanced Technologies",
title = "Tetracyclic triterpenoids from Euphorbia nicaeensis All, Tetraciklični triterpenoidi iz vrste Euphorbia nicaeensis All",
volume = "8",
number = "2",
pages = "37-45",
doi = "10.5937/savteh1902037K"
}
Krstić, G., Novaković, M., Jadranin, M.,& Tešević, V.. (2019). Tetracyclic triterpenoids from Euphorbia nicaeensis All. in Advanced Technologies
Leskovac: University of Niš - Faculty of Technology, Leskovac., 8(2), 37-45.
https://doi.org/10.5937/savteh1902037K
Krstić G, Novaković M, Jadranin M, Tešević V. Tetracyclic triterpenoids from Euphorbia nicaeensis All. in Advanced Technologies. 2019;8(2):37-45.
doi:10.5937/savteh1902037K .
Krstić, Gordana, Novaković, Miroslav, Jadranin, Milka, Tešević, Vele, "Tetracyclic triterpenoids from Euphorbia nicaeensis All" in Advanced Technologies, 8, no. 2 (2019):37-45,
https://doi.org/10.5937/savteh1902037K . .
2

Jatrophane Diterpenoids With Protective Effect on Human Lymphocytes DNA

Krstić, Gordana; Jadranin, Milka; Stanković, Miroslava; Aljančić, Ivana; Vujisić, Ljubodrag V.; Mandić, Boris; Tešević, Vele

(SAGE Journals, 2019)

TY  - JOUR
AU  - Krstić, Gordana
AU  - Jadranin, Milka
AU  - Stanković, Miroslava
AU  - Aljančić, Ivana
AU  - Vujisić, Ljubodrag V.
AU  - Mandić, Boris
AU  - Tešević, Vele
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3143
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3514
AB  - Two sets of structurally different jatrophanes (1-11 and 13-16), jatrophane 12, and latex extract of 2 Euphorbia species (17 and 18) were tested for in vitro protective effect against chromosome aberrations in peripheral human lymphocytes using the cytokinesis-block micronucleus (CBMN) assay. Jatrophanes 1-6 in minimal doses of 1 µg/mL prominently decreased micronuclei (MN) frequency in the range 44.86% to 34.29% and manifested considerable protective effect. From the other set of jatrophanes, 13 in the same minimal dose notably decreased MN frequency by 31.05%, while extracts 17 and 18 at a concentration of 4 µg/mL remarkably decreased the frequency of MN by 37.94% and 36.12%, respectively. Jatrophanes 12, 14, and 16 showed moderate protection, while 7-11 and 15 were less active than positive control. The structure-activity relationship (SAR) studies of the tested jatrophanes (1-16) indicated the favorable position of benzoate at C-8 or C-9 (3, 4, and 13) and a preference of isobutanoyloxy group at C-3 (1-3) rather than propanoyloxy at the same position (4-6) for pronounced protective effect on human lymphocytes DNA. In a previous SAR study on 11 jatrophanes (1, 3-8, and 13-16), the same structural features in 3, 4, and 13 influenced powerful inhibition of P-gp, while growth inhibition of cancer cells was more than doubled in 1 (isobutanoyloxy group at C-3) compared to 6 (propanoyloxy at C-3).
PB  - SAGE Journals
T2  - Natural Product Communications
T1  - Jatrophane Diterpenoids With Protective Effect on Human Lymphocytes DNA
VL  - 14
IS  - 5
DO  - 10.1177/1934578X19848168
ER  - 
@article{
author = "Krstić, Gordana and Jadranin, Milka and Stanković, Miroslava and Aljančić, Ivana and Vujisić, Ljubodrag V. and Mandić, Boris and Tešević, Vele",
year = "2019",
abstract = "Two sets of structurally different jatrophanes (1-11 and 13-16), jatrophane 12, and latex extract of 2 Euphorbia species (17 and 18) were tested for in vitro protective effect against chromosome aberrations in peripheral human lymphocytes using the cytokinesis-block micronucleus (CBMN) assay. Jatrophanes 1-6 in minimal doses of 1 µg/mL prominently decreased micronuclei (MN) frequency in the range 44.86% to 34.29% and manifested considerable protective effect. From the other set of jatrophanes, 13 in the same minimal dose notably decreased MN frequency by 31.05%, while extracts 17 and 18 at a concentration of 4 µg/mL remarkably decreased the frequency of MN by 37.94% and 36.12%, respectively. Jatrophanes 12, 14, and 16 showed moderate protection, while 7-11 and 15 were less active than positive control. The structure-activity relationship (SAR) studies of the tested jatrophanes (1-16) indicated the favorable position of benzoate at C-8 or C-9 (3, 4, and 13) and a preference of isobutanoyloxy group at C-3 (1-3) rather than propanoyloxy at the same position (4-6) for pronounced protective effect on human lymphocytes DNA. In a previous SAR study on 11 jatrophanes (1, 3-8, and 13-16), the same structural features in 3, 4, and 13 influenced powerful inhibition of P-gp, while growth inhibition of cancer cells was more than doubled in 1 (isobutanoyloxy group at C-3) compared to 6 (propanoyloxy at C-3).",
publisher = "SAGE Journals",
journal = "Natural Product Communications",
title = "Jatrophane Diterpenoids With Protective Effect on Human Lymphocytes DNA",
volume = "14",
number = "5",
doi = "10.1177/1934578X19848168"
}
Krstić, G., Jadranin, M., Stanković, M., Aljančić, I., Vujisić, L. V., Mandić, B.,& Tešević, V.. (2019). Jatrophane Diterpenoids With Protective Effect on Human Lymphocytes DNA. in Natural Product Communications
SAGE Journals., 14(5).
https://doi.org/10.1177/1934578X19848168
Krstić G, Jadranin M, Stanković M, Aljančić I, Vujisić LV, Mandić B, Tešević V. Jatrophane Diterpenoids With Protective Effect on Human Lymphocytes DNA. in Natural Product Communications. 2019;14(5).
doi:10.1177/1934578X19848168 .
Krstić, Gordana, Jadranin, Milka, Stanković, Miroslava, Aljančić, Ivana, Vujisić, Ljubodrag V., Mandić, Boris, Tešević, Vele, "Jatrophane Diterpenoids With Protective Effect on Human Lymphocytes DNA" in Natural Product Communications, 14, no. 5 (2019),
https://doi.org/10.1177/1934578X19848168 . .
5
4
6

Evaluation of the universality of NMR metabolic fingerprints of schizophrenia

Simić, Katarina; Todorović, Nina; Miladinović, Zoran; Ivanović, Stefan; Trifunović, Snežana; Vujisić, Ljubodrag; Tešević, Vele; Jovanović, Vesna B.; Avramović, Nataša; Gavrilović, Aleksandra; Jovanović, Silvana; Costa, Tássia Brena Barroso Carneiro; Huan Liu, Leticia; Barros, Pedro; Stanišić, Danijela; Mandić, Boris; Tasić, Ljubica

(University of Belgrade - Faculty of Chemistry, 2019)

