TY  - JOUR
AU  - Assaleh, Mohamed H.
AU  - Božić, Aleksandra R.
AU  - Bjelogrlić, Snežana
AU  - Milošević, Milena D.
AU  - Simić, Milena R.
AU  - Marinković, Aleksandar D.
AU  - Cvijetić, Ilija
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3037
AB  - Thiocarbohydrazones (TCHs) and structurally related molecules are versatile organic compounds which exert antioxidant, anticancer, and other beneficial health effects. The combination of UV/Vis, NMR spectroscopy, and quantum chemical calculations was used to rationalize the experimentally observed increase in the radical scavenging activity upon the addition of water in DMSO solution of TCHs. Mono- and bis(salicylaldehyde) TCHs (compounds 1 and 2) undergo water-induced E-to-Z isomerization which is followed by disruption of intramolecular hydrogen bond, ground state destabilization, and 11 kcal/mol decrease in the bond dissociation enthalpy (BDE). Electron spin delocalization is more pronounced in Z-isomers of 1 and 2. On the other hand, 2-acetylpyridine TCHs (compounds 3 and 4) undergo thione-to-thiol tautomerism which also decreases the BDE and facilitates the hydrogen atom transfer to 2,2-diphenyl-1-picrylhydrazyl radical (DPPH∙). The appearance of thiolic –SH group as another reactive site toward free radicals improves the antioxidant activity of 3 and 4. The spin density of 3- and 4-thiol radicals is delocalized over the entire thiocarbohydrazide moiety compared to more localized spin of thione radicals. Additional stabilization of thiol radicals corroborates with the increased antioxidant activity. This study provides the new insights on the solution structure of TCHs, and also highlights the importance of solution structure determination when studying the structure-antioxidant relationships of isomerizable compounds.
PB  - Springer
T2  - Structural Chemistry
T1  - Water-induced isomerism of salicylaldehyde and 2-acetylpyridine mono- and bis-(thiocarbohydrazones) improves the antioxidant activity: spectroscopic and DFT study
VL  - 30
SP  - 2447
EP  - 2457
DO  - 10.1007/s11224-019-01371-4
ER  - 

@article{
author = "Assaleh, Mohamed H. and Božić, Aleksandra R. and Bjelogrlić, Snežana and Milošević, Milena D. and Simić, Milena R. and Marinković, Aleksandar D. and Cvijetić, Ilija",
year = "2019",
abstract = "Thiocarbohydrazones (TCHs) and structurally related molecules are versatile organic compounds which exert antioxidant, anticancer, and other beneficial health effects. The combination of UV/Vis, NMR spectroscopy, and quantum chemical calculations was used to rationalize the experimentally observed increase in the radical scavenging activity upon the addition of water in DMSO solution of TCHs. Mono- and bis(salicylaldehyde) TCHs (compounds 1 and 2) undergo water-induced E-to-Z isomerization which is followed by disruption of intramolecular hydrogen bond, ground state destabilization, and 11 kcal/mol decrease in the bond dissociation enthalpy (BDE). Electron spin delocalization is more pronounced in Z-isomers of 1 and 2. On the other hand, 2-acetylpyridine TCHs (compounds 3 and 4) undergo thione-to-thiol tautomerism which also decreases the BDE and facilitates the hydrogen atom transfer to 2,2-diphenyl-1-picrylhydrazyl radical (DPPH∙). The appearance of thiolic –SH group as another reactive site toward free radicals improves the antioxidant activity of 3 and 4. The spin density of 3- and 4-thiol radicals is delocalized over the entire thiocarbohydrazide moiety compared to more localized spin of thione radicals. Additional stabilization of thiol radicals corroborates with the increased antioxidant activity. This study provides the new insights on the solution structure of TCHs, and also highlights the importance of solution structure determination when studying the structure-antioxidant relationships of isomerizable compounds.",
publisher = "Springer",
journal = "Structural Chemistry",
title = "Water-induced isomerism of salicylaldehyde and 2-acetylpyridine mono- and bis-(thiocarbohydrazones) improves the antioxidant activity: spectroscopic and DFT study",
volume = "30",
pages = "2447-2457",
doi = "10.1007/s11224-019-01371-4"
}

Assaleh, M. H., Božić, A. R., Bjelogrlić, S., Milošević, M. D., Simić, M. R., Marinković, A. D.,& Cvijetić, I.. (2019). Water-induced isomerism of salicylaldehyde and 2-acetylpyridine mono- and bis-(thiocarbohydrazones) improves the antioxidant activity: spectroscopic and DFT study. in Structural Chemistry
Springer., 30, 2447-2457.
https://doi.org/10.1007/s11224-019-01371-4

Assaleh MH, Božić AR, Bjelogrlić S, Milošević MD, Simić MR, Marinković AD, Cvijetić I. Water-induced isomerism of salicylaldehyde and 2-acetylpyridine mono- and bis-(thiocarbohydrazones) improves the antioxidant activity: spectroscopic and DFT study. in Structural Chemistry. 2019;30:2447-2457.
doi:10.1007/s11224-019-01371-4 .

Assaleh, Mohamed H., Božić, Aleksandra R., Bjelogrlić, Snežana, Milošević, Milena D., Simić, Milena R., Marinković, Aleksandar D., Cvijetić, Ilija, "Water-induced isomerism of salicylaldehyde and 2-acetylpyridine mono- and bis-(thiocarbohydrazones) improves the antioxidant activity: spectroscopic and DFT study" in Structural Chemistry, 30 (2019):2447-2457,
https://doi.org/10.1007/s11224-019-01371-4 . .

