Dioncophylline E from Dioncophyllum thollonii, the first 7,3′-coupled dioncophyllaceous naphthylisoquinoline alkaloid
| Autor: | Kim Messer, Reto Brun, Jörg Mühlbacher, Gerhard Bringmann, Adriaan M. Louis, Matthias Grüne, Kristina Wolf |
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| Rok vydání: | 2002 |
| Předmět: |
Steric effects
Trypanosoma Magnetic Resonance Spectroscopy Spectrophotometry Infrared Stereochemistry Plasmodium falciparum Antiprotozoal Agents Plant Science Horticulture Trypanosoma brucei Biochemistry Mass Spectrometry Inhibitory Concentration 50 Magnoliopsida chemistry.chemical_compound Alkaloids Parasitic Sensitivity Tests parasitic diseases Animals Humans heterocyclic compounds Isoquinoline Muscle Skeletal Molecular Biology Chromatography High Pressure Liquid Plants Medicinal biology Plant Extracts Circular Dichroism Alkaloid Stereoisomerism Biological activity General Medicine Isoquinolines biology.organism_classification Rats Dioncophyllaceae Kinetics chemistry Africa Triphyophyllum Thermodynamics |
| Zdroj: | Phytochemistry. 60:389-397 |
| ISSN: | 0031-9422 |
| DOI: | 10.1016/s0031-9422(02)00109-7 |
| Popis: | The isolation and structural elucidation of dioncophylline E, a novel naphthylisoquinoline alkaloid from the rare West African liana Dioncophyllum thollonii, is described. The alkaloid displays an unusual 7,3'-linkage between the naphthalene and the isoquinoline portions. Due to the resulting medium degree of steric hindrance exerted by the ortho-substituents next to the biaryl axis, the compound undergoes slow rotation about the axis at room temperature and thus is the first such alkaloid that occurs as a mixture of two configurationally semi-stable atropo-diastereomers. Dioncophylline E exhibits good antimalarial activity against both chloroquine-sensitive and -resistant strains of Plasmodium falciparum while its antitrypanosomal activity against Trypanosoma cruzi is weak and that against T. brucei rhodesiense is moderate. Furthermore, four additional naphthylisoquinoline alkaloids previously known from the related plant species Triphyophyllum peltatum, have been identified in D. thollonii. |
| Databáze: | OpenAIRE |
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