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Lanosterol (Synonyms: 8,24-Lanostadien-3β-ol, 3β-hydroxy-8,24-Lanostadiene, NSC 60677)

Catalog No.GC19477 Copy One-Click Copy Product Info

Lanosterol is a triterpenoid intermediate in the biosynthesis of cholesterol, which can induce the ubiquitination and degradation of HMG CoA reductase.

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Lanosterol  Chemical Structure

Cas No.: 79-63-0

Size Price Stock Qty
1mg
$68.00
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5mg
$170.00
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10mg
$263.00
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25mg
$402.00
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Sample solution is provided at 25 µL, 10mM.



Description of Lanosterol

Lanosterol is a triterpenoid intermediate in the biosynthesis of cholesterol, which can induce the ubiquitination and degradation of HMG CoA reductase [1]. Defects in Lanosterol can lead to various diseases, including the formation of cataracts [2]. Lanosterol can inhibit the aggregation and toxicity of misfolded proteins related to neurodegenerative diseases [3].

In vitro, treatment with Lanosterol (5μM; 24h) significantly inhibited the cell death of dopaminergic neurons induced by 1-methyl-4-phenylpyridine (MPP+), increased autophagy in neurons, and induced uncoupling of mitochondria in neurons [4]. Treatment with Lanosterol (20μM; 48h) increased the endogenous level of 20S proteasome in A549 and Cos-7 cell lines, promoted proteasome degradation of misfolded proteins, and reduced the aggregation of mutant GFP-Δ9CAT protein [5].

In vivo, oral administration of Lanosterol (1 or 2%, w/w; 10 weeks) significantly inhibited the formation of abnormal crypts and multiple crypts in rat colon induced by nitrosomethane (AOM), and 2% Lanosterol significantly increased serum high-density lipoprotein and cholesterol levels [6]. Local ocular administration of Lanosterol (25mM; 6 weeks) improved the clarity of canine lenses and alleviated cataracts [7].

References:
[1] Chen N, et al. Biosynthetic Mechanism of Lanosterol: Cyclization. Angew Chem Int Ed Engl. 2015 Jul 20;54(30):8693-6.
[2] Zhao L, Chen X J, Zhu J, et al. Lanosterol reverses protein aggregation in cataracts[J]. Nature, 2015, 523(7562): 607-611. 
[3] Upadhyay A, Amanullah A, Mishra R, et al. Lanosterol suppresses the aggregation and cytotoxicity of misfolded proteins linked with neurodegenerative diseases[J]. Molecular neurobiology, 2018, 55(2): 1169-1182. 
[4] Lim L, Jackson-Lewis V, Wong L C, et al. Lanosterol induces mitochondrial uncoupling and protects dopaminergic neurons from cell death in a model for Parkinson's disease[J]. Cell Death & Differentiation, 2012, 19(3): 416-427.
[5] Kinger S, Jagtap Y A, Dubey A R, et al. Lanosterol elevates cytoprotective response through induced-proteasomal degradation of aberrant proteins[J]. Biochimica et Biophysica Acta (BBA)-Molecular Cell Research, 2024, 1871(2): 119631. 
[6] Rao C V, Newmark H L, Reddy B S. Chemopreventive effect of farnesol and lanosterol on colon carcinogenesis[J]. Cancer detection and prevention, 2002, 26(6): 419-425.
[7] Zhao L, Chen X J, Zhu J, et al. Lanosterol reverses protein aggregation in cataracts[J]. Nature, 2015, 523(7562): 607-611.

Protocol of Lanosterol

Cell experiment [1]:

Cell lines

Rat hippocampal neuron cells

Preparation Method

Neurons were plated on a wax-dotted coverslip coated with 1mg/ml of poly-D-lysine. Two hours after plating, when neurons had attached, the coverslips were flipped into a six-well plate containing a glia feeder layer. Hippocampal neuron cultures plated on 12mm coverslips were treated for 24h with 10μM 1-methyl-4-phenylpyridinium (MPP+) with or without 5μM cholesterol or 5μM Lanosterol liposome. Cells were washed three times with PBS, then fixed with 4% paraformaldehyde for 20min, followed by permeabilization and blocking in 5% fetal bovine serum in 0.1% TritonX-100 for 30min. TUJ1-positive and TH-positive cells were counted with an Olympus fluorescence microscope with FITC and TRITC filter sets. Every neuron on the 12mm coverslip was counted.

Reaction Conditions

5μM; 24h

Applications

Lanosterol treatment significantly inhibited the cell death of dopaminergic neurons induced by MPP+.
Animal experiment [2]:

Animal models

Weanling male F344 rats (aberrant crypt foci (ACF) model)

Preparation Method

At 7 weeks of age, groups of rats were fed the modified AIN-76A (control) or experimental diets containing 1.5% farnesol, or 1 or 2% Lanosterol. At 8 weeks of age, all animals except the vehicle-treated rats received azoxymethane (AOM) s.c. once weekly for 2 weeks at a dose rate of 15mg/kg body weight per week. Animals intended for vehicle treatment were given an equal volume of normal saline. The rats were continued on control and experimental diets until the termination of the study when they were 17 weeks of age. All animals were sacrificed by CO2 euthanasia. Blood samples were collected from individual rats (AOM-treated) to analyze for cholesterol and High-density lipoprotein.

Dosage form

1 or 2%, w/w; 10 weeks

Applications

Lanosterol treatment significantly inhibited the formation of multiple recessive lesions in rats, and 2% of wool sterol significantly increased the levels of serum high-density lipoprotein and cholesterol.

References:
[1] Lim L, Jackson-Lewis V, Wong L C, et al. Lanosterol induces mitochondrial uncoupling and protects dopaminergic neurons from cell death in a model for Parkinson's disease[J]. Cell Death & Differentiation, 2012, 19(3): 416-427.
[2] Rao C V, Newmark H L, Reddy B S. Chemopreventive effect of farnesol and lanosterol on colon carcinogenesis[J]. Cancer detection and prevention, 2002, 26(6): 419-425.

Chemical Properties of Lanosterol

Cas No. 79-63-0 SDF
Synonyms 8,24-Lanostadien-3β-ol, 3β-hydroxy-8,24-Lanostadiene, NSC 60677
Chemical Name Lanosta-8,24-dien-3-ol, (3β)-
Canonical SMILES C[C@]12C3=C(CC[C@@]1([C@]([C@H](C)CC/C=C(C)/C)([H])CC2)C)[C@@]4([C@@](C(C)([C@@H](O)CC4)C)([H])CC3)C
Formula C₃₀H₅₀O M.Wt 426.72
Solubility DMF: 3 mg/ml,Ethanol : 6 mg/ml Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of Lanosterol

Prepare stock solution
1 mg 5 mg 10 mg
1 mM 2.3435 mL 11.7173 mL 23.4346 mL
5 mM 468.7 μL 2.3435 mL 4.6869 mL
10 mM 234.3 μL 1.1717 mL 2.3435 mL
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Average Rating: 5 ★★★★★ (Based on Reviews and 16 reference(s) in Google Scholar.)

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