TY  - DATA
AU  - Vlajic, Marina D
AU  - Trifunović, Snežana
AU  - Simić, Milena R.
AU  - Vujisić, Ljubodrag V.
AU  - Vučković, Ivan
AU  - Novaković, Miroslav
AU  - Nikolic-Mandic, Snezana D
AU  - Tešević, Vele
AU  - Vajs, Vlatka
AU  - Milosavljević, Slobodan
AU  - Mandić, Boris
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4466
AB  - Experimental details relating to the article: Mandić, B., Vlajic, M. D., Trifunović, S., Simić, M. R., Vujisić, L. V., Vučković, I., Novaković, M., Nikolic-Mandic, S. D., Tešević, V., Vajs, V.,& Milosavljević, S. (2015). Optimisation of isolation procedure for pyrrolizidine alkaloids from Rindera umbellata Bunge. Natural Product Research, 29(9), 887-890. https://doi.org/10.1080/14786419.2014.991929. Figure S1. Structures of monitored PAs from R. umbellata (1 - 6). Figure S2. Yields of PAs in relation to days of maceration in the methanol. Figure S3. Yields of PAs extracted with methanol, ethanol and sulphuric acid during four days at dark place and room temperature. Figure S4. Yields of PAs (1-6) in relation to molarity of sulphuric acid used for their extraction. Figure S5. Yields of PAs (1-6) in relation to days of maceration with 1 M sulphuric acid, at room temperature. Figure S6. Yields of PAs (1-6) in relation to days of ultrasonic assisted extraction with 1 M sulphuric acid. Figure S7. Yields of PAs (1-6) in relation to days of extraction with 1 M sulphuric acid by overhead rotary mixer.  Figure S8. Comparison of yields of PAs (1-6) accomplished after four days of maceration, three days of extraction by ultrasonic bath and overhead rotary mixer assisted extractions of plant material with 1M sulphuric acid. Figure S9. Yields of PAs (1-6) isolated from 1.00 g of the plant material (with 1M sulphuric acid during the extraction by overhead rotary mixer for three days) in relation to the volume (ml) of sulphuric acid. Figure S10. Yields of isolated PAs (1-6) in relation to pH values of aqueous solutions for alkaline extraction of PAs with CH2Cl2. Figure S11. Yields of isolated PAs in relation to the number of continuous alkaline re-extractions with CH2Cl2 at pH 9.
PB  - Taylor & Francis
T2  - Natural Product Research
T1  - Supplementary material for: "Optimisation of isolation procedure for pyrrolizidine alkaloids from Rindera umbellata Bunge"
DO  - 10.6084/m9.figshare.1276004.v2
ER  - 

@misc{
author = "Vlajic, Marina D and Trifunović, Snežana and Simić, Milena R. and Vujisić, Ljubodrag V. and Vučković, Ivan and Novaković, Miroslav and Nikolic-Mandic, Snezana D and Tešević, Vele and Vajs, Vlatka and Milosavljević, Slobodan and Mandić, Boris",
year = "2015",
abstract = "Experimental details relating to the article: Mandić, B., Vlajic, M. D., Trifunović, S., Simić, M. R., Vujisić, L. V., Vučković, I., Novaković, M., Nikolic-Mandic, S. D., Tešević, V., Vajs, V.,& Milosavljević, S. (2015). Optimisation of isolation procedure for pyrrolizidine alkaloids from Rindera umbellata Bunge. Natural Product Research, 29(9), 887-890. https://doi.org/10.1080/14786419.2014.991929. Figure S1. Structures of monitored PAs from R. umbellata (1 - 6). Figure S2. Yields of PAs in relation to days of maceration in the methanol. Figure S3. Yields of PAs extracted with methanol, ethanol and sulphuric acid during four days at dark place and room temperature. Figure S4. Yields of PAs (1-6) in relation to molarity of sulphuric acid used for their extraction. Figure S5. Yields of PAs (1-6) in relation to days of maceration with 1 M sulphuric acid, at room temperature. Figure S6. Yields of PAs (1-6) in relation to days of ultrasonic assisted extraction with 1 M sulphuric acid. Figure S7. Yields of PAs (1-6) in relation to days of extraction with 1 M sulphuric acid by overhead rotary mixer.  Figure S8. Comparison of yields of PAs (1-6) accomplished after four days of maceration, three days of extraction by ultrasonic bath and overhead rotary mixer assisted extractions of plant material with 1M sulphuric acid. Figure S9. Yields of PAs (1-6) isolated from 1.00 g of the plant material (with 1M sulphuric acid during the extraction by overhead rotary mixer for three days) in relation to the volume (ml) of sulphuric acid. Figure S10. Yields of isolated PAs (1-6) in relation to pH values of aqueous solutions for alkaline extraction of PAs with CH2Cl2. Figure S11. Yields of isolated PAs in relation to the number of continuous alkaline re-extractions with CH2Cl2 at pH 9.",
publisher = "Taylor & Francis",
journal = "Natural Product Research",
title = "Supplementary material for: "Optimisation of isolation procedure for pyrrolizidine alkaloids from Rindera umbellata Bunge"",
doi = "10.6084/m9.figshare.1276004.v2"
}

Vlajic, M. D., Trifunović, S., Simić, M. R., Vujisić, L. V., Vučković, I., Novaković, M., Nikolic-Mandic, S. D., Tešević, V., Vajs, V., Milosavljević, S.,& Mandić, B.. (2015). Supplementary material for: "Optimisation of isolation procedure for pyrrolizidine alkaloids from Rindera umbellata Bunge". in Natural Product Research
Taylor & Francis..
https://doi.org/10.6084/m9.figshare.1276004.v2

Vlajic MD, Trifunović S, Simić MR, Vujisić LV, Vučković I, Novaković M, Nikolic-Mandic SD, Tešević V, Vajs V, Milosavljević S, Mandić B. Supplementary material for: "Optimisation of isolation procedure for pyrrolizidine alkaloids from Rindera umbellata Bunge". in Natural Product Research. 2015;.
doi:10.6084/m9.figshare.1276004.v2 .

