TY  - JOUR
AU  - Novaković, Miroslav M.
AU  - Ilić-Tomić, Tatjana
AU  - Đorđević, Iris
AU  - Anđelković, Boban D.
AU  - Tešević, Vele
AU  - Milosavljević, Slobodan M.
AU  - Asakawa, Yoshinori
PY  - 2023
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6259
AB  - Bisbibenzyls are specialized metabolites found exclusively in liverworts, until recently; they represent chemical markers of liverworts. Their occurrence in vascular plants was noticed in 2007, when they were found in Primula veris subsp. macrocalyx from Russia. This report prompted us to chemically analyze the two most common Serbian Primula species, P. veris subsp. columnae and P. acaulis, in order to determine the presence of bisbibenzyls in them. Our study revealed nine structurally distinct bisbibenzyls (1–9), identified based on 1D and 2D NMR, IR, UV and HRESIMS data. Among them were five previously undescribed compounds (2–6). The remaining com­ pounds found and previously described in the literature were: the bisbibenzyls riccardin C (1), isoperrottetin A (7), isoplagiochin E (8) and 11-O-demethylmarchantin I (9), as well as 4-hydroxyphenylmethylketone (10) and 4-hydroxy-3-methoxyphenylmethylketone (11). Riccardin C was the most dominant bisbibenzyl in both species studied. Previously, it was the first bisbibenzyl found in vascular plants (P. veris subsp. macrocalyx). An assessment of the cytotoxic activity of the isolated compounds against A549 lung cancer and healthy MRC5 cell lines was also the subject of our study. Compounds 6 and 9 exhibited significant cytotoxic activity expressed by IC50 values of 12 μM, but the selectivity was not satisfactory.
PB  - Elsevier
T2  - Phytochemistry
T1  - Bisbibenzyls from Serbian Primula veris subsp. Columnae (Ten.) Lȕdi and P. acaulis (L.) L
VL  - 212
EP  - 113719
DO  - 10.1016/j.phytochem.2023.113719
ER  - 

@article{
author = "Novaković, Miroslav M. and Ilić-Tomić, Tatjana and Đorđević, Iris and Anđelković, Boban D. and Tešević, Vele and Milosavljević, Slobodan M. and Asakawa, Yoshinori",
year = "2023, 2023",
abstract = "Bisbibenzyls are specialized metabolites found exclusively in liverworts, until recently; they represent chemical markers of liverworts. Their occurrence in vascular plants was noticed in 2007, when they were found in Primula veris subsp. macrocalyx from Russia. This report prompted us to chemically analyze the two most common Serbian Primula species, P. veris subsp. columnae and P. acaulis, in order to determine the presence of bisbibenzyls in them. Our study revealed nine structurally distinct bisbibenzyls (1–9), identified based on 1D and 2D NMR, IR, UV and HRESIMS data. Among them were five previously undescribed compounds (2–6). The remaining com­ pounds found and previously described in the literature were: the bisbibenzyls riccardin C (1), isoperrottetin A (7), isoplagiochin E (8) and 11-O-demethylmarchantin I (9), as well as 4-hydroxyphenylmethylketone (10) and 4-hydroxy-3-methoxyphenylmethylketone (11). Riccardin C was the most dominant bisbibenzyl in both species studied. Previously, it was the first bisbibenzyl found in vascular plants (P. veris subsp. macrocalyx). An assessment of the cytotoxic activity of the isolated compounds against A549 lung cancer and healthy MRC5 cell lines was also the subject of our study. Compounds 6 and 9 exhibited significant cytotoxic activity expressed by IC50 values of 12 μM, but the selectivity was not satisfactory.",
publisher = "Elsevier",
journal = "Phytochemistry",
title = "Bisbibenzyls from Serbian Primula veris subsp. Columnae (Ten.) Lȕdi and P. acaulis (L.) L",
volume = "212",
pages = "113719",
doi = "10.1016/j.phytochem.2023.113719"
}

