Ćirić, Ana

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Application of LC-MS/MS with ion mobility for chemical analysis of propolis extracts with antimicrobial potential

Sofrenić, Ivana; Ljujić, Jovana; Simić, Katarina; Ivanović, Stefan; Stanković Jeremić, Jovana; Ćirić, Ana; Soković, Marina; Andjelković, Boban

(Serbian Chemical Society, 2021)

TY  - JOUR
AU  - Sofrenić, Ivana
AU  - Ljujić, Jovana
AU  - Simić, Katarina
AU  - Ivanović, Stefan
AU  - Stanković Jeremić, Jovana
AU  - Ćirić, Ana
AU  - Soković, Marina
AU  - Andjelković, Boban
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4909
AB  - The objective of this study was to test four-dimensional LC-ESI-MS/MS chromatography in analysis of complex mixture such as ethanol extracts of different propolis samples. In total more than 1200 picks were identified and only for 185 literature conformation was found. The given data represent the result of tentative identification, and summarized results are given in the text. Comparing the samples, from different altitudes, 96 components were detected as characteristic in high altitude samples and 18 in samples collected at low altitudes. Antimicrobial activity of ethanol extracts of propolis (EEP) and pro­pyl­ene glycol extracts of propolis (PGEP) were carried out on S. aureus, B. cereus, M. flavus, L. monocytogenes, P. aeruginosa, S. typhimurium, E. coli and E. cloacae bacterial strains and compared with broad-spectrum antibiotics, streptomycin and ampicillin. Anti-quorum sensing activity was performed on P. aeruginosa by testing the effect of representative propolis extracts on bio­film formation, twitching and motility activity and production of pyocyanin. We demonstrated that the majority of explored propolis extracts have greater or equal minimal inhibitory concentration and minimum bactericidal concen­tra­tion values compared to antibiotics, independently of the solvent used for the extraction. The samples collected from the highest altitude emerged as least active antimicrobial agents but with the greatest potential as anti-quorum sen­sing agents.
AB  - Циљ овог истраживања је билo тестирање четвородимензионалне LC–ESI-MS/MS хроматографије у анализи комплексних смеша, као што су етанолни екстракти различитих узорака прополиса. Укупно је идентификовано више од 1200 пикова, а самo за 185 смо нашли литературну потврду. Приказани подаци представљају тентативну идентификацију и сумирани резултат је дат у тексту. Поређењем узорака са различитих надморских висина, за 96 једињења је утврђено да се налазе само у узорцима са високе надморске висине и 18 само у узорцима прикупљеним на нижим надморским висинама. Антибактеријске активности етанолних и пропиленгликолних екстрактата прополиса (EEP и PGEP, редом) тестиране су на S. aureus, B. cereus, M. flavus, L. monocytogenes, P. aeruginosa, S. typhimurium, E. coli и E. cloacae бактеријским линијама и поређене са анти- биотицима широког спектра деловања, стрептомицином и ампицилином. Anti-quorum sensing активност је тестирана на P. aeruginosa испитивањем ефекта репрезентативних екстраката прополиса на формирање биофилма, тестовима покретљивости руба коло- није (twitching и mobility) и производње пиоцианина. Показали смо да највећи број, коришћених екстраката прополиса, има истe и/или мање MIC и MBC вредности, у поре- ђењу са атибиотицима, независно од растварача коришћеног за екстракцију. Узорци прикупљени на високим надморским висинама су се показали као најмање активни антибактерициди али имају велики anti-quorum sensing потенцијал.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Application of LC-MS/MS with ion mobility for chemical analysis of propolis extracts with antimicrobial potential
T1  - Примена lc–ms/ms технике са јонском покретљивошћу за хемијску анализу екстраката прополиса са антимикробним потенцијалом.
IS  - 12
SP  - 1205
EP  - 1218
DO  - 10.2298/JSC210812086S
ER  - 
@article{
author = "Sofrenić, Ivana and Ljujić, Jovana and Simić, Katarina and Ivanović, Stefan and Stanković Jeremić, Jovana and Ćirić, Ana and Soković, Marina and Andjelković, Boban",
year = "2021",