Vlajic, Marina D, Trifunović, Snežana, Simić, Milena R., Vujisić, Ljubodrag V., Vučković, Ivan, Novaković, Miroslav, Nikolic-Mandic, Snezana D, Tešević, Vele, Vajs, Vlatka, Milosavljević, Slobodan, Mandić, Boris, "Supplementary material for: "Optimisation of isolation procedure for pyrrolizidine alkaloids from Rindera umbellata Bunge"" in Natural Product Research (2015),
https://doi.org/10.6084/m9.figshare.1276004.v2 . .

TY  - JOUR
AU  - Mandić, Boris
AU  - Vlajic, Marina D
AU  - Trifunović, Snežana
AU  - Simić, Milena R.
AU  - Vujisić, Ljubodrag V.
AU  - Vučković, Ivan
AU  - Novaković, Miroslav
AU  - Nikolic-Mandic, Snezana D
AU  - Tešević, Vele
AU  - Vajs, Vlatka
AU  - Milosavljević, Slobodan
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1780
AB  - Procedure for isolation of pyrrolizidine alkaloids (PAs) from Rindera umbellata Bunge plant species was optimised. Different extraction media (methanol, ethanol and sulphuric acid), concentration and volume of sulphuric acid, pH of PA solution for alkaline extraction, extraction time and techniques (maceration, ultrasonic and overhead rotary mixer assisted extraction) were investigated. The yields of six PAs (7-angeloyl heliotridane, 7-angeloyl heliotridine, lindelofine, 7-angeloyl rinderine, punctanecine and heliosupine) were monitored by GC-MS/FID. The best results for the isolation all of six PAs were obtained when the extraction was performed with 1M sulphuric acid (30mL per 1.00g of dried sample) by overhead rotary mixer during three days. Optimal pH value for alkaline extraction of PAs with CH2Cl2 was 9, and the extraction should be performed with four portions of 30mL of CH2Cl2. This procedure could be also useful for a plant sample preparation for GC and LC analyses of PAs.
PB  - Taylor & Francis Ltd, Abingdon
T2  - Natural Product Research
T1  - Optimisation of isolation procedure for pyrrolizidine alkaloids from Rindera umbellata Bunge
VL  - 29
IS  - 9
SP  - 887
EP  - 890
DO  - 10.1080/14786419.2014.991929
ER  - 

@article{
author = "Mandić, Boris and Vlajic, Marina D and Trifunović, Snežana and Simić, Milena R. and Vujisić, Ljubodrag V. and Vučković, Ivan and Novaković, Miroslav and Nikolic-Mandic, Snezana D and Tešević, Vele and Vajs, Vlatka and Milosavljević, Slobodan",
year = "2015",
abstract = "Procedure for isolation of pyrrolizidine alkaloids (PAs) from Rindera umbellata Bunge plant species was optimised. Different extraction media (methanol, ethanol and sulphuric acid), concentration and volume of sulphuric acid, pH of PA solution for alkaline extraction, extraction time and techniques (maceration, ultrasonic and overhead rotary mixer assisted extraction) were investigated. The yields of six PAs (7-angeloyl heliotridane, 7-angeloyl heliotridine, lindelofine, 7-angeloyl rinderine, punctanecine and heliosupine) were monitored by GC-MS/FID. The best results for the isolation all of six PAs were obtained when the extraction was performed with 1M sulphuric acid (30mL per 1.00g of dried sample) by overhead rotary mixer during three days. Optimal pH value for alkaline extraction of PAs with CH2Cl2 was 9, and the extraction should be performed with four portions of 30mL of CH2Cl2. This procedure could be also useful for a plant sample preparation for GC and LC analyses of PAs.",
publisher = "Taylor & Francis Ltd, Abingdon",
journal = "Natural Product Research",
title = "Optimisation of isolation procedure for pyrrolizidine alkaloids from Rindera umbellata Bunge",
volume = "29",
number = "9",
pages = "887-890",
doi = "10.1080/14786419.2014.991929"
}

Mandić, B., Vlajic, M. D., Trifunović, S., Simić, M. R., Vujisić, L. V., Vučković, I., Novaković, M., Nikolic-Mandic, S. D., Tešević, V., Vajs, V.,& Milosavljević, S.. (2015). Optimisation of isolation procedure for pyrrolizidine alkaloids from Rindera umbellata Bunge. in Natural Product Research
Taylor & Francis Ltd, Abingdon., 29(9), 887-890.
https://doi.org/10.1080/14786419.2014.991929

Mandić B, Vlajic MD, Trifunović S, Simić MR, Vujisić LV, Vučković I, Novaković M, Nikolic-Mandic SD, Tešević V, Vajs V, Milosavljević S. Optimisation of isolation procedure for pyrrolizidine alkaloids from Rindera umbellata Bunge. in Natural Product Research. 2015;29(9):887-890.
doi:10.1080/14786419.2014.991929 .

