Cephalotanins A-D, Four Norditerpenoids Represent Three Highly Rigid Carbon Skeletons from Cephalotaxus sinensis

Chemistry. 2016 Oct 4;22(41):14648-54. doi: 10.1002/chem.201603373. Epub 2016 Aug 19.

Abstract

Four polycyclic norditerpenoids, cephalotanins A-D (1-4) representing three unprecedented carbon skeletons with highly rigid ring systems, were isolated from Cephalotaxus sinensis and structurally characterized by a combination of various methods. Compounds 1 and 2 are new skeletal norditerpenoid trilactones, while 3 and 4 are two norditerpenoids featuring different new carbon skeletons. Biosynthetic pathways for 1-4 were proposed by involving diverse and very fascinating chemical events with the coexisting cephalotane troponoids as the precursors. Compound 1 exhibited good NF-κB inhibition with an IC50 value of 4.12±0.61 μΜ.

Keywords: biosynthetic pathways; cephalotanins; cephalotaxus norditerpenoid; nf-κb inhibition; structural elucidation.

MeSH terms

  • Carbon / chemistry*
  • Cephalotaxus / chemistry*
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology
  • HEK293 Cells
  • Humans
  • Molecular Docking Simulation
  • Molecular Structure
  • NF-kappa B / antagonists & inhibitors
  • Plant Extracts / chemistry*
  • Plant Leaves / chemistry
  • Structure-Activity Relationship

Substances

  • Diterpenes
  • NF-kappa B
  • Plant Extracts
  • Carbon