Monoterpenoid 5-methylcoumarins from Centrapalus pauciflorus with antiproliferative activity
Аутори
Saidu, Muhammad BelloKrstić, Gordana B.
Todorović, Nina
Berkecz, Róbert
Ali, Hazhmat
Zupkó, István
Hohmann, Judit
Rédei, Dóra
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Thirteen undescribed monoterpene-fused 5-methylcoumarins, named centrapalus coumarins A–M, were isolated from the aerial parts of the Centrapalus pauciflorus together with seven known compounds. The structures were established by extensive spectroscopic analyses, including 1D NMR, 2D NMR, and HR-ESI-MS experiments. The compounds represent a wide range of chemical diversity depending on the connection of the head-to-tail coupled diisoprene unit. Centrapalus coumarins A–H and I–L are based on 6–6–6- and 6–6-7-membered tricyclic ring systems, respectively. Centrapalus coumarins D and E exhibit cyclic hemiketal structures, while centrapalus coumarins F is unique because its monoterpene part forms an additional lactone ring. Centrapalus coumarin L is the only compound containing a modified trinor-monoterpene part. Centrapalus coumarin M is unprecedented as it contains a pentacyclic heterocyclic ring system. Sixteen isolated compounds were investigated for antiproliferative activity on the h...uman breast (MCF-7 and MDA-MB-231), cervical (HeLa and SiHa), and ovarian (A2780) cancer-cell lines by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay, and a few of them exhibited substantial activity. Centrapalus coumarin F demonstrated the highest potency against MCF-7, HeLa, and A2780 cells with IC50 values of 6.59, 2.28, and 15.41 μM, respectively. The cytotoxic activity of centrapalus coumarin F showed moderate cancer selectivity, as determined using intact fibroblast cells (NIH-3 T3). The antiproliferative activity of these 5-methylcoumarin derivatives provides evidence for the establishment of structure–activity relationships.
Кључне речи:
Antiproliferative activity / Asteraceae / Monoterpenoid 5-methylcoumarins / MTT assayИзвор:
Arabian Journal of Chemistry, 2023, 16, 6, 104777-Издавач:
- Elsevier
Финансирање / пројекти:
- National Research, Development and Innovation Office, Hungary (NKFIH; K-143690)
- Ministry of Innovation and Technology of Hungary from NKFIH Fund, project no. TKP2021-EGA-32
- University of Szeged Open Access Fund, grant number 5948
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Saidu, Muhammad Bello AU - Krstić, Gordana B. AU - Todorović, Nina AU - Berkecz, Róbert AU - Ali, Hazhmat AU - Zupkó, István AU - Hohmann, Judit AU - Rédei, Dóra PY - 2023 UR - http://cherry.chem.bg.ac.rs/handle/123456789/6186 AB - Thirteen undescribed monoterpene-fused 5-methylcoumarins, named centrapalus coumarins A–M, were isolated from the aerial parts of the Centrapalus pauciflorus together with seven known compounds. The structures were established by extensive spectroscopic analyses, including 1D NMR, 2D NMR, and HR-ESI-MS experiments. The compounds represent a wide range of chemical diversity depending on the connection of the head-to-tail coupled diisoprene unit. Centrapalus coumarins A–H and I–L are based on 6–6–6- and 6–6-7-membered tricyclic ring systems, respectively. Centrapalus coumarins D and E exhibit cyclic hemiketal structures, while centrapalus coumarins F is unique because its monoterpene part forms an additional lactone ring. Centrapalus coumarin L is the only compound containing a modified trinor-monoterpene part. Centrapalus coumarin M is unprecedented as it contains a pentacyclic heterocyclic ring system. Sixteen isolated compounds were investigated for antiproliferative activity on the human breast (MCF-7 and MDA-MB-231), cervical (HeLa and SiHa), and ovarian (A2780) cancer-cell lines