Morroniside cinnamic acid conjugate as an anti-inflammatory agent

Bioorg Med Chem Lett. 2010 Aug 15;20(16):4855-7. doi: 10.1016/j.bmcl.2010.06.095. Epub 2010 Jun 20.

Abstract

A morroniside cinnamic acid conjugate was prepared and evaluated on E-selectin mediated cell-cell adhesion as an important role in inflammatory processes. 7-O-Cinnamoylmorroniside exhibited excellent anti-inflammatory activity (IC(50)=49.3 microM) by inhibiting the expression of E-selectin; further, it was more active than another cinnamic-acid-conjugated iridoid glycoside (harpagoside; IC(50)=88.2 microM), 7-O-methylmorroniside, and morroniside itself. As a result, 7-O-cinnamoylmorroniside was observed to be a potent inhibitor of TNF-alpha-induced E-selectin expression.

MeSH terms

  • Anti-Inflammatory Agents / chemical synthesis
  • Anti-Inflammatory Agents / chemistry*
  • Anti-Inflammatory Agents / pharmacology
  • Cell Line
  • Cinnamates / chemistry
  • E-Selectin / chemistry
  • E-Selectin / metabolism
  • Glycosides / chemistry
  • Humans
  • Phenylpropionates / chemical synthesis
  • Phenylpropionates / chemistry
  • Phenylpropionates / pharmacology*
  • Pyrans / chemical synthesis
  • Pyrans / chemistry
  • Pyrans / pharmacology*
  • Tumor Necrosis Factor-alpha / metabolism

Substances

  • Anti-Inflammatory Agents
  • Cinnamates
  • E-Selectin
  • Glycosides
  • Phenylpropionates
  • Pyrans
  • Tumor Necrosis Factor-alpha
  • morroniside
  • cinnamic acid