ABSTRACT
Four new polyoxygenated sterol derivatives (1-4) along with the compounds (5-7) previously known from other biological sources were isolated from the gorgonian Menella woodin, collected from the Vietnamese waters. Structures of 1-4 were elucidated by the detailed NMR spectroscopic and mass-spectrometric analyses as well as comparison with those reported in literature data. Compounds 1, 4, and 6 decrease the production of reactive oxygen species (ROS) by the murine macrophages of RAW 264.7 line at induction by endotoxic lipopolysaccharide (LPS) from Escherichia coli.
Subject(s)
Anthozoa/chemistry , Lipopolysaccharides/pharmacology , Macrophages/drug effects , Macrophages/metabolism , Reactive Oxygen Species/metabolism , Steroids/pharmacology , Animals , Cell Line , Cell Survival/drug effects , Dose-Response Relationship, Drug , Mice , Molecular Conformation , Reactive Oxygen Species/antagonists & inhibitors , Steroids/chemistry , Steroids/isolation & purification , Structure-Activity RelationshipABSTRACT
Six new triterpenoids (1-6) and the previously known penasterone, acetylpenasterol, and ergosta-4,24(28)-dien-3-one were isolated from a Penares sp. sponge collected from Vietnamese waters. Structures of the obtained compounds were established by extensive 1D and 2D NMR spectroscopy and mass spectrometry. Configurations of the triterpene epoxy lactones (1-4) were determined on the basis of NOESY and CD data and calculation of spin coupling constants and confirmed by X-ray crystallographic analysis of compound 2. The isolated triterpenoid 6 was cytotoxic against human leukemia HL-60 cells (IC50 = 9.7 µM).
Subject(s)
Antineoplastic Agents/isolation & purification , Antineoplastic Agents/pharmacology , Porifera/chemistry , Triterpenes/isolation & purification , Triterpenes/pharmacology , Animals , Antineoplastic Agents/chemistry , Crystallography, X-Ray , Drug Screening Assays, Antitumor , HL-60 Cells , Humans , Lanosterol/analogs & derivatives , Marine Biology , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Triterpenes/chemistry , VietnamABSTRACT
Three new diarylheptanoids, (3S,5R)-3-hydroxy-5-methoxy-1,7-bis(4-hydroxyphenyl)-6E-heptene (1), (3S,5S)-3-hydroxy-5-methoxy-1,7-bis(4-hydroxyphenyl)-6E-heptene (2), and (3S)-3-hydroxy-1,7-bis(4-hydroxyphenyl)-6E-hepten-5-one (3), four new flavonoid glycosides, 3,7,3'-tri-O-methylquercetin-4'-O-ß-d-apiofuranosyl-(1â2)-O-ß-d-glucopyranoside (4), 7,3'-di-O-methylquercetin-4'-O-ß-d-glucopyranosyl-3-O-[6â´-(3-hydroxy-3-methylglutaroyl)]-α-d-glucopyranoside (5), 7,3'-di-O-methylquercetin-4'-O-ß-d-glucopyranosyl-3-O-[(6'''''â5'''')-O-1'''''-(sinap-4-yl)-ß-d-glucopyranosyl-6â´-(3-hydroxy-3-methylglutaroyl)]-α-d-glucopyranoside (6), and (2S)-5-hydroxy-7,3'-dimethoxyflavanone-4'-O-ß-d-apiofuranosyl-(1â5)-O-ß-d-apiofuranosyl-(1â2)-O-ß-d-glucopyranoside (9), and 17 known compounds were isolated from the leaves and twigs of Viscum album. Compounds 1, 4, and 19 significantly inhibited LPS-stimulated production of TNF-α, IL-6, and IL-12p40 with IC50 values ranging from 0.09 ± 0.01 to 8.96 ± 0.45 µM. (+)-Medioresinol (13) showed inhibitory effects on LPS-stimulated production of IL-12p40 with an IC50 value of 2.00 ± 0.15 µM.
Subject(s)
Anti-Inflammatory Agents/isolation & purification , Anti-Inflammatory Agents/pharmacology , Diarylheptanoids/isolation & purification , Diarylheptanoids/pharmacology , Flavonoids/isolation & purification , Flavonoids/pharmacology , Glycosides/isolation & purification , Glycosides/pharmacology , Viscum album/chemistry , Animals , Anti-Inflammatory Agents/chemistry , Bone Marrow Cells/drug effects , Cytokines/antagonists & inhibitors , Dendritic Cells/drug effects , Diarylheptanoids/chemistry , Flavonoids/chemistry , Glycosides/chemistry , Inhibitory Concentration 50 , Interleukin-12 Subunit p40/antagonists & inhibitors , Interleukin-6/antagonists & inhibitors , Lipopolysaccharides/pharmacology , Mice , Mice, Inbred C57BL , Plant Leaves/chemistry , Plant Stems/chemistry , Stereoisomerism , Tumor Necrosis Factor-alpha/antagonists & inhibitorsABSTRACT
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), 3ß,6ß,23-trihydroxyolean-12-en-28-oic acid 28-O-ß-D-glucopyranoside (3), 3-O-[2,3-di-O-acetyl-α-L-arabinopyranosyl]hederagenin 28-O-α-L-rhamnopyranosyl-(1â4)-ß-D-glucopyranosyl-(1â6)-ß-D-glucopyranoside (4), and 3-O-[3,4-di-O-acetyl-α-L-arabinopyranosyl]hederagenin 28-O-α-L-rhamnopyranosyl-(1â4)-ß-D-glucopyranosyl-(1â6)-ß-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.