Anti-cancer thymoquinone from Nigella sativa

Ww, Li; Rosa, JO; Siddique,; Bajaña, Burgos; Sulé-Suso, Josep; Richardson, Alan

doi:10.1055/s-0033-1351896

Cited by 3 publications

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“…However, no anticancer activity of extracts of T. subcordata constituent alkaloids or further phytochemical study has been reported. Therefore, in continuation of our search for anticancer compounds from medicinal plants (Johnson‐Ajinwo et al ., ; Li et al , ; Li et al ., ), this study aimed to evaluate the in vitro anti‐ovarian cancer activities of the crude extracts and pure compounds of T. subcordata , and bioassay‐guided fractionation was used to isolate the bioactive compound. Furthermore, the cytotoxic effects and possible signalling pathways of cycleanine and tetrandrine involved in their cytotoxity on Ovcar‐8, A2780, Ovcar‐4, and Igrov‐1 ovarian cancer cell lines were investigated.…”

Section: Introductionmentioning

confidence: 99%

Cytotoxicity Effects and Apoptosis Induction by Bisbenzylisoquinoline Alkaloids fromTriclisia subcordata

et al. 2016

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Triclisia subcordata Oliv (Menispermeaceae) is a medicinal plant traditionally used for the treatment of various diseases in West Africa. The ethanol extract of T. subcordata and its fractions were screened for in vitro anti-ovarian cancer activities using the Sulforhodamine B assay. The crude alkaloids showed the strongest activity in cell growth assays on Ovcar-8 and A2780 cell lines (IC50 < 2.4 µg/mL). A bisbenzylisoquinoline alkaloid-cycleanine was isolated using HPLC and identified by mass spectrometry and nuclear magnetic resonance analyses. The IC50 values of cycleanine and tetrandrine (an alkaloid previously reported from this plant) ranged from 7 to 14 μM on Ovcar-8, A2780, Ovcar-4, and Igrov-1 ovarian cancer cell lines. The IC50 of cycleanine on human normal ovarian surface epithelial cells was 35 ± 1 μM, hinting at modest selectivity toward cancer cells. Both cycleanine and tetrandrine caused apoptosis as shown by activation of caspases 3/7 and cleavage of poly(ADP-ribose) polymerase to form poly(ADP-ribose) polymerase-1 by using western blot analysis. Flow cytometry analyses showed that the percentages of apoptotic cells and cells in subG1 phase increased after exposure of cycleanine and tetrandrine to Ovcar-8 cells for 48 h compared with control. Cycleanine, like its isomer tetrandrine isolated from T. subcordata, could be a potential new anti-ovarian cancer agent acting through the apoptosis pathway. Copyright © 2016 John Wiley & Sons, Ltd.

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Section: Introductionmentioning

confidence: 99%

Cytotoxicity Effects and Apoptosis Induction by Bisbenzylisoquinoline Alkaloids fromTriclisia subcordata

et al. 2016

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“…Cross-validation using standard addition confirms the accuracy and reliability of the SIDA method, which can quantify a large number of black cumin seed oil products for their quality control in high-throughput means. Synthetic deuteriated thymoquinone and the SID GC-MS method should also be useful in the studies on the mechanism of binding thymoquinone to proteins, ,− in vitro and in vivo pharmacokinetics of thymoquinone, which are ongoing in our laboratory …”

Section: Resultsmentioning

confidence: 99%

Stable Isotope Dilution Gas Chromatography–Mass Spectrometry for Quantification of Thymoquinone in Black Cumin Seed Oil

Johnson-Ajinwo

2014

J. Agric. Food Chem.

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Black cumin seed (Nigella sativa L.) is a widely used spice and herb, where thymoquinone (2-isopropyl-5-methyl-1,4-benzoquinone) is the major bioactive compound. Here, a stable isotope dilution (SID) gas chromatography-mass spectrometry (GC-MS) technique was developed for the quantification of thymoquinone. A doubly deuterated thymoquinone ([(2)H2]-thymoquinone) was synthesized for the first time with more than 93% deuteration degree shown by mass spectrometry and proton nuclear magnetic resonance ((1)H NMR). This compound was used as an internal standard for the quantification of thymoquinone using a SID GC-MS method. The validation experiment showed a recovery rate of 99.1 ± 1.1% relative standard deviation (RSD). Standard addition and external calibration methods have also been used to quantify thymoquinone, which cross-validated the developed stable isotope dilution assay (SIDA). In comparison to external calibration and standard addition methods, the SIDA method is robust and accurate. The concentration of thymoquinone in five marketed black cumin seed oils ranged between 3.34 and 10.8 mg/mL by use of SID GC-MS.

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The synthesis and evaluation of thymoquinone analogues as anti-ovarian cancer and antimalarial agents

Johnson-Ajinwo

Ullah

Mbye

et al. 2018

Bioorganic & Medicinal Chemistry Letters

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Thymoquinone (TQ), 2-isopropyl-5-methyl-1,4-benzoquinone, a natural product isolated from Nigella sativa L., has previously been demonstrated to exhibit antiproliferative activity in vitro against a range of cancers as well as the human malarial parasite Plasmodium falciparum. We describe here the synthesis of a series of analogues of TQ that explore the potential for nitrogen-substitution to this scaffold, or reduction to a hydroquinone scaffold, in increasing the potency of this antiproliferative activity against ovarian cancer cell lines and P. falciparum. In addition, alkyl or halogen-substituted analogues were commercially sourced and tested in parallel. Several TQ analogues with improved potency against ovarian cancer cells and P. falciparum were found, although this increase is suggested to be moderate. Key aspects of the structure activity relationship that could be further explored are highlighted.

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Anti-cancer thymoquinone from Nigella sativa

Cited by 3 publications

References 0 publications

Cytotoxicity Effects and Apoptosis Induction by Bisbenzylisoquinoline Alkaloids fromTriclisia subcordata

Cytotoxicity Effects and Apoptosis Induction by Bisbenzylisoquinoline Alkaloids fromTriclisia subcordata

Stable Isotope Dilution Gas Chromatography–Mass Spectrometry for Quantification of Thymoquinone in Black Cumin Seed Oil

The synthesis and evaluation of thymoquinone analogues as anti-ovarian cancer and antimalarial agents

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