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Molecules 2013, 18(7), 8275-8288; doi:10.3390/molecules18078275
Article

Differential Growth Inhibitory Effects of Highly Oxygenated Guaianolides Isolated from the Middle Eastern Indigenous Plant Achillea falcata in HCT-116 Colorectal Cancer Cells

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Received: 21 May 2013; in revised form: 20 June 2013 / Accepted: 8 July 2013 / Published: 15 July 2013
(This article belongs to the Special Issue Bioassay-Guided Isolation of Natural Products)
Download PDF [297 KB, uploaded 18 June 2014]
Abstract: Medicinal plants play a crucial role in traditional medicine and in the maintenance of human health worldwide. Sesquiterpene lactones represent an interesting group of plant-derived compounds that are currently being tested as lead drugs in cancer clinical trials. Achillea falcata is a medicinal plant indigenous to the Middle Eastern region and belongs to the Asteraceae family, which is known to be rich in sesquiterpene lactones. We subjected Achillea falcata extracts to bioassay-guided fractionation against the growth of HCT-116 colorectal cancer cells and identified four secotanapartholides, namely 3-β-methoxy- isosecotanapartholide (1), isosecotanapartholide (2), tanaphallin (3), and 8-hydroxy-3-methoxyisosecotanapartholide (4). Three highly oxygenated guaianolides were isolated for the first time from Achillea falcata, namely rupin A (5), chrysartemin B (6), and 1β, 2β-epoxy- 3β,4α,10α-trihydroxyguaian- 6α,12-olide (7). These sesquiterpene lactones showed no or minor cytotoxicity while exhibiting promising anticancer effects against HCT-116 cells. Further structure-activity relationship studies related the bioactivity of the tested compounds to their skeleton, their lipophilicity, and to the type of functional groups neighboring the main alkylating center of the molecule.
Keywords: Achillea falcata; sesquiterpene lactones; guaianolides; colorectal cancer cells; bioassay-guided fractionation; structure-activity relationship Achillea falcata; sesquiterpene lactones; guaianolides; colorectal cancer cells; bioassay-guided fractionation; structure-activity relationship
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Tohme, R.; Al Aaraj, L.; Ghaddar, T.; Gali-Muhtasib, H.; Saliba, N.A.; Darwiche, N. Differential Growth Inhibitory Effects of Highly Oxygenated Guaianolides Isolated from the Middle Eastern Indigenous Plant Achillea falcata in HCT-116 Colorectal Cancer Cells. Molecules 2013, 18, 8275-8288.

AMA Style

Tohme R, Al Aaraj L, Ghaddar T, Gali-Muhtasib H, Saliba NA, Darwiche N. Differential Growth Inhibitory Effects of Highly Oxygenated Guaianolides Isolated from the Middle Eastern Indigenous Plant Achillea falcata in HCT-116 Colorectal Cancer Cells. Molecules. 2013; 18(7):8275-8288.

Chicago/Turabian Style

Tohme, Rita; Al Aaraj, Lamis; Ghaddar, Tarek; Gali-Muhtasib, Hala; Saliba, Najat A.; Darwiche, Nadine. 2013. "Differential Growth Inhibitory Effects of Highly Oxygenated Guaianolides Isolated from the Middle Eastern Indigenous Plant Achillea falcata in HCT-116 Colorectal Cancer Cells." Molecules 18, no. 7: 8275-8288.


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