TY  - CONF
AU  - Simić, Katarina
AU  - Todorović, Nina
AU  - Miladinović, Zoran
AU  - Ivanović, Stefan
AU  - Trifunović, Snežana
AU  - Vujisić, Ljubodrag
AU  - Tešević, Vele
AU  - Jovanović, Vesna B.
AU  - Avramović, Nataša
AU  - Gavrilović, Aleksandra
AU  - Jovanović, Silvana
AU  - Costa, Tássia Brena Barroso Carneiro
AU  - Huan Liu, Leticia
AU  - Barros, Pedro
AU  - Stanišić, Danijela
AU  - Mandić, Boris
AU  - Tasić, Ljubica
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7536
AB  - Schizophrenia (SCZ) is a very disabling mental disorder whose molecular basis is a combination of many factors still not completely understood, with a diagnosis based on observed behavior, the person's reported experiences and reports of others that are familiar with the person, with no objective test. Also, up to date, there are no reliable markers for monitoring the SCZ. NMR-metabolomics [1] reported in 2017 bring some of the possible markers from blood serum of SCZ individuals linked strongly with known dopamine, glutamate and GABA dysfunction in SCZ. As to verify if these findings are universal, we have compared the SCZ patients from geographically different environments and cited interesting SCZ characteristics.  
The first set of samples was collected in Belgrade, Serbia. 14 mental health patients (50% male) with 52.86 ± 7.27 years of age had a confirmed diagnosis of SCZ. The control group of 13 healthy individuals (69% male) had none of psychotic disorders, and individuals were 23.07 ± 2.79 years of age. Blood serum samples were collected and prepared for the analysis following the published methodology [1, 2]. NMR spectra were measured on a Bruker AVANCE III spectrometer (500.26 MHz for 1H). The spectra were acquired at 298 K with 128 scans and 32 k. The serum samples were prepared and measured as triplicates.  
On the other side, the group of individuals from Brazil that was matched in number, age, gender and history of mental illness with individuals from Serbia was previously described [1].  
1H NMR spectra were phase and baseline corrected using MestreNova and the lactate doublet was used as the chemical shift reference. The data were binned (0.005 ppm) in a spectral range 0.50 - 9.00 ppm, while the residual HDO peak (4.50-5.00 ppm) was excluded. Then, the data were normalized by the sum equal to 1000, the variables were mean centered and PCA and PLS-DA were performed using MATLAB.  
It was shown that the mental health patients have clearly different blood serum metabolites when compared to the healthy ones independently from where the samples were obtained with almost identical marker set. Also, it was shown that the samples are different metabolically when Brazilian and Serbian samples were compared. 
1] L. Tasic et al., Schizophrenia Research 2017, 185, 182.
[2] J. Pontes et al., Analytical Methods 2017, 9, 1078.
PB  - University of Belgrade - Faculty of  Chemistry
PB  - Institute of Chemistry, Technology and Metallurgy, National Institute
C3  - Book of Abstracts - 21st Central European NMR Symposium &  Bruker Users Meeting, 21st CEUM, September 4-5, 2019, Belgrade, Serbia
T1  - Evaluation of the universality of NMR metabolic fingerprints of schizophrenia
SP  - 31
EP  - 32
UR  - https://hdl.handle.net/21.15107/rcub_cer_7536
ER  - 
@conference{
author = "Simić, Katarina and Todorović, Nina and Miladinović, Zoran and Ivanović, Stefan and Trifunović, Snežana and Vujisić, Ljubodrag and Tešević, Vele and Jovanović, Vesna B. and Avramović, Nataša and Gavrilović, Aleksandra and Jovanović, Silvana and Costa, Tássia Brena Barroso Carneiro and Huan Liu, Leticia and Barros, Pedro and Stanišić, Danijela and Mandić, Boris and Tasić, Ljubica",
year = "2019",
abstract = "Schizophrenia (SCZ) is a very disabling mental disorder whose molecular basis is a combination of many factors still not completely understood, with a diagnosis based on observed behavior, the person's reported experiences and reports of others that are familiar with the person, with no objective test. Also, up to date, there are no reliable markers for monitoring the SCZ. NMR-metabolomics [1] reported in 2017 bring some of the possible markers from blood serum of SCZ individuals linked strongly with known dopamine, glutamate and GABA dysfunction in SCZ. As to verify if these findings are universal, we have compared the SCZ patients from geographically different environments and cited interesting SCZ characteristics.  
The first set of samples was collected in Belgrade, Serbia. 14 mental health patients (50% male) with 52.86 ± 7.27 years of age had a confirmed diagnosis of SCZ. The control group of 13 healthy individuals (69% male) had none of psychotic disorders, and individuals were 23.07 ± 2.79 years of age. Blood serum samples were collected and prepared for the analysis following the published methodology [1, 2]. NMR spectra were measured on a Bruker AVANCE III spectrometer (500.26 MHz for 1H). The spectra were acquired at 298 K with 128 scans and 32 k. The serum samples were prepared and measured as triplicates.  
On the other side, the group of individuals from Brazil that was matched in number, age, gender and history of mental illness with individuals from Serbia was previously described [1].  
1H NMR spectra were phase and baseline corrected using MestreNova and the lactate doublet was used as the chemical shift reference. The data were binned (0.005 ppm) in a spectral range 0.50 - 9.00 ppm, while the residual HDO peak (4.50-5.00 ppm) was excluded. Then, the data were normalized by the sum equal to 1000, the variables were mean centered and PCA and PLS-DA were performed using MATLAB.  
It was shown that the mental health patients have clearly different blood serum metabolites when compared to the healthy ones independently from where the samples were obtained with almost identical marker set. Also, it was shown that the samples are different metabolically when Brazilian and Serbian samples were compared. 
1] L. Tasic et al., Schizophrenia Research 2017, 185, 182.
[2] J. Pontes et al., Analytical Methods 2017, 9, 1078.",
publisher = "University of Belgrade - Faculty of  Chemistry, Institute of Chemistry, Technology and Metallurgy, National Institute",
journal = "Book of Abstracts - 21st Central European NMR Symposium &  Bruker Users Meeting, 21st CEUM, September 4-5, 2019, Belgrade, Serbia",
title = "Evaluation of the universality of NMR metabolic fingerprints of schizophrenia",
pages = "31-32",
url = "https://hdl.handle.net/21.15107/rcub_cer_7536"
}
Simić, K., Todorović, N., Miladinović, Z., Ivanović, S., Trifunović, S., Vujisić, L., Tešević, V., Jovanović, V. B., Avramović, N., Gavrilović, A., Jovanović, S., Costa, T. B. B. C., Huan Liu, L., Barros, P., Stanišić, D., Mandić, B.,& Tasić, L.. (2019). Evaluation of the universality of NMR metabolic fingerprints of schizophrenia. in Book of Abstracts - 21st Central European NMR Symposium &  Bruker Users Meeting, 21st CEUM, September 4-5, 2019, Belgrade, Serbia
University of Belgrade - Faculty of  Chemistry., 31-32.
https://hdl.handle.net/21.15107/rcub_cer_7536
Simić K, Todorović N, Miladinović Z, Ivanović S, Trifunović S, Vujisić L, Tešević V, Jovanović VB, Avramović N, Gavrilović A, Jovanović S, Costa TBBC, Huan Liu L, Barros P, Stanišić D, Mandić B, Tasić L. Evaluation of the universality of NMR metabolic fingerprints of schizophrenia. in Book of Abstracts - 21st Central European NMR Symposium &  Bruker Users Meeting, 21st CEUM, September 4-5, 2019, Belgrade, Serbia. 2019;:31-32.
https://hdl.handle.net/21.15107/rcub_cer_7536 .
Simić, Katarina, Todorović, Nina, Miladinović, Zoran, Ivanović, Stefan, Trifunović, Snežana, Vujisić, Ljubodrag, Tešević, Vele, Jovanović, Vesna B., Avramović, Nataša, Gavrilović, Aleksandra, Jovanović, Silvana, Costa, Tássia Brena Barroso Carneiro, Huan Liu, Leticia, Barros, Pedro, Stanišić, Danijela, Mandić, Boris, Tasić, Ljubica, "Evaluation of the universality of NMR metabolic fingerprints of schizophrenia" in Book of Abstracts - 21st Central European NMR Symposium &  Bruker Users Meeting, 21st CEUM, September 4-5, 2019, Belgrade, Serbia (2019):31-32,
https://hdl.handle.net/21.15107/rcub_cer_7536 .

