A fungal metabolite asperparaline a strongly and selectively blocks insect nicotinic acetylcholine receptors: The first report on the mode of action

PLoS ONE

Volumn 6, Issue 4, 2011, Pages

  Hirata, Koichi ^a,c   Kataoka, Saori ^a,d   Furutani, Shogo ^a   Hayashi, Hideo ^b   Matsuda, Kazuhiko ^a  

^a KINKI UNIVERSITY   (Japan)

^b Osaka City University   (Japan)

^c NIPPON SODA CO LTD   (Japan)

^d NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOBUTYRIC ACID; 4 AMINOBUTYRIC ACID RECEPTOR; ACETYLCHOLINE; ALKALOID; ASPERPARALINE A; BUNGAROTOXIN RECEPTOR; FIPRONIL; GLUTAMATE RECEPTOR; GLUTAMIC ACID; MECAMYLAMINE; NICOTINIC RECEPTOR; NICOTINIC RECEPTOR ALPHA3BETA4; NICOTINIC RECEPTOR ALPHA4BETA2; UNCLASSIFIED DRUG; AGENTS INTERACTING WITH TRANSMITTER, HORMONE OR DRUG RECEPTORS; ASPERGILLIMIDE; NICOTINIC RECEPTOR BLOCKING AGENT; PIPERAZINE DERIVATIVE; SPIRO COMPOUND;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CHANNEL GATING; CHEMICAL STRUCTURE; CHICKEN; FUNGAL METABOLISM; IC 50; INSECT; NERVE CELL MEMBRANE POTENTIAL; NONHUMAN; PATCH CLAMP; PROTEIN EXPRESSION; PROTEIN TARGETING; RECEPTOR BLOCKING; SILKWORM; XENOPUS LAEVIS; ANIMAL; ASPERGILLUS; CELL MEMBRANE; CELL MEMBRANE POTENTIAL; CYTOLOGY; DRUG EFFECT; ENZYME SPECIFICITY; FEMALE; GENETICS; METABOLISM; NERVE CELL; OOCYTE;

ASPERGILLUS JAPONICUS; BOMBYX; BOMBYX MORI; HEXAPODA; VERTEBRATA; XENOPUS LAEVIS;

ACETYLCHOLINE; ALKALOIDS; ANIMALS; ASPERGILLUS; BOMBYX; CELL MEMBRANE; CHICKENS; FEMALE; MEMBRANE POTENTIALS; NEURONS; NEUROTRANSMITTER AGENTS; NICOTINIC ANTAGONISTS; OOCYTES; PIPERAZINES; RECEPTORS, NICOTINIC; SPIRO COMPOUNDS; SUBSTRATE SPECIFICITY; XENOPUS LAEVIS;

EID: 79953650220     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0018354     Document Type: Article

References (14)

1. Hayashi H, Nishimoto Y, Nozaki H, (1997) Asperparaline A, a new paralytic alkaloid rom Aspergillus japonicus JV-23. Tetrahedron Lett 38: 5655-5658.
2. Hayashi H, Nishimoto Y, Akiyama K, Nozaki H, (2000) New paralytic alkaloids, asperparalines A, B and C, from Aspergillus japonicus JV-23. Biosci Biotechnol Biochem 64: 111-115.
3. Williams RM, Cox RJ, (2003) Paraherquamides, brevianamides, and asperparalines: laboratory synthesis and biosynthesis. An interim report. Acc Chem Res 36: 127-139.
4. Hamill OP, Marty A, Neher E, Sakmann B, Sigworth FJ, (1981) Improved patch-clamp techniques for high-resolution current recording from cells and cell-free membrane patches. Pflügers Arch 391: 85-100.
5. Matsuda K, Shimomura M, Kondo Y, Ihara M, Hashigami K, et al. (2000) Role of loop D of the α7 nicotinic acetylcholine receptor in its interaction with the insecticide imidacloprid and related neonicotinoids. Br J Pharmacol 130: 981-986.
6. Matsuda K, Buckingham SD, Freeman JC, Squire MD, Baylis HA, et al. (1998) Effects of the α subunit on imidacloprid sensitivity of recombinant nicotinic acetylcholine receptors. Br J Pharmacol 123: 518-524.
7. Shimomura M, Yokota M, Ihara M, Akamatsu M, Sattelle DB, et al. (2006) Role in the selectivity of neonicotinoids of insect-specific basic residues in loop D of the nicotinic acetylcholine receptor agonist binding site. Mol Pharmacol 70: 1255-1263.
8. Hirata K, Ishida C, Eguchi Y, Sakai K, Ozoe F, et al. (2008) Role of a serine residue (S278) in the pore-facing region of the housefly L-glutamate-gated chloride channel in determining sensitivity to noncompetitive antagonists. Insect Mol Biol 17: 341-350.
9. Ikeda T, Zhao X, Kono Y, Yeh JZ, Narahashi T, (2003) Fipronil modulation of glutamate-induced chloride currents in cockroach thoracic ganglion neurons. Neurotoxicology 24: 807-815.
10. Zhao X, Yeh JZ, Salgado VL, Narahashi T, (2004) Fipronil is a potent open channel blocker of glutamate-activated chloride channels in cockroach neurons. J Pharmacol Exp Ther 310: 192-201.
11. Salgado VL, Saar R, (2004) Desensitizing and non-desensitizing subtypes of alpha-bungarotoxin-sensitive nicotinic acetylcholine receptors in cockroach neurons. J Insect Physiol 50: 867-879.
12. Strømgaard K, Jensen LS, Vogensen SB, (2005) Polyamine toxins: development of selective ligands for ionotropic receptors. Toxicon 45: 249-254.
13. Shao YM, Dong K, Zhang CX, (2007) The nicotinic acetylcholine receptor gene family of the silkworm, Bombyx mori. BMC Genomics 8: 324.
14. Millar NS, Gotti C, (2009) Diversity of vertebrate nicotinic acetylcholine receptors. Neuropharmacology 56: 237-246.