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Gyphothamnium pinifolium Phil. is an evergreen Chilean native bush with white-violet flowers growing in Paposo valley in the cost of the Atacama Desert. The combination of high-speed counter-current chromatography (HSCCC) and medium pressure column chromatography allowed the fast isolation and purification of one rare phenolic derivative: 2-Nor-1,2-secolycoserone, one 5-methyl-coumarin: Aphyllodenticulide, one ent-labdane: ent-labda-8,13-E-diene-15-ol (compounds 1-3) and a inseparable mixture of common sterols (mainly composed of lupeol and taraxerol) from this Chilean species. In order to prepare the main individual compounds, a rapid enrichment step (only 100 min) was achieved by HSCCC using the solvent system n-hexane: ethyl acetate: acetonitrile 5:2:5 v:v:v, followed by a fast final purification step of the mentioned compounds by normal phase medium pressure column chromatography (MPC). The isolated compounds were evaluated against breast cancer MCF-7 cells, showing good cytotoxic activity (<50% cell viability at 100 mu M). Besides, compound 1 showed the best cytotoxicity, (IC50 = 15.12 mu M), but was also toxic against its normal counterpart MCF-10F cells (IC50=13.79 mu M). Based on these results, it is concluded that HSCCC is a viable separation method for the purification of novel compounds from Gyphotamnium pinifolium with cytotoxic activity in cancer cells. Furthermore, the X-ray crystal-structure for compound 2 is reported in this paper for the first time. (C) 2015 Elsevier B.V. All rights reserved.