Bioactive Glycosides from the Twigs of Litsea cubeba

J Nat Prod. 2017 Jun 23;80(6):1808-1818. doi: 10.1021/acs.jnatprod.6b01189. Epub 2017 May 25.

Abstract

The air-dried twigs of Litsea cubeba, a traditional Chinese medicinal tree, afforded 10 new aromatic glycosides (1-10) and 26 known analogues. Their structures were assigned by extensive 1D and 2D NMR experiments, and the absolute configurations were resolved by chemical methods, electronic circular dichroism, specific rotation, and X-ray crystallographic analysis. Compound 4 is the first example of a naturally occurring homoneolignan glucoside. Compounds 4, 6-8, and the known neolignan glucosides (11, 12, and 14) at respective 10 μM concentrations were found to reduce acetaminophen-induced HepG2 cell injury with 30.5-46.0% inhibitions. Furthermore, compounds 12 and 15 demonstrated moderate inhibitory activities against HDAC1, with IC50 values of 3.6 and 4.6 μM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetaminophen / pharmacology
  • Algorithms
  • Crystallography, X-Ray
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology*
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology*
  • Hep G2 Cells
  • Humans
  • Inhibitory Concentration 50
  • Lignans / chemistry
  • Lignans / isolation & purification
  • Lignans / pharmacology
  • Lipopolysaccharides / pharmacology
  • Litsea / chemistry*
  • Molecular Conformation
  • Molecular Structure
  • Nitric Oxide / biosynthesis
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Roots / chemistry
  • Plant Stems / chemistry*

Substances

  • Drugs, Chinese Herbal
  • Glycosides
  • Lignans
  • Lipopolysaccharides
  • Nitric Oxide
  • Acetaminophen