Anti-oxidative and inhibitory activities on nitric oxide (NO) and prostaglandin E2 (COX-2) production of flavonoids from seeds of Prunus tomentosa Thunberg.
Chemical investigation of the 80% Me(2)CO extract from the seeds of Prunus tomentosa led to the isolation and identification of six flavonoids: kaempferol (1), kaempferol 3-O-alpha-L-rhamnopyranoside (2; afzelin), kaempferol 3-O-beta-D-(6-acetyl)-glucopyranosyl(1-->4)-alpha-L-rhamnopyranoside (3; multiflorin A), kaempferol 3-O-beta-D-glucopyranosyl(1-->4)-alpha-L-rhamnopyranoside (4; multiflorin B), quercetin 3-O-alpha-L-rhamnopyranoside (5; quercitrin), and quercetin 3-O-beta-D-glucopyranosyl (1-->4)-alpha-L-rhamnopyranoside (6; multinoside A). Anti-oxidative and inhibitory activities on nitric oxide (NO) and prostaglandin E(2) production in interferon-gamma (INF-gamma) and lipopolysaccharide (LPS)-activated RAW 264.7 cells in vitro (COX-2) of the isolated compounds were evaluated. Compounds 1, 5, and 6 exhibited potent anti-oxidative activity in the DPPH radical scavenging assay with IC(50) values of 57.2, 59.4, and 54.3 microg/mL respectively. The positive control, ascorbic acid, had an IC(50) of 55.5 mug/mL. Compounds 1, 5, and 6 also reduced COX-2 levels in a dose dependent manner with IC(50) values of 10.2, 8.7, and 9.6 microg/mL respectively, with the positive control, indomethacin, having an IC(50) of 5.1 microg/mL. All six compounds inhibited NO production in a dose dependent manner with IC(50) values of 35.1, 42.8, 40.0, 44.8, 43.7, and 43.9 microg/mL respectively, while the positive control, L-NMMA, had an IC(50) of 42.1 microg/mL.
Kim
Sung Kyu
SK
College of Pharmacy, Chung-Ang University, Seoul, 156-756, Korea.
Kim
Hyun Jung
HJ
Choi
Sun Eun
SE
Park
Kwan Hee
KH
Choi
Hyung Kyun
HK
Lee
Min Won
MW
D000818:Animals; D002470:Cell Survival / Q000187:drug effects; D002867:Chromones / Q000494:pharmacology; D051546:Cyclooxygenase 2 / Q000378:metabolism*; D052246:Cyclooxygenase 2 Inhibitors / Q000302:isolation & purification / Q000494:pharmacology*; D015232:Dinoprostone / Q000378:metabolism*; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000302:isolation & purification / Q000494:pharmacology*; D005419:Flavonoids / Q000302:isolation & purification / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000302:isolation & purification / Q000494:pharmacology*; D006027:Glycosides / Q000494:pharmacology; D007213:Indomethacin / Q000494:pharmacology; D007371:Interferon-gamma / Q000378:metabolism; D044949:Kaempferols / Q000494:pharmacology; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects / Q000201:enzymology; D008362:Mannosides / Q000494:pharmacology; D051379:Mice; D015394:Molecular Structure; D009569:Nitric Oxide / Q000378:metabolism*; D019001:Nitric Oxide Synthase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D044945:Proanthocyanidins / Q000494:pharmacology; D027861:Prunus / Q000737:chemistry; D011794:Quercetin / Q000031:analogs & derivatives / Q000494:pharmacology; D012639:Seeds; D019323:omega-N-Methylarginine / Q000494:pharmacology
D002867:Chromones; D052246:Cyclooxygenase 2 Inhibitors; D004791:Enzyme Inhibitors; D005419:Flavonoids; D016166:Free Radical Scavengers; D006027:Glycosides; D044949:Kaempferols; D008070:Lipopolysaccharides; D008362:Mannosides; D044945:Proanthocyanidins; C087919:kaempferol-3-O-glucopyranosyl-1-4-rhamnopyranoside; D019323:omega-N-Methylarginine; C012526:quercitrin; D009569:Nitric Oxide; C477954:afzelin; C087918:multiflorin A; C006552:kaempferol; D007371:Interferon-gamma; D011794:Quercetin; D019001:Nitric Oxide Synthase; C077623:Ptgs2 protein, mouse; D051546:Cyclooxygenase 2; D015232:Dinoprostone; D007213:Indomethacin