Novaković, M. M., Ilić-Tomić, T., Đorđević, I., Anđelković, B. D., Tešević, V., Milosavljević, S. M.,& Asakawa, Y.. (2023). Bisbibenzyls from Serbian Primula veris subsp. Columnae (Ten.) Lȕdi and P. acaulis (L.) L. in Phytochemistry
Elsevier., 212.
https://doi.org/10.1016/j.phytochem.2023.113719

Novaković MM, Ilić-Tomić T, Đorđević I, Anđelković BD, Tešević V, Milosavljević SM, Asakawa Y. Bisbibenzyls from Serbian Primula veris subsp. Columnae (Ten.) Lȕdi and P. acaulis (L.) L. in Phytochemistry. 2023;212:null-113719.
doi:10.1016/j.phytochem.2023.113719 .

Novaković, Miroslav M., Ilić-Tomić, Tatjana, Đorđević, Iris, Anđelković, Boban D., Tešević, Vele, Milosavljević, Slobodan M., Asakawa, Yoshinori, "Bisbibenzyls from Serbian Primula veris subsp. Columnae (Ten.) Lȕdi and P. acaulis (L.) L" in Phytochemistry, 212 (2023),
https://doi.org/10.1016/j.phytochem.2023.113719 . .

TY  - DATA
AU  - Novaković, Miroslav M.
AU  - Simić, Stefan
AU  - Koračak, Ljiljana
AU  - Zlatović, Mario
AU  - Ilić-Tomič, Tatjana
AU  - Asakawa, Yoshinori
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3889
PB  - Elsevier
T2  - Fitoterapia
T1  - Supplementary data for the article: Novakovic, M.; Simić, S.; Koračak, L.; Zlatović, M.; Ilic-Tomic, T.; Asakawa, Y.; Nikodinovic-Runic, J.; Opsenica, I. Chemo- and Biocatalytic Esterification of Marchantin A and Cytotoxic Activity of Ester Derivatives. Fitoterapia 2020, 142. https://doi.org/10.1016/j.fitote.2020.104520.oxic activity of ester derivatives http://cherry.chem.bg.ac.rs/handle/123456789/3867
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3889
ER  - 

@misc{
author = "Novaković, Miroslav M. and Simić, Stefan and Koračak, Ljiljana and Zlatović, Mario and Ilić-Tomič, Tatjana and Asakawa, Yoshinori and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2020",
publisher = "Elsevier",
journal = "Fitoterapia",
title = "Supplementary data for the article: Novakovic, M.; Simić, S.; Koračak, L.; Zlatović, M.; Ilic-Tomic, T.; Asakawa, Y.; Nikodinovic-Runic, J.; Opsenica, I. Chemo- and Biocatalytic Esterification of Marchantin A and Cytotoxic Activity of Ester Derivatives. Fitoterapia 2020, 142. https://doi.org/10.1016/j.fitote.2020.104520.oxic activity of ester derivatives http://cherry.chem.bg.ac.rs/handle/123456789/3867",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3889"
}

Novaković, M. M., Simić, S., Koračak, L., Zlatović, M., Ilić-Tomič, T., Asakawa, Y., Nikodinović-Runić, J.,& Opsenica, I.. (2020). Supplementary data for the article: Novakovic, M.; Simić, S.; Koračak, L.; Zlatović, M.; Ilic-Tomic, T.; Asakawa, Y.; Nikodinovic-Runic, J.; Opsenica, I. Chemo- and Biocatalytic Esterification of Marchantin A and Cytotoxic Activity of Ester Derivatives. Fitoterapia 2020, 142. https://doi.org/10.1016/j.fitote.2020.104520.oxic activity of ester derivatives http://cherry.chem.bg.ac.rs/handle/123456789/3867. in Fitoterapia
Elsevier..
https://hdl.handle.net/21.15107/rcub_cherry_3889

Novaković MM, Simić S, Koračak L, Zlatović M, Ilić-Tomič T, Asakawa Y, Nikodinović-Runić J, Opsenica I. Supplementary data for the article: Novakovic, M.; Simić, S.; Koračak, L.; Zlatović, M.; Ilic-Tomic, T.; Asakawa, Y.; Nikodinovic-Runic, J.; Opsenica, I. Chemo- and Biocatalytic Esterification of Marchantin A and Cytotoxic Activity of Ester Derivatives. Fitoterapia 2020, 142. https://doi.org/10.1016/j.fitote.2020.104520.oxic activity of ester derivatives http://cherry.chem.bg.ac.rs/handle/123456789/3867. in Fitoterapia. 2020;.
https://hdl.handle.net/21.15107/rcub_cherry_3889 .

Novaković, Miroslav M., Simić, Stefan, Koračak, Ljiljana, Zlatović, Mario, Ilić-Tomič, Tatjana, Asakawa, Yoshinori, Nikodinović-Runić, Jasmina, Opsenica, Igor, "Supplementary data for the article: Novakovic, M.; Simić, S.; Koračak, L.; Zlatović, M.; Ilic-Tomic, T.; Asakawa, Y.; Nikodinovic-Runic, J.; Opsenica, I. Chemo- and Biocatalytic Esterification of Marchantin A and Cytotoxic Activity of Ester Derivatives. Fitoterapia 2020, 142. https://doi.org/10.1016/j.fitote.2020.104520.oxic activity of ester derivatives http://cherry.chem.bg.ac.rs/handle/123456789/3867" in Fitoterapia (2020),
https://hdl.handle.net/21.15107/rcub_cherry_3889 .

TY  - JOUR
AU  - Novaković, Miroslav M.
AU  - Simić, Stefan
AU  - Koračak, Ljiljana
AU  - Zlatović, Mario
AU  - Ilić-Tomič, Tatjana
AU  - Asakawa, Yoshinori
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3890
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 M. and Simić, Stefan and Koračak, Ljiljana and Zlatović, Mario and Ilić-Tomič, 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. M., Simić, S., Koračak, L., Zlatović, M., Ilić-Tomič, 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 MM, Simić S, Koračak L, Zlatović M, Ilić-Tomič 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 M., Simić, Stefan, Koračak, Ljiljana, Zlatović, Mario, Ilić-Tomič, 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 . .

TY  - JOUR
AU  - Novaković, Miroslav M.
AU  - Simić, Stefan
AU  - Koračak, Ljiljana
AU  - Zlatović, Mario
AU  - Ilić-Tomič, Tatjana
AU  - Asakawa, Yoshinori
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3867
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 M. and Simić, Stefan and Koračak, Ljiljana and Zlatović, Mario and Ilić-Tomič, 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. M., Simić, S., Koračak, L., Zlatović, M., Ilić-Tomič, 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 MM, Simić S, Koračak L, Zlatović M, Ilić-Tomič 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 M., Simić, Stefan, Koračak, Ljiljana, Zlatović, Mario, Ilić-Tomič, 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 . .

TY  - JOUR
AU  - Novaković, Miroslav M.
AU  - Bukvicki, Danka
AU  - Anđelković, Boban D.
AU  - Ilić-Tomić, Tatjana
AU  - Veljić, Milan
AU  - Tešević, Vele
AU  - Asakawa, Yoshinori
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3096
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 IC 50 values of 5.0, 5.0, and 2.5 μM, respectively.
PB  - American Chemical Society and American Society of Pharmacognosy
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 M. 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 IC 50 values of 5.0, 5.0, and 2.5 μM, respectively.",
publisher = "American Chemical Society and American Society of Pharmacognosy",
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. 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 and American Society of Pharmacognosy., 82(4), 694-701.
https://doi.org/10.1021/acs.jnatprod.8b00390

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

TY  - DATA
AU  - Novaković, Miroslav M.
AU  - Bukvicki, Danka
AU  - Anđelković, Boban D.
AU  - Ilić-Tomić, Tatjana
AU  - Veljić, Milan
AU  - Tešević, Vele
AU  - Asakawa, Yoshinori
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3097
PB  - American Chemical Society and American Society of Pharmacognosy
T2  - Journal of Natural Products
T1  - Supplementary data for article:   	Novakovic, M.; Bukvicki, D.; Andjelkovic, B.; Ilic-Tomic, T.; Veljic, M.; Tesevic, V.; Asakawa, Y. Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia Cruciata. Journal of Natural Products 2019, 82 (4), 694–701. https://doi.org/10.1021/acs.jnatprod.8b00390
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3097
ER  - 

