Itosides J−N from Itoa orientalis and Structure−Anti-COX-2 Activity Relationship of Phenolic Glycosides

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2008-05, Vol.71 (5), p.814-819
• Main Authors: Chai, Xing Yun, Song, Yue Lin, Xu, Zheng Ren, Shi, Hai Ming, Bai, Chang Cai, Bi, Dan, Wen, Jing, Li, Fei Fei, Tu, Peng Fei
• Format: Article
• Language: English
• Subjects: anti-inflammatory activity; Anti-Inflammatory Agents, Non-Steroidal - chemistry; Anti-Inflammatory Agents, Non-Steroidal - isolation & purification; Anti-Inflammatory Agents, Non-Steroidal - pharmacology; Biological and medical sciences; chemical structure; Cyclooxygenase 2 Inhibitors - chemistry; Cyclooxygenase 2 Inhibitors - isolation & purification; Cyclooxygenase 2 Inhibitors - pharmacology; Drugs, Chinese Herbal - chemistry; Drugs, Chinese Herbal - isolation & purification; Drugs, Chinese Herbal - pharmacology; enzyme inhibition; Flacourtiaceae - chemistry; General pharmacology; glycosides; Glycosides - chemistry; Glycosides - isolation & purification; Glycosides - pharmacology; Itoa orientalis; itoside; Medical sciences; Molecular Structure; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; phenolic compounds; Phenols - chemistry; Phenols - isolation & purification; Phenols - pharmacology; phytochemicals; Plants, Medicinal - chemistry; prostaglandin synthase; Salicaceae; spectral analysis; stereochemistry; Structure-Activity Relationship
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np800014s

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 µM.