Available from stock

Nimbolide

SKU: N0360

Category: Phytochemicals

Synonyms: NSC 309909; 25990-37-8
CAS-Number: C₂₇H₃₀O₇
Molecular Formula: 466.52
Molecular Weight

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥98% (HPLC)
Appearance: White to faint yellow powder
Identity: 1H-NMR

Properties

Solvents: Soluble in DMSO or DMF (10mg/ml).

Shipping: AMBIENT
Short Term Storage: -20°C
Long Term Storage: -20°C
Handling Advice: Protect from light and moisture.
Use / Stability: Stable for at least 2 years after receipt when stored at -20°C.

Hazard statements: H302
Precautionary statements: P301 + P312 + P330
GHS Symbol: GHS07
Signal word: Warning

Description: Nimbolide is a limonoid tetranortriterpenoid shown to exhibit anti-malarial, anti-bacterial, anti-inflammatory, anti-obesity and anti-cancer activities. Nimbolide induces cell cycle arrest, DNA damage and apoptosis, and modulates autophagy in cancer cell lines. It inhibits pancreatic cancer cell growth and metastasis by inducing the excessive generation of ROS, reducing PI3K/Akt/mTOR and ERK signaling, and upregulating the pro-apoptotic proteins Bax, caspase-3 and PARP. Nimbolide inhibits auto-ubiquitination of the E3 ligase RNF114 and p21 ubiquitination in vitro. This compound impairs proliferation of triple-negative breast cancer cell lines. Nimbolide also induces apoptotic cell death in a Waldenstroms macroglobulinemia cell line (BCWM1) and inhibits tumor growth in a xenograft model of Waldenstroms macroglobulinemia. Nimbolide can be used for the development of Degraders that utilize RNF114 as an E3 ligase for Targeted Protein Degradation. Nimbolide exerts protective effects in complete Freund's adjuvant induced inflammatory arthritis via abrogation of STAT-3/NF-?B/Notch-1 signaling. Nimbolide suppresses high fat diet (HFD) induced obesity via the Nrf2/HO-1 pathway.
Smiles: CC1=C2[C@](CC1C3=COC=C3)([H])O[C@]([C@]2(C)[C@@H]4CC(OC)=O)([H])[C@@]5([H])C6[C@]4(C)C(C=C[C@@]6(C)C(O5)=O)=O
InChi Key: JZIQWNPPBKFOPT-FTCZZEDLSA-N
References: [1] M.K. Roy, et al., Phytother. Res. 21, 245 (2007) , [2] R.V. Priyadarsini, et al., Free Radic. Res. 44, 624 (2010) , [3] S.C. Gupta, et al., J. Biol. Chem. 286, 1134 (2011) , [4] S. Babykutty, et al., Mol. Carcinogen. 51, 475 (2012) , [5] K. Chitta, et al, Blood Cancer J. 4, 260 (2014) , [6] L.N. Bodduluru, et al., Toxicol. In Vitro 28, 1026 (2014) (Review) , [7] R. Subramani, et al., Sci. Rep. 6, 19819 (2016) , [8] P. Sakar, et al., J. Med. Microbiol. 65, 1205 (2016) , [9] J. Sophia, et al., Cell Death Dis. 9, 1087 (2018) , [10] N. Mahmoud, et al., Oncotarget 9, 35762 (2018) , [11] J.N. Spradin, et al., Nat. Chem. Biol. 15, 747 (2019) , [12] B. Tong, et al., ACS Chem. Biol. 15, 1788 (2020) , [13] P. Anchi, et al., Life Sci. 266, 118911 (2021) , [14] S. Nagini, et al., J. Med. Chem. 64, 3560 (2021) (Review) , [15] L. Zhang, et al., J. Oleo Sci. 71, 709 (2022) , [16] P.K. Jaiswara & A. Kumar, Environ. Toxicol. 37, 1445 (2022)
InChi: 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

Nimbolide is a limonoid tetranortriterpenoid shown to exhibit anti-malarial, anti-bacterial, anti-inflammatory, anti-obesity and anti-cancer activities. Nimbolide induces cell cycle arrest, DNA damage and apoptosis, and modulates autophagy in cancer cell lines. It inhibits pancreatic cancer cell growth and metastasis by inducing the excessive generation of ROS, reducing PI3K/Akt/mTOR and ERK signaling, and upregulating the pro-apoptotic proteins Bax, caspase-3 and PARP. Nimbolide inhibits auto-ubiquitination of the E3 ligase RNF114 and p21 ubiquitination in vitro. This compound impairs proliferation of triple-negative breast cancer cell lines. Nimbolide also induces apoptotic cell death in a Waldenstroms macroglobulinemia cell line (BCWM1) and inhibits tumor growth in a xenograft model of Waldenstroms macroglobulinemia. Nimbolide can be used for the development of Degraders that utilize RNF114 as an E3 ligase for Targeted Protein Degradation. Nimbolide exerts protective effects in complete Freund’s adjuvant induced inflammatory arthritis via abrogation of STAT-3/NF-?B/Notch-1 signaling. Nimbolide suppresses high fat diet (HFD) induced obesity via the Nrf2/HO-1 pathway.

SKU: N0360 Category: Phytochemicals

Additional information

Additional information

Synonyms	NSC 309909
Purity	≥98% (HPLC)
Appearance	White to faint yellow powder
CAS-Number	25990-37-8
Molecular Formula	C27H30O7
Molecular Weight	466.52
Identity	1H-NMR
Solvents	Soluble in DMSO or DMF (10mg/ml).
Smiles	CC1=C2[C@](CC1C3=COC=C3)([H])O[C@]([C@]2(C)[C@@H]4CC(OC)=O)([H])[C@@]5([H])C6[C@]4(C)C(C=C[C@@]6(C)C(O5)=O)=O
InChi Key	JZIQWNPPBKFOPT-FTCZZEDLSA-N
Shipping	AMBIENT
Short Term Storage	-20°C
Long Term Storage	-20°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at -20°C.
Hazard statements	H302
Precautionary statements	P301 + P312 + P330
GHS Symbol	GHS07
Signal word	Warning
References	[1] M.K. Roy, et al., Phytother. Res. 21, 245 (2007), [2] R.V. Priyadarsini, et al., Free Radic. Res. 44, 624 (2010), [3] S.C. Gupta, et al., J. Biol. Chem. 286, 1134 (2011), [4] S. Babykutty, et al., Mol. Carcinogen. 51, 475 (2012), [5] K. Chitta, et al, Blood Cancer J. 4, 260 (2014), [6] L.N. Bodduluru, et al., Toxicol. In Vitro 28, 1026 (2014) (Review), [7] R. Subramani, et al., Sci. Rep. 6, 19819 (2016), [8] P. Sakar, et al., J. Med. Microbiol. 65, 1205 (2016), [9] J. Sophia, et al., Cell Death Dis. 9, 1087 (2018), [10] N. Mahmoud, et al., Oncotarget 9, 35762 (2018), [11] J.N. Spradin, et al., Nat. Chem. Biol. 15, 747 (2019), [12] B. Tong, et al., ACS Chem. Biol. 15, 1788 (2020), [13] P. Anchi, et al., Life Sci. 266, 118911 (2021), [14] S. Nagini, et al., J. Med. Chem. 64, 3560 (2021) (Review), [15] L. Zhang, et al., J. Oleo Sci. 71, 709 (2022), [16] P.K. Jaiswara & A. Kumar, Environ. Toxicol. 37, 1445 (2022)
InChi	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
Quantity	5 mg, Bulk