@misc{
author = "Novaković, Miroslav M. and Bukvicki, Danka and Anđelković, Boban D. and Ilić-Tomić, Tatjana and Veljić, Milan and Tešević, Vele and Asakawa, Yoshinori",
year = "2019",
publisher = "American Chemical Society and American Society of Pharmacognosy",
journal = "Journal of Natural Products",
title = "Supplementary data for article:   	Novakovic, M.; Bukvicki, D.; Andjelkovic, B.; Ilic-Tomic, T.; Veljic, M.; Tesevic, V.; Asakawa, Y. Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia Cruciata. Journal of Natural Products 2019, 82 (4), 694–701. https://doi.org/10.1021/acs.jnatprod.8b00390",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3097"
}

Novaković, M. M., Bukvicki, D., Anđelković, B. D., Ilić-Tomić, T., Veljić, M., Tešević, V.,& Asakawa, Y.. (2019). Supplementary data for article:   	Novakovic, M.; Bukvicki, D.; Andjelkovic, B.; Ilic-Tomic, T.; Veljic, M.; Tesevic, V.; Asakawa, Y. Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia Cruciata. Journal of Natural Products 2019, 82 (4), 694–701. https://doi.org/10.1021/acs.jnatprod.8b00390. in Journal of Natural Products
American Chemical Society and American Society of Pharmacognosy..
https://hdl.handle.net/21.15107/rcub_cherry_3097

Novaković MM, Bukvicki D, Anđelković BD, Ilić-Tomić T, Veljić M, Tešević V, Asakawa Y. Supplementary data for article:   	Novakovic, M.; Bukvicki, D.; Andjelkovic, B.; Ilic-Tomic, T.; Veljic, M.; Tesevic, V.; Asakawa, Y. Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia Cruciata. Journal of Natural Products 2019, 82 (4), 694–701. https://doi.org/10.1021/acs.jnatprod.8b00390. in Journal of Natural Products. 2019;.
https://hdl.handle.net/21.15107/rcub_cherry_3097 .

Novaković, Miroslav M., Bukvicki, Danka, Anđelković, Boban D., Ilić-Tomić, Tatjana, Veljić, Milan, Tešević, Vele, Asakawa, Yoshinori, "Supplementary data for article:   	Novakovic, M.; Bukvicki, D.; Andjelkovic, B.; Ilic-Tomic, T.; Veljic, M.; Tesevic, V.; Asakawa, Y. Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia Cruciata. Journal of Natural Products 2019, 82 (4), 694–701. https://doi.org/10.1021/acs.jnatprod.8b00390" in Journal of Natural Products (2019),
https://hdl.handle.net/21.15107/rcub_cherry_3097 .

TY  - JOUR
AU  - Novaković, Miroslav M.
AU  - Bukvicki, Danka
AU  - Vajs, Vlatka
AU  - Tešević, Vele
AU  - Milosavljević, Slobodan M.
AU  - Marin, Petar D.
AU  - Asakawa, Yoshinori
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2150
AB  - A number of potentially useful compounds with various biological activities can be obtained from plant metabolites by microorganisms. In present research, essential oil of Calamintha glandulosa was subjected to the biotransformation process by mycromicete Aspergillus niger. GC/MS analyses of the original and biotransformed essential oil have revealed six(1-6) biotransformed compounds from one of the main component-limonene and one biotransformed product (7) originating from the less abundant component-thymol. Piperitone epoxide and piperitenone epoxide, the most abundant components of the original oil, were not biotransformed but gave three artefacts (A1, A2, B1) due to the acidic conditions formed in A. niger medium. Compounds 5, 6 as well as 7 have not been previously found as a biotransformation products of limonene (5 and 6) and thymol (7), respectively. New products (5, 6, and 7) together with the artefacts, were isolated by silica gel column chromatography followed by preparative silica gel thin layer chromatography, and their structures were established by a combination of 1D and 2D NMR spectra and GC/MS data. Biotransformation has one more confirmed as useful method, complementary to synthesis, for obtaining different type of molecules.
PB  - Natural Products Inc, Westerville
T2  - Natural Product Communications
T1  - Microbial Transformation of Calamintha glandulosa Essential Oil by Aspergillus niger
VL  - 13
IS  - 4
SP  - 479
EP  - 482
UR  - https://hdl.handle.net/21.15107/rcub_cherry_2150
ER  - 

