11141-17-6
Chemical Structure
Azadirachtin
- CAS. Nr.: 11141-17-6
- Formula:C35H44O16
- Molecular Weight:720.71
IUPAC Name: dimethyl (2aR,2a1R,3S,4S,4aR,5S,7aS,8S,10R,10aS)-10-acetoxy-3,5-dihydroxy-4-((1aR,2S,3aS,6aS,7S,7aS)-6a-hydroxy-7a-methyl-3a,6a,7,7a-tetrahydro-2,7-methanofuro[2,3-b]oxireno[2,3-e]oxepin-1a(2H)-yl)-4-methyl-8-(((E)-2-methylbut-2-enoyl)oxy)octahydro-1H,7H-naphtho[1,8-bc:4,4a-c']difuran-5,10a(8H)-dicarboxylate
InChIKey: FTNJWQUOZFUQQJ-NDAWSKJSSA-N
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
Biological Activity: 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].
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Azadirachtin | 99.06% | 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. | ||||||||||||||||||||
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Azadirachtin (Standard) | 99.10% | Azadirachtin (Standard) is the analytical standard of Azadirachtin. This product is intended for research and analytical applications. Azadirachtin, one of the most promising botanical insecticides, is widely used for pest control. Azadirachtin induces apoptosis in insect cell lines, including Sf9, SL-1 and BTI-Tn-5B1-4. | ||||||||||||||||||||
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- [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. [Content Brief]
- [2]. Fernandes SR, et al. Chemistry, bioactivities, extraction and analysis of azadirachtin: State-of-the-art. Fitoterapia. 2019 Apr;134:141-150. [Content Brief]
- [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. [Content Brief]
- [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. [Content Brief]
- [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. [Content Brief]
- [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. [Content Brief]
Keywords