Mandić, Boris, Vlajic, Marina D, Trifunović, Snežana, Simić, Milena R., Vujisić, Ljubodrag V., Vučković, Ivan, Novaković, Miroslav, Nikolic-Mandic, Snezana D, Tešević, Vele, Vajs, Vlatka, Milosavljević, Slobodan, "Optimisation of isolation procedure for pyrrolizidine alkaloids from Rindera umbellata Bunge" in Natural Product Research, 29, no. 9 (2015):887-890,
https://doi.org/10.1080/14786419.2014.991929 . .

TY  - JOUR
AU  - Mandić, Boris
AU  - Simić, Milena R.
AU  - Vučković, Ivan
AU  - Vujisić, Ljubodrag V.
AU  - Novaković, Miroslav
AU  - Trifunović, Snežana
AU  - Nikolic-Mandic, Snezana D.
AU  - Tešević, Vele
AU  - Vajs, Vlatka
AU  - Milosavljević, Slobodan
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1241
AB  - The examination of the aerial parts, roots, and seeds of the endemic plant Rindera umbellata is reported in this paper for the first time. Phytochemical investigation of R. umbellata led to the isolation and characterization of ten pyrrolizidine alkaloids and eleven fatty acids in the form of triglycerides. Pyrrolizidine alkaloids 1-9 were found in the aerial parts, 7 and 8 in the roots, and 6-10, together with eleven fatty acids, in the seeds of this plant species. The structures of compounds 1-10 were established based on spectroscopic studies (H-1- and C-13-NMR, 2D NMR, IR and CI-MS). After trans-esterification, methyl esters of the fatty acids were analyzed using GC-MS. The effect of lindelofine-N-oxide (7) on tubulin polymerization was determined.
PB  - MDPI
T2  - Molecules
T1  - Pyrrolizidine Alkaloids and Fatty Acids from the Endemic Plant Species Rindera umbellata and the Effect of Lindelofine-N-oxide on Tubulin Polymerization
VL  - 18
IS  - 9
SP  - 10694
EP  - 10706
DO  - 10.3390/molecules180910694
ER  - 

@article{
author = "Mandić, Boris and Simić, Milena R. and Vučković, Ivan and Vujisić, Ljubodrag V. and Novaković, Miroslav and Trifunović, Snežana and Nikolic-Mandic, Snezana D. and Tešević, Vele and Vajs, Vlatka and Milosavljević, Slobodan",
year = "2013",
abstract = "The examination of the aerial parts, roots, and seeds of the endemic plant Rindera umbellata is reported in this paper for the first time. Phytochemical investigation of R. umbellata led to the isolation and characterization of ten pyrrolizidine alkaloids and eleven fatty acids in the form of triglycerides. Pyrrolizidine alkaloids 1-9 were found in the aerial parts, 7 and 8 in the roots, and 6-10, together with eleven fatty acids, in the seeds of this plant species. The structures of compounds 1-10 were established based on spectroscopic studies (H-1- and C-13-NMR, 2D NMR, IR and CI-MS). After trans-esterification, methyl esters of the fatty acids were analyzed using GC-MS. The effect of lindelofine-N-oxide (7) on tubulin polymerization was determined.",
publisher = "MDPI",
journal = "Molecules",
title = "Pyrrolizidine Alkaloids and Fatty Acids from the Endemic Plant Species Rindera umbellata and the Effect of Lindelofine-N-oxide on Tubulin Polymerization",
volume = "18",
number = "9",
pages = "10694-10706",
doi = "10.3390/molecules180910694"
}

Mandić, B., Simić, M. R., Vučković, I., Vujisić, L. V., Novaković, M., Trifunović, S., Nikolic-Mandic, S. D., Tešević, V., Vajs, V.,& Milosavljević, S.. (2013). Pyrrolizidine Alkaloids and Fatty Acids from the Endemic Plant Species Rindera umbellata and the Effect of Lindelofine-N-oxide on Tubulin Polymerization. in Molecules
MDPI., 18(9), 10694-10706.
https://doi.org/10.3390/molecules180910694

Mandić B, Simić MR, Vučković I, Vujisić LV, Novaković M, Trifunović S, Nikolic-Mandic SD, Tešević V, Vajs V, Milosavljević S. Pyrrolizidine Alkaloids and Fatty Acids from the Endemic Plant Species Rindera umbellata and the Effect of Lindelofine-N-oxide on Tubulin Polymerization. in Molecules. 2013;18(9):10694-10706.
doi:10.3390/molecules180910694 .

Mandić, Boris, Simić, Milena R., Vučković, Ivan, Vujisić, Ljubodrag V., Novaković, Miroslav, Trifunović, Snežana, Nikolic-Mandic, Snezana D., Tešević, Vele, Vajs, Vlatka, Milosavljević, Slobodan, "Pyrrolizidine Alkaloids and Fatty Acids from the Endemic Plant Species Rindera umbellata and the Effect of Lindelofine-N-oxide on Tubulin Polymerization" in Molecules, 18, no. 9 (2013):10694-10706,
https://doi.org/10.3390/molecules180910694 . .

