Fast isolation of cytotoxic compounds from the native Chilean species Gypothamnium pinifolium Phil. collected in the Atacama Desert, northern Chile
2015
Simirgiotis, Mario J. | Bórquez, Jorge | Neves-Vieira, Mariana | Brito, Iván | Alfaro-Lira, Susana | Winterhalter, Peter | Echiburú-Chau, Carlos | Jerz, Gerold | Cárdenas, Alejandro
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 100min) 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 100μM). Besides, compound 1 showed the best cytotoxicity, (IC50=15.12μM), but was also toxic against its normal counterpart MCF-10F cells (IC50=13.79μM). 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.
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