title: Isoeugenin, a Novel Nitric Oxide Synthase Inhibitor Isolated from the Rhizomes of Imperata cylindrica.
abstract: Phytochemical studies on the constituents of the rhizomes of Imperata cylindrica (Gramineae) were performed using high-performance liquid chromatography (HPLC). We also aimed to search for any biologically active substance capable of inhibiting nitric oxide (NO) formation in lipopolysaccharide (LPS)-activated macrophage 264.7 cells, by testing four compounds isolated from this plant. Four compounds, including a new chromone, isoeugenin, along with ferulic acid, p-coumaric acid, and caffeic acid were isolated and identified by NMR spectroscopy. The structure of isoeugenin was determined as 7-hydroxy-5-methoxy-2-methylchromone by the 2D-NMR technique. Among the four compounds, isoeugenin has the lowest IC50 value on the inhibition of NO production in LPS-activated macrophage RAW264.7 cells (IC50, 9.33 μg/mL). In addition, isoeugenin significantly suppressed the LPS-induced expressions of inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), and proinflammatory cytokines mRNA levels. Taken together, these results suggest that the anti-inflammatory activity of isoeugenin is associated with the down-regulation of iNOS, COX-2, and pro-inflammatory cytokines in RAW264.7 cells. Accordingly, our results suggest that the new chromone isoegenin should be considered a potential treatment for inflammatory disease.
authors.affiliation: Department of Pharmacology, College of Korean Medicine, Sangji University, Wonju 220-702, Korea. hjan@sj.ac.kr.
authors.forename: Hyo-Jin
authors.initials: HJ
authors.lastname: An
authors.affiliation: Department of Agro-Industrial Technology, Faculty of Agriculture, Lambung Mangkurat University, Indonesia 70712, Indonesia. agung_tin@yahoo.com.
authors.forename: Agung
authors.initials: A
authors.lastname: Nugroho
authors.affiliation: Department of Forest Science, College of Life Science and Natural Resources, Sangji University, Wonju 220-702, Korea. bmsong@sangji.ac.kr.
authors.forename: Byong-Min
authors.initials: BM
authors.lastname: Song
authors.affiliation: Department of Pharmaceutical Engineering, College of Health Science, Sangji University, Wonju 220-702, Korea. hjpark@sangji.ac.kr.
authors.forename: Hee-Juhn
authors.initials: HJ
authors.lastname: Park
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000302:isolation & purification / Q000494:pharmacology*; D002867:Chromones / Q000737:chemistry / Q000494:pharmacology*; D051546:Cyclooxygenase 2 / Q000737:chemistry; D016207:Cytokines / Q000235:genetics; D004791:Enzyme Inhibitors / Q000302:isolation & purification / Q000494:pharmacology*; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000166:cytology / Q000187:drug effects* / Q000378:metabolism; D051379:Mice; D009569:Nitric Oxide / Q000378:metabolism; D052247:Nitric Oxide Synthase Type II / Q000037:antagonists & inhibitors*; D010936:Plant Extracts / Q000494:pharmacology*; D006109:Poaceae / Q000737:chemistry*; D000067996:RAW 264.7 Cells; D012333:RNA, Messenger / Q000235:genetics; D060888:Real-Time Polymerase Chain Reaction; D020133:Reverse Transcriptase Polymerase Chain Reaction; D027343:Rhizome / Q000737:chemistry*
chemical_list: D000893:Anti-Inflammatory Agents; D002867:Chromones; D016207:Cytokines; D004791:Enzyme Inhibitors; D008070:Lipopolysaccharides; D010936:Plant Extracts; D012333:RNA, Messenger; C000610632:isoeugenin; D009569:Nitric Oxide; D052247:Nitric Oxide Synthase Type II; D051546:Cyclooxygenase 2
keywords: HPLC; Imperata cylindrica; NO; RAW264.7 macrophages; isoeugenin