The Cytotoxic Cardiac Glycoside (-)-Cryptanoside A from the Stems of Cryptolepis dubia and Its Molecular Targets

J Nat Prod. 2023 Jun 23;86(6):1411-1419. doi: 10.1021/acs.jnatprod.3c00094. Epub 2023 May 22.

Abstract

A cardiac glycoside epoxide, (-)-cryptanoside A (1), was isolated from the stems of Cryptolepis dubia collected in Laos, for which the complete structure was confirmed by analysis of its spectroscopic and single-crystal X-ray diffraction data, using copper radiation at a low temperature. This cardiac glycoside epoxide exhibited potent cytotoxicity against several human cancer cell lines tested, including HT-29 colon, MDA-MB-231 breast, OVCAR3 and OVCAR5 ovarian cancer, and MDA-MB-435 melanoma cells, with the IC50 values found to be in the range 0.1-0.5 μM, which is comparable with that observed for digoxin. However, it exhibited less potent activity (IC50 1.1 μM) against FT194 benign/nonmalignant human fallopian tube secretory epithelial cells when compared with digoxin (IC50 0.16 μM), indicating its more selective activity toward human cancer versus benign/nonmalignant cells. (-)-Cryptanoside A (1) also inhibited Na+/K+-ATPase activity and increased the expression of Akt and the p65 subunit of NF-κB but did not show any effects on the expression of PI3K. A molecular docking profile showed that (-)-cryptanoside A (1) binds to Na+/K+-ATPase, and thus 1 may directly target Na+/K+-ATPase to mediate its cancer cell cytotoxicity.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents* / pharmacology
  • Apoptosis
  • Cardiac Glycosides* / chemistry
  • Cardiac Glycosides* / pharmacology
  • Cell Line, Tumor
  • Cryptolepis / metabolism
  • Digoxin / pharmacology
  • Female
  • Humans
  • Molecular Docking Simulation
  • Ovarian Neoplasms*
  • Sodium-Potassium-Exchanging ATPase

Substances

  • Cardiac Glycosides
  • Sodium-Potassium-Exchanging ATPase
  • Antineoplastic Agents
  • Digoxin