TY  - JOUR
AU  - Novaković, Miroslav
AU  - Ilić-Tomić, Tatjana
AU  - Đorđević, Iris
AU  - Anđelković, Boban
AU  - Tesević, Vele
AU  - Milosavljević, Slobodan
AU  - Asakawa, Yoshinori
PY  - 2023
UR  - https://www.sciencedirect.com/science/article/pii/S0031942223001358
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/1862
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 compounds 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.
T2  - Phytochemistry
T2  - PhytochemistryPhytochemistry
T1  - Bisbibenzyls from Serbian Primula veris subsp. Columnae (Ten.) Lȕdi and P. acaulis (L.) L
SP  - 113719
VL  - 212
DO  - 10.1016/j.phytochem.2023.113719
ER  - 

@article{
author = "Novaković, Miroslav and Ilić-Tomić, Tatjana and Đorđević, Iris and Anđelković, Boban and Tesević, Vele and Milosavljević, Slobodan and Asakawa, Yoshinori",
year = "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 compounds 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.",
journal = "Phytochemistry, PhytochemistryPhytochemistry",
title = "Bisbibenzyls from Serbian Primula veris subsp. Columnae (Ten.) Lȕdi and P. acaulis (L.) L",
pages = "113719",
volume = "212",
doi = "10.1016/j.phytochem.2023.113719"
}

Novaković, M., Ilić-Tomić, T., Đorđević, I., Anđelković, B., Tesević, V., Milosavljević, S.,& Asakawa, Y.. (2023). Bisbibenzyls from Serbian Primula veris subsp. Columnae (Ten.) Lȕdi and P. acaulis (L.) L. in Phytochemistry, 212, 113719.
https://doi.org/10.1016/j.phytochem.2023.113719

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

Novaković, Miroslav, Ilić-Tomić, Tatjana, Đorđević, Iris, Anđelković, Boban, Tesević, Vele, Milosavljević, Slobodan, Asakawa, Yoshinori, "Bisbibenzyls from Serbian Primula veris subsp. Columnae (Ten.) Lȕdi and P. acaulis (L.) L" in Phytochemistry, 212 (2023):113719,
https://doi.org/10.1016/j.phytochem.2023.113719 . .

TY  - JOUR
AU  - Ivković, Ivana
AU  - Novaković, Miroslav
AU  - Veljić, Milan
AU  - Mojsin, Marija
AU  - Stevanović, Milena
AU  - Marin, Petar D.
AU  - Bukvicki, Danka
PY  - 2021
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/1428
AB  - Based on previous investigations where bis-bibenzyls isolated from liverworts showed various biological activities (cytotoxic, antimicrobial, and antiviral), we investigated their cytotoxic activity in several human cancer cell lines. From the methylene-chloride/methanol extract of the liverwort Pellia endiviifolia, three bis-bibenzyls of the perrottetin type were isolated, namely perrottetin E, 10 '-hydroxyperrottetin E, and 10,10 '-dihydroxyperrottetin E. The last two were found for the first time in this species. Their structures were resolved using 1D and 2D NMR, as well as by comparison with data in the literature. Cytotoxic activity of the isolated compounds was tested on three human leukemia cell lines, HL-60 (acute promyelocytic leukemia cells), U-937 (acute monocytic leukemia cells), and K-562 (human chronic myelogenous leukemia cells), as well as on human embryonal teratocarcinoma cell line (NT2/D1) and human glioblastoma cell lines A-172 and U-251, and compared to the previously isolated bis-bibenzyls (perrottetins) of similar structure. The isolated compounds exhibited modest activity against leukemia cells and significant activity against NT2/D1 and A-172. Overall, the most active cytotoxic compounds in this investigation were perrottetin E (1), isolated in this work from Pellia endiviifolia, and perrottetin F phenanthrene derivative (7), previously isolated from Lunularia cruciata and added for a comparison of their cytotoxic activity.
PB  - MDPI, Basel
T2  - Plants-Basel
T1  - Bis-Bibenzyls from the Liverwort Pellia endiviifolia and Their Biological Activity
IS  - 6
VL  - 10
DO  - 10.3390/plants10061063
ER  - 