Electrochemical and spectroscopic study of l‑dopa interaction with avarol

Nakarada, Đura; Pejin, Boris; Dimić, Dušan; Ivanović-Šašić, Ana; Mojović, Zorica; Mojović, Miloš

(Springer, 2019)

TY  - JOUR
AU  - Nakarada, Đura
AU  - Pejin, Boris
AU  - Dimić, Dušan
AU  - Ivanović-Šašić, Ana
AU  - Mojović, Zorica
AU  - Mojović, Miloš
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3027
AB  - The electrochemistry of catecholamine neurotransmitters and their precursor l-dopa has been widely studied due to their relevance as biologically important compounds. The detection of these compounds from aqueous solution is hindered by the coexistence of quinone or hydroquinone. However, it was suggested that quinones adsorbed on the electrode surface can enhance catechol detection. In order to estimate the degree of interaction between quinones and l-dopa, cyclic voltammetry and UV-Vis spectroscopic study was performed. A sesquiterpenoid hydroquinone, isolated from the marine sponge Dysidea avara (avarol), has been used in this study. The change of apparent heterogeneous rate constant with different avarol/l-dopa ratio indicated that charge transfer could be enhanced at some extent. In addition to this, the obtained results for avarol and hydroquinone (its structural element) were compared. UV-Vis spectroscopic analysis confirmed interaction between l-dopa and avarol or hydroquinone. Taken all together, the interaction of l-dopa was stronger with hydroquinone than with avarol, presumably reflecting the conformational restrains of avarol caused by its terpenoid moiety.
PB  - Springer
T2  - Reaction Kinetics, Mechanisms and Catalysis
T1  - Electrochemical and spectroscopic study of l‑dopa interaction with avarol
VL  - 127
IS  - 1
SP  - 219
EP  - 229
DO  - 10.1007/s11144-019-01575-z
ER  - 
@article{
author = "Nakarada, Đura and Pejin, Boris and Dimić, Dušan and Ivanović-Šašić, Ana and Mojović, Zorica and Mojović, Miloš",
year = "2019",
abstract = "The electrochemistry of catecholamine neurotransmitters and their precursor l-dopa has been widely studied due to their relevance as biologically important compounds. The detection of these compounds from aqueous solution is hindered by the coexistence of quinone or hydroquinone. However, it was suggested that quinones adsorbed on the electrode surface can enhance catechol detection. In order to estimate the degree of interaction between quinones and l-dopa, cyclic voltammetry and UV-Vis spectroscopic study was performed. A sesquiterpenoid hydroquinone, isolated from the marine sponge Dysidea avara (avarol), has been used in this study. The change of apparent heterogeneous rate constant with different avarol/l-dopa ratio indicated that charge transfer could be enhanced at some extent. In addition to this, the obtained results for avarol and hydroquinone (its structural element) were compared. UV-Vis spectroscopic analysis confirmed interaction between l-dopa and avarol or hydroquinone. Taken all together, the interaction of l-dopa was stronger with hydroquinone than with avarol, presumably reflecting the conformational restrains of avarol caused by its terpenoid moiety.",
publisher = "Springer",
journal = "Reaction Kinetics, Mechanisms and Catalysis",
title = "Electrochemical and spectroscopic study of l‑dopa interaction with avarol",
volume = "127",
number = "1",
pages = "219-229",
doi = "10.1007/s11144-019-01575-z"
}
Nakarada, Đ., Pejin, B., Dimić, D., Ivanović-Šašić, A., Mojović, Z.,& Mojović, M.. (2019). Electrochemical and spectroscopic study of l‑dopa interaction with avarol. in Reaction Kinetics, Mechanisms and Catalysis
Springer., 127(1), 219-229.
https://doi.org/10.1007/s11144-019-01575-z
Nakarada Đ, Pejin B, Dimić D, Ivanović-Šašić A, Mojović Z, Mojović M. Electrochemical and spectroscopic study of l‑dopa interaction with avarol. in Reaction Kinetics, Mechanisms and Catalysis. 2019;127(1):219-229.
doi:10.1007/s11144-019-01575-z .
Nakarada, Đura, Pejin, Boris, Dimić, Dušan, Ivanović-Šašić, Ana, Mojović, Zorica, Mojović, Miloš, "Electrochemical and spectroscopic study of l‑dopa interaction with avarol" in Reaction Kinetics, Mechanisms and Catalysis, 127, no. 1 (2019):219-229,
https://doi.org/10.1007/s11144-019-01575-z . .
1
1

Sinteza, karakterizacija i biološka aktivnost derivata steroidnih hidrazona

Živković, Marijana

(Универзитет у Београду, Хемијски факултет, 2019)

