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SMB00586

Sigma-Aldrich

Nimbolide

from Azadirachta indica, ≥98%

Sinónimos:

NSC-309909

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About This Item

Fórmula empírica (notación de Hill):
C27H30O7
Número de CAS:
25990-37-8
Peso molecular:
466.52
UNSPSC Code:
12352205
PubChem Substance ID:
329825074
NACRES:
NA.25

Quality Level

200

assay

≥98%

form

powder

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

[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

InChI key

JZIQWNPPBKFOPT-LSYMHUITSA-N

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General description

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.

Biochem/physiol Actions

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Molay Kumar Roy et al.
Phytotherapy research : PTR, 21(3), 245-250 (2006-12-14)
Nimbolide, a triterpenoid extracted from the flowers of the neem tree (Azadirachta indica), was found to have antiproliferative activity against some cancer cell lines. Treatment of cells with 0.5-5.0 microm concentrations of nimbolide resulted in moderate to very strong growth
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
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)
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
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