Isolation of cytotoxic diterpenoids from the Chilean medicinal plantAzorella compactaPhil from the Atacama Desert by high-speed counter-current chromatography
| Autor: | Carlos Echiburú-Chau, Gerold Jerz, Javier Vallejos, Nandy López Bartolucci, Peter Winterhalter, Mario J. Simirgiotis, Jorge Bórquez |
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| Rok vydání: | 2015 |
| Předmět: |
Nutrition and Dietetics
Apiaceae biology Traditional medicine 010405 organic chemistry Azorella Fractionation biology.organism_classification 01 natural sciences 0104 chemical sciences 010404 medicinal & biomolecular chemistry Countercurrent chromatography Botany Cytotoxic T cell Azorellane Agronomy and Crop Science MCF7 Cells Food Science Biotechnology |
| Zdroj: | Journal of the Science of Food and Agriculture. 96:2832-2838 |
| ISSN: | 0022-5142 |
| DOI: | 10.1002/jsfa.7451 |
| Popis: | BACKGROUND Azorella compacta (Apiaceae) is a native Chilean cushion shrub which produces a resin containing mulinane and azorellane diterpenoids. This plant has been used since pre-Colombian times to treat inflammation and dental neuralgias. In this work the first preparative fractionation of diterpenoids present in this plant by means of high-speed counter-current chromatography (HSCCC) was applied, and cytotoxic effects of the isolated compounds were evaluated for the first time against a panel of MCF7 cells. RESULTS The major compounds isolated were identified by means of spectroscopy as azorellanol, 13α, 14α-dihydroxymulin-11-en-20-oic acid, mulinolic acid, mulin-11,13-dien-20-oic acid, 17-acetoxy-mulin-11,13-dien-20 oic acid, and 17-acetoxy-mulinic acid (compounds 7, 9–11 and 13, respectively), and four minor diterpenoids [7-deacetyl-azorellanol (6), 13-epi-azorellanol, 7-acetoxy-mulin-9,12-diene, and 17-acetoxy-mulin-11,13-dien-20-oic acid (compounds 4, 8 and 12)], together with three new minor diterpenoids: 13β,14β-dihydroxymulin-11-en-20-oic acid (1), 13-epiazorellanone (2) and 13-epi-7-deacetyl-azorellanol (3) were identified. Besides, compounds 4, 6, 7, 8 and 11 displayed good cytotoxic activity (less than 50% cell viability at 100 µM). Among them, compound 7, an acetylated azorellane, was the most active. CONCLUSIONS HSCCC allowed the isolation of 13 diterpenoids present in A. compacta. Three compounds are reported for the first time. Isolated azorellanes are more potent cytotoxic agents than are mulinanes. © 2015 Society of Chemical Industry |
| Databáze: | OpenAIRE |
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