TY  - THES
AU  - Živković, Marijana
PY  - 2019
UR  - http://eteze.bg.ac.rs/application/showtheses?thesesId=7090
UR  - https://fedorabg.bg.ac.rs/fedora/get/o:20739/bdef:Content/download
UR  - http://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=51729935
UR  - http://nardus.mpn.gov.rs/123456789/11807
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3424
AB  - U potrazi za biološki aktivnim jedinjenjima, počev od progesterona i 3-okso-α,β-nezasićenih androstenskih steroida, u okviru ove disertacije sintetisano je i potpunookarakterisano pedeset novih derivata steroidnih hidrazona, od kojih po jedanaesttiosemikarbazona, tijadiazolina i semikarbazona, dvanaest tiazolidin-4-ona i petkarbazatnih estara.Po prvi put je urađena detaljna analiza stereohemije steroidnih hidrazona u položajimaC-3/17 androstenskih, odnosno C-3/20 progesteronskih derivata. Struktura istereohemija potvrđene su rezultatima rendgenske strukturne analize za tijadiazolin 7a,prvo okarakterisano steroidno jedinjenje koje sadrži šestočlani ugljenični prstenkondenzovan sa spiro-tijadiazolinskim prstenom, i tiazolidinon 9b-E, prvi steroidniderivat sa poznatom konfiguracijom dvostruke veze u položaju C-3 hidrazonotiazolidin-4-onskog fragmenta.Sintetisana jedinjenja su ispoljila najjaču citotoksičnost prema HeLa ćelijamaadenokarcinoma cerviksa i prema K562 ćelijama hronične mijeloidne leukemije, a posvojoj aktivnosti istakli su se tiosemikarbazoni 2a, 2b, 2c i 2f, tijadiazolini 8a i 8e itiazolidin-4-oni 9a i 10a. Pritom su koeficijenti selektivnosti u antikancerskom dejstvuprema malignim ćelijama u odnosu na normalne humane PBMC, kako na nestimulisanetako i na mitogenom stimulisane, bili daleko veći od vrednosti 2,5 što ova jedinjenjasvrstava u potencijalne kandidate za in vivo ispitivanja. Sumporni derivati bili su dalekoaktivniji od kiseoničnih. Najaktivniji derivati indukovali su apoptozu posredstvomkaspaza-3, -8 i -9 i inhibirali angiogezu in vitro zbog čega se smatra da posedujuznačajan antikancerski potencijal.
AB  - Searching for biologically active compounds, within this doctoraldissertation fifty new steroidal hydrazone derivatives, of which 11 thiosemicarbazones,11 thiadiazolines, 12 thiazolidin-4-ones, 11 semicarbazones and 5 carbazate esters, weresynthesized starting with progesterone and 3-oxo-α,β-unsaturated androstene steroids,and fully characterized.For the first time, detailed stereochemistry analyses of steroidal hydrazones in the C-3/17 positions of androstene derivatives, or C-3/20 positions of progesterone derivativeswas done. Structure and stereochemistry were confirmed by the results of X-rayanalyses for thiadiazoline 7a, the first characterized steroid compound that contains sixmemberedcarbon ring condensed with the spiro-thiadiazoline ring, and thiazolidinone9b-E, the first steroidal derivative with known configuration of double bond in C-3position of the hydrazono-thiazolidin-4-one fragment.Synthesised compounds manifested the best cytotoxicity towards HeLa cervixadenocarcinoma cells, and K562 cells of chronic myeloide leukemia, the best activitybeing showed by thiosemicarbazones 2a, 2b, 2c and 2f, thiadiazolines 8a and 8e, andthiazolidin-4-ones 9a and 10a. All of these compounds exhibited considerably higherintensities of cytotoxic action against malignant cells when compared with normalhuman PBMC, both resting and mitogen-stimulated, with coefficient of selectivityhigher than 2.5, which makes these compounds potential candidates for in vivoexperiments. Sulfur derivatives were much more active than oxygen derivatives. Themost active derivatives induced apoptosis mediated by caspase-3, -8 and -9, and theyinhibited angiogenesis in vitro, because of what they are considered to have significantanticancer potential.
PB  - Универзитет у Београду, Хемијски факултет
T2  - Универзитет у Београду
T1  - Sinteza, karakterizacija i biološka aktivnost derivata steroidnih hidrazona
UR  - https://hdl.handle.net/21.15107/rcub_nardus_11807
ER  - 
@phdthesis{
author = "Živković, Marijana",
year = "2019",
abstract = "U potrazi za biološki aktivnim jedinjenjima, počev od progesterona i 3-okso-α,β-nezasićenih androstenskih steroida, u okviru ove disertacije sintetisano je i potpunookarakterisano pedeset novih derivata steroidnih hidrazona, od kojih po jedanaesttiosemikarbazona, tijadiazolina i semikarbazona, dvanaest tiazolidin-4-ona i petkarbazatnih estara.Po prvi put je urađena detaljna analiza stereohemije steroidnih hidrazona u položajimaC-3/17 androstenskih, odnosno C-3/20 progesteronskih derivata. Struktura istereohemija potvrđene su rezultatima rendgenske strukturne analize za tijadiazolin 7a,prvo okarakterisano steroidno jedinjenje koje sadrži šestočlani ugljenični prstenkondenzovan sa spiro-tijadiazolinskim prstenom, i tiazolidinon 9b-E, prvi steroidniderivat sa poznatom konfiguracijom dvostruke veze u položaju C-3 hidrazonotiazolidin-4-onskog fragmenta.Sintetisana jedinjenja su ispoljila najjaču citotoksičnost prema HeLa ćelijamaadenokarcinoma cerviksa i prema K562 ćelijama hronične mijeloidne leukemije, a posvojoj aktivnosti istakli su se tiosemikarbazoni 2a, 2b, 2c i 2f, tijadiazolini 8a i 8e itiazolidin-4-oni 9a i 10a. Pritom su koeficijenti selektivnosti u antikancerskom dejstvuprema malignim ćelijama u odnosu na normalne humane PBMC, kako na nestimulisanetako i na mitogenom stimulisane, bili daleko veći od vrednosti 2,5 što ova jedinjenjasvrstava u potencijalne kandidate za in vivo ispitivanja. Sumporni derivati bili su dalekoaktivniji od kiseoničnih. Najaktivniji derivati indukovali su apoptozu posredstvomkaspaza-3, -8 i -9 i inhibirali angiogezu in vitro zbog čega se smatra da posedujuznačajan antikancerski potencijal., Searching for biologically active compounds, within this doctoraldissertation fifty new steroidal hydrazone derivatives, of which 11 thiosemicarbazones,11 thiadiazolines, 12 thiazolidin-4-ones, 11 semicarbazones and 5 carbazate esters, weresynthesized starting with progesterone and 3-oxo-α,β-unsaturated androstene steroids,and fully characterized.For the first time, detailed stereochemistry analyses of steroidal hydrazones in the C-3/17 positions of androstene derivatives, or C-3/20 positions of progesterone derivativeswas done. Structure and stereochemistry were confirmed by the results of X-rayanalyses for thiadiazoline 7a, the first characterized steroid compound that contains sixmemberedcarbon ring condensed with the spiro-thiadiazoline ring, and thiazolidinone9b-E, the first steroidal derivative with known configuration of double bond in C-3position of the hydrazono-thiazolidin-4-one fragment.Synthesised compounds manifested the best cytotoxicity towards HeLa cervixadenocarcinoma cells, and K562 cells of chronic myeloide leukemia, the best activitybeing showed by thiosemicarbazones 2a, 2b, 2c and 2f, thiadiazolines 8a and 8e, andthiazolidin-4-ones 9a and 10a. All of these compounds exhibited considerably higherintensities of cytotoxic action against malignant cells when compared with normalhuman PBMC, both resting and mitogen-stimulated, with coefficient of selectivityhigher than 2.5, which makes these compounds potential candidates for in vivoexperiments. Sulfur derivatives were much more active than oxygen derivatives. Themost active derivatives induced apoptosis mediated by caspase-3, -8 and -9, and theyinhibited angiogenesis in vitro, because of what they are considered to have significantanticancer potential.",
publisher = "Универзитет у Београду, Хемијски факултет",
journal = "Универзитет у Београду",
title = "Sinteza, karakterizacija i biološka aktivnost derivata steroidnih hidrazona",
url = "https://hdl.handle.net/21.15107/rcub_nardus_11807"
}
Živković, M.. (2019). Sinteza, karakterizacija i biološka aktivnost derivata steroidnih hidrazona. in Универзитет у Београду
Универзитет у Београду, Хемијски факултет..
https://hdl.handle.net/21.15107/rcub_nardus_11807
Živković M. Sinteza, karakterizacija i biološka aktivnost derivata steroidnih hidrazona. in Универзитет у Београду. 2019;.
https://hdl.handle.net/21.15107/rcub_nardus_11807 .
Živković, Marijana, "Sinteza, karakterizacija i biološka aktivnost derivata steroidnih hidrazona" in Универзитет у Београду (2019),
https://hdl.handle.net/21.15107/rcub_nardus_11807 .

Leaf-surface guaianolides from Amphoricarpos neumaeyri showing protective effect on human lymphocytes DNA

Cvetković, Mirjana; Đorđević, Iris; Jadranin, Milka; Stanković, Miroslava; Mandić, Boris; Milosavljević, Slobodan; Vujisić, Ljubodrag V.