by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay, and a few of them exhibited substantial activity. Centrapalus coumarin F demonstrated the highest potency against MCF-7, HeLa, and A2780 cells with IC50 values of 6.59, 2.28, and 15.41 μM, respectively. The cytotoxic activity of centrapalus coumarin F showed moderate cancer selectivity, as determined using intact fibroblast cells (NIH-3 T3). The antiproliferative activity of these 5-methylcoumarin derivatives provides evidence for the establishment of structure–activity relationships. PB - Elsevier T2 - Arabian Journal of Chemistry T1 - Monoterpenoid 5-methylcoumarins from Centrapalus pauciflorus with antiproliferative activity VL - 16 IS - 6 SP - 104777 DO - 10.1016/j.arabjc.2023.104777 ER -
@article{ author = "Saidu, Muhammad Bello and Krstić, Gordana B. and Todorović, Nina and Berkecz, Róbert and Ali, Hazhmat and Zupkó, István and Hohmann, Judit and Rédei, Dóra", year = "2023", abstract = "Thirteen undescribed monoterpene-fused 5-methylcoumarins, named centrapalus coumarins A–M, were isolated from the aerial parts of the Centrapalus pauciflorus together with seven known compounds. The structures were established by extensive spectroscopic analyses, including 1D NMR, 2D NMR, and HR-ESI-MS experiments. The compounds represent a wide range of chemical diversity depending on the connection of the head-to-tail coupled diisoprene unit. Centrapalus coumarins A–H and I–L are based on 6–6–6- and 6–6-7-membered tricyclic ring systems, respectively. Centrapalus coumarins D and E exhibit cyclic hemiketal structures, while centrapalus coumarins F is unique because its monoterpene part forms an additional lactone ring. Centrapalus coumarin L is the only compound containing a modified trinor-monoterpene part. Centrapalus coumarin M is unprecedented as it contains a pentacyclic heterocyclic ring system. Sixteen isolated compounds were investigated for antiproliferative activity on the human breast (MCF-7 and MDA-MB-231), cervical (HeLa and SiHa), and ovarian (A2780) cancer-cell lines by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay, and a few of them exhibited substantial activity. Centrapalus coumarin F demonstrated the highest potency against MCF-7, HeLa, and A2780 cells with IC50 values of 6.59, 2.28, and 15.41 μM, respectively. The cytotoxic activity of centrapalus coumarin F showed moderate cancer selectivity, as determined using intact fibroblast cells (NIH-3 T3). The antiproliferative activity of these 5-methylcoumarin derivatives provides evidence for the establishment of structure–activity relationships.", publisher = "Elsevier", journal = "Arabian Journal of Chemistry", title = "Monoterpenoid 5-methylcoumarins from Centrapalus pauciflorus with antiproliferative activity", volume = "16", number = "6", pages = "104777", doi = "10.1016/j.arabjc.2023.104777" }
Saidu, M. B., Krstić, G. B., Todorović, N., Berkecz, R., Ali, H., Zupkó, I., Hohmann, J.,& Rédei, D.. (2023). Monoterpenoid 5-methylcoumarins from Centrapalus pauciflorus with antiproliferative activity. in Arabian Journal of Chemistry Elsevier., 16(6), 104777. https://doi.org/10.1016/j.arabjc.2023.104777
Saidu MB, Krstić GB, Todorović N, Berkecz R, Ali H, Zupkó I, Hohmann J, Rédei D. Monoterpenoid 5-methylcoumarins from Centrapalus pauciflorus with antiproliferative activity. in Arabian Journal of Chemistry. 2023;16(6):104777. doi:10.1016/j.arabjc.2023.104777 .
Saidu, Muhammad Bello, Krstić, Gordana B., Todorović, Nina, Berkecz, Róbert, Ali, Hazhmat, Zupkó, István, Hohmann, Judit, Rédei, Dóra, "Monoterpenoid 5-methylcoumarins from Centrapalus pauciflorus with antiproliferative activity" in Arabian Journal of Chemistry, 16, no. 6 (2023):104777, https://doi.org/10.1016/j.arabjc.2023.104777 . .