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The aim of this study was to investigate the anticancer activities of five chloroform extracts prepared from the aerial parts of <i>C</i><i>enteura</i><i> </i><i>kilaea</i><i> </i>Boiss. (CKC), <i>C.</i><i> </i><i>cuneifolia</i> Sm. (CCC), <i>C. salicifolia</i><i> </i>M.Bieb. ex Willd. (CSAC), <i>C. </i><i>stenolepis</i><i> </i>Kerner (CSC1 and CSC2) against hepatocellular cancer HepG2 cell line. At the same time, antioxidant and anti-inflammatory activities of the extracts were examined. Anticancer, anti-inflammatory, antioxidant activities of extracts were carried out by MTT, lipoxygenase, DPPH-ABTS methods, respectively. CCC, CSAC and CKC have the highest anticancer activity when compared to other extracts. Similarly, CSAC and CCC had the best antioxidant capacity, while CSAC and CKC showed strong anti-lipoxygenase activity. Among all the tested extracts, the highest amounts of total phenolic were found in the CSAC. The study revealed that CSAC and CCC displays remarkable antioxidant, anticancer and anti-inflammatory activity.