Distinct sesquiterpene pyridine alkaloids from in Salvadoran and Peruvian Celastraceae species

Phytochemistry. 2017 Oct:142:21-29. doi: 10.1016/j.phytochem.2017.06.013. Epub 2017 Jun 27.

Abstract

As part of a bioprospecting program aimed at the discovery of undescribed natural products from Salvadoran and Peruvian flora, the phytochemical investigations of four Celastraceae species, Celastrus vulcanicola, Maytenus segoviarum, Maytenus jeslkii, and Maytenus cuzcoina, were performed. The current study reports the isolation and structural characterization of five previously undescribed macrolide sesquiterpene pyridine alkaloids, named vulcanicoline-A, cuzcoinine, vulcanicoline-B, jelskiine, and vulcanicoline-C, along with sixteen known alkaloids. The structures of the alkaloids were established by spectrometric and extensive 1D and 2D NMR spectroscopic analysis, including COSY, HSQC, HMBC, and ROESY experiments. The absolute configurations of alkaloids were proposed based on optical rotation sign, and biogenetic considerations. This study represents the first phytochemical analysis of Maytenus segoviarum.

Keywords: Celastraceae; Celastrus vulcanicola; Maytenus cuzcoina; Maytenus jeslkii; Maytenus segoviarum; Sesquiterpene pyridine alkaloids.

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Celastraceae / chemistry*
  • Celastrus
  • El Salvador
  • Maytenus / chemistry
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Peru
  • Pyridines / chemistry
  • Pyridines / isolation & purification*
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*

Substances

  • Alkaloids
  • Pyridines
  • Sesquiterpenes