title: Morroniside cinnamic acid conjugate as an anti-inflammatory agent.
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.
authors.affiliation: Department of Chemistry, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan.
authors.forename: Yoshinori
authors.initials: Y
authors.lastname: Takeda
authors.forename: Naomi
authors.initials: N
authors.lastname: Tanigawa
authors.forename: Fortunatus
authors.initials: F
authors.lastname: Sunghwa
authors.forename: Masayuki
authors.initials: M
authors.lastname: Ninomiya
authors.forename: Makoto
authors.initials: M
authors.lastname: Hagiwara
authors.forename: Kenji
authors.initials: K
authors.lastname: Matsushita
authors.forename: Mamoru
authors.initials: M
authors.lastname: Koketsu
mesh_terms: D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D002460:Cell Line; D002934:Cinnamates / Q000737:chemistry; D019040:E-Selectin / Q000737:chemistry / Q000378:metabolism; D006027:Glycosides / Q000737:chemistry; D006801:Humans; D010666:Phenylpropionates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D014409:Tumor Necrosis Factor-alpha / Q000378:metabolism
chemical_list: D000893:Anti-Inflammatory Agents; D002934:Cinnamates; D019040:E-Selectin; D006027:Glycosides; D010666:Phenylpropionates; D011714:Pyrans; D014409:Tumor Necrosis Factor-alpha; C488401:morroniside; C029010:cinnamic acid