ABSTRACT
A new resveratrol trimer, vateriferol (1), having four cis-oriented methine protons and constituting four contiguous stereocenters, was isolated from the bark extract of Vateria copallifera by bioassay-guided fractionation using a combination of normal, reversed phase, and size exclusion column chromatography. The structure was established based on its spectroscopic data. Vateriferol (1) was evaluated in vitro for its antioxidant capacity, enzyme inhibitory activity, growth inhibitory activity on a number of cancer cell lines, neuroprotective activity, and anti-inflammatory activity. Vateriferol (1) exhibited AChE inhibitory activity (IC50 8.4 ± 0.2 µM), ORAC activity (2079 ± 0.20 TE/g), and neuroprotective activity at 1.5 µM using PC12 cells deprived of oxygen and glucose and lowered NO levels in lipopolysaccharide-stimulated SIM-A9 microglial cells at 14.7 and 73.6 µM. Vateriferol (1) exhibited weak cytotoxic potency (<50% growth inhibition) against the tested cell lines at 147.2 µM.
Subject(s)
Dipterocarpaceae/chemistry , Resveratrol/chemistry , Animals , Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Antioxidants/chemistry , Antioxidants/isolation & purification , Antioxidants/pharmacology , Drug Screening Assays, Antitumor , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/isolation & purification , Enzyme Inhibitors/pharmacology , Molecular Structure , Neuroprotective Agents/chemistry , Neuroprotective Agents/isolation & purification , Neuroprotective Agents/pharmacology , PC12 Cells , Plant Bark/chemistry , Rats , Sri LankaABSTRACT
From the ethanolic extract of Caesalpinia bonduc, one new diterpene, neocaesalpin P (1) and six known diterpenoids, neocaesalpin H (2), cordylane A (3), caesalpinin B (4), bonducellpin E (5), caesalpinolide A (6), and 17-methylvouacapane-8(14),-9(11)-diene (7) were isolated. Structures of these compounds were determined from NMR spectroscopic studies. Compounds 1-7 exhibited modest antibacterial activities. All of these compounds were weakly active in glutathione S-transferase inhibition assays.
Subject(s)
Caesalpinia/chemistry , Diterpenes/analysis , Diterpenes/isolation & purification , Diterpenes/metabolism , Ethanol , Glutathione Transferase/metabolism , Magnetic Resonance Spectroscopy , Molecular StructureABSTRACT
From the bark of Vitex pinnata, one new iridoid glucoside, pinnatoside (1) and three known flavonoids, viscioside (2), apigenin (3), and luteolin (4), were isolated. Structures of these compounds were determined from NMR spectroscopic studies. Compound 1 exhibited modest antifungal activity against Candida albicans.
Subject(s)
Flavones/chemistry , Iridoids/chemistry , Vitex/chemistry , Antifungal Agents/pharmacology , Candida albicans/drug effects , Iridoids/pharmacology , Molecular Structure , Plant Bark/chemistryABSTRACT
BACKGROUND: The insecticidal activity of essential oil of Mentha piperita L. emend. Huds. against local mosquitoes as disease vectors was recognized and found to be due to the presence of menthol, which is the major aroma compound of the oil. The minor compounds of the oil, i.e. menthone, beta-caryophyllene, menthyl acetate, limonene, alpha-pinene and pulegone, showed either less or no activity against the mosquitoes tested. L-Menthol derivatives were synthesized and their knockdown effect and mortality were evaluated against local mosquitoes of Culex quinquefasciatus Say, Aedes aegypti L. and Anopheles tessellatus Theobald as disease vectors. This is the first report of mosquitocidal activity of menthol and its derivatives against Cx. quinquefasciatus, Ae. aegypti and An. tessellatus. RESULTS: Derivative synthesis followed by structure-activity relationship studies identified several derivatives, i.e. menthyl chloroacetate, menthyl dichloroacetate, menthyl cinnamate, menthone glyceryl acetal, thymol, alpha-terpineol and mugetanol, with enhanced mosquitocidal activity against Cx. quinquefasciatus, Ae. aegypti and An. tessellatus relative to the parent compound L-menthone. CONCLUSION: In ester derivatives of L-menthol the optimum activity is dependent on the size and shape of the ester group and the presence of chlorine atoms in the ester group. In structurally related derivatives of L-menthol the optimum activity is dependent on the aromaticity, the degree of unsaturation, the position of the hydroxy group and the type of functional group.
Subject(s)
Culicidae/drug effects , Insect Vectors/drug effects , Insecticides/toxicity , Mentha piperita/chemistry , Menthol/analogs & derivatives , Oils, Volatile/toxicity , Animals , Biological Assay , Chromatography, Gas/methods , Insecticides/chemistry , Lethal Dose 50 , Magnetic Resonance Spectroscopy/methods , Menthol/chemistry , Structure-Activity RelationshipABSTRACT
Glutathione S-transferase inhibition assay-guided fractionations on the ethanolic extract of the bark of Caesalpinia bonduc resulted in the isolation of a new sterol, 17-hydroxy-campesta-4,6-dien-3-one (1) along with four known compounds, 13,14-seco-stigmasta-5,14-dien-3alpha-ol (2), 13,14-seco-stigmasta-9(11),14-dien-3alpha-ol (3), caesaldekarin J (4) and pipataline (5) as active constituents. Structures of compounds 1-5 were established on the basis of extensive NMR spectroscopic studies. The compounds (1-5) were isolated on the basis of their inhibitory activity against glutathione S-transferase, an enzyme that has been implicated in resistances during treatment of cancer and parasitic infections. Efforts to study structure-activity relationships of compounds 2 and 3 were also made by modifying their structures. The IC50 values of these compounds and their derivatives ranged from 57-380 microM and were compared to the inhibitory effects due to sodium taurocholate, an isoprene-derived GST inhibitor (IC50=398 microM). A plausible biosynthesis of 13,14-seco-steroids has also been proposed.