(Informa UK Limited, 2019)

TY  - JOUR
AU  - Cvetković, Mirjana
AU  - Đorđević, Iris
AU  - Jadranin, Milka
AU  - Stanković, Miroslava
AU  - Mandić, Boris
AU  - Milosavljević, Slobodan
AU  - Vujisić, Ljubodrag V.
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3266
AB  - Analysis of composition of CH2Cl2 surface extract of leaves of Amphoricarpos neumayeri Vis. revealed 16 sesquiterpene lactones with guaianolide skeleton, so called amphoricarpolides, typical for this genus. Four of them, 13–16, were new derivatives and their structures were elucidated by detailed analyses of IR, NMR and MS data. Amphoricarpolide (9), its 15-O-acetyl derivative (5), and two 9β-hydroxyamphoricarpolides, 3,15-di-O-acetyl- and 3-O-acetyl-15-O-isovaleroyl derivatives (3 and 6, respectively) were tested for in vitro protective effect on chromosome aberrations in peripheral human lymphocytes using cytochalasin-B blocked micronucleus (CBMN) assay. The tested compound exerted a beneficial effect by decreasing DNA damage of human lymphocytes.
PB  - Informa UK Limited
T2  - Natural Product Research
T1  - Leaf-surface guaianolides from Amphoricarpos neumaeyri                    showing protective effect on human lymphocytes DNA
SP  - 1
EP  - 9
DO  - 10.1080/14786419.2019.1687470
ER  - 
@article{
author = "Cvetković, Mirjana and Đorđević, Iris and Jadranin, Milka and Stanković, Miroslava and Mandić, Boris and Milosavljević, Slobodan and Vujisić, Ljubodrag V.",
year = "2019",
abstract = "Analysis of composition of CH2Cl2 surface extract of leaves of Amphoricarpos neumayeri Vis. revealed 16 sesquiterpene lactones with guaianolide skeleton, so called amphoricarpolides, typical for this genus. Four of them, 13–16, were new derivatives and their structures were elucidated by detailed analyses of IR, NMR and MS data. Amphoricarpolide (9), its 15-O-acetyl derivative (5), and two 9β-hydroxyamphoricarpolides, 3,15-di-O-acetyl- and 3-O-acetyl-15-O-isovaleroyl derivatives (3 and 6, respectively) were tested for in vitro protective effect on chromosome aberrations in peripheral human lymphocytes using cytochalasin-B blocked micronucleus (CBMN) assay. The tested compound exerted a beneficial effect by decreasing DNA damage of human lymphocytes.",
publisher = "Informa UK Limited",
journal = "Natural Product Research",
title = "Leaf-surface guaianolides from Amphoricarpos neumaeyri                    showing protective effect on human lymphocytes DNA",
pages = "1-9",
doi = "10.1080/14786419.2019.1687470"
}
Cvetković, M., Đorđević, I., Jadranin, M., Stanković, M., Mandić, B., Milosavljević, S.,& Vujisić, L. V.. (2019). Leaf-surface guaianolides from Amphoricarpos neumaeyri                    showing protective effect on human lymphocytes DNA. in Natural Product Research
Informa UK Limited., 1-9.
https://doi.org/10.1080/14786419.2019.1687470
Cvetković M, Đorđević I, Jadranin M, Stanković M, Mandić B, Milosavljević S, Vujisić LV. Leaf-surface guaianolides from Amphoricarpos neumaeyri                    showing protective effect on human lymphocytes DNA. in Natural Product Research. 2019;:1-9.
doi:10.1080/14786419.2019.1687470 .
Cvetković, Mirjana, Đorđević, Iris, Jadranin, Milka, Stanković, Miroslava, Mandić, Boris, Milosavljević, Slobodan, Vujisić, Ljubodrag V., "Leaf-surface guaianolides from Amphoricarpos neumaeyri                    showing protective effect on human lymphocytes DNA" in Natural Product Research (2019):1-9,
https://doi.org/10.1080/14786419.2019.1687470 . .
3
3
2

Halofitne biljne vrste - izolovanje i karakterizacija sekundarnih metabolita

Stanković, Jovana

(Универзитет у Београду, Хемијски факултет, 2019)

