Monoterpenoid 5-methylcoumarins from Centrapalus pauciflorus with antiproliferative activity

Saidu, Muhammad Bello; Krstić, Gordana; Todorović, Nina; Berkecz, Róbert; Ali, H. Abu; Zupkó, István; Hohmann, Judit; Rédei, Dóra

doi:10.1016/j.arabjc.2023.104777

Cited by 2 publications

(4 citation statements)

References 19 publications

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“… a Inhibition values lower than 20% are considered negligible and not given numerically. b Not determined. c Results from ref . …”

Section: Resultsmentioning

confidence: 99%

“…The cell culturing and evaluation of the antiproliferative effects of the isolated compounds against a panel of human cancer cell lines derived from gynecological origin were conducted using a methodology described previously. 20 …”

Section: Methodsmentioning

confidence: 99%

“…Continuing our ongoing investigation on the metabolites of Centrapalus pauciflorus (Willd.) H.Rob., , this study reports the isolation and structure determination of eight chromone-meroterpenoids named pauciflorins F–M ( 1 – 10 ) and two 5-methyl-2,4-chromadione-meroterpenoids pauciflorins N and O ( 10 – 11 ), extracted from the leaves of C . pauciflorus .…”

Section: Introductionmentioning

confidence: 99%

“…In folklore medicine, its leaves are cooked in porridge or brewed as tea to alleviate chest pain. The plant is also used to relieve stomach pain …”

Section: Introductionmentioning

confidence: 99%

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Anticancer Meroterpenoids from Centrapalus pauciflorus leaves: Chromone- and 2,4-Chromadione-Monoterpene Derivatives

et al. 2023

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Eight previously undescribed chromones, named pauciflorins F–M and two 5-methyl-2,4-chromadione derivatives named as pauciflorins N and O, were isolated from the methanol extract of the leaves of Centrapalus pauciflorus (Willd.) H.Rob. together with the known (+)-spiro-ethuliacoumarin. The structures were determined via extensive spectroscopic analyses, including HRESIMS, 1D NMR (1H, 13C JMOD), and 2D NMR (HSQC, HMBC, 1H–1H COSY, and NOESY) experiments. Through an MTT assay, seven isolated compounds were tested for their antiproliferative properties against human adherent breast (MCF-7, MDA-MB-231), cervical (HeLa, SiHa), and ovarian (A2780) cancer cell lines. Pauciflorin F was effective against MCF-7 breast cancer cells, its activity (IC50 5.78 μM) was comparable to that of the reference agent cisplatin (IC50 5.78 μM).

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“… a Inhibition values lower than 20% are considered negligible and not given numerically. b Not determined. c Results from ref . …”

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…In folklore medicine, its leaves are cooked in porridge or brewed as tea to alleviate chest pain. The plant is also used to relieve stomach pain …”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Anticancer Meroterpenoids from Centrapalus pauciflorus leaves: Chromone- and 2,4-Chromadione-Monoterpene Derivatives

et al. 2023

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New Members of the Centrapalus Coumarin and Pauciflorin Series from Centrapalus pauciflorus

Saidu,

Krstić,

Bombicz

et al. 2024

Pharmaceutics

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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–monoterpene 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 > 10 µM) but selective activity against A2780 cells.

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Monoterpenoid 5-methylcoumarins from Centrapalus pauciflorus with antiproliferative activity

Cited by 2 publications

References 19 publications

Anticancer Meroterpenoids from Centrapalus pauciflorus leaves: Chromone- and 2,4-Chromadione-Monoterpene Derivatives

Anticancer Meroterpenoids from Centrapalus pauciflorus leaves: Chromone- and 2,4-Chromadione-Monoterpene Derivatives

New Members of the Centrapalus Coumarin and Pauciflorin Series from Centrapalus pauciflorus

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