Betulin

For research use only.

Catalog No.S4754 Synonyms: betulinol, betuline, betulinic alcohol

Betulin Chemical Structure

CAS No. 473-98-3

Betulin (BE), also known as betulinol, betuline, or betulinic alcohol, is a pentacyclic lupane-type triterpenoid naturally distributed in many plants and displays a broad spectrum of biological and pharmacological properties such as anticancer and chemopreventive activity. Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line.

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Biological Activity

Description Betulin (BE), also known as betulinol, betuline, or betulinic alcohol, is a pentacyclic lupane-type triterpenoid naturally distributed in many plants and displays a broad spectrum of biological and pharmacological properties such as anticancer and chemopreventive activity. Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line.
In vitro

Betulin significantly inhibits cell viability in cervix carcinoma HeLa cells, hepatoma HepG2 cells, lung adenocarcinoma A549 cells, and breast cancer MCF-7 cells with IC50 values ranging from 10 to 15 mg/mL. While betulin exhibits only moderate anticancer activity in other human cancer cells such as hepatoma SK-HEP-1 cells, prostate carcinoma PC-3, and lung carcinoma NCI-H460, with IC50 values ranging from 20 to 60 mg/mL, it shows minor growth inhibition in human erythroleukemia K562 cells (IC50>100 mg/mL). Betulin does not directly trigger mitochondrial cytochrome c release in isolated mitochondria. Bax and Bak are rapidly translocated to the mitochondria 30 min after betulin treatment[1]. In vitro, Betulin inhibits LPS-induced tumor necrosis factor α (TNF-α) and (interleukin) IL-6 levels and up-regulates the level of IL-10. Also Betulin suppresses the phosphorylation of nuclear factor-kB (NF-kB) p65 protein in LPS-stimulated RAW 264.7 cells[2].

In vivo In vivo, Betulin alleviates LPS-induced acute lung injury. Treatment with Betulin diminishes pro-inflammatory cytokines, myeloperoxidase activity and bacterial loads in lung tissue during gramnegative pneumonia. In HFD-fed apoE−/− mice, betulin administration significantly reduces lesions in en face aortas and aortic sinuses. Furthermore, betulin administration significantly increases ABCA1 expression and suppresses macrophage positive areas in the aortic sinuses. Moreover, betulin administration improves plasma lipid profiles and enhances fecal cholesterol excretion in the mice[3].

Protocol

Animal Research:[2]
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  • Animal Models: C57BL/6J male mice aged 8 weeks
  • Dosages: 4 or 8 mg/kg
  • Administration: i.p.
    (Only for Reference)

Solubility (25°C)

In vitro DMSO 22 mg/mL (49.69 mM)
Water Insoluble
Ethanol Insoluble

* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Chemical Information

Molecular Weight 442.72
Formula

C30H50O2

CAS No. 473-98-3
Storage powder
in solvent
Synonyms betulinol, betuline, betulinic alcohol
Smiles CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)CO

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Clinical Trial Information

NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT01657292 Completed Drug: Oleogel-S10 ointment|Device: Octenilin® wound gel Burns Birken AG|Amryt Pharma August 2012 Phase 3

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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID