Cytotoxic Stilbenes and Canthinone Alkaloids from Brucea antidysenterica (Simaroubaceae)

Molecules. 2019 Dec 3;24(23):4412. doi: 10.3390/molecules24234412.

Abstract

A phytochemical study of the root and bark of Brucea antidysenterica J. F. Mill. (Simaroubaceae) afforded three new compounds, including a stilbene glycoside bruceanoside A (1), and two canthinone alkaloids bruceacanthinones A (3) and B (4), along with ten known secondary metabolites, rhaponticin (2), 1,11-dimethoxycanthin-6-one (5), canthin-6-one (6), 1-methoxycanthin-6-one (7), 2-methoxycanthin-6-one (8), 2-hydroxy-1,11-dimethoxycanthin-6-one (9), β-carboline-1-propionic acid (10), cleomiscosin C (11), cleomiscosin A (12), and hydnocarpin (13). The structures of all the compounds were determined using spectrometric and spectroscopic methods including 1D and 2D NMR, and HRSEIMS. The identities of the known compounds were further confirmed by comparison of their data with those reported in the literature. The root and bark methanolic extracts, the dichloromethane and ethyl acetate soluble fractions, and the isolated compounds (3-13), were assessed for their cytotoxicity against the cancer cell lines A-549, MCF-7, and PC-3. The results suggested that compounds in the extracts might possess a synergic action in their cytotoxicity.

Keywords: Brucea antidysenterica; Simaroubaceae; bruceacanthinones A–B; bruceanoside A; cytotoxicity.

MeSH terms

  • A549 Cells
  • Alkaloids / chemistry
  • Alkaloids / pharmacology*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Brucea / chemistry*
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Drug Synergism
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / pharmacology*
  • Humans
  • MCF-7 Cells
  • Molecular Structure
  • PC-3 Cells
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology
  • Secondary Metabolism
  • Stilbenes / chemistry
  • Stilbenes / pharmacology*

Substances

  • Alkaloids
  • Antineoplastic Agents, Phytogenic
  • Drugs, Chinese Herbal
  • Plant Extracts
  • Stilbenes
  • canthinone