| Autor: |
Clement JA; a Department of Chemistry and Physics , Western Carolina University , Cullowhee , NC , USA.; b Natural Products Discovery Institute , Baruch S. Blumberg Institute , Doylestown , PA , USA., Bleich RM; a Department of Chemistry and Physics , Western Carolina University , Cullowhee , NC , USA., Campbell HE; a Department of Chemistry and Physics , Western Carolina University , Cullowhee , NC , USA., Naylor K; a Department of Chemistry and Physics , Western Carolina University , Cullowhee , NC , USA., Flood MJ; a Department of Chemistry and Physics , Western Carolina University , Cullowhee , NC , USA., Kelly RM; c Bent Creek Institute , Asheville NC , USA., Wu SB; d Department of Biological Sciences, Lehman College , City University of New York , Bronx , NY , USA., Kennelly EJ; d Department of Biological Sciences, Lehman College , City University of New York , Bronx , NY , USA., Schmitt JD; c Bent Creek Institute , Asheville NC , USA. |
| Abstrakt: |
Pale Indian plantain (Arnoglossum atriplicifolium (L.) H. Rob.) is a plant with traditional medicinal usage among the Cherokee Native American tribe for treating cancer. Two oplopane sesquiterpenoids were isolated from an extract of A. atriplicifolium from Western North Carolina. The compounds were isolated by bioassay-guided fractionation using an MCF-7 breast tumour cell line assay. The known compound (1S,6R,7R,8R)-1-acetoxy-6,7-diangeloxy-8,10-epoxy-2-oxo-oplopa-3,14Z,11,12-dien-13-al (1) had an EC50 value of 9.0 μM against MCF-7 cells, while the new compound (1S,3R,6R,7R,8R,11S)-1-acetoxy-6,7-diangeloxy-8,10,11,13-bisepoxyoplopan-2-one (2) had an EC50 value of 96 μM. The compounds were characterised by 1D and 2D NMR spectroscopy and by comparison with literature values in the case for 1. Based on NOESY analysis, a correction of the relative configuration for 1 is presented. The presence of these compounds may help to explain the folk remedy usage of this plant as an anticancer agent. |
