Monoterpenoid 5-methylcoumarins from Centrapalus pauciflorus with antiproliferative activity
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...
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| Format: | Article |
| Language: | English |
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Elsevier
2023-06-01
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| Series: | Arabian Journal of Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535223002393 |
| _version_ | 1797846336550207488 |
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| author | Muhammad Bello Saidu Gordana Krstić Nina Todorović Róbert Berkecz Hazhmat Ali István Zupkó Judit Hohmann Dóra Rédei |
| author_facet | Muhammad Bello Saidu Gordana Krstić Nina Todorović Róbert Berkecz Hazhmat Ali István Zupkó Judit Hohmann Dóra Rédei |
| author_sort | Muhammad Bello Saidu |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-09T17:54:20Z |
| format | Article |
| id | doaj.art-1e912f13dfa84f22a446ed9b8004d83b |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-04-09T17:54:20Z |
| publishDate | 2023-06-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-1e912f13dfa84f22a446ed9b8004d83b2023-04-15T05:52:18ZengElsevierArabian Journal of Chemistry1878-53522023-06-01166104777Monoterpenoid 5-methylcoumarins from Centrapalus pauciflorus with antiproliferative activityMuhammad Bello Saidu0Gordana Krstić1Nina Todorović2Róbert Berkecz3Hazhmat Ali4István Zupkó5Judit Hohmann6Dóra Rédei7Department of Pharmacognosy, University of Szeged, 6720 Szeged, HungaryDepartment of Pharmacognosy, University of Szeged, 6720 Szeged, Hungary; University of Belgrade, Faculty of Chemistry, 11000 Belgrade, SerbiaUniversity of Belgrade, Institute of Chemistry, Technology, and Metallurgy, Department of Chemistry, 11000 Belgrade, SerbiaInstitute of Pharmaceutical Analysis, University of Szeged, 6720 Szeged, HungaryInstitute of Pharmacodynamics and Biopharmacy, University of Szeged, 6720 Szeged, HungaryInstitute of Pharmacodynamics and Biopharmacy, University of Szeged, 6720 Szeged, HungaryDepartment of Pharmacognosy, University of Szeged, 6720 Szeged, Hungary; ELKH-USZ Biologically Active Natural Products Research Group, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary; Corresponding authors at: Institute of Pharmacognosy, University of Szeged, 6720 Szeged, Hungary.Department of Pharmacognosy, University of Szeged, 6720 Szeged, Hungary; Corresponding authors at: Institute of Pharmacognosy, University of Szeged, 6720 Szeged, Hungary.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.http://www.sciencedirect.com/science/article/pii/S1878535223002393Centrapalus pauciflorusAsteraceaeMonoterpenoid 5-methylcoumarinsAntiproliferative activityMTT assay |
| spellingShingle | Muhammad Bello Saidu Gordana Krstić Nina Todorović Róbert Berkecz Hazhmat Ali István Zupkó Judit Hohmann Dóra Rédei Monoterpenoid 5-methylcoumarins from Centrapalus pauciflorus with antiproliferative activity Arabian Journal of Chemistry Centrapalus pauciflorus Asteraceae Monoterpenoid 5-methylcoumarins Antiproliferative activity MTT assay |
| title | Monoterpenoid 5-methylcoumarins from Centrapalus pauciflorus with antiproliferative activity |
| title_full | Monoterpenoid 5-methylcoumarins from Centrapalus pauciflorus with antiproliferative activity |
| title_fullStr | Monoterpenoid 5-methylcoumarins from Centrapalus pauciflorus with antiproliferative activity |
| title_full_unstemmed | Monoterpenoid 5-methylcoumarins from Centrapalus pauciflorus with antiproliferative activity |
| title_short | Monoterpenoid 5-methylcoumarins from Centrapalus pauciflorus with antiproliferative activity |
| title_sort | monoterpenoid 5 methylcoumarins from centrapalus pauciflorus with antiproliferative activity |
| topic | Centrapalus pauciflorus Asteraceae Monoterpenoid 5-methylcoumarins Antiproliferative activity MTT assay |
| url | http://www.sciencedirect.com/science/article/pii/S1878535223002393 |
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