@article{
author = "Ivković, Ivana and Novaković, Miroslav and Veljić, Milan and Mojsin, Marija and Stevanović, Milena and Marin, Petar D. and Bukvicki, Danka",
year = "2021",
abstract = "Based on previous investigations where bis-bibenzyls isolated from liverworts showed various biological activities (cytotoxic, antimicrobial, and antiviral), we investigated their cytotoxic activity in several human cancer cell lines. From the methylene-chloride/methanol extract of the liverwort Pellia endiviifolia, three bis-bibenzyls of the perrottetin type were isolated, namely perrottetin E, 10 '-hydroxyperrottetin E, and 10,10 '-dihydroxyperrottetin E. The last two were found for the first time in this species. Their structures were resolved using 1D and 2D NMR, as well as by comparison with data in the literature. Cytotoxic activity of the isolated compounds was tested on three human leukemia cell lines, HL-60 (acute promyelocytic leukemia cells), U-937 (acute monocytic leukemia cells), and K-562 (human chronic myelogenous leukemia cells), as well as on human embryonal teratocarcinoma cell line (NT2/D1) and human glioblastoma cell lines A-172 and U-251, and compared to the previously isolated bis-bibenzyls (perrottetins) of similar structure. The isolated compounds exhibited modest activity against leukemia cells and significant activity against NT2/D1 and A-172. Overall, the most active cytotoxic compounds in this investigation were perrottetin E (1), isolated in this work from Pellia endiviifolia, and perrottetin F phenanthrene derivative (7), previously isolated from Lunularia cruciata and added for a comparison of their cytotoxic activity.",
publisher = "MDPI, Basel",
journal = "Plants-Basel",
title = "Bis-Bibenzyls from the Liverwort Pellia endiviifolia and Their Biological Activity",
number = "6",
volume = "10",
doi = "10.3390/plants10061063"
}

Ivković, I., Novaković, M., Veljić, M., Mojsin, M., Stevanović, M., Marin, P. D.,& Bukvicki, D.. (2021). Bis-Bibenzyls from the Liverwort Pellia endiviifolia and Their Biological Activity. in Plants-Basel
MDPI, Basel., 10(6).
https://doi.org/10.3390/plants10061063

Ivković I, Novaković M, Veljić M, Mojsin M, Stevanović M, Marin PD, Bukvicki D. Bis-Bibenzyls from the Liverwort Pellia endiviifolia and Their Biological Activity. in Plants-Basel. 2021;10(6).
doi:10.3390/plants10061063 .

Ivković, Ivana, Novaković, Miroslav, Veljić, Milan, Mojsin, Marija, Stevanović, Milena, Marin, Petar D., Bukvicki, Danka, "Bis-Bibenzyls from the Liverwort Pellia endiviifolia and Their Biological Activity" in Plants-Basel, 10, no. 6 (2021),
https://doi.org/10.3390/plants10061063 . .

TY  - JOUR
AU  - Bukvicki, Danka
AU  - Novaković, Miroslav
AU  - Ilić-Tomić, Tatjana
AU  - Nikodinović-Runić, Jasmina
AU  - Todorović, Nina
AU  - Veljić, Milan
AU  - Asakawa, Yoshinori
PY  - 2021
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/1418
AB  - Biotransformation of bis-bibenzyl perrottetin F (1), isolated from the liverwort Lunularia cruciata by Aspergillus niger, has been investigated. New metabolites (2-4) have been isolated using reversed phase semipreparative HPLC and their structures were established to be 8-hydroxyperrottetin F, C-7-C-8 cleaved product, and perrottetin F 6'-sulfate using 1D and 2D NMR, HR-ESI-MS, IR and UV spectroscopy. The antimicrobial and cytotoxic properties of these compounds were also evaluated. Given the suggested cytotoxic properties of the parent compound, antiproliferative activity against healthy human lung fibroblasts (MRC5) and human lung carcinoma (A549) of three metabolites were evaluated revealing their lower cytotoxic properties in comparison to the starting compound - perrottetin F. The antimicrobial properties of these compounds were also evaluated, with the inhibitory activity against the Pseudomonas aeruginosa PAO1 and Staphylococcus aureus determined between 100 mu M and 450 mu M. The metabolites showed remarkable ability to inhibit synthesis of bacterial quorum-sensing signal molecules such as short chain acyl homoserine lactones (AHLs). Therefore, biotransformation method represents fast and effective tool for obtaining new bioactive structures.
PB  - ACG Publications, Gebze-Kocaeli
T2  - Records of Natural Products
T1  - Biotransformation of Perrottetin F by Aspergillus niger: New Bioactive Secondary Metabolites
EP  - 292
IS  - 4
SP  - 281
VL  - 15
DO  - 10.25135/rnp.215.20.09.1812
ER  - 