abstract = "The objective of this study was to test four-dimensional LC-ESI-MS/MS chromatography in analysis of complex mixture such as ethanol extracts of different propolis samples. In total more than 1200 picks were identified and only for 185 literature conformation was found. The given data represent the result of tentative identification, and summarized results are given in the text. Comparing the samples, from different altitudes, 96 components were detected as characteristic in high altitude samples and 18 in samples collected at low altitudes. Antimicrobial activity of ethanol extracts of propolis (EEP) and pro­pyl­ene glycol extracts of propolis (PGEP) were carried out on S. aureus, B. cereus, M. flavus, L. monocytogenes, P. aeruginosa, S. typhimurium, E. coli and E. cloacae bacterial strains and compared with broad-spectrum antibiotics, streptomycin and ampicillin. Anti-quorum sensing activity was performed on P. aeruginosa by testing the effect of representative propolis extracts on bio­film formation, twitching and motility activity and production of pyocyanin. We demonstrated that the majority of explored propolis extracts have greater or equal minimal inhibitory concentration and minimum bactericidal concen­tra­tion values compared to antibiotics, independently of the solvent used for the extraction. The samples collected from the highest altitude emerged as least active antimicrobial agents but with the greatest potential as anti-quorum sen­sing agents., Циљ овог истраживања је билo тестирање четвородимензионалне LC–ESI-MS/MS хроматографије у анализи комплексних смеша, као што су етанолни екстракти различитих узорака прополиса. Укупно је идентификовано више од 1200 пикова, а самo за 185 смо нашли литературну потврду. Приказани подаци представљају тентативну идентификацију и сумирани резултат је дат у тексту. Поређењем узорака са различитих надморских висина, за 96 једињења је утврђено да се налазе само у узорцима са високе надморске висине и 18 само у узорцима прикупљеним на нижим надморским висинама. Антибактеријске активности етанолних и пропиленгликолних екстрактата прополиса (EEP и PGEP, редом) тестиране су на S. aureus, B. cereus, M. flavus, L. monocytogenes, P. aeruginosa, S. typhimurium, E. coli и E. cloacae бактеријским линијама и поређене са анти- биотицима широког спектра деловања, стрептомицином и ампицилином. Anti-quorum sensing активност је тестирана на P. aeruginosa испитивањем ефекта репрезентативних екстраката прополиса на формирање биофилма, тестовима покретљивости руба коло- није (twitching и mobility) и производње пиоцианина. Показали смо да највећи број, коришћених екстраката прополиса, има истe и/или мање MIC и MBC вредности, у поре- ђењу са атибиотицима, независно од растварача коришћеног за екстракцију. Узорци прикупљени на високим надморским висинама су се показали као најмање активни антибактерициди али имају велики anti-quorum sensing потенцијал.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Application of LC-MS/MS with ion mobility for chemical analysis of propolis extracts with antimicrobial potential, Примена lc–ms/ms технике са јонском покретљивошћу за хемијску анализу екстраката прополиса са антимикробним потенцијалом.",
number = "12",
pages = "1205-1218",
doi = "10.2298/JSC210812086S"
}
Sofrenić, I., Ljujić, J., Simić, K., Ivanović, S., Stanković Jeremić, J., Ćirić, A., Soković, M.,& Andjelković, B.. (2021). Application of LC-MS/MS with ion mobility for chemical analysis of propolis extracts with antimicrobial potential. in Journal of the Serbian Chemical Society
Serbian Chemical Society.(12), 1205-1218.
https://doi.org/10.2298/JSC210812086S
Sofrenić I, Ljujić J, Simić K, Ivanović S, Stanković Jeremić J, Ćirić A, Soković M, Andjelković B. Application of LC-MS/MS with ion mobility for chemical analysis of propolis extracts with antimicrobial potential. in Journal of the Serbian Chemical Society. 2021;(12):1205-1218.
doi:10.2298/JSC210812086S .
Sofrenić, Ivana, Ljujić, Jovana, Simić, Katarina, Ivanović, Stefan, Stanković Jeremić, Jovana, Ćirić, Ana, Soković, Marina, Andjelković, Boban, "Application of LC-MS/MS with ion mobility for chemical analysis of propolis extracts with antimicrobial potential" in Journal of the Serbian Chemical Society, no. 12 (2021):1205-1218,
https://doi.org/10.2298/JSC210812086S . .
2

