Further C-15-acyl phragmalin derivatives from Chukrasia tabularis A. Juss

Phytochemistry. 2015 Sep:117:410-416. doi: 10.1016/j.phytochem.2015.05.014. Epub 2015 Jul 14.

Abstract

Relying on characteristic double UV absorptions (210 and 270 nm), sixteen phragmalins with three types of enolic acyl substituents at C-15 were isolated directly from EtOH extracts of the seeds of Chukrasia tabularis A. Juss. Eight of these compounds possessed a C-15-acetyl phragmalin skeleton, and the basic carbon skeleton and absolute configuration of one of these was determined by NMR and X-ray diffraction analysis, while the structures of the other phragmalins were determined via NMR, HR-MS, and CD spectra. Additionally, all of the isolates were tested for inhibition against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 macrophages and cytotoxicity in SMMC-7721, MCF-7 and U2OS tumor cells.

Keywords: Absolute configuration; C-15 enolic acyl phragmalin; Chukrasia tabularis A. Juss.; Meliaceae; UV-guided isolation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line / drug effects
  • Circular Dichroism
  • Crystallography, X-Ray
  • Drug Evaluation, Preclinical / methods
  • Humans
  • Limonins / chemistry*
  • Limonins / pharmacology
  • Lipopolysaccharides / pharmacology
  • MCF-7 Cells / drug effects
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Magnetic Resonance Spectroscopy
  • Meliaceae / chemistry*
  • Mice
  • Molecular Structure
  • Nitric Oxide / metabolism
  • Spectrophotometry, Ultraviolet

Substances

  • Limonins
  • Lipopolysaccharides
  • phragmalin
  • Nitric Oxide