TY  - JOUR
AU  - Tasić, Gordana
AU  - Simić, Milena R.
AU  - Popović, Stanimir
AU  - Husinec, Suren
AU  - Maslak, Veselin
AU  - Savić, Vladimir
PY  - 2013
UR  - http://farfar.pharmacy.bg.ac.rs/handle/123456789/1973
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3503
AB  - Double bond migration in N-allylindoles has been investigated as a method to access N-vinyl derivatives of this heterocycle. The optimal reaction conditions employed t-BuOK or NaH in DMSO as the solvent at room temperature to afford the products in yields ranging from 51 to 99%. Although in some cases a high degree of stereoselectivity was observed, preferential formation of either the Z- or E-isomer was not predictable. The developed methodology was employed in the synthesis of (+/-)-debromoarborescidine B.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron-Asymmetry
T1  - Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (+/-)-debromoarborescidine B
VL  - 54
IS  - 34
SP  - 4536
EP  - 4539
DO  - 10.1016/j.tetlet.2013.06.069
ER  - 

@article{
author = "Tasić, Gordana and Simić, Milena R. and Popović, Stanimir and Husinec, Suren and Maslak, Veselin and Savić, Vladimir",
year = "2013",
abstract = "Double bond migration in N-allylindoles has been investigated as a method to access N-vinyl derivatives of this heterocycle. The optimal reaction conditions employed t-BuOK or NaH in DMSO as the solvent at room temperature to afford the products in yields ranging from 51 to 99%. Although in some cases a high degree of stereoselectivity was observed, preferential formation of either the Z- or E-isomer was not predictable. The developed methodology was employed in the synthesis of (+/-)-debromoarborescidine B.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron-Asymmetry",
title = "Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (+/-)-debromoarborescidine B",
volume = "54",
number = "34",
pages = "4536-4539",
doi = "10.1016/j.tetlet.2013.06.069"
}

Tasić, G., Simić, M. R., Popović, S., Husinec, S., Maslak, V.,& Savić, V.. (2013). Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (+/-)-debromoarborescidine B. in Tetrahedron-Asymmetry
Oxford : Pergamon-Elsevier Science Ltd., 54(34), 4536-4539.
https://doi.org/10.1016/j.tetlet.2013.06.069

Tasić G, Simić MR, Popović S, Husinec S, Maslak V, Savić V. Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (+/-)-debromoarborescidine B. in Tetrahedron-Asymmetry. 2013;54(34):4536-4539.
doi:10.1016/j.tetlet.2013.06.069 .

Tasić, Gordana, Simić, Milena R., Popović, Stanimir, Husinec, Suren, Maslak, Veselin, Savić, Vladimir, "Indirect N-vinylation of indoles via isomerisation of N-allyl derivatives: synthesis of (+/-)-debromoarborescidine B" in Tetrahedron-Asymmetry, 54, no. 34 (2013):4536-4539,
https://doi.org/10.1016/j.tetlet.2013.06.069 . .

TY  - JOUR
AU  - Husinec, Suren
AU  - Petković, Miloš
AU  - Savić, Vladimir
AU  - Simić, Milena
PY  - 2012
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4173
AB  - pi-Allylpalladium intermediates are known to participate efficiently in transformations involving nucleophilic species. Exploring these processes, we have developed a method for the preparation of allyl acetates via palladium-catalysed functionalisation of allenes and 1,3-dienes. Reactions of aryl iodides with either of these two classes of compounds and excess sodium acetate in the presence of Pd(OAc) (2) and Ph3P as the catalytic system afforded the respective allyl acetates in moderate to good yields. The scope of this process has been investigated. The described method is an addition to the synthetic repertoire for the preparation of allyl acetates, and may be useful, in particular, for the synthesis of structurally complex compounds of this type.
PB  - Stuttgart : Georg Thieme Verlag Kg
T2  - Synthesis
T1  - Synthesis of Allyl Acetates via Palladium-Catalysed Functionalisation of Allenes and 1,3-Dienes
VL  - 44
IS  - 3
SP  - 399
EP  - 408
DO  - 10.1055/s-0031-1289658
ER  - 

@article{
author = "Husinec, Suren and Petković, Miloš and Savić, Vladimir and Simić, Milena",
year = "2012",
abstract = "pi-Allylpalladium intermediates are known to participate efficiently in transformations involving nucleophilic species. Exploring these processes, we have developed a method for the preparation of allyl acetates via palladium-catalysed functionalisation of allenes and 1,3-dienes. Reactions of aryl iodides with either of these two classes of compounds and excess sodium acetate in the presence of Pd(OAc) (2) and Ph3P as the catalytic system afforded the respective allyl acetates in moderate to good yields. The scope of this process has been investigated. The described method is an addition to the synthetic repertoire for the preparation of allyl acetates, and may be useful, in particular, for the synthesis of structurally complex compounds of this type.",
publisher = "Stuttgart : Georg Thieme Verlag Kg",
journal = "Synthesis",
title = "Synthesis of Allyl Acetates via Palladium-Catalysed Functionalisation of Allenes and 1,3-Dienes",
volume = "44",
number = "3",
pages = "399-408",
doi = "10.1055/s-0031-1289658"
}

Husinec, S., Petković, M., Savić, V.,& Simić, M.. (2012). Synthesis of Allyl Acetates via Palladium-Catalysed Functionalisation of Allenes and 1,3-Dienes. in Synthesis
Stuttgart : Georg Thieme Verlag Kg., 44(3), 399-408.
https://doi.org/10.1055/s-0031-1289658

Husinec S, Petković M, Savić V, Simić M. Synthesis of Allyl Acetates via Palladium-Catalysed Functionalisation of Allenes and 1,3-Dienes. in Synthesis. 2012;44(3):399-408.
doi:10.1055/s-0031-1289658 .

