Lupeol

Catalog No.S3614 Synonyms: (3β,13ξ)-Lup-20(29)-en-3-ol, Clerodol, Monogynol B, Fagarasterol, Farganasterol

For research use only.

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 Chemical Structure

CAS No. 545-47-1

Selleck's Lupeol has been cited by 1 Publication

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Biological Activity

Description 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.
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. Lupeol 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. Lupeol 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. Lupeol also inhibits the proliferation of the ERα-negative breast cancer cells MDA-MB-231. Lupeol (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. Lupeol 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]. Lupeol 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 Lupeol (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. Lupeol 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, Lupeol 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, Lupeol itself being non-toxic to normal cells could be used as a chemopreventive as well chemotherapeutic agent against skin cancer. Lupeol has been shown to inhibit the generation of ROS and restore the depleted antioxidant levels within prostatic tissue of androgen pretreated mice. Lupeol is a non-toxic but highly potent chemopreventive and chemotherapeutic agent[1].

Protocol (from reference)

Cell Research:

[3]

  • Cell lines: LNCaP cells
  • Concentrations: 20 μM
  • Incubation Time: 48 h
  • Method:

    Microarray analysis: LNCaP cells were treated with subtoxic dose (20 μM) of Lupeol. After 48 h of incubation, cells were harvested and RNA was isolated by using RNeasy kit. Next, 4 μg of RNA was enzymatically converted into complementary RNA, labeled and hybridized with the microarrays followed by detection with the chemiluminescent reagents and X-ray film.

Animal Research:

[2]

  • Animal Models: CD-1 mice
  • Dosages: 1 or 2 mg/0.2 ml acetone/animal, w/v
  • Administration: topical

Solubility (25°C)

In vitro

Chemical Information

Molecular Weight 426.72
Formula

C30H50O

CAS No. 545-47-1
Storage 3 years -20°C powder
2 years -80°C in solvent
Smiles CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)C

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