Chemical Constituents of and Anti-Inflammatory, Cytotoxic, and Apoptotic Activities of Eupatoriopicrin on Cancer Stem Cells.

Thunb. of the plant family Asteraceae is a popular traditional herb in Vietnam. However, its chemical constituents as well as bioactive principles have not been investigated yet. We investigated the phytochemistry of in Vietnam and isolated seventeen compounds including phytosterols, terpenoids, phenolic acids, flavonoids, fatty alcohols, and fatty acids. They were structurally determined by MS and NMR analysis. Except for compounds and , all the other compounds were identified for the first time from . Since many sesquiterpene lactones with -methylene -lactone ring are reported as anti-inflammatory and anticancer agents, eupatoriopicrin , 1-hydroxy-8-(4,5-dihydroxytigloyloxy)eudesma-4(15),11(13)-dien-6,12-olide were selected among the isolates for biological assays. Compound was identified as the main bioactive sesquiterpene lactone of showing its potent anti-inflammatory and cytotoxic activity through inhibiting NO production and the growth of HepG2 and MCF-7 human cancer cell lines. For the first time, eupatoriopicrin was demonstrated to strongly inhibit NTERA-2 human cancer stem cell (CSC) line . It is noticeable that the cytotoxicity of eupatoriopicrin against NTERA-2 cells is mediated by its apoptosis-inducing capability of as demonstrated by the results of Hoechst 33342 staining, flow cytometry apoptosis analysis, and caspase-3 activity assays. The biological activities of the main bioactive constituents -, , , and supported the reported anti-inflammatory and anticancer properties of extracts from .