Husinec, Suren, Petković, Miloš, Savić, Vladimir, Simić, Milena, "Synthesis of Allyl Acetates via Palladium-Catalysed Functionalisation of Allenes and 1,3-Dienes" in Synthesis, 44, no. 3 (2012):399-408,
https://doi.org/10.1055/s-0031-1289658 . .

TY  - JOUR
AU  - Husinec, Suren
AU  - Savić, Vladimir
AU  - Simić, Milena R.
AU  - Tešević, Vele
AU  - Vidović, Dragoslav
PY  - 2011
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1342
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3505
UR  - http://farfar.pharmacy.bg.ac.rs/handle/123456789/1567
AB  - Annulation processes of isoquinoline and p-carboline compounds have been investigated leading to synthetic routes for the preparation of 8-oxoprotoberberine derivatives. The key steps combined a diene formation/Diels-Alder cycloaddition reaction to afford the targeted polycyclic skeletons. Further oxidative transformations of the cycloadducts produced the 8-oxoprotoberberine type products. The alkaloids of this class are important natural products with a wide range of biological activity and the synthethic methodology described in this paper could prove to be useful for the preparation of the D-ring functionalised derivatives.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron Letters
T1  - Annulations of isoquinoline and beta-carboline ring systems: synthesis of 8-oxoprotoberberine derivatives
VL  - 52
IS  - 21
SP  - 2733
EP  - 2736
DO  - 10.1016/j.tetlet.2011.03.085
ER  - 

@article{
author = "Husinec, Suren and Savić, Vladimir and Simić, Milena R. and Tešević, Vele and Vidović, Dragoslav",
year = "2011",
abstract = "Annulation processes of isoquinoline and p-carboline compounds have been investigated leading to synthetic routes for the preparation of 8-oxoprotoberberine derivatives. The key steps combined a diene formation/Diels-Alder cycloaddition reaction to afford the targeted polycyclic skeletons. Further oxidative transformations of the cycloadducts produced the 8-oxoprotoberberine type products. The alkaloids of this class are important natural products with a wide range of biological activity and the synthethic methodology described in this paper could prove to be useful for the preparation of the D-ring functionalised derivatives.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron Letters",
title = "Annulations of isoquinoline and beta-carboline ring systems: synthesis of 8-oxoprotoberberine derivatives",
volume = "52",
number = "21",
pages = "2733-2736",
doi = "10.1016/j.tetlet.2011.03.085"
}

Husinec, S., Savić, V., Simić, M. R., Tešević, V.,& Vidović, D.. (2011). Annulations of isoquinoline and beta-carboline ring systems: synthesis of 8-oxoprotoberberine derivatives. in Tetrahedron Letters
Oxford : Pergamon-Elsevier Science Ltd., 52(21), 2733-2736.
https://doi.org/10.1016/j.tetlet.2011.03.085

Husinec S, Savić V, Simić MR, Tešević V, Vidović D. Annulations of isoquinoline and beta-carboline ring systems: synthesis of 8-oxoprotoberberine derivatives. in Tetrahedron Letters. 2011;52(21):2733-2736.
doi:10.1016/j.tetlet.2011.03.085 .

Husinec, Suren, Savić, Vladimir, Simić, Milena R., Tešević, Vele, Vidović, Dragoslav, "Annulations of isoquinoline and beta-carboline ring systems: synthesis of 8-oxoprotoberberine derivatives" in Tetrahedron Letters, 52, no. 21 (2011):2733-2736,
https://doi.org/10.1016/j.tetlet.2011.03.085 . .

TY  - JOUR
AU  - Mandić, Boris
AU  - Gođevac, Dejan
AU  - Beškoski, Vladimir
AU  - Simić, Milena R.
AU  - Trifunović, Snežana
AU  - Tešević, Vele
AU  - Vajs, Vlatka
AU  - Milosavljević, Slobodan
PY  - 2009
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/502
AB  - The genus Senecio (family Asteraceae) is one of the largest in the world. It comprises about 1100 species which are the rich source of pyrrolizidine alkaloids. Plants containing pyrrolizidine alkaloids are among the most important sources of human and animal exposure to plant toxins and carcinogens. The pyrrolizidine alkaloids of seven Senecio species (S. erucifolius, S. othonnae, S. wagneri, S. subalpinus, S. carpathicus, S. paludosus and S. rupestris) were studied. Fourteen alkaloids were isolated and their structures determined from spectroscopic data (1H- and 13C-NMR, IR and MS). Five of them were identified in S. erucifolius, four in S. othonnae, two in S. wagneri, four in S. subalpinus, two in S. carpathicus, three in S. paludosus and three in S. rupestris. Seven pyrrolizidine alkaloids were found for the first time in particular species. The results have chemotaxonomic importance. The cytotoxic activity and antimicrobial activity of some alkaloids were also studied.
AB  - Jedan od najbrojnijih rodova na svetu je rod Senecio (familija Asteraceae). Obuhvata oko 1100 vrsta koje predstavljaju bogat izvor pirolizidinskih alkaloida. Najznačajnija izloženost ljudi i životinja biljnim toksinima i karcinogenima potiče od biljaka koje sadrže pirolizidinske alkaloide. U ovom radu izolovani su pirolizidinski alkaloidi iz sedam vrsta roda Senecio (S. erucifolius, S. othonnae, S. wagneri, S. subalpinus, S. carpathicus, S. paludosus i S. rupestris), a njihove strukture određene na bazi spektroskopskih podataka (1H- i 13C-NMR, IR i MS). Izolovano je ukupno 14 alkaloida, pet iz S. erucifolius, četiri iz S. othonnae, dva iz S. wagneri, četiri iz S. subalpinus, dva iz S. carpathicus, tri iz S. paludosus i tri iz S. rupestris. Sedam pirolizidinskih alkaloida je po prvi put izolovano iz nekih pojedinačnih vrsta. Dobijeni rezultati imaju hemotaksonomski značaj. Ispitana je citotoksičnost i antimikrobna aktivnost izolovanih alkaloida.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Pyrrolizidine alkaloids from seven wild-growing Senecio species in Serbia and Montenegro
T1  - Pirolizidinski alkaloidi iz sedam samoniklih biljnih vrsta roda Senecio koje rastu u Srbiji i Crnoj Gori
VL  - 74
IS  - 1
SP  - 27
EP  - 34
DO  - 10.2298/JSC0901027M
ER  - 

