Morroniside cinnamic acid conjugate as an anti-inflammatory agent.
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.
Takeda
Yoshinori
Y
Department of Chemistry, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan.
Tanigawa
Naomi
N
Sunghwa
Fortunatus
F
Ninomiya
Masayuki
M
Hagiwara
Makoto
M
Matsushita
Kenji
K
Koketsu
Mamoru
M
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
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