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Lanosterol skeletal.svg
Ball-and-stick model of lanosterol
IUPAC name
Preferred IUPAC name
3D model (JSmol)
ECHA InfoCard 100.001.105 Edit this at Wikidata
MeSH Lanosterol
  • 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 ?N
  • 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
  • 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
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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Infobox references

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 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.

Simplified version of the lanosterol synthesis pathway with the intermediates isopentenyl pyrophosphate (IPP), dimethylallyl pyrophosphate (DMAPP), geranyl pyrophosphate (GPP), and squalene shown. Some intermediates are omitted.


Description Illustration Enzyme
Two molecules of farnesyl pyrophosphate condense with reduction by NADPH to form squalene Cholesterol-Synthesis-Reaction10.png squalene synthase
Squalene is oxidized to 2,3-oxidosqualene (squalene epoxide) Squalene epoxide biosynthesis.png squalene monooxygenase
2,3-Oxidosqualene is converted to a protosterol cation and finally to lanosterol Cholesterol-Synthesis-Reaction12.png lanosterol synthase
(step 2) Cholesterol-Synthesis-Reaction13.png (step 2)


Lanosterol has been identified as a key component in maintaining eye lens clarity.[2] Pre-clinical research has identified Lanosterol as a possible agent for the reversal and prevention of cataracts. In vivo experiments on dogs showed significant reversal of cataracts within 6 weeks of lanosterol injection.[3] In 2018, Lanosterol was shown to improve lens clarity in subjects with lens clouding due to aging or physical stressors.[4]

See also


  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. PMID 12689617.
  2. ^ Huff, M; Telford, D (July 2005). "Lord of the rings - the mechanism for oxidosqualene:lanosterol cyclase becomes crystal clear". Trends in Pharmacological Sciences. 26 (7): 335-340. doi:10.1016/ PMID 15951028.
  3. ^ Zhao, Ling; Chen, Xiang-Jun; Zhu, Jie; Xi, Yi-Bo; Yang, Xu; Hu, Li-Dan; Ouyang, Hong; Patel, Sherrina H.; Jin, Xin; Lin, Danni; Wu, Frances; Flagg, Ken; Cai, Huimin; Li, Gen; Cao, Guiqun; Lin, Ying; Chen, Daniel; Wen, Cindy; Chung, Christopher; Wang, Yandong; Qiu, Austin; Yeh, Emily; Wang, Wenqiu; Hu, Xun; Grob, Seanna; Abagyan, Ruben; Su, Zhiguang; Tjondro, Harry Christianto; Zhao, Xi-Juan; Luo, Hongrong; Hou, Rui; Jefferson, J.; Perry, P.; Gao, Weiwei; Kozak, Igor; Granet, David; Li, Yingrui; Sun, Xiaodong; Wang, Jun; Zhang, Liangfang; Liu, Yizhi; Yan, Yong-Bin; Zhang, Kang (July 2015). "Lanosterol reverses protein aggregation in cataracts". Nature. 523 (7562): 607-611. Bibcode:2015Natur.523..607Z. doi:10.1038/nature14650. PMID 26200341. S2CID 4469138.
  4. ^ Shen, Xinyue; Zhu, Manhui; Kang, Lihua; Tu, Yuanyuan; Li, Lele; Zhang, Rutan; Qin, Bai; Yang, Mei; Guan, Huaijin (11 July 2018). "Lanosterol Synthase Pathway Alleviates Lens Opacity in Age-Related Cortical Cataract". Journal of Ophthalmology. 2018: 1-9. doi:10.1155/2018/4125893. PMC 6079410. PMID 30116630.

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. 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.

External links

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