Phenolic Glycosides from the Twigs of Salix glandulosa

J Nat Prod. 2014 Aug 22;77(8):1955-61. doi: 10.1021/np500488v. Epub 2014 Aug 6.

Abstract

As a part of an ongoing search for bioactive constituents from Korean medicinal plants, the phytochemical investigations of the twigs of Salix glandulosa afforded 12 new phenolic glycosides (1-12) and a known analogue (13). The structures of 1-13 were characterized by a combination of NMR methods ((1)H and (13)C NMR, (1)H-(1)H COSY, HMQC, and HMBC), chemical hydrolysis, and GC/MS. The absolute configuration of 13 [(1R,2S)-2-hydroxycyclohexyl-2'-O-trans-p-coumaroyl-β-d-glucopyranoside] was determined for the first time. Compounds 1-3, 6, and 7 exhibited inhibitory effects on nitric oxide production in lipopolysaccharide-activated murine microglial cells (IC50 values in the range 6.6-20.5 μM).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Mice
  • Molecular Structure
  • Nitric Oxide / biosynthesis
  • Nuclear Magnetic Resonance, Biomolecular
  • Phenols / chemistry
  • Phenols / isolation & purification*
  • Phenols / pharmacology
  • Plant Stems / chemistry
  • Plants, Medicinal / chemistry*
  • Republic of Korea
  • Salix / chemistry*
  • Stereoisomerism

Substances

  • Glycosides
  • Lipopolysaccharides
  • Phenols
  • Nitric Oxide