TY  - 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 . .

TY  - JOUR
AU  - Krstić, Gordana B.
AU  - Saidu, Muhammad Bello
AU  - Bombicz, Petra
AU  - De, Sourav
AU  - Ali, Hazhmat
AU  - Zupkó, István
AU  - Berkecz, Róbert
AU  - Gallah, Umar Shehu
AU  - Rédei, Dóra
AU  - Hohmann, Judit
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6197
AB  - Five unusual meroterpenoids based on new carbon skeletons, pauciflorins A–E (1–5), were isolated by multistep chromatographic separations of a methanol extract of the aerial parts of Centrapalus pauciflorus. Compounds 1–3 are derived by the connection of a 2-nor-chromone and a monoterpene unit, whereas 4 and 5 are dihydrochromone–monoterpene adducts with a rarely occurring orthoester functionality. The structures were solved using 1D and 2D NMR, HRESIMS, and single-crystal X-ray diffraction. Pauciflorins A–E were evaluated for antiproliferative activity against human gynecological cancer cell lines, but were inactive (IC50 < 10 μM) in each case.
PB  - American Chemical Society
T2  - Journal of Natural Products
T1  - Pauciflorins A–E, Unexpected Chromone–Monoterpene-Derived Meroterpenoids from Centrapalus pauciflorus
VL  - 86
IS  - 4
SP  - 891
EP  - 896
DO  - 10.1021/acs.jnatprod.2c01132
ER  - 

@article{
author = "Krstić, Gordana B. and Saidu, Muhammad Bello and Bombicz, Petra and De, Sourav and Ali, Hazhmat and Zupkó, István and Berkecz, Róbert and Gallah, Umar Shehu and Rédei, Dóra and Hohmann, Judit",
year = "2023",
abstract = "Five unusual meroterpenoids based on new carbon skeletons, pauciflorins A–E (1–5), were isolated by multistep chromatographic separations of a methanol extract of the aerial parts of Centrapalus pauciflorus. Compounds 1–3 are derived by the connection of a 2-nor-chromone and a monoterpene unit, whereas 4 and 5 are dihydrochromone–monoterpene adducts with a rarely occurring orthoester functionality. The structures were solved using 1D and 2D NMR, HRESIMS, and single-crystal X-ray diffraction. Pauciflorins A–E were evaluated for antiproliferative activity against human gynecological cancer cell lines, but were inactive (IC50 < 10 μM) in each case.",
publisher = "American Chemical Society",
journal = "Journal of Natural Products",
title = "Pauciflorins A–E, Unexpected Chromone–Monoterpene-Derived Meroterpenoids from Centrapalus pauciflorus",
volume = "86",
number = "4",
pages = "891-896",
doi = "10.1021/acs.jnatprod.2c01132"
}

Krstić, G. B., Saidu, M. B., Bombicz, P., De, S., Ali, H., Zupkó, I., Berkecz, R., Gallah, U. S., Rédei, D.,& Hohmann, J.. (2023). Pauciflorins A–E, Unexpected Chromone–Monoterpene-Derived Meroterpenoids from Centrapalus pauciflorus. in Journal of Natural Products
American Chemical Society., 86(4), 891-896.
https://doi.org/10.1021/acs.jnatprod.2c01132

Krstić GB, Saidu MB, Bombicz P, De S, Ali H, Zupkó I, Berkecz R, Gallah US, Rédei D, Hohmann J. Pauciflorins A–E, Unexpected Chromone–Monoterpene-Derived Meroterpenoids from Centrapalus pauciflorus. in Journal of Natural Products. 2023;86(4):891-896.
doi:10.1021/acs.jnatprod.2c01132 .

Krstić, Gordana B., Saidu, Muhammad Bello, Bombicz, Petra, De, Sourav, Ali, Hazhmat, Zupkó, István, Berkecz, Róbert, Gallah, Umar Shehu, Rédei, Dóra, Hohmann, Judit, "Pauciflorins A–E, Unexpected Chromone–Monoterpene-Derived Meroterpenoids from Centrapalus pauciflorus" in Journal of Natural Products, 86, no. 4 (2023):891-896,
https://doi.org/10.1021/acs.jnatprod.2c01132 . .

TY  - JOUR
AU  - Krstić, Gordana B.
AU  - Saidu, Muhammad Bello
AU  - Barta, Anita
AU  - Vágvölgyi, Máté
AU  - Ali, Hazhmat
AU  - Zupkó, István
AU  - Berkecz, Róbert
AU  - Gallah, Umar Shehu
AU  - Rédei, Dóra
AU  - Hohmann, Judit
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6330
AB  - 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).
PB  - American Chemical Society
T2  - ACS Omega
T1  - Anticancer Meroterpenoids from Centrapalus pauciflorus leaves: Chromone- and 2,4-Chromadione-Monoterpene Derivatives
VL  - 8
IS  - 34
SP  - 31389
EP  - 31398
DO  - 10.1021/acsomega.3c03884
ER  - 

@article{
author = "Krstić, Gordana B. and Saidu, Muhammad Bello and Barta, Anita and Vágvölgyi, Máté and Ali, Hazhmat and Zupkó, István and Berkecz, Róbert and Gallah, Umar Shehu and Rédei, Dóra and Hohmann, Judit",
year = "2023",
abstract = "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).",
publisher = "American Chemical Society",
journal = "ACS Omega",
title = "Anticancer Meroterpenoids from Centrapalus pauciflorus leaves: Chromone- and 2,4-Chromadione-Monoterpene Derivatives",
volume = "8",
number = "34",
pages = "31389-31398",
doi = "10.1021/acsomega.3c03884"
}

Krstić, G. B., Saidu, M. B., Barta, A., Vágvölgyi, M., Ali, H., Zupkó, I., Berkecz, R., Gallah, U. S., Rédei, D.,& Hohmann, J.. (2023). Anticancer Meroterpenoids from Centrapalus pauciflorus leaves: Chromone- and 2,4-Chromadione-Monoterpene Derivatives. in ACS Omega
American Chemical Society., 8(34), 31389-31398.
https://doi.org/10.1021/acsomega.3c03884

Krstić GB, Saidu MB, Barta A, Vágvölgyi M, Ali H, Zupkó I, Berkecz R, Gallah US, Rédei D, Hohmann J. Anticancer Meroterpenoids from Centrapalus pauciflorus leaves: Chromone- and 2,4-Chromadione-Monoterpene Derivatives. in ACS Omega. 2023;8(34):31389-31398.
doi:10.1021/acsomega.3c03884 .

Krstić, Gordana B., Saidu, Muhammad Bello, Barta, Anita, Vágvölgyi, Máté, Ali, Hazhmat, Zupkó, István, Berkecz, Róbert, Gallah, Umar Shehu, Rédei, Dóra, Hohmann, Judit, "Anticancer Meroterpenoids from Centrapalus pauciflorus leaves: Chromone- and 2,4-Chromadione-Monoterpene Derivatives" in ACS Omega, 8, no. 34 (2023):31389-31398,
https://doi.org/10.1021/acsomega.3c03884 . .