Dibenzofuran, 4-Chromanone, Acetophenone, and Dithiecine Derivatives: Cytotoxic Constituents from Eupatorium fortunei

Int J Mol Sci. 2021 Jul 12;22(14):7448. doi: 10.3390/ijms22147448.

Abstract

Five new compounds, eupatodibenzofuran A (1), eupatodibenzofuran B (2), 6-acetyl-8-methoxy-2,2-dimethylchroman-4-one (3), eupatofortunone (4), and eupatodithiecine (5), have been isolated from the aerial part of Eupatorium fortunei, together with 11 known compounds (616). Compounds 1 and 2 featured a new carbon skeleton with an unprecedented 1-(9-(4-methylphenyl)-6-methyldibe nzo[b,d]furan-2-yl)ethenone. Among the isolates, compound 1 exhibited potent inhibitory activity with IC50 values of 5.95 ± 0.89 and 5.55 ± 0.23 μM, respectively, against A549 and MCF-7 cells. The colony-formation assay demonstrated that compound 1 (5 μM) obviously decreased A549 and MCF-7 cell proliferation, and Western blot test confirmed that compound 1 markedly induced apoptosis of A549 and MCF-7 cells through mitochondrial- and caspase-3-dependent pathways.

Keywords: Eupatorium fortunei; apoptosis; cytotoxity; dibenzofuran.

MeSH terms

  • Acetophenones / chemistry
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Apoptosis
  • Benzofurans / chemistry
  • Cell Proliferation
  • Chromones / chemistry
  • Eupatorium / chemistry*
  • Humans
  • Molecular Structure
  • Neoplasms / drug therapy*
  • Neoplasms / pathology
  • Phytochemicals / chemistry*
  • Phytochemicals / pharmacology*
  • Plant Extracts / pharmacology*
  • Structure-Activity Relationship
  • Tumor Cells, Cultured

Substances

  • Acetophenones
  • Antineoplastic Agents, Phytogenic
  • Benzofurans
  • Chromones
  • Phytochemicals
  • Plant Extracts
  • 4-chromanone
  • dibenzofuran
  • acetophenone