Diarylheptanoids and flavonoids from viscum album inhibit LPS-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells

J Nat Prod. 2013 Apr 26;76(4):495-502. doi: 10.1021/np300490v. Epub 2013 Mar 13.

Abstract

Three new diarylheptanoids, (3S,5R)-3-hydroxy-5-methoxy-1,7-bis(4-hydroxyphenyl)-6E-heptene (1), (3S,5S)-3-hydroxy-5-methoxy-1,7-bis(4-hydroxyphenyl)-6E-heptene (2), and (3S)-3-hydroxy-1,7-bis(4-hydroxyphenyl)-6E-hepten-5-one (3), four new flavonoid glycosides, 3,7,3'-tri-O-methylquercetin-4'-O-β-d-apiofuranosyl-(1→2)-O-β-d-glucopyranoside (4), 7,3'-di-O-methylquercetin-4'-O-β-d-glucopyranosyl-3-O-[6‴-(3-hydroxy-3-methylglutaroyl)]-α-d-glucopyranoside (5), 7,3'-di-O-methylquercetin-4'-O-β-d-glucopyranosyl-3-O-[(6'''''→5'''')-O-1'''''-(sinap-4-yl)-β-d-glucopyranosyl-6‴-(3-hydroxy-3-methylglutaroyl)]-α-d-glucopyranoside (6), and (2S)-5-hydroxy-7,3'-dimethoxyflavanone-4'-O-β-d-apiofuranosyl-(1→5)-O-β-d-apiofuranosyl-(1→2)-O-β-d-glucopyranoside (9), and 17 known compounds were isolated from the leaves and twigs of Viscum album. Compounds 1, 4, and 19 significantly inhibited LPS-stimulated production of TNF-α, IL-6, and IL-12p40 with IC50 values ranging from 0.09 ± 0.01 to 8.96 ± 0.45 μM. (+)-Medioresinol (13) showed inhibitory effects on LPS-stimulated production of IL-12p40 with an IC50 value of 2.00 ± 0.15 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification*
  • Anti-Inflammatory Agents / pharmacology*
  • Bone Marrow Cells / drug effects
  • Cytokines / antagonists & inhibitors
  • Dendritic Cells / drug effects
  • Diarylheptanoids / chemistry
  • Diarylheptanoids / isolation & purification*
  • Diarylheptanoids / pharmacology*
  • Flavonoids / chemistry
  • Flavonoids / isolation & purification*
  • Flavonoids / pharmacology*
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology*
  • Inhibitory Concentration 50
  • Interleukin-12 Subunit p40 / antagonists & inhibitors
  • Interleukin-6 / antagonists & inhibitors
  • Lipopolysaccharides / pharmacology
  • Mice
  • Mice, Inbred C57BL
  • Plant Leaves / chemistry
  • Plant Stems / chemistry
  • Stereoisomerism
  • Tumor Necrosis Factor-alpha / antagonists & inhibitors
  • Viscum album / chemistry*

Substances

  • Anti-Inflammatory Agents
  • Cytokines
  • Diarylheptanoids
  • Flavonoids
  • Glycosides
  • Interleukin-12 Subunit p40
  • Interleukin-6
  • Lipopolysaccharides
  • Tumor Necrosis Factor-alpha