Lanceoleins A-G, hydroxychalcones, from the flowers of Coreopsis lanceolata and their chemopreventive effects against human colon cancer cells

Bioorg Chem. 2019 Apr:85:274-281. doi: 10.1016/j.bioorg.2019.01.003. Epub 2019 Jan 4.

Abstract

Seven new chalcones, lanceolein A-G (compounds 5 and 7-12), as well as five known chalcones (1-4 and 6), were isolated from the methanolic extract of Coreopsis lanceolata flowers. The chemical structures of 5 and 7-12 were determined on the basis of spectroscopic data interpretation. All compounds inhibited the production of nitrite oxide (NO) induced by LPS in RAW264.7 macrophage cells. Also, compounds 1-6 showed moderated cytotoxicity against human colon cancer cell lines, while compounds 7-12 hardly showed the cytotoxicity. Especially, compounds 2, 5, and 6 exhibited a little higher cytotoxicity on HCT15 cells, with IC50 values of 43.7 ± 2.17 μM, 35.6 ± 0.24 μM, and 47.9 ± 1.18 μM, respectively. In the Tali assay, compounds 2 and 5 increased the numeral of apoptotic cells. These compounds also significantly promoted the expression of apoptotic proteins including PARP and caspase-3.

Keywords: Apoptosis; Chalcone; Coreopsis lanceolata; Cytotoxicity; Lanceoleins A−G; Nitric oxide; RAW264.7 macrophages; Western blot.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anticarcinogenic Agents / chemistry
  • Anticarcinogenic Agents / isolation & purification
  • Anticarcinogenic Agents / pharmacology*
  • Apoptosis / drug effects
  • Cell Line, Tumor
  • Chalcones / chemistry
  • Chalcones / isolation & purification
  • Chalcones / pharmacology*
  • Coreopsis / chemistry*
  • Flowers / chemistry*
  • Humans
  • Mice
  • Nitric Oxide / antagonists & inhibitors
  • RAW 264.7 Cells

Substances

  • Anticarcinogenic Agents
  • Chalcones
  • Nitric Oxide