Itosides J-N from Itoa orientalis and structure - anti-COX-2 activity relationship of phenolic glycosides.
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.
Chai
Xing Yun
XY
Department of Natural Medicines, School of Pharmaceutical Sciences, Peking University Health Science Center, Haidian District, Beijing, PR China.
Song
Yue Lin
YL
Xu
Zheng Ren
ZR
Shi
Hai Ming
HM
Bai
Chang Cai
CC
Bi
Dan
D
Wen
Jing
J
Li
Fei Fei
FF
Tu
Peng Fei
PF
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
D000894:Anti-Inflammatory Agents, Non-Steroidal; D052246:Cyclooxygenase 2 Inhibitors; D004365:Drugs, Chinese Herbal; D006027:Glycosides; D010636:Phenols