Bioactive sesquiterpene lactones isolated from the whole plants of Vernonia cinerea

Authors: ZHANG, M. - University Of Hawaii; YANG, XI - Wuhan University; WEI, YANXHANG - Clemson University; Wall, Marisa; SONGSAK, THANAPAT - University Of Hawaii; WONGWIWATTHANANUKIT, SUPAKIT - Rangsit University; CHANG, LENG CHEE - University Of Hawaii

Submitted to: Journal of Natural Products
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 7/24/2019
Publication Date: 8/14/2019
Citation: Zhang, M., Yang, X., Wei, Y., Wall, M.M., Songsak, T., Wongwiwatthananukit, S., Chang, L. 2019. Bioactive sesquiterpene lactones isolated from the whole plants of Vernonia cinerea. Journal of Natural Products. 82(8):2124-2131. https://doi.org/10.1021/acs.jnatprod.8b01078.
DOI: https://doi.org/10.1021/acs.jnatprod.8b01078

Interpretive Summary: Vernonia cinerea, commonly known as iron weed, is a perennial herbaceous plant mainly distributed in tropical areas. The stem, bark, roots, leaves and flowers have been used traditionally as a folk remedy for many diseases. The plant parts are known to be rich sources of sesquiterpene lactones, a diverse group of biologically active plant chemicals. In this study, human cervical cancer HeLa cells were used to evaluate the anticancer and anti-inflammatory effects of sesquiterpene lactones in vitro. We report the isolation, structure elucidation, cytotoxicity against these cells, and anti-inflammatory activities of sesquiterpene lactones. Eight new compounds, along with four known derivatives were isolated and identified. These natural products derived from V. cinerea expand our cache of biologically active constituents from tropical plants.

Technical Abstract: Twelve sesquiterpene lactones were isolated from the whole plants of Vernonia cinerea. These included eight new compounds (1-8), along with four known derivatives (9-12). The structures of the new compounds were determined by 1D- and 2D- NMR experiments, mass spectroscopic methods, and the absolute configurations of compounds 1-8 were determined by Mosher experiments and ECD data. Compounds 1–4, 6, 8, 10, and 12 were evaluated for their anti-cancer and anti-inflammatory activities. Compounds (3, 10, and 12) demonstrated inhibitory effects against human cervical carcinoma HeLa cells in a dose-dependent manner. Compounds 10 and 12 exhibited inhibitory effects against lipopolysaccharide (LPS)-activated nitrite oxide (NO) production in RAW 264.7 macrophage cells at a dose of as low as 10 ug/mL.