ABSTRACT
Eight new aphanamixoid-type aphanamixoids (C-J, 1-8) and six new prieurianin-type limonoids, aphanamixoids K-P (9-14), along with 10 known terpenoids were isolated from Aphanamixis polystachya, and their structures were established by spectroscopic data analysis. Among the new limonoids, 13 compounds exhibited antifeedant activity against the generalist Helicoverpa armigera, a plant-feeding insect, at various concentration levels. In particular, compounds 1, 4, and 5 showed potent activities with EC50 values of 0.017, 0.008, and 0.012 µmol/cm(2), respectively. On the basis of a preliminary structure-activity relationship analysis, some potential active sites in the aphanamixoid-type limonoid molecules are proposed.
Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Drugs, Chinese Herbal/isolation & purification , Drugs, Chinese Herbal/pharmacology , Feeding Behavior/drug effects , Limonins/isolation & purification , Limonins/pharmacology , Meliaceae/chemistry , Algorithms , Animals , Antineoplastic Agents, Phytogenic/chemistry , Drug Screening Assays, Antitumor , Drugs, Chinese Herbal/chemistry , HL-60 Cells , Humans , Larva/drug effects , Lepidoptera/drug effects , Limonins/chemistry , Molecular Structure , Moths/drug effects , Nuclear Magnetic Resonance, Biomolecular , Spodoptera/physiology , Structure-Activity RelationshipABSTRACT
Four new Daphniphyllum alkaloids, daphnimacropodines A-D (1-4), together with three known ones, daphnilactone B and daphnezomines H and I, were isolated from the fruits of Daphniphyllum macropodum. Their structures were determined by spectroscopic methods, especially 2D NMR techniques.
Subject(s)
Alkaloids/isolation & purification , Drugs, Chinese Herbal/isolation & purification , Plants, Medicinal/chemistry , Saxifragaceae/chemistry , Alkaloids/chemistry , Alkaloids/pharmacology , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/pharmacology , Fruit/chemistry , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Platelet Aggregation/drug effectsABSTRACT
[structure: see text]. A new hexacyclic alkaloid, calydaphninone (1), containing a 4-azatricyclo[5.2.2.0(1,4)]undecan ring system, has been isolated from the leaves and twigs of Daphniphyllum calycillum (Daphniphyllaceae). Its structure was elucidated by spectral and crystallographic means. Furthermore, conformations of calydaphninone (1) in solution are discussed on the basis of NMR spectral analysis and computational (B3LYP/6-31G*) results.