Nimbolide

Names

[ Name ]:
Nimbolide

[Synonym ]:
Methyl [8-(3-furyl)-2a,5a,6a,7-tetramethyl-2,5-dioxo-2a,5a,6,6a,8,9,9a,10a,10b,10c-decahydro-2H,5H-cyclopenta[b]furo[2',3',4':4,5]naphtho[2,3-d]furan-6-yl]acetate
2H,5H-Cyclopenta[d]naphtho[2,3-b:1,8-b'c']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
(4S,4aS,8aS)-4-(tert-Butyl-dimethylsilyl)oxy-7,7-dimethoxy-4a-methyl-3,4,5,6,8,8a-hexahydro-2H-naphthalen-1-one
(4S,4aS,8aS)-4-(dimethyl-tert-butyl-silyl)oxy-7,7-dimethoxy-4a-methyl-decalin-1-one

Biological Activity

[Description]:

Nimbolide is a triterpene derived from the leaves and flowers of neem (Azadirachta indica L). Nimbolide induces apoptosis through inactivation of NF-κB. Nimbolide inhibits CDK4/CDK6 kinase activity. Nimbolide suppresses the NF-κB, Wnt, PI3K-Akt, MAPK and JAK-STAT signaling pathways[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> CDK

[Target]

NF-κB

CDK4

CDK6

[References]

[1]. Bodduluru LN, et al. Chemopreventive and therapeutic effects of nimbolide in cancer: the underlying mechanisms. Toxicol In Vitro. 2014 Aug;28(5):1026-35.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
608.6±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₇H₃₀O₇

[ Molecular Weight ]:
466.52

[ Flash Point ]:
321.9±31.5 °C

[ Exact Mass ]:
466.199158

[ PSA ]:
92.04000

[ LogP ]:
2.66

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.597

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GY2370000

CAS REGISTRY NUMBER :: 25990-37-8

LAST UPDATED :: 199106

DATA ITEMS CITED :: 8

MOLECULAR FORMULA :: C27-H30-O7

MOLECULAR WEIGHT :: 466.57

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >600 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 30,159,1986

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >600 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 30,159,1986

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >600 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 30,159,1986

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 225 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 30,159,1986

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >600 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 30,159,1986

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 24 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 30,159,1986

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >600 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 30,159,1986

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: >500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 30,159,1986

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Precautionary Statements ]:
P301 + P312 + P330

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
GY2370000

Articles

Nimbolide Induces ROS-Regulated Apoptosis and Inhibits Cell Migration in Osteosarcoma.

Int. J. Mol. Sci. 16 , 23405-24, (2015)

Osteosarcoma (OS) is a primary malignant tumor of bone and is most prevalent in children and adolescents. OS is frequently associated with pulmonary metastasis, which is the main cause of OS-related m...

Nimbolide, a constituent of Azadirachta indica, inhibits Plasmodium falciparum in culture.

Southeast Asian J. Trop. Med. Public Health 16(1) , 66-72, (1985)

The terpenoid lactone nimbolide, the structure of which has been unambiguously established, was found to inhibit Plasmodium falciparum in culture with a moderate potency. The EC50 against the parasite...

Induction of cell cycle arrest, DNA damage, and apoptosis by nimbolide in human renal cell carcinoma cells.

Tumour Biol. 36(10) , 7539-47, (2015)

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 ...