title: Anti-oxidative and anti-inflammatory activities of caffeoyl hemiterpene glycosides from Spiraea prunifolia.
abstract: Activity guided isolation of a Spiraea prunifolia extract yielded five caffeoyl hemiterpene glycosides: 4'-(6-O-caffeoyl-β-D-glucopyranosyl)-2'-methyl butyric acid, 1-O-caffeoyl-6-O-(4'-hydroxy-2'-methylene-butyroyl)-β-D-glucopyranoside, 1,2-O-dicaffeoyl-6-O-(4'-hydroxy-2'-methylene-butyroyl)-β-D-glucopyranoside, 1-O-caffeoyl-6-O-(4'-caffeoyl-2'-methylene-butyroyl)-β-D-glucopyranoside, and 1-O-caffeoyl-6-O-(4'-caffeoyl-3'-hydroxy-2'-methylene-butyroyl)-β-D-glucopyranoside, and nine known compounds. Structures were elucidated by analysis of 1D and 2D NMR spectra and FAB-MS. To evaluate the anti-oxidative and anti-inflammatory properties of all fourteen compounds, DPPH radical scavenging, NBT superoxide scavenging, and inhibition of nitric oxide production in LPS-stimulated RAW264.7 cells were examined. Three of the caffeoyl hemiterpene glycosides exhibited potent anti-oxidative and anti-inflammatory activities compared with Vitamin C and l-NMMA, which were used as positive controls.
authors.affiliation: Department of Pharmacognosy, College of Pharmacy, Chung-Ang University, Seoul 156-756, Republic of Korea.
authors.forename: Sang Hee
authors.initials: SH
authors.lastname: Park
authors.forename: Kwan Hee
authors.initials: KH
authors.lastname: Park
authors.forename: Myeong Hwan
authors.initials: MH
authors.lastname: Oh
authors.forename: Han Hyuk
authors.initials: HH
authors.lastname: Kim
authors.forename: Kang In
authors.initials: KI
authors.lastname: Choe
authors.forename: So Ra
authors.initials: SR
authors.lastname: Kim
authors.forename: Kwang Jun
authors.initials: KJ
authors.lastname: Park
authors.forename: Min Won
authors.initials: MW
authors.lastname: Lee
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001713:Biphenyl Compounds / Q000494:pharmacology; D002109:Caffeic Acids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000737:chemistry / Q000494:pharmacology; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D045782:Hemiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects; D051379:Mice; D015394:Molecular Structure; D009569:Nitric Oxide / Q000096:biosynthesis; D019906:Nuclear Magnetic Resonance, Biomolecular; D010851:Picrates / Q000494:pharmacology; D031992:Spiraea / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000893:Anti-Inflammatory Agents; D000975:Antioxidants; D001713:Biphenyl Compounds; D002109:Caffeic Acids; D016166:Free Radical Scavengers; D006027:Glycosides; D045782:Hemiterpenes; D008070:Lipopolysaccharides; D010851:Picrates; D009569:Nitric Oxide; C004931:1,1-diphenyl-2-picrylhydrazyl
keywords: Caffeoyl hemiterpenes; DPPH radical scavenging activity; Hemiterpene glycosides; NBT superoxide scavenging activity; NO production; Rosaceae; Spiraea prunifolia