Four Yellow Monoterpenoid Quinoline Alkaloids from the Stem of Tabernaemontana bovina

Org Lett. 2019 Jun 21;21(12):4554-4558. doi: 10.1021/acs.orglett.9b01453. Epub 2019 Jun 10.

Abstract

Four unprecedented yellow alkaloids named as taberbovines A-D (1-4) were isolated from stems of Tabernaemontana bovina Lour. Their structures were elucidated by the comprehensive spectroscopic data, computational chemistry, and X-ray crystal diffraction. Alkaloids 1-4 possessed a unique 6/6/5/6/5 ring system and were assigned to monoterpenoid quinolines. Biosynthetically, the isolated alkaloids may be derived from Aspidosperma-type alkaloid by oxidation and rearrangements. Taberbovines A-D exhibited the good inhibitory activities of formation NO in LPS induced RAW264.7 macrophages.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • Animals
  • Crystallography, X-Ray
  • Lipopolysaccharides / antagonists & inhibitors
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Mice
  • Models, Molecular
  • Molecular Structure
  • Nitric Oxide / antagonists & inhibitors*
  • Nitric Oxide / biosynthesis
  • Quinolines / chemistry
  • Quinolines / isolation & purification
  • Quinolines / pharmacology*
  • RAW 264.7 Cells
  • Tabernaemontana / chemistry*

Substances

  • Alkaloids
  • Lipopolysaccharides
  • Quinolines
  • Nitric Oxide
  • quinoline yellow