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 . .