Bisbibenzyls from Serbian Primula veris subsp. Columnae (Ten.) Lȕdi and P. acaulis (L.) L
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2023
Authors
Novakovic, MiroslavIlic-Tomic, Tatjana
Djordjevic, Iris
Andjelkovic, Boban
Tesevic, Vele
Milosavljevic, Slobodan
Asakawa, Yoshinori
Article (Published version)
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Show full item recordAbstract
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
studie...d. 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.
Keywords:
Primula species / 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)
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Fakultet veterinarske medicineTY - JOUR AU - Novakovic, Miroslav AU - Ilic-Tomic, Tatjana AU - Djordjevic, Iris AU - Andjelkovic, Boban AU - Tesevic, Vele AU - Milosavljevic, Slobodan AU - Asakawa, Yoshinori PY - 2023 UR - https://vet-erinar.vet.bg.ac.rs/handle/123456789/3135 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. 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 = "Novakovic, Miroslav and Ilic-Tomic, Tatjana and Djordjevic, Iris and Andjelkovic, Boban and Tesevic, Vele and Milosavljevic, 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.", 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" }
Novakovic, M., Ilic-Tomic, T., Djordjevic, I., Andjelkovic, B., Tesevic, V., Milosavljevic, 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
Novakovic M, Ilic-Tomic T, Djordjevic I, Andjelkovic B, Tesevic V, Milosavljevic 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 .
Novakovic, Miroslav, Ilic-Tomic, Tatjana, Djordjevic, Iris, Andjelkovic, Boban, Tesevic, Vele, Milosavljevic, 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 . .