Bisbibenzyls from Serbian Primula veris subsp. Columnae (Ten.) Lȕdi and P. acaulis (L.) L
Само за регистроване кориснике
2023
Аутори
Novaković, MiroslavIlić-Tomić, Tatjana
Đorđević, Iris
Anđelković, Boban
Tesević, Vele
Milosavljević, Slobodan
Asakawa, Yoshinori
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
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. Previ...ously, 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.
Кључне речи:
A549 lung cancer cell lines / Bisbibenzyls / Chemotaxonomy / Cytotoxic activity / Semipreparative HPLC / speciesИзвор:
Phytochemistry, 2023, 212, 113719-Финансирање / пројекти:
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200026 (Универзитет у Београду, Институт за хемију, технологију и металургију - ИХТМ) (RS-MESTD-inst-2020-200026)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200042 (Универзитет у Београду, Институт за молекуларну генетику и генетичко инжењерство) (RS-MESTD-inst-2020-200042)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200168 (Универзитет у Београду, Хемијски факултет) (RS-MESTD-inst-2020-200168)
- Serbian Academy of Sciences and Arts (Grant No. F188)
URI
https://www.sciencedirect.com/science/article/pii/S0031942223001358https://imagine.imgge.bg.ac.rs/handle/123456789/1862
Институција/група
Institut za molekularnu genetiku i genetičko inženjerstvoTY - 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 . .