Lanosterol
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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 | |
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ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.001.105 |
EC Number |
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KEGG | |
MeSH | Lanosterol |
PubChemCID
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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 theirstandard state(at 25 °C [77 °F], 100 kPa).
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Lanosterolis atetracyclictriterpenoidand is the compound from which all animal and fungalsteroidsare derived. By contrast, plant steroids are produced viacycloartenol.[1]In the eyes of vertebrates, lanosterol is a natural constituent, having a role in maintaining health of thelens.Lanosterol is the precursor tocholesterol.[2]
Biosynthesis
[edit]The biosynthesis of lanosterol has been intensively investigated.[2]
Description | Illustration | Enzyme |
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Two molecules offarnesyl pyrophosphatecondense with reduction byNADPHto formsqualene | ![]() |
squalene synthase |
Squalene is oxidized to2,3-oxidosqualene(squalene epoxide) | ![]() |
squalene monooxygenase |
2,3-Oxidosqualene is converted to a protosterol cation and finally to lanosterol | ![]() |
lanosterol synthase |
(step 2) | ![]() |
(step 2) |
Elaboration of lanosterol under enzyme catalysis leads to other steroids. 14-Demethylationof lanosterol byCYP51eventually yieldscholesterol.
![](https://upload.wikimedia.org/wikipedia/commons/thumb/1/18/Sterol_synthesis.svg/350px-Sterol_synthesis.svg.png)
Research as an eye drop supplement
[edit]As a molecule naturally enriched in the eye lens, lanosterol is a component involved in maintenance of lens clarity.[3][4]Its proposedmechanism of actionis to inhibit the aggregation ofcrystallin proteins,which contribute to the clouding of vision by formingcataracts.[3][4]
Lanosterol is under research for its potential as a therapeutic additive ineye dropsto inhibit the aggregation of crystallin proteins and dissolvecataracts.[3][4]However, supplemental lanosterol in eye drops appears to have limited solubility and poorbioavailabilityin the eye, and has not proved effective for inhibiting cataracts, as of 2020.[3][4]
See also
[edit]- Cycloartenol
- CYP51
- Other tetracyclictriterpenes:cycloartenol,euphol,tirucallol,andcucurbitacin.[2]
References
[edit]- ^Schaller, Hubert (May 2003). "The role of sterols in plant growth and development".Progress in Lipid Research.42(3): 163–175.doi:10.1016/S0163-7827(02)00047-4.PMID12689617.
- ^abcNes, W. David (2011)."Biosynthesis of cholesterol and other sterols".Chemical Reviews.111(10): 6423–6451.doi:10.1021/cr200021m.PMC3191736.
- ^abcdDaszynski DM, Santhoshkumar P, Phadte AS, et al. (June 2019)."Failure of oxysterols such as lanosterol to restore lens clarity from cataracts".Scientific Reports.9(1): 8459.doi:10.1038/s41598-019-44676-4.PMC6560215.PMID31186457.
- ^abcdXu J, Fu Q, Chen X, Yao K (November 2020)."Advances in pharmacotherapy of cataracts".Annals of Translational Medicine.8(22): 1552.doi:10.21037/atm-20-1960.PMC7729355.PMID33313297.