TY  - THES
AU  - Stanković, Jovana
PY  - 2019
UR  - http://eteze.bg.ac.rs/application/showtheses?thesesId=7015
UR  - https://fedorabg.bg.ac.rs/fedora/get/o:20623/bdef:Content/download
UR  - http://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=51738383
UR  - http://nardus.mpn.gov.rs/123456789/11672
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3425
AB  - Predmet proučavanja ove doktorske disertacije su sekundarni metaboliti halofita(biljaka koje naseljavaju staništa sa visokim sadržajem soli). U Srbiji se zaslanjenastaništa uglavnom javljaju na teritoriji Vojvodine. U ovom radu izolovani su i hemijskiokarakterisani flavonoidni glikozidi i saponini iz halofitnih vrsta roda Atriplex (A.littoralis, A. tatarica i A. prostrata) i određena je njihova različita biološka aktivnost.Pored biljaka iz roda Atriplex ispitivana je halofitna biljna vrsta Artemisia santonicum izkoje je izolovano etarsko ulje, određen hemijski sastav i ispitana biološka aktivnost.Halofitne biljne vrste se u tradicionalnoj medicini koriste u brojne svrhe kaoantiseptici, diuretici, antiparazitici, antipiretici, purgativi, laksativi, za lečenjedijabetesa, visokog krvnog pritiska, astme, gihta i reumatizma. Ekstrakti i jedinjenjaizolovana iz vrsta roda Atriplex pokazuju antioksidativnu, antimikrobnu, citotoksičnu,antiparazitsku, i insekticidnu aktivnost. Etarska ulja vrsta roda Artemisia su pokazalaantioksidativnu, antibakterijsku, antifungalnu, antiparazitsku, hepatoprotektivnu,neuroprotektivnu i antimalarijsku aktivnost.Vrste roda Atriplex su bogat izvor sekundarnih metabolita prvenstvenoflavonoida, saponina i alkaloida. U okviru ove disertacije izolovano je i okarakterisanoukupno 13 jedinjenja, od kojih je 7 novih prirodnih proizvoda (43-45, 51-54). Iz vrste A.littoralis izolovano je 6 jedinjenja, četiri flavonoidna glikozida (43-46) i dva fenolnajedinjenja (47, 48). Iz A. tatarica izolovano je 6 jedinjenja, tri flavonoidna glikozida(49-51) i tri triterpenska saponina oleanolnog tipa (52-54). Iz etarskog ulja Artemisiasantonicum izolovan je oksigenovani monoterpen (55)...
AB  - The subject of this doctoral dissertation are the secondary metabolites ofhalophytes (plants wild growing at saline habitats). In Serbia such habitats are mainlyfound in Vojvodina. Flavonoid glycosides and saponins from halophytic speciesAtriplex (A. littoralis, A. tatarica and A. prostrata) were isolated, chemicallycharacterized and their various biological activities were determined. In addition, ahalophyte species from the genus Artemisia (A. santonicum) was examined. Its essentialoil was isolated, the chemical composition determined and various biological activitiesof this were tested.Several halophytic plant species are used in many traditional formulations asantiseptics, diuretics, antiparasitics, antipyretics, purgatives, laxatives, for the treatmentof diabetes, high blood pressure, asthma, gout and rheumatism. Extracts and compoundsisolated from the genus Atriplex show antiparasitic, insecticidal, antimicrobial,cytotoxic and antioxidant activity. Essential oils of the genus Artemisia have shownantioxidant, antibacterial, antifungal, antiparasitic, hepatoprotective, neuroprotectiveand antimalarial activity.Atriplex species are a rich source of secondary metabolites, primarily flavonoids,saponins and alkaloids. In this study, a total of 13 compounds were isolated andcharacterized by means of spectroscopic techniques (1D and 2D NMR, IR and MS).Among them seven (43-45, 51-54) were the new compounds. At the same time, in theextract of A. littoralis, six compounds, four flavonoid glycosides (43-46) and twophenolic compounds (47, 48) were identified. From A. tatarica six compounds, threeflavonoid glycosides (49-51) and three triterpene saponins of an oleanane type (52-54)were isolated. An oxygenated monoterpene (55) was isolated from Artemisiasantonicum essential oil...
PB  - Универзитет у Београду, Хемијски факултет
T2  - Универзитет у Београду
T1  - Halofitne biljne vrste - izolovanje i karakterizacija sekundarnih metabolita
UR  - https://hdl.handle.net/21.15107/rcub_nardus_11672
ER  - 
@phdthesis{
author = "Stanković, Jovana",
year = "2019",
abstract = "Predmet proučavanja ove doktorske disertacije su sekundarni metaboliti halofita(biljaka koje naseljavaju staništa sa visokim sadržajem soli). U Srbiji se zaslanjenastaništa uglavnom javljaju na teritoriji Vojvodine. U ovom radu izolovani su i hemijskiokarakterisani flavonoidni glikozidi i saponini iz halofitnih vrsta roda Atriplex (A.littoralis, A. tatarica i A. prostrata) i određena je njihova različita biološka aktivnost.Pored biljaka iz roda Atriplex ispitivana je halofitna biljna vrsta Artemisia santonicum izkoje je izolovano etarsko ulje, određen hemijski sastav i ispitana biološka aktivnost.Halofitne biljne vrste se u tradicionalnoj medicini koriste u brojne svrhe kaoantiseptici, diuretici, antiparazitici, antipiretici, purgativi, laksativi, za lečenjedijabetesa, visokog krvnog pritiska, astme, gihta i reumatizma. Ekstrakti i jedinjenjaizolovana iz vrsta roda Atriplex pokazuju antioksidativnu, antimikrobnu, citotoksičnu,antiparazitsku, i insekticidnu aktivnost. Etarska ulja vrsta roda Artemisia su pokazalaantioksidativnu, antibakterijsku, antifungalnu, antiparazitsku, hepatoprotektivnu,neuroprotektivnu i antimalarijsku aktivnost.Vrste roda Atriplex su bogat izvor sekundarnih metabolita prvenstvenoflavonoida, saponina i alkaloida. U okviru ove disertacije izolovano je i okarakterisanoukupno 13 jedinjenja, od kojih je 7 novih prirodnih proizvoda (43-45, 51-54). Iz vrste A.littoralis izolovano je 6 jedinjenja, četiri flavonoidna glikozida (43-46) i dva fenolnajedinjenja (47, 48). Iz A. tatarica izolovano je 6 jedinjenja, tri flavonoidna glikozida(49-51) i tri triterpenska saponina oleanolnog tipa (52-54). Iz etarskog ulja Artemisiasantonicum izolovan je oksigenovani monoterpen (55)..., The subject of this doctoral dissertation are the secondary metabolites ofhalophytes (plants wild growing at saline habitats). In Serbia such habitats are mainlyfound in Vojvodina. Flavonoid glycosides and saponins from halophytic speciesAtriplex (A. littoralis, A. tatarica and A. prostrata) were isolated, chemicallycharacterized and their various biological activities were determined. In addition, ahalophyte species from the genus Artemisia (A. santonicum) was examined. Its essentialoil was isolated, the chemical composition determined and various biological activitiesof this were tested.Several halophytic plant species are used in many traditional formulations asantiseptics, diuretics, antiparasitics, antipyretics, purgatives, laxatives, for the treatmentof diabetes, high blood pressure, asthma, gout and rheumatism. Extracts and compoundsisolated from the genus Atriplex show antiparasitic, insecticidal, antimicrobial,cytotoxic and antioxidant activity. Essential oils of the genus Artemisia have shownantioxidant, antibacterial, antifungal, antiparasitic, hepatoprotective, neuroprotectiveand antimalarial activity.Atriplex species are a rich source of secondary metabolites, primarily flavonoids,saponins and alkaloids. In this study, a total of 13 compounds were isolated andcharacterized by means of spectroscopic techniques (1D and 2D NMR, IR and MS).Among them seven (43-45, 51-54) were the new compounds. At the same time, in theextract of A. littoralis, six compounds, four flavonoid glycosides (43-46) and twophenolic compounds (47, 48) were identified. From A. tatarica six compounds, threeflavonoid glycosides (49-51) and three triterpene saponins of an oleanane type (52-54)were isolated. An oxygenated monoterpene (55) was isolated from Artemisiasantonicum essential oil...",
publisher = "Универзитет у Београду, Хемијски факултет",
journal = "Универзитет у Београду",
title = "Halofitne biljne vrste - izolovanje i karakterizacija sekundarnih metabolita",
url = "https://hdl.handle.net/21.15107/rcub_nardus_11672"
}
Stanković, J.. (2019). Halofitne biljne vrste - izolovanje i karakterizacija sekundarnih metabolita. in Универзитет у Београду
Универзитет у Београду, Хемијски факултет..
https://hdl.handle.net/21.15107/rcub_nardus_11672
Stanković J. Halofitne biljne vrste - izolovanje i karakterizacija sekundarnih metabolita. in Универзитет у Београду. 2019;.
https://hdl.handle.net/21.15107/rcub_nardus_11672 .
Stanković, Jovana, "Halofitne biljne vrste - izolovanje i karakterizacija sekundarnih metabolita" in Универзитет у Београду (2019),
https://hdl.handle.net/21.15107/rcub_nardus_11672 .

Metabolomička studija balkanskih vrsta roda Amphoricarpos Vis. (Asteraceae)

Cvetković, Mirjana

(Универзитет у Београду, Хемијски факултет, 2019)