@article{
author = "Mandić, Boris and Gođevac, Dejan and Beškoski, Vladimir and Simić, Milena R. and Trifunović, Snežana and Tešević, Vele and Vajs, Vlatka and Milosavljević, Slobodan",
year = "2009",
abstract = "The genus Senecio (family Asteraceae) is one of the largest in the world. It comprises about 1100 species which are the rich source of pyrrolizidine alkaloids. Plants containing pyrrolizidine alkaloids are among the most important sources of human and animal exposure to plant toxins and carcinogens. The pyrrolizidine alkaloids of seven Senecio species (S. erucifolius, S. othonnae, S. wagneri, S. subalpinus, S. carpathicus, S. paludosus and S. rupestris) were studied. Fourteen alkaloids were isolated and their structures determined from spectroscopic data (1H- and 13C-NMR, IR and MS). Five of them were identified in S. erucifolius, four in S. othonnae, two in S. wagneri, four in S. subalpinus, two in S. carpathicus, three in S. paludosus and three in S. rupestris. Seven pyrrolizidine alkaloids were found for the first time in particular species. The results have chemotaxonomic importance. The cytotoxic activity and antimicrobial activity of some alkaloids were also studied., Jedan od najbrojnijih rodova na svetu je rod Senecio (familija Asteraceae). Obuhvata oko 1100 vrsta koje predstavljaju bogat izvor pirolizidinskih alkaloida. Najznačajnija izloženost ljudi i životinja biljnim toksinima i karcinogenima potiče od biljaka koje sadrže pirolizidinske alkaloide. U ovom radu izolovani su pirolizidinski alkaloidi iz sedam vrsta roda Senecio (S. erucifolius, S. othonnae, S. wagneri, S. subalpinus, S. carpathicus, S. paludosus i S. rupestris), a njihove strukture određene na bazi spektroskopskih podataka (1H- i 13C-NMR, IR i MS). Izolovano je ukupno 14 alkaloida, pet iz S. erucifolius, četiri iz S. othonnae, dva iz S. wagneri, četiri iz S. subalpinus, dva iz S. carpathicus, tri iz S. paludosus i tri iz S. rupestris. Sedam pirolizidinskih alkaloida je po prvi put izolovano iz nekih pojedinačnih vrsta. Dobijeni rezultati imaju hemotaksonomski značaj. Ispitana je citotoksičnost i antimikrobna aktivnost izolovanih alkaloida.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Pyrrolizidine alkaloids from seven wild-growing Senecio species in Serbia and Montenegro, Pirolizidinski alkaloidi iz sedam samoniklih biljnih vrsta roda Senecio koje rastu u Srbiji i Crnoj Gori",
volume = "74",
number = "1",
pages = "27-34",
doi = "10.2298/JSC0901027M"
}

Mandić, B., Gođevac, D., Beškoski, V., Simić, M. R., Trifunović, S., Tešević, V., Vajs, V.,& Milosavljević, S.. (2009). Pyrrolizidine alkaloids from seven wild-growing Senecio species in Serbia and Montenegro. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 74(1), 27-34.
https://doi.org/10.2298/JSC0901027M

Mandić B, Gođevac D, Beškoski V, Simić MR, Trifunović S, Tešević V, Vajs V, Milosavljević S. Pyrrolizidine alkaloids from seven wild-growing Senecio species in Serbia and Montenegro. in Journal of the Serbian Chemical Society. 2009;74(1):27-34.
doi:10.2298/JSC0901027M .

Mandić, Boris, Gođevac, Dejan, Beškoski, Vladimir, Simić, Milena R., Trifunović, Snežana, Tešević, Vele, Vajs, Vlatka, Milosavljević, Slobodan, "Pyrrolizidine alkaloids from seven wild-growing Senecio species in Serbia and Montenegro" in Journal of the Serbian Chemical Society, 74, no. 1 (2009):27-34,
https://doi.org/10.2298/JSC0901027M . .

