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Revision as of 03:50, 28 October 2010 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - updated 'UNII_Ref') per Chem/Drugbox validation (report errors or bugs)← Previous edit		Latest revision as of 03:31, 19 August 2024 edit undoOAbot (talk | contribs)Bots441,761 editsm Open access bot: pmc updated in citation with #oabot.
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	{{chembox		{{chembox
			| Verifiedfields = changed
	| verifiedrevid = 310564561
			| Watchedfields = changed
			| verifiedrevid = 393354387
	| ImageFile = Lanosterol skeletal.svg		| ImageFile = Lanosterol skeletal.svg
	| ImageSize =		| ImageSize = 250
	| ImageFile2 = Lanosterol-3D-sticks.png		| ImageFile2 = Lanosterol molecule ball.png
			| ImageSize2 = 250
	| IUPACName = lanosta-8,24-dien-3-ol
			| ImageAlt2 = Ball-and-stick model of lanosterol
	| OtherNames =
			| IUPACName = Lanosta-8,24-dien-3β-ol
	| Section1 = {{Chembox Identifiers
			| SystematicName = (1''R'',3a''R'',5a''R'',7''S'',9a''S'',11a''R'')-3a,6,6,9a,11a-Pentamethyl-1--2,3,3a,4,5,5a,6,7,8,9,9a,10,11,11a-tetradecahydro-1''H''-cyclopentaphenanthren-7-ol
	| CASNo_Ref = {{cascite|correct|CAS}}
			| OtherNames =
			|Section1={{Chembox Identifiers
			| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 79-63-0		| CASNo = 79-63-0
	| PubChem = 4861		| Beilstein = 2226449
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| SMILES = C(CCC=C(C)C)1CC<br>2(C)C1CCC3=C2CC<br>4C(C)(C)(O)CC34C
			| ChEBI = 16521
	| MeSHName = Lanosterol
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
			| ChEMBL = 225111
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| ChemSpiderID = 216175
			| DrugBank = DB03696
			| EC_number = 201-214-9
			| IUPHAR_ligand = 2746
			| KEGG = C01724
			| MeSHName = Lanosterol
			| PubChem = 246983
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = 1J05Z83K3M
			| 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
			| InChIKey = CAHGCLMLTWQZNJ-BQNIITSRBP
			| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			| StdInChI = 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
			| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
			| StdInChIKey = CAHGCLMLTWQZNJ-BQNIITSRSA-N
			| SMILES = C(CCC=C(C)C)1CC2(C)C1CCC3=C2CC4C(C)(C)(O)CC34C
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| Formula = C<sub>30</sub>H<sub>50</sub>O		| Formula = C<sub>30</sub>H<sub>50</sub>O
	| MolarMass = 426.71 g/mol		| MolarMass = 426.71 g/mol
			| Appearance =
	| ExactMass = 426.386166
	| Appearance =		| Density =
	| Density =		| MeltingPtC = 138 to 140
			| MeltingPt_notes =
	| MeltingPt = 138-140 °C
	| BoilingPt =		| BoilingPt =
	}}
	| Section3 = {{Chembox Hazards
	| Solubility =
	| MainHazards =
	| FlashPt =
	| Autoignition =
	}}		}}
			|Section3={{Chembox Hazards
			| MainHazards =
			| FlashPt =
			| AutoignitionPt =
			}}
	}}		}}
			'''Lanosterol''' is a ] ] and is the compound from which all animal and fungal ]s are derived. By contrast, plant steroids are produced via ].<ref>{{cite journal|last1=Schaller|first1=Hubert|title=The role of sterols in plant growth and development|journal=Progress in Lipid Research|date=May 2003|volume=42|issue=3|pages=163–175|doi=10.1016/S0163-7827(02)00047-4|pmid=12689617}}</ref> In the eyes of vertebrates, lanosterol is a natural constituent, having a role in maintaining health of the ]. Lanosterol is the precursor to ].<ref name=Nes/>
	'''Lanosterol''' is a tetracyclic ], which is the compound from which all ]s are derived.
	==Role in creation of steroids==
	Elaboration of lanosterol under enzyme catalysis leads to the core structure of steroids. 14-Demethylation of lanosterol by ] eventually yields ].
	] (IPP), ] (DMAPP), ] (GPP), and ] shown. Some intermediates are omitted.]]
