195966-93-9

195966-93-9 structure

Name: (rel)-Asperparaline A
Chemical Name: aspergillimide
CAS Number: 195966-93-9
Molecular Formula: C₂₀H₂₉N₃O₃
Molecular Weight: 359.463
Catalog: Signaling Pathways Membrane Transporter/Ion Channel nAChR
Create Date: 2021-01-13 20:16:11
Modify Date: 2024-01-03 12:52:07
(rel)-Asperparaline A ((rel)-Aspergillimide), an anthelmintic metabolite, is isolated from okara that has been fermented with Aspergillus japonicas JV-23. (rel)-Asperparaline A is also a potent and selective antagonist of nAChR. (rel)-Asperparaline A exhibits paralytic activity in silk worms[1][2].

Name	aspergillimide
Synonyms	(3S,5S,7S,12S)-1',4,4,12,14-Pentamethyl-2'H,5'H,13H-spiro[9,14-diazatetracyclo[5.5.2.01,9.03,7]tetradecane-5,3'-pyrrolidine]-2',5',13-trione aspergillimide

Description	(rel)-Asperparaline A ((rel)-Aspergillimide), an anthelmintic metabolite, is isolated from okara that has been fermented with Aspergillus japonicas JV-23. (rel)-Asperparaline A is also a potent and selective antagonist of nAChR. (rel)-Asperparaline A exhibits paralytic activity in silk worms[1][2].
Related Catalog	Signaling Pathways >> Membrane Transporter/Ion Channel >> nAChR Signaling Pathways >> Neuronal Signaling >> nAChR Research Areas >> Neurological Disease
In Vitro	Asperparaline A (1 μM; 1 min) markedly and reversibly blocks the acetylcholine (Ach; 10 µM)-induced current in the silkworm larval neurons[2]. Asperparaline A (1-1000 nM; 1 min) differentially blocks the peak and slowly desensitizing currents, with IC50s of 20.2 and 39.6 nM, respectively[2]. Asperparaline A (10 μM; 1 min) reduces the peak current amplitude of the ACh (100 µM)-induced response of α3β4 nAChR by 33.4%, while barely influencing the amplitudes of the responses to ACh of the α4β2 and α7 nAChRs in X. laevis oocytes[2].
In Vivo	Asperparaline A (10 μg/g; p.o.) exhibits paralysis against silk worms within 1 h and lasts for 7 to 10 h[1]. Asperparaline A (3 μg/g; injection with a micro-syringe) exhibits paralysis activity against silk worms within 20 min and lasts for 4 to 5 h[1].
References	[1]. Hayashi H, et, al. New paralytic alkaloids, asperparalines A, B and C, from Aspergillus japonicus JV-23. Biosci Biotechnol Biochem. 2000 Jan;64(1):111-5. [2]. Hirata K, et, al. A fungal metabolite asperparaline a strongly and selectively blocks insect nicotinic acetylcholine receptors: the first report on the mode of action. PLoS One. 2011 Apr 1;6(4):e18354.

Density	1.3±0.1 g/cm3
Boiling Point	546.1±50.0 °C at 760 mmHg
Molecular Formula	C₂₀H₂₉N₃O₃
Molecular Weight	359.463
Flash Point	244.6±22.5 °C
Exact Mass	359.220886
LogP	1.11
Vapour Pressure	0.0±1.5 mmHg at 25°C
Index of Refraction	1.615

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