title: Itosides J-N from Itoa orientalis and structure - anti-COX-2 activity relationship of phenolic glycosides.
abstract: Two new phenolic glycosides, itosides J (1) and K (2), two new cylcohexenoyl glycosides, itosides L (3) and M (4), a new flavone glycoside, itoside N (5), and echitin (6) were isolated from the extract of the bark, twigs, and leaves of Itoa orientalis, together with 22 known compounds. The structures were elucidated by means of UV, IR, MS, and NMR techniques, and the relative configuration of compound 3 was confirmed by X-ray crystallography. NMR data for 6 are reported for the first time. Compounds 1, 3, 5, and phenolic glycosides 7- 22 were also assayed for anti-inflammatory activity against COX-2. Compounds 8, 10, 12- 14, 16, 19, 24, 26, and 27 showed significant inhibitory effects, with inhibitory rates of 49.7-85.3% at 10 microM.
authors.affiliation: Department of Natural Medicines, School of Pharmaceutical Sciences, Peking University Health Science Center, Haidian District, Beijing, PR China.
authors.forename: Xing Yun
authors.initials: XY
authors.lastname: Chai
authors.forename: Yue Lin
authors.initials: YL
authors.lastname: Song
authors.forename: Zheng Ren
authors.initials: ZR
authors.lastname: Xu
authors.forename: Hai Ming
authors.initials: HM
authors.lastname: Shi
authors.forename: Chang Cai
authors.initials: CC
authors.lastname: Bai
authors.forename: Dan
authors.initials: D
authors.lastname: Bi
authors.forename: Jing
authors.initials: J
authors.lastname: Wen
authors.forename: Fei Fei
authors.initials: FF
authors.lastname: Li
authors.forename: Peng Fei
authors.initials: PF
authors.lastname: Tu
mesh_terms: D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D052246:Cyclooxygenase 2 Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D010946:Plants, Medicinal / Q000737:chemistry*; D031308:Salicaceae / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D052246:Cyclooxygenase 2 Inhibitors; D004365:Drugs, Chinese Herbal; D006027:Glycosides; D010636:Phenols