@article{
author = "Bukvicki, Danka and Novaković, Miroslav and Ilić-Tomić, Tatjana and Nikodinović-Runić, Jasmina and Todorović, Nina and Veljić, Milan and Asakawa, Yoshinori",
year = "2021",
abstract = "Biotransformation of bis-bibenzyl perrottetin F (1), isolated from the liverwort Lunularia cruciata by Aspergillus niger, has been investigated. New metabolites (2-4) have been isolated using reversed phase semipreparative HPLC and their structures were established to be 8-hydroxyperrottetin F, C-7-C-8 cleaved product, and perrottetin F 6'-sulfate using 1D and 2D NMR, HR-ESI-MS, IR and UV spectroscopy. The antimicrobial and cytotoxic properties of these compounds were also evaluated. Given the suggested cytotoxic properties of the parent compound, antiproliferative activity against healthy human lung fibroblasts (MRC5) and human lung carcinoma (A549) of three metabolites were evaluated revealing their lower cytotoxic properties in comparison to the starting compound - perrottetin F. The antimicrobial properties of these compounds were also evaluated, with the inhibitory activity against the Pseudomonas aeruginosa PAO1 and Staphylococcus aureus determined between 100 mu M and 450 mu M. The metabolites showed remarkable ability to inhibit synthesis of bacterial quorum-sensing signal molecules such as short chain acyl homoserine lactones (AHLs). Therefore, biotransformation method represents fast and effective tool for obtaining new bioactive structures.",
publisher = "ACG Publications, Gebze-Kocaeli",
journal = "Records of Natural Products",
title = "Biotransformation of Perrottetin F by Aspergillus niger: New Bioactive Secondary Metabolites",
pages = "292-281",
number = "4",
volume = "15",
doi = "10.25135/rnp.215.20.09.1812"
}

Bukvicki, D., Novaković, M., Ilić-Tomić, T., Nikodinović-Runić, J., Todorović, N., Veljić, M.,& Asakawa, Y.. (2021). Biotransformation of Perrottetin F by Aspergillus niger: New Bioactive Secondary Metabolites. in Records of Natural Products
ACG Publications, Gebze-Kocaeli., 15(4), 281-292.
https://doi.org/10.25135/rnp.215.20.09.1812

Bukvicki D, Novaković M, Ilić-Tomić T, Nikodinović-Runić J, Todorović N, Veljić M, Asakawa Y. Biotransformation of Perrottetin F by Aspergillus niger: New Bioactive Secondary Metabolites. in Records of Natural Products. 2021;15(4):281-292.
doi:10.25135/rnp.215.20.09.1812 .

Bukvicki, Danka, Novaković, Miroslav, Ilić-Tomić, Tatjana, Nikodinović-Runić, Jasmina, Todorović, Nina, Veljić, Milan, Asakawa, Yoshinori, "Biotransformation of Perrottetin F by Aspergillus niger: New Bioactive Secondary Metabolites" in Records of Natural Products, 15, no. 4 (2021):281-292,
https://doi.org/10.25135/rnp.215.20.09.1812 . .

TY  - JOUR
AU  - Novaković, Miroslav
AU  - Simić, Stefan
AU  - Koracak, Ljiljana
AU  - Zlatović, Mario
AU  - Ilić-Tomić, Tatjana
AU  - Asakawa, Yoshinori
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2020
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/1755
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, Amsterdam
T2  - Fitoterapia
T1  - Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives
VL  - 142
DO  - 10.1016/j.fitote.2020.104520
ER  - 

@article{
author = "Novaković, Miroslav and Simić, Stefan and Koracak, 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, Amsterdam",
journal = "Fitoterapia",
title = "Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives",
volume = "142",
doi = "10.1016/j.fitote.2020.104520"
}

Novaković, M., Simić, S., Koracak, 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, Amsterdam., 142.
https://doi.org/10.1016/j.fitote.2020.104520

Novaković M, Simić S, Koracak 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.
doi:10.1016/j.fitote.2020.104520 .

