An isoprenyl indole alkaloid with diverse biological activities
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Neoechinulin A

Item No. 43283

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3Z-[[2-(1,1-dimethyl-2-propen-1-yl)-1H-indol-3-yl]methylene]-6S-methyl-2,5-piperazinedione
CAS Number
51551-29-2
Molecular Formula
C19H21N3O2
Formula Weight
323.4
Purity
≥85%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: Slightly soluble: 0.1-1 mg/ml
SMILES
C=CC(C)(C)C1=C(C2=CC=CC=C2N1)/C=C3C(N[C@H](C(N/3)=O)C)=O
InChi Code
InChI=1S/C19H21N3O2/c1-5-19(3,4)16-13(12-8-6-7-9-14(12)21-16)10-15-18(24)20-11(2)17(23)22-15/h5-11,21H,1H2,2-4H3,(H,20,24)(H,22,23)/b15-10-/t11-/m0/s1
InChi Key
MYRPIYZIAHOECW-SAIXKJTDSA-N
Origin
Fungi/Aspergillus chevalieri
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $76

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    5 mg

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    10 mg

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    Product Description

    Neoechinulin A is an isoprenyl indole alkaloid that has been found in Eurotium and has diverse biological activities.1,2,3,4 It is active against B. cereus and P. vulgaris (MICs = 6.25 and 25 µM, respectively).1 Neoechinulin A (100 µM) induces apoptosis in HeLa cervical cancer cells and inhibits LPS-induced nitrite, prostaglandin E2 (PGE2; Item No. 14010), IL-1β, and TNF-α production in RAW 264.7 macrophages.2,3 It reduces the formation of nitrotyrosine induced by SIN-1 (Item No. 82220) in primary rat neurons when used at a concentration of 200 µM.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Zhao, D., Cao, F., Guo, X.-J., et al. Antibacterial indole alkaloids and anthraquinones from sewage-derived fungus Eurotium sp. Chem. Nat. Compd. 54(2), 399-401 (2018).

    2. Wijesekara, I., Li, Y.-X., Vo, T.-S., et al. Induction of apoptosis in human cervical carcinoma HeLa cells by neoechinulin A from marine-derived fungus Microsporum sp. Proc. Biochem. 48(1), 68-72 (2014).

    3. Kim, K.-S., Cui, X., Lee, D.-S., 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 18(11), 13245-13259 (2013).

    4. Maruyama, K., Ohuchi, T., Yoshida, K., et al. Protective properties of neoechinulin A against SIN-1-induced neuronal cell death. J. Biochem. 136(1), 81-87 (2004).