@article{
author = "Novaković, Miroslav M. and Bukvicki, Danka and Vajs, Vlatka and Tešević, Vele and Milosavljević, Slobodan M. and Marin, Petar D. and Asakawa, Yoshinori",
year = "2018",
abstract = "A number of potentially useful compounds with various biological activities can be obtained from plant metabolites by microorganisms. In present research, essential oil of Calamintha glandulosa was subjected to the biotransformation process by mycromicete Aspergillus niger. GC/MS analyses of the original and biotransformed essential oil have revealed six(1-6) biotransformed compounds from one of the main component-limonene and one biotransformed product (7) originating from the less abundant component-thymol. Piperitone epoxide and piperitenone epoxide, the most abundant components of the original oil, were not biotransformed but gave three artefacts (A1, A2, B1) due to the acidic conditions formed in A. niger medium. Compounds 5, 6 as well as 7 have not been previously found as a biotransformation products of limonene (5 and 6) and thymol (7), respectively. New products (5, 6, and 7) together with the artefacts, were isolated by silica gel column chromatography followed by preparative silica gel thin layer chromatography, and their structures were established by a combination of 1D and 2D NMR spectra and GC/MS data. Biotransformation has one more confirmed as useful method, complementary to synthesis, for obtaining different type of molecules.",
publisher = "Natural Products Inc, Westerville",
journal = "Natural Product Communications",
title = "Microbial Transformation of Calamintha glandulosa Essential Oil by Aspergillus niger",
volume = "13",
number = "4",
pages = "479-482",
url = "https://hdl.handle.net/21.15107/rcub_cherry_2150"
}

Novaković, M. M., Bukvicki, D., Vajs, V., Tešević, V., Milosavljević, S. M., Marin, P. D.,& Asakawa, Y.. (2018). Microbial Transformation of Calamintha glandulosa Essential Oil by Aspergillus niger. in Natural Product Communications
Natural Products Inc, Westerville., 13(4), 479-482.
https://hdl.handle.net/21.15107/rcub_cherry_2150

Novaković MM, Bukvicki D, Vajs V, Tešević V, Milosavljević SM, Marin PD, Asakawa Y. Microbial Transformation of Calamintha glandulosa Essential Oil by Aspergillus niger. in Natural Product Communications. 2018;13(4):479-482.
https://hdl.handle.net/21.15107/rcub_cherry_2150 .

Novaković, Miroslav M., Bukvicki, Danka, Vajs, Vlatka, Tešević, Vele, Milosavljević, Slobodan M., Marin, Petar D., Asakawa, Yoshinori, "Microbial Transformation of Calamintha glandulosa Essential Oil by Aspergillus niger" in Natural Product Communications, 13, no. 4 (2018):479-482,
https://hdl.handle.net/21.15107/rcub_cherry_2150 .

