Clemochinenosides C and D, two new macrocyclic glucosides from Clematis chinensis

J Asian Nat Prod Res. 2018 Nov;20(11):1038-1044. doi: 10.1080/10286020.2017.1387780. Epub 2017 Oct 23.

Abstract

The EtOH extract of the roots and rhizomes of Clematis chinensis afforded two new macrocyclic glucosides clemochinenosides C (1) and D (2). Their structures were elucidated on the basis of spectroscopic means and hydrolysis products. These compounds were evaluated for inhibitory activity against lipopolysaccharides-induced TNF-α production in RAW 246.7 macrophages. Compounds 1 and 2 showed moderate inhibitory activity with IC50 values of 12.9 ± 2.3 and 18.4 ± 2.7 μM, respectively. In addition, a proliferation study was used to evaluate the anti-angiogenic effects of these compounds in vitro (VEGF-induced human umbilical vein endothelial cell proliferation). Compounds 1 and 2 displayed weak inhibitory effects with inhibition rates of 26.3 ± 1.8 and 19.2 ± 2.6% at 50 μM, respectively.

Keywords: Ranunculaceae; TNF-α production inhibitory activity; anti-angiogenic effects; macrocyclic glucosides.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / pharmacology
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Cell Proliferation / drug effects
  • Clematis / chemistry*
  • Glucosides / chemistry*
  • Human Umbilical Vein Endothelial Cells / drug effects
  • Humans
  • Lipopolysaccharides / toxicity
  • Macrocyclic Compounds / chemistry*
  • Mice
  • Molecular Structure
  • RAW 264.7 Cells
  • Tumor Necrosis Factor-alpha / antagonists & inhibitors
  • Tumor Necrosis Factor-alpha / metabolism

Substances

  • Anti-Inflammatory Agents
  • Antineoplastic Agents, Phytogenic
  • Glucosides
  • Lipopolysaccharides
  • Macrocyclic Compounds
  • Tumor Necrosis Factor-alpha
  • clemochinenoside D