TY  - THES
AU  - Cvetković, Mirjana
PY  - 2019
UR  - http://eteze.bg.ac.rs/application/showtheses?thesesId=7045
UR  - https://fedorabg.bg.ac.rs/fedora/get/o:20666/bdef:Content/download
UR  - http://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=51737615
UR  - http://nardus.mpn.gov.rs/123456789/11706
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3429
AB  - Metabolomika je nova naučna multidisciplinarna oblast koja obuhvata različiteaspekte biologije, hemije i matematike. Koristi moderne spektroskopske ihromatografske tehnike (NMR, IC, UV, MS, GC, LC) i multivarijantnu statističkuanalizu podataka sa ciljem da se izmere kvantitativno i kvalitativno svi metaboliti uispitivanom organizmu i na taj način dobije jasna metabolomička slika pod ispitivanimuslovima. Primena metabolomike nije ograničena samo na biljni svet, već se možeprimeniti na sve žive organizme, pa tako i na ljude. Posebno je značajna mogućnostprimene u medicini kao dijagnostičke metode ili u farmakognoziji za otkrivanje novihlekovitih sirovina. U ovoj disertaciji primena metabolomike na endemski biljni rodAmphoricarpos Vis. imala je dva cilja: (a) sticanje novih saznanja o mogućnostiprimene dobijenih rezultata u diferencijaciji balkanskih vrsta ovog roda i (b) razvojmetode za brzo otkrivanje novih farmakološki aktivnih sastojaka u biljnom materijalu.Vrste roda Amphoricarpos Vis. rasprostranjene su na Balkanskom poluostrvu.Anatoliji i Kavkazu. Da bi se dobilo više uvida u taksonomski status balkanskih taksonaovog roda, koji nije do kraja raščišćen, primenjena je metabolomička studija. Po Blečićui Mayeru1 postoje tri taksona: dve vrste A. neumayeri Vis. i A. autariatus Blečić etMayer, koja se deli na dve podvrste - ssp. autariatus i ssp. bertisceus Blečić et Mayer. Sdruge strane, Webb2 priznaje samo jednu vrstu - A. neumayeri Vis., koja sadrži dvepodvrste - ssp. neumayeri i ssp. murbeckii Bošnjak. U novije vreme, na osnovuispitivanja genoma vrsta ovog roda predložena je samo jedna vrsta, А. neumayerianus(Vis.) Greuter.3 U ovom radu analizirana su sva tri taksona (prema Blečiću i Mayeru), auzorci su sakupljeni na različitim lokalitetima u Crnoj Gori u fazi cvetanja. Primenjenaje 1H NMR spektroskopija kombinovana sa multivarijantnom analizom podataka.Pokazano je da je OPLS-DA (engl. Orthogonal Partial Least Squares-DiscriminantAnalysis) najefikasniji metod za diskriminaciju ispitivanih uzoraka na osnovumetabolita prisutnih u ekstraktima. Utvrđeno je da je glavna razlika između A.autariatus i A. neumayeri prisustvo karakterističnih seskviterpenskih laktonagvajanolidnog tipa (amforikarpolida). Glavni seskviterpenski lakton vrste A. neumayerije oksidovan u položaju 2, dok laktoni prisutni u obe podvrste A. autariatus suoksidovani u poziciji 9, što potvrđuje da seskviterpenski laktoni mogu bitihemotaksonomski markeri u porodici Asteraceae...
AB  - Metabolomics is a new scientific multidisciplinary field that includes variousaspects of biology, chemistry and mathematics. It uses modern spectroscopic andchromatographic techniques (NMR, IC, UV, MS, GC, LC) and multivariate statisticaldata analysis to measure quantitatively and qualitatively all of the metabolites in the testorganism and thereby obtain a clear metabolic profile under test conditions. The use ofmetabolomics is not limited to the plant world, but can be applied to all livingorganisms as well as humans. A particularly important possibility is the application inmedicine as a diagnostic method or in pharmacognosy for the discovery of new naturalsources of drugs. In this thesis, the application of metabolomics to the endemic plantgenus Amphoricarpos Vis. was applied with two objectives: (a) acquiring newknowledge of the systematization of the genus, and (b) developing a method for rapiddetection of new pharmacologically active ingredients in plant material.Genus Amphoricarpos Vis. is an endemic of the western part of the BalkanPeninsula. In order to gain more insight into the taxonomic status of the genus that isstill ambiguous, a metabolomic study was applied. Blečić and Mayer1 proposed threetaxa: two species A. neumayeri Vis. and A. autariatus Blečić et Mayer, the latter dividedinto two subspecies, ssp. autariatus i ssp. bertisceus Blečič et Mayer. On the other hand,Webb2 recognizeed only one species, A. neumayeri Vis. divided into two subspecies,ssp. neumayeri i ssp. murbeckii Bošnjak. Recently, on the basis of a genomeexamination of the taxa from the West Balkans, only one species was proposed, A.neumayerianus (Vis.) Greuter.3In this dissertation all three taxa (according to Blečić and Mayer)1 were analysed. Thesamples were collected at different locations in Montenegro at the stage of flowering.1H NMR spectroscopy combined with multivariate data analysis was applied.Orthogonal Partial Least Squares-Discriminant Analysis (OPLS-DA) has been shown tobe the most effective method for discrimination of the tested samples, based on themetabolites present in the extracts. It was found that the main difference between A.autariatus and A. neumayeri was the presence of characteristic guaianolidesesquiterpene lactones (amforicarpolides). The major sesquiterpene lactones in theextract of A. neumayeri were oxidized in position 2, while the lactones present in bothsubspecies of A. autariatus were oxidized at position 9, which confirms thatsesquiterpene lactones may be chemotaxonomic markers in the Asteraceae family...
PB  - Универзитет у Београду, Хемијски факултет
T2  - Универзитет у Београду
T1  - Metabolomička studija balkanskih vrsta roda Amphoricarpos Vis. (Asteraceae)
UR  - https://hdl.handle.net/21.15107/rcub_nardus_11706
ER  - 
@phdthesis{
author = "Cvetković, Mirjana",
year = "2019",
abstract = "Metabolomika je nova naučna multidisciplinarna oblast koja obuhvata različiteaspekte biologije, hemije i matematike. Koristi moderne spektroskopske ihromatografske tehnike (NMR, IC, UV, MS, GC, LC) i multivarijantnu statističkuanalizu podataka sa ciljem da se izmere kvantitativno i kvalitativno svi metaboliti uispitivanom organizmu i na taj način dobije jasna metabolomička slika pod ispitivanimuslovima. Primena metabolomike nije ograničena samo na biljni svet, već se možeprimeniti na sve žive organizme, pa tako i na ljude. Posebno je značajna mogućnostprimene u medicini kao dijagnostičke metode ili u farmakognoziji za otkrivanje novihlekovitih sirovina. U ovoj disertaciji primena metabolomike na endemski biljni rodAmphoricarpos Vis. imala je dva cilja: (a) sticanje novih saznanja o mogućnostiprimene dobijenih rezultata u diferencijaciji balkanskih vrsta ovog roda i (b) razvojmetode za brzo otkrivanje novih farmakološki aktivnih sastojaka u biljnom materijalu.Vrste roda Amphoricarpos Vis. rasprostranjene su na Balkanskom poluostrvu.Anatoliji i Kavkazu. Da bi se dobilo više uvida u taksonomski status balkanskih taksonaovog roda, koji nije do kraja raščišćen, primenjena je metabolomička studija. Po Blečićui Mayeru1 postoje tri taksona: dve vrste A. neumayeri Vis. i A. autariatus Blečić etMayer, koja se deli na dve podvrste - ssp. autariatus i ssp. bertisceus Blečić et Mayer. Sdruge strane, Webb2 priznaje samo jednu vrstu - A. neumayeri Vis., koja sadrži dvepodvrste - ssp. neumayeri i ssp. murbeckii Bošnjak. U novije vreme, na osnovuispitivanja genoma vrsta ovog roda predložena je samo jedna vrsta, А. neumayerianus(Vis.) Greuter.3 U ovom radu analizirana su sva tri taksona (prema Blečiću i Mayeru), auzorci su sakupljeni na različitim lokalitetima u Crnoj Gori u fazi cvetanja. Primenjenaje 1H NMR spektroskopija kombinovana sa multivarijantnom analizom podataka.Pokazano je da je OPLS-DA (engl. Orthogonal Partial Least Squares-DiscriminantAnalysis) najefikasniji metod za diskriminaciju ispitivanih uzoraka na osnovumetabolita prisutnih u ekstraktima. Utvrđeno je da je glavna razlika između A.autariatus i A. neumayeri prisustvo karakterističnih seskviterpenskih laktonagvajanolidnog tipa (amforikarpolida). Glavni seskviterpenski lakton vrste A. neumayerije oksidovan u položaju 2, dok laktoni prisutni u obe podvrste A. autariatus suoksidovani u poziciji 9, što potvrđuje da seskviterpenski laktoni mogu bitihemotaksonomski markeri u porodici Asteraceae..., Metabolomics is a new scientific multidisciplinary field that includes variousaspects of biology, chemistry and mathematics. It uses modern spectroscopic andchromatographic techniques (NMR, IC, UV, MS, GC, LC) and multivariate statisticaldata analysis to measure quantitatively and qualitatively all of the metabolites in the testorganism and thereby obtain a clear metabolic profile under test conditions. The use ofmetabolomics is not limited to the plant world, but can be applied to all livingorganisms as well as humans. A particularly important possibility is the application inmedicine as a diagnostic method or in pharmacognosy for the discovery of new naturalsources of drugs. In this thesis, the application of metabolomics to the endemic plantgenus Amphoricarpos Vis. was applied with two objectives: (a) acquiring newknowledge of the systematization of the genus, and (b) developing a method for rapiddetection of new pharmacologically active ingredients in plant material.Genus Amphoricarpos Vis. is an endemic of the western part of the BalkanPeninsula. In order to gain more insight into the taxonomic status of the genus that isstill ambiguous, a metabolomic study was applied. Blečić and Mayer1 proposed threetaxa: two species A. neumayeri Vis. and A. autariatus Blečić et Mayer, the latter dividedinto two subspecies, ssp. autariatus i ssp. bertisceus Blečič et Mayer. On the other hand,Webb2 recognizeed only one species, A. neumayeri Vis. divided into two subspecies,ssp. neumayeri i ssp. murbeckii Bošnjak. Recently, on the basis of a genomeexamination of the taxa from the West Balkans, only one species was proposed, A.neumayerianus (Vis.) Greuter.3In this dissertation all three taxa (according to Blečić and Mayer)1 were analysed. Thesamples were collected at different locations in Montenegro at the stage of flowering.1H NMR spectroscopy combined with multivariate data analysis was applied.Orthogonal Partial Least Squares-Discriminant Analysis (OPLS-DA) has been shown tobe the most effective method for discrimination of the tested samples, based on themetabolites present in the extracts. It was found that the main difference between A.autariatus and A. neumayeri was the presence of characteristic guaianolidesesquiterpene lactones (amforicarpolides). The major sesquiterpene lactones in theextract of A. neumayeri were oxidized in position 2, while the lactones present in bothsubspecies of A. autariatus were oxidized at position 9, which confirms thatsesquiterpene lactones may be chemotaxonomic markers in the Asteraceae family...",
publisher = "Универзитет у Београду, Хемијски факултет",
journal = "Универзитет у Београду",
title = "Metabolomička studija balkanskih vrsta roda Amphoricarpos Vis. (Asteraceae)",
url = "https://hdl.handle.net/21.15107/rcub_nardus_11706"
}
Cvetković, M.. (2019). Metabolomička studija balkanskih vrsta roda Amphoricarpos Vis. (Asteraceae). in Универзитет у Београду
Универзитет у Београду, Хемијски факултет..
https://hdl.handle.net/21.15107/rcub_nardus_11706
Cvetković M. Metabolomička studija balkanskih vrsta roda Amphoricarpos Vis. (Asteraceae). in Универзитет у Београду. 2019;.
https://hdl.handle.net/21.15107/rcub_nardus_11706 .
Cvetković, Mirjana, "Metabolomička studija balkanskih vrsta roda Amphoricarpos Vis. (Asteraceae)" in Универзитет у Београду (2019),
https://hdl.handle.net/21.15107/rcub_nardus_11706 .

