title: Phenylpropanoid ester from Zingiber officinale and their inhibitory effects on the production of nitric oxide.
abstract: A new phenylpropanoid ester mixture, (E)-geranylferulic acid (1a) and (Z)-geranylferulic acid (1b), along with 13 known compounds, [6]-gingerol (2), [8]-gingerol (3), [10]-gingerdione (4), 1-dehydro-[6]-gingerdione (5), 1-dehydro-[8]-gingerdione (6), [6]-paradol (7), [8]-paradol (8), [6]-gingeroldiacetate (9), 6-hydroxy-[6]-shogaol (10), galanolactone (11), trans-®-sesquiphellandrol (12), trans-sesquipiperitol (13), and 4α,5β-dihydroxybisabola-2,10-diene (14) were isolated from ethanol extract of Zingiber officinale. Their structures were determined based on the spectroscopic (1D, 2D-NMR and MS) and chemical evidence. All of the isolates were evaluated for their potential to inhibit LPS-induced production of nitric oxide in murine macrophage RAW264.7 cells. Compounds 1-12 were found to inhibit nitric oxide production with IC(50) values ranging from 5.5 to 28.5 μM.
authors.affiliation: Natural Products Research Institute, Gyeonggi Institute of Science & Technology Promotion, Suwon 443-766, Korea.
authors.forename: Seong Su
authors.initials: SS
authors.lastname: Hong
authors.forename: Joa Sub
authors.initials: JS
authors.lastname: Oh
mesh_terms: D000818:Animals; D002470:Cell Survival / Q000187:drug effects; D002478:Cells, Cultured; D003373:Coumaric Acids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004952:Esters / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D020939:Zingiber officinale / Q000737:chemistry*; D008264:Macrophages / Q000187:drug effects; D051379:Mice; D009569:Nitric Oxide / Q000096:biosynthesis; D052247:Nitric Oxide Synthase Type II / Q000037:antagonists & inhibitors*; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: C572971:(E)-geranylferulic acid; D003373:Coumaric Acids; D004791:Enzyme Inhibitors; D004952:Esters; D010936:Plant Extracts; D009569:Nitric Oxide; D052247:Nitric Oxide Synthase Type II