Bruceadysentoside A, a new pregnane glycoside and others secondary metabolites with cytotoxic activity from brucea antidysenterica J. F. Mill. (simaroubaceae)

Nat Prod Res. 2021 Jun;35(12):2037-2043. doi: 10.1080/14786419.2019.1655024. Epub 2019 Aug 21.

Abstract

The chemical investigation of the root barks leaves and stem barks of Brucea antidysenterica J. F. Mill. (Simaroubaceae) led to the isolation of a new pregnane glycoside, named Bruceadysentoside A or 3-O-β-L-arabinopyranosyl-pregn-5-en-20-one (1) together with seventeen known compounds. Their structures were established from spectral data, mainly HRESIMS, 1 D and 2 D NMR and by comparison with literature data. Compounds 1, 2, 5, 6, 8, 10, 12 and 13 were tested in vitro for their effects on the viability of two different human cancer cell lines, namely prostate PC-3 adenocarcinoma cells and colorectal HT-29 adenocarcinoma cells. No substantial activities were recorded for 2, 10, 12 and 13 (up to 10 μM concentration). 1, 5 and 8 did not show strong anti-proliferative effects up to 100 μM, however, 6 exhibited a stronger anti-proliferative effect with IC50 values of ∼ 100 μM against PC-3 and ∼ 200 μM against HT-29.

Keywords: Brucea antidysenterica; Bruceadysentoside A; Simaroubaceae; cytotoxic activities; hydnocarpin; pregnane glycoside.

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry*
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Brucea / chemistry
  • Brucea / metabolism*
  • Drug Screening Assays, Antitumor
  • Glycosides / chemistry
  • HT29 Cells
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • PC-3 Cells
  • Plant Extracts / chemistry
  • Plant Leaves / chemistry
  • Pregnanes / chemistry
  • Secondary Metabolism
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Antineoplastic Agents, Phytogenic
  • Glycosides
  • Plant Extracts
  • Pregnanes
  • pregnane glycoside