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Lanosterol

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Lanosterol
Ball-and-stick model of lanosterol
Names
IUPAC name
Lanosta-8,24-dien-3β-ol
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)
2226449
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.001.105Edit this at Wikidata
EC Number
  • 201-214-9
KEGG
MeSH Lanosterol
UNII
  • InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1checkY
    Key: CAHGCLMLTWQZNJ-BQNIITSRSA-NcheckY
  • InChI=1/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1
    Key: CAHGCLMLTWQZNJ-BQNIITSRBP
  • C[C@H](CCC=C(C)C)[C@H]1CC[C@]2(C)C1CCC3=C2CC[C@H]4C(C)(C)[C@@H](O)CC[C@]34C
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).

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

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The biosynthesis of lanosterol has been intensively investigated.[2]

Description Illustration Enzyme
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.

Simplified version of the lanosterol synthesis pathway with the intermediatesisopentenyl pyrophosphate(IPP),dimethylallyl pyrophosphate(DMAPP),geranyl pyrophosphate(GPP), andsqualeneshown. Some intermediates are omitted.

Research as an eye drop supplement

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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

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References

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  1. ^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.
  2. ^abcNes, W. David (2011)."Biosynthesis of cholesterol and other sterols".Chemical Reviews.111(10): 6423–6451.doi:10.1021/cr200021m.PMC3191736.
  3. ^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.
  4. ^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.
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