Contents

Lanosterol

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
CAS Number	79-63-0 Y
3D model (JSmol)	Interactive image
Beilstein Reference	2226449
ChEBI	CHEBI:16521 Y
ChEMBL	ChEMBL225111 Y
ChemSpider	216175 Y
DrugBank	DB03696
ECHA InfoCard	100.001.105
EC Number	201-214-9
IUPHAR/BPS	2746
KEGG	C01724
MeSH	Lanosterol
PubChem CID	246983
UNII	1J05Z83K3M Y
CompTox Dashboard (EPA)	DTXSID1040744
InChI 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/s1 Y Key: CAHGCLMLTWQZNJ-BQNIITSRSA-N Y 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
SMILES 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
Chemical formula	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). N verify (what is YN ?) Infobox references

Chemical compound

Lanosterol is a tetracyclic triterpenoid and is the compound from which all animal and fungal steroids are derived. By contrast, plant steroids are produced via cycloartenol.^[1]

Role in the biosynthesis of other steroids[edit]

Elaboration of lanosterol under enzyme catalysis leads to the core structure of steroids. 14-Demethylation of lanosterol by CYP51 eventually yields cholesterol.^[2]

Biosynthesis[edit]

Description	Illustration	Enzyme
Two molecules of farnesyl pyrophosphate condense with reduction by NADPH to form squalene		squalene synthase
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[edit]

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[edit]

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[edit]

• Cycloartenol
• CYP51

References[edit]

Further reading[edit]

• 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. doi:10.1021/ja00972a056. 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. doi:10.1021/cr00022a009.
• 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. doi:10.1002/hlca.19550380728.
• 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. doi:10.1167/iovs.63.5.15. ISSN 1552-5783. PMC 9123516. PMID 35575904.

External links[edit]