Phenolic compounds from the aerial parts of Clematis viticella L. and their in vitro anti-inflammatory activities

Nat Prod Res. 2019 Sep;33(17):2541-2544. doi: 10.1080/14786419.2018.1448815. Epub 2018 Mar 12.

Abstract

Phytochemical investigations on the EtOH extract of Clematis viticella led to the isolation of six flavonoid glycosides, isoorientin (1), isoorientin 3'-O-methyl ether (2), quercetin 7-O-α-L-rhamnopyranoside (3), quercetin 3,7-di-O-α-L-rhamnopyranoside (4), manghaslin (5) and chrysoeriol 7-O-β-D-glucopyranoside (6), one phenylethanol derivative, hydroxytyrosol (7), along with three phenolic acids, caffeic acid (8), (E)-p-coumaric acid (9) and p-hydroxybenzoic acid (10). The structures of the isolates were elucidated on the basis of NMR and HR-MS data. All compounds were isolated from C. viticella for the first time. Compounds 7 and 8 showed significant anti-inflammatory activity at 100 μM by reducing the release of NO in LPS-stimulated macrophages comparable to positive control indomethacin. Compounds 3 and 7 exhibited anti-inflammatory activity through lowering the levels of TNF-α while 1, 3 and 5 decreased the levels of neopterin better than the positive controls.

Keywords: anti-inflammatory activity; flavonoid glycosides; hydroxytyrosol; phenolic acids.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification*
  • Anti-Inflammatory Agents / pharmacology
  • Clematis / chemistry*
  • Flavonoids / chemistry
  • Flavonoids / isolation & purification*
  • Flavonoids / pharmacology
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology
  • Humans
  • Macrophages / metabolism
  • Mice
  • Molecular Structure
  • Nitric Acid / metabolism
  • Phenols / chemistry
  • Phenols / isolation & purification*
  • Phenols / pharmacology
  • Plant Components, Aerial / chemistry
  • Plant Extracts / chemistry
  • RAW 264.7 Cells
  • Spectrum Analysis
  • Tumor Necrosis Factor-alpha / drug effects
  • Tumor Necrosis Factor-alpha / metabolism

Substances

  • Anti-Inflammatory Agents
  • Flavonoids
  • Glycosides
  • Phenols
  • Plant Extracts
  • Tumor Necrosis Factor-alpha
  • Nitric Acid