Fruit as a substrate for a wine: A case study of selected berry and drupe fruit wines

Cakar, Uros; Petrovic, Aleksandar; Pejin, Boris; Cakar, Mira; Živković, Marijana; Vajs, Vlatka; Djordjević, Brizita

(Elsevier, 2019)

TY  - JOUR
AU  - Cakar, Uros
AU  - Petrovic, Aleksandar
AU  - Pejin, Boris
AU  - Cakar, Mira
AU  - Živković, Marijana
AU  - Vajs, Vlatka
AU  - Djordjević, Brizita
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2504
AB  - This study aimed to estimate the potential of the selected berry (strawberry) and drupe (apricot, plum and sweet cherry) fruits as the substrates for the production of new fruit wines enriched with phenolic compounds. Sweet cherry wine (cultivar Burlat) stood out both for the profound content of phenolics (followed by their chemical profile) and potent anti-DPPH radical activity. The same fruit wine samples exhibited high redox potentials, slightly lower than strawberry and plum wine samples. Therefore, sweet cherry cultivar Burlat may be well recommended for development of novel fruit-based products endowed with naturally occurring phenolics. In any case, the remaining four cultivars are also worth further research efforts, particularly apricot cultivar Keckemetska ruza, which is one of the representatives of greatly underestimated fruit type thus far as a substrate for the production of the relevant fruit wines.
PB  - Elsevier
T2  - Scientia Horticulturae
T1  - Fruit as a substrate for a wine: A case study of selected berry and drupe fruit wines
VL  - 244
SP  - 42
EP  - 49
DO  - 10.1016/j.scienta.2018.09.020
ER  - 
@article{
author = "Cakar, Uros and Petrovic, Aleksandar and Pejin, Boris and Cakar, Mira and Živković, Marijana and Vajs, Vlatka and Djordjević, Brizita",
year = "2019",
abstract = "This study aimed to estimate the potential of the selected berry (strawberry) and drupe (apricot, plum and sweet cherry) fruits as the substrates for the production of new fruit wines enriched with phenolic compounds. Sweet cherry wine (cultivar Burlat) stood out both for the profound content of phenolics (followed by their chemical profile) and potent anti-DPPH radical activity. The same fruit wine samples exhibited high redox potentials, slightly lower than strawberry and plum wine samples. Therefore, sweet cherry cultivar Burlat may be well recommended for development of novel fruit-based products endowed with naturally occurring phenolics. In any case, the remaining four cultivars are also worth further research efforts, particularly apricot cultivar Keckemetska ruza, which is one of the representatives of greatly underestimated fruit type thus far as a substrate for the production of the relevant fruit wines.",
publisher = "Elsevier",
journal = "Scientia Horticulturae",
title = "Fruit as a substrate for a wine: A case study of selected berry and drupe fruit wines",
volume = "244",
pages = "42-49",
doi = "10.1016/j.scienta.2018.09.020"
}
Cakar, U., Petrovic, A., Pejin, B., Cakar, M., Živković, M., Vajs, V.,& Djordjević, B.. (2019). Fruit as a substrate for a wine: A case study of selected berry and drupe fruit wines. in Scientia Horticulturae
Elsevier., 244, 42-49.
https://doi.org/10.1016/j.scienta.2018.09.020
Cakar U, Petrovic A, Pejin B, Cakar M, Živković M, Vajs V, Djordjević B. Fruit as a substrate for a wine: A case study of selected berry and drupe fruit wines. in Scientia Horticulturae. 2019;244:42-49.
doi:10.1016/j.scienta.2018.09.020 .
Cakar, Uros, Petrovic, Aleksandar, Pejin, Boris, Cakar, Mira, Živković, Marijana, Vajs, Vlatka, Djordjević, Brizita, "Fruit as a substrate for a wine: A case study of selected berry and drupe fruit wines" in Scientia Horticulturae, 244 (2019):42-49,
https://doi.org/10.1016/j.scienta.2018.09.020 . .
25
14
24

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

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

(American Chemical Society (ACS), 2019)

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 . .
1
23
8
24

Nuclear magnetic resonance as a tool for the assessment of postharvest changes in the metabolome of the skin of sweet cherry ( Prunus avium L.)

Kokalj, Doris; Gođevac, Dejan; Anđelković, Boban D.; Cigić, Blaž; Zlatić, Emil; Hribar, Janez; Vidrih, Rajko

(International Society for Horticultural Science (ISHS), 2019)

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 . .