9,10-Dihydrophenanthrene derivatives and one 1,4-anthraquinone firstly isolated from Dioscorea zingiberensis C. H. Wright and their biological activities

Fitoterapia. 2016 Mar:109:20-4. doi: 10.1016/j.fitote.2015.11.022. Epub 2015 Nov 30.

Abstract

Two new phenanthrene derivatives, 2,5,7-trimethoxy-9,10-dihydrophenanthrene-1,4-dione (1) and 2,5,6-trihydroxy-3,4-dimethoxy-9,10-dihydrophenanthrene (3), one new anthracenedione, 2,5,7-trimethoxyanthracene-1,4-dione (2), together with two known 9,10-dihydrophenanthrenes (4-5) were isolated from the rhizomes of Dioscorea zingiberensis C. H. Wright. The structures of these new compounds were established based on extensive NMR spectroscopy. Several isolated compounds were evaluated for the inhibition against nitric oxide (NO) production in the lipopolysaccharide (LPS)-activated RAW 264.7 macrophage cell line, DPPH radical scavenging, and inhibitory activity on Free Fatty Acids (FFAs) induced triglyceride accumulation in HepG2 cells. Compound 2 exhibited moderate anti-inflammatory activity, compound 3 possessed comparable DPPH radical scavenging activity as Vitamin C, compounds 2 and 4 showed potent inhibitory activities on triglyceride accumulation.

Keywords: Anthracenedione; Anti-inflammatory; DPPH radical scavenging; Dihydrophenanthrene; Dioscorea zingiberensis C. H. Wright; Triglyceride accumulation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthraquinones / chemistry*
  • Anthraquinones / isolation & purification
  • Anti-Inflammatory Agents / chemistry*
  • Anti-Inflammatory Agents / isolation & purification
  • Dioscorea / chemistry*
  • Free Radical Scavengers / chemistry*
  • Free Radical Scavengers / isolation & purification
  • Hep G2 Cells
  • Humans
  • Macrophages / drug effects
  • Mice
  • Molecular Structure
  • Nitric Oxide / metabolism
  • Phenanthrenes / chemistry*
  • Phenanthrenes / isolation & purification
  • RAW 264.7 Cells
  • Rhizome / chemistry
  • Triglycerides / metabolism

Substances

  • Anthraquinones
  • Anti-Inflammatory Agents
  • Free Radical Scavengers
  • Phenanthrenes
  • Triglycerides
  • Nitric Oxide
  • 1,4-anthraquinone