Rare excitatory amino acid from flowers of zonal geranium responsible for paralyzing the Japanese beetle
| Autor: | Jonathan M. Frantz, Rudolph E. K. Winter, Ajay P. Singh, Christopher M. Ranger, James C. W. Locke, Michael E. Reding, Charles R. Krause |
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| Jazyk: | angličtina |
| Rok vydání: | 2011 |
| Předmět: |
Magnetic Resonance Spectroscopy
Stereochemistry Excitatory Amino Acids Geranium Flowers Biology chemistry.chemical_compound Popillia Excitatory Amino Acid Agonists Animals Quisqualic acid Excitatory Amino Acid Agonist Chromatography High Pressure Liquid chemistry.chemical_classification Multidisciplinary Dose-Response Relationship Drug Molecular Structure Japanese beetle Quisqualic Acid Stereoisomerism biology.organism_classification Amino acid Coleoptera Biochemistry chemistry Heteronuclear molecule Physical Sciences Petal |
| Popis: | The Japanese beetle (JB), Popillia japonica , exhibits rapid paralysis after consuming flower petals of zonal geranium, Pelargonium x hortorum . Activity-guided fractionations were conducted with polar flower petal extracts from P. x hortorum cv. Nittany Lion Red, which led to the isolation of a paralysis-inducing compound. High-resolution–MS and NMR ( 1 H, 13 C, COSY, heteronuclear sequential quantum correlation, heteronuclear multiple bond correlation) analysis identified the paralytic compound as quisqualic acid (C 5 H 7 N 3 O 5 ), a known but rare agonist of excitatory amino acid receptors. Optical rotation measurements and chiral HPLC analysis determined an l -configuration. Geranium-derived and synthetic l -quisqualic acid demonstrated the same positive paralytic dose–response. Isolation of a neurotoxic, excitatory amino acid from zonal geranium establishes the phytochemical basis for induced paralysis of the JB, which had remained uncharacterized since the phenomenon was first described in 1920. |
| Databáze: | OpenAIRE |
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