Lupeol Immunology & Inflammation related chemical

Cat.No.S3614

Lupeol (Clerodol, Monogynol B, Fagarasterol, Farganasterol) is a significant lupane-type triterpene represented in the plant, fungi and animal kingdoms with anticancer, antiprotozoal, chemopreventive and anti-inflammatory properties.
Lupeol Immunology & Inflammation related chemical Chemical Structure

Chemical Structure

Molecular Weight: 426.72

Quality Control

Chemical Information, Storage & Stability

Molecular Weight 426.72 Formula

C30H50O

Storage (From the date of receipt)
CAS No. 545-47-1 Download SDF Storage of Stock Solutions

Synonyms (3β,13ξ)-Lup-20(29)-en-3-ol, Clerodol, Monogynol B, Fagarasterol, Farganasterol Smiles CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)C

Solubility

In vitro
Batch:

DMSO : 3 mg/mL (7.03 mM)
(Moisture-contaminated DMSO may reduce solubility. Use fresh, anhydrous DMSO.)

Water : Insoluble

Ethanol : Insoluble

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Mass Concentration Volume Molecular Weight

In vivo
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Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O, mix and clarify.

Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.

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Mechanism of Action

In vitro
Lupeol is a multi-target agent with immense anti-inflammatory potential targeting key molecular pathways which involve nuclear factor kappa B (NFκB), cFLIP, Fas, Kras, phosphatidylinositol-3-kinase (PI3K)/Akt and Wnt/β-catenin in a variety of cells. This compound can induce apoptosis of human promyelotic HL-60 leukemia cells and induce the formation of hypodiploid nuclei and fragmentation of DNA in a dose and time dependent manner. It induces death of cancer cell lines of various histopathological origins, including T-lymphoblastic leukemia CEM (IC50 = 50 μM), breast carcinoma MCF-7 (IC50 = 50 μM), lung carcinoma A-549 (IC50 = 50 μM), multiple myeloma RPMI 8226 (IC50 = 50 μM), cervical carcinoma HeLa (IC50 = 37 μM), and malignant melanoma G361 (IC50 = 50 μM) when treated for 72 h. This agent also inhibits the proliferation of the ERα-negative breast cancer cells MDA-MB-231. This chemical (50-30 μg/ml) exhibits anti-angiogenic property in an in vitro tube formation model of human umbilical venous endothelial cells. It inhibits the PI3K/Akt, NFκB signaling network, and decreases the activity of Ras protein (GTP-bound Ras) in pancreatic cancer cells. The compound modulates the microtubule assembly and the protein level of its regulatory molecules such as Stathmin and Survivin in prostate cancer cells thus causing G2/M cell cycle arrest[1]. It has been shown to act as a potent inhibitor of protein kinases and serine proteases and inhibit the activity of DNA topoisomerase II, a target for anticancer chemotherapy[2].
In vivo
Topical application of Lupeol decreases myeloperoxidase levels thus causing reduction in cell infiltration into inflamed tissues in mice. Oral administration of this compound (12.5-200 mg/kg) results in the significant reduction in CD4+ T and CD8+ T cell counts and the level of cytokines (IL-2, IFN-gamma and IL-4) in arthritic mice. Its administration causes a significant reduction in cellularity and eosinophil levels in the broncho-alveolar fluid. It also exerts its wound healing effect by decreasing the level of monocytes and docking with GSK3β protein. For cancer, this agent significantly inhibits the NFκB translocation and its DNA binding activity in a mouse model of skin tumorigenesis. It inhibits growth of highly metastatic tumors of human melanoma origin by modulating ratio of Bcl-2 and Bax protein levels in vitro and in vivo. Thus, this compound itself being non-toxic to normal cells could be used as a chemopreventive as well chemotherapeutic agent against skin cancer. It has been shown to inhibit the generation of ROS and restore the depleted antioxidant levels within prostatic tissue of androgen pretreated mice. This chemical is a non-toxic but highly potent chemopreventive and chemotherapeutic agent[1].
References

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