TY  - JOUR
AU  - Bukvicki, Danka
AU  - Ćirić, Ana D.
AU  - Soković, Marina
AU  - Vannini, Lucia
AU  - Nissen, Lorenzo
AU  - Novaković, Miroslav M.
AU  - Vujisić, Ljubodrag V.
AU  - Asakawa, Yoshinori
AU  - Marin, Petar D.
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2374
AB  - The chemical composition, antimicrobial and antiquorum sensing activity of the essential oil of Micromeria thymifolia (Scop.) Fritsch were investigated. Limonene, piperitone epoxide and piperitenone epoxide were found as the main constituents using a gas chromatography-mass spectrometry technique. In vitro antimicrobial activity of the oil was tested against six bacterial and seven fungal strains and high antimicrobial potential was noticed. Minimum inhibitory concentration varied from 0.031 mg/mL to 0.5 mg/mL for bacterial and 0.062 mg/mL to 0.5 mg/mL for fungal strains. The antiquorum properties of the essential oil were evaluated on Pseudomonas aeruginosa PAO1. The oil was tested at subMiC concentrations for anti-quorum sensing activity. The analyses on quorum-sensing functions have been carried out by evaluating twitching and swarming of bacterial cultures and the total amount of pyocyanin production produced by P. aeruginosa. This study showed that M thymifolia essential oil exhibited antiquorum sensing activity and may be used as an antipathogenic drug.
PB  - Natural Products Inc, Westerville
T2  - Natural Product Communications
T1  - Micromeria thymifolia Essential Oil Suppresses Quorum-sensing Signaling in Pseudomonas aeruginosa
VL  - 11
IS  - 12
SP  - 1903
EP  - 1906
UR  - https://hdl.handle.net/21.15107/rcub_cherry_2374
ER  - 

@article{
author = "Bukvicki, Danka and Ćirić, Ana D. and Soković, Marina and Vannini, Lucia and Nissen, Lorenzo and Novaković, Miroslav M. and Vujisić, Ljubodrag V. and Asakawa, Yoshinori and Marin, Petar D.",
year = "2016",
abstract = "The chemical composition, antimicrobial and antiquorum sensing activity of the essential oil of Micromeria thymifolia (Scop.) Fritsch were investigated. Limonene, piperitone epoxide and piperitenone epoxide were found as the main constituents using a gas chromatography-mass spectrometry technique. In vitro antimicrobial activity of the oil was tested against six bacterial and seven fungal strains and high antimicrobial potential was noticed. Minimum inhibitory concentration varied from 0.031 mg/mL to 0.5 mg/mL for bacterial and 0.062 mg/mL to 0.5 mg/mL for fungal strains. The antiquorum properties of the essential oil were evaluated on Pseudomonas aeruginosa PAO1. The oil was tested at subMiC concentrations for anti-quorum sensing activity. The analyses on quorum-sensing functions have been carried out by evaluating twitching and swarming of bacterial cultures and the total amount of pyocyanin production produced by P. aeruginosa. This study showed that M thymifolia essential oil exhibited antiquorum sensing activity and may be used as an antipathogenic drug.",
publisher = "Natural Products Inc, Westerville",
journal = "Natural Product Communications",
title = "Micromeria thymifolia Essential Oil Suppresses Quorum-sensing Signaling in Pseudomonas aeruginosa",
volume = "11",
number = "12",
pages = "1903-1906",
url = "https://hdl.handle.net/21.15107/rcub_cherry_2374"
}

Bukvicki, D., Ćirić, A. D., Soković, M., Vannini, L., Nissen, L., Novaković, M. M., Vujisić, L. V., Asakawa, Y.,& Marin, P. D.. (2016). Micromeria thymifolia Essential Oil Suppresses Quorum-sensing Signaling in Pseudomonas aeruginosa. in Natural Product Communications
Natural Products Inc, Westerville., 11(12), 1903-1906.
https://hdl.handle.net/21.15107/rcub_cherry_2374

Bukvicki D, Ćirić AD, Soković M, Vannini L, Nissen L, Novaković MM, Vujisić LV, Asakawa Y, Marin PD. Micromeria thymifolia Essential Oil Suppresses Quorum-sensing Signaling in Pseudomonas aeruginosa. in Natural Product Communications. 2016;11(12):1903-1906.
https://hdl.handle.net/21.15107/rcub_cherry_2374 .

Bukvicki, Danka, Ćirić, Ana D., Soković, Marina, Vannini, Lucia, Nissen, Lorenzo, Novaković, Miroslav M., Vujisić, Ljubodrag V., Asakawa, Yoshinori, Marin, Petar D., "Micromeria thymifolia Essential Oil Suppresses Quorum-sensing Signaling in Pseudomonas aeruginosa" in Natural Product Communications, 11, no. 12 (2016):1903-1906,
https://hdl.handle.net/21.15107/rcub_cherry_2374 .