TY  - JOUR
AU  - Došlov-Kokoruš, Z R
AU  - Ivanović, I D
AU  - Simić, Milena R.
AU  - Vajs, Vlatka
AU  - Kovačević, N N
PY  - 2006
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2781
AB  - The aporphine alkaloid magnoflorine, known as a constituent of Asian Epimedium species, was isolated for the first time from the wild growing European species, Epimedium alpinum L. Identification was done by comparison with literature data. The HPLC method was applied for the determination of the content of the alkaloid in methanolic extracts of plant material. The underground part of E. alpinum contains 1-2 % of magnoflorine, while its content in methanolic extracts was 9.2-11.8 %. The aerial part of the plant contains less alkaloid (0.06-0.12 %), while the magnoflorine content in methanolic extracts of the aerial part was 0.4-0.8 %. Probably, the high content of magnoflorine in the methanolic extracts of underground parts of E. alpinum influences its dose-dependent cytotoxic activity (300 μg/ml; 39 % survival of cells in an experimental K562 cell culture).
AB  - Aporfinski alkaloid magnoflorin, poznat kao sastojak drugih vrsta roda Epimedium, po prvi put je izolovan iz evropske vrste Epimedium alpinum L. i identifikovan pore|ewem sa literaturnim podacima. Ovo jediwewe je kori{}eno kao standard u HPLC analizi metanolnih ekstrakata E. alpinum. Sadr`aj magnoflorina je znatno vi- {i u ekstraktima podzemnih organa (9,2–11,8 %, {to odgovara sadr`aju od 1–2 % magnoflorina u biqnom materijalu), nego u ekstraktima nadzemnih organa prevolca (0,4–0,8 %, {to odgovara sadr`aju od 0,06–0,12 % magnoflorina u biqnom materijalu). Sasvim je verovatno da je potvr|ena citotoksi~na aktivnost metanolnog ekstrakta podzemnih organa (300 g/ml; 39 % pre`ivelih }elija K562 kulture maligno-transformisanih }elija), kao i imunomodulatorna aktivnost, povezana sa visokom koncentracijom ovog alkaloida u ispitivanom ekstraktu.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - The HPLC determination of the content of magnoflorine in Epimedium alpinum L.
T1  - HPLC одређивање садржаја магнофлорина у преволцу Epimedium alpinum L.
VL  - 71
IS  - 3
SP  - 251
EP  - 255
DO  - 10.2298/JSC0603251D
ER  - 

@article{
author = "Došlov-Kokoruš, Z R and Ivanović, I D and Simić, Milena R. and Vajs, Vlatka and Kovačević, N N",
year = "2006",
abstract = "The aporphine alkaloid magnoflorine, known as a constituent of Asian Epimedium species, was isolated for the first time from the wild growing European species, Epimedium alpinum L. Identification was done by comparison with literature data. The HPLC method was applied for the determination of the content of the alkaloid in methanolic extracts of plant material. The underground part of E. alpinum contains 1-2 % of magnoflorine, while its content in methanolic extracts was 9.2-11.8 %. The aerial part of the plant contains less alkaloid (0.06-0.12 %), while the magnoflorine content in methanolic extracts of the aerial part was 0.4-0.8 %. Probably, the high content of magnoflorine in the methanolic extracts of underground parts of E. alpinum influences its dose-dependent cytotoxic activity (300 μg/ml; 39 % survival of cells in an experimental K562 cell culture)., Aporfinski alkaloid magnoflorin, poznat kao sastojak drugih vrsta roda Epimedium, po prvi put je izolovan iz evropske vrste Epimedium alpinum L. i identifikovan pore|ewem sa literaturnim podacima. Ovo jediwewe je kori{}eno kao standard u HPLC analizi metanolnih ekstrakata E. alpinum. Sadr`aj magnoflorina je znatno vi- {i u ekstraktima podzemnih organa (9,2–11,8 %, {to odgovara sadr`aju od 1–2 % magnoflorina u biqnom materijalu), nego u ekstraktima nadzemnih organa prevolca (0,4–0,8 %, {to odgovara sadr`aju od 0,06–0,12 % magnoflorina u biqnom materijalu). Sasvim je verovatno da je potvr|ena citotoksi~na aktivnost metanolnog ekstrakta podzemnih organa (300 g/ml; 39 % pre`ivelih }elija K562 kulture maligno-transformisanih }elija), kao i imunomodulatorna aktivnost, povezana sa visokom koncentracijom ovog alkaloida u ispitivanom ekstraktu.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "The HPLC determination of the content of magnoflorine in Epimedium alpinum L., HPLC одређивање садржаја магнофлорина у преволцу Epimedium alpinum L.",
volume = "71",
number = "3",
pages = "251-255",
doi = "10.2298/JSC0603251D"
}

Došlov-Kokoruš, Z. R., Ivanović, I. D., Simić, M. R., Vajs, V.,& Kovačević, N. N.. (2006). The HPLC determination of the content of magnoflorine in Epimedium alpinum L.. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 71(3), 251-255.
https://doi.org/10.2298/JSC0603251D

Došlov-Kokoruš ZR, Ivanović ID, Simić MR, Vajs V, Kovačević NN. The HPLC determination of the content of magnoflorine in Epimedium alpinum L.. in Journal of the Serbian Chemical Society. 2006;71(3):251-255.
doi:10.2298/JSC0603251D .

Došlov-Kokoruš, Z R, Ivanović, I D, Simić, Milena R., Vajs, Vlatka, Kovačević, N N, "The HPLC determination of the content of magnoflorine in Epimedium alpinum L." in Journal of the Serbian Chemical Society, 71, no. 3 (2006):251-255,
https://doi.org/10.2298/JSC0603251D . .