Lanosterol
Names | |
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IUPAC name
Lanosta-8,24-dien-3β-ol
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Systematic IUPAC name
(1R,3aR,5aR,7S,9aS,11aR)-3a,6,6,9a,11a-Pentamethyl-1-[(2R)-6-methylhept-5-en-2-yl]-2,3,3a,4,5,5a,6,7,8,9,9a,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-ol | |
Identifiers | |
3D model (
JSmol ) |
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2226449 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard
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100.001.105 |
EC Number |
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IUPHAR/BPS |
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KEGG | |
MeSH | Lanosterol |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C30H50O | |
Molar mass | 426.71 g/mol |
Melting point | 138 to 140 °C (280 to 284 °F; 411 to 413 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Lanosterol is a
Role in the biosynthesis of other steroids
Elaboration of lanosterol under enzyme catalysis leads to the core structure of steroids. 14-Demethylation of lanosterol by CYP51 eventually yields cholesterol.[2]
Biosynthesis
Description | Illustration | Enzyme |
Two molecules of NADPH to form squalene |
squalene synthase
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Squalene is oxidized to 2,3-oxidosqualene (squalene epoxide) |
squalene monooxygenase | |
2,3-Oxidosqualene is converted to a protosterol cation and finally to lanosterol | lanosterol synthase | |
(step 2) | (step 2) |
Research
Lanosterol has been identified as a key component in maintaining eye lens clarity.[3] Pre-clinical research has identified Lanosterol as a possible agent for the reversal and prevention of cataracts.[4] In vivo experiments on dogs showed significant reversal of cataracts within 6 weeks of lanosterol injection.[5] In 2018, Lanosterol was shown to improve lens clarity in cells with lens clouding due to aging or physical stressors.[6] A subsequent study in 2022 by Kehao Wang, Hoshino, Kentaro Uesugi, Naoto Yagi, Pierscionek and Andley found positive results on the optics of the lens in mice with cataracts.[7]
Use
Lanosterol is an ingredient in over-the-counter ophthalmic products to prevent cataracts. However, the solubility and bioavailability of lanosterol is not conducive to aqueous formulations.[8] Heliostatix Biotechnology claims to have a method of solubilizing lanosterol for use in aqueous products.[9]
See also
- Cycloartenol
- CYP51
References
Further reading
- Corey, E. J.; Russey, William E.; de Montellano, Paul R. Ortiz (October 1966). "2,3-Oxidosqualene, an Intermediate in the Biological Synthesis of Sterols from Squalene". Journal of the American Chemical Society. 88 (20): 4750–4751. PMID 5918046.
- Abe, Ikuro.; Rohmer, Michel.; Prestwich, Glenn D. (1 September 1993). "Enzymatic cyclization of squalene and oxidosqualene to sterols and triterpenes". Chemical Reviews. 93 (6): 2189–2206. .
- Eschenmoser, A.; Ruzicka, L.; Jeger, O.; Arigoni, D. (1955). "Zur Kenntnis der Triterpene. 190. Mitteilung. Eine stereochemische Interpretation der biogenetischen Isoprenregel bei den Triterpenen" [For knowledge of the triterpenes. Part 190. A stereochemical interpretation of the biogenetic isoprene rule in triterpenes]. Helvetica Chimica Acta (in German). 38 (7): 1890–1904. .
- Wang, Kehao; Hoshino, Masato; Uesugi, Kentaro; Yagi, Naoto; Pierscionek, Barbara K.; Andley, Usha P. (2022-05-16). "Oxysterol Compounds in Mouse Mutant αA- and αB-Crystallin Lenses Can Improve the Optical Properties of the Lens". Investigative Ophthalmology & Visual Science. 63 (5): 15. PMID 35575904.