Cardiac glycosides from the bark of Antiaris toxicaria

Fitoterapia. 2014 Sep:97:71-7. doi: 10.1016/j.fitote.2014.05.013. Epub 2014 May 28.

Abstract

Five new cardiac glycosides (1-5, namely antiaroside Y-ZC) together with 19 known compounds were obtained from the bark of Antiaris toxicaria. Their chemical structures were determined by IR, HR-ESI-MS, 1D and 2D NMR (HSQC, (1)H-(1)H COSY, HMBC, ROESY). The absolute configuration of sugar unit was defined by acid hydrolysis and appropriate derivatization. Compound 1 was rare 5β-H-10β-H-19-nor-cardenolide, which might derive from decarboxylative derivative of 19-COOH cardenolide. The inhibitory effects of cardiac glycosides 1-11 on the viability of NIH-H460 lung cancer cells and their induction of Nur77 expression were evaluated and preliminary structure-activity relationship (SAR) was also discussed.

Keywords: Antiaris toxicaria; Cardiac glycoside; Chemical constituents; Cytotoxicity; Expression of Nur77.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiaris / chemistry*
  • Cardiac Glycosides / chemistry
  • Cardiac Glycosides / isolation & purification*
  • Cardiac Glycosides / therapeutic use
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Humans
  • Lung Neoplasms / drug therapy*
  • Lung Neoplasms / metabolism
  • Nuclear Receptor Subfamily 4, Group A, Member 1 / metabolism*
  • Plant Bark / chemistry
  • Structure-Activity Relationship

Substances

  • Cardiac Glycosides
  • NR4A1 protein, human
  • Nuclear Receptor Subfamily 4, Group A, Member 1