Novaković, Miroslav, Simić, Stefan, Koracak, 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),
https://doi.org/10.1016/j.fitote.2020.104520 . .

TY  - JOUR
AU  - Novaković, Miroslav
AU  - Simić, Stefan
AU  - Koracak, Ljiljana
AU  - Zlatović, Mario
AU  - Ilić-Tomić, Tatjana
AU  - Asakawa, Yoshinori
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2020
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/1367
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, Amsterdam
T2  - Fitoterapia
T1  - Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives
VL  - 142
DO  - 10.1016/j.fitote.2020.104520
ER  - 

@article{
author = "Novaković, Miroslav and Simić, Stefan and Koracak, 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, Amsterdam",
journal = "Fitoterapia",
title = "Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives",
volume = "142",
doi = "10.1016/j.fitote.2020.104520"
}

Novaković, M., Simić, S., Koracak, 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, Amsterdam., 142.
https://doi.org/10.1016/j.fitote.2020.104520

Novaković M, Simić S, Koracak 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.
doi:10.1016/j.fitote.2020.104520 .

Novaković, Miroslav, Simić, Stefan, Koracak, 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),
https://doi.org/10.1016/j.fitote.2020.104520 . .

TY  - JOUR
AU  - Novaković, Miroslav
AU  - Bukvicki, Danka
AU  - Anđelković, Boban
AU  - Ilić-Tomić, Tatjana
AU  - Veljić, Milan
AU  - Tešević, Vele
AU  - Asakawa, Yoshinori
PY  - 2019
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/1281
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 mu M, respectively.
PB  - Amer Chemical Soc, Washington
T2  - Journal of Natural Products
T1  - Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia cruciata
EP  - 701
IS  - 4
SP  - 694
VL  - 82
DO  - 10.1021/acs.jnatprod.8b00390
ER  - 

@article{
author = "Novaković, Miroslav and Bukvicki, Danka and Anđelković, Boban 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 mu M, respectively.",
publisher = "Amer Chemical Soc, Washington",
journal = "Journal of Natural Products",
title = "Cytotoxic Activity of Riccardin and Perrottetin Derivatives from the Liverwort Lunularia cruciata",
pages = "701-694",
number = "4",
volume = "82",
doi = "10.1021/acs.jnatprod.8b00390"
}

Novaković, M., Bukvicki, D., Anđelković, B., 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
Amer Chemical Soc, Washington., 82(4), 694-701.
https://doi.org/10.1021/acs.jnatprod.8b00390

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

TY  - JOUR
AU  - Ilić-Tomić, Tatjana
AU  - Soković, Marina
AU  - Vojnović, Sandra
AU  - Cirić, Ana
AU  - Veljić, Milan
AU  - Nikodinović-Runić, Jasmina
AU  - Novaković, Miroslav
PY  - 2017
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/1059
AB  - Diarylheptanoids from the barks of Alnus viridis ssp. viridis (green alder) and Alnus glutinosa (black alder) were explored for anti-quorum sensing activity. Chemicals with anti-quorum sensing activity have recently been examined for antimicrobial applications. The anti-quorum sensing activity of the selected diarylheptanoids was determined using two biosensors, namely Pseudomonas aeruginosa PAO1 and Chromobacterium violaceum CV026. Although all of the investigated compounds negatively influenced the motility of P. aeruginosa PAO1, four were able to inhibit biofilm formation of this human opportunistic pathogen for 40-70%. Three of the diarylheptanoids (3, 4, and 5) negatively influenced the biosynthesis of pyocyanin, which is under the control of quorum sensing. Platyphyllenone (7) and hirsutenone (5) were able to inhibit the biosynthesis of violacein in C. violaceum CV026, with 5 being able to inhibit the synthesis of both biopigments. Only one of the tested diarylheptanoids (1) was shown to significantly decrease the production of acyl homoserine lactones (AHL) in P. aeruginosa PAO1, more specifically, production of the long chain N-(3-oxododecanoyl)- l-HSL. On the other side, four diarylheptanoids (2-5) significantly reduced the synthesis of 2-alkyl-4-quinolones, part of the P. aeruginosa quinolone-mediated signaling system. To properly assess therapeutic potential of these compounds, their in vitro antiproliferative effect on normal human lung fibroblasts was determined, with doses affecting cell proliferation between 10 and 100 mu g/mL. This study confirms that the barks of green and black alders are rich source of phytochemicals with a wide range of biological activities that could further be exploited as natural agents against bacterial contaminations and infections.
PB  - Georg Thieme Verlag Kg, Stuttgart
T2  - Planta Medica
T1  - Diarylheptanoids from Alnus viridis ssp viridis and Alnus glutinosa: Modulation of Quorum Sensing Activity in Pseudomonas aeruginosa
EP  - 125
IS  - 01-02
SP  - 117
VL  - 83
DO  - 10.1055/s-0042-107674
ER  - 

