Unusual metal complex of cadinane sesquiterpene alkaloid and new neolignan glycosides from Alangium alpinum

Fitoterapia. 2018 Mar:125:18-23. doi: 10.1016/j.fitote.2017.12.008. Epub 2017 Dec 11.

Abstract

One unusual metal complex of cadinane sesquiterpene alkaloid (1), one new cadinane sesquiterpene alkaloid (2) and two new neolignan glycosides (3-4) along with six known cadinane sesquiterpene derivatives (5-10), nineteen known phenolic glycosides (11-29) were isolated from the aerial parts of Alangium alpinum. Structures of new crystals of metal complex were characterized by X-Ray diffraction and ICP-AES analysis. Other new compounds were elucidated by combined use and detailed analysis of HR-ESIMS, 1D and 2D NMR and CD spectroscopic method. In addition, all isolated compounds were tested for their inhibitory effects against TNF-α induced NF-κB activation in Hela cells and NO production in RAW 264.7 macrophages.

Keywords: Alangium alpinum; Cadinane sesquiterpene alkaloid; Metal complex.

MeSH terms

  • Alangiaceae / chemistry*
  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Animals
  • Glycosides / isolation & purification*
  • HeLa Cells
  • Humans
  • Lignans / isolation & purification*
  • Metals / chemistry
  • Mice
  • Molecular Structure
  • NF-kappa B / metabolism
  • Nitric Oxide / metabolism
  • Plant Components, Aerial / chemistry
  • Polycyclic Sesquiterpenes
  • RAW 264.7 Cells
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Tumor Necrosis Factor-alpha / metabolism

Substances

  • Alkaloids
  • Glycosides
  • Lignans
  • Metals
  • NF-kappa B
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes
  • Tumor Necrosis Factor-alpha
  • cadinane
  • Nitric Oxide