ABSTRACT
A chemical investigation of K. heteroclite led to isolation of two new dibenzocyclooctadienes (1 and 2) together with 14 known compounds (3-16) by using multiple chromatographic techniques. New compounds (1 and 2) were obtained and identified by spectroscopic methods (HR-ESI-MS, 1D and 2D NMR, and ECD) as well as by comparison of their experimental data with those reported in the literatures. All the isolates were evaluated for their ability to modulate TNF-α production in lipopolysaccharide (LPS) stimulated RAW264.7 cells. Among them, compound 5 displayed the most inhibition against tumor necrosis factor (TNF)-α production with IC50 value of 6.16±0.14â µM. Whereas, compounds (1, 3, and 6) showed the significant inhibition (IC50 values ranging from 9.41 to 14.54â µM), and compounds (2, 4, 9, 10, 13, 15, and 16) exhibited moderate inhibition (IC50 values ranging from 19.27 to 40.64â µM) toward TNF-α production, respectively.
Subject(s)
Kadsura , Lignans , Kadsura/chemistry , Tumor Necrosis Factor-alpha , Lignans/pharmacology , Lignans/chemistry , Anti-Inflammatory Agents/pharmacology , Phenols , Molecular StructureABSTRACT
From the fruits of Schisandra cauliflora, five new dimethylbutyrylated dibenzocyclooctadiene lignans, named schisandracaurins A-E, were isolated using separation and chromatographic techniques. Their structures were determined by extensive analyses of HR-ESI-MS, NMR, and ECD spectra. The schisandracaurins A-E potentially inhibited NO production in LPS-activated RAW264.7 cells with their IC50 values from 21.4 to 30.3â µM.
Subject(s)
Lignans , Schisandra , Schisandra/chemistry , Lipopolysaccharides/pharmacology , Molecular Structure , Fruit/chemistry , Lignans/chemistry , Cyclooctanes/pharmacology , Cyclooctanes/analysis , Cyclooctanes/chemistryABSTRACT
Using various chromatographic methods, five new steroidal saponins named taccavietnamosides A-E (1-5) and three known, (24S,25R)-spirost-5-en-3ß,24-diol 3-O-α-l-rhamnopyranosyl-(1â2)-[α-l-rhamnopyranosyl-(1â3)]-ß-d-glucopyranoside (6), (24S,25R)-spirost-5-en-3ß,24-diol 3-O-α-l-rhamnopyranosyl-(1â2)-[ß-d-glucopyranosyl-(1â4)-α-l-rhamnopyranosyl-(1â3)]-ß-d-glucopyranoside (7), and chantrieroside A (8) were isolated from the rhizomes of Tacca vietnamensis Thin et Hoat. Their chemical structures were elucidated by physical and chemical methods. All compounds were evaluated for the inhibitory activities of nitric oxide production in LPS-stimulated RAW 264.7 macrophages and BV2 cells. As the results, compounds 3-5 showed moderate inhibition on NO production in LPS-stimulated BV2 cells and RAW 264.7 macrophages with the IC50 values ranging from 37.0 to 60.7µM.
Subject(s)
Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Dioscoreaceae/chemistry , Nitric Oxide/antagonists & inhibitors , Saponins/pharmacology , Spirostans/pharmacology , Animals , Anti-Inflammatory Agents, Non-Steroidal/chemistry , Anti-Inflammatory Agents, Non-Steroidal/isolation & purification , Cell Line , Dose-Response Relationship, Drug , Lipopolysaccharides/antagonists & inhibitors , Lipopolysaccharides/pharmacology , Macrophages/drug effects , Macrophages/metabolism , Mice , Molecular Structure , Nitric Oxide/biosynthesis , RAW 264.7 Cells , Saponins/chemistry , Saponins/isolation & purification , Spirostans/chemistry , Spirostans/isolation & purification , Structure-Activity RelationshipABSTRACT
Five new lupane triterpene coumaroyl esters (1-5), together with betulin (6) and a known Buxus alkaloid, N-3-benzoyldihydrocyclomicrophylline F (7), were isolated from a CHCl3-soluble partition of a methanol extract of Buxus cochinchinensis Pierre ex Gagnep. (Buxaceae) collected in Vietnam. Isolation work was monitored using human colon cancer cells (HT-29). The structures of the new compounds (1-5) were determined on the basis of spectroscopic data interpretation. In addition to their cytotoxicity against HT-29 cells and nuclear factor-kappa B (p65) inhibitory activity in an enzyme-linked immunosorbent assay, all isolates as well as two semisynthetic compounds derived from betulin and 5, respectively, were also evaluated for their in vitro antiplasmodial activities against the drug-resistant Dd2 strain of Plasmodium falciparum and antifungal effects on the growth of the pathogenic yeast Candida albicans. The new lupane triterpene coumaroyl esters (1-5), along with a betulin derivative and the known Buxus alkaloid, were found to show significant in vitro antimalarial activities, with IC50 values ranging from 0.26 to 2.07 µM.
Subject(s)
Alkaloids/chemistry , Antimalarials/chemistry , Buxus/chemistry , Plant Extracts/chemistry , Triterpenes/chemistry , Alkaloids/isolation & purification , Alkaloids/pharmacology , Antimalarials/isolation & purification , Antimalarials/pharmacology , Esters/chemistry , Esters/isolation & purification , Esters/pharmacology , HT29 Cells , Humans , Inhibitory Concentration 50 , Molecular Structure , Plant Extracts/isolation & purification , Plant Extracts/pharmacology , Plasmodium falciparum/drug effects , Triterpenes/isolation & purification , Triterpenes/pharmacology , VietnamABSTRACT
A new dibenzocyclooctadiene lignan, acetylepigomisin R ( 1), and a new 3,4-seco-lanostane-type triterpene, seco-coccinic acid F ( 2), along with three known dibenzocyclooctadiene lignans, isovaleroylbinankadsurin A ( 3), kadsuralignan J ( 4), and binankadsurin A ( 5), and one lanostane-type triterpene, 20( R),24( E)-3-oxo-9 beta-lanosta-7,24-dien-26-oic acid ( 6), were isolated from the methanol extract of the Kadsura coccinea roots. Their structures were elucidated on the basis of spectroscopic evidence including ESI-MS, HR-EI-MS, 1D and 2D NMR. The protective effects of these compounds were evaluated in primary cultured rat hepatocytes intoxicated with 1.2 mM T-butyl hydroperoxide. Compounds 1, 3, and 5 showed protective effects with ED (50) values of 135.7, 26.1, and 79.3 microM, respectively.
