Lanosterol

Lanosterol
Ball-and-stick model of lanosterol
Names
IUPAC name
lanosta-8,24-dien-3-ol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.105
MeSH Lanosterol
UNII
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 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 creation of 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.

Recent research suggests that lanosterol might be instrumental in prevention of formation of cataracts in mammals.[2]

Biosynthesis

DescriptionIllustrationEnzyme
Two molecules of farnesyl pyrophosphate condense with reduction by NADPH to form squalenesqualene synthase
Squalene is oxidized to 2,3-oxidosqualene (squalene epoxide)squalene monooxygenase
2,3-Oxidosqualene is converted to a protosterol cation and finally to lanosterollanosterol synthase
(step 2)(step 2)

See also

References

  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.
  2. ↑ Ling Zhao; Xiang-Jun Chen; Jie Zhu; Yi-Bo Xi; Xu Yang; Li-Dan Hu; Hong Ouyang; Sherrina H. Patel; Xin Jin; Danni Lin; Frances Wu; Ken Flagg; Huimin Cai; Gen Li; Guiqun Cao; Ying Lin; Daniel Chen; Cindy Wen; Christopher Chung; Yandong Wang; Austin Qiu; Emily Yeh; Wenqiu Wang; Xun Hu; Seanna Grob; et al. (July 2015). "Lanosterol reverses protein aggregation in cataracts". Nature. doi:10.1038/nature14650.
  • E. J. Corey, W. E. Russey, P. R. Ortiz de Montellano (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.
  • I. Abe; M. Rohmer; G. D. Prestwich (1993). "Enzymatic cyclization of squalene and oxidosqualene to sterols and triterpenes". Chemical Reviews. 93 (6): 2189–2206. doi:10.1021/cr00022a009.
  • A. Eschenmoser, L. Ruzicka, O. Jeger, D. Arigoni (1955). "Zur Kenntnis der Triterpene. 190. Mitteilung. Eine stereochemische Interpretation der biogenetischen Isoprenregel bei den Triterpenen". Helvetica Chimica Acta. 38 (7): 1890–1904. doi:10.1002/hlca.19550380728.
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