A new diarylheptanoid and a new diarylheptanoid glycoside isolated from the roots of Juglans mandshurica and their anti-inflammatory activities

Nat Prod Res. 2019 Mar;33(5):701-707. doi: 10.1080/14786419.2017.1408100. Epub 2017 Dec 5.

Abstract

A new diarylheptanoid, (2S,3S,5S)-2,3,5-trihydroxy-1,7-bis(4-hydroxy- 3-methoxyphenyl)heptane (1), and a new diarylheptanoid glycoside, (2S,3S,5S)-2,3-dihydroxy-5-O-β-d-xylopyranosyl-7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)heptane (2), together with three known compounds, rhoiptelol C (3), rhoiptelol B (4) and 3',4″-epoxy-2-O-β-d-glucopyanosyl-1-(4-hydroxyphenyl)- 7-(3-methoxyphenyl)heptan-3-one (5) were isolated from the roots of Juglans mandshurica (Juglandaceae). The structures of compounds 1 and 2 were identified based on HR-ESI-MS, 1D and 2D NMR spectroscopic methods. Compounds 1-5 were assayed for their inhibitory effects on the production of NO, TNF-α and IL-6 in LPS-stimulated RAW264.7 cells.

Keywords: IL-6 production; Juglandaceae; NO production; TNF-α production; diarylheptanoids.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology*
  • China
  • Diarylheptanoids / isolation & purification
  • Diarylheptanoids / pharmacology*
  • Glycosides / isolation & purification
  • Glycosides / pharmacology*
  • Juglans / chemistry*
  • Magnetic Resonance Spectroscopy
  • Mice
  • Molecular Structure
  • Phytochemicals / isolation & purification
  • Phytochemicals / pharmacology
  • Plant Roots / chemistry
  • RAW 264.7 Cells

Substances

  • Anti-Inflammatory Agents
  • Diarylheptanoids
  • Glycosides
  • Phytochemicals