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Key Documents

SMB00586

Sigma-Aldrich

Nimbolide

from Azadirachta indica, ≥98%

Synonyme(s) :

NSC-309909

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About This Item

Formule empirique (notation de Hill):
C27H30O7
Numéro CAS:
Poids moléculaire :
466.52
Code UNSPSC :
12352205
ID de substance PubChem :
Nomenclature NACRES :
NA.25

Niveau de qualité

Pureté

≥98%

Forme

powder

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Température de stockage

−20°C

Chaîne SMILES 

[H][C@@]12C[C@@H](C3=COC=C3)C(C)=C1[C@]([C@H](CC(OC)=O)[C@](C(C=C[C@]45C)=O)(C)[C@@]4([H])[C@@]6([H])OC5=O)(C)[C@]6([H])O2

InChI

1S/C27H30O7/c1-13-15(14-7-9-32-12-14)10-16-20(13)27(4)17(11-19(29)31-5)26(3)18(28)6-8-25(2)22(26)21(23(27)33-16)34-24(25)30/h6-9,12,15-17,21-23H,10-11H2,1-5H3/t15-,16-,17-,21-,22+,23-,25-,26+,27-/m1/s1

Clé InChI

JZIQWNPPBKFOPT-LSYMHUITSA-N

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Description générale

Nimbolide is a limonoid tetranortriterpenoid with an α,β-unsaturated ketone system, and a δ-lactone ring. It is usually isolated from Azadirachta indica (Neem).

Application

Nimbolide has been used as an anticancer agent to study its effects on the proliferation, migration, and invasion of human bladder cancer cell lines (EJ and 5637). It has also been used as a treatment to target RNF114 and trap PARP1 inhibitor(PARPi) and PARylation-dependent DNA repair factors.

Actions biochimiques/physiologiques

Nimbolide exhibits anti-malarial, anti-bacterial, and anti-cancer activities. It has been shown to induce apoptosis in osteosarcoma cells and inhibits cell migration of these cells by modulating the expression of integrin αvβ5. In human renal carcinoma cells, nimbolide induced cell cycle arrest, DNA damage, and apoptosis.It has been shown to modulate autophagy and apoptosis in pancreatic cancer.

Pictogrammes

Exclamation mark

Mention d'avertissement

Warning

Mentions de danger

Conseils de prudence

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


Certificats d'analyse (COA)

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Les clients ont également consulté

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Nimbolide inhibits pancreatic cancer growth and metastasis through ROS-mediated apoptosis and inhibition of epithelial-to-mesenchymal transition.
Subramani R, et al.
Scientific Reports, 6, 19819-19819 (2016)
Panawan Suttiarporn et al.
Molecules (Basel, Switzerland), 25(12) (2020-07-01)
Nimbolide, a limonoid present in leaves of the neem tree (Azadirachta indica), is an anticancer compound against a panel of human cancer cell lines. The rapid process of extraction and purification of the nimbolide from the leaves of neem tree
Seung-Shick Shin et al.
Evidence-based complementary and alternative medicine : eCAM, 2019, 3753587-3753587 (2019-08-09)
Nimbolide, an active chemical constituent of Azadirachta indica, reportedly has several physiological effects. Here, we assessed novel anticancer effects of nimbolide against bladder cancer EJ and 5637 cells. Nimbolide treatment inhibited the proliferation of both bladder cancer cell lines with
Yi-Hsien Hsieh et al.
Tumour biology : the journal of the International Society for Oncodevelopmental Biology and Medicine, 36(10), 7539-7547 (2015-04-29)
Nimbolide is a tetranortriterpenoid isolated from the leaves and flowers of Azadirachta indica which has been shown to exhibit anticancer, antioxidant, anti-inflammatory, and anti-invasive properties in a variety of cancer cells. However, the anti-tumor effect on human renal cell carcinoma
Nimbolide Targets RNF114 to Induce the Trapping of PARP1 and Poly-ADP-Ribosylation-Dependent DNA Repair Factors
Li Peng et al.,
bioRxiv : the preprint server for biology (2022)

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