Nimbolide
[CAS# 25990-37-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Lactone compound
• Name: Nimbolide
• Synonyms: methyl 2-[6-(furan-3-yl)-7,9,11,15-tetramethyl-12,16-dioxo-3,17-dioxapentacyclo[9.6.1.02,9.04,8.015,18]octadeca-7,13-dien-10-yl]acetate
• Molecular Formula: C₂₇H₃₀O₇
• Molecular Weight: 466.52
• CAS Registry Number: 25990-37-8
• EC Number: 874-681-5
• SMILES: CC1=C2C(CC1C3=COC=C3)OC4C2(C(C5(C6C4OC(=O)C6(C=CC5=O)C)C)CC(=O)OC)C

Properties

• Solubility: 20.82 mg/L (25 ºC water)
• Density: 1.3±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.597, Calc.^*
• Melting point: 239.73 ºC
• Boiling Point: 558.08 ºC, 608.6±55.0 ºC (760 mmHg), Calc.^*
• Flash Point: 321.9±31.5 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302
• Precautionary Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

Nimbolide is a natural compound derived from the neem tree (*Azadirachta indica*), which is native to India and widely known for its medicinal properties. The active ingredient, nimbolide, is primarily found in the seeds, bark, and leaves of the neem tree. It has been studied for its potential therapeutic benefits in a variety of medical conditions due to its biological activities, including its anti-inflammatory, antioxidant, antimicrobial, and anticancer properties.

The discovery of nimbolide dates back to traditional medicine, where various parts of the neem tree have been used for centuries in Ayurvedic and other traditional healing practices. It is only in recent decades that scientific studies have focused on the isolation and characterization of nimbolide and its biological effects. Researchers have sought to understand the mechanisms by which nimbolide exerts its therapeutic effects, leading to its investigation in modern medicine.

Nimbolide is known to exert its effects through multiple mechanisms of action, which make it a promising candidate for the treatment of various diseases. One of its most notable properties is its ability to inhibit the growth and spread of cancer cells. In particular, studies have shown that nimbolide can suppress the proliferation of several types of cancer cells, including breast, colon, and prostate cancer cells. It has been demonstrated to induce apoptosis (programmed cell death) in cancer cells, which is a critical mechanism for controlling tumor growth. Additionally, nimbolide has been shown to interfere with the metastatic spread of cancer by inhibiting key signaling pathways involved in cell migration and invasion.

In addition to its anticancer properties, nimbolide has anti-inflammatory effects. Chronic inflammation is linked to the development of many diseases, including cardiovascular diseases, diabetes, and certain types of cancer. Nimbolide has been shown to reduce the production of pro-inflammatory cytokines and inhibit the activation of inflammatory pathways, making it a potential therapeutic agent for conditions characterized by excessive inflammation. Its anti-inflammatory effects have been attributed to its ability to modulate the activity of nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB), a protein complex involved in regulating the immune response.

Another important application of nimbolide is its antioxidant activity. Free radicals are highly reactive molecules that can cause oxidative damage to cells and tissues, contributing to aging and the development of various diseases. Nimbolide has been found to scavenge free radicals, thereby protecting cells from oxidative stress and damage. This antioxidant property adds to its potential therapeutic effects in conditions such as neurodegenerative diseases, where oxidative damage is a key factor in disease progression.

Nimbolide also has antimicrobial properties, demonstrating activity against a variety of pathogens, including bacteria, fungi, and viruses. Its ability to inhibit the growth of these microorganisms makes it a potential candidate for the development of new antimicrobial agents, particularly in an era of increasing antibiotic resistance.

The use of nimbolide in clinical settings is still in the early stages, and while its potential therapeutic applications are promising, further studies are needed to better understand its pharmacokinetics, safety profile, and efficacy. In preclinical studies, nimbolide has shown promising results in animal models, but human clinical trials are necessary to confirm its effectiveness and safety in humans. Researchers are also exploring various formulations of nimbolide to enhance its bioavailability and optimize its therapeutic potential.

In conclusion, nimbolide is a bioactive compound derived from the neem tree, with significant potential in the treatment of a variety of diseases, including cancer, inflammation, and infections. Its ability to modulate key biological pathways makes it an attractive candidate for further research and development in medicinal chemistry. However, as with many natural compounds, additional clinical studies are required to fully assess its therapeutic potential and establish its clinical applications.

References

2008. Nimbolide a limonoid from Azadirachta indica inhibits proliferation and induces apoptosis of human choriocarcinoma (BeWo) cells. Investigational New Drugs, 27(3).
DOI: 10.1007/s10637-008-9170-z

2022. Nimbolide inhibits 2D and 3D prostate cancer cells migration, affects microtubules and angiogenesis and suppresses B-RAF/p.ERK-mediated in vivo tumor growth. Phytomedicine, 94.
DOI: 10.1016/j.phymed.2021.153826

2023. Nimbolide targets RNF114 to induce the trapping of PARP1 and synthetic lethality in BRCA-mutated cancer. Science Advances, 9(43).
DOI: 10.1126/sciadv.adg7752