	==Biosynthesis==		==Biosynthesis==
			The biosynthesis of lanosterol has been intensively investigated.<ref name=Nes>{{cite journal |doi=10.1021/cr200021m |title=Biosynthesis of cholesterol and other sterols |date=2011 |last1=Nes |first1=W. David |journal=Chemical Reviews |volume=111 |issue=10 |pages=6423–6451 |pmc=3191736 }}</ref>
	{| class="wikitable"		{| class="wikitable"
	| '''Description''' || '''Illustration''' || '''Enzyme'''		! Description !! Illustration !! Enzyme
	|-		|-
	| Two molecules of ] condense with reduction by ] to form ] || ] || ]		| Two molecules of ] condense with reduction by ] to form ] || ] || ]
	|-		|-
	| Squalene is oxidized to ] (squalene epoxide) || ] || ]		| Squalene is oxidized to ] (squalene epoxide) || ] || ]
	|-		|-
	| 2,3-Oxidosqualene is converted to a protosterol cation and finally to lanosterol || ] || ]		| 2,3-Oxidosqualene is converted to a protosterol cation and finally to lanosterol || ] || ]
	|-		|-
	| (step 2) || ] || (step 2)		| (step 2) || ] || (step 2)
	|}		|}
			Elaboration of lanosterol under enzyme catalysis leads to other steroids. 14-] of lanosterol by ] eventually yields ].
			] (IPP), ] (DMAPP), ] (GPP), and ] shown. Some intermediates are omitted.]]
			==Research as an eye drop supplement==
			As a molecule naturally enriched in the eye lens, lanosterol is a component involved in maintenance of lens clarity.<ref name="das">{{cite journal |vauthors=Daszynski DM, Santhoshkumar P, Phadte AS, Sharma KK, Zhong HA, Lou MF, Kador PF|display-authors=3 |title=Failure of oxysterols such as lanosterol to restore lens clarity from cataracts |journal=Scientific Reports |volume=9 |issue=1 |pages=8459 |date=June 2019 |pmid=31186457 |pmc=6560215 |doi=10.1038/s41598-019-44676-4}}</ref><ref name="xu">{{cite journal |vauthors=Xu J, Fu Q, Chen X, Yao K |title=Advances in pharmacotherapy of cataracts |journal=Annals of Translational Medicine |volume=8 |issue=22 |pages=1552 |date=November 2020 |pmid=33313297 |pmc=7729355 |doi=10.21037/atm-20-1960|doi-access=free}}</ref> Its proposed ] is to inhibit the aggregation of ], which contribute to the clouding of vision by forming ]s.<ref name=das/><ref name=xu/>
			Lanosterol is under research for its potential as a therapeutic additive in ]s to inhibit the aggregation of crystallin proteins and dissolve ]s.<ref name=das/><ref name=xu/> However, supplemental lanosterol in eye drops appears to have limited solubility and poor ] in the eye, and has not proved effective for inhibiting cataracts, as of 2020.<ref name=das/><ref name=xu/>
	==See also==		==See also==
	*]		*]
	*]		*]
			*Other tetracyclic ]s: ], ], ], and ].<ref name=Nes/>
	==References==
	*{{cite journal
	| author = ], W. E. Russey, P. R. Ortiz de Montellano
	| title = 2,3-Oxidosqualene, an Intermediate in the Biological Synthesis of Sterols from Squalene
	| journal = ]
	| volume = 88
	| issue = 20
	| year = 1966
	| pages = 4750–4751
	| doi = 10.1021/ja00972a056}}
	*{{cite journal
	| author = I. Abe, M. Rohmer, G. D. Prestwich
	| title = Enzymatic cyclization of squalene and oxidosqualene to sterols and triterpenes
	| journal = ]
	| volume = 93
	| issue = 6
	| year = 1993
	| pages = 2189–2206
	| doi = 10.1021/cr00022a009}}
	*{{cite journal
	| author = ], ], O. Jeger, D. Arigoni
	| title = Zur Kenntnis der Triterpene. 190. Mitteilung. Eine stereochemische Interpretation der biogenetischen Isoprenregel bei den Triterpenen
	| journal = ]
	| volume = 38
	| issue = 7
	| year = 1955
	| pages = 1890–1904
	| doi = 10.1002/hlca.19550380728}}
	==External links==		==References==
			{{Reflist}}
	{{Sterols}}		{{Sterols}}
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	]