Diarylheptanoid glycosides from Tacca plantaginea and their effects on NF-κB activation and PPAR transcriptional activity

Bioorg Med Chem Lett. 2012 Nov 1;22(21):6681-7. doi: 10.1016/j.bmcl.2012.08.099. Epub 2012 Sep 13.

Abstract

In the screening search for NF-κB inhibitory and PPAR transactivational agents from medicinal plants, a methanol extract of the whole plant of Tacca plantaginea and its aqueous fraction showed the significant activities. Bioassay-guided fractionation combined with repeated chromatographic separation of the aqueous fraction of the methanol extract of T. plantaginea resulted in the isolation of two new diarylheptanoid glycosides, plantagineosides A (1) and B (2), an unusual new cyclic diarylheptanoid glycoside, plantagineoside C (3), and three known compounds (4-6). Their structures were determined by extensive spectroscopic and chemical methods. Compounds 3-6 significantly inhibited TNFα-induced NF-κB transcriptional activity in HepG2 cells in a dose-dependent manner, with IC(50) values ranging from 0.9 to 9.4 μM. Compounds 1-6 significantly activated the transcriptional activity of PPARs in a dose-dependent manner, with EC(50) values ranging from 0.30 to 10.4 μM. In addition, the transactivational effects of compounds 1-6 were evaluated on three individual PPAR subtypes, including PPARα, γ, and β(δ). Compounds 1-6 significantly enhanced the transcriptional activity of PPARβ(δ), with EC(50) values in a range of 11.0-30.1 μM. These data provide the rationale for using T. plantaginea and its components for the prevention and treatment of inflammatory and metabolic diseases.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antimetabolites / chemistry
  • Antimetabolites / pharmacology
  • Diarylheptanoids / chemistry*
  • Diarylheptanoids / pharmacology
  • Dioscoreaceae / chemistry*
  • Enzyme Activation / drug effects
  • Glycosides / chemistry*
  • Glycosides / pharmacology
  • Hep G2 Cells
  • Humans
  • Magnetic Resonance Spectroscopy
  • Methanol / chemistry
  • Molecular Structure
  • NF-kappa B / metabolism*
  • Peroxisome Proliferator-Activated Receptors / metabolism*
  • Transcription, Genetic / drug effects*

Substances

  • Antimetabolites
  • Diarylheptanoids
  • Glycosides
  • NF-kappa B
  • Peroxisome Proliferator-Activated Receptors
  • plantagineoside A
  • plantagineoside B
  • plantagineoside C
  • Methanol