Synthesis, Molecular Mechanism and Pharmacokinetic Studies of New Epoxy Lignan-Based Derivatives

Arch Pharm (Weinheim). 2016 Nov;349(11):848-852. doi: 10.1002/ardp.201600069. Epub 2016 Oct 4.

Abstract

The oxidative demethylation procedure for a new epoxy lignan isolated from Piper nigrum was applied to the synthesis of 3'-methoxy-3",4"-(methylenedioxy)-2,5-epoxylignan-4'-ol-6'-one. This compound inhibited the mRNA expression of the protein patched homolog (Ptch) in human pancreatic cancer cells (PANC1) and therefore might be valuable as a probe for tumor-related disease. The pharmacokinetic profile of 3'-methoxy-3",4"-(methylenedioxy)-2,5-epoxylignan-4'-ol-6'-one was rapidly determined using ultra-fast liquid chromatography. The compound was rapidly absorbed in blood.

Keywords: Epoxy lignan; Glioma; Pharmacokinetics profile; Ptch mRNA expression; UFLC.

MeSH terms

  • Cell Line, Tumor
  • Down-Regulation / drug effects
  • Humans
  • Lignans / blood
  • Lignans / chemical synthesis
  • Lignans / pharmacokinetics*
  • Lignans / pharmacology
  • Patched-1 Receptor / genetics
  • RNA, Messenger / biosynthesis
  • RNA, Messenger / genetics

Substances

  • 3'-methoxy-3',4'-(methylenedioxy)-2,5-epoxylignan-4'-ol-6'-one
  • Lignans
  • PTCH1 protein, human
  • Patched-1 Receptor
  • RNA, Messenger