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nimbolide

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nimbolide Basic information

Product Name:
nimbolide
Synonyms:
  • nimbolide
  • (17R)-7α,15β:21,23-Diepoxy-6α-hydroxy-4,8-dimethyl-1-oxo-11-methoxycarbonyl-18,24-dinor-11,12-seco-5α-chola-2,13,20,22-tetrene-4α-carboxylic acid γ-lactone
  • NSC 309909
  • 2H,5H-Cyclopenta[d']naphtho[1,8-bc:2,3-b']difuran-6-acetic acid, 8-(3-furanyl)-2a,5a,6,6a,8,9,9a,10a,10b,10c-decahydro-2a,5a,6a,7-tetramethyl-2,5-dioxo-, methyl ester, (2aR,5aR,6S,6aR,8R,9aR,10aS,10bR,10cR)-
  • methyl [(2aR,5aR,6S,6aR,8R,9aR,10aS,10bR,10cR)-8-furan-3-yl-2a,5a,6a,7-tetramethyl-2,5-dioxo-2a,5a,6,6a,8,9,9a,10a,10b,10c-decahydro-2H,5H-cyclopenta[d]naphtho[2,3-b:1,8-b''c'']difuran-6-yl]acetate
  • Nimbolide (25 mg)
  • Nimbolide, CyclinA and ERK1/2 inhibitor
  • Nimbolide, 10 mM in DMSO
CAS:
25990-37-8
MF:
C27H30O7
MW:
466.52
Product Categories:
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
Mol File:
25990-37-8.mol
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nimbolide Chemical Properties

Melting point:
>223°C (dec.)
Boiling point:
608.6±55.0 °C(Predicted)
Density 
1.32±0.1 g/cm3(Predicted)
storage temp. 
Hygroscopic, -20°C Freezer, Under Inert Atmosphere
solubility 
Chloroform, Ethyl Acetate
form 
powder
color 
Light Beige to Yellow
Major Application
metabolomics
vitamins, nutraceuticals, and natural products
InChIKey
KMTFKEPRKBPCJW-UHFFFAOYSA-N
SMILES
C12C3(C)C=CC(=O)C1(C)C(CC(=O)OC)C1(C)C4C(C(C=C4C)C4=COC=C4)OC1C2OC3=O
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Safety Information

WGK Germany 
WGK 3
RTECS 
GY2370000
Storage Class
11 - Combustible Solids
Hazard Classifications
Acute Tox. 4 Oral
Toxicity
hamster,LD50,intraperitoneal,> 500mg/kg (500mg/kg),Toxicology Letters. Vol. 30, Pg. 159, 1986.
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nimbolide Usage And Synthesis

Chemical Properties

Light Beige Solid

Uses

Nimbolide, a natural triterpenoid present in the edible parts of the neem tree (Azadirachta indica), was found to be growth-inhibitory in human colon carcinoma HT-29 cells. Nimbolide treatment of cells at 2.5 - 10 μM resulted in moderate to very strong growth inhibition.

Biological Activity

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.

in vivo

Nimbolide (10 mg/kg, i.v., daily, 7 days) inhibits glioblastoma multiforme tumor growth in U87EGFRvⅢ xenografted mouse model[2].
Nimbolide (5 mg/kg, 20 mg/kg; i.p.; daily, 10 days), inhibits tumor growth in HCT-116-derived xenograft mouse, reduces the expression of proteins involved in invasion, metastasis, and angiogenesis (MMP-9, CXCR4, ICAM-1, and VEGF)[5].

Animal Model:HCT-116-derived xenograft mouse[5]
Dosage:5 mg/kg, 20 mg/kg
Administration:Intraperitoneal injection (i.p.), daily, 10 days
Result:Suppressed tumor growth in nude mice at a dose as low as 5 mg/kg.
Reduced tumor growth by almost 90% on day 10 at a dose as low as 20 mg/kg.
Didn’t affect the body weight of mice.

IC 50

NF-κB; CDK4; CDK6

storage

Store at -20°C

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