title: Cyclooxygenase-2 inhibitory phenylbutenoids from the rhizomes of Zingiber cassumunar.
abstract: Phenylbutenoids isolated previously from the CHCl3 extracts of the rhizomes of Zingiber cassumunar, were evaluated for their cyclooxygenase-2 (COX-2) inhibitory activity along with a new isolate, from the n-BuOH extracts of this plant. The COX-2 inhibitory assay was performed by measuring prostaglandin E2 production in lipopolysaccharide-stimulated mouse macrophage RAW 264.7 cells. Two phenylbutenoid dimers, and, exhibited considerable activity with IC50 values of 2.71 and 3.64 microM. Two phenylbutenoid monomers, and, showed moderate activity (IC50 14.97, 20.68 microM, respectively). The other three phenylbutenoids, were found to be inactive. Compound was elucidated as a new phenylbutenoid glycoside, namely, (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-O-beta-D-glucopyranoside by spectral analysis including various 1D- and 2D-NMR experiments.
authors.affiliation: College of Pharmacy, Ewha Womans University, Seoul, Korea.
authors.forename: Ah-Reum
authors.initials: AR
authors.lastname: Han
authors.forename: Moon-Sun
authors.initials: MS
authors.lastname: Kim
authors.forename: Yeon Hee
authors.initials: YH
authors.lastname: Jeong
authors.forename: Sang Kook
authors.initials: SK
authors.lastname: Lee
authors.forename: Eun-Kyoung
authors.initials: EK
authors.lastname: Seo
mesh_terms: D000818:Animals; D000068579:Celecoxib; D002460:Cell Line; D051546:Cyclooxygenase 2; D016861:Cyclooxygenase Inhibitors / Q000302:isolation & purification* / Q000494:pharmacology*; D015232:Dinoprostone / Q000378:metabolism; D020939:Zingiber officinale / Q000737:chemistry*; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism; D008968:Molecular Conformation; D010654:Phenylbutyrates / Q000302:isolation & purification* / Q000494:pharmacology*; D018517:Plant Roots / Q000737:chemistry; D011720:Pyrazoles / Q000494:pharmacology; D051381:Rats; D013329:Structure-Activity Relationship; D013449:Sulfonamides / Q000494:pharmacology
chemical_list: D016861:Cyclooxygenase Inhibitors; D010654:Phenylbutyrates; D011720:Pyrazoles; D013449:Sulfonamides; D051546:Cyclooxygenase 2; D000068579:Celecoxib; D015232:Dinoprostone