New Structurally Diverse Limonoids from the Seeds of Khaya senegalensis

Planta Med. 2017 Feb;83(3-04):341-350. doi: 10.1055/s-0042-117114. Epub 2016 Sep 20.

Abstract

Twelve new limonoids (khasenegasins O-Z; 1-12) with three different kinds of skeletons, including eight mexicanolides, two gedunins, and two andirobins, together with four known limonoids (13-16) were isolated from the seeds of Khaya senegalensis. Their structures were determined by extensive spectroscopic analyses (HR-ESI-MS, 1D/2D NMR), and the absolute configurations of 1 and 2 were established by the electronic circular dichroism exciton chirality method. Moreover, a new andirobin-type limonoid (12) showed significant neuroprotective activity against glutamate-induced injury in primary rat cerebellar granule neuronal cells with increased viability of 83.3 ± 6.0 % at 10 µM and 80.3 ± 3.2 % at 1 µM.

MeSH terms

  • Animals
  • Cell Survival / drug effects
  • Circular Dichroism
  • Limonins / chemistry*
  • Limonins / isolation & purification
  • Limonins / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Meliaceae / chemistry*
  • Molecular Structure
  • Neuroprotective Agents / chemistry
  • Neuroprotective Agents / pharmacology
  • Nuclear Magnetic Resonance, Biomolecular / methods
  • Rats
  • Rats, Sprague-Dawley
  • Seeds / chemistry

Substances

  • Limonins
  • Neuroprotective Agents
  • mexicanolide