@article{
author = "Ilić-Tomić, Tatjana and Soković, Marina and Vojnović, Sandra and Cirić, Ana and Veljić, Milan and Nikodinović-Runić, Jasmina and Novaković, Miroslav",
year = "2017",
abstract = "Diarylheptanoids from the barks of Alnus viridis ssp. viridis (green alder) and Alnus glutinosa (black alder) were explored for anti-quorum sensing activity. Chemicals with anti-quorum sensing activity have recently been examined for antimicrobial applications. The anti-quorum sensing activity of the selected diarylheptanoids was determined using two biosensors, namely Pseudomonas aeruginosa PAO1 and Chromobacterium violaceum CV026. Although all of the investigated compounds negatively influenced the motility of P. aeruginosa PAO1, four were able to inhibit biofilm formation of this human opportunistic pathogen for 40-70%. Three of the diarylheptanoids (3, 4, and 5) negatively influenced the biosynthesis of pyocyanin, which is under the control of quorum sensing. Platyphyllenone (7) and hirsutenone (5) were able to inhibit the biosynthesis of violacein in C. violaceum CV026, with 5 being able to inhibit the synthesis of both biopigments. Only one of the tested diarylheptanoids (1) was shown to significantly decrease the production of acyl homoserine lactones (AHL) in P. aeruginosa PAO1, more specifically, production of the long chain N-(3-oxododecanoyl)- l-HSL. On the other side, four diarylheptanoids (2-5) significantly reduced the synthesis of 2-alkyl-4-quinolones, part of the P. aeruginosa quinolone-mediated signaling system. To properly assess therapeutic potential of these compounds, their in vitro antiproliferative effect on normal human lung fibroblasts was determined, with doses affecting cell proliferation between 10 and 100 mu g/mL. This study confirms that the barks of green and black alders are rich source of phytochemicals with a wide range of biological activities that could further be exploited as natural agents against bacterial contaminations and infections.",
publisher = "Georg Thieme Verlag Kg, Stuttgart",
journal = "Planta Medica",
title = "Diarylheptanoids from Alnus viridis ssp viridis and Alnus glutinosa: Modulation of Quorum Sensing Activity in Pseudomonas aeruginosa",
pages = "125-117",
number = "01-02",
volume = "83",
doi = "10.1055/s-0042-107674"
}

Ilić-Tomić, T., Soković, M., Vojnović, S., Cirić, A., Veljić, M., Nikodinović-Runić, J.,& Novaković, M.. (2017). Diarylheptanoids from Alnus viridis ssp viridis and Alnus glutinosa: Modulation of Quorum Sensing Activity in Pseudomonas aeruginosa. in Planta Medica
Georg Thieme Verlag Kg, Stuttgart., 83(01-02), 117-125.
https://doi.org/10.1055/s-0042-107674

Ilić-Tomić T, Soković M, Vojnović S, Cirić A, Veljić M, Nikodinović-Runić J, Novaković M. Diarylheptanoids from Alnus viridis ssp viridis and Alnus glutinosa: Modulation of Quorum Sensing Activity in Pseudomonas aeruginosa. in Planta Medica. 2017;83(01-02):117-125.
doi:10.1055/s-0042-107674 .

Ilić-Tomić, Tatjana, Soković, Marina, Vojnović, Sandra, Cirić, Ana, Veljić, Milan, Nikodinović-Runić, Jasmina, Novaković, Miroslav, "Diarylheptanoids from Alnus viridis ssp viridis and Alnus glutinosa: Modulation of Quorum Sensing Activity in Pseudomonas aeruginosa" in Planta Medica, 83, no. 01-02 (2017):117-125,
https://doi.org/10.1055/s-0042-107674 . .

