Rare excitatory amino acid from flowers of zonal geranium responsible for paralyzing the Japanese beetle.

Autor: Ranger CM; United States Department of Agriculture-Agricultural Research Service, Application Technology Research Unit, Wooster, OH 44691, USA. christopher.ranger@ars.usda.gov, Winter RE, Singh AP, Reding ME, Frantz JM, Locke JC, Krause CR
Jazyk: angličtina
Zdroj: Proceedings of the National Academy of Sciences of the United States of America [Proc Natl Acad Sci U S A] 2011 Jan 25; Vol. 108 (4), pp. 1217-21. Date of Electronic Publication: 2011 Jan 04.
DOI: 10.1073/pnas.1013497108
Abstrakt: 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: MEDLINE