ABSTRACT
A new flavan-3-ol, (+)-afzelechin 5-O-ß-d-glucopyranoside (2), together with 13 known flavonoids (1, 3-14), was isolated from the fruit peels of Wisteria floribunda. Their structures were assigned by detailed interpretation of NMR, MS, and CD spectroscopic data, as well as by comparing with published reports. The in vitro anti-inflammatory activity of the isolated compounds (1-14) was examined. Among them, compounds 3, 6, and 9 produced highest inhibitory effects on tumor necrosis factor alpha (TNF-α)-induced nuclear factor kappa-B activation in HepG2 cells with IC(50) values of 14.1, 16.5, and 11.9 µM, respectively. With the exception of compound 6, the compounds significantly inhibited the accumulation of pro-inflammatory inducible nitric oxide synthase and cyclooxygenase-2 proteins in TNF-α-stimulated HepG2 cells at a concentration as low as 0.1 µM.
Subject(s)
Anti-Inflammatory Agents, Non-Steroidal/isolation & purification , Cyclooxygenase 2/metabolism , Flavonoids/isolation & purification , Flavonoids/pharmacology , Glucosides/isolation & purification , Glucosides/pharmacology , Wisteria/chemistry , Anti-Inflammatory Agents, Non-Steroidal/chemistry , Anti-Inflammatory Agents, Non-Steroidal/immunology , Base Sequence , Dose-Response Relationship, Drug , Flavonoids/chemistry , Flavonoids/immunology , Fruit/chemistry , Glucosides/chemistry , Glucosides/immunology , Hep G2 Cells , Humans , Inhibitory Concentration 50 , Korea , NF-kappa B/immunology , Nitric Oxide/antagonists & inhibitors , Nitric Oxide Synthase Type II/metabolism , Nuclear Magnetic Resonance, Biomolecular , Phenols/chemistry , Phenols/isolation & purification , Phenols/pharmacology , Tumor Necrosis Factor-alpha/antagonists & inhibitorsABSTRACT
Rosmarinic acid, its analogues, and a phenolic compound were obtained from G. hederacea var. longituba. There were two new compounds, methyl isoferuloyl-7-(3,4-dihydroxyphenyl) lactate (1) and benzyl-4'-hydroxy-benzoyl-3'-O-ß-D-glucopyranoside (4), and four known compounds (2, 3, 5 and 6). The structures of these compounds were determined on the basis of spectroscopic methods. Each compound was tested by NF-κB luciferase assay and three rosmarinic acid analogues inhibited NF-κB production and the induction of COX-2 and iNOS mRNA in HepG2 cells.
