title: Anti-inflammatory triterpenoid saponins from the stem bark of Kalopanax pictus.
abstract: Five new compounds, 16,23,29-trihydroxy-3-oxo-olean-12-en-28-oic acid (1), 4,23,29-trihydroxy-3,4-seco-olean-12-en-3-oate-28-oic acid (2), 3β,6β,23-trihydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranoside (3), 3-O-[2,3-di-O-acetyl-α-L-arabinopyranosyl]hederagenin 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (4), and 3-O-[3,4-di-O-acetyl-α-L-arabinopyranosyl]hederagenin 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (5), as well as 10 known compounds (6-15), were isolated from the stem bark of Kalopanax pictus. Compounds 1-5 and 7-14 inhibited TNFα-induced NF-κB transcriptional activity in HepG2 cells in a dose-dependent manner, with IC50 values ranging from 0.6 to 16.4 μM. Furthermore, the transcriptional inhibitory function of these compounds was confirmed on the basis of decreases in COX-2 and iNOS gene expression in HepG2 cells. The structure-activity relationship of the compounds with respect to anti-inflammatory activity is also discussed.
authors.affiliation: College of Pharmacy, Chungnam National University, Daejeon 305-764, Korea.
authors.forename: Tran H
authors.initials: TH
authors.lastname: Quang
authors.forename: Nguyen T T
authors.initials: NT
authors.lastname: Ngan
authors.forename: Chau V
authors.initials: CV
authors.lastname: Minh
authors.forename: Phan V
authors.initials: PV
authors.lastname: Kiem
authors.forename: Nguyen X
authors.initials: NX
authors.lastname: Nhiem
authors.forename: Bui H
authors.initials: BH
authors.lastname: Tai
authors.forename: Nguyen P
authors.initials: NP
authors.lastname: Thao
authors.forename: Nguyen H
authors.initials: NH
authors.lastname: Tung
authors.forename: Seok B
authors.initials: SB
authors.lastname: Song
authors.forename: Young H
authors.initials: YH
authors.lastname: Kim
mesh_terms: D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001483:Base Sequence; D052246:Cyclooxygenase 2 Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D056945:Hep G2 Cells; D006801:Humans; D036882:Kalopanax / Q000737:chemistry*; D007723:Korea; D015394:Molecular Structure; D016328:NF-kappa B / Q000187:drug effects; D052247:Nitric Oxide Synthase Type II / Q000037:antagonists & inhibitors; D024301:Plant Bark / Q000737:chemistry; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
chemical_list: D000893:Anti-Inflammatory Agents; D052246:Cyclooxygenase 2 Inhibitors; D016328:NF-kappa B; D012503:Saponins; D014315:Triterpenes; D052247:Nitric Oxide Synthase Type II