Phenolic compounds and their anti-oxidative properties and protein kinase inhibition from the Chinese mangrove plant Laguncularia racemosa

Phytochemistry. 2010 Mar;71(4):435-42. doi: 10.1016/j.phytochem.2009.11.008. Epub 2009 Dec 18.

Abstract

Phenolic compounds, named integracin D (1), (7'R, 8'S, 8S)-8-hydroxyisoguaiacin (3), (2R, 3R) pinobanksin-3-caffeoylate (5) and threo-8S-7-methoxysyringylglycerol (6), respectively, were isolated from the Chinese mangrove plant Laguncularia racemosa (L) Gaertn. f. (Combretaceae), together with 23 known phenolic metabolites. Their structures were elucidated on the basis of extensive spectroscopic analyses including that of IR, UV, MS, CD, 1D and 2D NMR spectra as well as by comparison with literature data. Compound 5 showed significant anti-oxidative activity in the DPPH and TEAC free-radical-scavenging assays, while several of the phenolic compounds were tested for protein kinase inhibitory activity in an assay involving 24 different human tumor related protein kinases. Compounds 5, 7, and 23 showed potential inhibition with IC(50) values between 2.2 and 3.6microg/mL toward individual kinases. The ellagic acid derivatives were tested for insecticidal activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antioxidants / chemistry*
  • Antioxidants / isolation & purification
  • Antioxidants / pharmacology*
  • Biphenyl Compounds / chemistry
  • Cell Line, Tumor
  • Combretaceae / chemistry*
  • Humans
  • Models, Molecular
  • Molecular Conformation
  • Neoplasms / enzymology
  • Phenol / chemistry*
  • Phenol / isolation & purification
  • Phenol / pharmacology*
  • Picrates / chemistry
  • Protein Kinase Inhibitors / chemistry*
  • Protein Kinase Inhibitors / isolation & purification
  • Protein Kinase Inhibitors / pharmacology*
  • Rats
  • Spodoptera / drug effects

Substances

  • Antioxidants
  • Biphenyl Compounds
  • Picrates
  • Protein Kinase Inhibitors
  • Phenol
  • 1,1-diphenyl-2-picrylhydrazyl