Azadirachtin

Azadirachtin is an oral active triterpenoid compound with anticancer, antimalarial, anti-inflammatory, and insecticidal activities. Azadirachtin induces cell apoptosis through the mitochondrial pathway (by inhibiting Bcl-2/Bax ratio or activating Apaf-1 and caspase-3) or through death receptors (by inhibiting TNFR activation) . Additionally, Azadirachtin exerts its anti-inflammatory effects by inhibiting NF-кB signaling pathway activation, and it exhibits insecticidal activity by inducing apoptosis in insect cells[1][2][3][4][5][6].

Product Specifications

CAS Number

[11141-17-6]

UNSPSC

12352005

Hazard Statement

H317, H410

Target

Apoptosis; Bcl-2 Family; Caspase; NF-κB; Parasite

Type

Natural Products

Related Pathways

Anti-infection; Apoptosis; NF-κB

Field of Research

Cancer; Infection; Inflammation/Immunology

Assay Protocol

https://www.medchemexpress.com/azadirachtin.html

Purity

99.06

Solubility

DMSO : ≥ 100 mg/mL

Smiles

C[C@@]1([C@@]([C@@]2(O)C(OC)=O)([H])[C@]([C@H](C[C@H]3OC(C)=O)OC(/C(C)=C/C)=O)(CO2)[C@@]4([H])[C@](OC[C@@]43C(OC)=O)([H])[C@H]1O)[C@]([C@@H](O[C@]5([H])OC=C6)C[C@H]7[C@]56O)(O8)[C@]78C

Molecular Formula

C35H44O16

Molecular Weight

720.71

Precautions

H317, H410

References & Citations

[1]Shu B, Jia J, Zhang J, Sethuraman V, Yi X, Zhong G. DnaJ homolog subfamily A member1 (DnaJ1) is a newly discovered anti-apoptotic protein regulated by azadirachtin in Sf9 cells. BMC Genomics. 2018;19 (1) :413. Published 2018 May 29.|[2]Fernandes SR, et al. Chemistry, bioactivities, extraction and analysis of azadirachtin: State-of-the-art. Fitoterapia. 2019 Apr;134:141-150.|[3]Thoh M, et al. Azadirachtin interacts with retinoic acid receptors and inhibits retinoic acid-mediated biological responses. J Biol Chem. 2011 Feb 11;286 (6) :4690-702. doi: 10.1074/jbc.M110.169334. Epub 2010 Dec 2. Retraction in: J Biol Chem. 2013 Mar 22;288 (12) :8563. |[4]Priyadarsini RV, et al. The neem limonoids azadirachtin and nimbolide inhibit hamster cheek pouch carcinogenesis by modulating xenobiotic-metabolizing enzymes, DNA damage, antioxidants, invasion and angiogenesis. Free Radic Res. 2009 May;43 (5) :492-504.|[5]Priyadarsini RV, et al. The neem limonoids azadirachtin and nimbolide induce cell cycle arrest and mitochondria-mediated apoptosis in human cervical cancer (HeLa) cells.|[6]Tapanelli S, et al. Transmission blocking effects of neem (Azadirachta indica) seed kernel limonoids on Plasmodium berghei early sporogonic development. Fitoterapia. 2016 Oct;114:122-126.