Regioselective synthesis and structures of anti-cancer 20(R)-ginsenoside Rg3 derivatives

Nat Prod Res. 2020 Jul;34(14):1962-1970. doi: 10.1080/14786419.2019.1569007. Epub 2019 May 15.

Abstract

Regioselective synthesis of three novel palmitates of 20(R)-ginsenoside Rg3 was accomplished via a facile strategy, along with complete assignment of their 1H and 13C NMR resonances by 1D and 2D NMR (1H-1H COSY, DEPT 135, HSQC, HMBC, and NOESY) techniques. The derivatives were tested for in vitro anti-proliferative activities against pancreatic cancer PANC-1 cells. Compounds 2, 3, and 4 exhibited more potent activity than did 20(R)-ginsenoside Rg3.

Keywords: 20(R)-ginsenoside Rg3; Anti-cancer; regioselective synthesis.

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemical synthesis*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Cell Line, Tumor
  • Ginsenosides / chemical synthesis*
  • Ginsenosides / chemistry
  • Ginsenosides / pharmacology
  • Humans
  • Magnetic Resonance Spectroscopy
  • Pancreatic Neoplasms / drug therapy

Substances

  • Antineoplastic Agents, Phytogenic
  • Ginsenosides
  • ginsenoside Rg3