{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,4]],"date-time":"2025-11-04T11:14:53Z","timestamp":1762254893305,"version":"build-2065373602"},"reference-count":30,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2024,7,6]],"date-time":"2024-07-06T00:00:00Z","timestamp":1720224000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Nemzeti Kutat\u00e1si Fejleszt\u00e9si \u00e9s Innov\u00e1ci\u00f3s Hivatal (NKFIH)","award":["TKP2021-EGA-32"],"award-info":[{"award-number":["TKP2021-EGA-32"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Pharmaceutics"],"abstract":"<jats:p>Monoterpene and 5-methylcoumarin- or 5-methylchromone-coupled meroterpenoids occurring mainly in the Asteraceae species proved to have high potency against protozoans, worms, and various tumor cells, which make them interesting targets for searching for new bioactive compounds. The African plant Centrapalus pauciflorus was applied in traditional medicine for healing chest pain and stomach aches. Three new meroterpenoids named centrapalus coumarin N (2), pauciflorins P (3), and Q (4), and the already known cyclohoehnelia coumarin (1), were isolated from the chloroform extract of C. pauciflorus, together with centrapalus coumarin O (5), which was obtained for the first time from a natural source. The structures were established from HRESIMS, 1D (1H NMR, 13C NMR JMOD) and 2D NMR (HSQC, HMBC, 1H-1H COSY, NOESY) spectroscopies, and the absolute stereochemistry of 5 was determined by single-crystal X-ray diffraction. Compounds 1, 2, and 5 are hybrid molecules of 5-methylcoumarin\u2013monoterpene origin. Centrapalus coumarin N is the first example of meroterpenoids, where a monoterpene is fused with a coumarin and an acetophenone unit. Pauciflorins P and Q are dimeric meroterpenoid isomers. Centrapalus coumarins N and O were tested for antiproliferative activity against human adherent breast (MCF-7, MDA-MB-231), cervical (HeLa, SiHa), and ovarian (A2780) cancer cell lines, and were additionally included to obtain data concerning cancer selectivity. Both compounds exhibited moderate (IC50 &gt; 10 \u00b5M) but selective activity against A2780 cells.<\/jats:p>","DOI":"10.3390\/pharmaceutics16070907","type":"journal-article","created":{"date-parts":[[2024,7,8]],"date-time":"2024-07-08T14:40:50Z","timestamp":1720449650000},"page":"907","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["New Members of the Centrapalus Coumarin and Pauciflorin Series from Centrapalus pauciflorus"],"prefix":"10.3390","volume":"16","author":[{"given":"Muhammad Bello","family":"Saidu","sequence":"first","affiliation":[{"name":"Department of Pharmacognosy, University of Szeged, E\u00f6tv\u00f6s u. 6, 6720 Szeged, Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Gordana","family":"Krsti\u0107","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, University of Belgrade, Studentski trg 12-16, 11158 Belgrade, Serbia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5509-1515","authenticated-orcid":false,"given":"Petra","family":"Bombicz","sequence":"additional","affiliation":[{"name":"Centre for Structural Science, HUN-REN Research Centre for Natural Sciences, Magyar Tud\u00f3sok k\u00f6r\u00fatja 2, 1117 Budapest, Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3014-8084","authenticated-orcid":false,"given":"Sourav","family":"De","sequence":"additional","affiliation":[{"name":"Centre for Structural Science, HUN-REN Research Centre for Natural Sciences, Magyar Tud\u00f3sok k\u00f6r\u00fatja 2, 1117 Budapest, Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0606-2766","authenticated-orcid":false,"given":"Anita","family":"Barta","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, University of Szeged, E\u00f6tv\u00f6s u. 6, 6720 Szeged, Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2553-8443","authenticated-orcid":false,"given":"Hazhmat","family":"Ali","sequence":"additional","affiliation":[{"name":"Institute of Pharmacodynamics and Biopharmacy, University of Szeged, E\u00f6tv\u00f6s u. 6, 6720 Szeged, Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3243-5300","authenticated-orcid":false,"given":"Istv\u00e1n","family":"Zupk\u00f3","sequence":"additional","affiliation":[{"name":"Institute of Pharmacodynamics and Biopharmacy, University of Szeged, E\u00f6tv\u00f6s u. 6, 6720 Szeged, Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9076-2177","authenticated-orcid":false,"given":"R\u00f3bert","family":"Berkecz","sequence":"additional","affiliation":[{"name":"Institute of Pharmaceutical Analysis, University of Szeged, Somogyi u. 4, 6720 Szeged, Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Umar Shehu","family":"Gallah","sequence":"additional","affiliation":[{"name":"Bioresource Department, National Research Institute for Chemical Technology (NARICT), Zaria PMB 1052, Nigeria"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5013-247X","authenticated-orcid":false,"given":"D\u00f3ra","family":"R\u00e9dei","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, University of Szeged, E\u00f6tv\u00f6s u. 6, 6720 Szeged, Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Judit","family":"Hohmann","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, University of Szeged, E\u00f6tv\u00f6s u. 6, 6720 Szeged, Hungary"},{"name":"HUN-REN\u2013USZ Biologically Active Natural Products Research Group, University of Szeged, E\u00f6tv\u00f6s u. 6, 6720 Szeged, Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2024,7,6]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"e000285","DOI":"10.1136\/esmoopen-2017-000285","article-title":"Global cancer control: Responding to the growing burden, rising costs and inequalities in access","volume":"3","author":"Prager","year":"2018","journal-title":"ESMO Open"},{"key":"ref_2","first-page":"102","article-title":"Terpenoid biosynthesis","volume":"4","author":"Cornforth","year":"1968","journal-title":"Chem. 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