51551-29-2

51551-29-2 structure

Name: Neoechinulin A
Chemical Name: (3S,6Z)-3-Methyl-6-{[2-(2-methyl-3-buten-2-yl)-1H-indol-3-yl]meth ylene}-2,5-piperazinedione
CAS Number: 51551-29-2
Molecular Formula: C₁₉H₂₁N₃O₂
Molecular Weight: 323.389
Catalog: Natural product Alkaloid
Create Date: 2016-07-01 09:17:26
Modify Date: 2024-01-09 19:11:38
Neoechinulin A is an isoprenyl indole alkaloid that exhibits scavenging, neurotrophic factor-like, and anti-apoptotic activities. Neoechinulin A induces memory improvements and antidepressant-like effects in mice[1][2].

Name	(3S,6Z)-3-Methyl-6-{[2-(2-methyl-3-buten-2-yl)-1H-indol-3-yl]meth ylene}-2,5-piperazinedione
Synonyms	2,5-Piperazinedione, 3-[[2-(1,1-dimethyl-2-propen-1-yl)-1H-indol-3-yl]methylene]-6-methyl-, (3Z,6S)- (3S,6Z)-3-Methyl-6-{[2-(2-methyl-3-buten-2-yl)-1H-indol-3-yl]methylene}-2,5-piperazinedione (3S,6Z)-3-methyl-6-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene}piperazine-2,5-dione

Description	Neoechinulin A is an isoprenyl indole alkaloid that exhibits scavenging, neurotrophic factor-like, and anti-apoptotic activities. Neoechinulin A induces memory improvements and antidepressant-like effects in mice[1][2].
Related Catalog	Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Neurological Disease
In Vitro	Neoechinulin A (RAW264.7 macrophages; 3 hours; cells then stimulated with LPS (1 μg/mL) for 18 hours) suppresses PGE2, TNF-α, and IL-1β production in a dose-dependent manner[2]. Neoechinulin A can suppress the production of pro-inflammatory mediators and cytokines including NO, PGE2, TNF-α, and IL-1β. Further, it reduced the expression of iNOS and COX-2 in LPS-stimulated RAW264.7 macrophages by inhibiting the NF-κB and p38 MAPK signaling pathways[2]. Neoechinulin A suppresses amyloid-β oligomer-induced microglia activation and thereby protects PC-12 cells from inflammation-mediated toxicity[3].
In Vivo	In the Y-maze test, the intracerebroventicular (i.c.v.) administration of LPS (10 μg/mouse) significantly decreased spontaneous alternation behavior, which was prevented by the prior administration of neoechinulin A (300ng/mouse, i.c.v.)[1].
References	[1]. Humbert M, et al. Masitinib combined with standard gemcitabine chemotherapy: in vitro and in vivo studies in human pancreatic tumour cell lines and ectopic mouse model. PLoS One. 2010;5(3):e9430. Published 2010 Mar 4. [2]. Kim KS, et al. Anti-inflammatory effect of neoechinulin a from the marine fungus Eurotium sp. SF-5989 through the suppression of NF-кB and p38 MAPK Pathways in lipopolysaccharide-stimulated RAW264.7 macrophages. Molecules. 2013;18(11):13245-13259. Published 2013 Oct 25. [3]. Dewapriya P, et al. Neoechinulin A suppresses amyloid-β oligomer-induced microglia activation and thereby protects PC-12 cells from inflammation-mediated toxicity. Neurotoxicology. 2013;35:30-40.

Density	1.2±0.1 g/cm3
Boiling Point	655.7±55.0 °C at 760 mmHg
Molecular Formula	C₁₉H₂₁N₃O₂
Molecular Weight	323.389
Flash Point	350.4±31.5 °C
Exact Mass	323.163391
PSA	73.99000
LogP	2.55
Vapour Pressure	0.0±2.0 mmHg at 25°C
Index of Refraction	1.628

Hazard Codes	Xi

51551-29-2	55179-54-9
57765-86-3	109232-77-1
138860-83-0	110187-24-1
115655-86-2	2390067-58-8
121935-04-4	701-70-2
1158522-08-7	2172616-26-9
940364-43-2	134104-43-1
131615-57-1	6906-52-1
930439-75-1	1018584-77-4
1375289-11-4	849349-65-1