TY  - JOUR
AU  - Novaković, Miroslav
AU  - Nikodinović-Runić, Jasmina
AU  - Veselinović, Jovana
AU  - Ilić-Tomić, Tatjana
AU  - Vidaković, Vera
AU  - Tešević, Vele
AU  - Milosavljević, Slobodan
PY  - 2017
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/1081
AB  - Seven derivatives of pentacyclic triterpene acids (1-7) were isolated from the bark of Alnus viridis ssp. viridis using a combination of column chromatography and semipreparative HPLC. Compounds 1-3, 6, and 7 were determined to be new after spectroscopic data interpretation and were assigned as 27-hydroxyalphitolic acid derivatives (1-3), a 27-hydroxybetulinic acid derivative (6), and a 3-epi-maslinic acid derivative (7), respectively. Pentacyclic triterpenoids with a C-27 hydroxymethyl group have been found in species of the genus Alnus for the first time. These compounds were subjected to cytotoxicity testing against a number of canter cell lines. Also, selected pentacyclic triterpenoids were selected as potential inhibitors of topoisomerases I and Ha for an in silico investigation.
PB  - Amer Chemical Soc, Washington
T2  - Journal of Natural Products
T1  - Bioactive Pentacyclic Triterpene Ester Derivatives from Alnus viridis ssp viridis Bark
EP  - 1263
IS  - 5
SP  - 1255
VL  - 80
DO  - 10.1021/acs.jnatprod.6b00805
ER  - 

@article{
author = "Novaković, Miroslav and Nikodinović-Runić, Jasmina and Veselinović, Jovana and Ilić-Tomić, Tatjana and Vidaković, Vera and Tešević, Vele and Milosavljević, Slobodan",
year = "2017",
abstract = "Seven derivatives of pentacyclic triterpene acids (1-7) were isolated from the bark of Alnus viridis ssp. viridis using a combination of column chromatography and semipreparative HPLC. Compounds 1-3, 6, and 7 were determined to be new after spectroscopic data interpretation and were assigned as 27-hydroxyalphitolic acid derivatives (1-3), a 27-hydroxybetulinic acid derivative (6), and a 3-epi-maslinic acid derivative (7), respectively. Pentacyclic triterpenoids with a C-27 hydroxymethyl group have been found in species of the genus Alnus for the first time. These compounds were subjected to cytotoxicity testing against a number of canter cell lines. Also, selected pentacyclic triterpenoids were selected as potential inhibitors of topoisomerases I and Ha for an in silico investigation.",
publisher = "Amer Chemical Soc, Washington",
journal = "Journal of Natural Products",
title = "Bioactive Pentacyclic Triterpene Ester Derivatives from Alnus viridis ssp viridis Bark",
pages = "1263-1255",
number = "5",
volume = "80",
doi = "10.1021/acs.jnatprod.6b00805"
}

Novaković, M., Nikodinović-Runić, J., Veselinović, J., Ilić-Tomić, T., Vidaković, V., Tešević, V.,& Milosavljević, S.. (2017). Bioactive Pentacyclic Triterpene Ester Derivatives from Alnus viridis ssp viridis Bark. in Journal of Natural Products
Amer Chemical Soc, Washington., 80(5), 1255-1263.
https://doi.org/10.1021/acs.jnatprod.6b00805

Novaković M, Nikodinović-Runić J, Veselinović J, Ilić-Tomić T, Vidaković V, Tešević V, Milosavljević S. Bioactive Pentacyclic Triterpene Ester Derivatives from Alnus viridis ssp viridis Bark. in Journal of Natural Products. 2017;80(5):1255-1263.
doi:10.1021/acs.jnatprod.6b00805 .

Novaković, Miroslav, Nikodinović-Runić, Jasmina, Veselinović, Jovana, Ilić-Tomić, Tatjana, Vidaković, Vera, Tešević, Vele, Milosavljević, Slobodan, "Bioactive Pentacyclic Triterpene Ester Derivatives from Alnus viridis ssp viridis Bark" in Journal of Natural Products, 80, no. 5 (2017):1255-1263,
https://doi.org/10.1021/acs.jnatprod.6b00805 . .