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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]

Lanosterol
Lanosterol skeletal.svg
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

Role in biosynthesis of other steroidsEdit

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.

BiosynthesisEdit

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)

See alsoEdit

ReferencesEdit

  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.

External linksEdit