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.
Yoshinori Takeda  1 ,  Naomi Tanigawa ,  Fortunatus Sunghwa ,  Masayuki Ninomiya ,  Makoto Hagiwara ,  Kenji Matsushita ,  Mamoru Koketsu
Affiliations
  • 1. Department of Chemistry, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan.
PMID: 20621474 DOI: 10.1016/j.bmcl.2010.06.095
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.