Bisbibenzyls from Serbian Primula veris subsp. Columnae (Ten.) Lȕdi and P. acaulis (L.) L
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2023
Authors
Novaković, MiroslavIlić-Tomić, Tatjana
Đorđević, Iris
Anđelković, Boban D.
Tešević, Vele
Milosavljević, Slobodan
Asakawa, Yoshinori
Article (Published version)
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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. Pre...viously, 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.
Keywords:
bisbibenzyls / chemotaxonomy / semipreparative HPLC / cytotoxic activity / A549 lung cancer cell linesSource:
Phytochemistry, 2023, 212, 113719-Publisher:
- Elsevier
Funding / projects:
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200026 (University of Belgrade, Institute of Chemistry, Technology and Metallurgy - IChTM) (RS-MESTD-inst-2020-200026)
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200168 (University of Belgrade, Faculty of Chemistry) (RS-MESTD-inst-2020-200168)
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200042 (University of Belgrade, Institute of Molecular Genetics and Genetic Engineering) (RS-MESTD-inst-2020-200042)
- Serbian Academy of Sciences and Arts (Grant No. F188)
DOI: 10.1016/j.phytochem.2023.113719
ISSN: 0031-9422
WoS: 001000581900001
Scopus: 2-s2.0-85159057345
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IHTMTY - JOUR AU - Novaković, Miroslav AU - Ilić-Tomić, Tatjana AU - Đorđević, Iris AU - Anđelković, Boban D. AU - Tešević, Vele AU - Milosavljević, Slobodan AU - Asakawa, Yoshinori PY - 2023 PY - 2023 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/7188 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 SP - 113719 DO - 10.1016/j.phytochem.2023.113719 ER -
@article{ author = "Novaković, Miroslav and Ilić-Tomić, Tatjana and Đorđević, Iris and Anđelković, Boban D. and Tešević, Vele and Milosavljević, Slobodan 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., Ilić-Tomić, T., Đorđević, I., Anđelković, B. D., Tešević, V., Milosavljević, S.,& Asakawa, Y.. (2023). Bisbibenzyls from Serbian Primula veris subsp. Columnae (Ten.) Lȕdi and P. acaulis (L.) L. in Phytochemistry Elsevier., 212, 113719. https://doi.org/10.1016/j.phytochem.2023.113719
Novaković M, Ilić-Tomić T, Đorđević I, Anđelković BD, Tešević 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 D., Tešević, 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 . .