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

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

(American Chemical Society (ACS), 2019)

TY  - JOUR
AU  - Stanković, Jovana
AU  - Gođevac, Dejan
AU  - Tešević, Vele
AU  - Dajić-Stevanović, Zora
AU  - Ćirić, Ana
AU  - Soković, Marina
AU  - Novaković, Miroslav
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2995
AB  - A new flavonoid glucoside derivative, patuletin 3-O-(2-O-feruloyl)-β-D-glucuronopyranosyl-(1→2)-β-Dglucopyranoside, named atriplexin IV (1), and three new triterpenoid saponin derivatives, two sulfonylated, β-Dglucopyranosyl-3-O-(2-O-sulfo-β-D-galactopyranosyl)-(1→2)-α-L arabinopyranoside-30-alolean-12-en-28-oate (2), named atriplexogenin I, β-D-glucopyranosyl-3-O-(2-O-sulfo-β-D-galactopyranosyl)-(1→2)-α-L-arabinopyranoside)-30-hydroxyolean-12-en-
28-oate (3), named atriplexogenin II, and β-D-glucopyranosyl-3-O-(β-D-glucopyranosyl-(1→2)-β-D-galactopyranosyl-(1→2)-α-L-arabinopyranoside)-30-alolean-12-en-28-oate (4), named atriplexogenin III, were isolated by silica gel column and semipreparative HPLC chromatography from the n-butanol extract of the salt marsh plant Atriplex tatarica. In addition, two known secondary metabolites, patuletin3-O-β-D-apiofuranosyl-(1‴→2″)-β-D-glucopyranoside (5) and patuletin 3-O-5‴-Oferuloyl-β-D-apiofuranosyl-(1‴→2″)-β-D-glucopyranoside (6), were isolated for the first time from A. tatarica. The structures of the isolated compounds were elucidated by 1D and 2D NMR, HRESIMS, IR, and UV data. Antibacterial activity by the microdilution method and antibiofilm activity against P. aeruginosa were assessed. Compound 5 possesses significant
antibacterial activity, while the most potent antibiofilm agent is compound 2.
PB  - American Chemical Society (ACS)
T2  - Journal of Natural Products
T1  - Antibacterial and Antibiofilm Activity of Flavonoid and Saponin Derivatives from Atriplex tatarica against Pseudomonas aeruginosa
VL  - 82
SP  - 1487
EP  - 1495
DO  - 10.1021/acs.jnatprod.8b00970
ER  - 
@article{
author = "Stanković, Jovana and Gođevac, Dejan and Tešević, Vele and Dajić-Stevanović, Zora and Ćirić, Ana and Soković, Marina and Novaković, Miroslav",
year = "2019",
abstract = "A new flavonoid glucoside derivative, patuletin 3-O-(2-O-feruloyl)-β-D-glucuronopyranosyl-(1→2)-β-Dglucopyranoside, named atriplexin IV (1), and three new triterpenoid saponin derivatives, two sulfonylated, β-Dglucopyranosyl-3-O-(2-O-sulfo-β-D-galactopyranosyl)-(1→2)-α-L arabinopyranoside-30-alolean-12-en-28-oate (2), named atriplexogenin I, β-D-glucopyranosyl-3-O-(2-O-sulfo-β-D-galactopyranosyl)-(1→2)-α-L-arabinopyranoside)-30-hydroxyolean-12-en-
28-oate (3), named atriplexogenin II, and β-D-glucopyranosyl-3-O-(β-D-glucopyranosyl-(1→2)-β-D-galactopyranosyl-(1→2)-α-L-arabinopyranoside)-30-alolean-12-en-28-oate (4), named atriplexogenin III, were isolated by silica gel column and semipreparative HPLC chromatography from the n-butanol extract of the salt marsh plant Atriplex tatarica. In addition, two known secondary metabolites, patuletin3-O-β-D-apiofuranosyl-(1‴→2″)-β-D-glucopyranoside (5) and patuletin 3-O-5‴-Oferuloyl-β-D-apiofuranosyl-(1‴→2″)-β-D-glucopyranoside (6), were isolated for the first time from A. tatarica. The structures of the isolated compounds were elucidated by 1D and 2D NMR, HRESIMS, IR, and UV data. Antibacterial activity by the microdilution method and antibiofilm activity against P. aeruginosa were assessed. Compound 5 possesses significant
antibacterial activity, while the most potent antibiofilm agent is compound 2.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Natural Products",
title = "Antibacterial and Antibiofilm Activity of Flavonoid and Saponin Derivatives from Atriplex tatarica against Pseudomonas aeruginosa",
volume = "82",
pages = "1487-1495",
doi = "10.1021/acs.jnatprod.8b00970"
}
Stanković, J., Gođevac, D., Tešević, V., Dajić-Stevanović, Z., Ćirić, A., Soković, M.,& Novaković, M.. (2019). Antibacterial and Antibiofilm Activity of Flavonoid and Saponin Derivatives from Atriplex tatarica against Pseudomonas aeruginosa. in Journal of Natural Products
American Chemical Society (ACS)., 82, 1487-1495.
https://doi.org/10.1021/acs.jnatprod.8b00970
Stanković J, Gođevac D, Tešević V, Dajić-Stevanović Z, Ćirić A, Soković M, Novaković M. Antibacterial and Antibiofilm Activity of Flavonoid and Saponin Derivatives from Atriplex tatarica against Pseudomonas aeruginosa. in Journal of Natural Products. 2019;82:1487-1495.
doi:10.1021/acs.jnatprod.8b00970 .
Stanković, Jovana, Gođevac, Dejan, Tešević, Vele, Dajić-Stevanović, Zora, Ćirić, Ana, Soković, Marina, Novaković, Miroslav, "Antibacterial and Antibiofilm Activity of Flavonoid and Saponin Derivatives from Atriplex tatarica against Pseudomonas aeruginosa" in Journal of Natural Products, 82 (2019):1487-1495,
https://doi.org/10.1021/acs.jnatprod.8b00970 . .
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